CN117700418A - Phthalocyanine compound, preparation and application thereof - Google Patents
Phthalocyanine compound, preparation and application thereof Download PDFInfo
- Publication number
- CN117700418A CN117700418A CN202311721704.3A CN202311721704A CN117700418A CN 117700418 A CN117700418 A CN 117700418A CN 202311721704 A CN202311721704 A CN 202311721704A CN 117700418 A CN117700418 A CN 117700418A
- Authority
- CN
- China
- Prior art keywords
- parts
- compound
- phthalocyanine
- resin composition
- photosensitive resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 41
- -1 Phthalocyanine compound Chemical class 0.000 title claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 238000002156 mixing Methods 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 239000013067 intermediate product Substances 0.000 claims description 15
- 230000003287 optical effect Effects 0.000 claims description 14
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 7
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 claims description 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
- SKIDNYUZJPMKFC-UHFFFAOYSA-N 1-iododecane Chemical compound CCCCCCCCCCI SKIDNYUZJPMKFC-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- UZJZIZFCQFZDHP-UHFFFAOYSA-N 3-nitrobenzene-1,2-dicarbonitrile Chemical compound [O-][N+](=O)C1=CC=CC(C#N)=C1C#N UZJZIZFCQFZDHP-UHFFFAOYSA-N 0.000 claims description 4
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 claims description 4
- NTZMSBAAHBICLE-UHFFFAOYSA-N 4-nitrobenzene-1,2-dicarbonitrile Chemical compound [O-][N+](=O)C1=CC=C(C#N)C(C#N)=C1 NTZMSBAAHBICLE-UHFFFAOYSA-N 0.000 claims description 4
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 4
- 239000004246 zinc acetate Substances 0.000 claims description 4
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 claims description 3
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 claims description 3
- FQKFPGMGQXQHLP-UHFFFAOYSA-N 1-hydroxytriazole Chemical compound ON1C=CN=N1 FQKFPGMGQXQHLP-UHFFFAOYSA-N 0.000 claims description 3
- MACMNSLOLFMQKL-UHFFFAOYSA-N 1-sulfanyltriazole Chemical compound SN1C=CN=N1 MACMNSLOLFMQKL-UHFFFAOYSA-N 0.000 claims description 3
- FHTDDANQIMVWKZ-UHFFFAOYSA-N 1h-pyridine-4-thione Chemical compound SC1=CC=NC=C1 FHTDDANQIMVWKZ-UHFFFAOYSA-N 0.000 claims description 3
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 claims description 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 3
- KGUSKLNAJNYHCQ-UHFFFAOYSA-N 4-(dimethylamino)-2-methylbutanoyl bromide Chemical compound BrC(=O)C(C)CCN(C)C KGUSKLNAJNYHCQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 claims description 3
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 claims description 3
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 claims description 3
- 229940071125 manganese acetate Drugs 0.000 claims description 3
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229920006391 phthalonitrile polymer Polymers 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- DXFHVUUGWSXHQY-UHFFFAOYSA-N propyl 3-bromopropanoate Chemical compound CCCOC(=O)CCBr DXFHVUUGWSXHQY-UHFFFAOYSA-N 0.000 claims description 3
- WIOAODPBBXZVNV-UHFFFAOYSA-N propyl 3-chloropropanoate Chemical compound CCCOC(=O)CCCl WIOAODPBBXZVNV-UHFFFAOYSA-N 0.000 claims description 3
- CNTHQHNTVHYYJW-UHFFFAOYSA-N propyl 3-iodopropanoate Chemical compound CCCOC(=O)CCI CNTHQHNTVHYYJW-UHFFFAOYSA-N 0.000 claims description 3
- FFWJHVGUAKWTKW-UHFFFAOYSA-N pyridine-3-thiol Chemical compound SC1=CC=CN=C1 FFWJHVGUAKWTKW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- ADHUNGXRESHDRX-UHFFFAOYSA-N 4-(4-aminophenyl)benzene-1,2-dicarbonitrile Chemical compound NC1=CC=C(C=C1)C1=CC(=C(C=C1)C#N)C#N ADHUNGXRESHDRX-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 52
- 239000007787 solid Substances 0.000 abstract description 40
- 239000001007 phthalocyanine dye Substances 0.000 abstract description 21
- 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 abstract description 17
- 238000004220 aggregation Methods 0.000 abstract description 6
- 230000002776 aggregation Effects 0.000 abstract description 6
- 125000002091 cationic group Chemical class 0.000 abstract description 3
- 150000001768 cations Chemical class 0.000 abstract description 3
- 230000003993 interaction Effects 0.000 abstract description 3
- 239000011342 resin composition Substances 0.000 description 106
- 239000002904 solvent Substances 0.000 description 70
- 239000000654 additive Substances 0.000 description 64
- 230000000996 additive effect Effects 0.000 description 64
- 239000000178 monomer Substances 0.000 description 64
- 239000003086 colorant Substances 0.000 description 34
- 239000011347 resin Substances 0.000 description 32
- 229920005989 resin Polymers 0.000 description 32
- 239000000463 material Substances 0.000 description 31
- 238000011161 development Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000049 pigment Substances 0.000 description 9
- 230000008859 change Effects 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical compound C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-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
- GNBRZRRANUHHGT-UHFFFAOYSA-N 1-phenylcyclohexa-2,4-dien-1-ol Chemical compound C=1C=CC=CC=1C1(O)CC=CC=C1 GNBRZRRANUHHGT-UHFFFAOYSA-N 0.000 description 2
- BAJQRLZAPXASRD-UHFFFAOYSA-N 4-Nitrobiphenyl Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CC=CC=C1 BAJQRLZAPXASRD-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000000149 argon plasma sintering Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000001259 photo etching Methods 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000283014 Dama Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 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
- 238000002835 absorbance Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- JNSGIVNNHKGGRU-JYRVWZFOSA-N diethoxyphosphinothioyl (2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetate Chemical compound CCOP(=S)(OCC)OC(=O)C(=N/OC)\C1=CSC(N)=N1 JNSGIVNNHKGGRU-JYRVWZFOSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004434 industrial solvent Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- BEAZKUGSCHFXIQ-UHFFFAOYSA-L zinc;diacetate;dihydrate Chemical compound O.O.[Zn+2].CC([O-])=O.CC([O-])=O BEAZKUGSCHFXIQ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
