WO2024021988A1 - Organometallic complex, formulation, organic optoelectronic device, and display or lighting apparatus - Google Patents
Organometallic complex, formulation, organic optoelectronic device, and display or lighting apparatus Download PDFInfo
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- WO2024021988A1 WO2024021988A1 PCT/CN2023/103790 CN2023103790W WO2024021988A1 WO 2024021988 A1 WO2024021988 A1 WO 2024021988A1 CN 2023103790 W CN2023103790 W CN 2023103790W WO 2024021988 A1 WO2024021988 A1 WO 2024021988A1
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- 230000005693 optoelectronics Effects 0.000 title claims abstract description 28
- 125000002524 organometallic group Chemical group 0.000 title claims abstract description 23
- 238000009472 formulation Methods 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title abstract 2
- 239000010410 layer Substances 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 150000004696 coordination complex Chemical class 0.000 claims description 18
- 239000012044 organic layer Substances 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 230000005525 hole transport Effects 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 8
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 8
- 125000005264 aryl amine group Chemical group 0.000 claims description 8
- 125000005013 aryl ether group Chemical group 0.000 claims description 8
- 125000005104 aryl silyl group Chemical group 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 125000001033 ether group Chemical group 0.000 claims description 8
- 125000005253 heteroarylacyl group Chemical group 0.000 claims description 8
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 8
- 125000005251 aryl acyl group Chemical group 0.000 claims description 7
- 229910052763 palladium Chemical group 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- SJJUQUCHRHSNHX-UHFFFAOYSA-N 1-(cyanoamino)-1-nitroguanidine Chemical compound C(#N)NN(C(N)=N)[N+](=O)[O-] SJJUQUCHRHSNHX-UHFFFAOYSA-N 0.000 claims description 4
- IRUFLAAZAAOXHM-UHFFFAOYSA-N 1-tert-butyl-2-phenylbenzene Chemical group CC(C)(C)C1=CC=CC=C1C1=CC=CC=C1 IRUFLAAZAAOXHM-UHFFFAOYSA-N 0.000 claims description 4
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 4
- 150000007857 hydrazones Chemical class 0.000 claims description 4
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 2
- 238000013086 organic photovoltaic Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 230000002035 prolonged effect Effects 0.000 abstract 1
- -1 hexadecyl Alkyl Chemical group 0.000 description 32
- 125000001424 substituent group Chemical group 0.000 description 20
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- 125000000753 cycloalkyl group Chemical group 0.000 description 10
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 239000000243 solution Substances 0.000 description 3
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
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- 235000010290 biphenyl Nutrition 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
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- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 2
- 238000010345 tape casting Methods 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000001931 thermography Methods 0.000 description 2
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- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
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- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
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- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
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- BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
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- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000532 dioxanyl group Chemical group 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 238000010348 incorporation Methods 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical compound NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007650 screen-printing Methods 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
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- 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
- C07F15/006—Palladium compounds
Definitions
- the present invention relates to an organic metal complex, in particular to an organic metal complex, a preparation, an organic optoelectronic device and a display or lighting device, and belongs to the field of organic optoelectronics.
- Organic optoelectronic devices especially organic electroluminescent diodes (OLED) have the characteristics of self-illumination, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, fast response speed, wide applicable temperature range, low driving voltage, and can be manufactured in flexible and The unique advantages of curved and transparent display panels and environmental friendliness can be applied to flat panel displays and new generation lighting, and can also be used as backlight sources for LCDs.
- OLED organic electroluminescent diodes
- OLED Since its invention in the late 1980s, OLED has been used in industry. OLED emits light in two ways: fluorescence and phosphorescence. According to theoretical speculation, the difference between the singlet excited state and the triplet excited state generated by carrier recombination The ratio is 1:3, so when using small molecule fluorescent materials, only 25% of the total energy can be used to emit light, and the remaining 75% of the energy is lost due to the non-luminescent mechanism of the triplet excited state, so it is generally considered that fluorescent materials The internal quantum efficiency limit is 25%. In 1998, Professor Forrest and others discovered that triplet phosphorescence could be utilized at room temperature, and raised the upper limit of the original internal quantum efficiency to 100%.
- Triplet phosphors are often complexes composed of heavy metal atoms, and use the heavy atom effect to strongly
- the spin-orbit coupling effect causes the originally forbidden triplet energy to emit light in the form of phosphorescence, and the quantum efficiency is also greatly improved.
- the luminescent layers in organic OLED components almost all use the host-guest luminescent system mechanism, that is, the host material is doped with the guest luminescent material.
- the energy system of the organic host material is larger than that of the guest material, that is, the energy is transferred from the host to the guest material.
- the object causes the object material to be excited and emit light.
- Commonly used phosphorescent organic host materials have high triplet energy levels. When the organic host material is excited by an electric field, the triplet energy can be effectively transferred from the organic host material to the guest phosphorescent material.
- Commonly used organic guest materials are iridium and platinum metal compounds. However, there are still some technical difficulties in the development of platinum and palladium complex materials and devices. For example, OLED requires high efficiency, long life, and lower operating voltage.
- the object of the present invention is to provide a novel organic metal complex and an organic optoelectronic device (especially an organic electroluminescent diode) containing the same.
- Applying the organic metal complex of the present invention to an organic optoelectronic device can improve the current efficiency of the device, reduce the operating voltage of the device, and extend the life of the device.
- the invention provides an organic metal complex, the structure of which is shown in Formula I:
- M is selected from platinum or palladium
- R 1 , R 2 , R 3 and R are each independently selected from hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group Or its salt, phosphate group or its salt, C1 ⁇ C18 alkyl group, C1 ⁇ C18 alkoxy group, C1 ⁇ C18 alkylsilyl group, C1 ⁇ C18 alkoxysilyl group, C6 ⁇ C40 substituted or unsubstituted aromatic group group, C6 to C40 heteroaryl group, C6 to C60 substituted or unsubstituted heterospirocyclic ring, C6 to C60 substituted or unsubstituted spirocyclic ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl group ether group, substituted or unsubstituted arylamine group, Substituted
- n is an integer from 0 to 10;
- n is an integer from 0 to 4.
- the coordination group on the pyridine side is selected from any one of the following structures:
- R is hydrogen, deuterium, halogen, C1 ⁇ C18 alkyl group, C1 ⁇ C18 alkoxy group, C1 ⁇ C18 alkylsilyl group, C1 ⁇ C18 alkoxysilyl group, C6 ⁇ C40 substituted or unsubstituted aryl group , C6 ⁇ C40 heteroaryl group, C6 ⁇ C60 substituted or unsubstituted heterospirocyclic ring, C6 ⁇ C60 substituted or unsubstituted spirocyclic ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl group Ether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroarylsilyl group, substituted or unsubstituted Aryloxysilyl, substituted or un unsub
- n is an integer from 0 to 10;
- n is an integer from 0 to 4.
- R 1 , R 2 , R 3 and R are each independently selected from hydrogen, methyl, ethyl, tert-butyl or tert-butylbiphenyl.
- formula (I) is selected from any one of the following structures:
- the present invention also provides a preparation comprising the organometallic complex and at least one solvent, wherein the solvent is an unsaturated hydrocarbon solvent, a saturated hydrocarbon solvent, an ether solvent or an ester solvent.
- the invention also provides an organic optoelectronic device, which includes a cathode layer, an anode layer and an organic layer.
- the organic layer is a hole injection layer, a hole transport layer, a light-emitting layer (active layer), a hole blocking layer, an electron layer, and a hole injection layer. At least one of an injection layer or an electron transport layer, wherein the organic layer contains the organic metal complex.
- the organic layer is a light-emitting layer
- the light-emitting layer contains the organic metal complex and the corresponding host material, wherein the mass percentage of the organic metal complex is between 1% and 50%, and the host material has no limit.
- the organic optoelectronic device is an organic photovoltaic device, an organic light-emitting device (OLED), an organic solar cell (OSC), an electronic paper (e-paper), an organic photoreceptor (OPC), an organic thin film transistor (OTFT) or an organic Memory device (Organic Memory Element).
- OLED organic light-emitting device
- OSC organic solar cell
- e-paper electronic paper
- OPC organic photoreceptor
- OFT organic thin film transistor
- OFT organic thin film transistor
- Organic Memory Element Organic Memory Element
- the invention also provides an organic optoelectronic device, which includes a cathode layer, an anode layer and an organic layer.
- the organic layer is a light-emitting layer, wherein the light-emitting layer contains an organic metal complex, and the structure of the organic metal complex is as follows Formula I shows:
- M is selected from platinum or palladium
- R 1 , R 2 , R 3 and R are each independently selected from hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group Or its salt, phosphate group or its salt, C1 ⁇ C18 alkyl group, C1 ⁇ C18 alkoxy group, C1 ⁇ C18 alkylsilyl group, C1 ⁇ C18 alkoxysilyl group, C6 ⁇ C40 substituted or unsubstituted aromatic group Base, C6 ⁇ C40 heteroaryl group, C6 ⁇ C60 substituted or unsubstituted heterospirocyclic ring, C6 ⁇ C60 substituted or unsubstituted spirocyclic ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl group ether group, substituted or unsubstituted arylamine group, substituted or unsub
- n is an integer from 0 to 10;
- n is an integer from 0 to 4.
- the coordination group on the pyridine side is selected from any one of the following structures:
- R is hydrogen, deuterium, halogen, C1 ⁇ C18 alkyl group, C1 ⁇ C18 alkoxy group, C1 ⁇ C18 alkylsilyl group, C1 ⁇ C18 alkoxysilyl group, C6 ⁇ C40 substituted or unsubstituted aryl group , C6 ⁇ C40 heteroaryl group, C6 ⁇ C60 substituted or unsubstituted heterospirocyclic ring, C6 ⁇ C60 substituted or unsubstituted spirocyclic ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl group Ether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroarylsilyl group, substituted or unsubstituted Aryloxysilyl, substituted or un unsub
- n is an integer from 0 to 10;
- n is an integer from 0 to 4.
- R 1 , R 2 , R 3 and R are each independently selected from hydrogen, methyl, ethyl, tert-butyl or tert-butylbiphenyl.
- the present invention further provides a display or lighting device including the organic optoelectronic device.
- the spiro ring-containing organometallic complex of the present invention has good thermal stability. By introducing a rigid spirocyclic structure into the organometallic complex and increasing steric hindrance, the interaction between planar Pt complex molecules can be effectively suppressed, thereby improving device efficiency.
- the spiro ring-containing organometallic complex of the present invention has good electron and hole receiving capabilities, and can improve the energy transmission between the host and the guest.
