Phosphorus-containing metal complexes

1. A compound of the formula (1)

M(L) n (L′) m   formula (1)

where the compound contains a moiety M(L) n is selected from the formulae (36) to (59)

wherein

X is CR 1 ;

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 , 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 or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylakoxy 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 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 is substituted by one or more radicals R 2 , or an aryloxy, arylalkoxy, alkylaryloxy 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 aryiheteroarylamino 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;

M is iridium or platinum;

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

W is, identically or differently on each occurrence, a radical of the formulae (3) and (4)

where V is equal to S or O;

R 4 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R 2 ) 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, alkylalkoxy 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 is substituted by one or more radicals R 2 , or an aryloxy, arylalkoxy, alkylaryloxy 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 4 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, alkylalkoxy 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 , C≡C, 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 is substituted by one or more radicals R 3 , or an aryloxy, arylalkoxy, alkylaryloxy 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 optionally also forms a mono- or polycyclic, aliphatic or aromatic ring system with one another;

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

m is 0, 1, 2 for M equal to iridium and is 0 or 1 for M equal to platinum;

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.

2. The compound according to claim 1 , wherein the moiety M(L) n is selected from the formulae (36), (40), (44), (48), (52), and (56).

3. The compound according to claim 1 , wherein the radical W is given by the formulae (110) to (115)

where

R 5 is, identically or differently on each occurrence, H, D, a straight-chain alkyl 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 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 is 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 optionally also forms a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one another.

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

5. The compound according to claim 1 , wherein m=0.

6. 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 (344), with metal ketoketonates of the formula (345) or with metal halides of the formula (346)

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

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