DE102012007810A1 - Electronic device, preferably organic electroluminescent device comprises a transition metal compound exhibiting a transition metal-tin bond - Google Patents

Electronic device, preferably organic electroluminescent device comprises a transition metal compound exhibiting a transition metal-tin bond

Info

Publication number
DE102012007810A1
DE102012007810A1 DE102012007810A DE102012007810A DE102012007810A1 DE 102012007810 A1 DE102012007810 A1 DE 102012007810A1 DE 102012007810 A DE102012007810 A DE 102012007810A DE 102012007810 A DE102012007810 A DE 102012007810A DE 102012007810 A1 DE102012007810 A1 DE 102012007810A1
Authority
DE
Germany
Prior art keywords
snb
transition metal
ag
sn
electronic device
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.)
Withdrawn
Application number
DE102012007810A
Other languages
German (de)
Inventor
Esther Breuning
Dominik Joosten
Hartmut Schubert
Phllipp Stoessel
Lars Wesemann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to EP11004024 priority Critical
Priority to EPEP11004024.3 priority
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of DE102012007810A1 publication Critical patent/DE102012007810A1/en
Application status is Withdrawn legal-status Critical

Links

Classifications

    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/0077Coordination compounds, e.g. porphyrin
    • H01L51/0091Metal complexes comprising a IB-metal (Cu, Ag, Au)
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/0077Coordination compounds, e.g. porphyrin
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/0077Coordination compounds, e.g. porphyrin
    • H01L51/0084Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H01L51/0085Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising Iridium
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/0077Coordination compounds, e.g. porphyrin
    • H01L51/0084Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H01L51/0087Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/0032Selection of organic semiconducting materials, e.g. organic light sensitive or organic light emitting materials
    • H01L51/0077Coordination compounds, e.g. porphyrin
    • H01L51/009Polynuclear complexes, i.e. complexes having two or more metal centers
    • HELECTRICITY
    • H01BASIC ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES; ELECTRIC SOLID STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H01L51/00Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof
    • H01L51/50Solid state devices using organic materials as the active part, or using a combination of organic materials with other materials as the active part; Processes or apparatus specially adapted for the manufacture or treatment of such devices, or of parts thereof specially adapted for light emission, e.g. organic light emitting diodes [OLED] or polymer light emitting devices [PLED];
    • H01L51/5012Electroluminescent [EL] layer
    • H01L51/5016Triplet emission

Abstract

The invention relates to an electronic device, in particular an organic electroluminescent device comprising at least one transition metal compound having at least one transition metal-tin bond.

