WO2006046980A1 - Organic light emitting materials and devices - Google Patents
Organic light emitting materials and devices Download PDFInfo
- Publication number
- WO2006046980A1 WO2006046980A1 PCT/US2005/023254 US2005023254W WO2006046980A1 WO 2006046980 A1 WO2006046980 A1 WO 2006046980A1 US 2005023254 W US2005023254 W US 2005023254W WO 2006046980 A1 WO2006046980 A1 WO 2006046980A1
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- Prior art keywords
- compound
- group
- ring
- methyl
- phenyl
- Prior art date
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- 239000000463 material Substances 0.000 title description 92
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 239000003446 ligand Substances 0.000 claims abstract description 51
- 229910052751 metal Inorganic materials 0.000 claims abstract description 46
- 229910052741 iridium Inorganic materials 0.000 claims description 45
- 239000002184 metal Substances 0.000 claims description 43
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- -1 keto, amino Chemical group 0.000 claims description 21
- 125000004122 cyclic group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 12
- 229910052697 platinum Inorganic materials 0.000 claims description 12
- 229910052797 bismuth Inorganic materials 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 229910052738 indium Inorganic materials 0.000 claims description 11
- 229910052745 lead Inorganic materials 0.000 claims description 11
- 229910052702 rhenium Inorganic materials 0.000 claims description 11
- 229910052703 rhodium Inorganic materials 0.000 claims description 11
- 229910052709 silver Inorganic materials 0.000 claims description 11
- 229910052718 tin Inorganic materials 0.000 claims description 11
- 125000006565 (C4-C7) cyclic group Chemical group 0.000 claims description 10
- 229910052787 antimony Inorganic materials 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 229910052762 osmium Inorganic materials 0.000 claims 10
- 229910052707 ruthenium Inorganic materials 0.000 claims 10
- 229910052716 thallium Inorganic materials 0.000 claims 9
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- 239000012044 organic layer Substances 0.000 abstract description 20
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- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 36
- 238000002347 injection Methods 0.000 description 31
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- 239000002019 doping agent Substances 0.000 description 25
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- 230000000052 comparative effect Effects 0.000 description 18
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 17
- 230000000903 blocking effect Effects 0.000 description 15
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- 238000001194 electroluminescence spectrum Methods 0.000 description 13
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 12
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 10
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 10
- 239000011368 organic material Substances 0.000 description 10
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
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- 230000015572 biosynthetic process Effects 0.000 description 8
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
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- OQJQPIWVCBJVAZ-UHFFFAOYSA-N 1-methyl-2-phenylimidazole Chemical compound CN1C=CN=C1C1=CC=CC=C1 OQJQPIWVCBJVAZ-UHFFFAOYSA-N 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
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- 230000007246 mechanism Effects 0.000 description 7
- 125000002524 organometallic group Chemical group 0.000 description 7
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- YXVFYQXJAXKLAK-UHFFFAOYSA-M 4-phenylphenolate Chemical compound C1=CC([O-])=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-M 0.000 description 6
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000000412 dendrimer Substances 0.000 description 6
- 229920000736 dendritic polymer Polymers 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 6
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 5
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
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- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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- 125000004429 atom Chemical group 0.000 description 4
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical group C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 3
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 3
- SCZWJXTUYYSKGF-UHFFFAOYSA-N 5,12-dimethylquinolino[2,3-b]acridine-7,14-dione Chemical compound CN1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3N(C)C1=C2 SCZWJXTUYYSKGF-UHFFFAOYSA-N 0.000 description 3
- XHLKOHSAWQPOFO-UHFFFAOYSA-N 5-phenyl-1h-imidazole Chemical compound N1C=NC=C1C1=CC=CC=C1 XHLKOHSAWQPOFO-UHFFFAOYSA-N 0.000 description 3
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- 238000004821 distillation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
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- 150000002602 lanthanoids Chemical class 0.000 description 3
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
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- 238000002207 thermal evaporation Methods 0.000 description 3
- 238000004832 voltammetry Methods 0.000 description 3
- KTGYDKACJATEDM-UHFFFAOYSA-N 1-methyl-4-phenylimidazole Chemical compound CN1C=NC(C=2C=CC=CC=2)=C1 KTGYDKACJATEDM-UHFFFAOYSA-N 0.000 description 2
- SSABEFIRGJISFH-UHFFFAOYSA-N 2-(2,4-difluorophenyl)pyridine Chemical compound FC1=CC(F)=CC=C1C1=CC=CC=N1 SSABEFIRGJISFH-UHFFFAOYSA-N 0.000 description 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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- 229920000144 PEDOT:PSS Polymers 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
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- 238000006243 chemical reaction Methods 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
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- 238000010586 diagram Methods 0.000 description 2
- 125000004212 difluorophenyl group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- 230000001815 facial effect Effects 0.000 description 2
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- 150000002460 imidazoles Chemical class 0.000 description 2
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- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 238000001296 phosphorescence spectrum Methods 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
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- 238000006467 substitution reaction Methods 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- 150000003536 tetrazoles Chemical class 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000002061 vacuum sublimation Methods 0.000 description 2
- QQLRSCZSKQTFGY-UHFFFAOYSA-N (2,4-difluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(F)C=C1F QQLRSCZSKQTFGY-UHFFFAOYSA-N 0.000 description 1
- JNZXFLAEEPPCSN-UHFFFAOYSA-N 1,2-diphenylimidazole Chemical compound N=1C=CN(C=2C=CC=CC=2)C=1C1=CC=CC=C1 JNZXFLAEEPPCSN-UHFFFAOYSA-N 0.000 description 1
- GWGODZWLKFUEOY-UHFFFAOYSA-N 1,4,5-trimethyl-2-phenylimidazole Chemical compound CN1C(C)=C(C)N=C1C1=CC=CC=C1 GWGODZWLKFUEOY-UHFFFAOYSA-N 0.000 description 1
- SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 description 1
- RSWOJEDGRFCGFR-UHFFFAOYSA-N 2,3,6,7,10,11-hexakis-phenyltriphenylene Chemical group C1=CC=CC=C1C1=CC(C2=CC(=C(C=3C=CC=CC=3)C=C2C2=CC(=C(C=3C=CC=CC=3)C=C22)C=3C=CC=CC=3)C=3C=CC=CC=3)=C2C=C1C1=CC=CC=C1 RSWOJEDGRFCGFR-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229940076286 cupric acetate Drugs 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- FSEUPUDHEBLWJY-UHFFFAOYSA-N diacetylmonoxime Chemical compound CC(=O)C(C)=NO FSEUPUDHEBLWJY-UHFFFAOYSA-N 0.000 description 1
- JAONJTDQXUSBGG-UHFFFAOYSA-N dialuminum;dizinc;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Al+3].[Al+3].[Zn+2].[Zn+2] JAONJTDQXUSBGG-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
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- 239000003822 epoxy resin Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- BSUMMDQYOKWWFG-UHFFFAOYSA-N iridium(3+) 2-phenylquinoline Chemical compound [Ir+3].C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1.C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 BSUMMDQYOKWWFG-UHFFFAOYSA-N 0.000 description 1
- URMNGDORJKJIIK-UHFFFAOYSA-N iridium(3+) 3-methyl-2-phenylquinoline Chemical compound [Ir+3].CC1=CC2=CC=CC=C2N=C1C1=CC=CC=C1.CC1=CC2=CC=CC=C2N=C1C1=CC=CC=C1 URMNGDORJKJIIK-UHFFFAOYSA-N 0.000 description 1
- DKERXAPXOULUNA-UHFFFAOYSA-N iridium;2-phenyl-1h-imidazole Chemical class [Ir].C1=CNC(C=2C=CC=CC=2)=N1 DKERXAPXOULUNA-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000005610 quantum mechanics Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- 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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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- 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
Definitions
- the present invention relates to organic light emitting devices (OLEDs), and specifically to phosphorescent organic materials used in such devices. More specifically, the present invention relates to arylimidazole, aryltriazole, and aryltetrazole derivative complexes incorporated into OLEDs.
