CONNECTIONS USABLE IN AN ORGANIC ELECTRONIC DEVICE

Abstract

The present invention relates to compounds, particularly for use in electronic devices. The invention further relates to a method for producing the compounds according to the invention, and to electronic devices comprising the same.

Description

[0001] Compounds for Use in Organic Electronic Devices The present invention describes compounds, particularly for use in electronic devices. The invention further relates to a method for producing the compounds according to the invention and to electronic devices containing these compounds. The construction of organic electroluminescent devices in which organic semiconductors are used as functional materials is described, for example, in US 4539507, US 5151629, EP 0676461, WO 98 / 27136 and WO 2010 / 151006 A1. Organometallic complexes exhibiting phosphorescence are frequently used as emitting materials. For quantum mechanical reasons, up to four times the energy and power efficiency is possible when using organometallic compounds as phosphor emitters.In general, there is still room for improvement in electroluminescent devices, especially those exhibiting phosphorescence, for example, regarding efficiency, operating voltage, and lifetime. Furthermore, organic electroluminescent devices are known that include fluorescent emitters or emitters exhibiting TADF (thermally activated delayed fluorescence). The properties of organic electroluminescent devices are not solely determined by the emitters used. The other materials employed, such as host / matrix materials, hole-blocking materials, electron transport materials, and electron / exciton blocking materials, are of particular importance. Improvements to these materials can lead to significant enhancements in electroluminescent devices.In general, there is still room for improvement with these materials, for example, for use as matrix materials, hole transport materials, or electron transport materials, particularly with regard to lifetime, but also with regard to the efficiency and operating voltage of the device. Furthermore, the compounds should exhibit high color purity. Another object of the present invention is to provide compounds suitable for use in an organic electronic device, especially an organic electroluminescent device, as fluorescent emitters or emitters exhibiting TADF (thermally activated delayed fluorescence), and which, when used in this device, lead to good device properties, as well as to provide the corresponding electronic device.The object of the present invention is therefore to provide compounds suitable for use in an organic electronic device, in particular an organic electroluminescence device, which, when used in this device, lead to good device properties, as well as to provide the corresponding electronic device. In particular, it is an object of the present invention to provide compounds that result in a long lifetime, good efficiency, and low operating voltage. The properties of the matrix materials, the hole transport materials, and the electron transport materials also have a significant influence on the lifetime and efficiency of the organic electroluminescence device.A further object of the present invention is to provide compounds suitable for use in phosphorescent or fluorescent electroluminescent devices, particularly as matrix materials. Specifically, it is an object of the present invention to provide matrix materials suitable for red and yellow phosphorescent electroluminescent devices. Furthermore, the compounds, especially when used as matrix materials, hole transport materials, or electron transport materials in organic electroluminescent devices, should lead to devices exhibiting excellent color purity. Additionally, the compounds should be as easy to process as possible, exhibiting good solubility and film formation. For example, the compounds should show increased oxidation stability and an improved glass transition temperature.Another challenge is to provide electronic devices with excellent performance at the lowest possible cost and with consistent quality. Furthermore, these electronic devices should be adaptable to a wide range of applications. In particular, their performance should be maintained over a broad temperature range. Surprisingly, it has been found that certain compounds, described in more detail below, solve these problems and eliminate the limitations of the prior art. The use of these compounds results in very good properties for organic electronic devices, especially organic electroluminescent devices, particularly with regard to lifetime, efficiency, and operating voltage.Electronic devices, in particular organic electroluminescent devices, containing such compounds, as well as the corresponding preferred embodiments, are therefore the subject of the present invention. The subject of the present invention is therefore a compound comprising at least one structure of formulas (Ia), (Ib), (Ic), (Id), (Ie) and / or (If), preferably the compound having a structure of the aforementioned formulas.

[0002] where: X is the same or different from CR or N in each occurrence, preferably CR; Y is the same or different from a bridge selected from B(R), C(R)2, Si(R)2, C=O, C=NR, C=C(R)2, O, S, Se, S=O, SO2, N(R), N(Ar), P(R) and P(=O)R, preferably O, S, B(R), C=O, N(R) and N(Ar), particularly preferably O, S, N(Ar); R is the same or different from H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar)2, N(R) 1 )2, C(=O)N(Ar)2, C(=O)N(R 1)2, Si(Ar)3, Si(R 1 )3, B(Ar)2, B(R 1 )2, C(=O)Ar, C(=O)R 1 , P(=O)(Ar)2, P(=O)(R 1 )2, P(Ar)2, P(R 1 )2, S(=O)Ar, S(=O)R 1 , S(=O)2Ar, S(=O)2R 1 , OSO2Ar, OSO2R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 40 carbon atoms, or an alkenyl or alkynyl group with 2 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group with 3 to 20 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group is each linked to one or more R groups 1 can be substituted, with one or more non-adjacent CH2 groups being replaced by R 1 C=CR 1 , C≡C, Si(R 1 )2, C=O, C=S, C=Se, C=NR 1 , -C(=O)O-, -C(=O)NR 1 -, NR 1 , P(=O)(R 1), -O-, -S-, SO or SO2 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each replaced by one or more R groups 1 may be substituted, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, separated by one or more R groups 1 It can be substituted; two R groups can also form a ring system together; Ar is, in each occurrence, the same or different aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which is coupled with one or more R groups. 1 can be substituted, whereby two Ar residues bonding to the same Si atom, N atom, P atom or B atom can also be connected by a single bond or a bridge selected from B(R) 1 ), C(R 1 )2, Si(R 1 )2, C=O, C=NR 1 , C=C(R 1 )2, O, S, S=O, SO2, N(R 1 ), P(R 1 ) and P(=O)R 1, be bridged together; R 1 is the same or different in each occurrence H, D, F, Cl, Br, I, CN, NO2, N(Ar) 1 )2, N(R 2 )2, C(=O)Ar 1 , C(=O)R 2 , P(=O)(Ar 1 )2, P(Ar 1 )2, B(Ar 1 )2, B(R 2 )2, Si(Ar 1 )3, Si(R 2 )3, a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group with 3 to 40 C atoms or an alkenyl group with 2 to 40 C atoms, each with one or more R groups 2 can be substituted, where one or more non-adjacent CH2 groups are replaced by -R 2 C=CR 2 -, -C≡C-, Si(R 2 )2, C=O, C=S, C=Se, C=NR 2 , -C(=O)O-, -C(=O)NR 2 -, NR 2 , P(=O)(R 2), -O-, -S-, SO or SO2 may be replaced and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which is replaced by one or more R groups 2 may be substituted, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, separated by one or more R groups 2 may be substituted, or an aralkyl or heteroaralkyl group with 5 to 60 aromatic ring atoms, coupled with one or more R groups 2 may be substituted, or a combination of these systems; in this case, two or more, preferably adjacent residues R may be used. 1 together form a ring system; one or more residues R can be involved. 1 form a ring system with another part of the compound; Ar 1In each occurrence, it is the same or different: an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, coupled with one or more non-aromatic residues R 2 It can be substituted, in which case two residues Ar 1 , which bond to the same Si atom, N atom, P atom or B atom, also by a single bond or a bridge, selected from B(R 2 ), C(R 2 )2, Si(R 2 )2, C=O, C=NR 2 , C=C(R 2 )2, O, S, S=O, SO2, N(R 2 ), P(R 2 ) and P(=O)R 2 , be bridged together; R 2is selected in each occurrence, either the same or different, from the group consisting of H, D, F, CN, an aliphatic hydrogen carbonate residue with 1 to 20 C atoms, or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D, F, Cl, Br, I or CN, and which may be substituted by one or more alkyl groups with 1 to 4 carbon atoms each, wherein two or more, preferably adjacent, substituents R 2together form a ring system. Preferably, the present compounds can be used as active compounds in electronic devices. Active compounds are generally the organic or inorganic materials that are introduced, for example, in an organic electronic device, in particular in an organic electroluminescent device, between the anode and cathode, such as charge injection, charge transport, or charge blocking materials, but especially emission materials and matrix materials. Organic materials are preferred. Preferably, a compound according to the invention is a purely organic compound. A purely organic compound is a compound that is not in contact with a metal atom, i.e., it neither forms a coordination compound with a metal atom nor a covalent bond with a metal atom.In this context, a purely organic compound preferably does not include any metal atoms used in phosphorescent emitters. These metals, such as copper, molybdenum, etc., and in particular rhenium, ruthenium, osmium, rhodium, iridium, and palladium, will be described in detail later. The compound that can be used as an active compound in an organic electronic device may preferably be selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF (thermally activated delayed fluorescence), host materials, electron transport materials, exciton blocking materials, electron injection materials, hole transport materials, hole injection materials, n-dopeds, p-dopeds, wide-band-gap materials, electron blocking materials, and / or hole blocking materials.Fluorescent emitters, emitters exhibiting TADF (thermally activated delayed fluorescence), host materials, electron transport materials, exciton blocking materials, electron injection materials, hole transport materials, hole injection materials, n-dopeds, p-dopeds, wide-band-gap materials, electron blocking materials, and / or hole blocking materials are preferred. Adjacent carbon atoms, as used in the present invention, are carbon atoms that are directly linked to one another. Furthermore, "adjacent residues" in the definition of residues means that these residues are bonded to the same carbon atom or to adjacent carbon atoms. These definitions apply accordingly, among others, to the terms "adjacent groups" and "adjacent substituents."The phrase "two or more residues can form a ring" in this description means, among other things, that the two residues are linked to each other by a chemical bond involving the formal elimination of two hydrogen atoms. This is illustrated by the following scheme. 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 diagram: A condensed aryl group, a condensed aromatic ring system, or a condensed heteroaromatic ring system within the meaning of the present invention is a group in which two or more aromatic groups are fused, i.e., fused, to one another via a common edge, such that, for example, two carbon atoms belong to the at least two aromatic or heteroaromatic rings, as in naphthalene. In contrast, fluorene, for example, is not a condensed aryl group within the meaning of the present invention, since in fluorene the two aromatic groups do not share a common edge. Corresponding definitions apply to heteroaryl groups as well as to condensed ring systems, which may, but need not, also contain heteroatoms. If two or more, preferably adjacent, residues R, R' are present, the following applies: 1 and / or R 2When these elements combine to form a ring system, a monocyclic or polycyclic, aliphatic, aromatic, or heteroaromatic ring system can be formed. An aryl group according to this invention contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, and particularly preferably 6 to 30 carbon atoms; a heteroaryl group according to this invention contains 2 to 60 carbon atoms, preferably 2 to 40 carbon atoms, and particularly preferably 2 to 30 carbon atoms, and at least one heteroatom, provided that the sum of the carbon 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 fused aryl or heteroaryl group, for example, naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc.An aromatic ring system according to this invention contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, and particularly preferably 6 to 30 carbon atoms in the ring system. A heteroaromatic ring system according to this invention contains 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and particularly preferably 1 to 30 carbon atoms, and at least one heteroatom in the ring system, provided that the sum of the carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from nitrogen, oxygen, and / or sulfur. An aromatic or heteroaromatic ring system according to this invention is understood to be a system that does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups are also replaced by a non-aromatic unit (preferably less than 10% of the atoms other than hydrogen), such as... B. a C, N or O atom or a carbonyl group may be interrupted.For example, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc., are to be 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 biphenyl, terphenyl, quaterphenyl, or bipyridine, are also to be understood as aromatic or heteroaromatic ring systems, respectively. A cyclic alkyl, alkoxy, or thioalkoxy group within the meaning of this invention is understood to be a monocyclic, a bicyclic, or a polycyclic group. Within the scope of the present invention, a C1 to C1 group is defined as a group consisting of a cyclic alkyl group, a bicyclic group, or a polycyclic group. 20- Alkylgruppe, in der auch einzelne H-Atome oder CH2-Gruppen durch die oben genannten Gruppen substituiert sein können, beispielsweise die Reste 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, Trifluor- methyl, Pentafluorethyl, 2,2,2-Trifluorethyl, 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- are understood. Examples of alkenyl groups include ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, and cyclooctadienyl. Examples of alkynyl groups include ethinyl, propynyl, butynyl, pentinyl, hexynyl, heptynyl, and octynyl. C1 to C, 40-Alkoxy groups include, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy. An aromatic or heteroaromatic ring system with 5 to 60, preferably 5 to 40, aromatic ring atoms, particularly preferably 5 to 30 aromatic ring atoms, which may each be further substituted with the aforementioned substituents and which may be linked via any positions on the aromatic or heteroaromatic compound, includes, 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, Spirotruxen,Spiroisotruxen, Furan, Benzofuran, Isobenzofuran, Dibenzofuran, Thiophen, Benzothiophen, Isobenzothiophen, Dibenzothiophen, Pyrrol, Indol, Isoindol, Carbazol, Indolocarbazol, Indenocarbazol, Pyridin, Chinolin, Isochinolin, Acridin, Phenanthridin, 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, Aza- carbazol, 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-Thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine, and benzothiadiazole. In a preferred embodiment, the compound according to the invention can comprise at least one structure of formulas (IIa), (IIb), (IIc), (IId), (IIe), and / or (IIf); preferably, the compound has a structure of the aforementioned formulas.

[0003] wherein the substituents X, Y and R have the meanings given above, particularly for formulas (Ia) to (If), the index m is equal to or different from 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, more preferably 0 or 1, and the index o is equal to or different from 0, 1 or 2, more preferably 0 or 1, wherein the sum of the indices o and m is preferably 1 or 2, more preferably 1. Preferably, the compound according to the invention may comprise at least one structure of formulas (IIIa), (IIIb), (IIIc), (IIId), (IIIe) and / or (IIIf), more preferably the compound has a structure of the aforementioned formulas.

[0004] wherein the substituents X, Y and R have the meanings given above, particularly for formulas (Ia) to (If), the index m is equal to or different from 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, more preferably 0 or 1, and the index n is equal to or different from 0, 1, 2 or 3, more preferably 0, 1 or 2, more preferably 0 or 1, wherein the sum of the indices n and m is preferably 1 or 2, more preferably 1. Preferably, it may be provided that in formulas (Ia) to (If), (IIa) to (IIf) and / or (IIIa) to (IIIf) at most two groups X per ring represent N, more preferably at least one, more preferably at least two of the groups X per ring are selected from CH and CD.Preferably, in formulas (Ia) to (If), (IIa) to (IIf) and / or (IIIa) to (IIIf), no more than four, preferably no more than two, groups X represent N, and particularly preferably all groups X represent CR, wherein preferably at most 4, particularly preferably at most 3, and especially preferably at most 2 of the groups CR, for which X represents, are not equal to group CH. In a further embodiment, the compound may comprise at least one structure of (IVa), (IVb), (IVc), (IVd), (IVe), and / or (IVf), and preferably the compound has a structure of the aforementioned formulas.