- the specific performance is as follows:
- the invented spiro ring-containing organometallic complex is used as a functional layer (organic layer), especially as an organic optoelectronic device produced as a light-emitting layer. Its current efficiency is increased, the lighting voltage is reduced, and the life of the device is greatly improved, indicating that most After the electrons and holes recombine, the energy is effectively transferred to the organometallic complex to emit light instead of heat.
- Figure 1 is a schematic structural diagram of an organic optoelectronic device of the present invention, in which 110 represents the substrate, 120 represents the anode, 130 represents the hole injection layer, 140 represents the hole transport layer, 150 represents the light-emitting layer, 160 represents the hole blocking layer, 170 Indicates the electron transport layer, 180 indicates the electron injection layer, and 190 indicates the cathode.
- permissible substituents include cyclic and acyclic, branched and unbranched, carbocyclic and heterocyclic, aromatic and nonaromatic substituents of organic compounds.
- exemplary substituents include those described below.
- the permissible substituents may be one or more, the same or different.
- a heteroatom eg, nitrogen
- the present invention is not intended to be limited in any way by the permissible substituents of organic compounds.
- substituted or “substituted with” includes the implicit proviso that such substitution is consistent with the permissible valence bonds of the substituting atom and the substituent, and that the substitution results in a stable compound (e.g., one that does not spontaneously undergo transformation) For example, compounds by rearrangement, cyclization, elimination, etc.).
- individual substituents can be further optionally substituted (ie, further substituted or unsubstituted) unless expressly stated to the contrary.
- R1", R2”, R3", “R4", “R5" and “R” are used as general symbols in the present invention to represent various specific substituents. These symbols can be any substituent, not limited to those disclosed in the present invention, and when they are defined as certain substituents in one example, they can also be defined as some other substituents in another example.
- alkyl used in the present invention refers to a branched or unbranched saturated hydrocarbon group of 1 to 18 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl Alkyl, eicosyl, tetradecyl, etc.
- the alkyl group may be cyclic or acyclic.
- the alkyl group may be branched or unbranched.
- the alkyl group may also be substituted or unsubstituted.
- the alkyl group can substitute one or more groups, including but not limited to optionally substituted alkyl, cycloalkyl, alkoxy, amino, ether, halogen, hydroxyl, nitro, methyl as described in the present invention.
- a "lower alkyl” group is an alkyl group containing 1 to 6 (eg, 1 to 4) carbon atoms.
- alkyl generally refers to both unsubstituted and substituted alkyl groups; however, substituted alkyl groups are also specifically referred to herein by identifying the specific substituents on the alkyl group.
- halogenated alkyl or “haloalkyl” specifically refers to an alkyl group substituted with one or more halogens (eg, fluorine, chlorine, bromine, or iodine).
- alkoxyalkyl specifically refers to an alkyl group substituted with one or more alkoxy groups, as described below.
- alkylamino specifically refers to an alkyl group substituted with one or more amino groups, as described below, etc.
- alkyl is used in one context and a specific term such as “alkyl alcohol” is used in another context, it is not meant to imply that the term “alkyl” does not also refer to a specific term such as “alkyl” Alcohol” etc.
- aryl as used herein is a substituted or unsubstituted phenyl group of 6 to 60 carbon atoms, such as methylphenyl, ethylphenyl, n-propylphenyl, isopropylphenyl, n-butyl phenyl, isobutylphenyl, sec-butylphenyl, tert-butylphenyl, tert-butylbiphenyl, n-pentylphenyl, isopentylphenyl, sec-pentylphenyl, neopentyl Phenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, dodecylphenyl, tetradecylphenyl, hexadecylphenyl, eicosanyl Alkylphenyl,
- alkoxy and “alkoxy group” as used herein refer to an alkyl or cycloalkyl group of 1 to 18 carbon atoms bonded through ether bonds; that is, “alkoxy” may be defined as— OR1, where R1 is alkyl or cycloalkyl as defined above.
- Alkoxy also includes the alkoxy polymers just described; i.e., the alkoxy group may be a polyether, such as -OR1-OR2 or -OR1-(OR2)a-OR3, where "a” is an integer from 1 to 500 , and R1, R2 and R3 are each independently an alkyl group, a cycloalkyl group or a combination thereof.
- aryl used in the present invention refers to any carbon-based aromatic group with 60 carbon atoms or less, including but not limited to benzene, naphthalene, phenyl, biphenyl, phenoxybenzene, etc.
- aryl also includes "heteroaryl” which is defined as an aromatic-containing group that The ring contains at least one heteroatom. Examples of heteroatoms include, but are not limited to, nitrogen, oxygen, sulfur, or phosphorus.
- non-heteroaryl (which is also included in the term “aryl”) defines an aromatic-containing group that does not contain heteroatoms.
- Aryl groups may be substituted or unsubstituted.
- the aryl group may be substituted with one or more groups, including but not limited to alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, Aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halogen, hydroxyl, ketone, azido, nitro, silyl, thio-oxo group or mercapto group.
- bias is a specific type of aryl group and is included in the definition of "aryl”. Biaryl refers to two aryl groups joined together by a fused ring structure, as in naphthalene, or by one or more carbon-carbon bonds, as in biphenyl.
- amine or “amino” used in the present invention is represented by the formula -NR1R2, wherein R1 and R2 can be independently selected from hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aromatic Choose from base or heteroaryl.
- carboxylic acid as used herein is represented by the formula -C(O)OH.
- ether used in the present invention is represented by the formula R1OR2, wherein R1 and R2 can independently be alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or Heteroaryl.
- polyether used in the present invention is represented by the formula - (R1O-R2O)a-, wherein R1 and R2 can independently be alkyl, cycloalkyl, alkenyl, cycloalkenyl or alkynyl as described in the present invention. , cycloalkynyl, aryl or heteroaryl and "a" is an integer from 1 to 500.
- halogen refers to the halogens fluorine, chlorine, bromine and iodine.
- heterocyclic group refers to monocyclic and polycyclic non-aromatic ring systems
- heteroaryl refers to monocyclic and polycyclic non-aromatic ring systems of not more than 60 carbon atoms.
- the term includes azetidinyl, dioxanyl, furyl, imidazolyl, isothiazolyl, isoxazolyl, morpholinyl, oxazolyl (including 1,2,3-oxadiazolyl, 1,2,5-oxadiazolyl and 1,3,4-oxadiazolyl (oxazolyl), piperazinyl, piperidinyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridyl, Pyrimidinyl, pyrrolyl, pyrrolidinyl, tetrahydrofuryl, tetrahydropyranyl, tetrazinyl including 1,2,4,5-tetrazinyl, including 1,2,3,4-tetrazolyl and 1 , 2,4,5-tetrazolyl tetrazolyl, including 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl and 1,3,4-thiadia
- hydroxyl as used herein is represented by the formula -OH.
- nitro as used herein is represented by the formula -NO2.
- nitrile as used herein is represented by the formula -CN.
- R1", “R2", “R3”, and “Rn” (where n is an integer) used in the present invention may independently have one or more of the groups listed above.
- R1 is a straight chain alkyl group
- one hydrogen atom of the alkyl group may be optionally substituted with hydroxyl, alkoxy, alkyl, halogen, etc.
- the first group may be incorporated within the second group, or the first group may be pendant (ie, attached) to the second group.
- the amino group may be bonded within the backbone of the alkyl group.
- the amino group may be attached to the backbone of the alkyl group. The nature of the selected group will determine whether the first group is embedded in or linked to the second group.
- the compounds described herein may contain "optionally substituted” moieties.
- substituted (whether preceded by the term “optionally” or not) means that one or more hydrogens of the specified moiety are substituted with a suitable substituent.
- an "optionally substituted” group may have a suitable substituent at each substitutable position of the group, and when more than one position in any given structure may be selected from one of the specified groups When the above substituents are substituted, the substituents may be the same or different at each position.
- Combinations of substituents contemplated by this invention are preferably combinations that form stable or chemically feasible compounds. It is also contemplated that, in certain aspects, each substituent may be further optionally substituted (ie, further substituted or unsubstituted) unless expressly stated to the contrary.
- R1, R2, R3, R4, R5, R, etc. are mentioned several times in the chemical structures and units disclosed and described herein. Any description of R1, R2, R3, R4, R5, R, etc. in the specification applies to any structure or unit referencing R1, R2, R3, R4, R5, R, etc., respectively, unless otherwise stated.
- the preparation of the present invention contains an organic metal complex represented by formula (I) and one or more solvents.
- the solvent used is not particularly limited.
- Unsaturated hydrocarbon solvents well known to those skilled in the art such as toluene, xylene, Mesitylene, tetralin, decalin, dicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, etc.
- halogenated saturated hydrocarbon solvents such as carbon tetrachloride, chloroform, methylene chloride, Dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, etc.
- halogenated unsaturated hydrocarbon solvents such as chlorobenzene , dichlorobenzene, trichlorobenzene, etc.
- ether solvents such as tetrahydrofuran, tetrahydropyran, etc. or
- the invention also provides an organic optoelectronic device, which includes: a first electrode;
- An organic layer is sandwiched between the first electrode and the second electrode; wherein the organic layer contains the organic metal complex of the present invention.
- the organometallic complex (platinum, palladium metal compound) of the present invention can effectively reduce the interaction between luminescent molecules due to steric hindrance by introducing a tetradentate ligand unit containing a rigid spiro ring ( Figure 1).
- the quenching caused by the triplet state improves the luminous efficiency of the device.
- Applying the organic metal complex of the present invention to organic optoelectronic devices, especially in organic electroluminescent devices can improve the current efficiency of the device, reduce the operating voltage of the device, and extend the life of the device.
- the organic optoelectronic device can use sputter coating, electron beam evaporation, vacuum evaporation and other methods to evaporate metal or conductive oxides and their alloys on the substrate to form an anode; in the prepared anode
- the surface is prepared by sequentially evaporating a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer and an electron transport layer, and then evaporating a cathode.
- organic optoelectronic devices can also be produced by evaporating the cathode, organic layer, and anode in sequence on the substrate.
- the organic layer can include a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, etc. Multi-layer structure.
- the organic layer of the present invention adopts polymer materials according to solvent engineering (spin-coating, tape-casting, doctor-blading, screen-printing, spraying). Ink printing or thermal imaging (Thermal-Imaging, etc.) can replace the evaporation method and can reduce the number of device layers.
- the materials used in the organic optoelectronic devices according to the present invention can be classified into top-emitting, bottom-emitting or double-sided emitting.
- the organometallic complex of the present invention can be applied to organic solar cells, lighting OLEDs, flexible OLEDs, organic photoreceptors, organic thin film transistors and the like on similar principles to organic optoelectronic devices.
