CN101115762A - 金属络合物 - Google Patents
金属络合物 Download PDFInfo
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- CN101115762A CN101115762A CNA2006800039471A CN200680003947A CN101115762A CN 101115762 A CN101115762 A CN 101115762A CN A2006800039471 A CNA2006800039471 A CN A2006800039471A CN 200680003947 A CN200680003947 A CN 200680003947A CN 101115762 A CN101115762 A CN 101115762A
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- 229910052751 metal Inorganic materials 0.000 title claims abstract description 14
- 239000002184 metal Substances 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 229910052741 iridium Inorganic materials 0.000 claims description 31
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical group [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 31
- -1 salicyl imines Chemical class 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000003446 ligand Substances 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 229910052698 phosphorus Inorganic materials 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000000468 ketone group Chemical group 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 229930194542 Keto Natural products 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004327 boric acid Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 230000021615 conjugation Effects 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 239000003205 fragrance Substances 0.000 claims description 3
- 125000005842 heteroatom Chemical group 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
- 238000004246 ligand exchange chromatography Methods 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 238000010791 quenching Methods 0.000 claims description 3
- 230000000171 quenching effect Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 125000002029 aromatic hydrocarbon 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
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 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
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 229920000548 poly(silane) polymer Polymers 0.000 claims description 2
- 229920001088 polycarbazole Polymers 0.000 claims description 2
- 229920001470 polyketone Polymers 0.000 claims description 2
- 229920000123 polythiophene Polymers 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 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
