METAL COMPLEX

Description

[0001] The present invention relates to binuclear metal complexes which are suitable for use as emitters in organic electroluminescent devices.

[0002] According to the state of the art, ortho-metalated iridium complexes with aromatic ligands are primarily used as triplet emitters in phosphorescent organic electroluminescent devices (OLEDs). The ligands bind to the metal via a negatively charged carbon atom and a neutral nitrogen atom. Binuclear iridium complexes, especially for red emission, are known from WO 2018 / 041769, and can be processed from solution.

[0003] In general, the external quantum efficiency of OLED components can be significantly increased if the transition dipole moment of the emission of the emitters contained therein is oriented as horizontally as possible, i.e., in the plane of the emission layer. This effect is known for vacuum-processed singlet and triplet emitters, as well as for solution-processed singlet emitters. The orientation of solution-processed polymers is also known. In contrast, the orientation of triplet emitters from solution is still an unsolved technical problem. It is known that emitters that orient themselves during evaporation do not do so from solution (e.g., Lampe et al., Chem. Mater. 2016, 28, 712-715). A 2019 review article (Watanabe et al., Bull. Chem. Soc. Jpn. 2019, 92, 716-728) also describes orientation from solution as an outstanding problem.The fact that compounds that can be evaporated in an oriented manner form non-oriented films from solution is attributed to differences in the film formation mechanism with regard to kinetic stability and molecular dynamics in solution.

[0004] In vacuum-processed triplet emitters, orientation and thus an improvement in the external quantum efficiency of the OLED can be achieved by substituting the optically active ligand with groups that lead to orientation through interaction with the surface during the vapor deposition process. Suitable substituents here include biphenyl groups or similar groups that are attached to the ligand in the direction of the transition dipole moment. However, such substituents, which already ensure orientation in vacuum-processed triplet emitters, do not lead to significant orientation in solution-processed triplet emitters, so this concept cannot be directly transferred to triplet emitters that are to be processed from solution. Complexes with an acetylacetonate ligand also often lead to orientation during vapor deposition, but not during processing from solution.

[0005] EP 3507294 A1 describes bi- and trinuclear metal complexes which are suitable for use as emitters in OLEDs.

[0006] The object of the present invention is to provide novel metal complexes that can be processed from solution and are suitable as emitters for use in OLEDs. In particular, the object is to provide emitters that lead to orientation when applied from solution, thus improving the external quantum efficiency of the OLED.

[0007] Surprisingly, it was found that the binuclear iridium complexes described below, which are substituted with linear, long-chain aromatic groups, lead to alignment when processed from solution and thus to a significant improvement in the external quantum efficiency in the OLED. These complexes and organic electroluminescent devices containing these complexes are therefore the subject of the present invention.

[0008] The invention relates to a compound according to the following formula (1), where the symbols and indices used are: X is, at each occurrence, the same or different, a group of the formula -(Ar) n -R; Y is, at each occurrence, the same or different, R or X; Z is, at each occurrence, the same or different, R or X; Ar is, at each occurrence, the same or different, a bivalent group selected from the structures (Ar1) to (Ar7), where the dashed bond represents the linkage between the units and V represents CR 2 , O, S or NR; n is, identically or differently, at each occurrence an integer from 3 to 20, with the proviso that in each unit -(Ar) n -R at least 5 phenyl and / or cyclohexyl groups are linked to one another in a linear manner;R can occur once or more than once and is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R 1< ) 2 , CN, NO 2 , OR 1< , SR 1< , COOH, C(=O)N(R 1< ) 2 , Si(R 1< ) 3 , B(OR 1< ) 2 , C(=O)R 1< , P(=O)(R 1< ) 2 , S(=O)R 1< , S(=O) 2 R 1< , OSO 2 R 1< , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl, Alkenyl or alkynyl group may each be substituted by one or more radicals R 1<, where one or more non-adjacent CH 2 groups may be replaced by Si(R 1<) 2, C=O, NR 1<, O, S or CONR 1<, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more radicals R 1<; two radicals R may also form a ring system with one another;R 1< is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R 2< ) 2 , CN, NO 2 , OR 2< , SR 2< , Si(R 2< ) 3 , B(OR 2< ) 2 , C(=O)R 2< , P(=O)(R 2< ) 2 , S(=O)R 2< , S(=O) 2 R 2< , OSO 2 R 2< , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl, alkenyl or alkynyl group may each be substituted by one or more radicals R 2<, where one or more non-adjacent CH 2 groups may be replaced by Si(R 2< ) 2 , C=O, NR 2< , O, S or CONR 2<, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more radicals R 2<; two or more radicals R 1< may form a ring system with one another;R 2< is, identically or differently, at each occurrence H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, in particular a hydrocarbon radical, having 1 to 20 C atoms, in which one or more H atoms may be replaced by F. ;

[0009] The characterizing feature of the compound according to the invention is the presence of two groups X, which are linearly linked aromatic or heteroaromatic groups, or cyclic aliphatic groups. In the definition of n, "provided that in each -(Ar) n -R unit, at least 5 phenyl and / or cyclohexyl groups are linearly linked to one another" means that the structure X has at least 5 linked phenyl or cyclohexane groups, whereby only the phenyl or cyclohexane groups linked directly one after the other are counted, but not potential substituents on these structures.The structures (Ar1) and (Ar3) each contribute one phenyl group, the structures (Ar2), (Ar4) and (Ar5) each contribute two phenyl groups, and the structures (Ar6) and (Ar7) each contribute one cyclohexane group, whereby the structure (Ar7) is also considered to be a cyclohexane group for the purposes of this invention, even if aromatic groups are also fused to this structure. Therefore, if the group X is composed, for example, only of groups (Ar1), n ​​must be ≥ 5 so that X has at least 5 interconnected phenyl groups. If, on the other hand, X is composed, for example, of a combination of groups (Ar1) and (Ar2), n can also be 3 if one group (Ar1) and two groups (Ar2) are present.

[0010] When two radicals R or R 1< form a ring system with one another, this ring system can be mono- or polycyclic, aliphatic, heteroaliphatic, aromatic, or heteroaromatic. The radicals forming a ring system can be adjacent, i.e., these radicals are bonded to the same carbon atom or to carbon atoms that are directly bonded to one another, or they can be further apart. Such ring formation is preferred for radicals that are bonded to carbon atoms that are directly bonded to one another or to the same carbon atom.

[0011] For the purposes of this description, the phrase "two or more residues can form a ring" is understood to mean, among other things, that the two residues are linked by a chemical bond with the formal elimination of two hydrogen atoms. This is illustrated by the following scheme.

[0012] Furthermore, the above formulation should also be understood to mean that if one of the two residues represents hydrogen, the second residue binds to the position to which the hydrogen atom was bonded, forming a ring. This is illustrated by the following scheme:

[0013] The formation of an aromatic or heteroaromatic ring system is illustrated by the following scheme:

[0014] An aryl group within the meaning of this invention contains 6 to 40 C atoms, a heteroaryl group within the meaning of this invention contains 2 to 40 C atoms and at least one heteroatom, with the proviso that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aryl group or heteroaryl group is understood to be either a simple aromatic cycle, i.e. benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a condensed aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc.

[0015] An aromatic ring system within the meaning of this invention contains 6 to 40 C atoms in the ring system. A heteroaromatic ring system within the meaning of this invention contains 1 to 40 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O, and / or S. An aromatic or heteroaromatic ring system within the meaning of this invention is understood to mean a system that does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups can also be interrupted by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as a C, N, or O atom or a carbonyl group. For example, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc.are understood as aromatic ring systems within the meaning of this invention, as are systems in which two or more aryl groups are interrupted, for example, by a linear or cyclic alkyl group or by a silyl group. Furthermore, systems in which two or more aryl or heteroaryl groups are directly bonded to one another, such as, for example, biphenyl, terphenyl, quaterphenyl or bipyridine, are also to be understood as aromatic or heteroaromatic ring systems. The aromatic or heteroaromatic ring system is preferably a system in which two or more aryl or heteroaryl groups are directly linked to one another via a single bond, or is fluorene, spirobifluorene or another aryl or heteroaryl group to which an optionally substituted indene group is fused, such as, for example, indenocarbazole.

[0016] In the context of the present invention, the term "alkyl group" is used as a generic term for linear, branched, and cyclic alkyl groups. Analogously, the terms "alkenyl group" and "alkynyl group" are used as generic terms for linear, branched, and cyclic alkenyl and alkynyl groups, respectively.

[0017] In the context of the present invention, a C 1 - to C 20 -alkyl group, in which individual H atoms or CH 2 groups can also be substituted by the above-mentioned groups, is understood to mean, for example, the radicals methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, Cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, trifluoromethyl, pentafluoroethyl, 2,2,2-Trifluoroethyl, 1,1-Dimethyl-n-hex-1-yl-, 1,1-Dimethyl-n-hept-1-yl-, 1,1-Dimethyl-n-oct-1-yl-, 1,1-Dimethyl-n-dec-1-yl-, 1,1-Dimethyl-n-dodec-1-yl-, 1,1-Dimethyl-n-tetradec-1-yl-, 1,1-Dimethyl-n-hexadec-1-yl-, 1,1-Dimethyl-n-octadec-1-yl-, 1,1-Diethyl-n-hex-1-yl-, 1,1-Diethyl-n-hept-1-yl-, 1,1-Diethyl-n-oct-1-yl-, 1,1-Diethyl-n-dec-1-yl-, 1,1-Diethyl-n-dodec-1-yl-, 1,1-Diethyl-n-tetradec-1-yl-, 1,1-Diethyln-n-hexadec-1-yl-, 1,1-Diethyl-n-octadec-1-yl-, 1-(n-propyl)-cyclohex-1-yl-, 1-(n-butyl)-cyclohex-1-yl-, 1-(n-hexyl)-cyclohex-1-yl-, 1-(n-Octyl)-cyclohex-1-yl- and 1-(n-Decyl)-cyclohex-1-yl- An alkenyl group is understood to mean, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, or cyclooctadienyl. An alkynyl group is understood to mean, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, or octynyl. A C 1 - to C 20 -alkoxy group, as present for OR 1< or OR 2<, is understood to mean, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, or 2-methylbutoxy.

[0018] An aromatic or heteroaromatic ring system with 5 - 40 aromatic ring atoms, which can also be substituted with the above-mentioned radicals and which can be linked to the aromatic or heteroaromatic ring via any position, is understood to mean, for example, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzfluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-monobenzoindenofluorene, cis- or trans-dibenzoindenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, Isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine,Benzo-5,6-chinolin, Benzo-6,7-chinolin, Benzo-7,8-chinolin, Phenothiazin, Phenoxazin, Pyrazol, Indazol, Imidazol, Benzimidazol, Naphthimidazol, Phenanthrimidazol, Pyridimidazol, Pyrazinimidazol, Chinoxalinimidazol, Oxazol, Benzoxazol, Naphthoxazol, Anthroxazol, Phenanthroxazol, Isoxazol, 1,2-Thiazol, 1,3-Thiazol, Benzothiazol, Pyridazin, Benzopyridazin, Pyrimidin, Benzpyrimidin, Chinoxalin, 1,5-Diazaanthracen, 2,7-Diazapyren, 2,3-Diazapyren, 1,6-Diazapyren, 1,8-Diazapyren, 4,5-Diazapyren, 4,5,9,10-Tetraazaperylen, Pyrazin, Phenazin, Phenoxazin, Phenothiazin, Fluorubin, Naphthyridin, Azacarbazol, Benzocarbolin, Phenanthrolin, 1,2,3-Triazol, 1,2,4-Triazol, Benzotriazol, 1,2,3-Oxadiazol, 1,2,4-Oxadiazol, 1,2,5-Oxadiazol, 1,3,4-Oxadiazol, 1,2,3-Thiadiazol, 1,2,4-Thiadiazol, 1,2,5-Thiadiazol, 1,3,4-Thiadiazol, 1,3,5-Triazin, 1,2,4-Triazin, 1,2,3-Triazin, Tetrazol, 1,2,4,5-Tetrazin, 1,2,3,4-Tetrazin, 1,2,3,5-Tetrazin, Purin, Pteridin, Indolizin und Benzothiadiazol.,

[0019] For illustrative purposes, the compound according to the invention is explained in more detail below: The compound contains a pyrimidine group, which coordinates to one iridium atom via each of the two nitrogen atoms. Two phenyl groups are bonded to the pyrimidine, each of which coordinates to one of the two iridium atoms via a carbon atom. A 1,3,5-tris(ortho-phenyl)benzene group is bonded to each of these two phenyl groups, each of which represents the bridgehead of the polypodal complex. Two optionally substituted phenylpyridine partial ligands are bonded to each of these 1,3,5-tris(ortho-phenyl)benzene groups. Each of the two iridium atoms is thus coordinated to two phenylpyridine partial ligands and one phenylpyrimidine partial ligand, with the pyrimidine group coordinating to both iridium atoms.

