CN101243099A - 金属络合物 - Google Patents
金属络合物 Download PDFInfo
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- CN101243099A CN101243099A CNA2006800300508A CN200680030050A CN101243099A CN 101243099 A CN101243099 A CN 101243099A CN A2006800300508 A CNA2006800300508 A CN A2006800300508A CN 200680030050 A CN200680030050 A CN 200680030050A CN 101243099 A CN101243099 A CN 101243099A
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- 150000004696 coordination complex Chemical class 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 239000003446 ligand Substances 0.000 claims description 26
- -1 salicyl imines Chemical class 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 229910052741 iridium Inorganic materials 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000000412 dendrimer Substances 0.000 claims description 7
- 229920000736 dendritic polymer Polymers 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 7
- 229910052697 platinum Inorganic materials 0.000 claims description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000003205 fragrance Substances 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 230000021615 conjugation Effects 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229930194542 Keto Natural products 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 229910052703 rhodium Inorganic materials 0.000 claims description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
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- 125000004122 cyclic group Chemical group 0.000 claims description 3
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 claims description 3
- 230000010354 integration Effects 0.000 claims description 3
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- 238000010791 quenching Methods 0.000 claims description 3
- 230000000171 quenching effect Effects 0.000 claims description 3
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- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
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- MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical compound C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910000765 intermetallic Inorganic materials 0.000 claims description 2
- 229910001507 metal halide Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 125000005259 triarylamine group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
- 150000005309 metal halides Chemical class 0.000 claims 1
- 239000008204 material by function Substances 0.000 abstract description 2
- 238000000151 deposition Methods 0.000 description 14
- 230000008021 deposition Effects 0.000 description 14
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- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 12
- 239000013522 chelant Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 150000002466 imines Chemical group 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OVFJHQBWUUTRFT-UHFFFAOYSA-N 1,2,3,4-tetrahydrotetrazine Chemical compound C1=CNNNN1 OVFJHQBWUUTRFT-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- VDULMXJUOWIPGE-UHFFFAOYSA-N 1-phenylisoquinoline quinoline Chemical compound N1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12 VDULMXJUOWIPGE-UHFFFAOYSA-N 0.000 description 2
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 2
- BAGQBTMEEISJLK-UHFFFAOYSA-N 2-fluoronaphthalene Chemical compound C1=CC=CC2=CC(F)=CC=C21 BAGQBTMEEISJLK-UHFFFAOYSA-N 0.000 description 2
