CN110016057A - 硫桥联的喹唑啉类四齿铂配合物磷光材料及其制备方法 - Google Patents
硫桥联的喹唑啉类四齿铂配合物磷光材料及其制备方法 Download PDFInfo
- Publication number
- CN110016057A CN110016057A CN201910302583.6A CN201910302583A CN110016057A CN 110016057 A CN110016057 A CN 110016057A CN 201910302583 A CN201910302583 A CN 201910302583A CN 110016057 A CN110016057 A CN 110016057A
- Authority
- CN
- China
- Prior art keywords
- phenyl
- substituted
- formula
- potassium
- represented
- 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.)
- Granted
Links
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 96
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 42
- 239000000463 material Substances 0.000 title claims abstract description 37
- 239000005864 Sulphur Substances 0.000 title claims abstract description 32
- KVSLPQXJQYNHIK-UHFFFAOYSA-N c1ccc2ncncc2c1.Cc1ccc(cc1)S(O)(=O)=O.Cc1ccc(cc1)S(O)(=O)=O Chemical compound c1ccc2ncncc2c1.Cc1ccc(cc1)S(O)(=O)=O.Cc1ccc(cc1)S(O)(=O)=O KVSLPQXJQYNHIK-UHFFFAOYSA-N 0.000 title claims abstract description 26
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- -1 substituted-phenyl Chemical group 0.000 claims abstract description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 238000006467 substitution reaction Methods 0.000 claims abstract description 7
- BRUWSFUBFQYNPG-UHFFFAOYSA-N 1-phenoxypiperidine Chemical compound C1CCCCN1OC1=CC=CC=C1 BRUWSFUBFQYNPG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003368 amide group Chemical group 0.000 claims abstract description 5
- 239000001273 butane Substances 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 239000011737 fluorine Substances 0.000 claims abstract description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical group CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims abstract description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims abstract description 5
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims abstract description 4
- KAHVZNKZQFSBFW-UHFFFAOYSA-N n-methyl-n-trimethylsilylmethanamine Chemical compound CN(C)[Si](C)(C)C KAHVZNKZQFSBFW-UHFFFAOYSA-N 0.000 claims abstract description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 32
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 28
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 28
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000003446 ligand Substances 0.000 claims description 26
- 239000002798 polar solvent Substances 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 16
- 229910052763 palladium Inorganic materials 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 150000003057 platinum Chemical class 0.000 claims description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000003513 alkali Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 12
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003444 phase transfer catalyst Substances 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 10
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 239000001103 potassium chloride Substances 0.000 claims description 8
- 235000011164 potassium chloride Nutrition 0.000 claims description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 8
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
- 239000011591 potassium Substances 0.000 claims description 7
- 229910052700 potassium Inorganic materials 0.000 claims description 7
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 235000019441 ethanol Nutrition 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims description 5
