WO2006122630A1 - Verbindungen für organische elektronische vorrichtungen - Google Patents
Verbindungen für organische elektronische vorrichtungen Download PDFInfo
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- WO2006122630A1 WO2006122630A1 PCT/EP2006/003670 EP2006003670W WO2006122630A1 WO 2006122630 A1 WO2006122630 A1 WO 2006122630A1 EP 2006003670 W EP2006003670 W EP 2006003670W WO 2006122630 A1 WO2006122630 A1 WO 2006122630A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 125
- 239000000463 material Substances 0.000 claims description 70
- -1 C = O Chemical compound 0.000 claims description 63
- 230000005525 hole transport Effects 0.000 claims description 57
- 125000003118 aryl group Chemical group 0.000 claims description 56
- 229910052760 oxygen Inorganic materials 0.000 claims description 31
- 238000002347 injection Methods 0.000 claims description 30
- 239000007924 injection Substances 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical class C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000000412 dendrimer Substances 0.000 claims description 7
- 229920000736 dendritic polymer Polymers 0.000 claims description 7
- 239000011159 matrix material Substances 0.000 claims description 7
- 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 claims description 6
- 229910052787 antimony Inorganic materials 0.000 claims description 6
- 229910052785 arsenic Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 229930192474 thiophene Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 230000000903 blocking effect Effects 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 5
- 125000005259 triarylamine group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229920000547 conjugated polymer Polymers 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Chemical class 0.000 claims description 4
- 150000003462 sulfoxides Chemical class 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 150000008365 aromatic ketones Chemical class 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 150000001716 carbazoles Chemical class 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 150000002987 phenanthrenes Chemical class 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 229910052714 tellurium Inorganic materials 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 150000003577 thiophenes Chemical class 0.000 claims description 2
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 239000002019 doping agent Substances 0.000 abstract description 10
- 230000006872 improvement Effects 0.000 abstract description 3
- 238000001228 spectrum Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 17
- 150000003254 radicals Chemical class 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 238000000859 sublimation Methods 0.000 description 14
- 230000008022 sublimation Effects 0.000 description 14
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 13
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- 239000007983 Tris buffer Substances 0.000 description 12
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 12
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 238000007429 general method Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- NSRBXXWZFGGDPX-UHFFFAOYSA-N 2,8-dibromo-6,6,12,12-tetramethylindeno[1,2-b]fluorene Chemical compound C1=C2C3=CC=C(Br)C=C3C(C)(C)C2=CC2=C1C(C)(C)C1=CC(Br)=CC=C12 NSRBXXWZFGGDPX-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 6
- 238000001194 electroluminescence spectrum Methods 0.000 description 6
- IFYXDUXOWSLKPL-UHFFFAOYSA-N indeno[2,1-a]fluorene-5,11-dione Chemical compound C1=C2C(C=3C(=CC(C4=C5C=CC=CC5=CC=34)=O)C2=CC=C1)=O IFYXDUXOWSLKPL-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 6
- MTUBTKOZCCGPSU-UHFFFAOYSA-N 2-n-naphthalen-1-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 MTUBTKOZCCGPSU-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- OCHLUUFRAVAYIM-UHFFFAOYSA-N bis(9,9'-spirobi[fluorene]-2-yl)methanone Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1(C1=C2)C3=CC=CC=C3C1=CC=C2C(=O)C1=CC=C(C=2C(=CC=CC=2)C23C4=CC=CC=C4C4=CC=CC=C43)C2=C1 OCHLUUFRAVAYIM-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- VMDDQHKTCPOZNM-UHFFFAOYSA-N 6,6,12,12-tetramethylindeno[1,2-b]fluorene Chemical compound C12=CC=CC=C2C(C)(C)C2=C1C=C1C(C)(C)C3=CC=CC=C3C1=C2 VMDDQHKTCPOZNM-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- OPPSYCGZHQVDPM-UHFFFAOYSA-N 2-bromo-4-tert-butyl-1-(4-tert-butylphenyl)benzene Chemical group C1=CC(C(C)(C)C)=CC=C1C1=CC=C(C(C)(C)C)C=C1Br OPPSYCGZHQVDPM-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- CMJXNUDSBHMDJM-UHFFFAOYSA-N n,n-diphenyl-1,1'-spirobi[fluorene]-2'-amine Chemical compound C12=CC=CC=C2C=C2C1=CC=CC21C2=CC3=CC=CC=C3C2=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 CMJXNUDSBHMDJM-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- VOIVTTPPKHORBL-UHFFFAOYSA-N 1-naphthalen-1-ylanthracene Chemical compound C1=CC=C2C(C=3C4=CC5=CC=CC=C5C=C4C=CC=3)=CC=CC2=C1 VOIVTTPPKHORBL-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
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- GWNJZSGBZMLRBW-UHFFFAOYSA-N 9,10-dinaphthalen-1-ylanthracene Chemical compound C12=CC=CC=C2C(C=2C3=CC=CC=C3C=CC=2)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 GWNJZSGBZMLRBW-UHFFFAOYSA-N 0.000 description 2
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910052786 argon Inorganic materials 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
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 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
- 239000003086 colorant Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- MCRSZLVSRGTMIH-UHFFFAOYSA-N ditert-butyl(chloro)phosphane Chemical compound CC(C)(C)P(Cl)C(C)(C)C MCRSZLVSRGTMIH-UHFFFAOYSA-N 0.000 description 2
- 239000012039 electrophile Substances 0.000 description 2
- 230000008570 general process Effects 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- SWGQKRKXZZPKJA-UHFFFAOYSA-N indeno[2,1-a]fluorene-1,2-diamine Chemical class C1=CC=C2C=C3C4=CC5=C(N)C(N)=CC=C5C4=CC=C3C2=C1 SWGQKRKXZZPKJA-UHFFFAOYSA-N 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-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
- 239000002243 precursor Substances 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical class C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 description 1
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- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
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- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- C07D215/38—Nitrogen atoms
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- C07D279/18—[b, e]-condensed with two six-membered rings
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Definitions
- the present invention describes novel compounds and their use in organic electronic devices.
- the operating voltage is quite high, especially with fluorescent OLEDs, and should therefore be further reduced to improve power efficiency. This is especially important for mobile applications.
- organic electroluminescent devices which contain certain compounds listed below as blue-emitting dopants in a host material, have significant improvements over the prior art. With these materials it is possible to obtain longer lifetimes with higher efficiency. In addition, unlike prior art materials, these compounds can also be sublimated in significant quantities without appreciable decomposition, and are therefore much easier to handle than prior art materials.
- Ar 1 , Ar 2 , Ar 3 is the same or different at each occurrence and is an aryl or heteroaryl group having 5 to 24 aromatic ring atoms, which may be substituted by one or more R 1 ;
- Ar 4 , Ar 5 , Ar 6 , Ar 7 is identical or different at each occurrence and is an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 1 ;
- R 2 is the same or different at each occurrence, H or an aliphatic or aromatic hydrocarbon radical having 1 to 20 carbon atoms;
- q, r is 1 for each occurrence, if the corresponding central atom of the group Y or Z is an element of the 5th main group, and is 0 for each occurrence, if the corresponding central atom of the group Y or Z is an element of the 4th or 6th main group;
- s is 1, 2 or 3;
- An aryl group or a heteroaryl group in the context of this invention is understood as meaning an aromatic group or heteroaromatic group having a common aromatic electron system, where an aryl group has 6 to 24 C atoms and a heteroaryl group has 2 to 24 C atoms and a total of at least 5 aromatic ring atoms includes.
- the heteroatoms are preferably selected from N, O and / or S.
- this may be a simple homo- or heterocycle, for example benzene, pyridine, thiophene, etc., or it may be a fused aromatic ring system which at least two aromatic or heteroaromatic rings, for example benzene rings, are "fused" together, ie fused together by annulation, ie have at least one common edge and thus also a common aromatic system
- systems such as naphthalene, anthracene, phenanthrene, pyrene, etc. as aryl groups and quinoline, acridine, benzothiophene, carbazole, etc. are to be seen as heteroaryl groups in the context of this invention, while, for example, biphenyl, fluorene, spirobifluorene, etc. are not aryl groups, since these are separate aromatic electron systems.
- An aromatic ring system in the sense of this invention contains 6 to 40 carbon atoms in the ring system.
- a heteroaromatic ring system in the sense of this invention contains 2 to 40 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of the 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 several aryls are also present - or heteroaryl groups by a short, non-aromatic unit (less than 10% of the atoms other than H, preferably less than 5% of the atoms other than H), such as.
- a C, N or O atom can be interrupted.
- systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ethers, etc. are also to be understood as aromatic ring systems in the context of this invention.
- a C 1 - to C 40 -alkyl group in which individual H atoms or C 1 -C 4 groups may also 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, cyclopentyl, n -hexyl, cyclohexyl, n -heptyl, cycloheptyl, n-octyl, cyclooctyl , 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, cyclopen
- a C 1 to C 40 alkoxy group is more preferably understood as meaning methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy or 2-methylbutoxy.
- aryl or heteroaryl group which may be monovalent or bivalent depending on the use, which may be substituted in each case with the abovementioned radicals R 1 and which may be linked via any position on the aromatic or heteroaromatic, are especially groups which are derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, Indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo
- aromatic and heteroaromatic ring systems are understood to mean in particular biphenyls, terphenyls, fluorene, spirobifluorene, dihydrophenanthrene, tetrahydropyrenes and cis- or trans-indenofluorene, in addition to the abovementioned aryl and heteroaryl groups.
- the direct link between Y, Ar 1 , Ar 2 , Ar 3 and Z is particularly preferably via the para-positions of the benzene (or the corresponding positions of the other aromatics).
- Ar 4 , Ar 5 , Ar 6 and Ar 7 are identical or different at each occurrence of phenyl, 1-naphthyl or 2-naphthyl, which may each be substituted by one or two radicals R 1 .
- R 1 is identical or different at each occurrence for H, F, CN, a straight-chain alkyl group having 1 to 5 C atoms or a branched alkyl group having 3 to 5 C
- radicals R 1 may be, or a monovalent aryl or heteroaryl group having 5 to 16 aromatic ring atoms which may be substituted with one or more non-aromatic radicals R 1 ; it is also possible for two radicals R 1 to form a ring system with one another.
- radicals R 1 are selected from straight-chain alkyl groups having 1 to 4 C atoms or branched alkyl groups having 3 or 4 C atoms, in particular methyl groups, or phenyl groups; In this case, two or more radicals R 1 together form a ring system.
- radicals R 1 together form a ring system, a spiro-structure is thereby formed. This may be particularly preferred when the radicals R 1 are phenyl groups. This then results in structures of the general formula (1e),
- Examples of preferred compounds according to formula (1) are the structures (1) to (104) depicted below.
- Another object of the invention are thus conjugated, partially conjugated and non-conjugated polymers, oligomers or dendrimers containing one or more compounds of formula (1), wherein one or more radicals R 1 represent bonds of the compound of formula (1) to the polymer or dendrimer.
- the unit according to formula (1) is preferably bonded via the groups Ar 4 , Ar 5 , Ar 6 and / or Ar 7 into the polymer.
- These polymers may contain additional repeat units. These further repeating units are preferably selected from the group consisting of fluorenes (for example according to EP 842208 or WO 00/22026), spirobifluorenes (for example according to EP 707020, EP 894107 or EP 04028865.6), triarylamines, para-phenylenes (for example in accordance with WO 92/18552), carbazoles (for example according to WO 04/070772 and WO 04/113468), thiophenes (for example according to EP 1028136), dihydrophenanthrenes (for example according to US Pat WO 05/014689), indenofluorenes (for example according to WO 04/041901 and WO 04/113412), aromatic ketones (for example according to WO 05/040302), phenanthrenes (for example according to WO 05/104264) and / or metal complexes, in particular ortho-metallated iridium complexes. It
- the compounds of the invention can according to the expert known synthesis steps, such as. Bromination, Suzuki coupling,
- the indenofluorene precursors can be prepared as depicted in Synthetic Scheme 1: by Suzuki coupling of a benzoic boronic acid and 1,4-dibromo-2,5-bis (methylcarboxylate) benzene followed by ring closure on exposure to a strong acid and reduction the unsubstituted trans indenofluorene, which can be alkylated with alkylating agents. This can either be halogenated, for example brominated, or be converted by nitration and reduction into the corresponding amino compound.
- the synthesis of bis-diarylamino-indenofluorenes can be accomplished by Hartwig-Buchwald coupling of the dibromo compound as shown in Synthetic Scheme 2.
