KR101796612B1 - Dipyrromethene-based metal complex compound, coloring composition including the same, and color filter including the coloring composition - Google Patents
Dipyrromethene-based metal complex compound, coloring composition including the same, and color filter including the coloring composition Download PDFInfo
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- KR101796612B1 KR101796612B1 KR1020150176645A KR20150176645A KR101796612B1 KR 101796612 B1 KR101796612 B1 KR 101796612B1 KR 1020150176645 A KR1020150176645 A KR 1020150176645A KR 20150176645 A KR20150176645 A KR 20150176645A KR 101796612 B1 KR101796612 B1 KR 101796612B1
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- color filter
- present
- coloring composition
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- -1 metal complex compound Chemical class 0.000 title claims abstract description 50
- 239000000203 mixture Substances 0.000 title claims abstract description 31
- 238000004040 coloring Methods 0.000 title claims abstract description 23
- OVTCUIZCVUGJHS-UHFFFAOYSA-N dipyrrin Chemical compound C=1C=CNC=1C=C1C=CC=N1 OVTCUIZCVUGJHS-UHFFFAOYSA-N 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000004973 liquid crystal related substance Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 description 45
- 125000003118 aryl group Chemical group 0.000 description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 125000002252 acyl group Chemical group 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- 125000001424 substituent group Chemical group 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 15
- 125000003545 alkoxy group Chemical group 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 15
- 125000004093 cyano group Chemical group *C#N 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 125000003710 aryl alkyl group Chemical group 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 125000003282 alkyl amino group Chemical group 0.000 description 11
- ABSOMGPQFXJESQ-UHFFFAOYSA-M cesium;hydroxide;hydrate Chemical compound O.[OH-].[Cs+] ABSOMGPQFXJESQ-UHFFFAOYSA-M 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 239000002808 molecular sieve Substances 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 150000003573 thiols Chemical class 0.000 description 6
- 239000003086 colorant Substances 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 230000008033 biological extinction Effects 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 230000031700 light absorption Effects 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IHZXTIBMKNSJCJ-UHFFFAOYSA-N 3-{[(4-{[4-(dimethylamino)phenyl](4-{ethyl[(3-sulfophenyl)methyl]amino}phenyl)methylidene}cyclohexa-2,5-dien-1-ylidene)(ethyl)azaniumyl]methyl}benzene-1-sulfonate Chemical compound C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 IHZXTIBMKNSJCJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229910052740 iodine Inorganic materials 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
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000005548 pyrenylene group Chemical group 0.000 description 3
- FJBHGWADYLMEJG-UHFFFAOYSA-M sodium;3-[[4-[[4-(diethylamino)phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]cyclohexa-2,5-dien-1-ylidene]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC=1C=C(C=CC=1)S([O-])(=O)=O)=C(C=C1)C=CC1=[N+](CC)CC1=CC=CC(S([O-])(=O)=O)=C1 FJBHGWADYLMEJG-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-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
- 239000011362 coarse particle Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 125000004986 diarylamino group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- FWIROFMBWVMWLB-UHFFFAOYSA-N 1-bromo-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Br)=C1 FWIROFMBWVMWLB-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- TWOSGOLFNJPHJX-UHFFFAOYSA-N 1-ethylchrysene Chemical group C1=CC2=C3C=CC=CC3=CC=C2C2=C1C(CC)=CC=C2 TWOSGOLFNJPHJX-UHFFFAOYSA-N 0.000 description 1
- ODVKGGNHRSKARU-UHFFFAOYSA-N 1-fluoro-4-(4-propylphenyl)benzene Chemical group C1=CC(CCC)=CC=C1C1=CC=C(F)C=C1 ODVKGGNHRSKARU-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- KWMDHCLJYMVBNS-UHFFFAOYSA-N 2-bromo-4,6-dinitroaniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KWMDHCLJYMVBNS-UHFFFAOYSA-N 0.000 description 1
- ZKUYSJHXBFFGPU-UHFFFAOYSA-N 2516-95-2 Chemical compound OC(=O)C1=CC(Cl)=CC=C1[N+]([O-])=O ZKUYSJHXBFFGPU-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- GNHMRTZZNHZDDM-UHFFFAOYSA-N 3-chloropropionitrile Chemical compound ClCCC#N GNHMRTZZNHZDDM-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- DBJUEJCZPKMDPA-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O DBJUEJCZPKMDPA-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000006177 alkyl benzyl group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 1
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical group C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000005578 chrysene group Chemical group 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000005583 coronene group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 description 1
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003824 heptacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC6=CC7=CC=CC=C7C=C6C=C5C=C4C=C3C=C12)* 0.000 description 1
- ACJRMEVDTSKFDP-UHFFFAOYSA-N heptaphene Chemical group C1=CC=C2C=C(C=C3C4=CC5=CC6=CC=CC=C6C=C5C=C4C=CC3=C3)C3=CC2=C1 ACJRMEVDTSKFDP-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- PKIFBGYEEVFWTJ-UHFFFAOYSA-N hexaphene Chemical group C1=CC=C2C=C3C4=CC5=CC6=CC=CC=C6C=C5C=C4C=CC3=CC2=C1 PKIFBGYEEVFWTJ-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- LNKHTYQPVMAJSF-UHFFFAOYSA-N pyranthrene Chemical group C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC3=C(C=CC=C4)C4=CC4=CC=C1C2=C34 LNKHTYQPVMAJSF-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- PGXOVVAJURGPLL-UHFFFAOYSA-N trinaphthylene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C4=CC5=CC=CC=C5C=C4C3=CC2=C1 PGXOVVAJURGPLL-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel 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
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
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- Chemical & Material Sciences (AREA)
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Abstract
A coloring composition comprising the dipyramethylene-based metal complex compound, and a color filter comprising the coloring composition.