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 3
- 229910001507 metal halide Inorganic materials 0.000 claims 2
- 150000005309 metal halides Chemical class 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- 239000008204 material by function Substances 0.000 abstract description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 150000002220 fluorenes Chemical class 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- 125000003963 dichloro group Chemical group Cl* 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 239000003960 organic solvent 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
- 239000000758 substrate Substances 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 238000005304 joining Methods 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 230000003245 working effect Effects 0.000 description 3
- 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
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- 150000004868 1,2,5-thiadiazoles Chemical class 0.000 description 1
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- 150000000182 1,3,5-triazines Chemical class 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 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
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- SZXUTTGMFUSMCE-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)pyridine Chemical class C1=CNC(C=2N=CC=CC=2)=N1 SZXUTTGMFUSMCE-UHFFFAOYSA-N 0.000 description 1
- PRQUBDQDCAULSW-UHFFFAOYSA-N 2-(2h-triazol-4-yl)pyridine Chemical group N1N=NC(C=2N=CC=CC=2)=C1 PRQUBDQDCAULSW-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- 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
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-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
- OXIKKRXUVAYLKR-UHFFFAOYSA-N C1(C=CC=C2C3=CC=CC=C3C=C12)=O.N1C=CC=CC=C1 Chemical compound C1(C=CC=C2C3=CC=CC=C3C=C12)=O.N1C=CC=CC=C1 OXIKKRXUVAYLKR-UHFFFAOYSA-N 0.000 description 1
- GBXSXMQPRACWIK-UHFFFAOYSA-N C12(C=CC=C3C4=CC=CC=C4C=C13)C=CC=C1C3=CC=CC=C3C=C12.N1C=CC=CC=C1 Chemical class C12(C=CC=C3C4=CC=CC=C4C=C13)C=CC=C1C3=CC=CC=C3C=C12.N1C=CC=CC=C1 GBXSXMQPRACWIK-UHFFFAOYSA-N 0.000 description 1
- ATFWTIRXJLAFPI-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3CC12.N1C=CC=CC=C1 Chemical class C1=CC=CC=2C3=CC=CC=C3CC12.N1C=CC=CC=C1 ATFWTIRXJLAFPI-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