- Opto-electronic devices that make use of organic materials are becoming increasingly desirable for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices, hi addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the organic materials may have performance advantages over conventional materials. For example, the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.
- OLEDs organic light emitting devices
- the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.
- organic includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices.
- Small molecule refers to any organic material that is not a polymer, and "small molecules” may actually be quite large. Small molecules may include repeat units in some circumstances. For example, using a long chain alkyl group as a substituent does not remove a molecule from the "small molecule” class. Small molecules may also be incorporated into polymers, for example as a pendent group on a polymer backbone or as a part of the backbone.
- Small molecules may also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety.
- the core moiety of a dendrimer may be a fluorescent or phosphorescent small molecule emitter.
- a dendrimer may be a "small molecule," and it is believed that all dendrimers currently used in the field of OLEDs are small molecules, hi general, a small molecule has a well-defined chemical formula with a single molecular weight, whereas a polymer has a chemical formula and a molecular weight that may vary from molecule to molecule. [004] OLEDs make use of thin organic films that emit light when voltage is applied across the device.
- OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting.
- Several OLED materials and configurations are described in U.S. Patent Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.
- OLED devices are generally (but not always) intended to emit light through at least one of the electrodes, and one or more transparent electrodes may be useful in organic opto ⁇ electronic devices.
- a transparent electrode material such as indium tin oxide (ITO)
- ITO indium tin oxide
- a transparent top electrode such as disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entireties, may also be used.
- the top electrode does not need to be transparent, and maybe comprised of a thick and reflective metal layer having a high electrical conductivity.
- the bottom electrode may be opaque and / or reflective. Where an electrode does not need to be transparent, using a thicker layer may provide better conductivity, and using a reflective electrode may increase the amount of light emitted through the other electrode, by reflecting light back towards the transparent electrode. Fully transparent devices may also, be fabricated, where both electrodes are transparent. Side emitting OLEDs may also be fabricated, and one or both electrodes may be opaque or reflective in such devices. [006] As used herein, "top” means furthest away from the substrate, while “bottom” means closest to the substrate. For example, for a device having two electrodes, the bottom electrode is the electrode closest to the substrate, and is generally the first electrode fabricated.
- the bottom electrode has two surfaces, a bottom surface closest to the substrate, and a top surface further away from the substrate.
- a first layer is described as “disposed over” a second layer, the first layer is disposed further away from substrate.
- a cathode maybe described as “disposed over” an anode, even though there are various organic layers in between.
- solution processible means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.
- a first "Highest Occupied Molecular Orbital” (HOMO) or “Lowest Unoccupied Molecular Orbital” (LUMO) energy level is "greater than” or "higher than” a second HOMO or LUMO energy level if the first energy level is ' closer to the vacuum energy level. Since ionization potentials (IP) are measured as a negative energy relative to a vacuum level, a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative).
- IP ionization potentials
- EA electron affinity
- the LUMO energy level of a material is higher than the HOMO energy level of the same material.
- a "higher” HOMO or LUMO energy level appears closer to the top of such a diagram than a "lower” HOMO or LUMO energy level.
- An organic light emitting device has an anode, a cathode and an organic layer disposed between the anode and the cathode.
- the organic layer comprises a compound further comprising one or more arylimidazole, aryltriazole, or dryltetrazole derivative ligands coordinated to a metal center.
- the ligand has the structure:
- ring A is a 5- membered heterocyclic ring having at least 2 nitrogen atoms, with one nitrogen atom coordinated to metal M, wherein ring A can be optionally substituted with one or more substituents R and additionally or alternatively, any two substituted positions on ring A together form, independently a cyclic ring, wherein the cyclic ring is not an aromatic ring, and the cyclic ring may be optionally substituted', ring B is an aromatic ring with at least one carbon atom coordinated to metal M,
- Fig. 1 shows an organic light emitting device having separate electron transport, hole transport, and emissive layers, as well as other layers.
- ⁇ Fig. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer.
- Fig. 3 shows plots of current density vs. voltage for example 7 and comparative example 1.
- Fig. 4 shows plots of external quantum efficiency vs. current density for example
- Fig. 5 shows the normalized electroluminescence spectra of example 7 and comparative example 1 taken at a current density of 10 mA/cm 2 .
- Fig. 6 shows plots of current density vs. voltage for example 8 and example 9.
- Fig. 7 shows plots of external quantum efficiency vs. current density for example
- Fig. 8 shows the normalized electroluminescence spectra of example 8 and example 9 taken at a current density of 10 mA/cm 2 .
- Fig. 9 shows plots of current density vs. voltage for example 10 and example 11.
- Fig. 10 shows plots of external quantum efficiency vs. current density for example
- Fig. 11 shows the normalized electroluminescence spectra for example 10 and example 11 at a current density of 10 mA/cm 2 .
- Fig. 12 shows the normalized electroluminescence spectra for devices containing dopant emitters hr(pq) 2 (acac), hr(3'-Mepq) 2 (acac), Ir(3'-Meppy) 3 , and Ir(ppy) 3 .
- Fig. 13 shows plots of current density vs. voltage for example 12 and comparative example 2.
- Fig. 14 shows plots of external quantum efficiency vs. current density for example
- Fig. 15 shows the normalized electroluminescence spectra of example 12 and comparative example 2 taken at a current density of 10 mA/cm .
- an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode.
- the anode injects holes and the cathode injects electrons into the organic layer(s).
- the injected holes and electrons each migrate toward the oppositely charged electrode.
- an "exciton” which is a localized electron-hole pair having an excited energy state, is formed.
- Light is emitted when the exciton relaxes via a photoemissive mechanism.
- the exciton may be localized on an excimer or an exciplex. Non-radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.
- the initial OLEDs used emissive molecules that emitted light from their singlet states ("fluorescence") as disclosed, for example, in U.S. Patent No. 4,769,292, which is incorporated by reference in its entirety. Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.