- MTUBTKOZCCGPSU-UHFFFAOYSA-N 2-n-naphthalen-1-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 MTUBTKOZCCGPSU-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- 241000790917 Dioxys <bee> Species 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
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- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- 150000002902 organometallic compounds Chemical class 0.000 description 2
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
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- 238000001953 recrystallisation Methods 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
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- 238000003786 synthesis reaction Methods 0.000 description 2
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 2
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- RJXNZBKNKLNXLX-UHFFFAOYSA-N 1,2-oxazole;1,3-oxazole Chemical compound C=1C=NOC=1.C1=COC=N1 RJXNZBKNKLNXLX-UHFFFAOYSA-N 0.000 description 1
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- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 1
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- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
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- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- HCCNHYWZYYIOFM-UHFFFAOYSA-N 3h-benzo[e]benzimidazole Chemical class C1=CC=C2C(N=CN3)=C3C=CC2=C1 HCCNHYWZYYIOFM-UHFFFAOYSA-N 0.000 description 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 1
- LCOMFVDNVLHUEK-UHFFFAOYSA-N C(C)C(=O)C(=O)C.C1(=CC=CC=C1)C1=CC=CC=C1 Chemical compound C(C)C(=O)C(=O)C.C1(=CC=CC=C1)C1=CC=CC=C1 LCOMFVDNVLHUEK-UHFFFAOYSA-N 0.000 description 1
- MSJMEQRRQOBTRB-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3NC12.N1C=CC=CC=C1 Chemical compound C1=CC=CC=2C3=CC=CC=C3NC12.N1C=CC=CC=C1 MSJMEQRRQOBTRB-UHFFFAOYSA-N 0.000 description 1
- 241000555268 Dendroides Species 0.000 description 1
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- ZSTLPJLUQNQBDQ-UHFFFAOYSA-N azanylidyne(dihydroxy)-$l^{5}-phosphane Chemical compound OP(O)#N ZSTLPJLUQNQBDQ-UHFFFAOYSA-N 0.000 description 1
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- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
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- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
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- 125000006038 hexenyl group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 125000002524 organometallic group Chemical group 0.000 description 1
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- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
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- 125000005981 pentynyl group Chemical group 0.000 description 1
- 150000005053 phenanthridines Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
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- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 230000005610 quantum mechanics Effects 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
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- 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
- C07F15/0033—Iridium compounds
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
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- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
