Metal complexes

Patent metadata

Field	Value
Publication number	US-9831448-B2
Application number	US-201415021076-A
Country	US
Kind code	B2
Filing date	Aug 12, 2014
Priority date	Sep 11, 2013
Publication date	Nov 28, 2017
Grant date	Nov 28, 2017

Abstract

The invention relates to metal complexes and to electronic devices, in particular organic electroluminescence devices, containing said metal complexes.

First claim

The invention claimed is:

1. A compound of formula (1):
[Ir(L) n (L′) m ]  (1)

wherein the compound of formula (1) comprises a substructure Ir(L) n of formula (2):

wherein
Y is the same or different in each instance and is CR or N, with the proviso that not more than one Y per cycle is N, or two adjacent Y together are a group of formula (3):

wherein the dotted bonds denote the linkage of this group in the ligand;

X is the same or different in each instance and is CR or N, with the proviso that not more than two X per ligand are N;
R is the same or different in each instance and is H, D, F, Cl, Br, I, N(R 1 ) 2 , CN, Si(R 1 ) 3 , B(OR 1 ) 2 , C(═O)R 1 , a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 40 carbon atoms, a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms, or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, or thioalkoxy group having 3 to 40 carbon atoms, each of which is optionally substituted by one or more R 1 radicals, wherein one or more nonadjacent CH 2 groups are optionally replaced by R 1 C═CR 1 , Si(R 1 ) 2 , C═O, NR 1 , O, S, or CONR 1 and wherein one or more hydrogen atoms are optionally replaced by D, F, or CN, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and is optionally substituted by one or more R 1 radicals, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms and is optionally substituted by one or more R 1 radicals, or a diarylamino group, diheteroarylamino group, or arylheteroarylamino group having 10 to 40 aromatic ring atoms and is optionally substituted by one or more R 1 radicals; and wherein two or more adjacent R radicals together optionally define a mono- or polycyclic, aliphatic, aromatic and/or benzofused ring system;
R 1 is the same or different in each instance and is H, D, F, Cl, Br, I, N(R 2 ) 2 , CN, Si(R 2 ) 3 , B(OR 2 ) 2 , C(═O)R 2 , a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 40 carbon atoms, or a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms, or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, or thioalkoxy group having 3 to 40 carbon atoms, each of which is optionally substituted by one or more R 2 radicals, wherein one or more nonadjacent CH 2 groups are optionally replaced by R 2 C═CR 2 , Si(R 2 ) 2 , C═O, NR 2 , O, S, or CONR 2 and wherein one or more hydrogen atoms are optionally replaced by D, F, or CN, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and is optionally substituted by one or more R 2 radicals, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms and is optionally substituted by one or more R 2 radicals, or a diarylamino group, diheteroarylamino group, or arylheteroarylamino group having 10 to 40 aromatic ring atoms and is optionally substituted by one or more R 2 radicals; and wherein two or more adjacent R 1 radicals together optionally define a mono- or polycyclic, aliphatic ring system;
R 2 is the same or different in each instance and is H, D, F, or an aliphatic, aromatic, and/or heteroaromatic organic radical having 1 to 20 carbon atoms, wherein one or more hydrogen atoms are optionally replaced by D or F; and wherein two or more R 2 substituents together optionally define a mono- or polycyclic, aliphatic or aromatic ring system;
L′ is the same or different in each instance and is a mono- or bidentate ligand;
n is 1, 2, or 3;
m is 0, 1, 2, 3, or 4;
wherein, in the substructure of formula (2), two adjacent Y are CR and the respective R radicals together with the carbon atoms to which they are attached define a ring of formula (4) or formula (5) and/or two adjacent Y are a group of formula (3) and two adjacent X in the group of formula (3) are CR and the respective R radicals together with the carbon atoms to which they are attached define a ring of formula (4) or formula (5):

wherein
the dotted bonds denote the linkage of the two carbon atoms in the ligand;
A 1 and A 3
are the same or different in each instance and are C(R 3 ) 2 , O, S,
NR 3 , or C(═O);

A 2 is C(R 1 ) 2 , O, S, NR 3 , or C(═O);
G is an alkylene group having 1, 2, or 3 carbon atoms and is optionally substituted by one or more R 2 radicals, —CR 2 ═CR 2 —, or an ortho-bonded arylene or heteroarylene group having 5 to 14 aromatic ring atoms and is optionally substituted by one or more R 2 radicals;
R 3 is the same or different in each instance and is F, a straight-chain alkyl or alkoxy group having 1 to 10 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 10 carbon atoms, each of which is optionally substituted by one or more R 2 radicals, wherein one or more nonadjacent 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 , and wherein one or more hydrogen atoms are optionally replaced by D or F, an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms and is optionally substituted by one or more R 2 radicals, an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms and is optionally substituted by one or more R 2 radicals, or an aralkyl or heteroaralkyl group having 5 to 24 aromatic ring atoms and is optionally substituted by one or more R 2 radicals; and wherein two R 3 radicals bonded to the same carbon atom together optionally define an aliphatic or aromatic ring system and thus form a spiro system; and wherein R 3 with an adjacent R or R 1 radical optionally defines an aliphatic ring system;

with the proviso that no two heteroatoms in A 1 -A 2 -A 1 are bonded directly to one another and no two C═O groups are bonded directly to one another.

2. The compound of claim 1 , wherein
n is 3 and m is 0, or
n is 2 and m is 1,
wherein L′ is a bidentate ligand which coordinates to the iridium via one carbon atom and one nitrogen atom, one carbon atom and one oxygen atom, two oxygen atoms, two nitrogen atoms, or one oxygen atom and one nitrogen atom, or

n is 1 and m is 2,
where L′ is an ortho-metalated ligand which coordinates to the iridium via one carbon atom and one nitrogen or oxygen atom.

3. The compound of claim 1 , wherein the substructure Ir(L) n is selected from the group consisting of structures of formulae (6) through (15):

wherein Y is the same or different in each instance and is CR or N.

4. The compound of claim 1 , wherein a total of 0, 1, or 2 of Y and, if present, X in L are N.

5. The compound of claim 1 , wherein the substructure Ir(L) n is selected from the group consisting of structures of formulae (6-1) through (6-7), (7-1) through (7-6), (8-1) through (8-5), (9-1) through (9-5), (10-1) through (10-5), (11-1) through (11-6), (12-1) through (12-4), (13-1) through (13-3), (14-1) through (14-4), and (15-1) through (15-3):

Assignees

• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Koenen Nils
• Breuning Esther

Classifications

• C07D221/20

  Spiro-condensed ring systems · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C07F15/0033

  Iridium compounds · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title