- Phosphorescence has been demonstrated. Baldo et al., "Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices," Nature, vol. 395, 151-154, 1998; (“Baldo-F') and Baldo et al., “Very high-efficiency green organic light-emitting devices based on electrophosphorescence," Appl. Phys. Lett., vol. 75, No. 3, 4-6 (1999) (“Baldo-II”), which are incorporated by reference in their entireties. Phosphorescence may be referred to as a "forbidden” transition because the transition requires a change in spin states, and quantum mechanics indicates that such a transition is not favored.
- phosphorescence generally occurs in a time frame exceeding at least 10 nanoseconds, and typically greater than 100 nanoseconds. If the natural radiative lifetime of phosphorescence is too long, triplets may decay by a non-radiative mechanism, such that no light is emitted. Organic phosphorescence is also often observed in molecules containing heteroatoms with unshared pairs of electrons at very low temperatures. 2,2' ⁇ bipyridine is such a molecule. Non-radiative decay mechanisms are typically temperature dependent, such that an organic material that exhibits phosphorescence at liquid nitrogen temperatures typically does not exhibit phosphorescence at room temperature. But, as demonstrated by Baldo, this problem may be addressed by selecting phosphorescent compounds that do phosphoresce at room temperature.
- Representative emissive layers include doped or un- doped phosphorescent organo-metallic materials such as disclosed in U.S. Patent Nos. 6,303,238 and 6,310,360; U.S. Patent Application Publication Nos. 2002-0034656; 2002-0182441; 2003- 0072964; and WO-02/074015.
- Phosphorescence may be preceded by a transition from a triplet excited state to an intermediate non-triplet state from which the emissive decay occurs.
- organic molecules coordinated to lanthanide elements often phosphoresce from excited states localized on the lanthanide metal. However, such materials do not phosphoresce directly from a triplet excited state but instead emit from an atomic excited state centered on the lanthanide metal ion.
- the europium diketonate complexes illustrate one group of these types of species.
- Phosphorescence from triplets can be enhanced over fluorescence by confining, preferably through bonding, the organic molecule in close proximity to an atom of high atomic number.
- This phenomenon is created by a mechanism known as spin-orbit coupling.
- a phosphorescent transition may be observed from an excited metal-to-ligand charge transfer (MLCT) state of an organometallic molecule such as tris(2-phenylpyridine)iridium(IH).
- MLCT excited metal-to-ligand charge transfer
- triplet energy refers to an energy corresponding to the highest energy feature discernable in the phosphorescence spectrum of a given material.
- the highest energy feature is not necessarily the peak having the greatest intensity in the phosphorescence spectrum, and could, for example, be a local maximum of a clear shoulder on the high energy side of such a peak.
- organometallic as used herein is as generally understood by one of ordinary skill in the art and as given, for example, in “Inorganic Chemistry” (2nd Edition) by Gary L. Miessler and Donald A. Tarr, Prentice Hall (1998).
- organometallic refers to compounds which have an organic group bonded to a metal through a carbon-metal bond.
- This class does not include per se coordination compounds, which are substances having only donor bonds from heteroatoms, such as metal complexes of amines, halides, pseudohalides (CN, etc.), and the like.
- organometallic compounds generally comprise, in addition to one or more carbon-metal bonds to an organic species, one or more donor bonds from a heteroatom.
- the carbon-metal bond to an organic species refers to a direct bond between a metal and a carbon atom of an organic group, such as phenyl, alkyl, alkenyl, etc., but does not refer to a metal bond to an "inorganic carbon," such as the carbon of CN or CO.
- Fig. 1 shows an organic light emitting device 100.
- Device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emissive layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, and a cathode 160.
- Cathode 160 is a compound cathode having a first conductive layer 162 and a second conductive layer 164.
- Device 100 maybe fabricated by depositing the layers described, in order.
- Substrate 110 may be any suitable substrate that provides desired structural properties.
- Substrate 110 may be flexible or rigid.
- Substrate 110 may be transparent, translucent or opaque.
- Plastic and glass are examples of preferred rigid substrate materials.
- Plastic and metal foils are examples of preferred flexible substrate materials.
- Substrate 110 may be a semiconductor material in order to facilitate the fabrication of circuitry.
- substrate 110 maybe a silicon wafer upon which circuits are fabricated, capable of controlling OLEDs subsequently deposited on the substrate. Other substrates may be used.
- the material and thickness of substrate 110 may be chosen to obtain desired structural and optical properties.
- Anode 115 may be any suitable anode that is sufficiently conductive to transport holes to the organic layers.
- the material of anode 115 preferably has a work function higher than about 4 eV (a "high work function material").
- Preferred anode materials include conductive metal oxides, such as indium tin oxide (ITO) and indium zinc oxide (IZO), aluminum zinc oxide (AlZnO) 1 , and metals.
- Anode 115 (and substrate 110) may be sufficiently transparent to create a bottom-emitting device.
- a preferred transparent substrate and anode combination is commercially available ITO (anode) deposited on glass or plastic (substrate).
- a flexible and transparent substrate-anode combination is disclosed in United States Patent Nos. 5,844,363 and 6,602,54,0 B2, which are incorporated by reference in their entireties.
- Anode 115 may be opaque and / or reflective.
- a reflective anode 115 may be preferred for some top-emitting devices, to increase the amount of light emitted from the top of the device.
- the material and thickness of anode 115 maybe chosen to obtain desired conductive and optical properties. Where anode 115 is transparent, there may be a range of thickness for a particular material that is thick enough to provide the desired conductivity, yet thin enough to provide the desired degree of transparency. Other anode materials and structures may be used.
- Hole transport layer 125 may include a material capable of transporting holes.
- Hole transport layer 130 maybe intrinsic (undoped), or doped. Doping maybe used to enhance conductivity.
- ⁇ -NPD and TPD are examples of intrinsic hole transport layers.
- An example of a p-doped hole transport layer is m-MTDATA doped with F 4 -TCNQ at a molar ratio of 50:1, as disclosed in United States Patent Application Publication No. 2002-0071963 Al to Forrest et al, which is incorporated by reference in its entirety. Other hole transport layers may be used.
- Emissive layer 135 may include an organic material capable of emitting light when a current is passed between anode 115 and cathode 160.
- emissive layer 135 contains a phosphorescent emissive material, although fluorescent emissive materials may also be used. Phosphorescent materials are preferred because of the higher luminescent efficiencies associated with such materials. Emissive layer 135 may also comprise a host material capable of transporting electrons and / or holes, doped with an emissive material that may trap electrons, holes, and / or excitons, such that excitons relax from the emissive material via a photoemissive mechanism. Emissive layer 135 may comprise a single material that combines transport and emissive properties.
- emissive layer 135 may comprise other materials, such as dopants that tune the emission of the emissive material.
- Emissive layer 135 may include a plurality of emissive materials capable of, in combination, emitting a desired spectrum of light. Examples of phosphorescent emissive materials include Ir(ppy) 3 . Examples of fluorescent emissive materials include DCM and DMQA. Examples of host materials include AIq 3 , CBP and mCP. Examples of emissive and host materials are disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety.
- Emissive material may be included in emissive layer 135 in a number of ways.
