CN112940043A - Organic metal complex and organic photoelectric element containing same - Google Patents
Organic metal complex and organic photoelectric element containing same Download PDFInfo
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- CN112940043A CN112940043A CN202110123457.1A CN202110123457A CN112940043A CN 112940043 A CN112940043 A CN 112940043A CN 202110123457 A CN202110123457 A CN 202110123457A CN 112940043 A CN112940043 A CN 112940043A
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- organometallic complex
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- 150000004696 coordination complex Chemical class 0.000 title abstract description 28
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 29
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 17
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052751 metal Inorganic materials 0.000 claims abstract description 14
- 239000002184 metal Substances 0.000 claims abstract description 14
- -1 palladium metals Chemical class 0.000 claims abstract description 11
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 8
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 7
- 239000010410 layer Substances 0.000 claims description 53
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- 229910052717 sulfur Inorganic materials 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 9
- 239000012044 organic layer Substances 0.000 claims description 7
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 6
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- 239000002346 layers by function Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 3
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 claims description 3
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 claims description 3
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 claims description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims description 3
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 claims description 3
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 3
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 claims description 3
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 claims description 3
- 229940117389 dichlorobenzene Drugs 0.000 claims description 3
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 claims description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 claims description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 229910019950 S—O Inorganic materials 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000005693 optoelectronics Effects 0.000 claims description 2
- 238000013086 organic photovoltaic Methods 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 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 claims 1
- 229910052741 iridium Inorganic materials 0.000 abstract description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 abstract description 3
- 150000002902 organometallic compounds Chemical class 0.000 abstract 1
- 238000001228 spectrum Methods 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 24
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 16
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- 238000000034 method Methods 0.000 description 15
- 238000000921 elemental analysis Methods 0.000 description 14
- 230000009918 complex formation Effects 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 150000002736 metal compounds Chemical class 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000005281 excited state Effects 0.000 description 4
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
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- 238000004020 luminiscence type Methods 0.000 description 3
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- 238000002360 preparation method Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000010345 tape casting Methods 0.000 description 3
- 229940125773 compound 10 Drugs 0.000 description 2
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 239000000243 solution Substances 0.000 description 2
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- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 1
- CSDXMOBPFIGGIG-UHFFFAOYSA-N 2-hydrazinylguanidine Chemical compound NNNC(N)=N CSDXMOBPFIGGIG-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an organic metal complex and an organic photoelectric element containing the same, in particular to an organic electroluminescent diode, wherein the structure of the organic metal complex is shown as the formula (I):
m is selected from platinum (Pt) or palladium (Pd); detailed information of the organometallic complex and the organic photoelectric element can be understood by the specific description provided herein. The organometallic compound provided by the invention can obtain OLED devices with high efficiency and long service life, the light-emitting spectrum is between 490 nanometers and 750 nanometers, and the organometallic complex is shown on green light to red light OLEDsPotential applications of (1). The platinum and palladium metals are rich in earth crust, can replace rare metal iridium to form sustainable organic metal complexes, and have good commercial application prospect.
Description
Technical Field
The invention belongs to the field of organic photoelectricity, and particularly relates to an organic metal complex and an organic photoelectric element comprising the same, in particular to an organic electroluminescent diode.
Background
As a novel display technology, the organic light-emitting diode (OLED) has the unique advantages of self luminescence, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, high response speed, wide applicable temperature range, low driving voltage, capability of manufacturing flexible, bendable and transparent display panels, environmental friendliness and the like, can be applied to flat panel displays and new generation illumination, and can also be used as a backlight source of an LCD.
The OLED emission is divided into two modes of fluorescence emission and phosphorescence emission, and it is theorized that the ratio of a singlet excited state to a triplet excited state due to charge binding is 1: 3. Professor Baldo and Forrest in 1998 discovered that triplet phosphorescence can be utilized at room temperature, and the upper limit of the original internal quantum efficiency is increased to 100%, and triplet phosphors are often heavy metal atoms and are formed by complexes, and the strong spin-orbit coupling effect causes the energy levels of a singlet excited state and a triplet excited state to be mixed with each other by utilizing the heavy atom effect, so that the originally forbidden triplet energy is relieved to emit light in the form of phosphorescence, and the quantum efficiency is greatly improved.
At present, a host-guest light emitting system mechanism is almost completely used for a light emitting layer in an OLED assembly, namely, a guest light emitting material is doped in a host material, a commonly used organic guest material is an iridium metal compound, the iridium metal compound is mainly applied to commercial OLED materials at present, but the iridium metal is very expensive and has insufficient content in earth crust, an organic metal complex is required to replace the expensive iridium metal complex, and the alternative scheme of the OLED light emitting material is expanded.
