CN107428766B - Compound, photosensitive resin composition containing same and color filter - Google Patents
Compound, photosensitive resin composition containing same and color filter Download PDFInfo
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- CN107428766B CN107428766B CN201580077258.4A CN201580077258A CN107428766B CN 107428766 B CN107428766 B CN 107428766B CN 201580077258 A CN201580077258 A CN 201580077258A CN 107428766 B CN107428766 B CN 107428766B
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- compound
- photosensitive resin
- resin composition
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 131
- 239000011342 resin composition Substances 0.000 title claims abstract description 67
- 239000000126 substance Substances 0.000 claims abstract description 227
- 239000000049 pigment Substances 0.000 claims description 28
- 239000003999 initiator Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 11
- 229920005989 resin Polymers 0.000 claims description 11
- 239000001046 green dye Substances 0.000 claims description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 238000002834 transmittance Methods 0.000 claims description 4
- 239000001052 yellow pigment Substances 0.000 claims description 4
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims 2
- 150000004706 metal oxides Chemical class 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 73
- 238000003786 synthesis reaction Methods 0.000 description 73
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 32
- 239000007787 solid Substances 0.000 description 24
- -1 nitro, cyano, amino Chemical group 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 239000007788 liquid Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 238000004440 column chromatography Methods 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 13
- YCOZMDJJLOTREI-UHFFFAOYSA-N 3,4,6-trichloro-5-(2,6-dimethoxyphenoxy)benzene-1,2-dicarbonitrile Chemical compound ClC1=C(C(C#N)=C(C(=C1Cl)OC1=C(C=CC=C1OC)OC)Cl)C#N YCOZMDJJLOTREI-UHFFFAOYSA-N 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 11
- 239000000975 dye Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000004593 Epoxy Substances 0.000 description 10
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 10
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 10
- LHTVMBMETNGEAN-UHFFFAOYSA-N pent-1-en-1-ol Chemical compound CCCC=CO LHTVMBMETNGEAN-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 239000004246 zinc acetate Substances 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 9
- 239000004925 Acrylic resin Substances 0.000 description 8
- 229920000178 Acrylic resin Polymers 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- VSTXCZGEEVFJES-UHFFFAOYSA-N 1-cycloundecyl-1,5-diazacycloundec-5-ene Chemical compound C1CCCCCC(CCCC1)N1CCCCCC=NCCC1 VSTXCZGEEVFJES-UHFFFAOYSA-N 0.000 description 6
- XQLMIXAHLGHYRM-UHFFFAOYSA-N Clc1c(Cl)c(C#N)c(C#N)c(Cl)c1Oc1ccccc1-c1ccccc1 Chemical compound Clc1c(Cl)c(C#N)c(C#N)c(Cl)c1Oc1ccccc1-c1ccccc1 XQLMIXAHLGHYRM-UHFFFAOYSA-N 0.000 description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 5
- OQHXZZGZASQSOB-UHFFFAOYSA-N 3,4,5,6-tetrachlorobenzene-1,2-dicarbonitrile Chemical compound ClC1=C(Cl)C(Cl)=C(C#N)C(C#N)=C1Cl OQHXZZGZASQSOB-UHFFFAOYSA-N 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- ICKZBUCPDQLYFF-UHFFFAOYSA-N 3,4,6-trichloro-5-(3-methylbutoxy)benzene-1,2-dicarbonitrile Chemical compound ClC1=C(C(C#N)=C(C(=C1Cl)OCCC(C)C)Cl)C#N ICKZBUCPDQLYFF-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- REAOHBGEAROASO-UHFFFAOYSA-N 3,4,6-trichloro-5-(4-methoxyphenoxy)benzene-1,2-dicarbonitrile Chemical compound C1=CC(OC)=CC=C1OC1=C(Cl)C(Cl)=C(C#N)C(C#N)=C1Cl REAOHBGEAROASO-UHFFFAOYSA-N 0.000 description 3
- OHNZJDALBVYSKL-UHFFFAOYSA-N 4-(2-tert-butylphenoxy)-3,5,6-trichlorobenzene-1,2-dicarbonitrile Chemical compound C(C)(C)(C)C1=C(OC=2C(=C(C(C#N)=C(C=2Cl)Cl)C#N)Cl)C=CC=C1 OHNZJDALBVYSKL-UHFFFAOYSA-N 0.000 description 3
- YEXYWEKNTNVLDO-UHFFFAOYSA-N 4-(4-tert-butylphenoxy)-3,5,6-trichlorobenzene-1,2-dicarbonitrile Chemical compound C(C)(C)(C)C1=CC=C(OC=2C(=C(C(C#N)=C(C=2Cl)Cl)C#N)Cl)C=C1 YEXYWEKNTNVLDO-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 description 2
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical compound COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 2
- SFAMKDPMPDEXGH-UHFFFAOYSA-N 2-hydroxyethyl propanoate Chemical compound CCC(=O)OCCO SFAMKDPMPDEXGH-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 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 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- WBODDOZXDKQEFS-UHFFFAOYSA-N 1,2,3,4-tetramethyl-5-phenylbenzene Chemical group CC1=C(C)C(C)=CC(C=2C=CC=CC=2)=C1C WBODDOZXDKQEFS-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
- PYKHTOHGCVJJMZ-UHFFFAOYSA-N 1-(4-phenylsulfanylphenyl)butan-1-one Chemical compound C1=CC(C(=O)CCC)=CC=C1SC1=CC=CC=C1 PYKHTOHGCVJJMZ-UHFFFAOYSA-N 0.000 description 1
- IFIRNFOLTIJZIL-UHFFFAOYSA-N 1-(4-phenylsulfanylphenyl)butane-1,2-dione Chemical compound C1=CC(C(=O)C(=O)CC)=CC=C1SC1=CC=CC=C1 IFIRNFOLTIJZIL-UHFFFAOYSA-N 0.000 description 1
- VQYUAFDBUVMFKD-UHFFFAOYSA-N 1-(4-phenylsulfanylphenyl)octane-1,2-dione Chemical compound C1=CC(C(=O)C(=O)CCCCCC)=CC=C1SC1=CC=CC=C1 VQYUAFDBUVMFKD-UHFFFAOYSA-N 0.000 description 1
- IMDHDEPPVWETOI-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-2,2,2-trichloroethanone Chemical compound CC(C)(C)C1=CC=C(C(=O)C(Cl)(Cl)Cl)C=C1 IMDHDEPPVWETOI-UHFFFAOYSA-N 0.000 description 1
- VMCRQYHCDSXNLW-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-2,2-dichloroethanone Chemical compound CC(C)(C)C1=CC=C(C(=O)C(Cl)Cl)C=C1 VMCRQYHCDSXNLW-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical group CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
- 150000003903 lactic acid esters Chemical class 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
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- PPFNAOBWGRMDLL-UHFFFAOYSA-N methyl 2-ethoxyacetate Chemical compound CCOCC(=O)OC PPFNAOBWGRMDLL-UHFFFAOYSA-N 0.000 description 1
- YVWPDYFVVMNWDT-UHFFFAOYSA-N methyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OC YVWPDYFVVMNWDT-UHFFFAOYSA-N 0.000 description 1
- AKWHOGIYEOZALP-UHFFFAOYSA-N methyl 2-methoxy-2-methylpropanoate Chemical compound COC(=O)C(C)(C)OC AKWHOGIYEOZALP-UHFFFAOYSA-N 0.000 description 1
- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- AGADEVQOWQDDFX-UHFFFAOYSA-N methyl 3-oxopropanoate Chemical compound COC(=O)CC=O AGADEVQOWQDDFX-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 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
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 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 1
- YDZANNORUSYHFB-UHFFFAOYSA-N phenacyl benzoate Chemical compound C=1C=CC=CC=1C(=O)COC(=O)C1=CC=CC=C1 YDZANNORUSYHFB-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920006391 phthalonitrile polymer Polymers 0.000 description 1
- 229940067265 pigment yellow 138 Drugs 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
Abstract
The invention provides a compound represented by a specific chemical formula, a photosensitive resin composition containing the compound and a color filter manufactured by using the photosensitive resin composition.
