Metal complexes

Patent metadata

Field	Value
Publication number	US-11322696-B2
Application number	US-201716341596-A
Country	US
Kind code	B2
Filing date	Oct 9, 2017
Priority date	Oct 12, 2016
Publication date	May 3, 2022
Grant date	May 3, 2022

Abstract

The present invention relates to binuclear metal complexes and electronic devices, in particular organic electroluminescent devices containing said metal complexes of the formula (1):

First claim

The invention claimed is:

1. A compound of formula (1):

wherein
M 1 and M 2
is the same or different and is iridium or rhodium;

V is a group of formula (2) or (3):

wherein the dotted bonds in the 1, 3, and 5 positions denote bonds to L 1 and the dotted bonds in the 2, 4, and 6 positions denote bonds to L 2 ;

L 1 and L 2
is the same or different at each instance and is a bidentate monoanionic sub-ligand;

A is the same or different in each instance and is —CR═CR—, —C(═O)—NR′—, —C(═O)—O—, —CR 2 —CR 2 —, —CR 2 —O—, or a group of formula (4):

wherein the dotted bond denotes the position of the bond of one bidentate sub-ligand L 1 or L 2 to this structure and * denotes the position of the linkage of the unit of formula (4) to the benzene or cyclohexane group in formula (2) or (3);

X 1 is the same or different in each instance and is CR or N or two adjacent X 1 groups together are NR, O, or S, so as to define a five-membered ring, and the remaining X 1 are the same or different in each instance and are CR or N; or two adjacent X 1 groups together are CR or N when one of the X 2 groups in the cycle is N, so as to define a five-membered ring; with the proviso that not more than two adjacent X 1 groups are N;
X 2 is C in each instance or one X 2 group is N and the other X 2 group in the same cycle is C; with the proviso that two adjacent X 1 groups together are CR or N when one of the X 2 groups in the cycle is N;
R is the same or different in each instance and is 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 , COO(cation), SO 3 (cation), OSO 3 (cation), OPO 3 (cation) 2 , O(cation), N(R 1 ) 3 (anion), P(R 1 ) 3 (anion), a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein the alkyl, alkenyl, or alkynyl group in each case is optionally substituted by one or more R 1 radicals, wherein one or more nonadjacent CH 2 groups is optionally replaced by Si(R 1 ) 2 , C═O, NR 1 , O, S, or CONR 1 , or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is optionally substituted in each case by one or more R 1 radicals; and wherein two R radicals together optionally define a ring system;
R′ is the same or different in each instance and is H, D, a straight-chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein the alkyl group in each case is optionally substituted by one or more R 1 radicals and wherein one or more nonadjacent CH 2 groups is optionally replaced by Si(R 1 ) 2 , or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is optionally substituted in each case by one or more R 1 radicals;
R 1 is the same or different in each instance and is 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 , COO(cation), SO 3 (cation), OSO 3 (cation), OPO 3 (cation) 2 , O(cation), N(R 2 ) 3 (anion), P(R 2 ) 3 (anion), a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, wherein the alkyl, alkenyl, or alkynyl group in each case is optionally substituted by one or more R 2 radicals, wherein one or more nonadjacent CH 2 groups are optionally replaced by Si(R 2 ) 2 , C═O, NR 2 , O, S, or CONR 2 , or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is optionally substituted in each case by one or more R 2 radicals; and wherein two or more R 1 radicals together optionally define a ring system;
R 2 is the same or different in each instance and is H, D, F, or an aliphatic, aromatic, or heteroaromatic organic radical having 1 to 20 carbon atoms, wherein one or more hydrogen atoms is also optionally replaced by F;
cation is the same or different in each instance and is selected from the group consisting of proton, deuteron, alkali metal ions, alkaline earth metal ions, ammonium, tetraalkylammonium, and tetraalkylphosphonium; and
anion is the same or different at each instance and is selected from the group consisting of halides, carboxylates R 2 —COO − , cyanide, cyanate, isocyanate, thiocyanate, thioisocyanate, hydroxide, BF 4 − , PF 6 − , B(C 6 F 5 ) 4 − , carbonate, and sulfonates.

2. The compound of claim 1 , wherein M 1 and M 2 are Ir(III) and the compound is uncharged.

3. The compound of claim 1 , wherein the group of formula (4) is selected from the group consisting of structures of Formulae (5) through (29):

4. The compound of claim 1 , wherein the group of formula (2) is selected from the group consisting of Formulae (2a) through (2e) and wherein the group of formula (3) is selected from the group consisting of Formulae (3a) through (3e):

5. The compound of claim 1 , wherein the group of formula (2) is selected from the group consisting of Formula (2a′) and the group of Formula (3) is selected from the group consisting of Formula (3a′):

6. The compound of claim 1 , wherein the group of formula (2) is selected from the group consisting of Formula (2a″) and the group of formula (3) is selected from the group consisting of Formula (3a″):

7. The compound of claim 1 , wherein all three sub-ligands L 1 are the same and all three sub-ligands L 2 are the same, wherein L 1 =L 2 or L 1 ≠L 2 .

8. The compound of claim 1 , wherein all sub-ligands L 1 and L 2 have one carbon atom and one nitrogen atom or two carbon atoms as coordinating atoms.

9. The compound of claim 1 , wherein at least two of sub-ligands L 1 and at least two of sub-ligands L 2 are the same or different in each instance and are selected from the group consisting of structures of Formulae (L-1), (L-2), and (L-3):

wherein
the dotted bond denotes the bond of sub-ligand L 1 or L 2 to V;
CyC is the same or different in each instance and is a substituted or unsubstituted aryl or heteroaryl group which has 5 to 14 aromatic

Assignees

• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Koenen Nils
• Ehrenreich Christian

Classifications

• H10K85/342

  comprising iridium · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K2211/185

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

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C07F15/0073

  Rhodium compounds · CPC title