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 5
- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 5
- 235000011009 potassium phosphates Nutrition 0.000 claims description 5
- 239000012312 sodium hydride Substances 0.000 claims description 5
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- AJSHDAOMUKXVDC-UHFFFAOYSA-N butan-1-amine;sulfuric acid Chemical compound CCCC[NH3+].OS([O-])(=O)=O AJSHDAOMUKXVDC-UHFFFAOYSA-N 0.000 claims description 4
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 claims description 4
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- 150000003246 quinazolines Chemical class 0.000 claims description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 4
- 150000003457 sulfones Chemical group 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 235000011056 potassium acetate Nutrition 0.000 claims description 3
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 2
- 239000005751 Copper oxide Substances 0.000 claims description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 2
- 229910000431 copper oxide Inorganic materials 0.000 claims description 2
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 2
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 claims description 2
- 125000005909 ethyl alcohol group Chemical group 0.000 claims description 2
- 238000003682 fluorination reaction Methods 0.000 claims description 2
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical group [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims description 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 2
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 claims description 2
- 229940099427 potassium bisulfite Drugs 0.000 claims description 2
- 235000011181 potassium carbonates Nutrition 0.000 claims description 2
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 claims description 2
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 2
- 239000012286 potassium permanganate Substances 0.000 claims description 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims description 2
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 2
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 claims description 2
- GNBVPFITFYNRCN-UHFFFAOYSA-M sodium thioglycolate Chemical compound [Na+].[O-]C(=O)CS GNBVPFITFYNRCN-UHFFFAOYSA-M 0.000 claims description 2
- 229940046307 sodium thioglycolate Drugs 0.000 claims description 2
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 229910000166 zirconium phosphate Inorganic materials 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 claims 2
- 235000019270 ammonium chloride Nutrition 0.000 claims 2
- SXGBREZGMJVYRL-UHFFFAOYSA-N butan-1-amine;hydrobromide Chemical compound [Br-].CCCC[NH3+] SXGBREZGMJVYRL-UHFFFAOYSA-N 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 238000003408 phase transfer catalysis Methods 0.000 claims 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 229910000103 lithium hydride Inorganic materials 0.000 claims 1
- 150000002918 oxazolines Chemical class 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- SDLBJIZEEMKQKY-UHFFFAOYSA-M silver chlorate Chemical compound [Ag+].[O-]Cl(=O)=O SDLBJIZEEMKQKY-UHFFFAOYSA-M 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 238000004587 chromatography analysis Methods 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 9