Description
Technical Field
The invention relates to a compound, a photosensitive resin composition containing the compound and a color filter.
Background
A color filter manufactured by using a pigment-type photosensitive resin composition has limitations in brightness and contrast ratio due to pigment particle size. In addition, the imaging sensor device requires a small dispersed particle size to form a fine pattern. To meet the demand, attempts have been made to realize a color filter having improved color characteristics (such as brightness, contrast ratio, etc.) by manufacturing a photosensitive resin composition by introducing a dye that does not form particles instead of a pigment.
Therefore, it is necessary to study a suitable compound as a dye for producing a photosensitive resin composition.
Disclosure of Invention
[ technical Direction ]
One embodiment provides a novel compound.
Another embodiment provides a photosensitive resin composition comprising the compound.
Still another embodiment provides a color filter manufactured using the photosensitive resin composition.
[ means for solving the problems ]
One embodiment of the present invention provides a compound represented by chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, the first and second,
m is Cu, Zn, Co or Mo,
R1to R16Independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and
R1to R16At least one of which is represented by chemical formula 2,
[ chemical formula 2]
Wherein, in chemical formula 2,
R17and R18Independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.
Chemical formula 2 may be represented by chemical formula 3.
[ chemical formula 3]
In the chemical formula 3, the first and second,
R17and R18Independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.
R1To R16At least one of which may be represented by chemical formula 2, and R1To R16At least one of which may be represented by one of chemical formulas 4 to 7.
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 6]
[ chemical formula 7]
In chemical formula 6 and chemical formula 7,
L1is a substituted or unsubstituted C1 to C10 alkylene, and
R19is a substituted or unsubstituted C1 to C10 alkyl group.
R1To R4At least one of which may be represented by chemical formula 2, R5To R8At least one of which may be represented by one of chemical formulas 4 to 7, R9To R12At least one of which may be represented by one of chemical formulas 4 to 7, and R13To R16At least one of which may be represented by one of chemical formulas 4 to 7.
R1To R4At least one of which may be represented by chemical formula 2, R5To R8At least one of which may be represented by chemical formula 2, R9To R12At least one of which may be represented by chemical formulas 4 to 7, and R13To R16At least one of which may be represented by one of chemical formulas 4 to 7.
R1To R4At least one of which may be represented by chemical formula 2, R5To R8At least one of which may be represented by one of chemical formulas 4 to 7, R9To R12At least one of which may be represented by chemical formula 2, and R13To R16At least one of which may be represented by one of chemical formulas 4 to 7.
R1To R4At least one of which may be represented by chemical formula 2, R5To R8At least one of which may be represented by chemical formula 2, R9To R12At least one of which may be represented by chemical formula 2, and R13To R16At least one of which may be represented by one of chemical formulas 4 to 7.
R1To R4At least one of which may be represented by chemical formula 2, R5To R8At least one of which may be represented by chemical formula 2, R9To R12ToAt least one of which is represented by chemical formula 2, and R13To R16At least one of which may be represented by chemical formula 2.
The compound represented by chemical formula 1 may be represented by one of chemical formulas 8 to 16.
[ chemical formula 8]
[ chemical formula 9]
[ chemical formula 10]
[ chemical formula 11]
[ chemical formula 12]
[ chemical formula 13]
[ chemical formula 14]
[ chemical formula 15]
[ chemical formula 16]
The compound may be a green dye.
The green dye may have a maximum light transmittance in a wavelength of 445nm to 560 nm.
Another embodiment provides a photosensitive resin composition comprising the compound.
The photosensitive resin composition may further include an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.
The photosensitive resin composition may further include a pigment.
The pigment may be a yellow pigment.
Another embodiment provides a color filter manufactured using the photosensitive resin composition.
Other embodiments of the present invention are included in the following embodiments.
[ advantageous effects ]
The compound according to one embodiment has excellent green spectral characteristics, a high mohr extinction coefficient, and improved organic solvent solubility, and thus may be used as a dye during the preparation of a photosensitive resin composition for a green filter, and a color filter including the dye may have excellent brightness and contrast ratio.
Detailed Description
Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, and the present invention is not limited thereto.
As used herein, the term "substituted", when a specific definition is not otherwise provided, means substituted with a substituent selected from the group consisting of: halogen (F, Br, Cl or I), hydroxy, nitro, cyano, amino (NH)2、NH(R200) Or N (R)201)(R202) Wherein R is200、R201And R202Is the same or different and is independently C1 to C10 alkyl), carbamimidoyl, hydrazine, hydrazone group, carboxyl group, substituted or unsubstituted alkyl group, substituted or unsubstitutedIn place of the functional group of the present invention, an alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic organic group, a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group may be used.
As used herein, when a specific definition is not otherwise provided, the term "alkyl" refers to C1 to C20 alkyl and specifically C1 to C15 alkyl, the term "cycloalkyl" refers to C3 to C20 cycloalkyl and specifically C3 to C18 cycloalkyl, the term "alkoxy" refers to C1 to C20 alkoxy and specifically C1 to C18 alkoxy, the term "aryl" refers to C6 to C20 aryl and specifically C6 to C18 aryl, the term "alkenyl" refers to C2 to C20 alkenyl and specifically C2 to C18 alkenyl, the term "alkylene" refers to C1 to C20 alkylene and specifically C1 to C18 alkylene, and the term "arylene" refers to C6 to C20 arylene and specifically C6 to C16 arylene.
As used herein, "(meth) acrylate" means "acrylate" or "methacrylate" and "(meth) acrylic acid" means "acrylic acid" or "methacrylic acid" when a specific definition is not otherwise provided.
As used herein, the term "combination" when a definition is not otherwise provided means mixing or copolymerization. Further, "copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymer or random copolymer.
In the chemical formulae of the present specification, unless a specific definition is otherwise provided, when a chemical bond is not shown at the position that should be given, the hydrogen bonds at the position.
As used herein, "a" indicates a point of attachment of the same or different atom or chemical formula when a specific definition is not otherwise provided.
One embodiment provides a compound represented by chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, the first and second,
m is Cu, Zn, Co or Mo,
R1to R16Independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and
R1to R16At least one of which is represented by chemical formula 2,
[ chemical formula 2]
Wherein, in chemical formula 2,
R17and R18Independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.
The compound represented by chemical formula 1 has excellent green spectral characteristics and a high molar extinction coefficient. In addition, the compound represented by chemical formula 1 must include a substituent represented by chemical formula 2 and thus may have improved solubility in an organic solvent and show excellent brightness when applied to a color filter.
In one exemplary embodiment, M may be Zn.
Chemical formula 2 may be represented by chemical formula 3.