[0005] wherein the remainders Y and R have the meaning previously mentioned, in particular for formulas (Ia) to (If), the index k is equal to or different from 0 or 1, preferably 0, the index o is equal to or different from 0, 1 or 2, preferably 0 or 1, the index n is equal to or different from 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably 0 or 1 and the index m is equal to or different from 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably 0 or 1, wherein the sum of the indices k, m, n and o is preferably 1 or 2, particularly preferably 1. Preferably, the sum of the indices k, m, n and o in formulas (IIa) to (IIf), (IIIa) to (IIIf) and / or (IVa) to (IVf) may be at most 6, preferably at most 4, and particularly preferably at most 2. Furthermore, it is preferred that the sum of the indices o and n in formulas (IIa) to (IIf), (IIIa) to (IIIf) and / or (IVa) to (IVf) is at least 1.Particularly preferably, the sum of the indices o and n in formulas (IIa) to (IIf), (IIIa) to (IIIf) and / or (IVa) to (IVf) is 1 or 2, and especially preferably exactly 1. Furthermore, it can be provided that the compound comprises at least one structure of formulas (Va), (Vb), (Vc), (Vd), (Ve), (Vf), (Vg), (Vh), (Vi), (Vj) and / or (Vk), preferably the compound has a structure of the aforementioned formulas.

[0006] where the remainders Y and R have the meaning mentioned above, especially for formulas (Ia) to (If), and the following also applies: R a is the same or different in each occurrence: OH, F, Cl, Br, I, CN, NO2, N(Ar)2, N(R 1 )2, C(=O)N(Ar)2, C(=O)N(R 1 )2, Si(Ar)3, Si(R 1 )3, B(Ar)2, B(R 1 )2, C(=O)Ar, C(=O)R 1 , P(=O)(Ar)2, P(=O)(R 1 )2, P(Ar)2, P(R 1 )2, S(=O)Ar, S(=O)R 1 , S(=O)2Ar, S(=O)2R 1 , OSO2Ar, OSO2R 1, a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 20 carbon atoms, or an alkenyl or alkynyl group with 2 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group with 3 to 40 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group is each linked to one or more R groups 1 can be substituted, with one or more non-adjacent CH2 groups being replaced by R 1 C=CR 1 , C≡C, Si(R 1 )2, C=O, C=S, C=Se, C=NR 1 , -C(=O)O-, -C(=O)NR 1 -, NR 1 , P(=O)(R 1 ), -O-, -S-, SO or SO2 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each replaced by one or more R groups 1 may be substituted, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, separated by one or more R groups 1It may be substituted; in this case, residues R a also form a ring system with a residue R, where the residues Ar and R 1the meanings mentioned above, particularly for formulas (Ia) to (If); k is equal to or different from 0 or 1, preferably 0; o is equal to or different from 0, 1, or 2, preferably 0 or 1; n is equal to or different from 0, 1, 2, or 3, preferably 0, 1, or 2, particularly preferably 0 or 1; and m is equal to or different from 0, 1, 2, 3, or 4, preferably 0, 1, or 2, particularly preferably 0 or 1. Preferably, it may be provided that in formulas (Va) to (Vk), the sum of the indices k, m, n, and o is at most 6, preferably at most 4, particularly preferably at most 2, especially preferably at most 1, and most preferably 0. In a preferred embodiment, it may be provided that the two remainders Y in the formulas set out above and below are the same. Furthermore, in another preferred embodiment, it may be provided that the two residues Y in the formulas set out above and below are different.Preferably, at least one of the residues is R and / or R'. a Selected from the group consisting of fluorenes, indenofluorenes, spirobifluorenes, carbazoles, indenocarbazoles, indolocarbazoles, spirocarbazoles, pyrimidines, triazines, lactams, triarylamines, dibenzofurans, dibenzothienes, imidazoles, benzimidazoles, benzoxazoles, benzthiazoles, 5-aryl-phenanthridin-6-ones, 9,10-dehydrophenanthrenes, fluoranthenes, anthracenes, benzanthracenes, and fluoradenes. It may preferably be provided that a residue R directly bonded to a nitrogen atom does not represent a group selected from OH, F, Cl, Br, I, CN, NO₂, N(Ar)₂, or N(R). 1 )2, where R 1 which has the meaning mentioned above, especially for formulas (Ia) to (If). Accordingly, in formulas (Vf) to (Vk), the group R represents a preferably no OH-, F-, Cl-, Br-, I-, CN-, NO2-, N(Ar)2-, N(R 1 )2-remainder, where R 1the meaning mentioned above, particularly for formulas (Ia) to (If). In a further preferred embodiment, the structures of formulas (Ia) to (If) and the preferred embodiments of these structures described above and below do not exhibit any NN bonding. Furthermore, it may be provided that at least one of the residues R and / or R' aselected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 9,9'-diaryl-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, pyrenyl, triazinyl, imidazolyl, benzimidazolyl, benzoxazolyl, benzthiazolyl, 1-, 2-, 3- or 4-carbazolyl, 1- or 2-napthyl, anthracenyl, preferably 9-anthracenyl, trans- and cis-indienofluorenyl, indenocarbazolyl, Indolocarbazolyl, spirocarbazolyl, 5-aryl-phenanthridin-6-on-yl, 9,10-dehydrophenanthrenyl, fluoranthenyl, tolyl, mesityl, phenoxytolulyl, anisolyl, triarylaminyl, bis-triarylaminyl, tris-triarylaminyl, hexamethylindanyl, tetralinyl, monocycloalkyl, Biscycloalkyl, tricycloalkyl, alkyl, such astert-Butyl, methyl, propyl, alkoxyl, alkylsulfanyl, alkylaryl, triarylsilyl, trialkylsilyl, xanthenyl, 10-aryl-phenoxazinyl, phenanthrenyl and / or triphenylenyl, each of which may be substituted by one or more substituents, but preferably are unsubstituted, wherein phenyl, spirobifluorene, fluorene, dibenzofuran, dibenzothiophene, anthracene, phenanthrene, and triphenylene groups are particularly preferred. If the structures described above and below are modified by substituents R and / or R. a If they are substituted, then these substituents are R and / or R'. a preferably selected from the group consisting of H, D, F, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, a straight-chain alkyl or alkoxy group with 1 to 10 C atoms, or a branched or cyclic alkyl or alkoxy group with 3 to 10 C atoms, or an alkenyl group with 2 to 10 C atoms, each with one or more R groups 1may be substituted, wherein one or more non-adjacent CH2 groups may be replaced by O and wherein one or more H atoms may be replaced by D or F, an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, each with one or more R groups 1 may be substituted, but preferably is unsubstituted, or an aralkyl or heteroaralkyl group with 5 to 25 aromatic ring atoms coupled with one or more R groups 1 can be substituted; optionally, two substituents R and / or R can be used. a , which are preferably bonded to adjacent carbon atoms, form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which is joined with one or more R groups 1The substituent can be substituted, with the group Ar having the meaning previously mentioned, especially for formulas (Ia) to (If). These substituents R and / or R are particularly preferred. a selected from the group consisting of H, D, F, CN, N(Ar)2, a straight-chain alkyl group with 1 to 8 C atoms, preferably with 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group with 3 to 8 C atoms, preferably with 3 or 4 C atoms, or an alkenyl group with 2 to 8 C atoms, preferably with 2, 3 or 4 C atoms, each with one or more R groups 1 may be substituted, but preferably is unsubstituted, or an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably with 6 to 13 aromatic ring atoms, each of which is coupled with one or more non-aromatic residues R 1can be substituted, but is preferably unsubstituted; optionally, two substituents R can be used. 1 , preferably those bonded to adjacent carbon atoms, forming a monocyclic or polycyclic aliphatic ring system, which is joined with one or more R groups 2 Ar can be substituted, but preferably unsubstituted, where Ar can have the meaning set forth above. Particularly preferably, the substituents R are selected from the group consisting of H or an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, each of which is coupled with one or more non-aromatic residues R. 1may be substituted, but preferably is unsubstituted. Examples of suitable substituents R are selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, triazinyl, quinazolinyl, quinoxalinyl, quinolinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, 1-, 2-, 3- or 4-carbazolyl and indenocarbazolyl, each of which is modified by one or more R groups. 1 They can be substituted, but are preferably unsubstituted. The substituents R are particularly preferred. a selected from the group consisting of an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, each with one or more non-aromatic residues R 1It can be substituted, but is preferably unsubstituted. Examples of suitable substituents R a are selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, triazinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, 1-, 2-, 3- or 4-carbazolyl and indenocarbazolyl, each of which is modified by one or more R groups 1 They may be substituted, but are preferably unsubstituted. Furthermore, it may be stipulated that the substitutes R and / or R' aThe structures described above and below, preferably structures according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk), do not form a condensed aromatic or heteroaromatic ring system among themselves, preferably not a condensed ring system. This excludes the formation of a condensed ring system with possible substituents R 1 and R 2 one that is attached to the residues R and / or R a or at R 1 can be bound. According to a further embodiment, the connection according to the invention may comprise a hole transport group, preferably comprising at least one of the previously described groups R and / or R. a, which may be contained in a structure according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk), preferably comprises a hole transport group. Hole transport groups are known in the art, preferably comprising triarylamine or carbazole groups. Preferably, the hole transport group may comprise a group, preferably representing a group selected from formulas (H-1) to (H-3), where the dashed line marks the attachment position and the symbols have the following meaning; Ar 2 , Ar 3 , Ar 4 Each is independently an aromatic ring system with 6 to 40 carbon atoms or a heteroaromatic ring system with 3 to 40 carbon atoms, each of which is separated by one or more R groups. 1 can be substituted; p is 0 or 1; Z represents a bond or C(R) 1 )2, Si(R 1)2, C=O, NR 1 , N-Ar 1 , BR 1 , PR 1 , PO(R 1 ), SO, SO2, Se, O or S, preferably for a bond or C(R 1 )2, N-Ar 1 , O or S; where the symbols Ar 1 and R 1 the meaning mentioned above, in particular for formulas (Ia) to (If). Here, the presence of an N-N bond is preferably excluded. Furthermore, it may be provided that the hole transport group comprises a group, preferably a group, selected from formulas (H-4) to (H-26).

[0007] where Y 1 O, S, C(R 1 )2, NR 1 or NAr 1 The dashed line represents the attachment position, e is 0, 1 or 2, j is 0, 1, 2 or 3, h is the same or different for each occurrence 0, 1, 2, 3 or 4, p is 0 or 1, Ar 1 and R 1the previously mentioned, especially for formulas (Ia) to (If) and Ar 2 the meanings mentioned above, in particular for formula (H-1) or (H-2). The presence of a non-neighbor bond is preferably excluded. It is evident from the above formulation that if the index p = 0, the corresponding group Ar 2 is not present and a bond is formed. Preferably, the group Ar 2 with the aromatic or heteroaromatic residue or the nitrogen atom to which the group Ar is attached 2 which can be bound according to formulas (H-1) to (H-26), form a continuous conjugation. In a further preferred embodiment of the invention, Ar 2 for an aromatic or heteroaromatic ring system with 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system with 6 to 12 carbon atoms, which is modified by one or more R groups 1can be substituted, but is preferably unsubstituted, where R 1 which can have the meaning mentioned above, especially for formulas (Ia) to (If). Ar is particularly preferred. 2 for an aromatic ring system with 6 to 10 aromatic ring atoms or a heteroaromatic ring system with 6 to 13 heteroaromatic ring atoms, each of which is separated by one or more R groups 1 can be substituted, but is preferably unsubstituted, where R 1 which may have the meaning mentioned above, in particular for formulas (Ia) to (If). Furthermore, the symbol Ar, shown inter alia in formulas (H-1) to (H-26), is preferred. 2for an aryl or heteroaryl residue with 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 ring atoms, such that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is directly bonded, i.e., via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group. Furthermore, it can be provided that the group Ar shown in formulas (H-1) to (H-26) 2The aromatic ring system comprises at most two fused aromatic and / or heteroaromatic six-membered rings, preferably no fused aromatic or heteroaromatic ring system with fused six-membered rings. Accordingly, naphthyl structures are preferred over anthracene structures. Furthermore, fluorenyl, spirobifluorenyl, dibenzofuranyl, and / or dibenzothienyl structures are preferred over naphthyl structures. Particularly preferred are structures that do not exhibit condensation, such as phenyl, biphenyl, terphenyl, and / or quaterphenyl structures. Furthermore, it may be provided that the group Ar, set out inter alia in formulas (H-1) to (H-26), is represented. 2 at most 1 nitrogen atom, preferably at most 2 heteroatoms, particularly preferably at most one heteroatom, and particularly preferably no heteroatom. In a further preferred embodiment of the invention, Ar 3 and / or Ar 4the same or different in each occurrence for an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably for an aromatic ring system with 6 to 12 aromatic ring atoms or a heteroaromatic ring system with 6 to 13 aromatic ring atoms, each of which is further divided by one or more R groups 1 can be substituted, but is preferably unsubstituted, where R 1 which may have the meaning shown above, in particular in formulas (Ia) to (If). According to a further embodiment, the compound according to the invention may comprise a residue comprising an electron transport group, preferably at least one of the groups R and / or R' described above. a, which may be contained in a structure according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk), preferably comprises an electron transport group-containing residue. Electron transport groups are well known in the field and enhance the ability of compounds to transport and / or conduct electrons. Furthermore, compounds according to the invention exhibit surprising advantages, comprising at least one structure selected from the group consisting of pyridines, pyrimidines, pyrazines, pyridazines, triazines, quinazolines, quinoxalines, quinolines, isoquinolines, imidazoles and / or benzimidazoles, with pyrimidines, triazines and quinazolines being particularly preferred. These structures generally enhance the ability of compounds to transport and / or conduct electrons.In a preferred embodiment of the present invention, it can be provided that the electron transport group-comprising residue represents a group that can be represented by the formula (QL). in which L 1 a bond or an aromatic or heteroaromatic ring system with 5 to 40, preferably 5 to 30 aromatic ring atoms, which is articulated by one or more R groups 1 can be substituted, Q is an electron transport group, where R 1 the meaning mentioned above, especially for formulas (Ia) to (If), and the dashed line marks the connection position. Preferably, the group L 1 with group Q and the atom, preferably the carbon or nitrogen atom, to which group L 1According to formula (QL), a continuous conjugation forms. A continuous conjugation of aromatic or heteroaromatic systems is formed as soon as direct bonds are formed between adjacent aromatic or heteroaromatic rings. Further linkage between the aforementioned conjugated groups, for example via an S, N, or O atom or a carbonyl group, does not impair conjugation. In a fluorene system, the two aromatic rings are directly bonded, with the sp 3 Although the hybridized carbon atom in position 9 prevents condensation of these rings, conjugation can still occur because this sp 3The hybridized carbon atom in position 9 is not necessarily located between the electron-transporting group Q and the atom via which the group of formula (QL) binds to further structural elements of a compound according to the invention. In contrast, in a second spirobifluorene structure, continuous conjugation can be formed if the bond between group Q and the aromatic or heteroaromatic residue to which group L is attached is located. 1 The bonding according to formula (QL) occurs via the same phenyl group of the spirobifluorene structure or via phenyl groups of the spirobifluorene structure that are directly bonded to each other and lie in one plane. If the bonding is between group Q and the aromatic or heteroaromatic residue to which group L is attached, 1 The bonding according to formula (QL) occurs via various phenyl groups of the second spirobifluorene structure, which is connected via the sp 3When hybridized carbon atoms are connected at position 9, the conjugation is interrupted. In another preferred embodiment of the invention, L 1 for a bond or for an aromatic or heteroaromatic ring system with 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system with 6 to 12 carbon atoms, which is divided by one or more R groups 1 can be substituted, but is preferably unsubstituted, where R 1 which can have the meaning mentioned above, especially for formulas (Ia) to (If). L is particularly preferred. 1 for an aromatic ring system with 6 to 10 aromatic ring atoms or a heteroaromatic ring system with 6 to 13 heteroaromatic ring atoms, each of which is separated by one or more R groups 2 can be substituted, but is preferably unsubstituted, where R 2which can have the meaning mentioned above, especially for formulas (Ia) to (If). The symbol L, as shown, among other things, in formula (QL), is also preferred. 1 the same or different for each occurrence for a bond or an aryl or heteroaryl residue with 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 ring atoms, such that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is directly bonded, i.e., via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group. Furthermore, it may be provided that the group L shown in formula (QL) 1The aromatic ring system comprises at most two fused aromatic and / or heteroaromatic six-membered rings, preferably no fused aromatic or heteroaromatic ring system. Accordingly, naphthyl structures are preferred over anthracene structures. Furthermore, fluorenyl, spirobifluorenyl, dibenzofuranyl, and / or dibenzothienyl structures are preferred over naphthyl structures. Particularly preferred are structures that do not exhibit condensation, such as phenyl, biphenyl, terphenyl, and / or quaterphenyl structures. Examples of suitable aromatic or heteroaromatic ring systems L 1are selected from the group consisting of ortho-, meta- or para-phenylenes, ortho-, meta- or para-biphenylenes, terphenylenes, in particular branched terphenylenes, quaterphenylenes, in particular branched quaterphenylenes, fluorenylenes, spirobifluorenylenes, dibenzofuranyles, dibenzothienylenes and carbazolylenes, each of which is further divided by one or more R groups 1 They may be substituted, but are preferably unsubstituted. Furthermore, it may be provided that the group L set out, inter alia, in formula (QL) 1 The structure comprises at most one nitrogen atom, preferably at most two heteroatoms, particularly preferably at most one heteroatom, and most preferably no heteroatom. Preferably, the group Q, or the electron transport group, as represented, inter alia, in formula (QL), can be selected from structures of formulas (Q-1), (Q-2), (Q-4), (Q-5), (Q-6).

[0008] where the dashed line marks the attachment position, Q' is the same or different at each occurrence CR 1 or represents N, and Q'' NR 1 , O or S; where at least one Q' is equal to N and R 1 as defined above, in particular in formulas (Ia) to (If). Furthermore, the group Q or the electron transport group shown, among others, in formula (QL) may preferably be selected from a structure of formulas (Q-11), (Q-12), (Q-13), (Q-14) and / or (Q-15).

[0009] where the symbol R 1 which has the meaning previously mentioned for formulas (Ia) to (If), X' N or CR 1where the dashed bond marks the bonding position, and X' preferably represents a nitrogen atom. In a further embodiment, the group Q or the electron transport group shown, inter alia, in formula (QL) can be selected from structures of formulas (Q-16), (Q-17), (Q-18), (Q-19), (Q-20), (Q-21) and / or (Q-22).

[0010] in which the symbol R 1the meaning previously set out, inter alia, for formulas (Ia) to (If), the dashed bond marks the bonding position, and m is 0, 1, 2, 3, or 4, preferably 0, 1, or 2; n is 0, 1, 2, or 3, preferably 0, 1, or 2; and o is 0, 1, or 2, preferably 1 or 2. The structures of formulas (Q-16), (Q-17), (Q-18), and (Q-19) are preferred. In a further embodiment, the group Q or the electron transport group set out, inter alia, in formula (QL), can be selected from structures of formulas (Q-23), (Q-24), and / or (Q-25).

[0011] in which the symbol R 1the meaning previously explained, inter alia, for formulas (Ia) to (If), and the dashed bond marks the bonding position. In a further embodiment, the group Q or the electron transport group shown, inter alia, in formula (QL) can be selected from structures of formulas (Q-26), (Q-27), (Q-28), (Q-29) and / or (Q-30),

[0012] where symbols Ar 1 and R 1 which previously have the meaning mentioned above for formula (Ia) to (If), X' N or CR 1The dashed bond indicates the bonding position. Preferably, in the structures of formulas (Q-26), (Q-27), and (Q-28), exactly one X' represents a nitrogen atom. Preferably, the group Q or the electron transport group shown, among others, in formula (QL) can be selected from structures of formulas (Q-31), (Q-32), (Q-33), (Q-34), (Q-35), (Q-36), (Q-37), (Q-38), (Q-39), (Q-40), (Q-41), (Q-42), (Q-43), and / or (Q-44).

[0013] in which the symbols Ar 1 and R 1 the meaning previously set out, inter alia, for formulas (Ia) to (If), the dashed line marks the connection position, and m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, n is 0, 1, 2 or 3, preferably 0 or 1, n is 0, 1, 2 or 3, preferably 0, 1 or 2, and l is 1, 2, 3, 4 or 5, preferably 0, 1 or 2. In a further preferred embodiment of the invention, Ar 1the same or different for each occurrence for an aromatic or heteroaromatic ring system, preferably an aryl or heteroaryl residue with 5 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably for an aromatic ring system, preferably an aryl residue with 6 to 12 aromatic ring atoms or a heteroaromatic ring system, preferably a heteroaryl group with 5 to 13 aromatic ring atoms, each of which is further divided by one or more residues R 2 can be substituted, but is preferably unsubstituted, where R 2 which may have the meaning previously described, in particular in formulas (Ia) to (If). Preferably, the symbol Ar 1for an aryl or heteroaryl residue, such that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is directly bonded, i.e., via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group, for example, a C or N atom of the previously described groups (H-1) to (H-26) or (Q-26) to (Q-44). Advantageously, Ar 1 in the formulas (H-1) to (H-26) or (Q-26) to (Q-44) represents an aromatic ring system with 6 to 12 aromatic ring atoms, which is coupled with one or more R groups 2 may be substituted, but preferably is unsubstituted, where R 2 which can have the meaning described above, especially for formulas (Ia) to (If). Preferably, the residues R 1 or R 2 in the formulas (H-1) to (H-26) or (Q-1) to (Q-44) with the ring atoms of the aryl group or heteroaryl group Ar 1 , Ar 2 , Ar 3 and / or Ar4 , to which the remains of R 1 or R 2 Since the substituents are bound, no condensed ring system is formed. This excludes the formation of a condensed ring system with possible substituents R. 2 one that is attached to the remains of R 1 may be bound. Furthermore, it may be provided that the group Ar, Ar 1 , Ar 2 , Ar 3 and / or Ar 4 selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, pyrenyl, triazinyl, imidazolyl, benzimidazolyl, benzoxazolyl, benzthiazolyl, 1-, 2-, 3- or 4-carbazolyl, indenocarbazolyl, 1- or 2-napthyl, anthracenyl, preferably 9-anthracenyl, phenanthrenyl and / or triphenylenyl, each of which is modified by one or more R groups1 and / or R 2 The groups may be substituted, but are preferably unsubstituted, with phenyl, spirobifluorene, fluorene, dibenzofuran, dibenzothiophene, anthracene, phenanthrene, and triphenylene groups being particularly preferred. In a preferred embodiment, it may be provided that at least two substituents R and / or R' are present. a in a structure according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk), each comprising a hole transport group, preferably. Furthermore, it may be provided that at least one of the residues R and / or R' a in a structure according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) comprising two hole transport groups. Here, one hole transport group can be a residue R. 1 are considered, in this case the substituents R shown in the structures of formulas (H-1) to (H-26). 1 through residues R2 to be replaced. Furthermore, it may be stipulated that at least one of the remaining R 1 in a structure according to one of the formulas (Vg) to (Vk) comprises a hole transport group, in this case the substituents R shown in the structures of formulas (H-1) to (H-26) 1 through residues R 2 to be replaced. In a preferred embodiment, it may be provided that at least two residues R and / or R' are to be replaced. a in a structure according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk), each comprising an electron transport group-containing residue, preferably. Furthermore, it may be provided that at least one of the residues R and / or R' ain a structure according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) comprising two electron transport group-containing residues. Here, one electron transport group-containing residue can be designated as residue R. 1 are considered, in this case the substituents R shown in the structures of formulas (QL) and / or (Q-1) to (Q-44). 1 through residues R 2 to be replaced. Furthermore, it may be stipulated that at least one of the remaining R 1 in a structure according to one of the formulas (Vg) to (Vk) includes an electron transport group-containing residue, in this case the substituents R shown in the structures of formulas (H-1) to (H-26) 1 through residues R 2 to be replaced, in this case by the substituents R shown in the structures of formulas (QL) and / or (Q-1) to (Q-44). 1 through residues R 2to be replaced. In a further embodiment, it may be provided that at least one of the residues R and / or R' is replaced. a in a structure according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) comprising a hole transport group, preferably representing, and at least one of the residues R and / or R a a residue comprising an electron transport group, preferably represents. Furthermore, it can be provided that at least one of the residues R and / or R's a in a structure according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) includes both an electron transport group-containing residue and a hole transport group. Here, an electron transport group-containing residue or a hole transport group can be represented as residue R. 1are considered, in this case the substituents R shown in the structures of formulas (QL), (Q-1) to (Q-44) or (H-1) to (H-26). 1 through residues R 2 to be replaced. In a further embodiment, it may be provided that at least one of the residues R and / or R' is replaced. a at least one group that leads to wide-band-gap materials. The term "group that leads to wide-band-gap materials" indicates that the compounds can be used as wide-band-gap materials, so the compounds have corresponding groups. Wide-band-gap materials are explained in more detail later. Furthermore, it may be provided that at least one of the residues R and / or R's aThe compound comprises at least one group that leads to materials used as host materials. The term "group that leads to materials used as host materials" indicates that the compounds can be used as host materials, and therefore possess corresponding groups. Host materials are described in more detail later. In a further embodiment, the compound may comprise a condensed aromatic or heteroaromatic ring system with at least two, preferably three, condensed rings, which may optionally be substituted. Preferably, at least one of the substituents comprises R and / or R'. ain structures of formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) at least one aromatic or heteroaromatic ring system with two, preferably with three, fused aromatic or heteroaromatic rings. Preferably, the aromatic or heteroaromatic ring system with two, preferably with three, fused aromatic or heteroaromatic rings may be selected from the groups of formulas (Ar-1) to (Ar-11).

[0014] where X' N or CR 1 , preferably CR 1 is, L 1 a bond or an aromatic or heteroaromatic ring system with 5 to 40, preferably 5 to 30 aromatic ring atoms, which is articulated by one or more R groups 1 can be substituted, where R 1the meaning previously explained, particularly for formulas (Ia) to (If), and the dashed bond marks the attachment position. It is particularly preferred that the aromatic or heteroaromatic ring system with two, preferably three, fused aromatic or heteroaromatic rings is selected from the groups of formulas (Ar'-1) to (Ar'-11).

[0015] where L 1 a bond or an aromatic or heteroaromatic ring system with 5 to 40, preferably 5 to 30 aromatic ring atoms, which is articulated by one or more R groups 1 can be substituted, where R 1the meaning previously set out, in particular for formulas (Ia) to (If), the dashed line marks the connection position and the following applies to the indices: p is 0 or 1; e is 0, 1 or 2, preferably 0 or 1; j is 0, 1, 2 or 3 in each occurrence, preferably 0, 1 or 2, particularly preferably 0 or 1; h is 0, 1, 2, 3 or 4 in each occurrence, preferably 0, 1 or 2, particularly preferably 0 or 1; i is 0, 1 or 2 in each occurrence; m is an integer in the range of 0 to 7, preferably 0, 1, 2, 3, 4, 5 or 6, particularly preferably 0, 1, 2, 3 or 4, especially preferably 0, 1 or 2. Preferably, the sum of the indices p, e, i, j, h and m in the structures of formula (Ar'-1) to (Ar'-11) is at most 3, preferably at most 2 and particularly preferably at most 1.The structures of formulas (Ar-1) to (Ar-11) and / or (Ar'-1) to (Ar'-11) described above are particularly preferred residues for compounds suitable for use as fluorescent emitters or as blue OLED materials. In a preferred embodiment of the present invention, one of the structures of formulas (Ar-1) to (Ar-11) and / or (Ar'-1) to (Ar'-11) described above constitutes a residue R. a in a structure of formulas (Vb) to (Vk), preferably (Vc) to (Ve). In a further preferred embodiment of the present invention, the group L represents 1 in the previously presented structures of formulas (Ar-1) to (Ar-11) and / or (Ar'-1) to (Ar'-11) represents an aromatic or heteroaromatic ring system with 5 to 40, preferably 5 to 30 aromatic ring atoms, which is articulated by one or more R groups 1 can be substituted, where R 1the meaning previously explained, particularly for formulas (Ia) to (If). In a further variant, compounds are specifically excluded from protection which have structures of formula (Va) where the residue Ra represents a structure of formula (Ar-5) or (Ar'-5), where the residue L 1 represents a bond. If X 1 for CR 1 stands or when the aromatic and / or heteroaromatic groups are replaced by substituents R 1 If they are substituted, then these substituents are R 1 preferably chosen from the group consisting of H, D, F, CN, N(Ar 1 )2, C(=O)Ar 1 , P(=O)(Ar 1 )2, a straight-chain alkyl or alkoxy group with 1 to 10 C atoms, or a branched or cyclic alkyl or alkoxy group with 3 to 10 C atoms, or an alkenyl group with 2 to 10 C atoms, each with one or more R groups 2may be substituted, wherein one or more non-adjacent CH2 groups may be replaced by O and wherein one or more H atoms may be replaced by D or F, an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, each with one or more R groups 2 may be substituted, but preferably is unsubstituted, or an aralkyl or heteroaralkyl group with 5 to 25 aromatic ring atoms coupled with one or more R groups 2 can be substituted; optionally, two substituents R can be used. 1 , which are preferably bonded to adjacent carbon atoms, form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which is joined with one or more R groups 1 can be substituted, whereby the group Ar 1the meaning mentioned above, especially for formulas (Ia) to (If). These substituents R are particularly preferred. 1 selected from the group consisting of H, D, F, CN, N(Ar 1 )2, a straight-chain alkyl group with 1 to 8 carbon atoms, preferably with 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group with 3 to 8 carbon atoms, preferably with 3 or 4 carbon atoms, or an alkenyl group with 2 to 8 carbon atoms, preferably with 2, 3 or 4 carbon atoms, each of which is linked to one or more R groups 2 may be substituted, but preferably is unsubstituted, or an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably with 6 to 13 aromatic ring atoms, each of which is coupled with one or more non-aromatic residues R 1 can be substituted, but is preferably unsubstituted; optionally, two substituents R can be used.1 , preferably those bonded to adjacent carbon atoms, forming a monocyclic or polycyclic aliphatic ring system, which is joined with one or more R groups 2 may be substituted, but is preferably unsubstituted, where Ar 1 which can have the significance described above. The substituents R are particularly favored. 1 selected from the group consisting of H or an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, each with one or more non-aromatic residues R 2 It can be substituted, but is preferably unsubstituted. Examples of suitable substituents R 1are selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, 1-, 2-, 3- or 4-carbazolyl and indenocarbazolyl, each of which is modified by one or more R groups 2 They can be substituted, but are preferably unsubstituted. Furthermore, it can be stipulated that the substitutes R 1 of an aromatic or heteroaromatic ring system with further ring atoms of the aromatic or heteroaromatic ring system, preferably not forming a condensed aromatic or heteroaromatic ring system. This excludes the formation of a condensed ring system with possible substituents R 2 one that is attached to the remains of R 1may be bound. Furthermore, it may be provided that in a structure according to formula (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) at least one residue R 1 or Ar 1 represents a group that is selected from the formulas (R 1 -1) to (R 1 - 43), or in a structure according to formula (H-1) to (H-26), (QL), (Q-1) to (Q-44), (Ar-1) to (Ar-11) and / or (Ar'-1) to (Ar'-11) at least one residue Ar 1 or R 1 represents a group that is selected from the formulas (R 1 -1) to (R 1 - 43)

[0016] where the following applies to the symbols used: Y 1 is O, S or NR 2, preferably O or S; k is independently 0 or 1 in each occurrence; i is independently 0, 1, or 2 in each occurrence; j is independently 0, 1, 2, or 3 in each occurrence; h is independently 0, 1, 2, 3, or 4 in each occurrence; g is independently 0, 1, 2, 3, 4, or 5 in each occurrence; R 2 can have the meaning mentioned above, especially for formulas (Ia) to (If), and the dashed line marks the connection position. Here, the groups of formulas R 1 -1 to R 1 -28 preferred, with the groups R 1 -1, R 1 -3, R 1 -4, R 1 -10, R 1 -11, R 1 -12, R 1 -13, R 1 -14, R 1 -16, R 1 -17, R 1 -18, R 1 -19, R 1 -20, R 1 -21 and / or R 1 -22 are particularly preferred. Preferably, it can be provided that the sum of the indices k, i, j, h and g in the structures of the formula (R 1-1) to (R 1 -43) each at most 3, preferably at most 2 and particularly preferably at most 1. Preferably the residues R 2 in the formulas (R 1 -1) to (R 1 -43) with the ring atoms of the aryl group or heteroaryl group to which the R residues are attached 2 are bound, not a condensed aromatic or heteroaromatic ring system, preferably not a condensed ring system. The previously stated residues of the formulas (R 1 -1) to (R 1 -43) represent preferred residues Ar according to formulas (Ia) to (If) respectively Ar 3 , Ar 4 according to formulas (H-1) to (H-3) or preferred embodiments of these formulas, wherein in this case the formulas (R 1 -1) to (R 1 -43) presented groups R 2 through residues R 1 to be replaced. The previously stated preferences regarding the formulas (R 1 -1) to (R 1-43) apply accordingly. Preferably, the compound may be provided to include at least one bonding group selected from the formulas (L 1 -1) to (L 1 -73), preferably in the structure according to formulas (H-1) to (H-26) the group Ar 2 selected from the formulas (L 1 -1) to (L 1 -73) or the electron transport group is connected to other structural elements via a connecting group selected from the formulas (L 1 -1) to (L 1 -73) or the remainder L 1 in formulas (QL), (Ar-1) to (Ar-11) and / or (Ar'-1) to (Ar'-11) represents a group selected from the formulas (L 1 -1) to (L 1 -73),

[0017] where the dashed lines mark the attachment positions, the index k is 0 or 1, the index l is 0, 1 or 2, the index j is 0, 1, 2 or 3 regardless of occurrence; the index h is 0, 1, 2, 3 or 4 regardless of occurrence, the index g is 0, 1, 2, 3, 4 or 5; the symbol Y 2 O, S or NR 1 , preferably O or S; and the symbol R 1 the meaning mentioned above, in particular for formulas (Ia) to (If). Preferably, it can be provided that the sum of the indices k, l, g, h and j in the structures of formula (L 1 -1) to (L 1 -73) each at most 3, preferably at most 2 and particularly preferably at most 1. Preferred compounds according to the invention with a group of formulas (H-1) to (H-26) comprise a group Ar 2 , which is selected from one of the formulas (L 1 -1) to (L 1 -46) and / or (L 1 -57) to (L 1-73), preferably the formula (L 1 -1) to (L 1 -32) and / or (L 1 -57) to (L 1 -73), especially preferred the formula (L 1 -1) to (L 1 -10) and / or (L 1 -57) to (L 1 - 68). Advantageously, the sum of the indices k, l, g, h and j can be used in the structures of the formulas (L 1 -1) to (L 1 -46) and / or (L 1 -57) to (L 1 -73), preferably the formula (L 1 -1) to (L 1 -32) and / or (L 1 -57) to (L 1 -73), especially preferred the formula (L 1 -1) to (L 1 -10) and / or (L 1 -57) to (L 1 -68) each amount to at most 3, preferably at most 2 and particularly preferably at most 1. Preferred compounds according to the invention with a group of formula (QL) comprise a group L 1 , which represents a bond or which is selected from one of the formulas (L 1 -1) to (L 1-46) and / or (L 1 -57) to (L 1 -73), preferably the formula (L 1 -1) to (L 1 -32) and / or (L 1 -57) to (L 1 - 73), especially preferred the formula (L 1 -1) to (L 1 -10) and / or (L 1 -57) to (L 1 -68). Advantageously, the sum of the indices k, l, g, h and j can be used in the structures of the formulas (L 1 -1) to (L 1 -46) and / or (L 1 -57) to (L 1 -73), preferably the formula (L 1 -1) to (L 1 -32) and / or (L 1 -57) to (L 1 -73), especially preferred the formula (L 1 -1) to (L 1 -10) and / or (L 1 -57) to (L 1 -68) each amount to at most 3, preferably at most 2 and particularly preferably at most 1. Preferred compounds according to the invention with a group of formulas (Ar-1) to (Ar-11) and / or (Ar'-1) to (Ar'-11) comprise a group L 1, which represents a bond or which is selected from one of the formulas (L 1 -1) to (L 1 -46) and / or (L 1 -57) to (L 1 -73), preferably the formula (L 1 -1) to (L 1 -32) and / or (L 1 -57) to (L 1 -73), especially preferred the formula (L 1 -1) to (L 1 -10) and / or (L 1 -57) to (L 1 -68). Advantageously, the sum of the indices k, l, g, h and j can be used in the structures of the formulas (L 1 -1) to (L 1 -46) and / or (L 1 -57) to (L 1 -73), preferably the formula (L 1 -1) to (L 1 - 32) and / or (L 1 -57) to (L 1 -73), especially preferred the formula (L 1 -1) to (L 1 -10) and / or (L 1 -57) to (L 1 -68) each amount to at most 3, preferably at most 2, and particularly preferably at most 1. Preferably, the residues R 2 in the formulas (L1 -1) to (L 1 -73) with the ring atoms of the aryl group or heteroaryl group to which the R residues are attached 2The compounds are bound in a non-condensed aromatic or heteroaromatic ring system, preferably not a condensed ring system at all. According to a preferred embodiment, a compound according to the invention can be represented by at least one of the structures according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk). Preferably, compounds comprising structures according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) have a molecular weight of less than or equal to 5000 g / mol, preferably less than or equal to 4000 g / mol, particularly preferably less than or equal to 3000 g / mol, especially preferably less than or equal to 2000 g / mol and most preferably less than or equal to 1200 g / mol. Furthermore, preferred compounds according to the invention are characterized by being sublimable. These compounds generally have a molar mass of less than approximately 1200 g / mol.If the compound according to the invention contains aromatic or hetero-aromatic groups R. 1 or R 2If the substituent is a group of compounds, it is preferred that these groups do not contain aryl or heteroaryl groups with more than two directly fused aromatic six-membered rings. Particularly preferred are the substituents that do not contain any aryl or heteroaryl groups with directly fused six-membered rings at all. This preference is due to the low triplet energy of such structures. Condensed aryl groups with more than two directly fused aromatic six-membered rings that are nevertheless suitable according to the invention are phenanthrene and triphenylene, since these also exhibit a high triplet energy level. In embodiments of the compounds according to the invention for use as fluorescent emitters or as blue OLED materials, preferred compounds can contain corresponding groups, for example, fluorene, anthracene, and / or pyrene groups, which are fused to groups R. 1 or R 2can be substituted or which are affected by appropriate substitution of the groups (L 1 -1) to (L 1 -73) or (R 1 -1) to (R 1 -43) with the substituents R 1 or R 2 are formed. In another preferred embodiment of the invention, R 2, for example, in a structure according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk), as well as preferred embodiments of this structure or the structures to which reference is made, in each occurrence the same or different selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbon residue with 1 to 10 C atoms, preferably with 1, 2, 3 or 4 C atoms, or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, preferably with 5 to 24 aromatic ring atoms, particularly preferably with 5 to 13 aromatic ring atoms, which may be substituted by one or more alkyl groups, each with 1 to 4 carbon atoms, but is preferably unsubstituted. Preferably, the residues R 2 with the ring atoms of the aryl group or heteroaryl group, to which the R residues are attached 2The compounds are not bound to a condensed aromatic or heteroaromatic ring system, preferably not a condensed ring system. Furthermore, the compound according to the invention may not be in direct contact with a metal atom, preferably not representing a ligand for a metal complex. Compounds according to the invention with structures of formula (Va) are particularly preferred, as they have the following properties:

[0018] Particularly preferred are compounds according to the invention with structures of formula (Vb) which have the following properties: Particularly preferred are compounds according to the invention with structures of formula (Vc) which have the following properties:

[0019] Particularly preferred are compounds according to the invention with structures of formula (Vd) which have the following properties: Particularly preferred are compounds according to the invention with structures of formula (Ve) which have the following properties:

[0020] Particularly preferred are compounds according to the invention with structures of formula (Vf) which have the following properties: Particularly preferred are compounds according to the invention with structures of formula (Vk) which have the following properties:

[0021] The remainders of formulas H-1 to H-26 in the tables presented above are preferably selected according to the following criteria: The remainders of the formula QL in the tables presented above are preferably selected according to the following criteria: Examples of suitable connections according to the above-mentioned design forms are the connections listed in the following table:

[0022] Preferred embodiments of the compounds according to the invention are described in more detail in the examples, and these compounds can be used alone or in combination with others for all purposes according to the invention. Provided that the conditions specified in claim 1 are met, the preferred embodiments mentioned above can be combined with one another as desired. In a particularly preferred embodiment of the invention, the preferred embodiments mentioned above apply simultaneously. The compounds according to the invention can, in principle, be produced by various methods. However, the methods described below have proven to be particularly suitable.Therefore, a further object of the present invention is a method for preparing the compounds according to the invention, preferably compounds comprising structures of formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk), in which a compound comprising a heterocyclic structure is coupled to a compound comprising at least one aromatic or heteroaromatic group in a coupling reaction. Suitable compounds comprising at least one heterocyclic structure can often be obtained commercially, and the starting compounds set out in the examples are obtainable by known methods, to which reference is made.These compounds can be reacted with other compounds comprising at least one aromatic or heteroaromatic group via known coupling reactions. The necessary conditions for this are known to those skilled in the art, and detailed information in the examples assists them in carrying out these reactions. Particularly suitable and preferred coupling reactions, all of which lead to C-C and / or CN couplings, are those described by Buchwald, Suzuki, Yamamoto, Stille, Heck, Negishi, Sonogashira, and Hiyama. These reactions are widely known, and the examples provide further guidance to those skilled in the art. The principles of the preparation methods described above are known from the literature for similar compounds and can be easily adapted by those skilled in the art to prepare the compounds according to the invention. Further information can be found in the examples.By these processes, optionally followed by purification, such as recrystallization or sublimation, the compounds according to the invention, comprising structures according to formula (Ia) to (If), can be obtained in high purity, preferably more than 99% (determined by means of. 1The compounds according to the invention can also have suitable substituents, for example, longer alkyl groups (approximately 4 to 20 carbon atoms), in particular branched alkyl groups, or optionally substituted aryl groups, for example, xylyl, mesityl, or branched terphenyl or quaterphenyl groups, which effect solubility in common organic solvents, such that the compounds are soluble in, for example, toluene or xylene at room temperature in sufficient concentration to allow processing from solution. These soluble compounds are particularly well suited for processing from solution, for example, by printing processes. Furthermore, it should be noted that the compounds according to the invention, comprising at least one structure of formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf), and / or (Va) to (Vk), already possess increased solubility in these solvents.Furthermore, the compounds of the present invention can contain one or more crosslinkable groups. A "crosslinkable group" is a functional group capable of irreversible reaction, resulting in the formation of a crosslinked material that is insoluble. Crosslinking can typically be aided by heat or by UV, microwave, X-ray, or electron radiation. This crosslinking process produces very little byproduct. Moreover, the crosslinkable groups that may be present in the functional compounds crosslink very readily, requiring lower energy levels for crosslinking (e.g., < 200°C for thermal crosslinking). Examples of crosslinkable groups include units containing a double bond, a triple bond, a precursor capable of in situ formation of a double or triple bond, or a heterocyclic, addition-polymerizable residue.Crosslinkable groups include, among others, vinyl, alkenyl, preferably ethenyl and propenyl, C. 4-20 -Cycloalkenyl, azide, oxirane, oxetane, di(hydrocarbyl)amino, cyanate ester, hydroxy, glycidyl ether, C 1-10 -Alkyl acrylate, C 1-10 -Alkyl methacrylate, alkenyloxy, preferably ethenyloxy, perfluoroalkenyloxy, preferably perfluoroethenyloxy, alkynyl, preferably ethinyl, maleimide, cyclobutylphenyl, tri(C 1-4 )-alkylsiloxy and Tri(C 1-4)-alkylsilyl. Cyclobutylphenyl, vinyl, and alkenyl are particularly preferred. The compounds according to the invention can also be mixed with a polymer. It is also possible to covalently incorporate these compounds into a polymer. This is particularly possible with compounds substituted with reactive leaving groups, such as bromine, iodine, chlorine, boronic acid, or boronic esters, or with reactive, polymerizable groups, such as olefins or oxetanes. These can be used as monomers to produce corresponding oligomers, dendrimers, or polymers. The oligomerization or polymerization preferably occurs via the halogen functionality or the boronic acid functionality, or via the polymerizable group. It is also possible to crosslink the polymers via such groups. The compounds and polymers according to the invention can be used as crosslinked or uncrosslinked layers. A further aspect of the invention is therefore oligomers,Polymers or dendrimers containing one or more of the structures listed above with formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk), or compounds according to the invention, wherein one or more bonds of the compounds according to the invention or of the structures with formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) are present to form the polymer, oligomer, or dendrimer. Depending on the linkage of the structures with formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) or of the compounds, these therefore form a side chain of the oligomer or polymer or are linked in the main chain. The polymers, oligomers, or dendrimers can be conjugated, partially conjugated, or non-conjugated. The oligomers or polymers can be linear, branched, or dendritic. For the repeating units of the compounds according to the invention in oligomers,Dendrimers and polymers are subject to the same advantages as described above. To produce the oligomers or polymers, the monomers according to the invention are homopolymerized or copolymerized with further monomers. Copolymers are preferred, wherein the units according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk), or the previously and subsequently described preferred embodiments, are present in amounts of 0.01 to 99.9 mol%, preferably 5 to 90 mol%, and particularly preferably 20 to 80 mol%. Suitable and preferred comonomers forming the polymer backbone are selected from fluorenes (e.g., according to EP 842208 or WO 2000 / 022026), spirobifluorenes (e.g., according to EP 707020, EP 894107 or WO 2006 / 061181), para-phenylenes (e.g., according to WO 92 / 18552), carbazoles (e.g., according to WO 2004 / 070772 or WO 2004 / 113468), thiophenes (e.g., according to EP 1028136), dihydrophenanthrenes (e.g., according to WO 2005 / 014689).cis- and trans-indenofluorenes (e.g., according to WO 2004 / 041901 or WO 2004 / 113412), ketones (e.g., according to WO 2005 / 040302), phenanthrenes (e.g., according to WO 2005 / 104264 or WO 2007 / 017066), or several of these units. The polymers, oligomers, and dendrimers may contain further units, for example, hole transport units, in particular those based on triarylamines, and / or electron transport units. Compounds according to the invention that are characterized by a high glass transition temperature are also of particular interest. In this context, compounds according to the invention are particularly preferred, comprising structures according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) or the previously and subsequently described preferred embodiments, which have a glass transition temperature of at least 70 °C, particularly preferably at least 110 °C.The liquid phase is most preferably at least 125 °C and particularly preferably at least 150 °C, as determined according to DIN 51005 (version 2005-08). For processing the compounds according to the invention from the liquid phase, for example by spin coating or by printing processes, formulations of the compounds according to the invention are required. These formulations can be, for example, solutions, dispersions, or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents include, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrol, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, and acetophenone.^- Terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecyl benzene, ethyl benzoate, indane, NMP, p-cymene, phenetol, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, Diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, 2-methylbiphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, Sebabic acid diethyl ester, octyl octanoate, heptylbenzene, menthyl isovalerate, cyclohexyl hexanoate, or mixtures of these solvents. A further object of the present invention is therefore a formulation or composition,comprising at least one compound according to the invention and at least one further compound. The further compound may, for example, be a solvent, in particular one of the solvents mentioned above or a mixture of these solvents. If the further compound comprises a solvent, this mixture shall be referred to herein as a formulation. The further compound may also be at least one further organic or inorganic compound that is also used in the electronic device.For example, an emitting compound and / or another matrix material. Suitable emitting compounds and other matrix materials are listed later in connection with the organic electroluminescence device. The other compound can also be polymeric. A further object of the present invention is therefore a composition comprising a compound according to the invention and at least one other organically functional material. Functional materials are generally the organic or inorganic materials that are introduced between the anode and the cathode. Preferably, the organically functional material is selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF (thermally activated delayed fluorescence), host materials, electron transport materials, electron injection materials, hole transport materials, and hole injection materials.Electron-blocking materials, hole-blocking materials, wide-band-gap materials, and n-dopeds. A further object of the present invention is a composition comprising at least one compound according to the invention, preferably a compound comprising at least one structure according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf), and / or (Va) to (Vk), or the preferred embodiments described above and below, as well as at least one wide-band-gap material, wherein a wide-band-gap material is understood to be a material as defined in US 7,294,849. These systems exhibit particularly advantageous performance characteristics in electroluminescent devices. Preferably, the additional compound can have a band gap of 2.5 eV or more, more preferably 3.0 eV or more, and most preferably 3.exhibiting 3 eV or more. The band gap can be calculated, among other things, from the energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO). Molecular orbitals, in particular the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), their energy levels, as well as the energy of the lowest triplet state T1 or the lowest excited singlet state S1 of the materials, are determined via quantum chemical calculations. To calculate organic substances without metals, a geometry optimization is first performed using the method "Ground State / Semi-empirical / Default Spin / AM1 / Charge 0 / Spin Singlet". Subsequently, an energy calculation is performed based on the optimized geometry. Here, the method "TD-SCF / DFT / Default Spin / B3PW91" with the basis set "6-31G(d)" is used (Charge 0,Spin Singlet). For metal-containing compounds, the geometry is optimized using the method "Ground State / Hartree-Fock / Default Spin / LanL2MB / Charge 0 / Spin Singlet". The energy calculation is analogous to the method described above for organic substances, with the difference that the basis set "LanL2DZ" is used for the metal atom and the basis set "6-31G(d)" for the ligands. From the energy calculation, the HOMO energy level HEh or LUMO energy level LEh in Hartree units is obtained. From this, the HOMO and LUMO energy levels, calibrated using cyclic voltammetry measurements, are determined in electron volts as follows: HOMO(eV) = ((HEh*27.212)-0.9899) / 1.1206 LUMO(eV) = ((LEh*27.212)-2.0041) / 1.385 These values ​​are to be considered, for the purposes of this application, as the HOMO and LUMO energy levels of the materials, respectively. The lowest triplet state T1 is defined as the energy of the triplet state with the lowest energy.which results from the described quantum chemical calculation. The lowest excited singlet state S1 is defined as the energy of the lowest-energy excited singlet state resulting from the described quantum chemical calculation. The method described herein is independent of the software package used and always yields the same results. Examples of commonly used programs for this purpose are "Gaussian09W" (Gaussian Inc.) and Q-Chem 4.1 (Q-Chem, Inc.). The present invention also relates to a composition comprising at least one compound comprising structures according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) or the preferred embodiments described above and below, as well as at least one phosphorescent emitter,The term phosphorescent emitters also includes phosphorescent dopants. In a system containing a matrix material and a dopant, a dopant is understood to be the component with the smaller proportion in the mixture. Similarly, in a system containing a matrix material and a dopant, a matrix material is understood to be the component with the larger proportion in the mixture. Preferred phosphorescent dopants for use in matrix systems, preferably mixed-matrix systems, are those listed below. The term phosphorescent dopants typically encompasses compounds in which light emission occurs via a spin-forbidden transition, for example, a transition from an excited triplet state or a state with a higher spin quantum number.For example, a quintet state. Suitable phosphorescent compounds (= triplet emitters) are, in particular, compounds that emit light, preferably in the visible range, upon suitable excitation and also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, and especially preferably greater than 56 and less than 80, particularly a metal with this atomic number. Compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are preferred as phosphor emitters, especially compounds containing iridium or platinum. Examples of the issuers 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 / 001990, WO 2018 / 019687, WO 2018 / 019688, WO 2018 / 041769, WO 2018 / 054798, WO 2018 / 069196, WO 2018 / 069197, WO 2018 / 069273, WO 2018 / 178001, WO 2018 / 177981, WO 2019 / 020538, WO 2019 / 115423, WO 2019 / 158453 and WO 2019 / 179909. In general, all phosphorescent complexes used in phosphorescent electroluminescence devices according to the prior art and known to those skilled in the art in the field of organic electroluminescence are suitable, and those skilled in the art can use other phosphorescent complexes without inventive effort. Examples of phosphorescent dopants are listed in the following table.

[0023] When the compound according to the invention is used as a matrix material for a phosphorescent compound in an emitting layer, it is preferably used in combination with one or more phosphorescent materials (triplet emitters). Phosphorescence within the meaning of this invention is understood to mean luminescence from an excited state with higher spin multiplicity, i.e., a spin state > 1, in particular from an excited triplet state. For the purposes of this application, all luminescent complexes with transition metals or lanthanides, in particular all iridium, platinum, and copper complexes, are to be considered phosphorescent compounds. The mixture of the compound according to the invention and the emitting compound contains between 99 and 1 vol%, preferably between 98 and 10 vol%, particularly preferably between 97 and 60 vol%, and in particular between 95 and 80 vol%.-% of the compound according to the invention based on the total mixture of emitter and matrix material. Accordingly, the mixture contains between 1 and 99 vol%, preferably between 2 and 90 vol%, particularly preferably between 3 and 40 vol%, and especially between 5 and 20 vol% of the emitter based on the total mixture of emitter and matrix material. In one embodiment of the invention, the compound according to the invention is used as the sole matrix material ("single host") for the phosphorescent emitter. In a preferred embodiment of the invention, the organic electroluminescent device contains the compound according to the invention, preferably a compound comprising structures according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk).The preferred embodiments listed above are used as matrix materials, preferably as electron-conducting matrix materials in one or more emitting layers, preferably in combination with a further matrix material, preferably a hole-conducting matrix material. In a further preferred embodiment of the invention, the further matrix material is an electron-transporting compound. In yet another preferred embodiment, the further matrix material is a large-bandgap compound that is not involved, or not to a significant extent, in hole and electron transport in the layer. An emitting layer comprises at least one emitting compound.In a further particularly preferred embodiment of the present invention, an organic electroluminescence device according to the invention comprises the compound according to the invention, preferably a compound comprising structures according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) or the preferred embodiments listed above in a hole transport layer or an electron transport layer. The present invention therefore also relates to a composition comprising at least one compound according to the invention, preferably a compound comprising structures according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) or the preferred embodiments described above, as well as at least one further matrix material.Suitable matrix materials which can be used in combination with the compounds according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) or according to the preferred embodiments are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680, triarylamines, carbazole derivatives, etc. B. CBP (N,N-Biscarbazolylbiphenyl) or those in WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or WO 2013 / 041176, indolocarbazole derivatives, e.g. according to WO 2007 / 063754 or WO 2008 / 056746, indenocarbazole derivatives, e.g. according to WO 2010 / 136109, WO 2011 / 000455, WO 2013 / 041176 or WO 2013 / 056776, azacarbazole derivatives, e.g. B. 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, azaborols or boron esters, e.g.according to WO 2006 / 117052, triazine derivatives, e.g. according to WO 2007 / 063754, WO 2008 / 056746, WO 2010 / 015306, WO 2011 / 057706, WO 2011 / 060859 or WO 2011 / 060877, zinc complexes, e.g. according to EP 652273 or WO 2009 / 062578, diazasilol or tetraazasilol derivatives, e.g. according to WO 2010 / 054729, diazaphosphole derivatives, e.g. according to WO 2010 / 054730, bridged carbazole derivatives, e.g. B. according to WO 2011 / 042107, WO 2011 / 060867, WO 2011 / 088877 and WO 2012 / 143080, triphenylene derivatives, e.g. according to WO 2012 / 048781, dibenzofuran derivatives, e.g. according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO 2017 / 148565 or biscarbazoles, e.g. according to JP 3139321 B2, lactams, e.g. B. according to WO 2011 / 116865, WO 2011 / 137951 or WO 2013 / 064206, 4-spirocarbazole derivatives, e.g. according to WO 2014 / 094963 or WO 2015 / 192939. Likewise, another phosphorescent emitter, which emits at a shorter wavelength than the actual emitter, may be present as a co-host in the mixture.Preferred co-host materials are triazines, quinazolines, quinoxalines, triarylamine derivatives, in particular monoamines, indenocarbazole derivatives, 4-spirocarbazole derivatives, lactams, and carbazole derivatives. Preferred triarylamine derivatives used as co-host materials with the compounds according to the invention are selected from the compounds of the following formula (TA-1). Formula (TA-1) where Ar 5 The aromatic or heteroaromatic ring system with 6 to 40 carbon atoms, each with one or more R groups, is the same or different in each occurrence. 1 can be substituted, representing, optionally two or more adjacent substituents R 1 can form a mono- or polycyclic, aliphatic ring system, which is joined with one or more R residues 2 can be substituted, where the symbols R 1 and R 2the meaning mentioned above, in particular for formulas (Ia) to (If). Preferably, Ar 5 The group, whether identical or different in each occurrence, represents an aryl or heteroaryl group with 5 to 24, preferably 5 to 12, aromatic ring atoms, each with one or more R substituents. 1 may be substituted, but preferably is unsubstituted. Examples of suitable groups Ar 5 are selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, indenocarbazolyl, 1-, 2-, 3- or 4-dibenzothienyl and 1-, 2-, 3- or 4-carbazolyl, each of which is modified by one or more R groups 1 They can be substituted, but are preferably unsubstituted. The preferred groups are Ar 5same or different for each occurrence, selected from the above-mentioned groups R 1 -1 to R 1 -43, especially preferred R 1 -1 to R 1 -28. In a preferred embodiment of the compounds of formula (TA- 1), at least one group Ar 5 selected from a biphenyl group, which may be an ortho-, meta- or para-biphenyl group. In a further preferred embodiment of the compounds of formula (TA-1), at least one group is Ar 5 selected from a fluorene group or spirobifluorene group, wherein these groups may each be bonded to the nitrogen atom in the 1-, 2-, 3- or 4-position. In yet another preferred embodiment of the compounds of formula (TA-1), at least one group Ar 5selected from a phenylene or biphenyl group, wherein the ortho-, meta-, or para-linked group is substituted with a dibenzofuran group, a dibenzothiophene group, or a carbazole group, in particular a dibenzofuran group, wherein the dibenzofuran or dibenzothiophene group is linked to the phenylene or biphenyl group via the 1-, 2-, 3-, or 4-position, and wherein the carbazole group is linked to the phenylene or biphenyl group via the 1-, 2-, 3-, or 4-position or via the nitrogen atom. In a particularly preferred embodiment of the compounds of formula (TA-1), a group Ar 5 selected from a fluorene or spirobifluorene group, in particular a 4-fluorene or 4-spirobifluorene group, and a group Ar 5 is selected from a biphenyl group, in particular a para-biphenyl group, or a fluorene group, in particular a 2-fluorene group, and the third group Ar 5is selected from a para-phenylene group or a para-biphenyl group substituted with a dibenzofuran group, in particular a 4-dibenzofuran group, or a carbazole group, in particular an N-carbazole group or a 3-carbazole group. Preferred indenocarbazole derivatives used as co-host materials together with the compounds according to the invention are selected from the compounds of the following formula (TA-2), where Ar 5 and R 1 the meanings listed above, particularly for formulas (I) and / or (TA-1). Preferred embodiments of group Ar are 5 the structures listed above R 1 -1 to R 1 -43, especially preferred R 1 -1 to R 1 -28. A preferred embodiment of the compounds of formula (TA-2) are the compounds of the following formula (TA-2a), where Ar 5 and R 1the meanings listed above, especially for formulas (I) and / or (TA-1). The two groups R are represented here. 1 , which are bonded to the indeno carbon atom, preferably the same or different for an alkyl group with 1 to 4 carbon atoms, in particular for methyl groups, or for an aromatic ring system with 6 to 12 carbon atoms, in particular for phenyl groups. The two groups R are particularly preferred 1 , which are bonded to the indeno carbon atom, represent methyl groups. Furthermore, the substituent R is preferentially used. 1, which is bound to the indenocarbazole core in formula (TA-2a), for H or for a carbazole group which may be bound to the indenocarbazole core via the 1-, 2-, 3- or 4-position or via the N atom, in particular via the 3-position. Preferred 4-spirocarbazole derivatives, which are used as co-host materials together with the compounds according to the invention, are selected from the compounds of the following formula (TA-3), where Ar 5 and R 1 the meanings listed above, in particular for formulas (I) and / or (TA-1). Preferred embodiments of group Ar are 5 the structures listed above R 1 -1 to R 1 -43, especially preferred R 1 -1 to R 1 -28. A preferred embodiment of the compounds of formula (TA-3) are the compounds of the following formula (TA-3a),

[0024] where Ar 5 and R 1the meanings listed above, in particular for formulas (I) and / or (TA-1), have meanings. Preferred embodiments of group Ar are 5 the structures listed above R 1 -1 to R 1 -43, especially preferred R 1 -1 to R 1 -28. Preferred lactams used as co-host materials together with the compounds according to the invention are selected from the compounds of the following formula (LAC-1), where R 1 the meaning listed above, particularly for formulas (I). A preferred embodiment of the compounds of formula (LAC-1) are the compounds of the following formula (LAC-1a),

[0025] where R 1 the meaning mentioned above, especially for formulas (Ia) to (If). Here, R stands for 1preferably the same or different in each occurrence for H or an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, which is joined with one or more R groups 2 can be substituted, where R 2 which can have the meaning mentioned above, especially for formula (I). The substituents R are particularly preferred. 1 selected from the group consisting of H or an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, each with one or more non-aromatic residues R 2 It can be substituted, but is preferably unsubstituted. Examples of suitable substituents R 1are selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl and 1-, 2-, 3- or 4-carbazolyl, each of which is modified by one or more R groups 2 They can be substituted, but are preferably unsubstituted. Suitable structures are R. 1 the same structures as previously shown for R-1 to R-79, especially preferred R 1 -1 to R 1-51. It may also be preferred 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. Equally preferred is the use of a mixture of a charge-transporting matrix material and an electrically inert matrix material that does not participate, or does not participate to a significant extent, in charge transport, as described, for example, in WO 2010 / 108579. In particular, compounds with a large band gap that do not participate, or at least do not participate to a significant extent, in charge transport of the emitting layer are suitable as co-matrix materials in combination with the compound according to the invention. Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009 / 124627 or in WO 2010 / 006680.It is further preferred to use a mixture of two or more triplet emitters together with a matrix. The triplet emitter with the shorter-wavelength emission spectrum serves as a co-matrix for the triplet emitter with the longer-wavelength emission spectrum. Particularly preferably, a compound according to the invention comprising structures according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) can be used in a preferred embodiment as a matrix material in an emission layer of an organic electronic device, in particular in an organic electroluminescent device, for example in an OLED or OLEC. The matrix material comprising the compound includes structures according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk).The preferred embodiments described above and below are present in the electronic device in combination with one or more dopants, preferably phosphorescent dopants. In this case, the proportion of matrix material in the emitting layer is between 50.0 and 99.9 vol.%, preferably between 80.0 and 99.5 vol.%, and particularly preferably between 92.0 and 99.5 vol.% for fluorescent emitting layers and between 85.0 and 97.0 vol.% for phosphorescent emitting layers. Correspondingly, the proportion of the dopant is between 0.1 and 50.0 vol.%, preferably between 0.5 and 20.0 vol.%, and particularly preferably between 0.5 and 8.0 vol.% for fluorescent emitting layers and between 3.0 and 15.0 vol.% for phosphorescent emitting layers.An emitting layer of an organic electroluminescent device can also contain systems comprising several matrix materials (mixed-matrix systems) and / or several dopants. In this case, too, the dopants are generally those materials with the smaller proportion in the system, and the matrix materials are those materials with the larger proportion in the system. In individual cases, however, the proportion of a single matrix material in the system can be smaller than the proportion of a single dopant. In a further preferred embodiment of the invention, the compounds comprising structures according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk), or the preferred embodiments described above and below, are used as a component of mixed-matrix systems.The mixed-matrix systems preferably comprise two or three different matrix materials, and more preferably two different matrix materials. Preferably, one of the two materials is a material with hole-transporting properties and the other is a material with electron-transporting properties. However, the desired electron-transporting and hole-transporting properties of the mixed-matrix components can also be combined mainly or completely in a single mixed-matrix component, with the other mixed-matrix component(s) fulfilling different functions. The two different matrix materials can be present in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, more preferably 1:10 to 1:1, and most preferably 1:4 to 1:1. Mixed-matrix systems are preferably used in phosphorescent organic electroluminescence devices.More detailed information on mixed-matrix systems is contained, inter alia, in application WO 2010 / 108579. A further object of the present invention is the use of a compound according to the invention in an electronic device, in particular in an organic electroluminescent device. A further object of the present invention is the use of a compound and / or an oligomer, polymer, or dendrimer according to the invention in an electronic device as a fluorescent emitter, an emitter exhibiting TADF (thermally activated delayed fluorescence), a host material, an electron transport material, an electron injection material, a hole transport material, a hole injection material, an electron blocking material, a hole blocking material, and / or a wide-bandgap material, preferably as a fluorescent emitter (singulet emitter), a host material, a hole transport material, and / or an electron transport material.A further object of the present invention is an electronic device comprising at least one compound according to the invention. An electronic device within the meaning of the present invention is a device comprising an anode, a cathode, and at least one intermediate layer containing at least one organic compound. The component may also contain inorganic materials or layers composed entirely of inorganic materials. The electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.).), preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes based on small molecules (sOLEDs), organic light-emitting diodes based on polymers (PLEDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), “organic plasmon emitting devices” (DM Koller et al., Nature Photonics 2008, 1-4); 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), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs) and organic electrical sensors, preferably organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.).), particularly preferably organic light-emitting diodes (OLEDs), small-molecule organic light-emitting diodes (sOLEDs), polymer-based organic light-emitting diodes (PLEDs), and especially phosphorescent OLEDs. The organic electroluminescent device comprises a cathode, 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, and / or charge-generation layers. Interlayers, which may, for example, have an exciton-blocking function, may also be introduced between two emitting layers. It should be noted, however, that not all of these layers are necessarily required.The organic electroluminescent device can contain one or more emitting layers. If multiple emission layers are present, they preferably exhibit several emission maxima between 380 nm and 750 nm, resulting in overall white emission. This means that different emitting compounds capable of fluorescence or phosphorescence are used in the emitting layers. Systems with three emitting layers exhibiting blue, green, and orange or red emission are particularly preferred. The organic electroluminescent device according to the invention can also be a tandem electroluminescent device, especially for white-emitting OLEDs.In a further embodiment of the invention, the organic electroluminescent device according to the invention does not contain a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer; i.e., the emitting layer is directly adjacent to the hole injection layer or the anode, and / or the emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode, as described, for example, in WO 2005 / 053051. Furthermore, it is possible to use a metal complex that is identical or similar to the metal complex in the emitting layer directly adjacent to the emitting layer as a hole transport or hole injection material, as described, for example, in WO 2009 / 030981. The compound according to the invention can be used in different layers, depending on the precise structure.A preferred organic electroluminescent device comprises a compound according to formulas (Ia) to (If) or the preferred embodiments described above in an emitting layer as a matrix material for phosphorescent emitters, for emitters exhibiting TADF (thermally activated delayed fluorescence), particularly for fluorescent or phosphorescent emitters. Furthermore, the compound according to the invention can also be used in an electron transport layer and / or in a hole transport layer and / or in an exciton blocking layer and / or in a hole blocking layer. The compound according to the invention is particularly preferably used as a matrix material for red, orange, or yellow phosphorescent emitters, particularly for red phosphorescent emitters, in an emitting layer or as an electron transport or hole blocking material in an electron transport or hole blocking layer.Furthermore, the present invention relates to an electronic device, preferably an organic electroluminescent device, comprising one or more compounds according to the invention and / or at least one oligomer, polymer, or dendrimer according to the invention in one or more electron-conducting layers, as the electron-conducting compound. In the further layers, generally all materials as used for the layers according to the prior art can be used, and a person skilled in the art can combine any of these materials with the materials according to the invention in an electronic device without any inventive effort. The device is structured accordingly (depending on the application), contacted, and finally hermetically sealed, since the service life of such devices is drastically reduced in the presence of water and / or air.A further preferred option is an electronic device, in particular an organic electroluminescence device, characterized in that one or more layers are coated using a sublimation process. The materials are sublimated in vacuum sublimation systems at an initial pressure typically less than 10 bar. -5 mbar, preferably less than 10 -6 The initial pressure is vapor-deposited at mbar. It is also possible that the initial pressure is even lower or higher, for example less than 10 mbar. -7 mbar. An electronic device, in particular an organic electroluminescence device, is also preferred, characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or with the aid of carrier gas sublimation. The materials are coated at a pressure between 10 -5mbar and 1 bar. A special case of this process is OVJP (Organic Vapor Jet Printing), in which the materials are applied directly through a nozzle and thus structured (e.g., BMS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301). A further preferred method is an electronic device, in particular an organic electroluminescent device, characterized in that one or more layers are produced from solution, e.g., by spin coating, or by any printing method, such as screen printing, flexographic printing, offset printing, or nozzle printing, but especially preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing. Soluble compounds are required for this, which can be obtained, for example, by suitable substitution.Hybrid processes are also possible, in which, for example, one or more layers of solution are applied and one or more further layers are vapor-deposited. These processes are generally known to those skilled in the art and can be applied by them without inventive effort to organic electroluminescent devices containing the compounds according to the invention. The electronic devices according to the invention, in particular organic electroluminescent devices, are characterized by one or more of the following surprising advantages over the prior art: 1. Electronic devices, in particular organic electroluminescent devices containing compounds, oligomers, polymers or dendrimers according to the invention, or...The preferred embodiments described above and below, in particular as electron-conducting materials and / or hole transport materials or as matrix materials, exhibit a very good lifetime. 2. Electronic devices, in particular organic electroluminescent devices containing compounds, oligomers, polymers, or dendrimers according to the invention, or the preferred embodiments described above and below, in particular as electron transport materials, hole transport materials, and / or as host materials, exhibit excellent efficiency. In particular, the efficiency is significantly higher compared to analogous compounds that do not contain a structure according to the invention. The compounds, oligomers, polymers, or dendrimers according to the invention, or the preferred embodiments described above and below, result in a low operating voltage when used in electronic devices.These compounds, in particular, result in a low roll-off, i.e., a low drop in the power efficiency of the device at high luminance levels. 3. Electronic devices, especially organic electroluminescent devices containing compounds, oligomers, polymers, or dendrimers, or the preferred embodiments described above and below, as electron transport materials, hole transport materials, and / or host materials, exhibit excellent color purity. 4. The compounds, oligomers, polymers, or dendrimers according to the invention, or the preferred embodiments described above and below, exhibit very high thermal and photochemical stability and result in compounds with a very long lifetime. 5. With compounds, oligomers, polymers, or dendrimers, orIn the preferred embodiments described above and below, the formation of optical loss channels can be avoided in electronic devices, particularly organic electroluminescent devices. This results in these devices exhibiting high PL and thus high EL efficiency of emitters, or excellent energy transfer from the matrices to the dopants. 6. Compounds, oligomers, polymers, or dendrimers, or the preferred embodiments described above and below, exhibit excellent glass film formation. 7. Compounds, oligomers, polymers, or dendrimers, or the preferred embodiments described above and below, form very good films from solutions. These advantages mentioned above generally do not result in a deterioration of the other electronic properties.In the further layers of the organic electroluminescent device according to the invention, all materials commonly used in the prior art can be employed. Therefore, without any inventive effort, a person skilled in the art can use all materials known for organic electroluminescent devices in combination with the compounds according to the invention, which can be used as active compounds in an organic electronic device, preferably compounds comprising structures according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk), or according to the preferred embodiments. The compounds according to the invention generally exhibit very good properties when used in organic electroluminescent devices.In particular, when the compounds according to the invention are used in organic electroluminescent devices, the lifetime is significantly better compared to similar compounds according to the prior art. Furthermore, the other properties of the organic electroluminescent device, especially the efficiency and the voltage, are also better or at least comparable. It should be noted that variations of the embodiments described in the present invention fall within the scope of this invention. Unless explicitly excluded, each feature disclosed in the present invention can be replaced by alternative features serving the same, an equivalent, or a similar purpose. Thus, unless otherwise stated, each feature disclosed in the present invention is to be considered as an example of a generic series or as an equivalent or similar feature.All features of the present invention can be combined with one another in any way, unless certain features and / or steps are mutually exclusive. This applies in particular to preferred features of the present invention. Likewise, features of non-essential combinations can be used separately (and not in combination). It should also be noted that many of the features, and in particular those of the preferred embodiments of the present invention, are themselves inventive and not merely part of the embodiments of the present invention. Independent protection can be sought for these features in addition to or as an alternative to any currently claimed invention. The teaching on technical action disclosed in the present invention can be abstracted and combined with other examples.The invention is further explained by the following examples, without being intended to limit it. A person skilled in the art can, from these descriptions, produce further electronic devices according to the invention without any inventive effort and thus implement the invention in its entire claimed scope.

[0026] Examples: Unless otherwise stated, the following syntheses are carried out under a protective gas atmosphere in dried solvents. The metal complexes are additionally handled in the absence of light or under yellow light. The solvents and reagents can be obtained, for example, from Sigma-Aldrich or ABCR. The information in square brackets and the numbers given for individual compounds refer to the CAS numbers of the compounds known from the literature. For compounds that can have several enantiomeric, diastereomeric, or tautomeric forms, one form is shown as a representative example. The following scheme serves to better understand the synthetic route described in more detail below. Reaction conditions: a) XPhos Pd G3, K3PO4, RF, THF, H2O, RF, 24 h, 62%; b) NBS, DCM, RT, 2 h, 95%; c) Pd(PPh3)2Cl2, Trimethylsilylacetylene, TEA, RF, 24 h, 66%; d) K2CO3, MeOH, RT, 0.5 h, 93%; e) Au(SPhos)(NTf2), meta-xylene, RF, 20 h, 48%; f) Pd(PCy3)2Cl2, K2CO3, DMF, RF, 50 h, 70%. Synthesis of Synthons S: Example S1: A well-stirred mixture of 22.7 g (100 mmol) 3-bromo-5-methoxybenzofuran [333385-25-4], 27.9 g (110 mmol) bis(pinacolato)diborane [73183-34-3], 29.5 g (300 mmol) anhydrous potassium acetate, 50 g glass beads (3 mm diameter), and 500 ml THF is treated with 841 mg (3 mmol) tricyclohexylphosphine and then with 224 mg (1 mmol) palladium(II) acetate and heated under reflux for 16 h. While still warm, the mixture is filtered through a Celite bed pre-flourished with THF, the solvent is removed under vacuum, and the residue is dissolved in 100 ml of hot methanol. Allow to cool to room temperature while stirring, filter off the precipitated product, wash it once with 30 ml of methanol, and dry under vacuum. Yield: 19.3 g (70 mmol) 70%; Purity: approx. 95% n.a. 1 H-NMR.

[0027] Example G1: Synthesis of base compound G1, see reaction scheme step a): Compound 1 A mixture of 28.1 g (100 mmol) 1-bromo-9-chlorodibenzofuran [2179279-83-3], 16.3 g (100 mmol) 3-benzofuranylboronic acid [317830-83-4], 53.1 g (250 mmol) tripotassium phosphate, 3.4 g (4 mmol) XPhos Pd G3 [1445058-55-1], 800 ml THF, and 200 ml water is heated under reflux for 24 h. The reaction mixture is then concentrated under vacuum, and the residue is dissolved in 800 ml ethyl acetate. The organic phase is washed three times with 200 ml of water each time, once with 300 ml saturated saline, and then concentrated under vacuum to dryness. The black, oily residue is dissolved in 500 ml of n-heptane and fractionally filtered over silica gel. After removal of the n-heptane under vacuum, the product is obtained as a colorless oil. Yield: 19.8 g (62 mmol) 62%; Purity: approx. 95% n-heptane. 1 H-NMR. Stage b): Compound 2 A well-stirred solution of 33.9 g (100 mmol) of compound 1 in 300 ml of dichloromethane (DCM) is mixed with 18.0 g (100 mmol) of NBS at room temperature and stirred for 2 h. The solvent is then removed under vacuum, the oily residue is dissolved in 500 ml of n-heptane, and filtered through silica gel. After removal of the n-heptane under vacuum, the product is obtained as a colorless oil: yield: 37.8 g (95 mmol) 95%; purity: approx. 95% n. 1 H-NMR. Stage c): Compound 3 A well-degassed mixture of 39.7 g (100 mmol) of compound 2, 42.4 ml (300 mmol) of trimethylsilylacetylene, 1000 ml of DMF, and 500 ml of triethylamine is treated with 1.2 g (6 mmol) of copper iodide and then with 4.0 g (4 mmol) of tetrakistriphenylphosphinopalladium(0) and stirred for 24 h at 80°C. After cooling, the reaction mixture is filtered through a Celite bed suspended with DMF. The filtrate is removed from the solvent under vacuum at 30°C, and the residue is dissolved with 500 ml of DCM to ISOLUTE.® The sample was drawn up and chromatographed with n-heptane / ethyl acetate using a column chromatograph (Torrent, A. Semrau). Yield: 25.3 g, (66 mmol) 66%, purity: approx. 95% n.g. 1 H-NMR. Stage d): Compound 4 A well-stirred solution of 41.7 g (100 mmol) of compound 3 in 500 ml of MeOH is mixed with 27.6 g (200 mmol) of potassium carbonate at room temperature and stirred for 30 minutes. The potassium carbonate is filtered off, the MeOH is removed under vacuum at 30 °C, the residue is dissolved in 300 ml of DCM, washed three times with 100 ml of water, once with 100 ml of saturated saline, dried over sodium sulfate, filtered off the drying agent, and the filtrate is concentrated under vacuum to dryness. Yield: 32.1 g (93 mmol), 93%; Purity: approx. 95%. 1 H-NMR. Stage e): Compound 5 A well-stirred solution of 17.2 g (50 mmol) of compound 4 in 1000 ml m-xylene is heated under reflux, then treated dropwise for 8 h with a solution of 4.4 g (5 mmol) of SPhosAuNTf2 [1121960-90-4] in 200 ml m-xylene, and finally heated under reflux for a further 12 h. After cooling, the solvent is removed under vacuum. The oily residue is reconstituted in 300 ml DCM and isolated on ISOLUTE. ® The sample was drawn up and chromatographed with n-heptane using a column chromatograph (Torrent, A. Semrau). Yield: 8.3 g (48 mmol), 48%; Purity: approx. 95% n. 1 H-NMR. Stage f): Base body G1 A well-stirred mixture of 17.2 g (50 mmol) of compound 5, 27.6 g (200 mmol) of potassium carbonate, 1.9 g (2.5 mmol) of Pd(PCy3)2Cl2 [29934-17-6], 50 g of glass beads, and 1000 ml of DMF is heated under gentle reflux for 50 h. After cooling, the DMF is removed under vacuum, the residue is dissolved in 1000 ml of hot chlorobenzene, filtered through a pre-flourished aloxic acid bed, concentrated under vacuum to dryness, and the beige residue is stirred twice with 300 ml of hot n-heptane. Yield: 10.9 g (35 mmol), 70%; Purity: approx. 95% n. 1 H-NMR. The following compounds can be represented analogously: Example G10: A mixture of 16.8 g (50 mmol) of G2 and 115.6 g (1 mol) of pyridinium hydrochloride [628-13-7] is melted and heated with good stirring in a water separator for 3 h at 230 °C (heating bowl temperature), with the pyridine formed being drained off from time to time. The reaction mixture is allowed to cool to about 100 °C and 500 ml of water is carefully added dropwise. After cooling, the precipitated solid is filtered off, washed three times with 100 ml of warm water and once with 50 ml of cold methanol, and dried under vacuum. Yield: 16.1 g (48 mmol), 96%; Purity: about 95% n.a. 1 H-NMR. The following compounds can be represented analogously: Example G20: A well-stirred suspension of 16.1 g (50 mmol) of G10 in 300 ml DCM, cooled to 0 °C, is treated with 12 ml of pyridine and then dropwise with 16.8 ml (100 mmol) of trifluoromethanesulfonic anhydride [358-23-6] and stirred for 2 h at 0 °C. The reaction mixture is allowed to warm to room temperature, stirred for 2 h, then poured onto 500 g of ice and stirred for 30 min. The organic phase is separated, washed twice with 100 ml saturated sodium chloride solution, and the solvent is removed under vacuum. Yield: 21.7 g (47.5 mmol), 95%; Purity: approx. 95% n.a. 1 H-NMR. The following compounds can be represented analogously: Example G30: A suspension of 3.06 g (10.0 mmol) of G1 in 100 ml of chloroform is treated with 3.53 g (11 mmol) of pyridinium perbromide under exclusion of light and then stirred for 24 h at 60 °C. After cooling, 30 ml of 10 wt% sodium sulfite solution is added, the mixture is stirred for 30 min, the organic phase is separated, the mixture is concentrated under vacuum to dryness, the residue is stirred twice with 25 ml of hot methanol, and recrystallizes from a small amount of chlorobenzene. Yield: 3.05 g (7.8 mmol), 78%; Purity: approx. 95%. 1 H-NMR. Example TMM1: A mixture of 4.54 g (10 mmol) G20, 3.83 g (12 mmol) 3,6-diphenylcarbazole [56525-79-2], 5.31 g (25 mmol) tripotassium phosphate, 20 g glass beads (3 mm diameter), and 100 ml o-xylene is stirred at room temperature with 289 mg (0.5 mmol) XantPhos and 112 mg (0.5 mmol) palladium(II) acetate and then stirred under reflux for 36 h. The solvent is largely removed under vacuum, the solid is stirred twice with 200 ml of hot water each time, the precipitated product is filtered by suction, washed three times with 100 ml of water each time, three times with 30 ml of methanol, and dried under vacuum. The crude product is dissolved in 300 ml of DCM and filtered through a keel gel bed pre-floured with DCM. The filtrate is mixed with 100 ml of methanol, the DCM is removed under vacuum, the precipitated solid is filtered off, and dried under vacuum. Purification is carried out by repeated hot extraction with toluene, using a feed volume of 150 ml and Whatman cellulose extraction pods.Alternatively, other solvents can be used. Finally, the product is sterilized under high vacuum (p ~ 10). -5 (mbar) fractionally sublimed. Yield: 3.93 g (6.3 mmol), 63%; Purity: > 99.9% y n. HPLC. The following compounds can be prepared analogously:

[0028] A mixture of 4.54 g (10 mmol) G20, 5.34 g (12 mmol) 9-[1,1'- Biphenyl]-3-yl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole [1533406-38-0], 6.9 g (30 mmol) tripotassium phosphate monohydrate [27176- 10-9], 20 g glass beads (3 mm diameter), 347 mg (0.3 mmol) tetrakis-triphenylphosphinopalladium(0) and 100 ml DMSO is stirred for 24 h at 100 °C. The warm reaction mixture is poured into 300 ml of hot water, stirred for 20 minutes, and the precipitated product is filtered off. This product is washed three times with 50 ml of water and three times with 30 ml of methanol, and then dried under vacuum. The crude product is dissolved in 300 ml of DCM and filtered through a keel gel bed pre-floured with DCM. The filtrate is mixed with 100 ml of methanol, the DCM is removed under vacuum, the precipitated solid is filtered off, and the product is dried under vacuum. Purification is carried out by repeated hot extraction with toluene, using a feed volume of 150 ml and Whatman cellulose extraction pods.Alternatively, other solvents can be used. Finally, the product is sterilized under high vacuum (p ~ 10). -5 (mbar) fractionally sublimed. Yield: 2.8 g (4.5 mmol), 45%; Purity: > 99.9% y n. HPLC. The following compounds can be prepared analogously: TMM20: A well-stirred mixture of 4.32 g (10 mmol) G30, 2.22 g (11 mmol) 2-bromonitrobenzene [577-19-5], 4.15 g (30 mmol) potassium carbonate, 116 mg (0.1 mmol) tetrakistriphenylphosphinopalladium(0), 150 ml THF, and 30 ml water is heated under reflux for 16 h. The still-warm reaction mixture is treated with 200 ml water, concentrated under vacuum to approximately 100 ml, filtered off the precipitated solid, washed three times with 50 ml of water, twice with 30 ml of methanol, and dried under vacuum. Yield: 3.99 g (9.3 mmol), 93%; Purity: approximately 95%. 1 H-NMR. Stage b): Analogous to SH Smitrovich et al., Org. Lett, 2004, 6, 4, 533. A mixture of 4.27 g (10 mmol) TMM20 step a), 72 mg (0.4 mmol) 1,10-phenanthroline, 45 mg (0.2 mmol) palladium(II) acetate, and 50 ml DMF is stirred in an autoclave under 5 bar CO pressure for 16 h at 140 °C. After cooling, the DMF is removed under vacuum, the residue is dissolved in 100 ml of boiling chlorobenzene, and while still hot, filtered through a silica gel bed pre-flourished with chlorobenzene. The filtrate is then concentrated under vacuum at 80 °C until crystallization begins and stirred at room temperature to complete crystallization. The product is filtered by suction, washed three times with 30 ml of methanol, and dried under vacuum. Yield: 3.44 g (8.7 mmol), 87%; Purity: approx. 95% n.g. 1H-NMR. Step c): TMM20 A mixture of 3.95 g (10 mmol) TMM20 Step b), 3.27 g (14 mmol) 3-bromobiphenyl [2113-57-7], 1.44 g (15 mmol) sodium tert-butanoate, 41.0 mg (0.1 mmol) S-Phos, 22.5 mg (0.1 mmol) palladium(II) acetate and 100 ml o-xylene is stirred under reflux for 24 h. After cooling, the o-xylene is removed under vacuum and the residue is stirred hot with 100 ml of a 1:2 water / methanol mixture, filtered from the solid, washed three times with 30 ml of methanol each time, and dried under vacuum. The residue is dissolved in 100 ml of boiling chlorobenzene and filtered while still hot through a silica gel bed pre-flourished with chlorobenzene. The filtrate is then concentrated under vacuum at 80 °C until crystallization begins, and stirred at room temperature to complete crystallization. The product is filtered by suction, washed three times with 30 ml of methanol, and dried under vacuum.Purification is carried out by repeated hot extraction with toluene, using a feed volume of 150 ml and Whatman cellulose extraction pods. Alternatively, other solvents can be used. Finally, the product is extracted under high vacuum (p ~ 10). -5 (mbar) fractionally sublimed. Yield: 3.84 g (7.0 mmol), 70%; Purity: > 99.9% y n. HPLC.

[0029] A well-stirred mixture of 4.32 g (10 mmol) G30, 5.05 g (11 mmol) 10-(4-(1-Naphthenyl)phenyl)-9-bromoanthracene [1092390-01-6], 6.37 g (30 mmol) tripotassium phosphate, 183 mg (0.6 mmol) tri-o-tolylphosphine, 22.5 mg (0.1 mmol) palladium(II) acetate, 100 ml toluene, 50 ml dioxane, and 100 ml water is heated under reflux for 16 h. After cooling, the precipitated solid is filtered off, washed three times with 50 ml of water, three times with 30 ml of methanol, and dried under vacuum. The solid is taken up in 200 ml of DCM, filtered through a silica gel bed pre-flourished with DCM, the filtrate is mixed with 100 ml of methanol, and concentrated under vacuum until crystallization begins. The crystallizate is filtered off, washed twice with 30 ml of methanol, and dried under vacuum. Purification is carried out by repeated hot extraction with toluene, using a feed volume of 150 ml, and Whatman cellulose extraction hulls. Alternatively, other solvents can be used.Finally, the product is tested in a high vacuum (p ~ 10. -5 (mbar) fractionally sublimed. Yield: 4.60 g (6.7 mmol), 67%; Purity: > 99.9% y n. HPLC. The following compounds can be prepared analogously: Vacuum-processed devices: The fabrication of OLEDs according to the invention, as well as OLEDs according to the prior art, is carried out according to a general method according to WO 2004 / 058911, which is adapted to the conditions described here (layer thickness variation, materials used). The following examples present the results for various OLEDs. Cleaned glass slides (cleaned in a Miele laboratory dishwasher, using Merck Extran cleaner), coated with 50 nm thick structured ITO (indium tin oxide), are pretreated with UV ozone for 25 minutes (UV ozone generator PR-100, UVP) and coated within 30 minutes with 20 nm PEDOT:PSS (poly(3,4-ethylenedioxythiophene) poly(styrenesulfonate), sourced as CLEVIOS™ P VP AI 4083 from Heraeus Precious Metals GmbH Germany, centrifuged from aqueous solution) for improved processing and then baked out at 180°C for 10 minutes.These coated glass plates form the substrates onto which the OLEDs are deposited. The OLEDs generally have the following layer structure: Substrate / Hole injection layer 1 (HIL1) consisting of Ref-HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm / Hole transport layer 1 (HTL1) consisting of 200 nm Ref-HTM1 / Hole transport layer 2 (HTL2) consisting of 10 nm Ref-HTM2 / Emission layer (EML) 30 nm / Hole blocking layer (HBL) 10 nm / Electron transport layer (ETL) 30 nm / Optional electron injection layer (EIL) and finally a cathode. The cathode is formed by a 100 nm thick aluminum layer. First, vacuum-processed OLEDs are described. For this process, all materials are thermally vapor-deposited in a vacuum chamber. The emission layer always consists of at least one matrix material (host material) and an emitting dopant (doped, emitter), which corresponds to the matrix material orThe matrix materials are added in a specific volume fraction via co-evaporation. A specification such as Ref-TMM1:Ref-TMM2:Ir1 (55%:35%:10%) means that Ref-TMM1 is present in the layer at a volume fraction of 55%, Ref-TMM2 at 35%, and IrL1 at 10%. Similarly, the electron transport layer can also consist of a mixture of two materials. The exact structure of the OLEDs can be found in Table 1. The materials used to fabricate the OLEDs are shown in Table 3. The OLEDs are characterized according to standard procedures. For this purpose, the electroluminescence spectra, the current efficiency (measured in cd / A), the power efficiency (measured in lm / W) and the external quantum efficiency (EQE, measured in percent) as a function of the luminance, calculated from current-voltage-luminance characteristics (IUL characteristics) assuming a Lambertian emission characteristic, as well as the lifetime are determined.The electroluminescence spectra are determined at a luminance of 1000 cd / m², and the CIE 1931 x and y color coordinates are calculated from them. The lifetime LD90 is defined as the time after which the luminance has decreased to 90% of the initial luminance when operating at a starting brightness of 10000 cd / m². The OLEDs can initially be operated at other starting luminances. The lifetime values ​​can then be converted to values ​​for other starting luminances using conversion formulas known to those skilled in the art. Use of compounds according to the invention as materials in phosphorescent OLEDs: The compounds according to the invention can be used, among other things, as TMM (triplet matrix material), ETM (electron transport material), and as host materials SMM (singulet matrix material) in the emission layer of OLEDs. For comparison, compounds according to the prior art are used in Table 3.The results for the OLEDs are summarized in Table 2. Table 1: Structure of the OLEDs.

[0030] Table 3: Structural formulas of the materials used

[0031] The examples and comparative examples presented above show that the compounds according to the invention achieve unexpected improvements with regard to lifetime, quantum efficiency (EQE), and the required operating voltage. For example, a comparison of reference example Ref. D1 with examples D1, D2, D7, D8, D10, and D11, each of which has compound Ir1 as the emitter, shows that the examples according to the invention achieve significant improvements in the aforementioned criteria without incurring any significant disadvantages. Example D11, in particular, shows surprising advantages with regard to quantum efficiency. The advantages of structures according to formulas (Vf) to (Vk), especially (Vh), are confirmed by comparing example D12 with examples D15 and D16. A similar result is obtained by comparing reference example Ref.D2 is compared with examples D3, D4, D5, and D6, each of which features the compound Ir2 as the emitter. The same applies to a comparison of reference example Ref.D3 with examples D9, D12, D13, D14, D15, and D16, each of which features the compound Ir3 as the emitter. Here, example D9 shows that, compared to Ref.D3, the lifetime is more than doubled, while simultaneously improving the quantum efficiency (EQE) and the required operating voltage. Furthermore, a comparison of examples D12, D13, and D14 shows that unexpectedly strong improvements can be achieved by using materials according to the invention in a hole-blocking layer (HBL). The use of materials according to the invention in an electron transport layer (ETM) also leads to improvements.

Claims

Claim 1. Compound comprising at least one structure of formulas (Ia), (Ib), (Ic), (Id), (Ie) and / or (If) where: X is, in each occurrence, either the same or different from CR or N, preferably CR; Y is, in each occurrence, either the same or different from a bridge selected from B(R), C(R)₂, Si(R)₂, C=O, C=NR, C=C(R)₂, O, S, Se, S=O, SO₂, N(R), N(Ar), P(R) and P(=O)R, preferably O, S, B(R), C=O, N(R) and N(Ar), particularly preferably O, S, N(Ar); R is, in each occurrence, either the same or different from H, D, OH, F, Cl, Br, I, CN, NO₂, N(Ar)₂, N(R) 1 )2, C(=O)N(Ar)2, C(=O)N(R 1 )2, Si(Ar)3, Si(R 1 )3, B(Ar)2, B(R 1 )2, C(=O)Ar, C(=O)R 1 , P(=O)(Ar)2, P(=O)(R 1 )2, P(Ar)2, P(R 1 )2, S(=O)Ar, S(=O)R 1 , S(=O)2Ar, S(=O)2R 1 , OSO2Ar, OSO2R 1, a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 40 carbon atoms, or an alkenyl or alkynyl group with 2 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group with 3 to 20 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group is each linked to one or more R groups 1 can be substituted, with one or more non-adjacent CH2 groups being replaced by R 1 C=CR 1 , C≡C, Si(R 1 )2, C=O, C=S, C=Se, C=NR 1 , -C(=O)O-, -C(=O)NR 1 -, NR 1 , P(=O)(R 1 ), -O-, -S-, SO or SO2 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each replaced by one or more R groups 1 may be substituted, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, separated by one or more R groups 1It can be substituted; two R groups can also form a ring system together; Ar is, in each occurrence, the same or different aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which is coupled with one or more R groups. 1 can be substituted, whereby two Ar residues bonding to the same Si atom, N atom, P atom or B atom can also be connected by a single bond or a bridge selected from B(R) 1 ), C(R 1 )2, Si(R 1 )2, C=O, C=NR 1 , C=C(R 1 )2, O, S, S=O, SO2, N(R 1 ), P(R 1 ) and P(=O)R 1 , be bridged together; R 1 is the same or different in each occurrence H, D, F, Cl, Br, I, CN, NO2, N(Ar) 1 )2, N(R 2 )2, C(=O)Ar 1 , C(=O)R 2 , P(=O)(Ar 1 )2, P(Ar 1 )2, B(Ar 1 )2, B(R 2 )2, Si(Ar 1 )3, Si(R 2)3, a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group with 3 to 40 C atoms or an alkenyl group with 2 to 40 C atoms, each with one or more R groups 2 can be substituted, where one or more non-adjacent CH2 groups are replaced by -R 2 C=CR 2 -, -C≡C-, Si(R 2 )2, C=O, C=S, C=Se, C=NR 2 , -C(=O)O-, -C(=O)NR 2 -, NR 2 , P(=O)(R 2 ), -O-, -S-, SO or SO2 may be replaced and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which is replaced by one or more R groups 2 may be substituted, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, separated by one or more R groups 2may be substituted, or an aralkyl or heteroaralkyl group with 5 to 60 aromatic ring atoms, coupled with one or more R groups 2 may be substituted, or a combination of these systems; in this case, two or more, preferably adjacent residues R may be used. 1 together form a ring system; one or more residues R can be involved. 1 form a ring system with another part of the compound; Ar 1 In each occurrence, it is the same or different: an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, coupled with one or more non-aromatic residues R 2 It can be substituted, in which case two residues Ar 1 , which bond to the same Si atom, N atom, P atom or B atom, also by a single bond or a bridge, selected from B(R 2 ), C(R 2 )2, Si(R 2 )2, C=O, C=NR 2 , C=C(R 2 )2, O, S, S=O, SO2, N(R2 ), P(R 2 ) and P(=O)R 2 , be bridged together; R 2 is selected in each occurrence, either the same or different, from the group consisting of H, D, F, CN, an aliphatic hydrogen carbonate residue with 1 to 20 C atoms, or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D, F, Cl, Br, I or CN, and which may be substituted by one or more alkyl groups, each with 1 to 4 carbon atoms, wherein two or more, preferably adjacent, substituents R 2 together form a ring system.

2. Compound according to claim 1, characterized in that the compound comprises at least one structure of formulas (IIa), (IIb), (IIc), (IId), (IIe) and / or (IIf). wherein the substituents X, Y and R have the meaning specified in claim 1, the index m is equal to or different from 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, more preferably 0 or 1, and the index o is equal to or different from 0, 1 or 2, more preferably 0 or 1, wherein the sum of the indices o and m is preferably 1 or 2, more preferably 1.

3. Compound according to claim 1 or 2, characterized in that the compound comprises at least one structure of formulas (IIIa), (IIIb), (IIIc), (IIId), (IIIe) and / or (IIIf). wherein the substituents X, Y and R have the meaning specified in claim 1, the index m is equal to or different from 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, more preferably 0 or 1, and the index n is equal to or different from 0, 1, 2 or 3, more preferably 0, 1 or 2, more preferably 0 or 1, wherein the sum of the indices n and m is preferably 1 or 2, more preferably 1.

4. Compound according to at least one of the preceding claims, characterized in that no more than four, preferably no more than two groups X represent N, more preferably all groups X represent CR, wherein preferably at most 4, more preferably at most 3 and more preferably at most 2 of the groups CR, for which X represents, are not equal to the group CH.

5. Compound according to one or more of the preceding claims, characterized in that the compound comprises at least one structure of (IVa), (IVb), (IVc), (IVd), (IVe) and / or (IVf) wherein the residues Y and R have the meaning specified in claim 1, the index k being equal to or different from 0 or 1, preferably 0 is, the index o is equal to or different from 0, 1 or 2, preferably 0 or 1, the index n is equal to or different from 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably 0 or 1, and the index m is equal to or different from 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably 0 or 1, wherein the sum of the indices k, m, n and o is preferably 1 or 2, particularly preferably 1.

6. Compound according to one or more of the preceding claims 2 to 6, characterized in that the sum of the indices k, m, n and o is at most 6, preferably at most 4, particularly preferably at most 2 and preferably at least 1 and particularly preferably exactly 1.

7. Compound according to one or more of the preceding claims, characterized in that the compound comprises at least one structure of formulas (Va), (Vb), (Vc), (Vd), (Ve), (Vf), (Vg) and / or (Vh). wherein the residues Y and R have the meaning stated in claim 1 and furthermore: R a is the same or different in each occurrence: OH, F, Cl, Br, I, CN, NO2, N(Ar)2, N(R 1 )2, C(=O)N(Ar)2, C(=O)N(R 1 )2, Si(Ar)3, Si(R 1 )3, B(Ar)2, B(R 1 )2, C(=O)Ar, C(=O)R 1 , P(=O)(Ar)2, P(=O)(R 1 )2, P(Ar)2, P(R 1 )2, S(=O)Ar, S(=O)R 1 , S(=O)2Ar, S(=O)2R 1 , OSO2Ar, OSO2R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 20 carbon atoms, or an alkenyl or alkynyl group with 2 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group with 3 to 40 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group is each linked to one or more R groups 1 can be substituted, with one or more non-adjacent CH2 groups being replaced by R 1 C=CR 1 , C≡C, Si(R 1)2, C=O, C=S, C=Se, C=NR 1 , -C(=O)O-, -C(=O)NR 1 -, NR 1 , P(=O)(R 1 ), -O-, -S-, SO or SO2 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each replaced by one or more R groups 1 may be substituted, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, separated by one or more R groups 1 It may be substituted; in this case, residues R a also form a ring system with a residue R, where the residues Ar and R 1 the meaning mentioned in claim 1; k is equal to or different from 0 or 1, preferably 0; o is equal to or different from 0, 1, or 2, preferably 0 or 1; n is equal to or different from 0, 1, 2, or 3, preferably 0, 1, or 2, particularly preferably 0 or 1; and m is equal to or different from 0, 1, 2, 3, or 4, preferably 0, 1, or 2, particularly preferably 0 or 1.

8. Compound according to claim 7, characterized in that the sum of the indices k, m, n, and o is at most 6, preferably at most 4, particularly preferably at most 2, especially preferably at most 1, and most particularly preferably 0.

9. Compound according to at least one of the preceding claims, characterized in that at least one of the residues R and / or R' is aThe compound is selected from the group consisting of fluorenes, indenofluorenes, spirobifluorenes, carbazoles, indenocarbazoles, indolocarbazoles, spirocarbazoles, pyrimidines, triazines, lactams, triarylamines, dibenzofurans, dibenzothienes, imidazoles, benzimidazoles, benzoxazoles, benzthiazoles, 5-aryl-phenanthridin-6-ones, 9,10-dehydrophenanthrenes, fluoranthenes, anthracenes, benzanthracenes, and fluoradenes. The compound is defined as follows:

10. A compound according to at least one of the preceding claims, characterized in that at least one of the R and / or R' residues is defined as... a at least one group comprising wide-band-gap materials.

11. Connection according to at least one of the preceding claims, characterized in that the connection comprises a hole transport group, preferably one of the groups R and / or R'. a a hole transport group comprising, preferably represents.

12. Connection according to at least one of the preceding claims, characterized in that the connection comprises a comprising an electron transport group, preferably comprising one of the groups R and / or R a a compound comprising, preferably representing, an electron transport group.

13. Compound according to at least one of the preceding claims, characterized in that at least one of the residues R and / or R's a14. Compound according to at least one of the preceding claims, characterized in that the compound can be represented by a structure according to formulas (Ia) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf), (Va) to (Vk).

15. Oligomer, polymer, or dendrimer comprising one or more compounds according to any one of claims 1 to 13, wherein, instead of a hydrogen atom or a substituent, one or more bonds of the compounds to the polymer, oligomer, or dendrimer are present. 16.A composition comprising at least one compound according to one or more of claims 1 to 14 or an oligomer, polymer, or dendrimer according to claim 15, and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF (thermally activated delayed fluorescence), host materials, electron transport materials, electron injection materials, hole transport materials, hole injection materials, electron blocking materials, hole blocking materials, wide-band gap materials, and n-dopeds. A formulation comprising at least one compound according to one or more of claims 1 to 14 or an oligomer, polymer, or dendrimer according to claim 15 or a composition according to claim 16, and at least one solvent.

18. Use of a compound according to one or more of claims 1 to 14, an oligomer, polymer or dendrimer according to claim 15 or a composition according to claim 16 in an electronic device as an emitter, preferably a fluorescent emitter, an emitter exhibiting TADF (thermally activated delayed fluorescence), host material, electron transport material, electron injection material, hole transport material, hole injection material, electron blocking material, hole blocking material and / or wide-bandgap material, particularly preferably as a fluorescent emitter (singulet emitter), host material, hole transport material and / or electron transport material. 19.A method for producing a compound according to one or more of claims 1 to 14 or an oligomer, polymer and / or dendrimer according to claim 15, characterized in that a compound comprising a heterocyclic structure is coupled to a compound comprising at least one aromatic or heteroaromatic group in a coupling reaction. 20.Electronic device comprising at least one compound according to one or more of claims 1 to 14, an oligomer, polymer or dendrimer according to claim 15 or a composition according to claim 16, wherein the electronic device is preferably selected from the group consisting of organic electroluminescent devices, organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, organic optical detectors, organic photoreceptors, organic field quench devices, light-emitting electrochemical cells or organic laser diodes.