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 6
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 5
- SKJCWIFHLDWPEO-UHFFFAOYSA-N 3-benzyl-4-phenylbutan-2-one Chemical class C=1C=CC=CC=1CC(C(=O)C)CC1=CC=CC=C1 SKJCWIFHLDWPEO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- MNJBXBVJLMRDSC-UHFFFAOYSA-N 2-(3-bromophenyl)-4-chloroquinazoline Chemical compound ClC1=NC(=NC2=CC=CC=C12)C1=CC=CC(Br)=C1 MNJBXBVJLMRDSC-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- SDJHDRMYZQFJJO-UHFFFAOYSA-N ethanethioic s-acid;potassium Chemical compound [K].CC(S)=O SDJHDRMYZQFJJO-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000004575 stone Substances 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 description 1
- MRWOWYVASUOIKP-UHFFFAOYSA-N BrC1=CC=CC(C(C2)NCCC2C2=NC3=CC=CC=C3C=N2)=C1 Chemical compound BrC1=CC=CC(C(C2)NCCC2C2=NC3=CC=CC=C3C=N2)=C1 MRWOWYVASUOIKP-UHFFFAOYSA-N 0.000 description 1
- WZHKCFDUDKJGBA-UHFFFAOYSA-N N1CCNCC1.S1C=CC=C1 Chemical compound N1CCNCC1.S1C=CC=C1 WZHKCFDUDKJGBA-UHFFFAOYSA-N 0.000 description 1
- 241000083879 Polyommatus icarus Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- LGZXYFMMLRYXLK-UHFFFAOYSA-N mercury(2+);sulfide Chemical compound [S-2].[Hg+2] LGZXYFMMLRYXLK-UHFFFAOYSA-N 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical class [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Abstract
本发明公开了一类硫桥联的喹唑啉类四齿铂配合物磷光材料及其制备方法。其结构通式由下述式(Ι)和式(Ⅱ)表示。其中R可以是苯基、4‑氟取代苯基、2,4‑二氟取代苯基、3,4,5‑三氟取代苯基、4‑三氟甲基取代苯基、2‑三氟甲基取代苯基、2,6‑二甲基取代苯基、4‑甲氧基取代苯基、4‑硝基取代苯基、4‑N,N‑二甲胺取代苯基、2‑苯并噻吩基、2‑苯并呋喃基、9‑(4‑取代苯基)咔唑、9‑(4‑取代苯基)吩噻嗪、2取代9,9‑二甲基芴基、叔丁烷氧基、2,6‑二甲基取代苯氧基、六氢吡啶基、N‑咔唑基、N‑二苯胺基、N‑二(4‑叔丁基苯基)胺基、N‑吩噻嗪基、9,9‑二甲基氢化吖啶基中的一种。
Description
技术领域
本发明涉及电致发光技术领域,是一类基于具有刚性结构的硫桥联的喹唑啉类四齿铂配合物磷光材料。
背景技术
由于有机电致发光二极管(OLEDs)拥有自发光、可弯曲、轻薄、发光效率和亮度高、驱动电压低、全固态、温度适应范围广等优点,因此被广泛应用于平板显示、固体照明和各种电子设备中。与此同时,对OLEDS功能材料,特别是对OLEDs的效率寿命起决定性作用的发光层材料的需求也在快速增长。
在全彩显示和照明领域中蓝光材料都是不可缺少,一方面蓝光材料不仅可以直接制备三基色显示器,实现全彩显色,另一方面可以与橘红色或红色发光材料制备混合白光OLEDs,降低制作成本。目前有多种方法制备蓝色发光材料。普通的蓝色荧光材料仅能利用25%的单线态激子,内量子效率(IQE)理论上最高为25%,在电致发光过程中又存在各种能量损失和稳定性差等问题;重金属磷光材料,如Ir、Pt配合物,具有重原子自旋轨道耦合(SOC)效应,使三线态激子以辐射跃迁方式回到基态,充分利用单线态和三线态激子,使内量子效率理论上达到100%,并且可以利用丰富的配位方式实现光谱调节。因此制备重金属配位的磷光材料成为实现高性能蓝光材料的重要途径,吸引越来越多的研究人员来探索。其中铂配合物具有平面结构,与八面体结构的铱等重金属配合物相比,在配体选择性上具有更好的灵活性,可以设计出二齿、三齿、四齿的配体结构,同时其合成的可控性也较好。
四齿配合物具有比二齿和三齿铂配合物更强的刚性结构,可以有效的降低非辐射衰减,大幅度提高发光效率和热稳定,而且可以灵活调节配体结构改变发光颜色。最初四齿铂配合物是以氮原子连接配体,虽然达到了发光蓝移的效果,但是量子效率较低。目前四齿铂配合物主要以咔唑基、芴等作为桥将配体连接起来为主,但是其发光颜色普遍达不到深蓝光,近年来,为实现深蓝光发射,一般将桥连基团换成低共轭的氧原子、碳原子等。硫作为与氧同一主族的元素,两者有许多相似性,将其应用到四齿铂配合物桥连单元中是对有机光电材料领域一种新的探索。并且硫原子具有丰富的价态变化、能够形成多种桥键单元,调节发光颜色。由于硫的特殊性能,其可以与Hg、Cu等金属离子络合,因此同样可以应用于生物传感领域。
发明内容
技术问题:本发明的目的是开发出一类具有制备简便、成本低廉并且具有优异光电性能、稳定性、溶解性等优点的硫桥联的喹唑啉类四齿铂配合物磷光材料。
技术方案:本发明的硫桥联的喹唑啉类四齿铂配合物磷光材料,该铂配合物具体是由硫原子、砜桥联的喹唑啉类四齿铂配合物,其结构通式为下述式(I)和式(II)所表示的化合物:
其中R是苯基、4-氟取代苯基、2,4-二氟取代苯基、3,4,5-三氟取代苯基、4-三氟甲基取代苯基、2-三氟甲基取代苯基、2,6-二甲基取代苯基、4-甲氧基取代苯基、4-硝基取代苯基、4-N,N-二甲胺取代苯基、2-苯并噻吩基、2-苯并呋喃基、9-(4-取代苯基)咔唑、9-(4-取代苯基)吩噻嗪、2取代9,9-二甲基芴基、叔丁烷氧基、2,6-二甲基取代苯氧基、六氢吡啶基、N-咔唑基、N-二苯胺基、N-二(4-叔丁基苯基)胺基、N-吩噻嗪基或9,9-二甲基氢化吖啶基中的一种。
本发明的硫桥联的喹唑啉类四齿铂配合物磷光材料的制备方法,所述的式(Ι)和式(II)所示的硫桥联的喹唑啉类四齿铂配合物磷光材料的制备方法包含以下步骤:
步骤1)2-(3-卤代苯基)-4-氯喹唑啉与RH溶于极性溶剂中,在碱、催化剂的存在下,25~120℃反应6~24h,得到如式(1)所表示的喹唑啉类衍生物,其中X是-Br、-I;
步骤2)如式(1)所表示的喹唑啉类衍生物溶于极性溶剂中,加入硫化试剂、碱、钯催化剂,在100~150℃下反应6~12h,得到如式(2)所表示的硫原子桥联的配体;
步骤3)如式(2)所表示的硫原子桥联的配体溶于极性溶剂中,加入氧化剂、催化剂,25~50℃下反应3~24h,得到如式(3)所表示的砜桥配体;
步骤4)如式(2)所表示的硫原子桥联的配体溶于极性溶剂中,加入铂盐、相转移催化剂,先室温搅拌12~24h,然后升温至120~150℃下反应24h~72h,得到如式(4)所表示的硫原子桥联的喹唑啉类四齿铂配合物;
