Cerium-ethylenediamineketone and cerium-salen-type compounds and their use in organic electronics

Description

[0001] The present invention relates to an electronically doped semiconductor material and an electronic component comprising cerium-ethylenediamine ketone-type and cerium-salen-type complexes. The invention further relates to the use of the cerium-ethylenediamine ketone-type and cerium-salen-type complexes as electron acceptors, especially as p-dopants and electron-transport materials in organic electronic components. The invention further relates to novel cerium-ethylenediamine ketone-type and cerium-salen-type complexes. BACKGROUND OF THE INVENTION

[0002] Organic electronics deals with the development, characterization, and application of new materials, both based on small organic molecules and polymers, with specific desired electronic properties for the production of electronic components. These include, for example, organic field-effect transistors (OFETs), such as organic thin-film transistors (OTFTs); organic electroluminescent devices, such as organic light-emitting diodes (OLEDs); organic solar cells (OSCs), such as exciton solar cells, dye-sensitized solar cells (DSSCs), or perovskite solar cells; electrophotography, such as photoconductive materials in organic photoconductors (OPCs); organic optical detectors, organic photoreceptors, light-emitting electrochemical cells (LECs), and organic laser diodes.

[0003] It is known that the electrical conductivity of organic semiconductor matrices can be significantly influenced by doping. Such organic semiconductor matrix materials can be constructed either from compounds with electron-donating properties (p-type conductors) or from compounds with electron-accepting properties (n-type conductors). Unlike inorganic semiconductors, organic semiconductors have only a very low intrinsic charge carrier concentration. To achieve good semiconductor properties, organic semiconductor matrix materials are therefore usually doped. Strong electron donors (n-type dopants) are used for n-type doping, which transfer an electron to the LUMO of the semiconductor matrix (n-type doping), thereby creating a free electron on the matrix (SOMO).For p-type doping, strong electron acceptors (p-dopants) are used, which remove an electron from the HOMO of the semiconductor matrix (p-doping), leaving a hole. In other words, with p-doping, the LUMO of the dopant must be below the HOMO energy of the matrix. The dopant acts as an acceptor, leaving a mobile hole (SOMO) in the matrix.

[0004] Known p-dopants for electron donor materials are electron acceptors such as tetracyanoquinonemethane (TCNQ), 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonemethane (F4TCNQ), trinaphthylenes (HATNA), metal oxides such as MoOs or WO 3 , or radialenes, as described in EP 2180029. The acceptor molecules generate so-called holes (hole transport materials) in the semiconductor matrix materials through electron transfer processes, and the conductivity of the semiconductor matrix material (hole transport material) is changed to a greater or lesser extent depending on the number and mobility of the holes.

[0005] However, the compounds or classes of compounds described above have disadvantages for technical use in the production of doped semiconductors or corresponding electronic components with such doped layers. For example, these compounds or classes of compounds are too volatile, have too high an absorption coefficient, exhibit an unstable evaporation rate, and / or exhibit low thermal stability. In addition, some of these substance classes have very high production costs.

[0006] There is therefore still a great need for compounds that are readily available or producible, suitable for doping electron donor materials and do not have the disadvantages described above.

[0007] Only a few cerium-ethylenediamine ketone-like complexes and no cerium-salen-like (cerium-bis(salicylidene)ethylenediamine-like) complexes are known. Thus, a few complexes of cerium(IV) have been described in the literature. J. Schläfer et al., Inorg. Chem., 2016, 55, 5422-5429 describes homopleptic cerium(IV) complexes containing the following ligands: N,N'-bis(4,4,4,-trifluorobut-1-en-3-one)ethylenediamine, N,N'-bis(4,4,5,5,5-pentafluoropent-1-en-3-one)ethylenediamine, N,N'-bis(4,4,5,5,6,6,6-heptafluorohex-1-en-3-one)ethylenediamine and N,N'-bis(4,4,4,-trifluorobut-1-en-3-one)propylenediamine.

[0008] SCHLÄFER J. ET AL: "Fluorinated Cerium(IV) Enaminolates: Alternative Precursors for Chemical Vapor Deposition of CeO 2 Thin Films",INORGANIC CHEMISTRY,Vol. 55, No. 11, 6 June 2016 (2016-06-06), pages 5422-5429 discloses cerium(IV) complexes.

[0009] WO00 / 32719 (A1) discloses an electronic component comprising a cerium (IV) compound.

[0010] In DW Wester et al.: "Electrochemical studies of cerium chelate complexes", Inorg. Chem. 1985, 24, 4435-4437, the following homopleptic cerium(IV) complexes are described:

[0011] NK Dutt et al. (Chemistry of Lanthanons - XIX Ethylenediamine bis-Acetylacetone Complexes of Rare-Earths, J. Inorg. Nucl. Chem., 1968, Vol. 30, pp. 3273-3280) describe the synthesis of ethylenediamine bis-acetylacetone complexes of rare earths. Among them are Ce(III) complexes, [Ce(ethylenediamine bis-acetylacetone))Cl 3 ] and [Ce(ethylenediamine bis-acetylacetone))NO 3 ]. In these complexes, the ligand is neutral and thus carries no charge. According to the invention, the ligand is doubly negatively charged.

[0012] V. Balasubramanian et al. (Synthesis and Reactivity of Quadridentate Schiff Base Chelates of Lanthanide(III) Ions, Asian Journal of Chemistry 2003, Vol. 15, No. 1, pp. 139-143) describe the synthesis of lanthanide(III) chelate complexes. Among them are Ce(III) complexes, [Ce(ethylenediamine-bis-acytylacetone)Cl 3 ] and [Ce(ethylenediamine-bis-acytylacetone-α-naphthylisocyanate))Cl 3 ], in which the ethylenediamine-bis-acytylacetone ligand is present in the keto form. In these complexes, the ligand is neutral and thus carries no charge. According to the invention, the ligand is doubly negatively charged.

[0013] JH Timmons (Template Synthesis and Crystal and Molecular Structure of Bis[1,1,1,12,12,12-hexafluoro-2, 11-bis(trifluoromethyl)-4,9-dimethyl-2,11-diolato-5,8-diazadodeca-4,8-diene(2-)]cerium(IV), CeC28H28F24O4N4, a fluorinated Schiff base complex of eight-coordinate Cerium (IV), Inorganic Chemistry 1980, Vol. 19, No. 12, pp. 3553-3557) describes a cerium(IV) complex. The ligand of this complex exhibits a different connectivity of the atoms. In other words, the ligand is not based on an acetylacetone structure.

[0014] WO 2021 / 048044 describes cerium(IV) diketonate complexes as electron acceptors, especially as p-dopants and electron transport materials in organic electronic components.

[0015] Until now, the use of cerium(IV)-ethylenediamineketone-type and / or cerium(IV)-salen-type and / or (cerium(IV)-bis(salicylidene)ethylenediamine-type) complexes (hereinafter referred to as cerium(IV) complexes) in organic semiconductor materials was unknown. In particular, the use of such cerium(IV) complexes as p-dopants, as electron-transport materials, or as electron acceptors has not yet been described.

[0016] Surprisingly, it has now been discovered that such cerium(IV) complexes are excellent candidates for use as p-dopants. Furthermore, such cerium(IV) complexes have been found to be suitable for use as electron transport materials (ETMs) in organic electronic components, such as organic light-emitting diodes (OLEDs), photovoltaic cells, organic solar cells (OPVs), organic diodes, or organic transistors.

[0017] Furthermore, many of these cerium(IV) complexes can be easily evaporated in a vacuum and sometimes exhibit high thermal stability. Thus, they are fundamentally suitable for both processing methods for organic electronic components: vacuum deposition (vapor deposition) and solvent-based processing (solution processing). SUMMARY OF THE INVENTION

[0018] A first subject of the invention is an electronic component comprising at least one compound of the general formula (I) Ce 4+< [L 1 L 2 ] 4-< (I), where L 1 and L 2 are each a tetradentate ligand, which are independently selected from ligands of the formula (I.1) where X independently represents O or S; Z represents a bridging group which has 2 or 3 carbon atoms between the nitrogen atoms, where the carbon atoms are each unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R 12<, where two adjacent carbon atoms can also be connected to one another by a double bond, or 2 or 3 of the carbon atoms are part of a mononuclear, dinuclear or trinuclear aromatic or heteroaromatic C 6 -C 14 ring system, where the heteroaromatic ring system has 4 to 13 carbon atoms and has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members which are selected from N, NR 8< , O, S, SO and SO 2 and where the aromatic or heteroaromatic ring system is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different residues R 9< is substituted;A and B independently represent N or CR 7<; R 1< and R 6< are independently selected from hydrogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 7 -cycloalkyl, where C 3 -C 7 -cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R 11<, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 -aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<;or R 1< and A, together with the carbon atom to which they are attached, form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<, or R 6< and B, together with the carbon atom to which they are attached, form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, or 4 identical or different radicals R 9<;R 2< and R 5< are independently selected from hydrogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 7 -cycloalkyl, where C 3 -C 7 -cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R 11<, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 -aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<;R 2< and A, together with the carbon atom to which they are bonded, form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<, or R 5< and B, together with the carbon atom to which they are bonded, form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<;R 4a< R 4b< are independently selected from hydrogen, C 1 -C 6 alkyl and C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<; R 7< is selected from hydrogen, CN, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<;R 8< is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl and C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<; R 9< is selected from CN, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl and C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; R 10< is selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl; R 11< is selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl;R 12< are independently selected from halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R 11<, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<. ;

[0019] A further subject of the invention is an electronic component comprising at least one compound of the general formula (I) Ce 4+< [L 1 L 2 ] 4-< (I), where L 1 and L 2 are each a tetradentate ligand, which are independently selected from ligands of the formula (II) where - - - - - -between the group CR 3< -CR 4< stands for a single or double bond, X independently of one another stands for O or S; A and B independently of one another stand for N or CR 7<; R 1< and R 6< are independently selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<, or R 1< and A together with the carbon atom to which they are attached, form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl is 1,has 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<, or R 6< and B together with the carbon atom to which they are bonded form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 3< and R 4< are independently selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< ,C 6 -C 14 -aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<, or R 3< and R 4< together with the carbons to which they are attached form a C 6 -C 14 -aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or are substituted by 1, 2, 3, or 4 identical or different radicals R 9<; R 2< and R 5< are independently selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy,C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 -aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<; R 4a< R 4b< are independently selected from hydrogen, C 1 -C 6 alkyl and C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<; R 7< is selected from hydrogen, CN, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1,has 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<; R 8< is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl and C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<; R 9< is selected from CN, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl and C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; R 10< is selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl. ,

[0020] The invention further relates to a doped semiconductor matrix material comprising at least one electron donor and at least one compound of formula (I), wherein L 1 and L 2 are each a tetradentate ligand which are independently selected from ligands of formula (1.1) or formula (II), wherein the radicals X, Z, A, B, R 1< , R 2< , R 3< , R 4< , R 5< and R 6< have the meanings defined above and as follows.

[0021] A further object of the invention is the use of a compound (I), wherein L 1 and L 2 are each a tetradentate ligand, which are independently selected from ligands of the formula (1.1) or formula (II), wherein the radicals X, Z, A, B, R 1< , R 2< , R 3< , R 4< , R 5< and R 6< have the meanings defined above and as follows, as an organic semiconductor, as a dopant in organic semiconductor matrix materials, in particular as a p-dopant in hole transport layers, as a charge injector in a charge injection layer, as an electron transport layer, as a cathode material in organic batteries, as an electrochromic material, as an electron acceptor.

