Metal complexes

A compound of formula (1):

• [Ir(L)n(L′)m] (1)
• wherein the compound comprises a moiety Ir(L)n of formula (2):
• wherein
• one of the radicals R2 and R3 is a group of formula —(Ar)p-HetAr and the other of the radicals R2 and R3 has the same meaning as defined for R, R1, R4, R5, and R6;
• HetAr is a group of formula (3)
• wherein the dashed bond indicates the bond to Ar or, for p=0, the bond to the pyridine group of the ligand;
• X is on each occurrence, identically or differently, CR or N, with the proviso that at least one and at most three groups X are N;
• Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which are optionally substituted by one or more radicals R;
• p is on each occurrence, identically or differently, 0 or 1;
• Cy is on each occurrence, identically or differently, a group of formula (4), (5), (6), (7), (8), (9), or (10),
• wherein the dashed bonds indicate the linking of the two carbon atoms in the ligand and:
• A1 and A3 are, identically or differently on each occurrence, C(R8)2, O, S, NR8, or C(═O);
• A2 is C(R7)2, O, S, NR8, or C(═O);
• G is an alkylene group having 1, 2, or 3 C atoms, which is optionally substituted by one or more radicals R9, —CR9═CR9—, or an ortho-linked arylene or heteroarylene group having 5 to 14 aromatic ring atoms, which is optionally substituted by one or more radicals R9;
• with the proviso that no two heteroatoms in these groups are bonded directly to one another and no two groups C═O are bonded directly to one another;
• R, R1, R4, R5, R6, R7
• are on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R9)2, CN, Si(R9)3, B(OR9)2, C(═O)R9, 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 R9, wherein one or more non-adjacent CH2 groups are optionally replaced by R9C═CR9, Si(R9)2, C═O, NR9, O, S, or CONR9 and wherein one or more H atoms are optionally replaced by D, F, or CN, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R9, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R9, or a diarylamino group, diheteroarylamino group, or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which are optionally substituted by one or more radicals R9;
• wherein two adjacent radicals R optionally define an aliphatic, aromatic, or heteroaromatic ring system with one another, and wherein the radicals R4 and R optionally define an aliphatic, aromatic, or heteroaromatic ring system with one another;
• and wherein the radicals R3 and R4 optionally define an aliphatic, aromatic, or heteroaromatic ring system with one another if the group R2 is a group of formula —(Ar)p-HetAr;
• R8 is, identically or differently on each occurrence, F, a straight-chain alkyl or alkoxy group having 1 to 10 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, each of which is optionally substituted by one or more radicals R9, wherein one or more non-adjacent CH2 groups are optionally replaced by R9C═CR9, C≡C, Si(R9)2, C═O, NR9, O, S, or CONR9 and wherein one or more H atoms may be replaced by D or F, an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which is optionally substituted by one or more radicals R9, an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms, which is optionally substituted by one or more radicals R9, or an aralkyl or heteroaralkyl group having 5 to 24 aromatic ring atoms, which are optionally substituted by one or more radicals R9;
• and wherein two radicals R8 bonded to the same carbon atom optionally define an aliphatic or aromatic ring system with one another and thus form a spiro system;
• and wherein R8 optionally defines an aliphatic ring system with an adjacent radical R7;
• R9 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 R9 optionally define an aliphatic or aromatic ring system with one another;
• L′ is, identically or differently on each occurrence, a mono- or bidentate ligand;
• n is 1, 2, or 3;
• and
• m is 0, 1, 2, 3, or 4.