Metal complexes

Patent metadata

Field	Value
Publication number	US-9469667-B2
Application number	US-201214009445-A
Country	US
Kind code	B2
Filing date	Mar 7, 2012
Priority date	Apr 4, 2011
Publication date	Oct 18, 2016
Grant date	Oct 18, 2016

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 the formula (1),
[M(L) n (L′) m ] w x+/x− [A] y z−/z+   formula (1)

where the compound of the general formula (1) contains a moiety M(L) n of the formula (2):

where the following applies to the symbols and indices used:
M is a transition metal;
Q is on each occurrence, identically or differently, N;
X is on each occurrence, identically or differently, CR or N;
Y is on each occurrence, identically or differently, a substituted or unsubstituted diatomic bridge containing, as bridge atoms, two atoms selected, identically or differently on each occurrence, from the group consisting of C, N, O, S, Si or P;
W is on each occurrence, identically or differently, CR═CR or CR═N;
Z is C;
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 is optionally substituted by one or more radicals R 1 , where one or more non-adjacent CH 2 groups is optionally replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , C═O, NR 1 , O, S or CONR 1 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I or CN, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which optionally in each case be substituted by one or more radicals R 1 , or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 , or an aralkyl or heteroaralkyl group having 5 to 40 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 ; two adjacent radicals R here may also form 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 is optionally substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups is optionally replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , C═O, NR 2 , O, S or CONR 2 and where one or more H atoms is 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, which may in each case be substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or an aralkyl or heteroaralkyl group having 5 to 40 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 optionally substituted by one or more radicals R 2 ; two or more adjacent radicals R 2 here may form a mono- or polycyclic, aliphatic ring system with one another;
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, in which, in addition, one or more H atoms is optionally replaced by F; two or more substituents R 2 here may also form a mono- or polycyclic, aliphatic ring system with one another;
L′ is, identically or differently on each occurrence, any desired co-ligand;
A is a counterion;
n is 1, 2 or 3;
m is 0, 1, 2, 3 or 4;
w is 1, 2 or 3;
x, y, z are on each occurrence, identically or differently, 0, 1, 2 or 3; where (w·x)=(y·z);
a plurality of ligands L here may also be linked to one another or L is optionally linked to L′ via any desired bridge V and thus form a tridentate, tetradentate, pentadentate or hexadentate ligand system;
furthermore, a substituent R may also additionally be coordinated to the metal.

2. The compound according to 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 according to claim 1 , wherein one of the two bridge atoms in the group Y represents a carbon atom and in that the other bridge atom is selected from C, N or O, where the atoms may in each case be substituted by radicals R.

4. The compound according to claim 1 , wherein the bridge Y is selected from the structures —CR═CR—, —CR═N—, —C(═O)—CR 2 —, —C(═O)—NR—, —C(═O)—O— or —CR 2 —CR 2 — or from the structures of the formulae (A) to (E),

where R has the meaning given in claim 1 and the dashed bonds in each case indicate the bonding of this group in the corresponding ligand.

5. The compound according to claim 1 , wherein X stands for CR or CH.

6. A compound of the formula (1),
[M(L) n (L′) m ] w x+/x− [A] y z−/z+   formula (1)

where the compound of the general formula (1) contains a moiety M(L) n of the formula (2):

where the following applies to the symbols and indices used:
M is a transition metal;
Q is on each occurrence, identically or differently, N;
X is on each occurrence, identically or differently, CR or N;
Y is on each occurrence, identically or differently, a substituted or unsubstituted diatomic bridge containing, as bridge atoms, two atoms selected, identically or differently on each occurrence, from the group consisting of C, N, O, S, Si or P;
W is on each occurrence, identically or differently, CR, N, CR═CR or CR═N if Q stands for N, with the proviso that W stands for CR═CR or CR═N if Y stands for CR═CR or for CR═N;
or W is NR if Q stands for C;
Z is C if W in this ligand stands for CR═CR or CR═N; or one Z stands for C and the other Z stands for N if W in this ligand stands for CR or N or NR;
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 is optionally substituted by one or more radicals R 1 , where one or more non-adjacent CH 2 groups is optionally replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , C═O, NR 1 , O, S or CONR 1 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I or CN, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which optionally in each case be substituted by one or more radicals R 1 , or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more ra

Assignees

• Pan Junyou
• Parham Amir Hossain
• Merck Patent Gmbh

Inventors

• Pan Junyou
• Parham Amir Hossain

Classifications

• C07F15/0033

  Iridium compounds · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• H01L51/5016

  Electricity · mapped topic