CN109970714A - Four tooth platinum (II) complexs of one kind and application - Google Patents
Four tooth platinum (II) complexs of one kind and application Download PDFInfo
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- CN109970714A CN109970714A CN201811567623.1A CN201811567623A CN109970714A CN 109970714 A CN109970714 A CN 109970714A CN 201811567623 A CN201811567623 A CN 201811567623A CN 109970714 A CN109970714 A CN 109970714A
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- Prior art keywords
- atom
- halogen
- substituted
- alkyl
- complex
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- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000000463 material Substances 0.000 claims abstract description 17
- 239000002019 doping agent Substances 0.000 claims abstract description 6
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000005266 diarylamine group Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 6
- -1 pinacol borate Ester Chemical class 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 150000003222 pyridines Chemical class 0.000 claims description 4
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 125000005504 styryl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910019029 PtCl4 Inorganic materials 0.000 claims description 2
- 238000010520 demethylation reaction Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- 239000002243 precursor Substances 0.000 claims 3
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 241001597008 Nomeidae Species 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 229910052757 nitrogen Inorganic materials 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- 239000007787 solid Substances 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 238000006073 displacement reaction Methods 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000003810 ethyl acetate extraction Methods 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 13
- 238000003809 water extraction Methods 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 239000002585 base Substances 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- BMQDAIUNAGXSKR-UHFFFAOYSA-N (3-hydroxy-2,3-dimethylbutan-2-yl)oxyboronic acid Chemical compound CC(C)(O)C(C)(C)OB(O)O BMQDAIUNAGXSKR-UHFFFAOYSA-N 0.000 description 3
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 101000687716 Drosophila melanogaster SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 homolog Proteins 0.000 description 3
- 101000687741 Mus musculus SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily A containing DEAD/H box 1 Proteins 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 210000003739 neck Anatomy 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000002061 vacuum sublimation Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 2
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- 150000004753 Schiff bases Chemical class 0.000 description 2
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 150000003851 azoles Chemical class 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229940126543 compound 14 Drugs 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- 229940126142 compound 16 Drugs 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
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- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- ROEQGIFOWRQYHD-UHFFFAOYSA-N (2-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC=C1B(O)O ROEQGIFOWRQYHD-UHFFFAOYSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
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- 230000032683 aging Effects 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002473 indoazoles Chemical class 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K77/00—Constructional details of devices covered by this subclass and not covered by groups H10K10/80, H10K30/80, H10K50/80 or H10K59/80
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- 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
-
- 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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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
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present invention relates to a kind of four tooth platinum (II) complexs and application, which has N^N^N^O configuration, and shown in structure such as formula (3), wherein A1-A5 is five-membered ring replace or non-substituted, hexatomic ring, condensed cyclic structure.The complex can be used as a kind of phosphorescence dopant material and apply in the field OLED.Platinum (II) complex have high fluorescence quantum efficiency, good thermal stability and it is low constant is quenched, high-luminous-efficiency, the low orange-red light OLED device roll-offed can be manufactured.
Description
Technical field
The present invention relates to a kind of novel N^N^N^O tetra- tooth platinum (II) complex metallo organic materials, in particular for OLED
Play the phosphorescence dopant material of photon transmitting in the luminescent layer of luminescent device.
Background technique
Since Organic Light Emitting Diode (OLED, Organic Light-Emitting Diode) display technology self-discovery,
Because its have low energy consumption, visual angle is big, can the unique performance such as flexibility be constantly subjected to widely to pay close attention to and research, in recent years
Even more gradually applied on the electronic products such as mobile phone, TV, laptop.But compared with traditional display technology, OLED
There are service lifes it is short, color purity is poor, easy to aging the disadvantages of cause its cost high, hinder pushing away for OLED technology
Extensively with development.Therefore, novel OLED material how is designed, then is the emphasis and difficult point of OLED area research.
In OLED material field, phosphorescent OLED Materials more rapidly with maturation.Phosphorescent OLED material is mainly based upon
Some heavy metal organic coordination compounds, such as iridium, platinum, europium, osmium.Phosphor material can make full use of singlet in luminescence process
With the energy of triplet excitons, therefore theoretically its quantum efficiency can reach 100%, and which greatly enhances the hairs of OLED device
Light efficiency is that current industry uses wider luminescent material.
Wherein, in recent years based on the phosphorescent OLED material of platinum (II) gradually develop and achieve preferable research at
Fruit.Platinum (II) is generally four-coordination point, thus can form the metal organic platinum with unique configuration by design tetradentate ligands
(II) complex.In general, common tetradentate ligands mainly have O^N^N^O (such as formula (1)), O^N^C^O (such as formula (2)) class
Type,
Wherein, O^N^N^O class four tooth platinum (II) complex is mainly schiff bases (Schiff base) class, relatively conventional, but
Stability is relatively poor；O^N^C^O class four tooth platinum (II) complex is comparatively stable, but performance have it is to be hoisted.
