Metal complexes

Patent metadata

Field	Value
Publication number	US-12479873-B2
Application number	US-202318204416-A
Country	US
Kind code	B2
Filing date	Jun 1, 2023
Priority date	Jul 14, 2016
Publication date	Nov 25, 2025
Grant date	Nov 25, 2025

Abstract

The present invention relates to metal complexes and to electronic devices, in particular organic electroluminescent devices, containing these metal complexes.

First claim

The invention claimed is:

1 . A monometallic compound comprising a hexadentate tripodal ligand wherein three bidentate part-ligands, which may be identical or different, are coordinated to a metal and the three bidentate part-ligands are linked to one another via a bridge of formula (1):

wherein
the dashed bonds are the bonds from the bidentate part-ligands to the structure of formula;
X 1 is on each occurrence, identically or differently, CR 2 or O;
X 2 is on each occurrence, identically or differently, CR, P═O, B, or Si, which is optionally substituted, with the proviso that, when X 2 is P=O, B, or Si, which is optionally substituted, X 1 is O; and wherein substituents optionally present on X 1 and X 2 optionally define an aliphatic or heteroaliphatic ring system with themselves or with one another;
X 3 is on each occurrence, identically or differently, —CR=CR—, —CR=N—, —CR—NR″—, —C(═O)—O—, —C(═O)—NR″—, —C(═O)—S—, —C(═S)—O—, —C(═S)—NR″—, —C(═S)—S—;
R is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R 1 ) 2 , CN, NO 2 , OR 1 , SR 1 , COOH, C(═O)N(R 1 ) 2 , Si(R 1 ) 3 , B(OR 1 ) 2 , C(═O)R 1 , P(═O)(R 1 ) 2 , S(═O)R 1 , S(═O) 2 R 1 , OSO 2 R 1 , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl, or alkynyl group in each case is optionally substituted by one or more radicals R 1 , wherein one or more non-adjacent CH 2 groups are optionally replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , C═O, NR 1 , O, S, or CONR 1 , or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R 1 ; and wherein two or more radicals R which are bonded to X 1 and/or X 2 optionally define an aliphatic or heteroaliphatic ring system with one another; and wherein two radicals R when X 3 is —CR=CR-optionally define an aliphatic, heteroaliphatic, aromatic, or heteroaromatic ring system with one another; and wherein radicals R and R″ when X 3 is —CR—NR″-define a heteroaromatic ring system with one another;
R″ is on each occurrence, identically or differently, H, D, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 C atoms, wherein the alkyl or alkenyl group in each case is optionally substituted by one or more radicals R 1 and wherein one or more non-adjacent CH 2 groups are optionally replaced by Si(R 1 ) 2 , or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R 1 ;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R 2 ) 2 , CN, NO 2 , OR 2 , SR 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)R 2 , P(═O)(R 2 ) 2, S(═O)R 2 , S(═O) 2 R 2 , OSO 2 R 2 , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl, or alkynyl group in each case is optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2, C═O, NR 2 , O, S, or CONR 2 , or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R 2 ; wherein a plurality of substituents R 1 optionally define an aliphatic, heteroaliphatic, aromatic, or heteroaromatic ring system with one another; furthermore, the groups R or R substituted with R 1 optionally form a ring system, and groups R and R 1 optionally form a ring system with one another;
R 2 is on each occurrence, identically or differently, H, D, F, or an aliphatic, aromatic, and/or heteroaromatic organic radical having 1 to 20 C atoms, wherein one or more H atoms are optionally replaced by F;
wherein the bidentate part-ligands are selected, identically or differently on each occurrence, from the group consisting of structures of formulae (L-1), (L-2), (L-3), and (L-4):

wherein
the dashed bond is the bond from the part-ligand to the bridge of formula (1);
CyC is, identically or differently on each occurrence, an optionally substituted aryl or heteroaryl group having 5 to 14 aromatic ring atoms, which is coordinated to the metal via a carbon atom and which is connected to CyD via a covalent bond;
CyD is, identically or differently on each occurrence, an optionally substituted heteroaryl group having 5 to 14 aromatic ring atoms, which is coordinated to the metal via a nitrogen atom or via a carbene carbon atom and which is connected to CyC via a covalent bond; and
wherein a plurality of the optional substituents optionally defines a ring system with one another; and
the three bidentate ligands are optionally cyclised by a further bridge, in addition to the bridge of formula (1), to define a cryptate.

2 . The monometallic compound of claim 1 , wherein the bridge of formula (1) is selected from the group consisting of structures of formulae (2) through (6):

wherein
R′ is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R 1 ) 2 , CN, NO 2 , OR 1 , SR 1 , COOH, C(═O)N(R 1 ) 2 , C(═O)R 1 , P(═O)(R 1 ) 2 , S(═O)R 1 , S(═O) 2 R 1 , OSOR 1 , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl, alkenyl, or alkynyl group in each case is optionally substituted by one or more radicals R 1 , wherein one or more non-adjacent CH 2 groups are optionally replaced by R 1 C═CR 1 , C≡C, C═O, NR 1 , O, S, or CONR 1 , or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which in each case are optionally substituted by one or more radicals R 1 .

3 . The monometallic compound of claim 1 , wherein the bridge of formula (1) is selected from the structures of the formulae (2a) and (2b),

4 . The monometallic compound of claim 1 , wherein the metal is selected from the group consisting of aluminium, gallium, indium, tin, chromium, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, iron, cobalt, nickel, palladium, platinum, copper, silver, and gold.

5 . The monometallic compound of claim 1 , wherein the bidentate part-ligands are each monoanionic and wherein the three bidentate part-ligands are either selected identically or two bidentate part-ligands are selected identically and the third bidentate part-ligand is selected differently from the first two bidentate part-ligands and wherein the coordinating atoms of the bidentate part-ligands are selected, identically or differently on each occurrence, from C and N.

6 . The monometallic compound of claim 1 , wherein the metal is Ir(III) and two of the bidentate part-ligands are coordinated to the iridium in each case via one carbon atom and one nitrogen atom or via two carbon atoms and the third of the bidentate part-ligands is coordinated to the iridium via one carbon atom and one nitrogen atom or via two carbon atoms or via two nitrogen atoms.

7 . The

Assignees

• Udc Ireland Ltd
• UDC Ireland

Inventors

• Stoessel Philipp
• Ehrenreich Christian

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/342

  comprising iridium · CPC title

• H10K50/156

  comprising a multilayered structure · CPC title

• H10K50/16

  Electron transporting layers · CPC title