- C09B47/0675—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having oxygen or sulfur linked directly to the skeleton
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
- C09B47/0676—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having nitrogen atom(s) linked directly to the skeleton
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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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/32—Cationic phthalocyanine dyes
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/542—Dye sensitized solar cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Optical Filters (AREA)
Abstract
The invention relates to the technical field of compounds, in particular to a phthalocyanine compound and preparation and application thereof. The present invention proposes the following two strategies for applying phthalocyanine dyes to filters: firstly, aiming at the problem of poor solubility of phthalocyanine, the solubility group is modified on the phthalocyanine nucleus, so that the solubility of the phthalocyanine dye is effectively improved; secondly, aiming at the problem that phthalocyanine dye is easy to aggregate, a series of cationic phthalocyanines are prepared, and aggregation of the dye in a solid state is inhibited by utilizing repulsive interaction between cations, so that the photo-thermal stability of the phthalocyanine dye is further improved.
Description
Technical Field
The invention relates to the technical field of compounds, in particular to a phthalocyanine compound and preparation and application thereof.
Background
With the rapid popularization of flat panel display products such as liquid crystal displays (Liquid Crystal Display, abbreviated as LCDs), organic light emitting diode displays (Organic light Emitting Diode, abbreviated as OLEDs), the requirements of people on color display of the displays are continuously increasing, and color filters are key raw materials for color display of flat panel display products such as LCD panels and OLEDs. There are various methods for manufacturing color filters, such as: dyeing, pigment dispersion, printing, etc., wherein the method for preparing the color filter by adopting the pigment dispersion method is as follows: coating a colored photosensitive resin composition on a colored glass substrate on which a black matrix has been prepared: the method comprises the steps of forming a pattern of the color filter through photoetching processes such as exposure and development, heating and the like, repeating the processes to form the pattern of all the colors of the color filter, and finally forming an indium tin oxide conductive layer to finally obtain the color filter with various color patterns.
Currently, a pigment dispersion method of forming red, green and blue (RGB) pattern pixels using photolithography has been widely adopted to manufacture a filter because a filter having excellent stability can be obtained. The optical filter produced by the method has good thermal stability and photochemical stability, but the particle shape can lead to light scattering so as to reduce brightness, contrast and resolution, and the aggregation behavior of molecules in the pigment and the influence of the aggregation behavior on the optical properties of the pigment are difficult to predict, so that the accurate regulation of the color purity is challenged, and the realization of high color purity and wide color gamut is not facilitated. Dyes can overcome this limitation as attractive alternatives because they are dissolved in the medium and exist in molecular form, thereby reducing light scattering, and the dye has a well-defined molecular structure with a well-defined structure-activity relationship between the molecular structure and photophysical properties, thus being advantageous in achieving excellent optical performance. The dye generally produces a color filter having high transmittance and high contrast, but has poor heat resistance and light resistance, and is liable to cause a chromaticity change when heated at a high temperature in the color filter step. In addition, they should be highly soluble in industrial solvents and have sharp absorption peaks to obtain excellent optical properties. Specifically:
(1) Conventional dyes exhibit low solubility in alkaline aqueous solutions or organic solvents, and thus it is difficult to obtain colored curable compositions with a desired spectrum.
(2) Dyes in the molecularly dispersed state are more prone to aggregation, resulting in a change in optical properties.
(3) The dye in a molecular dispersion state has poor light resistance and heat resistance, and is easy to change optical properties under the high-temperature postbaking process for preparing subsequent devices and long-time illumination after service.
In order to solve the above problems, it is known to use a phthalocyanine dye as a colorant (for example, refer to patent document 1). If a phthalocyanine dye is used as the colorant, the color purity of the phthalocyanine dye itself or the vividness of the color tone thereof can improve the color tone or brightness of the display image at the time of image display. Meanwhile, the phthalocyanine nucleus is modified by groups such as alkyl chains, so that the solubility of the phthalocyanine dye in an organic solvent can be effectively improved.
Conventional zinc phthalocyanine dyes, copper phthalocyanine dyes and the like have various dye precursors (CN 202080008015.6, CN202180044374.1, CN202180038558.7, CN202211637638.7, CN 202310360311.8). In the case of using a dye for a colored image obtained by a liquid crystal display or an image sensor, it is generally required that the colored photosensitive composition is formed in a thin layer and that the formed layer has high coloring strength. In addition to the optical properties required, the dyes are required to have good thermal and light stability in view of the high Wen Liucheng experienced when they are prepared into devices and the long-term illumination during subsequent service.