- an emissive small molecule maybe incorporated into a polymer. This may be accomplished by several ways: by doping the small molecule into the polymer either as a separate and distinct molecular species; or by incorporating the small molecule into the backbone of the polymer, so as to form a co-polymer; or by bonding the small molecule as a pendant group on the polymer.
- Other emissive layer materials and structures may be used.
- a small molecule emissive material may be present as the core of a dendrimer.
- Many useful emissive materials include one or more ligands bound to a metal center.
- a ligand maybe referred to as "photoactive” if it contributes directly to the luminescent properties of an organometallic emissive material.
- a "photoactive" ligand may provide, in conjunction with a metal, the energy levels from which and to which an electron moves when a photon is emitted.
- Other ligands may be referred to as "ancillary.”
- Ancillary ligands may modify the photoactive properties of the molecule, for example by shifting the energy levels of a photoactive ligand, but ancillary ligands do not directly provide the energy levels directly involved in light emission.
- Electron transport layer 140 may include a material capable of transporting electrons. Electron transport layer 140 may be intrinsic (undoped), or doped. Doping may be used to enhance conductivity. AIq 3 is an example of an intrinsic electron transport layer. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1 : 1 , as disclosed in United States Patent Application Publication No. 2002-0071963 Al to Forrest et al., which is incorporated by reference in its entirety. Other electron transport layers may be used.
- the charge carrying component of the electron transport layer may be selected such that electrons can be efficiently injected from the cathode into the LUMO (Lowest Unoccupied Molecular Orbital) energy level of the electron transport layer.
- the "charge carrying component” is the material responsible for the LUMO energy level that actually transports electrons. This component may be the base material, or it may be a dopant.
- the LUMO energy level of an organic material may be generally characterized by the electron affinity of that material and the relative electron injection efficiency of a cathode may be generally characterized in terms of the work function of the cathode material.
- the preferred properties of an electron transport layer and the adjacent cathode may be specified in terms of the electron affinity of the charge carrying component of the ETL and the work function of the cathode material.
- the work function of the cathode material is preferably not greater than the electron affinity of the charge carrying component of the electron transport layer by more than about 0.75 eV, more preferably, by not more than about 0.5 eV. Similar considerations apply to any layer into which electrons are being injected.
- Cathode 160 may be any suitable material or combination of materials known to the art, such that cathode 160 is capable of conducting electrons and injecting them into the organic layers of device 100.
- Cathode 160 may be transparent or opaque, and may be reflective.
- Metals and metal oxides are examples of suitable cathode materials.
- Cathode 160 maybe a single layer, or may have a compound structure.
- Figure 1 shows a compound cathode 160 having a thin metal layer 162 and a thicker conductive metal oxide layer 164.
- preferred materials for the thicker layer 164 include ITO, IZO, and other materials known to the art.
- cathodes including compound cathodes having a thin layer of metal such as Mg: Ag with an overlying transparent, electrically- conductive, sputter-deposited ITO layer.
- the part of cathode 160 that is in contact with the .underlying organic layer, whether it is a single layer cathode 160, the thin metal layer 162 of a compound cathode, or some other part, is preferably made of a material having a work function lower than about 4 eV (a "low work function material").
- Other cathode materials and structures may be used.
- Blocking layers may be used to reduce the number of charge carriers (electrons or holes) and / or excitons that leave the emissive layer.
- An electron blocking layer 130 may be disposed between emissive layer 135 and the hole transport layer 125, to block electrons from leaving emissive layer 135 in the direction of hole transport layer 125.
- a hole blocking layer 140 maybe disposed between emissive Iayerl35 and electron transport layer 145, to block holes from leaving emissive layer 135 in the direction of electron transport layer 140.
- Blocking layers may also be used to block excitons from diffusing out of the emissive layer. The theory and use of blocking layers is described in more detail in United States Patent No. 6,097,147 and United States Patent Application Publication No. 2002-0071963 Al to Forrest et al., which are incorporated by reference in their entireties.
- blocking layer means that the layer provides a barrier that significantly inhibits transport of charge carriers and/or excitons through the device, without suggesting that the layer necessarily completely blocks the charge carriers and/or excitons.
- the presence of such a blocking layer in a device may result in substantially higher efficiencies as compared to a similar device lacking a blocking layer.
- a blocking layer may be used to confine emission to a desired region of an OLED.
- injection layers are comprised of a material that may improve the injection of charge carriers from one layer, such as an electrode or an organic layer, into an adjacent organic layer. Injection layers may also perform a charge transport function.
- hole injection layer 120 may be any layer that improves the injection of holes from anode 115 into hole transport layer 125.
- CuPc is an example of a material that may be used as a hole injection layer from an ITO anode 115, and other anodes.
- electron injection layer 150 maybe any layer that improves the injection of electrons into electron transport layer 145.
- LiF / Al is an example of a material that may be used as an electron injection layer into an electron transport layer from an adjacent layer.
- a hole injection layer may comprise a solution deposited material, such as a spin-coated polymer, e.g., PEDOT:PSS, or it may be a vapor deposited small molecule material, e.g., CuPc or MTDATA.
- a solution deposited material such as a spin-coated polymer, e.g., PEDOT:PSS, or it may be a vapor deposited small molecule material, e.g., CuPc or MTDATA.
- a hole injection layer may planarize or wet the anode surface so as to provide efficient hole injection from the anode into the hole injecting material.
- a hole injection layer may also have a charge carrying component having HOMO (Highest Occupied Molecular Orbital) energy levels that favorably match up, as defined by their herein-described relative ionization potential (IP) energies, with the adjacent anode layer on one side of the HIL and the hole transporting layer on the opposite side of the HIL.
- the "charge carrying component” is the material responsible for the HOMO energy level that actually transports holes. This component may be the base material of the HIL, or it may be a dopant.
- a doped HIL allows the dopant to be selected for its electrical properties, and the host to be selected for morphological properties such as wetting, flexibility, toughness, etc.
- Preferred properties for the HIL material are such that holes can be efficiently injected from the anode into the HIL material.
- the charge carrying component of the HIL preferably has an IP not more than about 0.7 eV greater that the IP of the anode material. More preferably, the charge carrying component has an IP not more than about 0.5 eV greater than the anode material. Similar considerations apply to any layer into which holes are being injected.
- HIL materials are further distinguished from conventional hole transporting materials that are typically used in the hole transporting layer of an OLED in that such HIL materials may have a hole conductivity that is substantially less than the hole conductivity of conventional hole transporting materials.
- the thickness of the HIL of the present invention may be thick enough to help planarize or wet the surface of the anode layer. For example, an HIL thickness of as little as 10 nm maybe acceptable for a very smooth anode surface. However, since anode surfaces tend to be very rough, a thickness for the HIL of up to 50 nm may be desired in some cases.
- a protective layer may be used to protect underlying layers during subsequent fabrication processes.
- the processes used to fabricate metal or metal oxide top electrodes may damage organic layers, and a protective layer may be used to reduce or eliminate such damage.
- protective layer 155 may reduce damage to underlying organic layers during the fabrication of cathode 160.
- a protective layer has a high carrier mobility for the type of carrier that it transports (electrons in device 100), such that it does not significantly increase the operating voltage of device 100.
- CuPc, BCP, and various metal phthalocyanines are examples of materials that may be used in protective layers. Other materials or combinations of materials maybe used.
- protective layer 155 is preferably thick enough that there is little or no damage to underlying layers due to fabrication processes that occur after organic protective layer 160 is deposited, yet not so thick as to significantly increase ⁇ the operating voltage of device 100.
- Protective layer 155 maybe doped to increase its conductivity.
- a CuPc or BCP protective layer 160 may be doped with Li.
- a more detailed description of protective layers may be found in U.S. Patent Application Serial No. 09/931,948 to Lu et al., which is incorporated by reference in its entirety.
- Figure 2 shows an inverted OLED 200.
- the device includes a substrate 210, an cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230.
- Device 200 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has a cathode disposed over the anode, and device 200 has cathode 215 disposed under anode 230, device 200 may be referred to as an "inverted" OLED. Materials similar to those described with respect to device 100 maybe used in the corresponding layers of device 200. Figure 2 provides one example of how some layers may be omitted from the structure of device 100.
- FIG. 1 and 2 The simple layered structure illustrated in Figures 1 and 2 is provided by way of non-limiting example, and it is understood that embodiments of the invention may be used in connection with a wide variety of other structures.
- the specific materials and structures described are exemplary in nature, and other materials and structures may be used.
- Functional OLEDs maybe achieved by combining the various layers described in different ways, or layers may be omitted entirely, based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of host and dopant, or more generally a mixture, may be used. Also, the layers may have various sublayers.
- hole transport layer 225 transports holes and injects holes into emissive layer 220, and maybe described as a hole transport layer or a hole injection layer.
- an OLED may be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to Figures 1 and 2. [0049] Structures and materials not specifically described may also be used, such as QLEDs comprised of polymeric materials (PLEDs) such as disclosed in U.S. Pat. No.
- OLEDs having a single organic layer may be used.
- OLEDs may be stacked, for example as described in U.S. Patent No. 5,707,745 to Forrest et al, which is incorporated by reference in its entirety.
- the OLED structure may deviate from the simple layered structure illustrated in Figures 1 and 2.
- the substrate may include an angled reflective surface to improve out- coupling, such as a mesa structure as described in U.S. Patent No. 6,091,195 to Forrest et al., and / or a pit structure as described in U.S. Patent No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entireties.
- any of the layers of the various embodiments may be deposited by any suitable method.
- preferred methods include thermal evaporation, ink-jet, such as described in U.S. Patent Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties, organic vapor phase deposition (OVPD), such as described in U.S. Patent No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety, and deposition by organic vapor jet printing (OVJP), such as described in U.S. Patent Application No. 10/233,470, which is incorporated by reference in its entirety.
- OVPD organic vapor phase deposition
- OJP organic vapor jet printing
- Other suitable deposition methods include spin coating and other solution based processes.
- Solution based processes are preferably carried out in nitrogen or an inert atmosphere.
- preferred methods include thermal evaporation.
- Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. Patent Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entireties, and patterning associated with some of the deposition methods such as ink-jet and OVJD. Other methods may also be used.
- the materials to be deposited may be modified to make them compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing.
- Substituents having 20 carbons or more may be used, and 3-20 carbons is a preferred range. Materials with asymmetric structures may have better solution processibility than those having symmetric structures, because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing. [0051] ⁇
- substituents may be added to a compound having three bidentate ligands, such that after the substituents are added, one or more of the bidentate ligands are linked together to form, for example, a tetradentate or hexadentate ligand. Other such linkages may be formed. It is believed that this type of linking may increase stability relative to a similar compound without linking, due to what is generally understood in the art as a "chelating effect.”
- Devices fabricated in accordance with embodiments of the invention may be incorporated into a wide variety of consumer products, including flat panel displays, computer monitors, televisions, billboards, lights for interior or exterior illumination and / or signaling, heads up displays, fully transparent displays, flexible displays, laser printers, telephones, cell phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, micro-displays, vehicles, a large area wall, theater or stadium screen, or a sign.
- PDAs personal digital assistants
- Various control mechanisms may be used to control devices fabricated in accordance with the present invention, including passive matrix and active matrix. Many of the devices are intended for use in a temperature range comfortable to humans, such as 18 degrees C to 30 degrees C, and more preferably at room temperature (20 - 25 degrees C).
- halo or halogen as used herein includes fluorine, chlorine, bromine and iodine.
- alkyl as used herein contemplates both straight and branched chain alkyl radicals.
- Preferred alkyl groups are those containing from one to fifteen carbon atoms and includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, and the like. Additionally, the alkyl group may be optionally substituted with one or more substituents selected from halo, CN, CO 2 R, C(O)R, NR 2 , cyclic-amino, NO 2 , and OR.
- cycloalkyl as used herein contemplates cyclic alkyl radicals.
- Preferred cycloalkyl groups are those containing 3 to 7 carbon atoms and includes cyclopropyl, cyclopentyl, cyclohexyl, and the like. Additionally, the cycloalkyl group may be optionally substituted with one or more substituents selected from halo, CN, CO 2 R, C(O)R, NR 2 , cyclic- amino, NO 2 , and OR.
- alkenyl as used herein contemplates both straight and branched chain alkene radicals.
- Preferred alkenyl groups are those containing two to fifteen carbon atoms.
- alkenyl group may be optionally substituted with one or more substituents selected from halo, CN, CO 2 R, C(O)R, NR 2 , cyclic-amino, NO 2 , and OR.
- alkynyl as used herein contemplates both straight and branched chain alkyne radicals.
- Preferred alkyl groups are those containing two to fifteen carbon atoms.
- alkynyl group may be optionally substituted with one or more substituents selected from halo, CN, CO 2 R, C(O)R, NR 2 , cyclic-amino, NO 2 , and OR.
- alkylaryl as used herein contemplates an alkyl group that has as a substituent an aromatic group. Additionally, the alkylaryl group may be optionally substituted on the aryl with one or more substituents selected from halo, CN, CO 2 R, C(O)R, NR 2 , cyclic-amino,
- heterocyclic group contemplates non-aromatic cyclic radicals.
- Preferred heterocyclic groups are those containing 3 or 7 ring atoms which includes at least one hetero atom, and includes cyclic amines such as morpholino, piperdino, pyrrolidino, and the like, and cyclic ethers, such as tetrahydrofuran, tetrahydropyran, and the like.
- aryl or "aromatic group” as used herein contemplates single-ring groups and polycyclic ring systems.
- the polycyclic rings may have two or more rings in which two atoms are common by two adjoining rings (the rings are "fused") wherein at least one " of the rings is aromatic, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles and/or heteroaryls.
- heteroaryl as used herein contemplates single-ring hetero-aromatic groups that may include from one to four heteroatoms, for example, pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole, tetrazole, pyrazole, pyridine, pyrazine and pyrimidine, and the like.