[0020] For the purposes of this application, the term "partial ligand" for the two phenylpyridine ligands means that these would be bidentate ligands if the 1,3,5-tris(ortho-phenyl)benzene group were not present. However, due to the formal abstraction of a hydrogen atom on the phenylpyridine and the linkage to the 1,3,5-tris(ortho-phenyl)benzene group, the phenylpyridine is not a separate ligand, but rather a part of the resulting dodecadentate ligand, i.e., a ligand with a total of 12 coordination sites, so the term "partial ligand" is used for this purpose.

[0021] The bond between the ligand and the iridium can be either a coordination bond or a covalent bond, and the covalent portion of the bond can vary depending on the ligand. Whenever this application refers to the ligand or partial ligand coordinating or binding to Ir, this refers, for the purposes of this application, to any type of bond between the ligand or partial ligand and the Ir, regardless of the covalent portion of the bond.

[0022] A preferred embodiment of the invention are the compounds of the following formula (1a), where the symbols used have the meanings given above.

[0023] In a preferred embodiment of the invention, both substituents X are the same.

[0024] In one embodiment of the invention, Y and Z are H. In a further embodiment of the invention, both groups Y are a group of the formula -(Ar) n -R, where the two groups Y are preferably the same but can be the same or different from the groups X, and Z is H. In yet another embodiment of the invention, both groups Y are H and Z is a group of the formula -(Ar) n -R, which can be the same or different from the groups X.

[0025] Preferred embodiments of formula (1) or (1a) are therefore the structures of the following formulas (1a-1), (1a-2) or (1a-3), where both groups X are each selected to be identical, and where the groups Y in formula (1a-2) each represent a group -(Ar) n -R and are selected to be identical, and where the group Z in formula (1a-3) represents a group -(Ar) n -R. Particular preference is given to the compounds of formula (1a-1).

[0026] The radical R in the group -(Ar) n -R preferably represents, identically or differently at each occurrence, H, a linear alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, in particular H.

[0027] Preferred Ar groups are listed below, which form the structures X or, where appropriate, also Y and Z. As described above, these are the bivalent structures (Ar1) to (Ar7), which can each be the same or different. What groups (Ar1) to (Ar7) have in common is that they lead to a linear linkage of the units within the group X, Y, or Z through the para linkage, or in formula (Ar3), a linkage similar to the para linkage. This is important because only then do the compounds according to the invention exhibit orientation upon deposition from solution.

[0028] Preferred embodiments of the structures (Ar1) are the following structures (Ar1a) to (Ar1f), where the dashed bonds represent the linkage of the structures, W stands for C(R 1< ) 2 , O, S or NR 1< and R and R 1< have the meanings given above. W preferably stands for O or S.

[0029] Preferred substituents R in the structures (Ar1b) to (Ar1d) are selected, identically or differently on each occurrence, from the group consisting of a linear alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, which may in each case be substituted by one or more radicals R 1<, but is preferably unsubstituted, or an aromatic ring system having 6 to 12 aromatic ring atoms, which may be substituted by one or more radicals R 1<, where R 1< preferably represents a linear alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, or a group OR 1<, where R 1< represents a linear alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms.

[0030] When W in formula (Ar1f) is C(R 1< ) 2 , R 1< preferably represents a linear alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms. When W in formula (Ar1f) is NR 1<, R 1< preferably represents an aromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 12 aromatic ring atoms, which may also be substituted by one or more alkyl groups each having 1 to 20 C atoms.

[0031] Preferred embodiments of the structures (Ar2) are the structures (Ar2a) and (Ar2b), where the dashed bonds represent the linkage of the structures and R and V have the meanings given above.

[0032] Particularly preferred embodiments of the structure (Ar2) are the following structures (Ar2a-1) to (Ar2a-5) and (Ar2b-1), where the dashed bonds represent the linkage of the structure and R and R 1< have the meanings given above.

[0033] Preferred substituents R in the structures (Ar2a-1) and (Ar2b-1) are selected, identically or differently at each occurrence, from the group consisting of a linear alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, each of which may be substituted by one or more radicals R 1<, but is preferably unsubstituted, or an aromatic ring system having 6 to 12 aromatic ring atoms, which may be substituted by one or more radicals R 1<, where R 1< preferably represents a linear alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms.

[0034] Preferred substituents R 1< in the structures (Ar2a-2) are, identically or differently at each occurrence, selected from the group consisting of H, a linear alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, each of which may be substituted by one or more radicals R 2<, but is preferably unsubstituted.

[0035] Preferred substituents R in the structures (Ar2a-5) are selected, identically or differently on each occurrence, from the group consisting of an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, which may be substituted by one or more radicals R 1<, preferably an aromatic ring system having 6 to 12 aromatic ring atoms, which may be substituted by one or more radicals R 1<, where R 1< preferably represents a linear alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms.

[0036] Preferred embodiments of the structures (Ar3) are the following structures (Ar3a), where the dashed bonds represent the linkage of the structure.

[0037] Preferred embodiments of the structures (Ar4) are the following structures (Ar4a) and (Ar4b), where the dashed bonds represent the linkage of the structure and R has the meanings given above.

[0038] Preferred substituents R in the structures (Ar4b) are selected, identically or differently on each occurrence, from the group consisting of a linear alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, each of which may be substituted by one or more radicals R 1<, but is preferably unsubstituted, or an aromatic ring system having 6 to 12 aromatic ring atoms, which may be substituted by one or more radicals R 1<, where R 1< preferably represents a linear alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms.

[0039] Preferred embodiments of the structures (Ar5) are the following structures (Ar5a) and (Ar5b), where the dashed bonds represent the linkage of the structure and R has the meanings given above.

[0040] Preferred substituents R in the structures (Ar5b) are, identically or differently at each occurrence, selected from the group consisting of H, a linear alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, each of which may be substituted by one or more radicals R 1<, but is preferably unsubstituted.

[0041] Preferred embodiments of the structures (Ar7) are the following structures (Ar7a), where the dashed bonds represent the linkage of the structure.

[0042] In a preferred embodiment of the invention, at least one Ar group is selected, identically or differently on each occurrence, from the structures (Ar1) and / or (Ar2), particularly preferably at least two Ar groups and very particularly preferably at least 3 Ar groups. Particularly preferably, all Ar groups are selected from the structures (Ar1) and / or (Ar2). The structures (Ar1) are preferably selected, identically or differently on each occurrence, from the structures (Ar1a) to (Ar1d), and the structures (Ar2) are selected from the structures (Ar2a), particularly preferably the structures (Ar2a-1).

[0043] If the radicals R or R 1< in the structures (Ar1) to (Ar7) or in the preferred structures described above represent linear, branched or cyclic alkyl groups, the alkyl groups preferably have 1 to 15 C atoms, particularly preferably 1 to 12 C atoms and very particularly preferably 1 to 10 C atoms. Examples of suitable alkyl groups as substituents R or R 1< in the structures (Ar1) to (Ar7) or in the preferred structures are methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n-Octyl, 2-Ethylhexyl, Cyclooctyl, 1-Bicyclo[2,2,2]octyl, 2-Bicyclo[2,2,2]octyl, 2-(2,6-Dimethyl)octyl, 3-(3,7-Dimethyl)octyl, Adamantyl, 1,1-Dimethyl-n-hex-1-yl-, 1,1-Dimethyl-n-hept-1-yl-, 1,1-Dimethyl-n-oct-1-yl-, 1,1-Dimethyl-n-dec-1-yl-, 1,1-Dimethyl-n-dodec-1-yl-, 1,1-Dimethyl-n-tetradec-1-yl-, 1,1-Dimethyl-n-hexadec-1-yl-, 1,1-Dimethyl-n-octadec-1-yl-, 1,1-Diethyl-n-hex-1-yl-, 1,1-Diethyl-n-hept-1-yl-, 1,1-Diethyl-n-oct-1-yl-, 1,1-Diethyl-n-dec-1-yl-, 1,1-Diethyl-n-dodec-1-yl-, 1,1-Diethyl-n-tetradec-1-yl-, 1,1-Diethyln-n-hexadec-1-yl-, 1,1-Diethyl-n-octadec-1-yl, 1-(n-propyl)-cyclohex-1-yl, 1-(n-butyl)-cyclohex-1-yl, 1-(n-hexyl)-cyclohex-1-yl, 1-(n-octyl)-cyclohex-1-yl, and 1-(n-decyl)-cyclohex-1-yl. The alkyl groups can each have one or more stereocenters, in which case both the enantiomerically or diastereomerically pure structures and the corresponding racemates can be used.

[0044] As described above, n is an integer from 3 to 20, with the proviso that at least 5 phenyl or cyclohexane groups are linked to one another in a linear fashion. In a preferred embodiment of the invention, n is an integer from 5 to 20, in particular from 5 to 15. Particularly preferably, n is chosen such that a total of 8 to 24 phenyl or cyclohexane groups are linked to one another in a linear fashion, particularly preferably 12 to 24 phenyl or cyclohexane groups, and very particularly preferably 15 to 20 phenyl or cyclohexane groups. As described above, the structures (Ar2), (Ar4), and (Ar5) each contribute two phenyl groups.

[0045] Preferred embodiments of the phenylpyridine partial ligands are described below. If the phenylpyridine partial ligands in formula (1) are substituted with one or more R radicals, then these substituents are preferably bonded as shown in the following formula (2), where the symbols used have the meanings listed above.

[0046] The same preferred positions of the R residues on the phenylpyridine subligands also apply in the preferred structures.

[0047] Preferred are the structures of the following formula (2a), where the symbols used have the meanings given above.

[0048] For the substituents on the phenylpyridine partial ligands, it is preferred that each of the four partial ligands is substituted identically. Furthermore, each phenylpyridine partial ligand preferably contains a maximum of three substituents R other than H, particularly preferably a maximum of two substituents R. If two substituents R other than H are bonded to the pyridine ring, preferably at least one of the two substituents is an alkyl group. Particularly preferably, a maximum of one substituent R on the pyridine represents a group other than H.In a further preferred embodiment of the invention, the phenyl group of the phenylpyridine partial ligand contains a substituent R which is bonded in the para position to the iridium, wherein this substituent R is preferably selected from aromatic ring systems having 6 to 24 aromatic ring atoms, preferably having 6 to 12 aromatic ring atoms, each of which may be substituted by one or more radicals R 1<, wherein R 1< is preferably selected from linear alkyl groups having 1 to 10 C atoms or branched or cyclic alkyl groups having 3 to 10 C atoms, wherein R is in particular an unsubstituted phenyl group.In a further preferred embodiment of the invention, the pyridine group of the phenylpyridine partial ligand contains a substituent R which is bonded in the para position to the nitrogen atom, wherein this substituent R is preferably selected from a linear alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, in particular a methyl group.

