Metal complexes and use thereof in electronic devices

Patent metadata

Field	Value
Publication number	US-10050218-B2
Application number	US-201414783642-A
Country	US
Kind code	B2
Filing date	Mar 14, 2014
Priority date	Apr 11, 2013
Publication date	Aug 14, 2018
Grant date	Aug 14, 2018

Abstract

The present invention relates metal complexes and to electronic devices, particularly organic electroluminescent devices containing said metal complexes.

First claim

The invention claimed is:

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

containing a moiety M(L) n of formula (2):

wherein
M is a transition metal;
A is on each occurrence, identically or differently, O, S, or NR;
X is on each occurrence, identically or differently, CR or N;
or two adjacent groups X are group of formula (3) or (4):

wherein
Y is on each occurrence, identically or differently, CR or N; and
E is on each occurrence, identically or differently, CR 2 , NR, O, or S;

R is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R 1 ) 2 , P(R 1 ) 2 , CN, NO 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 , OH, SH, a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 40 C atoms, a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms, or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, or thioalkoxy group having 3 to 40 C atoms, each of which 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 , Ge(R 1 ) 2 , Sn(R 1 ) 2 , C═O, C═S, C═Se, C═NR 1 , P(═O)(R 1 ), SO, SO 2 , NR 1 , O, S, or CONR 1 , 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, which is optionally substituted by one or more radicals R 1 , an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 , an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is 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, which is optionally substituted by one or more radicals R 1 ; and wherein two or more adjacent radicals R optionally define a mono- or polycyclic, aliphatic, aromatic, and/or benzo-fused 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 40 C atoms, a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms, or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, or thioalkoxy group having 3 to 40 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 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , 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 , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is 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, which is substituted by one or more radicals R 2 ; and wherein two or more adjacent radicals R 1 optionally define a mono- or polycyclic, aliphatic, or aromatic 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 D or F; and wherein two or more substituents R 2 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
L′ is, identically or differently on each occurrence, any desired co-ligand;
n is 1, 2, or 3; and
m is 0, 1, 2, 3, or 4; and
wherein a plurality of ligands L are optionally linked to one another or L is optionally linked to L′ via any desired bridge V so as to define a tridentate, tetradentate, pentadentate or hexadentate ligand system.

2. The compound of claim 1 , wherein R 2 is a hydrocarbon radical.

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

4. The compound of claim 1 , wherein the moiety of formula (2) is selected from the group consisting of the structures of formulae (5) to (17):

wherein
X is, identically or differently on each occurrence, for CR or N.

5. The compound of claim 1 , wherein a maximum of two groups X are nitrogen and the other groups X in the ring are CR and a maximum of two groups Y are nitrogen and the other groups Y in the ring are CR.

6. The compound of claim 5 , wherein a maximum of one group X per ring is nitrogen and a maximum of one group Y per ring is nitrogen.

7. The compound of claim 1 , wherein the moiety of formula (2) is selected from the group consisting of the structures of formulae (5a) to (5d), (7a) to (7c), and (5a) to (8c):

8. The compound of claim 1 , wherein A is O or S.

9. The compound of claim 1 , wherein, if one or more X is N, at least one R which is not H or D is bonded adjacent to this N atom.

10. The compound of claim 9 , wherein R is an alkyl group, an alkoxy group, a substituted amino group, an aralkyl group or an aromatic or heteroaromatic ring system.

11. The compound of claim 1 , wherein L has two adjacent carbon atoms, each of which are substituted by radicals R, wherein the respective radicals R, together with the C atoms, define a ring selected from the group consisting of formulae (18), (19), (20), and (20a) to (20c):

wherein
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, identically or differently on each occurrence, C(R 1 ) 2 , O, S, NR 3 , or C(═O);
or the two groups A 2 in formula (20) together define a group of formula (21) or (22):

G is an alkylene group having 1, 2, or 3 C atoms, which is optionally substituted by one or more radicals R 2 , —CR 2 ═:═CR 2 —, or an ortho-linked arylene or heteroarylene group having 5 to 14 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 ;
R 3 is, identically or differently on each occurrence, F, a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, each of which is optionally substituted by one or more radical

Assignees

• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Koenen Nils
• Breuning Esther

Classifications

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1011

  Condensed systems · CPC title