Heteroleptic carbene complexes and the use thereof in organic electronics

Patent metadata

Field	Value
Publication number	US-12376484-B2
Application number	US-202318517812-A
Country	US
Kind code	B2
Filing date	Nov 22, 2023
Priority date	Oct 28, 2009
Publication date	Jul 29, 2025
Grant date	Jul 29, 2025

Abstract

The present invention relates to heteroleptic complexes comprising a phenylimidazole or phenyltriazole unit bonded via a carbene bond to a central metal atom, and phenylimidazole ligands attached via a nitrogen-metal bond to the central atom, to OLEDs which comprise such heteroleptic complexes, to light-emitting layers comprising at least one such heteroleptic complex, to a device selected from the group consisting of illuminating elements, stationary visual display units and mobile visual display units comprising such an OLED, to the use of such a heteroleptic complex in OLEDs, for example as emitter, matrix material, charge transport material and/or charge blocker.

First claim

The invention claimed is:

1. A heteroleptic complex of the general formula (I)

wherein:
M is a metal atom selected from the group consisting of Ir and Pt,
A 1 , A 2 are each independently N or C,
n, m are each independently 1 or 2, where, if M is Pt, the sum of n and m is 2, or, if M is Ir, the sum of n and m is 3,
R 1 is a linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 20 carbon atoms, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 5 to 18 carbon atoms and/or heteroatoms,
R 2 , R 3 are each independently hydrogen, linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 20 carbon atoms, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 5 to 18 carbon atoms and/or heteroatoms,
R 4 , R 5 , R 6 , R 7 are each independently hydrogen, substituent with donor or acceptor action, linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 20 carbon atoms, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 5 to 18 carbon atoms and/or heteroatoms,
or
R 4 and R 5 or R 5 and R 6 and/or R 6 and R 7 together form a saturated, unsaturated or aromatic carbon ring optionally interrupted by at least one heteroatom and having a total of 5 to 30 carbon atoms or heteroatoms,
R 8 , R 9 are each independently a free electron pair if A 1 or A 2 is N, or, if A 1 or A 2 is C, hydrogen, linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 20 carbon atoms, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 5 to 18 carbon atoms and/or heteroatoms,
R 10 is a linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 20 carbon atoms, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 5 to 18 carbon atoms and/or heteroatoms,
R 11 , R 12 , R 13 , R 14 are each independently hydrogen, substituent with donor or acceptor action, linear or branched alkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 1 to 20 carbon atoms, cycloalkyl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 3 to 20 carbon atoms, substituted or unsubstituted aryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical optionally interrupted by at least one heteroatom, optionally bearing at least one functional group and having 5 to 18 carbon atoms and/or heteroatoms,
or
R 11 and R 12 or R 12 and R 13 and/or R 13 and R 14 together form a saturated, unsaturated or aromatic carbon ring optionally interrupted by at least one heteroatom and having a total of 5 to 30 carbon atoms and/or heteroatoms
R 1 and R 14 optionally together form a saturated or unsaturated, linear or branched bridge optionally comprising heteroatoms, aromatic units, heteroaromatic units and/or functional groups and having a total of 1 to 30 carbon atoms and/or heteroatoms, to which a substituted or unsubstituted, five to eight-membered ring comprising carbon atoms and/or heteroatoms is optionally fused,
if A 1 is C, then R 7 and R 8 optionally together form a saturated or unsaturated, linear or branched bridge optionally comprising heteroatoms, aromatic units, heteroaromatic units and/or functional groups and having a total of 1 to 30 carbon atoms and/or heteroatoms, to which a substituted or unsubstituted, five to eight-membered ring comprising carbon atoms and/or heteroatoms is optionally fused, and
wherein at least one pair of substituents selected from the group consisting of R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 11 and R 12 , R 12 and R 13 , and R 13 and R 14 together form a saturated, unsaturated or aromatic carbon ring optionally interrupted by at least one heteroatom and having a total of 5 to 30 carbon atoms or heteroatoms.

2. The heteroleptic complex according to claim 1 , wherein M,
M is Ir,
A 1 , A 2 is C,
n, m are each independently 1 or 2, where the sum of n and m is 3,
R 1 is a linear or branched alkyl radical having 1 to 20 carbon atoms, substituted or unsubstituted aryl radical having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical having 5 to 18 carbon atoms and/or heteroatoms,
R 2 , R 3 are each independently hydrogen, linear or branched alkyl radical having 1 to 20 carbon atoms, substituted or unsubstituted aryl radical having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl radical having 5 to 18 carbon atoms and/or heteroatoms,
R 4 , R 5 ,
R 6 , R 7 are each hydrogen
or
R 4 and R 5 or R 5 and R 6 or R 6 and R 7 together form a saturated, unsaturated or aromatic ring optionally interrupted by at least one heteroatom and having a total of 5 to 30 carbon atoms and/or heteroatoms,
R 8 , R 9 are each hydrogen,
R 10 is a linear or branched alkyl radical having 1 to 20 carbon atoms, substituted or unsubstituted aryl radical having 6 to 30 carbon atoms, and
R 11 , R 12 , R 13 , R 14 are each independently hydrogen or linear or branched alkyl radical having 1 to 20 carbon atoms,
R 1 and R 14 optionally together form a saturated or unsaturated, linear or branched bridge optio

Assignees

• Basf Se
• Oledworks Gmbh
• Osram Oled Gmbh

Inventors

• Fuchs Evelyn
• Molt Oliver
• Dormann Korinna
• Gessner Thomas
• Langer Nicolle
• Muenster Ingo
• Qu Jianqiang
• Lennartz Christian
• Schildknecht Christian
• Watanabe Soichi
• Wagenblast Gerhard
• Schmid Guenter
• Boerner Herbert Friedrich
• Van Elsbergen Volker

Classifications

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K85/40

  Organosilicon compounds, e.g. TIPS pentacene · CPC title

• H10K50/14

  Carrier transporting layers · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/361

  Polynuclear complexes, i.e. complexes comprising two or more metal centers · CPC title