步骤5)如式(3)所表示的砜桥配体溶于极性溶剂中,加入铂盐、相转移催化剂,先室温搅拌12~24h,然后升温至120~150℃下反应24h~72h,得到如式(5)所表示的砜桥联的喹唑啉类四齿铂配合物。
其中:
步骤1)中:反应物用量是,按摩尔份数计,2-(3-溴苯基)-4-氯喹唑啉1份,带有活性基团的化合物RH 1~4份,催化剂0.01~0.1份,极性溶剂10~50份,碱0.1~10份;所述R是苯基、4-氟取代苯基、2,4-二氟取代苯基、3,4,5-三氟取代苯基、4-三氟甲基取代苯基、2-三氟甲基取代苯基、2,6-二甲基取代苯基、4-甲氧基取代苯基、4-硝基取代苯基、4-N,N-二甲胺取代苯基、2-苯并噻吩基、2-苯并呋喃基、9-(4-取代苯基)咔唑、9-(4-取代苯基)吩噻嗪、2取代9,9-二甲基芴基、叔丁烷氧基、2,6-二甲基取代苯氧基、六氢吡啶基、N-咔唑基、N-二苯胺基、N-二(4-叔丁基苯基)胺基、N-吩噻嗪基或9,9-二甲基氢化吖啶基;所述的催化剂是四三苯基磷钯、双(二亚芐基丙酮)钯、三(二亚芐基丙酮)二钯、二(三苯基膦)二氯化钯或1,1'-二(二苯膦基)二茂铁二氯化钯;所述的碱是碳酸钾、碳酸钠、叔丁醇钠、叔丁醇钾、正丁基锂或氢化钠;所述有机溶剂是乙醇、乙二醇二甲醚、甲苯,四氢呋喃、二甲基亚砜、N,N—二甲基甲酰胺、N,N—二甲基乙酰胺或1,4-二氧六环中的一种或几种的混合物。
步骤2)中:反应物用量是,按摩尔份数计,如式(1)所表示的化合物1份,硫化试剂0.5~1份,碱0.6~1份,钯催化剂0.05~0.1份,有机溶剂10~30份;所述的硫化试剂是硫代乙酸钾、硫代乙酸钠、硫脲、硫化钠、硫氰化钾或硫;所述催化剂是四三苯基磷钯、双(二亚芐基丙酮)钯、三(二亚芐基丙酮)二钯、二(三苯基膦)二氯化钯、1,1'-二(二苯膦基)二茂铁二氯化钯、碘化亚铜或氧化铜;所述的碱是氢氧化钠、氢氧化钾、碳酸钾、磷酸钾、乙酸钾、氟化钾、碳酸铯、叔丁醇钠或叔丁醇钾;所述极性溶剂是甲苯、丙酮、聚乙二醇、二甲基亚砜、N,N—二甲基甲酰胺、N,N—二甲基乙酰胺或四氢呋喃中的一种或几种的混合物。
步骤3)中:反应物用量是,按摩尔份数计,如式(2)所表示的硫桥配体1份,氧化剂5~50份,催化剂0-0.1份,极性溶剂10~30份;所述氧化剂是双氧水、硝酸铜、硝酸银、氯化银、高锰酸钾、亚硫酸氢钾、次氯酸钠、高碘酸、铬酸酐、过氧乙酸或过氧苯甲酸中的一种或几种的混合物;所述催化剂是氯化铁、钨酸钠或钒酸钠;所述极性溶剂是乙酸、乙酸酐、乙腈、水、丙酮、二氯甲烷或乙醚中的一种或几种的混合物。
步骤4)中:反应物用量是,按摩尔份数计,如式(2)所表示的硫桥配体1份,铂盐1.1~2份,相转移催化剂0~0.5份,极性溶剂10~30份;所述铂盐是四氯铂酸钾、四氯铂酸铵、三氯氨合铂酸钾、二氯二(二甲基亚砜)化铂或二氯二(四氢噻吩)化铂;所述相转移催化剂是四丁基溴化铵、三辛基甲基氯化铵、苄基三乙基氯化铵、四丁基氯化铵、四丁基硫酸氢铵、十二烷基三甲基氯化铵、十四烷基三甲基氯化铵或18—冠—6;所述极性溶剂是乙酸、二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷、乙二醇乙醚、甘油、缩水甘油醚、乙醇、甲醇或水中的一种或几种的混合物。
步骤5)中:反应物用量是,按摩尔份数计,如式(3)所表示的砜桥配体1份,铂盐1.1~2份,相转移催化剂0~0.5份,极性溶剂10~30份;所述铂盐是四氯铂酸钾、四氯铂酸铵、三氯氨合铂酸钾、二氯二(二甲基亚砜)化铂或二氯二(四氢噻吩)化铂;所述相转移催化剂是四丁基溴化铵、三辛基甲基氯化铵、苄基三乙基氯化铵、四丁基氯化铵、四丁基硫酸氢铵、十二烷基三甲基氯化铵、十四烷基三甲基氯化铵或18—冠—6;所述极性溶剂是乙酸、二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷、乙二醇乙醚、甘油、缩水甘油醚、乙醇、甲醇或水中的一种或几种的混合物。
有益效果:与现有技术相比,本发明具有以下优点:
本发明的硫桥联的喹唑啉类四齿铂配合物磷光材料,最有益的效果是通过在配体骨架上引入硫原子包裹铂核的刚性非共轭结构,硫原子将分子共轭打断,发光波长减小,实现蓝移,在很大程度上的提高了该磷光材料的发光效率和色纯度。通过对作为桥键的硫原子进行氧化,能够使材料发光产生不同程度的蓝移现象。本发明中用含活性基团的化合物取代卤原子,进一步提高配合物的溶解性、空穴传输能力、热稳定性,另外这些基团的引入可以产生一定的空间效应,从而减少配合物发光中心之间的相互作用,减少三重态激子的自淬灭现象,提高材料的发光性能。与部分金属离子有络合作用的硫原子的引入赋予化合物分子具有检测金属离子的效果,使得该材料不仅能应用于有机光电材料领域,也能应用到生物传感中。
附图说明
图1为实施例3中,硫桥联的喹唑啉类四齿铂配合物磷光材料S(qba)2Pt在二氯甲烷中的紫外吸收(UV)光谱和荧光发射(PL)光谱。
图2为实施例6中,硫桥联的喹唑啉类四齿铂配合物磷光材料S(qcz)2Pt在二氯甲烷中的紫外吸收(UV)光谱和荧光发射(PL)光谱。
图3为实施例9中,硫桥联的喹唑啉类四齿铂配合物磷光材料S(qpd)2Pt在二氯甲烷中的紫外吸收(UV)光谱和荧光发射(PL)光谱。
图4为实施例11中,硫桥联的喹唑啉类四齿铂配合物磷光材料S(qbao)2Pt在二氯甲烷中的紫外吸收(UV)光谱和荧光发射(PL)光谱。
具体实施方式
为了更好地理解本发明专利的内容,下面通过具体的实例和图例来进一步说明本发明的技术方案,具体包括合成、性质测定等。这些实施实例只是对本发明的说明,并不限制本发明。
实施例1、2-(3-溴苯基)-4-二苯胺基喹唑啉qba的制备
称取2-(3-溴苯基)-4-氯喹唑啉0.35g(1mmol)、60%氢化钠0.08g(2mmol)、二苯胺0.25g(1.5mmol)于两口瓶中,氮气保护下加入溶剂二甲基亚砜,30℃反应10h。反应结束后将反应液倒入水中,有大量白色沉淀生产,抽滤,柱层析,用石油醚:乙酸乙酯=20:1展开剂层析分离,得到白色固体qba 0.3g(0.67mmol),产率为67%。1H NMR(400MHz,CDCl3)δ7.93(m,8H),7.46(dd,J=5.3,3.2Hz,4H),7.12(dd,J=5.4,3.1Hz,4H),5.84(S,2H).
实施例2、配体硫原子桥连的喹唑啉S(qba)2的制备
称取2-(3-溴苯基)-4-二苯胺基喹唑啉qba 0.225g(0.5mmol)、磷酸钾0.064g(0.3mmol)、硫代乙酸钾0.029g(0.25mmol)、双(二亚苄基丙酮)钯0.023g(0.025mmol),1,1-双(二苯基膦)二茂铁0.02g(0.035mmol),氮气保护下加入甲苯3ml、丙酮1.5ml混合溶剂,110℃反应7h。反应结束后冷却至室温,二氯甲烷萃取,加入无水硫酸钠干燥,柱层析,用石油醚:乙酸乙酯=10:1展开剂层析分离,得到0.1g白色固体S(qba)2,产率为52%。1H NMR(400MHz,CDCl3)δ=8.38(S,2H),8.11(d,J=7.6,2H),7.96(d,J=7.9,2H),7.65(t,J=7.7,2H),7.39–7.28(m,17H),7.17(t,J=11.1,16H).
实施例3、配合物S(qba)2Pt的制备
称取硫原子桥连的喹唑啉S(qba)20.077g(0.1mmol)、四氯铂酸钾0.05g(0.1mmol)、四丁基溴化铵4mg,氮气保护下加入5ml乙酸,室温搅拌12小时,升温至120℃反应70h。反应结束后冷却至室温,加入15ml去离子水,有沉淀析出,抽滤,干燥,柱层析,用二氯甲烷:乙酸乙酯=5:1展开剂层析分离,得到0.032g橙红色固体S(qba)2Pt,产率为25%。1H NMR(400MHz,CDCl3)δ=8.14–8.07(m,2H),7.47(t,J=7.7,4H),7.42–7.28(m,9H),7.09(t,J=7.6,1H),6.99–6.93(m,2H).MALDI-TOF-MS(m/z):calcd for[M]+C52H34N6SPt:969.37,found:969.594.