The phthalocyanine nucleus has good optical property and good photo-thermal stability, and is suitable for being used in optical filters. However, phthalocyanine dyes have two problems as follows: first, the poor solubility of phthalocyanines, especially some solvents commonly used in industrial production such as Propylene Glycol Monomethyl Ether Acetate (PGMEA), etc., can result in the inability of the subsequently prepared thinner colored layers to have high color strength and to meet industry standards; secondly, the large planar structure of the phthalocyanine makes the phthalocyanine easy to aggregate, so that the change of the optical property of the dye is caused, and the photo-thermal stability of the dye is directly influenced.
Disclosure of Invention
In order to solve the problems, the invention aims to provide a phthalocyanine compound and a preparation method and application thereof. The present invention proposes the following two strategies for applying phthalocyanine dyes to filters: firstly, aiming at the problem of poor solubility of phthalocyanine, the solubility group is modified on the phthalocyanine nucleus, so that the solubility of the phthalocyanine dye is effectively improved; secondly, aiming at the problem that phthalocyanine dye is easy to aggregate, a series of cationic phthalocyanines are prepared, and aggregation of the dye in a solid state is inhibited by utilizing repulsive interaction between cations, so that the photo-thermal stability of the phthalocyanine dye is further improved.
The aim of the invention can be achieved by the following technical scheme:
a first object of the present invention is to provide a phthalocyanine compound having a chemical structural formula as shown below:
wherein M is a metal atom; r is R 1 ～R 4 Independently selected from one of substituted or unsubstituted condensed heterocyclic groups, monocyclic aromatic heterocyclic groups or polycyclic aromatic heterocyclic groups.
In one embodiment of the invention, the M is selected from one of Cu, zn, fe, mn or Ni.
In one embodiment of the invention, R 1 ～R 4 Independently selected from one of formulas (A-1) to (A-6):
wherein the dotted line represents R 1 ～R 4 A linkage to a parent nucleus of formula (I); l (L) 1 ～L 9 Independently selected from one of a hydrogen atom or an alkane; x is selected from one of N, O or S; y is selected from one of halogen atoms.
In one embodiment of the invention, L 1 ～L 9 Independently selected from one of the groups represented by the following formulas (B-1) to (B-5):
wherein the dotted line represents L 1 ～L 9 And R is R 1 ～R 4 The bond of the group and n is an integer of 0 to 36.
In one embodiment of the present invention, the phthalocyanine compound is selected from one of the following formulas (1-1) to (1-125), and n is an integer of 0 to 36:
a second object of the present invention is to provide a process for producing the above phthalocyanine compound, comprising the steps of:
(S1) uniformly mixing a first compound and a second compound, then reacting, and performing aftertreatment to obtain a first intermediate product;
(S2) uniformly mixing the first intermediate product obtained in the step (S1) with a third compound, reacting, and performing post-treatment to obtain a second intermediate product;
(S3) uniformly mixing the second intermediate product obtained in the step (S2) with a fourth compound, reacting, and carrying out post-treatment to obtain the phthalocyanine compound.
In one embodiment of the present invention, in step (S1), the first compound is selected from one of 4-nitrophthalonitrile, 3-nitrophthalonitrile, 4' -bromo [1,1' -biphenyl ] -3, 4-dicyano-ne, 1-hydroxy [1,1' -biphenyl ] -3, 4-dicyano-ne, 4-isoquinolinyl-1, 2-phthalonitrile, 4' -nitro [1,1' -biphenyl ] -3, 4-dicyano-ne, 4' -amino [1,1' -biphenyl ] -3, 4-dicyano-ne;
the second compound is selected from one of 4-hydroxypyridine, 3-hydroxypyridine, imidazole, 2-methylimidazole, 4-pyridinethiol, 3-pyridinethiol, 1-hydroxy-1, 2, 3-triazole and 1-mercapto-1, 2, 3-triazole;
the molar ratio of the first compound to the second compound is 1:1 to 1.2;
in the reaction process, the temperature is 20-80 ℃ and the time is 3-24 hours;
in the step (S2), the third compound is selected from one of zinc acetate, copper chloride, manganese acetate and iron acetate;
the mole ratio of the first intermediate product to the third compound is 2-3: 1, a step of;
in the reaction process, the temperature is 20-135 ℃ and the time is 18-24 hours;
in the step (S3), the fourth compound is selected from one of iododecane, bromodecane, chlorodecane, isopropyl iodide, isopropyl bromide, isopropyl chloride, propyl 3-iodopropionate, propyl 3-bromopropionate, propyl 3-chloropropionate, 4- (dimethylamino) -2-methylbutanoyl bromide, 4- (dimethylamino) -2-methylbutanoyl chloride, 4- (dimethylamino) -2-methylbutanoyl iodide, 5-iodo-N, N, N-trimethyl-1-pentaamine, 5-bromo-N, N, N-trimethyl-1-pentaamine, 5-N, N, N-trimethyl-1-pentaamine;
the molar ratio of the second intermediate to the fourth compound is 1: 10-20 parts;
in the reaction process, the temperature is 20-120 ℃ and the time is 48-72 h.
A third object of the present invention is to provide the use of a phthalocyanine compound for the preparation of a dye.
It is a fourth object of the present invention to provide a dye containing the above phthalocyanine compound.
A fifth object of the present invention is to provide a use of the dye in the preparation of a filter.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides an ionic phthalocyanine dye with excellent performance, which can be used for a color filter, wherein the solubility of the phthalocyanine dye in an organic solvent is improved by modifying a solubility group, and the aggregation of the dye in a solid state is inhibited by converting a neutral phthalocyanine structure into positive-charge cationic phthalocyanine and utilizing the repulsive interaction between cations, so that the photo-thermal stability of the phthalocyanine dye is further improved. The phthalocyanine dye has good solubility and high photo-thermal stability, and can effectively improve the image performance and the service life of the device when being applied to a color filter.
