EP3956338A1 - Metal complexes - Google Patents
Metal complexesInfo
- Publication number
- EP3956338A1 EP3956338A1 EP20716842.8A EP20716842A EP3956338A1 EP 3956338 A1 EP3956338 A1 EP 3956338A1 EP 20716842 A EP20716842 A EP 20716842A EP 3956338 A1 EP3956338 A1 EP 3956338A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- group
- aromatic
- radicals
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 39
- 239000002184 metal Substances 0.000 title claims abstract description 39
- 125000003118 aryl group Chemical group 0.000 claims description 78
- 239000003446 ligand Substances 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 67
- -1 heteroaliphatic Chemical group 0.000 claims description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 34
- 239000011159 matrix material Substances 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 125000001931 aliphatic group Chemical group 0.000 claims description 16
- 229910052741 iridium Inorganic materials 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical group [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 150000001450 anions Chemical class 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052697 platinum Chemical group 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 229910001507 metal halide Inorganic materials 0.000 claims description 2
- 150000005309 metal halides Chemical class 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 77
- 150000003254 radicals Chemical class 0.000 description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000463 material Substances 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 230000000903 blocking effect Effects 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N NMP Substances CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 238000000605 extraction Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 150000002503 iridium Chemical class 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000000859 sublimation Methods 0.000 description 6
- 230000008022 sublimation Effects 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 150000003918 triazines Chemical class 0.000 description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000011229 interlayer Substances 0.000 description 4
- 229960004592 isopropanol Drugs 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000007717 exclusion Effects 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000005496 tempering Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- LBNXAWYDQUGHGX-UHFFFAOYSA-N 1-Phenylheptane Chemical compound CCCCCCCC1=CC=CC=C1 LBNXAWYDQUGHGX-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
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 2
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 2
- NPDIDUXTRAITDE-UHFFFAOYSA-N 1-methyl-3-phenylbenzene Chemical group CC1=CC=CC(C=2C=CC=CC=2)=C1 NPDIDUXTRAITDE-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 2
- XGOHIDPYTAHUIW-UHFFFAOYSA-N 3-pyridin-2-ylbenzonitrile Chemical compound N#CC1=CC=CC(C=2N=CC=CC=2)=C1 XGOHIDPYTAHUIW-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 229910021640 Iridium dichloride Inorganic materials 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- 101100457453 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) MNL1 gene Proteins 0.000 description 2
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- 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
- 125000005580 triphenylene group Chemical group 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-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
- 238000001947 vapour-phase growth Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0046—Ruthenium compounds
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0086—Platinum compounds
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- H10K2101/10—Triplet emission
Definitions
- the present invention relates to metal complexes which are suitable for use as emitters in organic electroluminescent devices.
- OLEDs organic electroluminescent devices
- organometallic complexes which show phosphorescence instead of fluorescence are often used as emitting materials.
- Iridium and platinum complexes in particular are used as triplet emitters.
- the iridium complexes used are in particular bis- and tris-ortho-metallated complexes with aromatic ligands, the ligands binding to the metal via a negatively charged carbon atom and a neutral nitrogen atom. Examples of such complexes are imidazoisoquinoline complexes, e.g. B.
- WO 2010/086089 or WO 201 1/157339, or imidazophenanthridine complexes, e.g. B. according to US 2012/0153816 or US 2015/0295189, in which the ligand coordinate to the iridium via a six-membered ring and a five-membered ring.
- the object of the present invention is to provide new metal complexes which are suitable as emitters for use in OLEDs, in particular for emission colors in the range from green to red, and which lead to good efficiency and service life.
- the invention relates to a compound of the formula (1),
- M is iridium or platinum
- D is C or N, one D being C and the other D being N;
- X is on each occurrence, identically or differently, CR or N;
- NR 2 , O, S or CONR 2 can be replaced and where one or more H atoms in the alkyl, alkenyl or alkynyl group can be replaced by D, F, CI, Br, I or CN, or an aromatic or heteroaromatic one Ring system with 5 to 40 aromatic ring atoms, which can in each case be substituted by one or more radicals R 2 ; two or more radicals R 1 here can form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system with one another;
- R 2 is on each occurrence, identically or differently, H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical, in particular a hydrocarbon radical, with 1 to 20 carbon atoms, in which one or more F1 atoms are also replaced by F could be;
- L ’ is, identically or differently, a ligand at each occurrence; n is 1, 2 or 3; m is 0, 1, 2, 3, or 4; Several ligands L can also be linked to one another or L with L 'via a single bond or a bivalent or trivalent bridge and thus create a tridentate, tetradentate, pentadentate or hexadentate ligand system.
- an aryl group contains 6 to 40 carbon atoms;
- a heteroaryl group contains 2 to 40 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5.
- the heteroatoms are preferably selected from N, O and / or S.
- the heteroaryl group preferably contains 1, 2 or 3 heteroatoms, no more than one of which is selected from O or S.
- An aryl group or heteroaryl group is either a simple aromatic group Cycle, that is benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a condensed aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc., understood.
- An aromatic ring system for the purposes of this invention contains 6 to 60 carbon atoms in the ring system.
- a heteroaromatic ring system in the context of this invention contains 1 to 60 carbon atoms and at least one heteroatom in the ring system, with the proviso that the sum of carbon atoms and heteroatoms is at least 5.
- the heteroatoms are preferably selected from N, O and / or S.
- An aromatic or heteroaromatic ring system in the context 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 aryl groups or heteroaryl groups through a non-aromatic unit (preferably less than 10% of the atoms other than H), such as. B.