- 239000004471 Glycine Substances 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 241000254158 Lampyridae Species 0.000 description 1
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- Glass Compositions (AREA)
Abstract
本发明描述了能在最广义上归于电子工业应用的大量不同场合中用作功能材料的新型金属络合物。本发明的化合物通过通式(1)和(1a)描述。
Description
本发明描述了新型的材料,其在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的化合物,在不久的将来能在在最广义上归于电子工业的大量不同的应用中用作功能材料,例如有机电致发光器件。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。在该领域中已有(产品)引入市场,如由具有“有机显示器”的Pioneer汽车收音机和Pioneer和SNMD的移动电话所证实。该类型的其他产品不久将引入(市场)。
最近几年中进行的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等人,Appl.Phys.Lett.1999,75,4-6)。 出于量子力学的理由,使用有机金属化合物作为磷光发光体可以实现最高达4倍的能量和功率效率的增加。 该开发的成功与否取决于能否发现对应的也能在OLED中实现这些优点(和单线态发光=荧光相比,三重态发光=磷光)的器件组合物。在这里可以提到的基本条件特别是该络合物长的使用寿命和高的热稳定性。
然而,在显示三重态发光的OLED中仍有相当多的迫切需要改进的问题。 这同样特别适用于三线态发光体本身。文献中已知的大部分络合物包括基于苯基吡啶的配位体或者相关的与铱或者铂配位的结构(例如WO 02/068435,WO 04/026886)。该结构的特征在于在两个环之间没有桥键(通式A)或者含有2-20个碳原子的亚烷基桥键,其任选可以被杂原子取代(WO 03/000661,通式B)。
通式A 通式B
在实践中,要求改进具有一些关键缺点的该类型化合物:
一个关键缺陷是上述化合物的热稳定性不够。尽管在有机电致发光器件生产期间,例如同配络合物面式-三(2-苯基吡啶基-C2,N)铱(III)(通常称为Ir(PPy)3)能够蒸汽沉积而不分解,然而该蒸汽沉积过程仅能在低的蒸汽沉积速率下进行,然而在纯化该材料的升华作用期间,需要明显更高的升华速率并从而同样需要明显较高的温度。 在升华作用期间该材料的热稳定性仍是不够的,其导致材料部分分解,以及相关的由于被分解的组分引起的络合物污染。
使用寿命通常仍太短,这迄今为止影响将磷光OLED引入具有长寿命的高质量器件中。
由于叠层,平面四方型的络合物特别倾向于形成激态复合物,它们以不希望的方式要么熄灭发光要么使发光颜色改变。
该络合物通常在有机溶剂中仅具有低的溶解度,这使得通过重结晶或者色谱分离法高效纯化变得更加困难或被阻止。 按照显示器制造的需要,这特别适用于相对大量的纯化。 特别是能用于例如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。
特别是,同时改进络合物寿命和热稳定性是有利的。 因此,需要没有上述提到缺点的化合物,但效率和发光颜色至少等于已知的金属络合物。
现在意想不到地发现,作为OLED三线态发光体,某些新型的具有桥键、准确地说是在两个环之间具有一个桥原子的化合物具有优异的性能。
已经提到具有铑的含该类型配位体的络合物(JP 2004/311405,JP2004/319438),其中各个申请同样描述了许多其他不具有这种桥键或者具有其他较大的桥键的铑络合物。 没有描述在两个环之间准确地具有一个桥原子的络合物相对于其他络合物具体的优点。 与许多其它的实施方式一起,这种结构仅作为一种可能的实施方式提出,与铑(配位)没有表现出特别的优点。
本发明涉及通式(1)的化合物:
M(L)n(L‘)m(L“)o
通式(1)
包括通式(2)的亚结构M(L)n,
通式(2)
其中以下适用于使用的符号和标记:
M在每一次出现中是铱,铂,钯,金,钨,铼,钌或者锇;
D在每一次出现中是相同或者不同的,是具有与M配位的非键电子对的sp2-杂化的杂原子;
C在每一次出现中是与M键合的sp2-杂化的碳原子;
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;
Y在每一次出现中是相同或者不同的,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;
Cy1在每一次出现中是相同或者不同的,任选为R1-取代的经由sp2-杂化的碳原子与M键合的碳环或者杂环;
Cy2在每一次出现中是相同或者不同的,任选为R1-取代的经由原子D与M配位的杂环;
R 在每一次出现中是相同或者不同的,为H,F,CN,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,其中在每一情况下,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或者具有1-30个碳原子的芳族或者杂芳族体系或者芳氧基或者杂芳氧基取代,其各自可被一个或多个基团R1取代;在本发明中两个基团R也可以彼此形成其他脂族或者芳香环系;