The invention finds that an organic metal compound (Pt or Pd) can improve the luminous efficiency of the organic metal compound by introducing a specific cyclic structure, a substituent group and the like, ensures that the organic metal compound has high-efficiency luminous characteristics, and can obtain high current efficiency and reduce the operating voltage of components when being applied to organic photoelectric elements, particularly organic electroluminescent devices.
Disclosure of Invention
The invention aims to provide an organic metal complex and a photoelectric device comprising the same, in particular to an organic light-emitting diode.
The structure of the organic metal complex provided by the invention is shown as the formula (I):
wherein, in formula (I), M is platinum (Pt) or palladium (Pd); at least one of X1 to X5 is independently selected from the group consisting of a bond, O, S, N-R6, B-R6, P-R6, O ═ P-R6, (C-R6R7) n, C ═ O, S ═ O, S (═ O)2Or one of Si-R6R 7; x6 to X7 are absent or independently selected from the group consisting of a bond, O, S, N-R6, B-R6, P-R6, O ═ P-R6, (C-R6R7) n, C ═ O, S ═ O, S (═ O)2Or one of Si-R6R 7; t is independently selected from one of N-R6, B-R6, P-R6, O-P-R6, C-R6R7 or Si-R6R 7; y1 to Y13 are independently selected from C or N; l1 is independently selected from a bond, or C O, S O, S (═ O)2L2 is independently selected from chemical bond, or one of O, N-R6 and S, and when L1 and L2 are chemical bonds at the same time, Y1 or Y7 is directly bonded to metal M; rings CY1 to CY5 each independently form a C6 to C40 ring group and a C1 to C40 heterocyclic group with the corresponding Y1 to Y13, CY6 being a five-membered ring; r1 to R7 are each independently selected from hydrogen, deuterium, CN, halogen, hydroxyl, nitro, salts of carboxylic acids, sulfonic acid groups or salts thereof, phosphoric acid groups or salts thereof, hydrazino, amidino, amide, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C2 to C60 alkenyl, substituted or unsubstituted C1 to C60 alkoxy, substituted or unsubstituted C1 to C60 cycloalkyl, substituted or unsubstituted C1 to C60 heteroalkyl, substituted or unsubstituted C6 to C60 aryl, substituted or unsubstituted C1 to C60 heteroaryl, substituted or unsubstituted C1 to C60 amine, substituted or unsubstituted C1 to C60 silicon, substituted or unsubstituted C6 to C60 aromatic fused ring, and substituted or unsubstituted C1 to C60 heteroaromatic fused ring; r1 to R7 each independently may be partially or fully deuterated, each independently may be partially or fully fluorinated; r1 to R7 may be unsubstituted or polysubstituted according to the valence bond principle.
Preferably, the organometallic complex of the present invention has two atoms bonded to the metal M to form covalent bonds and two atoms to form coordinate bonds, so that the organometallic complex is in a neutral state.
Preferably, the organometallic complex of the invention, of the formula (I)
Moieties are independently selected from one of the following representative groups, but not representative of the group:
wherein X8 is independently selected from O, S, N-R6, B-R6, P-R6, O ═ P-R6, C-R6R7, C ═ O, S ═ O, S (═ O)2Or one of Si-R6R 7; y is N or C-R8, R6, R7, R8 are the same as R1 in claim 1, and when R8 is 2 or more, the same or different from each other, adjacent R1 to R8 may form a ring.
Preferably, the organometallic complex of the invention, of the formula (I)
Moieties are independently selected from one of the following representative groups, but not representative of the group:
wherein T, Y3 and Y4 are the same as defined in claim 1, Y is N or C-R8, R6, R7 and R8 are the same as defined in claim 1 for R1, and when R8 is 2 or more, the same or different from each other, adjacent R1 to R8 may form a ring.
Preferably, the organometallic complex of the invention, of the formula (I)
The moiety is typically selected from one of the following groups, but does not represent a limitation thereto:
wherein Y11 is the same as in claim 1; x9 and X10 are independently selected from one of O, S, N-R6, B-R6, P-R6, O-P-R6, C-R6R7, C-O, S-O, S (═ O)2, or Si-R6R 7; y is N or C-R8, R6, R7, R8 are the same as R1 in claim 1, and when R8 is 2 or more, the same or different from each other, adjacent R1 to R8 may form a ring.
