Phosphorus-containing metal complexes

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 CR1;
• R1 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R2)2, CN, NO2, Si(R2)3, B(OR2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, S(═O)2R2, OSO2R2, 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 R2, where one or more non-adjacent CH2 groups is optionally replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, P(═O)(R2), SO2, NR2, O, S or CONR2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, 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 R2, or an aryloxy, arylalkoxy, alkylaryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, 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 R2, or a combination of two or more of these groups;
• two or more radicals R1 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;
• R4 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R2)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 R2, where one or more non-adjacent CH2 groups is optionally replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, 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 R2, or an aryloxy, arylalkoxy, alkylaryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, 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 R2, or a combination of two or more of these groups;
• two or more radicals R4 here may also form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one another;
• R2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R3)2, CN, NO2, Si(R3)3, B(OR3)2, C(═O)R3, P(═O)(R3)2, S(═O)R3, S(═O)2R3, OSO2R3, 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 R3, where one or more non-adjacent CH2 groups is optionally replaced by R3C═CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, P(═O)(R3), SO, SO2, NR3, O, S or CONR3 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, 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 R3, or an aryloxy, arylalkoxy, alkylaryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R3, 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 R3, or a combination of two or more of these groups;
• two or more adjacent radicals R2 here may form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
• R3 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 R3 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.