[0049] The R radicals on the phenylpyridine partial ligands in formula (1) or the preferred embodiments are preferably selected, identically or differently at each occurrence, from the group consisting of H, D, F, OR 1< , CN, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, where the alkyl group may in each case be substituted by one or more R 1< radicals, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more R 1< radicals; two adjacent R radicals may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another.These R radicals are particularly preferably selected, identically or differently at each occurrence, from the group consisting of H, D, F, OR 1< , a straight-chain alkyl group having 1 to 6 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, where one or more H atoms may be replaced by D or F, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, preferably having 6 to 13 aromatic ring atoms, each of which may be substituted by one or more R 1< radicals; two adjacent R radicals may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another. Particularly preferred aromatic ring systems are phenyl, which may also be substituted by one or two alkyl groups each having 1 to 6 C atoms, or biphenyl.

[0050] Preferred radicals R 1< which are bonded to R are, on each occurrence, identically or differently, H, D, F, CN, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 2<, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2<; two or more adjacent radicals R 1< may form a mono- or polycyclic, aliphatic ring system with one another.Particularly preferred radicals R 1< which are bonded to R are, on each occurrence, identically or differently, H, F, CN, a straight-chain alkyl group having 1 to 5 C atoms or a branched or cyclic alkyl group having 3 to 5 C atoms, each of which may be substituted by one or more radicals R 2<, or an aromatic or heteroaromatic ring system having 5 to 13 aromatic ring atoms, each of which may be substituted by one or more radicals R 2<; two or more adjacent radicals R 1< can form a mono- or polycyclic, aliphatic ring system with one another.

[0051] Preferred radicals R 2< are, identically or differently at each occurrence, H, F or an aliphatic hydrocarbon radical having 1 to 5 C atoms or an aromatic hydrocarbon radical having 6 to 12 C atoms; two or more substituents R 2< can also form a mono- or polycyclic, aliphatic ring system with one another.

[0052] The above-mentioned preferred embodiments can be combined with one another as desired within the scope of the claims. In a particularly preferred embodiment of the invention, the above-mentioned preferred embodiments apply simultaneously.

[0053] The compounds of the invention are chiral structures. Depending on the precise structure of the complexes and ligands, the formation of diastereomers and multiple enantiomer pairs is possible. The complexes of the invention then comprise both mixtures of the various diastereomers or the corresponding racemates as well as the individual isolated diastereomers or enantiomers. The diastereomer pairs can be separated using conventional methods, e.g., chromatography or fractional crystallization. Racemate resolution can be achieved via fractional crystallization of diastereomeric salt pairs or on chiral columns using conventional methods.

[0054] Examples of suitable compounds according to the invention are listed below. In these example structures, the groups X have the following general structure:

[0055] Structures 1 to 34 listed below are suitable structures for A 1 to A 10 . A 1 bonds to the metal complex via the dashed bond, and in the structures in the table below, the last A n group has a hydrogen atom instead of the dashed bond. Asymmetric groups (groups 3, 4, 6, 9, 10, and 18) can be linked to the previous group via either of the two dashed lines. For clarity, only one isomeric form has been shown in these cases.

[0056] From the structures 1 to 34 listed above, the suitable groups X shown in the following table can be constructed: X A1 A2 A3 A4 A5 A6 A7 A8 A9 A10 1 1 17 18 18 - - - - - - 2 2 17 18 18 - - - - - - 3 3 17 18 18 - - - - - - 4 4 17 18 18 - - - - - - 5 5 17 18 18 - - - - - - 6 6 17 18 18 - - - - - - 7 7 17 18 18 - - - - - - 8 10 17 18 18 - - - - - - 9 14 17 18 18 - - - - - - 10 15 17 18 18 - - - - - - 11 19 17 18 18 - - - - - - 11 20 17 18 18 - - - - - - 13 21 17 18 18 - - - - - - 14 22 17 18 18 - - - - - - 15 23 17 18 18 - - - - - - 16 24 17 18 18 - - - - - - 17 25 17 18 18 - - - - - - 18 26 17 18 18 - - - - - - 19 27 17 18 18 - - - - - - 20 1 17 18 18 18 - - - - - 21 2 17 18 18 18 - - - - - 22 3 17 18 18 18 - - - - - 23 4 17 18 18 18 - - - - - 24 5 17 18 18 18 - - - - - 25 6 17 18 18 18 - - - - - 26 7 17 18 18 18 - - - - - 27 10 17 18 18 18 - - - - - 28 14 17 18 18 18 - - - - - 29 15 17 18 18 18 - - - - - 30 19 17 18 18 18 - - - - - 31 20 17 18 18 18 - - - - - 32 21 17 18 18 18 - - - - - 33 22 17 18 18 18 - - - - - 34 23 17 18 18 18 - - - - - 35 24 17 18 18 18 - - - - - 36 25 17 18 18 18 - - - - - 37 26 17 18 18 18 - - - - - 38 27 17 18 18 18 - - - - - 39 1 4 1 8 1 8 18 - - - 40 2 4 1 8 1 8 18 - - - 41 3 4 1 8 1 8 18 - - - 42 4 4 1 8 1 8 18 - - - 43 5 4 1 8 1 8 18 - - - 44 6 4 1 8 1 8 18 - - - 45 7 4 1 8 1 8 18 - - - 46 10 4 1 8 1 8 18 - - - 47 14 4 1 8 1 8 18 - - - 48 15 4 1 8 1 8 18 - - - 49 19 4 1 8 1 8 18 - - - 50 20 4 1 8 1 8 18 - - - 51 21 4 1 8 1 8 18 - - - 52 22 4 1 8 1 8 18 - - - 53 23 4 1 8 1 8 18 - - - 54 24 4 1 8 1 8 18 - - - 55 25 4 1 8 1 8 18 - - - 56 26 4 1 8 1 8 18 - - - 57 27 4 1 8 1 8 18 - - - 58 1 1 13 1 21 13 21 13 - - 59 1 2 13 1 21 13 21 13 - - 60 1 3 13 1 21 13 21 13 - - 61 1 4 13 1 21 13 21 13 - - 62 1 6 13 1 21 13 21 13 - - 63 1 7 13 1 21 13 21 13 - - 64 1 9 13 1 21 13 21 13 - - 65 1 23 1 21 22 16 - - - - 66 1 24 1 21 22 16 - - - - 67 1 25 1 21 22 16 - - - - 68 1 26 1 21 22 16 - - - - 69 1 27 1 21 22 16 - - - - 70 4 13 14 13 14 13 14 13 14 13 71 4 13 1 13 1 13 1 13 1 13 72 4 13 2 13 2 13 2 13 2 13 73 4 13 4 13 4 13 4 13 4 13 74 4 13 7 13 7 13 7 13 7 13 75 4 13 23 13 23 13 23 13 23 13 76 4 13 26 13 26 13 26 13 26 13 77 1 13 14 13 14 13 14 13 14 13 78 1 13 1 13 1 13 1 13 1 13 79 1 13 2 13 2 13 2 13 2 13 80 1 13 4 13 4 13 4 13 4 13 81 1 13 7 13 7 13 7 13 7 13 82 1 13 23 13 23 13 23 13 23 13 83 1 13 26 13 26 13 26 13 26 13 84 4 27 14 27 14 27 14 27 14 27 85 4 27 1 27 1 27 1 27 1 27 86 4 27 2 27 2 27 2 27 2 27 87 4 27 4 27 4 27 4 27 4 27 88 4 27 7 27 7 27 7 27 7 27 89 4 27 23 27 23 27 23 27 23 27 90 4 27 26 27 26 27 26 27 26 27 91 1 27 14 27 14 27 14 27 14 27 92 1 27 1 27 1 27 1 27 1 27 93 1 27 2 27 2 27 2 27 2 27 94 1 27 4 27 4 27 4 27 4 27 95 1 27 7 27 7 27 7 27 7 27 96 1 27 23 27 23 27 23 27 23 27 97 1 27 26 27 26 27 26 27 26 27 98 4 11 14 11 14 11 14 11 14 11 99 4 11 1 11 1 11 1 11 1 11 100 4 11 2 11 2 11 2 11 2 11 101 4 11 4 11 4 11 4 11 4 11 102 4 11 7 11 7 11 7 11 7 11 103 4 11 23 11 23 11 23 11 23 11 104 4 11 26 11 26 11 26 11 26 11 105 1 11 14 11 14 11 14 11 14 11 106 1 11 1 11 1 11 1 11 1 11 107 1 11 2 11 2 11 2 11 2 11 108 1 11 4 11 4 11 4 11 4 11 109 1 11 7 11 7 11 7 11 7 11 110 1 11 23 11 23 11 23 11 23 11 111 1 11 26 11 26 11 26 11 26 11 112 1 17 1 18 18 - - - - - 113 2 17 2 18 18 - - - - - 114 3 17 3 18 18 - - - - - 115 4 17 4 18 18 - - - - - 116 5 17 5 18 18 - - - - - 117 6 17 6 18 18 - - - - - 118 7 17 7 18 18 - - - - - 119 10 17 10 18 18 - - - - - 120 14 17 14 18 18 - - - - - 121 15 17 15 18 18 - - - - - 122 19 17 19 18 18 - - - - - 123 20 17 20 18 18 - - - - - 124 21 17 21 18 18 - - - - - 125 22 17 22 18 18 - - - - - 126 23 17 23 18 18 - - - - - 127 24 17 24 18 18 - - - - - 128 25 17 25 18 18 - - - - - 129 26 17 26 18 18 - - - - - 130 27 17 27 18 18 - - - - - 131 1 21 18 18 - - - - - - 132 2 21 18 18 - - - - - - 133 3 21 18 18 - - - - - - 134 4 21 18 18 - - - - - - 135 5 21 18 18 - - - - - - 136 6 21 18 18 - - - - - - 137 7 21 18 18 - - - - - - 138 10 21 18 18 - - - - - - 139 14 21 18 18 - - - - - - 140 15 21 18 18 - - - - - - 141 19 21 18 18 - - - - - - 142 20 21 18 18 - - - - - - 143 21 21 18 18 - - - - - - 144 22 21 18 18 - - - - - - 145 23 21 18 18 - - - - - - 146 24 21 18 18 - - - - - - 147 25 21 18 18 - - - - - - 148 26 21 18 18 - - - - - - 149 27 21 18 18 - - - - - - 150 1 22 18 18 - - - - - - 151 2 22 18 18 - - - - - - 152 3 22 18 18 - - - - - - 153 4 22 18 18 - - - - - - 154 5 22 18 18 - - - - - - 155 6 22 18 18 - - - - - - 156 7 22 18 18 - - - - - - 157 10 22 18 18 - - - - - - 158 14 22 18 18 - - - - - - 159 15 22 18 18 - - - - - - 160 19 22 18 18 - - - - - - 161 20 22 18 18 - - - - - - 162 21 22 18 18 - - - - - - 163 22 22 18 18 - - - - - - 164 23 22 18 18 - - - - - - 165 24 22 18 18 - - - - - - 166 25 22 18 18 - - - - - - 167 26 22 18 18 - - - - - - 168 27 22 18 18 - - - - - - 169 18 1 18 18 - - - - - - 170 18 2 18 18 - - - - - - 171 18 3 18 18 - - - - - - 172 18 4 18 18 - - - - - - 173 18 5 18 18 - - - - - - 174 18 6 18 18 - - - - - - 175 18 7 18 18 - - - - - - 176 18 10 18 18 - - - - - - 177 18 14 18 18 - - - - - - 178 18 15 18 18 - - - - - - 179 18 19 18 18 - - - - - - 180 18 20 18 18 - - - - - - 181 18 21 18 18 - - - - - - 182 18 22 18 18 - - - - - - 183 18 23 18 18 - - - - - - 184 18 24 18 18 - - - - - - 185 18 25 18 18 - - - - - - 186 18 26 18 18 - - - - - - 187 18 27 18 18 - - - - - - 188 18 28 18 18 - - - - - - 189 18 29 18 18 - - - - - - 190 18 30 18 18 - - - - - - 191 18 31 18 18 - - - - - - 192 18 32 18 18 - - - - - - 193 18 33 18 18 - - - - - - 194 18 34 18 18 - - - - - - 195 28 28 18 18 - - - - - - 196 29 29 18 18 - - - - - - 197 30 30 18 18 - - - - - - 198 31 31 18 18 - - - - - - 199 32 32 18 18 - - - - - - 200 33 33 18 18 - - - - - - 201 34 34 18 18 - - - - - - 202 1 28 1 28 11 28 - - - - 203 1 29 1 29 11 29 - - - - 204 1 30 1 30 11 30 - - - - 205 1 31 1 31 11 31 - - - - 206 1 32 1 32 11 32 - - - - 207 1 33 1 33 11 33 - - - - 208 1 34 1 34 11 34 - - - - 209 1 8 1 8 1 - - - - - 210 2 8 2 8 2 - - - - - 211 3 8 3 8 3 - - - - - 212 4 8 4 8 4 - - - - - 213 5 8 5 8 5 - - - - - 214 6 8 6 8 6 - - - - - 215 7 8 7 8 7 - - - - - 216 8 8 8 8 8 - - - - - 217 9 8 9 8 9 - - - - - 218 10 8 10 8 10 - - - - - 219 11 8 11 8 11 - - - - - 220 12 8 12 8 12 - - - - - 221 13 8 13 8 13 - - - - - 222 14 8 14 8 14 - - - - - 223 15 8 15 8 15 - - - - - 224 16 8 16 8 16 - - - - - 225 1 8 1 8 1 8 - - - - 226 2 8 2 8 2 8 - - - - 227 3 8 3 8 3 8 - - - - 228 4 8 4 8 4 8 - - - - 229 5 8 5 8 5 8 - - - - 230 6 8 6 8 6 8 - - - - 231 7 8 7 8 7 8 - - - - 232 8 8 8 8 8 8 - - - - 233 9 8 9 8 9 8 - - - - 234 10 8 10 8 10 8 - - - - 235 11 8 11 8 11 8 - - - - 236 12 8 12 8 12 8 - - - - 237 13 8 13 8 13 8 - - - - 238 14 8 14 8 14 8 - - - - 239 15 8 15 8 15 8 - - - - 240 16 8 16 8 16 8 - - - - 241 1 8 1 8 1 11 - - - - 242 2 8 2 8 2 11 - - - - 243 3 8 3 8 3 11 - - - - 244 4 8 4 8 4 11 - - - - 245 5 8 5 8 5 11 - - - - 246 6 8 6 8 6 11 - - - - 247 7 8 7 8 7 11 - - - - 248 8 8 8 8 8 11 - - - - 249 9 8 9 8 9 11 - - - - 250 10 8 10 8 10 11 - - - - 251 11 8 11 8 11 11 - - - - 252 12 8 12 8 12 11 - - - - 253 13 8 13 8 13 11 - - - - 254 14 8 14 8 14 11 - - - - 255 15 8 15 8 15 11 - - - - 256 16 8 16 8 16 11 - - - - 257 1 11 1 11 1 11 - - - - 258 2 11 2 11 2 11 - - - - 259 3 11 3 11 3 11 - - - - 260 4 11 4 11 4 11 - - - - 261 5 11 5 11 5 11 - - - - 262 6 11 6 11 6 11 - - - - 263 7 11 7 11 7 11 - - - - 264 8 11 8 11 8 11 - - - - 265 9 11 9 11 9 11 - - - - 266 10 11 10 11 10 11 - - - - 267 11 11 11 11 11 11 - - - - 268 12 11 12 11 12 11 - - - - 269 13 11 13 11 13 11 - - - - 270 14 11 14 11 14 11 - - - - 271 15 11 15 11 15 11 - - - - 272 16 11 16 11 16 11 - - - - 273 1 18 1 20 20 - - - - - 274 1 18 1 20 20 1 - - - - 275 1 18 1 20 20 2 - - - - 276 1 18 1 20 20 3 - - - - 277 1 18 1 20 20 4 - - - - 278 1 18 1 20 20 5 - - - - 279 1 18 1 20 20 6 - - - - 280 1 18 1 20 20 7 - - - - 281 1 18 1 20 20 8 - - - - 282 1 18 1 20 20 9 - - - - 283 1 18 1 20 20 10 - - - - 284 1 18 1 20 20 11 - - - - 285 1 18 1 20 20 12 - - - -