[0022] A further object of the invention is the use of Ce(III) complex anions obtained by reduction of a compound (I), as defined above and below, or of charge transfer complexes of a compound (I), as defined above and below, with electron donors, as an organic conductor, in particular as an organic conductor, as an electrochromic material, as a charge-transfer complex or as a ferromagnet.

[0023] The invention further relates to compounds of the general formula (I) Ce 4+< [L 1 L 2 ] 4-< (I), their charge transfer complexes, their reduction products, and mixtures thereof, where L 1 and L 2 are each a tetradentate ligand, which are independently selected from ligands of the formula (I.1) where X independently of one another represents O or S; Z represents a bridging group which has 2 or 3 carbon atoms between the nitrogen atoms, where the carbon atoms are each unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R 12<, where two adjacent carbon atoms may also be connected to one another by a double bond, or 2 or 3 of the carbon atoms are part of a mononuclear, dinuclear or trinuclear aromatic or heteroaromatic C 6 -C 14 ring system, where the heteroaromatic ring system has 4 to 13 carbon atoms and has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members which are selected from N, NR 8<, O, S, SO and SO 2 and where the aromatic or heteroaromatic ring system is unsubstituted or substituted by 1, 2, 3,4 or 5 identical or different radicals R 9<; A and B independently of one another represent N or CR 7<; R 1< and R 6< are independently selected from hydrogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 7 -cycloalkyl, where C 3 -C 7 -cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R 11<, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 -aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<, or R 1< and Ag together with the carbon atom to which they are attached,form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<, or R 6< and B together with the carbon atom to which they are bonded form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or are substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 2< and R 5< are independently selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy,C 3 -C 7 -cycloalkyl, where C 3 -C 7 -cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R 11<, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 -aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<; R 2< and A together with the carbon atom to which they are bonded form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2,3 or 4 identical or different radicals R 9< are substituted, or R 5< and B together with the carbon atom to which they are bonded form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 4a< R 4b< are independently selected from hydrogen, C 1 -C 6 alkyl and C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<; R 7< is selected from hydrogen, CN, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< ,C 6 -C 14 -aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<; R 8< is selected from hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 6 -C 14 -aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<; , R 9< is selected from CN, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl and C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; R 10< is selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl; R 11< is selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl;R 12< are independently selected from halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R 11<, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<; ; The following compounds and their reduction products are excluded:

[0024] The invention further relates to compounds of the general formula (I) Ce 4+< [L 1 L 2 ] 4-< (I), their charge transfer complexes, their reduction products, and mixtures thereof, where L 1 and L 2 are each a tetradentate ligand, which are independently selected from ligands of the formula (II) where - - - - - -between the group CR 3< -CR 4< stands for a single or double bond, X independently of one another stands for O or S; A and B independently of one another stand for N or CR 7<; R 1< and R 6< are independently selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<, or R 1< and A together with the carbon atom to which they are attached, form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl is 1,has 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<, or R 6< and B together with the carbon atom to which they are bonded form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 3< and R 4< are independently selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< ,C 6 -C 14 -aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<, or R 3< and R 4< together with the carbons to which they are attached form a C 6 -C 14 -aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or are substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 2< and R 5< are independently selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy,C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 -aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<; , R 4a< R 4b< are independently selected from hydrogen, C 1 -C 6 alkyl and C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<; R 7< is selected from hydrogen, CN, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<;R 8< is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl and C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<; R 9< is selected from CN, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl and C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals selected from C 1 -C 4 alkyl and C 1 -C 4 haloalkyl; R 10< is selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl;

[0025] the following compounds and their reduction products of formula (I) being excluded, wherein L 1 = L 2 = N,N'-bis(4,4,4,-trifluorobut-1-en-3-one)-ethylenediamine, L 1 = L 2 = N,N'-bis(4,4,5,5,5-pentafluoropent-1-en-3-one)-ethylenediamine, L 1 = L 2 = N,N'-bis(4,4,5,5,6,6,6-heptafluorohex-1-en-3-one)-ethylenediamine and the following compounds and their reduction products

[0026] The invention has the following advantages: The cerium(IV) complexes according to the invention have low production costs. The cerium(IV) complexes according to the invention are advantageously suitable as electron acceptors for use as p-dopants and as electron-transport materials in organic electronic components. The cerium(IV) complexes according to the invention exhibit better conductivity than known electron acceptors. The cerium(IV) complexes according to the invention exhibit improved thermal stability of the doped layers compared to the prior art. Furthermore, the cerium(IV) complexes according to the invention are characterized by higher doping efficiency. The cerium(IV) complexes according to the invention exhibit only low absorption of the doped layer. Thus, parasitic absorptions and emissions can be reduced or even prevented.The cerium(IV) complexes according to the invention are suitable for the production of organic and hybrid optoelectronic components, both by solvent processing and by vacuum processing.

[0027] The terms cerium compound and cerium complex are used synonymously and are defined by formula (I). The ligands in the absence of the metal atom (cerium atom) are defined by formula (II).

[0028] The term reduction products of a compound (I) refers to anion complexes, especially Ce(III) anion complexes, where the corresponding counterion is donated by the hole-transporting material (HTL) of the matrix. Semiconductor matrix materials are defined below.

[0029] For the purposes of the invention, [Ce(ac 2 en)Cl 3 ], [Ce(enac) 2 Cl 3 ] and [Ce(enac) 2 (NO 3 ) 3 ] are not reduction products of the compound (I), where ac 2 en and enac have the same meanings and in particular ac 2 en stands for bis(acetylacetone)ethylenediamine in the keto form and enac stands for ethylenediamine-bis-acetylacetone.

[0030] The term charge transfer complexes of a compound (I) refers to its ionic pairings with the radical cations of the matrix material (hole transport material, HTL).

[0031] In the context of the invention, formula (II) represents an exemplary mesomeric boundary structure to which the ligands L 1 and L 2 are not restricted. Further mesomeric boundary structures are selected from the formula a, b, c and d

[0032] The mesomeric limit structures a, b, c and d also apply analogously to the ligands of formula (I.1).

[0033] Preferably, L 1 and L 2 have the mesomeric limit structure of formula a.

[0034] In the context of the invention, a tetradentate ligand (also called tetradentate) is a ligand that binds to the metal atom (cerium atom) with four atoms.

[0035] In the context of the invention, a homoleptic cerium(IV) compound is a complex in which all ligands are identical (L 1 = L 2 ).

[0036] In the context of the invention, a heteroleptic cerium(IV) compound is a complex where one ligand has a different meaning than the other ligand (L 1 ≠ L 2 ).

[0037] In the context of the invention, the prefix C n -C m indicates the number of carbon atoms that a molecule or radical designated thereby may have.

[0038] In the context of the present invention, the term "C 1 -C 6 alkyl" stands for unbranched and branched saturated hydrocarbon radicals having 1 to 6 carbon atoms. Examples of C 1 -C 6 alkyl are methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-Dimethylpropyl, 1-Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, 1,1-Dimethylbutyl, 1,2-Dimethylbutyl, 1,3-Dimethylbutyl, 2,2-Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1-Ethylbutyl, 2-Ethylbutyl, 1,1,2-Trimethylpropyl, 1,2,2-Trimethylpropyl, 1-Ethyl-1-methylpropyl or 1-Ethyl-2-methylpropyl. C1-C4-Alkyl means, for example, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, or 1,1-dimethylethyl.

[0039] In the context of the present invention, the term "C 1 -C 6 -alkoxy" stands for an unbranched or branched saturated C 1 -C 6 -alkyl group, as defined above, which is bonded via an oxygen atom. Preference is given to alkoxy radicals having 1 to 4 carbon atoms, particularly preferably having 1 or 2 carbon atoms. C 1 -C 2 -alkoxy is methoxy or ethoxy. C 1 -C 4 -alkoxy is, for example, methoxy, ethoxy, n-propoxy, 1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy). C 1 -C 6 -alkoxy includes the meanings given for C 1 -C 4 -alkoxy and additionally, for example, B. Pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-Dimethylbutoxy, 1,3-Dimethylbutoxy, 2,2-Dimethylbutoxy, 2,3-Dimethylbutoxy and 3,3-Dimethylbutoxy.

[0040] In the context of the present invention, the term "C 1 -C 6 -alkylsulfanyl" stands for a straight-chain or branched saturated C 1 -C 6 -alkyl group, as defined above, which is bonded via a sulfur atom. Alkylsulfanyl radicals having 1 to 4 carbon atoms are preferred, particularly preferably having 1 or 2 carbon atoms. C 1 -C 2 -alkylsulfanyl is methylsulfanyl or ethylsulfanyl. C 1 -C 4 alkylsulfanyl is, for example, methylsulfanyl, ethylsulfanyl, n-propylsulfanyl, 1-methylethylsulfanyl (isopropylsulfanyl), butylsulfanyl, 1-methylpropylsulfanyl (sec-butylsulfanyl), 2-methylpropylsulfanyl (isobutylsulfanyl) or 1,1-Dimethylethylsulfanyl (tert-butylsulfanyl).C 1 -C 6 -Alkylthio beinhaltet die für C 1 -C 4 -Alkylsulfanyl angegebenen Bedeutungen und zusätzlich beispielsweise auch Pentylsulfanyl, 1-Methylbutylsulfanyl, 2-Methylbutylsulfanyl, 3-Methylbutylsulfanyl, 1,1-Dimethylpropylsulfanyl, 1,2-Dimethylpropylsulfanyl, 2,2-Dimethylpropylsulfanyl, 1-Ethylpropylsulfanyl, Hexylsulfanyl, 1-Methylpentylsulfanyl, 2-Methylpentylsulfanyl, 3-Methylpentylsulfanyl, 4-Methylpentylsulfanyl, 1,1-Dimethylbutylsulfanyl, 1,2-Dimethylbutylsulfanyl, 1,3-Dimethylbutylsulfanyl, 2,2-Dimethylbutylsulfanyl, 2,3-Dimethylbutylsulfanyl, 3,3-Dimethylbutylsulfanyl, 1-Ethylbutylsulfanyl, 2-Ethylbutylsulfanyl, 1,1,2-Trimethylpropylsulfanyl, 1,2,2-Trimethylpropylsulfanyl, 1-Ethyl-1-methylpropylsulfanyl oder 1-Ethyl-2-methylpropylsulfanyl.

[0041] For the purposes of the invention, the terms haloalkyl, haloalkoxy, and haloalkylsulfanyl represent partially or fully halogenated alkyl, alkoxy, or alkylsulfanyl. In other words, one or more hydrogen atoms, e.g., 1, 2, 3, 4, or 5, bonded to one or more carbon atoms of alkyl, alkoxy, or alkylsulfanyl, are replaced by a halogen atom, in particular by fluorine or chlorine.

[0042] In the context of the invention, the term "cycloalkyl" stands for carbocyclic, monocyclic radicals having 3 to 7 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl; preferred are cyclopentyl, cyclohexyl, and cycloheptyl, whereby the bond to the remainder of the molecule can be via any suitable C atom. In the case of substitution, these can generally bear 1, 2, 3, 4, 5, or 6, preferably 1, 2, or 3, and particularly preferably 1, "substituent" as defined above.

[0043] In the context of the invention, the term "alkylene" refers to alkanediyl groups, ie hydrocarbon bridging groups having 2 or 3 carbon atoms, such as -(CH 2 ) 2 -, -(CH 2 ) 3 -, -CH 2 -CH-CH 2 -. In the case of substitution, these can generally bear 1, 2 or 3 substituents R 12< as defined above.

[0044] In the context of the invention, the term "alkenylene" stands for the mono- or polyunsaturated, in particular monounsaturated, analogues of alkylene groups having 2 or 3 carbon atoms, such as -CH=CH-, -CH=CH-CH 2 -, -CH 2 -CH=CH-. In the case of substitution, these can generally bear 1, 2, or 3 substituents R 12< as defined above.