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- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
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- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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Abstract
本发明描述了新型的金属络合物。该类型的化合物可以在许多不同的最广义可归于电子工业应用中用作功能材料。
Description
本发明描述新型的材料,其在有机电致发光元件中的用途和基于其的显示器。
有机金属化合物,特别是Ir和Pt化合物,在许多不同的最广义上可归于电子工业的应用例如在有机电致发光器件中用作功能材料。这样的器件的一般结构例如描述在US 4,539,507和US 5,151,629中。最近几年中进行的一项开发是使用显示磷光而不是荧光的有机金属络合物(M.A.Baldo等,Appl.Phys.Lett.1999,75,4-6)。出于量子力学原因,利用有机金属化合物作为磷光发光体可以实现最高达四倍的能量和功率效率增加。这种研制的成功与否取决于是否发现同样能在OLEDs中实现这些优点的对应的器件组合物(与单线态发光=荧光相比较,三重态发光=磷光)。此处可提及的主要条件特别是长操作寿命和络合物高的热稳定性。
然而,因为在显示三重态发光的OLEDs中仍存在相当大的问题,所以需要迫切改进。这同样特别是适用三线态发光体本身。在文献中已知的大部分络合物包括基于苯基吡啶或相关结构的配位体,它们与铱或铂配位(例如WO 02/068435,WO 04/026886和EP1211257)。
在实践中,要求改进具有一些关键缺点的该类型化合物:
1.关键缺陷是上面描述的化合物的热稳定性低。因此,例如均配型络合的面式-三(1-苯基异喹啉-C2,N)铱(III)(Ir(piq)3)在不分解的情况下不能升华。甚至在典型的高真空条件(p<10-7毫巴)下,观察到这种化合物相当大的分解,其中,除占使用的Ir(piq)3量约30wt%的包含铱的灰分之外,可检测到1-苯基异喹啉及其他低分子量化合物的释放。这种热分解导致器件的特性实际上不可能再现,特别是对寿命产生不利的影响。因为分解导致络合物大量损失,因此同样需要在通过升华纯化金属络合物期间络合物具有更高的温度稳定性。
2.操作寿命通常太短,其同样至今妨碍了将磷光OLEDs引入高性能和长寿命的器件中。
3.该络合物通常在有机溶剂中仅具有低的溶解度,使得通过重结晶或色谱分离法进行高效纯化变得更加困难或被阻止。这特别是适用于如显示器制造中要求的相对大量的纯化。特别是例如能用于制备聚合物的溴化络合物仅显示低的溶解度,因此难以在聚合期间处理。
4.根据现有技术体系,特别是用于发红光络合物的配位体,仅能在复杂的多步过程中获得。
因此,需要这样的化合物,其不具有上述提及的缺点,但至少具有相当于已知的金属络合物的效率和发光颜色。
US 2004/241493描述了亚胺化合物和铱的5-元螯合环作为白色到发白的发光体。如何使用这些络合物实现其他的颜色不是显而易见的。
令人惊讶地,已经发现特定的新型化合物,其使用具有改进的作为OLEDs中的三线态发光体性能的、具有亚胺化合物的六元螯合环,代替上面描述的五元螯合环。为了解释起见,五元铱螯合环和六元铱螯合环显示如下,其中D代表配位原子,例如氮,C照常代表碳:
在一些情况下,用于OLEDs中包括六元和七元螯合环的金属络合物已经描述在文献中:
EP 1211257描述了包括在配位体的苯基和氮苯环之间的非共轭单元X,例如O、S、CR2等的金属络合物,得到具有不连续共轭的配位体体系的六元螯合环状络合物。如上述提及申请中实施例所揭示的,这些络合物显示蓝色到橙红色发光,但显然地可能是由于缺乏共轭配位体而不适合于产生深红色发光。
JP 2003/342284描述了类似的六元螯合环状络合物,其中单元X是较大环系的一部分。特别是,X是咔唑体系的氮或者在芴9-位上的碳。此处,再次形成了具有非共轭配位体的体系。
JP 2004/111193描述了共轭和非共轭的七元螯合环状络合物。
本发明涉及通式(1)的化合物:
M(L)n(L‘)m(L“)o
通式(1)
包含通式(2)的亚结构M(L)n,
其中以下说明适用于使用的符号和标记:
M是过渡金属;
A在每一次出现中是相同或者不同的,为NR或O;
D,对于A=NR,是与M结合的sp2-杂化的碳原子,且对于A=O,是具有与M配位的非键电子对的杂原子,
E在每一次出现中是相同或者不同的,是sp2-杂化的碳或者氮原子;
Cy在每一次出现中是相同的或不同的,是经由sp2-杂化碳原子或具有任选结合一个或多个基团R的非键电子对的杂原子,与M结合的碳环或者杂环;
Y,对于A=NR,相同或者不同的在每一次出现中是CR2,C(=O),C(=NR),C(=N-NR2),C(=CR2),SiR2,O,S,S(=O),S(=O)2,Se,NR,PR,P(=O)R,AsR,As(=O)R或BR,和对于A=O为CR-;
R,R1在每一次出现中是相同或者不同的,为H,F,Cl,Br,I,CN,B(OH)2,B(OR2)2,NO2,具有1-40个碳原子的直链烷基或者烷氧基,或者具有3-40个碳原子的支链或者环烷基或者烷氧基,其中一个或多个非相邻的CH2基团可以被-R2C=CR2-,-C≡C-,Si(R2)2,Ge(R2)2,Sn(R2)2,-O-,-S-,-NR2-,-(C=O)-,-(C=NR2)-,-P=O(R2)-或-CONR2-取代,其中一个或多个H原子可以被F、Cl、Br或I取代,或具有5-40个碳原子的芳香或杂芳香环系或芳氧基或杂芳氧基,它们可被一个或多个非芳基R取代;此处R也可以与Cy形成另外的脂族或芳香环系;
R2相同或者不同的在每一次出现中是H或具有1-20个碳原子的脂族或芳烃基团,其中单个H原子也可以被F取代;此处两个或多个基团R2也可以彼此形成环系;
n是1,2或3;
此处通式(1)中的配位体L′和L″是单阴离子双齿的螯合配位体;m和o在每一次出现中是相同的或不同的,为0、1或2;此处对于正方形平面的配位,n+m+o=2,例如铂和钯,对于具有八面体配位的金属,例如铱,n+m+o=3。
杂化认为是指原子轨道的线性组合。因此,一个2s和两个2p轨道的线性组合产生三个等同的sp2杂化轨道,它们彼此形成120°的角度。其余p轨道例如在芳族体系中能够形成π键。
对于本发明的目的,其中单个H原子或CH2基团也可以被上述提到的基团取代的C1-C40烷基特别优选认为是指如下的基团:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、环戊基、正己基、环己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基或辛炔基。C1-C40-烷氧基特别优选认为是指甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基或2-甲基丁氧基。具有5-40个芳香环原子的芳族或杂芳族体系,它们在每一情况下也可以被上述提到的基团R1取代以及可以通过任何希望的位置连接至芳烃或杂芳族环上,特别是指来源于如下的基团:苯、萘、蒽、菲、嵌二萘、屈、茈、荧蒽、丁省、戊省、苯并芘、联苯、亚联苯基、三联苯、亚三联苯、芴、螺二芴、三聚茚、异三聚茚、二氢菲、二氢芘、四氢芘、顺式的或者反式的茚并芴、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、硫芴、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、噁唑、苯并噁唑、萘并噁唑、蒽并噁唑、菲并噁唑、异噁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、吡嗪、二氮蒽、1.5-二氮杂萘、氮杂咔唑、苯并咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,3,4-噁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲嗪和苯并噻二唑。