Description
The present invention relates to a dipyrromethene-based metal complex compound, a coloring composition comprising the dipyramethylene-based metal complex compound, and a color filter comprising the coloring composition.
The manufacturing techniques of the color filters are classified into a dyeing method, a vapor deposition method, a printing method, and a pigment dispersion method. Particularly, the pigment dispersion method is applied as the most general technique of producing a color filter. In the conventional pigment dispersion method, scattering due to coarse particles of the pigment occurs, viscosity is increased due to defective dispersion stability, and it is often difficult to further improve the contrast and brightness.
Therefore, use of a colorant as a dye has been studied. The use of a dye as a coloring agent is advantageous in that the color and brightness of a display image at the time of image display can be increased owing to the color purity of the dye itself and the sharpness of the color thereof and contrast can be improved because coarse particles are eliminated It is being considered.
The dyes have excellent advantages in spectral characteristics such as color purity and transparency due to molecular behavior but they are difficult to maintain the inherent color of RGB in the liquid crystal alignment film process because the stability against heat is lower than that of the pigments and the durability is weak, Improvement of the heat resistance, which is a necessary condition for commercialization of the filter, is the main issue.
Korean Patent Laid-Open No. 10-2008-0028823 discloses a compound or a tautomer thereof, a metal complex compound, a colored photosensitive curing composition, a color filter, and a preparation thereof.
Accordingly, the present invention is intended to provide a novel difromethene-based metal complex compound, a coloring composition comprising the dipyramethylene-based metal complex compound, and a color filter comprising the coloring composition.
However, the problems to be solved by the present invention are not limited to the above-mentioned problems, and other problems not mentioned can be clearly understood by those skilled in the art from the following description.
An aspect of the present invention provides a dipyrromethene-based metal complex compound represented by the following formula (1): < EMI ID =
[Chemical Formula 1]
In the above formulas,
R 1 to R 6 each independently represent hydrogen, a linear or branched alkyl group which may be substituted, a saturated or unsaturated cycloalkoxycarbonyl group which may be substituted, an aryl group which may be substituted, an arylalkyl group which may be substituted, An optionally substituted acyl group, an optionally substituted amino group, an ester group, an optionally substituted alkylcarbonyloxy group, or an alkylamino group,
M is Zn, Cu, or Ni.
Another aspect of the present invention provides a coloring composition comprising a dipyrromethene-based metal complex compound according to one aspect of the present invention.
According to another aspect of the present invention, there is provided a color filter comprising a dipyrromethene metal complex compound according to one aspect of the present invention.
According to another aspect of the present invention, there is provided a liquid crystal display device including a color filter according to one aspect of the present invention.
According to any one of the above-mentioned means for solving the problems, when a dye is used in a color filter for display, the heat resistance and light resistance are likely to be lowered as compared with the case of using a pigment. However, The color filter using the romethene metal complex compound is excellent in color purity, has a high extinction coefficient capable of thinning, and is excellent in solubility and reliability.
1 is a light absorption spectrum of I-31 in one embodiment of the present invention.
2 is a light absorption spectrum of V-1 in one embodiment of the present invention.
3 is a light absorption spectrum of V-2 in one embodiment of the present invention.
Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings so that those skilled in the art can easily carry out the present invention. It should be understood, however, that the present invention may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. In the drawings, the same reference numbers are used throughout the specification to refer to the same or like parts.
Throughout this specification, when a part is referred to as being "connected" to another part, it is not limited to a case where it is "directly connected" but also includes the case where it is "electrically connected" do.
Throughout this specification, when a member is "on " another member, it includes not only when the member is in contact with the other member, but also when there is another member between the two members.
Throughout this specification, when an element is referred to as "including " an element, it is understood that the element may include other elements as well, without departing from the other elements unless specifically stated otherwise.
The terms "about "," substantially ", etc. used to the extent that they are used throughout the specification are intended to be taken to mean the approximation of the manufacturing and material tolerances inherent in the stated sense, Accurate or absolute numbers are used to help prevent unauthorized exploitation by unauthorized intruders of the referenced disclosure.
The word " step (or step) "or" step "used to the extent that it is used throughout the specification does not mean" step for.
Throughout this specification, the term "combination (s) thereof " included in the expression of the machine form means a mixture or combination of one or more elements selected from the group consisting of the constituents described in the expression of the form of a marker, Quot; means at least one selected from the group consisting of the above-mentioned elements.
Throughout this specification, the description of "A and / or B" means "A or B, or A and B".
Throughout this specification, the term "substituted" means to include all permissible substituents of organic compounds. Acceptable substituents may include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, aromatic and nonaromatic substituents of organic compounds, and the permissible substituents may be one or more. The term "substituted" when used in combination with any of the above groups refers to an acyl, amino (including simple amino, mono and dialkylamino, mono and diarylamino and alkylarylamino), acylamino Aryl, arylcarbonyloxy, alkoxycarbonyloxy, alkoxycarbonyl, carboxy, carboxylate, aminocarbonyl, mono and dialkylaminocarbonyl, aryloxy, Lower alkyl, lower alkenyl, cycloalkyl, heteroaryl, heteroaryl, heteroaryl, heteroaryl, heteroaryl, heteroaryl, heteroaryl, Aryl, heteroaryl, lower alkoxy, aryloxy, aryloxycarbonyloxy, benzyloxy, benzyl, sulfinyl, alkylsulfinyl, sulfonyl, sulfate, sulfonate, sulfonamide, phosphate, Ney soil, force Pinero Ito, oxo, guanidine, already but can be to mean a group substituted with a substituent such as a furnace, formyl, without being limited thereto. Any of the above substituents may be further substituted, for example, but not limited to, when they contain, for example, a gig alkyl group, an aryl group, or the like.