R1在每一次出现中是相同或者不同的,为H,F,Cl,Br,I,OH,NO2,CN,N(R2)2,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,其中在每一情况下,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)-,-COOR2-或-CONR2-取代,其中一个或多个H原子可以被F或者具有1-30个碳原子的芳族或者杂芳族体系或者芳氧基或者杂芳氧基取代,其可被一个或多个非芳基R1取代,其中在相同环以及在不同环上多个取代基R1随后一起可以形成其他的单或者多环的脂族或者芳香环系;
R2在每一次出现中是相同或者不同的,是H或者具有1-20个碳原子的脂族或者芳烃基团;
n是1,2或3;
在本发明通式(1)中的配位体L′和L″是单阴离子双齿螯合配位体;m和o在每一次出现中相同或者不同的是0,1或者2。
在本发明中对于具有平面四方型配位的金属,例如铂和钯,n+m+o=2,对于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,其彼此形成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原子或者CH2基团也可以被上述提到的基团取代的C1-到C40-烷基特别优选是指如下基团: 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,己炔基或者辛炔基。 C1-到C40-烷氧基特别优选是指甲氧基,乙氧基,正丙氧基,异丙氧基,正丁氧基,异丁氧基,仲丁氧基,叔丁氧基或者2-甲基丁氧基。 在每一情况下也可以被上述提到的基团R1取代、以及可以经由任何希望位置与芳族或者杂芳族环连接的、具有1-30个碳原子的芳族或者杂芳族体系特别是指来源于如下的基团:苯,萘,蒽,菲,嵌二萘,屈,茈,萤蒽,丁省,戊省,苯并芘,联苯,亚联苯基,三联苯,亚三联苯,芴,螺二芴,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,吩嗪,1.5-二氮杂萘,氮咔唑,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,中氮茚和苯并噻二唑。
Cy1和Cy2优选是芳族或者杂芳族体系。在本发明中Cy1和Cy2也可以包括多个彼此稠合的环。
优选通式(1)的化合物包括通式(2a)的亚结构M(L)n,
通式(2a)
其中M,Y,R,R1,R2,L’,L”和n具有与上述相同的含义,及以下说明适用于其他符号:
D在每一次出现中相同或者不同的是氮或者磷;
X在每一次出现中相同或者不同的是CR1,N或P;或(X-X)或(X=X)(即两个相邻的X)代表NR1,S或O;或如果相应环中的符号E代表N,则(X-X)或(X=X)(即两个相邻的X)代表CR1,N或P;
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,则确切地在相应环中的一个单元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)
包括至少一个通式(2b)的亚结构M(L)n,
通式(2b)
和任选包括通式(3)的亚结构M(L′)M,
通式(3)
其中M,D,R,R1,R2,L”,n,m和o具有与上述相同的含义,而且:
X在每一次出现中相同或者不同的是CR1,N或P;或(X-X)或(X=X)(即两个相邻的X)代表NR1,S或O;
A在每一次出现中是相同或者不同的是:-CR1=CR1-,-N=CR1-,-P=CR1-,-N=N-,-P=N-,NR1,O或S;
条件是两个环各自是五或者六元环。
本发明的单阴离子二齿配位体L″是衍生自1,3-二酮类的1,3-二酮酸酯(ketonate),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, 衍生自3-酮酯类的3-三酮酸酯,比如乙酰醋酸乙酯,衍生自氨基羧酸类的羧化物,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-一甲基丙氨酸,衍生自水杨基亚胺类的水杨基亚胺化物,比如甲基水杨基亚胺,乙基水杨基亚胺,苯基水杨基亚胺, 或经由中性氮原子和阴离子氮配位体例如吡啶基吡唑、吡啶基咪唑、或吡啶基三唑结合的含氮杂环硼酸酯配位体,例如四(1-咪唑啉基)硼酸酯和四(1-吡唑基)硼酸酯。
优选通式(1)和通式(1a)的化合物,其中符号n=2或3,其中对于平面四方型的络合物n=3是不可能的。特别优选其中符号o=0的化合物。尤其特别优选其中符号m=o=0的化合物。特别优选的是,对于平面四方型的络合物n=2和m=o=0,对于八面体的络合物n=3和m=o=0。尤其特别优选同配型的络合物,即其中m=o=0的络合物,其中所有存在的配位体是相同的,并还能被相同地取代。优选同配型络合物是由于容易合成的易得性。
优选通式(1)和通式(1a)的化合物,其中符号Y代表CR2,C(=O),C(=CR2),O,S,NR,PR,P(=O)R或BR。特别优选通式(1)和通式(1a)的化合物,其中符号Y代表CR2,O,S,NR或P(=O)R。