实施例4、2-(3-溴苯基)-4-咔唑基喹唑啉qcz的制备
称取2-(3-溴苯基)-4-氯喹唑啉0.35g(1mmol)、60%氢化钠0.08g(2mmol)、咔唑0.28g(1.5mmol)于两口瓶中,氮气保护下加入溶剂二甲基亚砜10mL,30℃反应8h。反应结束后将反应液倒入水中,有大量黄色沉淀生产,抽滤,柱层析,用石油醚:乙酸乙酯=20:1展开剂层析分离,得到黄色固体qcz 0.36g(0.8mmol),产率为80%。1H NMR(400MHz,DMSO)δ=8.32(d,J=7.1,2H),8.27(d,J=8.2,1H),8.15–8.08(m,2H),8.06(d,J=9.3,1H),7.75(d,J=8.4,1H),7.67(dd,J=9.5,6.8,1H),7.50–7.36(m,7H),7.14(dd,J=8.2,3.6,1H).
实施例5、配体硫原子桥连的喹唑啉S(qcz)2的制备
称取2-(3-溴苯基)-4-咔唑基喹唑啉qcz 0.23g(0.5mmol)、磷酸钾0.064g(0.3mmol)、硫代乙酸钾0.029g(0.25mmol)、双(二亚苄基丙酮)钯0.023g(0.025mmol),1,1-双(二苯基膦)二茂铁0.02g(0.035mmol),氮气保护下加入甲苯3ml、丙酮1.5ml混合溶剂,110℃反应8h。反应结束后冷却至室温,二氯甲烷萃取,加入无水硫酸钠干燥,柱层析,用石油醚:乙酸乙酯=10:1展开剂层析分离,得到0.16g黄色固体S(qcz)2,产率为72%。1H NMR(400MHz,CDCl3)δ=8.77(s,1H),8.53(d,J=6.8,1H),8.22(d,J=9.1,1H),8.13(d,J=7.2,2H),7.94(t,J=7.2,1H),7.82(d,J=8.0,1H),7.55–7.45(m,3H),7.43(d,J=7.3,2H),7.35(dd,J=14.9,6.3,4H).
实施例6、配合物S(qcz)2Pt的制备
称取硫原子桥连的喹唑啉S(qcz)2 0.08g(0.1mmol)、四氯铂酸钾0.05g(0.12mmol)、四丁基溴化铵4mg,氮气保护下加入5ml乙酸,0.5ml去离子水,室温搅拌12小时,升温至120℃反应70h。反应结束后冷却至室温,加入20ml去离子水,有沉淀析出,抽滤,干燥,柱层析,用二氯甲烷:石油醚=5:1展开剂层析分离,得到0.023g橙红色固体S(qcz)2Pt,产率为19%。1H NMR(400MHz,CDCl3)δ=8.78(s,2H),8.53(d,J=7.8,2H),8.22(d,J=8.6,4H),8.13(d,J=6.9,4H),7.94(d,J=8.4,2H),7.82(d,J=8.4,2H),7.43(s,7H),7.38–7.31(m,10H).MALDI-TOF-MS(m/z):calcd for[M]+C44H30N6SPt:869.91,found:869.77.MALDI-TOF-MS(m/z):calcd for[M]+C52H30N6SPt:966.00,found:965.448.
实施例7、2-(3-溴苯基)-4-哌啶基喹唑啉qpd的制备
称取2-(3-溴苯基)-4-氯喹唑啉0.35g(1mmol)、60%氢化钠0.08g(2mmol)于两口瓶中,氮气保护下加入溶剂二甲基亚砜10mL、哌啶0.12mL(1.5mmol),在30℃条件下反应6h。反应结束后将反应液倒入水中,有大量白色沉淀生产,抽滤,柱层析,用石油醚:乙酸乙酯=50:1展开剂层析分离,得到白色固体qpd 0.25g(0.68mmol),产率为68%。1H NMR(400MHz,DMSO)δ=8.58(s,1H),8.45(d,J=7.9,1H),7.94(d,J=8.1,1H),7.86(d,J=9.4,1H),7.80(t,J=7.1,1H),7.68(d,J=9.0,1H),7.49(dt,J=15.7,8.0,2H),3.77(s,4H),1.72(s,6H).
实施例8、配体硫原子桥连的喹唑啉S(qpd)2的制备
称取2-(3-溴苯基)-4-哌啶基喹唑啉qpd 0.18g(0.5mmol)、磷酸钾0.064g(0.3mmol)、硫代乙酸钾0.029g(0.25mmol)、双(二亚苄基丙酮)钯0.023g(0.025mmol),1,1-双(二苯基膦)二茂铁0.02g(0.035mmol),氮气保护下加入甲苯3ml、丙酮1.5ml混合溶剂,110℃反应7h。反应结束后冷却至室温,二氯甲烷萃取,加入无水硫酸钠干燥,柱层析,用石油醚:乙酸乙酯=20:1展开剂层析分离,得到0.10g白色固体S(qpd)2,产率为57%。1H NMR(400MHz,CDCl3)δ=8.65(s,2H),8.48(d,J=7.6,2H),7.91(dd,J=27.0,8.6,4H),7.74–7.67(m,2H),7.51–7.38(m,7H),3.77–3.68(m,8H),1.84–1.72(m,15H).
实施例9、配合物S(qpd)2Pt的制备
称取硫原子桥连的喹唑啉S(qpd)2 0.06g(0.1mmol)、四氯铂酸钾0.05g(0.12mmol)、四丁基溴化铵4mg,氮气保护下加入5ml乙酸,0.5ml去离子水,室温搅拌12小时,升温至120℃反应70h。反应结束后冷却至室温,加入20ml去离子水,有沉淀析出,抽滤,干燥,柱层析,用二氯甲烷:石油醚=5:1展开剂层析分离,得到0.012g橙红色固体S(qpd)2Pt,产率为12%。1H NMR(400MHz,CDCl3)δ=8.17–8.06(m,2H),7.96–7.69(m,4H),7.64–7.37(m,4H),7.23–7.14(m,2H),7.11–6.98(m,2H),4.11(d,J=22.2,8H),1.94(dd,J=41.7,11.1,12H).MALDI-TOF-MS(m/z):calcd for[M]+C38H34N6SPt:801.88,found:801.398.