[ chemical formula 3]
In the chemical formula 3, the first and second,
R17and R18Independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.
The compound represented by chemical formula 1 according to one embodiment must include a substituent represented by chemical formula 2, for example, chemical formula 3 and cause a red shift, and thus the compound represented by chemical formula 1 according to one embodiment shows excellent brightness compared to a composition including a pigment, for example, a green pigment.
In addition, the compound represented by chemical formula 1 according to one embodiment must include a substituent represented by chemical formula 2, for example, chemical formula 3, and show greatly improved solubility in an organic solvent, while the solubility of the phthalocyanine-based dye compound including an amide substituent in an organic solvent is drastically deteriorated.
R1To R16Can be represented by chemical formula 2, and R1To R16At least one of which may be represented by one of chemical formulas 4 to 7.
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 6]
[ chemical formula 7]
In chemical formula 6 and chemical formula 7,
L1is a substituted or unsubstituted C1 to C10 alkylene, and
R19is a substituted or unsubstituted C1 to C10 alkyl group.
For example, L1May be a substituted or unsubstituted methylene group, a substituted or unsubstituted ethylene group, a substituted or unsubstituted propylene group, a substituted or unsubstituted butylene group, a substituted or unsubstituted pentylene group, a substituted or unsubstituted hexylene group, a substituted or unsubstituted heptylene group, a substituted or unsubstituted hexylene groupUnsubstituted octylene, substituted or unsubstituted nonylene, or substituted or unsubstituted decylene.
The compound according to one embodiment includes a substituent represented by one of chemical formulas 4 to 7 in addition to the substituent represented by chemical formula 2 and may increase solubility in an organic solvent and improve coloring characteristics.
For example, in chemical formula 1, R1To R4Can be represented by chemical formula 2, R5To R8At least one of which may be represented by one of chemical formulas 4 to 7, R9To R12At least one of which may be represented by one of chemical formulas 4 to 7, and R13To R16At least one of which may be represented by one of chemical formulas 4 to 7.
For example, in chemical formula 1, R1To R4Can be represented by chemical formula 2, R5To R8At least one of which may be represented by chemical formula 2, R9To R12At least one of which may be represented by one of chemical formulas 4 to 7, and R13To R16At least one of which may be represented by one of chemical formulas 4 to 7.
For example, in chemical formula 1, R1To R4Can be represented by chemical formula 2, R5To R8At least one of which may be represented by one of chemical formulas 4 to 7, R9To R12At least one of which may be represented by chemical formula 2, and R13To R16At least one of which may be represented by one of chemical formulas 4 to 7.
For example, in chemical formula 1, R1To R4Can be represented by chemical formula 2, R5To R8At least one of which may be represented by chemical formula 2, R9To R12At least one of which may be represented by chemical formula 2, and R13To R16At least one of which may be represented by one of chemical formulas 4 to 7.
For example, in chemical formula 1, R1To R4Can be represented by chemical formula 2Shown as R5To R8At least one of which may be represented by chemical formula 2, R9To R12At least one of which may be represented by chemical formula 2, and R13To R16At least one of which may be represented by chemical formula 2.
For example, the compound represented by chemical formula 1 may be represented by one of chemical formulas 8 to 16, but is not limited thereto.
[ chemical formula 8]
[ chemical formula 9]
[ chemical formula 10]
[ chemical formula 11]
[ chemical formula 12]
[ chemical formula 13]
[ chemical formula 14]
[ chemical formula 15]
[ chemical formula 16]
Since the compound according to one embodiment can achieve clearer colors even in smaller amounts due to the substituent represented by chemical formula 2, e.g., chemical formula 3, a display device having excellent color characteristics, such as excellent brightness, contrast ratio, and the like, can be manufactured by using the compound as a colorant. For example, the compound may be a colorant, such as a dye, for example a green dye that may have, for example, a maximum light transmittance in a wavelength of 445nm to 560 nm.
In general, dyes are the most expensive of the components used in color filters. Thus, it may be necessary to use more expensive dyes to achieve the desired effect, such as high brightness, high contrast ratio, etc. and thus increase the unit production cost. However, when the compound according to one embodiment is used as a dye for a color filter, the compound can achieve excellent color characteristics, such as color characteristics of high brightness, high contrast ratio, and the like, even when used in a small amount, and reduce unit production costs.
Further, the compound according to one embodiment may include a substituent represented by one of chemical formulas 4 to 7 in addition to the substituent represented by chemical formula 2, for example, chemical formula 3, and thus may exhibit improved solubility in an organic solvent and improved coloring characteristics.
According to one embodiment, a photosensitive resin composition comprising the compound according to the above embodiment is provided.
For example, the photosensitive resin composition includes the compound according to the above embodiment, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.
The compound according to one embodiment functions as a colorant (e.g., a dye such as a green dye) in the photosensitive resin composition and can realize excellent color characteristics.
The compound according to one embodiment may be included in an amount of 1 to 10 wt%, for example, 3 to 7 wt%, based on the total amount of the photosensitive resin composition. When the compounds within the range are included, color reproducibility and contrast ratio become excellent.
The photosensitive resin composition may further include a pigment, such as a yellow pigment.
The yellow pigment may be c.i. pigment yellow 139, c.i. pigment yellow 138, c.i. pigment yellow 150, etc. in Color Index (Color Index), and these pigments may be used alone or in a mixture of two or more.
The pigment may be contained in the photosensitive resin composition in the form of a pigment dispersion.
The pigment dispersion liquid may include a solid pigment, a solvent, and a dispersant for uniformly dispersing the pigment in the solvent.
The solid pigment may be included in an amount of 1 to 20 wt%, such as 8 to 15 wt%, such as 10 to 20 wt%, and such as 10 to 15 wt%, based on the total amount of the pigment dispersion.
The dispersant may be a nonionic dispersant, an anionic dispersant, a cationic dispersant, and the like. Specific examples of the dispersant may be polyalkylene glycol and esters thereof, polyalkylene oxide, polyol ester alkylene oxide addition products, alcohol alkylene oxide addition products, sulfonic acid esters, sulfonic acid salts, carboxylic acid esters, carboxylic acid salts, alkylamide alkylene oxide addition products, alkylamines, and the like, and may be used alone or in a mixture of two or more thereof.
Commercially available examples of the dispersant may include DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165, DISPERBYK-166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001, and the like, manufactured by BYK, Inc.; EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400, EFKA-450, and the like, manufactured by EFKA chemical company; solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 28000, and the like, manufactured by Zernia corporation; or PB711, PB821 manufactured by Ajinomoto Co.
The dispersant may be included in an amount of 1 to 20 wt% based on the total amount of the pigment dispersion liquid. When the dispersant is included within the range, the dispersion of the photosensitive resin composition can be improved due to appropriate viscosity, and thus the optical and physicochemical qualities of the article can be maintained.
The solvent used for the pigment dispersion liquid may be ethylene glycol acetate, ethylene glycol ethyl ether, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, or the like.
The pigment dispersion may be included in an amount of 10 to 20 wt%, for example, 12 to 18 wt%, based on the total amount of the photosensitive resin composition. When the pigment dispersion liquid in the range is contained, a process margin is advantageously secured and color reproducibility and contrast ratio become excellent.
The alkali soluble resin may be an acrylic resin.
The acrylic resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and is a resin comprising at least one acrylic repeating unit.