[0057] These groups X listed above can, for example, be linked to the following bimetallic complexes via the dashed bonds: H1 H2 H3 H4 H5 H6 H7 H8 H9 H10

[0058] H1-H10 in the table above are each linked to the X groups via both dashed lines. All X groups listed above can be linked to any of the complexes H1 to H10. This is shown as an example for H1 and the groups X1-X285 in the table below: H X H X 1 H1 X1 144 H1 X144 2 H1 X2 145 H1 X145 3 H1 X3 146 H1 X146 4 H1 X4 147 H1 X147 5 H1 X5 148 H1 X148 6 H1 X6 149 H1 X149 7 H1 X7 150 H1 X150 8 H1 X8 151 H1 X151 9 H1 X9 152 H1 X152 10 H1 X10 153 H1 X153 11 H1 X11 154 H1 X154 12 H1 X12 155 H1 X155 13 H1 X13 156 H1 X156 14 H1 X14 157 H1 X157 15 H1 X15 158 H1 X158 16 H1 X16 159 H1 X159 17 H1 X17 160 H1 X160 18 H1 X18 161 H1 X161 19 H1 X19 162 H1 X162 20 H1 X20 163 H1 X163 21 H1 X21 164 H1 X164 22 H1 X22 165 H1 X165 23 H1 X23 166 H1 X166 24 H1 X24 167 H1 X167 25 H1 X25 168 H1 X168 26 H1 X26 169 H1 X169 27 H1 X27 170 H1 X170 28 H1 X28 171 H1 X171 29 H1 X29 172 H1 X172 30 H1 X30 173 H1 X173 31 H1 X31 174 H1 X174 32 H1 X32 175 H1 X175 33 H1 X33 176 H1 X176 34 H1 X34 177 H1 X177 35 H1 X35 178 H1 X178 36 H1 X36 179 H1 X179 37 H1 X37 180 H1 X180 38 H1 X38 181 H1 X181 39 H1 X39 182 H1 X182 40 H1 X40 183 H1 X183 41 H1 X41 184 H1 X184 42 H1 X42 185 H1 X185 43 H1 X43 186 H1 X186 44 H1 X44 187 H1 X187 45 H1 X45 188 H1 X188 46 H1 X46 189 H1 X189 47 H1 X47 190 H1 X190 48 H1 X48 191 H1 X191 49 H1 X49 192 H1 X192 50 H1 X50 193 H1 X193 51 H1 X51 194 H1 X194 52 H1 X52 195 H1 X195 53 H1 X53 196 H1 X196 54 H1 X54 197 H1 X197 55 H1 X55 198 H1 X198 56 H1 X56 199 H1 X199 57 H1 X57 200 H1 X200 58 H1 X58 201 H1 X201 59 H1 X59 202 H1 X202 60 H1 X60 203 H1 X203 61 H1 X61 204 H1 X204 62 H1 X62 205 H1 X205 63 H1 X63 206 H1 X206 64 H1 X64 207 H1 X207 65 H1 X65 208 H1 X208 66 H1 X66 209 H1 X209 67 H1 X67 210 H1 X210 68 H1 X68 211 H1 X211 69 H1 X69 212 H1 X212 70 H1 X70 213 H1 X213 71 H1 X71 214 H1 X214 72 H1 X72 215 H1 X215 73 H1 X73 216 H1 X216 74 H1 X74 217 H1 X217 75 H1 X75 218 H1 X218 76 H1 X76 219 H1 X219 77 H1 X77 220 H1 X220 78 H1 X78 221 H1 X221 79 H1 X79 222 H1 X222 80 H1 X80 223 H1 X223 81 H1 X81 224 H1 X224 82 H1 X82 225 H1 X225 83 H1 X83 226 H1 X226 84 H1 X84 227 H1 X227 85 H1 X85 228 H1 X228 86 H1 X86 229 H1 X229 87 H1 X87 230 H1 X230 88 H1 X88 231 H1 X231 89 H1 X89 232 H1 X232 90 H1 X90 233 H1 X233 91 H1 X91 234 H1 X234 92 H1 X92 235 H1 X235 93 H1 X93 236 H1 X236 94 H1 X94 237 H1 X237 95 H1 X95 238 H1 X238 96 H1 X96 239 H1 X239 97 H1 X97 240 H1 X240 98 H1 X98 241 H1 X241 99 H1 X99 242 H1 X242 100 H1 X100 243 H1 X243 101 H1 X101 244 H1 X244 102 H1 X102 245 H1 X245 103 H1 X103 246 H1 X246 104 H1 X104 247 H1 X247 105 H1 X105 248 H1 X248 106 H1 X106 249 H1 X249 107 H1 X107 250 H1 X250 108 H1 X108 251 H1 X251 109 H1 X109 252 H1 X252 110 H1 X110 253 H1 X253 111 H1 X111 254 H1 X254 112 H1 X112 255 H1 X255 113 H1 X113 256 H1 X256 114 H1 X114 257 H1 X257 115 H1 X115 258 H1 X258 116 H1 X116 259 H1 X259 117 H1 X117 260 H1 X260 118 H1 X118 261 H1 X261 119 H1 X119 262 H1 X262 120 H1 X120 263 H1 X263 121 H1 X121 264 H1 X264 122 H1 X122 265 H1 X265 123 H1 X123 266 H1 X266 124 H1 X124 267 H1 X267 125 H1 X125 268 H1 X268 126 H1 X126 269 H1 X269 127 H1 X127 270 H1 X270 128 H1 X128 271 H1 X271 129 H1 X129 272 H1 X272 130 H1 X130 273 H1 X273 131 H1 X131 274 H1 X274 132 H1 X132 275 H1 X275 133 H1 X133 276 H1 X276 134 H1 X134 277 H1 X277 135 H1 X135 278 H1 X278 136 H1 X136 279 H1 X279 137 H1 X137 280 H1 X280 138 H1 X138 281 H1 X281 139 H1 X139 282 H1 X282 140 H1 X140 283 H1 X283 141 H1 X141 284 H1 X284 142 H1 X142 285 H1 X285 143 H1 X143

[0059] The complexes according to the invention can be prepared in particular by the method described below. For this purpose, the 12-dentate ligand is prepared, which contains reactive leaving groups instead of the groups X and optionally Y and / or Z, and then coordinated to the iridium metals by an ortho-metalation reaction. Alternatively, it is also possible to first synthesize the metal complex, which does not yet contain any reactive leaving groups, and then introduce the reactive leaving groups onto the complex. Suitable reactive leaving groups include, for example, halogen, in particular chlorine, bromine or iodine, triflate, tosylate or a boronic acid derivative, for example boronic acid or a boronic acid ester. The groups X and optionallyY and / or Z can then be reacted by a coupling reaction with a compound A-(Ar) n -R, where A represents a reactive leaving group, for example halogen, especially chlorine, bromine or iodine, triflate, tosylate, or a boronic acid derivative, for example boronic acid or a boronic acid ester. Generally, all CC coupling reactions are suitable, especially the Suzuki coupling. Such reactions are known to the person skilled in the art, and they will have no difficulty applying them to the compounds of the invention.