实施例10、配体S(qbao)2的制备
称取硫原子桥连的喹唑啉S(qba)2 0.22g(0.3mmol)、30%双氧水3ml,加入1ml乙酸和2ml乙酸酐,室温搅拌12小时。反应结束后除去溶剂,干燥,柱层析,用乙酸乙酯:石油醚=5:1展开剂层析分离,得到0.052g黄色色固体S(qbao)2,产率为23%。1H NMR(400MHz,CDCl3)δ=8.74(s,2H),7.82(d,J=6.5,2H),7.72(dd,J=7.0,3.5,2H),7.40(dd,J=9.1,4.0,9H),7.34(d,J=3.3,4H),7.26(s,15H).
实施例11、配合物S(qbao)2Pt的制备
称取硫原子桥连的喹唑啉S(qbao)2 0.16g(0.1mmol)、四氯铂酸钾0.1g(0.12mmol)、四丁基溴化铵4mg,氮气保护下加入5ml乙酸,0.5ml去离子水,室温搅拌12小时,升温至120℃反应70h。反应结束后冷却至室温,加入20ml去离子水,有沉淀析出,抽滤,干燥,柱层析,用二氯甲烷:石油醚=5:1展开剂层析分离,得到0.05g橙黄色色固体S(qbao)2Pt,产率为20%。1H NMR(400MHz,CDCl3)δ=7.73(dd,J=9.2,6.3,2H),7.54(dd,J=16.4,11.4,8H),7.40(dd,J=13.8,7.4,13H),7.24–7.14(m,9H).MALDI-TOF-MS(m/z):calcd for[M]+C38H34N6SPt:1002.03,found:1001.901.
Claims (7)
1.一类硫桥联的喹唑啉类四齿铂配合物磷光材料,其特征在于该铂配合物具体是由硫原子、砜桥联的喹唑啉类四齿铂配合物,其结构通式为下述式(I)和式(II)所表示的化合物:
R=
其中R是苯基、4-氟取代苯基、2,4-二氟取代苯基、3,4,5-三氟取代苯基、4-三氟甲基取代苯基、2-三氟甲基取代苯基、2,6-二甲基取代苯基、4-甲氧基取代苯基、4-硝基取代苯基、4-N,N-二甲胺取代苯基、2-苯并噻吩基、2-苯并呋喃基、9-(4-取代苯基)咔唑、9-(4-取代苯基)吩噻嗪、2取代9,9-二甲基芴基、叔丁烷氧基、2,6-二甲基取代苯氧基、六氢吡啶基、N-咔唑基、N-二苯胺基、N-二(4-叔丁基苯基)胺基、N-吩噻嗪基或9,9-二甲基氢化吖啶基中的一种。
2.一类如权利要求1所述的硫桥联的喹唑啉类四齿铂配合物磷光材料的制备方法,其特征在于所述的式(I)和式(II)所示的硫桥联的喹唑啉类四齿铂配合物磷光材料的制备方法包含以下步骤:
步骤1)2-(3-卤代苯基)-4-氯喹唑啉与RH溶于极性溶剂中,在碱、催化剂的存在下,25~120℃反应6~24h,得到如式(1)所表示的喹唑啉类衍生物,其中X是-Br、-I;
步骤2)如式(1)所表示的喹唑啉类衍生物溶于极性溶剂中,加入硫化试剂、碱、钯催化剂,在100~150℃下反应6~12h,得到如式(2)所表示的硫原子桥联的配体;
步骤3)如式(2)所表示的硫原子桥联的配体溶于极性溶剂中,加入氧化剂、催化剂,25~50℃下反应3~24h,得到如式(3)所表示的砜桥配体;
步骤4)如式(2)所表示的硫原子桥联的配体溶于极性溶剂中,加入铂盐、相转移催化剂,先室温搅拌12~24h,然后升温至120~150℃下反应24h~72h,得到如式(4)所表示的硫原子桥联的喹唑啉类四齿铂配合物;
步骤5)如式(3)所表示的砜桥配体溶于极性溶剂中,加入铂盐、相转移催化剂,先室温搅拌12~24h,然后升温至120~150℃下反应24h~72h,得到如式(5)所表示的砜桥联的喹唑啉类四齿铂配合物。
3.根据权利要求2所述的硫桥联的喹唑啉类四齿铂配合物磷光材料的制备方法,其特征是:步骤1)中:反应物用量是,按摩尔份数计,2-(3-溴苯基)-4-氯喹唑啉1份,带有活性基团的化合物RH 1~4份,催化剂0.01~0.1份,极性溶剂10~50份,碱0.1~10份;所述R是苯基、4-氟取代苯基、2,4-二氟取代苯基、3,4,5-三氟取代苯基、4-三氟甲基取代苯基、2-三氟甲基取代苯基、2,6-二甲基取代苯基、4-甲氧基取代苯基、4-硝基取代苯基、4-N,N-二甲胺取代苯基、2-苯并噻吩基、2-苯并呋喃基、9-(4-取代苯基)咔唑、9-(4-取代苯基)吩噻嗪、2取代9,9-二甲基芴基、叔丁烷氧基、2,6-二甲基取代苯氧基、六氢吡啶基、N-咔唑基、N-二苯胺基、N-二(4-叔丁基苯基)胺基、N-吩噻嗪基或9,9-二甲基氢化吖啶基;所述的催化剂是四三苯基磷钯、双(二亚苄基丙酮)钯、三(二亚苄基丙酮)二钯、二(三苯基膦)二氯化钯或1,1′-二(二苯膦基)二茂铁二氯化钯;所述的碱是碳酸钾、碳酸钠、叔丁醇钠、叔丁醇钾、正丁基锂或氢化钠;所述有机溶剂是乙醇、乙二醇二甲醚、甲苯,四氢呋喃、二甲基亚砜、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺或1,4-二氧六环中的一种或几种的混合物。
4.根据权利要求2所述的硫桥联的喹唑啉类四齿铂配合物磷光材料的制备方法,其特征是:步骤2)中:反应物用量是,按摩尔份数计,如式(1)所表示的化合物1份,硫化试剂0.5~1份,碱0.6~1份,钯催化剂0.05~0.1份,有机溶剂10~30份;所述的硫化试剂是硫代乙酸钾、硫代乙酸钠、硫脲、硫化钠、硫氰化钾或硫;所述催化剂是四三苯基磷钯、双(二亚苄基丙酮)钯、三(二亚苄基丙酮)二钯、二(三苯基膦)二氯化钯、1,1′-二(二苯膦基)二茂铁二氯化钯、碘化亚铜或氧化铜;所述的碱是氢氧化钠、氢氧化钾、碳酸钾、磷酸钾、乙酸钾、氟化钾、碳酸铯、叔丁醇钠或叔丁醇钾;所述极性溶剂是甲苯、丙酮、聚乙二醇、二甲基亚砜、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺或四氢呋喃中的一种或几种的混合物。
5.根据权利要求2所述的硫桥联的喹唑啉类四齿铂配合物磷光材料的制备方法,其特征是:步骤3)中:反应物用量是,按摩尔份数计,如式(2)所表示的硫桥配体1份,氧化剂5~50份,催化剂0-0.1份,极性溶剂10~30份;所述氧化剂是双氧水、硝酸铜、硝酸银、氯化银、高锰酸钾、亚硫酸氢钾、次氯酸钠、高碘酸、铬酸酐、过氧乙酸或过氧苯甲酸中的一种或几种的混合物;所述催化剂是氯化铁、钨酸钠或钒酸钠;所述极性溶剂是乙酸、乙酸酐、乙腈、水、丙酮、二氯甲烷或乙醚中的一种或几种的混合物。
6.根据权利要求2所述的硫桥联的喹唑啉类四齿铂配合物磷光材料的制备方法,其特征是:步骤4)中:反应物用量是,按摩尔份数计,如式(2)所表示的硫桥配体1份,铂盐1.1~2份,相转移催化剂0~0.5份,极性溶剂10~30份;所述铂盐是四氯铂酸钾、四氯铂酸铵、三氯氨合铂酸钾、二氯二(二甲基亚砜)化铂或二氯二(四氢噻吩)化铂;所述相转移催化剂是四丁基溴化铵、三辛基甲基氯化铵、苄基三乙基氯化铵、四丁基氯化铵、四丁基硫酸氢铵、十二烷基三甲基氯化铵、十四烷基三甲基氯化铵或18-冠-6;所述极性溶剂是乙酸、二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷、乙二醇乙醚、甘油、缩水甘油醚、乙醇、甲醇或水中的一种或几种的混合物。