Summary of the invention
The present invention devises a kind of novel N^N^N^O configuration four tooth platinum (II) complex, can be used as a kind of phosphorescence doping
Material is applied in the field OLED, is a kind of new ligands mode, is shown preferable stability and luminescent properties.
A kind of N^N^N^O configuration four tooth platinum (II) complex has the basic structure as shown in formula (3):
Wherein, A1-A5 is five-membered ring replace or non-substituted, hexatomic ring, condensed cyclic structure.
The present invention also provides the preparation methods of novel N^N^N^O configuration four tooth platinum (II) complex.
It is preferred that: the structure as shown in formula (4):
Wherein R1- R17It is independent to be selected from hydrogen, deuterium, halogen, hydroxyl, acyl group, alkoxy, acyloxy, amino, nitro, acyl
Base amino, carboxyl, styryl, amino carbonyl, carbamoyl, benzyloxycarbonyl group, aryloxy group, diaryl-amine base, contains 1- at cyano
The saturated alkyl of 30 C atoms, the unsaturated alkyl containing 1-20 C atom, replace containing 5-30 C atom or it is unsubstituted
Aryl, contain the substituted or unsubstituted heteroaryl of 5-30 C atom or adjacent R1- R17Each other by covalent key connection
Cyclization；Wherein, X1- X27For carbon, the halogen is F, Cl, Br.
It is preferred that: wherein R1- R17It is independent to be selected from hydrogen, halogen, amino, nitro, cyano, diaryl-amine base, contain 1-10 C
The saturated alkyl of atom, containing 5-20 C atom by halogen or one or more C1-C4 be alkyl-substituted or unsubstituted virtue
Base, containing 5-20 C atom by halogen or one or more C1-C4 be alkyl-substituted or unsubstituted heteroaryl or adjacent
R1- R17Cyclization is connected each other by covalent bond, the halogen is F, Cl.
It is preferred that: for having structure
Wherein R1'-R5' it is independent selected from hydrogen, halogen, diaryl-amine base, the saturated alkyl containing 1-10 C atom, containing 5-
10 C atoms by halogen or one or more C1-C4 be alkyl-substituted or unsubstituting aromatic yl, the quilt containing 5-10 C atom
Halogen or one or more C1-C4 is alkyl-substituted or unsubstituted heteroaryl or adjacent R1- R17Each other by covalent bond
Connection cyclization.
It is preferred that: R1'-R5' 5 groups in, wherein thering is 0-3 group is independent to be expressed as diaryl-amine base, containing 5-10
A C atom by halogen or one to three C1-C4 be alkyl-substituted or unsubstituted aryl, containing 5-10 C atom by halogen
Or one to three C1-C4 is alkyl-substituted or unsubstituted heteroaryl；Other groups are independent to be expressed as hydrogen or containing 1-8
The saturated alkyl of a C atom, the halogen are F.
It is preferred that: R1'-R5' 5 groups in, wherein have 0-3 group it is independent be expressed as hexichol amido, benzene, pyridine,
Carbazyl, other groups are independent to be expressed as hydrogen, isopropyl or tert-butyl.
For the purpose of the application, unless otherwise specified, term halogen, alkyl, alkenyl, aryl, acyl group, alkoxy and miscellaneous
Ring aromatic systems or heterocyclic aromatic group can have following meanings:
Above-mentioned halogen or it is halogenated include fluorine, chlorine, bromine and iodine, preferably F, Cl, Br, particularly preferred F or Cl, most preferably F.
It include that there is 5-30 carbon atom, preferably 5-20 carbon above by covalent bond connection cyclization, aryl, heteroaryl
Atom, more preferable 5-10 carbon atom and the aryl being made of the aromatic ring of an aromatic ring or multiple thick sums.Suitable aryl
For, such as phenyl, naphthalene, acenaphthenyl (acenaphthenyl), dihydro-acenaphthylene base (acenaphthenyl), anthryl, fluorenyl, phenanthryl
(phenalenyl).The aryl can be for unsubstituted (i.e. all carbon atoms that can replace have hydrogen atom) or the one of aryl
It is substituted on a, more than one or all substitutive positions.Suitable substituent group is such as halogen, preferably F, Br or Cl；Alkane
Base preferably has the alkyl of 1-20,1-10 or 1-8 carbon atom, particularly preferred methyl, ethyl, isopropyl or uncle
Butyl；Aryl, preferably can substituted again or unsubstituted C5, C6Aryl or fluorenyl；Heteroaryl preferably contains at least one nitrogen
The heteroaryl of atom, particularly preferred pyridyl group；Aryl especially particularly preferably with the substituent group selected from F and tert-butyl, preferably may be used
For given aryl or optionally to be replaced by least one above-mentioned substituent group be C5, C6The aryl of aryl, C5, C6Aryl is especially excellent
Choosing has 0,1 or 2 above-mentioned substituent group, C5, C6The especially particularly preferred unsubstituted phenyl of aryl or substituted phenyl, such as join
Phenyl, the phenyl preferably replaced in meta position by two tert-butyls.