[0045] In the context of the invention, the expression "part of a mononuclear, dinuclear or trinuclear aromatic or heteroaromatic C 6 -C 14 ring system" corresponds to the corresponding doubly or multiply linked analogues of the aryls or hetaryls.

[0046] In the context of the invention, the expression "bridging group having 2 or 3 carbon atoms between the nitrogen atoms" means that 2 or 3 carbon atoms are located in a direct line between the flanking bonds (nitrogen atoms).

[0047] For the purposes of the invention, halogen means fluorine, chlorine, bromine and iodine.

[0048] In the context of the present invention, the term "aryl" encompasses mono- or polynuclear aromatic hydrocarbon radicals having typically 6 to 14, particularly preferably 6 to 10, carbon atoms. Examples of aryl are, in particular, phenyl, naphthyl, indenyl, fluorenyl, anthracenyl, phenanthrenyl, naphthacenyl, chrysenyl, pyrenyl, etc., and especially phenyl or naphthyl.

[0049] The term "hetaryl" in the context of the present invention encompasses mono- or polynuclear aromatic hydrocarbon radicals having 4 to 13 carbon atoms, where 1, 2, or 3 carbon atoms have been replaced by 1, 2, or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, where the heteroatoms and heteroatom-containing groups are selected from N, NR 8< , O, S, SO, and SO 2 . The hetaryl group can be bonded to the remainder of the molecule via a ring carbon or a ring nitrogen.Examples of 5- or 6-membered aromatic heterocyclic rings (also called heteroaromatic rings or hetaryl) are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-Pyrimidinyl and 2-pyrazinyl. Examples of 8-, 9-, or 10-membered aromatic heterobicyclic rings are hetaryl, which has one of the aforementioned 5- or 6-membered heteroaromatic rings and another aromatic carbocycle or 5- or 6-membered heterocycle fused thereto, for example, a fused benzene, thiophene, furan, pyrrole, pyrazole, imidazole, pyridine, or pyrimidine ring.These bicyclic hetaryls include, for example, quinolinyl, isoquinolinyl, cinnolinyl, indolyl, indolizynyl, isoindolyl, indazolyl, benzofuryl, in particular 2-benzofuryl, benzothienyl, in particular 2-benzothienyl, benzo[b]thiazolyl, in particular 2-benzo[b]thiazolyl, benzoxazolyl, in particular 2-benzoxazolyl, benzthiazolyl, in particular 2-benzthiazolyl, benzimidazolyl, in particular 2-benzimidazole, imidazo[1,2-a]pyridin-2-yl, thieno[3,2-b]pyridin-5yl, imidazo-[2,1-b]-thiazol-6-yl and 1,2,4-triazolo[1,5-a]pyridin-2-yl.

[0050] In the context of the invention, the term "CN" is understood to mean a cyano group (-C=N).

[0051] When # appears in a formula showing a preferred substructure of a compound of the present invention, it denotes the bond to the remaining molecule. Cerium compounds of formula (I)

[0052] Suitable cerium(IV) compounds within the meaning of the invention are the compounds of the general formula (I) Ce 4+< [L 1 L 2 ] 4-< (I), where L 1 and L 2 comprise the ligands defined above and below, where L 1 and L 2 have the same meaning, L 1 and L 2 each have a different meaning and mixtures of two or more compounds of formula (I).

[0053] Preferred compounds are those of formula (I) where L 1 and L 2 have the same meaning.

[0054] The homoleptic compounds of formula (I) are prepared by reacting the ligand of formula (I.1) or formula (II) with a cerium salt. The cerium salt is normally soluble in the reaction medium. Suitable salts are cerium ammonium nitrate and cerium ammonium sulfate. The ligands are either commercially available or can be prepared by a synthesis known to those skilled in the art.

[0055] The heteroleptic compounds of formula (I) are prepared by Mixing of two different homoleptic cerium compounds in a suitable solvent, mixing of a homoleptic cerium compound with a ligand or its alkali / alkaline earth salt that differs from the ligands of the cerium compound used, gas phase deposition of two different homoleptic cerium compounds, vapor deposition (vapor co-condensation) of homoleptic cerium compounds with a ligand that differs from the ligands of the cerium compound used.

[0056] In the cerium compound of formula (I), L 1 and L 2 are tetradentate ligands which are independently selected from ligands of formula (I.1) or formula (II) where the radicals X, Z, A, B, R 1< , R 2< , R 3< , R 4< , R 5< and R 6< have the meanings defined above and as follows.

[0057] In a preferred embodiment, Z represents C 2 -C 3 alkylene, C 2 -C 3 alkenylene, where alkylene or alkenylene is unsubstituted or substituted by 1, 2, 3, 4, 5, or 6 identical or different radicals R 12<; or 2 or 3 of the carbon atoms of the bridging group are part of a mononuclear or dinuclear aromatic or heteroaromatic C 6 -C 10 ring system, wherein the heteroaromatic ring system has 4 to 13 carbon atoms and has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members which are selected from N, NR 8< , O, S, SO and SO 2 and wherein the aromatic or heteroaromatic ring system is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<, wherein R 12< and R 9< have the above and following definitions.

[0058] Preferred are cerium compounds of the formula (I), wherein the ligands L 1 and L 2 are independently selected ligands of the formula (II).

[0059] Preferred ligands are those of the formula (II.1) or (II), where R 1< , R 2< , R 5< and R 6< are independently selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< and the group A, consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 where # denotes the bond to the group of formula (I.1) or (II), where RA< , RB< , RC< , RD< and RE< are independently selected from hydrogen, CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl; or R 1< and A together with the carbon atom to which they are bonded form a C 6 -C 14 aryl group, where aryl is unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<; or R 6< and B together with the carbon atom to which they are bonded form a C 6 -C 14 aryl group, where aryl is unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 4a< , R 4b< are independently selected from hydrogen, C 1 -C 6 alkyl and C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<;R 9< is selected from CN, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl and C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals selected from C 1 -C 4 alkyl and C 1 -C 4 haloalkyl; and R 10< is selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl. ;

[0060] Regardless of their occurrence, the radicals RA< , RB< , RC< , RD< and RE< are preferably selected from hydrogen, CN, fluorine, chlorine, C 1 -C 4 alkyl, C 1 -C 4 fluoroalkyl and C 1 -C 4 chloroalkyl.

[0061] Particularly preferably, the radicals RA<, RB<, RC<, RD<, and RE< are independently selected from hydrogen, CN, C 1 -C 4 -fluoroalkyl, fluorine, and chlorine. In particular, the radicals RA<, RB<, RC<, RD<, and RE< are independently hydrogen or CF 3 .

[0062] In one embodiment, in formula (I.1) or (II), the radicals R 1< , R 2< , R 5< and R 6< are independently selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and A1 where # denotes the bond to the remaining molecule of formula (II), and where RA<, RB<, RC<, RD< and RE< are independently selected from hydrogen, CN, fluorine, chlorine, C 1 -C 4 alkyl, C 1 -C 4 fluoroalkyl and C 1 -C 4 chloroalkyl, preferably from hydrogen, CN, fluorine and chlorine; or R 1< and A together with the carbon atom to which they are bonded form a phenyl ring, where phenyl is unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<; or R 6< and B together with the carbon atom to which they are bonded form a phenyl ring, where phenyl is unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 9< is selected from CN, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and phenyl, where phenyl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl. 。

[0063] In a further embodiment, in formula (I.1) or (II), R 1< and R 6< are independently selected from CF 3 and A1, wherein RA<, RB<, RC<, RD< and RE< are independently selected from CN, CF 3 , fluorine and chlorine; R 2< and R 5< are independently selected from hydrogen, CF 3 and A1, wherein RA< , RB< , RC< , RD< and RE< are independently selected from hydrogen, CN, CF 3 , fluorine and chlorine; or R 1< and A together with the carbon atom to which they are attached form a phenyl ring, where phenyl is unsubstituted or substituted by 1 or 2 identical or different radicals R 9<; or R 6< and B together with the carbon atom to which they are attached form a phenyl ring, where phenyl is unsubstituted or substituted by 1 or 2 identical or different radicals R 9<; R 9< is selected from CN, halogen, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl.

[0064] In a specific embodiment, in formula (I.1) or (II), R 1< and R 6< are independently selected from hydrogen, CF 3 and A1, wherein RA< , RB< , RC< , RD< and RE< are independently selected from hydrogen and CF 3 ; R 2< and R 5< are independently selected from hydrogen, CF 3 and A1, wherein RA< , RB< , RC< , RD< and RE< are independently selected from hydrogen and CF 3 ; R 1< and A together with the carbon atom to which they are attached form a phenyl ring, where phenyl is unsubstituted or substituted by 1 or 2 identical or different radicals R 9<; R 6< and B together with the carbon atom to which they are attached form a phenyl ring, where phenyl is unsubstituted or substituted by 1 or 2 identical or different radicals R 9<; R 9< is selected from CN, F, Cl and CF 3 .

[0065] In another specific embodiment, in formula (I.1) or (II), R 2< and R 5< are independently selected from hydrogen and CF 3 and R 1< and R 6< are independently selected from CF 3 and A1, wherein RA< , RB< , RC< , RD< and RE< are hydrogen or CF 3, or R 1< and A together with the carbon atom to which they are attached form a phenyl ring, where phenyl is unsubstituted or substituted by 1 or 2 identical or different radicals R 9<; or R 6< and B together with the carbon atom to which they are attached form a phenyl ring, where phenyl is unsubstituted or substituted by 1 or 2 identical or different radicals R 9<; R 9< is selected from CN, F, Cl and CF 3 .

[0066] Preferred ligands are those of the formula (II), where in the formula (II) R 3< and R 4< are independently selected from hydrogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy, or R 3< and R 4< together with the carbon atoms to which they are attached form a C 6 -C 14 aryl group, where aryl is unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 9< is selected from CN, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl.

[0067] Particularly preferred ligands are those of the formula (II), where in the formula (II) R 3< and R 4< are independently selected from hydrogen, CN, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl and phenyl, where phenyl is unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<, or R 3< and R 4< together with the carbon atoms to which they are attached form a phenyl ring, where phenyl is unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 9< is selected from CN, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or phenyl, where phenyl is unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl.

[0068] Particularly preferred ligands are those of formula (II), wherein in formula (II) R 3< and R 4< are independently selected from hydrogen, CN, C 1 -C 2 -alkyl and CF 3 ; R 3< and R 4< together with the carbon atoms to which they are bonded form a phenyl group, wherein phenyl is unsubstituted.

[0069] Preferred ligands are those of the formula (I.1) or (II), where in the formula (II) A and B independently of one another represent a radical CR 7< and R 7< is selected from hydrogen, CN, nitro, halogen and the group B, consisting of B1, B2, B3, B4, B5, B6, B7, B8, B9, B10, B11, B12, B13, B14 and B15 where # denotes the bond to the group of formula (II), and where RF< , RG< , RH< , RI< and RJ< are independently selected from hydrogen, CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl.

[0070] Regardless of their occurrence, the radicals RF< , RG< , RH< , RI< and RJ< are preferably selected from hydrogen, CN, fluorine, chlorine, C 1 -C 4 alkyl, C 1 -C 4 fluoroalkyl and C 1 -C 4 chloroalkyl. In a preferred embodiment, the radicals RF< , RG< , RH< , and RJ< independently of one another represent hydrogen, CN, fluorine or chlorine.

[0071] Preferred ligands are those of the formula (I.1) or (II), where in the formula (II) A and B independently of one another represent a radical CR 7< and R 7< is selected from hydrogen, CN, nitro, halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl and B1, where RF< , RG< , RH< , RI< and RJ< are independently selected from hydrogen, CN, fluorine and chlorine.