Cy优选是芳香或杂芳族体系。
优选的通式(1)化合物包括通式(2a)的亚结构M(L)n,
其中M,A,Y,R,R1,R2,L′,L″,n,m和o具有如上面描述相同的含义,以下说明适用于其他的符号:
D,对于A=NR,是与M结合的sp2-杂化碳原子,对于A=O,是经由非键电子对与M配位的氮或磷,优选氮;
X在每一次出现中是相同或者不同,是CR1,N或P;或
(X-X)或(X=X)(即,两个相邻的X)代表NR1,S或O;或
(X-X)或(X=X)(即,两个相邻的X)如果符号E代表N,则代表CR1、N或P;条件是Cy代表5或6元环;
E在每一次出现中相同或者不同的是C或N,条件是如果符号E代表N,则确切地在Cy中一个单元X-X(即两个相邻的X)等于CR1、N或P。
本发明一种特别优选的实施方案包括通式(1a)的化合物:
M(L)n(L′)m(L″)o
通式(1a)
包含至少一种通式(2b)和/或(2c)的亚结构M(L)n,
和任选包括通式(3)的亚结构M(L′),
其中M、Y、D、R、R1、R2,L″、n、m和o具有如上面描述的相同含义,而且此外:
X在每一次出现中是相同或者不同的,是CR1或N;或者
(X-X)或(X=X)(即,两个相邻的X)代表NR1、S或O;条件是Cy代表五元或者六元环;
Q在每一次出现中是相同或者不同的,是-CR1=CR1-、-N=CR1-、-N=N-、NR1、O或S。
优选通式(1)或通式(1a)的化合物,其中符号Y,对于A=NR,相同或者不同的是CR2,C(=O),C(=CR2),O,S,NR,PR,P(=O)R或BR,对于A=O为CR-。特别优选通式(1)或通式(1a)的化合物,其中符号Y,对于A=NR,相同或者不同的是CR2,O,S,NR或P(=O)R;对于A=O,为CR-。非常特别优选通式(1)或通式(1a)的化合物,其中符号Y,对于A=NR,等于CR2或NR;对于A=O,等于CR-。
本发明的单阴离子二齿配位体L″是来源于1,3-二酮的1,3-二酮酸酯,比如乙酰丙酮、苯甲酰丙酮、1,5-二苯基乙酰丙酮、双(1,1,1-三氟乙酰基)甲烷,来源于3-酮酯的3-酮酸酯,例如乙酰醋酸乙酯,来源于氨基羧酸的羧化物,比如吡啶-2-羧酸、喹啉-2-羧酸、甘氨酸、N,N-二甲基甘氨酸、丙氨酸、N,N-二甲基丙氨酸,来源于水杨基亚胺的水杨基亚胺化物,比如甲基水杨基亚胺、乙基水杨基亚胺、苯基水杨基亚胺,或含氮杂环化合物的硼酸酯,比如四(1-咪唑基)硼酸酯和四(1-吡唑基)硼酸酯。
本发明特别优选的实施方式涉及通式(2d)-(2f)的刚性体系,其中Y的取代基R与环Cy和/或基团R1形成五元环或六元环,
其中符号和标记具有如上所述的相同的含义。
非常特别优选包含通式(2g)、通式(2h)或通式(2i)的亚结构M(L)n的通式(1)或通式(1a)的化合物,
其中M、X、R、R1、R2和n具有如上面描述的相同的含义,以下说明适用于符号Z:
Z在每一次出现中相同或者不同的是二价基团-C(R1)2-,-C(=O)-,-C[=C(R1)2]-,-C(R1)2-C(R1)2-,-C(R1)2-C(R1)2-C(R1)2-,-C(R1)2-O-C(R1)2-,-C(R1)2-N(R1)-,-C(R1)=C(R1)-,-C(R1)=N-,-O-,-S-,-N(R1)-,-P(R1)-,-P(=O)(R1)-或-B(R1)-。
在本发明另外的优选实施方式中,以这样一种方法产生和取代配位体以使得在与金属配位时不能由其形成五元螯合环。
而且优选通式(1)或通式(1a)的化合物,其中符号M=Rh、Ir、Pd或Pt;特别优选,M=Ir或Pt,特别是Ir。
而且优选通式(1)或通式(1a)的化合物,其中符号n=2或3。特别优选其中符号o=0的化合物。非常特别优选其中符号m=o=0的化合物。特别优选,对于钯和铂络合物,n=2和m=o=0,对于铑和铱络合物,n=3和m=o=0。
而且优选其中符号X代表CR1的通式(1)或通式(1a)的化合物。
优选本发明通式(1)或通式(1a)的化合物,其中通式(2g)、(2h)或(2i)中的符号Z代表二价基团-C(R1)2-,-C(=O)-,-C(R1)2-C(R1)2-,-C(R1)2-N(R1)-,-C(R1)=C(R1)-,-C(R1)=N-,-O-,-S-或-N(R1)-。符号Z特别优选代表-C(R1)2-,-C(R1)2-C(R1)2-,-C(R1)=C(R1)-,-S-或-N(R1)-。
制备通式(2)或通式(2a)-(2i)的亚结构的相应配位体,以及配位体L′和L″可以通过有机合成领域普通技术人员熟知的通用有机化学方法制备。亚胺合成的前体通常是可商业获得的β-酮化合物,它们与胺起反应脱水得到亚胺。该合成比现有技术常规的配位体合成显著地更简单。
本发明的金属络合物原则上可以通过各种各样的方法制备;然而,如下所述的方法证明是特别适合的。
因此,本发明还涉及制备本发明金属络合物的方法,包括使相应的自由配位体与通式(4)的金属醇盐反应,与通式(5)的金属酮酮化物或与通式(6)、(7)或(8)的单或者多环的金属卤化物反应,
其中符号M和R2具有如上述的含义,p=1或者2,Hal=F、Cl,Br或者I。
同样可以使用金属化合物,优选铑和铱的化合物,它们载带醇盐和/或卤化物和/或羟基以及酮酮酸酯基团。这些化合物也可以是带电的。特别适合作为原料的对应的铱化合物公开在WO 04/085449中。
优选如WO 02/060910和WO 04/085449中描述的进行络合物的合成。如WO 05/042548中描述的,例如同样能够合成异片段络合物。
这些工艺能够得到高纯度、优选大于99%(通过1H-NMR和/或高效液相色谱法确定)的本发明通式(1)的化合物。
此处阐明的合成方法特别能够制备用于通式(1)化合物的以下显示的结构(1)-(33),所述的结构也可以被取代基R1取代。为清楚起见,此处这些取代基在大多数场合下未给出。
上面描述的本发明的化合物,例如化合物(11)、(14)和(25),也可以用作用于制备相应的共轭、部分共轭或非共轭低聚物、聚合物或树枝状聚合物的共聚单体。此处的聚合优选通过溴官能度进行。该聚合物的其他重复单元优选选自芴(例如根据EP 842208或WO00/22026)、螺二芴(例如根据EP 707020或EP 894107)、二氢菲(例如根据WO 05/014689)、茚并芴(例如根据WO 04/041901和WO 04/113412)、菲(例如根据WO 05/104264)、对亚苯基(例如根据WO 92/18552)、咔唑(例如根据WO 04/070772或WO 04/113468)、酮(例如根据WO05/040302)、硅烷(例如根据WO 05/111113)、三芳基胺或噻吩(例如根据EP 1028136)亦或其多个不同的单元。此处它们或者可以被引入聚合物的侧链或主链,或也可以代表聚合物链的支化点(例如根据WO06/003000)。
因此本发明进一步涉及包括一个或多个通式(1)或通式(1a)的化合物的共轭、部分共轭或非共轭的低聚物、聚合物或树枝状聚合物,其中至少一个上述定义的基团R或R1,优选R1代表与聚合物或树枝状聚合物的结合。对于通式(1)或通式(1a)的单元,如上面已经描述的优选同样适用于聚合物和树枝状高分子。
上述提及的低聚物、聚合物、共聚物和树枝状聚合物的特征在于在有机溶剂中良好的溶解度,和在有机电致发光器件中的高效率和稳定性。
本发明通式(1)的化合物,特别是那些通过卤素官能化的化合物,此外还可通过通用的反应类型进一步官能化,并从而转变为通式(1)的延伸化合物。此处可提及的例子是使用芳基硼酸的Suzuki官能化,或使用胺的Hartwig-Buchwald官能化。