在本发明一个特别优选实施方案中,能产生通式(2)或通式(2a)或通式(2b)结构的配位体是螺环化合物,其中符号Y代表螺原子,特别是氮杂螺二芴的衍生物,即其中符号Y代表CR2的结构,其中两个基团R代表取代或未取代的苯基,其能彼此形成其他的环系。
进一步优选其中符号D=N的通式(1)和通式(1a)的化合物。
进一步优选其中符号X=CR1或N,特别是X=CR1的通式(1)和通式(1a)的化合物。
进一步优选如下通式(1)和通式(1a)的化合物,其中对于能够经气相沉积处理的体系以下适用于符号R1:
R1在每一次出现中相同或者不同的是H,F,CN,甲基,叔丁基,苯基,CF3或具有1-4个碳原子的稠合环烷氧基。
对于从溶液中进行处理、因此在有机溶剂中必须具有良好溶解度的通式(1)和通式(1a)的化合物,取代基R和/或R1的至少一个包含具有至少4个碳原子的烷基和/或烷氧基链。
特别是对于平面四方型的络合物,即例如含有铂或钯的络合物,优选Y代表CR2且基团R是大体积的例如代表螺环系,因为该络合物是空间掩蔽的因此防止形成激态复合物(exciplexe)。
通式(1)和通式(1a)的八面体化合物可以是面式和经式的。 本发明涉及纯面式以及纯经式的络合物,并涉及既包括面式又包括经式的混合物。
能够通过有机合成领域普通技术人员熟知的标准有机化工工艺制备产生通式(2)或通式(2a)或(2b)亚结构的相应的配位体,以及配位体L′和L″。对于氮杂芴衍生物和相应的氮杂螺二芴衍生物,氮杂咔唑等配位体合成的适当反应与文献中的反应类似(例如A.-S.Rebstock等人,Tetrahedron 2003,59,4973-4977中的4-氮杂-9-芴酮的合成;T.Iwaki等人,J.Chem.Soc.,Perkin 1 1999,1505-1510关于4-氮咔唑的合成;A.Degl’Innocenti等人,J.Chem.Soc.,Perkin 1 1996,2561-2563关于4-氮杂二苯并噻吩的合成;W.S.Yue等人,Org.Lett.2002,4,2201-2203关于4-氮杂二苯并呋喃的合成)。 以与从芴酮合成螺二芴类似的方式,能够从氮杂芴酮合成氮杂螺二芴。
本发明进一步涉及能在络合物中产生通式(2)或通式(2a)或通式(2b)的亚结构的配位体在制备本发明通式(1)或通式(1a)化合物中的用途。
原则上,本发明的金属络合物能通过各种工艺制备;然而已经证明如下所述的工艺是特别适当的。
因此,本发明进一步涉及通过使相应的自由配位体与通式(4)的金属醇盐与通式(5)的金属酮酮化物,或与通式(6)、(7)或(8)的单或者多核金属卤化物的反应,制备通式(1)和通式(1a)金属络合物化合物的方法:
通式(4) 通式(5) 通式(6)
通式(7) 通式(8)
其中符号M,n和R2具有上述的含义,对于二价金属p=1,对于三价金属p=2,和Hal=F,Cl,Br或I。
同样可以使用载带醇盐和/或卤化物和/或羟基以及酮酮化物基团的金属化合物,特别是铱化合物。 这些化合物也可以是带电的。 特别适当作为原料的相应的铱化合物公开在WO 04/085449中。
优选如WO 02/060910和WO 04/085449中的描述进行络合物的合成。例如,按照WO 05/042548中描述的也能够合成混配络合物。
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。
在本发明中说明的合成方法能够制备特别是下面示出的结构(1)-(159)的通式(1)的化合物。
上面描述的本发明的化合物,例如实施例9,16,65,84和91的化合物,也可以用作制备相应共轭、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。 在本发明中优选经由溴官能度进行聚合。因此,它们特别可以是共聚为聚芴(例如见EP 842208或WO 00/22026),聚螺二芴(例如见EP 707020或EP 894107),聚二氢菲(例如见WO 05/014689),聚茚并芴(例如见WO 04/041901和WO 04/113468),聚菲(例如见WO 05/104264),对聚苯(例如见WO 92/18552),聚咔唑(例如见WO 04/070772或WO 04/113468),聚酮(例如见WO 05/040302),聚硅烷(例如见DE 102004023278)或聚噻吩(例如见EP 1028136),或也可以包含这些各种单元的共聚物存在。 在本发明中它们能够或者被引入聚合物的侧链或主链,或也可以代表所述聚合物链的支化点(例如见DE 102004032527.8)。
因此本发明进一步涉及包括一种或多种通式(1)或通式(1a)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,其中上述定义的基团R和R1的至少一个,优选R1,代表与聚合物或树枝状聚合物结合的键。对于通式(1)或通式(1a)的单元,如上面所述的优选同样适用于聚合物和树枝状高分子。除了上述提到的单元,低聚物,聚合物或树枝状聚合物可以包括例如选自具有空穴传输特性或电子传递特性的重复单元的其他单元。现有技术已知的材料适于这种目的。