[0072] Particularly preferred are ligands of formula (II.1) or (II), where in formula (II) A and B independently of one another represent a radical CR 7< and R 7< is selected from hydrogen, CN, nitro, halogen, C 1 -C 2 -alkyl and C 1 -C 2 -haloalkyl. In particular, R 7< is selected from hydrogen, CN, nitro, fluorine and chlorine, in particular hydrogen, fluorine and CN.

[0073] In one embodiment A, ligands of formula (II) are selected from the formula (IA) where X stands for O, R 1< is selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< and the group A, consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 are as defined above, R 2< is selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< and the group A,consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 as defined above, R 5< is selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 -Haloalkylsulfanyl, NR 4a< R 4b< and the group A, consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 as defined above, R 6< is selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy,C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, NR 4a< R 4b< and the group A, consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 as defined above, R 7< is selected from hydrogen, CN, nitro, halogen, C 1 -C 2 -alkyl and C 1 -C 2 -haloalkyl. ,

[0074] In one embodiment B, ligands of formula (II) are selected from the formula (IB) where X represents O; R 1< and A, together with the carbon atom to which they are attached, form a C 6 -C 14 aryl group or hetaryl group having 3 to 6 carbon atoms, where hetaryl has 1, 2 or 3 heteroatoms or heteroatom-containing groups as ring members selected from N and NR 8< , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 2< is selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< and the group A, consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 as defined above;R 5< is selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< and the group A, consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 are as defined above; R 6< and B together with the carbon atom to which they are attached form a C 6 -C 14 aryl group or hetaryl group having 3 to 6 carbon atoms, where hetaryl has 1, 2 or 3 heteroatoms or heteroatom-containing groups as ring members which are selected from N and NR 8< , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<. ;

[0075] In one embodiment C, ligands of formula (II) are selected from the formula (IC) where X stands for O; R 1< is selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< and the group A, consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 are as defined above; R 2< and A, together with the carbon atom to which they are attached, form a C 6 -C 14 aryl group or hetaryl group having 3 to 6 carbon atoms, where hetaryl has 1, 2 or 3 heteroatoms or heteroatom-containing groups as ring members selected from N and NR 8< , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<;R 5< and B, together with the carbon atom to which they are attached, form a C 6 -C 14 aryl group or hetaryl group having 3 to 6 carbon atoms, where hetaryl has 1, 2 or 3 heteroatoms or heteroatom-containing groups as ring members selected from N and NR 8< , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 6< is selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< and the group A, consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 as defined above. ;

[0076] In one embodiment D, ligands of formula (II) are selected from the formula (ID) R 1< is selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< and the group A, consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 as defined above;R 2< is selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< and the group A, consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 are as defined above; R 3< and R 4< together with the carbon atom to which they are attached form a C 6 -C 14 aryl group or hetaryl group having 3 to 6 carbon atoms, where hetaryl has 1, 2 or 3 heteroatoms or heteroatom-containing groups as ring members which are selected from N and NR 8< , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<;R 5< is selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< and the group A, consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 as defined above;R 6< is selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< and the group A, consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 are as defined above; R7< is selected from hydrogen, CN, nitro, halogen, C1-C2-alkyl and C1-C2-haloalkyl. ;

[0077] In one embodiment E, ligands of formula (II) are selected from the formula (IE) where R 1< and A, together with the carbon atom to which they are attached, form a C 6 -C 14 aryl group or hetaryl group having 3 to 6 carbon atoms, where hetaryl has 1, 2 or 3 heteroatoms or heteroatom-containing groups as ring members which are selected from N and NR 8< , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 2< is selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< and the group A, consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 as defined above;R 3< and R 4< together with the carbon atom to which they are attached form a C 6 -C 14 aryl group or hetaryl group having 3 to 6 carbon atoms, where hetaryl has 1, 2 or 3 heteroatoms or heteroatom-containing groups as ring members which are selected from N and NR 8< , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 5< is selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< and the group A, consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 as defined above;R 6< and B, together with the carbon atom to which they are attached, form a C 6 -C 14 aryl group or hetaryl group having 3 to 6 carbon atoms, where hetaryl has 1, 2 or 3 heteroatoms or heteroatom-containing groups as ring members, which are selected from N and NR 8< , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<. ;

[0078] In one embodiment F, ligands of formula (II) are selected from the formula (IF) where R 1< is selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< and the group A, consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 are as defined above; R 2< and A, together with the carbon atom to which they are attached, form a C 6 -C 14 aryl group or hetaryl group having 3 to 6 carbon atoms, where hetaryl has 1, 2 or 3 heteroatoms or heteroatom-containing groups as ring members selected from N and NR 8< , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<;R 3< and R 4< together with the carbon atom to which they are attached form a C 6 -C 14 aryl group or hetaryl group having 3 to 6 carbon atoms, where hetaryl has 1, 2 or 3 heteroatoms or heteroatom-containing groups as ring members which are selected from N and NR 8< , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<;R 5< and B together with the carbon atom to which they are attached form a C 6 -C 14 aryl group or hetaryl group having 3 to 6 carbon atoms, where hetaryl has 1, 2 or 3 heteroatoms or heteroatom-containing groups as ring members which are selected from N and NR 8< , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9< R 6< is selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, NR 4a< R 4b< and the group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 as defined above. ;

[0079] In a preferred embodiment, the compounds are of formula (I), wherein in the ligands of formula (II), where ------ between the group CR 3< -CR 4< stands for a single or double bond, X stands for O; A and B independently of one another stand for CR 7<, where R 7< is selected from H and CN; R 1< and R 6< are independently selected from hydrogen, CH 3 , CF 3 , C 2 F 5 and phenyl, or R 1< and A together with the carbon atom to which they are attached form [4-(trifluoromethyl)phenyl], or R 6< and B together with the carbon atom to which they are attached form [4-(trifluoromethyl)phenyl]; R 3< and R 4< stand for hydrogen, or R 3< and R 4< together with the carbons to which they are attached form phenyl or (3,4-difluorophenyl); R 2< and R 5< are independently selected from hydrogen, CH 3 , CF 3 , C 2 F 5 , phenyl and [3-chloro-4-(trifluoromethyl)phenyl].

[0080] In particular, the compounds are selected under

[0081] Regardless of their occurrence, the radicals R 4a< and R 4b< are preferably selected from hydrogen and C 1 -C 4 alkyl.

[0082] Regardless of its occurrence, the radical R 8< is preferably selected from C 1 -C 4 alkyl and C 1 -C 4 haloalkyl.

[0083] Regardless of its occurrence, the radical R 9< is preferably selected from CN, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and phenyl, where phenyl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl. In particular, R 9< is selected from CN, halogen, C 1 -C 2 alkyl and C 1 -C 2 haloalkyl. In particular, R 9< is selected from CN, F, Cl and CF 3 .

[0084] Regardless of its occurrence, the radical R 12< is preferably selected from halogen, CN, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl and phenyl, where phenyl is unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9< component

[0085] For the purposes of the invention, an electronic component is understood to mean a discrete or integrated electrical component that utilizes the properties of the compounds of general formula (I) or of semiconductor matrix materials containing a compound of general formula (I). In a specific embodiment, the electronic component has a layer structure that comprises, in particular, 2, 3, 4, 5, 6, 7 or more layers, wherein at least one of the layers contains at least one compound of general formula (I). However, each of the layers can also contain inorganic materials, or the component can also comprise layers composed entirely of inorganic materials.

[0086] The electronic component is preferably selected from organic field-effect transistors (OFETs), organic electroluminescent devices, organic solar cells (OSCs), devices for electrophotography, organic optical detectors, organic photoreceptors, light-emitting electrochemical cells (LECs), and organic laser diodes. Preferred organic field-effect transistors (OFETs) are organic thin-film transistors (OTFTs). Preferred organic electroluminescent devices are organic light-emitting diodes (OLEDs). Preferred organic solar cells are exciton solar cells, dye-sensitized solar cells (DSSCs), or perovskite solar cells. Preferred devices for electrophotography are photoconductive materials in organic photoconductors (OPCs).

[0087] The electronic component according to the invention is preferably in the form of an organic light-emitting diode, an organic solar cell, a photovoltaic cell, an organic sensor, an organic diode or an organic transistor, preferably a field-effect transistor or thin-film transistor or perovskite solar cell.

[0088] The electronic component can specifically be an organic electroluminescent device, in particular in the form of an organic light-emitting diode (OLED). An organic electroluminescent device comprises a cathode, an anode, and at least one emitting layer. In addition to these layers, it can also comprise further layers, e.g., one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, and / or charge generation layers. Intermediate layers, which, for example, have an exciton blocking function, can also be introduced between two emitting layers. Not all of these layers necessarily have to be present.

[0089] A preferred embodiment is an electronic component, in particular in the form of an OLED, wherein the layer comprising the compound of formula (I) is a hole-transport layer or a hole-injection layer. A hole-injection layer is generally a layer that facilitates electron injection from the anode into the organic semiconductor matrix material. The hole-injection layer can be arranged directly adjacent to the anode. A hole-transport layer transports the holes from the anode to the emitting layer and is located between a hole-injection layer and an emitting layer.

[0090] A preferred embodiment is an electronic component in the form of an organic solar cell. Organic solar cells are generally constructed in layers and typically comprise at least the following layers: anode, at least one photoactive layer, and cathode. These layers are generally applied to a substrate customary for this purpose. The photoactive region of the solar cell can comprise two layers, each of which has a homogeneous composition and forms a "flat" donor-acceptor heterojunction. A photoactive region can also comprise a mixed layer and form a donor-acceptor heterojunction in the form of a donor-acceptor bulk heterojunction. In addition to these layers, the organic solar cell can also comprise further layers, e.g., selected from Layers with electron-conducting properties (electron transport layer, ETL), layers containing a hole-conducting material (hole transport layer, HTL), these do not have to absorb radiation, exciton and hole-blocking layers (e.g. EBLs), these must not absorb, and multiplier layers.

[0091] A further preferred embodiment is an electronic component in the form of an organic solar cell, wherein the layer comprising the compound of formula (I) is a layer with electron-conducting properties (electron transport layer, ETL).

[0092] A specific embodiment is an electronic component, especially in the form of an organic solar cell, wherein the layer comprising at least one of the compounds of formula (I) is part of a pn junction connecting a light-absorbing unit to an additional light-absorbing unit in a tandem device or in a multi-stacked device and / or a pn junction connecting a cathode or an anode to a light-absorbing unit.

[0093] A further preferred embodiment is an electronic component comprising an electron transport layer comprising at least one compound of formula (I). Semiconductor matrix materials

[0094] The compounds of formula (I) according to the invention and used according to the invention, as well as their charge-transfer complexes and their reduction products, can be used as dopants in organic semiconductor matrix materials, in particular as p-dopants in hole-transport layers. The doped semiconductor matrix material preferably comprises at least one electron donor and at least one compound of formula (I), as defined above.

[0095] Suitable diaminoterphenyls are described in DE 102012007795. Diaminotrimethylphenylindanes are described in WO 2018 / 206769.