Unsaturated alkyl containing 1-20 C atom, preferably alkenyl, more preferably with the alkenyl of a double bond, particularly preferably
Alkenyl with double bond and 1-8 carbon atom.
Abovementioned alkyl includes having 1-30 carbon atom, preferably 1-10 carbon atom, the alkane of preferably 1-4 carbon atom
Base.The alkyl can be branch or straight chain, be also possible to annular, and can be by one or more hetero atoms, preferably N, O or S
Interruption.Moreover, the alkyl can be replaced one or more halogens or the above-mentioned substituent group about aryl.Equally, for alkane
For base, be with one or more aryl it is possible, all above-mentioned aryl are suitable for the purpose, and alkyl is particularly preferred
From methyl, ethyl, isopropyl, n-propyl, isobutyl group, normal-butyl, tert-butyl, sec-butyl, isopentyl, cyclopropyl, cyclopenta,
Cyclohexyl.
Above-mentioned acyl group is that CO group is connected to singly-bound, alkyl as used herein.
Above-mentioned alkoxy is connected directly with singly-bound and oxygen, alkyl as used herein.
Above-mentioned heteroaryl group is understood to and aromatics, C3- C8Ring group is related, and also comprising an oxygen or sulphur atom or
The combination of 1-4 nitrogen-atoms or an oxygen or sulphur atom and most two nitrogen-atoms and their substituted and benzo and
The derivative of the thick sum of pyrido, for example, being connected via one of ring carbons, the heteroaryl group can be by one or more
Replaced a substituent group about aryl mentioned.
In certain embodiments, heteroaryl can be to carry above independent five containing 0,1 or 2 substituent group, hexa-atomic
Aromatic heterocyclic ring systems.The representative instance of heteroaryl includes but is not limited to unsubstituted furans, benzofuran, thiophene, benzo thiophene
Pheno, pyrroles, pyridine, indoles, azoles, benzothiazole, isoxazole, benzo isoxazole, thiazole, benzothiazole, isothiazole, imidazoles, benzo miaow
Azoles, pyrazoles, indazole, tetrazolium, quinoline, isoquinolin, pyridazine, pyrimidine, purine and pyrazine, furans, 1,2,3- diazole, 1,2,3- thiophene
Diazole, 1,2,4- thiadiazoles, triazole, benzotriazole, pyridine of talking endlessly, benzothiazole, diazole, benzopyrazoles, quinolizine, cinnolines, phthalazines, quinoline
Azoles and quinoxaline and its mono- or di-substituted derivative.In certain embodiments, substituent group be halogenated, hydroxyl, cyano,
O-C1~6Alkyl, C1~6Alkyl, hydroxyl C1~6Alkyl and amino-C1~6Alkyl.
Specific example as follows, including but not limited to flowering structure:
The preparation method of above-mentioned complex, includes the following steps:
As follows, carbazole analog derivative S1 obtains substrate S2 through bromo-reaction, and S2 is reacted with connection pinacol borate
It reacts to obtain S5 through Suzuki with pyridine derivatives S4 to corresponding pinacol ester derivative S3, S3, S5 and pyridines are derivative
Object S6 reacts to obtain S7 through Suzuki, and corresponding ligand S8, S8 and K are obtained after S7 demethylation2PtCl4Reaction obtains target production
Object P.
Wherein, R'1~R'5For aromatic radical or non-aromatic substituent group.
N^N^N^O tetra- tooth platinum (II) complex can be used in OLED luminescent device, and photon transmitting is played in luminescent layer
The phosphorescence dopant material of effect.
Using platinum (II) complex with above structure, the OLED device of heat deposition and solution processing can be manufactured.
Organic luminescent device including containing one or more complexs.
The complex is wherein applied in the device in the form of layer by heat deposition.
Wherein apply the complex in the form of layer by being spin-coated in the device.
The complex is wherein applied in the device in the form of layer by inkjet printing.
Above-mentioned organic luminescent device, when applying electric current, the device is emitted as orange red.
Platinum (II) complex in the present invention has a high fluorescence quantum efficiency, good thermal stability and it is low constant is quenched,
High-luminous-efficiency, the low orange-red light OLED device roll-offed can be manufactured.
Detailed description of the invention
Fig. 1 organic electroluminescence device structural schematic diagram of the present invention,
Specific embodiment
The present invention will be further described in detail below with reference to the embodiments.
