Metal complexes

Patent metadata

Field	Value
Publication number	US-9831446-B2
Application number	US-201314434167-A
Country	US
Kind code	B2
Filing date	Sep 11, 2013
Priority date	Oct 9, 2012
Publication date	Nov 28, 2017
Grant date	Nov 28, 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 formula (2) or formula (3):

wherein
M is a transition metal selected from the group consisting of chromium, molybdenum, tungsten, rhenium, osmium, rhodium, iridium, nickel, platinum, copper, silver, and gold;
X is selected on each occurrence, identically or differently, from the group consisting of CR and N;
Y is selected on each occurrence, identically or differently, from the group consisting of C(R 1 ) 2 , Si(R 1 ) 2 , PR 1 , P(═O)R 1 , and BR 1 ;
Z is selected on each occurrence, identically or differently, from the group consisting of NR 1 and C(R 1 ) 2 , or —Y-Z— is selected on each occurrence, identically or differently, from the group consisting of —Si(R 1 ) 2 —O—, —P(═O)R 1 —O—, and —BR 1 —O—;
D is on each occurrence, identically or differently, C or N, with the proviso that at least one D is N;
E is on each occurrence, identically or differently, C or N, with the proviso that at least one of E or D in the five-membered ring is N;
R and R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R 2 ) 2 , CN, NO 2 , OH, COOH, C(═O)N(R 2 ) 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 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 , and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, or CN, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms optionally substituted by one or more radicals R 2 , an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 2 , 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 adjacent radicals R or two adjacent radicals R 1 optionally define a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another; and wherein a radical R and a radical R 1 optionally define a mono- or polycyclic, aliphatic or heteroaromatic ring system with one another;
R 2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R 3 ) 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , S(═O) 2 R 3 , OSO 2 R 3 , 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 is optionally substituted by one or more radicals R 3 , wherein one or more non-adjacent CH 2 groups are optionally replaced by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , C═O, NR 3 , O, S, or CONR 3 , and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms optionally substituted by one or more radicals R 3 , an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 3 , an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 3 , or a diarylamino group, diheteroarylamino group, or arylheteroarylamino group having 10 to 40 aromatic ring atoms optionally be substituted by one or more radicals R 3 ; and wherein two or more adjacent radicals R 2 with one another or a radical R 2 and a radical R or a radical R 1 optionally define a mono- or polycyclic, aliphatic, aromatic, or heteroaromatic ring system;
R 3 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 is optionally replaced by F; and wherein two or more substituents R 3 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 with one another or a ligand L with a ligand L′ are optionally linked via a single bond or a divalent or trivalent bridge to form a tridentate, tetradentate, pentadentate, or hexadentate ligand system, wherein L′ is not a separate co-ligand, but instead a coordinating group; and
wherein a substituent R is optionally additionally coordinated to M.

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

3. The compound of claim 1 , wherein the moiety of formula (2) is selected from the group consisting of moieties of formulae (2a), (2b), and (2c) and the moiety of formula (3) is selected from the group consisting of moieties of formulae (3a), (3b), and (3c):

4. The compound of claim 1 , wherein the group —Y—Z— is, identically or differently on each occurrence, —C(R 1 ) 2 —NR 1 —, —Si(R 1 ) 2 —NR 1 —, —Si(R 1 ) 2 —O—, or —C(R 1 ) 2 —C(R 1 ) 2 —.

5. The compound of claim 1 , wherein R 1 is selected, identically or differently on each occurrence, from the group consisting of F, CN, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, each of which 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 , and wherein one or more H atoms are optionally replaced by F, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R 2 , an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R 2 , 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 30 aromatic ring atoms optionally substituted by one or more radicals R 2 ; and wherein two adjacent radicals R 1 optionally define a mono- or polycyclic, aliphatic, aromatic, or heteroaromatic ring system with one another; and wherein a radical R and a radical R 1 optionally define a mono- or polycyclic, aliphatic or heteroaromatic ring system with one another.

6. The compound of claim 1 , wherein 0, 1, or 2 groups X in the ligand L is N.

7. The compound of claim 1 , wherein the moiety of formula (2) is selected from the group consisting of moieties of formulae (2-A) to (2-G) and the moiety of formula (3) is selected from the group consisting of moieties of formulae (3-A) to (3-H):

Assignees

• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Kaiser Joachim
• Joosten Dominik
• Koenen Nils
• Breuning Esther

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C07F15/0086

  Platinum compounds · CPC title

• C07F9/65846

  the phosphorus atom being part of a six-membered ring which may be condensed with another ring system · CPC title

• C07F9/6584

  having one phosphorus atom as ring hetero atom · CPC title

• C07D498/20

  Spiro-condensed systems · CPC title