- a C, N or O atom or a carbonyl group can be interrupted.
- systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc. are to be understood as aromatic ring systems for the purposes of this invention, and likewise systems in which two or more aryl groups are, for example, replaced by one linear or cyclic alkyl group or are interrupted by a silyl group.
- systems in which two or more aryl or heteroaryl groups are bonded directly to one another, such as.
- biphenyl or terphenyl also if understood as an aromatic or heteroaromatic ring system.
- a cyclic alkyl, alkoxy or thioalkoxy group in the context of this invention is understood to mean a monocyclic, a bicyclic or a polycyclic group. If several substituents form an aliphatic ring system with one another, the term includes “Aliphatic ring system” in the context of the present invention also includes heteroaliphatic ring systems.
- a C1 to C40 alkyl group in which individual H atoms or CH2 groups can also be substituted by the groups mentioned above, for example the radicals methyl, ethyl, n-propyl, i-propyl, Cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1 -methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-
- alkenyl group is understood to mean, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.
- An alkynyl group is understood to mean, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
- a C1 to C40 alkoxy group is understood to mean, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy.
- aromatic or heteroaromatic ring system with 5 - 60 aromatic ring atoms which can also be substituted by the above-mentioned radicals and which can be linked via any positions on the aromatic or heteroaromatic, is understood as meaning, for example, groups which are derived from benzene, Naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, Chrysene, perylene, fluoranthene, benzfluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-lindenofluorene, cis- or trans-lindenofluorene, cis- or trans-lindenoflu
- Anthroxazole phenanthroxazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzpyrimidine, quinoxaline,
- the abovementioned formulation is also intended to mean that in the event that one of the two radicals is hydrogen, the second radical binds to the position to which the hydrogen atom was bound to form a ring.
- the indices n and m are chosen so that the coordination number on the metal M as a whole, depending on the metal, corresponds to the coordination number customary for this metal.
- this is the coordination number 6
- no X or at most one X per cycle stands for N and the other groups X stand for CR.
- the symbols X in the two six rings stand for CR or a symbol X in the six rings that coordinates via the carbon atom stands for N and the other symbols X in the two six rings stand for CR, and exactly one symbol X in the Five-membered ring stands for N.
- Preferred embodiments of the formula (3) are the structures of the following formulas (3a) to (3f)
- preferred embodiments of the formula (4) are the structures of the following formulas (4a) to (4f)
- the symbols and indices used have the meanings given above. It is preferred if the structure of the formula (2) stands for a structure according to the following formulas (3a- 1) to (4M),
- the structures of the formulas (3) or (3a) to (3c) are preferred.
- the structures of the formula (3a) are particularly preferred.
- two adjacent radicals R on the five-membered ring form a condensed benzo group with one another, which can be substituted by one or more radicals R 1 .
- Preferred embodiments are the structures of formulas (3a-2) to (4a-6),
- Preferred radicals R on each occurrence are selected from the group consisting of H, D, F, Br, I, N (R 1 ) 2, CN, Si (R 1 ) 3, B (OR 1 ) 2, one straight-chain alkyl group with 1 to 10 carbon atoms or one
- radicals R are particularly preferably selected identically or differently on each occurrence from the group consisting of H, D, F, N (R 1 ) 2, CN, a straight-chain alkyl group with 1 to 6 carbon atoms or an alkenyl group with 2 to 6 C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, where one or more Fl atoms can be replaced by D or F, or an aromatic or heteroaromatic ring system with 6 to 13 aromatic ring atoms, each by one or more radicals R 1 can be substituted; two adjacent radicals R can also form an aliphatic or aromatic ring system with one another.
- Preferred radicals R 1 are H, D, F, CN, a straight-chain alkyl group with 1 to 10 carbon atoms or an alkenyl group with 2 to 20 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, identically or differently Atoms, each of which can be substituted by one or more radicals R 2 , where one or more H atoms can be replaced by F, or an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, each by one or more radicals R 2 may be substituted; two or more adjacent radicals R 1 here can form an aliphatic, aromatic or heteroaromatic ring system with one another.
- radicals R 1 are on each occurrence, identically or differently, H, D, F, a straight-chain alkyl group with 1 to 4 carbon atoms or a branched or cyclic alkyl group with 3 to 6 carbon atoms or an aromatic or heteroaromatic ring system with 6 up to 13 aromatic ring atoms, each of which can be substituted by one or more radicals R 2 , but is preferably unsubstituted; two or more adjacent radicals R 1 here can form an aliphatic or aromatic ring system with one another.
- Preferred radicals R 2 are selected from the group consisting of H, D, F, CN, an alkyl group with 1 to 6 carbon atoms or an aromatic ring system with 6 to 12 carbon atoms.
- two adjacent radicals R form an aliphatic ring system with one another. This is possible with neighbors on one or both of the six-membered rings and / or on the five-membered ring.
- Preferred aliphatic ring systems are selected from the structures of the following formulas (5) to (11),
- Formula (11) where R 1 and R 2 have the meanings given above, the broken lines indicate the linkage of the two carbon atoms in the ligand and the following applies:
- R 3 identically or differently on each occurrence, is F, OR 2 , a straight-chain alkyl group with 1 to 10 C atoms, a branched or cyclic alkyl group with 3 to 10 C atoms, the alkyl group each having one or more radicals R 2 may be substituted, one or more non-adjacent CH2 groups by
- a double bond is formally formed between the two carbon atoms. This represents a simplification of the chemical structure when these two carbon atoms are integrated into an aromatic or heteroaromatic system and thus the bond between them two carbon atoms formally lies between the degree of bond of a single bond and that of a double bond.