Preferably, the organometallic complex of the invention, of the formula (I)
Moieties are independently selected from one of the following representative groups, but not representative of the group:
wherein Y8 is the same as in claim 1; x11 is independently selected from one of O, S, N-R6, B-R6, P-R6, O ═ P-R6, C-R6R7, C ═ O, S ═ O, S (═ O)2, or Si — R6R 7; y is N or C-R8, R6, R7, R8 are the same as R1 in claim 1, and when R8 is 2 or more, the same or different from each other, adjacent R1 to R8 may form a ring.
Preferably, the organometallic complex of the invention formula (I) is selected from one of the following representative structures, but does not represent a limitation thereto:
the present invention relates to an organometallic complex comprising a compound represented by the formula (I) and one or more preparation(s) formed with a solvent, the solvent used is not particularly limited, and there can be used unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decahydronaphthalene, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, etc., halogenated saturated hydrocarbon solvents such as carbon tetrachloride, chloroform, dichloromethane, 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., ester solvents such as alkyl benzoate, etc., which are well known to those skilled in the art.
The present invention claims an organic optoelectronic component,
the method comprises the following steps: a first electrode; a second electrode facing the first electrode; the organic functional layer is clamped between the first electrode and the second electrode;
wherein the organic functional layer comprises the organometallic complex.
The Organic photoelectric Element of the present invention is any one of an Organic photovoltaic device, an Organic Light Emitting Device (OLED), an Organic Solar Cell (OSC), electronic paper (e-paper), an Organic Photoreceptor (OPC), an Organic Thin Film Transistor (OTFT), an Organic Memory device (Organic Memory Element), a lighting device, and a display device.
The invention also relates to an organic electroluminescent device which comprises a cathode layer, an anode layer and an organic layer, wherein the organic layer comprises at least one of a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron injection layer and an electron transport layer, and the light-emitting layer of the device contains the organic metal complex.
The organic electroluminescent device light-emitting layer contains the organic metal complex and a corresponding main material, wherein the mass percent of the organic metal complex is 0.1-50%.
In the present invention, the organic photoelectric device is an anode which can be formed by depositing a metal or an oxide having conductivity and an alloy thereof on a substrate by a sputtering method, electron beam evaporation, vacuum evaporation, or the like; and sequentially evaporating a hole injection layer, a hole transport layer, a luminescent layer, a hole blocking layer and an electron transport layer on the surface of the prepared anode, and then evaporating a cathode. The organic electroluminescent device is prepared by vapor deposition of the cathode, the organic layer and the anode on the substrate except the above method. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, and an electron transport layer. In the invention, the organic layer is prepared by adopting a high polymer material according to a solvent engineering (spin-coating), tape-casting (tape-casting), doctor-blading (sector-Printing), Screen-Printing (Screen-Printing), ink-jet Printing or Thermal-Imaging (Thermal-Imaging) method instead of an evaporation method, so that the number of the device layers can be reduced.
The materials used for the organic electroluminescent device according to the present invention may be classified into top emission, low emission, or double-sided emission. The compounds of the organic electroluminescent device according to the embodiment of the present invention can be applied to the aspects of organic solar cells, illuminating OLEDs, flexible OLEDs, organic photoreceptors, organic thin film transistors and other electroluminescent devices by a similar principle of the organic light emitting device.
The invention has the beneficial effects that:
the organic metal complex has high luminous efficiency, and the proper ligand structure can improve the energy transmission between a host and an object, and the organic metal complex is particularly characterized in that the organic electroluminescent device manufactured by taking the organic metal complex as a functional layer, especially as a luminous layer, has high current efficiency and reduced lighting voltage. After most of electrons and holes are recombined, energy is effectively transferred to the organic metal complex for luminescence, and a novel organic metal complex with excellent luminescence property is provided.
Drawings
FIG. 1 is a structural diagram of an organic electroluminescent diode device according to the present invention.
Where 110 denotes a substrate, 120 denotes an anode, 130 denotes a hole injection layer, 140 denotes a hole transport layer, 150 denotes a light emitting layer or an active layer, 160 denotes a hole blocking layer, 170 denotes an electron transport layer, 180 denotes an electron injection layer, and 190 denotes a cathode.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
In a preferred embodiment of the present invention, the OLED device according to the invention comprises a hole transport layer, which may preferably be selected from known or unknown materials, particularly preferably from the following structures, without representing the present invention being limited to the following structures:
in a preferred embodiment of the present invention, the hole transport layer contained in the OLED device of the present invention comprises one or more p-type dopants. Preferred p-type dopants of the present invention are, but do not represent a limitation of the present invention to:
in a preferred embodiment of the present invention, the electron transport layer may be selected from at least one of the compounds ET-1 to ET-13, but does not represent that the present invention is limited to the following structures:
the electron transport layer may be formed from an organic material in combination with one or more n-type dopants (e.g., LiQ).
