WO2010069442A1 - Organische elektrolumineszenzvorrichtung - Google Patents
Organische elektrolumineszenzvorrichtung Download PDFInfo
- Publication number
- WO2010069442A1 WO2010069442A1 PCT/EP2009/008196 EP2009008196W WO2010069442A1 WO 2010069442 A1 WO2010069442 A1 WO 2010069442A1 EP 2009008196 W EP2009008196 W EP 2009008196W WO 2010069442 A1 WO2010069442 A1 WO 2010069442A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- aromatic
- compound
- organic electroluminescent
- atoms
- Prior art date
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- 238000005401 electroluminescence Methods 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 239000011159 matrix material Substances 0.000 claims abstract description 31
- 125000003118 aryl group Chemical group 0.000 claims description 74
- -1 aromatic phosphine oxides Chemical class 0.000 claims description 47
- 229940126062 Compound A Drugs 0.000 claims description 32
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 239000003446 ligand Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 150000008365 aromatic ketones Chemical class 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 5
- 229910052741 iridium Inorganic materials 0.000 claims description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 238000007639 printing Methods 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 238000005424 photoluminescence Methods 0.000 claims description 3
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052693 Europium Inorganic materials 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical class [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000012159 carrier gas Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 2
- 238000009472 formulation Methods 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
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 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
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Chemical class 0.000 claims description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 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
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 238000004528 spin coating Methods 0.000 claims description 2
- 238000000859 sublimation Methods 0.000 claims description 2
- 230000008022 sublimation Effects 0.000 claims description 2
- 238000005092 sublimation method Methods 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- 238000001947 vapour-phase growth Methods 0.000 claims description 2
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 abstract description 8
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 abstract description 6
- 239000010410 layer Substances 0.000 description 58
- 150000003254 radicals Chemical class 0.000 description 20
- 239000002019 doping agent Substances 0.000 description 17
- 125000001072 heteroaryl group Chemical group 0.000 description 13
- 238000004020 luminiscence type Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- 238000000103 photoluminescence spectrum Methods 0.000 description 7
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound 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 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 0 CC*1(*(c(*2c3cc(C(C)(C)C)cc(C(C)(C)C)c3)ccc3)c3-c3ccccc13)*1c2cccc1-c1ccccc1* Chemical compound CC*1(*(c(*2c3cc(C(C)(C)C)cc(C(C)(C)C)c3)ccc3)c3-c3ccccc13)*1c2cccc1-c1ccccc1* 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 150000001716 carbazoles Chemical class 0.000 description 5
- 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 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- OWPJBAYCIXEHFA-UHFFFAOYSA-N 1-phenyl-3-(3-phenylphenyl)benzene Chemical compound C1=CC=CC=C1C1=CC=CC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 OWPJBAYCIXEHFA-UHFFFAOYSA-N 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 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
- 125000005259 triarylamine group Chemical group 0.000 description 4
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 3
- YAVCXSHORWKJQQ-UHFFFAOYSA-N 1-phenyl-2-(2-phenylphenyl)benzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 YAVCXSHORWKJQQ-UHFFFAOYSA-N 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- IERDDDBDINUYCD-UHFFFAOYSA-N 1-[4-[4-(9h-carbazol-1-yl)phenyl]phenyl]-9h-carbazole Chemical group C12=CC=CC=C2NC2=C1C=CC=C2C(C=C1)=CC=C1C(C=C1)=CC=C1C1=C2NC3=CC=CC=C3C2=CC=C1 IERDDDBDINUYCD-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-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
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- GODFYRLYJQMVAD-UHFFFAOYSA-N C1=CC=CC=C1C1=CC=CN=C1[Ir](C=1C(=CC=CN=1)C=1C=CC=CC=1)C1=NC=CC=C1C1=CC=CC=C1 Chemical compound C1=CC=CC=C1C1=CC=CN=C1[Ir](C=1C(=CC=CN=1)C=1C=CC=CC=1)C1=NC=CC=C1C1=CC=CC=C1 GODFYRLYJQMVAD-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-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
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 238000010276 construction Methods 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
- 238000000295 emission spectrum Methods 0.000 description 2
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- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical compound C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
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- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
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- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
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- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 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
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
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- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
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- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
Definitions
- the present invention relates to phosphorescent organic electroluminescent devices which contain two phosphorescent dopants.