Description

  • The present invention relates to an electronic device, in particular an organic electroluminescent device, which comprises at least one transition metal compound having at least one transition metal-tin bond and the use of such a transition metal compound in an electronic device.
  • In the literature, a variety of transition metal compounds having at least one transition metal-tin bond is known, for. [Pt 3 Sn 8 Cl 20 ] 4- or [(COD) 3 Pt 3 Sn 2 Cl 6 ] ( Inorg. Chem. 1966, 5, 109-110 ) or Pd and Pt complexes containing a SnCl 3 group ( J. Chem. Soc. A 1971, 3765-3769 ). In general, little is known about the luminescence properties of these compounds from the literature.
  • The construction of organic electroluminescent devices (OLEDs) in which organic semiconductors are used as functional materials is described, for example, in US Pat US 4539507 . US 5151629 . EP 0676461 and WO 98/27136 described. However, further improvements are desirable. The triplet emitters used are predominantly mononuclear iridium or platinum complexes. The compounds used to date for emitter systems, in particular triplet emitter systems, for OLEDs still have to be improved in terms of their lifetime, efficiency and color purity in order to be used, for example in color television sets. There is therefore a need for further, in particular improved emitter systems for organic electroluminescent devices.
  • The invention relates to an electronic device, in particular an organic electroluminescent device comprising at least one transition metal compound having at least one transition metal-tin bond.
  • Surprisingly, the transition metal compound having at least one transition metal-tin bond leads to good stability and to further positive properties of the OLEDs. The transition metal compound which has at least one transition metal-tin bond is also referred to below as "transition metal compound having at least one transition metal-tin bond".
  • Most general formula for a transition metal compound according to the invention can be a compound of the following formula (TM) n ("Sn") o (L) p where ÜM stands for a transition metal, "Sn" for a tin-containing ligand, which coordinates via a tin atom to the transition metal and L is another ligand, which may be monodentate or polydentate. Furthermore, for the indices it holds that n ≥ 1, o ≥ 1 and p ≥ 0.
  • The transition metal compound having at least one transition metal-tin bond is thus a transition metal complex containing one or more transition metals and one or more tin-containing ligands, wherein at least one tin atom is coordinated to at least one transition metal. The tin-containing ligand may be mono- or polydentate.
  • For the purposes of the invention, a tin-containing ligand is preferably defined as a hetero-closo-dodecaborate of the formula [SnB 11 R 11 ] 2- , [SnCB 10 R 11 ] - or [Sn 2 B 10 R 10 ] 2- , wherein R is as defined below, or as a stannane of the formula [η 1 -SnY 3 ] - , [μ 2 -SnY 2 ] - or [μ 3 -SnY] - , wherein Y is the same or different at each occurrence for F, Cl , Br, I, aryloxy, alkoxy, aryl, heteroaryl or alkyl. These ligands coordinate to the transition metal with the coordination mode η 1 , μ 2 , μ 3 or μ 4 . Here, as is common practice in coordination chemistry, η 1 means that the tin atom is coordinated to exactly one transition metal atom, and μ 2 means that the tin atom is simultaneously coordinated to two transition metal atoms, and μ 3 that the tin atom is simultaneously coordinated to three transition metal atoms , and μ 4 that the tin atom is simultaneously coordinated to four transition metal atoms.
  • An electronic device, in particular an organic electroluminescent device, is understood to mean a device which comprises an anode, a cathode and at least one emitting layer, which is arranged between the anode and the cathode, wherein at least one layer between the anode and the cathode is at least contains an organic or organometallic compound. Preferably, an emissive layer of an organic electroluminescent device contains the transition metal compound described herein having at least one transition metal-tin bond and optionally a matrix material. An organic electroluminescent device need not necessarily contain only layers composed of organic or organometallic materials. So it is also possible that one or more layers contain inorganic materials or are constructed entirely of inorganic materials.
  • In one embodiment of the invention, the transition metal compound having at least one transition metal-tin bond can have exactly one transition metal-tin bond.
  • In a further embodiment, the transition metal compound having at least one transition metal-tin bond may have more than one transition metal-tin bond.
  • The transition metal compound may contain n transition metals, where n is a natural number. The following cases may occur:
    • a) n = 1: it is a mononuclear transition metal complex with one or more tin-containing ligands; and
    • b) n> 1: it is a polynuclear transition metal complex with one or more tin-containing ligands. In particular, n = 2 to 10, preferably n = 2, 3, 4, 5 or 6.
  • In one embodiment of the invention, the transition metal compound, as listed above, contains two or more transition metals. In this case, one, several or each transition metal can not be bound or coordinated to a tin atom, bound or coordinated to a tin atom or bound or coordinated to a plurality of tin atoms, wherein the tin atom may be the same or different, with the proviso that at least one tin atom is bonded or coordinated to at least one transition metal.
  • In one embodiment, the transition metal compound having at least one transition metal-tin bond may comprise n transition metals, wherein the transition metals are partially or completely bonded to each other through one or more transition metal-transition metal bonds. However, it is also possible that the transition metals are not bound to each other by transition metal-transition metal bonds or only a portion of the transition metals are bound together by such bonds. In a further embodiment, the transition metal compound having at least one transition metal-tin bond may comprise exactly one transition metal.
  • If n = 2, ie the compound has 2 transition metals, these transition metals are arranged linearly. When n = 3, that is, the compound has 3 transition metals, a typical arrangement of transition metals is trigonal. When n = 4, that is, the compound has 4 transition metals, a typical arrangement of the transition metals is tetrahedral or approximately tetrahedral. Thus, when n = 5, the compound thus has 5 transition metals, a typical arrangement of the transition metals is trigonal-bipyramidal or approximately trigonal-bipyramidal. When n = 6, that is, the compound has 6 transition metals, a typical arrangement of the transition metals is octahedral or approximately octahedral.
  • According to a further embodiment, the transition metal compound may contain n transition metals with n> 2, in particular n = 3 to 6, where at least three or all transition metals are partially or completely bonded to one another.
  • In further embodiments, the tin of the transition metal-tin bond may be a coordinating atom of a monodentate or polydentate ligand. A ligand that forms only one coordinating bond is called monodentate or monodentate, while a ligand that forms multiple coordinating bonds is polydentate or multidentate, e.g. B. bidentate for two bonds, is called.
  • The ligand may, as listed above, be selected from the group of the hetero-closo-dodecaborate of the formula [SnB 11 R 11 ] 2- , [SnCB 10 R 11 ] - or [Sn 2 B 10 R 10 ] 2- in coordination mode η 1 , μ 2 , μ 3 or μ 4 , wherein R is the same or different at each occurrence for H, D, halogen, alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms or OH. Preferred hetero-closo-dodecaborates are [SnB 11 R 11 ] 2- and [SnCB 10 R 11 ] - , and more preferably [SnB 11 R 11 ] 2- . In these ligands, the tin is part of the hetero-closo-dodecaborate, so it is a closo-stanna borate. Particular preference is given to R = H. It is therefore particularly preferable for [SnB 11 H 11 ] 2- and [SnCB 10 H 11 ] - ; most preferred is [SnB 11 H 11 ] 2- .
  • The ligand may furthermore, as listed above, be selected from the group consisting of a stannane [η 1 -SnY 3 ] - , [μ 2 -SnY 2 ] - or [μ 3 -SnY] - with Y in each occurrence identical or different, F, Cl, Br, I, aryloxy, alkoxy, aryl, heteroaryl or alkyl, preferably Cl, Br, alkyl or aryl and particularly preferably Cl, methyl or phenyl. An alkyl or alkoxy group preferably has 1 to 10 C atoms and an aryl or aryloxy group 6 to 20 C atoms and a heteroaryl group preferably 5 to 20 aromatic ring atoms. Furthermore, these groups may also be substituted.
  • In the organic electroluminescent device, according to embodiments, at least one of the transition metals may be selected from the group consisting of Zr, Hf, Nb, Ta, Mo, W, Re, Ru, Os, Rh, Ir, Ni, Pd, Pt, Cu, Ag, Au and Zn, preferably Ru, Os, Rh, Ir, Ni, Pd, Pt, Cu, Ag and Au. Particularly preferred are Pt, Cu, Ag and Au.
  • When the transition metal compound contains more than one transition metal, it is preferred that all transition metals be the same.
  • When the ligand is a hetero-closo-dodecaborate of the formula [SnB 11 H 11 ] 2- , [SnCB 10 H 11 ] - or [Sn 2 B 10 H 10 ] 2- , it is preferred that the or the transition metals are identically or differently selected from the group consisting of Pt, Cu, Ag, Au, Rh, Ni and Pd, preferably Pt, Cu, Ag or Au.
  • Preferred transition metals having at least one tin ligand are selected from the group consisting of: [(Ph 3 P) 2 Au 2 (SnB 11 H 11 ) 2 ] 2- , [(Ph 3 P) 2 Au 2 (SnB 11 H 11 ) 3 ] 4-, [(Et 3 P) 3 Au 3 (SnB 11 H 11) 3] 3-, [(dppm) 2 4 Au (SNB 1 1 H 11) 4] 4-, [(Ph 3 P) 2 Ag 2 (SnB 11 H 11 ) 2 ] 2- , [(Et 3 P) 3 Ag 3 (SnB 11 H 11 ) 3 ] 3- , [(Me 3 P) 4 Ag 4 (SnB 11 H 11 ) 4 ] 4- , [Ag 4 (SnB 11 H 11 ) 6 ] 8- , [Au (SnB 11 H 11 ) 4 ] 5- , [(dppm) 2 Au 2 (SnB 11 H 10 (OEt)) 2 ] - , [(dppm) 2 Au 2 (SnB 11 H 11 )], [(Ph 3 P) 2 Au (SnB 11 H 11 )] - , [(Ph 3 P) 2 Ag 2 (SnB 11 H 11 ) 2 ] 2 - , [(Ph 3 P) 2 Cu 2 (SnB 11 H 11 ) 2 ] 2- , [(iPr 3 P) 2 Cu 2 (SnB 11 H 11 ) 2 ] 2- , [(Me 3 P) 4 Cu 2 (SnB 11 H 11 ) 2 ] 2- , [Ag 2 (SnB 11 H 11 ) 2 (PMe 3 ) 4 ] 2- , [Ag 4 (SnB 11 H 11 ) 4 (pyridine) 4 ] 4- , [ Ag 2 (SnB 11 H 11 ) 2 (bipy) 2 ] 2- , [Ag 2 (SnB 11 H 11 ) 2 (phenanthroline) 2 ] 2- , [Ag 2 (SnB 11 H 11 ) 2 (MeBipy) 2 ] 2- , [Au 2 (SnB 11 H 11 ) 4 ] 4- , [Ag (SnB 11 H 11 ) 3 ] 5- , [Cu (SnB 11 H 11 ) 3 (CH 3 CN)] 5- , [Ag 2 (SnB 11 H 11 ) 2 (IprNHC) 2 ] , [Ag 5 (SnB 11 H 11 ) 6 (DPI) 1.5 ] 7- , which may be present as a polymer, [Ag 4 (SnB 11 H 11 ) 4 (DPI) 3 ] - , which may be present as a coordination network, and [ Ag 4 (SnB 11 H 11 ) 4 (t-BuNC) 4 ] 4- , the compounds each still containing suitable counterions. The abbreviations used have the following meanings:
    Figure 00060001
  • In this case, the transition metals in structures containing two or more transition metals may be partially or completely bonded to each other, wherein the tin-containing ligand binds to a transition metal or bridging to a plurality of transition metals.
  • Suitable cationic counterions are preferably selected from the group consisting of trialkylammonium cations or tetraalkylammonium cations, the alkyl group preferably containing between 1 and 10 C atoms, particularly preferably between 1 and 4 C atoms, tetraalkylphosphonium cations, the alkyl group preferably having between 1 and 10 C atoms. Contains atoms, more preferably between 1 and 4 carbon atoms, tetraarylphosphonium cations, alkali metal ions, in particular lithium, sodium or potassium, or alkaline earth metal cations, in particular magnesium or calcium.
  • Examples of suitable compounds are the compounds listed below: [Bu 3 NH] 2 [(Ph 3 P) 2 Au 2 (SnB 11 H 11 ) 2 ]; [Bu 3 MeN] 4 [(Ph 3 P) 2 Au 2 (SnB 11 H 11 ) 3 ]; [Bu 3 NH] 3 [(Et 3 P) 3 Au 3 (SnB 11 H 11 ) 3 ]; [Bu 3 MeN] 4 [(dppm) 2 Au 4 (SnB 11 H 11 ) 4 ]; [Bu 3 MeN] 2 [(Ph 3 P) 2 Ag 2 (SnB 11 H 11 ) 2 ]; [Bu 3 NH] 3 [(Et 3 P) 3 Ag 3 (SnB 11 H 11 ) 3 ]; [Bu 3 NH] 4 [(Me 3 P) 4 Ag 4 (SnB 11 H 11 ) 4 ]; [Et 4 N] 8 [Ag 4 (SnB 11 H 11 ) 6 ]; [Bu 3 NH] 5 [Au (SnB 11 H 11 ) 4 ]; [Bu 3 MeN] [(dppm) 2 Au 2 (SnB 11 H 10 (OEt) 2 ]; [(dppm) 2 Au 2 (SnB 11 H 11 )]; [Bu 3 MeN] [(Ph 3 P) 2 Au (SnB 11 H 11 )]; [Bu 3 NH] 2 [(Ph 3 P) 2 Ag 2 (SnB 11 H 11 ) 2 ]; [Bu 3 MeN] 2 [(Ph 3 P) 2 Cu 2 (SnB 11 H 11 ) 2 ]; [Bu 3 MeN] 2 [(iPr 3 P) 2 Cu 2 (SnB 11 H 11 ) 2 ]; [Bu 3 MeN] 2 [(Me 3 P) 4 Cu 2 (SnB 11 H 11 ) 2 ]; [Bu 3 NH] 2 [Ag 2 (SnB 11 H 11 ) 2 (PMe 3 ) 4 ]; [Et 3 NMe] 4 [Ag 4 (SnB 11 H 11 ) 4 (pyridine) 4 ]; [Et 4 N] 2 [Ag 2 (SnB 11 H 11 ) 2 (bipy) 2 ]; [Et 4 N] 2 [Ag 2 (SnB 11 H 11 ) 2 (phenanthroline) 2 ]; [Et 4 N] 2 [Ag 2 (SnB 11 H 11 ) 2 (MeBipy) 2 ]; [Et 4 N] 4 [Au 2 (SnB 11 H 11 ) 4 ]; [Et 4 N] 5 [Ag (SnB 11 H 11 ) 3 ]; [Et 4 N] 5 [Cu (SnB 11 H 11 ) 3 (CH 3 CN)]; [Et 4 N] [MeIMIpr] [Ag 2 (SnB 11 H 11 ) 2 (IprNHC) 2 ]; [Et 4 N] 7 [Ag 5 (SnB 11 H 11 ) 6 (DPI) 1.5 ], which may be present as a polymer; [Me 4 N] [Ag 4 (SnB 11 H 11 ) 4 (DPI) 3 ], which may be present as a coordination network, and [Et 4 N] 4 [Ag 4 (SnB 11 H 11 ) 4 (t-BuNC) 4 ].
  • The following is an example of the abovementioned complexes containing hetero-closo-dodecaborate as ligands, the structure of the anions of [Bu 3 NMe] 4 [(Ph 3 P) 2 Au 2 (SnB 11 H 11 ) 3 ] ( S. Hagen, I. Pantenburg, F. Weigend, C. Wickleder, L. Wesemann Angew. Chem. 2003, 115, 1539-1543 ), [Et 4 N] 2 [Ag 2 (SnB 11 H 11 ) 2 L 2 ] with L = 2,2'-bipyridine and [Et 4 N] 4 [Au 2 (SnB 11 H 11 ) 4 ] ,
    Figure 00080001
    [(Ph 3 P) 2 Au 2 (SnB 11 H 11 ) 3 ]
    Figure 00080002
    [Ag 2 (SnB 11 H 11 ) 2 L 2 ] with L = 2,2'-bipyridine
    Figure 00090001
    [Au 2 (SnB 11 H 11 ) 4 ]
  • In the organic electroluminescent device, the transition metal compound may emit in the blue, green, red, orange and / or yellow wavelength range. Preferably, the transition metal compound is contained in an emitting layer of the organic electroluminescent device.
  • In the organic electroluminescent device of the present invention, the transition metal compound may be used in combination with a matrix material. Suitable matrix materials are ketones, phosphine oxides, sulfoxides and sulfones, e.g. B. according to WO 2004/013080 . WO 2004/093207 . WO 2006/005627 or WO 2010/006680 , Triarylamines, carbazole derivatives, e.g. B. CBP (N, N-Biscarbazolylbiphenyl), m-CBP or in WO 2005/039246 . US 2005/0069729 . JP 2004/288381 . EP 1205527 . WO 2008/086851 or US 2009/0134784 disclosed carbazole derivatives, indolocarbazole derivatives, e.g. B. according to WO 2007/063754 or WO 2008/056746 , Indenocarbazole derivatives, e.g. B. according to WO 2010/136109 and WO 2011/000455 , Azacarbazoles, e.g. B. according to EP 1617710 . EP 1617711 . EP 1731584 . JP 2005/347160 , bipolar matrix materials, e.g. B. according to WO 2007/137725 , Silane, z. B. according to WO 2005/111172 , Azaborole or Boronester, z. B. according to WO 2006/117052 , Diazasilolderivete, z. B. according to WO 2010/054729 , Diazaphospholderivate, z. B. according to WO 2010/054730 , Triazine derivatives, e.g. B. according to WO 2010/015306 . WO 2007/063754 or WO 2008/056746 , Zinc complexes, e.g. B. according to EP 652273 or WO 2009/062578 , Dibenzofuran derivatives, e.g. B. according to WO 2009/148015 , or bridged carbazole derivatives, e.g. B. according to US 2009/0136779 . WO 2010/050778 . WO 2011/042107 or WO 2011/088877 ,
  • In a further embodiment, the transition metal compound comprises a Pt or Ir complex which contains, in addition to the or the tin-containing ligand, one or two phenyl-pyridine-type ligands L 'or derivatives thereof and optionally one or more further ligands L to the Pt or Ir coordinated, where L and L 'may be different. For example, the tin-containing ligand is one of the aforementioned ligands, preferably a hetero-closo-dodecaborate. The term "phenylpyridine type" means that the ligand L 'comprises a phenylpyridine structure or a phenylpyridine-like structure.
  • Preferably, the Pt or Ir complex is selected from L'Pt ("Sn") L, (L ') 2 Ir ("Sn") L and dimeric structures L'Pt ("Sn") 2 PtL' or (L ') 2 Ir ("Sn") 2 Ir (L') 2 . In this case, two Pt atoms or two Ir atoms are bridged in the dimeric structures via two tin-containing ligands, wherein in each case the tin atom coordinates to both Pt atoms or to both Ir atoms. "Sn" stands for a tin-containing ligand as described above, in particular for a hetero-closo-dodecaborate, as described above, and L stands for a monodentate ligand.
  • L 'in the abovementioned structures can be defined as follows: Preference is given to bidentate monoanionic, neutral or dianionic ligands L', in particular monoanionic ligands having with a metal a cyclometallierten five-membered or six-membered ring with at least one metal-carbon bond, in particular a cyclometallierten five ring. These are, in particular, ligands commonly used in the field of phosphorescent metal complexes for organic electroluminescent devices, e.g. B. ligands of the type phenylpyridine, naphthylpyridine, phenylquinoline, phenylisoquinoline, etc., which may each be substituted by one or more radicals R. The two coordinating rings of the ligand may also be bridged together by radicals R. It is particularly suitable for the combination of two groups, as shown below with formulas, where a group preferably binds via a neutral nitrogen atom or a carbene carbon atom and the other group preferably binds via a negatively charged carbon atom or a negatively charged nitrogen atom.
  • For example, when L 'is phenylpyridine, the above formulas have the following structures:
    Figure 00110001
    wherein Sn represents a tin-containing ligand as described above, in particular a hetero-closo-dodecaborate. Instead of phenylpyridine, the complexes may analogously also have other ortho-metalated ligands, and the ligands may also be substituted.
  • These complexes are new. Another object of the present invention are therefore such complexes.
  • The ligand L 'can comprise a combination of two groups of the formulas shown below, one group preferably bonding via a neutral nitrogen atom or a carbene carbon atom and the other group preferably binding via a negatively charged carbon atom or a negatively charged nitrogen atom. In this case, the ligand L 'is formed from the groups by these groups each bind to each other at the position indicated by # and coordinate to the position indicated by * to the Pt or Ir.
    Figure 00120001
    X is the same or different at each occurrence and is CR or N; preferably a maximum of three symbols X in each group represent N, more preferably at most two symbols X in each group represent N, very particularly preferably at most one symbol X in each group represents N, in particular preferably all the symbols X stand for CR;
    V is the same or different at each occurrence and stands for S or O;
    R is the same or different at each occurrence and is H, D, F, Cl, Br, I, CHO, N (Ar 1 ) 2 , C (= O) Ar 1 , P (= O) (Ar 1 ) 2 , S (= O) Ar 1 , S (= O) 2 Ar 1 , CR 1 = CR 1 Ar 1 , CN, NO 2 , Si (R 1 ) 3 , B (OAr 1 ) 2 , B (Ar 1 ) 2 , B (N (Ar 1 ) 2 ) 2 , B (OR 1 ) 2 , B (R 1 ) 2 , B (N (R 1 ) 2 ) 2 , OSO 2 R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having from 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having from 3 to 40 carbon atoms, each of which may be substituted with one or more R 1 radicals, one or more non-adjacent CH 2 - Groups by R 1 C = CR 1 , C≡C, Si (R 1 ) 2 , C = O, C = NR 1 , P (= O) (R 1 ), SO, SO 2 , NR 1 , O, S or CONR 1 may be replaced and wherein one or more H atoms may be replaced by F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each by one or more R 1 may be substituted, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1 , or a combination of these systems; two or more adjacent substituents R may also together form a mono- or polycyclic, aliphatic or aromatic ring system;
    Ar 1 is the same or different at each occurrence and is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 1 ; in this case, two radicals Ar 1 , which bind to the same nitrogen, phosphorus or boron atom, by a single bond or a bridge selected from B (R 1 ), C (R 1 ) 2 , Si (R 1 ) 2 , C = O, C = NR 1 , C = C (R 1 ) 2 , O, S, S = O, SO 2 , N (R 1 ), P (R 1 ) and P (= O) R 1 , linked together be; and
    R 1 is the same or different at each occurrence and is H, D or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 carbon atoms, in which also H atoms may be replaced by F; two or more adjacent substituents R 1 may also together form a mono- or polycyclic, aliphatic or aromatic ring system.
  • Preferred neutral, monodentate ligands L are selected from the group consisting of carbon monoxide, nitrogen monoxide, alkyl cyanides, such as. For example, acetonitrile, aryl cyanides, such as. B. benzonitrile, alkyl isocyanides, such as. For example, methylisononitrile, aryl isocyanides, such as. B. benzoisonitrile, amines, such as. For example, trimethylamine, triethylamine, morpholine, phosphines, in particular halogenophosphines, 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. For example, trimethyl phosphite, triethyl phosphite, arsines, such as. Trifluorarsine, trimethylarsine, tricyclohexylarsine, tri-tert-butylarsine, triphenylarsine, tris (pentafluorophenyl) arsine, stibines, such as. Trifluorostibine, trimethylstibine, tricyclohexylstibine, tri-tert-butylstibine, triphenylstibine, tris (pentafluorophenyl) stibine, nitrogen-containing heterocycles, such as. As pyridine, pyridazine, pyrazine, pyrimidine, triazine, and carbenes, in particular Arduengo carbenes.
  • Preferred monoanionic, monodentate ligands L are selected from hydride, deuteride, the halides F - , Cl - , Br - and I - , alkyl acetylides, such as. B. Methyl-C≡C -, tert-butyl-C≡C -, Arylacetyliden such. As phenyl C≡C - , cyanide, cyanate, isocyanate, thiocyanate, isothiocyanate, aliphatic or aromatic alcoholates, such as. For example, methanolate, ethanolate, propoxide, iso-propanolate, tert-butylate, phenolate, aliphatic or aromatic thioalcoholates such. As methanethiolate, ethanethiolate, propanethiolate, iso-propanethiolate, tert-thiobutylate, thiophenolate, amides, such as. For example, dimethylamide, diethylamide, di-iso-propylamide, morpholide, carboxylates, such as. For example, acetate, trifluoroacetate, propionate, benzoate, aryl groups, such as. Phenyl, naphthyl, and anionic nitrogen-containing heterocycles such as pyrrolidine, imidazolide, pyrazolide. The alkyl groups in these groups are preferably C 1 -C 20 -alkyl groups, particularly preferably C 1 -C 10 -alkyl groups, very particularly preferably C 1 -C 4 -alkyl groups. An aryl group is also understood to mean heteroaryl groups.
  • An aryl group in the sense of this invention contains at least 6 C atoms; For the purposes of this invention, a heteroaryl group contains at least 2 C atoms and at least 1 heteroatom, with the proviso that the sum of C atoms and heteroatoms gives at least 5. The heteroatoms are preferably selected from N, O and / or S. Here, under an aryl group or heteroaryl either a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a condensed aryl or heteroaryl understood. An aryloxy group in the context of this invention means a group in which an aryl radical binds via an oxygen atom bound to the aryl radical. For the purposes of this invention, a fused aryl or heteroaryl group means an aryl or heteroaryl group in which at least two aromatic or heteroaromatic rings, for example benzene rings, are fused together by annulation, ie at least one common edge and thus also a common aromatic system exhibit. Thus, for example, systems such as naphthalene, anthracene, phenanthrene, benzanthracene, pyrene, etc. as condensed aryl groups and quinoline, acridine, benzothiophene, carbazole, etc. are to be seen as condensed heteroaryl groups in the context of this invention.
  • An aromatic ring system in the context of this invention contains at least 6 C atoms in the ring system. A heteroaromatic ring system in the sense of this invention contains at least 2 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of C atoms and heteroatoms gives at least 5. The heteroatoms are preferably selected from N, O and / or S. An aromatic or heteroaromatic ring system in the context of this invention is to be understood as meaning a system which is not necessarily contains only aryl or heteroaryl groups, but in which also several aryl or heteroaryl groups by a short, non-aromatic unit (preferably less than 10% of the atoms other than H), such as. As a C, N or O atom can be interrupted. For example, systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, benzophenone, etc. are also to be understood as aromatic ring systems in the context of this invention. Likewise, an aromatic or heteroaromatic ring system is understood as meaning systems in which a plurality of aryl or heteroaryl groups are linked together by single bonds, for example biphenyl, terphenyl or bipyridine.
  • By an aromatic or heteroaromatic ring system having 5-60 aromatic ring atoms, which may be substituted in each case with the abovementioned radicals R and which may be linked via any position on the aromatic or heteroaromatic, are understood in particular groups which are derived from benzene, Naphthalene, anthracene, phenanthrene, benzanthracene, pyrene, chrysene, perylene, fluoranthene, benzfluoranthene, naphthacene, pentacene, benzpyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, benzofluorene, dibenzofluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans Indenofluorene, cis or trans indolocarbazole, cis- or trans-indenocarbazole, cis- or trans-monobenzoindenofluorene, cis- or trans-dibenzoindenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene , Isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, Quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole, Pyrazine imidazole, quinoxaline imidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzpyrimidine, quinoxaline, 1,5-diazaanthracene, 2,7- Diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorubin, naphthyridine, azacarbazole, Benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3, 4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4- Triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole.
  • In the context of the present invention, an alkyl group, for. B. a C 1 -C 10 alkyl groups, a C 1 -C 4 alkyl group or an alkyl group having 1 to 40 carbon atoms, in which also individual H atoms or CH 2 groups substituted by further or the above groups particularly preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, tert-pentyl , 2-pentyl, cyclopentyl, n-hexyl, s -hexyl, tert -hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl , 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo [2,2,2] octyl, 2-bicyclo [2,2,2] octyl, 2- (2,6-dimethyl) octyl, 3- (3,7-dimethyl) octyl, trifluoromethyl, pentafluoroethyl and 2,2,2-trifluoroethyl understood. An alkenyl group is particularly preferably understood to mean the radicals ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl and cyclooctenyl. An alkynyl group is particularly preferably understood to mean the radicals ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. An alkoxy group is particularly preferably understood as meaning methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy or 2-methylbutoxy.
  • The invention also provides the use of one of the transition metal compounds described herein in an organic electronic device, in particular in an emitting layer of an electronic device, in particular an organic electroluminescent device, for. B. as an emitter.
  • In addition to the cathode, anode and one or more emitting layers, the organic electroluminescent device may contain further layers. These are, for example, selected from in each case one or more charge transport layers, hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, charge generation layers ( IDMC 2003, Taiwan; Session 21 OLED (5), T. Matsumoto, T. Nakada, J. Endo, K. Mori, N. Kawamura, A. Yokoi, J. Kido, Multiphoton Organic EL Device Having Charge Generation Layer ) and / or organic or inorganic p / n transitions. In addition, further layers may be present which influence the charge balance in the device. Furthermore, the layers, in particular charge transport layers, can also be doped. The doping of the layers may be advantageous for improved charge transport. It should be noted, however, that not necessarily each of these additional layers must be present and that the choice of layers always depends on the compounds used.
  • In a further embodiment of the invention, the organic electroluminescent device contains a plurality of emitting layers. Particularly preferably, these emission layers have a total of several emission maxima between 380 nm and 750 nm, so that a total of white emission results, ie in the emitting layers, different emitting compounds are used which emit blue and yellow, orange, green and / or red light. Particular preference is given to three-layer systems, that is to say systems having three emitting layers, the three layers exhibiting blue, green and orange or red emission (for the basic structure see, for example, FIG. WO 2005/011013 ). The use of more than three emitting layers may also be preferred.
  • Further, the transition metal compound of some embodiments described herein may be sublimable, especially when using small additional ligands. The transition metal compound of embodiments may also be soluble.
  • Preferably, an organic electroluminescent device is obtainable or obtained by coating one or more layers with a sublimation method. In the associated production process, the materials are vapor-deposited in vacuum sublimation plants at a pressure of less than 10 -5 mbar, preferably less than 10 -6 mbar. It should be noted, however, that the pressure may be even lower, for example less than 10 -7 mbar.
  • An organic electroluminescent device is likewise obtainable or obtained in that one or more layers are coated with the OVPD (Organic Vapor Phase Deposition) method or with the aid of a carrier gas sublimation. In such a manufacturing process, the materials are applied at a pressure between 10 -5 mbar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured (for example MS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301 ).
  • An organic electroluminescent device is furthermore preferably obtainable or obtained in that one or more layers of solution, such as e.g. B. by spin coating, or with any printing process, such. B. screen printing, flexographic printing or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or ink-jet printing (ink jet printing) can be produced. For this purpose, soluble compounds are needed. High solubility can be achieved by suitable substitution of the compounds. Not only solutions of individual materials can be applied, but also solutions containing several compounds, for example matrix materials and dopants.
  • The organic electroluminescent device, in one embodiment, may also be fabricated as a hybrid system by applying one or more layers of solution and depositing one or more other layers.
  • Another object of the present invention is therefore a method for producing an organic electroluminescent device according to the invention, characterized in that at least one layer is applied by a sublimation or at least one layer is applied by the OVPD method or the carrier gas sublimation or at least one layer of Solution or by any printing process is applied.
  • The organic electroluminescent devices and transition metal compounds according to embodiments or examples described herein lead to the following surprising favorable effects: The organic electroluminescent devices which comprise the transition metal compounds described here have a high efficiency. The organic electroluminescent devices may further have a good lifetime. The organic electroluminescent devices additionally show good color purity.
  • All non-mutually exclusive features of embodiments described herein may be combined. Elements of one embodiment may be used in the other embodiments without further mention.
  • The invention will be described in more detail by the following examples without wishing to limit them thereby. The person skilled in the art, without being inventive, can produce further electronic devices according to the invention, in particular organic electroluminescent devices, and thus work in the entire claimed range.
  • Examples
  • Complex K1-K16:
  • The synthesis of the complexes K1-K16 is carried out according to the literature given in Table 1: TABLE 1 complex connection literature K1 [Bu 3 MeN] 4 [Au 2 (SnB 11 H 11 ) 3 (PPh 3 ) 2 ] Angew. Chem. Int. Ed. 2003, 42, 1501 , K2 [Et 4 N] 5 [Ag (SnB 11 H 11 ) 3 ] Inorg. Chem. 2011, 50, 664 , K3 [Et 4 N] 6 [Au 2 (SnB 11 H 11 ) 4 ] Inorg. Chem. 2011, 50, 664 , K4 [Et 4 N] 2 [Ag 2 (SnB 11 H 11 ) 2 (bipy) 2 ] Organometallics 2010, 29, 4906 , K5 [Et 4 N] 2 [Ag 2 (SnB 11 H 11 ) 2 (mbipy) 2 ] Organometallics 2010, 29, 4906 , K6 [Et 4 N] 2 [Ag 2 (SnB 11 H 11 ) 2 (phen) 2 ] Organometallics 2010, 29, 4906 , K7 [Ru (SnPh 3 ) 2 (CO) 2 ('Pr-dab)] Chem. Eur. J. 1996, 2, 1556 , K8 [Ru (SnPh 3) (SnMe 3) (CO) 2 ( 'Pr-DAB)] Chem. Eur. J. 1996, 2, 1556 , K9 [Ru (SnPh 3 ) 2 (CO) 2 (dmb)] Inorg. Chem. 2001, 40, 277 , K10 [Os (SnPh 3 ) 2 (CO) 2 (dmb)] Inorg. Chem. 2001, 40, 277 , K11 [ClSn (crown-P 2 ) Ir (CO) Cl] (SnCl 3 ) Inorg. Chem. 1991, 30, 3395 , K12 [CH 3 PPh 3 ] 2 [PtCl 2 (SnCl 3 ) 2 ] Inorg. Chem. 1996, 35, 883 , K13 [NBu 4 ] 2 [Pt 2 (μ-Cl) 2 (SnCl 3 ) 2 (C 6 Cl 5 ) 2] Inorganica Chimica Acta 2005, 358, 315 , K14 [Ir 2 (SnCl) (CO) 2 Cl 2 (μ-dpma) 2 ] [SnCl 3 ] J. Am. Chem. Soc. 1989, 111, 4021 , K15 [PtMe 2 (Ph 2 Sn S) 2 ( t bu 2 bpy)] Organometallics 1996, 15, 1749 , K16 Ru 3 (CO) 9 (μ-SnPh 2 ) 3 J. Am. Chem. Soc. 2007, 129, 12328 ,
    Explanation of the used abbreviations:
    Figure 00220001
  • In the following, the anions of the transition metal compounds K1 to K16 are shown schematically:
    Figure 00220002
    Figure 00230001
    Figure 00240001
  • It stands
    Figure 00240002
    each for a ligand of the formula [SnB 11 H 11 ] 2- . Complex K17 Scheme of the anion:
    Figure 00240003
  • Synthesis:
  • 2 g (3.0 mmol) of [Bu 3 NMe] 2 [SnB 11 H 11 ] and 0.8 g (0.75 mmol) of [Ir (μ-Cl) (ppy) 2 ] 2 are dissolved in 100 ml of dichloromethane and stirred at room temperature for 12 hours , Repeated overlaying of the reaction mixture with heptane gives a total of 2.13 g (89%) of the complex K17, which has as cation [Bu 3 NMe], as a fine crystalline powder.
  • Example 1-17: Preparation and Characterization of Organic Electroluminescent Devices from Solution
  • The production of OLEDs was carried out according to the general procedure outlined below. In individual cases, this can be adapted to the respective circumstances (eg layer thickness variation in order to achieve optimum efficiency or color).
  • General procedure for the preparation of the OLEDs:
  • The preparation of such components is based on the production of polymeric light-emitting diodes (PLEDs), which has already been described many times in the literature, for. B. in the WO 2004/037887 A2 , In the present case, the transition metal Sn compounds are dissolved together with the listed matrix materials or matrix material combinations in toluene, chlorobenzene or DMF. The typical solids content of such solutions is between 10 and 25 g / L, if, as here, the typical layer thickness of 80 nm for a device should be achieved by means of spincoating.
  • According to the above-mentioned general method, OLEDs are produced with the following structure and layer thicknesses: PEDOT 20 nm, spun from water; PEDOT purchased from BAYER AG; Poly [3,4-ethylenedioxy-2,5-thiophene] Matrix + emitter 80 nm, 10 wt .-% emitter concentration, spin-on from toluene, chlorobenzene or DMF, Baal 10 nm Ba / 150 nm Al as the cathode.
  • Structured ITO substrates and the material for the so-called buffer layer of PEDOT, PEDOT: PSS, were purchased. The ITO was from Technoprint, PEDOT: PPS as an aqueous dispersion was Clevios Baytron P from H.C. Starck.
  • As matrix materials M1 and M2 are used, as shown below with reference to literature:
    Figure 00260001
  • The emission layer of matrix and emitter is spun in an inert gas atmosphere, in this case argon, on the respective ITO substrates and baked at 120 ° C for 10 min. Finally, a cathode of barium and aluminum is vapor-deposited in vacuo. The solution-processed devices are characterized by default. Table 2 shows the efficiency and the stress at 100 cd / m 2 and the color of the respective examples. Table 2: Results for the devices Ex. Matrix A: Matrix B emitter EQE at 100 cd / m 2 [%] Voltage at 100 cd / m 2 [V] colour 1 M1 (30%): M2 (60%) K1 4.2 5.9 red 2 M1 (30%): M2 (60%) K2 2.2 6.3 orange 3 M1 (30%): M2 (60%) K3 1.8 7.8 red 4 M1 (30%): M2 (60%) K4 3.4 7.1 green 5 M1 (30%): M2 (60%) K5 3.7 5.8 green 6 M1 (30%): M2 (60%) K6 4.1 5.8 green 7 M1 (30%): M2 (60%) K7 5.0 6.1 red 8th M1 (30%): M2 (60%) K8 4.6 4.9 red 9 M1 (30%): M2 (60%) K9 3.9 5.3 orange 10 M1 (30%): M2 (60%) K10 4.3 5.7 yellow 11 M1 (30%): M2 (60%) K11 2.7 5.6 red 12 M1 (30%): M2 (60%) K12 2.1 7.5 red 13 M1 (30%): M2 (60%) K13 2.3 7.9 red 14 M1 (30%): M2 (60%) K14 4.7 6.1 red 15 M1 (30%): M2 (60%) K15 3.4 6.7 red 16 M1 (30%): M2 (60%) K16 3.6 6.2 red 17 M1 (30%): M2 (60%) K17 5.4 5.0 green
  • QUOTES INCLUDE IN THE DESCRIPTION
  • This list of the documents listed by the applicant has been generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.
  • Cited patent literature
    • US 4539507 [0003]
    • US 5151629 [0003]
    • EP 0676461 [0003]
    • WO 98/27136 [0003]
    • WO 2004/013080 [0029]
    • WO 2004/093207 [0029]
    • WO 2006/005627 [0029]
    • WO 2010/006680 [0029]
    • WO 2005/039246 [0029]
    • US 2005/0069729 [0029]
    • JP 2004/288381 [0029]
    • EP 1205527 [0029]
    • WO 2008/086851 [0029]
    • US 2009/0134784 [0029]
    • WO 2007/063754 [0029, 0029]
    • WO 2008/056746 [0029, 0029]
    • WO 2010/136109 [0029]
    • WO 2011/000455 [0029]
    • EP 1617710 [0029]
    • EP 1617711 [0029]
    • EP 1731584 [0029]
    • JP 2005/347160 [0029]
    • WO 2007/137725 [0029]
    • WO 2005/111172 [0029]
    • WO 2006/117052 [0029]
    • WO 2010/054729 [0029]
    • WO 2010/054730 [0029]
    • WO 2010/015306 [0029]
    • EP 652273 [0029]
    • WO 2009/062578 [0029]
    • WO 2009/148015 [0029]
    • US 2009/0136779 [0029]
    • WO 2010/050778 [0029]
    • WO 2011/042107 [0029]
    • WO 2011/088877 [0029]
    • WO 2005/011013 [0044]
    • WO 2004/037887 A2 [0059]
  • Cited non-patent literature
    • Inorg. Chem. 1966, 5, 109-110 [0002]
    • J. Chem. Soc. A 1971, 3765-3769 [0002]
    • S. Hagen, I. Pantenburg, F. Weigend, C. Wickleder, L. Wesemann Angew. Chem. 2003, 115, 1539-1543 [0027]
    • IDMC 2003, Taiwan; Session 21 OLED (5), T. Matsumoto, T. Nakada, J. Endo, K. Mori, N. Kawamura, A. Yokoi, J. Kido, Multiphoton Organic EL Device Having Charge Generation Layer [0043]
    • MS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301 [0047]
    • Angew. Chem. Int. Ed. 2003, 42, 1501 [0054]
    • Inorg. Chem. 2011, 50, 664 [0054]
    • Inorg. Chem. 2011, 50, 664 [0054]
    • Organometallics 2010, 29, 4906 [0054]
    • Organometallics 2010, 29, 4906 [0054]
    • Organometallics 2010, 29, 4906 [0054]
    • Chem. Eur. J. 1996, 2, 1556 [0054]
    • Chem. Eur. J. 1996, 2, 1556 [0054]
    • Inorg. Chem. 2001, 40, 277 [0054]
    • Inorg. Chem. 2001, 40, 277 [0054]
    • Inorg. Chem. 1991, 30, 3395 [0054]
    • Inorg. Chem. 1996, 35, 883 [0054]
    • Inorganica Chimica Acta 2005, 358, 315 [0054]
    • J. Am. Chem. Soc. 1989, 111, 4021 [0054]
    • Organometallics 1996, 15, 1749 [0054]
    • J. Am. Chem. Soc. 2007, 129, 12328 [0054]

Claims (15)

  1. Electronic device, in particular an organic electroluminescent device, comprising at least one transition metal compound having at least one transition metal-tin bond.
  2. Electronic device according to claim 1, characterized in that the transition metal compound is a compound of the following formula (TM) n ("Sn") o (L) p wherein UM stands for a transition metal, "Sn" for a tin-containing ligand which coordinates via a tin atom to the transition metal, L is another ligand which may be monodentate or polydentate, and for the indices: n ≥ 1, o ≥ 1 and p ≥ 0.
  3. Electronic device according to claim 1 or 2, characterized in that the transition metal compound has exactly one transition metal-tin bond or that the transition metal compound has more than one transition metal-tin bond.
  4. Electronic device according to one or more of claims 1 to 3, characterized in that the transition metal compound has 1 to 10 transition metals, preferably 1, 2, 3, 4, 5 or 6 transition metals.
  5. Electronic device according to one or more of claims 1 to 4, characterized in that the transition metal compound has more than one transition metal, wherein the transition metals are partially or completely bound together by one or more transition metal-transition metal bonds to each other.
  6. Electronic device according to one or more of claims 1 to 5, characterized in that the tin-containing ligand is selected from the group of hetero-closo-dodecaborate of the formula [SnB 11 R 11 ] 2- , [SnCB 10 R 11 ] - or [Sn 2 B 10 R 10 ] 2- with coordination mode η 1 , μ 2 , μ 3 or μ 4 , where R is identical or different at each occurrence for H, D, halogen, alkyl having 1 to 10 C atoms, alkoxy with 1 to 10 C atoms or OH, preferably [SnB 11 H 11 ] 2- , [SnCB 10 H 11 ] - or [Sn 2 B 10 H 10 ] 2- ; or that the tin-containing ligand is selected from the group consisting of a stannane [η 1 -SnY 3 ] - , [μ 2 -SnY 2 ] - or [μ 3 -SnY] - with Y on each occurrence equal to or different F, Cl, Br, I, aryloxy, alkoxy, aryl, heteroaryl or alkyl, preferably Cl, Br, alkyl or aryl.
  7. Electronic device according to one or more of claims 1 to 6, characterized in that at least one of the transition metals is selected from the group consisting of Zr, Hf, Nb, Ta, Mo, W, Re, Ru, Os, Rh, Ir , Ni, Pd, Pt, Cu, Ag, Au and Zn, preferably Ru, Os, Rh, Ir, Ni, Pd, Pt, Cu, Ag and Au.
  8. Electronic device according to one or more of claims 1 to 7, characterized in that, when the transition metal compound contains more than one transition metal, all the transition metals are the same.
  9. Electronic device according to one or more of claims 1 to 8, characterized in that the transition metal compound is selected from the group consisting of: [(Ph 3 P) 2 Au 2 (SnB 11 H 11 ) 2 ] 2- , [(Ph 3 P) 2 Au 2 (SnB 11 H 11 ) 3 ] 4- , [(Et 3 P) 3 Au 3 (SnB 11 H 11 ) 3 ] 3- , [(dppm) 2 Au 4 (SnB 11 H 11 ) 4 ] 4- , [(Ph 3 P) 2 Ag 2 (SnB 11 H 11 ) 2 ] 2- , [(Et 3 P) 3 Ag 3 (SnB 11 H 11 ) 3 ] 3- , [(Me 3 P) 4 Ag 4 (SnB 11 H 11 ) 4 ] 4- , [Ag 4 (SnB 11 H 11 ) 6 ] 8- , [Au (SnB 11 H 11 ) 4 ] 5- , [(dppm) 2 Au 2 (SnB 11 H 10 (OEt)) 2 ] - , [(dppm) 2 Au 2 (SnB 11 H 11 )], [(Ph 3 P) 2 Au (SnB 11 H 11 )] - , [(Ph 3 P) 2 Ag 2 (SnB 11 H 11) 2] 2 [(Ph 3 P) 2 Cu 2 (SnB 11 H 11) 2] 2-, [(iPr 3 P) 2 Cu 2 (SnB 1 1 H 11) 2] 2- , [(Me 3 P) 4 Cu 2 (SnB 11 H 11 ) 2 ] 2- , [Ag 2 (SnB 11 H 11 ) 2 (PMe 3 ) 4 ] 2- , [Ag 4 (SnB 11 H 11 ) 4 (pyridine) 4] 4-, [Ag 2 (SnB 11 H 11) 2 (bipy) 2] 2-, [Ag 2 (SNB 11 H (11) 2 phenanthroline) 2] 2 , [Ag 2 (SnB 11 H 11) 2 (MeBipy) 2] 2-, [Au 2 (SnB 11 H 11) 4] 4-, [Ag (SnB 11 H 11) 3] 5-, [Cu (SnB 11 H 11 ) 3 (CH 3 CN)] 5- , [Ag 2 (SnB 11 H 11 ) 2 (IprNHC) 2 ], [Ag 5 (SnB 11 H 11 ) 6 (DPI) 1.5 ] 7- , [Ag 4 (SnB 11 H 11 ) 4 (DPI) 3 ] - and [Ag 4 (SnB 11 H 11 ) 4 (t-BuNC) 4 ] 4- , the compounds each still containing counterions.
  10. Electronic device according to one or more of claims 2 to 9, characterized in that the ligands L are the same or different at each occurrence selected from the group consisting of carbon monoxide, nitrogen monoxide, alkyl cyanides, aryl cyanides, alkyl isocyanides, aryl isocyanides, amines, phosphines, phosphites, arsines, stibines, nitrogen-containing heterocycles, hydride, deuteride, the halides F -, Cl -, Br - and I -, Alkylacetyliden, Arylacetyliden, cyanide, cyanate, isocyanate, thiocyanate, Isothiocyanate, aliphatic or aromatic alcoholates, aliphatic or aromatic thioalcoholates, amides, carboxylates and aryl groups.
  11. Electronic device according to one or more of claims 1 to 10, characterized in that it is an organic electroluminescent device and the transition metal compound is contained in an emitting layer.
  12. The organic electroluminescent device according to claim 11, characterized in that the transition metal compound is used in combination with a matrix material, wherein the matrix material is selected from the group consisting of ketones, phosphine oxides, sulfoxides, sulfones, triarylamines, carbazole derivatives, indolocarbazole derivatives, indenocarbazole derivatives, azacarbazoles, bipolar matrix materials , Azaboroles, boronic esters, diazasilol derivatives, diazaphosphole derivatives, triazine derivatives, zinc complexes, dibenzofuran derivatives and bridged carbazole derivatives.
  13. Electronic device according to one or more of claims 1 to 12, characterized in that the transition metal complex is a complex according to one of the formulas L'Pt ("Sn") L, (L ') 2 Ir ("Sn") L, L'Pt ("Sn") 2 PtL 'or (L') 2 Ir ("Sn") 2 Ir (L ') 2 , where "Sn" stands for a tin-containing ligand, in particular for a hetero-closo-dodecaborate, L is a monodentate ligand and L 'is a bidentate monoanionic ligand which forms with the metal a cyclometallated five-membered or six-membered ring having at least one metal-carbon bond.
  14. Compound according to one of the formulas L'Pt ("Sn") L, (L ') 2 Ir ("Sn") L, L'Pt ("Sn") 2 PtL' or (L ') 2 Ir ("Sn" ) 2 Ir (L ') 2 , where "Sn" is a tin-containing ligand, in particular a hetero-closo-dodecaborate, L is a monodentate ligand, and L' is a bidentate monoanionic ligand which binds with the Metal forms a cyclometallierten five-membered or six-membered ring with at least one metal-carbon bond.
  15. Method for producing an electronic device according to one or more of Claims 1 to 13, characterized in that at least one layer is applied by a sublimation method or at least one layer is applied by the OVPD method or the carrier gas sublimation or at least one layer of solution or applied by a printing process.
DE102012007810A 2011-05-16 2012-04-18 Electronic device, preferably organic electroluminescent device comprises a transition metal compound exhibiting a transition metal-tin bond Withdrawn DE102012007810A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP11004024 2011-05-16
EPEP11004024.3 2011-05-16

Publications (1)

Publication Number Publication Date
DE102012007810A1 true DE102012007810A1 (en) 2012-11-22

Family

ID=47088219

Family Applications (1)

Application Number Title Priority Date Filing Date
DE102012007810A Withdrawn DE102012007810A1 (en) 2011-05-16 2012-04-18 Electronic device, preferably organic electroluminescent device comprises a transition metal compound exhibiting a transition metal-tin bond

Country Status (1)

Country Link
DE (1) DE102012007810A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102013109451A1 (en) 2013-08-30 2015-01-29 Osram Opto Semiconductors Gmbh Method for producing an optoelectronic component and optoelectronic component

Citations (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4539507A (en) 1983-03-25 1985-09-03 Eastman Kodak Company Organic electroluminescent devices having improved power conversion efficiencies
US5151629A (en) 1991-08-01 1992-09-29 Eastman Kodak Company Blue emitting internal junction organic electroluminescent device (I)
EP0652273A1 (en) 1993-11-09 1995-05-10 Shinko Electric Industries Co. Ltd. Organic material for electroluminescent device and electroluminescent device
EP0676461A2 (en) 1994-04-07 1995-10-11 Hoechst Aktiengesellschaft Spiro compounds and their application as electroluminescence materials
WO1998027136A1 (en) 1996-12-16 1998-06-25 Aventis Research & Technologies Gmbh & Co Kg ARYL-SUBSTITUTED POLY(p-ARYLENE VINYLENES), METHOD FOR THE PRODUCTION AND USE THEREOF IN ELECTROLUMINESCENT COMPONENTS
EP1205527A1 (en) 2000-03-27 2002-05-15 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
WO2004013080A1 (en) 2002-08-01 2004-02-12 Covion Organic Semiconductors Gmbh Spirobifluorene derivatives, their preparation and uses thereof
WO2004037887A2 (en) 2002-10-25 2004-05-06 Covion Organic Semiconductors Gmbh Conjugated polymers containing arylamine units, the representation thereof and the use of the same
JP2004288381A (en) 2003-03-19 2004-10-14 Konica Minolta Holdings Inc Organic electroluminescent element
WO2004093207A2 (en) 2003-04-15 2004-10-28 Covion Organic Semiconductors Gmbh Mixtures of matrix materials and organic semiconductors capable of emission, use of the same and electronic components containing said mixtures
WO2005011013A1 (en) 2003-07-21 2005-02-03 Covion Organic Semiconductors Gmbh Organic electroluminescent element
US20050069729A1 (en) 2003-09-30 2005-03-31 Konica Minolta Holdings, Inc. Organic electroluminescent element, illuminator, display and compound
WO2005111172A2 (en) 2004-05-11 2005-11-24 Merck Patent Gmbh Novel material mixtures for use in electroluminescence
JP2005347160A (en) 2004-06-04 2005-12-15 Konica Minolta Holdings Inc Organic electroluminescent element, lighting device, and display device
EP1617710A1 (en) 2003-04-23 2006-01-18 Konica Minolta Holdings, Inc. Material for organic electroluminescent device, organic electroluminescent device, illuminating device and display
WO2006005627A1 (en) 2004-07-15 2006-01-19 Merck Patent Gmbh Oligomeric derivatives of spirobifluorene, their preparation and use
WO2006117052A1 (en) 2005-05-03 2006-11-09 Merck Patent Gmbh Organic electroluminescent device and boric acid and borinic acid derivatives used therein
EP1731584A1 (en) 2004-03-31 2006-12-13 Konica Minolta Holdings, Inc. Organic electroluminescent device material, organic electroluminescent device, display and illuminating device
WO2007063754A1 (en) 2005-12-01 2007-06-07 Nippon Steel Chemical Co., Ltd. Compound for organic electroluminescent element and organic electroluminescent element
WO2007137725A1 (en) 2006-05-31 2007-12-06 Merck Patent Gmbh New materials for organic electroluminescent devices
WO2008056746A1 (en) 2006-11-09 2008-05-15 Nippon Steel Chemical Co., Ltd. Compound for organic electroluminescent device and organic electroluminescent device
WO2008086851A1 (en) 2007-01-18 2008-07-24 Merck Patent Gmbh Carbazole derivatives for organc electroluminescent devices
WO2009062578A1 (en) 2007-11-12 2009-05-22 Merck Patent Gmbh Organic electroluminescent devices comprising azomethine-metal complexes
US20090134784A1 (en) 2004-10-21 2009-05-28 Universal Display Corporation Carbazole-containing materials in phosphorescent light emitting diodes
US20090136779A1 (en) 2007-11-26 2009-05-28 Chien-Hong Cheng Conjugated compounds containing hydroindoloacridine structural elements, and their use
WO2009148015A1 (en) 2008-06-05 2009-12-10 出光興産株式会社 Halogen compound, polycyclic compound, and organic electroluminescence element comprising the polycyclic compound
WO2010006680A1 (en) 2008-07-18 2010-01-21 Merck Patent Gmbh Materials for organic electroluminescence devices
WO2010015306A1 (en) 2008-08-08 2010-02-11 Merck Patent Gmbh, Organic electroluminescence device
WO2010050778A1 (en) 2008-10-31 2010-05-06 Gracel Display Inc. Novel compounds for organic electronic material and organic electronic device using the same
WO2010054730A1 (en) 2008-11-11 2010-05-20 Merck Patent Gmbh Organic electroluminescent devices
WO2010054729A2 (en) 2008-11-11 2010-05-20 Merck Patent Gmbh Materials for organic electroluminescence devices
WO2010136109A1 (en) 2009-05-29 2010-12-02 Merck Patent Gmbh Materials for organic electroluminescent devices
WO2011000455A1 (en) 2009-06-30 2011-01-06 Merck Patent Gmbh Materials for organic electroluminescence devices
WO2011042107A2 (en) 2009-10-08 2011-04-14 Merck Patent Gmbh Materials for organic electroluminescent devices
WO2011088877A1 (en) 2010-01-25 2011-07-28 Merck Patent Gmbh Compounds for electronic devices

Patent Citations (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4539507A (en) 1983-03-25 1985-09-03 Eastman Kodak Company Organic electroluminescent devices having improved power conversion efficiencies
US5151629A (en) 1991-08-01 1992-09-29 Eastman Kodak Company Blue emitting internal junction organic electroluminescent device (I)
EP0652273A1 (en) 1993-11-09 1995-05-10 Shinko Electric Industries Co. Ltd. Organic material for electroluminescent device and electroluminescent device
EP0676461A2 (en) 1994-04-07 1995-10-11 Hoechst Aktiengesellschaft Spiro compounds and their application as electroluminescence materials
WO1998027136A1 (en) 1996-12-16 1998-06-25 Aventis Research & Technologies Gmbh & Co Kg ARYL-SUBSTITUTED POLY(p-ARYLENE VINYLENES), METHOD FOR THE PRODUCTION AND USE THEREOF IN ELECTROLUMINESCENT COMPONENTS
EP1205527A1 (en) 2000-03-27 2002-05-15 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
WO2004013080A1 (en) 2002-08-01 2004-02-12 Covion Organic Semiconductors Gmbh Spirobifluorene derivatives, their preparation and uses thereof
WO2004037887A2 (en) 2002-10-25 2004-05-06 Covion Organic Semiconductors Gmbh Conjugated polymers containing arylamine units, the representation thereof and the use of the same
JP2004288381A (en) 2003-03-19 2004-10-14 Konica Minolta Holdings Inc Organic electroluminescent element
WO2004093207A2 (en) 2003-04-15 2004-10-28 Covion Organic Semiconductors Gmbh Mixtures of matrix materials and organic semiconductors capable of emission, use of the same and electronic components containing said mixtures
EP1617710A1 (en) 2003-04-23 2006-01-18 Konica Minolta Holdings, Inc. Material for organic electroluminescent device, organic electroluminescent device, illuminating device and display
EP1617711A1 (en) 2003-04-23 2006-01-18 Konica Minolta Holdings, Inc. Organic electroluminescent device and display
WO2005011013A1 (en) 2003-07-21 2005-02-03 Covion Organic Semiconductors Gmbh Organic electroluminescent element
US20050069729A1 (en) 2003-09-30 2005-03-31 Konica Minolta Holdings, Inc. Organic electroluminescent element, illuminator, display and compound
WO2005039246A1 (en) 2003-09-30 2005-04-28 Konica Minolta Holdings, Inc. Organic electroluminescent device, illuminating device, and display
EP1731584A1 (en) 2004-03-31 2006-12-13 Konica Minolta Holdings, Inc. Organic electroluminescent device material, organic electroluminescent device, display and illuminating device
WO2005111172A2 (en) 2004-05-11 2005-11-24 Merck Patent Gmbh Novel material mixtures for use in electroluminescence
JP2005347160A (en) 2004-06-04 2005-12-15 Konica Minolta Holdings Inc Organic electroluminescent element, lighting device, and display device
WO2006005627A1 (en) 2004-07-15 2006-01-19 Merck Patent Gmbh Oligomeric derivatives of spirobifluorene, their preparation and use
US20090134784A1 (en) 2004-10-21 2009-05-28 Universal Display Corporation Carbazole-containing materials in phosphorescent light emitting diodes
WO2006117052A1 (en) 2005-05-03 2006-11-09 Merck Patent Gmbh Organic electroluminescent device and boric acid and borinic acid derivatives used therein
WO2007063754A1 (en) 2005-12-01 2007-06-07 Nippon Steel Chemical Co., Ltd. Compound for organic electroluminescent element and organic electroluminescent element
WO2007137725A1 (en) 2006-05-31 2007-12-06 Merck Patent Gmbh New materials for organic electroluminescent devices
WO2008056746A1 (en) 2006-11-09 2008-05-15 Nippon Steel Chemical Co., Ltd. Compound for organic electroluminescent device and organic electroluminescent device
WO2008086851A1 (en) 2007-01-18 2008-07-24 Merck Patent Gmbh Carbazole derivatives for organc electroluminescent devices
WO2009062578A1 (en) 2007-11-12 2009-05-22 Merck Patent Gmbh Organic electroluminescent devices comprising azomethine-metal complexes
US20090136779A1 (en) 2007-11-26 2009-05-28 Chien-Hong Cheng Conjugated compounds containing hydroindoloacridine structural elements, and their use
WO2009148015A1 (en) 2008-06-05 2009-12-10 出光興産株式会社 Halogen compound, polycyclic compound, and organic electroluminescence element comprising the polycyclic compound
WO2010006680A1 (en) 2008-07-18 2010-01-21 Merck Patent Gmbh Materials for organic electroluminescence devices
WO2010015306A1 (en) 2008-08-08 2010-02-11 Merck Patent Gmbh, Organic electroluminescence device
WO2010050778A1 (en) 2008-10-31 2010-05-06 Gracel Display Inc. Novel compounds for organic electronic material and organic electronic device using the same
WO2010054730A1 (en) 2008-11-11 2010-05-20 Merck Patent Gmbh Organic electroluminescent devices
WO2010054729A2 (en) 2008-11-11 2010-05-20 Merck Patent Gmbh Materials for organic electroluminescence devices
WO2010136109A1 (en) 2009-05-29 2010-12-02 Merck Patent Gmbh Materials for organic electroluminescent devices
WO2011000455A1 (en) 2009-06-30 2011-01-06 Merck Patent Gmbh Materials for organic electroluminescence devices
WO2011042107A2 (en) 2009-10-08 2011-04-14 Merck Patent Gmbh Materials for organic electroluminescent devices
WO2011088877A1 (en) 2010-01-25 2011-07-28 Merck Patent Gmbh Compounds for electronic devices

Non-Patent Citations (16)

* Cited by examiner, † Cited by third party
Title
Angew. Chem. Int. Ed. 2003, 42, 1501
Chem. Eur. J. 1996, 2, 1556
IDMC 2003, Taiwan; Session 21 OLED (5), T. Matsumoto, T. Nakada, J. Endo, K. Mori, N. Kawamura, A. Yokoi, J. Kido, Multiphoton Organic EL Device Having Charge Generation Layer
Inorg. Chem. 1966, 5, 109-110
Inorg. Chem. 1991, 30, 3395
Inorg. Chem. 1996, 35, 883
Inorg. Chem. 2001, 40, 277
Inorg. Chem. 2011, 50, 664
Inorganica Chimica Acta 2005, 358, 315
J. Am. Chem. Soc. 1989, 111, 4021
J. Am. Chem. Soc. 2007, 129, 12328
J. Chem. Soc. A 1971, 3765-3769
M. S. Arnold et al., Appl. Phys. Lett. 2008, 92, 053301
Organometallics 1996, 15, 1749
Organometallics 2010, 29, 4906
S. Hagen, I. Pantenburg, F. Weigend, C. Wickleder, L. Wesemann Angew. Chem. 2003, 115, 1539-1543

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102013109451A1 (en) 2013-08-30 2015-01-29 Osram Opto Semiconductors Gmbh Method for producing an optoelectronic component and optoelectronic component
DE102013109451B4 (en) * 2013-08-30 2017-04-13 Osram Oled Gmbh Method for producing an optoelectronic component
DE102013109451B9 (en) * 2013-08-30 2017-07-13 Osram Oled Gmbh Method for producing an optoelectronic component
US9960390B2 (en) 2013-08-30 2018-05-01 Osram Oled Gmbh Method of producing an optoelectronic device and optoelectronic device

Similar Documents

Publication Publication Date Title
EP2712001B1 (en) Materials for Organic Electroluminescent Devices
JP6556629B2 (en) Metal complex
KR101839627B1 (en) Materials for organic light emitting devices
EP2371016B1 (en) Organic light emitting evices comprising triazine derivatives
JP5345322B2 (en) Metal complex
KR101758388B1 (en) Metal complexes
KR101719014B1 (en) Materials for organic electroluminescence devices
JP6125492B2 (en) Metal complex
KR20130038218A (en) Organic electroluminescent device
US20150171348A1 (en) Metal Complexes
EP2102309B1 (en) Carbazole derivatives for organic electroluminescent devices
JP6556628B2 (en) Metal complex
US9273080B2 (en) Metal complexes
US9217006B2 (en) Materials for organic electroluminescent devices
TWI660959B (en) Metal complexes
JP5774487B2 (en) Materials for organic electroluminescent devices
CN102317407B (en) Metal complexes having azaborol ligands and electronic device having the same
TWI447121B (en) Materials for organic electroluminescent devices
EP2311111B1 (en) Organic electroluminescence device
JP5744724B2 (en) Electronic devices containing metal complexes
TWI568739B (en) Metal complexes
JP5705719B2 (en) Metal complex
US20080161567A1 (en) Metal Complexes
EP1924590B1 (en) Metal complexes
TWI638819B (en) Metal complexes

Legal Events

Date Code Title Description
R119 Application deemed withdrawn, or ip right lapsed, due to non-payment of renewal fee