Organoboron complexes and their use in organic electroluminescent devices

A formulation comprising at least one compound of the formula (1),

• where the following applies to the symbols and indices used:
• Ar1 is a heteroaryl group comprising at least one nitrogen which is represented in formula (1), having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R1;
• X stands, on each occurrence, identically or differently, for CR2 or N;
• or two adjacent groups X form together a ring condensed on the structure of formula (1), wherein the condensed ring is selected from an aryl or heteroaryl group having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R2;
• ArB is, on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R3;
• W is on each occurrence, identically or differently, CR1 or N;
• or two adjacent groups W stand for a group of formula (W-1) or (W-2),
• where the dashed bonds indicate the bonding to the groups of formula (1);
• Z is on each occurrence, identically or differently, CR1 or N;
• E1, E2 are, on each occurrence, identically or differently, selected from a single bond, B(R0), C(R0)2, Si(R0)2, C═O, C═NR0, C═C(R0)2, O, S, S═O, SO2, N(R0), P(R0) and P(═O)R0, where at least one of the groups E1 and E2, present in the same ring, is not a single bond;
• R0 stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40 C atoms, each of which may be substituted by one or more radicals R4, where in each case one or more non-adjacent CH2 groups may be replaced by R4C═CR4, C≡C, Si(R4)2, Ge(R4)2, Sn(R4)2, C═O, C═S, C═Se, P(═O)(R4), SO, SO2, O, S or CONR4 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R4, or an aryloxy groups having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R4, where two adjacent substituents R0 may form an aliphatic or aromatic ring system together, which may be substituted by one or more radicals R4;
• R1, R2, R3 stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, C(═O)Ar3, P(═O)(Ar3)2, S(═O)Ar3, S(═O)2Ar3, N(Ar3)2, NO2, Si(R4)3, B(OR4)2, OSO2R4, a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40 C atoms, each of which may be substituted by one or more radicals R4, where in each case one or more non-adjacent CH2 groups may be replaced by R4C═CR4, C≡C, Si(R4)2, Ge(R4)2, Sn(R4)2, C═O, C═S, C═Se, P(═O)(R4), SO, SO2, O, S or CONR4 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R4, or an aryloxy groups having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R4;
• where two adjacent substituents R1, two adjacent substituents R2 and/or two adjacent substituents R3 may form an aliphatic or aromatic ring system together, which may be substituted by one or more radicals R4;
• Ar3 is, on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case also be substituted by one or more radicals R4;
• R4 stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl groups having 3 to 20 C atoms, where in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 24 C atoms and at least one solvent.

An electronic device comprising at least one compound of the formula (1),

• where the following applies to the symbols and indices used:
• Ar1 is a heteroaryl group comprising at least one nitrogen which is represented in formula (1), having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R1;
• X stands, on each occurrence, identically or differently, for CR2 or N;
• or two adjacent groups X form together a ring condensed on the structure of formula (1), wherein the condensed ring is selected from an aryl or heteroaryl group having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R2;
• ArB is, on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R3;
• W is on each occurrence, identically or differently, CR1 or N;
• or two adjacent groups W stand for a group of formula (W-1) or (W-2),
• where the dashed bonds indicate the bonding to the groups of formula (1);
• Z is on each occurrence, identically or differently, CR1 or N;
• E1, E2 are, on each occurrence, identically or differently, selected from a single bond, B(R0), C(R0)2, Si(R0)2, C═O, C═NR0, C═C(R0)2, O, S, S═O, SO2, N(R0), P(R0) and P(═O)R0, where at least one of the groups E1 and E2, present in the same ring, is not a single bond;
• R0 stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40 C atoms, each of which may be substituted by one or more radicals R4, where in each case one or more non-adjacent CH2 groups may be replaced by R4C═CR4, C≡C, Si(R4)2, Ge(R4)2, Sn(R4)2, C═O, C═S, C═Se, P(═O)(R4), SO, SO2, O, S or CONR4 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R4, or an aryloxy groups having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R4, where two adjacent substituents R0 may form an aliphatic or aromatic ring system together, which may be substituted by one or more radicals R4;
• R1, R2, R3 stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, C(═O)Ar3, P(═O)(Ar3)2, S(═O)Ar3, S(═O)2Ar3, N(Ar3)2, NO2, Si(R4)3, B(OR4)2, OSO2R4, a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40 C atoms, each of which may be substituted by one or more radicals R4, where in each case one or more non-adjacent CH2 groups may be replaced by R4C═CR4, C≡C, Si(R4)2, Ge(R4)2, Sn(R4)2, C═O, C═S, C═Se, P(═O)(R4), SO, SO2, O, S or CONR4 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R4, or an aryloxy groups having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R4;
• where two adjacent substituents R1, two adjacent substituents R2 and/or two adjacent substituents R3 may form an aliphatic or aromatic ring system together, which may be substituted by one or more radicals R4;
• Ar3 is, on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case also be substituted by one or more radicals R4;
• R4 stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl groups having 3 to 20 C atoms, where in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 24 C atoms.