[0060] Therefore, the present invention further provides a process for preparing the compound according to the invention by reacting a compound which is substituted with reactive leaving groups instead of X and optionally Y and / or Z, with a compound A-(Ar) n -R, where A represents a reactive leaving group. The reaction is preferably a Suzuki coupling.

[0061] For processing the compounds of the invention from the liquid phase, for example by spin coating or printing processes, formulations of the compounds of the invention are required. These formulations can be, for example, solutions, dispersions, or emulsions. It may be preferable to use mixtures of two or more solvents for this purpose. The solvents are preferably selected from hydrocarbons, alcohols, esters, ethers, ketones, and amines. Suitable and preferred solvents are, for example, selected from toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, verartrol, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 1-ethylnaphthalene, decylbenzene, phenylnaphthalene, menthyl isovalerate, para-tolyl isobutyrate, cyclohexyl hexanoate, ethyl para-toluate, ethyl ortho-toluate, ethyl meta-toluate,Decahydronaphthalin, Ethyl-2-methoxybenzoat, Dibutylanilin, Dicyclohexylketon, Isosorbid-dimethylether, Decahydronaphthalin, 2-Methylbiphenyl, Ethyl-octanoat, Octyl-octanoat, Diethyl-sebacat, 3,3-Dimethylbiphenyl, 1,4-Dimethylnaphthalin, 2,2'-Dimethylbiphenyl, 2-Methylbenzothiazol, 2-Phenoxyethanol, 2-Pyrrolidinon, 3-Methylanisol, 4-Methylanisol, 3,4-Dimethylanisol, 3,5-Dimethylanisol, Acetophenon, α-Terpineol, Benzothiazol, Butylbenzoat, Cumol, Cyclohexanol, Cyclohexanon, Cyclohexylbenzol, Decalin, Dodecylbenzol, Ethyl-benzoat, Indan, NMP, p-Cymol, Phenetol, 1,4-Diisopropylbenzol, Dibenzylether, Diethylenglycolbutylmethylether, Triethylenglycolbutylmethylether, Diethylenglycoldibutylether, Triethylenglycoldimethylether, Diethylenglycolmonobutylether, Tripropylenglycoldimethylether, Tetraethylenglycoldimethylether, 2-Isopropylnaphthalin, Pentylbenzol, Hexylbenzol, Heptylbenzol, Octylbenzol, 1,1-Bis-(3,4-dimethylphenyl)ethan oder Mischungen dieser Lösemittel.,

[0062] The present invention therefore further provides a formulation comprising at least one compound according to the invention and at least one further compound. The further compound can be, for example, a solvent, in particular one of the above-mentioned solvents or a mixture of these solvents. However, the further compound can also be another organic or inorganic compound that is also used in the electronic device, for example, a matrix material. This further compound can also be polymeric.

[0063] The compound according to the invention described above or the preferred embodiments listed above can be used as an active component in an electronic device. The present invention thus further relates to the use of a compound according to the invention in an electronic device. The present invention further relates to an electronic device comprising at least one compound according to the invention.

[0064] An electronic device is understood to be a device that contains an anode, a cathode, and at least one layer, wherein this layer contains at least one organic or organometallic compound. The electronic device according to the invention thus contains an anode, a cathode, and at least one layer containing at least one compound according to the invention.Preferred electronic devices are selected from the group consisting of organic electroluminescent devices (OLEDs, PLEDs), organic infrared electroluminescent sensors, organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), which include both purely organic solar cells and dye-sensitized solar cells (Grätzel cells), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), light-emitting electrochemical cells (LECs), oxygen sensors, or organic laser diodes (O-lasers), comprising at least one compound according to the invention in at least one layer. Organic electroluminescent devices are particularly preferred.Active components are generally the organic or inorganic materials introduced between the anode and cathode, for example, charge injection, charge transport, or charge blocking materials, but especially emission materials and matrix materials. The compounds of the invention exhibit particularly good properties as emission materials in organic electroluminescent devices. A preferred embodiment of the invention is therefore organic electroluminescent devices.

[0065] The organic electroluminescent device contains a cathode, an anode, and at least one emitting layer. In addition to these layers, it may contain further layers, for example, one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, charge generation layers, and / or organic or inorganic p / n junctions. It is possible for one or more hole transport layers to be p-doped, for example with metal oxides such as MoO3 or WO3 or with (per)fluorinated electron-poor aromatics, and / or for one or more electron transport layers to be n-doped. Interlayers can also be introduced between two emitting layers, which, for example, have an exciton-blocking function and / or control the charge balance in the electroluminescent device.It should be noted, however, that not every one of these layers necessarily has to be present.

[0066] The organic electroluminescent device can contain one emitting layer or it can contain multiple emitting layers. If multiple emitting layers are present, these preferably have a total of multiple emission maxima between 380 nm and 750 nm, resulting in overall white emission, i.e. different emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. Particular preference is given to three-layer systems, wherein the three layers exhibit blue, green and orange or red emission (for the basic structure see, for example, WO 2005 / 011013), or systems that have more than three emitting layers. It can also be a hybrid system, wherein one or more layers fluoresce and one or more other layers phosphoresce.White-emitting organic electroluminescent devices can be used for lighting applications or, with a color filter, for full-color displays. White-emitting OLEDs can also be realized using tandem OLEDs. Furthermore, white-emitting OLEDs can also be realized by combining two or more emitters that emit light in different colors, at least one of which is a compound according to the invention, in an emitting layer, so that the emitted light from the individual emitters adds up to white light.

[0067] In a preferred embodiment of the invention, the organic electroluminescent device contains the compound according to the invention as an emitting compound in one or more emitting layers.

[0068] Many of the compounds of the invention emit light in the red spectral range. However, by appropriately selecting the ligands and substitution patterns, it is also possible to shift the emission into the infrared range on the one hand and to shift it hypsochromically, preferably into the orange or yellow range on the other.

[0069] When the compound according to the invention is used as an emitting compound in an emitting layer, it is preferably used in combination with one or more matrix materials, the terms "matrix material" and "host material" being used synonymously below. The mixture of the compound according to the invention and the matrix material contains between 0.1 and 99 wt. %, preferably between 3 and 90 wt. %, particularly preferably between 5 and 40 wt. %, in particular between 10 and 25 wt. %, of the compound according to the invention, based on the total mixture of emitter and matrix material. Accordingly, the mixture contains between 99.9 and 1 wt. %, preferably between 97 and 10 wt. %, particularly preferably between 95 and 60 wt. %, in particular between 90 and 75 wt. % of the matrix material, based on the total mixture of emitter and matrix material.

[0070] In general, any materials known in the art can be used as the matrix material. Preferably, the triplet level of the matrix material is higher than the triplet level of the emitter.

[0071] Suitable matrix materials for the compounds according to the invention are ketones, phosphine oxides, sulfoxides and sulfones, e.g. according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680, triarylamines, carbazole derivatives, e.g. CBP (N,N-bis-carbazolylbiphenyl), m-CBP or the carbazole derivatives disclosed in WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or US 2009 / 0134784, indolocarbazole derivatives, e.g. according to WO 2007 / 063754 or WO 2008 / 056746, indenocarbazole derivatives, e.g. according to WO 2010 / 136109 or WO 2011 / 000455, azacarbazoles, e.g. according to EP 1617710, EP 1617711, EP 1731584, JP 2005 / 347160, bipolar matrix materials, e.g. according to WO 2007 / 137725, silanes, e.g. according to WO 2005 / 111172, azaboroles or boronic esters, e.g. according to WO 2006 / 117052, diazasilole derivatives, e.g. according to WO 2010 / 054729, diazaphosphole derivatives, e.g. B. according to WO 2010 / 054730, triazine derivatives, e.g. according to WO 2010 / 015306, WO 2007 / 063754 or WO 2008 / 056746, zinc complexes, e.g.according to EP 652273 or WO 2009 / 062578, dibenzofuran derivatives, e.g. according to WO 2009 / 148015 or WO 2015 / 169412, carbazolamines or bridged carbazole derivatives, e.g. according to US 2009 / 0136779, WO 2010 / 050778, WO 2011 / 042107 or WO 2011 / 088877.

[0072] It may also be preferable to use several different matrix materials as a mixture, in particular at least one electron-conducting matrix material and at least one hole-conducting matrix material. A preferred combination is, for example, the use of a triazine, pyrimidine, quinazoline, or quinoxaline derivative with a triarylamine derivative or a carbazole derivative as a mixed matrix for the metal complex according to the invention. Likewise preferred is the use of a mixture of a charge-transporting matrix material and an electrically inert matrix material (so-called "wide bandgap host"), which is not involved or not significantly involved in charge transport, as described, for example, in WO 2010 / 108579 or WO 2016 / 184540. Likewise preferred is the use of two electron-transporting matrix materials, for example, triazine derivatives and lactam derivatives, as described, for example, in WO 2014 / 094964.

[0073] Examples of compounds suitable as matrix materials for the compounds according to the invention are shown below.

[0074] Preferred electron-transporting matrix materials are selected from the group consisting of triazine derivatives, pyrimidine derivatives, quinazoline derivatives, and quinoxaline derivatives. Preferred triazine, pyrimidine, quinazoline, or quinoxaline derivatives, which can be used as a mixture together with the compounds according to the invention, are the compounds of the following formulas (19), (20), (21), and (22), where R and R 1< have the meanings given above and Ar 1<, identical or different on each occurrence, represents an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more radicals R 1<.

[0075] Particularly preferred are the triazine derivatives of formula (19) and the quinazoline derivatives of formula (21), in particular the triazine derivatives of formula (19).

[0076] In a preferred embodiment of the invention, Ar 1< in the formulas (19) to (22) is, on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, in particular having 6 to 24 aromatic ring atoms, which may be substituted by one or more radicals R 1<.

[0077] Examples of suitable triazine compounds which can be used as matrix materials together with the compounds according to the invention are the compounds shown in the following table.

[0078] Examples of suitable quinazoline compounds are those shown in the following table:

[0079] Preferred biscarbazoles are the structures of the following formulas (23) and (24), where Ar 1< and R have the meanings given above and A 1< stands for CR 2 , NR, O or S. In a preferred embodiment of the invention, A 1< stands for CR 2 .

[0080] Preferred embodiments of the compounds of formulas (23) and (24) are the compounds of the following formulas (23a) and (24a), where the symbols used have the meanings given above.

[0081] Examples of suitable compounds according to formula (23) or (24) are the compounds shown below.

[0082] Preferred bridged carbazoles are the structures of the following formula (25), where A 1< and R have the meanings given above and A 1< is preferably selected, identically or differently on each occurrence, from the group consisting of NAr 1< and CR 2 .

[0083] Preferred dibenzofuran derivatives are the compounds of the following formula (26), where the oxygen can also be replaced by sulfur to form a dibenzothiophene, L represents a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which can also be substituted by one or more radicals R, and R and Ar 1< have the meanings given above. The two groups Ar 1<, which bond to the same nitrogen atom, or a group Ar 1< and a group L, which bond to the same nitrogen atom, can also be linked to one another, for example to form a carbazole.

[0084] Examples of suitable dibenzofuran derivatives are the compounds shown below.

[0085] Suitable compounds that can be used as wide bandgap matrix materials are the compounds of the following formula (27), where R has the meanings given above and preferably, identically or differently on each occurrence, represents H, D, a linear alkyl group having 1 to 10 C atoms, a branched or cyclic alkyl group having 3 to 10 C atoms or an aromatic ring system having 6 to 24 aromatic ring atoms, which may also be substituted by one or more alkyl groups having 1 to 10 C atoms, but is preferably unsubstituted.

[0086] Examples of materials that can be used as wide bandgap matrix materials:

[0087] It is further preferred to use a mixture of two or more triplet emitters, in particular two triplet emitters, together with one or more matrix materials. The triplet emitter with the shorter-wavelength emission spectrum serves as a co-matrix for the triplet emitter with the longer-wavelength emission spectrum. In the present case, the compound of formula (1) is generally the triplet emitter with the longer-wavelength emission maximum. For example, the compounds according to the invention can be combined with a shorter-wavelength metal complex, e.g., one that emits blue, green, or yellow, as a co-matrix.

[0088] A preferred mixture in the emitting layer contains an electron-transporting host material, a so-called "wide bandgap" host material, which due to its electronic properties is not or not significantly involved in the charge transport in the layer, a co-dopant which is a triplet emitter emitting at a shorter wavelength than the compound according to the invention, and a compound according to the invention.

[0089] A further preferred mixture in the emitting layer contains an electron-transporting host material, a so-called "wide band gap" host material, which due to its electronic properties is not or not significantly involved in the charge transport in the layer, a hole-transporting host material, a co-dopant, which is a triplet emitter emitting at a shorter wavelength than the compound according to the invention, and a compound according to the invention.

[0090] Examples of the emitters described above can be found in applications WO 00 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 05 / 033244, WO 05 / 019373, US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, WO 2010 / 102709, WO 2011 / 032626, WO 2011 / 066898, WO 2011 / 157339, WO 2012 / 007086, WO 2014 / 008982, WO 2014 / 023377, WO 2014 / 094961, WO 2014 / 094960, WO 2015 / 036074, WO 2015 / 104045, WO 2015 / 117718, WO 2016 / 015815, WO 2016 / 124304, WO 2017 / 032439, WO 2018 / 011186, WO 2018 / 041769, WO 2019 / 020538, WO 2018 / 178001, WO 2019 / 115423, and WO 2019 / 158453. In general, all phosphorescent complexes as used in the prior art for phosphorescent OLEDs and as known to the person skilled in the art in the field of organic electroluminescence are suitable, and the person skilled in the art can use further phosphorescent complexes without inventive step.

[0091] Examples of suitable triplet emitters which can be used as co-dopants for the compounds according to the invention are shown in the following table.

[0092] Metals with a low work function, metal alloys, or multilayer structures made of different metals are preferred as the cathode, such as alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Alloys made of an alkali or alkaline earth metal and silver, for example, an alloy of magnesium and silver, are also suitable. In multilayer structures, other metals with a relatively high work function, such as Ag, can also be used in addition to the metals mentioned, in which case combinations of the metals, such as Mg / Ag, Ca / Ag, or Ba / Ag, are generally used. It may also be preferable to introduce a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor.Suitable materials for this purpose include alkali metal or alkaline earth metal fluorides, as well as the corresponding oxides or carbonates (e.g., LiF, Li 2 O, BaF 2 , MgO, NaF, CsF, Cs 2 CO 3 , etc.). Organic alkali metal complexes, such as Liq (lithium quinolinate), are also suitable. The thickness of this layer is preferably between 0.5 and 5 nm.

[0093] Materials with a high work function are preferred as the anode. The anode preferably has a work function greater than 4.5 eV vs. vacuum. Metals with a high redox potential, such as Ag, Pt, or Au, are suitable for this purpose. Metal / metal oxide electrodes (e.g., Al / Ni / NiO x , Al / PtO x ) may also be preferred. For some applications, at least one of the electrodes must be transparent or partially transparent to enable either the irradiation of the organic material (O-SC) or the coupling out of light (OLED / PLED, O-LASER). Preferred anode materials here are conductive mixed metal oxides. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred. Also preferred are conductive, doped organic materials, in particular conductive doped polymers, e.g., PEDOT, PANI, or derivatives of these polymers.It is also preferred if a p-doped hole-transport material is applied to the anode as a hole-injection layer. Suitable p-dopants are metal oxides, for example MoO 3 or WO 3 , or (per)fluorinated electron-deficient aromatics. Other suitable p-dopants are HAT-CN (hexacyanohexaazatriphenylene) or the compound NPD9 from Novaled. Such a layer simplifies hole injection into materials with a deep HOMO, i.e., a large HOMO.

[0094] In the further layers, it is generally possible to use all materials as used for the layers according to the prior art, and the person skilled in the art can combine any of these materials with the materials according to the invention in an electronic device without inventive step.

[0095] The device is structured, contacted and finally hermetically sealed accordingly (depending on the application), since the lifetime of such devices is drastically reduced in the presence of water and / or air.

[0096] Also preferred is an organic electroluminescent device characterized in that one or more layers are coated using a sublimation process. The materials are vapor-deposited in vacuum sublimation systems at an initial pressure of typically less than 10 -5 mbar, preferably less than 10 -6 mbar. It is also possible for the initial pressure to be even lower or higher, for example, less than 10 -7 mbar.

[0097] Also preferred is an organic electroluminescent device, characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or by means of carrier gas sublimation. The materials are applied at a pressure between 10 -5 mbar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus patterned.

[0098] Also preferred is an organic electroluminescent device, characterized in that one or more layers are produced from solution, such as by spin coating, or by any printing process, such as screen printing, flexographic printing, offset printing, or nozzle printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing. Soluble compounds are required for this purpose, which are obtained, for example, by suitable substitution. In a preferred embodiment of the invention, the layer containing the compound according to the invention is applied from solution.

[0099] The organic electroluminescent device can also be manufactured as a hybrid system by applying one or more layers from solution and vapor-depositing one or more other layers. For example, it is possible to apply a hole-transport layer and an emitting layer containing a compound according to the invention and a matrix material from solution, and then vacuum-deposit a hole-blocking layer and / or an electron-transport layer thereon.

[0100] These processes are generally known to the person skilled in the art and can be applied by him without problems to organic electroluminescent devices containing compounds according to formula (1) or the preferred embodiments listed above.

[0101] The electronic devices according to the invention, in particular organic electroluminescent devices, are distinguished from the prior art in that they can be applied in an oriented manner even when applied from solution, which leads to oriented emission and thus to an improvement in external quantum efficiency. This applies compared to complexes that are otherwise identical in structure but lack X groups. This advantage is not accompanied by a deterioration in other electronic properties.

[0102] The invention is further illustrated by the following examples, without intending to limit it. Those skilled in the art can use the descriptions to produce further electronic devices according to the invention without inventive step and thus implement the invention within the entire scope of the claims. Examples:

[0103] Unless otherwise stated, the following syntheses are carried out under a protective gas atmosphere in dried solvents. The metal complexes are also handled in the absence of light or under yellow light. The solvents and reagents can be obtained from Sigma-ALDRICH or ABCR, for example. The respective information in square brackets or the numbers given for individual compounds refer to the CAS numbers of the known compounds. Synthesis of groups X:

[0104] Synthesis of B1

[0105] 26 g (33.7 mmol) A1(CAS 2171483-83-1) are dissolved in 600 mL of dichloromethane. Then, 7.2 g (44 mmol) of N-bromosuccinimide are added portionwise and stirred at room temperature with the addition of a drop of HBr. After 48 h, 200 ml of aqueous sodium bisulfite solution (30%) are added and stirred for 1 h. The two phases are then separated, the organic phase is extracted with water and then concentrated under reduced pressure. The residue is treated with 300 mL of n-heptane and refluxed for 1 h. After the mixture has cooled, the colorless solid is filtered and dried under reduced pressure. Yield: 25.3 g (32 mmol) corresponds to 97% of theory).

[0106] The following connections can be made analogously: reactant product B2 CAS 1221237-90-6 B3 CAS 1221237-82-6 B4 CAS1706803-15-7 B5 CAS 929198-27-6 With NCS instead of NBS B6 C1 B7 C2 B8 C3 B9 C4 B10 C5 B11 C6 B12 C7 B13 C8 B14 C13 Synthesis of C1:

[0107] 28.0 g (35.5 mmol) B1, 33.6 g (35.5 mmol) of CAS 2171483-74-0 and 9.8 g (71 mmol) of potassium carbonate were treated with 1100 mL of THF and 550 mL of water. Then, 373 mg (1.4 mmol) of triphenylphosphine and 325 mg (0.4 mmol) of tri(dibenzylideneacetone)dipalladium were added, and the mixture was refluxed for 16 h. Water and toluene were then added to the reaction mixture, and the phases were separated. The aqueous phase was extracted twice with toluene, and the combined organic phases were extracted once with water. The organic phase was filtered through aluminum oxide and then concentrated under reduced pressure. The product was purified by repeated crystallization from toluene / n-heptane 1:10, yielding it as a solid. Yield: 41.0 g (28.8 mmol), 81% of theory.

[0108] The following connections can be made analogously: Boron esters bromide product C2 CAS 2171483-74-0 B4 C3 CAS 2171483-74-0 B5 C4 CAS 1813574-72-9 B3 C5 CAS 1813574-72-9 B1 C6 CAS 2171483-74-0 2244910-28-7 C7 CAS 2171483-74-0 53220-82-9 C8 CAS 85072-44-2 B5 C9 CAS 85072-44-2 B11 C10 CAS 85072-44-2 B12 C11 CAS 85072-44-2 B13 C12 CAS 1256619-36-9 D6 C13 CAS 1813574-72-9 CAS 2268821-67-4 C14 CAS 24388-23-6 CAS 198289-16-6 Synthesis of D1:

[0109] 25.3 g (18.7 mmol) of C1, 8.6 g (33.7 mmol) of bis(pinacolato)diboron, 5.5 g (56 mmol) of potassium acetate, and 830 mg (1.1 mmol) of trans-dichlorobis(tricyclohexylphosphine)palladium(II) were treated with 750 mL of dioxane and refluxed for 48 h. Toluene and water were then added to the reaction mixture, and the phases were separated. The aqueous phase was extracted twice with toluene, the combined organic phases were extracted twice with water, then filtered through aluminum oxide and concentrated under reduced pressure. The residue was triturated with hot ethanol, and the product was obtained as a solid. Yield: 16.0 g (11.1 mmol), 60% of theory.

[0110] The following connections can be made analogously: reactant D2 C2 D3 C3 D4 C4 D5 C5 D6 E17 D7 C12 D8 C13 D9 C14 D10 CAS 2179264-15-2 Synthesis of E1:

[0111] 5 g (6.4 mmol) B1, 9.8 g (6.8 mmol) D1 and 1.8 g (13 mmol) of potassium carbonate are treated with 800 mL of THF and 400 mL of water. Then 67 mg (0.26 mmol) of triphenylphosphine and 59 mg (0.06 mmol) of tri(dibenzylideneacetone)dipalladium are added and the mixture is refluxed for 16 h. The reaction mixture is then treated with water and toluene and the phases are separated. The aqueous phase is extracted twice with toluene and the combined organic phases once with water. The organic phase is filtered through aluminum oxide and then concentrated under reduced pressure. The product is obtained by chromatography (SiO 2 , heptane / THF 1:20 > 1:10) and by repeated extraction from hot toluene and as a solid. Yield: 8.5 g (4.2 mmol) 66% of theory.

[0112] The following connections can be made analogously: E reactant Boron esters product 2 B1 D2 3 B1 D3 4 B1 D4 5 B1 D5 6 B11 D1 7 B12 D1 8 B13 D1 9 B5 D1 10 B6 D1 11 B7 D1 12 B8 D1 13 B9 D1 14 B10 D1 15 CAS 19828 9-16-6 D4 16 CAS 19828 9-16-6 CAS 21714 83-74-0 17 CAS 18812 30-18-7 D2 18 CAS 53220-829 D6 19 CAS 18812 30-18-7 D7 20 CAS 19828 9-16-6 D8 21 CAS 19828 9-16-6 D9 22 B14 D8 23 B1 D10 Synthesis of the intermediate Int-1

[0113] 3 g (13.2 mmol) of CAS 68797-61-5, 10.4 g (13.2 mmol) of D4, 3.7 g (27 mmol) of potassium carbonate, and 0.76 g (0.66 mmol) of tetrakis(triphenylphosphine)palladium(0) are mixed in 500 ml of toluene / ethanol / water (2:1:1) and heated under reflux for 18 h. After complete conversion, the reaction mixture is cooled to room temperature. The organic phase is diluted with toluene and washed twice with water and once with saturated aqueous sodium chloride solution. The organic phases are combined and concentrated on a rotary evaporator. The product is purified by column chromatography (SiO2; THF / heptane). Yield: 4.3 g (5.3 mmol; 40%). Synthesis of the intermediate Int-2

[0114] 15.0 g (100.7 mmol) of 4,6-dichloropyrimidine, 38.5 g of (4-chloro-3-methoxyphenyl)boronic acid, 55.7 g (402.7 mmol) of potassium carbonate, and 2.8 g (4.0 mmol) of bis(triphenylphosphine)Pd(II) chloride were dissolved in 300 mL of acetonitrile / ethanol (2:1) and heated under reflux for 16 h. After complete conversion, the reaction mixture was allowed to cool to room temperature. The precipitated solid was filtered off with suction and washed with toluene and methanol. The filtrate was concentrated on a rotary evaporator. The resulting solid was purified by crystallization from dichloromethane / methanol. Yield: 20.9 g (57.9 mmol; 58%)

[0115] Analogously, the following compound can be prepared from the corresponding boronate ester: Boronic acid reactant product Int-2b CAS 1679-18-1 Int-1 Synthesis of the intermediate Int-3

[0116] 16.0 g (44.3 mmol) of Int-2, 24.3 g (95.7 mmol) of bis(pinacolato)diborane, and 17.4 g (177.2 mmol) of potassium acetate were dissolved in 1000 mL of THF. After addition of 1.87 g (2.2 mmol) of Xphos Pd G3, the reaction mixture was heated under reflux for 48 h. The reaction mixture was then cooled to room temperature, and the solid was filtered off. The filtrate was concentrated on a rotary evaporator and purified by column chromatography (SiO 2 , heptane / ethyl acetate), and the product was isolated. Yield: 12.4 g (22.7 mmol; 51%).

[0117] Analogously, the following compound can be prepared from the corresponding boronate ester: chloride product Int-3b Int-2b Synthesis of the emitter basic structure step 1

[0118] 39.2 g (81 mmol) of EC1 (2202712-51-2), 54.0 g (170 mmol) of 2-bromo-4-chloro-1-iodobenzene, 44.8 g (324 mmol) of potassium carbonate, and 570 mg (0.81 mmol) of bis(triphenylphosphine)palladium(II) chloride are placed in 600 ml of toluene and stirred at 80 °C. After 16 h, 300 mL of water are added. The phases are separated, the aqueous phase is extracted several times with toluene, and the organic phase is washed several times with water. The organic phases are combined and concentrated under reduced pressure. The resulting residue is stirred several times with hot ethanol. The resulting solid is extracted hot with toluene over aluminum oxide. The precipitated solid is filtered. Yield: 35.1 g (57.5 mmol) 71% of theory.

[0119] Analogously, the following compounds can be prepared from the corresponding boronate esters: Boron esters product EC2b Int-3 EC2c Int-3b Synthesis of the emitter basic structure step 2

[0120] 34.6 g (57 mmol) of EC2, 78.8 g (118 mmol) of 1989597-72-9, and 24 g (226 mmol) of sodium carbonate were suspended in 1.2 L of THF / water (2:1). After adding 400 mg (0.57 mmol) of Pd(amphos)Cl2, the reaction mixture was refluxed for 16 h. The solid that precipitated upon cooling to room temperature was filtered and purified by repeated hot extraction over aluminum oxide (using dichloromethane as eluent) followed by crystallization from dichloromethane / methanol. Yield: 52.3 g (34.4 mmol), 61% of theory.

[0121] Analogously, the following compounds can be prepared from the corresponding boronate esters Boron esters product EC3b 2245948-53-0 EC3c 2350247-89-9 EC3d 2202718-90-7 EC3e 2178101-83-0 EC3f 2178101-83-0 Bromide: EC2b EC3g 1989597-72-9 Bromide: EC2b EC3h 2178101-83-0 Bromide: EC2c Synthesis of the emitter core stage 2-Int

[0122] 28.2 g (18.1 mmol) of EC3g are dissolved in 250 mL of dichloromethane. After adding 9 mL of pyridine, the mixture is cooled to 0 °C, and 12 mL (73 mmol) of trifluoromethanesulfonic anhydride is added dropwise so that the temperature does not exceed 2 °C. The mixture is stirred at this temperature for a further hour and then stirred at room temperature for 16 h. The reaction mixture is then poured onto 600 mL of ice and stirred for 30 minutes. The mixture is transferred to a separatory funnel, and the organic phase is diluted with dichloromethane and washed three times with water. The combined aqueous phases are extracted twice with dichloromethane. The combined organic phases are filtered through silica gel and rinsed with ethyl acetate. After removing the solvents on a rotary evaporator, the residue is extracted several times with ethyl acetate heated to 60 °C.After cooling to room temperature, the solid was filtered off, yielding the product. Yield: 28.1 g (15.4 mmol; 85%).

[0123] Analogously, the following compound can be prepared from the corresponding boronate ester: reactant product EC3f-Int EC3f Synthesis of EC3i

[0124] 15.5 g (8.5 mmol) of EC3g-Int, 6.4 g (34.1 mmol) of 4-tert-butylphenylboronic acid, 4.7 g (34.1 mmol) of potassium carbonate, 0.73 g (1.7 mmol) of dppb, and 0.39 g (0.43 mmol) of tris(dibenzylideneacetone)dipalladium(0) were dissolved in 1000 mL of dioxane / water (3:1) and stirred at 90 °C for 16 h. After complete conversion, the organic phase was diluted with ethyl acetate, and the phases were separated. The aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were washed twice with water, dried over magnesium sulfate, and filtered through silica gel. The desired product was obtained after purification by column chromatography (SiO2; toluene / ethyl acetate). Yield: 6.1 g (3.4 mmol; 40%).

[0125] Analogously, the following compounds can be prepared from the corresponding boronate esters: reactants product EC3j Triflate: EC3g-Int Boron ester: D1 EC3k Triflate: EC3f-Int Boronic acid: 4-tert-butylphenylboronic acid Synthesis of the emitter basic structure step 3

[0126] 52.3 g (34.4 mmol) of EC3, 35 g (71.5 mmol) of tris(acetylacetonato)iridium(III), and 523 g of hydroquinone were initially charged, heated to 260 °C, and stirred at this temperature for 2 h. The reaction mixture was then allowed to cool, with 500 mL of ethylene glycol being added dropwise at 220 °C and 2 L of methanol at 120 °C. After cooling to room temperature, the precipitated solid was filtered through a reverse frit filter. The diastereomeric metal complex mixture containing ΔΔ and ΛΛ isomers (racemic) as well as the ΛΔ isomer (meso) in a molar ratio of 1:1 (determined by 1< H NMR) was dissolved in 300 mL dichloromethane, applied to 100 g of silica gel, and separated by chromatography on a silica gel column pre-slurried with toluene, if possible under exclusion of light. The leading spot, hereinafter referred to as isomer 1 (11), was eluted first, followed by the later-eluting isomer, hereinafter referred to as isomer 2 (12). After removal of the solvent, a deep red solid was obtained.Yield: I1: 29 g (15.2 mmol), 45% of theory. Th.; I2: 24.3 g (12.7 mmol), 37% of theory. Th.

[0127] The metal complexes shown below can in principle be purified by chromatography (typically using a column chromatography machine (Torrent from Axel Semrau), recrystallization or hot extraction. The images of complexes shown below usually show only one isomer. The isomer mixture can be separated, but can also be used as a mixture of isomers in the OLED. However, there are also ligand systems in which only one diastereomer pair is formed for steric reasons.

[0128] The following compounds can be synthesized analogously. The chromatographic separation of the resulting diastereomer mixture is carried out on flash silica gel on an automated column column (Torrent from Axel Semrau): reactant product EC4b EC3b EC4c EC3c EC4d EC3d EC4e EC3e EC4f EC3h EC4g EC3k EC4h EC3j EC4i EC3i Synthesis of the emitter basic structure step 4

[0129] 11.7 g (6.2 mmol) of EC4, 3.3 g (13 mmol) of bis(pinacolato)diboron, 2.4 g (25 mmol) of potassium acetate, and 453 mg (0.61 mmol) of trans-dichlorobis(tricylo-hexylphosphine)palladium(II) were placed in 600 mL of dioxane and refluxed for 16 h. After cooling to room temperature, 400 mL of water were added, followed by extraction with dichloromethane, and the combined organic phases were extracted with water several times. The organic phase was then filtered through silica gel (dichloromethane) and concentrated under reduced pressure. The resulting residue was crystallized from dichloromethane / methanol. Yield: 12.8 g (6.1 mmol), 98% of theory.

[0130] The following connections can be represented analogously: reactant product EC5b EC4b EC5c EC4c EC5d EC4d EC5e EC4e EC5f EC4f EC5g EC4g EC5h EC4h EC5i EC4i Synthesis of the emitter Em1

[0131] 2.7 g (1.3 mmol) EC5, 5.3 g (2.6 mmol) E1, 0.79 g (5.2 mmol) cesium fluoride, 97 mg (0.13 mmol) trans-dichlorobis(tricylohexylphosphine)palladium(II) are dissolved in 80 mL dioxane and refluxed for 16 h. After cooling to room temperature, the reaction mixture is treated with dichloromethane and water, and the organic phase is separated. The aqueous phase is extracted twice with dichloromethane, and the combined organic phases are extracted with water and then concentrated under reduced pressure. The residue is purified several times by chromatography (SiO2, heptane / dichloromethane) and then recrystallized from dichloromethane / methanol. The resulting solid is dried under reduced pressure at 200 °C. Yield: 2.7 g (0.47 mmol), 36% of theory. Th..

[0132] The following connections can be represented analogously: Educt A Educt B EC5b E1 EC5c E1 EC5d E1 EC5e E1 EC5a E7 EC5a B7 EC5a 2179264-15-2 EC5a E15 EC5a E16 EC5a E17 EC5a E18 E19 EC5a E20 EC5a EC5e E21 EC5e E22 EC5a E23 E20 EC5g C1 EC5h E1 EC5h E1 EC5f E1 EC5i Physics examples Production of OLEDs and films for photophysical characterization

[0133] The complexes according to the invention can be processed from solution. The production of completely solution-based OLEDs has been described many times in the literature, e.g., in WO 2004 / 037887 using spin coating. The production of vacuum-based OLEDs has also been described many times, including in WO 2004 / 058911. In the examples discussed below, solution-based and vacuum-based layers are combined within an OLED, so that processing up to and including the emission layer takes place from solution, and in the subsequent layers (hole-blocking layer and electron-transport layer) from vacuum. The general methods described above are adapted and combined to the conditions described here (layer thickness variation, materials) as described below.The general structure is as follows: substrate / ITO (50 nm) / hole injection layer (HIL) (60 nm) / hole transport layer (HTL) (20 nm) / emission layer (EML) (60 nm) / hole blocking layer (HBL) (10 nm) / electron transport layer (ETL) (40 nm) / cathode (aluminum, 100 nm). Glass plates coated with structured ITO (indium tin oxide) with a thickness of 50 nm serve as the substrate. For improved processing, these are coated with PEDOT:PSS (poly(3,4-ethylenedioxy-2,5-thiophene):polystyrenesulfonate, purchased from Heraeus Precious Metals GmbH & Co. KG, Germany). PEDOT:PSS is spin-coated from water in air and subsequently baked in air at 180 °C for 10 minutes to remove residual water. The hole-transport layer and the emission layer are applied to these coated glass plates. The hole-transport layer used is cross-linkable.A polymer according to the structure shown below is used, which can be synthesized according to WO 2013 / 156130: .

[0134] The hole-transporting polymer is dissolved in toluene. The typical solids content of such solutions is approximately 5 g / l if, as in this case, the layer thickness of 20 nm typical for a device is to be achieved by spin coating. The layers are spun in an inert gas atmosphere, in this case argon, and annealed for 30 minutes at 220 °C.

[0135] The emission layer always consists of at least one matrix material (host material) and one emitting dopant (dopant, emitter). Mixtures of multiple matrix materials and co-dopants can also be used. A specification such as TMM-A (92%) : dopant (8%) means that the TMM-A material is present in the emission layer at a weight fraction of 92% and the dopant at a weight fraction of 8%. The mixture for the emission layer is dissolved in toluene or, if necessary, chlorobenzene. The typical solids content of such solutions is approximately 17 g / l if, as here, the layer thickness of 60 nm typical for a device is to be achieved by spin coating. The layers are spun on in an inert gas atmosphere, in this case argon, and baked for 10 minutes at 160 °C. The materials used in this case are shown in Table 1.

[0136] The materials for the hole-blocking layer and electron-transport layer are thermally evaporated in a vacuum chamber. For example, the electron-transport layer can consist of more than one material, which are mixed together in a specific volume fraction by co-evaporation. A specification such as ETM1:ETM2 (50%:50%) means that the materials ETM1 and ETM2 each make up 50% of the layer. The materials used in this case are shown in Table 2. In the OLED components described here, ETM3 was used as the HBL material and ETM1:ETM2 (50:50) as the ETL mixture. Table 2: HBL and ETL materials used ETM1 ETM2 ETM3 [1819335-36-8] [25387-93-3] [2392900-45-5]

[0137] The cathode is formed by thermal evaporation of a 100 nm aluminum layer. The samples are encapsulated.

[0138] Films for photophysical characterization are fabricated as single layers on fused silica substrates according to the process described above for emissive layers. B1 is used as the host material, and 30 nm thick films are produced. The samples are encapsulated. Characterization: Measurement of emitter orientation in solution-processed film

[0139] In the measurement setup, the solution-processed film containing the complex is irradiated with a laser, the molecules are excited, and the emitted photoluminescence spectrum is then measured as an angle-dependent measure. From the measured optical properties of the pure matrix material, a result for a potential 100% horizontal and 100% vertical orientation of the molecules can be calculated using optical-physical laws. The measured values ​​are then fitted to the calculated extreme orientations, thus determining the orientation factor (optical orientation anisotropy). A perfect horizontal orientation of the molecules is described by Θ = 0, the isotropic case by Θ = 0.33, and the completely vertically aligned case by Θ = 1.This value reflects the averaged orientation of all molecules in the layer that were excited by the photoluminescence process, i.e., all complex molecules located within the measurement spot irradiated by the laser. Determining the orientation of a single molecule is not possible with this method. Frischeisen et al., Applied Physics Letters 96, 073302 (2010) and Schmidt et al., Phys. Rev. Appl. 8, 037001 (2017) describe the performance of such optical measurements to determine emitter orientation.

[0140] Table 3 summarizes the optical orientation of the comparison material and that of selected inventive materials. The inventive complexes are used in slightly higher wt. % to compensate for the higher molecular weight. It can be seen that the two comparison complexes exhibit an isotropic arrangement in the film, while the inventive complexes are more horizontally oriented. Table 3: Optical orientation anisotropy Θ Complex % in host B1 Θ V1 D1 10 0.33 E1 Em1 15 0.26 V2 D2 10 0.33 E2 Em4 15 0.26 E3 Em5 15 0.26 E4 Em8 15 0.29 E5 Em16 15 0.27 E6 Em13 15 0.26 E7 Em12 15 0.28 E8 Em6 15 0.26 E9 Em11 15 0.28 E10 Em15 15 0.25 E11 Em10 15 0.28 E12 Em7 15 0.24 E13 Em14 15 0.27 E14 Em2 15 0.26 E15 Em3 15 0.26 E16 Em9 15 0.26 E17 Em17 15 0.27 E30 Em18 15 0.27 E31 Em19 15 0.28 E32 Em20 15 0.25 E33 Em21 15 0.26 E34 Em22 15 0.26 OLED components:

[0141] OLEDs are characterized as standard. For this purpose, the electroluminescence spectra and the current-voltage-luminance (IUL) characteristics are determined, assuming a Lambertian radiation pattern, and the external quantum efficiency at a specific brightness is calculated as a key figure.

[0142] All tested components glow red. The EML mixtures used and the results obtained are summarized in Table 4. The inventive complexes are used in slightly higher wt. % to compensate for the higher molecular weight. It is shown that inventive complexes, with their more horizontal orientation, achieve a significantly increased quantum efficiency in the OLED component. In particular, it is evident that in a direct comparison with the same auxiliary ligand (D2 compared to Em4; D1 compared to Em1, Em13, Em12, Em7, Em14, Em9, and Em17), the inventive substituents lead to an increase in quantum efficiency.

[0143] All complexes according to the invention listed above can be used analogously and lead to comparable results. Table 4: Results of solution-processed OLEDs (measured at a brightness of 1000 cd / m 2<) e.g. Emitter EQE [%] Mixing ratio A1:B1:C1:Emitter V3 D1 18.7 40:35:17:8 E18 Em1 26.1 40:33:17:10 V4 D2 21.8 40:35:17:8 E19 Em4 26.5 40:33:17:10 E20 Em5 26.2 40:33:17:10 E21 Em13 25.9 40:33:17:10 E22 Em12 23.2 40:33:17:10 E23 Em15 26.3 40:33:17:10 E24 Em7 26.5 40:33:17:10 E25 Em14 23.9 40:33:17:10 E26 Em2 25.7 40:33:17:10 E27 Em3 26.0 40:33:17:10 E28 Em9 26.0 40:33:17:10 E29 Em17 24.1 40:33:17:10 E35 Em18 24.2 40:33:17:10 E36 Em19 23.4 40:33:17:10 E37 Em20 26.4 40:33:17:10 E38 Em22 26.2 40:33:17:10

Claims

1. A compound according to formula (1), wherein the symbols and indices used are as follows: X is the same or different at each occurrence, and is a group of the Formula -(Ar)n-R; Y is the same or different at each occurrence, and is R or X; Z is the same or different and is R or X; Ar is the same or different at each occurrence, and is a bivalent group selected from the structures (Ar1) to (Ar7), wherein the dashed bond represents the linkage of the structures and V is CR2, O, S or NR; n is the same or different at each occurrence, and is an integer from 3 to 20, with the proviso that in each unit -(Ar)n-R at least 5 phenyl and / or cyclohexyl groups are linearly connected to each other, wherein the structures (Ar1) and (Ar3) each contribute one phenyl group, structures (Ar2), (Ar4) and (Ar5) each contribute two phenyl groups, and structures (Ar6) and (Ar7) each contribute one cyclohexane group; R can occur once or more than once, and is the same or different at each occurrence, and is H, D, F, Cl, Br, I, N(R1)2, CN, NO2, OR1, SR1, COOH, C(=O)N(R1)2, Si(R1)3, B(OR1)2, C(=O)R1, P(=O)(R1)2, S(=O)R1, S(=O)2R1, OSO2R1, a linear-chain alkyl group having 1 to 20 C-atoms or an alkenyl or alkynyl group having 2 to 20 C-atoms or a branched or cyclic alkyl group having 3 to 20 C-atoms, wherein the alkyl, alkenyl or alkynyl group can each be substituted by one or more groups R', wherein one or more non-adjacent CH2-groups can be replaced by Si(R1)2, C=O, NR1, O, S or CONR1, or can be an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may each be substituted by one or more groups R1; and wherein two groups R can optionally together form a ring system; R 1 is the same or different at each occurrence, and is H, D, F, Cl, Br, I, N(R2)2, CN, NO2, OR2, SR2, Si(R2)3, B(OR2)2, C(=O)R2, P(=O)(R2)2, S(=O)R2, S(=O)2R2, OSO2R2, a straight-chain alkyl group having 1 to 20 C-atoms or an alkenyl or alkynyl group having 2 to 20 C-atoms or a branched or cyclic alkyl group having 3 to 20-C atoms, wherein the alkyl, alkenyl or alkynyl group may each be substituted with one or more R2 radicals, wherein one or more non-adjacent CH2 groups may be replaced by Si(R2)2, C=O, NR2, O, S or CONR2, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more radicals R2; and wherein two groups R1 together can form a ring system; R2 is the same or different at each occurrence, and is H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, in particular a hydrocarbon radical, having 1 to 20 C-atoms, in which one or more H-atoms may optionally be replaced by F.

2. The compound according to claim 1 according to formula (1a), wherein the symbols have the meanings set forth in claim 1.

3. The compound according to claim 1 or 2, characterized in that the two substituents X are the same.

4. The compound according to any one or more of claims 1 to 3, selected from the structures of the formulas (1a-1), (1a-2) and (1a-3), respectively, wherein both groups X are the same, and wherein groups Y in formula (1a-2) each represent a unit -(Ar)n-R and are the same, and wherein the group Z in formula (1a-3) is a unit -(Ar)n-R.

5. The compound according to any one or more of claims 1 to 4, characterized in that the R group in the unit -(Ar)n-R is, at each occurrence, the same or different and is H, a linear alkyl group having 1 to 10 C-atoms or a branched or cyclic alkyl group having 3 to 10 C-atoms.

6. The compound according to any one or more of claims 1 to 5, characterized in that the structures (Ar1) are selected from the structures (Ar1a) to (Ar1f), wherein the dashed bonds represent the linkage of the structures, W is C(R1)2, O, S, or NR1, and R and R1 have the meanings given in claim 1; and that the structures (Ar2) are selected from the structures (Ar2a) and (Ar2b), wherein the dashed bonds represent the linkage of the structures, and R and V have the meanings given in claim 1; and that the structures (Ar3) are selected from the structures (Ar3a), wherein the dashed bonds represent the linkage of the structure; and that the structures (Ar4) are selected from the structures (Ar4a) and (Ar4b), wherein the dashed bonds represent the linkage of the structure, and R has the meanings given in claim 1; and that the structures (Ar5) are selected from the structures (Ar5a) and (Ar5b), wherein the dashed bonds represent the linkage of the structure, and R has the meanings given in claim 1; and that the structures (Ar7) are selected from the structures (Ar7a), wherein the dashed bonds represent the linkage of the structure.

7. The compound according to any one or more of claims 1 to 6, characterized in that at least one group Ar is the same or different at each occurrence and is selected from the structures (Ar1) and / or (Ar2).

8. The compound according to any one or more of claims 1 to 7, characterized in that n is an integer from 5 to 20, in particular from 5 to 15, wherein the groups (Ar1) to (Ar7) are being chosen so that a total of 8 to 24 phenyl or cyclohexane groups are linearly connected to each other.

9. The compound according to any one or more of claims 1 to 8 according to Formula (2), wherein the symbols used have the meanings as set forth in claim 1.

10. The compound according to any one or more of claims 1 to 9, characterized in that all four phenylpyridine partial ligands are equally substituted.

11. A method for preparing a compound according to one or more of claims 1 to 10 by reacting a compound, which instead of X and optionally Y and / or Z is substituted with reactive leaving groups, with a compound A-(Ar)n-R, wherein A is a reactive leaving group.

12. A formulation comprising at least one compound according to any one or more of claims 1 to 10 and at least a further compound and / or at least a solvent.

13. A use of a compound according to any one or more of the claims 1 to 10 in an electronic device.

14. An electronic device comprising at least one compound according to any one or more of claims 1 to 10.

15. The electronic device of claim 14, wherein the device is an organic electroluminescent device, characterized in that the compound according to any one or more of claims 1 to 10 is used as an emitting compound in one or more emitting layers in combination with one or more matrix materials and / or in combination with one or more other triplet emitters.