DE102013225682A1 - Metal ion adducts of neutral phosphorescent emitters for use in light emitting organic optoelectronic devices - Google Patents
Metal ion adducts of neutral phosphorescent emitters for use in light emitting organic optoelectronic devices Download PDFInfo
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- DE102013225682A1 DE102013225682A1 DE102013225682.5A DE102013225682A DE102013225682A1 DE 102013225682 A1 DE102013225682 A1 DE 102013225682A1 DE 102013225682 A DE102013225682 A DE 102013225682A DE 102013225682 A1 DE102013225682 A1 DE 102013225682A1
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- 229910001887 tin oxide Inorganic materials 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
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- UFMOMJZZKFLOSJ-UHFFFAOYSA-M trifluoromethanesulfonate;1,2,3-trimethylimidazol-1-ium Chemical compound CC=1N(C)C=C[N+]=1C.[O-]S(=O)(=O)C(F)(F)F UFMOMJZZKFLOSJ-UHFFFAOYSA-M 0.000 description 1
- RFDGVZHLJCKEPT-UHFFFAOYSA-N tris(2,4,6-trimethyl-3-pyridin-3-ylphenyl)borane Chemical compound CC1=C(B(C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C(C)=CC(C)=C1C1=CC=CN=C1 RFDGVZHLJCKEPT-UHFFFAOYSA-N 0.000 description 1
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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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
- H10K50/135—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising mobile ions
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- H10K85/30—Coordination compounds
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Abstract
Die vorliegende Erfindung betrifft kationische Alkalimetallverbindungen von neutralen Übergangsmetallkomplexen, Verfahren zu deren Herstellung sowie deren Verwendung in optoelektronischen Bauelementen.The present invention relates to cationic alkali metal compounds of neutral transition metal complexes, to processes for their preparation and to their use in optoelectronic components.
Description
Die vorliegende Erfindung betrifft kationische Alkalimetallverbindungen von neutralen Übergangsmetallkomplexen, Verfahren zu deren Herstellung sowie deren Verwendung in optoelektronischen Bauelementen. The present invention relates to cationic alkali metal compounds of neutral transition metal complexes, to processes for their preparation and to their use in optoelectronic components.
Stand der Technik State of the art
Organische lichtemittierende Dioden (OLED) sind an der Schwelle zur Markteinführung. Es hat sich gezeigt, dass effiziente OLEDs nur mit Hilfe von Multilagen, die aus niedermolekularen Verbindungen hergestellt wurden, erhalten werden können. OLEDs aus Polymeren zeigen bisher nicht die erwarteten Effizienzen und Lebensdauern, obwohl deren Herstellung prinzipiell einfacher und kostengünstiger erfolgen könnte. Organic light-emitting diodes (OLEDs) are on the threshold of market introduction. It has been shown that efficient OLEDs can only be obtained with the aid of multilayers which have been prepared from low molecular weight compounds. Polymer OLEDs have not yet shown the expected efficiencies and lifetimes, although their production could in principle be simpler and less expensive.
In den letzten Jahren wurde ein neuer Bauteiltyp der organischen lichtemittierenden elektrochemischen Zellen (OLEECs) entdeckt und weiterentwickelt. Er zeigt das Potential, eine kostengünstige Fertigungsweise mit den Vorteilen niedermolekularer Verbindungen verbinden zu können. Zur Ausbildung der Dotierfronten im OLEEC-Bauteil ist es notwendig, dass die Verbindungen ionisch = salzartig sind. Negativ geladene Teile der salzartigen Verbindung orientieren sich bevorzugt in Richtung Anode, positiv geladene in Richtung Kathode. Damit bildet sich im Betrieb des elektrischen Feldes ein Bauteil mit der aus der OLED bekannten p-i-n (i = intrinsisches Material) Struktur aus. In recent years, a new type of organic light-emitting electrochemical cell (OLEEC) has been discovered and developed. He shows the potential to be able to combine a cost-effective manufacturing method with the advantages of low molecular weight compounds. To form the doping fronts in the OLEEC component, it is necessary that the compounds are ionic = salt-like. Negatively charged parts of the salt-like compound are preferably oriented in the direction of the anode, positively charged in the direction of the cathode. Thus, during operation of the electric field, a component is formed with the p-i-n (i = intrinsic material) structure known from the OLED.
Die bisher besten OLEECs im Hinblick auf Anschaltverhalten, Effizienz (Strom und Leistung) und Lebensdauer werden dadurch erhalten, dass ionische Flüssigkeiten in den ionischen Emitter eingemischt werden. Ein wesentlicher Nachteil dieses Systems besteht darin, dass die verwendeten ionischen Flüssigkeiten nicht zum Ladungstransport beitragen können und dürfen (Leckstromproblematik). Der Stromtransport erfolgt daher über den in hoher Konzentration vorhandenen Emitter, der dadurch a. stärker belastet wird, was seine Lebensdauer verringert, und b. bei hohen Leuchtdichten durch Triplett-Triplett-Annihilation seine Effizienz vermindert. The best OLEECs in terms of turn-on performance, efficiency (current and power) and lifetime are obtained by mixing ionic liquids into the ionic emitter. A major disadvantage of this system is that the ionic liquids used can not and should not contribute to charge transport (leakage current problem). The current transport therefore takes place via the high concentration emitter, which thereby a. is more heavily loaded, which reduces its life, and b. at high luminances by triplet triplet annihilation reduces its efficiency.
Zudem sind in OLEEC-Einschichtbauelementen die sich ausbildenden p-i-n Strukturen räumlich nicht abgegrenzt, sodass während des Betriebs die p- und n-Schichten auf Kosten der intrinsischen Schicht verdicken, bis sich sozusagen das Bauteil selbst zerstört. In addition, in OLEEC single-layer devices, the p-i-n structures that form are spatially not delimited, so that during operation the p- and n-layers thicken at the expense of the intrinsic layer until, as it were, the component itself is destroyed.
In der Patentfamilie
Die aktive Schicht in neueren Varianten einer OLEEC bestehen vornehmlich aus ionischen Komponenten. Der Emitter iTMC (ionic transition metal complex) wird in Matrizen aus ionischen Flüssigkeiten/Feststoffen eingebettet. Typische Beispiele ionischer metallorganischer Verbindungen sind Rutheniumtris-bipyridinhexafluorophosphat [Ru(bpy)3]2+(PF6 –)2 (
Die Anmeldung
Es besteht jedoch weiterhin ein Bedarf an Materialien, die die Leistungsfähigkeit von optoelektronischen Bauteilen, insbesondere OLEECs, OLEDs oder Hybrid-OLEEC/OLED-Bauelementen, verbessern können. However, there is still a need for materials that can improve the performance of optoelectronic devices, particularly OLEECs, OLEDs, or hybrid OLEEC / OLED devices.
Zusammenfassung der Erfindung Summary of the invention
Überraschend wurde gefunden, dass bestimmte Alkalimetallkationen Komplexe mit neutralen phosphoreszenten Emittern / neutralen Übergangsmetallkomplexen (nTMC = neutral transition metal complex) ausbilden. Diese Komplexe sind positiv geladen und können damit beispielsweise als iTMCs (ionic transition metal complex) der OLEECs interpretiert werden. Die Alkalimetallkationenkomlexe der nTNCs (Kat-n-TMC) können hierbei beispielsweise sowohl durch Lösungsprozessierung als auch durch Ko-verdampfung aus der Gasphase erhalten werden. Dies bedeutet, dass die p- und n-Transportschichten der OLEDs für die Nutzung in OLEECs erschlossen werden können. Surprisingly, it has been found that certain alkali metal cations form complexes with neutral phosphorescent emitters / neutral transition metal complexes (nTMC = neutral transition metal complex). These complexes are positively charged and can thus be interpreted as, for example, the iTMCs (ionic transition metal complex) of the OLEECs. The alkali metal cation complexes of nTNCs (Kat-n-TMC) can In this case, for example, be obtained both by solution processing and by co-evaporation from the gas phase. This means that the p and n transport layers of the OLEDs can be tapped for use in OLEECs.
Gemäß einem Aspekt betrifft die Erfindung eine Verbindung der Formel M+(n-TMC)x, wobei M aus Li, Na, K, Rb, Cs ausgewählt ist, n-TMC ein neutraler Übergangsmetallkomplex ist, und x = 1 oder 2 ist. In one aspect, the invention relates to a compound of the formula M + (n-TMC) x wherein M is selected from Li, Na, K, Rb, Cs, n-TMC is a neutral transition metal complex, and x = 1 or 2.