上述提到的低聚物,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,特别是那些被卤素官能化的化合物,还可以进一步由常见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。本发明中可以提到的例子有: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、树枝状聚合物或延伸化合物能在有机电子元件,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)、有机太阳能电池(O-SCs)、有机发光晶体管(O-LETs)、有机场猝熄器件(O-FQDs)、发光电化学电池(LECs)或有机激光二极管(O-lasers)中用作有源元件。
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、聚合物和树枝状聚合物、和通式(1)相应的延伸化合物在有机电子元件中用作有源元件、特别是作为发光化合物的应用。
本发明进一步涉及选自有机和聚合发光二极管(OLED,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)、有机太阳能电池(O-SCs)、有机发光晶体管(O-LETs)、有机场猝熄器件(O-FQDs)、发光电化学电池(LECs)和有机激光二极管(O-lasers)的电子元件,特别是有机和聚合发光二极管,所述电子元件包括特别是作为发光化合物的本发明通式(1)的一种或多种化合物、本发明的一种或多种低聚物、聚合物和树枝状聚合物和一种或多种通式(1)相应的延伸化合物。
特别是在本发明低分子量化合物的情况下,这些通常与基质材料一起用于发光层中。 在本发明中所述基质材料或者是低分子量的,或者是低聚的或是聚合的。
优选的基质材料是基于咔唑的那些,例如CBP(双(咔唑基)联苯),以及包括咔唑或咔唑衍生物的其他材料,如WO 00/057676,EP 1202358和WO 02/074015所述。 进一步优选酮和亚胺,例如描述在WO04/093207中,特别是基于螺二芴的那些,和氧化膦,硒化磷,磷腈,亚砜和砜,如WO 05/003253所述,特别是基于螺二芴的那些。进一步优选硅烷,多配体(polypodal)金属络合物,如WO 04/081017所述,和基于螺二芴的寡聚苯烯,如EP 676461和WO 99/40051所述。特别优选的基质材料是酮,氧化膦,亚砜和砜。尤其特别优选酮和氧化膦。
本发明的化合物相对于现有技术的化合物具有以下优点:
本发明化合物的特征在于较高的温度稳定性。因此,所述低分子量的化合物不仅能在有机电子器件生产期间在高真空中蒸发而不分解,它们也可以在高温下在更大的化合物纯化速率下升华而不分解。因此可以资源节约性地利用这些稀有金属的化合物。
由于所述络合物的空间掩蔽,防止了三重态-三重态的湮灭,者产生更高的效率。
本发明络合物在OLED中的使用寿命比现有技术络合物的寿命更长。
本发明化合物的特征在于在有机溶剂中良好的溶解度,这能大幅简化通过常见方法比如重结晶或色谱分离法对它们进行的纯化。因此,该化合物还能够从溶液中通过涂覆或印刷技术被加工。在通过蒸发的常规处理期间,这种特性同样是有利的,因为由此大幅简化了使用的设备或障板的清洗。
通过以下实施例更详细地说明本发明,但不希望将本发明限制于此。 改进本发明的描述,本领域普通技术人员不需要创造性劳动即能制备本发明的其他化合物,或使用本发明的方法。
实施例:
如文献中所述的合成4-氮杂芴酮(A.-S.Rebstock等人,Tetrahedron 2003,59,4973,M.T.DuPriest等人,J.Org.Chem.1986,51,2021),4-氮杂芴(M.T.DuPriest等人,J.Org.Chem.1986,51,2021),苯并呋喃[3,2-b]吡啶(J.Org.Chem.1983,48(5),690)和[1]苯并噻吩[3,2-b]吡啶(J.Chem.Soc.,Perkin.Trans.,1996,21,2561)。 按照未公开的申请EP 04019737.1中所述合成(双(乙酰丙酮合)二氯)铱合钠(III)。
实施例1:面式-三(4-氮杂芴-κN,κC)铱(III)
在180℃下加热在5ml乙二醇中的484mg(1.0mmol)的(双(乙酰丙酮合)二氯)铱合钠(III)和1.00g(6.0mmol)的4-氮杂芴的悬浮物150小时。冷却到60℃之后,加入25ml的1N盐酸水溶液和25ml乙醇的混合物。用抽吸过滤去沉淀固体,用10ml水洗涤三次,并用10ml乙醇洗涤三次,随后在真空中干燥。 产率:243mg(0.4mmol),理论值的35.2%;纯度:根据核磁共振为99.5%。
实施例2:面式-三(9,9′-二甲基-4-氮杂芴-κN,κC)铱(III)
a) 9,9′-二甲基-4-氮杂芴
将16.7g(100mmol)的4-氮杂芴和38.4g(400mmol)的叔丁醇钠悬浮在300ml的DMF中。该悬浮物在60℃下搅拌30分钟,然后逐滴地加入12.8ml(205mmol)的甲基碘。在60℃下搅拌混合物6h之后,加入500ml的水,过滤去沉淀固体,用100ml水洗涤三次,并用50ml乙醇洗涤三次,干燥并随后从DMF(1.5ml/g)中再结晶一次。产率:14.3g(73mmol),理论值的73.2%;纯度:根据核磁共振为99%。
b)面式-三(9,9′-二甲基-4-氮杂芴))-κN,κC)铱(III)
步骤类似于实施例1。批量:484mg(1.0mmol)的(双(乙酰丙酮合)二氯)铱合钠(III),1.17g(6.0mmol)的9,9′-二甲基-4-氮杂芴。产率:322mg(0.4mmol),理论值的41.5%;纯度:根据核磁共振为99.5%。
实施例3:面式-三(螺(二芴-9,9′-(4-氮杂芴))-κN,κC)铱(III)
a)螺二芴-9,9′-(4-氮杂芴)
从在100ml THF和50ml 1,2-二甲氧基乙烷的混合物中的19.0ml(110mmol)的2-溴二苯基和2.7g(112mmol)的镁制备相应的格利雅试剂。向该溶液中逐滴地加入在THF中的18.1g(100mmol)4-氮杂芴酮的悬浮物。在50℃下搅拌得到的混合物3h,然后在室温下搅拌15小时。用抽吸过滤去沉淀固体,用少许二乙醚洗涤,并引入300ml乙酸和15ml浓硫酸的混合物中。混合物回流5h,蒸馏去乙酸,将200ml水加入到残余物中。在添加500ml二氯甲烷之后,使用饱和的碳酸钾溶液使水相变成碱性(pH>10),分离去二氯甲烷相,用200ml二氯甲烷再次提取所述水相。用硫酸镁干燥合并的有机相并蒸发。使用二氯甲烷/甲醇/乙酸(1500∶100∶1)并利用硅胶进行色谱分离得到油性残余物。产率:13.0g(41mmol),理论值的41.1%;纯度:根据核磁共振为99%。
b) 面式-三(螺(二芴-9,9′-(4-氮杂芴))-κN,κC)铱(III)
步骤类似于实施例1。批量:484mg(1.0mmol)的(双(乙酰丙酮合)二氯)铱合钠(III),1.90g(6.0mmol)的螺二芴-9,9′-(4-氮杂芴)。产率:335mg(0.3mmol),理论值的29.4%;纯度:根据核磁共振为99.5%。
实施例4:面式-三(苯并呋喃[3,2-b]吡啶基-κN,κC)铱(III)
步骤类似于实施例1。批量:484mg(1.0mmol)的(双(乙酰丙酮合)二氯)铱合钠(III),1.02g(6.0mmol)的苯并呋喃[3,2-b]吡啶。产率:403mg(0.6mmol),理论值的57.8%;纯度:根据核磁共振为99.5%。
实施例5:面式-三([1]苯并噻吩[3,2-b]吡啶基-κN,κC)铱(III)
步骤类似于实施例1。批量:484mg(1.0mmol)的(双(乙酰丙酮合)二氯)铱合钠(III),1.11g(6.0mmol)的[1]苯并噻吩[3,2-b]吡啶。产率:458mg(0.6mmol),理论值的61.5%;纯度:根据核磁共振为99.5%。
Claims (19)
1.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
通式(2)
其中以下适用于使用的符号和标记:
M每次出现是铱、铂、钯、金、钨、铼、钌或者锇;
D 每次出现相同或者不同的是具有与M配位的非键电子对的sp2-杂化杂原子;
C 每次出现是与M键合的sp2-杂化碳原子;
E 每次出现相同或者不同的是sp2-杂化的碳或者氮原子;
Y 每次出现相同或者不同的是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;
Cy1每次出现相同或者不同的是任选R1-取代的通过sp2-杂化碳原子键合到M的碳环或者杂环;
Cy2每次出现相同或者不同的是任选R1-取代的通过原子D与M配位的杂环;
R 每次出现相同或者不同的是H,F,CN,具有1-40个碳原子的直链烷基或烷氧基,或者具有3-40个C原子的支链或者环烷基或者烷氧基,其中在每一情况下一个或多个非相邻的CH2基团可被-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取代,或者具有1-30个碳原子的芳香或者杂芳族体系或者芳氧基或者杂芳氧基,其各自可被一个或多个基团R1取代;此处两个基团R也可以彼此形成另外的脂族或者芳香环系;
R1 每次出现相同或者不同的是H,F,Cl,Br,I,OH,NO2,CN,N(R2)2,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C原子的支链或者环烷基或者烷氧基,其中在每一情况下一个或多个非相邻的CH2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)-、-COOR2-或-CONR2-取代,其中一个或多个H原子可以被F取代,或者具有1-30个C原子的芳香族或者杂芳族体系或者芳氧基或者杂芳氧基,它们可被一个或多个非芳基R1取代,其中在相同的环上以及在不同环上的多个取代基R1可以随后一起形成另外的单或者多环的、脂族或者芳香环体系;
R2每次出现相同或者不同的是H或者具有1-20个碳原子的脂族或者芳烃基团;
n 是1,2或3;
此处通式(1)中的配位体L′和L″是单阴离子双齿螯合配位体;m和o在每一次出现中相同或者不同地为0,1或者2。
2.权利要求1的化合物,其特征在于Cy1和Cy2代表芳香或者杂芳族体系。
5.根据权利要求1-4的一项或多项的化合物,其特征在于单阴离子二齿配位体L″选自衍生自1,3-二酮类的1,3-二酮酸酯,衍生自3-酮酯类的3-三酮,衍生自氨基羧酸类的羧化物,衍生自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。
6.根据权利要求1-5的一项或多项的化合物,其特征在于符号n=2或3。
7.根据权利要求6的化合物,其特征在于符号m=o=0。
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Y代表CR2,C(=O),C(=CR2),O,S,NR,PR,P(=O)R或BR。
9.根据权利要求8的化合物,其特征在于产生通式(2)或通式(2a)或通式(2b)结构的配位体是螺环化合物,其中符号Y代表CR2以及代表螺原子,特别是氮杂螺二芴的衍生物。
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D=N。
11.根据权利要求1-10的一项或多项的化合物,其特征在于符号X=CR1。
12.在络合物中产生权利要求1通式(2)或权利要求3通式(2a)或权利要求4通式(2b)的亚结构的配位体,在制备权利要求1通式(1)或权利要求4通式(1a)的化合物中的用途。
14.根据权利要求13的方法,其特征在于使用载带醇盐和/或卤化物和/或羟基以及酮酮化物基团的金属化合物,而且这些化合物也可以是带电的。
15.包括权利要求1-11的一项或多项的一种或多种化合物的共轭、部分共轭或非共轭低聚物,聚合物或树枝状聚合物,其中上述定义的基团R和R1的至少一个,优选R1,代表与聚合物或树枝状聚合物结合的键。
16.根据权利要求15的聚合物,其特征在于它们选自聚芴、聚螺二芴、聚二氢菲、聚茚并芴、聚菲、对聚苯、聚咔唑、聚酮、聚硅烷、或聚噻吩,或同样为包括各种这些单元的共聚物。
17.根据权利要求1-11和/或15-16的一项或多项的化合物、低聚物、聚合物和/或树枝状聚合物在有机电子元件中的用途。
18.包括根据权利要求1-11和/或15-16的一项或多项的一种或多种化合物、低聚物、聚合物和/或树枝状聚合物的有机电子元件。
19.权利要求18的有机电子元件,选自有机和聚合发光二极管(OLED,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),有机太阳能电池(O-SCs),有机发光晶体管(O-LETs),有机场猝熄器件(O-FQDs),发光电化学电池(LECs)和有机激光二极管(O-lasers)。
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- 2006-01-26 AT AT06706411T patent/ATE488522T1/de not_active IP Right Cessation
- 2006-01-26 US US11/814,707 patent/US20080161567A1/en not_active Abandoned
- 2006-01-26 JP JP2007553505A patent/JP2008528646A/ja not_active Withdrawn
- 2006-01-26 DE DE502006008326T patent/DE502006008326D1/de active Active
- 2006-01-26 KR KR1020077017898A patent/KR20070100965A/ko not_active Application Discontinuation
- 2006-01-26 EP EP06706411A patent/EP1844060B1/de not_active Not-in-force
- 2006-01-26 WO PCT/EP2006/000651 patent/WO2006081973A1/de active Application Filing
- 2006-01-26 CN CNA2006800039471A patent/CN101115762A/zh active Pending
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CN109641925A (zh) * | 2016-06-24 | 2019-04-16 | 国立研究开发法人产业技术综合研究所 | 环金属化铱配合物的制造方法、以及适用于该方法的新型铱化合物 |
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CN109790193A (zh) * | 2016-12-13 | 2019-05-21 | 广州华睿光电材料有限公司 | 过渡金属配合物及其应用、混合物、有机电子器件 |
CN109790193B (zh) * | 2016-12-13 | 2022-03-22 | 广州华睿光电材料有限公司 | 过渡金属配合物及其应用、混合物、有机电子器件 |
CN110903323A (zh) * | 2018-09-17 | 2020-03-24 | 上海和辉光电有限公司 | 一种有机电致磷光材料、其制备方法、用途及包含其的oled器件 |
CN114773397A (zh) * | 2022-04-29 | 2022-07-22 | 北京八亿时空液晶科技股份有限公司 | 金属配合物、包含其的有机电致发光元件及消费型产品 |
Also Published As
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WO2006081973A1 (de) | 2006-08-10 |
KR20070100965A (ko) | 2007-10-15 |
EP1844060A1 (de) | 2007-10-17 |
JP2008528646A (ja) | 2008-07-31 |
DE502006008326D1 (de) | 2010-12-30 |
ATE488522T1 (de) | 2010-12-15 |
US20080161567A1 (en) | 2008-07-03 |
EP1844060B1 (de) | 2010-11-17 |
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