Drawings
Fig. 1 is a nuclear magnetic spectrum of a phthalocyanine composition (1-84, n=10);
fig. 2 is an ultraviolet absorbance graph of phthalocyanine compositions (1-84, n=10).
Detailed Description
The invention provides a phthalocyanine compound, the chemical structural formula of which is shown as the following formula:
wherein M is a metal atom; r is R 1 ～R 4 Independently selected from one of substituted or unsubstituted condensed heterocyclic groups, monocyclic aromatic heterocyclic groups or polycyclic aromatic heterocyclic groups.
In one embodiment of the invention, the M is selected from one of Cu, zn, fe, mn or Ni.
In one embodiment of the invention, R 1 ～R 4 Independently selected from one of formulas (A-1) to (A-6):
wherein the dotted line represents R 1 ～R 4 A linkage to a parent nucleus of formula (I); l (L) 1 ～L 9 Independently selected from one of a hydrogen atom or an alkane; x is selected from one of N, O or S; y is selected from one of halogen atoms.
In one embodiment of the invention, L 1 ～L 9 Independently selected from one of the groups represented by the following formulas (B-1) to (B-5):
wherein the dotted line represents L 1 ～L 9 And R is R 1 ～R 4 The bond of the group and n is an integer of 0 to 36.
In one embodiment of the present invention, the phthalocyanine compound is selected from one of the following formulas (1-1) to (1-125), and n is an integer of 0 to 36:
the invention provides a preparation method of the phthalocyanine compound, which comprises the following steps:
(S1) uniformly mixing a first compound and a second compound, then reacting, and performing aftertreatment to obtain a first intermediate product;
(S2) uniformly mixing the first intermediate product obtained in the step (S1) with a third compound, reacting, and performing post-treatment to obtain a second intermediate product;
(S3) uniformly mixing the second intermediate product obtained in the step (S2) with a fourth compound, reacting, and carrying out post-treatment to obtain the phthalocyanine compound.
In one embodiment of the present invention, in step (S1), the first compound is selected from one of 4-nitrophthalonitrile, 3-nitrophthalonitrile, 4' -bromo [1,1' -biphenyl ] -3, 4-dicyano-ne, 1-hydroxy [1,1' -biphenyl ] -3, 4-dicyano-ne, 4-isoquinolinyl-1, 2-phthalonitrile, 4' -nitro [1,1' -biphenyl ] -3, 4-dicyano-ne, 4' -amino [1,1' -biphenyl ] -3, 4-dicyano-ne;
the second compound is selected from one of 4-hydroxypyridine, 3-hydroxypyridine, imidazole, 2-methylimidazole, 4-pyridinethiol, 3-pyridinethiol, 1-hydroxy-1, 2, 3-triazole and 1-mercapto-1, 2, 3-triazole;
the molar ratio of the first compound to the second compound is 1:1 to 1.2;
in the reaction process, the temperature is 20-80 ℃ and the time is 3-24 hours;
in the step (S2), the third compound is selected from one of zinc acetate, copper chloride, manganese acetate and iron acetate;
the mole ratio of the first intermediate product to the third compound is 2-3: 1, a step of;
in the reaction process, the temperature is 20-135 ℃ and the time is 18-24 hours;
in the step (S3), the fourth compound is selected from one of iododecane, bromodecane, chlorodecane, isopropyl iodide, isopropyl bromide, isopropyl chloride, propyl 3-iodopropionate, propyl 3-bromopropionate, propyl 3-chloropropionate, 4- (dimethylamino) -2-methylbutanoyl bromide, 4- (dimethylamino) -2-methylbutanoyl chloride, 4- (dimethylamino) -2-methylbutanoyl iodide, 5-iodo-N, N, N-trimethyl-1-pentaamine, 5-bromo-N, N, N-trimethyl-1-pentaamine, 5-N, N, N-trimethyl-1-pentaamine;
the molar ratio of the second intermediate to the fourth compound is 1: 10-20 parts;
in the reaction process, the temperature is 20-120 ℃ and the time is 48-72 h.
The invention provides an application of a phthalocyanine compound in preparing dyes.
The present invention provides a dye containing the above phthalocyanine compound.
The invention provides an application of the dye in preparing an optical filter.
The invention will now be described in detail with reference to the drawings and specific examples.
In the examples below, unless otherwise specified, all reagents used were commercially available, and all detection means and methods used were conventional in the art.
Example 1-1
This example provides the synthesis of phthalocyanine compositions (1-18, n=10).
4-nitrophthalonitrile (500 mg) and 4-hydroxypyridine (302 mg) were dissolved in N, N-dimethylformamide (15 mL) under an argon atmosphere, and stirred at room temperature for 10min. Then, potassium carbonate (2 g) was added, and the mixture was reacted at 80℃for 3 hours, treated with water (50 mL) and extracted with methylene chloride/methanol (5%) (two 50mL portions each). Purification by flash chromatography on silica gel, dichloromethane/methanol (10%) afforded compound (C-1-1) as a white solid in 66% yield.
Compound (C-1-1) (400 mg) and zinc (II) acetate dihydrate (110 mg) were dissolved in n-pentanol (15 mL) under an argon atmosphere, and stirred at room temperature for 10min. 1, 8-diazabicyclo [5.4.0] undec-7-ene (300. Mu.L) was then added and the mixture was refluxed for 18 hours. The reaction mixture was cooled to room temperature and precipitated with cyclohexane (50 mL). The solid was filtered and washed with water and hexane. The solid was recrystallized from methanol/water to give compound (C-1-2) as a green powder in 68% yield.
A mixture of compound (C-1-2) (240 mg), iododecane (20 mL) and acetone (10 mL) was stirred under reflux for 48h. The solvent was removed under vacuum. The solid was resuspended in cyclohexane and filtered. The solid was washed with hexane, diethyl ether and acetone to give a phthalocyanine composition as a green powder in 95% yield.
Example 2-1
This example provides the synthesis of phthalocyanine compositions (1-84, n=10).
3-nitrophthalonitrile (8.65 g) and imidazole (4.10 g) were dissolved in N, N-dimethylformamide (100 mL) under nitrogen, stirred at room temperature for 24h, during which time potassium carbonate (21 g total, once every 2 h) was added in five portions. After the reaction, ice water (500 mL) was added thereto, followed by suction filtration, drying and recrystallization to give the compound (C-2-1) as an off-white solid in a yield of about 40%.
Compound (C-1-1) (1.0 g) and zinc acetate (0.30 g) were dissolved in dry n-pentanol (70 mL) under an argon atmosphere, and 1, 8-diazabicyclo [5.4.0] undec-7-ene (2 mL) was added as a catalyst and stirred at 135℃for 24 hours. Subsequently cooled, n-hexane was added, and the green precipitate was collected by filtration and washed with n-pentanol and n-hexane. The dried crude product was dissolved in tetrahydrofuran and purified by column chromatography (silica gel) using tetrahydrofuran as the mobile phase to give compound (C-2-2), green powder in 80% yield.
Compound (C-2-2) (100 mg) and iododecane (20 mL) were dissolved in N, N-dimethylformamide (5 mL) under nitrogen, and reacted at 120℃for 72 hours. Then, after cooling to room temperature, ethanol (40 ml) was added to precipitate and filter out the product, to obtain a phthalocyanine composition (whose nuclear magnetic spectrum is shown in FIG. 1, and whose ultraviolet absorption is shown in FIG. 2), green powder, yield was 92%.
Examples 3-1 to 30-1
Examples 3-1 to 30-1 phthalocyanine compounds having chemical structural formulae as described in formulae 1-18, 1-84, 1-2, 1-5, 1-9, 1-13, 1-14, 1-16, 1-22, 1-23, 1-35, 1-42, 1-49, 1-51, 1-54, 1-59, 1-61, 1-64, 1-67, 1-68, 1-71, 1-75, 1-77, 1-81, 1-83, 1-88, 1-93, 1-94, 1-96, 1-97 were synthesized sequentially; wherein n is 10.
Examples 3-1 to 30-1 were synthesized in the same manner as in examples 1-1 and 2-1 except that the starting materials were changed.
EXAMPLE 1 preparation of Green photosensitive resin composition E1
Using the phthalocyanine dye formula prepared in example 1 above, a color photosensitive resin composition E1 was formulated and subjected to photolithographic development to compare the relevant properties of the photosensitive resin composition. In particular using lithographic imaging methods well known to those skilled in the art.
The green photosensitive resin composition E1 comprises the following components in parts by weight:
200 parts of a colorant L1 (consisting of 100 parts of the dye formula (1-18, n=10) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
The above materials were sufficiently dissolved and mixed, and the solid content was controlled to about 20%, to obtain a green photosensitive resin composition E1.
Wherein, the polyfunctional monomer M1: dipentaerythritol hexaacrylate (analytically pure, available from sand dama corporation);
polyfunctional monomer M2: trimethylolpropane trimethacrylate (analytically pure, commercially available from taiwan double bond chemical);
alkali-soluble resin N: trade name Sarbox SB400 (analytically pure, available from sand doma);
additive 01: trade name F-556 (available from DIC Co.);
additive 02: KH570 (γ -methacryloxypropyl trimethoxysilane, available from carbofuran);
photoinitiator P: trade name IRGACURE OXE 01 (available from Basf Co.);
solvent Q1: PGMEA (propylene glycol methyl ether acetate, available from dow chemical);
solvent Q2: PM (propylene glycol methyl ether, available from Dow chemical).
EXAMPLE 2 preparation of Green photosensitive resin composition E2
Using the phthalocyanine dye formula prepared in example 2 above, a color photosensitive resin composition E2 was formulated and subjected to photolithographic development to compare the relevant properties of the photosensitive resin composition. In particular using lithographic imaging methods well known to those skilled in the art.
The green photosensitive resin composition E2 comprises the following components in parts by weight:
200 parts of a colorant L2 (consisting of 100 parts of the dye formula (1-84, n=10) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
The above materials were sufficiently dissolved and mixed, and the solid content was controlled to about 20%, to obtain a green photosensitive resin composition E2.
EXAMPLE 3 preparation of Green photosensitive resin composition E3
The green photosensitive resin composition E3 comprises the following components in parts by weight:
200 parts of a colorant L3 (composed of 100 parts of the dye formula (1-2) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E3.
EXAMPLE 4 preparation of Green photosensitive resin composition E4
The green photosensitive resin composition E4 comprises the following components in parts by weight:
200 parts of a colorant L4 (composed of 100 parts of the dye formula (1-5) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
The above materials were uniformly mixed, and the solid content was controlled to about 20%, to obtain a green photosensitive resin composition E4.
EXAMPLE 5 preparation of Green photosensitive resin composition E5
The green photosensitive resin composition E5 comprises the following components in parts by weight: 200 parts of a colorant L5 (composed of 100 parts of the dye formula (1-9) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E5.
EXAMPLE 6 preparation of Green photosensitive resin composition E6
The green photosensitive resin composition E6 comprises the following components in parts by weight: 200 parts of a colorant L6 (composed of 100 parts of the dye formula (1-13) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E6.
EXAMPLE 7 preparation of Green photosensitive resin composition E7
The green photosensitive resin composition E7 comprises the following components in parts by weight: 200 parts of a colorant L7 (composed of 100 parts of the dye formula (1-14) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
The above materials were uniformly mixed, and the solid content was controlled to about 20%, to obtain a green photosensitive resin composition E7.
EXAMPLE 8 preparation of Green photosensitive resin composition E8
The green photosensitive resin composition E8 comprises the following components in parts by weight: 200 parts of a colorant L8 (consisting of 100 parts of the dye formula (1-16, n=10) and 100 parts of a solvent Q1); 50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E8.
EXAMPLE 9 preparation of Green photosensitive resin composition E9
The green photosensitive resin composition E9 comprises the following components in parts by weight: 200 parts of a colorant L9 (consisting of 100 parts of the dye formula (1-22, n=10) and 100 parts of a solvent Q1); 50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E9.
EXAMPLE 10 preparation of Green photosensitive resin composition E10
The green photosensitive resin composition E10 includes the following components in parts by weight: 200 parts of a colorant L10 (consisting of 100 parts of the dye formula (1-23, n=10) and 100 parts of a solvent Q1); 50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
The above materials were uniformly mixed, and the solid content was controlled to about 20%, to obtain a green photosensitive resin composition E10.
EXAMPLE 11 preparation of Green photosensitive resin composition E11
The green photosensitive resin composition E11 comprises the following components in parts by weight: 200 parts of a colorant L11 (composed of 100 parts of the dye formula (1-35) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
The above materials were uniformly mixed, and the solid content was controlled to about 20%, to obtain a green photosensitive resin composition E11.
EXAMPLE 12 preparation of Green photosensitive resin composition E12
The green photosensitive resin composition E12 comprises the following components in parts by weight: 200 parts of colorant L12 (composed of 100 parts of dye formula (1-42) and 100 parts of solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E12.
EXAMPLE 13 preparation of Green photosensitive resin composition E13
The green photosensitive resin composition E13 comprises the following components in parts by weight: 200 parts of a colorant L13 (composed of 100 parts of the dye formula (1-49) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
The above materials were uniformly mixed, and the solid content was controlled to about 20%, to obtain a green photosensitive resin composition E13.
EXAMPLE 14 preparation of Green photosensitive resin composition E14
The green photosensitive resin composition E14 comprises the following components in parts by weight: 200 parts of a colorant L14 (composed of 100 parts of the dye formula (1-51) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E14.
EXAMPLE 15 preparation of Green photosensitive resin composition E15
The green photosensitive resin composition E15 comprises the following components in parts by weight: 200 parts of colorant L15 (consisting of 100 parts of dye formula (1-54) and 100 parts of solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E15.
EXAMPLE 16 preparation of Green photosensitive resin composition E16
The green photosensitive resin composition E16 comprises the following components in parts by weight: 200 parts of colorant L16 (composed of 100 parts of dye formula (1-59) and 100 parts of solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E16.
EXAMPLE 17 preparation of Green photosensitive resin composition E17
The green photosensitive resin composition E17 comprises the following components in parts by weight: 200 parts of colorant L17 (composed of 100 parts of the dye formula (1-61) and 100 parts of the solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E17.
EXAMPLE 18 preparation of Green photosensitive resin composition E18
The green photosensitive resin composition E18 comprises the following components in parts by weight: 200 parts of colorant L18 (composed of 100 parts of the dye formula (1-64) and 100 parts of the solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E18.
EXAMPLE 19 preparation of Green photosensitive resin composition E19
The green photosensitive resin composition E19 comprises the following components in parts by weight: 200 parts of a colorant L19 (composed of 100 parts of the dye formula (1-67) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E19.
EXAMPLE 20 preparation of Green photosensitive resin composition E20
The green photosensitive resin composition E20 comprises the following components in parts by weight: 200 parts of a colorant L20 (composed of 100 parts of the dye formula (1-68) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E20.
EXAMPLE 21 preparation of Green photosensitive resin composition E21
The green photosensitive resin composition E21 comprises the following components in parts by weight: 200 parts of a colorant L21 (composed of 100 parts of the dye formula (1-71) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
The above materials were uniformly mixed, and the solid content was controlled to about 20%, to obtain a green photosensitive resin composition E21.
EXAMPLE 22 preparation of Green photosensitive resin composition E22
The green photosensitive resin composition E22 comprises the following components in parts by weight: 200 parts of a colorant L22 (composed of 100 parts of the dye formula (1-75) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
The above materials were uniformly mixed, and the solid content was controlled to about 20%, to obtain a green photosensitive resin composition E22.
EXAMPLE 23 preparation of Green photosensitive resin composition E23
The green photosensitive resin composition E23 comprises the following components in parts by weight: 200 parts of a colorant L23 (composed of 100 parts of the dye formula (1-77, n=10) and 100 parts of a solvent Q1); 50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E23.
EXAMPLE 24 preparation of Green photosensitive resin composition E24
The green photosensitive resin composition E24 comprises the following components in parts by weight: 200 parts of a colorant L24 (consisting of 100 parts of the dye formula (1-81, n=10) and 100 parts of a solvent Q1); 50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E24.
EXAMPLE 25 preparation of Green photosensitive resin composition E25
The green photosensitive resin composition E25 comprises the following components in parts by weight: 200 parts of a colorant L25 (consisting of 100 parts of the dye formula (1-83, n=10) and 100 parts of a solvent Q1); 50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E25.
EXAMPLE 26 preparation of Green photosensitive resin composition E26
The green photosensitive resin composition E26 comprises the following components in parts by weight: 200 parts of colorant L26 (composed of 100 parts of dye formula (1-88) and 100 parts of solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
The above materials were uniformly mixed, and the solid content was controlled to about 20%, to obtain a green photosensitive resin composition E26.
EXAMPLE 27 preparation of Green photosensitive resin composition E27
The green photosensitive resin composition E27 comprises the following components in parts by weight: 200 parts of a colorant L27 (composed of 100 parts of the dye formula (1-93) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E27.
EXAMPLE 28 preparation of Green photosensitive resin composition E28
The green photosensitive resin composition E28 comprises the following components in parts by weight: 200 parts of colorant L28 (composed of 100 parts of the dye formula (1-94) and 100 parts of the solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
The above materials were uniformly mixed, and the solid content was controlled to about 20%, to obtain a green photosensitive resin composition E94.
EXAMPLE 29 preparation of Green photosensitive resin composition E29
The green photosensitive resin composition E29 comprises the following components in parts by weight:
200 parts of a colorant L29 (composed of 100 parts of the dye formula (1-96) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
The above materials were uniformly mixed, and the solid content was controlled to about 20%, to obtain a green photosensitive resin composition E29.
EXAMPLE 30 preparation of Green photosensitive resin composition E30
The green photosensitive resin composition E30 comprises the following components in parts by weight:
200 parts of a colorant L30 (composed of 100 parts of a dye formula (1-97, n=10) and 100 parts of a solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2.
Mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition E30.
Comparative example 1 preparation of Green photosensitive resin composition R1
Color photosensitive resin composition R1 was formulated using pigment green 36 and subjected to photolithographic development to compare the relevant properties of the photosensitive resin composition. In particular using lithographic imaging methods well known to those skilled in the art.
The green photosensitive resin composition R1 comprises the following components in parts by weight:
200 parts of colorant R (consisting of 100 parts of pigment green 36 and 100 parts of solvent Q1);
50 parts of polyfunctional monomer M1;
50 parts of a polyfunctional monomer M2;
100 parts of alkali-soluble resin N;
0.2 parts of additive 01;
0.3 parts of additive 02;
5 parts of a photoinitiator P;
50 parts of solvent Q2;
mixing the above materials, and controlling solid content at about 20% to obtain green photosensitive resin composition R1.
Performance test:
the method for imaging by adopting the micro-image comprises the following steps:
cleaning and drying the glass sheet, and coating the glass sheet with a rotary coating machine to obtain a uniform film layer with the thickness of 1.5-2.0 mu m; pre-baking at 90deg.C for 120s, exposing with 365nm ultraviolet light with exposure of 40mJ/cm 2 The mask plate and the coating film are 180 μm apart, developed at 23 ℃ for 50s, post-baked at 230 ℃ for 20min, and the subsequent related properties are tested, and the results are shown in Table 1.
Performance testing and evaluation method:
(1) Chromaticity: and detecting by adopting a Konica Minolta CM-5 spectrocolorimeter.
(2) System compatibility (denoted by "a" in table 1): the photosensitive resin composition is placed in an environment of 0-10 ℃ and kept in a dark place, the viscosity change (at least six months) of the photosensitive resin composition is tested, and photoetching is carried out according to the process conditions, and whether particles appear on the surface of a color film is inspected under an optical microscope (Optical Microscope, which is called OM hereinafter) of which the x500 times is used.
The evaluation criteria were as follows:
o: viscosity change value < + -5% mpa.s and no particles on x500 surface;
delta: viscosity change value < + -10% mpa.s and no particles on x500 surface;
x: viscosity change value > + -10% mPa.s or x500 surface has particles;
(3) Heat resistance test: verifying heat resistance of the photosensitive resin composition by chromatic aberration, post-baking at 230 ℃ for 20min, repeating the post-baking twice, and measuring the film thickness by an XP-2 step instrument; the color difference is the color difference value between the second post-baked sample and the first post-baked sample, and is measured by Meinada CM-5, if delta E ab Less than 3, the heat resistance is better;
(4) Solvent resistance evaluation:
soaking post-baked sample in isopropanol at room temperature for 5min, and baking at 150deg.C in ovenAfter 30min, the color difference before and after the measurement is carried out, if delta E ab < 3, good solvent resistance is indicated.
(5) Evaluation of anti-transfer dyeing properties:
according to the manufacturing process of the color filter, green or blue pixels A are firstly prepared on TFT glass. Then coating the sample, drying the surface of the color filter after development is finished, measuring the color difference before and after the pixel A, and if delta E ab And < 3, it shows good transfer resistance.
(6) Line width, edge trim, and development process margin:
line width and edge uniformity were tested by 500 times OM, and mask line width was 140 μm.
During process margin evaluation, other process conditions are fixed, and edge uniformity and edge residue or edge peeling conditions of images obtained in the development time of 40s-100s are examined, wherein peeling performance judgment is judged by referring to a measuring method of adhesive force in the field.
The evaluation criteria for edge uniformity (denoted by "B" in table 1) are as follows:
o: the development 50s has neat edge line and no residue at the edge;
delta: the edge of the developed 50s image has burrs, and is irregular or has residues at the edge;
x: the image is missing.
The specific criteria for evaluation of the development process margin (denoted by "C" in table 1) are as follows:
o: the development is carried out for 40-100s, the edge lines are neat, no residue and no stripping are generated at the edge;
delta: the development is carried out for 50-80s, the edge lines are neat, no residue and no stripping are generated at the edge;
x: the development 50-80s has irregular edge, or has residues at the edge, or has stripping at the edge;
the above alkaline developer is aqueous solution of alkaline compound such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, calcium carbonate, ammonia water, diethylamine or tetramethylammonium hydroxide, [ OH ] - ]The concentration is 0.2-1.0%, preferably 0.4-0.6%.
The evaluation results are shown in the following table:
TABLE 1 summary of Performance analysis of Green photosensitive resin compositions prepared in examples 1 to 30 and comparative example
Comparison of experimental results shows that c.i. pigment green 36 of comparative example is insoluble in PGMEA, while the dyes of examples 1-30 have good solubility in the color photoresist solvent PGMEA and a higher green color purity in the color photoresist solvent PGMEA; meanwhile, the photosensitive resin compositions E1 to E30 obtained using these 30 dyes have good process properties such as system compatibility, edge line uniformity, development process margin, and the like, similar to comparative example 1 (photosensitive resin composition R1 using c.i. pigment green 36).
The previous description of the embodiments is provided to facilitate a person of ordinary skill in the art in order to make and use the present invention. It will be apparent to those skilled in the art that various modifications can be readily made to these embodiments and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above-described embodiments, and those skilled in the art, based on the explanation of the present invention, should make improvements and modifications without departing from the scope of the present invention.
Claims (10)
1. A phthalocyanine compound, characterized in that the chemical structural formula of the phthalocyanine compound is represented by the following formula:
wherein M is a metal atom; r is R 1 ～R 4 Independently selected from substituted or unsubstitutedAnd one of substituted condensed heterocyclic group, monocyclic aromatic heterocyclic group or polycyclic aromatic heterocyclic group.
2. A phthalocyanine compound according to claim 1, wherein M is selected from one of Cu, zn, fe, mn or Ni.
3. A phthalocyanine compound according to claim 1, wherein R 1 ～R 4 Independently selected from one of formulas (A-1) to (A-6):
wherein the dotted line represents R 1 ～R 4 A linkage to a parent nucleus of formula (I); l (L) 1 ～L 9 Independently selected from one of a hydrogen atom or an alkane; x is selected from one of N, O or S; y is selected from one of halogen atoms.
4. A phthalocyanine compound according to claim 3, wherein L 1 ～L 9 Independently selected from one of the groups represented by the following formulas (B-1) to (B-5):
wherein the dotted line represents L 1 ～L 9 And R is R 1 ～R 4 The bond of the group and n is an integer of 0 to 36.
5. A phthalocyanine compound according to claim 1, wherein said phthalocyanine compound is selected from one of the following formulae (1-1) to (1-125), n being an integer of 0 to 36:
6. a process for producing the phthalocyanine compound as claimed in any one of claims 1 to 5, comprising the steps of:
(S1) uniformly mixing a first compound and a second compound, then reacting, and performing aftertreatment to obtain a first intermediate product;
(S2) uniformly mixing the first intermediate product obtained in the step (S1) with a third compound, reacting, and performing post-treatment to obtain a second intermediate product;
(S3) uniformly mixing the second intermediate product obtained in the step (S2) with a fourth compound, reacting, and carrying out post-treatment to obtain the phthalocyanine compound.
7. The method for producing a phthalocyanine compound according to claim 6, wherein in the step (S1), the first compound is selected from the group consisting of 4-nitrophthalonitrile, 3-nitrophthalonitrile, 4' -bromo [1,1' -biphenyl ] -3, 4-dinitrile, 1-hydroxy [1,1' -biphenyl ] -3, 4-dinitrile, 4-isoquinolinyl-1, 2-phthalonitrile, 4' -nitro [1,1' -biphenyl ] -3, 4-dinitrile, 4' -amino [1,1' -biphenyl ] -3, 4-dinitrile;
the second compound is selected from one of 4-hydroxypyridine, 3-hydroxypyridine, imidazole, 2-methylimidazole, 4-pyridinethiol, 3-pyridinethiol, 1-hydroxy-1, 2, 3-triazole and 1-mercapto-1, 2, 3-triazole;
the molar ratio of the first compound to the second compound is 1:1 to 1.2;
in the reaction process, the temperature is 20-80 ℃ and the time is 3-24 hours;
in the step (S2), the third compound is selected from one of zinc acetate, copper chloride, manganese acetate and iron acetate;
the mole ratio of the first intermediate product to the third compound is 2-3: 1, a step of;
in the reaction process, the temperature is 20-135 ℃ and the time is 18-24 hours;
in the step (S3), the fourth compound is selected from one of iododecane, bromodecane, chlorodecane, isopropyl iodide, isopropyl bromide, isopropyl chloride, propyl 3-iodopropionate, propyl 3-bromopropionate, propyl 3-chloropropionate, 4- (dimethylamino) -2-methylbutanoyl bromide, 4- (dimethylamino) -2-methylbutanoyl chloride, 4- (dimethylamino) -2-methylbutanoyl iodide, 5-iodo-N, N, N-trimethyl-1-pentaamine, 5-bromo-N, N, N-trimethyl-1-pentaamine, 5-N, N, N-trimethyl-1-pentaamine;
the molar ratio of the second intermediate to the fourth compound is 1: 10-20 parts;
in the reaction process, the temperature is 20-120 ℃ and the time is 48-72 h.
8. Use of a phthalocyanine compound as claimed in any one of claims 1 to 5 for the preparation of a dye.
9. A dye comprising the phthalocyanine compound according to any one of claims 1 to 5.
10. Use of the dye according to claim 9 for the preparation of optical filters.
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