- heteroaryl also includes polycyclic hetero-aromatic systems having two or more rings in which two atoms are common to two adjoining rings (the rings are "fused") wherein at least one of the rings is a heteroaryl, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles and/or heteroaryls.
- M is a metal having an atomic weight greater than 40; the dotted lines inside the rings represent optional double bonds; Z is carbon or nitrogen; each R, R' and R'" is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, trialkylsilyl, cyano, trifluoromethyl, ester, keto, amino, nitro, alkoxy, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; R" is H or F; ring A is a 5-niembered heterocyclic ring having at least 2 nitrogen atoms, with one nitrogen atom coordinated to metal M, wherein ring A can be optionally substituted with one or more substituents R and additionally or alternatively, any two substituted positions on ring A together form, independently a cyclic ring, wherein the cyclic ring is not an aromatic ring, and the cyclic ring may be optionally substituted; ring B is an aromatic
- the above compound includes a photoactive ligand having the following structure:
- M may be any metal having an atomic weight greater than 40.
- Preferred metals include Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag. More preferably, the metal is Lr or Pt. Most preferably, the metal is Ir.
- ring A is an imidazole ring. More preferred embodiments include compounds having one of the following structures:
- 2-phenylimidazole and 4-phenylimidazole have higher triplet energy than the most commonly used ligand, 2-phenyl ⁇ yridine, in phosphorescent organometallic complexes.
- a metal such as iridium
- the unsubstituted iridium 2- phenylimidazole and 4-phenylimidazole complexes exhibit higher triplet energy (i.e., bluer phosphorescence), and higher LUMO energy (i.e., harder to reduce) when compared to the unsubstituted iridium 2-phenylpyridine complex.
- tris(N-methyl-2- phenylimidazole)iridium(IH) has a peak wavelength of 470 nm in a dilute CH 2 Cl 2 solution.
- Tris(2-phenylpyridine)iridium(i ⁇ ) has a peak wavelength of 515 nm in a dilute CH 2 Cl 2 solution.
- FIG. 3-5 compare device data for a tris(N-methyl-2- phenylimidazole)iridium(IH) dopant and an existing blue emitting Ir[2-(4,6- difluorophenyl)pyridine] 3 , abbreviated as Ir(F 2 ppy) 3 .
- Figure 5 shows that these two compounds ' have similar triplet energy (highest energy emission peak) corresponding to similar wavelengths in the electroluminescence spectra.
- the compounds were used as dopants in the same device structure, which is ITO/CuPc(100 A)/NPD(300 A)/CBP:dopant(6%, 300 A)/BA1Q(4OO A)/LiF(10 A) /Al(IOOO A).
- the tris(N-methyl-2- phenylimidazole)iridium(irf) device which exhibited an external quantum efficiency of about 5%, is significantly more efficient than the Ir(F 2 ppy) 3 device, which has an external quantum efficiency of less than 1%.
- Substitutions of certain groups and modifications to the photoactive ligand may lower the triplet energy of the complex, which in some cases may be undesirable in certain QLED applications.
- the most relevant application for this invention maybe towards blue phosphorescence.
- the unsubstituted tris(N-methyl- 2-phenylimidazole)iridium(ffl) already phosphoresces as blue as Ir(F 2 ppy) 3 , in which the phosphorescence is blue-shifted from the unsubstituted fr(ppy) 3 by strongly electron withdrawing fluoro groups.
- the emission peaks for Ir(pq) 2 (acac) and Ir(3'-Mepq) 2 (acac) are 600 nm and 618 nm respectively, whereas the emission peaks for Ir(ppy) 3 and Ir(3'-Meppy) 3 are 514 nm and 522 nm respectively.
- the structural difference within the red pair and the green pair of compounds is only the absence and presence of the 3 '-methyl group in the top ring. It is believed that the presence of the methyl group, which is a weak electron donating group, at the 3 -position does not by itself account for the red-shifting effect in the phosphorescence.
- red-shift in the phosphorescence may be partially due to the twisting between the top and bottom rings exerted by the steric hindrance from the presence of a bulky substituent at the 3 ' -methyl group such as a methyl group. Similar effect is expected when the 6-position of the bottom ring is substituted by a bulky group as shown in a generic structure below.
- the top ring is a 5- membered ring.
- the steric bulkiness of the R'" group therefore, may have less effect on the twisting.
- R'" may be groups other than H and F (H and F are believed to be the smallest possible substituents). However, the R" is most preferably H or F to minimize the twisting.
- triplet energy it may be desirable to decrease triplet energy.
- certain compounds may have triplet energies that are slightly higher than the energy corresponding to e.g. a saturated green emission. In this particular example, it would be desirable to lower the energy to obtain a compound that would emit at a wavelength corresponding to saturated green.
- R 1 is H, phenyl, or methyl.
- the phenyl may be substituted or unsubstituted.
- M is iridium and the compound has a tris configuration wherein m is 3 and n is zero.
- the compound has the structure
- More preferred embodiments include compounds having the following structures:
- the ligands for these embodiments have the corresponding structures:
- the imidazole compound has the structure:
- Preferred embodiments include compounds with the following structures:
- the compound has the structure , in which the ligand has the structure
- One embodiment has a compound with the
- the compound is a triazole having one of the following structures:
- the ligand has a structure selected from:
- R 1 is H, phenyl, or methyl.
- the phenyl may be substituted or unsubstituted.
- M is Iridium and the compound has a tris configuration wherein m is 3 and n is zero.
- the triazole compounds have the following structures:
- the compound is a tetrazole having one of the following structures: , in which the ligand has a structure selected from the following structures:
- R 1 is H, phenyl, or methyl.
- the phenyl may be substituted or unsubstituted.
- M is Mdium and the compound has a tris configuration wherein m is 3 and n is zero.
- the compound has the structure:
- CBP 4,4'-N,N-dicarbazole-biphenyl m-MTDATA 4,4',4"- ⁇ s(3-memylphenylpheniyamino)triphenylamine
- AIq 3 8-tris-hydroxyquinoline aluminum
- Bphen 4,7-diphenyl- 1 , 10-phenanthroline n-BPhen: n-doped BPhen (doped with lithium)
- F 4 -TCNQ tetrafluoro-tetracyano-quinodimethane
- p-MTDATA ⁇ -doped m-MTDATA (doped with F 4 -TCNQ)
- Ir(ppy) 3 tris(2-phenylpyridine)-iridium
- Ir( ⁇ z) 3 tris(l-phenylpyrazoloto,N,C(2')iridium( ⁇ i)
- BCP 2,9-dimethyl-4,7-diphenyl-l,10-phenanthroline
- ITO indium tin oxide
- NPD N,N'-diphenyl-N-N'-di(l-naphmyl)-benzidine
- TPD N,N'-diphenyl-N-N'-di(3-toly)-benzidine
- BAIq aluminum( ⁇ i)bis(2-methyl-8-hydroxyquinolinato)4-ph.enylphenolate mCP: 1 ,3-N,N-dicarbazole-benzene
- DCM 4-(dicyanoethylene)-6-(4-dimethylaminostyryl-2-rnethyl)-4H-pyran
- PEDOT:PSS an aqueous dispersion of poly(3,4-ethylenedioxythiophene) with polystyrenesulfonate (PSS)
- Certain of the iridium complexes may be subject to photo-oxidation in air and therefore should be protected from light and / or air during synthesis, isolation, and subsequent use in fabricating devices.