The present invention also provides a preparation comprising the organometallic complex and a solvent, and the solvent used is not particularly limited, and an unsaturated hydrocarbon solvent such as toluene, xylene, mesitylene, tetrahydronaphthalene, decahydronaphthalene, bicyclohexyl, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, etc., a halogenated saturated hydrocarbon solvent such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, etc., a halogenated unsaturated hydrocarbon solvent such as chlorobenzene, dichlorobenzene, trichlorobenzene, etc., an ether solvent such as tetrahydrofuran, tetrahydropyran, etc., an ester solvent such as alkyl benzoate, etc., which are well known to those skilled in the art can be used. The preparation is directly used for preparing photoelectric devices.
According to the literature and the relevant technical reserves of the inventors, the synthesis of organometallic complexes of the formula (I) is referred to, for example, as follows:
example 1: synthesis of Compound 1
(1) S-1(10 mmol) and S-2(11 mmol) were completely dissolved in tetrahydrofuran/water (2:1, 80 ml) in a round-bottom flask under nitrogen atmosphere, potassium carbonate (5 g), palladium tetrakis (triphenylphosphine) acetate (0.1 g) were added, and the mixture was heated under reflux for 10-12 hours. After cooling to room temperature, acetic acid (2 ml) was added and stirred for 1 hour, the upper tetrahydrofuran layer was separated, filtered through celite, and the solvent was concentrated in vacuo and then extracted with petroleum ether: ethyl acetate (20: 1-2: 1) was purified and separated as eluent on a silica gel column to give S-3 (yield 82%), LC-MS, 692.4.
(2) In a round-bottom flask, S-1(10 mmol), nickel chloride (10 mmol) and acetic acid (8 ml) were heated under nitrogen atmosphere to reflux for 3 days. After cooling to room temperature, filtration gave a yellow solid, which was purified using petroleum ether: dichloromethane (20: 1-2: 1) was purified and isolated as eluent on silica gel column to give compound 1 (73% yield), which was further purified by vacuum sublimation. LC-MS: theory 885.31, found: 885.3, respectively; elemental analysis C65.09; h is 4.89; n is 3.16; actually measuring: c, 65.00; h is 5.03; and N is 3.11.
Example 2: synthesis of Compound 2
The synthesis procedure of compound 2 was similar to that of compound 1, with a final metal complex formation yield of 76%, LC-MS: theory 941.37, found: 941.3, respectively; elemental analysis C: 66.31; h is 5.46; 2.97 of N; actually measuring: c, 66.26; h, 5.48; and N is 3.02.
Example 3: synthesis of Compound 3
The synthesis procedure of compound 3 was similar to that of compound 1, with a final metal complex formation yield of 75%, LC-MS: theory 944.36, found: 944.4, respectively; elemental analysis C: 66.09; h is 5.44; n is 4.45; actually measuring: c, 66.12; h, 5.48; n: 4.56.
Example 4: synthesis of Compound 4
The synthesis procedure of compound 4 was similar to that of compound 1, with a final metal complex formation yield of 75%, LC-MS: theory 972.43, found: 972.4, respectively; elemental analysis C: 67.88; h is 6.11; n is 4.32; actually measuring: 67.93; h is 6.18; n is 4.31.
Example 5: synthesis of Compound 5
The synthesis procedure of compound 5 was similar to that of compound 1, with a final metal complex formation yield of 73%, LC-MS: theory 966.38, found: 966.4, respectively; elemental analysis C: 68.31; h is 5.52; n is 4.34; actually measuring: 68.26 parts of C; h is 5.57; n: 4.26.
Example 6: synthesis of Compound 6
The synthesis procedure of compound 6 was similar to that of compound 1, with a final metal complex formation yield of 71%, LC-MS: theory 908.36, found: 908.4, respectively; elemental analysis C: 64.74; h is 5.66; n is 4.62; actually measuring: c, 64.70; h is 5.73; and N is 4.57.