- a bridging unit can also be present in the compounds according to the invention, which links the ligand L with one or more other ligands L or L '.
- a bridging unit instead of one of the radicals R which are on one of the coordinating six-membered rings in the ortho or meta position to the coordinating atom, in particular in the meta position to the coordinating atom, a bridging unit is present, so that the ligands have three or more teeth or poly-podal character. There can also be two such bridging units. This leads to the formation of macrocyclic ligands or to the formation of cryptates.
- Preferred structures with multidentate ligands or with polydentate ligands are the metal complexes of the following formulas (12) to (15),
- L preferably stands for a bidentate partial ligand, in particular for a monoanionic bidentate partial ligand which coordinates via a carbon atom and a nitrogen atom.
- V in the structures of formulas (12) and (13) is preferably a group of the following formula (26), the dashed bonds representing the position of the linkage of the partial ligands L and L ‘,
- X 1 is on each occurrence, identically or differently, CR or N;
- A is identically or differently on each occurrence CR2-CR2 or a group of the formula (27).
- the following embodiments are preferred:
- One group A stands for a group of the formula (27), and the two other groups A stand for the same group CR2-CR2; or
- the group of the formula (27) represents an aromatic or heteroaromatic six-membered ring.
- the group of the formula (27) contains a maximum of one fleteroatom in the aryl or fleteroaryl group. This does not exclude the possibility that substituents which are optionally bound to this group can also contain fleteroatoms. Furthermore, this definition does not exclude the formation of condensed aromatic or heteroaromatic structures, such as naphthalene, benzimidazole, etc ..
- the group of formula (27) is preferably selected from benzene, pyridine, pyrimidine and pyrazine and pyridazine.
- Preferred embodiments of the group of the formula (27) are the structures of the following formulas (28) to (35),
- the optionally substituted groups of the formulas (28) to (32) are particularly preferred.
- Orthophenylene that is to say a group of the formula (28), is very particularly preferred.
- adjacent substituents can also form a ring system with one another, so that condensed structures, including condensed aryl and fleteroaryl groups, such as naphthalene, quinoline, benzimidazole, carbazole, dibenzofuran or dibenzothiophene, can arise.
- condensed structures including condensed aryl and fleteroaryl groups, such as naphthalene, quinoline, benzimidazole, carbazole, dibenzofuran or dibenzothiophene
- Preferred embodiments of the group of the formula (26) are the structures of the following formulas (36) to (39),
- the groups of formulas (36) to (39) are particularly preferably selected from the structures of the following formulas (36b) to (39b), where R, identically or differently on each occurrence, represents H or D, preferably H.
- ligands L are described as they occur in formula (1).
- the ligands L ' are preferably neutral, monoanionic, dianionic or trianionic ligands, particularly preferably neutral or monoanionic ligands, in particular monoanionic ligands. They can be monodentate, bidentate, tridentate or tetradentate and are preferably bidentate, ie preferably have two coordination points. As described above, the ligands L ’can also be bound to L via a bridging group V. The ligands lobidentate and monoanionic are particularly preferred.
- Preferred neutral, monodentate ligands L ' are selected from the group consisting of carbon monoxide, nitrogen monoxide, alkyl cyanides, such as. B. acetonitrile, aryl cyanides, such as. B. benzonitrile, alkyl isocyanides, such as. B. methylisonitrile, aryl isocyanides, such as. B. benzoisonitrile, amines, such as B. trimethylamine, triethylamine, morpholine, phosphines, in particular special halophosphines, trialkylphosphines, triarylphosphines or alkylarylphosphines, such as. B.
- trifluorophosphine trimethylphosphine, tricyclohexylphosphine, tri-tert-butylphosphine, triphenylphosphine, tris (pentafluorophenyl) phosphine, dimethylphenylphosphine, methyldiphenylphosphine, bis (tert-butyl) phenylphosphine, phosphites, such as. B. trimethyl phosphite, triethyl phosphite, arsines, such as. B.
- trifluoroarsine trimethylarsine, tricyclohexylarsine, tri-ie / T-butylarsine, triphenylarsine, tris (pentafluorophenyl) arsine, stibines, such as. B. trifluorostibine, trimethylstibine, tricyclohexylstibine, tri-tert-butylstibine, triphenylstibine, tris (pentafluorophenyl) stibine, nitrogen-containing heterocycles, such as. B. pyridine, pyridazine, pyrazine, pyrimidine, triazine, and carbenes, especially Arduengo carbenes.
- Carboxylates such as B. acetate, trifluoroacetate, propionate, benzoate, aryl groups, such as. B. phenyl, naphthyl, and anionic, nitrogen-containing heterocycles such as pyrrolide, imidazolide, pyrazolide.
- the alkyl groups in these groups are preferably Ci-C2o-alkyl groups, particularly preferably Ci-Cio-alkyl groups, very particularly preferably Ci-C4-alkyl groups.
- An aryl group is also understood to mean heteroaryl groups. These groups are as defined above.