- Example 1 Synthesis of/ ⁇ c-tris(2-phenyl-N-methyIimidazolato-N,C 2 ')iridium(III)
- N-Methyl-2-phenylimidazole (9.30 g, 59 mmol) and tris(acetylacetonate)iridium(III) (4.90 g, 10 mmol) were added to a flask containing 20 mL of tridecane. The mixture was heated to reflux and stirred under a nitrogen atmosphere for 24 hours. After cooling, the precipitate which formed was filtered and washed with absolute ethanol followed by hexane.
- Example 2 Synthesis of fac tris(N-methyl-4-phenylimidazolato-N,C 2 )iridium(III)
- N-Methyl-4-phenylimidazole (930 mg, 6 mmol) and tris(acetylacetonate)iridium(i ⁇ ) (490 mg, 1 mmol) are added to a flask containing 5 mL of tridecane.
- the reaction mixture is heated to reflux and stirred under a nitrogen atmosphere for 24 hours. After cooling, the precipitate which forms is filtered and washed with absolute ethanol followed by hexane. The residue is further purified by a silica gel column to give ⁇ c-tris[N-methyl-4-phenylimidazolato-N,C 2 ]iridium(IH).
- Example 3 Synthesis of/ ⁇ c-tiis[ ⁇ r -phenyl-2-phenylimidazolato-N,C 2 ']iridium(III)
- Step 2 iV-Phenyl-2-phenylimidazole (0.44 g, 2.0 mmol) and tris(acetylacetonate)iridium(IH) (0.25 g, 0.5 mmol) were added to a flask containing 5 mL of ethyleneglycol. The reaction mixture was heated to reflux and stirred under a nitrogen atmosphere for 24 hours. After cooling, the precipitate formed was filtered and washed first with absolute ethanol followed by hexane.
- N-memyl-2-bromoimidazole (6.50 g, 40 mmol),2,4- diflurophenylboronic acid (7.89g, 50 mmol), palladium(IT) acetate (0.28 g, 1.25 mmol), triphenylphosphine (1.31 g, 5 mmol), sodium carbonate (14.31 g, 135 mmol), and 200 mL of DME an ⁇ l 100 mL of water.
- the reaction was heated to reflux and stirred under a nitrogen atmosphere for 12 hours.
- the mixture was extracted with ethyl acetate and further purified by a silica gel column.
- N-methyl-2-(2,4-diflurophenyl)imidazole (0.39 g, 2.0 mmol) and tris(acetylacetonate)iridium(III) (0.25 g, 0.5 mmol) were added to a flask containing 5 mL of tridecane.
- the reaction mixture was heated to reflux and stirred under a nitrogen atmosphere for 24 hours. After cooling, the precipitate formed was filtered and washed first with absolute ethanol followed by hexane. The residue was further purified by a silica gel column chromatography to (2,4-diflurophenyl)imidazolato-N,C 2 ]iridium(IH) (0.02 g).
- iV-Phenyl-2-(2,4-difluro ⁇ henyl)imidazole (6.80 g, 26.5 mmol) and tris(acetylacetonate)iridium(IIT) (3.25 g, 6.6 mmol) were added to a flask containing 35 mL of ethylene glycol.
- the reaction mixture was heated to reflux and stirred ' under a nitrogen atmosphere for 48 hours. After cooling, the precipitate formed was filtered and washed first with absolute ethanol followed by hexane.
- ETL2 refers to the ETL adjacent to the emissive layer (EML) and ETLl refers to the ETL adjacent to ETL2.
- the organic stack consisted of sequentially, from the ITO surface, 100 A thick of copper phthalocyanine (CuPc) as the hole injection layer (HIL), 300 A of 4,4'-bis[N-(l-naphthyl)-N- phenylaminojbiphenyl ( ⁇ -NPD) as the hole transporting layer (HTL), 300 A of 4,4'-bis(N- carbazolyl)biphenyl (CBP) doped, with 6 wt% of the dopant emitter tris(N-methyl-2- phenylimidazolato-N,C 2 )iridium(III) as the emissive layer (EML), 400 A of aluminum(IH)bis(2- methyl-8-hydroxyquinolinato)4-phenyl ⁇ henolate (BAIq) as the ETL2. There was no ETLl.
- CuPc copper phthalocyanine
- HIL hole injection layer
- HTL hole transporting layer
- CBP 4,4'
- the organic stack consisted of sequentially, from the ITO surface, 100 A thick of copper phthalocyanine (CuPc) as the hole injection layer (HIL), 300 A of 4,4'-bis[N-(l-naphthyl)-N- phenylaminojbiphenyl ( ⁇ -NPD) as the hole transporting layer (HTL), 300 A of 4,4'-bis(N- carbazolyl)biphenyl (CBP) doped with 6 wt% of the dopant emitter tris(2-(4,6- difluorophenyl)pyridme)iridium(i ⁇ ) [Ir(F 2 ppy) 3 ] as the emissive layer (EML), 400 A of aluminum( ⁇ T)bis(2-methyl-8-hydroxyquinolinato)4- ⁇ henylphenolate (BAIq) as the ETL2. There was no ETLl.
- HIL hole injection layer
- ⁇ -NPD hole transporting layer
- CBP 4,4'-bis
- the organic stack consisted of sequentially, from the ITO surface, 100 A thick of copper phthalocyanine (CuPc) as the hole injection layer (HIL), 300 A of 4,4'-bis[N-(l-naphthyl)-N- phenylamino]biphenyl ( ⁇ -NPD),as the hole transporting layer (HTL), 300 A of 4,4'-bis(N- carbazolyl)biphenyl (CBP) doped with 6 wt% of the dopant emitter tris(N-phenyl-2- phenylimidazolato-N,C 2 )iridium(III) as the emissive layer (EML), 400 A of aluminum(IH)bis(2- methyl-8-hydroxyquinolinato)4-phenylphenolate (BAIq) as the ETL2. There was no ETLl.
- HIL hole injection layer
- HTL hole transporting layer
- CBP 4,4'-bis(N- carbazolyl)b
- the organic stack consisted of sequentially, from the ITO surface, 100 A thick of copper phthalocyanine (CuPc) as the hole injection layer (HIL), 300 A of 4,4'-bis[N-(l-naphthyl)-N- phenylaminojbiphenyl ( ⁇ -NPD), as the hole transporting layer (HTL), 300 A of 4,4'-bis(N- carbazolyl)biphenyl (CBP) doped with 6 wt% of the dopant emitter tris(N-phenyl-2- phenylimidazolato-N,C 2' )iridium(m) as the emissive layer (EML), 100 A of HPT as the ETL2, 300 A of aluminum(III)bis(2-methyl-8-hydroxyquinolinato)4-phenylphenolate (BAIq) as the ETLl .
- HIL hole injection layer
- HTL hole transporting layer
- CBP 4,4'-bis(N- carbazoly
- the organic stack consisted of sequentially, from the ITO surface, 100 A thick of copper phthalocyanine (CuPc) as the hole injection layer (HIL), 300 A of 4,4'-bis[N-(l-naphthyl)-N- phenylamino]biphenyl ( ⁇ -NPD), as the hole transporting iayer (HTL), 300 A of 4,4' -Ms(N- .
- CuPc copper phthalocyanine
- HIL hole injection layer
- ⁇ -NPD 4,4'-bis[N-(l-naphthyl)-N- phenylamino]biphenyl
- HTL hole transporting iayer
- CBP carbazolyl)biphenyl
- CBP carbazolyl)biphenyl
- BAIq alummum(nr)bis(2-methyl-8-hydroxyquinolinato)4-phenylphenolate
- the organic stack consisted of sequentially, from the ITO surface, 100 A thick of copper phthalocyanine (CuPc) as the hole injection layer (HIL), 300 A of 4,4'-bis[N-(l-naphthyl)-N- phenylammo]bi ⁇ henyl ( ⁇ -NPD), as the hole transporting layer (HTL), 300 A of 4,4'-bis(N- carbazolyl)biphenyl (CBP) doped with 6 wt% of the dopant emitter tris[N-methyl-2-(4,6- difluorophenyl)imidazolato-N,C 2 ]Mdium( ⁇ i) as the emissive layer (EML), 100 A of HPT as the ETL2, 300 A of aluminum( ⁇ r)bis(2-methyl-8-hydroxyqumolinato)4-phenylphenolate (BAIq) as the ETLl.
- HIL hole injection layer
- ⁇ -NPD 4,4'-bis[N-
- the organic stack consisted of sequentially, from the ITO surface, 100 A thick of copper phthalocyanine (CuPc) as the hole injection layer (HIL), 300 A of 4,4'-bis[N-(l-naphthyl)-N- phenylamino]biphenyl ( ⁇ -NPD) as the hole transporting layer (HTL), 300 A of l,3-N,N-dicarbazole- benzene (mCP) doped with 6 wt% of the dopant emitter tris(N-methyl-2-phenylimidazolato- N,C 2' )iridium(i ⁇ ) as the emissive layer (EML), 400 A of aluminum(III)bis(2-methyl-8- hydroxyquinolmato)4-phenylphenolate (BAIq) as the ETL2. There is no ETLl.
- HIL hole injection layer
- HTL hole transporting layer
- mCP l,3-N,N-dicarbazole-
- the organic stack consisted of sequentially, from the ITO surface, 100 A thick of copper.
- phthalocyanine (CuPc) as the hole injection layer (HIL)
- BAIq alunimi ⁇ m(Tir)bis(2-methyl-8-hydroxyquinolinato
- Fig. 3 shows plots of current density vs. voltage for example 7 and comparative example 1. The current- voltage characteristics are similar, with example 1 driving at slightly higher voltage at the same current density.
- Fig. 4 shows plots of external quantum efficiency vs. current density for example
- Fig. 5 shows the normalized electroluminescence spectra of example 7 and comparative example 1 taken at a current density of 10 niA/cm 2 . While the electroluminescence spectra are similar, the maximum external quantum efficiency of example 7 is 5.4% whereas that of comparative example 1 is ⁇ 1%. It demonstrates that the invention compounds are advantageously much more efficient in this device architecture. Without being limited to how it works, the better efficiency of example 7 may be partially due to the improved charge trapping, particularly hole trapping, of tris(N-methyl-2-phenylimidazolato- N,C 2 )iridium(IH) than Ir(F 2 ppy) 3 .
- Tris(N-methyl-2-phenylimidazolato-N,C 2' )iridium(III) is about 0.8 V easier to oxidize than Ir(F 2 ⁇ py) 3 in cylic voltammetry in the same solvent system. This may lead to better a hole trapping behavior of the former when used as a dopant at the same concentration in the same host (6% of dopant in CBP in this case), thus improving device efficiency.
- Fig. 6 shows plots of current density vs. voltage for example 8 and example 9.
- the current- voltage characteristics are similar in examples 8 and 9 which respectively has BAIq as the only ETL and HTP/BAlq as the ETL2 /ETLl .
- Fig. 7 shows plots of external quantum efficiency vs. current density for example
- Fig. 8 shows the normalized electroluminescence spectra of example 8 and example 9 taken at a current density of 10 niA/cm 2 .
- Example 8 has a maximum external quantum efficiency of 11% whereas example 9 has a maximum external quantum efficiency of 6.8%. It suggests, although the EML is the same in examples 8 and 9, the ETLs may have a significant effect on the device efficiency due to the electron injection, hole blocking and exciton blocking properties of the ETLs.
- Fig. 9 shows plots of current density vs. voltage for example 10 and example 11.
- the current-voltage characteristics are similar in examples 10 and 11 which respectively has BAIq as the only ETL and HTP/BAlq as the ETL2 /ETLl.
- Fig. 10 shows plots of external quantum efficiency vs. current density for example
- Fig. 11 shows the normalized electroluminescence spectra of example 10 and example 11 taken at a current density of 10 mA/cm 2 .
- Example 10 has a maximum external quantum efficiency of 1.3% whereas example 11 has a maximum external quantum efficiency of 1.8%.
- the EML is the same in examples 10 and 11, the ETLs may have a significant effect on the device efficiency due to the electron injection, hole blocking and exciton blocking proerties of the ETLs.
- Fig. 13 shows plots of current density vs. voltage for example 12 and comparative example 2.
- Fig. 14 shows plots of external quantum efficiency vs. current density for example 12 and comparative example 2.
- Fig. 15 shows the normalized electroluminescence spectra of example 12 and comparative example 2 taken at a current density of 10 mA/cm 2 . While the electroluminescence spectra are similar, the maximum external quantum efficiency of example 12 is 7.5% whereas that of comparative example is 4.0%.
- example 12 may be partially due to the improved charge trapping, particularly hole trapping, of tris(N-methyl-2-phenylimidazolato-N,C )iridium( ⁇ l) than Ir(F 2 p ⁇ y) 3 .
- Tris(N-methyl-2-phenylimidazolato-N,C 2 )iridium(IH) is about 0.8 V easier to oxidize than Ir(F 2 ppy) 3 in cylic voltammetry in the same solvent system. This may lead to better a hole trapping behavior of the former when used as a dopant at the same concentration in the same host (6% of dopant in mCP in this case), thus improving device efficiency.
- Example 12 consists of mCP as the host, whereas example 7 consists of CBP as the host.
- mCP is more suitable as a host than CBP in this case because of the higher triplet energy of the former which leads to reduced or no phosphorescence quenching of the dopant emitter tris(N-methyl-2- phenylimidazolato-N,C 2 )iridium(IIi).
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