7.根据权利要求2所述的硫桥联的喹唑啉类四齿铂配合物磷光材料的制备方法,其特征是:步骤5)中:反应物用量是,按摩尔份数计,如式(3)所表示的砜桥配体1份,铂盐1.1~2份,相转移催化剂0~0.5份,极性溶剂10~30份;所述铂盐是四氯铂酸钾、四氯铂酸铵、三氯氨合铂酸钾、二氯二(二甲基亚砜)化铂或二氯二(四氢噻吩)化铂;所述相转移催化剂是四丁基溴化铵、三辛基甲基氯化铵、苄基三乙基氯化铵、四丁基氯化铵、四丁基硫酸氢铵、十二烷基三甲基氯化铵、十四烷基三甲基氯化铵或18-冠-6;所述极性溶剂是乙酸、二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷、乙二醇乙醚、甘油、缩水甘油醚、乙醇、甲醇或水中的一种或几种的混合物。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910302583.6A CN110016057B (zh) | 2019-04-15 | 2019-04-15 | 硫桥联的喹唑啉类四齿铂配合物磷光材料及其制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910302583.6A CN110016057B (zh) | 2019-04-15 | 2019-04-15 | 硫桥联的喹唑啉类四齿铂配合物磷光材料及其制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN110016057A true CN110016057A (zh) | 2019-07-16 |
CN110016057B CN110016057B (zh) | 2022-03-29 |
Family
ID=67191426
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910302583.6A Active CN110016057B (zh) | 2019-04-15 | 2019-04-15 | 硫桥联的喹唑啉类四齿铂配合物磷光材料及其制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110016057B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110862350A (zh) * | 2019-12-02 | 2020-03-06 | 南京邮电大学 | 蝶烯哒嗪类四齿铂配合物磷光材料及其制备方法和应用 |
CN113683646A (zh) * | 2021-09-18 | 2021-11-23 | 广西民族大学 | 含单碳硼烷类金属铂配合物及其制备方法、应用 |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016025921A1 (en) * | 2014-08-15 | 2016-02-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Non-platinum metal complexes for excimer based single dopant white organic light emitting diodes |
CN106467560A (zh) * | 2015-08-18 | 2017-03-01 | 三星电子株式会社 | 有机金属化合物和包括其的有机发光器件 |
CN108218878A (zh) * | 2018-03-20 | 2018-06-29 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN108276452A (zh) * | 2018-03-20 | 2018-07-13 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN108299512A (zh) * | 2018-03-20 | 2018-07-20 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN108299513A (zh) * | 2018-03-20 | 2018-07-20 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN108383879A (zh) * | 2018-03-20 | 2018-08-10 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN108424427A (zh) * | 2011-07-25 | 2018-08-21 | 通用显示公司 | 四齿铂配合物 |
CN109021024A (zh) * | 2018-07-16 | 2018-12-18 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN109251223A (zh) * | 2017-07-14 | 2019-01-22 | 三星显示有限公司 | 有机金属化合物和包括其的有机发光器件 |
-
2019
- 2019-04-15 CN CN201910302583.6A patent/CN110016057B/zh active Active
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108424427A (zh) * | 2011-07-25 | 2018-08-21 | 通用显示公司 | 四齿铂配合物 |
WO2016025921A1 (en) * | 2014-08-15 | 2016-02-18 | Arizona Board Of Regents On Behalf Of Arizona State University | Non-platinum metal complexes for excimer based single dopant white organic light emitting diodes |
CN106467560A (zh) * | 2015-08-18 | 2017-03-01 | 三星电子株式会社 | 有机金属化合物和包括其的有机发光器件 |
CN109251223A (zh) * | 2017-07-14 | 2019-01-22 | 三星显示有限公司 | 有机金属化合物和包括其的有机发光器件 |
CN108218878A (zh) * | 2018-03-20 | 2018-06-29 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN108276452A (zh) * | 2018-03-20 | 2018-07-13 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN108299512A (zh) * | 2018-03-20 | 2018-07-20 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN108299513A (zh) * | 2018-03-20 | 2018-07-20 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN108383879A (zh) * | 2018-03-20 | 2018-08-10 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