本发明通式(1)的化合物,低聚物,聚合物,树枝状高分子或延伸化合物在电子元件,比如有机发光二极管(OLEDs),有机集成电路(O-ICs),有机场效应晶体管(O-FETs),有机薄膜晶体管(O-TFTs),有机场猝熄器件(O-FQDs),有机发光晶体管(O-LETs),发光电化学电池(LECs),有机太阳能电池(O-SCs),或有机激光器二极管(O-lasers)中被用作有源元件。
因此,本发明进一步涉及本发明通式(1)的化合物,本发明的低聚物、聚合物和树枝状高分子,和通式(1)相应的延伸化合物在电子元件中用作有源元件,特别是作为发光化合物的用途。
本发明还涉及电子元件,特别是有机和聚合发光二极管(OLEDs,PLEDs),有机场效应晶体管(O-FETs),有机薄膜晶体管(O-TFTs),有机集成电路(O-ICs),有机场猝熄器件(O-FQDs),有机发光晶体管(O-LETs),发光电化学电池(LECs),有机太阳能电池(O-SCs)和有机激光器二极管(O-lasers),其包括本发明通式(1)的一种或多种化合物,本发明的低聚物、聚合物和树枝状聚合物,和通式(1)相应的扩展化合物,特别是作为发光化合物。
本发明的化合物优选用作有机或聚合发光二极管的发光层中的发光化合物。特别是,如果它们是本发明的低分子量化合物,则它们通常与基质一起使用。在本发明中的基质要么是低分子量的,要么是低聚或聚合的。
优选的基质材料不仅是基于咔唑-例如CBP(双(咔唑基)联苯)-的那些,而且是包括咔唑或咔唑衍生物的其他材料,例如在WO 00/057676,EP 01/202358和WO 02/074015中描述的那些。此外优选酮和亚胺,例如在WO 04/093207中描述的,特别是基于螺二芴的那些,和氧化膦,硒化膦,磷腈,亚砜和砜,如在WO 05/003253中描述的,特别是基于螺二芴的那些。进一步优选硅烷,多配体金属络合物,例如描述于WO 04/081017中,和基于螺二芴的寡亚苯化合物,例如描述于EP 676461和WO 99/40051中。特别优选的基质是酮,氧化膦,亚砜和砜。尤其特别优选酮和氧化膦。
本发明化合物相对于现有技术的化合物具有以下优点:
1.本发明的化合物特征在于高温稳定性。因此,低分子量化合物能够在高真空下蒸发而不发生分解,低聚、树枝状和聚合物化合物同样是热稳定性非常好的,因此使得器件能够进行热处理而不被破坏。对于可重复地制造OLEDs,该特性是一个基础的先决条件,且尤其对操作寿命产生积极的影响。因此,这些稀有金属的化合物的资源节约性利用是可能的,因为所述络合物可以在纯化期间在实质上没有损失的情况下升华。
2.本发明的化合物特征在于在有机溶剂中良好的溶解度,这大幅简化了通过通用的方法比如重结晶或色谱法对它们的纯化。因此,所述化合物同样能够从溶液中通过涂敷或印刷技术加工。该特性在通过蒸发进行的常规处理期间同样是有利的,因为因此大幅简化了所使用的设备或荫罩的清洗。
3.本发明化合物的合成特征在于与现有技术的复杂体系相反,大大简化了配位体的合成。因此,这些配位体从可商业获得的化合物在几步中、有时甚至在一步合成中得到,而根据现有技术对于配位体的合成需要复杂的合成,特别是对于发红光的体系。
实施例:
除非另外指出,以下合成在保护气体气氛下进行。原料可购买自ALDRICH或ABCR。
实施例1:铱络合物Ir1的合成
a)合成配体L1
将25.1g(0.272mol)苯基溴化镁在100ml干燥THF中的溶液冷却到0℃。46.6g(0.272mol)的1-氰基-2-氟萘在700ml干燥THF中的溶液在15分钟之内加入到该溶液中。该反应混合物回流过夜,然后冷却到-78℃。187.5ml(0.3mol)正丁基锂(1.6M溶液,在己烷中)加入到该混合物中,搅拌该混合物30分钟。然后加入在200ml干燥THF中的18.7ml(0.3mol)的甲基碘。该反应混合物温热到室温,搅拌2小时。加入300ml的水和500ml的二乙醚,分离去水相,用二乙醚提取三次。用饱和的氯化钠溶液洗涤结合的有机相,并用MgSO4干燥。在分离去溶剂之后,产品通过柱色谱法在硅石上纯化(庚烷∶EtOAc为65∶35)。产率:43.3g(对应理论值的60.4%)。
b)氯代桥接铱络合物二聚物的合成
8.2g(17mmol)的NaIr(acac)2Cl2和21.8g(83mmol)的配位体L1在400ml三甘醇二甲醚中的脱气溶液回流48小时。该悬浮体冷却到室温,用抽吸过滤去沉淀,用三甘醇二甲醚和乙醇洗涤,并在减压下干燥。产率:9.7g(理论值的73.6%)。
c)合成络合物Ir1
2.4g(1.73mmol)实施例1b)的络合物,0.43g(4.29mmol)乙酰丙酮和1.95g(18.4mmol)碳酸钠在86ml甲氧基乙醇中的脱气混合物回流16小时。该反应混合物冷却到室温,用抽吸过滤去沉淀。用乙醇和己烷洗涤固体。
实施例2:合成铱络合物Ir2
a)合成配位体L2的前体
252ml(2mol)苯乙胺和230ml(2.24mol)三乙胺溶解在500ml的二氯甲烷中。232ml(2mol)2-氟萘基氯化物(溶解在200ml二氯甲烷中)以这样的速度逐滴地加入到0℃的溶液中,该速度要使温度不超越40℃。该混合物在室温下搅拌过夜。该白色固体沉淀溶解在3000ml的二氯甲烷中。加入700ml的2M NaOH。然后每一次用700ml稀释的NaOH洗涤该混合物两次,每一次用700ml的1M HCl洗涤三次,和每一次用700ml饱和的NaHCO3溶液洗涤两次。用MgSO4干燥有机相,在减压下除去溶剂。用少许二氯甲烷漂洗固体,在减压下干燥。产率:475.6g(理论值的81.1%)。
b)合成配位体L2
65.1g(0.222mol)实施例2a)的N-苯乙基-2-氟萘酰胺在90℃溶解在375ml的二甲苯中。随后分批加入75.5g(0.266mol)的P2O5,回流该反应混合物。将140ml(0.658mol)的POCl3逐滴地加入到热反应混合物中,该混合物回流另外的3小时。该热反应混合物倒在冰上,小心地加入固体NaOH直到达到pH为12。该沉淀磷酸盐溶解在4L的水中。分离相,每一次用300ml甲苯萃取该水相三次。混合的有机相每一次用300ml的HCl萃取三次(pH 1)。300ml的甲苯加入到该水相中,使用固体NaOH使pH回到12。随后每一次用150ml的甲苯萃取该水相三次。该结合的有机相用MgSO4干燥,在减压下除去溶剂。产率:89.7g(理论值的97.1%)。
c)合成络合物Ir2
类似实施例1b)和1c)的合成,进行Ir2的合成。
实施例3-5:包括化合物Ir1和Ir2的有机电致发光器件的制造和表征
本发明的电致发光器件可如WO 05/003253中描述的方法制造。此处比较两种不同的OLEDs的结果。为提供更好的可比较性,基本结构、使用的材料、掺杂度和它们的层厚度是相同的。仅仅改变发光层中的掺杂物。实施例3描述了现有技术的比较标准,其中发光层由基质CBP和客体材料三(苯基异喹啉)铱(Ir(piq)3)组成。此外描述了包括由基质CBP和客体材料Ir1和Ir2组成的发光体层的OLED(实施例4和5)。类似于上述提及通常的方法,制造具有以下结构的OLEDs:
PEDOT 60nm(从水中旋涂;PEDOT购买自H.C.Starck,Goslar;聚[3,4-亚乙基二氧基-2,5-噻吩])(HIL)
NaphDATA 20nm(气相沉积;NaphDATA从SynTec获得;4,4′,4″-三(N-1-萘基-N-苯基氨基)三苯胺)(HTL)
S-TAD 20nm(气相沉积;S-TAD,根据WO 99/12888合成;2,2′,7,7′-四(二苯胺)螺二芴)(HTL)
发光体层:(EML)
CBP 20nm(气相沉积;CBP从ALDRICH购得,并进一步纯化,最后升华两次;4,4′-双(N-咔唑基)联苯)
Ir1和Ir2(10%掺杂,气相沉积;根据实施例1和2合成)
或:
Ir(piq)3(10%掺杂,气相沉积;根据WO 03/0068526合成),比较例
BCP 10nm(气相沉积;BCP购买自ABCR,直接使用;2,9-二甲基-4,7-联苯基-1,10-菲咯啉)(HBL)
AlQ3 10nm(气相沉积;AlQ3购买自SynTec;三(喹啉)铝(III))(ETL)
LiF 1nm
Al 100nm.