The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group. Examples of the monomer include (meth) acrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.
The first ethylenically unsaturated monomer may be included in an amount of 5 to 50 wt%, for example 10 to 40 wt%, based on the total amount of the acrylic resin.
The second ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene, α -methylstyrene, vinyltoluene, vinylbenzylmethyl ether and the like, an unsaturated carboxylic acid ester compound such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, phenyl (meth) acrylate and the like, an unsaturated carboxylic acid aminoalkyl ester compound such as 2-aminoethyl (meth) acrylate, 2-dimethylaminoethyl (meth) acrylate and the like, a carboxylic acid vinyl ester compound such as vinyl acetate, vinyl benzoate and the like, an unsaturated carboxylic acid glycidyl ester compound such as glycidyl (meth) acrylate and the like, a vinyl cyanide compound such as (meth) acrylonitrile and the like, an unsaturated amide compound such as (meth) acrylamide and the like, and may be used alone or in a mixture of two or more than two.
Specific examples of the acrylic resin may be, but are not limited to, acrylic acid/benzyl methacrylate copolymer, methacrylic acid/benzyl methacrylate/styrene copolymer, methacrylic acid/benzyl methacrylate/2-hydroxyethyl methacrylate copolymer, methacrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymer, and the like. These may be used alone or in a mixture of two or more.
The weight average molecular weight of the acrylic resin can be 3,000 to 150,000g/mol, such as 5,000 to 50,000g/mol, and still more such as 20,000 to 30,000 g/mol. When the weight average molecular weight of the acrylic resin is within the range, the photosensitive resin composition for a color filter has good physical and chemical characteristics, an appropriate viscosity, and close contact characteristics with a substrate during color filter manufacturing.
The acid value of the acrylic resin may be 15mg KOH/g to 60mg KOH/g, for example 20mg KOH/g to 50mg KOH/g. When the acid value of the acrylic resin is within the range, the pixel pattern may have excellent resolution.
The alkali soluble resin may be included in an amount of 1 to 30 wt%, for example, 1 to 20 wt%, based on the total amount of the photosensitive resin composition for a color filter. When the alkali soluble resin is included within the above range, the developability may be improved and excellent surface smoothness may be improved due to improved crosslinking during the manufacture of a color filter.
The photopolymerizable compound may be a monofunctional ester or a multifunctional ester of (meth) acrylic acid containing at least one ethylenically unsaturated double bond.
The photopolymerizable compound has an ethylenically unsaturated double bond, and thus can cause sufficient polymerization during exposure of the pattern forming process and form a pattern having excellent heat resistance, light resistance and chemical resistance.
Specific examples of the photopolymerizable compound may be ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, bisphenol a di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (meth) acrylate, dipentaerythritol di (meth) acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol a epoxy (meth) acrylate, and the like, Ethylene glycol monomethyl ether (meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, novolac epoxy (meth) acrylate, and the like.
Commercially available examples of the photopolymerizable compounds are as follows. Examples of monofunctional (meth) acrylates may include AronixM-
M-
M-
(Toyo Synthesis chemical Co., Ltd.); KAYARAD TC-
TC-
(Nippon Kagaku Co., Ltd.); v-
V-
(Osaka Kagaku Co., Ltd.) and the like. Examples of difunctional (meth) acrylates may include Aronix M-
M-
M-
(Toyo Synthesis chemical Co., Ltd.); KAYARAD
HX-
R-
(Nippon Kagaku Co., Ltd.); v-
V-
V-
(Osaka Kagaku Co., Ltd.) and the like. Examples of trifunctional (meth) acrylates may include Aronix M-
M-
M-
M-
M-
M-
M-
(Toyo Synthesis chemical Co., Ltd.); KAYARAD
DPCA-
DPCA-
DPCA-
DPCA-
(Nippon Kagaku Co., Ltd.); v-
V-
V-
V-
V-
V-
(Osaka Kagaku Co., Ltd.) and the like. These may be used alone or in a mixture of two or more.
The photopolymerizable compound may be treated with an acid anhydride to improve developability.
The photopolymerizable compound may be included in an amount of 1 to 15 wt%, for example, 5 to 10 wt%, based on the total amount of the photosensitive resin composition. When the photopolymerizable compound is included within the range, the photopolymerizable compound is sufficiently cured during exposure of the pattern forming process and has excellent reliability, and the developability of the alkaline developer can be improved.
The photopolymerization initiator is an initiator commonly used for photosensitive resin compositions, such as acetophenone-based compounds, benzophenone-based compounds, thioxanthone-based compounds, benzoin-based compounds, triazine-based compounds, oxime-based compounds, or a combination thereof.
Examples of the acetophenone-based compound may be 2, 2 ' -diethoxyacetophenone, 2 ' -dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, p-tert-butyltrichloroacetophenone, p-tert-butyldichloroacetophenone, 4-chloroacetophenone, 2 ' -dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, and the like.
Examples of the benzophenone-based compound may be benzophenone, benzoyl benzoate, benzoylmethyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4 ' -bis (dimethylamino) benzophenone, 4 ' -bis (diethylamino) benzophenone, 4 ' -dimethylaminobenzophenone, 4 ' -dichlorobenzophenone, 3 ' -dimethyl-2-methoxybenzophenone and the like.
Examples of the thioxanthone-based compound may be thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2, 4-diethylthioxanthone, 2, 4-diisopropylthioxanthone, 2-chlorothioxanthone, and the like.
Examples of the benzoin-based compound may be benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, and the like.
Examples of the triazine-based compound may be 2, 4, 6-trichloro-s-triazine, 2-phenyl-4, 6-bis (trichloromethyl) -s-triazine, 2- (3 ', 4 ' -dimethoxystyryl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (4 ' -methoxynaphthyl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4, 6-bis (trichloromethyl) -s-triazine, 2-biphenyl 4, 6-bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphthol 1-yl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphthol 1-yl) -4, 6-bis (trichloromethyl) -s-triazine, 2-4-bis (trichloromethyl) -6-piperonyl-s-triazine, 2-4-bis (trichloromethyl) -6- (4-methoxystyryl) -s-triazine and the like.
Examples of the oxime-based compound may be O-acyloxime-based compound, 2- (O-benzoyloxime) -1- [4- (phenylthio) phenyl ] -1, 2-octanedione, 1- (O-acetyloxime) -1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] ethanone, O-ethoxycarbonyl- α -oxyamino-1-phenylpropan-1-one, and the like specific examples of the O-acyloxime-based compound may be 1, 2-octanedione, 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholin-4-yl-phenyl) -butan-1-one, 1- (4-phenylthiophenyl) -butane-1, 2-dione 2-oxime-O-benzoate, 1- (4-phenylthiophenyl) -octane-1, 2-dione 2-oxime-O-benzoate, 1- (4-phenylthiophenyl) -octan-1-O-acetate, 1- (4-phenylthiophenyl) -butan-1-one oxime-O-acetate, and the like.
The photopolymerization initiator may further contain a carbazole-based compound, a diketone-based compound, a sulfonium borate-based compound, a diazo-based compound, an imidazole-based compound, a bisimidazole-based compound, and the like, in addition to the above-mentioned compounds.
The photopolymerization initiator may be used together with a photosensitizer capable of causing a chemical reaction by absorbing light and becoming excited and then transferring its energy.
Examples of the sensitizer may be tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, dipentaerythritol tetrakis-3-mercaptopropionate, and the like.