Gemäß einem weiteren Aspekt betrifft die Erfindung ferner ein Verfahren zur Herstellung einer Verbindung der Formel M+(n-TMC)x, wobei n-TMC mit Mo +X– umgesetzt wird, wobei M aus Li, Na, K, Rb, Cs ausgewählt ist, X– ein Anion des Alkalimetallkations M+ darstellt, n-TMC ein neutraler Übergangsmetallkomplex ist, o der Wertigkeit des Anions entspricht und x = 1 oder 2 ist. According to a further aspect, the invention further relates to a process for the preparation of a compound of the formula M + (n-TMC) x , where n-TMC is reacted with M o + X - , where M is selected from Li, Na, K, Rb, Cs is selected, x - is an anion of the alkali metal cation M +, n-TMC is a neutral transition metal complex, o corresponds to the valency of the anion, and x = 1 or 2.
Zudem betrifft die vorliegende Erfindung gemäß weiteren Aspekten die Verwendung der erfindungsgemäßen Verbindung als ionischer Übergangsmetallkomplex in optoelektronischen Bauteilen, optoelektronische Bauelemente, welche die Verbindung umfassen sowie die Verwendung der Verbindung als Emitter von Licht. In addition, in other aspects, the present invention relates to the use of the compound according to the invention as an ionic transition metal complex in optoelectronic components, optoelectronic components comprising the compound and the use of the compound as an emitter of light.
Weitere Aspekte sowie bevorzugte Ausgestaltungen der Erfindung ergeben sich aus den abhängigen Ansprüchen sowie der folgenden detaillierten Beschreibung der Erfindung. Further aspects and preferred embodiments of the invention will become apparent from the dependent claims and the following detailed description of the invention.
Beschreibung der Figuren Description of the figures
Die beiliegenden Zeichnungen sollen Ausführungsformen der vorliegenden Erfindung veranschaulichen und ein weiteres Verständnis dieser vermitteln. Im Zusammenhang mit der Beschreibung dienen sie der Erklärung von Konzepten und Prinzipien der Erfindung. Andere Ausführungsformen und viele der genannten Vorteile ergeben sich im Hinblick auf die Zeichnungen. Die Elemente der Zeichnungen sind nicht notwendigerweise maßstabsgetreu zueinander dargestellt. Gleiche, funktionsgleiche und gleich wirkende Elemente, Merkmale und Komponenten sind in den Figuren der Zeichnungen, sofern nichts anderes ausgeführt ist, jeweils mit denselben Bezugszeichen versehen. The accompanying drawings are intended to illustrate embodiments of the present invention and to provide a further understanding thereof. In the context of the description, they serve to explain concepts and principles of the invention. Other embodiments and many of the stated advantages will become apparent with reference to the drawings. The elements of the drawings are not necessarily to scale. Identical, functionally identical and identically acting elements, features and components are in the figures of the drawings, unless otherwise stated, each provided with the same reference numerals.
Detaillierte Beschreibung der Erfindung Detailed description of the invention
Ein neutraler Übergangsmetallkomplex im Rahmen der Erfindung ist ein Komplex eines Übergangsmetalls, der nach außen hin ungeladen ist. Solche Komplexe sind in vielfältiger Weise bekannt, beispielsweise aus
Die Erfindung betrifft gemäß einem Aspekt eine Verbindung der Formel M+(n-TMC)x, wobei M aus Li, Na, K, Rb, Cs ausgewählt ist, n-TMC ein neutraler Übergangsmetallkomplex ist, und x = 1 oder 2 ist. Es sind somit Verbindungen offenbart, in denen ein oder zwei Übergangsmetallkomplexe an M binden, wobei diese gleich oder verschieden sein können. Bevorzugt sind hierbei cyclometallisierte neutrale Übergangsmetallkomplexe, also neutrale Übergangsmetallkomplexe, die durch Cyclometallierung hervorgegangen sind. Die Cyclometallierungsreaktion ist hierbei nicht besonders beschränkt. Bevorzugt handelt es sich bei n-TMC um ein cyclometalliertes Derivat des Eisens, Kobalts, Nickels, Rutheniums, Rhodiums, Silbers, Iridiums, Platins und/oder Gold, oder es ist ein cyclometalliertes Derivat des Eisens, Kobalts, Nickels, Rutheniums, Rhodiums, Silbers, Iridiums, Platins und/oder Gold umfasst. Weiter bevorzugt handelt es sich bei n-TMC um ein cyclometalliertes Derivat des Rutheniums, Rhodiums, Silbers, Iridiums, Platins und/oder Gold, oder es ist ein cyclometalliertes Derivat des Rutheniums, Rhodiums, Silbers, Iridiums, Platins und/oder Gold umfasst. The invention in one aspect relates to a compound of the formula M + (n-TMC) x , wherein M is selected from Li, Na, K, Rb, Cs, n-TMC is a neutral transition metal complex, and x = 1 or 2. There are thus disclosed compounds in which one or two transition metal complexes bind to M, which may be the same or different. Preferred here are cyclometallated neutral transition metal complexes, ie neutral transition metal complexes which have arisen by cyclometalation. The Cyclometalation reaction is not particularly limited here. N-TMC is preferably a cyclometallated derivative of iron, cobalt, nickel, ruthenium, rhodium, silver, iridium, platinum and / or gold, or it is a cyclometallated derivative of iron, cobalt, nickel, ruthenium, rhodium, Silver, iridium, platinum and / or gold. More preferably, n-TMC is a cyclometallated derivative of ruthenium, rhodium, silver, iridium, platinum and / or gold or it is a cyclometalated derivative of ruthenium, rhodium, silver, iridium, platinum and / or gold.
Erfindungsgemäß wird somit auch eine Formulierung bereitgestellt, deren Kernzusammensetzung aus einem löslichen Alkalimetallsalz und einem neutralen phosphoreszenten Emitter besteht Thus, according to the invention, a formulation is also provided whose core composition consists of a soluble alkali metal salt and a neutral phosphorescent emitter
Zur Herstellung einer Verbindung der Formel M+(n-TMC)x wird gemäß einem weiteren Aspekt der Erfindung ein neutraler Übergangsmetallkomplex n-TMC mit einer Verbindung Mo +X– umgesetzt, wobei M aus Li, Na, K, Rb, Cs ausgewählt ist, X– ein Anion des Alkalimetallkations M+ darstellt, n-TMC ein neutraler Übergangsmetallkomplex ist, o der Wertigkeit des Anions entspricht und x = 1 oder 2 ist. Gemäß bestimmten Ausführungsformen ist das Anion X– in der Verbindung Mo +X– ausgewählt aus BF4 –, PF6 –, CF3SO3 –, SO4 2– und PO4 3–. Die Alkalimetallionen werden gemäß bestimmten Ausführungsformen also in Form ihrer Salze zugesetzt. Besonders bevorzugte Anionen sind BF4 –, PF6 –, CF3SO3 –, SO4 2–, PO4 3–, fluorierte und nicht fluorierte aromatische, heteroaromatische oder aliphatische oder cycloaliphatische Carboxylate, Sulfonate etc. To prepare a compound of the formula M + (n-TMC) x , according to a further aspect of the invention, a neutral transition metal complex n-TMC is reacted with a compound M o + X - , wherein M is selected from Li, Na, K, Rb, Cs and x - represents an anion of the alkali metal cation M +, n-TMC is a neutral transition metal complex, o corresponds to the valency of the anion and x is 1 or the second According to certain embodiments, the anion X - in the compound M o + X - is selected from BF 4 - , PF 6 - , CF 3 SO 3 - , SO 4 2- and PO 4 3- . The alkali metal ions are thus added according to certain embodiments in the form of their salts. Particularly preferred anions are BF 4 - , PF 6 - , CF 3 SO 3 - , SO 4 2- , PO 4 3- , fluorinated and non-fluorinated aromatic, heteroaromatic or aliphatic or cycloaliphatic carboxylates, sulfonates etc.