这些仍没有优化的OLEDs通过标准方法表征;为此目的确定电致发光光谱、由电流/电压/明亮度特性线(IUL特性线)计算得到的作为明亮度函数的效率(以cd/A测定)和寿命。
使用掺杂物Ir(piq)3制造的OLEDs,在彩色坐标CIE:x=0.68,y=0.32处,在上面描述的条件下具有约6.5cd/A的最大效率。对于100cd/m2的参考亮度需要的电压为6.2V。在500cd/m2的初始亮度下寿命大约为250h(见表1)。
相反,使用本发明掺杂物Ir1和Ir2制造的OLEDs在彩色坐标(CIE)x=0.70、y=0.30处显示5.6-5.8cd/A的最大效率,其中对于100cd/m2的基准亮度下需要的电压为5.3-5.4V(见表1)。在500cd/m2的初始亮度下的寿命为390h-510h,超过参考材料Ir(piq)3的寿命(见表1)。
表1:以CBP作为基质使用本发明掺杂物得到的器件
实施例 | EML | 最大效率[cd/A] | 在100cd/m2的电压[V] | CIE(x,y) | 寿命[h](初始亮度500cd/m2) |
实施例3(比较) | CBP:10%Ir(piq)3(30nm) | 6.5 | 6.2 | 0.68/0.32 | 250 |
实施例4 | CBP:10%Ir1(30nm) | 5.8 | 5.4 | 0.70/0.30 | 390 |
实施例5 | CBP:10%Ir2(30nm) | 5.6 | 5.3 | 0.70/0.30 | 510 |
实施例6-8:使用本发明掺杂物的其他器件实施例
在包括如WO 04/093207中所述基质M1的OLEDs中试验本发明的掺杂物Ir1和Ir2和现有技术的比较材料Ir(piq)3。具有以下结构的OLEDs用类似于实施例3-5中描述的方法制造:
PEDOT 80nm(从水中旋涂;PEDOT购买自H.C.Starck,Goslar;聚[3,4-亚乙基二氧基-2,5-噻吩])(HIL)
NaphDATA 20nm(气相沉积;NaphDATA从SynTec获得;4,4′,4″-三(N-1-萘基-N-苯基氨基)三苯胺)(HTL)
S-TAD 20nm(气相沉积;S-TAD,根据WO 99/12888合成;2,2′,7,7′-四(二苯胺)螺二芴)(HTL)
发光体层:(EML)
M1双(9,9′-螺二芴-2-基)酮(气相沉积;根据WO 2004/093207合成)
Ir1和Ir2(10%掺杂,气相沉积;根据实施例1和2合成)
或者:
Ir(piq)3(10%掺杂,气相沉积;根据WO 03/0068526合成)
HBM12,7-双(4-联苯-1-基)-2′,7′-二叔丁基螺-9,9′-二芴(气相沉积;根据WO 05/011334合成)
AlQ3(气相沉积;AlQ3购买自SynTec;三(喹啉)铝(III))(ETL);
Ba/Al 3nm Ba,在顶部上150nm Al。
这些仍没有优化的OLEDs通过标准方法表征;为此目的确定电致发光光谱、由电流/电压/明亮度特性线(IUL特性线)计算的作为明亮度函数的效率(以cd/A测定)和寿命。在表2中总结了由这些OLEDs获得的结果。
为清楚起见,基质M1、空穴阻挡材料HBM1和比较的掺杂物Ir(piq)3显示如下:
表2:以M1作为基质使用本发明掺杂物得到的器件
实施例 | EML | 最大效率[cd/A] | 在100cd/m2的电压[V] | CIE(x,y) | 寿命[h](初始明亮度1000cd/m2) |
实施例6(比较) | M1:10%Ir(piq)3(30nm) | 7.4 | 5.8 | 0.68/0.32 | 8300 |
实施例7 | M1:10%Ir1(30nm) | 6.5 | 4.9 | 0.70/0.30 | 8500 |
实施例8 | M1:10%Ir2(30nm) | 5.7 | 4.8 | 0.70/0.30 | 9000 |
如表1和2可见,本发明的发光体比现有技术的比较材料显示出深红色发光,具有更好的彩色坐标,更低的工作电压,同时寿命提高。
Claims (17)
1.通式(1)的化合物
M(L)n(L‘)m(L“)o
通式(1)
其包含通式(2)的亚结构M(L)n,
其中以下适用于使用的符号和标记:
M是过渡金属;
A相同或者不同的在每一次出现中为NR或O;
D,对于A=NR是与M结合的sp2-杂化的碳原子,对于A=O是具有与M配位的非键电子对的杂原子,
E在每一次出现中相同或者不同,是sp2-杂化的碳或者氮原子;
Cy在每一次出现中相同或不同,是经由sp2-杂化的碳原子或杂原子与M结合的碳环或者杂环,所述杂原子具有任选结合一个或多个基团R的非键电子对;
Y,对于A=NR,相同或者不同的在每一次出现中是CR2,C(=O),C(=NR),C(=N-NR2),C(=CR2),SiR2,O,S,S(=O),S(=O)2,Se,NR,PR,P(=O)R,AsR,As(=O)R或BR,对于A=O等于CR-;
R,R1在每一次出现中相同或者不同,是H,F,Cl,Br,I,CN,B(OH)2,B(OR2)2,NO2,具有1-40个碳原子的直链烷基或烷氧基,或具有1-40个碳原子的支链或环烷基或烷氧基,其中一个或多个非相邻的CH2基团各自可以被-R2C=CR2-,-C≡C-,Si(R2)2,Ge(R2)2,Sn(R2)2,-O-,-S-,-NR2-,-(C=O)-,-(C=NR2)-,-P=O(R2)-或-CONR2-取代,其中一个或多个H原子可以被F、Cl、Br或I取代,或具有5-40个碳原子的芳香或杂芳香环系或芳氧基或杂芳氧基,它们可被一个或多个非芳基R取代;此处R也可以与Cy形成另外的脂族或芳香环系;
R2在每一次出现中相同或者不同,是H或具有1-20个碳原子的脂族或芳烃基团,其中单个H原子也可以被F取代;此处两个或多个基团R2也可以彼此形成环系;
n是1,2或3;
此处通式(1)中配位体L′和L″是单阴离子双齿的螯合配位体;m和o在每一次出现中相同的或不同的是0、1或2;此处对于具有正方形平面配位的金属,n+m+o=2,对于具有八面体配位的金属,n+m+o=3。
2.权利要求1的化合物,其特征在于Cy代表芳香或杂芳族体系。
3.权利要求1或2的通式(1)化合物,其包含通式(2a)的亚结构M(L)n,
其中M、A、Y、R1、R2、L′、L″、n、m和o具有如权利要求1所述的相同的含义,以下说明适用于其他符号:
D,对于A=NR,是与M结合的sp2-杂化碳原子,对于A=O,是经由非键电子对与M配位的氮或磷;
X在每一次出现中是相同或者不同的,是CR1,N或P;或
(X-X)或(X=X)(即,两个相邻的X)代表NR1,S或O;或
(X-X)或(X=X)(即,两个相邻的X)代表CR1,N或P,如果在相应环中符号E代表N;条件是Cy代表5或6元环;
E在每一次出现中是相同或者不同的是C或N,条件是如果符号E代表N,则确切地在Cy中一个单元X-X(即两个相邻的X)等于CR1、N或P。
6.根据权利要求的1-5的一项或多项的化合物,其特征在于配位体L″选自来源于1,3-二酮类的1,3-二酮酸酯,来源于3-酮酯类的3-三酮酸酯,来源于氨基羧酸类的羧化物,来源于水杨基亚胺类的水杨基亚胺化物,和含氮杂环化合物的硼酸酯。
7.权利要求1-6的一项或多项的化合物,其特征在于符号M=Rh,Ir,Pd或者Pt。
8.根据权利要求1-7的一项或多项的化合物,其特征在于符号n=2或3。