The term " alkyl " or "alkyl group ", as used throughout this specification, refers to an alkyl group having from 1 to 20 carbon atoms, from 1 to 10 carbon atoms, from 1 to 8 carbon atoms, from 1 to 5 carbon atoms, Lt; 2 >
When the alkyl group is substituted with an alkyl group, it is also used interchangeably as a "branched alkyl group ". Examples of the substituent which may be substituted on the alkyl group include halo (for example, F, Cl, Br, I), haloalkyl (for example, CCl 3 or CF 3 ), alkoxy, alkylthio, -C (O) -OH), alkyloxycarbonyl (-C (O) -OR), alkylcarbonyloxy (-OC (O) -R), amino (-NH 2), carbamoyl (-NHC (O) OR- or -OC (O) NHR-), urea (-NH-C (O) -NHR-) and thiol (-SH). . In addition, the alkyl group having 2 or more carbon atoms in the alkyl group described above may include, but not limited to, at least one carbon to carbon double bond or at least one carbon to carbon triple bond. For example, the alkyl group may be substituted with at least one substituent selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, , Nonadecyl, eicosanyl, or any of the possible isomers thereof, but is not limited thereto.
Throughout this specification, the term "aryl group" means that the aryl group contains at least one ring having at least 6 atoms, up to 5 of which contain up to 22 atoms, The double bonds alternate (resonate) between the dissociated atoms. For example, the aryl group refers to monocyclic or bicyclic aromatic rings such as fused bicycles such as, for example, naphthyl, phenanthrenyl, and the like as well as monocyclic such as phenyl, substituted phenyl, and the like. The aryl group is optionally substituted with at least one substituent selected from the group consisting of halogen, alkyl, alkoxy, hydroxy, carboxy, carbamoyl, alkyloxycarbonyl, nitro, trifluoromethyl, amino, cycloalkyl, cyano, alkylS Or 2), or one or more groups of groups which may be substituted by a thiol. For example, an aryl group having 6 to 50 carbon atoms, which is substituted or unsubstituted in the entire specification of the present specification, may be a benzene ring, a toluene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pentaren ring, an indene ring, A pyrenylene ring, a pyrenylene ring, a chrysene ring, an ethyl-chrysene ring, a picenan ring, a perylene ring, a pyrenylene ring, a phenanthrene ring, an azulen ring, a heptarenylene ring, an acenaphthylene ring, A pentaphene ring, a pentaphene ring, a tetraphenylene ring, a hexaphene ring, a hexasene ring, a rubisene ring, a coronene ring, a trinaphthylene ring, a heptaphene ring, a heptacene ring, a pyranthrene ring, Anthryl group, 9-phenanthryl group, 2-phenanthryl group, 1-pyrenyl group, klychenyl group, naphthacenylene group, and coronyl group ≪ / RTI > and derivatives thereof. ≪ RTI ID = 0.0 > However, the present invention is not limited thereto.
Throughout this specification, the term "arylalkyl group" means an aromatic ring group substituted by the alkyl group described above, i.e., an aryl group substituted by the alkyl group. Throughout the specification, the term "acyl group" means an acyl group having from 1 to 48 carbon atoms, from 1 to 24 carbon atoms, from 1 to 10 carbon atoms, from 1 to 5 carbon atoms, and from 1 to 3 carbon atoms, But are not limited to, formyl, acetyl, pivaloyl, benzoyl, tetradecanoyl, cyclohexanoyl, and the like.
Throughout the present specification, the term "alkylcarbonyloxy group" means an alkylcarbonyl group bonded through an oxygen linkage group.
The term "alkylcarbonyl group" throughout the specification refers to an alkyl group bonded through a carbonyl group.
Throughout this specification, the term "alkylamino group" means an amino group substituted by one alkyl group, wherein the alkyl group is as defined above. For example, the alkylamino group may include methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, 2-butylamino, iso-butylamino, But may not be limited thereto.
The term "cycloalkoxycarbonyl group" as used throughout the present specification refers to a cycloalkoxycarbonyl group having 3 to 48 carbon atoms, a cycloalkoxycarbonyl group having 3 to 24 carbon atoms, a cycloalkoxycarbonyl group having 3 to 15 carbon atoms, a cycloalkoxycarbonyl group having 3 to 10 carbon atoms, a cycloalkoxycarbonyl group having 3 to 10 carbon atoms To 6 cycloalkoxycarbonyl groups such as cyclohexyloxycarbonyl and 2,6-di-tert-butyl-4-methylcyclohexyloxycarbonyl, and the like.
Throughout the present specification, the substituent that the "saturated or unsaturated cycloalkoxycarbonyl group which may be substituted" may have is, for example, an alkyl group, a hydroxy group, an alkoxy group, a halo group, a nitrile group or a nitro group; Or an aryl group substituted by an alkyl group, a hydroxy group, an alkoxy group, a halo group, a nitrile group, or a nitro group, but the present invention is not limited thereto.
Throughout the specification, the term "amino" or "amino group" may include simple amino, monoalkylamino and dialkylamino, monoarylamino, and diarylamino or alkylarylamino, or an alkyl, aryl, An alkyl group, or an amino group substituted with an acylalkylene carbonyl group.
Throughout the specification of the present application, the term "ester" or "ester group" may be represented by the formula RCOOR ', where R and R' are each hydrogen or alkyl, but may not be limited thereto.
In the present specification, "substitution" may be substituted by one or more of the above-mentioned substituents, and when two or more substituents are substituted, the substituents may be the same or different from each other, but are not limited thereto
Hereinafter, embodiments of the present invention are described in detail, but the present invention is not limited thereto.