Example 7: synthesis of Compound 7
The synthesis procedure of compound 7 was similar to that of compound 1, with a yield of 79% of the final metal complex formed, LC-MS: theory 936.43, found: 936.4; elemental analysis C: 66.65; h is 6.35; n is 4.48; actually measuring: 66.69; h is 6.46; n is 4.42.
Example 8: synthesis of Compound 8
The synthesis procedure of compound 8 was similar to that of compound 1, with a final metal complex formation yield of 72%, LC-MS: theory 968.44, found: 968.4, respectively; elemental analysis C: 64.44; h is 6.55; n is 4.34; actually measuring: c, 64.47; 6.640 is the ratio of H to H; and 4.35 of N.
Example 9: synthesis of Compound 9
Synthesis of Compound 9S-3 is analogous to S-3 in Compound 1;
the synthesis steps of S-4 are as follows: compound S-3(10 mmol) was dissolved in acetic acid (100 ml), 2 ml of concentrated sulfuric acid was added dropwise, and the mixture was heated under reflux for 12 hours. After concentration and cooling, the mixture was poured into ice water and extracted with dichloromethane (50 ml X2). The dichloromethane layer is washed by saturated saline solution and saturated ammonium chloride aqueous solution and then concentrated to be dry, and crude products are treated by petroleum ether: purifying and separating ethyl acetate (20: 1-2: 1) serving as eluent on a silica gel column to obtain a compound S-4 (yield is 87%); LC-MS: 619.3; the yield of the finally formed metal complex compound 9 was 83%, LC-MS: theory 812.27, found: 812.3, respectively; elemental analysis C: 62.06; h is 4.84; n is 5.17; actually measuring: c, 62.10; h is 4.93; and 5.16 of N.
Example 10: synthesis of Compound 10
The synthesis procedure of compound 10 was similar to that of compound 9, with a final metal complex formation yield of 78%, LC-MS: theory 904.33, found: 904.3, respectively; elemental analysis C65.03; h is 5.23; n is 4.64; actually measuring: c, 65.12; h is 5.27; n: 4.68.
Example 11: synthesis of Compound 11
The synthesis procedure of compound 11 was similar to that of compound 1, with a final metal complex formation yield of 70%, LC-MS: theory 957.4, found: 957.4, respectively; elemental analysis C: 66.45; h is 5.79; 2.92 of N; actually measuring: 66.42; h is 5.88; and N is 3.03.
Example 12: synthesis of Compound 12
The synthesis procedure of compound 12 was similar to that of compound 1, with a final metal complex formation yield of 76%, LC-MS: theory 988.46, found: 988.5, respectively; elemental analysis C: 67.99; h is 6.42; n is 4.25; actually measuring: 68.04; h is 6.47; n is 4.23.
Example 13: synthesis of Compound 13
The synthesis procedure of compound 13 was similar to that of compound 1, with a final metal complex formation yield of 70%, LC-MS: theory 847.37, found: 847.4, respectively; elemental analysis C: 73.61; h is 7.01; n is 4.95; actually measuring: c, 73.65; h is 7.07; and N is 4.93.
Example 14: synthesis of Compound 14
The synthesis procedure of compound 14 was similar to compound 1, with a final metal complex formation yield of 70%, LC-MS: theory 854.32, found: 854.3, respectively; elemental analysis C: 63.22; h is 5.31; n is 4.91; actually measuring: 63.27; h is 5.37; and 4.90 percent of N.
A P-doped material P-1 to P-5 is vapor-deposited on the surface or anode of an ITO glass having a light emitting area of 2mm x 2mm or the P-doped material is co-vapor-deposited with a compound shown in the table at a concentration of 1% to 50% to form a Hole Injection Layer (HIL) of 5 to 100nm and a Hole Transport Layer (HTL) of 5 to 200nm, and then a light emitting layer (EML) (which may contain the compound) of 10 to 100nm is formed on the hole transport layer, and finally an Electron Transport Layer (ETL) of 20 to 200nm and a cathode of 50 to 200nm are sequentially formed using the compound, and if necessary, an Electron Blocking Layer (EBL) is added between the HTL and the EML, and an Electron Injection Layer (EIL) is added between the ETL and the cathode, thereby manufacturing an organic light emitting device.
OLED device examples:
the structure of the bottom-emitting OLED device is specifically implemented on ITO-containing glass, the HIL is HT-1: P-3(95:5 v/v%), and the thickness is 10 nanometers; HTL is HT-1, and the thickness is 90 nanometers; EBL is HT-10, thickness is 10 nm, EML is GH-1: organometallic complex (95:5 v/v%), thickness is 35 nm, ETL is ET-13: LiQ (50:50 v/v%) with a thickness of 35 nm, and then evaporation of cathode Al at 70 nm.