Embodiment 1:
Synthetic route:
The synthesis of compound 2: taking 6.50g (20.0mmol) compound 1, connection pinacol borate 12.70g (2.5eq.,
50.0mmol), potassium carbonate 5.18g (2.5eq., 50.0mmol) and Pd (dppf) Cl2292mg (0.02eq., 0.4 mmol),
It is added in three-neck flask, vacuumizes and be passed through nitrogen displacement repeatedly, be then injected into acetonitrile dioxane 150mL, be heated to 85
℃.It after reacting 12hr under nitrogen protection, is cooled to room temperature, revolving removes solvent, adds suitable quantity of water and ethyl acetate extraction
It takes, collects organic phase, proper silica gel is added after anhydrous magnesium sulfate is dry, revolving removes solvent, uses n-hexane/ethyl acetate
System column chromatography, obtains white solid 7.12g, yield 85%, purity 99.0%.
The synthesis of compound 3: 11.85g (50.0mmol) compound 2,6- dibromo pyridine, 2- methoxyphenylboronic acid 7.60 are taken
G (1.0eq., 50.0mmol), potassium carbonate 6.48g (1.25eq., 62.5mmol) and Pd (OAc)2 224mg(0.02 eq.,
1mmol), PPh31.31g (0.1eq., 5mmol) is added in three-neck flask, is vacuumized and is passed through nitrogen displacement repeatedly, then
Acetonitrile 150mL is injected, methanol 50mL is heated to 60 DEG C.It after reacting 12hr under nitrogen protection, is cooled to room temperature, revolving removes
Solvent adds suitable quantity of water and ethyl acetate extraction, collects organic phase, proper silica gel is added after anhydrous magnesium sulfate is dry, rotates
Solvent is removed, is chromatographed using n-hexane/ethyl acetate system column, obtains white solid 9.90g, yield 75%, purity
99.5%.
The synthesis of compound 4: taking 6.29g (15.0mmol) compound 2, and 3 3.96g of compound (1.0eq., 15.0
Mmol), potassium carbonate 3.45g (1.25eq., 25.0mmol) and Pd (PPh3)4347mg (0.02eq., 0.3mmol), is added to
In three-neck flask, vacuumizes and be passed through nitrogen displacement repeatedly, be then injected into acetonitrile 100mL and 50mL methanol, be heated to 60 DEG C.?
It after reacting 12hr under nitrogen protection, is cooled to room temperature, revolving removes solvent, adds suitable quantity of water and ethyl acetate extraction, collects
Organic phase, is added proper silica gel after anhydrous magnesium sulfate is dry, revolving removes solvent, uses n-hexane/ethyl acetate system column layer
Analysis, obtains white solid 4.28g, yield 60%, purity 99.5%.
The synthesis of compound 5: taking 3.81g (8.0mmol) compound 4,2- bromopyridine 1.37g (1.1eq., 8.8mmol),
Potassium carbonate 1.38g (1.25eq., 10.0mmol) and Pd (PPh3)4185mg (0.02eq., 0.16mmol) is added to three necks burning
In bottle, vacuumizes and be passed through nitrogen displacement repeatedly, be then injected into acetonitrile 60mL and 30mL methanol, be heated to 60 DEG C.In nitrogen protection
After lower reaction 12hr, it is cooled to room temperature, revolving removes solvent, and suitable quantity of water and ethyl acetate extraction are added, organic phase is collected,
Proper silica gel is added after anhydrous magnesium sulfate is dry, revolving removes solvent, chromatographs, obtains using n-hexane/ethyl acetate system column
White solid 3.07g, yield 90%, purity 99.9%.
The synthesis of compound 6: taking 2.14g (4.0mmol) compound 5, and pyridine hydrochloride 30g (PyHCl) is added to three
In neck flask, vacuumizes and be passed through nitrogen displacement repeatedly, be heated to 190 DEG C under nitrogen protection, after reacting 4hr, be cooled to room
Temperature, suitable quantity of water and ethyl acetate extraction are added, organic phase is collected, proper silica gel is added after anhydrous magnesium sulfate is dry, rotates
Solvent is removed, is chromatographed using n-hexane/ethyl acetate system column, obtains white solid 1.32g, yield 80%, purity 99.9%.
Mass spectrum (ESI-)([M-H]-)C28H18N3O theoretical value: 412.15；Measured value: 412.13.
The synthesis of compound P1: take 826mg (2.0mmol) compound 5 and 328mg anhydrous sodium acetate (2.0eq., 4.0
Mmol) be dissolved in 25mL DMSO, stir, be heated to 80 DEG C, then be added Platinous Potassium Chloride 830mg (1.0eq., 2.0
Mmol), vacuumize and be passed through nitrogen displacement for several times, be warming up to 120 DEG C of reaction 5hr.After reaction, 100ml water is added while hot,
Filtering is collected solid, is washed with suitable quantity of water and methanol, the solid re crystallization from toluene that will be obtained, then vacuum sublimation obtains depth
Red solid 788mg, gross production rate 65%, purity 99.9%.Mass spectrum (ESI-)([M-H]-)C28H16N3OPt theoretical value: 605.10；
Measured value: 605.08.