Weiterhin ist gemäß bestimmten Ausführungsformen zumindest ein n-TMC ein cyclometalliertes Derivat des Eisens, Kobalts, Nickels, Rutheniums, Rhodiums, Silbers, Iridiums, Platins und/oder Gold, bevorzugt ein cyclometalliertes Derivat des Rutheniums, Rhodiums, Silbers, Iridiums, Platins und/oder Gold. Als n-TMC werden bevorzugterweise die cyclometallierten Derivate des Iridiums, Platins und Golds verwendet. Bei der Cyclometallierung wird in den erfindungsgemäßen Verbindungen gemäß bevorzugten Ausführungsformen zumindest ein Fünfring oder ein Sechsring zwischen mindestens einem Liganden des Komplexes und dem Übergangsmetallatom gebildet. Bevorzugte Liganden in den neutralen Übergangsmetallkomplexen leiten sich beispielsweise von substituiertem oder nicht substituiertem 2-Phenylpyridin oder weiteren substituierten oder nicht substituierten Pyridinderivaten mit mindestens einem substituierten oder nicht substituierten cyclischen Rest an einem C-Atom des Pyridins oder von substituierten oder nicht substituierten Phenylderivaten mit mindestens einem substituierten oder nicht substituierten cyclischen Rest an einem C-Atom des Benzolrings oder von substituiertem oder nicht substituiertem Porphin oder von substituiertem oder nicht substituierten Chinolin und/oder Isochinolin ab, wobei mindestens ein solcher Ligand in einem bevorzugten neutralen Übergangsmetallkomplex enthalten ist. Furthermore, according to certain embodiments at least one n-TMC is a cyclometalated derivative of iron, cobalt, nickel, ruthenium, rhodium, silver, iridium, platinum and / or gold, preferably a cyclometallated derivative of ruthenium, rhodium, silver, iridium, platinum and / or gold. As the n-TMC, the cyclometalated derivatives of iridium, platinum and gold are preferably used. In the cyclometalation, in the compounds according to the invention according to preferred embodiments, at least one five-membered ring or one six-membered ring is formed between at least one ligand of the complex and the transition metal atom. Preferred ligands in the neutral transition metal complexes are derived, for example, from substituted or unsubstituted 2-phenylpyridine or other substituted or unsubstituted pyridine derivatives having at least one substituted or unsubstituted cyclic radical on a C atom of pyridine or substituted or unsubstituted phenyl derivatives with at least one substituted or unsubstituted cyclic radical on a carbon atom of the benzene ring or substituted or unsubstituted porphine or substituted or unsubstituted quinoline and / or isoquinoline, wherein at least one such ligand is contained in a preferred neutral transition metal complex.
Nicht einschränkende Beispiele für n-TMCs sind:
Tris(2-phenylpyridin)Iridium(III), Ir(ppy)2(acac) = Bis(2-phenylpyridin)(acetylacetonato)Iridium(III), Tris[2-(p-Tolyl)pyridin]Iridium(III), Bis(2-phenylpyridinato)[2-(biphenyl-3-yl)pyridinato]Iridium(III), fac-Tris(2-(3-p-xylyl)phenyl)pyridin Iridium(III), Bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)Iridium(III), Bis(2,4-difluorophenylpyridinato)tetrakis(1-pyrazolyl)borat Iridium(III), fac-Iridium(III)tris(1-phenyl-3-methylbenzimidazolin-2-yliden-C,C2'), mer-Iridium(III)tris(1-phenyl-3-methylbenzimidazolin-2-yliden-C,C2'), Bis(2,4-difluorophenylpyridinato)(5-(pyridin-2-yl)-1H-tetrazolat)Iridium(III), factris[(2,6-diisopropylphenyl)-2-phenyl-1H-imidazol[e]Iridium(III), fac-Tris(1-phenyl-3-methylimidazolin-2-yliden-C,C(2)'Iridium(III), mer-Tris(1-phenyl-3-methylimidazolin-2-yliden-C,C(2)'Iridium(III), Bis(1-phenyl-3-methylimdazolin-2-yliden-C,C2')(2-(2H-pyrazol-3-yl)-pyridin)Iridium(III), Bis(1-(4-methylphenyl)-3-methylimdazolin-2-yliden-C,C2')(2-(2H-pyrazol-3-yl)-pyridin)Iridium(III), Bis(1-(4-fluorophenyl)-3-methylimdazolin-2-yliden-C,C2')(2-(2H-pyrazol-3-yl)-pyridin)Iridiunm(III), Bis(1-(4-fluorophenyl)-3-methylimdazolin-2-yliden-C,C2')(2-(1H-imidazol-2-yl)pyridin)Iridiunm(III), Bis(1-(4-fluorophenyl)-3-methylimdazolin-2-yliden-C,C2')(2-(5-trifluoromathyl-2H-pyrazol-3-yl)-pyridin)Iridiunm(III), fac-Tris(1,3-diphenylbenzimidazolin-2-yliden-C,C2')Iridium(III), Bis(1-(4-fluorophenyl)-3-methylimdazolin-2-yliden-C,C2')(3,5-dimethyl-2-(1H-pyrazol-5-yl)pyridin)Iridium(III), Bis(1-(4-methylphenyl)-3-methylimdazolin-2-yliden-C,C2')(3,5-dimethyl-2-(1H-pyrazol-5-yl)pyridin)Iridium(III), Bis(2-benzo[b]thiophen-2-yl-pyridin)(acetylacetonato)Iridium(III), Bis(1-phenylisochinolin)(acetylacetonato)Iridium(III), Bis[1-(9,9-dimethyl-9H-fluoren-2-yl)-isochinolin](acetylacetonato)Iridium(III), Bis[2-(9,9-dimethyl-9H-fluoren-2-yl)chinolin](acetylacetonato)Iridium(III), Tris(2-phenylchinolin)Iridium(III), Bis(2-phenylchinolin)(acetylacetonato)Iridium(III), Bis(2-phenylbenzothiazolato)(acetylacetonato)Iridium(III), 5,10,15,20-tetraphenyltetrabenzoporphyrin Platin, Bis[2-(4-n-hexylphenyl)chinolin](acetylacetonato)Iridium(III), Tris[2-(4-n-hexylphenyl)chinolin)]Iridium(III), Tris[2-phenyl-4-methylchinolin)]Iridium(III), Bis(2-phenylchinolin)(2-(3-methylphenyl)pyridinato)Iridium(III), Bis(2-(9,9-diethyl-fluoren-2-yl)-1-phenyl-1H-benzo[d]imidazolato)(actylacetonato)Iridium(III), Bis(2-phenylpyridin)(3-(pyridin-2-yl)-2H-chromen-2-onato)Iridium(III), Bis(2-phenylchinolin)(2,2,6,6-tetramethylheptan-3,5-dionato)Iridium(III), Bis(phenylisochinolin)(2,2,6,6-tetramethylheptan-3,5-dionato)Iridium(III), Bis[(4-n-hexylphenyl)isochinolin](acetylacetonato)Iridium(III), Pt(II)octaethylporphin, Bis(2-methyldibenzo[f,h]chinoxalin)(acetylacetonato)Iridium(III), Tris[(4-n-hexylphenyl)isochinolin]Iridium(III), Bis(4-methyl-2-(thiophen-2-yl)chinolin)(acetylacetonato)Iridium(III), FCNIr-Pic (Bis[2-(5-cyano-4,6-difluorophenyl)pyridinato-C2,N](picolinato)Iridium(III)) und FK306. Weitere beispielhafte n-TMCs sind auch z.B. aus
Tris (2-phenylpyridine) iridium (III), Ir (ppy) 2 (acac) = bis (2-phenylpyridine) (acetylacetonato) iridium (III), tris [2- (p-tolyl) pyridine] iridium (III), Bis (2-phenylpyridinato) [2- (biphenyl-3-yl) pyridinato] iridium (III), fac-tris (2- (3-p-xylyl) phenyl) pyridine, iridium (III), bis (3,5-) difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (III), bis (2,4-difluorophenylpyridinato) tetrakis (1-pyrazolyl) borate, iridium (III), fac-iridium (III) tris (1 -phenyl-3-methylbenzimidazolin-2-ylidene-C, C2 '), mer-iridium (III) tris (1-phenyl-3-methylbenzimidazolin-2-ylidene-C, C2'), bis (2,4-difluorophenylpyridinato ) (5- (pyridin-2-yl) -1H-tetrazolate) iridium (III), factris [(2,6-diisopropylphenyl) -2-phenyl-1H-imidazole [e] iridium (III), fac-tris ( 1-phenyl-3-methylimidazolin-2-ylidene-C, C (2) 'iridium (III), mer-Tris (1-phenyl-3-methylimidazolin-2-ylidene-C, C (2)' iridium (III ), Bis (1-phenyl-3-methylimdazolin-2-ylidene-C, C2 ') (2- (2H-pyrazol-3-yl) -pyridine) iridium (III), bis (1- (4-methylphenyl) -3-methylimdazolin-2-ylidene-C, C2 ') (2- (2H-pyrazol-3-yl) -pyridine) Iri dium (III), bis (1- (4-fluorophenyl) -3-methylimdazolin-2-ylidene-C, C2 ') (2- (2H-pyrazol-3-yl) -pyridine) Iridium (III), bis ( 1- (4-fluorophenyl) -3-methylimdazolin-2-ylidene-C, C2 ') (2- (1H-imidazol-2-yl) pyridine) Iridium (III), bis (1- (4-fluorophenyl) - 3-methylimidazolin-2-ylidene-C, C2 ') (2- (5-trifluoromethyl-2H-pyrazol-3-yl) -pyridine) Iridiummine (III), fac-tris (1,3-diphenylbenzimidazolin-2-ylidene -C, C2 ') iridium (III), bis (1- (4-fluorophenyl) -3-methylimdazolin-2-ylidene-C, C2') (3,5-dimethyl-2- (1H-pyrazole-5-) yl) pyridine) iridium (III), bis (1- (4-methylphenyl) -3-methylimdazolin-2-ylidene-C, C2 ') (3,5-dimethyl-2- (1H-pyrazol-5-yl) pyridine) iridium (III), bis (2-benzo [b] thiophen-2-ylpyridine) (acetylacetonato) iridium (III), bis (1-phenylisoquinoline) (acetylacetonato) iridium (III), bis [1- ( 9,9-dimethyl-9H-fluoren-2-yl) -isoquinoline] (acetylacetonato) iridium (III), bis [2- (9,9-dimethyl-9H-fluoren-2-yl) quinoline] (acetylacetonato) iridium (III), tris (2-phenylquinoline) iridium (III), bis (2-phenylquinoline) (acetylacetonato) iridium (III), bis (2-phenylbenzotet hiazolato) (acetylacetonato) iridium (III), 5,10,15,20-tetraphenyltetrabenzoporphyrin platinum, bis [2- (4-n-hexylphenyl) quinoline] (acetylacetonato) iridium (III), tris [2- (4-n -hexylphenyl) quinoline)] iridium (III), tris [2-phenyl-4-methylquinoline]] iridium (III), bis (2-phenylquinoline) (2- (3-methylphenyl) pyridinato) iridium (III), bis ( 2- (9,9-diethyl-fluoren-2-yl) -1-phenyl-1H-benzo [d] imidazolato) (actylacetonato) iridium (III), bis (2-phenylpyridine) (3- (pyridine-2-yl) yl) -2H-chromen-2-onato) iridium (III), bis (2-phenylquinoline) (2,2,6,6-tetramethylheptane-3,5-dionato) iridium (III), bis (phenylisoquinoline) (2 , 2,6,6-tetramethylheptane-3,5-dionato) iridium (III), bis [(4-n-hexylphenyl) isoquinoline] (acetylacetonato) iridium (III), Pt (II) octaethylporphin, bis (2-methyldibenzo [f, h] quinoxaline) (acetylacetonato) iridium (III), tris [(4-n- hexylphenyl) isoquinoline] iridium (III), bis (4-methyl-2- (thiophen-2-yl) quinoline) (acetylacetonato) iridium (III), FCNIr-Pic (bis [2- (5-cyano-4,6 -difluorophenyl) pyridinato-C2, N] (picolinato) iridium (III)) and FK306. Further exemplary n-TMCs are also made, for example
Die Herstellung kann gemäß bestimmten Ausführungsformen durch Lösungsprozessierung, also durch Herstellen in Lösung, oder Ko-Verdampfung aus der Gasphase erfolgen, beispielsweise auch durch Elektrospray-Ionisation/Elektrospray (ESI). Die Alkalimetallkationenkomplexe der nTNCs (Kat-n-TMC) können somit sowohl durch Lösungsprozessierung als auch durch Ko-verdampfung aus der Gasphase erhalten werden. The preparation can be carried out according to certain embodiments by solution processing, ie by preparation in solution, or co-evaporation from the gas phase, for example by electrospray ionization / electrospray (ESI). The alkali metal cation complexes of the nTNCs (Kat-n-TMC) can thus be obtained both by solution processing and by co-evaporation from the gas phase.
Elektrospray ist die Bezeichnung für ein Verfahren zur Zerstäubung von Flüssigkeiten mit Hilfe eines elektrischen Feldes. Das resultierende Spray enthält feine, hoch unipolar geladene Tropfen mit einer schmalen Größenverteilung. Das physikalische Prinzip beruht auf der Instabilität eines Taylor-Kegels. Die erforderliche Feldstärke zur Zerstäubung der Flüssigkeit ist relativ hoch und stark abhängig von der elektrischen Leitfähigkeit und der Oberflächenspannung der Flüssigkeit. Ist die Leitfähigkeit und/oder die Oberflächenspannung der Flüssigkeit sehr hoch, kann es zur Teilentladung (Koronaentladung) oder zur vollständigen Entladung des Umgebungsgases kommen, bevor die Zerstäubung der Flüssigkeit einsetzt. Electrospray is the name of a process for atomizing liquids by means of an electric field. The resulting spray contains fine, highly unipolar charged drops with a narrow size distribution. The physical principle is based on the instability of a Taylor cone. The required field strength for atomizing the liquid is relatively high and strongly dependent on the electrical conductivity and the surface tension of the liquid. If the conductivity and / or the surface tension of the liquid is very high, partial discharge (corona discharge) or complete discharge of the ambient gas may occur before atomization of the liquid commences.
Als Taylor-Kegel (auch Taylor-Konus genannt) bezeichnet man die kegelförmige Deformation einer Flüssigkeitsoberfläche, die einem elektrischen Feld ausgesetzt wird. Die Deformation resultiert aus einem Kräftegleichgewicht zwischen der Gravitation, der Oberflächenspannung, dem inneren hydrostatischen Druck, dem äußeren Gasdruck und der elektrischen Kraft, die aus dem angelegten elektrischen Feld resultiert. The Taylor cone (also called Taylor cone) is the conical deformation of a liquid surface that is exposed to an electric field. The deformation results from a balance of forces between gravity, surface tension, internal hydrostatic pressure, external gas pressure, and electrical force resulting from the applied electric field.
Wird eine bestimmte kritische Feldstärke überschritten, so wird der Taylor-Kegel instabil und es bildet sich an der Kegelspitze ein dünner Flüssigkeitsfaden (sog. Jet), der unmittelbar nach der Emission in ein Spray aus feinen, hoch unipolar aufgeladenen Tropfen zerfällt (Elektrospray). Dieses Verfahren wird in der Praxis häufig benutzt, um monodisperse Aerosole (gasgetragene Tropfen mit einer schmalen Größenverteilung) oder auch Ionen zu erzeugen. If a certain critical field strength is exceeded, the Taylor cone becomes unstable and forms at the apex of a thin liquid thread (so-called jet), which disintegrates immediately after emission in a spray of fine, highly unipolar charged drops (electrospray). This method is often used in practice to produce monodisperse aerosols (gas-borne droplets with a narrow size distribution) or even ions.
Damit lassen sich nur Aggregate charakterisieren, wie sie beispielsweise auch in festen Schichten existieren können. Die Wechselwirkung innerhalb der Aggregate kann sehr schwach sein oder nur bei angelegtem elektrischem Feld auftreten. Für den Betrieb eines optoelektronischen Bauelements kann dies von entscheidender Bedeutung sein. Thus, only aggregates can be characterized, as they can exist, for example, in solid layers. The interaction within the aggregates can be very weak or occur only with an applied electric field. For the operation of an optoelectronic component, this may be of crucial importance.
Im Falle der Lösungsprozessierung wie auch bei einer Ko-Verdampfung ist hierbei das Lösungsmittel nicht besonders beschränkt. Auch ist das Verfahren ansonsten nicht weiter beschränkt, so lange ein neutraler Übergangsmetallkomplex mit einem Alkalimetallsalz zusammengebracht wird. Besonders bevorzugte Anionen des Alkalimetallsalzes sind BF4 –, PF6 –, CF3SO3 –, SO4 2–, PO4 3–, fluorierte und nicht fluorierte aromatische, heteroaromatische oder aliphatische oder cycloaliphatische Carboxylate, Sulfonate etc. In the case of solution processing as well as co-evaporation, the solvent is not particularly limited. Also, the process is otherwise not further limited as long as a neutral transition metal complex is contacted with an alkali metal salt. Particularly preferred anions of the alkali metal salt are BF 4 - , PF 6 - , CF 3 SO 3 - , SO 4 2- , PO 4 3- , fluorinated and non-fluorinated aromatic, heteroaromatic or aliphatic or cycloaliphatic carboxylates, sulfonates etc.