The photopolymerization initiator may be included in an amount of 0.01 to 10% by weight, for example, 0.1 to 5% by weight, based on the total amount of the photosensitive resin composition. When the photopolymerization initiator is included within the range, excellent reliability may be secured due to sufficient curing during exposure of a pattern forming process, a pattern may have excellent resolution and close contact characteristics as well as excellent heat resistance, light resistance, and chemical resistance, and light transmittance may be prevented from being deteriorated due to a non-reactive initiator.
The solvent is a material having compatibility with the compound, the alkali-soluble resin, the photopolymerizable compound and the photopolymerization initiator but not reacting therewith.
Examples of the solvent may include alcohols such as methanol, ethanol, and the like; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, tetrahydrofuran, and the like; glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, and the like; ethylene glycol ethyl acetate such as methyl ethylene glycol ethyl acetate, ethyl ethylene glycol ethyl acetate, diethyl ethylene glycol ethyl acetate, and the like; carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, and the like; propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate, and the like; aromatic hydrocarbons such as toluene, xylene, and the like; ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, 2-heptanone, and the like; saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, and the like; lactates such as methyl lactate, ethyl lactate, and the like; alkyl oxyacetates such as methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, and the like; alkyl alkoxyacetates such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate and the like; alkyl 3-oxopropionates such as methyl 3-oxopropionate, ethyl 3-oxopropionate, and the like; alkyl 3-alkoxypropionates such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, and the like; alkyl 2-oxopropanates such as methyl 2-oxopropanate, ethyl 2-oxopropanate, propyl 2-oxopropanate and the like; alkyl 2-alkoxypropionates such as methyl 2-methoxypropionate, ethyl 2-ethoxypropionate, methyl 2-ethoxypropionate, and the like; 2-oxo-2-methylpropionates such as methyl 2-oxo-2-methylpropionate, ethyl 2-oxo-2-methylpropionate and the like; alkyl 2-alkoxy-2-methylpropionates of alkyl monooxymonocarboxylates such as methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate and the like; esters such as 2-hydroxyethyl propionate, 2-hydroxy-2-methylethyl propionate, hydroxyethyl acetate, 2-hydroxy-3-methyl butyrate, and the like; ketoesters such as ethyl pyruvate and the like. In addition, high boiling point solvents such as N-methylformamide, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N-dimethylacetamide, N-methylpyrrolidinone, dimethyl sulfoxide, benzylethyl ether, dihexyl ether, acetylacetone, isophorone, hexanoic acid, octanoic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ -butyrolactone, ethylene carbonate, propylene carbonate, ethylene glycol phenyl ether acetate, and the like, may also be used.
In view of miscibility and reactivity, glycol ethers such as ethylene glycol monoethyl ether and the like; ethylene glycol alkyl ether acetates such as ethyl glycol ethyl acetate and the like; esters such as 2-hydroxyethyl propionate and the like; carbitols such as diethylene glycol monomethyl ether and the like; and propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate, and the like.
The solvent is used in a balance of, for example, 30 to 80% by weight based on the total amount of the photosensitive resin composition. When the solvent is included within the range, the photosensitive resin composition may have an appropriate viscosity, thereby causing improvement in coating characteristics of the color filter.
The photosensitive resin composition according to another embodiment may further include an epoxy compound to improve the close contact property with the substrate.
Examples of the epoxy compound may be a phenol novolac epoxy compound, a tetramethyl biphenyl epoxy compound, a bisphenol a epoxy compound, an alicyclic epoxy compound, or a combination thereof.
The epoxy compound may be included in an amount of 0.01 to 20 parts by weight, for example, 0.1 to 10 parts by weight, based on 100 parts by weight of the photosensitive resin composition. When the epoxy compound is contained in the range, the close contact property, the storage capacity, and the like can be improved.
The photosensitive resin composition may further include a silane coupling agent having a reactive substituent such as a carboxyl group, a methacryloyl group, an isocyanate group, an epoxy group, and the like to improve adhesion with the substrate.
Examples of the silane coupling agent include trimethoxysilylbenzoic acid, gamma-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, gamma-isocyanatopropyltriethoxysilane, gamma-glycidoxypropyltrimethoxysilane, β - (3, 4-epoxycyclohexyl) ethyltrimethoxysilane and the like.
The silane coupling agent may be included in an amount of 0.01 to 10 parts by weight, based on 100 parts by weight of the photosensitive resin composition. When the silane coupling agent is contained within the above range, the close contact characteristics, the storage characteristics, and the like can be improved.
The photosensitive resin composition may further include a surfactant to improve coating characteristics and suppress the generation of spots.
Examples of surfactants may include fluorene-based surfactants, such as BM-
And BM-
(BM chemical Co.); MEGAFACE F
F
F
And F
(Dainippon ink chemical Co., Ltd.); FULORAD FC-
FULORAD FC-
FULORAD FC-
And FULORAD FC-
(Sumitomo 3M Co.); SURLON S-
SURFLON S-
SURFLON S-
SURFLON S-
And SURFON S-
(Asahi glass company); andSH-
SH-
SH-
SZ-
and SF-
An analog thereof (Tollissicone corporation).
The surfactant may be included in an amount of 0.001 to 5 parts by weight, based on 100 parts by weight of the photosensitive resin composition. When the surfactant is included in the range, coating uniformity may be ensured, stains may not be generated, and wetting (wetting) characteristics of the glass substrate may be improved.
The photosensitive resin composition may further contain other additives such as an antioxidant, a stabilizer, and the like, in a predetermined amount at the time of its property reduction.
According to another embodiment of the present invention, there is provided a color filter manufactured using the photosensitive resin composition.
The process of patterning the color filter is as follows.
The process comprises applying a positive photosensitive resin composition onto a support substrate by spin coating, slit coating, ink-jet printing, or the like; drying the coated positive photosensitive resin composition to form a photosensitive resin composition film; exposing the positive photosensitive resin composition film; developing the exposed positive photosensitive resin composition film in an alkaline aqueous solution to obtain a photosensitive resin film; and heat-treating the photosensitive resin film. Conditions for the patterning process are well known in the related art and will not be described in detail in this specification.
[ embodiments of the invention ]
Hereinafter, the present invention is described in more detail with reference to examples and comparative examples. However, the following examples and comparative examples are provided for descriptive purposes and the present invention is not limited thereto.
(Compound Synthesis)
Synthesis example 1: synthesis of 4- (Biphenyl-2-yloxy) -3, 5, 6-trichloro-phthalonitrile
3, 4, 5, 6-tetrachlorophthalonitrile (3, 4, 5, 6-tetrachlorophthalonitrile) (5g), 2-phenylphenol (3.201g), K2CO3(3.898g) and acetonitrile (50ml) were placed in a 100ml flask and then heated and refluxed. When the reaction was completed, the resultant was filtered and washed with tetrahydrofuran, and then concentrated to obtain a solid. Herein, the obtained solid was washed several times with hexane, filtered and dried in vacuum to obtain 4- (biphenyl-2-yloxy) -3, 5, 6-trichloro-phthalonitrile.