[0096] In particular, the electron donors are selected from 4,4',4"-tris(N-(2-naphthyl)-N-phenyl-amino)triphenylamine, 4,4',4"-tris(N-3-methylphenyl-N-phenyl-amino)triphenylamine, N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine, (2,2',7,7'-tetrakis-(N,N-diphenylamino)-9,9'-spirobifluorene, N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)benzidine, N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)-9,9-spirobifluorene, 9,9-bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]-9H-fluorene, 2,2'-Bis[N,N-bis(biphenyl-4-yl)amino]-9,9-spiro-bifluorene, N,N'-((9H-fluoren-9,9-diyl)bis(4,1-phenylene))bis(N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine), N,N'-Bis(phenanthren-9-yl)-N,N'-bis(phenyl)-benzidine, 1,3,5-Tris{4-[bis(9,9-dimethyl-fluoren-2-yl)amino]phenyl}benzene, Tri(terphenyl-4-yl)amine, N-(4-(6-((9,9-Dimethyl-9H-fluoren-2-yl)(6-methoxy-[1,1'-biphenyl]-3-yl)amino)-1,3,3-trimethyl-2,3 -dihydro-1H-inden-1-yl)phenyl)-N-(6-methoxy-[1,1'-biphenyl]-3-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-([1,1'-Biphenyl]-4-yl)-N-(4-(6-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amin, N,N-Di([1,1'-biphenyl]-4-yl)-3-(4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amin, N-(4-(6-(Bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amin, N-(4-(6-(9,9'-Spirobi[fluoren]-2-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amin, N-(4-(6-(Dibenzo[b,d]furan-2-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-2-amin, 9-(4-(6-(9H-Carbazol-9-yl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-9H-carbazol, N-([1,1'-Biphenyl]-4-yl)-3-(4-([1,1'-biphenyl]-4-yl(4-methoxyphenyl)amino)phenyl)-N-(4-methoxyphenyl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amin, 3-(4-(Bis(6-methoxy-[1,1'-biphenyl]-3-yl)amino)phenyl)-N,N-bis(6-methoxy-[1,1'-biphenyl]-3-yl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amin, N1-([1,1'-Biphenyl]-4-yl)-N1-(4-(6-([1,1'-biphenyl]-4-yl(4-(diphenylamino)phenyl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N4,N4-diphenylbenzene-1,4-diamin, N,N-Di([1,1'-biphenyl]-4-yl)-4'-(6-(4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)-[1,1'-biphenyl]-4-amin, N-(4-(5-(Bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amin, N-(4-(6-(Bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amin, N,N'-bis(9,9-dimethyl-fluoren-2-yl)-N,N'-diphenyl-benzidin (BF-DPB), N,N'-((9H-fluoren-9,9-diyl)bis(4,1-phenylen))bis(N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amin) (BPAPF), N4,N4,N4',N4'-tetrakis(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-4,4'-diamine (TDMFB), N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine, (2,7-bis[N,N-bis(4-methoxyphenyl)amino]-9,9-spirobi[9H-fluorene] (spiro-MeO-TPD), a mixture of N-(4-(5-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine and N-(4-(6-(bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine and mixtures thereof.

[0097] It is understood that other suitable organic semiconductor matrix materials, in particular hole-conducting materials with semiconducting properties, can also be used. Endowment

[0098] The doping can in particular be carried out such that the molar ratio of matrix molecules to the compound of the general formula (I) is 10,000:1 to 1:1, preferably 1,000:1 to 2:1, particularly preferably 5:1 to 100:1. Production of the doped semiconductor matrix material

[0099] The doping of the respective matrix material (hereinafter also referred to as hole conductor matrix HT) with the compounds of the general formula (I) according to the invention and used according to the invention can be carried out by one or a combination of two or more than two of the following methods: a) Mixed evaporation in a vacuum with a source of HT and one of at least one compound of general formula (I). b) Sequential deposition of HT and at least one compound of general formula (I) followed by inward diffusion of the dopant by thermal treatment. c) Doping of an HT layer with a solution of at least one compound of general formula (I) followed by evaporation of the solvent by thermal treatment. d) Surface doping of an HT layer with a layer of at least one compound of general formula (I) applied to one or both surfaces of the HT layer. e) Preparing a solution of host and at least one compound of general formula (I) and forming a film from the solution, e.g. by coating, casting or printing techniques or other film production techniques known to a person skilled in the art.

[0100] Another object of the invention is the use of a compound (I) as defined above as an organic semiconductor, as a dopant in organic semiconductor matrix materials, in particular as a p-dopant in hole transport layers, as an electron transport layer, as a charge injector in a charge injection layer, as a cathode material in organic batteries, as an electrochromic material.

[0101] A further object of the invention is the use of Ce(III) complex anions obtained by reduction of a compound (I) as defined above or of charge transfer complexes of a compound (I) as defined above with electron donor conductors, in particular as organic semiconductors as charge transfer complexes or as electrochromic material.

[0102] The invention further relates to compounds of the general formula (I) Ce 4+< [L 1 L 2 ] 4-< (I), their charge transfer complexes, their reduction products, and mixtures thereof, where L 1 and L 2 are each a tetradentate ligand, which are independently selected from ligands of the formula (I.1) where X independently of one another represents O or S; Z represents a bridging group which has 2 or 3 carbon atoms between the nitrogen atoms, where the carbon atoms are each unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R 12<, where two adjacent carbon atoms may also be connected to one another by a double bond, or 2 or 3 of the carbon atoms are part of a mononuclear, dinuclear or trinuclear aromatic or heteroaromatic C 6 -C 14 ring system, where the heteroaromatic ring system has 4 to 13 carbon atoms and has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members which are selected from N, NR 8<, O, S, SO and SO 2 and where the aromatic or heteroaromatic ring system is unsubstituted or substituted by 1, 2, 3,4 or 5 identical or different radicals R 9<; A and B independently of one another represent N or CR 7<; R 1< and R 6< are independently selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R 11<, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<, or R 1< and Ag together with the carbon atom to which they are attached,form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<, or R 6< and B together with the carbon atom to which they are bonded form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or are substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 2< and R 5< are independently selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy,C 3 -C 7 -cycloalkyl, where C 3 -C 7 -cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R 11<, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 -aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<; R 2< and A, together with the carbon atom to which they are attached, form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2,3 or 4 identical or different radicals R 9< are substituted, or R 5< and B together with the carbon atom to which they are attached form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 4a< R 4b< are independently selected from hydrogen, C 1 -C 6 alkyl and C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<; R 7< is selected from hydrogen, CN, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< ,C 6 -C 14 -aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<; R 8< is selected from hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 6 -C 14 -aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<; R 9< is selected from CN, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl and C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; R 10< is selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl; R 11< is selected from CN, halogen,C 1 -C 4 alkyl and C 1 -C 4 haloalkyl; R 12< are independently selected from halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 7 cycloalkyl, where C 3 -C 7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R 11<, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<; , The following compounds and their reduction products are excluded:

[0103] The invention further relates to compounds of the general formula (I) Ce 4+< [L 1 L 2 ] 4-< (I), their charge transfer complexes, their reduction products, and mixtures thereof, where L 1 and L 2 are each a tetradentate ligand, which are independently selected from ligands of the formula (II) where ------ between the group CR 3< -CR 4< stands for a single or double bond, X independently stands for O or S; A and B independently stand for N or CR 7<; R 1< and R 6< are independently selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<, or R 1< and A together with the carbon atom to which they are attached, form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl is 1,has 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<, or R 6< and B together with the carbon atom to which they are bonded form a C 6 -C 14 aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 3< and R 4< are independently selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< ,C 6 -C 14 -aryl or hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<, or R 3< and R 4< together with the carbons to which they are attached form a C 6 -C 14 -aryl group or hetaryl group having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or are substituted by 1, 2, 3 or 4 identical or different radicals R 9<; R 2< and R 5< are independently selected from hydrogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy,C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 -aryl or hetaryl having 4 to 13 carbon atoms, where hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 9<; R 4a< R 4b< are independently selected from hydrogen, C 1 -C 6 alkyl or C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<; R 7< is selected from hydrogen, CN, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfanyl, C 1 -C 6 haloalkylsulfanyl, NR 4a< R 4b< , C 6 -C 14 aryl and hetaryl having 4 to 13 carbon atoms, where hetaryl has 1,has 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members, which are selected from N, NR 8< , O, S, SO and SO 2 , where aryl and hetaryl are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<; R 8< is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R 10<; R 9< is selected from CN, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 6 -C 14 aryl, where aryl is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals selected from C 1 -C 4 alkyl and C 1 -C 4 haloalkyl; R 10< is selected from CN, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl, where the following compounds and their reduction products of the formula (I) are excluded, where L 1 = L 2 = N,N'-bis(4,4,4,-trifluorobut-1-en-3-one)-ethylenediamine, L 1 = L 2 = N,N'-bis(4,4,5,5,5-pentafluoropent-1-en-3-one)-ethylenediamine, L 1 = L 2 = N,N'-bis(4,4,5,5,6,6,6-heptafluorohex-1-en-3-one)-ethylenediamine, and the following compounds and their reduction products: ,

[0104] The following examples serve to illustrate the invention without limiting it in any way. EXAMPLES Abbreviations:

[0105] APCI-MSatmospheric pressure chemical ionization mass spectrometer DCMDichloromethane DEMEthylene glycol dimethyl ether HTMLhole transport material MeCNAcetonitrile iPrOHIso-propanol EDTAEthylenediaminetetraacetic acid

[0106] Cerium isopropoxide was prepared according to " Gradeff, PS et al., Journal of the less common metals, Vol. 126, 1986, 335-338."

[0107] Sample preparation for conductivity measurements: Glass substrates with 50 nm thick, patterned Au electrodes with a channel length of 100 µm were used to prepare the doped thin-film samples. The films were deposited either by thermal evaporation or by liquid-phase deposition, e.g., by spin coating. Thermal evaporation took place at room temperature under high vacuum (base pressure < 5 x 10-7 mbar). Hole transport material (HTM) and dopant were co-evaporated at a dopant concentration of 20 wt%, with the evaporation rates being controlled using two independent quartz crystal microbalances.

[0108] The liquid-processed films were spin-coated from a chlorobenzene solution of HTM and dopant at 3000 rpm. The dopant concentration in the HTM was nominally 10 wt%. The films were then baked at 80°C for 5 min. The film thickness was verified by profilometry and was between 50 and 110 nm. Characterization:

[0109] The lateral conductivity of the films was determined from the increase in the current-voltage characteristics between -10 and 10 V. The measurements were performed in-situ under high vacuum immediately after sample preparation for thermally evaporated films and in air for liquid-processed films. Synthesis of 1:

[0110]

[0111] The synthesis was carried out according to the literature J. Schläfer, D. Graf, G. Fornalczyk, A. Mettenbörger, S. Mathur, Inorg. Chem. 2016, 55, 5422-5429.

[0112] Cyclic voltammetry of 1 in dichloromethane (DCM, 200 mV / s, 0.1M NBu 4 PF 6 ) gave the following: E ​​1 / 2 (vs. Fc / Fc +< ) = -0.51V.

[0113] Compound 1 sublimes without residue at an external temperature of 140°C and a pressure of 10 -2< mbar. Synthesis of 2:

[0114]

[0115] The preparation of 4,4,4-trifluoro-3-oxobutanenitrile was carried out according to WO2005 / 49033.

[0116] 4,4,4-Trifluoro-3-oxobutanenitrile (1.9 g, 13.9 mmol) was dissolved in acetic anhydride (Ac2O, 5 mL) and (EtO)3CH (2.05 g, 13.9 mmol). The reaction mixture was refluxed for 1 h. Subsequently, all volatile components were removed in vacuo. The brown residue was dissolved in dichloromethane (DCM, 20 mL) and 1,2-diaminoethane (0.2 mL) was added. The white precipitate was filtered off (0.079 g, 0.22 mmol, 1.6%). The mass spectrum of the ligand shows [MH] +< ; 353.