Die erfindungsgemäßen Verbindungen/Komplexe sind positiv geladen und können damit als iTMCs (ionic transition metal compex) der OLEECs interpretiert werden. Dies bedeutet, dass die p- und n-Transportschichten der OLEDs für die Nutzung in OLEECs erschlossen werden können. Die Emitterschichten/ lichtemittierenden Schichten solcher OLEECs bzw. auch von gewöhnlichen OLEDS können erfindungsgemäß die ionischen Kat-n-TMCs enthalten. Es wird beispielsweise damit auch ein Hybrid OLEEC/OLED Bauelement erhalten, das die Vorteile beiden Technologieaspekte für lichtemittierende Bauteile nutzen kann. The compounds / complexes according to the invention are positively charged and can thus be interpreted as iTMCs (ionic transition metal compex) of the OLEECs. This means that the p and n transport layers of the OLEDs can be tapped for use in OLEECs. According to the invention, the emitter layers / light-emitting layers of such OLEECs or also of ordinary OLEDs can contain the ionic Kat-n TMCs. For example, it also provides a hybrid OLEEC / OLED device that can take advantage of both technology aspects for light emitting devices.
Weiterhin betrifft die Erfindung gemäß bestimmten Aspekten somit die Verwendung der erfindungsgemäßen Verbindung als ionischer Übergangsmetallkomplex in optoelektronischen Bauteilen, insbesondere organischen lichtemittierenden elektrochemischen Zellen (OLEEC) oder organischen lichtemittierenden Dioden (OLED) oder Hybrid-OLEEC/OLED-Bauelementen. Darüber hinaus betrifft die Erfindung auch die Verwendung der erfindungsgemäßen Verbindung als Emitter von Licht, beispielsweise im UV-, sichtbaren und IR-Bereich. Hierbei wird beispielsweise Licht emittiert, dass im Wesentlichen, beispielsweise zu mehr als 50%, mehr als 70% oder mehr als 90%, dem Emissionsspektrum des neutralen Übergangsmetallkomplexes entspricht. Furthermore, according to certain aspects, the invention thus relates to the use of the compound according to the invention as an ionic transition metal complex in optoelectronic components, in particular organic light-emitting electrochemical cells (OLEEC) or organic light-emitting diodes (OLED) or hybrid OLEEC / OLED components. Moreover, the invention also relates to the use of the compound according to the invention as an emitter of light, for example in the UV, visible and IR range. In this case, for example, light is emitted that corresponds essentially, for example to more than 50%, more than 70% or more than 90%, to the emission spectrum of the neutral transition metal complex.
Zudem betrifft die vorliegende Erfindung ein optoelektronisches Bauelement, welches die erfindungsgemäße Verbindung umfasst. Gemäß bestimmten Ausführungsformen ist dieses Bauelement eine OLEEC oder eine OLED oder ein Hybrid-OLEEC/OLED-Bauelement. In solchen Bauelementen befindet sich die erfindungsgemäße Verbindung bevorzugt in einer lichtemittierenden Schicht. In addition, the present invention relates to an optoelectronic component which comprises the compound according to the invention. According to certain embodiments, this device is an OLEEC or an OLED or a hybrid OLEEC / OLED device. In such components, the compound of the invention is preferably in a light-emitting layer.
Ein beispielhafter Aufbau von OLEDs ist in den
Die in
Die in
In
Unterhalb der Anode ist Licht
Gemäß der Erfindung ist nunmehr vorgesehen, dass solche OLEDs bzw. solche OLEECs die erfindungsgemäßen Verbindungen umfassen, beispielsweise in der Emitterschicht. In diese können sie zusammen mit geeigneten Anionen eingebracht werden, beispielsweise mit BF4 –, PF6 –, CF3SO3 –, SO4 2–, PO4 3–, fluorierten und nicht fluorierten aromatischen, heteroaromatischen oder aliphatischen oder cycloaliphatischen Carboxylaten, Sulfonaten etc., beispielsweise BF4 –, PF6 –, CF3SO3 –, SO4 2–, PO4 3–. According to the invention, it is now provided that such OLEDs or such OLEECs comprise the compounds according to the invention, for example in the emitter layer. In this they can be introduced together with suitable anions, for example with BF 4 - , PF 6 - , CF 3 SO 3 - , SO 4 2- , PO 4 3- , fluorinated and non-fluorinated aromatic, heteroaromatic or aliphatic or cycloaliphatic carboxylates, Sulfonates etc., for example BF 4 - , PF 6 - , CF 3 SO 3 - , SO 4 2- , PO 4 3- .
In der lichtemittierenden Schicht können, beispielsweise in einer organischen Schicht
Typische Lochtransportmaterialien, die hier in Schicht
N, N'-Bis(naphthalin-1-yl)-N,N'-bis(phenyl)-9,9-dimethylfluoren, N, N'-Bis(3-methylphenyl)-N,N'-bis(phenyl)-9,9-diphenylfluoren, N, N'-Bis(naphthalin-1-yl)-N,N'-bis(phenyl)-9,9-diphenylfluoren, N, N'-Bis(naphthalin-1-yl)-N,N'-bis(phenyl)-2,2-dimethylbenzidin, N, N'-Bis(3-methylphenyl)-N,N'-bis(phenyl)-9,9-spirobifluoren, 2,2',7,7'-Tetrakis(N, N-diphenylamino)-9,9'-spirobifluoren, N, N'-Bis(naphthalin-1-yl)-N,N'-bis(phenyl)benzidin, N, N'-Bis(naphthalin-2-yl)-N,N'-bis(phenyl)benzidin, N, N'-Bis(3-methylphenyl)-N,N'-bis(phenyl)benzidin, N, N'-Bis(3-methylphenyl)-N,N'-bis(phenyl)-9,9-dimethylfluoren, N, N'-Bis(naphthalin-1-yl)-N,N'-bis(phenyl)-9,9-spirobifluoren, Di-[4-(N,N-ditolylamino)phenyl]cyclohexan, 2,2',7,7'-tetra(N, N-di-tolyl)aminospirobifluoren, 9,9-Bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]-9H-fluoren, 2,2',7,7'-Tetrakis[N-naphthalinyl(phenyl)-amino]-9,9-spirobifluoren, 2,7-Bis[N,N-bis(9,9-spiro-bifluoren-2-yl)-amino]-9,9-spirobifluoren, 2,2'-Bis[N,N-bis(biphenyl-4-yl)amino]-9,9-spirobifluoren, N, N'-bis(phenanthren-9-yl)-N,N'-bis(phenyl)benzidin, N, N,N',N'-tetranaphthalin-2-yl-benzidin, 2,2'-Bis(N,N-di-phenylamino)-9,9-spirobifluoren, 9,9-Bis[4-(N,N-bis-naphthalin-2-yl-amino)phenyl]-9H-fluoren, 9,9-Bis[4-(N, N'-bis-naphthalin-2-yl-N,N'-bis-phenylamino)-phenyl]-9H-fluoren, Titanoxidphthalocyanin, Kupfer-phthalocyanin, 2,3,5,6-Tetrafluoro-7,7,8,8,-tetracyanochinodimethan, 4,4',4"-Tris(N-3-methylphenyl-N-phenylamino)triphenylamin, 4,4',4"-Tris(N-(2-naphthyl)-N-phenylamino)triphenylamin, 4,4',4"-Tris(N-(1-naphthyl)-N-phenylamino)triphenylamin, 4,4',4"-Tris(N,N-diphenylamino)triphenylamin, Pyrazino[2,3-f][1,10]phenanthrolin-2,3-dicarbonitril, N,N,N',N'-Tetrakis(4-methoxyphenyl)benzidin. In the light-emitting layer, for example in an
Typical hole transport materials, here in
N, N'-bis (naphthalen-1-yl) -N, N'-bis (phenyl) -9,9-dimethylfluorene, N, N'-bis (3-methylphenyl) -N, N'-bis (phenyl ) -9,9-diphenylfluorene, N, N'-bis (naphthalen-1-yl) -N, N'-bis (phenyl) -9,9-diphenylfluorene, N, N'-bis (naphthalen-1-yl ) -N, N'-bis (phenyl) -2,2-dimethylbenzidine, N, N'-bis (3-methylphenyl) -N, N'-bis (phenyl) -9,9-spirobifluorene, 2,2 ' , 7,7'-Tetrakis (N, N-diphenylamino) -9,9'-spirobifluorene, N, N'-bis (naphthalen-1-yl) -N, N'-bis (phenyl) benzidine, N, N '- bis (naphthalen-2-yl) -N, N'-bis (phenyl) benzidine, N, N'-bis (3-methylphenyl) -N, N'-bis (phenyl) benzidine, N, N'- Bis (3-methylphenyl) -N, N'-bis (phenyl) -9,9-dimethylfluorene, N, N'-bis (naphthalen-1-yl) -N, N'-bis (phenyl) -9.9 -spirobifluorene, di- [4- (N, N-ditolylamino) phenyl] cyclohexane, 2,2 ', 7,7'-tetra (N, N-di-tolyl) aminospirobifluorene, 9,9-bis [4- (4-bis) N, N-bis-biphenyl-4-yl-amino) -phenyl] -9H-fluorene, 2,2 ', 7,7'-tetrakis [N -naphthalenyl (phenyl) -amino] -9,9-spirobifluorene, 2 , 7-bis [N, N-bis (9,9-spiro-bifluoren-2-yl) -amino] -9,9-spirobifluorene, 2,2'-bis [N, N-bis (biphenyl-4-) yl) amino] -9 9-spirobifluorene, N, N'-bis (phenanthren-9-yl) -N, N'-bis (phenyl) benzidine, N, N, N ', N'-tetranaphthalen-2-yl-benzidine, 2,2 Bis-bis (N, N-di-phenylamino) -9,9-spirobifluorene, 9,9-bis [4- (N, N-bis-naphthalen-2-yl-amino) -phenyl] -9H-fluorene, 9 , 9-bis [4- (N, N'-bis-naphthalen-2-yl-N, N'-bis-phenylamino) -phenyl] -9H-fluorene, titanium oxide phthalocyanine, copper phthalocyanine, 2,3,5, 6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane, 4,4 ', 4 "-tris (N-3-methylphenyl-N-phenylamino) triphenylamine, 4,4', 4" -tris (N- ( 2-naphthyl) -N-phenylamino) triphenylamine, 4,4 ', 4 "-tris (N- (1-naphthyl) -N-phenylamino) triphenylamine, 4,4', 4" -tris (N, N-diphenylamino ) triphenylamine, pyrazino [2,3-f] [1,10] phenanthroline-2,3-dicarbonitrile, N, N, N ', N'-tetrakis (4-methoxyphenyl) benzidine.
Typische Elektronentransportmaterialien, die hier in Schicht
2,2',2"-(1,3,5-Benzintriyl)-tris(1-phenyl-1-H-benzimidazol), 2-(4-Biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazol, 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthrolin, 8-Hydroxychinolinolato-Lithium, 4-(Naphthalin-1-yl)-3,5-diphenyl-4H-1,2,4-triazol, 1,3-Bis[2-(2,2'-bipyridin-6-yl)-1,3,4-oxadiazo-5-yl]benzol, 4,7-Diphenyl-1,10-phenanthrolin, 3-(4-Biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazol, Bis(2-methyl-8-chinolinolat)-4-(phenylphenolato)Aluminium, 6,6'-Bis[5-(biphenyl-4-yl)-1,3,4-oxadiazo-2-yl]-2,2'-bipyridyl, 2-phenyl-9,10-di(naphthalin-2-yl)anthracen, 2,7-Bis[2-(2,2'-bipyridin-6-yl)-1,3,4-oxadiazo-5-yl]-9,9-dimethylfluoren, 1,3-Bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazo-5-yl]benzol, 2-(naphthalin-2-yl)-4,7-diphenyl-1,10-phenanthrolin, 2,9-Bis(naphthalin-2-yl)-4,7-diphenyl-1,10-phenanthrolin, Tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)boran, 1-Methyl-2-(4-(naphthalin-2-yl)phenyl)-1H-imidazo[4,5-f][1,10]phenanthrolin. Typical electron transport materials, here in
2,2 ', 2 "- (1,3,5-benzyltriyl) -tris (1-phenyl-1-H-benzimidazole), 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1 , 3,4-oxadiazole, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 8-hydroxyquinolinolato lithium, 4- (naphthalen-1-yl) -3, 5-diphenyl-4H-1,2,4-triazole, 1,3-bis [2- (2,2'-bipyridin-6-yl) -1,3,4-oxadiazo-5-yl] benzene, 4 , 7-diphenyl-1,10-phenanthroline, 3- (4-biphenylyl) -4-phenyl-5-tert-butylphenyl-1,2,4-triazole, bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminum, 6,6'-bis [5- (biphenyl-4-yl) -1,3,4-oxadiazol-2-yl] -2,2'-bipyridyl, 2-phenyl-9,10- di (naphthalen-2-yl) anthracene, 2,7-bis [2- (2,2'-bipyridin-6-yl) -1,3,4-oxadiazo-5-yl] -9,9-dimethylfluorene, 1,3-bis [2- (4-tert-butylphenyl) -1,3,4-oxadiazo-5-yl] benzene, 2- (naphthalen-2-yl) -4,7-diphenyl-1,10- phenanthroline, 2,9-bis (naphthalen-2-yl) -4,7-diphenyl-1,10-phenanthroline, tris (2,4,6-trimethyl-3- (pyridin-3-yl) -phenyl) borane, 1-methyl-2- (4- (naphthalen-2-yl) phenyl) -1H-imidazo [4,5-f] [1,10] phenanthroline.
Damit eine OLEEC eine kurze Einschaltzeit besitzt, wird gemäß bestimmten Ausführungsformen zur Matrix, beispielsweise für die Emitterschicht
Beispielhaft sind ionische Flüssigkeiten auf der Basis von: Imidazolium-, Pyridinium-, Pyrollidinium-, Piperidinium-, organisch substituierte Phosphonium-, organisch substituierte Sulfonium-, Morpholinium, Guanidinium-Kationen, mit entsprechenden Anionen. Diese Anionen können Halogenide, oder komplexe Halogenide wie BF4 – oder PF6 –, Carboxylate, Sulfate, Triflate, Bis(trifluormethansulfon)imide, Carbonat oder Hydrogencarbonat, usw. sein. Exemplary are ionic liquids based on: imidazolium, pyridinium, pyrollidinium, piperidinium, organically substituted phosphonium, organically substituted sulfonium, morpholinium, guanidinium cations, with corresponding anions. These anions can halides or complex halides such as BF 4 - or PF 6 -, be carboxylates, sulfates, triflates, bis (trifluoromethanesulfone) imide, carbonate or bicarbonate, etc.
Beispiele für geeignete Guanidinium-Kationen umfassen solche der nachstehenden allgemeinen Formel (1): 
Heteroalkyl- und Heteroarylreste sowie auch die entsprechenden Bestandteile in Alkylheteroaryl- bzw. Heteroarlyalkylresten entsprechen hierbei Resten bzw. Bestandteilen, in denen ein C-Atom der Alkylkette bzw. der Arylgruppe durch ein Heteroatom, beispielsweise N, S oder O, ersetzt ist. Heteroalkyl and heteroaryl radicals and also the corresponding constituents in alkylheteroaryl or heteroarlyalkyl radicals in this case correspond to radicals or constituents in which a C atom of the alkyl chain or the aryl group is replaced by a heteroatom, for example N, S or O.
Beispielhafte Guanidinium-Kationen haben beispielsweise die folgende Formel (2): 
Weitere Beispiele für geeignete organische Kationen sind Bis-Guanidinium-Kationen der allgemeinen Formel (3) 
Die Substituenten R1–R11 können unabhängig voneinander lineare, verzweigte oder cyclische C1–C25 Alkyl-, C6–C25 Aryl-, C7–C25 Alkylaryl-, C7–C25 Arylalkyl-, C1–C20 Heteroalkyl-, oder C2–C25 Heteroaryl-, C3–C25 Alkylheteroaryl-, C3–C25 Heteroarylalkyl-, C7–C25 Heteroalkylaryl-, C7–C25 Arylheteroalkyl-, C3–C25 Heteroalyklheteroaryl-, C3–C25 Heteroarylheteroalkylreste, oder Wasserstoff sein und auch asymmetrische oder symmetrische Bis-Guanidinium-Kationen bilden. Desweiteren können mehrere der Substituenten auch über cyclische oder heterocyclische Verbindungen miteinander verbrückt sein. The substituents R 1 -R 11 can independently of one another be linear, branched or cyclic C 1 -C 25 -alkyl, C 6 -C 25 -aryl, C 7 -C 25 -alkylaryl, C 7 -C 25 -arylalkyl, C 1 -C 20 -heteroalkyl-, or C 2 -C 25 -heteroaryl -, C3-C25 alkyl heteroaryl, C3-C25 heteroarylalkyl, C7-C25 heteroalkylaryl, C7-C25 arylheteroalkyl, C3-C25 Heteroalyklheteroaryl-, C3-C25 Heteroarylheteroalkylreste, or be hydrogen and also asymmetric or symmetrical bis-guanidinium cations form. Furthermore, several of the substituents may also be bridged together via cyclic or heterocyclic compounds.
Beispiele für organisch substituierte Phosphoniumionen sind Verbindungen der allgemeinen Formel [RfRgRhRjP]+, wobei Rf, Rg, Rh und Rj unabhängig voneinander aus der Gruppe der linearen, verzweigten oder cyclischen C1–C25 Alkyl-, C6–C25 Aryl-, C7–C25 Alkylaryl-, C7–C25 Arylalkyl-, C1–C20 Heteroalkyl-, oder C2–C25 Heteroaryl-, C3–C25 Alkylheteroaryl-, C3–C25 Heteroarylalkyl-, C7–C25 Heteroalkylaryl-, C7–C25 Arylheteroalkyl-, C3–C25 Heteroalyklheteroaryl-, C3–C25 Heteroarylheteroalkylreste, oder Wasserstoff ausgewählt sein können, wobei mindestens eines von Rf, Rg, Rh und Rj nicht Wasserstoff ist. Diese können, wie auch die anderen genannten Kationen, ebenfalls auch bevorzugt in Elektrolyten im Kathodenraum eingesetzt werden. Examples of organically substituted phosphonium ions are compounds of the general formula [R f R g R h R j P] + , where R f , R g , R h and R j independently of one another from the group of linear, branched or cyclic C 1 -C 25 -alkyl C6-C25 aryl, C7-C25 alkylaryl, C7-C25 arylalkyl, C1-C20 heteroalkyl, or C2-C25 heteroaryl, C3-C25 alkylheteroaryl, C3-C25 heteroarylalkyl, C7-C25 heteroalkylaryl, , C7-C25 Arylheteroalkyl-, C3-C25 Heteroalyklheteroaryl-, C3-C25 Heteroarylheteroalkylreste, or hydrogen can be selected, wherein at least one of R f, R g, R h and R j is not hydrogen. These, like the other cations mentioned, may also preferably be used in electrolytes in the cathode compartment.
Beispiele für organisch substituierte Sulfoniumionen sind Verbindungen der allgemeinen Formel [RfRgRhS]+, wobei Rf, Rg, und Rh unabhängig voneinander aus der Gruppe der linearen, verzweigten oder cyclischen C1–C25 Alkyl-, C6–C25 Aryl-, C7–C25 Alkylaryl-, C7–C25 Arylalkyl-, C1–C20 Heteroalkyl-, oder C2–C25 Heteroaryl-, C3–C25 Alkylheteroaryl-, C3–C25 Heteroarylalkyl-, C7–C25 Heteroalkylaryl-, C7–C25 Arylheteroalkyl-, C3–C25 Heteroalyklheteroaryl-, C3–C25 Heteroarylheteroalkylreste, oder Wasserstoff ausgewählt sein können, wobei mindestens eines von Rf, Rg, und Rh nicht Wasserstoff ist. Diese können, wie auch die anderen genannten Kationen, ebenfalls auch bevorzugt in Elektrolyten im Kathodenraum eingesetzt werden. Examples of organically substituted sulfonium ions are compounds of the general formula [R f R g R h S] + , where R f , R g and R h independently of one another are selected from the group of the linear, branched or cyclic C 1 -C 25 -alkyl,
Beispiele für Pyridiniumionen sind Verbindungen der allgemeinen Formel [4], 
Beispiele für Morpholiniumionen sind Verbindungen der allgemeinen Formel [5], 
Beispiele für Pyrrolidiniumionen sind Verbindungen der allgemeinen Formel [6], 
Beispiele für Imidazoliumionen sind Verbindungen der allgemeinen Formel [7], 
Daneben sind auch folgende Verbindungen als ionische Flüssigkeiten denkbar:
1-Benzyl-3-methylimidazoliumhexafluorophosphat, 1-Butyl-2,3-dimethylimidazoliumhexafluorophosphat, 1-Butyl-3-methylimidazoliumhexafluorophosphat, 1-Ethyl-3-methylimidazoliumhexafluorophosphat, 1-Hexyl-3-methylimidazoliumhexafluorophosphat, 1-Butyl-1-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)imidazoliumhexafluorophosphat, 1-Methyl-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)imidazoliumhexafluorophosphat, 1-Methyl-3-octylimidazoliumhexafluorophosphat, 1-Butyl-2,3-dimethylimidazoliumtetrafluoroborat, 1-Butyl-3-methylimidazoliumtetrafluoroborat, 1-Ethyl-3-methylimidazoliumtetrafluoroborat, 1-Hexyl-3-methylimidazoliumtetrafluoroborat, 1-Methyl-3-octylimidazoliumtetrafluoroborat, 1-Butyl-3-methylimidazoliumtrifluoromethansulfonat, 1-Ethyl-3-methylimidazoliumtrifluoromethansulfonat, 1,2,3-Trimethylimidazoliumtrifluoromethansulfonat, 1-Ethyl-3-methyl-imidazoliumbis(pentafluoroethylsulfonyl)imid, 1-Butyl-3-methylimidazoliumbis(trifluoromethylsulfonyl)imid, 1-Butyl-3-methylimidazoliummethansulfonat, Tetrabutylammoniumbistrifluoromethansulfonimidat, Tetrabutylammoniummethansulfonat, Tetrabutylammoniumnonafluorobutansulfonat, Tetrabutylammoniumheptadecafluorooctansulfonat, Tetrahexylammoniumtetra-fluoroborat, Tetrabutylammoniumtrifluoromethansulfonat, Tetrabutylammoniumbenzoat, Tetrabutylammoniumchlorid, Tetrabu-tylammoniumbromid, 1-Benzyl-3-methylimidazoliumtetrafluoro-borat, Trihexyltetradecylphosphoniumhexafluorophosphat, Tetrabutylphosphoniummethansulfonat, Tetrabutylphosphoniumtetrafluoroborat, Tetrabutylphosphoniumbromid, 1-Butyl-3-methylpyridiniumbis(trifluoromethylsulfonyl)imid, 1-Butyl-4-methylpyridiniumhexafluorophosphat, 1-Butyl-4-methylpyridiniumtetrafluoroborat, Natriumtetraphenylborat, Tetrabutylammoniumtetraphenylborat, Natriumtetrakis(1-imidazolyl)borat, Caesiumtetraphenylborat. Anstelle der genannten Anionen der ionischen Flüssigkeiten können auch andere Anionen wie Hydrogencarbonat-, Sulfat-, Trifluormethansulfonat-, Bistrifluormethylsulfonylimid-, Tosylat-, Methylsulfat-, Dicyanamid-, oder Carbonat-, Hydrogencarbonat-, Alkylcarboantionen mit 1 bis 25 C-Atomen verwendet werden. In addition, the following compounds are also conceivable as ionic liquids:
1-Benzyl-3-methylimidazolium hexafluorophosphate, 1-butyl-2,3-dimethylimidazolium hexafluorophosphate, 1-butyl-3-methylimidazolium hexafluorophosphate, 1-ethyl-3-methylimidazolium hexafluorophosphate, 1-hexyl-3-methylimidazolium hexafluorophosphate, 1-butyl-1- (3 , 3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) imidazolium hexafluorophosphate, 1-methyl-3- (3,3,4,4,5,5,6, 6,7,7,8,8,8-tridecafluorooctyl) imidazolium hexafluorophosphate, 1-methyl-3-octylimidazolium hexafluorophosphate, 1-butyl-2,3-dimethylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-Hexyl-3-methylimidazolium tetrafluoroborate, 1-methyl-3-octylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1,2,3-trimethylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium bis ( pentafluoroethylsulfonyl) imide, 1-butyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide, 1-butyl-3-methylimidazolium met hansulfonat, Tetrabutylammoniumbistrifluoromethansulfonimidat, tetrabutylammonium methanesulfonate, Tetrabutylammoniumnonafluorobutansulfonat, Tetrabutylammoniumheptadecafluorooctansulfonat, Tetrahexylammoniumtetra fluoroborate, Tetrabutylammoniumtrifluoromethansulfonat, tetrabutylammonium benzoate, tetrabutylammonium chloride, Tetrabu-tylammoniumbromid, 1-benzyl-3-methylimidazoliumtetrafluoro-borate, Trihexyltetradecylphosphoniumhexafluorophosphat, Tetrabutylphosphoniummethansulfonat, Tetrabutylphosphoniumtetrafluoroborat, tetrabutylphosphonium bromide, 1-butyl-3-methylpyridiniumbis ( trifluoromethylsulfonyl) imide, 1-butyl-4-methylpyridinium hexafluorophosphate, 1-butyl-4-methylpyridinium tetrafluoroborate, sodium tetraphenylborate, tetrabutylammonium tetraphenylborate, sodium tetrakis (1-imidazolyl) borate, cesium tetraphenylborate. Instead of the abovementioned anions of the ionic liquids, it is also possible to use other anions such as bicarbonate, sulfate, trifluoromethanesulfonate, bistrifluoromethylsulfonylimide, tosylate, methylsulfate, dicyanamide, or carbonate, bicarbonate, alkylcarboantions having from 1 to 25 carbon atoms ,
Die Abscheidung der einzelnen Schichten für OLEDs, OLEECs oder OLED/OLEEC Hybridbauteile erfolgt gemäß bestimmten Ausführungsformen vornehmlich aus Lösung durch Drucken (Tintenstrahldruck, Tiefdruck, Rakeln etc.) oder Rotationsbeschichtung, wobei das Lösungsmittel folgende flüssige verdampfbare organische Substanzen beispielhaft, aber nicht einschränkend umfassen kann:
PGMEA = Propylenglykolmonoethyletheracetat, Tetrahydrofuran, Dioxan, Chlorbenzol, Diethylenglykoldiethylether, Diethylenglykolmonoethylether, gamma-Butyrolacton, N-Methylpyrrolidon, Ethoxyethanol, Xylol, Toluol, Anisol, Phenetol, Acetonitril etc., oder Gemische davon Deposition of the individual layers for OLEDs, OLEECs, or OLED / OLEEC hybrid devices, according to certain embodiments, is primarily solution through printing (ink jet printing, gravure printing, knife coating, etc.) or spin coating, which solvent may include, but is not limited to, the following liquid vaporizable organic substances :
PGMEA = propylene glycol monoethyl ether acetate, tetrahydrofuran, dioxane, chlorobenzene, diethylene glycol diethyl ether, diethylene glycol monoethyl ether, gamma-butyrolactone, N-methylpyrrolidone, ethoxyethanol, xylene, toluene, anisole, phenetole, acetonitrile, etc., or mixtures thereof
Die Lösung wird auf ein Substrat mit geeigneter leitfähiger Elektrode aufgebracht. Die Elektrode
Zusätzlich können polymere Verbindungen als Matrixmaterial beispielsweise für die Emitterschicht
Die obigen Ausführungsformen, Ausgestaltungen und Weiterbildungen lassen sich, sofern sinnvoll, beliebig miteinander kombinieren. Weitere mögliche Ausgestaltungen, Weiterbildungen und Implementierungen der Erfindung umfassen auch nicht explizit genannte Kombinationen von zuvor oder im Folgenden bezüglich der Ausführungsbeispiele beschriebenen Merkmalen der Erfindung. Insbesondere wird der Fachmann auch Einzelaspekte als Verbesserungen oder Ergänzungen zu der jeweiligen Grundform der vorliegenden Erfindung hinzufügen. The above embodiments, refinements and developments can, if appropriate, be combined with one another as desired. Further possible refinements, developments and implementations of the invention also include combinations of features of the invention which have not been explicitly mentioned above or described below with regard to the exemplary embodiments. In particular, the person skilled in the art will also add individual aspects as improvements or additions to the respective basic form of the present invention.
Beispiele Examples
In den Beispielen werden Ergebnisse von massenspektroskopischen Untersuchungen vorgestellt, die zeigen, dass bestimmte Alkalimetallkationen Komplexe mit neutralen phosphoreszenten Emittern (nTMC = neutral transition metal complex) ausbilden. In the examples results of mass spectroscopic investigations are presented which show that certain alkali metal cations form complexes with neutral phosphorescent emitters (nTMC = neutral transition metal complex).
Hierzu wurden verschiedene Alkalimetallkationen (Li+, Na+, K+, Rb+, Cs+) mit einem beispielhaften Übergangsmetallkomplex, Tris(2-phenyl-pyridin)Iridium(III) mittels Elektrospray (ESI) umgesetzt. Der Ligand 2-Phenylpyridin hat dabei die chemische Formel C11H8N– und somit ein Molekulargewicht von 154,19 g/mol (exakte Masse 154,07 g/mol). Als Referenz wurde eine Protonierung des Übergangsmetallkomplexes durchgeführt. For this purpose, various alkali metal cations (Li + , Na + , K + , Rb + , Cs + ) were reacted with an exemplary transition metal complex, tris (2-phenyl-pyridine) iridium (III) using electrospray (ESI). The ligand 2-phenylpyridine has the chemical formula C 11 H 8 N - and thus a molecular weight of 154.19 g / mol (exact mass 154.07 g / mol). As a reference, protonation of the transition metal complex was performed.
Die folgenden Ergebnisse, welche in
Überraschenderweise wurde festgestellt, dass immer wenn neutrale cyclometallierte phosphoreszente Iridiumkomplexe mittels ESI untersucht wurden, besonders stabile kationische Spezies entstehen, wo ein Alkalimetallion mit 1 bzw. 2 neutralen phosphoreszenten Emittereinheiten wechselwirkt. Surprisingly, it has been found that whenever neutral cyclometallated phosphorescent iridium complexes have been investigated by ESI, particularly stable cationic species are formed, where an alkali metal ion interacts with 1 or 2 neutral phosphorescent emitter units.
So sind in
In
In
In
Die Existenz der erfindungsgemäßen Verbindung (Komplexklasse) wurde somit durch massenspektroskopische Untersuchungen verifiziert. The existence of the compound of the invention (complex class) was thus verified by mass spectroscopic studies.
Im Sinne der Erfindung sind daher die positiven Ionen von neutralen phosphoreszenten Emitterkomplexen (n-TMC) der allgemeinen Formel:
Überraschenderweise koordinieren die Alkalimetallkationen an neutrale phosphoreszenten Emittermaterialien auf Basis von Übergangsmetallen (n-TMC). Auf diese Weise werden diese dann ionisch (Kat-n-TMC). Die so erhaltenen erfindungsgemäßen Verbindungen können in organischen lichtemittierenden elektrochemischen Zellen Verwendung finden. Surprisingly, the alkali metal cations coordinate to neutral phosphorescent emitter materials based on transition metals (n-TMC). In this way they become ionic (Kat-n-TMC). The compounds according to the invention thus obtained can be used in organic light-emitting electrochemical cells.
Somit ist es zudem im Rahmen der Erfindung, diese Addukte M+(n-TMC)x als phosphoreszente Emitter in einem optoelektronischen Bauelement wie einer OLEEC oder einer OLED oder einem Hybrid-OLEEC/OLED-Bauelement, bevorzugt in einer organischen lichtemittierenden elektrochemischen Zelle (OLEEC) oder einem Hybrid-OLEEC/OLED-Bauelement, zu verwenden. Eine organische lichtemittierende elektrochemische Zelle (OLEEC) oder ein Hybrid-OLEEC/OLED-Bauelement umfassend die erfindungsgemäße Verbindung sind somit ebenfalls bevorzugt. Thus, it is also within the scope of the invention to use these adducts M + (n-TMC) x as phosphorescent emitters in an optoelectronic component such as an OLEEC or an OLED or a hybrid OLEEC / OLED component, preferably in an organic light-emitting electrochemical cell ( OLEEC) or a hybrid OLEEC / OLED device. An organic light-emitting electrochemical cell (OLEEC) or a hybrid OLEEC / OLED component comprising the compound according to the invention are therefore likewise preferred.
ZITATE ENTHALTEN IN DER BESCHREIBUNG QUOTES INCLUDE IN THE DESCRIPTION
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- Holleman-Wiberg, Lehrbuch der Anorganischen Chemie, 101. Auflage, deGruyter, Berlin, 1995 [0024] Holleman-Wiberg, Textbook of Inorganic Chemistry, 101st Edition, deGruyter, Berlin, 1995 [0024]
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| DE102013225682.5A DE102013225682A1 (en) | 2013-12-12 | 2013-12-12 | Metal ion adducts of neutral phosphorescent emitters for use in light emitting organic optoelectronic devices |
| PCT/EP2014/076422 WO2015086400A1 (en) | 2013-12-12 | 2014-12-03 | Metal ion adducts of neutral phosphorescent emitters for use in light-emitting organic optoelectronic components |
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| DE102013225682.5A DE102013225682A1 (en) | 2013-12-12 | 2013-12-12 | Metal ion adducts of neutral phosphorescent emitters for use in light emitting organic optoelectronic devices |
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| DE102013225682A1 true DE102013225682A1 (en) | 2015-06-18 |
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