WO2011066898A1 - Elektronische vorrichtung enthaltend metallkomplexe - Google Patents
Elektronische vorrichtung enthaltend metallkomplexe Download PDFInfo
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- WO2011066898A1 WO2011066898A1 PCT/EP2010/006821 EP2010006821W WO2011066898A1 WO 2011066898 A1 WO2011066898 A1 WO 2011066898A1 EP 2010006821 W EP2010006821 W EP 2010006821W WO 2011066898 A1 WO2011066898 A1 WO 2011066898A1
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- 229910052751 metal Inorganic materials 0.000 title claims abstract description 48
- 239000002184 metal Substances 0.000 title claims abstract description 48
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- 125000003118 aryl group Chemical group 0.000 claims description 70
- 150000001875 compounds Chemical class 0.000 claims description 52
- -1 1,2-vinylene Chemical group 0.000 claims description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 229910052698 phosphorus Inorganic materials 0.000 claims description 29
- 125000004122 cyclic group Chemical group 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 23
- 230000007935 neutral effect Effects 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- 125000001931 aliphatic group Chemical group 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 18
- 239000011159 matrix material Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
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- 229910052802 copper Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 6
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- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 6
- 150000003003 phosphines Chemical class 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 5
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- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims description 5
- 150000007942 carboxylates Chemical class 0.000 claims description 5
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- 230000005525 hole transport Effects 0.000 claims description 5
- 150000004678 hydrides Chemical class 0.000 claims description 5
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 5
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- 239000012948 isocyanate Substances 0.000 claims description 5
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 5
- 125000003367 polycyclic group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
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- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004986 diarylamino group Chemical group 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
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- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical class C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 claims description 3
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- 238000010791 quenching Methods 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
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- 125000005259 triarylamine group Chemical group 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
- 239000013256 coordination polymer Substances 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 229910052745 lead Inorganic materials 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 150000004756 silanes Chemical class 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 150000003918 triazines Chemical class 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 150000003751 zinc Chemical class 0.000 claims description 2
- 238000005401 electroluminescence Methods 0.000 claims 3
- 125000005240 diheteroarylamino group Chemical group 0.000 claims 2
- DLZKBXWBIMOUJI-UHFFFAOYSA-N 4,5-dihydro-3h-azaborole Chemical compound C1CB=NC1 DLZKBXWBIMOUJI-UHFFFAOYSA-N 0.000 claims 1
- 150000001638 boron Chemical class 0.000 claims 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 150000007858 diazaphosphole derivatives Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
- 239000000243 solution Substances 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000010949 copper Substances 0.000 description 34
- 239000000203 mixture Substances 0.000 description 34
- 239000007787 solid Substances 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000012074 organic phase Substances 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 150000003254 radicals Chemical class 0.000 description 24
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
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- 238000000034 method Methods 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
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- 238000001816 cooling Methods 0.000 description 12
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- 238000003756 stirring Methods 0.000 description 10
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- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 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 9
- 0 C*1cc(****2)c2[o]1 Chemical compound C*1cc(****2)c2[o]1 0.000 description 8
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- 229910021645 metal ion Inorganic materials 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
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- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
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- 150000001721 carbon Chemical group 0.000 description 6
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000011133 lead Substances 0.000 description 5
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000011135 tin Substances 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical compound C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
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- 229910052741 iridium Inorganic materials 0.000 description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 4
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- KQJYQGMOBWPQGQ-UHFFFAOYSA-N 2-[1-(methoxymethyl)imidazol-2-yl]pyridine Chemical compound COCN1C=CN=C1C1=CC=CC=N1 KQJYQGMOBWPQGQ-UHFFFAOYSA-N 0.000 description 3
- KFTFTNLNHUOACP-UHFFFAOYSA-N 2-[fluoro-(6-methylpyridin-2-yl)methyl]-6-methylpyridine Chemical compound CC1=CC=CC(C(F)C=2N=C(C)C=CC=2)=N1 KFTFTNLNHUOACP-UHFFFAOYSA-N 0.000 description 3
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- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
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- 238000002360 preparation method Methods 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
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- AELPIDFIURROQN-UHFFFAOYSA-N (6-bromopyridin-2-yl)-bis(6-methylpyridin-2-yl)methanol Chemical compound CC1=CC=CC(C(O)(C=2N=C(C)C=CC=2)C=2N=C(Br)C=CC=2)=N1 AELPIDFIURROQN-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
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- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- HABOMNOJYJNVHE-UHFFFAOYSA-N 1h-indol-7-ylboronic acid Chemical compound OB(O)C1=CC=CC2=C1NC=C2 HABOMNOJYJNVHE-UHFFFAOYSA-N 0.000 description 2
- FEYDZHNIIMENOB-UHFFFAOYSA-N 2,6-dibromopyridine Chemical compound BrC1=CC=CC(Br)=N1 FEYDZHNIIMENOB-UHFFFAOYSA-N 0.000 description 2
- CHWJBMPGMPUBCD-UHFFFAOYSA-N 2-(1-pyridin-2-ylethyl)pyridine Chemical compound C=1C=CC=NC=1C(C)C1=CC=CC=N1 CHWJBMPGMPUBCD-UHFFFAOYSA-N 0.000 description 2
- SZXUTTGMFUSMCE-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)pyridine Chemical compound C1=CNC(C=2N=CC=CC=2)=N1 SZXUTTGMFUSMCE-UHFFFAOYSA-N 0.000 description 2
- TZXCNVCUQLKGGQ-UHFFFAOYSA-N 2-(methoxymethyl)-6-methylpyridine Chemical compound COCC1=CC=CC(C)=N1 TZXCNVCUQLKGGQ-UHFFFAOYSA-N 0.000 description 2
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- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- PORFVJURJXKREL-UHFFFAOYSA-N trimethylstibine Chemical compound C[Sb](C)C PORFVJURJXKREL-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 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
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
- QZBJYTDDWVXFDF-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)arsane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1[As](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F QZBJYTDDWVXFDF-UHFFFAOYSA-N 0.000 description 1
- FQLSDFNKTNBQLC-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)phosphane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1P(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F FQLSDFNKTNBQLC-UHFFFAOYSA-N 0.000 description 1
- QYWFCUVQKBNIRJ-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)stibane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1[Sb](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F QYWFCUVQKBNIRJ-UHFFFAOYSA-N 0.000 description 1
- NZJQTVDLVPHKGY-UHFFFAOYSA-N tritert-butylstibane Chemical compound CC(C)(C)[Sb](C(C)(C)C)C(C)(C)C NZJQTVDLVPHKGY-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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
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Definitions
- the present application relates to electronic devices, in particular organic electroluminescent devices containing metal complexes and the metal complexes preferred for use.
- OLEDs organic electroluminescent devices
- OLEDs organic electroluminescent devices
- organometallic complexes which exhibit phosphorescence instead of fluorescence are increasingly being used as emitting materials (M.A. Baldo et al., Appl. Phys. Lett. 1999, 75, 4-6).
- organometallic compounds For quantum mechanical reasons, up to four times energy and power efficiency is possible using organometallic compounds as phosphorescence emitters.
- organometallic compounds For quantum mechanical reasons, up to four times energy and power efficiency is possible using organometallic compounds as phosphorescence emitters.
- organometallic compounds as phosphorescence emitters.
- OLEDs showing triplet emissions are still in need of improvement.
- the physical properties of phosphorescent OLEDs in terms of efficiency, operating voltage and lifetime are still not sufficient for the use of triplet emitters in high-quality and durable electroluminescent devices.
- iridium and platinum complexes are used in phosphorescent OLEDs as triplet emitters in particular.
- these have the disadvantage that these are metals with a very low frequency and therefore also corresponding to expensive metals. To protect the natural resources of these metals, it would therefore be desirable to have emitters based on other metals available.
- Another disadvantage of the commonly used iridium and platinum complexes is that they are mostly organometallic complexes with metal-carbon bonds. Such metal-carbon bonds are sometimes difficult to access synthetically. Furthermore, these complexes sometimes have only a low thermal stability.
- the object of the present invention is therefore to provide metal complexes which are suitable as emitters or else as matrix materials or in other functions for use in OLEDs, where they lead to high efficiencies and long lifetimes and which are readily accessible synthetically.
- Organic electroluminescent devices containing these complexes as well as the preferred metal complexes are therefore the subject of the present invention.
- the subject of the present invention is thus an electronic device comprising anode, cathode and at least one compound according to formula (1),
- atom which is part of the heterocyclic group, binds to M; or is a cyclic or heterocyclic group having 1 to 20 C atoms, which binds to M via an exocyclic donor atom and which may be substituted by one or more R radicals;
- L2, L3 are, identically or differently, each occurrence a coordinating group which may be substituted by one or more radicals R and which binds to nitrogen via nitrogen, phosphorus, sulfur or a neutral carbon atom, where L2 and / or L3 are also the same or different L1 can be;
- L4 is any ligand which coordinates to the metal M and which may be substituted by one or more R; in this case, L4 can also be replaced by a direct bond or by a divalent group - (Y) n - with one or more of the partial ligands
- a partial ligand in the ligand of the formula (2) is understood as meaning the groups L1, L2 and L3, ie in each case the individual arms of the polypodal ligand, which respectively coordinate to the metal M and pass over the bridgehead V and if linked via Y
- the ligand L4 then binds correspondingly simultaneously to 2 or 3 metals M.
- a donor atom is understood to mean an atom which has at least one free electron pair and is therefore capable of binding to a metal atom or metal ion.
- the donor atom can be neutral or negatively charged.
- an exocyclic donor atom is understood to mean a donor atom which is not part of the cyclic or heterocyclic group L 1 but which is bonded as a substituent to L 1 and which has at least one free electron pair and is thereby able to bind to one To bind metal atom.
- exocyclic donor atoms are oxygen in the form of a phenolate, sulfur in the form of a thiolate, nitrogen in the form of an amine, imine, amide or imide and phosphorus in the form of a phosphine.
- An aryl group in the sense of this invention contains 6 to 60 C atoms;
- a heteroaryl group contains 2 to 60 C atoms and at least one 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.
- 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,
- Carbene in the context of this invention is a cyclic group which binds to the metal via a neutral carbon atom.
- the cyclic group may be saturated or unsaturated.
- Arduido carbenes ie those carbenes in which two nitrogen atoms are bonded to the carbene C atom, are preferred here.
- An aromatic ring system in the sense of this invention contains 6 to 60 carbon atoms in the ring system.
- a heteroaromatic ring system in the sense of this invention contains 2 to 60 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 Heteroaryl groups by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as.
- N or O atom may be interrupted.
- systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc. are to be understood as aromatic ring systems in the context of this invention, and also systems in which two or more aryl groups, for example by a linear or cyclic alkyl group or interrupted by a silyl group.
- the radicals methyl, ethyl, n-propyl, i-propyl are preferably selected from C to C 40 -alkyl groups in which individual H atoms or CH 2 groups may be substituted by the abovementioned groups , n-butyl, i-butyl, s-butyl, t-butyl, 2-methyl-butyl, n-pentyl, s-pentyl, neo-pentyl, cyclopentyl, n-hexyl, neo-hexyl, cyclohexyl, n-heptyl , Cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl and 2,2,2-trifluoroethyl.
- An alkenyl group is preferably understood to mean the radicals ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl and cyclooctenyl.
- An alkynyl group is preferably understood as meaning ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl and octynyl.
- a C 4 to C 4 o-alkoxy group is preferably understood to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy or 2-methylbutoxy.
- 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, naphthacene, pentacene, benzpyrene, biphenyl, biphenylene, terphenyl, terphenyls, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indenofluorene, Truxen , Isotruxene, spirotruxene, spiroisotruxene, furan, benzo
- the metal complexes of formula (1) may be complexes of polypodal ligands or cryptates, depending on whether ligand L4 is linked to partial ligands L1, L2 and L3 or not.
- a poly-podal ligand is understood as meaning a ligand in which three coordinating partial ligands L1, L2 and L3 are bound to one another by a group V.
- the ligands L are therefore polypodal ligands when no further ligand L4 is bound or when the ligand L4 is linked to only one of the part ligands L1, L2 or L3.
- a cryptate is understood as meaning a connection between a cryptand and a metal ion, in which the metal ion is surrounded three-dimensionally by the bridges of the complex-forming cryptand.
- a cryptand in the context of this invention is understood to mean a macrocyclic tripodal ligand.
- a cryptand can arise if the ligand L4 is linked to two or to all three of the part-ligands L1, L2 and / or L3.
- the group V may also be coordinated to M if the group V has a lone pair of electrons, that is, if it represents, for example, N or P.
- a 0 and the group V is coordinated to M.
- a 1, ie there is a ligand L4 and V does not coordinate to M.
- Partial ligand L1 is a heterocyclic group having at least one N atom which binds to M via a neutral or anionic nitrogen atom or via a neutral carbon atom which is part of the heterocyclic group, or it is a cyclic or heterocyclic group having one exocyclic donor atom which binds to M.
- the bond via a neutral carbon atom is possible in the form of a carbene.
- the cyclic or heterocyclic group has at least 5 and a maximum of 20 ring atoms. It may also be a condensed group, ie a group in which several rings are linked together via a common edge.
- the group L1 can be saturated, unsaturated or aromatic or heteroaromatic.
- L1 is a heteroaryl group or an aryl or heteroaryl group having an exocyclic donor atom or a cyclic, saturated or unsaturated carbene.
- the aryl or heteroaryl group has 5 to 14 aromatic ring atoms, very particularly preferably 5 to 10 aromatic ring atoms.
- Ligand L4 and the bridging unit V is chosen so that they compensate for the charge of the complexed metal ion M. Preference is furthermore given to compounds of the formula (1), characterized in that the sum of the valence electrons, d. H. the
- Electrons of the outermost shell to the metal atom, if it is a transition metal is 18. This preference is due to the particular stability of these metal complexes.
- the metals M are the metals described above, preference being given to Cu as Cu (I), Ag as Ag (I), Au as Au (I), Zn as Zn (II), Sn as Sn (IV), Pb as Pb (IV), Ni as Ni (0), Pd as Pd (0) and Pt as Pt (0).
- the value in brackets behind the metal indicates the oxidation state of the metal.
- the metals M are preferably selected from the group consisting of Cu (I), Ag (I), Ni (0), Pd (0) and Pt (0), particularly preferably Cu (I) and Ag (I), very particularly preferably Cu (I).
- L1 is selected from the groups according to the formulas (3) to (30):
- the groups of the formulas (3) to (30) coordinate to the metal M via the position indicated by * .
- the position indicated by # indicates the position where the sub-ligand adjoins Y and V, respectively
- the position indicated by (#) indicates the position where the part-ligand is bound to Y or L4, if necessary. If such a further bond to Y or to L4 is present, the corresponding symbol X is C and in the formulas (7), (8), (9), (21) and (23) is not a group R to the Nitrogen bound.
- a maximum of three symbols X in each group stand for N, more preferably at most two symbols X in each group represent N, very particularly preferably at most one symbol X in each group stands for N. More preferably, all symbols X stand for C.
- L2 and L3 are by definition coordinating groups, which may also be substituted by one or more radicals R and which bind to M via nitrogen, phosphorus, sulfur, oxygen or a neutral carbon atom, where L2 and L3 can also be identical or different ,
- L2 and L3 the same or different at each occurrence, are a coordinating group which binds to M via nitrogen, phosphorus or sulfur, or are the same or different L1.
- Preferred coordinating groups which bind to M via phosphorus are selected from the group consisting of -PR2, -PR (OR) and
- R has the abovementioned meanings. More preferably, R is the same or different at each occurrence an aromatic or heteroaromatic ring system which may be substituted with one or more R 1 radicals.
- Preferred coordinating groups which bind to M by means of sulfur are selected from the group consisting of -S " or -SR, where R has the abovementioned meanings.R particularly preferably, R is identical or different at each occurrence, an alkyl group having 1 to 10 C. - atoms which may be substituted by one or more radicals R 1 , or an aromatic or heteroaromatic ring system which may be substituted by one or more radicals R 1 .
- Particularly preferred compounds according to formula (1) characterized in that L2 is the same or different at each occurrence L1.
- Very particularly preferred compounds according to formula (1) characterized in that L2 and L3 are the same or different at each occurrence L1.
- the index n is identical or different at each occurrence 0, 1 or 2.
- the bridging unit V may be neutral or simply negative or simply positively charged.
- the charge of V is preferably chosen so that a total of a neutral complex is formed. So z. B. a neutral bridging unit V is preferred, if it is a monovalent metal ion M + and three neutral and a single negative (part) üganden L1, L2, L3 and L4.
- a single negative bridging unit V is preferred when it is a monovalent metal ion M + and four neutral (part) ligands L1, L2, L3 and L4.
- a single positive bridging unit V is preferred when it is a monovalent metal ion M + and two single negative and two neutral (partial) ligands L1, L2, L3 and L4. The same applies if the metal ion has a different valency.
- Formula (31) Formula (32)
- Formula (33) Formula (34) wherein the dashed bonds in each case indicate the bond to the partial ligands L1, L2 and L3 or to Y and R are the abovementioned
- L4 is selected from the group consisting of carbon monoxide, nitrogen monoxide, alkyl cyanides, such as. For example, acetonitrile, aryl cyanides, such as. B.
- alkyl isocyanides such as. Methylisonitrile, aryl isocyanides, such as z.
- B. benzoisonitrile amines, such as. Trimethylamine, triethylamine,
- Morpholine phosphines, in particular halogenophosphines, trialkyl phosphines, triarylphosphines or alkylarylphosphines, such as.
- Trifluorophosphine trimethylphosphine, tricyclohexylphosphine, tri-tert-butylphosphine, triphenylphosphine, tris (pentafluorophenyl) phosphine, phosphites, such as.
- trimethyl phosphite triethyl phosphite
- arsines such as.
- pyridine pyridazine, pyrazine, pyrimidine, triazine, carbenes, in particular Arduengo carbenes, hydride, deuteride, the halides F ⁇ Cr, ⁇ and ⁇ , alkyl acetylides, such as.
- Carboxylates such as. As acetate, trifluoroacetate, propionate, benzoate, anionic, nitrogen-containing heterocycles, such as pyrrolidone, imidazolide, pyrazolide.
- the alkyl groups in these groups are preferably C 1 -C 20 -alkyl groups, particularly preferably C 1 -C 10 -alkyl groups, very particularly preferably C 1 -C 4 -alkyl groups.
- An aryl group is also understood to mean heteroaryl groups. These groups are as defined above.
- Preferred ligands or partial ligands L4 are furthermore the ligands of the following formulas (35) to (61),
- Mean meanings and * indicate the position of coordination at M.
- the position indicated by (#) indicates the position at which L4, optionally over - (Y) n -, may be bound to one of the partial ligands L1, L2 or L3.
- the corresponding symbol X stands for C and in the formulas (38), (39), (40) and (55) no group R is attached to the nitrogen bound.
- Preferred structures according to formula (1) are structures in which the abovementioned preferences occur simultaneously, ie structures in which:
- L1 is selected from the above groups according to the
- L4 is selected from the group consisting of carbon monoxide, nitrogen monoxide, alkyl cyanides, aryl cyanides, alkyl isocyanides, aryl isocyanides, amines, halophosphines, trialkylphosphines, triarylphosphines, alkylarylphosphines, phosphites, arsines, stibines, neutral or anionic nitrogen-containing heterocycles,
- Particularly preferred structures according to formula (1) are structures in which:
- L1 is selected from the above groups according to the
- L2, L3 are the same or different at each occurrence L1;
- Y is the same or different at each occurrence as a bivalent
- the ligand L4 is linked via a direct bond or via a group - (Y) n - to at least one of the partial ligands L1, L2 and / or L3.
- the ligand L has a structure according to one of the formulas (62) to (66), the symbols and indices used having the meanings given above:
- Formula (64) Formula (65)
- ligands for complexes containing the abovementioned structures of the formulas (62) to (66), the same preferences apply as ligands, as mentioned above for structures of the formula (1).
- the partial ligand L4 in structures of the formula (62) or (63) is particularly preferably identically or differently defined as the above definition of the partial ligands L1 to L3 or, as above, the structures (35) to (61).
- the partial ligand L4 is in structures of formula (64) or (65) selected from the group consisting of -NR-, -N " -, -PR-, -P (OR) -, -S- or partial ligands of the following Formulas (67) to (90),
- the partial ligand L4 in structures of the formula (66) is N or P.
- R in these compounds particularly preferably stands for H, D, F, a straight-chain alkyl group having 1 to 4 C atoms or a branched alkyl group having 3 or 4 C atoms, each containing one or several radicals R 1 may be substituted, wherein one or more H atoms may be replaced by F, or an aryl group having 6 to 10 aromatic ring atoms or an aromatic ring system having 12 to 18 aromatic ring atoms, each by one or more radicals R 1 may be substituted; two or more substituents R may also together form a mono- or polycyclic, aliphatic, aromatic and / or benzoannellated ring system.
- complexes according to formula (1) or complexes with ligands of formula (62) to (66) or according to the above-mentioned preferred embodiments can be prepared in principle by various methods, but the methods described below have been found to be particularly suitable ,
- Another object of the present invention a method for preparing the complexes of formula (1) by reacting the ligands L according to formula (2) with metal salts or metal complexes of the corresponding metal M.
- suitable copper compounds which are used as starting materials can be CuF, CuCl, CuBr, CuI, Cu (OAc), Cu 2 (CO 3 ) or Cu (CH 3 CN) PF 6 .
- suitable gold compounds which can be used as starting materials are In addition, SR 2 , wherein Hal is a halide and R is an alkyl group having 1 to 5 carbon atoms.
- the synthesis can also be activated thermally, photochemically or by microwave radiation.
- the complexes can be obtained in high purity, preferably in a purity of> 99% by 1H-NMR or HPLC.
- Examples of preferred compounds according to formula (1) are the compounds depicted below. These complexes can be prepared, inter alia, with the synthesis methods explained above.
- organic electroluminescent devices organic light-emitting diodes, OLEDs, PLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), light-emitting electrochemical cells (LECs) or organic laser diodes (O-lasers).
- Active components are, for example, charge injection, charge transport or charge blocking materials, but especially emission materials and matrix materials. For these functions show the
- the electronic device is therefore selected from the group consisting of organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors ( O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), light-emitting electrochemical cells (LECs) or organic laser diodes (O-lasers), but especially organic ones Electroluminescent devices (OLEDs, PLEDs) containing one or more compounds of the formula (1). Preference is given to organic electroluminescent devices containing one or more compounds of the formula (1) or the abovementioned preferred embodiments.
- the organic electroluminescent device includes cathode, anode and at least one emitting layer. In addition to these layers, they may also contain further layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers and / or
- Charge Generation Layers (Charge Generation Layer).
- Interiayers which have, for example, an exciton-blocking function. It should be noted, however, that not necessarily each of these
- the organic electroluminescent device may contain an emitting layer, or it may contain a plurality of emitting layers, wherein at least one emitting layer contains at least one compound according to formula (1) or the preferred embodiments mentioned above.
- a plurality of emission layers are present, they preferably 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.
- Particular preference is given to three-layer systems (three emitting layers), the three layers exhibiting blue, green and orange or red emission (for the basic structure see, for example, WO 05/011013).
- the compound according to formula (1) or the preferred embodiments mentioned above is used as the emitting compound in an emitting layer, it is preferably used in combination with one or more matrix materials.
- the mixture of the compound according to formula (1) or the abovementioned preferred embodiments and the matrix material contains between 1 and 99% by weight, preferably between 2 and 90% by weight, particularly preferably between 3 and 40% by weight. , in particular between 5 and 15 wt .-% of the compound according to formula (1) or the above-mentioned preferred embodiments based on the total mixture of emitter and matrix material.
- the mixture contains between 99 and 1 wt .-%, preferably between 98 and 10 wt .-%, particularly preferably between 97 and 60 wt .-%, in particular between 95 and 85 wt .-% of the matrix material based on the total mixture of Emitter and matrix material.
- Suitable matrix materials for the compounds of the invention which can be used singly or as a mixture of two or more of these materials are ketones, phosphine oxides, sulfoxides and sulfones, e.g. Example, according to WO 04/013080, WO 04/093207, WO 06/005627 or WO 2010/006680, triarylamines, carbazole derivatives, for.
- CBP N, N-biscarbazolylbiphenyl
- WO 05/039246 US 2005/0069729, JP 2004/288381
- EP 1205527 or WO 08/086851 disclosed carbazole derivatives, indolocarbazole derivatives, z. B. according to WO 07/063754 or WO 08/056746, indenocarbazole derivatives, for. B. according to the unpublished applications DE 102009023155.2 and DE 102009031021.5, azabarbazoles, z. B. according to EP 1617710, EP 1617711, EP 1731584,
- bipolar matrix materials e.g. B. according to WO 07/137725, silanes, z. B. according to WO 05/111172, azaborole or boronic esters, for. B. according to WO 06/117052, triazine derivatives, z. B. according to WO 2010/015306, WO 07/063754, WO 08/056746 or not disclosed application DE 102009048791.3, zinc complexes, for. B. according to EP 652273 or WO 09/062578, diaza or tetraazasilol derivatives, for. B. according to WO
- the shorter-wave-emitting metal complex serving as a co-host for the longer-wavelength emitting metal complex.
- the compound according to formula (1) or the preferred embodiments mentioned above is used as the matrix material for an emitting compound in an emitting layer.
- the organic electroluminescent device may contain an emitting layer, or it may contain a plurality of emitting layers, wherein at least one emitting layer contains at least one compound according to formula (1) or the above-mentioned preferred embodiments as matrix material. If multiple emission layers are present, the above applies.
- the compound of the formula (1) or the above-mentioned preferred embodiments is used as a matrix material for an emitting compound in an emitting layer is preferred in combination with one or more
- the compound of the formula (1) or the abovementioned preferred embodiments is used as a hole-blocking material in a hole-blocking layer and / or as an electron-transport material in an electron-transport layer.
- the emitting layer may be fluorescent or phosphorescent.
- the emitting layer may be fluorescent or phosphorescent.
- an organic electroluminescent device characterized in that one or more layers are coated with a sublimation process.
- the materials jn vacuum sublimation at an initial pressure of usually less than 10 "5 mbar, preferably less than 10" evaporated.
- the initial pressure it is also possible for the initial pressure to be even lower, for example less than 10.sup.- 7 mbar.
- OVPD Organic Vapor Phase Deposition
- a carrier gas sublimation The materials are applied at a pressure between 10 "5 mbar and 1 bar.
- OVJP Organic Vapor Jet Printing
- the materials are applied directly through a nozzle and thus structured (for example, 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.
- 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
- hybrid processes in which, for example, one or more layers of solution are applied and one or more other layers are vapor-deposited.
- one or more layers of solution are applied and one or more other layers are vapor-deposited.
- Another object of the invention is therefore a compound according to formula ML '
- ligand L containing a metal M coordinated to a ligand L ', wherein the ligand L' corresponds to one of the formulas (62) to (66) and each of the part-ligands L1, L2, L3 and L4 coordinates to M,
- Another object of the invention is the use of a
- Blue luminescent complexes are available which have a long lifetime when used in organic electroluminescent devices. This is a significant advance over the prior art, since hitherto blue-luminescent metal complexes were only accessible with poor color coordinates and in particular a poor lifetime.
- the compounds of the invention used in organic electroluminescent devices lead to high efficiencies and steep current-voltage curves.
- the compounds according to formula (1) are not based on the rare metal iridium, which contributes to the conservation of the resources of this metal.
- the complexes according to formula (1) or according to the above-mentioned preferred embodiments are readily and synthetically accessible in high yields and high purities.
- a suspension of 12.0 g of silica gel in 50 ml of dichloromethane is treated dropwise with 3.0 ml of thionyl chloride and then stirred for 1 h at room temperature. Then, a solution of 6.4 g (20 mmol) of (6-formylpyridin-2-yl) bis- (6-methylpyridin-2-yl) fluoromethane and 2.4 g (22 mmol) of o-phenylenediamine are added dropwise and stirred h after.
- the mixture is filtered from the salts, washed twice with 100 ml of THF, the THF in vacuo, the oily residue in 500 ml of dichloromethane, the organic phase is washed three times with 200 ml of water and dried over magnesium sulfate. After filtering off the
- a mixture of 10 mmol of ligand and 2.5 g (10 mmol) of silver hexafluorophosphate in 100 ml of THF is mixed with 1.3 g (10 mmol) of diisopropylethylamine and stirred at 40 ° C for 24 h.
- Can 'chtept Elektrolumineszenzvorn present invention are represented for example as described in WO 05/003253. Here the results of different OLEDs are compared. The basic structure, the materials used, the degree of doping and their layer thicknesses are identical for better comparability.
- HIL Hole Injection Layer
- HTL1 Hole transport layer 5 nm NPB (N-naphthyl-N-phenyl-4,4'-diaminobiphenyl)
- EBM, M and TEB are shown below for the sake of clarity.
- OLEDs are characterized by default; For this purpose, the electroluminescence spectra, the external quantum efficiency (measured in%) as a function of the brightness, calculated from current-voltage-brightness characteristics (IUL characteristics) are determined.
- OLEDs are produced according to the general procedure outlined below. Of course, this has to be adapted in individual cases to the respective circumstances (eg layer thickness variation in order to achieve optimum efficiency or color).
- PLEDs polymeric light-emitting diodes
- the compounds of the invention are dissolved together with the listed matrix materials or Matrixmareialkombinationen in toluene, chlorobenzene or DMF.
- the typical solids content of such solutions is between 10 and 25 g / L, if, as here, the typical for a device layer thickness of 80 nm is to be achieved by spin coating.
- OLEDs are produced with the following structure: PEDOT 20 nm (spun from water, PEDOT supplied by BAYER AG; poly- [3,4-ethylenedioxy-2,5-thiophene]
- ITO substrates and the material for the so-called buffer layer are commercially available (ITO from Technoprint and others, PEDOT: PSS as aqueous dispersion Clevios Baytron P from HC Starck).
- the emission layer is spin-coated in an inert gas atmosphere, in this case argon, and baked at 120 ° C. for 10 minutes. Finally, a cathode of barium and aluminum is evaporated in vacuo.
- the solution-processed devices are characterized by default, the OLED examples mentioned are not yet optimized. Table 2 shows the efficiency and the voltage at 100 cd / m 2 and the color.
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Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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JP2012541333A JP5766712B2 (ja) | 2009-12-05 | 2010-11-09 | 金属錯体を含む電子素子 |
US13/513,592 US9634268B2 (en) | 2009-12-05 | 2010-11-09 | Electronic device comprising metal complexes |
CN201080055085.3A CN102648540B (zh) | 2009-12-05 | 2010-11-09 | 包含金属络合物的电子器件 |
DE112010004687T DE112010004687A5 (de) | 2009-12-05 | 2010-11-09 | Elektronische vorrichtung enthaltend metallkomplexe |
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DE102009057167.1 | 2009-12-05 | ||
DE102009057167A DE102009057167A1 (de) | 2009-12-05 | 2009-12-05 | Elektronische Vorrichtung enthaltend Metallkomplexe |
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WO2011066898A1 true WO2011066898A1 (de) | 2011-06-09 |
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PCT/EP2010/006821 WO2011066898A1 (de) | 2009-12-05 | 2010-11-09 | Elektronische vorrichtung enthaltend metallkomplexe |
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US (1) | US9634268B2 (de) |
JP (1) | JP5766712B2 (de) |
KR (1) | KR20120091443A (de) |
CN (1) | CN102648540B (de) |
DE (2) | DE102009057167A1 (de) |
TW (1) | TW201137083A (de) |
WO (1) | WO2011066898A1 (de) |
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Also Published As
Publication number | Publication date |
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US20120286254A1 (en) | 2012-11-15 |
KR20120091443A (ko) | 2012-08-17 |
CN102648540B (zh) | 2016-03-16 |
DE112010004687A5 (de) | 2012-09-20 |
CN102648540A (zh) | 2012-08-22 |
JP5766712B2 (ja) | 2015-08-19 |
JP2013513225A (ja) | 2013-04-18 |
US9634268B2 (en) | 2017-04-25 |
DE102009057167A1 (de) | 2011-06-09 |
TW201137083A (en) | 2011-11-01 |
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