[0117] The ligand (76 mg, 0.21 mmol) was added to a 0.3M solution of Ce 2 (OiPr) 8 (HOiPr) 2 (0.17 mL, 0.055 mmol) in ethylene glycol dimethyl ether / iPropanol (DME / iOrOH, 1:1 v / v) under N 2 . After 30 minutes, the solvent was removed. 0.078 mg of a red solid of compound 2 was obtained. The mass spectrum of compound 2 shows [MH] -< ; 843.

[0118] Cyclic voltammetry of 2 in acetonitrile (ACN, 200 mV / s, 0.1M NBu 4 PF 6 ) gave the following: E ​​1 / 2 (vs. Fc / Fc +< ) = +0.40V. Synthesis of 3:

[0119]

[0120] The synthesis of the ligand was carried out according to the literature Gurley, L.; Beloukhina, N.; Boudreau, K.; Klegeris, A.; McNeil, WS Journal of Inorganic Biochemistry 2011, 105, 6, 858 - 866.

[0121] To a 0.4M solution of Ce 2 (OiPr) 8 (HOiPr) 2 (0.33 mL, 0.131 mmol) in ethylene glycol dimethyl ether / ipropanol (DME / iPrOH) (1:1 v / v) was added 1 (120 mg, 0.26 mmol) under N 2 . After 30 minutes, the solvent was removed, and the solid was washed with diethyl ether (Et 2 O). This yielded 56 mg of a red solid of compound 3. The mass spectrum of compound 3 shows [MH]-; 1047.

[0122] Cyclic voltammetry of 3 in acetonitrile (ACN, 200 mV / s, 0.1M NBu 4 PF 6 ) gave the following: E ​​1 / 2 (vs. Fc / Fc +< ) = -0.36V. Synthesis of 4:

[0123]

[0124] 3,5-Bistrifluoromethylacetophenone (8 g, 31.3 mmol) was dissolved in ethanol (40 mL), and acetic acid (0.1 mL) was added. Then, 1,2-diaminoethane (0.94 g, 15.6 mmol) was added, and the solution was heated in a pressure tube at 90°C for 12 h. Upon cooling to -20°C, colorless crystals formed, which were filtered off. After drying in vacuo, 2.0 g (0.37 mmol, 24%) of a colorless solid was obtained: N1,N2-bis(1-(3,5-bis(trifluoromethyl)phenyl)vinyl)ethane-1,2-diamine, APCI-MS (positive): 537.3 [M+H] +< .

[0125] N1,N2-Bis(1-(3,5-bis(trifluoromethyl)phenyl)vinyl)ethane-1,2-diamine (9.72 g, 18.1 mmol) was suspended in DCM (50 ml) and trifluoroacetic anhydride (8.37 g, 39.8 mmol) was added. After stirring at room temperature for 12 h, the reaction solution was cooled to -20°C and the white solid was filtered off. The solid was recrystallized from acetonitrile (50 ml) and filtered off. White solid, 4.16 g (5.71 mmol, 31%): 4,4'-(ethane-1,2-diylbis(azanediyl))bis(4-(3,5-bis(trifluoromethyl)phenyl)-1,1,1-trifluorobut-3-en-2-one), APCI-MS (positive): 729.4 [M+H] +< .

[0126] 4,4'-(ethane-1,2-diylbis(azanediyl))bis(4-(3,5-bis(trifluoromethyl)phenyl)-1,1,1-trifluorobut-3-en-2-one) (2 g, 2.74 mmol) was added to a solution of cerium(IV) isopropoxide (0.32M in DME / iPrOH, 4.3 ml, 1.37 mmol). After stirring for 12 h, the suspension was filtered and washed with DME. Red solid, 1.9 g (1.19 mmol, 87%), cerium bis((2Z,2'Z,4Z,4'Z)-4,4'-(ethane-1,2-diylbis(azanyylide))bis(4-(3,5-bis(trifluoromethyl)phenyl)-1,1,1-trifluorobut-2-en-2-olate)) (4), APCI-MS (positive): 1593 [M+H] +< .

[0127] The metal complex (4) (538 mg) was sublimed at 200°C at 4·10 -6 < mbar. The yield was 335 mg (62%). The metal complex (4) decomposes at 260 °C.

[0128] Cyclic voltammetry of 4 in acetonitrile (ACN, 200 mV / s, 0.1M NBu 4 PF 6 ) gave the following: E ​​1 / 2 (vs. Fc / Fc +< ) = -0.12V.

[0129] When spiro-MeO-TAD (CAS No. 207739-72-8) was doped with 20 wt.% of the dopant (4), an increase in conductivity of up to 1.5 10 -6 S / cm was measured after solvent processing (spin coating). The intrinsic conductivity of spiro-MeO-TAD without doping was measured at 2 10 -8 S / cm. Synthesis of 5:

[0130]

[0131] 1-(2-hydroxy-5-(trifluoromethyl)phenyl)ethan-1-one (1.19 g, 0.583 mmol) and 1,2-diaminoethane (0.18 g, 0.29 mmol) were dissolved in DCM and stirred for 12 h. The solid was then filtered off. A white solid, 0.63 g (1.45 mmol, 50%), of 2,2'-(-(Ethan-1,2-diylbis(azaneylylidene))bis(ethan-1-yl-1-ylidene))bis(4-(trifluoromethyl)phenol) was obtained. APCI-MS (positive): 433.3 [M+H] +< .

[0132] 2,2'-(-(Ethan-1,2-diylbis(azaneylylidene))bis(ethan-1-yl-1-ylidene))bis(4-(trifluoromethyl)phenol) (0.59 g, 1.36 mmol) was added to a solution of cerium(IV) isopropoxide (0.32M in DME / iPrOH, 0.68 mmol, 2.12 mL). The solvent was removed and the residue washed with hexane. The residue was dissolved in CHCl 3 , filtered, and precipitated with hexane and collected by filtration. An orange-red solid, 0.42 g (0.42 mmol, 62%), cerium bis((2,2'-((1E,1'E)-(ethane-1,2-diylbis(azanylylidene))bis(ethan-1-yl-1-ylidene))bis(4-(trifluoromethyl)phenolate)) (5) was obtained. APCI-MS (positive): 1001 [M+H] +< .

[0133] The metal complex (5) (350 mg) was sublimed at 180-200°C at 4·10 -6 < mbar. The yield was 12 mg (0.3%).

[0134] Cyclic voltammetry of 5 in acetonitrile (ACN, 200 mV / s, 0.1M NBu 4 PF 6 ) gave the following: E ​​1 / 2 (vs. Fc / Fc +< ) = +0.3V. Synthesis of 6:

[0135]

[0136] Ethylenediamine (830 mg, 13.6 mmol) was added to a solution of 2-benzoyl-3-ethoxyacrylonitrile (5.54 g, 27.6 mmol) in 50 mL of dichloromethane and stirred at room temperature. After 2 h, a precipitate had formed, which was filtered off and washed with dichloromethane. After drying in vacuo, 2.75 g (7.43 mmol, 55%) of (2Z,2'E)-2,2'-((ethane-1,2-diylbis(azandiyl))bis(methanylylidene))bis(3-oxo-3-phenylpropanenitrile) was obtained.

[0137] To a solution of cerium isopropoxide (11.25 ml, 3.6 mmol) was added 2.67 g (7.2 mmol) of (2Z,2'E)-2,2'-((ethane-1,2-diylbis(azandiyl))bis(methanylylidene))bis(3-oxo-3-phenylpropanenitrile). The brown solid was filtered off and washed with DME (15 ml) and hexane (20 ml). The solid was then washed three times with a total of 200 ml of dichloromethane, and the washing solution was filtered. The washing solution was concentrated by half, and hexane (100 ml) was added. The resulting microcrystalline dark solid was filtered off and dried in vacuo. 1.80 g (2.05 mmol, 57%) of (6) was obtained. (6) decomposes at 170 °C.

[0138] Cyclic voltammetry of 6 in acetonitrile (ACN, 200 mV / s, 0.1M NBu 4 PF 6 ) gave the following: E ​​1 / 2 (vs. Fc / Fc +< ) = -0.1V. Synthesis of 7:

[0139]

[0140] Phenylenediamine (1.62 g, 15 mmol) and (E)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (5 g, 30 mmol) were combined and stirred in 100 mL of dichloromethane at room temperature for 2 days. The solution was evaporated to half, after which 100 mL of pentane was added. The microcrystalline solid, 4,4'-(1,2-phenylenebis(azanyylidene))bis(1,1,1-trifluorobut-2-en-2-ol) (2.04 g, 5.80 mmol), was filtered and dried in vacuo. 4.12 g (11.7 mmol, 78%) was isolated.

[0141] 4,4'-(1,2-Phenylenebis(azanyylidene))bis(1,1,1-trifluorobut-2-en-2-ol) (2.04 g, 5.80 mmol) was added to a solution of cerium(IV) isopropoxide (0.32 M in DME / iPrOH, 9 mL, 2.89 mmol). The resulting red solid was filtered off and washed with DME. Dark red solid (7) was obtained, 1.08 g (1.39 mmol, 48%). APCI-MS (positive): 841.1 [M+H] +< .

[0142] The metal complex (7) (1.00 g) was sublimed at 180-210 °C at 3 10 -6 < mbar. The yield was 205 mg (20%). The metal complex (7) decomposes at 237 °C.

[0143] Cyclic voltammetry of 7 in acetonitrile (ACN, 200 mV / s, 0.1M NBu 4 PF 6 ) gave the following: E ​​1 / 2 (vs. Fc / Fc +< ) = -0.09V. Synthesis of 8:

[0144]

[0145] 4,5-Difluorobenzene-1,2-diamine (2.14 g, 15 mmol) and (E)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (5 g, 30 mmol) were combined and stirred in 500 mL of dichloromethane at room temperature for 2 days. 100 mL of the dichloromethane was removed in vacuo, and 200 mL of pentane was added. The microcrystalline solid, (2Z,2'Z,4E,4'E)-4,4'-((4,5-difluoro-1,2-phenylene)bis(azanylylidene))bis(1,1,1-trifluorobut-2-en-2-ol), was filtered and dried in vacuo. 3.60 g (9.27 mmol, 62%) were isolated.

[0146] 4,4'-((4,5-Difluoro-1,2-phenylene)bis(azanyylidene))bis(1,1,1-trifluorobut-2-en-2-ol) (2.50 g, 6.44 mmol) was added to a solution of cerium(IV) isopropoxide (0.32 M in DME / iPrOH, 4.3 mL, 1.37 mmol). The suspension was filtered, and the red solid was washed with a little DME and hexane. A dark red solid, (8), 0.70 g (0.77 mmol, 12%), cerium bis((2Z,2'Z,4E,4'E)-4,4'-((4,5-difluoro-1,2-phenylene)bis(azanylylidene))bis(1,1,1-trifluorobut-2-en-2-olate)) was obtained, APCI-MS (positive): 913 [M+H] +< .

[0147] The metal complex (8) (700 mg) was sublimed at 180°C at 3 10 -6 < mbar. The yield was 150 mg (22%). The metal complex (8) decomposes at 244 °C.

[0148] Cyclic voltammetry of 8 in acetonitrile (ACN, 200 mV / s, 0.1M NBu 4 PF 6 ) gave the following: E ​​1 / 2 (vs. Fc / Fc +< ) = +0.08V.

[0149] When ZnPc (zinc phthalocyanine) was doped with 20 wt.% of the dopant (8), an increase in conductivity of up to 7.6 10 -5 S / cm was measured after co-evaporation in vacuum. The intrinsic conductivity of ZnPc without doping is <1 10 -8 S / cm. ( Tietze, ML, Pahner, P., Schmidt, K., Leo, K., & Lüssem, B. (2015). Advanced Functional Materials, 25(18), 2701-2707 ).