According to the above device embodiments, the External Quantum Efficiency (EQE), the turn-on voltage, the light emission peak, and the like of the OLED device are shown in table 1 below.
TABLE 1
| Examples | Compound (I) | Lighting voltage (volt) | EQE | Luminous peak (nanometer) | LT90 (hours) |
| Comparison device 1 | GD-1 | 2.8 | 20.5％ | 515 | 150 |
| Comparison device 2 | RD-1 | 2.5 | 18.7％ | 625 | 240 |
| Device example 1 | Compound 1 | 2.7 | 21.3％ | 520 | 170 |
| Device example 2 | Compound 2 | 2.6 | 22.2％ | 520 | 230 |
| Device example 3 | Compound 3 | 2.8 | 21.8％ | 522 | 180 |
| Device example 4 | Compound 4 | 2.6 | 21.6％ | 516 | 205 |
| Device example 5 | Compound 5 | 2.6 | 22.9％ | 523 | 195 |
| Device example 6 | Compound 6 | 2.6 | 23.1％ | 521 | 235 |
| Device example 7 | Compound 7 | 2.6 | 23.3％ | 525 | 220 |
| Device example 8 | Compound 8 | 2.8 | 22.4 | 518 | 211 |
| Device example 9 | Compound 9 | 2.7 | 23.6％ | 520 | 250 |
| Device example 10 | Compound 10 | 2.5 | 22.1％ | 625 | 280 |
| Device example 11 | Compound 11 | 2.4 | 22.3％ | 623 | 272 |
| Device example 12 | Compound 12 | 2.4 | 25.1％ | 620 | 260 |
| Device example 13 | Compound 13 | 2.6 | 22.7％ | 530 | 245 |
| Device example 14 | Compound 14 | 2.7 | 21.4％ | 518 | 155 |
According to the invention, platinum or palladium metal is formed into a novel organic metal compound, the novel organic metal compound is found to have good luminous property, and the novel organic metal compound is used as a guest material to be doped into a host material GH-1, so that an OLED device with the external quantum efficiency of 21.3-25.1% is obtained. In bottom-emitting OLED devices without any light extraction means, the external quantum efficiency exceeded 20%, indicating that the organometallic complexes of the present invention have an internal quantum efficiency in OLED devices approaching 100%. Meanwhile, the service life LT90 of the device reaches 280 hours at most, and compared with a reference green luminescent material GD-1, the efficiency and the service life of the device are improved. Device examples 10 to 12 are red phosphorescent OLED devices, and efficiencies exceeding 22% in external quantum efficiency were obtained. Device 13 also achieves a green device with an external quantum efficiency of over 22% with palladium metal complexes. The organic metal compound can obtain a green and red phosphorescent OLED device with long service life and high efficiency, and meanwhile, the platinum or palladium metal earth crust has rich content, has the potential of replacing iridium metal organic metal complexes, and has good commercial application prospect.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (14)
1. An organometallic complex having a structure represented by the formula (I):
wherein, in formula (I), M is platinum (Pt) or palladium (Pd); at least one of X1 to X5 is independently selected from the group consisting of a bond, O, S, N-R6, B-R6, P-R6, O ═ P-R6, (C-R6R7) n, C ═ O, S ═ O, S (═ O)2Or one of Si-R6R 7; x6 to X7 are absent or independently selected from the group consisting of a bond, O, S, N-R6, B-R6, P-R6, O ═ P-R6, (C-R6R7) n, C ═ O, S ═ O, S (═ O)2Or one of Si-R6R 7; t is independently selected from one of N-R6, B-R6, P-R6, O-P-R6, C-R6R7 or Si-R6R 7; y1 to Y13 are independently selected from C or N; l1 is independently selected from a bond, or C O, S O, S (═ O)2L2 is independently selected from chemical bond, or one of O, N-R6 and S, and when L1 and L2 are chemical bonds at the same time, Y1 or Y7 is directly bonded to metal M; rings CY1 to CY5 each independently form a C6 to C40 ring group and a C1 to C40 heterocyclic group with the corresponding Y1 to Y13, CY6 being a five-membered ring; r1 to R7 are each independently selected from hydrogen, deuterium, CN, halogen, hydroxyl, hydrazino, amidino, amido, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C2 to C60 alkenyl, substituted or unsubstituted C1 to C60 alkoxy, substituted or unsubstituted C1 to C60 cycloalkyl, substituted or unsubstituted C1 to C60 heteroalkyl, substituted or unsubstituted C6 to C60 aryl, substituted or unsubstituted C1 to C60 heteroaryl, substituted or unsubstituted C1 to C60 amine, substituted or unsubstituted C1 to C60 silicon, substituted or unsubstituted C6 to C60 aromatic fused ring, substituted or unsubstituted C1 to C60 heteroaromatic fused ring; r1 to R7 each independently may be partially or fully deuterated, each independently may be partially or fully fluorinated; r1 to R7 may be unsubstituted or polysubstituted according to valence bond rules; n is an integer of 1 to 6.