Synthesis example 2: synthesis of 3, 4, 6-trichloro-5- (2, 6-dimethoxy-phenoxy) -phthalonitrile
3, 4, 5, 6-tetrachlorophthalonitrile (5g), 2, 6-dimethoxyphenol (7.21g) and K2CO3(3.898g) and N, N-dimethylformamide (50ml) were placed in a 100ml flask and then heated and stirred at 70 ℃. When the reaction was completed, the resultant was extracted with Ethyl Acetate (EA). After extraction, the resultant was concentrated and purified via column chromatography, followed by concentration and vacuum drying to obtain 3, 4, 6-trichloro-5- (2, 6-dimethoxy-phenoxy) -phthalonitrile.
Synthesis example 3: synthesis of 4- (2-tert-butyl-phenoxy) -3, 5, 6-trichloro-phthalonitrile
3, 4, 5, 6-tetrachlorophthalonitrile (5g), 2-tert-butylphenol (6.64g) and K2CO3(3.898g) and acetonitrile (50ml) were placed in a 100ml flask and then heated and refluxed. When the reaction was complete, the resultant was extracted with EA (ethyl acetate). After extraction, the resultant was concentrated and purified via column chromatography, followed by concentration and vacuum drying to obtain 4- (2-tert-butyl-phenoxy) -3, 5, 6-trichloro-phthalonitrile.
Synthesis example 4: synthesis of 4- (4-tert-butyl-phenoxy) -3, 5, 6-trichloro-phthalonitrile
3, 4, 5, 6-tetrachlorophthalonitrile (5g), 4-tert-butylphenol (6.64g) and K2CO3(3.898g) and acetonitrile (50ml) were placed in a 100ml flask and then heated and refluxed. When the reaction was complete, the resultant was extracted with EA (ethyl acetate). After extraction, the resulting product was concentrated, purified via column chromatography, and then concentrated and dried in vacuo to obtain 4- (4-tert-butyl-phenoxy) -3, 5, 6-trichloro-phthalonitrile.
Synthesis example 5: synthesis of 3, 4, 6-trichloro-5- (3-methyl-butoxy) -phthalonitrile
3, 4, 5, 6-tetrachlorophthalonitrile (5g), isoamyl alcohol (5.9g), 1, 8-diazabicycloundecen-7-ene (3.898g), and acetonitrile (50ml) were placed in a 100ml flask and then heated and refluxed. When the reaction was complete, the resultant was extracted with EA (ethyl acetate). After extraction, the obtained product was concentrated and purified via column chromatography, followed by concentration and vacuum drying to obtain 3, 4, 6-trichloro-5- (3-methyl-butoxy) -phthalonitrile.
Synthesis example 6: synthesis of 3, 4, 6-trichloro-5- (4-methoxy-phenoxy) -phthalonitrile
3, 4, 5, 6-tetrachlorophthalonitrile (5g), 4-methoxyphenol (3.201g), and K2CO3(6.64g) and acetonitrile (50ml) were placed in a 100ml flask and then heated and refluxed. When the reaction was complete, the resultant was extracted with EA (ethyl acetate). After extraction, the obtained product was concentrated and purified via column chromatography, followed by concentration and vacuum drying to obtain 3, 4, 6-trichloro-5- (4-methoxy-phenoxy) -phthalonitrile.
Synthesis example 7: synthesis of Compound represented by chemical formula 8
4- (Biphenyl-2-yloxy) -3, 5, 6-trichloro-phthalonitrile of Synthesis example 1 (1.0g), 3, 4, 6-trichloro-5- (2, 6-dimethoxy-phenoxy) -phthalonitrile of Synthesis example 2 (0.32g), 1, 8-diazabicycloundec-7-ene (0.38g), 1-pentenol (7g) and zinc acetate (0.15g) were placed in a 100mL flask and heated and stirred at 140 ℃. When the reaction was complete, the resultant was concentrated and purified via column chromatography. Next, the liquid from the purification was concentrated to obtain a solid. The crystalline solid was dried in vacuum to obtain the compound represented by chemical formula 8.
[ chemical formula 8]
Maldi-tof MS：1647.95m/z
Synthesis example 8: synthesis of Compound represented by chemical formula 9
4- (Biphenyl-2-yloxy) -3, 5, 6-trichloro-phthalonitrile of Synthesis example 1 (1.0g), 3, 4, 6-trichloro-5- (2, 6-dimethoxy-phenoxy) -phthalonitrile of Synthesis example 2 (0.96g), 1, 8-diazabicycloundec-7-ene (0.58g), 1-pentenol (14g) and zinc acetate (0.23g) were placed in a 100mL flask and then heated and stirred at 140 ℃. When the reaction was complete, the resultant was concentrated and purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuum to obtain the compound represented by chemical formula 9.
[ chemical formula 9]
Maldi-tof MS：1631.91m/z
Synthesis example 9: synthesis of Compound represented by chemical formula 10
4- (Biphenyl-2-yloxy) -3, 5, 6-trichloro-phthalonitrile of Synthesis example 1 (0.5g), 3, 4, 6-trichloro-5- (2, 6-dimethoxy-phenoxy) -phthalonitrile of Synthesis example 2 (1.44g), 1, 8-diazabicycloundec-7-ene (0.58g), 1-pentenol (14g) and zinc acetate (0.23g) were placed in a 100mL flask and then heated and stirred at 140 ℃. When the reaction was complete, the resultant was concentrated and purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuum to obtain the compound represented by chemical formula 10.
[ chemical formula 10]
Maldi-tof MS：1615.86m/z
Synthesis example 10: synthesis of Compound represented by chemical formula 11
4- (4-tert-butyl-phenoxy) -3, 5, 6-trichloro-phthalonitrile of Synthesis example 4 (1g), 3, 4, 6-trichloro-5- (2, 6-dimethoxy-phenoxy) -phthalonitrile of Synthesis example 2 (0.33g), 1, 8-diazabicycloundec-7-ene (0.41g), 1-pentenol (14g) and zinc acetate (0.16g) were placed in a 100mL flask and subsequently heated and stirred at 140 ℃. When the reaction was complete, the resultant was concentrated and purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuum to obtain the compound represented by chemical formula 11.
[ chemical formula 11]
Maldi-tof MS：1587.98m/z
Synthesis example 11: synthesis of Compound represented by chemical formula 12
3, 4, 6-trichloro-5- (3-methyl-butoxy) -phthalonitrile (1g) of Synthesis example 5, 3, 4, 6-trichloro-5- (2, 6-dimethoxy-phenoxy) -phthalonitrile (0.40g) of Synthesis example 2, 1, 8-diazabicycloundecen-7-ene (0.48g), 1-pentenol (14g) and zinc acetate (0.19g) were placed in a 100mL flask and then heated and stirred at 140 ℃. When the reaction was complete, the resultant was concentrated and purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuum to obtain the compound represented by chemical formula 12.
[ chemical formula 12]
Maldi-tof MS：1401.77m/z
Synthesis example 12: synthesis of Compound represented by chemical formula 13
4- (Biphenyl-2-yloxy) -3, 5, 6-trichloro-phthalonitrile of Synthesis example 1 (1g), 3, 4, 6-trichloro-5- (3-methyl-butoxy) -phthalonitrile of Synthesis example 5 (0.4g), 3, 4, 6-trichloro-5- (2, 6-dimethoxy-phenoxy) -phthalonitrile of Synthesis example 2 (0.48g), 1, 8-diazabicycloundec-7-ene (0.58g), 1-pentenol (14g) and zinc acetate (0.22g) were placed in a 100mL flask and then heated and stirred at 140 ℃. When the reaction was complete, the resultant was concentrated and purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuum to obtain the compound represented by chemical formula 13.