- OLEDs organic electroluminescent devices
- OLEDs organic electroluminescent devices
- further improvements are needed.
- the so-called roll-off behavior of the OLEDs ie the efficiency as a function of the brightness of the OLED, there is still room for improvement, since it is often observed that the efficiency drops sharply at high brightness. This applies in particular to electroluminescent devices which are doped with a phosphorescent emitter.
- carbazole derivatives e.g. B. bis (carbazolyl) biphenyl
- a matrix material for the phosphorescent emitter used as a matrix material for the phosphorescent emitter.
- these matrix materials often lead to comparatively high operating voltages.
- electron-conducting materials including ketones (for example according to WO 04/093207 or according to the unpublished application DE 102008033943.1), phosphine oxides and sulfones (WO 05/003253) are used as matrix materials for phosphorescent emitters.
- ketones possibly due to the good electron transport properties, very low operating voltages and long lifetimes are achieved, which makes this class of compounds a very interesting matrix material.
- these matrix materials often lead to a stronger roll-off behavior of the OLED, ie a greater decrease in efficiency at high brightness than with other matrix materials. There is therefore still room for improvement here.
- these matrix materials sometimes show incompatibility with metal complexes containing ketoketonate ligands, for example, acetylacetonate. This is reflected in lower efficiency and lifetime.
- metal complexes especially these metal complexes have proven to be emitters with very good emission properties, so that many of the currently used phosphorescent emitters are of this type of structure. There is therefore still room for improvement here.
- the technical problem underlying this invention is therefore to provide an organic electroluminescent device which exhibits less high-brightness roll-off behavior.
- the object is furthermore to provide an organic electroluminescent device which contains a metal complex with ketoketonate ligands and which leads to good emission properties with this dopant, in particular to good efficiency, a long service life and a low operating voltage.
- an organic electroluminescent device which contains in the emitting layer an aromatic ketone or another of the matrix materials defined below which is substituted by two different phosphorescent emitters simultaneously has high efficiencies, long lifetimes and low Operating voltages, even with phosphorescent emitters containing Ketoketonatliganden show. Furthermore, these electroluminescent devices have a surprisingly low roll-off behavior, so that they can also be operated with good efficiency at high brightness.
- organic electroluminescent devices which contain two phosphorescent emitters in a matrix.
- organic electroluminescent devices which contain a host material and two phosphorescent dopants.
- CBP bis (carbazolyl) biphenyl
- these electroluminescent devices have very high operating voltages. The voltages are comparable or even higher than in
- Electroluminescent devices containing only one phosphorescent dopant An influence on the roll-off behavior of the electroluminescent device is not disclosed.
- organic electroluminescent devices which contain a host material, a phosphorescent dopant and a fluorescent or phosphorescent dopant, which emits longer wavelength.
- Triarylamine derivatives and carbazole derivatives are disclosed in particular as the host material. This results in better efficiencies and a better lifetime especially for combination with a fluorescent dopant.
- An influence on the lifetime is not disclosed for electroluminescent devices which contain two phosphorescent dopants.
- an influence on the roll-off behavior of the electroluminescent device is not disclosed.
- the invention thus relates to an organic electroluminescent devices comprising in at least one emitting layer
- (C) a matrix material selected from the group consisting of aromatic ketones, aromatic phosphine oxides, aromatic sulfoxides and aromatic sulfones.
- an aromatic ketone is understood to mean a carbonyl group to which two aromatic or heteroaryl aromatic groups or aromatic or heteroaromatic ring systems are directly bonded.
- an aromatic sulfone is understood to mean a group S (OO) 2, to which two aromatic or heteroaromatic groups or aromatic or heteroaromatic ring systems are directly bonded.