2. The organometallic complex according to claim 1, wherein two of the atoms bonded to the metal M form covalent bonds and two of the atoms form coordinate bonds.
3. The organometallic complex according to claims 1 to 2, characterized in that in the formula (I)
Moieties are independently selected from one of the following representative groups:
wherein X8 is independently selected from O, S, N-R6, B-R6, P-R6, O ═ P-R6, C-R6R7, C ═ O, S ═ O, S (═ O)2Or one of Si-R6R 7; y is N or C-R8, R6, R7, R8 are the same as R1 in claim 1, and when R8 is 2 or more, the same or different from each other, adjacent C-R8 may form a ring.
4. The organometallic complex according to claims 1 to 2, characterized in that in the formula (I)
Moieties are independently selected from one of the following representative groups:
wherein T, Y3 and Y4 are the same as defined in claim 1, Y is N or C-R8, R6, R7 and R8 are the same as defined in claim 1 for R1, and when R8 is 2 or more, they are the same as or different from each other, and adjacent R8 may form a ring.
5. The organometallic complex according to claims 1 to 2, characterized in that in the formula (I)
The moiety is typically selected from one of the following groups:
wherein Y11 is the same as in claim 1; x9 and X10 are independently selected from one of O, S, N-R6, B-R6, P-R6, O-P-R6, C-R6R7, C-O, S-O, S (═ O)2, or Si-R6R 7; y is N or C-R8, R6, R7, R8 are the same as R1 in claim 1, and when R8 is 2 or more, the same or different from each other, adjacent R8 may form a ring.
6. The organometallic complex according to claims 1 to 2, characterized in that in the formula (I)
Moieties are independently selected from one of the following representative groups:
wherein Y8 is the same as in claim 1; x11 is independently selected from one of O, S, N-R6, B-R6, P-R6, O ═ P-R6, C-R6R7, C ═ O, S ═ O, S (═ O)2, or Si — R6R 7; y is N or C-R8, R6, R7, R8 are the same as R1 in claim 1, and when R8 is 2 or more, the same or different from each other, adjacent R8 may form a ring.
7. The organometallic complex according to any one of claims 1 to, characterized in that the organometallic complex formula (I) is selected from one of the following representative structures:
8. a formulation comprising an organometallic complex according to any of claims 1 to 7 and at least one solvent.
9. A formulation according to claim 8, wherein the organometallic complex and the solvent are formulated in the form of a solvent, and the solvent used is not particularly limited, and a halogenated saturated hydrocarbon solvent such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane and the like, a halogenated unsaturated hydrocarbon solvent such as chlorobenzene, dichlorobenzene, trichlorobenzene and the like, an ether solvent such as tetrahydrofuran, tetrahydropyran and the like, an ester solvent such as alkyl benzoate and the like, which are known to those skilled in the art can be used.
10. An organic optoelectronic device, comprising:
a first electrode;
a second electrode facing the first electrode;
the organic functional layer is clamped between the first electrode and the second electrode;
wherein the organic functional layer comprises the organometallic complex according to any one of claims 1 to 7.
11. An organic photoelectric element comprising a cathode layer, an anode layer and an organic layer, the organic layer comprising at least one of a hole injection layer, a hole transport layer, a light emitting layer or an active layer, an electron injection layer, and an electron transport layer, wherein: an organometallic complex according to claims 1 to 7 contained in any one layer of the device.
12. The Organic photoelectric Element according to claim 7, wherein the Organic photoelectric Element 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), an Organic Memory device (Organic Memory Element), a lighting device, or a display device.
13. The organic photoelectric element according to claims 10 to 12, wherein the light-emitting layer contains the organometallic complex and a corresponding host material, wherein the organometallic complex is present in an amount of 1 to 50% by mass, and the host material is not limited.