[ chemical formula 13]
Maldi-tof MS：1565.89m/z
Synthesis example 13: synthesis of Compound represented by chemical formula 14
3, 4, 6-trichloro-5- (2, 6-dimethoxy-phenoxy) -phthalonitrile (1g), 1, 8-diazabicycloundecen-7-ene (0.30g), 1-pentenol (7g) and zinc acetate (0.12g) of Synthesis example 2 were placed in a 100mL flask and then heated and stirred at 140 ℃. When the reaction was complete, the resultant was concentrated and purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuum to obtain the compound represented by chemical formula 14.
[ chemical formula 14]
Maldi-tof MS：1599.82m/z
Synthesis example 14: synthesis of Compound represented by chemical formula 15
3, 4, 6-trichloro-5- (4-methoxy-phenoxy) -phthalonitrile of Synthesis example 6 (1g), 3, 4, 6-trichloro-5- (2, 6-dimethoxy-phenoxy) -phthalonitrile of Synthesis example 2 (0.50g), 1, 8-diazabicycloundecen-7-ene (0.65g), 1-pentenol (14g) and zinc acetate (0.26g) were placed in a 100mL flask and then heated and stirred at 140 ℃. When the reaction was complete, the resultant was concentrated and purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuum to obtain the compound represented by chemical formula 15.
[ chemical formula 15]
Maldi-tof MS：1509.74m/z
Synthesis example 15: synthesis of Compound represented by chemical formula 16
4- (2-tert-butyl-phenoxy) -3, 5, 6-trichloro-phthalonitrile of Synthesis example 3 (1g), 3, 4, 6-trichloro-5- (2, 6-dimethoxy-phenoxy) -phthalonitrile of Synthesis example 2 (0.33g), 1, 8-diazabicycloundec-7-ene (0.41g), 1-pentenol (14g) and zinc acetate (0.16g) were placed in a 100mL flask and subsequently heated and stirred at 140 ℃. When the reaction was complete, the resultant was concentrated and purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuum to obtain the compound represented by chemical formula 16.
[ chemical formula 16]
Maldi-tof MS：1587.98m/z
Comparative synthesis example 1: synthesis of Compound represented by chemical formula 17
4- (2-second butyl-phenoxy) -3, 5, 6-trichloro-phthalonitrile (1g), 1, 8-diazabicycloundecen-7-ene (0.30g), 1-pentenol (7g) and zinc acetate (0.12g) were placed in a 100mL flask and subsequently heated and stirred at 140 ℃. When the reaction was complete, the resultant was concentrated and then purified via column chromatography. Next, the liquid obtained therefrom was concentrated to obtain a solid. The crystalline solid was dried in vacuum to obtain the compound represented by chemical formula 17.
[ chemical formula 17]
Maldi-tof MS：1584.04m/z
(synthetic photosensitive resin composition)
Example 1
The photosensitive resin composition according to example 1 was prepared by mixing the components of the composition given in table 1 below.
Specifically, a photopolymerization initiator is dissolved in a solvent, stirred at room temperature for 2 hours, an alkali-soluble resin and a photopolymerizable compound are added thereto, and the mixture is stirred at room temperature for 2 hours. Subsequently, the compound according to synthesis example 7 (represented by chemical formula 8) and the pigment (in the form of a pigment dispersion) were added as colorants to the reactants, and the mixture was stirred at room temperature for one hour. Then, the product was filtered three times to remove impurities, to prepare a photosensitive resin composition.
[ Table 1]
(unit: wt%)
Example 2
A photosensitive resin composition was prepared according to the same method as example 1, except that the compound of synthesis example 8 (represented by chemical formula 9) was used instead of the compound of synthesis example 7 (represented by chemical formula 8).
Example 3
A photosensitive resin composition was prepared according to the same method as example 1, except that the compound of synthesis example 9 (represented by chemical formula 10) was used instead of the compound of synthesis example 7 (represented by chemical formula 8).
Example 4
A photosensitive resin composition was prepared according to the same method as example 1, except that the compound of synthesis example 10 (represented by chemical formula 11) was used instead of the compound of synthesis example 7 (represented by chemical formula 8).
Example 5
A photosensitive resin composition was prepared according to the same method as example 1, except that the compound of synthesis example 11 (represented by chemical formula 12) was used instead of the compound of synthesis example 7 (represented by chemical formula 8).
Example 6
A photosensitive resin composition was prepared according to the same method as example 1, except that the compound of synthesis example 12 (represented by chemical formula 13) was used instead of the compound of synthesis example 7 (represented by chemical formula 8).
Example 7
A photosensitive resin composition was prepared according to the same method as example 1, except that the compound of synthesis example 13 (represented by chemical formula 14) was used instead of the compound of synthesis example 7 (represented by chemical formula 8).
Example 8
A photosensitive resin composition was prepared according to the same method as example 1, except that the compound of synthesis example 14 (represented by chemical formula 15) was used instead of the compound of synthesis example 7 (represented by chemical formula 8).
Example 9
A photosensitive resin composition was prepared according to the same method as example 1, except that the compound of synthesis example 15 (represented by chemical formula 16) was used instead of the compound of synthesis example 7 (represented by chemical formula 8).
Comparative example 1
A photosensitive resin composition was prepared according to the same method as example 1, except that the compound of comparative synthesis example 1 (represented by chemical formula 17) was used instead of the compound of synthesis example 7 (represented by chemical formula 8).
Comparative example 2
A photosensitive resin composition was prepared according to the same method as example 1, except that the components of the composition provided in table 2 were mixed instead of the composition in table 1.
[ Table 2]
(unit: wt%)
Comparative example 3
A photosensitive resin composition was prepared in the same manner as in comparative example 2, except that the pigment G36 pigment dispersion liquid was used in place of the pigment G58 pigment dispersion liquid.
Evaluation: color coordinate, brightness and contrast ratio
Each of the photosensitive resin compositions according to examples 1 to 9 and comparative examples 1 to 3 was coated on a degreased glass substrate having a thickness of 1mm to a thickness of 1 μm to 3 μm and dried on a hot plate at 90 ℃ for 2 minutes to obtain a film. Subsequently, the film was exposed by using a high-pressure mercury lamp having a main wavelength of 365 nm. Subsequently, the film was dried in a forced convection drying oven at 200 ℃ for 5 minutes to obtain a sample. The pixel layers were measured for color coordinates (x, Y), luminance Y, and contrast ratio by using a spectrophotometer (MCPD3000, tsukamur electronics), and the results are provided in table 3.
[ Table 3]
| Color coordinate (x, y) | Luminance (Y) | Contrast ratio | |
| Example 1 | (0.284，0.576) | 63.0 | 15,700 |
| Example 2 | (0.279，0.576) | 62.3 | 15,300 |
| Example 3 | (0.281，0.576) | 62.9 | 15,100 |
| Example 4 | (0.278，0.576) | 62.7 | 15,800 |
| Example 5 | (0.280，0.576) | 63.3 | 15,600 |
| Example 6 | (0.278，0.576) | 63.1 | 15,500 |
| Example 7 | (0.277，0.576) | 62.1 | 15,900 |
| Example 8 | (0.279，0.576) | 62.2 | 15,700 |
| Example 9 | (0.282，0.576) | 62.8 | 15,800 |
| Comparative example 1 | (0.275，0.575) | 60.7 | 14,800 |
| Comparative example 2 | (0.275，0.577) | 61.4 | 14,400 |
| Comparative example 3 | (0.276，0.577) | 59.7 | 14,100 |
Referring to table 3, the photosensitive resin compositions of examples 1 to 9 including the compound according to one embodiment as a dye showed excellent color characteristics, compared to the photosensitive resin compositions according to comparative examples 1 to 3.
