Materials for organic electroluminescence devices

An electronic device, selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, light-emitting electrochemical cells, organic laser diodes, OLED sensors, gas and vapour sensors which are not hermetically screened from the outside, and organic plasmon emitting devices, comprising one or more of the compounds of the formula (I), (II), (III), (IV) or (VII):

• where * denotes the atom which forms the complex bond and # denotes the atom which is bonded to the second unit via B or B″,
• Z2-Z9 are on each occurrence, identically or differently, N or CR;
• L is, independently of one another, a monodentate phosphine or arsine ligand R3E (where E=P or As), where one ligand L or both ligands L may also be bonded to A-(B)—B, giving rise to a tetravalent ligand, or, if L is bound to B′ or B′″, is a bidentate ligand of formula R2E (where E=P or As);
• L-B′-L is a phosphanyl or arsanyl radical, which is bonded to a further radical L via a bridge B′ and thus forms a bidentate ligand;
• R is on each occurrence selected, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(R1)2, C(═O)R1, Si(R1)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which may be substituted by one or more radicals R1, where one or more non-adjacent CH2 groups may be replaced by R1C═CR1, C≡C, Si(R1)2, Ge(R1)2, Sn(R1)2, C═O, C═S, C═Se, C═NR1, P(═O)(R1), SO, SO2, NR1, O, S or CONR1 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R1, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R1, or a combination of these systems, where two or more adjacent substituents R may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more radicals R1;
• R1 is on each occurrence selected, identically or differently, from the group consisting of H, D, F CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D, F, Cl, Br, I or CN, where two or more adjacent substituents R3 may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
• Y is on each occurrence, identically or differently, O, S or NR;
• (B) is R2B, where R has the meaning given above;
• B′ is an alkylene or arylene group or a combination of the two, or —O—, —NR— or —SiR2—;
• B″ is a neutral bridge, and is on each occurrence, identically or differently, a divalent bridge selected from NR, BR, O, CR2, SiR2, C═NR, C═CR2, S, S═O, SO2, PR and P(═O)R;
• and
• B′″ is a mononegatively charged bridge.

A compound of the formula VII:

• where
• L is a monodentate phosphine or arsine ligand R2E (where E=P or As);
• and where the nitrogen ligands have the following formulae:
• where Z2-Z9 are on each occurrence, identically or differently, N or CR,
• where * denotes the atom which forms the complex bond and # denotes the atom which is bonded to the second unit via B and the following applies to the other symbols used:
• R is on each occurrence selected, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(R1)2, C(═O)R1, Si(R1)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which may be substituted by one or more radicals R1, where one or more non-adjacent CH2 groups may be replaced by R1C═CR1, C≡C, Si(R1)2, Ge(R1)2, Sn(R1)2, C═O, C═S, C═Se, C═NR1, P(═O)(R1), SO, SO2, NR1, O, S or CONR1 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R1, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R1, or a combination of these systems, where two or more adjacent substituents R may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more radicals R1;
• R1 is on each occurrence selected, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D, F, Cl, Br, I or CN, where two or more adjacent substituents R3 may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
• Y is on each occurrence, identically or differently, O, S or NR;
• B″ is a neutral bridge, and is on each occurrence, identically or differently, a divalent bridge selected from NR, BR, O, CR2, SiR2, C═NR, C═CR2, S, S═O, SO2, PR and P(═O)R;
• and
• B″′ is a mononegatively charged bridge.

A compound of the formula VIII:

• where
• L is a monodentate phosphine or arsine ligand R2E (where E=P or As);
• and where the nitrogen ligands have the following formulae:
• where Z2-Z9 are on each occurrence, identically or differently, N or CR,
• where * denotes the atom which forms the complex bond and # denotes the atom which is bonded to the second unit and the following applies to the other symbols used:
• R is on each occurrence selected, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(R1)2, C(═O)R1, Si(R1)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which may be substituted by one or more radicals R1, where one or more non-adjacent CH2 groups may he replaced by R1C═CR1, C≡C, Si(R1)2, Ge(R1)2 , Sn(R1)2, C═O, C═S, C═Se, C═NR1, P(═O)(R1), SO, SO2, NR1, O, S or CONR1 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R1, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R1, or a combination of these systems, where two or more adjacent substituents R may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which may he substituted by one or more radicals R1;
• R1 is on each occurrence selected, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D, F, Cl, Br, I or CN, where two or more adjacent substituents R3 may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
• Y is on each occurrence, identically or differently, O, S or NR;
• and
• B″′ is R2B(CH2)2 or carborane.

An electronic device, selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, light-emitting electrochemical cells, organic laser diodes, OLED sensors, gas and vapour sensors which are not hermetically screened from the outside, and organic plasmon emitting devices, comprising one or more of the compounds of the formula (V) or (VIII):

• where * denotes the atom which forms the complex bond and # denotes the atom which is bonded to the second unit,
• Z2-Z9 are on each occurrence, identically or differently, N or CR;
• L is, independently of one another, a monodentate phosphine or arsine ligand R3E (where E=P or As), or when L is bound to B′″, forming a bidentate L-B′″-L ligand, L is independently of one another R2E where E=P or As;
• R is on each occurrence selected, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(R1)2, C(═O)R1, Si(R1)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which may be substituted by one or more radicals R1, where one or more non-adjacent CH2 groups may be replaced by R1C═CR1, C≡C, Si(R1)2, Ge(R1)2, Sn(1)2, C═O, C═S, C═Se, C═NR1, P(═O)(R1), SO, SO2, NR1, O, S or CONR1 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R1, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R1, or a combination of these systems, where two or more adjacent substituents R may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more radicals R1;
• R1 is on each occurrence selected, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D, F, Cl, Br, I or CN, where two or more adjacent substituents R3 may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
• Y is on each occurrence, identically or differently, O, S or NR;
• B′″ is a mononegatively charged bridge.