An aspect of the present invention provides a dipyrromethene-based metal complex compound represented by the following formula (1): < EMI ID =
[Chemical Formula 1]
In the above formulas, each of R 1 to R 6 independently represents hydrogen, a linear or branched alkyl group which may be substituted, a saturated or unsaturated cycloalkoxycarbonyl group which may be substituted, an aryl group which may be substituted, aryl An alkyl group, an acyl group which may be substituted, an amino group which may be substituted, an ester group, an alkylcarbonyloxy group which may be substituted, or an alkylamino group, and M is Zn, Cu or Ni.
In one embodiment of the present invention, the alkyl group is a linear or branched C 1-20 alkyl group which may be substituted, a linear or branched C 1-15 alkyl group which may be substituted, a linear or branched A C 1-10 alkyl group, or a linear or branched C 1-5 alkyl group which may be substituted, but may not be limited thereto. The alkyl group may be substituted with at least one substituent selected from the group consisting of halo (e.g., F, Cl, Br, I), haloalkyl (e.g., CCl 3 or CF 3 ), alkoxy, alkylthio, OH), alkyloxycarbonyl (-C (O) -OR), alkylcarbonyloxy (-OC (O) -R), cyano, amino (-NH 2 ), carbamoyl (-NHC (O) NH-), urea (-NH-C (O) -NHR-) and thiol (-SH), for example, And may be substituted with at least one group selected from the group consisting of alkoxy, cyano, and acyl.
In one embodiment of the present invention, the cycloalkoxycarbonyl group is a saturated or unsaturated C 3-48 cycloalkoxycarbonyl group which may be substituted, a saturated or unsaturated C 3-40 cycloalkoxycarbonyl group which may be substituted, a saturated or unsaturated A C 3-30 cycloalkoxycarbonyl group which may be substituted, a saturated or unsaturated C 3-20 cycloalkoxycarbonyl group which may be substituted, a saturated or unsaturated C 3-10 cycloalkoxycarbonyl group which may be substituted, or a saturated or unsaturated C 3-5 Cycloalkoxycarbonyl group, but may not be limited thereto.
In one embodiment of the present invention, the aryl group may be a C 6-50 aryl group, a C 6-40 aryl group, a C 6-30 aryl group, a C 6-20 aryl group, or a C 6-10 aryl group, But may not be limited. Wherein the aryl group is optionally substituted with one or more substituents selected from the group consisting of halogen, alkyl, alkoxy, hydroxy, carboxy, carbamoyl, alkyloxycarbonyl, nitro, trifluoromethyl, amino, cycloalkyl, cyano, , Or 2), or one or more groups selected from the group consisting of, for example, alkyl, carboxy, nitro, amino, and cyano, But the present invention is not limited thereto.
In one embodiment of the present invention, the arylalkyl group may be a C 6-50 arylalkyl group, a C 6-40 arylalkyl group, a C 6-30 arylalkyl group, a C 6-20 arylalkyl group, or a C 6-10 arylalkyl group , But may not be limited thereto. Wherein said arylalkyl group is optionally substituted with one or more substituents independently selected from the group consisting of halogen, alkyl, alkoxy, hydroxy, carboxy, carbamoyl, alkyloxycarbonyl, nitro, trifluoromethyl, amino, cycloalkyl, cyano, 1, or 2), or one or more groups of groups that may be substituted by a thiol, such as, but not limited to, alkyl, carboxy, nitro, amino, and cyano May be substituted with one or more groups, but may not be limited thereto.
In one embodiment of the invention, the acyl groups are C 1-48 acyl group, a C 1-40 acyl group, a C 1-30 acyl group, a C 1-20 acyl group, a C 1-10 acyl group, or a C 1- 5 < / RTI > acyl group.
In one embodiment of the present invention, the alkylamino group may be a C 1-32 alkylamino group, a C 1-30 alkylamino group, a C 1-20 alkylamino group, a C 1-10 alkylamino group, or a C 1-5 alkylamino group , But may not be limited thereto. The alkylamino group may be substituted with at least one group selected from the group consisting of alkoxy, cyano, and acyl, but may not be limited thereto.
In one embodiment of the present invention, each of R 1 to R 6 may independently be hydrogen, phenyl, amine, C 3-8 cycloalkyloxycarbonyl, benzyl, benzylamine, C 1-5 alkylamine, But may not be limited thereto.
In one embodiment of the present invention, the dipyramethylene-based metal complex compound comprises a compound represented by the following general formula (2): < EMI ID =
(2)
In the above formulas, each of R 7 to R 10 independently represents hydrogen, an alkyl group which may be substituted, a linear or branched alkyl group which may have one or more hetero atoms, an aryl group which may be substituted, an arylalkyl group which may be substituted , Or an acylalkylene carbonyl group which may be substituted.
In one embodiment herein, the alkyl group may be a C 1-8 alkyl group, for example, the alkyl group includes methyl, ethyl, propyl, butyl, pentyl, heptyl, heptyl, or octyl, or isomers thereof , But may not be limited thereto. The alkyl group may be substituted with at least one substituent selected from the group consisting of halo (e.g., F, Cl, Br, I), haloalkyl (e.g., CCl 3 or CF 3 ), alkoxy, alkylthio, OH), alkyloxycarbonyl (-C (O) -OR), alkylcarbonyloxy (-OC (O) -R), cyano, amino (-NH 2 ), carbamoyl (-NHC (O) NH-), urea (-NH-C (O) -NHR-) and thiol (-SH), for example, And may be substituted with at least one group selected from the group consisting of alkoxy, cyano, and acyl. The alkyl group which may contain one or more heteroatoms may include, but not be limited to, one or more heteroatoms including O, N, or S.
In one embodiment herein, the aryl group which may be substituted is a C 6-50 aryl group, a C 6-40 aryl group, a C 6-30 aryl group, a C 6-20 aryl group, or a C 6-10 aryl group But may not be limited thereto. Wherein the aryl group is optionally substituted with one or more substituents selected from the group consisting of halogen, alkyl, alkoxy, hydroxy, carboxy, carbamoyl, alkyloxycarbonyl, nitro, trifluoromethyl, amino, cycloalkyl, cyano, , Or 2), or one or more groups selected from the group consisting of, for example, alkyl, carboxy, nitro, amino, and cyano, But the present invention is not limited thereto.
In one embodiment of the invention, the acyl in the acylalkylene carbonyl group is C 1-48 acyl, C 1-40 acyl, C 1-30 acyl, C 1-20 acyl, C 1-10 acyl, or C 1 -5 acyl group, and the alkylene may be C 1-20 , C 1-15 , or C 1-10 , but may not be limited thereto.
In one embodiment of the present invention, the arylalkyl group may be a benzyl group, a phenyl group, or a naphthyl group, but may not be limited thereto. Wherein said arylalkyl group is optionally substituted with one or more substituents independently selected from the group consisting of halogen, alkyl, alkoxy, hydroxy, carboxy, carbamoyl, alkyloxycarbonyl, nitro, trifluoromethyl, amino, cycloalkyl, cyano, 1, or 2), or one or more groups of groups that may be substituted by a thiol, such as, but not limited to, alkyl, carboxy, nitro, amino, and cyano May be substituted with one or more groups, but may not be limited thereto.
In one embodiment of the invention, the benzyl group may be, but is not limited to, alkyl benzyl, halogen benzyl.
In one embodiment of the present invention, when the substituents are substituted, they may be substituted by at least one substituent selected from the group consisting of an alkyl group, an arylalkyl group, an alkoxy group, a cyano group, an acyl group, an amino group, a nitro group, and a carboxyl group But may not be limited thereto.
In one embodiment of the present invention, the dipyramethylene-based metal complex compound may include, but is not limited to, for example, the following compounds:
Another aspect of the present invention provides a coloring composition comprising a dipyrromethene-based metal complex compound according to the above aspect.
In one embodiment of the present invention, the coloring composition may be a color filter having high color purity, not absorbing unnecessary portions as a color filter, having high transmittance, excellent in heat resistance and light resistance, but may not be limited thereto.
Although the detailed description of the parts overlapping with the dipyramethene-based metal complex compound of the present application has been omitted, the description of the dipyrammethene-based metal complex compound of the present application can be applied equally to the coloring composition of the present invention have.
According to another aspect of the present invention, there is provided a color filter comprising a dipyrromethene metal complex compound according to the above aspect.
In one embodiment of the present invention, the color filter may include a coloring pattern formed by forming a coloring composition in a predetermined coloring pattern, followed by exposure and development. In one embodiment of the present invention, the manufacturing method of the color filter includes a step of applying a solution of the coloring composition prepared according to the above aspect, and performing a patterning exposure on the dry film obtained by prebaking, followed by development A black matrix or a pixel corresponding to the color of the coloring agent which is a constituent component of the colored photosensitive resin composition may be obtained, but the present invention is not limited thereto. Further, the color filter can be manufactured by repeating the above process for the number of colors required for the color filter. The constitution and the manufacturing method of the color filter can be widely used in the art without any particular limitations.
In one embodiment of the present invention, the spectroscopic characteristic preferable as the color filter is such that the transparent ratio of the dominant wavelength of the color is high and the transmittance of the other wavelength region is low in the light emission bright line of the three-wavelength light source which is the backlight light source, The wavelengths of the emission luminescent lines of the wave tube are 580 nm and 610 nm (R), 490 nm and 540 to 545 nm (G), and 460 nm (B).
In one embodiment of the present invention, the coloring composition comprising the dipyramethylene-based metal complex compound may have a high color purity, do not absorb unnecessary portions as a color filter, have a high transmittance, and have excellent heat resistance and light resistance. But may not be limited.
According to another aspect of the present invention, there is provided a liquid crystal display including the color filter according to the above aspect.
In one embodiment of the present invention, the liquid crystal display device may be a liquid crystal display device or a liquid crystal display device in which a color filter and a black matrix are formed on an upper substrate, but the present invention is not limited thereto. A color filter on TFT (COT) type liquid crystal display device has a structure in which a color filter and a black matrix are not formed on an upper substrate but is formed on a lower substrate provided with a thin film transistor (TFT) Means a liquid crystal display device. The liquid crystal display device of the present invention has an advantage in that the transmittance and the aperture ratio are improved as compared with the structure in which the color filter and the black matrix are formed on the upper substrate. However, the liquid crystal display device must have a high resolution to easily form a contact hole in the color filter pattern, An excellent adhesion with the lower substrate is required.
Although a detailed description of parts overlapping with the color filter of the present application has been omitted, the description of the color filter of the present application can be applied equally to the liquid crystal display of the present application even if its description is omitted.
Hereinafter, the present invention will be described in more detail with reference to Examples. However, the following Examples are given for the purpose of helping understanding of the present invention, but the present invention is not limited to the following Examples.
[Example]
The dipyrromethene-based metal complex compound according to the present invention was prepared by a synthesis process as shown in the following reaction scheme:
< Example 1: Synthesis of intermediate 1 >
After dissolving 15.6 g (0.1 mol) of 2-chloroacetophenone (Richest Group) in 30.35 g (0.3 mol) of N-methyl-2-pyrrolidone (NMP, DAE-JUNG), 16.84 g (0.09 mol) Of potassium phthalimide were added. After stirring at room temperature for 5 hours, 100 mL of water was added and further stirred for 1 hour. The white solid produced according to the above procedure was filtered and washed with water. The white solid was again added to 100 mL of methanol and stirred for 30 minutes, followed by filtering and drying to obtain a white solid (yield 65%).
FTIR analysis (cm -1 ): (Ar CH) 3044, (CH) 2973, 2933 (NC = O) 1696
< Example 2: Synthesis of intermediate 2 >
141.49 g (0.6 mol) of 2.6-ditertiarybutyl-4-methylcyclohexanol and 56.71 g (0.66 mol) of cyanoacetic acid were dissolved in 331.7 g (3.6 mol) of toluene and stirred. 52.73 g (0.66 mol) of pyridine (JUNSEI Chemical) and 138.93 g (1.32 mol) of acetic anhydride (JT Baker) were successively added thereto, followed by stirring at room temperature for 4 hours. It was then stirred for 30 min in an aqueous 5% sodium bicarbonate solution (Samchun), then extracted with water and ethyl acetate. After treating with anhydrous magnesium sulfate (DAE JUNG), the organic layer was vacuum distilled and 400 mL of methanol was added. The white solid produced according to the above procedure was filtered, washed with 50 mL methanol and dried to yield a white solid (yield 77%).
FTIR analysis (m -1 ): (CH) 2948, 2870, (-CN) 2264 (-COO) 1730 (COC) 1209, 1188
< Example 3: Synthesis of Intermediate 3 >
27.07 g (0.1 mol) of Intermediate 1 prepared in Example 1 and 30.57 g (0.1 mol) of Intermediate 2 prepared in Example 2 were dissolved in 46.54 g (1 mol) of ethanol and stirred. To the stirred mixture was added 40 mL of sodium methoxide (JUNSEI CHEMICAL) at 5 캜 to 10 캜. The mixture was stirred at room temperature for 30 minutes, 4 mL of water was added, and the mixture was refluxed for 4 hours. After the temperature was cooled to room temperature, 100 mL of water was added, and the mixture was stirred for 1 hour. The resulting off-white solid was filtered off and washed with 50 mL of water. The off-white solid was stirred in 100 mL of hexane for 1 hour, filtered and dried to give an off-white solid (yield 60%).
FTIR analysis (m -1 ): (NH 2) 3429, 3343, 3247 (Ar CH) 3056, 3024, (CH) 2938, 2865, (COO) 1635, 1596
< Example 4: Synthesis of Intermediate 4 >
8.83 g (0.02 mol) of Intermediate 3 prepared in Example 3 was added to 24.14 g (0.4 mol) of acetic acid (OCI Company) and stirred. To this stirred solution was added 1.66 g (0.011 mol) of triethyl orthoformate (Alfa Aesar) and stirred at room temperature for 12 hours. The red solid produced according to the above procedure was filtered, washed with 50 mL of acetonitrile (Samchun) and dried to give a red solid (yield 23%).
FTIR analysis (m -1 ): (NH 2) 3395, 3321 (Ar CH) 3062, 3027, (CH) 2941, 2867, (COO) 1651, 1610
< Example 5: Synthesis of Intermediate 5 (I-31)
3.36 g (0.004 mol) of Intermediate 4 prepared in Example 4 was dissolved in a mixed solution of 42.53 g (0.48 mol) of ethyl acetate and 4.53 g (0.14 mol) of methanol, and 0.37 g (0.002 mol) of zinc Acetic acid (zinc acetate, Samchun) was added and stirred at room temperature for 8 hours. Then, 50 mL of water was added and stirred at room temperature for 2 hours. The purple solid prepared above was filtered off, washed with 30 mL of acetonitrile and dried to give a purple solid (31% yield).
MS (70mV): m / z = 1726 [M +, 100%].
FTIR analysis (m -1 ): (NH 2) 3480, 3358 (Ar CH) 3055, (CH) 2951, 2866, (COO) 1665, 1603, 1572
< Example 6: Synthesis of V-1 >
8.63 g (0.5 mmol) of Intermediate 5 prepared in Example 5 was dissolved in 50 ml of dimethylformamide (SAMCHUN). Then 0.29 g (2.1 mmol) of 1-bromobutane (KANTO), 0.3 g (2 mmol) of cesium hydroxide hydrate (Sigma Aldrich) and 1 g of molecular sieve (Sigma Aldrich) And stirred at 80 < 0 > C for 5 hours. After cooling to room temperature, 30 ml of water was added and stirred for 1 hour. The resulting purple solid was filtered and dried (71% yield).
MS (70mV): m / z = 1950.3 [M < + >, 100%].
FTIR analysis (m -1 ): (NH) 3353 (Ar CH) 3061, (CH) 2943, 2866, (COO) 1668, 1598,
< Example 7: Synthesis of V-2 >
8.63 g (0.5 mmol) of the intermediate 5 5 prepared in Example 5 was dissolved in 50 ml of dimethylformamide. Then, 0.36 g (2.1 mmol) of benzyl bromide (Aldrich), 0.3 g (2 mmol) of cesium hydroxide hydrate and 1 g of molecular sieve were added in this order, and the mixture was stirred at 80 ° C for 5 hours. After cooling to room temperature, 30 ml of water was added and stirred for 1 hour. The resulting purple solid was filtered and dried (yield 68%).
MS (70mV): m / z = 2086.2 [M +, 100%].
FTIR analysis (m -1 ): (NH) 3354 (Ar CH) 3060, (CH) 2942, 2866, (COO) 1716, 1661, 1578
< Example 8: Synthesis of V-3 >
8.63 g (0.5 mmol) of Intermediate 5 prepared in Example 5 was dissolved in 50 ml of dimethylformamide. Then, 0.45 g (2.1 mmol) of 4-fluoro-4'-propylbiphenyl, 0.3 g (2 mmol) of cesium hydroxide hydrate and 1 g of molecular sieve were added in this order and stirred at 80 ° C for 5 hours. After cooling to room temperature, 30 ml of water was added and stirred for 1 hour. The resulting purple solid was filtered and dried (yield 55%).