9.根据权利要求1-8的一项或多项的化合物,其特征在于对于A=NR,符号Y相同或者不同的是CR2,C(=O),C(=NR),C(=CR2),O,S,NR或BR,对于A=O等于CR-。
10.根据权利要求1-9的一项或多项的化合物,其特征在于符号X=CR1。
11.根据权利要求1-10的一项或多项的化合物,其特征在于它们选自可被R1取代或未取代的结构(1)-(33)。
13.一种包括权利要求1-11的一项或多项的一个或多个化合物的共轭、部分共轭或者非共轭低聚物、聚合物或者树枝状高分子,其中至少一个上述定义的基团R或者R1代表与聚合物或者树枝状聚合物的结合。
14.根据权利要求13的低聚物、聚合物或树枝状高分子,其特征在于另外的重复单元选自芴、螺二芴、二氢菲、茚并芴、菲、对亚苯基、咔唑、酮、硅烷、三芳基胺或噻吩,或还有多个它们的不同单元。
15.权利要求1-11和/或13和14的一项或多项的化合物、低聚物、聚合物或者树枝状高分子在电子元件中作为有源元件、特别是作为发光化合物的用途。
16.电子元件,其包括根据权利要求1-11的一项或多项的一种或多种化合物,和/或权利要求13和14的一项或多项的低聚物、聚合物和/或树枝状高分子。
17.权利要求16的电子元件,其选自有机和聚合发光二极管(OLEDs、PLEDs)、有机场效应晶体管(O-FETs)、有机薄膜晶体管(O-TFTs)、有机集成电路(O-ICs)、有机场猝熄器件(O-FQDs)、有机发光晶体管(O-LETs)、发光电化学电池(LECs)、有机太阳能电池(O-SCs)和有机激光器二极管(O-lasers)。
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105070837A (zh) * | 2015-08-26 | 2015-11-18 | 电子科技大学 | 一种铱类配合物掺杂的三元太阳能电池 |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7851579B2 (en) * | 2006-12-11 | 2010-12-14 | General Electric Company | Carbazolyl polymers for organic electronic devices |
CA2643394C (en) * | 2007-11-07 | 2013-12-31 | Chao-Jun Li | Ligands, their preparation and uses thereof in asymmetric reactions |
US9692077B2 (en) | 2012-07-27 | 2017-06-27 | Lockheed Martin Advanced Energy Storage, Llc | Aqueous redox flow batteries comprising matched ionomer membranes |
US9559374B2 (en) | 2012-07-27 | 2017-01-31 | Lockheed Martin Advanced Energy Storage, Llc | Electrochemical energy storage systems and methods featuring large negative half-cell potentials |
US9768463B2 (en) | 2012-07-27 | 2017-09-19 | Lockheed Martin Advanced Energy Storage, Llc | Aqueous redox flow batteries comprising metal ligand coordination compounds |
US9899694B2 (en) | 2012-07-27 | 2018-02-20 | Lockheed Martin Advanced Energy Storage, Llc | Electrochemical energy storage systems and methods featuring high open circuit potential |
US9382274B2 (en) | 2012-07-27 | 2016-07-05 | Lockheed Martin Advanced Energy Storage, Llc | Aqueous redox flow batteries featuring improved cell design characteristics |
US9865893B2 (en) | 2012-07-27 | 2018-01-09 | Lockheed Martin Advanced Energy Storage, Llc | Electrochemical energy storage systems and methods featuring optimal membrane systems |
US8691413B2 (en) | 2012-07-27 | 2014-04-08 | Sun Catalytix Corporation | Aqueous redox flow batteries featuring improved cell design characteristics |
US8753761B2 (en) | 2012-07-27 | 2014-06-17 | Sun Catalytix Corporation | Aqueous redox flow batteries comprising metal ligand coordination compounds |
US10164284B2 (en) | 2012-07-27 | 2018-12-25 | Lockheed Martin Energy, Llc | Aqueous redox flow batteries featuring improved cell design characteristics |
KR102512254B1 (ko) | 2014-11-26 | 2023-03-20 | 록히드 마틴 에너지, 엘엘씨 | 치환된 카테콜레이트의 금속 착물 및 이를 포함하는 레독스 플로우 배터리 |
US10253051B2 (en) | 2015-03-16 | 2019-04-09 | Lockheed Martin Energy, Llc | Preparation of titanium catecholate complexes in aqueous solution using titanium tetrachloride or titanium oxychloride |
US10644342B2 (en) | 2016-03-03 | 2020-05-05 | Lockheed Martin Energy, Llc | Coordination complexes containing monosulfonated catecholate ligands and methods for producing the same |