- the OLED device of the present invention contains a hole transport layer.
- the hole transport material can be preferably selected from known or unknown materials, and is particularly preferably selected from the following structures, but does not represent the present invention. Limited to the following structures:
- the hole transport layer contained in the OLED device of the present invention contains one or more p-type dopants.
- the preferred p-type dopant of the present invention has the following structure, but it does not mean that the present invention is limited to the following structure:
- the electron transport layer can be selected from at least one of the following compounds, but this does not mean that the present invention is limited to the following structures:
- organometallic complex i.e. guest compound represented by formula (I) of the present invention.
- Ligand 1 was prepared by methods well known in the art.
- organometallic complex ie, the guest compound
- luminescent properties of the device are explained in detail in conjunction with the following examples. However, these are only used to illustrate the embodiments of the present invention, and the scope of the present invention is not limited thereto.
- the evaporated HIL hole injection layer
- HTL The hole transport layer
- EBL electrostatic layer
- EML electrostatic layer
- the EML electrostatic layer
- the main material the organic metal complex of the present invention (94: 6, v/v%)
- the thickness is 35 nm
- the ETL electrostatic transport layer
- the cathode Al is evaporated to 70 nm.
- Examples 1 to 5 show good device performance due to the incorporation of a spiro ring structure into the ligand structure, indicating that the organometallic complex of the present invention has certain application value.
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Abstract
The present invention provides an organometallic complex, a formulation, an organic optoelectronic device, and a display or lighting apparatus. The organometallic complex has a structure represented by formula (I): . The organic photoelectric device of the present invention has good light-emitting efficiency, reduced driving voltage, and prolonged service life.
Description
本发明涉及一种有机金属配合物，尤其涉及一种有机金属配合物、制剂、有机光电器件及显示或照明装置，属于有机光电领域。The present invention relates to an organic metal complex, in particular to an organic metal complex, a preparation, an organic optoelectronic device and a display or lighting device, and belongs to the field of organic optoelectronics.
有机光电器件(特别是有机电致发光二极管(OLED))具有自发光、宽视角、低能耗、效率高、薄、色彩丰富、响应速度快，适用温度范围广、低驱动电压、可制作柔性可弯曲与透明的显示面板以及环境友好等独特优点，可以应用在平板显示器和新一代照明上，也可以作为LCD的背光源。Organic optoelectronic devices (especially organic electroluminescent diodes (OLED)) have the characteristics of self-illumination, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, fast response speed, wide applicable temperature range, low driving voltage, and can be manufactured in flexible and The unique advantages of curved and transparent display panels and environmental friendliness can be applied to flat panel displays and new generation lighting, and can also be used as backlight sources for LCDs.
20世纪80年代底发明以来，OLED已经在产业上有所应用，OLED发光分为荧光发光和磷光发光两种方式，根据理论推测，由载流子复合产生的单重激发态与三重激发态的比例为1:3，所以使用小分子荧光材料时，能用于发光的仅为全部能量的25％，其余的75％的能量因三重激发态的非发光机制而损失掉，故一般认为荧光材料的内部量子效率极限为25％。1998年Forrest教授等人发现三线态磷光可以在室温下利用，并将原来内量子效率的上限提升到100％，三重态磷光体常常都是重金属原子组成的络合物，利用重原子效应，强烈的自旋轨域耦合作用使得原本被禁止的三重态能量以磷光的形式发光，量子效率也随之大幅提升。Since its invention in the late 1980s, OLED has been used in industry. OLED emits light in two ways: fluorescence and phosphorescence. According to theoretical speculation, the difference between the singlet excited state and the triplet excited state generated by carrier recombination The ratio is 1:3, so when using small molecule fluorescent materials, only 25% of the total energy can be used to emit light, and the remaining 75% of the energy is lost due to the non-luminescent mechanism of the triplet excited state, so it is generally considered that fluorescent materials The internal quantum efficiency limit is 25%. In 1998, Professor Forrest and others discovered that triplet phosphorescence could be utilized at room temperature, and raised the upper limit of the original internal quantum efficiency to 100%. Triplet phosphors are often complexes composed of heavy metal atoms, and use the heavy atom effect to strongly The spin-orbit coupling effect causes the originally forbidden triplet energy to emit light in the form of phosphorescence, and the quantum efficiency is also greatly improved.
目前有机OLED组件中的发光层几乎全部使用主客体发光体系机制，即在主体材料中掺杂客体发光材料，一般来说，有机主体材料的能系要比客体材料大，即能量由主体传递给客体，使客体材料被激发而发光。常用的磷光有机主体材料具有高三线态能级，当有机主体材料被电场激发时，三线态能量能够有效地从有机主体材料转移到客体磷光材料。常用的有机客体材料为铱和铂金属化合物。然而铂，钯配合物材料和器件的开发仍然存在一些技术难点，比如OLED要求效率高，寿命长，操作电压更低。At present, the luminescent layers in organic OLED components almost all use the host-guest luminescent system mechanism, that is, the host material is doped with the guest luminescent material. Generally speaking, the energy system of the organic host material is larger than that of the guest material, that is, the energy is transferred from the host to the guest material. The object causes the object material to be excited and emit light. Commonly used phosphorescent organic host materials have high triplet energy levels. When the organic host material is excited by an electric field, the triplet energy can be effectively transferred from the organic host material to the guest phosphorescent material. Commonly used organic guest materials are iridium and platinum metal compounds. However, there are still some technical difficulties in the development of platinum and palladium complex materials and devices. For example, OLED requires high efficiency, long life, and lower operating voltage.
因此，迫切需要开发一种新颖的有机金属配合物。Therefore, there is an urgent need to develop novel organometallic complexes.
发明内容Contents of the invention
为了解决现有技术中存在的问题，本发明的目的是提供一种新颖的有机金属配合物及包含其的有机光电器件(特别是有机电致发光二极管)。将本发明的有机金属配合物应用于有机光电器件，可以提升该器件的电流效率、降低该器件的操作电压，且延长该器件的寿命。In order to solve the problems existing in the prior art, the object of the present invention is to provide a novel organic metal complex and an organic optoelectronic device (especially an organic electroluminescent diode) containing the same. Applying the organic metal complex of the present invention to an organic optoelectronic device can improve the current efficiency of the device, reduce the operating voltage of the device, and extend the life of the device.
为了实现本发明的目的，本发明的技术方案如下：In order to achieve the purpose of the present invention, the technical solutions of the present invention are as follows:
本发明提供了一种有机金属配合物，其结构如式I示：
The invention provides an organic metal complex, the structure of which is shown in Formula I:
The invention provides an organic metal complex, the structure of which is shown in Formula I:
在式I中，M选自铂或钯；In formula I, M is selected from platinum or palladium;
R1、R2、R3和R各自独立地选自氢、氘、卤素、羟基、氰基、硝基、脒基、肼基、腙基、羧酸基团或其盐、磺酸基团或其盐、磷酸基团或其盐、C1～C18烷基、C1～C18烷氧基、含C1～C18烷硅基、含C1～C18烷氧硅基、C6～C40取代或未取代的芳基、C6～C40的杂芳基、C6～C60取代或未取代的杂螺环、C6～C60取代或未取代的螺环、取代或未取代的芳基醚基、取代或未取代的杂芳基醚基、取代或未取代的芳基胺基、
取代或未取代的杂芳基胺基、取代或未取代的芳基硅基、取代或未取代的杂芳基硅基、取代或未取代的芳基氧硅基、取代或未取代的芳基酰基、取代或未取代的杂芳基酰基或取代或未取代的氧膦基；R 1 , R 2 , R 3 and R are each independently selected from hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group Or its salt, phosphate group or its salt, C1～C18 alkyl group, C1～C18 alkoxy group, C1～C18 alkylsilyl group, C1～C18 alkoxysilyl group, C6～C40 substituted or unsubstituted aromatic group group, C6 to C40 heteroaryl group, C6 to C60 substituted or unsubstituted heterospirocyclic ring, C6 to C60 substituted or unsubstituted spirocyclic ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl group ether group, substituted or unsubstituted arylamine group, Substituted or unsubstituted heteroarylamino group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroarylsilyl group, substituted or unsubstituted aryloxysilyl group, substituted or unsubstituted aryl group Acyl, substituted or unsubstituted heteroaryl acyl or substituted or unsubstituted phosphinyl;
n为0到10的整数；n is an integer from 0 to 10;
m为0到4的整数；m is an integer from 0 to 4;
上述所有基团可被部分氘代或全氘代。All the above groups may be partially or fully deuterated.
更优选地，其中吡啶侧的配位基团选自下列结构中任一者：
More preferably, the coordination group on the pyridine side is selected from any one of the following structures:
More preferably, the coordination group on the pyridine side is selected from any one of the following structures:
其中，R为氢、氘、卤素、C1～C18烷基、C1～C18烷氧基、含C1～C18烷硅基、含C1～C18烷氧硅基、C6～C40取代或未取代的芳基、C6～C40的杂芳基、C6～C60取代或未取代的杂螺环、C6～C60取代或未取代的螺环、取代或未取代的芳基醚基、取代或未取代的杂芳基醚基、取代或未取代的芳基胺基、取代或未取代的杂芳基胺基、取代或未取代的芳基硅基、取代或未取代的杂芳基硅基、取代或未取代的芳基氧硅基、取代或未取代的芳基酰基、取代或未取代的杂芳基酰基或取代或未取代的氧膦基；Wherein, R is hydrogen, deuterium, halogen, C1～C18 alkyl group, C1～C18 alkoxy group, C1～C18 alkylsilyl group, C1～C18 alkoxysilyl group, C6～C40 substituted or unsubstituted aryl group , C6~C40 heteroaryl group, C6~C60 substituted or unsubstituted heterospirocyclic ring, C6~C60 substituted or unsubstituted spirocyclic ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl group Ether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroarylsilyl group, substituted or unsubstituted Aryloxysilyl, substituted or unsubstituted arylacyl, substituted or unsubstituted heteroarylacyl or substituted or unsubstituted phosphinyl;
n为0到10的整数；n is an integer from 0 to 10;
m为0到4的整数；m is an integer from 0 to 4;
上述所有基团可被部分氘代或全氘代。All the above groups may be partially or fully deuterated.
更优选地，其中R1、R2、R3和R各自独立地选自氢、甲基、乙基、叔丁基或叔丁基联苯基。More preferably, wherein R 1 , R 2 , R 3 and R are each independently selected from hydrogen, methyl, ethyl, tert-butyl or tert-butylbiphenyl.