- Analogously convertible electrophiles AsCl 3 , SbCl 3 , BiCl 3 , ArylPCI, Aryl 2 PCI, SCI 2 , SOCl 2 , SO 2 Cl 2 ,
- the compounds according to formula (1) can be used in organic electroluminescent devices.
- the exact use of the compounds depends on the substituents and in particular on the choice of the groups Y and Z, but also on the choice of the groups X 1 to X 4 .
- the compound according to formula (1) is used in the emitting layer, preferably used in admixture with at least one further compound. It is preferable that the compound of the formula (1) in the mixture is the emitting compound (the dopant). This is especially true when the symbols Y and Z are nitrogen.
- Preferred host materials are organic compounds whose emission is shorter than that of the compound of formula (1) or which do not emit at all.
- the proportion of the compound of formula (1) in the mixture of the emitting layer is between 0.1 and 99.0 wt.%, Preferably between 0.5 and 50.0 wt.%, Particularly preferably between 1.0 and 20.0 wt.%, In particular between 1.0 and 10.0 wt. %. Accordingly, the proportion of host material in the layer is between 1.0 and 99.9 % By weight, preferably between 50.0 and 99.5% by weight, more preferably between 80.0 and 99.0% by weight, in particular between 90.0 and 99.0% by weight.
- Preferred host materials are selected from the classes of the oligo- arylenes (eg 2,2 ', 7,7'-tetraphenyl-spirobifluorene according to EP 676461 or dinaphthylanthracene), in particular the oligo-arylenes containing condensed aromatic groups, the oligo-arylenevinylenes (eg DPVBi or spiro-DPVBi according to EP 676461), the polypodal metal complexes (eg according to WO 04/081017), the hole-conducting compounds (eg according to WO 04/058911), the electron-conducting compounds, in particular Ketones, phosphine oxides, sulfoxides, etc. (eg according to WO 05/084081 or WO 05/084082), the atropisomers (eg according to the unpublished application EP 04026402.0) or the boronic acid derivatives (e.g.,
- Particularly preferred host materials are selected from the classes of the oligoarylenes containing naphthalene, anthracene and / or pyrene or atropisomers of these compounds, the oligo- arylenvinylene, the ketones, the phosphine oxides and the sulfoxides.
- Very particularly preferred host materials are selected from the classes of oligoarylenes containing anthracene and / or pyrene or atropisomers of these compounds, the phosphine oxides and the sulfoxides.
- the compounds according to formula (1) are used as hole transport material and / or as hole injection material. This is especially true when the symbols Y and Z and / or the symbols X 1 to X 4 are nitrogen.
- the compounds are then preferably used in a hole transport layer and / or in a hole injection layer.
- a hole injection layer in the sense of this invention is a layer which is directly adjacent to the anode.
- a hole transport layer in the sense of this invention is a layer that lies between the hole injection layer and the emission layer.
- the compounds according to formula (1) are used as hole-transporting or hole-injecting material, it may be preferable if they are doped with electron-accepting compounds, for example with F 4 -TCNQ or with compounds as described in EP 1476881 or EP 1596445.
- the compound according to formula (1) is used as hole transport material in a hole transport layer, a proportion of 100% may also be preferred, ie the use of this compound as a pure material.
- compounds of the formula (1) can be employed either as an emissive unit and / or as a hole-transporting unit and / or as an electron-transporting unit.
- organic electroluminescent devices characterized in that a plurality of emitting compounds are used in the same layer or in different layers, wherein at least one of these compounds has a structure according to formula (1). More preferably, these compounds have a total of several emission maxima between 380 nm and 750 nm, so that overall white emission results, d. H.
- at least one further emitting compound which can fluoresce or phosphoresce and which emits yellow, orange or red light is also used.
- broadband emitters can be used for white emitting OLEDs.
- the organic electroluminescent device may contain further layers. These may be, for example: hole injection layer, hole transport layer, hole blocking layer, electron transport layer, electron injection layer and / or a charge generation layer (T.Matsumoto et al., Multiphoton Organic EL Device Having Charge Generation Layer, IDMC 2003, Taiwan, Session 21 OLED (5)) , However, it should be noted at this point that not necessarily each of these layers must be present. Thus, particularly when using compounds according to formula (1) with electron-conducting host materials, very good results continue to be obtained if the organic electroluminescent device does not contain a separate electron transport layer and the emitting layer directly adjoins the electron injection layer or the cathode.
- the host material can also simultaneously serve as an electron transport material in an electron transport layer. It may likewise be preferred if the organic electroluminescent device does not contain a separate hole transport layer and the emitting layer directly adjoins the hole injection layer or the anode. Furthermore, it may be preferred if the compound of formula (1) is used simultaneously as a dopant in the emitting layer and as a hole-conducting compound (as a pure substance or as a mixture) in a hole transport layer and / or in a hole injection layer.
- an organic electroluminescent device characterized in that one or more layers are coated with a sublimation process.
- the materials are vacuum sublimation mbar, preferably less than 10 "6 mbar, particularly preferably less than 10" -7 mbar at a pressure below 10 -5 jn.
- 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 ⁇ 5 mbar and 1 bar.
- an organic electroluminescent device characterized in that one or more layers of solution, such. B. by spin coating, or with any printing process, such.
- screen printing flexographic printing or offset printing, but more preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing (inkjet printing), are produced. For this are soluble
- the compounds according to the invention When used in organic electroluminescent devices, the compounds according to the invention have the following surprising advantages over the prior art:
- the compounds can be sublimated well and without significant decomposition, thereby being easier to process and therefore more suitable for use in OLEDs than prior art materials. Without wishing to be bound by any particular theory, we suspect that the higher thermal stability is due to the absence of olefinic double bonds. In the present application text and also in the examples below, the use of the compounds according to the invention with respect to OLEDs and the corresponding displays is aimed at. Despite this limitation of the description, it is possible for the skilled person without further inventive step to use the compounds of the invention for other uses in other electronic devices, such.
- O-FETs organic field effect transistors
- O-TFTs organic thin-film transistors
- O-LETs organic light-emitting transistors
- O-ICs organic integrated circuits
- O-SCs organic solar cells
- O-FQDs organic FeId quench devices
- LOCs light-emitting electrochemical cells
- O-lasers organic laser diodes
- the starting materials can be obtained from the companies ALDRICH or ABCR (palladium (II) acetate, di-tert-butyl-chlorophosphine, amines, inorganics, solvents).
- ALDRICH or ABCR palladium (II) acetate, di-tert-butyl-chlorophosphine, amines, inorganics, solvents.
- 6,12-Dihydro- [1,2b] indenofluorene is prepared according to Hadizad et al., Org. Lett. 2005, 7 (5), 795-797
- [1, 2b] indenofluorene-6,12-dione is prepared according to Deuschel et al., HeIv. Chim.
- the preparation is analogous to the preparation of 9,9-dimethylfluorene from 6,12-dihydro-indeno [1, 2b] fluorene, dimethyl sulfate and sodium hydroxide solution according to JP 08113542. Yield 86.0% d. Th .; Purity 98% n. 1 H-NMR.
- EXAMPLE 46 Production of OLEDs with Indenofluorene Diamines as Hole Injection Material or Hole Transport Material in Fluorescent OLEDs
- OLEDs are produced by a general process according to WO 04/058911, which in individual cases depends on the respective conditions (eg layer thickness variation, for optimum efficiency or to achieve color) is adjusted.
- HIL Hole Injection Layer 20 nm PEDOT (spun from water, supplied by H.C.
- HTM1 Hole transport layer (HTM1) B2 (compound according to Example 2) or B1 (compound according to Example 1) or B9 (compound according to Example 9) or B15 (compound according to Example 15) or B37 (Compound according to Example 37) or: as Comparative Example 4.4 ', 4 "-Tris (N-1-naphthyl-N-phenylamino) -triphenylamine
- HTM2 Hole transport layer 20 nm NPB (N-naphthyl-N-phenyl-4,4'-diaminobiphenyl)
- the OLEDs can also be produced without PEDOT as hole injection layer. In these cases, then the inventive
- Indenofluorene-diamine derivative the hole injection compound. These OLEDs show comparably good properties.
- OLEDs are characterized by default; for this the electroluminescence spectra, the efficiency (measured in cd / A) and the Power efficiency (measured in Im / W) as a function of the brightness, calculated from the current-voltage-brightness characteristics (lUL characteristics).
- Table 1 summarizes the results of some OLEDs (Examples 47 to 62) in which the layer thickness of the hole transport layer (HTM1) is varied.
- HTM1 hole transport layer
- NaphDATA is used in Comparative Examples.
- the host material H1 is 9,10-bis (1-naphthyl) anthracene, D1 is used as the dopant. Both are shown below:
- OLEDs containing the hole transport material (HTM1) according to the invention show a significantly lower operating voltage than with naphDATA according to the prior art as hole transport material. Furthermore, the operating voltage is independent of the layer thickness of the hole transport layer. This property is of great advantage for the construction of full-color displays, since the thickness of the pixels of the primary colors blue, green and red can be made the same by varying the layer thickness of the hole-transport layer.
- the hole transport material according to the invention can therefore serve here as a thickness compensation layer without adversely affecting the electrooptical properties of the device. As can be seen from the comparative examples, this is for hole transport material (NaphDATA) according to the prior art Technology not the case: Here, with a larger layer thickness of the hole transport layer, a significantly higher operating voltage is required.
- OLEDs takes place according to a general method according to WO 04/093207, which in individual cases is adapted to the respective conditions (eg layer thickness variation in order to achieve optimum efficiency or color).
- HIL Hole Injection Layer 20 nm PEDOT (spin-on from water, supplied by H.C. Starck, Goslar, Germany; poly (3,4-ethylenedioxy-2,5-thiophene))
- Hole transport layer (HTM1) B2 compound according to Example 2 or: as Comparative Example 4,4 ', 4 "-Tris (N-1-naphthyl-N-phenylamino) -triphenylamine
- HTM2 Hole transport layer 20 nm (evaporated, S-TAD prepared according to WO99 / 12888, 2,2 ', 7 ) 7 I tetrakis
- Emission layer 40 nm Ketone-1 (bis (9,9'-spirobifluorene-2-yl) ketone (evaporated, synthesized acc
- the OLEDs can also be produced without PEDOT as hole injection layer.
- the inventive indenofluorene-diamine derivative is the hole injection compound.
- OLEDs are characterized by default; For this purpose, the electroluminescence spectra, the efficiency (measured in cd / A) and the power efficiency (measured in Im / W) as a function of the brightness, calculated from current-voltage-brightness characteristics (IUL characteristics) are determined.
- Table 2 summarizes the results of some OLEDs (Examples 64 to 68) in which the layer thickness of the hole transport layer (HTM1) is varied.
- HTM1 hole transport layer
- NaphDATA is used in Comparative Examples.
- OLEDs containing the hole transport material (HTM1) according to the invention show a significantly lower operating voltage and a higher efficiency than with naphDATA according to the prior art as hole transport material. Furthermore, the operating voltage is independent of the layer thickness of the hole transport layer.
- the hole transport material according to the invention can thus serve here as a thickness compensation layer without adversely affecting the electrooptical properties of the device.
- Example 69 Preparation of OLEDs with Indenofluorenketonen or Indenofluorenphosphinoxiden as an electron transport material in phosphorescent OLEDs
- OLEDs takes place according to a general method according to WO 04/093207, which in individual cases is adapted to the respective conditions (eg layer thickness variation in order to achieve optimum efficiency or color).
- HIL Hole injection layer 20 nm PEDOT (spun from water, referred to by HC Starck, Goslar, Germany; Poly (3,4-ethylenedioxy-2,5-thiophene))
- Hole Transport Layer (HTM1) 20nm 4,4 ', 4 "-tris (N-1-naphthyl-N-phenylamino) -triphenylamine (abbreviated as NaphDATA purchased from SynTec)
- Hole Transport Layer (HTM2) 20nm S-TAD (evaporated; -TAD prepared according to WO99 / 12888; 2,2 ', 7, T-tetrakis (diphenylamino) -spirobifluorene)
- Emission layer 40 nm ketone-1 (bis (9,9'-spirobifluorene-2-yl) ketone (vapor-deposited, synthesized according to WO 04/093207), doped with 15% triplet
- OLEDs are characterized by default; For this purpose, the electroluminescence spectra, the efficiency (measured in cd / A) and the power efficiency (measured in Im / W) as a function of the brightness, calculated from current-voltage-brightness characteristics (ILJL characteristics) are determined.
- Table 3 summarizes the results of some OLEDs (Examples 70 to 73) in which the electron transport layer (ETL) is varied.
- ETL electron transport layer
- Alq is used in Comparative Examples.
- the emitter E1 and the matrix material ketone-1 are shown in Example 63.
- Example 74 Preparation of red-phosphorescent OLEDs with indenofluoro ketones or indenofluorenephosphine oxides as triplet matrix material
- OLEDs takes place according to a general method according to WO 04/093207, which in individual cases is adapted to the respective conditions (eg layer thickness variation in order to achieve optimum efficiency or color).
- HIL Hole Injection Layer 20 nm PEDOT (spun from water, supplied by H.C.
- HTM1 Hole Transport Layer (HTM1) 20nm 4,4 ', 4 "-tris (N-1-naphthyl-N-phenylamino) -triphenylamine (abbreviated as
- HTM2 Hole transport layer 20 nm S-TAD (vapor-deposited; S-TAD prepared according to WO99 / 12888; 2,2 ', 7, T-tetrakis (diphenylamino) -spirobifluorene)
- Emission layer 20 nm B19 (compound according to Example 26) or 20 nm B26 (compound according to Example 31) or 20 nm B31 (compound according to Example 31) or ketone 1 (bis (9,9'-spirobifluoren-2-yl) ketone ( vapor-deposited, synthesized according to WO 04/093207) (comparison standard), each doped with 10% triplet emitter E2 (synthesized according to WO 05/033244)
- OLEDs Cathode 1 nm LiF, then 150 nm Al. These OLEDs are characterized by default; For this purpose, the electroluminescence spectra, the efficiency (measured in cd / A) and the power efficiency (measured in Im / W) as a function of the brightness, calculated from current-voltage-brightness characteristics (IUL characteristics) are determined.
- Table 4 summarizes the results of some OLEDs (Examples 75 to 78) in which the triplet matrix material of the emission layer (EML) is varied.
- EML emission layer
- ketone-1 is used in Comparative Examples.
- the emitter E1 and the triplet matrix material ketone-1 are shown below for the sake of clarity:
- OLEDs takes place according to a general method according to WO 04/058911, which in individual cases is adapted to the respective circumstances (eg layer thickness variation in order to achieve optimum efficiency or color).
- HIL Hole Injection Layer 20 nm PEDOT (spin-on from water, supplied by H.C. Starck, Goslar, Germany; poly (3,4-ethylenedioxy-2,5-thiophene))
- Hole transport layer (HTM1) 20 nm B2 (compound according to Example 2); Hole transport layer (HTM2) 20 nm NPB (N-naphthyl-N-phenyl-4,4 1 -diaminobiphenyl)
- OLEDs are characterized by default; For this purpose, the electroluminescence spectra, the efficiency (measured in cd / A) and the power efficiency (measured in Im / W) as a function of the brightness, calculated from current-voltage-brightness characteristics (ILJL characteristics) are determined.
- OLEDs containing the dopants B2 according to the invention exhibit efficient deep blue emission.
- B17 compound according to Example 17
- the internal quantum efficiency is close to 100%.
- Example 87 Bis (N- (4-tert-butylphenyl) -N- (4-bromophenyl) amino) -6,6,12,12-tetraocty-1-6,12-dihydroindeno [1, 2b] fluorene
- 6,12, dihydroindeno [1, 2b] fluoren can be used as monomer for the polymerization, for example for the polymerization according to Suzuki or according to Yamamoto.
- This compound is particularly well suited for incorporation in conjugated or partially conjugated polymers and is particularly useful as a hole-conducting compound in these polymers.
- the preparation is carried out analogously to the preparation of 9,9-dimethylfluorene from 12,15-dihydro-6H-diindeno [1, 2-b: 2 ', 1' -h] fluorene (Stauner et ai, Helv Chim Acta, 1970,.. 53 (6), 1311), dimethyl sulfate and sodium hydroxide solution according to JP 08113542. Yield 61.0% of theory Th .; Purity 97% n. 1 H-NMR.
- the reaction mixture is concentrated in vacuo to 200 ml volume, treated with 1000 ml of ethanol, the precipitate is filtered off with suction, stirred with 1000 ml of hot ethanol, filtered off with suction, washed three times with 300 ml of ethanol and dried in vacuo. Yield: 139.0 g (167 mmol), 83.6% of theory. Th .; Purity: 98% n. 1 H-NMR.
- EXAMPLE 91 Production of OLEDs with Indenofluorene Tetramines or Hexamines as Hole Injection Material or Hole Transport Material in Fluorescent OLEDs
- OLEDs are produced by a general process according to WO 04/058911, which in individual cases depends on the respective conditions (eg layer thickness variation to achieve optimum efficiency or color) is adjusted.
- HIL Hole Injection Layer
- PEDOT spun from water, obtained from HC Starck, Goslar, Germany
- HTM2 Hole transport layer 20 nm NPB (N-naphthyl-N-phenyl-4,4 1 -diaminobiphenyl)
- Emission layer 30 nm, doped layer of 9,10-bis (1-naphthylanthracene) as host material (abbreviated H1), doped with 5% Tris [4- (2,2-)] diphenylvinyl) -phenyl] amine as dopant
- the OLEDs can also be produced without PEDOT as hole injection layer. In these cases, the indenofluorene tetramine or hexamine derivative according to the invention is then the hole injection compound. These OLEDs show comparably good properties.
- OLEDs are characterized by default; For this purpose, the electroluminescence spectra, the efficiency (measured in cd / A) and the power efficiency (measured in Im / W) as a function of the brightness, calculated from current-voltage-brightness characteristics (LUL characteristic curves) are determined.
- Table 6 summarizes the results of some OLEDs (Examples 92 to 94) in which the layer thickness of the hole transport layer (HTM1) is varied.
- HTM1 hole transport layer
- NaphDATA is used in Comparative Examples.
- the host material H1 is 9,10-bis (1-naphthyl) anthracene, D1 is used as the dopant. Both are shown below:
- Host H1 Dotand D1 As can be seen from Examples 92 and 93 of the invention in Table 6, OLEDs containing the hole transport material (HTM1) according to the invention show a significantly higher efficiency than with naphDATA according to the prior art as hole transport material. Furthermore, the operating voltage is independent of the layer thickness of the hole transport layer. This property is of great advantage for the construction of full-color displays, since the thickness of the pixels of the primary colors blue, green and red can be made the same by varying the layer thickness of the hole-transport layer.
- the hole transport material according to the invention can therefore serve here as a thickness compensation layer without adversely affecting the electrooptical properties of the device. As can be seen from the comparative examples, this is not the case for hole transport material (NaphDATA) according to the prior art: Here, with a larger layer thickness of the hole transport layer, a significantly higher operating voltage is required.
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JP2008511579A JP5237090B2 (ja) | 2005-05-20 | 2006-04-21 | 有機電子素子のための化合物 |
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MX2007014449A MX2007014449A (es) | 2005-05-20 | 2006-04-21 | Compuestos para dispositivos electronicos organicos. |
US11/914,824 US8852756B2 (en) | 2005-05-20 | 2006-04-21 | Materials for organic electroluminescent devices |
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EP06724488.9A EP1883688B1 (de) | 2005-05-20 | 2006-04-21 | Verbindungen für organische elektronische vorrichtungen |
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AU2006246743A1 (en) | 2006-11-23 |
CA2608765A1 (en) | 2006-11-23 |
RU2007146793A (ru) | 2009-06-27 |
CA2608765C (en) | 2014-01-28 |
US8852756B2 (en) | 2014-10-07 |
AU2006246743B2 (en) | 2012-05-31 |
RU2419648C2 (ru) | 2011-05-27 |
CN101228250B (zh) | 2016-08-10 |
EP1883688A1 (de) | 2008-02-06 |
DE102005023437A1 (de) | 2006-11-30 |
TWI428424B (zh) | 2014-03-01 |
BRPI0610859A2 (pt) | 2010-08-03 |
MX2007014449A (es) | 2008-02-07 |
KR101346467B1 (ko) | 2014-01-02 |
KR20080015865A (ko) | 2008-02-20 |
JP5237090B2 (ja) | 2013-07-17 |
JP2008545630A (ja) | 2008-12-18 |
US9461249B2 (en) | 2016-10-04 |
US20150031896A1 (en) | 2015-01-29 |
CN101228250A (zh) | 2008-07-23 |
EP1883688B1 (de) | 2018-04-11 |
US20080220285A1 (en) | 2008-09-11 |
TW200706636A (en) | 2007-02-16 |
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