- diphosphines such as. B. bis (diphenylphosphino) methane, bis (diphenylphosphino) ethane, bis (diphenylphosphino) propane, bis (diphenylphosphino) butane, bis (dimethylphosphino) methane, bis (dimethylphosphino) ethane, bis (dimethylphosphino) propane, bis ( diethylphosphino) methane, bis (diethylphosphino) ethane, bis (diethylphosphino) propane, bis (di- te / t-butylphosphino) methane, bis (di-ferf-butylphosphino) ethane, bis (tert-butylphosphino) propane, 1 , 3-diketonates derived from 1,3-diketones, e.g. B. acetylphosphino) methan
- 3-ketoesters such as B. ethyl acetoacetate, carboxylates derived from aminocarboxylic acids, such as. B. pyridine-2-carboxylic acid, quinoline-2-carboxylic acid, glycine, N, N-dimethylglycine, alanine, N, N-dimethylamino alanine, salicyliminates derived from salicylimines, such as. B. methylsalicylimine, ethylsalicylimine, phenylsalicylimine, dialcoholates derived from dialcohols, such as. B. ethylene glycol, 1,3-propylene glycol, dithiolates derived from dithiols, such as.
- B 1,2-ethylenedithiol, 1,3-propylenedithiol, bis (pyrazolyl borates), bis (imidazolyl) borates, 3- (2-pyridyl) -diazoles or 3- (2-pyridyl) -triazoles.
- Preferred tridentate ligands are borates of nitrogen-containing heterocycles, such as. B. Tetrakis (1 -imidazolyl) borate and tetrakis (1 -pyrazolyl) borate.
- ligands L ' bidentate monoanionic, neutral or dianionic ligands L ', in particular monoanionic ligands which, with the metal, have a cyclometalated five-membered or six-membered ring with at least one metal-carbon bond, in particular a cyclometalated five-membered ring.
- ligands as they are generally used in the field of phosphorescent metal complexes for organic electroluminescent devices, i.e. ligands of the phenylpyridine, naphthylpyridine, phenylquinoline, phenylisoquinoline, etc. type, which can each be substituted by one or more radicals R.
- ligand L for compounds according to formula (1).
- the combination of two groups, as represented by the following formulas (40) to (88), is particularly suitable for this, one group preferably binding via a neutral nitrogen atom or a carbene carbon atom and the other group preferably binding via a negatively charged one Carbon atom or a negatively charged nitrogen atom.
- These groups can also be bound to the ligand L via one or two bridging units V.
- X and R have the meanings given above, and W stands for NR, O or S.
- a maximum of three symbols X in each group preferably stand for N, particularly preferably a maximum of two symbols X in each group stand for N, and very particularly preferably stand at most one symbol X in each group for N.
- all symbols X stand for CR.
- a condensed heteroaryl group which coordinates to M as a bidentate ligand L, can also be formed from the two individual aryl or heteroaryl groups by ring formation of neighboring substituents.
- radicals R on these structures are the same as have already been set out above for formula (2) as radicals R when X stands for CR .
- the complexes according to the invention can be facial or pseudofacial, or they can be meridional or pseudomeridional.
- the present invention further provides a process for the preparation of the metal complex compounds of the formula (1) by reacting the corresponding free ligands L and optionally L 'with metal alcoholates of the formula (79), with metal ketoketonates of the formula (80), with metal halides Formula (81), with dimeric metal complexes of the formula (82) or with metal complexes of the formula (83),
- Atoms or a nitrile, in particular acetonitrile or benzonitrile, and (anion) is a non-coordinating anion, such as, for example, triflate.
- ligand L coordinates via the two six-membered rings and not via a five- and a six-membered ring. More detailed information on the conduct of the reaction can be found in the examples. It is also possible to use metal compounds, in particular iridium compounds, which carry both alcoholate and / or halide and / or hydroxy as well as ketoketonate residues. These connections can also be loaded. Corresponding iridium compounds which are particularly suitable as starting materials are disclosed in WO 2004/085449.
- [IrCl2 (acac) 2] _ for example Na [IrCl2 (acac) 2]
- metal complexes with acetylacetonate derivatives as ligand for example Ir (acac) 3 or tris (2, 2,6, 6-tetramethylheptane-3) are particularly suitable , 5-dionato) iridium, and lrCl3-xH20, where x usually stands for a number between 2 and 4.
- Suitable platinum starting materials are, for example, PtCL, K2 [PtCl4],
- PtCl 2 (DMSO) 2 Pt (Me) 2 (DMSO) 2 or PtCl2 (benzonitrile).
- Heteroleptic complexes can also be synthesized according to WO 2005/042548, for example.
- the synthesis can for example also be activated thermally, photochemically and / or by microwave radiation.
- a Lewis acid for example a silver salt or AlC.
- solvents or melting aids can be added.
- Suitable solvents are protic or aprotic solvents such as aliphatic and / or aromatic alcohols (methanol, ethanol, iso-propanol, t-butanol, etc.), oligo- and polyalcohols (ethylene glycol, 1,2-propanediol, glycerine, etc.) , Alcohol ethers (ethoxyethanol, diethylene glycol, triethylene glycol, polyethylene glycol, etc.), ethers (di- and triethylene glycol dimethyl ether, diphenyl ether, etc.), aromatic, heteroaromatic and / or aliphatic hydrocarbons (toluene,
- protic or aprotic solvents such as aliphatic and / or aromatic alcohols (methanol, ethanol, iso-propanol, t-butanol, etc.), oligo- and polyalcohols (ethylene glycol, 1,2-propanediol
- Suitable melting aids are compounds that are solid at room temperature, however, melt when the reaction mixture is heated and the
- Biphenyl, m-terphenyl, triphenylene, 1, 2-, 1, 3-, 1, 4-bisphenoxybenzene, triphenylphosphine oxide, 18-crown-6, phenol, 1-naphthol, hydroquinone, etc. are particularly suitable.
- the compounds according to the invention of the formula (1) can be obtained in high purity, preferably more than 99% and particularly preferably more than 99.9% (determined by means of 1 H-NMR and / or HPLC).