更优选地，式(I)选自下列结构中任一者：
More preferably, formula (I) is selected from any one of the following structures:
More preferably, formula (I) is selected from any one of the following structures:
本发明还提供了一种制剂，其包含该有机金属配合物和至少一种溶剂，其中该溶剂为不饱和烃溶剂、饱和烃溶剂、醚类溶剂或酯类溶剂。The present invention also provides a preparation comprising the organometallic complex and at least one solvent, wherein the solvent is an unsaturated hydrocarbon solvent, a saturated hydrocarbon solvent, an ether solvent or an ester solvent.
本发明又提供了一种有机光电器件，其包括阴极层、阳极层和有机层，所述有机层为空穴注入层、空穴传输层、发光层(活性层)、空穴阻挡层、电子注入层或电子传输层中至少一者，其中所述有机层包含该有机金属配合物。The invention also provides an organic optoelectronic device, which includes a cathode layer, an anode layer and an organic layer. The organic layer is a hole injection layer, a hole transport layer, a light-emitting layer (active layer), a hole blocking layer, an electron layer, and a hole injection layer. At least one of an injection layer or an electron transport layer, wherein the organic layer contains the organic metal complex.
优选地，其中该有机层为发光层，该发光层中包含该有机金属配合物和相应的主体材料，其中该有机金属配合物的质量百分数在1％至50％，主体材料没有任何限制。Preferably, the organic layer is a light-emitting layer, and the light-emitting layer contains the organic metal complex and the corresponding host material, wherein the mass percentage of the organic metal complex is between 1% and 50%, and the host material has no limit.
优选地，其中该有机光电器件为有机光伏器件、有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-paper)、有机感光体(OPC)、有机薄膜晶体管(OTFT)或有机内存器件(Organic Memory Element)。Preferably, the organic optoelectronic device is an organic photovoltaic device, an organic light-emitting device (OLED), an organic solar cell (OSC), an electronic paper (e-paper), an organic photoreceptor (OPC), an organic thin film transistor (OTFT) or an organic Memory device (Organic Memory Element).
本发明还提供了一种有机光电器件，其包括阴极层、阳极层和有机层，所述有机层为发光层，其中所述发光层包含有机金属配合物，所述有机金属配合物的结构如式I所示：
The invention also provides an organic optoelectronic device, which includes a cathode layer, an anode layer and an organic layer. The organic layer is a light-emitting layer, wherein the light-emitting layer contains an organic metal complex, and the structure of the organic metal complex is as follows Formula I shows:
The invention also provides an organic optoelectronic device, which includes a cathode layer, an anode layer and an organic layer. The organic layer is a light-emitting layer, wherein the light-emitting layer contains an organic metal complex, and the structure of the organic metal complex is as follows Formula I shows:
在式I中，M选自铂或钯；In formula I, M is selected from platinum or palladium;
R1、R2、R3和R各自独立地选自氢、氘、卤素、羟基、氰基、硝基、脒基、肼基、腙基、羧酸基团或其盐、磺酸基团或其盐、磷酸基团或其盐、C1～C18烷基、C1～C18烷氧基、含C1～C18烷硅基、含C1～C18烷氧硅基、C6～C40取代或未取代的芳基，C6～C40的杂芳基、C6～C60取代或未取代的杂螺环、C6～C60取代或未取代的螺环、取代或未取代的芳基醚基、取代或未取代的杂芳基醚基、取代或未取代的芳基胺基、取代或未取代的杂芳基胺基、取代或未取代的芳基硅基、取代或未取代的杂芳基硅基、取代或未取代的芳基氧硅基、取代或未取代的芳基酰基、取代或未取代的杂芳基酰基或取代或未取代的氧膦基；R 1 , R 2 , R 3 and R are each independently selected from hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group Or its salt, phosphate group or its salt, C1～C18 alkyl group, C1～C18 alkoxy group, C1～C18 alkylsilyl group, C1～C18 alkoxysilyl group, C6～C40 substituted or unsubstituted aromatic group Base, C6~C40 heteroaryl group, C6~C60 substituted or unsubstituted heterospirocyclic ring, C6~C60 substituted or unsubstituted spirocyclic ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl group ether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroarylsilyl group, substituted or unsubstituted Aryloxysilyl, substituted or unsubstituted arylacyl, substituted or unsubstituted heteroarylacyl or substituted or unsubstituted phosphinyl;
n为0到10的整数；n is an integer from 0 to 10;
m为0到4的整数；m is an integer from 0 to 4;
上述所有基团可被部分氘代或全氘代。All the above groups may be partially or fully deuterated.
优选地，其中吡啶侧的配位基团选自下列结构中任一者：
Preferably, the coordination group on the pyridine side is selected from any one of the following structures:
Preferably, the coordination group on the pyridine side is selected from any one of the following structures:
其中，R为氢、氘、卤素、C1～C18烷基、C1～C18烷氧基、含C1～C18烷硅基、含C1～C18烷氧硅基、C6～C40取代或未取代的芳基、C6～C40的杂芳基、C6～C60取代或未取代的杂螺环、C6～C60取代或未取代的螺环、取代或未取代的芳基醚基、取代或未取代的杂芳基醚基、取代或未取代的芳基胺基、取代或未取代的杂芳基胺基、取代或未取代的芳基硅基、取代或未取代的杂芳基硅基、取代或未取代的芳基氧硅基、取代或未取代的芳基酰基、取代或未取代的杂芳基酰基或取代或未取代的氧膦基；Wherein, R is hydrogen, deuterium, halogen, C1～C18 alkyl group, C1～C18 alkoxy group, C1～C18 alkylsilyl group, C1～C18 alkoxysilyl group, C6～C40 substituted or unsubstituted aryl group , C6~C40 heteroaryl group, C6~C60 substituted or unsubstituted heterospirocyclic ring, C6~C60 substituted or unsubstituted spirocyclic ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl group Ether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroarylsilyl group, substituted or unsubstituted Aryloxysilyl, substituted or unsubstituted arylacyl, substituted or unsubstituted heteroarylacyl or substituted or unsubstituted phosphinyl;
n为0到10的整数；n is an integer from 0 to 10;
m为0到4的整数；m is an integer from 0 to 4;
上述所有基团可被部分氘代或全氘代。All the above groups may be partially or fully deuterated.
更优选地，其中R1、R2、R3和R各自独立地选自氢、甲基、乙基、叔丁基或叔丁基联苯基。More preferably, wherein R 1 , R 2 , R 3 and R are each independently selected from hydrogen, methyl, ethyl, tert-butyl or tert-butylbiphenyl.
本发明进一步提供了一种显示或照明装置，其包括该有机光电器件。The present invention further provides a display or lighting device including the organic optoelectronic device.
本发明的含螺环的有机金属配合物具有很好的热稳定性。通过在该有机金属配合物中引入刚性螺环结构，增加位阻，可以有效抑制平面型Pt配合物分子之间的相互作用，从而提高器件效率。本发明的含螺环的有机金属配合物具有较好的电子和空穴接收能力，可提升主体和客体之间的能量传输，具体表现为用本
发明的含螺环的有机金属配合物作为功能层(有机层)，尤其作为发光层制作的有机光电器件，其电流效率提升，起亮电压降低，同时器件的寿命有较大提升，说明大部分电子和空穴复合后，能量都有效地传递给该有机金属配合物用于发光，而非发热。The spiro ring-containing organometallic complex of the present invention has good thermal stability. By introducing a rigid spirocyclic structure into the organometallic complex and increasing steric hindrance, the interaction between planar Pt complex molecules can be effectively suppressed, thereby improving device efficiency. The spiro ring-containing organometallic complex of the present invention has good electron and hole receiving capabilities, and can improve the energy transmission between the host and the guest. The specific performance is as follows: The invented spiro ring-containing organometallic complex is used as a functional layer (organic layer), especially as an organic optoelectronic device produced as a light-emitting layer. Its current efficiency is increased, the lighting voltage is reduced, and the life of the device is greatly improved, indicating that most After the electrons and holes recombine, the energy is effectively transferred to the organometallic complex to emit light instead of heat.
图1为本发明的有机光电器件的结构示意图，其中，110代表基板，120表示阳极，130表示空穴注入层，140表示空穴传输层，150表示发光层，160表示空穴阻挡层，170表示电子传输层，180表示电子注入层，190表示阴极。Figure 1 is a schematic structural diagram of an organic optoelectronic device of the present invention, in which 110 represents the substrate, 120 represents the anode, 130 represents the hole injection layer, 140 represents the hole transport layer, 150 represents the light-emitting layer, 160 represents the hole blocking layer, 170 Indicates the electron transport layer, 180 indicates the electron injection layer, and 190 indicates the cathode.
为了使本发明的目的、技术方案及优点更加清楚明白，以下结合具体实施例，对本发明进行进一步详细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。In order to make the purpose, technical solutions and advantages of the present invention more clear, the present invention will be further described in detail below with reference to specific embodiments. It should be understood that the specific embodiments described here are only used to explain the present invention and are not intended to limit the present invention.
本发明使用的术语“取代的”或类似术语包含有机化合物的所有允许的取代基。广义上，允许的取代基包括有机化合物的环状和非环状、支链和非支链、碳环和杂环、芳香族和非芳香族取代基。例如，示例性取代基包括以下所述。对于合适的有机化合物来说，允许的取代基可为一个或多个，相同或不同。对于本发明的目的而言，杂原子(例如氮)能够具有氢取代基和/或本发明所述满足该杂原子价键的有机化合物的任何允许取代基。本发明不意图以任何方式用有机化合物允许的取代基来进行任何限制。同样，术语“取代”或“取代有”包含隐含条件是这种取代符合取代的原子和该取代基的允许的价键，和该取代导致稳定的化合物(例如，不会自发地进行转化(例如通过重排、环化、消去等)的化合物)。在某些方面，除非明确指出相反，否则，单独的取代基能够进一步任选地取代(即，进一步取代或未取代的)。The term "substituted" or similar terms as used herein encompasses all permissible substituents of organic compounds. Broadly speaking, permissible substituents include cyclic and acyclic, branched and unbranched, carbocyclic and heterocyclic, aromatic and nonaromatic substituents of organic compounds. For example, exemplary substituents include those described below. For suitable organic compounds, the permissible substituents may be one or more, the same or different. For the purposes of the present invention, a heteroatom (eg, nitrogen) can have a hydrogen substituent and/or any permissible substituent of the organic compounds described herein that satisfy the valence of this heteroatom. The present invention is not intended to be limited in any way by the permissible substituents of organic compounds. Likewise, the term "substituted" or "substituted with" includes the implicit proviso that such substitution is consistent with the permissible valence bonds of the substituting atom and the substituent, and that the substitution results in a stable compound (e.g., one that does not spontaneously undergo transformation) For example, compounds by rearrangement, cyclization, elimination, etc.). In certain aspects, individual substituents can be further optionally substituted (ie, further substituted or unsubstituted) unless expressly stated to the contrary.
在定义各种术语时，“R1”、“R2”、“R3”、“R4”、“R5”和“R”在本发明中作为通用符号来表示各种特定的取代基。这些符号能够是任何取代基，不限于本发明公开的那些，当它们在一个实例中被定义为某些取代基时，在另一个实例中也可以被定义为一些其他取代基。When defining various terms, "R1", "R2", "R3", "R4", "R5" and "R" are used as general symbols in the present invention to represent various specific substituents. These symbols can be any substituent, not limited to those disclosed in the present invention, and when they are defined as certain substituents in one example, they can also be defined as some other substituents in another example.
本发明使用的术语“烷基”是1至18个碳原子的支链或非支链的饱和烃基，例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、仲戊基、新戊基、己基、庚基、辛基、壬基、癸基、十二烷基、十四烷基、十六烷基、二十烷基、二十四烷基等。该烷基可为环状或非环状。该烷基可为支链或非支链的。该烷基也可为取代或未取代的。例如，该烷基可取代一个或多个基团，包括但不限于本发明所述的任选取代的烷基、环烷基、烷氧基、氨基、醚、卤素、羟基、硝基、甲硅烷基、硫-氧代基团和巯基。“低级烷基”基团是含有1至6个(例如1至4个)碳原子的烷基。The term "alkyl" used in the present invention refers to a branched or unbranched saturated hydrocarbon group of 1 to 18 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl Alkyl, eicosyl, tetradecyl, etc. The alkyl group may be cyclic or acyclic. The alkyl group may be branched or unbranched. The alkyl group may also be substituted or unsubstituted. For example, the alkyl group can substitute one or more groups, including but not limited to optionally substituted alkyl, cycloalkyl, alkoxy, amino, ether, halogen, hydroxyl, nitro, methyl as described in the present invention. Silyl groups, thio-oxo groups and mercapto groups. A "lower alkyl" group is an alkyl group containing 1 to 6 (eg, 1 to 4) carbon atoms.
在整个说明书中，“烷基”通常同时指未取代烷基和取代烷基；但是，取代烷基也在本发明中通过确定烷基上的特定取代基来具体地提及。例如，术语“卤化的烷基”或者“卤代烷基”具体是指取代有一个或多个卤素(例如，氟、氯、溴或碘)的烷基。术语“烷氧基烷基”具体是指取代有一个或多个烷氧基的烷基，如下所述。术语“烷基氨基”具体是指取代有一个或多个氨基的烷基，如下所述等。当在一种情况中使用“烷基”而在另一情况中使用具体的术语如“烷基醇”时，不意味着暗示该术语“烷基”不同时指代具体的术语如“烷基醇”等。Throughout this specification, "alkyl" generally refers to both unsubstituted and substituted alkyl groups; however, substituted alkyl groups are also specifically referred to herein by identifying the specific substituents on the alkyl group. For example, the term "halogenated alkyl" or "haloalkyl" specifically refers to an alkyl group substituted with one or more halogens (eg, fluorine, chlorine, bromine, or iodine). The term "alkoxyalkyl" specifically refers to an alkyl group substituted with one or more alkoxy groups, as described below. The term "alkylamino" specifically refers to an alkyl group substituted with one or more amino groups, as described below, etc. When "alkyl" is used in one context and a specific term such as "alkyl alcohol" is used in another context, it is not meant to imply that the term "alkyl" does not also refer to a specific term such as "alkyl" Alcohol" etc.
本发明使用的术语“芳基”是6至60个碳原子的取代或未取代的苯基，例如甲基苯基、乙基苯基、正丙基苯基、异丙基苯基、正丁基苯基、异丁基苯基、仲丁基苯基、叔丁基苯基、叔丁基联苯基、正戊基苯基、异戊基苯基、仲戊基苯基、新戊基苯基、己基苯基、庚基苯基、辛基苯基、壬基苯基、癸基苯基、十二烷基苯基、十四烷基苯基、十六烷基苯基、二十烷基苯基、二十四烷基苯基等。The term "aryl" as used herein is a substituted or unsubstituted phenyl group of 6 to 60 carbon atoms, such as methylphenyl, ethylphenyl, n-propylphenyl, isopropylphenyl, n-butyl phenyl, isobutylphenyl, sec-butylphenyl, tert-butylphenyl, tert-butylbiphenyl, n-pentylphenyl, isopentylphenyl, sec-pentylphenyl, neopentyl Phenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, dodecylphenyl, tetradecylphenyl, hexadecylphenyl, eicosanyl Alkylphenyl, tetradecylphenyl, etc.
这种做法也用于本发明所述的其它基团。也即，当术语如“环烷基”同时指代未取代的和取代的环烷基部分时，该取代的部分可另外具体地在本发明中确定；例如，具体取代的环烷基可称为例如“烷基环烷基”。类似的，取代的烷氧基可具体地称为例如“卤代烷氧基”，具体的取代烯基可为例如“烯醇”等。同样地，使用通用术语如“环烷基”和具体术语如“烷基环烷基”的不意味着该通用术语不同时包含该具体术语。This approach also applies to other groups described in this invention. That is, when a term such as "cycloalkyl" refers to both unsubstituted and substituted cycloalkyl moieties, the substituted moiety may otherwise be specifically identified in the present invention; for example, a specifically substituted cycloalkyl group may be referred to as For example, "alkylcycloalkyl". Similarly, a substituted alkoxy group may be specifically referred to as, for example, a "haloalkoxy group" and a specific substituted alkenyl group may be, for example, an "enol" or the like. Likewise, the use of a general term such as "cycloalkyl" and a specific term such as "alkylcycloalkyl" does not mean that the general term does not also encompass that specific term.
本发明使用的术语“烷氧基”和“烷氧基基团”是指通过醚键键合的1至18个碳原子的烷基或环烷基；即“烷氧基”可定义为—OR1，其中R1是如上定义的烷基或环烷基。“烷氧基”也包含刚刚描述的烷氧基聚合物；即烷氧基可为聚醚，如—OR1-OR2或—OR1-(OR2)a-OR3，其中“a”是整数1至500，而R1、R2和R3各自独立地为烷基、环烷基或其组合。The terms "alkoxy" and "alkoxy group" as used herein refer to an alkyl or cycloalkyl group of 1 to 18 carbon atoms bonded through ether bonds; that is, "alkoxy" may be defined as— OR1, where R1 is alkyl or cycloalkyl as defined above. "Alkoxy" also includes the alkoxy polymers just described; i.e., the alkoxy group may be a polyether, such as -OR1-OR2 or -OR1-(OR2)a-OR3, where "a" is an integer from 1 to 500 , and R1, R2 and R3 are each independently an alkyl group, a cycloalkyl group or a combination thereof.
本发明使用的术语“芳基”是指含有任何碳基芳香族的60个碳原子及以内的基团，包括但不限于苯、萘、苯基、联苯、苯氧基苯等。术语“芳基”也包括“杂芳基”，其被定义为含有芳香族的基团，所述芳香族基团
环内至少含有一个杂原子。杂原子的实例包括但不限于氮、氧、硫或磷。同样，术语“非杂芳基”(其也包括在术语“芳基”中)定义了含有芳香族的基团，所述芳香族基团不含杂原子。芳基可为取代或未取代的。芳基可取代有一个或多个基团，所述基团包括但不限于本发明所述的烷基、环烷基、烷氧基、烯基、环烯基、炔基、环炔基、芳基、杂芳基、醛、氨基、羧酸、酯、醚、卤素、羟基、酮、叠氮基、硝基、甲硅烷基、硫-氧代基团或巯基。术语“联芳基”是特定类型的芳基并且包含在“芳基”的定义中。联芳基是指经稠合的环结构结合在一起的两个芳基，如在萘中一样，或者经一个或多个碳-碳键连接的两个芳基，如在联苯中一样。The term "aryl" used in the present invention refers to any carbon-based aromatic group with 60 carbon atoms or less, including but not limited to benzene, naphthalene, phenyl, biphenyl, phenoxybenzene, etc. The term "aryl" also includes "heteroaryl" which is defined as an aromatic-containing group that The ring contains at least one heteroatom. Examples of heteroatoms include, but are not limited to, nitrogen, oxygen, sulfur, or phosphorus. Likewise, the term "non-heteroaryl" (which is also included in the term "aryl") defines an aromatic-containing group that does not contain heteroatoms. Aryl groups may be substituted or unsubstituted. The aryl group may be substituted with one or more groups, including but not limited to alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, Aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halogen, hydroxyl, ketone, azido, nitro, silyl, thio-oxo group or mercapto group. The term "biaryl" is a specific type of aryl group and is included in the definition of "aryl". Biaryl refers to two aryl groups joined together by a fused ring structure, as in naphthalene, or by one or more carbon-carbon bonds, as in biphenyl.
本发明使用的术语“胺”或“氨基”通过式—NR1R2表示，其中R1和R2可以独立的从氢、烷基、环烷基、烯基、环烯基、炔基、环炔基、芳基或杂芳基中选择。The term "amine" or "amino" used in the present invention is represented by the formula -NR1R2, wherein R1 and R2 can be independently selected from hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aromatic Choose from base or heteroaryl.
本发明使用的术语“羧酸”通过式—C(O)OH表示。The term "carboxylic acid" as used herein is represented by the formula -C(O)OH.
本发明使用的术语“醚”通过式R1OR2表示，其中R1和R2可独立地为本发明所述的烷基、环烷基、烯基、环烯基、炔基、环炔基、芳基或杂芳基。本发明使用的术语“聚醚”通过式—(R1O-R2O)a—表示，其中R1和R2可独立地为本发明所述的烷基、环烷基、烯基、环烯基、炔基、环炔基、芳基或杂芳基并且“a”为1至500的整数。The term "ether" used in the present invention is represented by the formula R1OR2, wherein R1 and R2 can independently be alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or Heteroaryl. The term "polyether" used in the present invention is represented by the formula - (R1O-R2O)a-, wherein R1 and R2 can independently be alkyl, cycloalkyl, alkenyl, cycloalkenyl or alkynyl as described in the present invention. , cycloalkynyl, aryl or heteroaryl and "a" is an integer from 1 to 500.
本发明使用的术语“卤素”是指卤素氟、氯、溴和碘。The term "halogen" as used herein refers to the halogens fluorine, chlorine, bromine and iodine.
本发明使用的术语“杂环基团”是指单环的和多环的非芳香族环系，并且本发明使用的“杂芳基”是指单环和多环的不多于60个碳原子的芳香族环系：其中环成员中的至少一个不为碳。该术语包括氮杂环丁烷基、二噁烷基、呋喃基、咪唑基、异噻唑基、异噁唑基、吗啉基、噁唑基(包括1,2,3-噁二唑基、1,2,5-噁二唑基和1,3,4-噁二唑基的噁唑基)、哌嗪基、哌啶基、吡嗪基、吡唑基、哒嗪基、吡啶基、嘧啶基、吡咯基、吡咯烷基、四氢呋喃基、四氢吡喃基、包括1,2,4,5-四嗪基的四嗪基、包括1,2,3,4-四唑基和1,2,4,5-四唑基的四唑基、包括1,2,3-噻二唑基、1,2,5-噻二唑基和1,3,4-噻二唑基的噻二唑基、噻唑基、噻吩基、包括1,3,5-三嗪基和1,2,4-三嗪基的三嗪基、包括1,2,3-三唑基和1,3,4-三唑基的三唑基等。As used herein, the term "heterocyclic group" refers to monocyclic and polycyclic non-aromatic ring systems, and "heteroaryl" as used herein refers to monocyclic and polycyclic non-aromatic ring systems of not more than 60 carbon atoms. Aromatic ring system of atoms in which at least one of the ring members is not carbon. The term includes azetidinyl, dioxanyl, furyl, imidazolyl, isothiazolyl, isoxazolyl, morpholinyl, oxazolyl (including 1,2,3-oxadiazolyl, 1,2,5-oxadiazolyl and 1,3,4-oxadiazolyl (oxazolyl), piperazinyl, piperidinyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridyl, Pyrimidinyl, pyrrolyl, pyrrolidinyl, tetrahydrofuryl, tetrahydropyranyl, tetrazinyl including 1,2,4,5-tetrazinyl, including 1,2,3,4-tetrazolyl and 1 , 2,4,5-tetrazolyl tetrazolyl, including 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl and 1,3,4-thiadiazolyl thiadiazolyl Diazolyl, thiazolyl, thienyl, triazinyl including 1,3,5-triazinyl and 1,2,4-triazinyl, including 1,2,3-triazolyl and 1,3, 4-triazolyl triazolyl, etc.
本发明使用的术语“羟基”通过式—OH表示。The term "hydroxyl" as used herein is represented by the formula -OH.
本发明使用的术语“硝基”通过式—NO2表示。The term "nitro" as used herein is represented by the formula -NO2.
本发明使用的术语“腈”通过式—CN表示。The term "nitrile" as used herein is represented by the formula -CN.
本发明使用的“R1”、“R2”、“R3”、“Rn”(其中n为整数)可独立地具有上面列举的基团中的一个或者多个。例如，如果R1为直链烷基，那么烷基的一个氢原子可任选取代有羟基、烷氧基、烷基、卤素等。取决于选择的基团，第一基团可结合在第二基团内，或者第一基团可侧连(即，连接)至第二基团。例如，对于短语“包含氨基的烷基”，氨基可结合在烷基的主链内。可选择地，氨基可连接至烷基的主链。所选基团的性质将决定是否第一基团嵌入或者连接至第二基团。"R1", "R2", "R3", and "Rn" (where n is an integer) used in the present invention may independently have one or more of the groups listed above. For example, if R1 is a straight chain alkyl group, then one hydrogen atom of the alkyl group may be optionally substituted with hydroxyl, alkoxy, alkyl, halogen, etc. Depending on the group selected, the first group may be incorporated within the second group, or the first group may be pendant (ie, attached) to the second group. For example, with respect to the phrase "alkyl group containing an amino group," the amino group may be bonded within the backbone of the alkyl group. Alternatively, the amino group may be attached to the backbone of the alkyl group. The nature of the selected group will determine whether the first group is embedded in or linked to the second group.
本发明所述化合物可含有“任选取代的”部分。通常，术语“取代的”(无论在前面是否存在术语“任选”)意味着指定部分的一个或多个氢被合适的取代基取代。除非另作说明，否则“任选取代的”基团可在基团的每个可取代位置具有合适的取代基，并且当任何给定结构中的一个以上位置可以被选自指定基团的一个以上取代基取代时，取代基可以在每个位置上相同或不同。本发明设想的取代基组合优选为形成稳定的或化学上可行的化合物的组合。还可以设想，在某些方面，除非明确指出相反，各个取代基可进一步任选被取代(即，进一步取代或未取代)。The compounds described herein may contain "optionally substituted" moieties. Generally, the term "substituted" (whether preceded by the term "optionally" or not) means that one or more hydrogens of the specified moiety are substituted with a suitable substituent. Unless otherwise stated, an "optionally substituted" group may have a suitable substituent at each substitutable position of the group, and when more than one position in any given structure may be selected from one of the specified groups When the above substituents are substituted, the substituents may be the same or different at each position. Combinations of substituents contemplated by this invention are preferably combinations that form stable or chemically feasible compounds. It is also contemplated that, in certain aspects, each substituent may be further optionally substituted (ie, further substituted or unsubstituted) unless expressly stated to the contrary.
在本发明公开和描述的化学结构和单元中数次提及R1、R2、R3、R4、R5、R等。在说明书中R1、R2、R3、R4、R5、R等的任何描述分别适用于引用R1、R2、R3、R4、R5、R等的任何结构或者单元，除非另作说明。本发明的制剂包含式(I)所示的有机金属配合物与一种或多种溶剂，所用的溶剂没有特别限制，可以使用本领域技术人员熟知的不饱和烃溶剂(例如甲苯、二甲苯、均三甲苯、四氢化萘、十氢萘、双环己烷、正丁基苯、仲丁基苯、叔丁基苯等)、卤化饱和烃溶剂(例如四氯化碳、氯仿、二氯甲烷、二氯乙烷、氯丁烷、溴丁烷、氯戊烷、溴戊烷、氯己烷、溴己烷、氯环己烷、溴环己烷等)、卤化不饱和烃溶剂(例如氯苯、二氯苯、三氯苯等)、醚类溶剂(例如四氢呋喃、四氢吡喃等)或酯类溶剂(苯甲酸烷基酯等)。所述的制剂直接用于制备光电器件。R1, R2, R3, R4, R5, R, etc. are mentioned several times in the chemical structures and units disclosed and described herein. Any description of R1, R2, R3, R4, R5, R, etc. in the specification applies to any structure or unit referencing R1, R2, R3, R4, R5, R, etc., respectively, unless otherwise stated. The preparation of the present invention contains an organic metal complex represented by formula (I) and one or more solvents. The solvent used is not particularly limited. Unsaturated hydrocarbon solvents well known to those skilled in the art (such as toluene, xylene, Mesitylene, tetralin, decalin, dicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, etc.), halogenated saturated hydrocarbon solvents (such as carbon tetrachloride, chloroform, methylene chloride, Dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, etc.), halogenated unsaturated hydrocarbon solvents (such as chlorobenzene , dichlorobenzene, trichlorobenzene, etc.), ether solvents (such as tetrahydrofuran, tetrahydropyran, etc.) or ester solvents (alkyl benzoate, etc.). The preparation is directly used to prepare optoelectronic devices.
本发明还提供了一种有机光电器件，其包括：第一电极；The invention also provides an organic optoelectronic device, which includes: a first electrode;
第二电极，与所述第一电极相面对；a second electrode facing the first electrode;
有机层，夹设于所述第一电极和所述第二电极之间；其中，该有机层包含本发明的有机金属配合物。An organic layer is sandwiched between the first electrode and the second electrode; wherein the organic layer contains the organic metal complex of the present invention.
本发明的有机金属配合物的结构式(I)中，与金属M相连的原子有两个形成共价键，有两个形成配位健。
In the structural formula (I) of the organometallic complex of the present invention, two atoms connected to the metal M form covalent bonds, and two atoms form coordination bonds.
本发明的有机金属配合物(铂，钯金属化合物)通过引入含刚性螺环的四齿配体单元(图1)，由于位阻的原因，可以有效地降低发光分子间的相互作用，抑制由三线态引起的淬灭，从而提高器件的发光效率。将本发明的有机金属配合物应用于有机光电器件，特别是在有机电致发光器件中，可以提升器件的电流效率、降低器件的操作电压且延长器件的寿命。The organometallic complex (platinum, palladium metal compound) of the present invention can effectively reduce the interaction between luminescent molecules due to steric hindrance by introducing a tetradentate ligand unit containing a rigid spiro ring (Figure 1). The quenching caused by the triplet state improves the luminous efficiency of the device. Applying the organic metal complex of the present invention to organic optoelectronic devices, especially in organic electroluminescent devices, can improve the current efficiency of the device, reduce the operating voltage of the device, and extend the life of the device.
在本发明中，有机光电器件可以利用喷溅涂覆法、电子束蒸发、真空蒸镀等方法在基板上蒸镀金属或具有导电性的氧化物以及它们的合金形成阳极；在制备得到的阳极表面按顺序蒸镀空穴注入层、空穴传输层、发光层、空穴阻挡层和电子传输层，随后再蒸镀阴极的方法制备。除了以上方法，基板上也可按阴极、有机层、阳极顺序蒸镀制作有机光电器件，该有机层可以包括空穴注入层、空穴传输层、发光层、空穴阻挡层及电子传输层等多层结构。本发明的有机层采用高分子材料按溶剂工程(旋转涂膜(spin-coating)、薄带成型(tape-casting)、刮片法(doctor-blading)、丝网印刷(Screen-Printing)、喷墨印刷或热成像(Thermal-Imaging)等)替代蒸镀方法制备，可以减少器件层数。In the present invention, the organic optoelectronic device can use sputter coating, electron beam evaporation, vacuum evaporation and other methods to evaporate metal or conductive oxides and their alloys on the substrate to form an anode; in the prepared anode The surface is prepared by sequentially evaporating a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer and an electron transport layer, and then evaporating a cathode. In addition to the above methods, organic optoelectronic devices can also be produced by evaporating the cathode, organic layer, and anode in sequence on the substrate. The organic layer can include a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, etc. Multi-layer structure. The organic layer of the present invention adopts polymer materials according to solvent engineering (spin-coating, tape-casting, doctor-blading, screen-printing, spraying). Ink printing or thermal imaging (Thermal-Imaging, etc.) can replace the evaporation method and can reduce the number of device layers.
根据本发明的有机光电器件所使用的材料可以分为顶发射、底发射或双面发射。本发明的有机金属配合物可以有机光电器件类似的原理适用于有机太阳能电池、照明的OLED、柔性OLED、有机感光体，有机薄膜晶体管等电。The materials used in the organic optoelectronic devices according to the present invention can be classified into top-emitting, bottom-emitting or double-sided emitting. The organometallic complex of the present invention can be applied to organic solar cells, lighting OLEDs, flexible OLEDs, organic photoreceptors, organic thin film transistors and the like on similar principles to organic optoelectronic devices.
在本发明的一种优选实施方式中，本发明的OLED器件中含有空穴传输层，空穴传输材料可以优选自已知或未知的材料，特别优选地选自以下结构，但并不代表本发明限于以下结构：
In a preferred embodiment of the present invention, the OLED device of the present invention contains a hole transport layer. The hole transport material can be preferably selected from known or unknown materials, and is particularly preferably selected from the following structures, but does not represent the present invention. Limited to the following structures:
In a preferred embodiment of the present invention, the OLED device of the present invention contains a hole transport layer. The hole transport material can be preferably selected from known or unknown materials, and is particularly preferably selected from the following structures, but does not represent the present invention. Limited to the following structures:
在本发明的一种优选实施方式中，本发明的OLED器件中含有的空穴传输层，其包含一种或多种p型掺杂剂。本发明优选的p型掺杂剂为以下结构，但并不代表本发明限于以下结构：
In a preferred embodiment of the present invention, the hole transport layer contained in the OLED device of the present invention contains one or more p-type dopants. The preferred p-type dopant of the present invention has the following structure, but it does not mean that the present invention is limited to the following structure:
In a preferred embodiment of the present invention, the hole transport layer contained in the OLED device of the present invention contains one or more p-type dopants. The preferred p-type dopant of the present invention has the following structure, but it does not mean that the present invention is limited to the following structure:
本发明的一种优选实施方式中，所述的电子传输层可以选自以下化合物的至少一种，但并不代表本发明限于以下结构：
In a preferred embodiment of the present invention, the electron transport layer can be selected from at least one of the following compounds, but this does not mean that the present invention is limited to the following structures:
In a preferred embodiment of the present invention, the electron transport layer can be selected from at least one of the following compounds, but this does not mean that the present invention is limited to the following structures:
实施例Example
本发明的具有式(I)所示的有机金属配合物(即客体化合物)，其通用的合成步骤如下：
The general synthesis steps of the organometallic complex (i.e. guest compound) represented by formula (I) of the present invention are as follows:
The general synthesis steps of the organometallic complex (i.e. guest compound) represented by formula (I) of the present invention are as follows:
将K2PtCl4(2.2mmol)，配体1(2.4mmol)，CHCl3(150mL)和AcOH(150mL)加入双口圆底烧瓶中，然后加热回流反应144小时，停止加热，降至室温，除去溶剂。将得到的固体溶解在二氯甲烷中，过硅胶短柱。在减压条件下除去溶剂，浓缩得到的固体先后用甲醇和石油醚洗涤，得到最终目标产品，收率24～53％。Add K 2 PtCl 4 (2.2mmol), ligand 1 (2.4mmol), CHCl 3 (150mL) and AcOH (150mL) into a double-necked round-bottomed flask, then heat to reflux for 144 hours, stop heating, and cool to room temperature. Remove solvent. The solid obtained was dissolved in methylene chloride and passed through a short silica gel column. The solvent was removed under reduced pressure, and the solid obtained by concentration was washed with methanol and petroleum ether successively to obtain the final target product with a yield of 24 to 53%.
配体1通过本领域公知的方法制备得到。Ligand 1 was prepared by methods well known in the art.
结合以下实施例详细地解释了有机金属配合物(即客体化合物)的制备方法以及器件的发光性能。但这些仅仅用于举例描述本发明的实施方式，所以本发明的范围并不限于此。The preparation method of the organometallic complex (ie, the guest compound) and the luminescent properties of the device are explained in detail in conjunction with the following examples. However, these are only used to illustrate the embodiments of the present invention, and the scope of the present invention is not limited thereto.
实施例1：化合物103的合成
Example 1: Synthesis of Compound 103
Example 1: Synthesis of Compound 103
参考通用合成路线，终产物的产率为32％。质谱m/z,理论值1144.56；实测值M+H：1145.58。Referring to the general synthetic route, the yield of the final product was 32%. Mass spectrum m/z, theoretical value 1144.56; measured value M+H: 1145.58.
实施例2：化合物93的合成
Example 2: Synthesis of Compound 93
Example 2: Synthesis of Compound 93
参考通用合成路线，终产物的产率为27％。质谱m/z,理论值1130.54；实测值M+H：1131.59。Referring to the general synthetic route, the yield of the final product was 27%. Mass spectrum m/z, theoretical value 1130.54; measured value M+H: 1131.59.
实施例3：化合物3的合成
Example 3: Synthesis of Compound 3
Example 3: Synthesis of Compound 3
参考通用合成路线，终产物的产率为36％。质谱m/z,理论值1074.48；实测值M+H：1075.53。Referring to the general synthetic route, the yield of the final product was 36%. Mass spectrum m/z, theoretical value 1074.48; measured value M+H: 1075.53.
实施例4：化合物107的合成
Example 4: Synthesis of Compound 107
Example 4: Synthesis of Compound 107
参考通用合成路线，终产物的产率为35％。质谱m/z,理论值1144.56；实测值M+H：1145.58。Referring to the general synthetic route, the yield of the final product was 35%. Mass spectrum m/z, theoretical value 1144.56; measured value M+H: 1145.58.
实施例5：化合物109的合成
Example 5: Synthesis of Compound 109
Example 5: Synthesis of Compound 109
参考通用合成路线，终产物的产率为41％。质谱m/z,理论值1170.57；实测值M+H：1171.62。Referring to the general synthetic route, the yield of the final product was 41%. Mass spectrum m/z, theoretical value 1170.57; measured value M+H: 1171.62.
实施例6：化合物111的合成
Example 6: Synthesis of Compound 111
Example 6: Synthesis of Compound 111
参考通用合成路线，终产物的产率为38％。质谱m/z,理论值1156.56；实测值M+H：1157.61。Referring to the general synthetic route, the yield of the final product was 38%. Mass spectrum m/z, theoretical value 1156.56; measured value M+H: 1157.61.
实施例7：化合物31的合成
Example 7: Synthesis of Compound 31
Example 7: Synthesis of Compound 31
参考通用合成路线，终产物的产率为42％。质谱m/z,理论值1130.54；实测值M+H：1131.58。Referring to the general synthetic route, the yield of the final product was 42%. Mass spectrum m/z, theoretical value 1130.54; measured value M+H: 1131.58.
实施例8：化合物43的合成
Example 8: Synthesis of Compound 43
Example 8: Synthesis of Compound 43
参考通用合成路线，终产物的产率为33％。质谱m/z,理论值1114.51；实测值M+H：1115.54。Referring to the general synthetic route, the yield of the final product was 33%. Mass spectrum m/z, theoretical value 1114.51; measured value M+H: 1115.54.
实施例9：化合物35的合成
Example 9: Synthesis of Compound 35
Example 9: Synthesis of Compound 35
参考通用合成路线，终产物的产率为36％。质谱m/z,理论值1144.56；实测值M+H：1145.59。Referring to the general synthetic route, the yield of the final product was 36%. Mass spectrum m/z, theoretical value 1144.56; measured value M+H: 1145.59.
实施例10：化合物36的合成
Example 10: Synthesis of Compound 36
Example 10: Synthesis of Compound 36
参考通用合成路线，终产物的产率为31％。质谱m/z,理论值1140.52；实测值M+H：1141.56。Referring to the general synthetic route, the yield of the final product was 31%. Mass spectrum m/z, theoretical value 1140.52; measured value M+H: 1141.56.
实施例11：化合物32的合成
Example 11: Synthesis of Compound 32
Example 11: Synthesis of Compound 32
参考通用合成路线，终产物的产率为38％。质谱m/z,理论值1144.56；实测值M+H：1145.57。Referring to the general synthetic route, the yield of the final product was 38%. Mass spectrum m/z, theoretical value 1144.56; measured value M+H: 1145.57.
OLED器件的制造：Manufacturing of OLED devices:
在发光面积为2mm×2mm大小的底发射OLED基板上，蒸镀HIL(空穴注入层)为HT-1:P-3(95:5,v/v％)，厚度为10纳米；HTL(空穴传输层)为HT-1，厚度为90纳米；EBL(电子阻挡层)为HT-8，厚度为10纳米，EML(发光层)为主体材料:本发明的有机金属配合物(94:6,v/v％)，厚度为35纳米，ETL(电子传输层)为ET-11：LiQ(50:50,v/v％)，厚度为35纳米，然后蒸镀阴极Al为70纳米。On a bottom-emitting OLED substrate with a light-emitting area of 2mm×2mm, the evaporated HIL (hole injection layer) is HT-1:P-3 (95:5, v/v%), with a thickness of 10 nanometers; HTL ( The hole transport layer) is HT-1 with a thickness of 90 nanometers; the EBL (electron blocking layer) is HT-8 with a thickness of 10 nanometers, and the EML (emitting layer) is the main material: the organic metal complex of the present invention (94: 6, v/v%), the thickness is 35 nm, the ETL (electron transport layer) is ET-11:LiQ (50:50, v/v%), the thickness is 35 nm, and then the cathode Al is evaporated to 70 nm.
其中对比的有机金属配合物及上述主体材料的结构如下：
The structures of the compared organometallic complexes and the above host materials are as follows:
The structures of the compared organometallic complexes and the above host materials are as follows:
依据上述实施例和对比例电流效率、电压和寿命等特性显示在下表1中。Characteristics such as current efficiency, voltage, and lifetime according to the above-described embodiments and comparative examples are shown in Table 1 below.
表1
Table 1
Table 1
由表1可以看出，从在配体结构上并入螺环结构，实施例1至实施例5展示了良好的器件性能，说明本发明的有机金属配合物具有一定的应用价值。As can be seen from Table 1, Examples 1 to 5 show good device performance due to the incorporation of a spiro ring structure into the ligand structure, indicating that the organometallic complex of the present invention has certain application value.
以上所述，仅为本发明较佳的具体实施方式，但本发明的保护范围并不局限于此，任何熟悉本技术领域的技术人员在本发明揭露的技术范围内，根据本发明的技术方案及其发明构思加以等同替换或改变，都应涵盖在本发明的保护范围之内。
The above are only preferred specific embodiments of the present invention, but the protection scope of the present invention is not limited thereto. Any person familiar with the technical field can, within the technical scope disclosed in the present invention, implement the technical solutions of the present invention. Equivalent substitutions or changes of the inventive concept thereof shall be included in the protection scope of the present invention.
Claims (12)
- 有机金属配合物，其结构如式I所示：
Organometallic complex, its structure is shown in Formula I:
在式I中，M选自铂或钯；In formula I, M is selected from platinum or palladium;R1、R2、R3和R各自独立地选自氢、氘、卤素、羟基、氰基、硝基、脒基、肼基、腙基、羧酸基团或其盐、磺酸基团或其盐、磷酸基团或其盐、C1～C18烷基、C1～C18烷氧基、含C1～C18烷硅基、含C1～C18烷氧硅基、C6～C40取代或未取代的芳基、C6～C40的杂芳基、C6～C60取代或未取代的杂螺环、C6～C60取代或未取代的螺环、取代或未取代的芳基醚基、取代或未取代的杂芳基醚基、取代或未取代的芳基胺基、取代或未取代的杂芳基胺基、取代或未取代的芳基硅基、取代或未取代的杂芳基硅基、取代或未取代的芳基氧硅基、取代或未取代的芳基酰基、取代或未取代的杂芳基酰基或取代或未取代的氧膦基；R 1 , R 2 , R 3 and R are each independently selected from hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group Or its salt, phosphate group or its salt, C1～C18 alkyl group, C1～C18 alkoxy group, C1～C18 alkylsilyl group, C1～C18 alkoxysilyl group, C6～C40 substituted or unsubstituted aromatic group group, C6 to C40 heteroaryl group, C6 to C60 substituted or unsubstituted heterospirocyclic ring, C6 to C60 substituted or unsubstituted spirocyclic ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl group ether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroarylsilyl group, substituted or unsubstituted Aryloxysilyl, substituted or unsubstituted arylacyl, substituted or unsubstituted heteroarylacyl or substituted or unsubstituted phosphinyl;n为0到10的整数；n is an integer from 0 to 10;m为0到4的整数；上述所有基团可被部分氘代或全氘代。m is an integer from 0 to 4; all the above groups may be partially or fully deuterated. - 根据权利要求1所述的有机金属配合物，其中吡啶侧的配位基团选自下列结构中任一者：
The organometallic complex according to claim 1, wherein the coordination group on the pyridine side is selected from any one of the following structures:
其中，R为氢、氘、卤素、C1～C18烷基、C1～C18烷氧基、含C1～C18烷硅基、含C1～C18烷氧硅基、C6～C40取代或未取代的芳基、C6～C40的杂芳基、C6～C60取代或未取代的杂螺环、C6～C60取代或未取代的螺环、取代或未取代的芳基醚基、取代或未取代的杂芳基醚基、取代或未取代的芳基胺基、取代或未取代的杂芳基胺基、取代或未取代的芳基硅基、取代或未取代的杂芳基硅基、取代或未取代的芳基氧硅基、取代或未取代的芳基酰基、取代或未取代的杂芳基酰基或取代或未取代的氧膦基；Wherein, R is hydrogen, deuterium, halogen, C1～C18 alkyl group, C1～C18 alkoxy group, C1～C18 alkylsilyl group, C1～C18 alkoxysilyl group, C6～C40 substituted or unsubstituted aryl group , C6~C40 heteroaryl group, C6~C60 substituted or unsubstituted heterospirocyclic ring, C6~C60 substituted or unsubstituted spirocyclic ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl group Ether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroarylsilyl group, substituted or unsubstituted Aryloxysilyl, substituted or unsubstituted arylacyl, substituted or unsubstituted heteroarylacyl or substituted or unsubstituted phosphinyl;n为0到10的整数；n is an integer from 0 to 10;m为0到4的整数；m is an integer from 0 to 4;上述所有基团可被部分氘代或全氘代。All the above groups may be partially or fully deuterated. - 根据权利要求1至2中任一项所述的有机金属配合物，其中R1、R2、R3和R各自独立地选自氢、甲基、乙基、叔丁基或叔丁基联苯基。The organometallic complex according to any one of claims 1 to 2, wherein R 1 , R 2 , R 3 and R are each independently selected from hydrogen, methyl, ethyl, tert-butyl or tert-butyl. phenyl.
- 根据权利要求1至2中任一项所述的有机金属配合物，其中式I选自下列结构中任一者：
The organometallic complex according to any one of claims 1 to 2, wherein formula I is selected from any one of the following structures:
- 制剂，其包含权利要求1至2中任一项所述的有机金属配合物和至少一种溶剂，其中所述溶剂为不饱和烃溶剂、饱和烃溶剂、醚类溶剂或酯类溶剂。A preparation comprising the organometallic complex according to any one of claims 1 to 2 and at least one solvent, wherein the solvent is an unsaturated hydrocarbon solvent, a saturated hydrocarbon solvent, an ether solvent or an ester solvent.
- 有机光电器件，其包括阴极层、阳极层和有机层，所述有机层为空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一者，其中所述有机层包含权利要求1至2任一项所述的有机金属配合物。Organic optoelectronic device, which includes a cathode layer, an anode layer and an organic layer, the organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer or an electron transport layer, wherein the organic layer Containing the organometallic complex according to any one of claims 1 to 2.
- 根据权利要求6所述的有机光电器件，其中所述有机层为发光层，所述发光层中包含权利要求1至2任一项所述的有机金属配合物和相应的主体材料，其中所述有机金属配合物的质量百分数在1％至50％。The organic optoelectronic device according to claim 6, wherein the organic layer is a luminescent layer, and the luminescent layer contains the organic metal complex according to any one of claims 1 to 2 and the corresponding host material, wherein the The mass percentage of the organic metal complex ranges from 1% to 50%.
- 根据权利要求6所述的有机光电器件，其中所述有机光电器件为有机光伏器件、有机发光器件、有机太阳电池、电子纸、有机感光体、有机薄膜晶体管或有机内存器件。The organic optoelectronic device according to claim 6, wherein the organic optoelectronic device is an organic photovoltaic device, an organic light emitting device, an organic solar cell, an electronic paper, an organic photoreceptor, an organic thin film transistor or an organic memory device.
- 有机光电器件，其包括阴极层、阳极层和有机层，所述有机层为发光层，其中所述发光层包含有机金属配合物，所述有机金属配合物的结构如式I所示：
Organic optoelectronic device, which includes a cathode layer, an anode layer and an organic layer, the organic layer is a light-emitting layer, wherein the light-emitting layer contains an organic metal complex, and the structure of the organic metal complex is as shown in Formula I:
在式I中，M选自铂或钯；In formula I, M is selected from platinum or palladium;R1、R2、R3和R各自独立地选自氢、氘、卤素、羟基、氰基、硝基、脒基、肼基、腙基、羧酸基团或其盐、磺酸基团或其盐、磷酸基团或其盐、C1～C18烷基、C1～C18烷氧基、含C1～C18烷硅基、含C1～C18烷氧硅基、C6～C40取代或未取代的芳基、C6～C40的杂芳基、C6～C60取代或未取代的杂螺环、C6～C60取代或未取代的螺环、取代或未取代的芳基醚基、取代或未取代的杂芳基醚基、取代或未取代的芳基胺基、取代或未取代的杂芳基胺基、取代或未取代的芳基硅基、取代或未取代的杂芳基硅基、取代或未取代的芳基氧硅基、取代或未取代的芳基酰基、取代或未取代的杂芳基酰基或取代或未取代的氧膦基；R 1 , R 2 , R 3 and R are each independently selected from hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group Or its salt, phosphate group or its salt, C1～C18 alkyl group, C1～C18 alkoxy group, C1～C18 alkylsilyl group, C1～C18 alkoxysilyl group, C6～C40 substituted or unsubstituted aromatic group group, C6 to C40 heteroaryl group, C6 to C60 substituted or unsubstituted heterospirocyclic ring, C6 to C60 substituted or unsubstituted spirocyclic ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl group ether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroarylsilyl group, substituted or unsubstituted Aryloxysilyl, substituted or unsubstituted arylacyl, substituted or unsubstituted heteroarylacyl or substituted or unsubstituted phosphinyl;n为0到10的整数；n is an integer from 0 to 10;m为0到4的整数；上述所有基团可被部分氘代或全氘代。m is an integer from 0 to 4; all the above groups may be partially or fully deuterated. - 根据权利要求9所述的有机光电器件，其中吡啶侧的配位基团选自下列结构中任一者：
The organic optoelectronic device according to claim 9, wherein the coordination group on the pyridine side is selected from any one of the following structures:
其中，R为氢、氘、卤素、C1～C18烷基、C1～C18烷氧基、含C1～C18烷硅基、含C1～C18烷氧硅基、C6～C40取代或未取代的芳基、C6～C40的杂芳基、C6～C60取代或未取代的杂螺环、C6～C60取代或未取代的螺环、取代或未取代的芳基醚基、取代或未取代的杂芳基醚基、取代或未取代的芳基胺基、取代或未取代的杂芳基胺基、取代或未取代的芳基硅基、取代或未取代的杂芳基硅基、取代或未取代的芳基氧硅基、取代或未取代的芳基酰基、取代或未取代的杂芳基酰基或取代或未取代的氧膦基；Wherein, R is hydrogen, deuterium, halogen, C1～C18 alkyl group, C1～C18 alkoxy group, C1～C18 alkylsilyl group, C1～C18 alkoxysilyl group, C6～C40 substituted or unsubstituted aryl group , C6~C40 heteroaryl group, C6~C60 substituted or unsubstituted heterospirocyclic ring, C6~C60 substituted or unsubstituted spirocyclic ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl group Ether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroarylsilyl group, substituted or unsubstituted Aryloxysilyl, substituted or unsubstituted arylacyl, substituted or unsubstituted heteroarylacyl or substituted or unsubstituted phosphinyl;n为0到10的整数；n is an integer from 0 to 10;m为0到4的整数；m is an integer from 0 to 4;上述所有基团可被部分氘代或全氘代。All the above groups may be partially or fully deuterated. - 根据权利要求9至10中任一项所述的有机光电器件，其中R1、R2、R3和R各自独立地选自氢、甲基、乙基、叔丁基或叔丁基联苯基。The organic optoelectronic device according to any one of claims 9 to 10, wherein R 1 , R 2 , R 3 and R are each independently selected from hydrogen, methyl, ethyl, tert-butyl or tert-butylbiphenyl base.
- 显示或照明装置，其包括权利要求8所述的有机光电器件。 A display or lighting device comprising the organic optoelectronic device of claim 8.
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