US10316047B2 (en) | 2016-03-03 | 2019-06-11 | Lockheed Martin Energy, Llc | Processes for forming coordination complexes containing monosulfonated catecholate ligands |
US9938308B2 (en) | 2016-04-07 | 2018-04-10 | Lockheed Martin Energy, Llc | Coordination compounds having redox non-innocent ligands and flow batteries containing the same |
US10377687B2 (en) | 2016-07-26 | 2019-08-13 | Lockheed Martin Energy, Llc | Processes for forming titanium catechol complexes |
US10343964B2 (en) | 2016-07-26 | 2019-07-09 | Lockheed Martin Energy, Llc | Processes for forming titanium catechol complexes |
US10065977B2 (en) | 2016-10-19 | 2018-09-04 | Lockheed Martin Advanced Energy Storage, Llc | Concerted processes for forming 1,2,4-trihydroxybenzene from hydroquinone |
US10930937B2 (en) | 2016-11-23 | 2021-02-23 | Lockheed Martin Energy, Llc | Flow batteries incorporating active materials containing doubly bridged aromatic groups |
US10497958B2 (en) | 2016-12-14 | 2019-12-03 | Lockheed Martin Energy, Llc | Coordinatively unsaturated titanium catecholate complexes and processes associated therewith |
US10741864B2 (en) | 2016-12-30 | 2020-08-11 | Lockheed Martin Energy, Llc | Aqueous methods for forming titanium catecholate complexes and associated compositions |
US10320023B2 (en) | 2017-02-16 | 2019-06-11 | Lockheed Martin Energy, Llc | Neat methods for forming titanium catecholate complexes and associated compositions |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0842208B2 (en) | 1995-07-28 | 2009-08-19 | Sumitomo Chemical Company, Limited | 2,7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers |
JP4154145B2 (ja) | 2000-12-01 | 2008-09-24 | キヤノン株式会社 | 金属配位化合物、発光素子及び表示装置 |
DE10104426A1 (de) | 2001-02-01 | 2002-08-08 | Covion Organic Semiconductors | Verfahren zur Herstellung von hochreinen, tris-ortho-metallierten Organo-Iridium-Verbindungen |
JP2004111193A (ja) | 2002-09-18 | 2004-04-08 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子及び表示装置 |
DE10249926A1 (de) * | 2002-10-26 | 2004-05-06 | Covion Organic Semiconductors Gmbh | Rhodium- und Iridium-Komplexe |
EP1566385B1 (en) * | 2002-11-26 | 2009-03-11 | Semiconductor Energy Laboratory Co., Ltd. | Phosphorescent compound and electroluminescent element including the same |
AU2003289000A1 (en) * | 2002-12-19 | 2004-07-14 | Semiconductor Energy Laboratory Co., Ltd. | Organometal complex, electroluminescent element containing the organometal complex and luminescent device including the electroluminescent element |
DE10314102A1 (de) | 2003-03-27 | 2004-10-14 | Covion Organic Semiconductors Gmbh | Verfahren zur Herstellung von hochreinen Organo-Iridium-Verbindungen |
GB0311234D0 (en) * | 2003-05-16 | 2003-06-18 | Isis Innovation | Organic phosphorescent material and organic optoelectronic device |
DE10350606A1 (de) | 2003-10-30 | 2005-06-09 | Covion Organic Semiconductors Gmbh | Verfahren zur Herstellung heteroleptischer, ortho-metallierter Organometall-Verbindungen |
US7118812B2 (en) * | 2003-12-05 | 2006-10-10 | Eastman Kodak Company | Organic element for electroluminescent devices |
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US8129554B2 (en) | 2012-03-06 |
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