Metal complexes

Patent metadata

Field	Value
Publication number	US-9837622-B2
Application number	US-201314414298-A
Country	US
Kind code	B2
Filing date	Jun 21, 2013
Priority date	Jul 13, 2012
Publication date	Dec 5, 2017
Grant date	Dec 5, 2017

Abstract

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

First claim

The invention claimed is:

1. A compound of formula (1)
M(L) n (L′) m   (1)

comprising a moiety M(L) n of formulae (2), (3), or (4):

wherein:
M is a transition metal;
X is selected, on each occurrence, identically or differently, from the group consisting of CR and N;
R is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R 1 ) 2 , CN, NO 2 , OH, 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, alkoxy, or thioalkoxy 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, alkoxy, or thioalkoxy group having 3 to 20 C atoms, each of which are optionally substituted by one or more radicals R 1 , and 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 , and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, or CN, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms optionally substituted by one or more radicals R 1 , or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 1 , or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 1 , or a diarylamino group, diheteroarylamino group, or arylheteroarylamino group having 10 to 40 aromatic ring atoms optionally substituted by one or more radicals R 1 ; and wherein two adjacent radicals R optionally define a mono- or polycyclic, aliphatic, aromatic, or heteroaromatic ring system with one another;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R 2 ) 2 , CN, NO 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, alkoxy, or thioalkoxy 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, alkoxy, or thioalkoxy group having 3 to 20 C atoms, each of which are optionally substituted by one or more radicals R 2 , and 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 , and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms optionally substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 , or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 , or a diarylamino group, diheteroarylamino group, or arylheteroarylamino group having 10 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 ; and wherein two or more adjacent radicals R 1 with one another or R 1 with R optionally define a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system;
R 2 is on each occurrence, identically or differently, H, D, F or an aliphatic, aromatic, and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, wherein one or more H atoms are optionally replaced by F; and wherein two or more substituents R 2 optionally define a mono- or polycyclic, aliphatic ring system with one another;
L′ is, identically or differently on each occurrence, any desired co-ligand;
n is 1, 2, or 3;
m is 0, 1, 2, 3, or 4;
wherein
a plurality of ligands L are optionally linked to one another or L is optionally linked to L′ via a single bond or a divalent or trivalent bridge and thus form a tridentate, tetradentate, pentadentate, or hexadentate ligand system;
a substituent R optionally additionally coordinates to the metal; and
two adjacent groups X are CR and the respective radicals R, together with the C atoms, form a ring of formula (5) or (6);

wherein
R 1 and R 2 are as defined above;
the dashed bonds indicate the linking of the two carbon atoms in the ligand;
A 1 and A 3
are, identically or differently, on each occurrence, 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 C atoms optionally substituted by one or more radicals R 2 , or is —CR 2 ═CR 2 — or an ortho-linked arylene or heteroarylene group having 5 to 14 aromatic ring atoms optionally substituted by one or more radicals R 2 ; and
R 3 is, identically or differently on each occurrence, F, a straight-chain alkyl or alkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms 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 and wherein one or more H atoms are optionally replaced by D or F, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R 2 , or an aralkyl or heteroaralkyl group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R 2 ; and wherein two radicals R 3 bonded to the same carbon atom optionally define an aliphatic or aromatic ring system with one another and thus form a spiro system; and wherein R 3 optionally defines an aliphatic ring system with an adjacent radical R or R 1 ; and
with the proviso that two heteroatoms are not bonded directly to one another in A 1 -A 2 -A 3 .

2. The compound of claim 1 , wherein M is selected from the group consisting of chromium, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, nickel, palladium, platinum, copper, silver, and gold.

3. The compound of claim 1 , wherein M is selected from the group consisting of molybdenum, tungsten, rhenium, ruthenium, osmium, iridium, copper, platinum, and gold.

4. The compound of claim 1 , wherein the moiety of formula (2) is selected from the group consisting of formulae (2-A) to (2-Q), the moiety of formula (3) is selected from the group consisting of formulae (3-A) to (3-F), the moiety of formula (4) is selected from the group consisting of formulae (4-A) to (4-F):

5. The compound of claim 1 , wherein the moiety of formula (2) is selected from the group consisting of formulae (2-1) to (2-5), the moiety of formula (3) is selected from the group consisting of formulae (3-1) to (3-3), and the moiety of formula (4) is selected from the group consisting of formulae (4-1) to (4-4):

Assignees

• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Joosten Dominik
• Breuning Esther
• Kaiser Joachim
• Ehrenreich Christian

Classifications

• C09K2211/1011

  Condensed systems · CPC title

• C07D519/00

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C07F5/025

  Boronic and borinic acid compounds · CPC title