Embodiment 2:
Synthetic route:
The synthesis of compound 7: take 16.72g carbazole (0.10mol) and 655mg aluminum trichloride (anhydrous) (5mmol) in three necks
It in flask, vacuumizes and is passed through nitrogen displacement repeatedly, be then added dropwise tert-butyl chloride 27.77g (3.0eq., 0.30mmol) and dry
Dry methylene chloride 250mL after being stirred to react 12hr under nitrogen protection, adds suitable quantity of water extraction, collects organic phase, rotation
Solvent is evaporated off, obtained solid is used into ethyl alcohol recrystallization, obtains white solid 23.20g, yield 83%, purity
99.5%.
The synthesis of compound 8: 13.97g (50.0mmol) compound 7 is taken, is dissolved in 750mL acetic acid, then instills bromine
19.98g (2.5eq., 125.0mmol), shading reaction.After about 4hr is stirred at room temperature, revolving removes solvent, adds suitable quantity of water
It is washed with solution of sodium bisulfite, ethyl acetate extraction, collects organic phase, proper silica gel is added after anhydrous magnesium sulfate is dry, revolves
Solvent is evaporated off, is chromatographed using n-hexane/ethyl acetate system column, obtains white solid 20.77g, yield 95%, purity
99.9%.
The synthesis of compound 9: taking 10.93g (25.0mmol) compound 8, connection pinacol borate 15.88g (2.5eq.,
62.5mmol), potassium carbonate 8.64g (2.5eq., 62.5mmol) and Pd (dppf) Cl2366mg (0.02eq., 0.5 mmol),
It is added in three-neck flask, vacuumizes and be passed through nitrogen displacement repeatedly, be then injected into dioxane 300mL, be heated to 85 DEG C.?
It after reacting 12hr under nitrogen protection, is cooled to room temperature, revolving removes solvent, adds suitable quantity of water and ethyl acetate extraction, collects
Organic phase, is added proper silica gel after anhydrous magnesium sulfate is dry, revolving removes solvent, uses n-hexane/ethyl acetate system column layer
Analysis, obtains white solid 9.56g, yield 72%, purity 99.9%.
The synthesis of compound 10: taking 7.97g (15.0mmol) compound 9, and 3 3.96g of compound (1.0eq., 15.0
Mmol), potassium carbonate 3.45g (1.25eq., 25.0mmol) and Pd (PPh3)4347mg (0.02eq., 0.3mmol), is added to
In three-neck flask, vacuumizes and be passed through nitrogen displacement repeatedly, be then injected into acetonitrile 100mL and 50mL methanol, be heated to 60 DEG C.?
It after reacting 12hr under nitrogen protection, is cooled to room temperature, revolving removes solvent, adds suitable quantity of water and ethyl acetate extraction, collects
Organic phase, is added proper silica gel after anhydrous magnesium sulfate is dry, revolving removes solvent, uses n-hexane/ethyl acetate system column layer
Analysis, obtains white solid 5.74g, yield 65%, purity 99.9%.
The synthesis of compound 11: taking 4.71g (8.0mmol) compound 10, and 2- bromopyridine 1.37g (1.1eq., 8.8
Mmol), potassium carbonate 1.38g (1.25eq., 10.0mmol) and Pd (PPh3)4185mg (0.02eq., 0.16mmol), is added to
In three-neck flask, vacuumizes and be passed through nitrogen displacement repeatedly, be then injected into acetonitrile 60mL and 30mL methanol, be heated to 60 DEG C.In nitrogen
It after reacting 12hr under gas shielded, is cooled to room temperature, revolving removes solvent, adds suitable quantity of water and ethyl acetate extraction, and collection has
Machine phase, is added proper silica gel after anhydrous magnesium sulfate is dry, revolving removes solvent, uses n-hexane/ethyl acetate system column layer
Analysis, obtains white solid 3.67g, yield 85%, purity 99.9%.
The synthesis of compound 12: taking 2.16g (4.0mmol) compound 11, and pyridine hydrochloride 30g (PyHCl) is added to
In three-neck flask, vacuumizes and be passed through nitrogen displacement repeatedly, be heated to 190 DEG C under nitrogen protection, after reacting 4hr, be cooled to room
Temperature, suitable quantity of water and ethyl acetate extraction are added, organic phase is collected, proper silica gel is added after anhydrous magnesium sulfate is dry, rotates
Solvent is removed, is chromatographed using n-hexane/ethyl acetate system column, obtains white solid 1.79g, yield 85%, purity 99.9%.
Mass spectrum (ESI-)([M-H]-)C36H34N3O theoretical value: 524.27；Measured value: 524.24.
