Metal complexes with organic ligands and use thereof in OLEDs

1. A compound of the formula (1)

M(L) n (L′) m   formula 1

where the compound contains a moiety M(L) n of the formulae (11) to (13)

where M is bonded to any desired bidentate ligand L via a nitrogen atom N and via a carbon atom C and

where the following applies to the symbols and indices used:

M is a metal selected from the group consisting of iridium, rhodium, platinum and palladium;

L′ is, identically or differently on each occurrence, a co-ligand;

W is equal to the formula (3)

where T is selected, identically or differently on each occurrence, from the group consisting of —C(R 1 ) 2 , —Si(R 1 ) 2 , N, —NR 1 , —O, —S, —C(═O), —S(═O), —SO 2 , —CF 2 , —SF 4 , —P, —P(═O)R 1 , —PF 2 , —P(═S)R 1 , —As, —As(═O), —As(═S), —Sb, —Ge, —Si, —Sb(═O), —C(R 1 ) 2 —C(R 1 ) 2 —, and —Sb(═S);

Q is R 1 C═CR 1 ;

Q′ is, identically or differently on each occurrence, R 1 C═CR 1 , R 1 C═N, O, S, Se or NR 1 ;

X is CR 1 ;

p is 0 or 1, where, for p=0, the central ring in formula (3) forms a five-membered ring;

n is 1, 2 or 3 for M equal to iridium or rhodium and is 1 or 2 for M equal to platinum or palladium;

m is 0, 1, 2, 3 or 4;

R 1 is, identically or differently on each occurrence, 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 , B(═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 or 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 , where one or more non-adjacent CH 2 groups is 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 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 optionally in each case be substituted by one or more radicals R 2 , or 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 optionally substituted by one or more radicals R 2 , or a combination of two or more of these groups; two or more radicals R 1 here may also form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one another;

R 2 is, identically or differently on each occurrence, 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 40 C atoms or 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 3 , where one or more non-adjacent CH 2 groups is optionally replaced by R 3 C═CR 3 , Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , O, S or CONR 3 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 optionally in each case be substituted by one or more radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is 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, which is optionally substituted by one or more radicals R 3 , or a combination of two or more of these groups; two or more adjacent radicals R 2 here may form a mono- or polycyclic, aliphatic or aromatic ring system with one another;

R 3 is, identically or differently on each occurrence, 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 3 here may also four a mono- or polycyclic, aliphatic or aromatic ring system with one another;

the indices n and m here are selected so that the coordination number on the metal corresponds to 6 for M equal to iridium or rhodium and corresponds to 4 for M equal to platinum or palladium;

a plurality of ligands L here may also be linked to one another or L is optionally linked to L′ via any desired bridge Z and thus form a tridentate, tetradentate, pentadentate or hexadentate ligand system.

2. The compound according to claim 1 , wherein the moiety M(L) n is selected from the formula (17) to (19)

3. The compound according to claim 1 , wherein the moiety M(L) n is selected from the formulae (23) to (25)

4. The compound according to claim 1 , wherein m is 1, 2, 3, or 4.

5. The compound according to claim 1 , wherein m=0 and M(L) n is selected from the formulae (29) to (31)

6. The compound according to claim 1 , wherein the radical W is given by the formulae (47) to (55)

where the line indicates the position at which the bonding of the radical W to the ligand takes place and where the symbols used correspond to the symbols defined in claim 1 .

7. The compound according to claim 1 , wherein moiety M(L) n is selected from the formulae (71) to (85)

8. The compound according to claim 1 , wherein R 1 , identically or differently on each occurrence, —H, —NH 2 or a radical of the formulae (86) to (224) where the radicals may also be mono- or polysubstituted by a radical R 3 , which, if they occur more than once, is optionally identical or independent of one another,

9. The compound according to claim 1 , wherein M is equal to iridium.

10. The compound according to claim 1 , wherein Q′ is R 1 C═CR 1 .

11. A formulation comprising at least one compound according to claim 1 and at least one solvent.

12. A process for the preparation of the compound according to claim 1 which comprises reacting the corresponding free ligands with metal alkoxides of the formula (282), with metal ketoketonates of the formula (283) or with metal halides of the formula (284)

where the symbols M, n and R 1 have the meanings indicated above and Hal=F, Cl, Br or I.