[0150] When MeO-TPD (CAS No. 122738-21-0) was doped with 20 wt.% of the dopant (8), an increase in conductivity of up to 1 10 -5 < S / cm was measured after co-evaporation in vacuum. The intrinsic conductivity of ZnPc without doping is 7 10 -8 < S / cm. (Sakai, N., Warren, R., Zhang, F., Nayak, S., Liu, J., Kesava, SV, Lin, Y.-H., Biswal, HS, Lin, (2021). Adduct-based p-doping of organic semiconductors. Nature Materials 2021 20:9, 20(9), 1248-1254. )

[0151] When spiro-MeO-TAD (CAS No. 207739-72-8) was doped with 20 wt.% of dopant (8), an increase in conductivity of up to 2.8 10 -6 S / cm was measured after solvent processing (spin coating). The intrinsic conductivity of spiro-MeO-TAD without doping was measured at 2 10 -8 S / cm. Synthesis of 9:

[0152]

[0153] 1-(3-Chloro-4-(trifluoromethyl)phenyl)-4,4,5,5,5-pentafluoropentane-1,3-dione (3.00 g, 8.13 mmol) was suspended in B(nBuO) 3 (9.35 g, 40.7 mmol), and 1,2-diaminophenylene (0.88 g, 8.13 mmol) was added. After 15 minutes, the white solid was filtered off and washed with a little hexane. A white solid, 2.2 g (4.79 mmol, 59%), of 1-((2-aminophenyl)amino)-1-(3-chloro-4-(trifluoromethyl)phenyl)-4,4,5,5,5-pentafluoropent-1-en-3-one was obtained. APCI-MS (positive): 459 [M+H] +< .

[0154] 4-Ethoxy-1,1,1-trifluorobut-3-en-2-one (0.73 g, 4.37 mmol) was dissolved in DCM, and 1-((2-aminophenyl)amino)-1-(3-chloro-4-(trifluoromethyl)phenyl)-4,4,5,5,5-pentafluoropent-1-en-3-one (2.0 g, 4.37 mmol) was added. The reaction mixture was stirred for 12 h, and then the solvent was removed. The residue was dissolved in acetonitrile, and copper(II) acetate (1.5 g) was added. Water was added to this dark green solution, and the solid was filtered off. The solid was purified by column chromatography (chloroform as eluent). The residue was treated with oxalic acid and EDTA, then concentrated HCl and chloroform, and the phases were separated. The organic phase was washed with saturated NaHCO 3 and saturated NaCl solution and dried (Na 2 SO 4 ). The solvent was removed.A white solid, 2.0 g (3.44 mmol, 79%), of 1-(3-chloro-4-(trifluoromethyl)phenyl)-4,4,5,5,5-pentafluoro-1-((2-((-4,4,4-trifluoro-3-oxobut-1-en-1-yl)amino)phenyl)amino)pent-1-en-3-one was obtained. APCI-MS (positive): 581.8 [M+H] +< .

[0155] 1-(3-Chloro-4-(trifluoromethyl)phenyl)-4,4,5,5,5-pentafluoro-1-((2-((-4,4,4-trifluoro-3-oxobut-1-en-1-yl)amino)phenyl)amino)pent-1-en-3-one (1.9 g, 3.2 mmol) was added to a solution of cerium(IV) isopropoxide (0.32 M in DME / iPrOH, 1.63 mmol, 5.1 mL). Hexane was added and the resulting solid was filtered off and washed with hexane. The residue was dissolved in chloroform, filtered, and recrystallized from chloroform / hexane to give a red solid (9), 0.41 g (0.316 mmol, 20%). APCI-MS (positive): 1296.8 [M+H] +< .

[0156] The metal complex (9) (313 mg) was sublimed at 180-190 °C at 3.10-6 mbar. The yield was 167 mg (53%). The metal complex (9) decomposes at 244 °C.

[0157] Cyclic voltammetry of 9 in acetonitrile (ACN, 200 mV / s, 0.1M NBu 4 PF 6 ) gave the following: E ​​1 / 2 (vs. Fc / Fc +< ) = +0.0V.

[0158] When ZnPc (zinc phthalocyanine) was doped with 20 wt.% of the dopant (9), an increase in conductivity of up to 1.1 10 -5 S / cm was measured after co-evaporation in vacuum. The intrinsic conductivity of ZnPc without doping is <1 10 -8 S / cm. ( Tietze, ML, Pahner, P., Schmidt, K., Leo, K., & Lüssem, B. (2015). Advanced Functional Materials, 25(18), 2701-2707 ).

[0159] When spiro-MeO-TAD (CAS No. 207739-72-8) was doped with 20 wt.% of the dopant (9), an increase in conductivity of up to 5.1 10 -6 S / cm was measured after solvent processing (spin coating). The intrinsic conductivity of the spiro-MeO-TAD without doping was measured at 2 10 -8 S / cm.

Claims

1. A electronic component comprising at least one compound of general formula (I)         Ce4+[L1L2]4-     (I), wherein L1 and L2 are each a tetradentate ligand independently selected from ligands of formula (1.1) wherein X independently from each other represents O or S; Z is a bridging group, which has 2 or 3 carbon atoms between the nitrogen atoms, wherein the carbon atoms each being unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R12, wherein two adjacent carbon atoms may be linked to one another by a double bond, or 2 or 3 of the carbon atoms are part of a mononuclear, 2-nuclear or 3-nuclear C6-C14 aromatic or heteroaromatic ring system, wherein the heteroaromatic ring system has 4 to 13 carbon atoms and has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2 and wherein the aromatic or heteroaromatic ring system is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R9; A and B independently from each other represent N or CR7; R1 and R6 are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C7 cycloalkyl, wherein C3-C7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R11, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4aR4b, C6-C14 aryl and hetaryl having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, wherein aryl and hetaryl being unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R9; or R1 and A together with the carbon atom to which they are attached form a C6-C14 aryl group or hetaryl group having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, aryl and hetaryl being unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9, or R6 und B together with the carbon atom to which they are attached form a C6-C14 aryl group or hetaryl group having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, aryl and hetaryl being unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9; R2 und R5 are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C7 cycloalkyl, wherein C3-C7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R11, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4aR4b, C6-C14 aryl and hetaryl having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, wherein aryl and hetaryl being unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R9; R2 and A together with the carbon atom to which they are attached form a C6-C14 aryl group or hetaryl group having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, aryl and hetaryl being unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9, or R5 and B together with the carbon atom to which they are attached form a C6-C14 aryl group or hetaryl group having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, aryl and hetaryl being unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9; R4aR4b are independently from each other selected from hydrogen, C1-C6 alkyl and C6-C14 aryl, wherein aryl is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R10; R7 is selected from hydrogen, CN, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4aR4b, C6-C14 aryl and hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, wherein aryl and hetaryl are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R10; R8 is selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl and C6-C14 aryl, wherein aryl is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R10; R9 is selected from CN, halogen, C1-C6 alkyl, C1-C6 haloalkyl and C6-C14 aryl, wherein aryl is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals selected from C1-C4 alkyl and C1-C4 haloalkyl; R10 is selected from CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl; R11 is selected from CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl; R12 independently selected from halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R11, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4aR4b, C6-C14 aryl and hetaryl having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, wherein aryl and hetaryl being unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R9.

2. The electronic component according to claim 1 comprising at least one compound of general formula (I)         Ce4+[L1L2]4-     (I), wherein L1 and L2 are each a tetradentate ligand independently selected from ligands of formula (II) wherein - - - - - - between the group CR3-CR4 represents a single or double bond; X independently from each other represents O or S; A and B independently from each other represent N or CR7; R1 and R6 are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4aR4b, C6-C14 aryl and hetaryl having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, wherein aryl and hetaryl being unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R9; or R1 and A together with the carbon atom to which they are attached form a C6-C14 aryl group or hetaryl group having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, aryl and hetaryl being unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9, or R6 und B together with the carbon atom to which they are attached form a C6-C14 aryl group or hetaryl group having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, aryl and hetaryl being unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9; R3 and R4 are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4aR4b, C6-C14 aryl and hetaryl having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, wherein aryl and hetaryl being unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R9, or R3 and R4 together with the carbon atom to which they are attached form a C6-C14 aryl group or hetaryl group having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, aryl and hetaryl being unsubstituted or substituted with 1, 2, 3 or 4 identical or different R9 radicals; R2 and R5 are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4aR4b, C6-C14 aryl and hetaryl having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, wherein aryl and hetaryl being unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R9; R4aR4b are independently from each other selected from hydrogen, C1-C6 alkyl and C6-C14 aryl, wherein aryl is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R10; R7 is selected from hydrogen, CN, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4aR4b, C6-C14 aryl and hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, wherein aryl and hetaryl are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R10; R8 is selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl and C6-C14 aryl, wherein aryl is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R10; R9 is selected from CN, halogen, C1-C6 alkyl, C1-C6 haloalkyl and C6-C14 aryl, wherein aryl is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals selected from C1-C4 alkyl and C1-C4 haloalkyl; R10 is selected from CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl.

3. The electronic component according to claim 1 or 2, wherein in formula (1.1) or formula (II) wherein R1, R2, R5 and R6 are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4aR4b and group A consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18 and A19 wherein # denotes the bond to the group of formula (I) wherein RA, RB, RC, RD and RE are independently selected from hydrogen, CN, halogen, C1-C4 alkyl and C1-C4 haloalkyl; or R1 and A together with the carbon atom to which they are attached form a C6-C14 aryl group, wherein aryl is unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9; or R6 and B together with the carbon atom to which they are attached form a C6-C14 aryl group, wherein aryl is unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9; R4a, R4b are independently selected from hydrogen, C1-C6 alkyl and C6-C14 aryl, wherein aryl is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R10; R9 is selected from CN, halogen, C1-C6 alkyl, C1-C6 haloalkyl and C6-C14 aryl, wherein aryl is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals selected from C1-C4 alkyl and C1-C4 haloalkyl; and R10 is selected from CN, halogen, C1-C4 alkyl and C1-C4 haloalkyl.

4. The electronic component according to any one of the preceding claims, wherein in formula (II) R3 and R4 are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy and phenyl, wherein phenyl is unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R9, or R3 and R4 together with the carbon atoms to which they are attached form a C6-C14 aryl group wherein aryl is unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9; R9 is selected from CN, halogen, C1-C6 alkyl, C1-C6 haloalkyl or C6-C14 aryl, wherein aryl is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different substituents selected from C1-C4 alkyl or C1-C4 haloalkyl.

5. The electronic component according to any one of the preceding claims, wherein in formula (1.1) or formula (II) A and B are independently a radical CR7 and R7 is selected from hydrogen, CN, nitro, halogen and group B consisting of B1, B2, B3, B4, B5, B6, B7, B8, B9, B10, B11, B12, B13, B14 and B15 wherein # denotes the bond to the group of formula (II), and wherein RF, RG, RH, RI and RJ are independently selected from hydrogen, CN, halogen, C1-C4 alkyl and C1-C4 haloalkyl.

6. The electronic component according to any one of the preceding claims, wherein in R1, R2, R5 and R6, in formula (1.1) or formula (II), are independently selected from hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, and A1 # denotes the bond to the remaining molecule of formula (1.1) or formula (II), and wherein RA, RB, RC, RD and RE are independently selected from hydrogen, CN, fluorine, chlorine, C1-C4 alkyl, C1-C4 fluoroalkyl and C1-C4 chloroalkyl, preferably selected from hydrogen, CN, fluorine and chlorine; or R1 and A together with the carbon atom to which they are attached form a phenyl ring, wherein phenyl is unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9; or R6 and B together with the carbon atom to which they are attached form a phenyl ring, wherein phenyl is unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9; R9 is selected from CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl and phenyl, wherein phenyl is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different substituents selected from C1-C4 alkyl or C1-C4 haloalkyl.