- X is C, P or S;
- Ar is the same or different at each occurrence, an aromatic or heteroaromatic ring system having 5 to 80 aromatic ring atoms, which may be substituted in each case with one or more groups R 1 ;
- R 1 is the same or different H, D, F, Cl, Br, I at each occurrence
- Ar 1 is the same or different at each occurrence, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 2 ;
- R 2 is identical or different at each occurrence H, D or an aliphatic, aromatic and / or heteroaromatic organic radical, in particular a hydrocarbon radical having 1 to 20 C atoms, in which also H atoms can be replaced by F; two or more adjacent substituents R 2 may also together form a mono- or polycyclic, aliphatic or aromatic ring system;
- neither Ar nor Ar 1 contains a triarylamine group or a carbazole group.
- An organic electroluminescent device is understood to mean a device which contains the anode, cathode and at least one emitting layer, which is arranged between the anode and the cathode, wherein at least one layer between the anode and the cathode contains at least one organic or organometallic compound.
- at least one emitting layer contains at least one phosphorescent emitter A, at least one phosphorescent emitter B and at least one compound of the above-mentioned formula (1).
- An organic electroluminescent device need not necessarily contain only layers composed of organic or organometallic materials. So it is also possible that one or more layers contain inorganic materials or are constructed entirely of inorganic materials.
- a phosphorescent compound in the context of this invention is a compound which exhibits luminescence at room temperature from an excited state with a higher spin multiplicity, ie a spin state> 1, in particular from an excited triplet state.
- all luminescent transition metal complexes in particular all luminescent iridium and platinum compounds, are to be regarded as phosphorescent compounds.
- An aryl group in the sense of this invention contains at least 6 C atoms;
- a heteroaryl group contains at least 2 C atoms and at least 1 heteroatom, with the proviso that the sum of C atoms and heteroatoms gives at least 5.
- the heteroatoms are preferably selected from N, O and / or S.
- aryl group or heteroaryl either a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl group, for example naphthalene, anthracene, pyrene, quinoline, isoquinoline, etc., understood.
- An aromatic ring system in the context of this invention contains at least 6 C atoms in the ring system.
- a heteroaromatic ring system in the sense of this invention contains at least 2 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of C atoms and heteroatoms gives at least 5.
- the heteroatoms are preferably selected from N, O and / or S.
- An aromatic or heteroaromatic ring system in the sense of this invention is to be understood as meaning a system which does not necessarily contain only aryl or heteroaryl groups but in which also several aryl or heteroaryl groups a short, non-aromatic moiety (preferably less than 10% of the atoms other than H), e.g.
- N or O atom may be connected.
- systems such as 9,9'-spirobifluorene, 9,9-diaryl fluorene, triarylamine, diaryl ether, stilbene, benzophenone, etc. are also to be understood as aromatic ring systems in the context of this invention.
- aromatic or heteroaromatic ring system is understood as meaning systems in which a plurality of aryl or heteroaryl groups are linked together by single bonds, for example biphenyl, terphenyl or bipyridine.
- a C 1 - to C 4 -alkyl group in which also individual H atoms or CH 2 groups can be substituted by the abovementioned groups particularly preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, tert-pentyl, 2-pentyl, cyclopentyl, n-hexyl, s -hexyl, tert -hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n- Octyl, 2-
- An alkynyl group is particularly preferably understood to mean the radicals ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl and octynyl.
- a C 1 to C 40 -alkoxy group particular preference is given to methoxy, trifluoromethoxy, ethoxy, n-
- an aromatic or heteroaromatic ring system having 5-60 aromatic ring atoms which may be substituted in each case with the abovementioned radicals R and which may be linked via any positions on the aromatic or heteroaromatic, are understood in particular groups which are derived from benzene, Naphthalene, anthracene, phenanthrene, benzanthracene, benzphenanthrene, pyrene, chrysene, perylene, fluoranthene, benzfluoranthene, naphthacene, pentacene, benzpyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, benzofluorene, dibenzofluorene, spirobifluorene, dihydrophenanthrene, dihydropyr
- the compounds of the formula (1) preferably have a glass transition temperature TQ of greater than 70 ° C., more preferably greater than 90 ° C., very particularly preferably greater than 110 ° C.
- the photoluminescence maximum of the phosphorescent compound A is at least 20 nm shorter wavelength than that of the phosphorescent compound B, particularly preferably at least 30 nm short-wave. This is especially true when compound A is a green phosphorescent compound and compound B is a red phosphorescent compound or when compound A is a blue phosphorescent compound and compound B is a green phosphorescent compound.
- compound A is a deep blue phosphorescent compound and the compound B is a light blue phosphorescent compound, it is preferred that the compound A emit at least 10 nm short wavelength than the compound B.
- the photoluminescence maximum is determined by measuring the photoluminescence spectrum of a 50 nm thick layer in which the compound A is doped in a proportion of 5% by volume or the compound B in a proportion of 5% by volume in the enrovende matrix material according to formula (1).
- the emission spectrum of the electroluminescent device as a whole predominantly corresponds to the emission spectrum of the longer-wavelength emitting compound, that is, the compound B.
- the phosphorescent compound A is a green-luminescent compound and the phosphorescent compound B is a red-luminescent compound.
- the phosphorescent compound A is a blue-luminescent compound and the phosphorescent compound B is a green-luminescent compound or a red-luminescent compound.
- the phosphorescent compound A is a deep blue luminescent or UV-emitting compound and the compound B is a light blue luminescent compound.
- Green luminescence is understood as meaning a luminescence with a maximum of the photoluminescence spectrum in the range from 490 to 560 nm.
- blue luminescence is meant a luminescence with a maximum of the photoluminescence spectrum in the range of 440 to 490 nm.
- Deep blue luminescence is understood as meaning a luminescence with a maximum of the photoluminescence spectrum in the range from 350 to 460 nm.
- light blue luminescence is meant a luminescence with a maximum of the photoluminescence spectrum in the range of 460 to 490 nm.
- the photoluminescence spectrum is measured as described above.
- the proportion of the phosphorescent compound A in the layer is preferably 5 to 50% by volume, particularly preferably 10 to 25% by volume, very particularly preferably 12 to 20% by volume.
- the proportion of phosphorescent compound B in the layer is preferably 1 to 20% by volume, more preferably 3 to 10% by volume, most preferably 4 to 7% by volume.
- the phosphorescent compound A is preferably a material capable of transporting holes. Since the location of the HOMO (highest occupied molecular orbital) is responsible for the hole transport properties of the material, compound A preferably has a HOMO of> -5.9 eV, more preferably> -5.7 eV and most preferably of> -5.5 eV.
- the HOMO can be determined by photoelectron spectroscopy using Model AC-2 photon electron spectrometer from Riken Keiki Co. Ltd. (Http://www.rikenkeiki.com/pages/AC2.htm).
- Particularly suitable phosphorescent compounds A and B are compounds which, when suitably excited, emit light, preferably in the visible range, and also contain at least one atom of atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80.
- Preferred phosphorescence emitters A and B are compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, especially compounds containing iridium or platinum.
- Particularly preferred organic electroluminescent devices contain as phosphorescent compound A and / or as phosphorescent compound B at least one compound of the formulas (2) to (5),
- DCy is, identically or differently on each occurrence, a cyclic group which contains at least one donor atom, preferably nitrogen, carbon in the form of a carbene or phosphorus, via which the cyclic group is bonded to the metal, and which in turn has one or more substituents R 1 can carry; the groups DCy and CCy are linked by a covalent bond;
- CCy is the same or different at each occurrence a cyclic
- A is the same or different at each occurrence as a mononionic, bidentate chelating ligand, preferably a diketonate ligand or a picolinate ligand.
- ring systems between a plurality of radicals R 1 there may also be a bridge between the groups DCy and CCy. Furthermore, by forming ring systems between a plurality of radicals R 1, there may also be a bridge between two or three ligands CCy-DCy or between one or two ligands CCy-DCy and the ligand A, so that it is a polydentate or polypodal ligand system ,
- the compound A is preferably a compound of the abovementioned formula (3), in particular tris (phenylpyridyl) iridium, which may be substituted by one or more radicals R 1 .
- the compound A is tris (phenylpyridyl) iridium.
- the compound B is preferably a compound of the above-mentioned formulas (2), (3) or (5), particularly preferably of the formulas (2) or (5), very particularly preferably of the formula (2).
- a in formula (2) is preferably acetylacetonate or an acetylacetonate derivative.
- Examples of preferred phosphorescent compounds A and B are listed in the following table.
- Suitable compounds according to formula (1) are the ketones disclosed in WO 04/093207 and the unpublished DE 102008033943.1 and the phosphine oxides, sulfoxides and sulfones disclosed in WO 05/003253. These are via quote part of the present invention.
- the symbol X is C or P, particularly preferably C. They are therefore preferably ketones or phosphine oxides, more preferably ketones.
- the definition of the compound according to formula (1) shows that it not only has to contain a carbonyl or phosphine oxide group, but can also contain several of these groups.
- the group Ar in compounds according to formula (1) is preferably an aromatic ring system having 6 to 40 aromatic ring atoms.
- the aromatic ring system need not necessarily have only aromatic groups, but also two aryl groups may be interrupted by a non-aromatic group, for example by another carbonyl group.
- the group Ar has no more than two condensed rings. It is therefore preferably composed only of phenyl and / or naphthyl groups, particularly preferably only of phenyl groups, but does not contain any larger condensed aromatics, such as, for example, anthracene.
- Preferred groups Ar which are bonded to the carbonyl group are phenyl, 2-, 3- or 4-tolyl, 3- or 4-o-xylyl, 2- or 4-m-xylyl, 2-p-xylyl, , m- or p-tert-butylphenyl, o-, m- or p-fluorophenyl, benzophenone, 1-, 2- or 3-phenylmethanone, 2-, 3- or 4-biphenyl, 2-, 3- or 4- o-terphenyl, 2-, 3- or 4-m-terphenyl, 2-, 3- or 4-p-terphenyl, 2 '-p-terphenyl, 2', 4 'or 5' - m-terphenyl, 3 '- or 4' -o-terphenyl, p, m, o, p, m, m, o, m- or o, o-quaterphenyl, quinquephenyl, sexiphen
- the groups Ar may be substituted by one or more radicals R 1 .
- the group Ar 1, identical or different at each occurrence is an aromatic ring system having 6 to 24 aromatic ring atoms which may be substituted by one or more radicals R 2 .
- Ar 1 is more preferably identical or different at each occurrence, an aromatic ring system having 6 to 12 aromatic ring atoms.
- Preferred aromatic ketones, phosphine oxides, sulfoxides and sulfones are therefore the compounds of the following formulas (6) to (30),
- Z is the same or different every occurrence CR 1 or N, with a maximum of 3 symbols Z per ring for N; preferably Z is CR 1 ;
- n 1, 2, 3, 4 or 5;
- n is the same or different at each occurrence 0, 1, 2, 3 or 4;
- p is the same or different 0 or 1 at each occurrence.
- Ar in the abovementioned formulas (6) to (30) is preferably an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms which may be substituted by one or more radicals R 1 .
- Particularly preferred are the abovementioned groups Ar.
- aromatic ketones are benzophenone derivatives which are each substituted at the 3,3 ', 5,5'-positions by an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which in turn is replaced by one or more radicals R 1 according to the above definition can be substituted.
- suitable compounds according to formula (1) are the compounds (1) to (72) depicted below.
- the organic electroluminescent device may contain further layers. These are selected, for example, from one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, charge generation layers (Charge Generation Layers, IDMC 2003, Taiwan, Session 21 OLED (5), T. Matsumoto, T. Nakada). J. Endo, K. Mori, N. Kawamura, A. Yokoi, J. Kido, Multiphoton Organic EL Device Having Charge Generation Layer) and / or Organic or Inorganic P / N Transitions.
- interlayers may be present, which control, for example, the charge balance in the device.
- the layers, in particular the charge transport layers may also be doped. The doping of the layers may be advantageous for improved charge transport. It should be noted, however, that not necessarily each of these layers must be present and the choice of layers always depends on the compounds used.
- the organic electroluminescent device contains a plurality of emitting layers, wherein at least one emitting layer contains at least one phosphorescent compound A, one phosphorescent compound B and one compound according to formula (1). Particularly preferably, these emission layers have a total of a plurality of emission maxima between 380 nm and 750 nm, so that overall white emission results, ie in the emitting layers different emitting compounds are used, which can fluoresce or phosphoresce and emit the blue and yellow, orange or red light.
- three-layer systems ie systems with three emitting layers, wherein at least one of these layers contains at least one phosphorescent compound A, a phosphorescent compound B and a compound according to formula (1) and wherein the three layers show blue, green and orange or red emission (For the basic structure see eg WO 05/011013).
- the use of more than three emitting layers may also be preferred.
- a matrix material is selected from compounds of the formula (1).
- Preferred hole-conducting matrix materials are triarylamines, carbazole derivatives, e.g. B. CBP (N, N-bis-carbazolylbiphenyl) or in WO 05/039246, US 2005/0069729, JP 2004/288381, EP 1205527 or WO 08/086851 disclosed carbazole derivatives, Azacarbazole, z. B. according to EP 1617710, EP 1617711,
- bipolar matrix materials e.g. B. according to WO 07/137725, and benzothiophene or Dibenzothiophenderivate, z. B. according to WO 09/021126.
- the mixture of matrix materials may also contain more than two matrix materials.
- two or more materials according to formula (1) can be used.
- an organic electroluminescent device characterized in that one or more layers are coated with a sublimation process.
- the materials become in vacuum sublimation at a pressure less than 10 "5 mbar, preferably less than 10 " 6 mbar evaporated. It should be noted, however, that the pressure can be even lower, for example less than 10 "7 mbar.
- organic electroluminescent device characterized in that one or more layers with the
- OVPD Organic Vapor Phase Deposition
- carrier gas sublimation a carrier gas sublimation
- the materials are applied at a pressure between 10 "applied 5 mbar and 1 bar.
- OVJP organic vapor jet printing
- the materials are applied directly through a nozzle and patterned (eg. BMS Arnold et al., Appl. Phys. Lett., 2008, 92, 053301).
- an organic electroluminescent device characterized in that one or more layers of solution, such. B. by spin coating, or with any printing process, such.
- any printing process such as screen printing, flexographic printing or offset printing, but more preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing (ink jet printing), are produced.
- LITI Light Induced Thermal Imaging, thermal transfer printing
- inkjet printing ink jet printing
- soluble compounds are needed. High solubility can be achieved by suitable substitution of the compounds.
- solutions of individual materials can be applied, but also solutions containing several compounds, for example matrix materials and dopants.
- the organic electroluminescent device may also be fabricated as a hybrid system by applying one or more layers of solution and depositing one or more other layers.
- a hybrid system by applying one or more layers of solution and depositing one or more other layers.
- the emitting layer comprising a compound of the formula (1) and the phosphorescent compounds A and B are evaporated in vacuo and one or more other layers can be applied from solution.
- Another object of the present invention are mixtures comprising at least one phosphorescent compound A, at least one phosphorescent compound B and at least one aromatic ketone, aromatic phosphine oxide, aromatic sulfoxide or aromatic sulfone, preferably a compound according to formula (1).
- Yet another object of the present invention are solutions or formulations containing at least one mixture according to the invention and at least one solvent.
- the organic electroluminescent devices according to the invention have a very high efficiency. This is especially true when phosphorescent metal complexes with Ketoketonatliganden, z. Acetylacetonate ligands.
- the organic electroluminescent devices according to the invention simultaneously have a very good service life. This is especially true when phosphorescent metal complexes are used with Ketoketonatliganden.
- the organic electroluminescent devices according to the invention simultaneously have a very low operating voltage. In particular, the operating voltage is significantly lower than with matrix materials based on carbazole derivatives. 4.
- the organic electroluminescent devices according to the invention have a very low roll-off behavior. Thus, the roll-off is significantly lower than with electroluminescent devices, which also contain a compound according to formula (1), but only a phosphorescent compound.
- Example 1-13 Preparation and characterization of organic electroluminescent devices according to the invention
- Electroluminescent devices according to the invention can be prepared as described, for example, in WO 05/003253. In the following, the results of different OLEDs are compared.
- Q Examples 1-13 describe red-emitting OLEDs that are realized by the following layer structure:
- HIL Hole Injection Layer 20 nm 2,2 ', 7,7'-tetrakis (di-para-tolylamino) spiro-9,9'-bifluorene
- HTL Hole transporting layer 20 nm NPB (N-naphthyl-N-phenyl-4,4 1 - diaminobiphenyl).
- Emission Layer 30 nm Matrix Material: Spiro-Ketone (SK)
- HBL Hole blocking layer
- ETL Electron conductor
- OLEDs are characterized by default; For this purpose, the electroluminescence spectra, the efficiency (measured in cd / A) as a function of the brightness, the operating voltage, calculated from current-voltage-luminance characteristic curves (LUL characteristic curves), and the service life are determined.
- Example 1 serves as a comparative example and contains TER-1 as dopant.
- Example 2 describes an inventive OLED, in addition to TER-1 lr (ppy) 3 as further dopant. From Table 1 it can be seen that the OLED of the invention compared to the comparative example has a significantly improved efficiency and life, without affecting the color or the operating voltage.
- Comparative Examples 12 and 13 show the effect of a second dopant using the prior art host material CBP.
- CBP prior art host material
- Example 14-16 Preparation and characterization of organic electroluminescent devices according to the invention
- Examples 14-16 describe blue and green emitting OLEDs that are realized by the following layer construction and can be generated by the general method mentioned above:
- HIL Hole Injection Layer 20 nm 2,2 ' ) 7,7'-tetrakis (di-para-tolylamino) spiro-9,9'-bifluorene
- HTL Hole transport layer 5 nm NPB (N-naphthyl-N-phenyl-4,4'-diaminobiphenyl).
- Emission layer 40 nm ketone (K)
- Dotand lr (ppy) 3 (fac-tris [2-phenylpyridyl] iridium) as a comparative example; in examples according to the invention dopant 1 doped with dopant 2 (degree of doping see table 2).
- Dotand 1 and Dotand 2 are TEB 1 Flrpic or Ir (ppy) 3 ;
- HBL Hole Blocking Layer
- K Ketone
- ETL Electron Conductor
- EBM, TEB, Flrpic, and K are shown below for the sake of clarity.
- the efficiency is increased by the introduction of the dopant Flrpic in a green Ir (ppy) 3 device. At the same time the color improves.
- This concept can also be implemented in a blue-green emitting device with high efficiency, as the example 16 shows.
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- Electroluminescent Light Sources (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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JP2011541133A JP2012512535A (ja) | 2008-12-17 | 2009-11-18 | 有機エレクトロルミネッセンス素子 |
EP09756676A EP2358841A1 (de) | 2008-12-17 | 2009-11-18 | Organische elektrolumineszenzvorrichtung |
US13/000,885 US20110108818A1 (en) | 2008-12-17 | 2009-11-18 | Organic electroluminescence device |
CN2009801251076A CN102076811A (zh) | 2008-12-17 | 2009-11-18 | 有机电致发光器件 |
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DE102008063470.0 | 2008-12-17 | ||
DE102008063470A DE102008063470A1 (de) | 2008-12-17 | 2008-12-17 | Organische Elektrolumineszenzvorrichtung |
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PCT/EP2009/008196 WO2010069442A1 (de) | 2008-12-17 | 2009-11-18 | Organische elektrolumineszenzvorrichtung |
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US (1) | US20110108818A1 (de) |
EP (1) | EP2358841A1 (de) |
JP (1) | JP2012512535A (de) |
KR (1) | KR20110108240A (de) |
CN (1) | CN102076811A (de) |
DE (1) | DE102008063470A1 (de) |
TW (1) | TW201038711A (de) |
WO (1) | WO2010069442A1 (de) |
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Also Published As
Publication number | Publication date |
---|---|
KR20110108240A (ko) | 2011-10-05 |
CN102076811A (zh) | 2011-05-25 |
DE102008063470A1 (de) | 2010-07-01 |
JP2012512535A (ja) | 2012-05-31 |
US20110108818A1 (en) | 2011-05-12 |
EP2358841A1 (de) | 2011-08-24 |
TW201038711A (en) | 2010-11-01 |
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