CN109021024A (zh) * | 2018-07-16 | 2018-12-18 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110862350A (zh) * | 2019-12-02 | 2020-03-06 | 南京邮电大学 | 蝶烯哒嗪类四齿铂配合物磷光材料及其制备方法和应用 |
CN110862350B (zh) * | 2019-12-02 | 2022-02-01 | 南京邮电大学 | 蝶烯哒嗪类四齿铂配合物磷光材料及其制备方法和应用 |
CN113683646A (zh) * | 2021-09-18 | 2021-11-23 | 广西民族大学 | 含单碳硼烷类金属铂配合物及其制备方法、应用 |
CN113683646B (zh) * | 2021-09-18 | 2024-04-05 | 广西民族大学 | 含单碳硼烷类金属铂配合物及其制备方法、应用 |
Also Published As
Publication number | Publication date |
---|---|
CN110016057B (zh) | 2022-03-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR102124227B1 (ko) | 금속 화합물, 방법, 및 이의 용도 | |
CN106459095B (zh) | 金属有机骨架(mof)黄色磷光体及其在白光发射器件中的应用 | |
CN106565781B (zh) | 含有膦的二苯酮类有机发光材料及其合成方法与应用 | |
Chen et al. | Synthesis, structure and luminescence properties of zinc (II) complexes with terpyridine derivatives as ligands | |
CN108084150B (zh) | 有机单分子白光材料及其制备方法与oled器件 | |
Gong et al. | Synthesis and device properties of mCP analogues based on fused-ring carbazole moiety | |
Zhang et al. | Photo-and electro-luminescence of four cuprous complexes with sterically demanding and hole transmitting diimine ligands | |
US20200295268A1 (en) | Organic light-emitting material, method for the preparation thereof and use thereof | |
CN110016057A (zh) | 硫桥联的喹唑啉类四齿铂配合物磷光材料及其制备方法 | |
CN107445996B (zh) | 蝶烯修饰的哒嗪类铱配合物磷光材料及其制备方法和应用 | |
Wang et al. | A facile way to synthesize high-triplet-energy hosts for blue phosphorescent organic light-emitting diodes with high glass transition temperature and low driving voltage | |
Yan et al. | Blue Electrophosphorescence from Iridium (III) Phosphors Bearing Asymmetric Di‐N‐Aryl 6‐(trifluoromethyl)‐2H‐imidazo [4, 5‐b] pyridin‐2‐ylidene Chelates | |
Hu et al. | The one-pot synthesis of homoleptic phenylphthalazine iridium (III) complexes and their application in high efficiency OLEDs | |
CN109824722B (zh) | 双氮单膦化合物及其制备方法和应用以及卤化亚铜配合物及其制备方法和应用 | |
CN108623639A (zh) | 蝶烯修饰的哒嗪类铂配合物磷光材料及其制备方法和应用 | |
CN109336932B (zh) | 两亲性铂(ⅱ)配合物及其制备和构筑白色发光体系的应用 | |
Zhao et al. | Fluoro-benzenesulfonyl-functionalized 2-phenylthiazole-type iridium (iii) complexes for efficient solution-processed organic light-emitting diodes | |
Tang et al. | Cost-effective synthesis of α-carboline/pyridine hybrid bipolar host materials with improved electron-transport ability for efficient blue phosphorescent OLEDs | |
Hao et al. | Synthesis and optoelectronic properties of dinuclear iridium (III) complexes containing deep blue fluorescence chromophore in the single-emissive-layer WPLEDs | |
CN111349119B (zh) | 蝶烯哒嗪类八齿双铂配合物磷光材料及其制备方法和应用 | |
Wang et al. | Neutral Pt (II) complexes containing diazafluorene derivative ligands and their electroluminescent properties | |
WO2020158689A1 (ja) | 有機電界発光素子用の有機イリジウム錯体 | |
Zhou et al. | Synthesis and properties of a series of iridium complexes with naphthalenyl imidazo [2, 1-b] thiazole derivatives as primary ligands | |
Si et al. | Synthesis and photoelectric properties of Ir III complexes using fluorobenzylimidazole [2, 1-b] thiazole derivatives as primary ligands | |
Zhang et al. | Yellow electrophosphorescent devices with hosts containing N 1-(naphthalen-1-yl)-N 1, N 4-diphenylnaphthalene-1, 4-diamine and tetraphenylsilane units |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |