Metal complexes

• US 8,617,723 B2
• Filed: 03/04/2009
• Issued: 12/31/2013
• Est. Priority Date: 03/25/2008
• Status: Active Grant

• Current Assignee: UDC Ireland Limited (Universal Display Corporation)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: Stoessel, Philipp
• Primary Examiner(s): Wilson, Michael H
• Application Number:
  US12/934,487
• Publication Number:
  US 20110012100A1
• Time in Patent Office: 1,763 Days
• Field of Search: None
• US Class Current: 428/690
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1022 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1033 with oxygen
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/182 of the rare earth metals, i.e. Sc, Y or lanthanide
• CPC Class Codes: C09K 2211/183 of the refractory metals, i.e. Ti, V, Cr, Zr, Nb, Mo, Hf, Ta or W
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: C09K 2211/186 of the light metals other than alkali metals and alkaline earth metals, i.e. Be, Al or Mg
• CPC Class Codes: C09K 2211/187 of the iron group metals, i.e. Fe, Co or Ni
• CPC Class Codes: C09K 2211/188 of other metals not provided for in one of the previous groups
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 50/18 : Carrier blocking layers
• CPC Class Codes: H10K 85/321 : Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
• CPC Class Codes: H10K 85/324 : comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/326 : comprising gallium
• CPC Class Codes: H10K 85/331 : Metal complexes comprising an iron-series metal, e.g. Fe, Co, Ni
• CPC Class Codes: H10K 85/342 : comprising iridium
• CPC Class Codes: H10K 85/346 : comprising platinum
• CPC Class Codes: H10K 85/348 : comprising osmium
• CPC Class Codes: H10K 85/351 : Metal complexes comprising lanthanides or actinides, e.g. comprising europium
• CPC Class Codes: H10K 85/361 : Polynuclear complexes, i.e. complexes comprising two or more metal centers
• CPC Class Codes: H10K 85/40 : Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: Y02E 10/549 : Organic PV cells

Abstract

The present invention relates to metal complexes of the formula (1) and to the use thereof in organic electroluminescent devices, and to organic electroluminescent devices which comprise these metal complexes.

Claims

1. A compound of the formula (1)

2. The compound according to claim 1, wherein the ligand L has a structure of the formula (6), (7), (8), (9) or (10), where the symbols and indices used have the meanings mentioned in claim 1:

3. The compound according to claim 1, wherein M is tungsten, rhenium, ruthenium, osmium, rhodium, iridium, platinum, gold, scandium, yttrium, lanthanum, aluminium, gallium or indium.

4. The compound according to claim 1, wherein Z on each occurrence, identically or differently, and is O, S, NR or C(═

O).

5. The compound according to claim 1, wherein the ligand moieties of the formula (5) are selected from substituted or unsubstituted β

-ketoketonates, β

-ketoesters, β

-diesters, carboxylates derived from aminocarboxylic acids, iminoacetoacetonates, hydroxamates, pyridylphosphines, α

-phosphinocarboxylates, glycol ethers, ether alcoholates, dialcoholates derived from dialcohols, dithiolates derived from dithiols, diamines, imines, diimines, diphosphines and salicyliminates derived from salicylimines.

6. A process for the preparation of the compound according to claim 1 which comprises reacting the ligands of the formula (2) or precursors of these ligands with metal alkoxides of the formula (47), with metal ketoketonates of the formula (48) or with metal halides of the formula (49)

7. The process as claimed in claim 6, wherein q is 0, 1 or 2.

8. An oligomer, polymer or dendrimer comprising one or more compounds according to claim 1, in which one or more bonds are present from the complex of the formula (1) to the polymer, oligomer or dendrimer.

9. An electronic component comprising the compounds according to claim 1.

10. The electronic component as claimed in claim 9, wherein the electronic component is an organic integrated circuit (O-IC), an organic field-effect transistors (O-FET), an organic thin-film transistor (O-TFT), an organic light-emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detector, an organic photoreceptor, an organic field-quench device (O-FQD), a light-emitting electrochemical cell (LEC) or an organic laser diode (O-laser), an organic electroluminescent device (OLED, PLED).

11. An organic electroluminescent device which comprises an emitting layer which comprises the compound according to claim 1.

12. An organic electroluminescent device which comprises an emitting layer which comprises the compound according to claim 1 in combination with a matrix material, employed as matrix material for an emitting compound in an emitting layer, employed as hole-blocking material in a hole-blocking layer or as electron-transport material in an electron-transport layer.

13. An organic electroluminescent device which comprises an emitting layer which comprises the compound according to claim 1 is employed as matrix material for a phosphorescent compound.

14. A compound of the following applies to the ligand moiety L1 thereof together with the metal and the bridging unit V of the formula (11):

15. The compound according to claim 14, wherein the ligand moiety L1, together with the metal and the bridging unit V, has a structure of the formulae (15) to (30):