MS (70mV): m / z = 2502.5 [M +, 100%].
FTIR analysis (m -1 ): (NH) 3355 (Ar CH) 3058, (CH) 2943, 2866, (COO) 1661, 1578
< Example 9: Synthesis of V-4>
8.63 g (0.5 mmol) of Intermediate 5 prepared in Example 5 was dissolved in 50 ml of dimethylformamide. Then, 0.3 g (2.1 mmol) of 2-bromoethyl methyl ether (Aldrich), 0.3 g (2 mmol) of cesium hydroxide hydrate and 1 g of molecular sieve were added in this order, and the mixture was stirred at 80 ° C for 5 hours. After cooling to room temperature, 30 ml of water was added and stirred for 1 hour. The resulting purple solid was filtered and dried (yield 58%).
MS (70mV): m / z = 1958.2 [M < + >, 100%].
FTIR analysis (m -1 ): (NH) 3352 (Ar CH) 3060, (CH) 2943, 2865, (COO) 1661, 1581 (Ar C = C) 1523, 1477, (COC) 1278, 1241
< Example 10: Synthesis of V-5 >
8.63 g (0.5 mmol) of Intermediate 5 prepared in Example 5 was dissolved in 50 ml of dimethylformamide. Then, 0.19 g (2.1 mmol) of 3-chloropropionitrile (Alfa), 0.3 g (2 mmol) of cesium hydroxide hydrate and 1 g of molecular sieve were added in this order, and the mixture was stirred at 80 DEG C for 5 hours. After cooling to room temperature, 30 ml of water was added and stirred for 1 hour. The resulting purple solid was filtered and dried (yield 30.5%).
MS (70mV): m / z = 1938.1 [M < + >, 100%].
FTIR analysis (m -1 ): (NH) 3353 (Ar CH) 3060, (CH) 2943, 2865, (-CN) 2206, (COO) 1663, 1580
< Example 11: Synthesis of V-6 >
8.63 g (0.5 mmol) of Intermediate 5 prepared in Example 5 was dissolved in 50 ml of dimethylformamide. Then, 0.5 g (2.1 mmol) of sebacoyl chloride (SAMCHUN), 0.3 g (2 mmol) of cesium hydroxide hydrate and 1 g of molecular sieve were added in this order, and the mixture was stirred at 80 DEG C for 5 hours. After cooling to room temperature, 30 ml of water was added and stirred for 1 hour. The resulting purple solid was filtered and dried (yield 50%).
MS (70mV): m / z = 2454.5 [M < + >, 100%].
FTIR analysis (m -1 ): (NH) 3348 (Ar CH) 3058, (CH) 2939, 2865, (COO) 1663, 1582
< Example 12: Synthesis of V-7>
8.63 g (0.5 mmol) of Intermediate 5 intermediate 5 prepared in Example 5 above was dissolved in 50 ml of dimethylformamide. Then, 0.27 g (2.1 mmol) of 3-chloroaniline (Alfa), 0.3 g (2 mmol) of cesium hydroxide hydrate and 1 g of molecular sieve were added in this order, and the mixture was stirred at 80 ° C for 5 hours. After cooling to room temperature, 30 ml of water was added and stirred for 1 hour. The resulting purple solid was filtered and dried (yield 32%).
MS (70mV): m / z = 2090.2 [M < + >, 100%].
FTIR analysis (m -1 ): (NH 2, NH) 3448, 3355 (Ar CH) 3060, (CH) 2943, 2865, (COO) 1662, 1582
< Example 13: Synthesis of V-8 >
8.63 g (0.5 mmol) of Intermediate 5 prepared in Example 5 was dissolved in 50 ml of dimethylformamide. Thereafter, 0.55 g (2.1 mmol) of 2-bromo-4,6-dinitroaniline, 0.3 g (2 mmol) of cesium hydroxide hydrate and 1 g of molecular sieve were added in this order and stirred at 80 ° C for 5 hours Respectively. After cooling to room temperature, 30 ml of water was added and stirred for 1 hour. The resulting purple solid was filtered and dried (yield 53%).
MS (70mV): m / z = 2450.1 [M < + >, 100%].
FTIR analysis (cm-1): (NH2) 3446 (NH) 3330 (ArC-H) 3089, (C-H) 2948, 2866, (COO) 1618, 1579
< Example 14: Synthesis of V-9>
8.63 g (0.5 mmol) of Intermediate 5 prepared in Example 5 was dissolved in 50 ml of dimethylformamide. Then 0.42 g (2.1 mmol) of 5-chloro-2-nitrobenzoic acid (Aldrich), 0.3 g (2 mmol) of cesium hydroxide hydrate and 1 g of molecular sieve were added in this order, Lt; / RTI > After cooling to room temperature, 30 ml of water was added and stirred for 1 hour. The resulting purple solid was filtered and dried (yield 35%).
MS (70mV): m / z = 2386.1 [M < + >, 100%
FTIR analysis (cm-1): (NH) 3344 (ArC-H) 3059, (C-H) 2946, 2866, (COO) 1662, 1583
< Example 15: Synthesis of V-10 >
8.63 g (0.5 mmol) of Intermediate 5 prepared in Example 5 was dissolved in 50 ml of dimethylformamide. Then, 0.42 g (2.1 mmol) of 3-bromonitrobenzene (Aldrich), 0.3 g (2 mmol) of cesium hydroxide hydrate and 1 g of molecular sieve were added in this order, and the mixture was stirred at 80 ° C for 5 hours. After cooling to room temperature, 30 ml of water was added and stirred for 1 hour. The resulting purple solid was filtered and dried (yield 52%).
MS (70mV): m / z = 2210.1 [M < + >, 100%].
FTIR analysis (cm-1): (NH) 3351 (ArC-H) 3056, (C-H) 2947, 2866, (COO) 1662, 1583
< Experimental Example 1: Absorption measurement>
In order to confirm the light absorption of the synthesized dipyramethyne (DPM) -based compounds, the DPM-based compounds V-1 to V-10 and I-31 (comparative examples) synthesized in Examples 6 to 15 Propylene glycol monomethyl ether acetate (1,000 ppm) was added thereto, followed by stirring for 10 minutes. Thereafter, propylene glycol monomethyl ether acetate was further added, the concentration was diluted to 20 ppm, and the absorbance was measured using a UV / Vis / NIR spectrophotometer (UV3600-shimadzu).
1 to 3 show the absorbance of the compounds I-31, V-1 and V-2, respectively. The absorbance of the dipyrromethene compound according to the present invention showed a high molar extinction coefficient and a narrow half width. Table 1 shows absorption wavelength (Λ max ) and molar extinction coefficient (ε) of V-1 to V-10 and I-31 (comparative example). As can be seen from Table 1, it can be seen that the wavelength has shifted to a longer wavelength as compared with I-31 and a new compound having a high molar extinction coefficient is synthesized.
< Experimental Example 2: Solubility evaluation>
(DPM) compounds V-1 to V-10 and Comparative Examples I-31, CI Acid Violet 17 and CI Acid Violet 49 synthesized in Examples 6 to 15 were mixed with propylene glycol monomethyl ether acetate (PGMEA) and methyl The solubility in methyl ethyl ketone was evaluated. The DMP compound and the solvent were mixed at a concentration of 3% in a 25 ml vial bottle, and the vial bottle was completely sealed and shaken for 15 minutes. After 30 minutes, the presence or absence of the liquid precipitate was visually observed and the results are shown in Table 2 below. When the precipitate was confirmed, it was judged that the solubility was poor. As a criterion for determining the solubility, it is represented by O when completely dissolved,? When partially dissolved, and X when not dissolved. As can be seen from the following Table 2, it can be seen that the compounds according to the present invention, V-1 to V-10, show excellent solubility in comparison with the compounds of the comparative examples.
< Example 16: Coloration Resist Preparation of solution >
As colorants V-1 to V-10, or comparative examples I-31, C.I. Acid Violet 17 (Sigma Aldich) or C.I. Acid Violet 49 (TCI) 20 weight ratio; 70 parts by weight of a methacrylic acid / benzyl methacrylate copolymer (molar ratio: 30/70, average molecular weight: 10,700) as a resin; As a polymerizable compound, 30 parts by weight of dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.); 15 weight ratio of benzyldimethylketal (Irgacure 651: manufactured by BASF Japan) as a photopolymerization initiator; And 680 parts by weight of propylene glycol monomethyl ether acetate as a solvent were mixed to obtain a coloring composition.
< Experimental Example 3: coloring Resist Evaluation of storage stability of solution>
The degree of precipitation of the colored resist solution prepared in Example 16 by observation of foreign matter after storage at room temperature for one month was evaluated by observation. As a criterion for determination, O is indicated when precipitation is not confirmed, X is indicated when precipitation is slightly observed, and when precipitation is confirmed. As can be seen from the following Table 3, it can be confirmed that the compounds according to the present invention are significantly improved in storage stability as compared with Comparative Examples 2 and 3, which are conventionally used dyes.
< Example 17 : Production of glass substrate for color filter>
V-1 to V-10 and Comparative Examples I-31 and C.I. Acid Violet 17 and C.I. A glass substrate for a color filter was prepared using a colored resist solution of Acid Violet 49. After the glass substrate was ultrasonically washed with 0.5% NaOH water, it was washed with water and dehydrated and baked (200 ° C / 20 minutes). Subsequently, the colored resist solution was coated on a cleaned glass substrate using a spin coater so as to have a film thickness of 2.0 mu m, and dried at 100 DEG C for 100 seconds to prepare a color filter glass substrate.
EXPERIMENTAL EXAMPLE 4 Evaluation of Heat Resistance and Light Resistance of Film for Color Filter [
Evaluation of heat resistance of glass substrate for color filter
The glass substrate for a color filter manufactured in Example 17 was heated by a hot plate at 230 DEG C for 20 minutes and then the color difference? Eab before and after the test was measured using a UV / Vis / NIR spectrophotometer (UV3600-shimadzu) And evaluated according to the following criteria. A smaller ΔEab value indicates that the heat resistance is good.
<Criteria>
5: ΔEab value <3
4: 3?? Eab value <5
3: 5?? Eab value <10
2: 10? Eab value <20
1: 20?
Evaluation of Light Resistance of Film for Color Filter
The color filter was irradiated with a xenon lamp at 550 W / m < 2 > at 65 DEG C for 20 hours, and a color difference DELTA Eab before and after the light resistance test was measured. A smaller ΔEab value indicates that the light resistance is good.
<Criteria>
5: ΔEab value <3
4: 3?? Eab value <5
3: 5?? Eab value <10
2: 10? Eab value <20
1: 20?
The results of the evaluation of the heat resistance and the light resistance are shown in Table 4. As can be seen from the following Table 4, it can be confirmed that the compounds according to Examples 6 to 15 exhibit excellent heat resistance and light resistance compared with the compounds of the Comparative Examples.
It will be understood by those of ordinary skill in the art that the foregoing description of the embodiments is for illustrative purposes and that those skilled in the art can easily modify the invention without departing from the spirit or essential characteristics thereof. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive. For example, each component described as a single entity may be distributed and implemented, and components described as being distributed may also be implemented in a combined form.
The scope of the present invention is defined by the appended claims rather than the detailed description, and all changes or modifications derived from the meaning and scope of the claims and their equivalents should be interpreted as being included in the scope of the present invention .
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