- the compounds according to the invention can also be made soluble by suitable substitution, for example by longer alkyl groups (approx. 4 to 20 carbon atoms), especially branched alkyl groups, or optionally substituted aryl groups, for example xylyl, mesityl or branched terphenyl or quaterphenyl groups.
- Such compounds are then soluble in common organic solvents such as toluene or xylene at room temperature in sufficient concentration to be able to process the complexes from solution.
- These soluble compounds are particularly suitable for processing from solution, for example by printing processes.
- formulations of the compounds according to the invention are required. These formulations can be, for example, solutions, dispersions or emulsions. It can be preferred to use mixtures of two or more solvents for this purpose.
- Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, ( -) - fenchone, 1, 2,3,5-tetramethylbenzene, 1, 2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, a-terpineol, benzothiazole, butyl benzoate, cumene, cyclo- hexanol, cyclohexanone, cyclohexylbenzene,
- the present invention therefore again further provides a formulation containing a compound according to the invention and at least one further compound.
- the further compound can be a solvent, for example.
- the further compound can, however, also be a further organic or inorganic compound which is also used in the electronic device, for example a matrix material.
- the above-described compounds of the formula (1) or the preferred embodiments listed above can be used as the active component in the electronic device.
- the invention therefore also relates to the use of a compound according to formula (1) or according to the preferred embodiment forms in an electronic device.
- An electronic device is understood to mean a device which contains anode, cathode and at least one layer, this layer containing at least one organic or organometallic compound.
- the electronic device according to the invention thus contains anode, cathode and at least one layer which contains at least one compound of the formula (1) listed above.
- Preferred electronic devices are selected from the group consisting of organic electroluminescent devices (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 photo receptors, organic field quench devices (O-FQDs), light-emitting electrochemical cells (LECs) or organic laser diodes (O -Laser), containing in at least one layer at least one compound according to the formula (1) listed above.
- Organic electroluminescent devices are particularly preferred.
- Active components are generally the organic or inorganic materials which are introduced between the anode and cathode, for example charge injection, charge transport or charge blocking materials, but especially emission materials and matrix materials. The compounds according to the invention show particularly good properties as
- Organic electroluminescent devices are therefore a preferred embodiment of the invention.
- the compounds according to the invention can be used to generate singlet oxygen, in photocatalysis or in light conversion, eg. B. in pixel color converters (PCC) can be used.
- PCC pixel color converters
- the organic electroluminescent device contains a cathode, anode and at least one emitting layer. In addition to these layers, it can 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, charge generation layers and / or organic or inorganic p / n junctions. It is possible that one or more hole transport layers are p-doped, for example with metal oxides such as MO3 or WO3 or with (per) fluorinated electron-poor aromatics, and / or that one or more electron transport layers are n-doped.
- interlayers can be introduced between two emitting layers which, for example, have an exciton-blocking function and / or control the charge balance in the electroluminescent device. It should be noted, however, that not necessarily each of these layers has to be present.
- the organic electroluminescent device can be a
- emitting layer or it can contain several emitting layers. If several emission layers are present, these preferably have a total of several emission maxima between 380 nm and 750 nm, so that overall white emission results, ie. H.
- Various emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. Three-layer systems are particularly preferred, the three layers showing blue, green and orange or red emission (for the basic structure see, for example, WO 2005/01 1013) or systems which have more than three emitting layers. It can also be a hybrid system in which one or more layers fluoresce and one or more other layers phosphoresce.
- the organic electroluminescent device contains the compound of the formula (1) or the preferred embodiments listed above as an emitting compound in one or more emitting layers.
- the compound of the formula (1) is used as an emitting compound in an emitting layer, it is preferably used in combination with one or more matrix materials.
- Mixture of the compound according to formula (1) and the matrix material contains between 0.1 and 99% by volume, preferably between 1 and 90% by volume, particularly preferably between 3 and 40% by volume, in particular between 5 and 15% by volume. -% of the compound according to formula (1) based on the total mixture of emitter and matrix material.
- the mixture contains between 99.9 and 1% by volume, preferably between 99 and 10% by volume, particularly preferably between 97 and 60% by volume, in particular between 95 and 85% by volume of the matrix material based on the Total mixture of emitter and matrix material.
- the triplet level of the matrix material is preferably higher than the triplet level of the emitter.
- Suitable matrix materials for the compounds according to the invention are ketones, phosphine oxides, sulfoxides and sulfones, e.g. B. according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO
- azaboroles or boronic esters for. B. according to WO 2006/1 17052, diazasilol derivatives, e.g. B. according to WO 2010/054729, diazaphosphole derivatives, e.g. B. according to WO 2010/054730, triazine derivatives, e.g. B. according to WO
- a preferred combination is, for example, the use of an aromatic ketone, a triazine derivative or a phosphine oxide derivative with a triarylamine derivative or a carbazole derivative as a mixed matrix for the metal complex according to the invention.
- a mixture of a charge-transporting matrix material and an electrically inert matrix material which is not or not to a significant extent involved in charge transport, such as, for. B. described in WO 2010/108579.
- Preferred biscarbazoles which can be used as matrix materials for the compounds according to the invention are the structures of the following formulas (84) and (85), where Ar 1 identically or differently stands for an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, preferably with 6 to 30 aromatic ring atoms, which can be substituted by one or more radicals R, A 1 for NR, CR2, O or S and R has the meanings given above. In a preferred embodiment of the invention, A 1 is CR2.
- Preferred embodiments of the compounds of the formulas (84) and (85) are the compounds of the following formulas (84a) and (85a),
- Examples of suitable compounds according to formula (84) or (85) are the compounds shown below.
- Preferred dibenzofuran derivatives are the compounds of the following formula (86),
- L stands for a single bond or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which can also be substituted by one or more radicals R, and R and Ar 1 have the meanings given above.
- the two groups Ar 1 which bind to the same nitrogen atom, or a group Ar 1 and a group L, which bind to the same nitrogen atom, can also be connected to one another, for example to form a carbazole.
- Preferred carbazolamines are the structures of the following formulas (87), (88) and (89),
- L stands for an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which can be substituted by one or more radicals R, and R and Ar 1 have the meanings given above.
- Preferred triazine, quinazoline or pyrimidine derivatives which can be used as a mixture together with the compounds according to the invention, are the compounds of the following formulas (90), (91) and (92),
- the triazine derivatives of the formula (90) and the quinazoline derivatives of the formula (92), in particular the triazine derivatives of the formula (90), are particularly preferred.
- Ar 1 in the formulas (90), (91) and (92) is, identically or differently, an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, in particular with 6 to 24 aromatic ring atoms, which can be substituted by one or more radicals R.
- Suitable aromatic or heteroaromatic ring systems Ar 1 are the same as those mentioned above as embodiments for Ar 1 , Ar 2 and Ar 3 , in particular the structures Ar-1 to Ar-76.
- Suitable triazine compounds which can be used as matrix materials together with the compounds according to the invention are the compounds shown in the table below.
- the triplet emitter with the shorter-wave emission spectrum serves as a co-matrix for the triplet emitter with the longer-wave emission spectrum.
- the complexes according to the invention according to formula (1) can be used as a co-matrix for triplet emitters emitting longer wavelengths, for example for green or red emitting triplet emitters.
- the compounds according to the invention can also be used in other functions in the electronic device, for example as hole transport material in a hole injection or hole transport layer, as charge generation material or as electron blocking material.
- the complexes according to the invention can also be used as matrix material for other phosphorescent metal complexes in an emitting layer.
- metal alloys or multi-layer structures made of different metals are preferred as cathodes, such as alkaline earth metals, alkali metals, main group metals or lanthanoids (e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.) .
- alloys of an alkali or alkaline earth metal and silver for example an alloy of magnesium and silver, are suitable.
- other metals can be used that have a relatively high work function, such as.
- B. Ag in which case combinations of the metals such as Mg / Ag, Ca / Ag or Ba / Ag are then usually used.
- a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor can also be preferred.
- a material with a high dielectric constant between a metallic cathode and the organic semiconductor for example, alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates (e.g. LiF, U2O, BaF2, MgO, NaF, CsF, CS2CO3, etc.) are suitable.
- Organic alkali metal complexes are also suitable for this purpose, e.g. B. Liq (lithium quinolinate).
- the layer thickness of this layer is preferably between 0.5 and 5 nm.
- the anode preferably has a work function greater than 4.5 eV vs. Vacuum on.
- metals with a high redox potential are suitable for this, such as Ag, Pt or Au.
- metal / metal oxide electrodes for example Al / Ni / NiOx, Al / PtOx
- at least one of the electrodes must be transparent or partially transparent in order to enable either the irradiation of the organic material (O-SC) or the coupling of light (OLED / PLED, O-LASER).
- Preferred anode materials here are conductive mixed ones Metal oxides.
- ITO Indium tin oxide
- IZO indium zinc oxide
- conductive, doped organic materials in particular conductive doped polymers, e.g. B. PEDOT, PANI or derivatives of these polymers.
- a p-doped hole transport material is applied as a hole injection layer to the anode, metal oxides, for example M0O3 or WO3, or (per) fluorinated electron-poor aromatics being suitable as p-dopants.
- metal oxides for example M0O3 or WO3
- fluorinated electron-poor aromatics being suitable as p-dopants.
- HAT-CN hexa-cyano-hexaazatriphenylen
- NPD9 compound NPD9 from Novaled.
- the device is structured accordingly (depending on the application), contacted and finally hermetically sealed, since the service life of such devices is drastically shortened in the presence of water and / or air.
- An organic electroluminescent device is also preferred, characterized in that one or more layers are coated with a sublimation process.
- the materials are vapor-deposited in vacuum sublimation systems at an initial pressure of usually less than 10 5 mbar, preferably less than 10 6 mbar. It is also possible for the initial pressure to be even lower or even higher, for example less than 10 7 mbar.
- An organic electroluminescent device is likewise preferred, characterized in that one or more layers are coated with the OVPD (Organic Vapor Phase Deposition) process or with the aid of a carrier gas sublimation.
- the materials are applied at a pressure between 10 5 mbar and 1 bar.
- this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured (e.g. BMS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).
- an organic electroluminescent device characterized in that one or more layers of solution, such as. B. by spin coating, or with any printing process, such as. B. screen printing, flexographic printing, offset printing or nozzle printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or ink-jet printing (inkjet printing) can be produced.
- LITI Light Induced Thermal Imaging, thermal transfer printing
- ink-jet printing inkjet printing
- the organic electroluminescent device can also be produced as a hybrid system in that one or more layers are applied from solution and one or more other layers are vapor-deposited.
- one or more layers are applied from solution and one or more other layers are vapor-deposited.
- the electronic devices according to the invention are distinguished by good color coordinates, good efficiency and good service life.
- the following syntheses are carried out under a protective gas atmosphere in dried solvents.
- the metal complexes are also handled with exclusion of light or under yellow light.
- the solvents and reagents can e.g. B. from Sigma-ALDRICH or ABCR.
- the respective information in square brackets or the numbers given for individual compounds relate to the CAS numbers of the compounds known from the literature. In the case of compounds which can have several enantiomeric, diastereomeric or tautomeric forms, one form is shown as a representative.
- Example TL1 A suspension, cooled to -78 ⁇ , of 15.2 g (50 mmol) of 6-chloro-benzimidazo [2,1 -f] benzo [h] [1,6] naphthyridine [1228276-32-0] in 200 ml of THF becomes 59.0 ml (100 mmol) of tert-butyllithium (1.7 M in n-pentane) were added dropwise and the mixture was stirred for 2 h.
- the desiccant is filtered off, the filtrate is evaporated to dryness in vacuo and the glass-like one is crystallized Crude product at the boiling point from acetonitrile (-150 ml) and then a second time from acetonitrile / ethyl acetate. Yield: 58.1 g (70 mmol), 70%; purity: approx. 95% according to 1 H-NMR.
- Variant A Tris-acetylacetonato-iridium (III) as iridium educt
- a mixture of 10 mmol of tris (2,2,6,6-tetramethyl-3,5-heptanedionato) iridium (III) [99581-86-9] and 60 mmol of the ligand L is under vacuum (10 5 mbar) melted into a 50 ml glass ampoule.
- the ampoule is heated for the specified time at the specified temperature, the melted mixture being stirred with the aid of a magnetic stirrer.
- a high boiling alkane e.g. B. Octa- decane, added.
- the solid is placed in a hot extractor on a 5 cm high Alox bed (Alox, basic activity level 1) and then extracted with the specified extraction agent (initial amount approx. 500 ml).
- the solid of the suspension obtained in this way is filtered off with suction, washed once with about 50 ml of methanol and dried. After drying, the purity of the metal complex is determined by means of NMR and / or HPLC. If the purity is below 99.5%, the hot extraction step is repeated. Is a purity of
- the metal complex is tempered or sublimed.
- the tempering takes place in a high vacuum (p approx. 10 6 mbar) in the temperature range from 200-350 O.
- the sublimation takes place in a high vacuum (p approx. 10 6 mbar) in the temperature range from approx. 320 to approx. 450 O, with sublimation is preferably carried out in the form of a fractionated sublimation.
- a well-stirred suspension of 5 mmol of the indicated iridium starting material of the type [l_2lrCl] 2, 10 mmol of the ligand L and 50 g of glass spheres (3 mm diameter) in 200 ml of 1,2-dichloromethane is mixed with 60 mmol of triethylamine and then 10 mmol of silver trifluoromethanesulfonate were added and the mixture was stirred at 90 ° C. for 24 h.
- the precipitated silver chloride is filtered off while still warm through a pre-slurried silica gel bed, washed with a little 1,2-dichloroethane and the filtrate is concentrated to dryness.
- the crude product is then chromatographed on silica gel (mobile phase: dichloromethane, toluene, ethyl acetate, acetone, THF, cyclohexane, n-heptane, etc. and / or mixtures thereof). Further cleaning is carried out as described under 1) by repeated hot extraction and tempering or fractionated sublimation in a high vacuum.
- the crude product is then chromatographed on silica gel (mobile phase: dichloromethane, toluene, ethyl acetate, acetone, THF, cyclohexane, n-heptane, etc. and / or mixtures thereof).
- the further cleaning takes place as described under 1) by repeated hot extraction and tempering or fractional sublimation in a high vacuum.
- a mixture of 10 mmol of the HL ligand, 4.90 g (10 mmol) of tris-acetyl-acetonato-iridium (III) [15635-87-7] and 120 g of hydroquinone [123-31-9] are added to a 1000 ml two-necked round bottom flask presented a glasummantel th magnetic core.
- the flask is equipped with a water separator (for media with a lower density than water) and an air cooler with an argon blanket.
- the flask is placed in a metal heating bowl.
- the apparatus is over the argon blanketing from above for 15 min. flushed with argon, the argon from the side neck of the
- Two-necked flask can flow out.
- a glass-encased Pt-100 thermocouple is inserted into the flask via the side neck of the two-necked flask and the end is placed just above the magnetic stir bar.
- the apparatus is thermally insulated with several loose windings of household aluminum foil, whereby the insulation is led to the middle of the riser pipe of the water separator.
- the apparatus is then quickly heated to 250-255 ⁇ using a laboratory stirrer, measured on the Pt-100 thermocouple, which is immersed in the melted, stirred reaction mixture. During the next 2 h the reaction mixture is kept at 250-255 h, with little condensate distilled and collects in the water separator.
- the core fraction is cut out and concentrated on a rotary evaporator, with MeOH being continuously added dropwise at the same time until crystallization. After suctioning off, washing with a little MeOH and drying in vacuo, the orange-colored product is further purified by four continuous hot extraction with dichloromethane / iso-propanol 1: 1 (vv) and then four hot extraction with dichloromethane / acetonitrile (initial amount approx. 200 ml, extraction thimble: standard Soxhlet thimbles made of cellulose from Whatman) with careful exclusion of air and light.
- the loss in the mother liquor can be adjusted via the ratio of dichloromethane (low boilers and good solvent): iso-propanol or acetonitrile (high boilers and poor solvent). Typically it should be 3-6% by weight of the amount used. Other solvents such as toluene, xylene, ethyl acetate, butyl acetate, etc. can also be used for hot extraction. Finally, the product is fractionally sublimated or tempered in a high vacuum at p ⁇ 10 6 mbar and T ⁇ 350-430 ⁇ . Typically> 99.7% purity.
- OLEDs according to the invention and OLEDs according to the prior art are produced by a general method according to WO 2004/058911, which is based on the conditions described here
- the OLEDs basically have the following layer structure: substrate / hole injection layer 1 (HIL1) consisting of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm / hole transport layer 1 (HTL1) consisting of HTM1, 220 nm for green / yellow devices,
- HIL1 substrate / hole injection layer 1
- NDP-9 commercially available from Novaled
- HTL1 hole transport layer 1
- the cathode is formed by a 100 nm thick aluminum layer.
- HTL2 hole transport layer 2
- EML emission layer
- HBL hole blocking layer
- ETL electron transport layer
- EIL optional electron injection layer
- the cathode is formed by a 100 nm thick aluminum layer.
- M1: M2: lr (L1) 55%: 35%: 10%
- M1: M2: lr (L1) 55%: 35%: 10%
- the electron transport layer can also consist of a mixture of two materials.
- the exact structure of the OLEDs is shown in Table 2.
- the materials used to produce the OLEDs are shown in Table 4.
- the OLEDs are characterized as standard.
- the electroluminescence spectra, the current efficiency (measured in cd / A), the power efficiency (measured in Im / W) and the external quantum efficiency (EQE, measured in percent) are calculated as a function of the luminance, calculated from current-voltage-luminance characteristics ( IUL characteristics) assuming a Lambertian radiation characteristic and the service life is determined.
- the electroluminescence spectra are determined at a luminance of 1000 cd / m 2 and the CIE 1931 x and y color coordinates are calculated from this.
- the service life LD50 is defined as the time after which the luminance has dropped to 50% of the starting luminance during operation with a starting brightness of 1000 cd / m 2 .
- the OLEDs can initially also be operated with other starting luminance levels.
- the values for the service life can then be converted to a specification for other starting luminance values with the aid of conversion formulas known to those skilled in the art.
- the compounds according to the invention can be used, inter alia, as phosphorescent emitter materials in the emission layer in OLEDs.
- the results of the OLEDs are summarized in Table 2.
- A Made of low molecular weight, soluble functional materials
- the iridium complexes according to the invention can also be processed from solution and lead to OLEDs which are technically much simpler in terms of process technology, compared to the vacuum-processed OLEDs, with nevertheless good properties.
- the manufacture of such components is based on the manufacture of polymer light-emitting diodes (PLEDs), which has already been described many times in the literature (e.g. in WO 2004/037887).
- the structure consists of substrate / ITO / hole injection layer (60 nm) / interlayer (20 nm) / emission layer (60 nm) / hole blocking layer (10 nm) / electron transport layer (40 nm) / cathode.
- substrates from Technoprint are used, to which the ITO structure (indium tin oxide, a transparent, conductive anode) is applied.
- the substrates are cleaned in the clean room with DI water and a detergent (Deconex 15 PF) and then activated by a UV / ozone plasma treatment.
- a 20 nm hole injection layer is applied by spin coating.
- the required spin rate depends on the degree of dilution and the specific spin coater geometry.
- the substrates are heated for 30 minutes at 200 on a heating plate.
- the interlayer used is used to transport holes in in this case HL-X from Merck is used.
- the interlayer can also be replaced by one or more layers, which only have to meet the condition that they cannot be removed again by the downstream processing step of EML deposition from solution.
- the 5 triplet emitters according to the invention are dissolved together with the matrix materials in toluene or chlorobenzene.
- the typical solids content of such solutions is between 16 and 25 g / L if, as here, the typical layer thickness of 60 nm for a device is to be achieved by means of spin coating.
- the solution-processed devices of type 1 contain an emission layer I O made of M4: M5: lrL (20%: 58%: 22%), those of type 2 contain an emission layer of M4: M5: lrLa: lrLb (30%: 34%: 29%) : 7%), ie they contain two different Ir complexes.
- the percentages for the materials processed from solution denote% by weight.
- the emission layer is spun on in an inert gas atmosphere, in the present case argon, for 15 and 10 minutes. baked out at 160 ⁇ .
- the hole blocking layer (10 nm ETM1) and the electron transport layer (40 nm ETM1 (50%) / ETM2 (50%)) are applied by vapor deposition (vapor deposition systems from Lesker oa, typical vapor deposition pressure 5 ⁇ 10 6 mbar). Finally, a cathode made of aluminum (100 nm) (high-purity metal from Aldrich) is vapor deposited. In order to protect the device from air and humidity, the device is finally encapsulated and then characterized. The OLED examples mentioned have not yet been optimized. Table 3 summarizes the data obtained.
- the service life LD50 is defined as the time after which the luminance drops to 50% of the starting luminance when operating with a starting brightness of 1000 cd / m 2 .
- CIE color coordinates of CIE x / y 0.19 / 0.28 are given for both complexes.
- the complexes which coordinate to the iridium via a five- and a six-membered ring thus show blue emission, while the complexes according to the invention show green, yellow or red emission.
Abstract
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- 2020-04-14 EP EP20716842.8A patent/EP3956338A1/en active Pending
- 2020-04-14 US US17/603,704 patent/US20220209141A1/en active Pending
- 2020-04-14 CN CN202080026042.6A patent/CN113646317A/en active Pending
- 2020-04-14 JP JP2021561051A patent/JP2022529926A/en active Pending
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JP2022529926A (en) | 2022-06-27 |
CN113646317A (en) | 2021-11-12 |
WO2020212296A1 (en) | 2020-10-22 |
US20220209141A1 (en) | 2022-06-30 |
WO2020212296A9 (en) | 2021-11-04 |
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