While the invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not to be limited to the disclosed embodiments, but on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.
Claims (14)
1. A compound represented by chemical formula 1:
[ chemical formula 1]
Wherein in the chemical formula 1, the metal oxide,
m is Cu, Zn, Co or Mo,
R1to R16Independently a chlorine atom,A C3 to C20 alkoxy group represented by chemical formula 6 or a C6 to C20 aryloxy group represented by one of chemical formula 2, chemical formula 4, chemical formula 5 and chemical formula 7, and
the limitation is that R1To R16Is represented by chemical formula 2, and R1To R16At least one of which is represented by one of chemical formulas 4 to 7,
[ chemical formula 2]
Wherein in the chemical formula 2, the metal oxide,
R17and R18Independently an unsubstituted C1 to C20 alkyl group,
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 6]
[ chemical formula 7]
Wherein in chemical formula 6 and chemical formula 7,
L1is unsubstituted C1 to C10 alkylene, and
R19is unsubstituted C1 to C10 alkyl.
2. The compound according to claim 1, wherein chemical formula 2 is represented by chemical formula 3:
[ chemical formula 3]
Wherein in the chemical formula 3, the,
R17and R18Independently an unsubstituted C1 to C20 alkyl group.
3. The compound of claim 1, wherein,
R1to R4At least one of which is represented by chemical formula 2,
R5to R8At least one of which is represented by one of chemical formulas 4 to 7,
R9to R12Is represented by one of chemical formulas 4 to 7, and
R13to R16At least one of which is represented by one of chemical formulas 4 to 7.
4. The compound of claim 1, wherein,
R1to R4At least one of which is represented by chemical formula 2,
R5to R8At least one of which is represented by chemical formula 2,
R9to R12Is represented by one of chemical formulas 4 to 7, and
R13to R16At least one of which is represented by one of chemical formulas 4 to 7.
5. The compound of claim 1, wherein,
R1to R4At least one of which is represented by chemical formula 2,
R5to R8At least one of which is represented by one of chemical formulas 4 to 7,
R9to R12Is represented by chemical formula 2, and
R13to R16At least one of which is represented by one of chemical formulas 4 to 7.
6. The compound of claim 1, wherein,
R1to R4At least one of which is represented by chemical formula 2,
R5to R8At least one of which is represented by chemical formula 2,
R9to R12Is represented by chemical formula 2, and
R13to R16At least one of which is represented by one of chemical formulas 4 to 7.
7. The compound of claim 1, wherein the compound is represented by one of chemical formula 8 to chemical formula 13, chemical formula 15, and chemical formula 16:
[ chemical formula 8]
[ chemical formula 9]
[ chemical formula 10]
[ chemical formula 11]
[ chemical formula 12]
[ chemical formula 13]
[ chemical formula 15]
[ chemical formula 16]
8. The compound of claim 1, wherein the compound is a green dye.
9. The compound of claim 8, wherein the green dye has a maximum light transmittance in a wavelength of 445nm to 560 nm.
10. A photosensitive resin composition comprising the compound according to any one of claims 1 to 9.
11. The photosensitive resin composition of claim 10, wherein the photosensitive resin composition further comprises an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.
12. The photosensitive resin composition of claim 11, wherein the photosensitive resin composition further comprises a pigment.
13. The photosensitive resin composition of claim 12, wherein the pigment is a yellow pigment.
14. A color filter produced using the photosensitive resin composition according to claim 10.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2015-0062056 | 2015-04-30 | ||
| KR1020150062056A KR101881942B1 (en) | 2015-04-30 | 2015-04-30 | Novel compound, photosensitive resin composition comprising the same and color filter |
| PCT/KR2015/008106 WO2016175390A1 (en) | 2015-04-30 | 2015-08-03 | Novel compound, photosensitive resin composition containing same and color filter |
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| CN107428766B true CN107428766B (en) | 2020-07-07 |
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| KR (1) | KR101881942B1 (en) |
| CN (1) | CN107428766B (en) |
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| KR102067083B1 (en) * | 2016-11-25 | 2020-01-16 | 삼성에스디아이 주식회사 | Photosensitive resin composition and photosensitive resin layer using the same and color filter |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060051685A1 (en) * | 2004-09-03 | 2006-03-09 | Fuji Photo Film Co., Ltd. | Negative dye-containing curable composition, color filter and method of producing the same |
| JP2013182214A (en) * | 2012-03-02 | 2013-09-12 | Fujifilm Corp | Colored curable composition and color filter |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001100040A (en) * | 1999-09-30 | 2001-04-13 | Fuji Photo Film Co Ltd | Polarizing sheet consisting of discotic liquid crystal film including disk-shaped coloring matter |
| WO2012108435A1 (en) | 2011-02-10 | 2012-08-16 | 富士フイルム株式会社 | Colored curable composition, and color filter |
| JP5914379B2 (en) * | 2012-03-02 | 2016-05-11 | 富士フイルム株式会社 | Colored curable composition and color filter |
| KR101988047B1 (en) * | 2012-09-17 | 2019-06-11 | 엘지디스플레이 주식회사 | High transmissional green dye for lcd and synthetic method thereof |
| JP2014132296A (en) | 2013-01-07 | 2014-07-17 | Toyo Ink Sc Holdings Co Ltd | Coloring composition for color filter, and color filter |
-
2015
- 2015-04-30 KR KR1020150062056A patent/KR101881942B1/en not_active Application Discontinuation
- 2015-08-03 WO PCT/KR2015/008106 patent/WO2016175390A1/en active Application Filing
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060051685A1 (en) * | 2004-09-03 | 2006-03-09 | Fuji Photo Film Co., Ltd. | Negative dye-containing curable composition, color filter and method of producing the same |
| JP2013182214A (en) * | 2012-03-02 | 2013-09-12 | Fujifilm Corp | Colored curable composition and color filter |
Non-Patent Citations (3)
| Title |
|---|
| Molecular engineering of zinc phthalocyanine sensitizers for efficient dye-sensitized solar cells;Takuro Ikeuchi，等;《Chem. Commun.》;20131209;第50卷(第16期);第1941-1943页 * |
| Sterically demanded unsymmetrical zinc phthalocyanines for dye-sensitized solar cells;Lingamallu Giribabu，等;《Dyes and Pigments》;20130415;第98卷(第3期);第518-529页 * |
| Sterically demanding zinc(II) phthalocyanines: synthesis, optical, electrochemical, nonlinear optical, excited state dynamics studies;Debasis Swain，等;《Journal of Materials Chemistry C》;20131203;第2卷(第9期);第1711-1722段 * |
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| Publication number | Publication date |
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| TWI576348B (en) | 2017-04-01 |
| KR101881942B1 (en) | 2018-07-26 |
| TW201638095A (en) | 2016-11-01 |
| CN107428766A (en) | 2017-12-01 |
| WO2016175390A1 (en) | 2016-11-03 |
| KR20160129619A (en) | 2016-11-09 |
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