The synthesis of compound P2: take 1.06g (2.0mmol) compound 5 and 328mg anhydrous sodium acetate (2.0eq., 4.0
Mmol) be dissolved in 25mL DMSO, stir, be heated to 80 DEG C, then be added Platinous Potassium Chloride 830mg (1.0eq., 2.0
Mmol), vacuumize and be passed through nitrogen displacement for several times, be warming up to 120 DEG C of reaction 5hr.After reaction, 100ml water is added while hot,
Filtering is collected solid, is washed with suitable quantity of water and methanol, the solid re crystallization from toluene that will be obtained, then vacuum sublimation obtains depth
Red solid 1.01g, gross production rate 70%, 99.9%.Mass spectrum (ESI-)([M-H]-)C36H33N3OPt theoretical value: 717.23；It is real
Measured value: 717.20.
Embodiment 3:
Synthetic route:
The synthesis of compound 14: taking 7.97g (15.0mmol) compound 9, and 13 7.63g of compound (1.0eq., 15.0
Mmol), potassium carbonate 3.45g (1.25eq., 25.0mmol) and Pd (PPh3)4347mg (0.02eq., 0.3mmol), is added to
In three-neck flask, vacuumizes and be passed through nitrogen displacement repeatedly, be then injected into acetonitrile 100mL and 50mL methanol, be heated to 60 DEG C.?
It after reacting 12hr under nitrogen protection, is cooled to room temperature, revolving removes solvent, adds suitable quantity of water and ethyl acetate extraction, collects
Organic phase, is added proper silica gel after anhydrous magnesium sulfate is dry, revolving removes solvent, uses n-hexane/ethyl acetate system column layer
Analysis, obtains white solid 7.50g, yield 60%, purity 99.5%.
The synthesis of compound 15: taking 6.66g (8.0mmol) compound 14, and 2- bromopyridine 1.37g (1.1eq., 8.8
Mmol), potassium carbonate 1.38g (1.25eq., 10.0mmol) and Pd (PPh3)4185mg (0.02eq., 0.16mmol), is added to
In three-neck flask, vacuumizes and be passed through nitrogen displacement repeatedly, be then injected into acetonitrile 60mL and 30mL methanol, be heated to 60 DEG C.In nitrogen
It after reacting 12hr under gas shielded, is cooled to room temperature, revolving removes solvent, adds suitable quantity of water and ethyl acetate extraction, and collection has
Machine phase, is added proper silica gel after anhydrous magnesium sulfate is dry, revolving removes solvent, uses n-hexane/ethyl acetate system column layer
Analysis, obtains white solid 6.27g, yield 80%, purity 99.9%.
The synthesis of compound 16: taking 3.14g (4.0mmol) compound 15, and pyridine hydrochloride 30g (PyHCl) is added to
In three-neck flask, vacuumizes and be passed through nitrogen displacement repeatedly, be heated to 190 DEG C under nitrogen protection, after reacting 4hr, be cooled to room
Temperature, suitable quantity of water and ethyl acetate extraction are added, organic phase is collected, proper silica gel is added after anhydrous magnesium sulfate is dry, rotates
Solvent is removed, is chromatographed using n-hexane/ethyl acetate system column, obtains white solid 2.77g, yield 90%, purity 99.9%.
Mass spectrum (ESI-)([M-H]-)C54H62N3O theoretical value: 768.50；Measured value: 768.47.
The synthesis of compound P105: take 1.54g (2.0mmol) compound 16 and 328mg anhydrous sodium acetate (2.0eq.,
4.0mmol) be dissolved in 25mL DMSO, stir, be heated to 80 DEG C, then be added Platinous Potassium Chloride 830mg (1.0eq.,
2.0mmol), it vacuumizes and is passed through nitrogen displacement for several times, be warming up to 120 DEG C of reaction 5hr.After reaction, 100ml is added while hot
Water, filtering are collected solid, are washed with suitable quantity of water and methanol, the solid re crystallization from toluene that will be obtained, then vacuum sublimation obtains
To dark red solid 1.25g, gross production rate 65%, purity 99.9%.Mass spectrum (ESI-)([M-H]-)C54H60N3OPt theoretical value:
961.44；Measured value: 961.42.
Pt (II) complex of embodiment shows apparent orange red light emitting in dichloromethane solution solution, as follows
Shown in table:
Here is the application example of the compounds of this invention.
Device preparation method:
The basic structure model of device are as follows: ITO/HTL-1 (60nm)/EML-1:Pt (II) (40nm)/ETL-1 (30nm)/
LiF (1nm)/Al(80nm)。
Successively using acetone, ethyl alcohol and distilled water to transparent anode tin indium oxide (ITO) 20 (10 Ω/sq) glass substrate 10
It is cleaned by ultrasonic, then is handled 5 minutes with oxygen plasma.
Then ITO substrate is mounted in the substrate holder of vacuum gas-phase evaporated device.In evaporated device, control volume
It is pressure 10-6torr.。
Hereafter, the 30 material HTL-1 of hole transmission layer with a thickness of 60nm is evaporated on ITO substrate.
Then the 40 material EML-1 of luminescent layer with a thickness of 40nm is evaporated, wherein the platinum (II) of doping different quality containing is matched
Close object dopant.
Then the 50 material ETL-1 of electron transfer layer with a thickness of 30nm is evaporated.
Then evaporating with a thickness of the LiF of 1nm is electron injecting layer 60.
The Al with a thickness of 80nm is finally evaporated as cathode 70 and completes device encapsulation.As shown in Figure 1.
Test device structure it is identical with production method, difference be successively using organometallic complex Pt0,
Pt1, Pt2, Pt105 are as the dopant and doping concentration in luminescent layer.Wherein, Pt0 is classical O^N^N^O class feux rouges material
Material.
Shown in device comparing result following table:
It is respectively 4wt% in four tooth platinum (II) complex doped concentration, under the conditions of 8wt%, 12wt%, with above-mentioned ITO/
HTL-1 (60nm)/EML-1:Pt (II) (40nm)/ETL-1 (30nm)/LiF (1nm)/Al (80nm) basic device structure preparation
Device.It is reference with the device performance based on Pt0, the device of four tooth platinum (II) complex Pt1, Pt2, Pt105 is in starting voltage
VonHave different degrees of reduction compared to the device of Pt0, be based especially on Pt105 device its start voltage be down to 3.0V.Together
When, under the conditions of 1000cd/A, it is based on Pt1, the device of Pt2, Pt105 are in current efficiency (CE), power efficiency (PE) and outer amount
Sub- efficiency (EQE) has different degrees of promotion, especially Pt105 relative to the device based on Pt-0, in current efficiency
(CE), it is promoted more obviously in power efficiency (PE) and external quantum efficiency (EQE).In four tooth platinum (II) complex doped concentration
When increase, the improved efficiency of Pt0, Pt1 are smaller or even efficiency has a degree of decline, but Pt105 has preferable efficiency to mention
It rises, current efficiency is promoted to 78.5cd/A by 73.5cd/A, and power efficiency is promoted to 78.5lm/W, outer amount by 67.8lm/W
Sub- efficiency is promoted to 18.7% by 17.8%.Pt105 has biggish steric group relative to Pt0, Pt1, Pt2, can be effectively reduced
Intermolecular aggtegation avoids the formation of exciplex, improves luminous efficiency.Meanwhile Pt1, Pt2 relative to Pt0 in performance
On also have different degrees of promotion.
In conclusion the performance of organic electroluminescence device prepared by the present invention has preferably relative to benchmark device
Performance boost, related novel tetra- tooth platinum (II) complex metallo organic material of N^N^N^O have biggish application value.
Claims (14)
1. a kind of N^N^N^O configuration four tooth platinum (II) complex has the basic structure as shown in formula (3):
Wherein, A1-A5 is five-membered ring replace or non-substituted, hexatomic ring, condensed cyclic structure.
2. complex according to claim 1 has the structure as shown in formula (4):
Wherein R1- R17It is independent to be selected from hydrogen, deuterium, halogen, hydroxyl, acyl group, alkoxy, acyloxy, amino, nitro, acyl group ammonia
Base, carboxyl, styryl, amino carbonyl, carbamoyl, benzyloxycarbonyl group, aryloxy group, diaryl-amine base, contains 1-30 C at cyano
The saturated alkyl of atom, the unsaturated alkyl containing 1-20 C atom, containing the substituted or unsubstituted aryl of 5-30 C atom,
Containing the substituted or unsubstituted heteroaryl of 5-30 C atom or adjacent R1- R17Cyclization is connected each other by covalent bond；Its
In, X1- X27For carbon, the halogen is F, Cl, Br.
3. the complex stated according to claim 2, wherein R1- R17It is independent to be selected from hydrogen, halogen, amino, nitro, cyano, two virtues
Amido, the saturated alkyl containing 1-10 C atom, being taken by halogen or one or more C1-C4 alkyl containing 5-20 C atom
It is generation or unsubstituting aromatic yl, alkyl-substituted or unsubstituted miscellaneous by halogen or one or more C1-C4 containing 5-20 C atom
Aryl or adjacent R1- R17Cyclization is connected each other by covalent bond, the halogen is F, Cl.
4. complex according to claim 3, has the following structure:
Wherein R1'-R5' it is independent selected from hydrogen, halogen, diaryl-amine base, the saturated alkyl containing 1-10 C atom, containing 5-10 C
Atom by halogen or one or more C1-C4 be alkyl-substituted or unsubstituting aromatic yl, containing 5-10 C atom by halogen or
One or more C1-C4 are alkyl-substituted or unsubstituted heteroaryl or adjacent R1- R17It is connected into each other by covalent bond
Ring.
5. complex according to claim 4, wherein R1'-R5' 5 groups in, wherein there is 0-3 group independent
Be expressed as diaryl-amine base, containing 5-10 C atom by halogen or one to three C1-C4 be alkyl-substituted or unsubstituted aryl,
Containing 5-10 C atom by halogen or one to three C1-C4 be alkyl-substituted or unsubstituted heteroaryl；Other groups are only
Vertical is expressed as hydrogen or the saturated alkyl containing 1-8 C atom, and the halogen is F.
6. complex according to claim 5, R1'-R5' 5 groups in, wherein there is the independent expression of 0-3 group
For hexichol amido, benzene, pyridine, carbazyl, other groups are independent to be expressed as hydrogen, isopropyl or tert-butyl.
7. complex according to claim 1, has the following structure:
8. complex according to claim 7, has the following structure:
9. the precursor of any complex of claim 1-8, i.e. ligand, have the following structure:
Wherein, A1-A5 is five-membered ring replace or non-substituted, hexatomic ring, condensed cyclic structure.
10. precursor according to claim 9 has the following structure:
Wherein R1- R17It is independent to be selected from hydrogen, deuterium, halogen, hydroxyl, acyl group, alkoxy, acyloxy, amino, nitro, acyl group ammonia
Base, carboxyl, styryl, amino carbonyl, carbamoyl, benzyloxycarbonyl group, aryloxy group, diaryl-amine base, contains 1-30 C at cyano
The saturated alkyl of atom, the unsaturated alkyl containing 1-20 C atom, containing the substituted or unsubstituted aryl of 5-30 C atom,
Containing the substituted or unsubstituted heteroaryl of 5-30 C atom or adjacent R1- R17Cyclization is connected each other by covalent bond；Its
In, X1- X27For carbon, the halogen is F, Cl, Br.
11. precursor according to claim 9 has the following structure:
Wherein R1'-R5' it is independent selected from hydrogen, halogen, diaryl-amine base, the saturated alkyl containing 1-10 C atom, containing 5-10 C
Atom by halogen or one or more C1-C4 be alkyl-substituted or unsubstituting aromatic yl, containing 5-10 C atom by halogen or
One or more C1-C4 are alkyl-substituted or unsubstituted heteroaryl or adjacent R1- R17It is connected into each other by covalent bond
Ring.
12. the preparation method of any complex of claim 4, includes the following steps:
Carbazole analog derivative S1 obtains substrate S2 through bromo-reaction, and S2 reacts to obtain corresponding pinacol with connection pinacol borate
Ester derivant S3, S3 react to obtain S5 through Suzuki with pyridine derivatives S4, and S5 is anti-through Suzuki with pyridine derivatives S6
S7 should be obtained, corresponding ligand S8, S8 and K are obtained after S7 demethylation2PtCl4Reaction obtains target product P；
13. application of any complex of claim 1-8 in OLED luminescent device.
14. application according to claim 13, any complex of claim 1-8 is in OLED luminescent device
Play the phosphorescence dopant material of photon transmitting in luminescent layer.
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| CN113698432A (en) * | 2020-05-21 | 2021-11-26 | 广东阿格蕾雅光电材料有限公司 | Preparation and application of tetradentate platinum (II) complex |
| WO2023284486A1 (en) * | 2021-07-13 | 2023-01-19 | 浙江工业大学 | Tetradentate cyclometal platinum(ii) and palladium(ii) complex luminescent material containing quinoline structural unit and application thereof |
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| CN113717229B (en) * | 2020-05-26 | 2022-08-19 | 广东阿格蕾雅光电材料有限公司 | Platinum complex containing ONCN tetradentate ligand and application thereof in organic light-emitting diode |
| CN113683646B (en) * | 2021-09-18 | 2024-04-05 | 广西民族大学 | Platinum complex containing monocarborane metal, preparation method and application thereof |
| CN115010763A (en) * | 2022-06-24 | 2022-09-06 | 深圳大学 | Circular polarization phosphorescence platinum (II) complex and preparation method and application thereof |
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| US20160240800A1 (en) * | 2015-02-13 | 2016-08-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
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| JP2023503673A (en) * | 2019-12-24 | 2023-01-31 | 広東阿格蕾雅光電材料有限公司 | O—C—N—N type tetradentate platinum (II) complex, preparation method and use thereof |
| JP7332809B2 (en) | 2019-12-24 | 2023-08-23 | 広東阿格蕾雅光電材料有限公司 | O—C—N—N type tetradentate platinum (II) complex, preparation method and use thereof |
| CN113698432A (en) * | 2020-05-21 | 2021-11-26 | 广东阿格蕾雅光电材料有限公司 | Preparation and application of tetradentate platinum (II) complex |
| CN113698432B (en) * | 2020-05-21 | 2024-03-08 | 广东阿格蕾雅光电材料有限公司 | Preparation and application of tetradentate platinum (II) complex |
| WO2023284486A1 (en) * | 2021-07-13 | 2023-01-19 | 浙江工业大学 | Tetradentate cyclometal platinum(ii) and palladium(ii) complex luminescent material containing quinoline structural unit and application thereof |
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