14. A display or lighting device comprising the organic photoelectric element according to any one of claims 10 to 13.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113793910A (en) * | 2021-10-22 | 2021-12-14 | 浙江华显光电科技有限公司 | Organic optoelectronic device and display or lighting device comprising same |
| CN114315914A (en) * | 2021-07-09 | 2022-04-12 | 浙江华显光电科技有限公司 | Organometallic complex, preparation, organic photoelectric device and display or lighting device |
| US20220127291A1 (en) * | 2020-10-26 | 2022-04-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| WO2024022294A1 (en) * | 2022-07-25 | 2024-02-01 | 浙江工业大学 | Spirochiral platinum(ii) and palladium(ii) complex circularly polarized luminescent material and use thereof |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3266790A1 (en) * | 2016-07-05 | 2018-01-10 | Samsung Electronics Co., Ltd | Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound |
| KR20180100898A (en) * | 2017-03-02 | 2018-09-12 | 삼성전자주식회사 | Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same |
| KR20190009876A (en) * | 2017-07-19 | 2019-01-30 | 삼성디스플레이 주식회사 | organic light emitting device |
| KR20190012063A (en) * | 2017-07-26 | 2019-02-08 | 삼성전자주식회사 | Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same |
| KR20190013105A (en) * | 2017-07-31 | 2019-02-11 | 삼성전자주식회사 | Organic light emitting device |
| KR20190060408A (en) * | 2017-11-24 | 2019-06-03 | 삼성전자주식회사 | Organic light emitting device and method for preparing the same |
| KR20190083984A (en) * | 2018-01-05 | 2019-07-15 | 삼성전자주식회사 | Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same |
| EP3617215A1 (en) * | 2018-08-31 | 2020-03-04 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound |
| KR20200040198A (en) * | 2018-10-08 | 2020-04-17 | 삼성전자주식회사 | Organometallic compound and organic light emitting device including the same |
| US20200266365A1 (en) * | 2017-11-08 | 2020-08-20 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| US20200381633A1 (en) * | 2019-05-31 | 2020-12-03 | Shijiazhuang Chengzhi Yonghua Display Material Co., Ltd. | Organic electroluminescent material and organic electroluminescent device |
-
2021
- 2021-01-29 CN CN202110123457.1A patent/CN112940043A/en active Pending
Patent Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3266790A1 (en) * | 2016-07-05 | 2018-01-10 | Samsung Electronics Co., Ltd | Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound |
| CN107573383A (en) * | 2016-07-05 | 2018-01-12 | 三星电子株式会社 | Organo-metallic compound including its organic luminescent device and the diagnosis composition including the organo-metallic compound |
| KR20180100898A (en) * | 2017-03-02 | 2018-09-12 | 삼성전자주식회사 | Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same |
| KR20190009876A (en) * | 2017-07-19 | 2019-01-30 | 삼성디스플레이 주식회사 | organic light emitting device |
| KR20190012063A (en) * | 2017-07-26 | 2019-02-08 | 삼성전자주식회사 | Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same |
| KR20190013105A (en) * | 2017-07-31 | 2019-02-11 | 삼성전자주식회사 | Organic light emitting device |
| US20200266365A1 (en) * | 2017-11-08 | 2020-08-20 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| KR20190060408A (en) * | 2017-11-24 | 2019-06-03 | 삼성전자주식회사 | Organic light emitting device and method for preparing the same |
| KR20190083984A (en) * | 2018-01-05 | 2019-07-15 | 삼성전자주식회사 | Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same |
| EP3617215A1 (en) * | 2018-08-31 | 2020-03-04 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound |
| KR20200040198A (en) * | 2018-10-08 | 2020-04-17 | 삼성전자주식회사 | Organometallic compound and organic light emitting device including the same |
| US20200381633A1 (en) * | 2019-05-31 | 2020-12-03 | Shijiazhuang Chengzhi Yonghua Display Material Co., Ltd. | Organic electroluminescent material and organic electroluminescent device |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20220127291A1 (en) * | 2020-10-26 | 2022-04-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN114315914A (en) * | 2021-07-09 | 2022-04-12 | 浙江华显光电科技有限公司 | Organometallic complex, preparation, organic photoelectric device and display or lighting device |
| CN113793910A (en) * | 2021-10-22 | 2021-12-14 | 浙江华显光电科技有限公司 | Organic optoelectronic device and display or lighting device comprising same |
| WO2024022294A1 (en) * | 2022-07-25 | 2024-02-01 | 浙江工业大学 | Spirochiral platinum(ii) and palladium(ii) complex circularly polarized luminescent material and use thereof |
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