7. The electronic component according to any one of the preceding claims, wherein in formula (1.1) or formula (II) A and B are independently a radical CR7 and R7 is selected from hydrogen, CN, nitro, halogen, C1-C2 alkyl and C1-C2 haloalkyl.

8. The electronic component according to any one of the preceding claims, wherein R3 and R4 are selected independently of one another from hydrogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, or R3 and R4 together with the carbon atoms to which they are attached form a phenyl ring, wherein phenyl is unsubstituted or substituted by 1, 2, 3 or 4 identical or different radicals R9; R9 is selected from CN, halogen, C1-C4-alkyl, C1-C4-haloalkyl and phenyl, where phenyl is unsubstituted or substituted by 1, 2, 3 or 4 identical or different substituents selected from C1-C4-alkyl or C1-C4-haloalky.

9. The electronic component according to any one of the preceding claims, wherein L1 and L2 have the same meanings.

10. The electronic component according to any one of the preceding claims, in the form of an organic light-emitting diode, an organic solar cell, a photovoltaic cell, an organic sensor, an organic diode or an organic field-effect transistor, preferably in form of a thin-film transistor.

11. The electronic component according to any one of the preceding claims, having a layer structure, which comprises 2, 3, 4, 5, 6, 7 or more layers.

12. The electronic component according to any one of the preceding claims, comprising an hole transport layer and / or a hole injection layer, which comprises at least one of the compound of formula (I).

13. The electronic component according to any one of the preceding claims, comprising an electron transport layer, which comprises at least one of the compound of formula (I).

14. Doped semiconductor matrix material comprising at least one electron donor and at least one compound of the formula (I) as defined in any one of claims 1 to 9, wherein the electron donor is preferably selected from 4,4',4"-tris(N-(2-naphthyl)-N-phenyl-amino)triphenylamine (2-TNATA), 4,4',4"-tris(N-3-methylphenyl-N-phenyl-amino)triphenylamine (m-MTDATA), N,N,N',N'-tetrakis(4-methoxy-phenyl)benzidine (MeO-TPD), (2,2',7,7'-tetrakis-(N,N-diphenylamino)-9,9'-spirobifluorene (spiro-TTB), N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-benzidine, N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-9,9-spiro-bifluorene, 9,9-bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]-9H-fluorene, 2,2'-bis[N,N-bis(biphenyl-4-yl)amino]-9,9-spiro-bifluorene, N,N'-((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine) (BPAPF), N,N'-bis(phenanthrene-9-yl)-N,N'-bis(phenyl)-benzidine, 1,3,5-tris{4-[bis(9,9-dimethyl-fluorene-2-yl)amino]phenyl}benzene, tri(terphenyl-4-yl)amine, N-(4-(6-((9,9-dimethyl-9H-fluorene-2-yl)(6-methoxy-[1,1'-biphenyl]-3-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-indene-1-yl)phenyl)-N-(6-methoxy-[1,1'-biphenyl]-3-yl)-9,9-dimethyl-9H-fluorene-2-amine, N-([1,1'-biphenyl]-4-yl)-N-(4-(6-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluorene-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-indene-1-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-amine, N,N-di([1,1'-biphenyl]-4-yl)-3-(4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)-1,1,3-trimethyl-2,3-dihydro-1H-indene-5-amine, N-(4-(6-(bis(9,9-dimethyl-9H-fluorene-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9-dimethyl-9H-fluorene-2-amine, N-(4-(6-(9,9'-spirobi[fluorene]-2-yl(9,9-dimethyl-9H-fluorene-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine, N-(4-(6-(dibenzo[b,d]furane-2-yl(9,9-dimethyl-9H-fluorene-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-indene-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluorene-2-yl)dibenzo[b,d]furan-2-amine, 9-(4-(6-(9H-carbazol-9-yl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-9H-carbazole, N-([1,1'-biphenyl]-4-yl)-3-(4-([1,1'-biphenyl]-4-yl(4-methoxyphenyl)amino)phenyl)-N-(4-methoxyphenyl)-1,1,3-trimethyl-2,3-dihydro-1H-inden-5-amine, 3-(4-(bis(6-methoxy-[1,1'-biphenyl]-3-yl)amino)phenyl)-N,N-bis(6-methoxy-[1,1'-biphenyl]-3-yl)-1,1,3-trimethyl-2,3-dihydro-1H-indene-5-amine, N1-([1,1'-biphenyl]-4-yl)-N1-(4-(6-([1,1'-biphenyl]-4-yl(4-(diphenylamino)phenyl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, N,N-di([1,1'-biphenyl]-4-yl)-4'-(6-(4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)-1,3,3-trimethyl-2,3-dihydro-1H-indene-1-yl)-[1,1'-biphenyl]-4-amine, N-(4-(5-(bis(9,9-dimethyl-9H-fluorene-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-indene-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9-dimethyl-9H-fluorene-2-amine, N-(4-(6-(bis(9,9-dimethyl-9H-fluorene-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-indene-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9-dimethyl-9H-fluorene-2-amine, N,N'-bis(9,9-dimethyl-fluorene-2-yl)-N,N'-diphenyl-benzidine (BF-DPB), N,N'-((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine) (BPAPF), N4,N4,N4',N4'-tetrakis(9,9-dimethyl-9H-fluorene-2-yl)-[1,1'-biphenyl]-4,4'-diamine (TDMFB), N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirobi[fluorene]-2-amine, (2,7-bis[N,N-bis(4-methoxyphenyl)amino]-9,9-spirobi[9H-fluorene] (spiro-MeO-TPD), a mixture of N-(4-(5-(bis(9,9-dimethyl-9H-fluorene-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9-dimethyl-9H-fluorene-2-amine and N-(4-(6-(bis(9,9-dimethyl-9H-fluorene-2-yl)amino)-1,3,3-trimethyl-2,3-dihydro-1H-inden-1-yl)phenyl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9-dimethyl-9H-fluorene-2-amine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine and mixtures thereof.

15. Use of a compound of formula (I) or mixtures thereof, as defined in any one of claims 1 to 9 - as organic semiconductor, - as a doping agent in organic semiconductor matrix materials, especially as p-dopant in hole transport layers, - as charge injector in a charge injection layer, - as electron transport layer, - as cathode material in organic batteries, - as electrochromic material - as electron acceptor.

16. Use of Ce(lll) complex anions obtained by reduction of a compound of formula (I) as defined in any one of claims 1 to 9 or of charge transfer complexes of a compound of formula (I) as defined in any one of claims 1 to 9 with electron donors as organic semiconductor, as electrochromic material or as ferromagnets.

17. A compound of general formula (I)         Ce4+[L1L2]4-     (I) , their charge transfer complexes, their reduction products and mixtures thereof, wherein L1 and L2 are each a tetradentate ligand independently selected from ligands of formula (1.1) wherein X independently from each other represents O or S; Z is a bridging group, which has 2 or 3 carbon atoms between the nitrogen atoms, wherein the carbon atoms each being unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R12, wherein two adjacent carbon atoms may be linked to one another by a double bond, or 2 or 3 of the carbon atoms are part of a mononuclear, 2-nuclear or 3-nuclear C6-C14 aromatic or heteroaromatic ring system, wherein the heteroaromatic ring system has 4 to 13 carbon atoms and has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2 and wherein the aromatic or heteroaromatic ring system is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different radicals R9; A and B independently from each other represent N or CR7; R1 and R6 are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C7 cycloalkyl, wherein C3-C7-cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R11, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4aR4b, C6-C14 aryl and hetaryl having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, wherein aryl and hetaryl being unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R9; or R1 and A together with the carbon atom to which they are attached form a C6-C14 aryl group or hetaryl group having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, aryl and hetaryl being unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9, or R6 and B together with the carbon atom to which they are attached form a C6-C14 aryl group or hetaryl group having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, aryl and hetaryl being unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9; R2 and R5 are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C7 cycloalkyl, wherein C3-C7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R11, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4aR4b, C6-C14 aryl and hetaryl having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, wherein aryl and hetaryl being unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R9; R2 and A together with the carbon atom to which they are attached form a C6-C14 aryl group or hetaryl group having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, aryl and hetaryl being unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9, or R5 and B together with the carbon atom to which they are attached form a C6-C14 aryl group or hetaryl group having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, aryl and hetaryl being unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9; R4aR4b are independently from each other selected from hydrogen, C1-C6 alkyl and C6-C14 aryl, wherein aryl is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R10; R7 is selected from hydrogen, CN, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4aR4b, C6-C14 aryl and hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, wherein aryl and hetaryl are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R10; R8 is selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl and C6-C14 aryl, wherein aryl is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R10; R9 is selected from CN, halogen, C1-C6 alkyl, C1-C6 haloalkyl and C6-C14 aryl, wherein aryl is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals selected from C1-C4 alkyl and C1-C4 haloalkyl; R10 is selected from CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl; R11 is selected from CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl; R12 independently selected from halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C7 cycloalkyl, where C3-C7 cycloalkyl is unsubstituted or substituted by 1, 2, 3, 4, 5 or 6 identical or different radicals R11, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4aR4b, C6-C14 aryl and hetaryl having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, wherein aryl and hetaryl being unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R9; with the proviso that the following compounds are excluded:

18. The compounds of general formula (I) according to claim 17         Ce4+[L1L2]4-     (I), their charge transfer complexes, their reduction products and mixtures thereof, wherein L1 and L2 are each a tetradentate ligand independently selected from ligands of formula (II) wherein - - - - - - between the group CR3-CR4 represents a single or double bond; X independently from each other represents O or S; A and B independently from each other represent N or CR7; R1 and R6 are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4aR4b, C6-C14 aryl and hetaryl having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, wherein aryl and hetaryl being unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R9; or R1 and A together with the carbon atom to which they are attached form a C6-C14 aryl group or hetaryl group having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, aryl and hetaryl being unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9, or R6 and B together with the carbon atom to which they are attached form a C6-C14 aryl group or hetaryl group having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, aryl and hetaryl being unsubstituted or substituted with 1, 2, 3 or 4 identical or different radicals R9; R3 and R4 are independently selected from hydrogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4aR4b, C6-C14 aryl and hetaryl having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, wherein aryl and hetaryl being unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R9, or R3 and R4 together with the carbon atom to which they are attached form a C6-C14 aryl group or hetaryl group having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, aryl and hetaryl being unsubstituted or substituted with 1, 2, 3 or 4 identical or different R9 radicals; R2 and R5 are independently selected from hydrogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, NR4aR4b, C6-C14 aryl and hetaryl having 4 to 13 carbon atoms, wherein hetaryl having 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, wherein aryl and hetaryl being unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R9; R4aR4b are independently from each other selected from hydrogen, C1-C6 alkyl and C6 C14 aryl, wherein aryl is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R10; R7 is selected from hydrogen, CN, nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 haloalkylsulfanyl, NR4aR4b, C6-C14 aryl and hetaryl having 4 to 13 carbon atoms, wherein hetaryl has 1, 2 or 3 identical or different heteroatoms or heteroatom-containing groups as ring members selected from N, NR8, O, S, SO and SO2, wherein aryl and hetaryl are unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R10; R8 is selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl and C6-C14 aryl, wherein aryl is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals R10; R9 is selected from CN, halogen, C1-C6 alkyl, C1-C6 haloalkyl and C6-C14 aryl, wherein aryl is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different radicals selected from C1-C4 alkyl and C1-C4 haloalkyl; R10 is selected from CN, halogen, C1-C4 alkyl, C1-C4 haloalkyl, with the proviso that the following compounds and their reaction products are excluded: