Materials for electronic devices

Abstract

The present invention relates to compounds that are suitable for use in electronic devices, and to electronic devices, more particularly organic electroluminescent devices, containing these compounds.

Description

Materials for electronic devices The present invention relates to materials for use in electronic devices, in particular in organic electroluminescent devices, and to electronic devices, in particular organic electroluminescent devices, containing these materials. Electronic devices containing organic, organometallic, and / or polymer semiconductors are gaining increasing importance, being used in many commercial products due to their cost and performance. Examples include organic-based charge transport materials (e.g., triarylamine-based hole transporters) in copiers, organic or polymeric light-emitting diodes (OLEDs or PLEDs) in display devices, and organic photoreceptors in copiers. Organic solar cells (O-SC), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic integrated circuits (O-ICs), organic optical amplifiers, and organic laser diodes (O-Lasers) are at an advanced stage of development and could become very important in the future. Electronic devices within the meaning of this invention are understood to be organic electronic devices which contain organic semiconductor materials as functional materials. In particular, the electronic devices are electroluminescent devices such as OLEDs. The structure of OLEDs, in which organic compounds are used as functional materials, is known to those skilled in the art. Generally, OLEDs are understood to be electronic devices that have one or more layers comprising organic compounds and emit light when a voltage is applied. In electronic devices, especially OLEDs, there is a great need for performance data, particularly lifespan and efficiency. and to improve operating voltage. No satisfactory solution has yet been found for these aspects. Electronic devices typically comprise a cathode, anode, and at least one functional, preferably emissive, layer. In addition to these layers, they 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. Hole transport layers and electron transport layers have a major influence on the performance data of electronic devices. The object of the present invention is to provide compounds that are suitable for use in an electronic device, in particular an OLED, especially as material for hole transport layers or material for electron transport layers, and that lead to good properties there. Surprisingly, it was found that certain triptycenes, described in more detail below, solve this problem and are well suited for use in electronic devices, especially OLEDs. These OLEDs exhibit, in particular, a long lifetime, high efficiency, and a lower operating voltage. These compounds, as well as electronic devices, especially organic electroluminescent devices containing these compounds, are therefore the subject of the present invention. The present invention relates to a compound according to formulas (1 ) and (2), where the following applies to the symbols used: X is the same or different for each occurrence CR or N, with the proviso that a maximum of two groups X per cycle represent N; Z represents a group of formula (2), where the dashed bond in formula (2) represents the bond to quaternary carbon; Y is the same or different at each occurrence CR' or N, with the proviso that 2 or 3 groups Y per cycle stand for N, or that 1, 2 or 3 groups Y stand for N, and two or more Y, which stand for CR', together form an aromatic or heteroaromatic ring system, preferably in each case 2 or 3 groups Y stand for N; Q represents a bivalent alkylene group with 1 to 4 carbon atoms, a bivalent alkenylene group with 2 to 4 carbon atoms, or a bivalent aryl or heteroaryl group with 5 to 60 ring atoms, whereby the alkylene, alkenylene, aryl or heteroaryl groups may be substituted with one or more groups R; R is the same or different in each occurrence H, D, F, CI, Br, I, OAr', SAr', B(OR) 1 )2, CHO, C(=O)R 1 , CR 1 =C(R 1 )2, CN, C(=O)OR 1 , C(=O)NR 1 , Si(R 1 )3, NO2, P(=O)(R 1 )2, OSO2R 1 , OR 1, S(=O)R 1 , S(=O)2R 1 , SR 1 , a straight-chain alkyl group with 1 to 20 carbon atoms, or an alkenyl or alkynyl group with 2 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein the alkyl, alkenyl or alkynyl group is each linked to one or several residues R 1 can be substituted, where one or more non-adjacent CH2 groups are replaced by -R 1 C=CR 1 -, -C=C-, Si(R 1 )2, CONR 1 , C=O, C=S, -C(=O)O-, P(=O)(R 1 ), -0-, -S-, SO or SO2 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, each of which is replaced by one or more R groups 1can be substituted, wherein two or more residues R preferentially bound to the same cycle can form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system, which can be combined with one or more residues R 1 may be substituted, wherein if R and associated residues comprise at least one heteroaromatic ring system comprising at least one nitrogen atom with three single bonds, for each of these heteroaromatic ring systems, that at least two of the residues bonded to the respective nitrogen atom via single bonds are always connected to the respective nitrogen atom and independently to the framework; R' is the same or different in each occurrence H, D, F, CI, Br, I, OAr', SAr', B(OR) 1 )2, CHO, C(=O)R 1 , CR 1 =C(R 1 )2, CN, C(=O)OR 1 , C(=O)NR 1 , Si(R 1 )3, NO2, P(=O)(R 1 )2, OSO2R 1 , OR 1 , S(=O)R1 , S(=O)2R 1 , SR 1 , a straight-chain alkyl group with 1 to 20 carbon atoms, or an alkenyl or alkynyl group with 2 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein the alkyl, alkenyl, or alkynyl group is each linked to one or more R groups 1 can be substituted, where one or more non-adjacent CH2 groups are replaced by -R 1 C=CR 1 -, -C=C-, Si(R 1 )2, CONR 1 , C=O, C=S, -C(=O)O-, 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, preferably with 5 to 40 aromatic ring atoms, each of which is replaced by one or more R groups 1can be substituted, wherein two or more residues R preferentially bound to the same cycle can form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system, which can be combined with one or more residues R 1 can be substituted, where if R' and associated residues comprising at least one heteroaromatic ring system comprising at least one nitrogen atom with three single bonds, for each of these heteroaromatic ring systems, that at least two of the residues bonded to the respective nitrogen atom via single bonds are always connected to the respective nitrogen atom and independently to the basic framework; Ar' is, in each occurrence, either the same or different, an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, separated by one or more R groups. 1 can be substituted, where two or more R 1together they can form an aromatic or heteroaromatic ring system; R 1 is the same or different in each occurrence H, D, F, I, B(OR) 2 )2, CHO, C(=O)R 2 , CR 2 =C(R 2 )2, CN, C(=O)OR 2 , Si(R 2 )3, NO2, P(=O)(R 2 )2, OSO2R 2 , SR 2 , OR 2 , S(=O)R 2 , S(=O)2R 2 , a straight-chain alkyl group with 1 to 20 carbon atoms, or an alkenyl or alkynyl group with 2 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein the alkyl, alkenyl, or alkynyl group is each linked to one or more R groups 2 can be substituted and where one or more CH2 groups in the above-mentioned groups are replaced by -R 2 C=CR 2 -, -C=C-, Si(R 2 )2, C=O, C=S, -C(=O)O-, CONR 2 , P(=O)(R 2), -O-, -S-, SO or SO2 may be replaced and wherein one or more H atoms in the above-mentioned groups may be replaced by D, F, CI, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, each of which is replaced by one or more R groups 2 can be substituted, with two or more residues R 1 together they can form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R 2 The substance is either the same or different in each occurrence: H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic residue with 1 to 20 C atoms, in which one or more H atoms may also be replaced by D or F; two or more substituents R may be present. 2 be linked together and form a ring. An aryl group according to this invention contains 6 to 40 carbon atoms; a heteroaryl group according to this invention contains 5 to 40 carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from nitrogen, oxygen, and / or sulfur. 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 (fused) aryl or heteroaryl group, for example, naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic compounds linked to each other by single bonds, such as biphenyl, are not referred to as aryl or heteroaryl groups, but rather as aromatic ring systems. An aromatic ring system according to this invention contains 6 to 60 carbon atoms, preferably 6 to 40 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 at least one heteroatom in the ring system, provided that the sum of 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 may also be linked by a non-aromatic unit (preferably less than 10% of the atoms other than hydrogen), such as a carbon, nitrogen, or oxygen atom or a carbonyl group. This also includes systems in which two or more aryl or...Heteroaryl groups are directly linked to one another, such as biphenyl, terphenyl, bipyridine, or phenylpyridine. For example, systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc., are also to be understood as aromatic ring systems within the meaning of this invention, as are systems in which two or more aryl groups are linked, for example, by a linear or cyclic alkyl group or by a silyl group. Preferred aromatic or Heteroaromatic ring systems are simple aryl or heteroaryl groups as well as groups in which two or more aryl or heteroaryl groups are directly linked together, for example biphenyl, terphenyl, quaterphenyl or bipyridine, as well as fluorene or spirobifluorene. An electron-rich heteroaromatic ring system is characterized by the fact that it is a heteroaromatic ring system that contains no electron-deficient heteroaryl groups. An electron-deficient heteroaryl group is a six-membered heteroaryl group with at least one nitrogen atom or a five-membered heteroaryl group with at least two heteroatoms, one of which is a nitrogen atom and the other oxygen, sulfur, or a substituted nitrogen atom, to which further aryl or heteroaryl groups may be fused. In contrast, electron-rich heteroaryl groups are five-membered heteroaryl groups with exactly one heteroatom selected from oxygen, sulfur, or substituted nitrogen, to which further aryl groups and / or further electron-rich five-membered heteroaryl groups may be fused.Examples of electron-rich heteroaryl groups include pyrrole, furan, thiophene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, and indenocarbazole. An electron-rich heteroaryl group is also referred to as an electron-rich heteroaromatic residue. An electron-deficient heteroaromatic ring system is characterized by containing at least one electron-deficient heteroaryl group, and in particular preferably no electron-rich heteroaryl groups. Within the scope of the present invention, the term alkyl group is used as a generic term for both linear or branched alkyl groups and cyclic alkyl groups. Similarly, the terms alkenyl group and alkynyl group are used as generic terms for both linear or branched alkenyl and alkynyl groups, respectively, and for cyclic alkenyl and alkynyl groups, respectively. For the purposes of this invention, a cyclic alkyl, alkoxy or thioalkoxy group is understood to be a monocyclic, a bicyclic or a polycyclic group. Within the scope of the present invention, the following are preferably used as the groupings of an aliphatic hydrocarbon residue or an alkyl group or an alkenyl or alkynyl group, which may contain 1 to 40 carbon atoms and in which individual hydrogen atoms or CH2 groups may also be substituted by the groups mentioned above: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 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, cyclooctyl, 2-ethylhexyl, 1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-Dimethyl)octyl, adamantyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hex-1-yl, 1,1-dimethyl-n-hept-1-yl, 1,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n-dec-1-yl, 1,1 -Dimethyl-n-dodec-1 -yl, 1 ,1 -Dimethyl-n-tetradec-1 - yl, 1 ,1 -Dimethyl-n-hexadec-1 -yl, 1 ,1 -Dimethyl-n-octadec-1 -yl, 1 ,1 -Diethyl- n-hex-1 -yl, 1 , 1 -Diethyl-n-hept-1 -yl, 1 , 1 -Diethyl-n-oct-1 -yl, 1 , 1 -Diethyl-n- dec-1 -yl, 1 ,1 -Diethyl-n-dodec-1 -yl, 1 ,1 -Diethyl-n-tetradec-1 -yl, 1 ,1 -Diethyl- n-hexadec-1 -yl, 1 ,1 -Diethyl-n-octadec-1 -yl, 1 -(n-Propyl)-cyclohex-1 -yl, 1 - (n-Butyl)-cyclohex-l -yl, 1 -(n-Hexyl)-cyclohex-l -yl, 1 -(n-Octyl)-cyclohex-l -yl und 1 -(n-Decyl)-cyclohex-1 -yl, Ethenyl, Propenyl, Butenyl, Pentenyl, Cyclopentenyl, Hexenyl, Cyclohexenyl, Heptenyl, Cycloheptenyl, Octenyl, Cyclooctenyl, Cyclooctadienyl, Ethinyl, Propinyl, Butinyl, Pentinyl, Hexinyl, Heptinyl oder Octinyl verstanden. Unter einer Alkoxygruppe OR, 1mit 1 bis 40 C-Atomen werden bevorzugt Methoxy, Trifluormethoxy, Ethoxy, n-Propoxy, i-Propoxy, n-Butoxy, i-Butoxy, s-Butoxy, t-Butoxy, n-Pentoxy, s-Pentoxy, 2-Methylbutoxy, n-Hexoxy, Cyclohexyloxy, n-Heptoxy, Cyclo- heptyloxy, n-Octyloxy, Cyclooctyloxy, 2-Ethylhexyloxy, Pentafluorethoxy und 2,2, 2-Trifluorethoxy verstanden. Unter einer Thioalkylgruppe SR 1 mit 1 bis 40 C-Atomen werden insbesondere Methylthio, Ethylthio, n- Propylthio, i-Propylthio, n-Butylthio, i-Butylthio, s-Butylthio, t-Butylthio, n- Pentylthio, s-Pentylthio, n-Hexylthio, Cyclohexylthio, n-Heptylthio, Cycloheptylthio, n-Octylthio, Cyclooctylthio, 2-Ethylhexylthio, Trifluor- The term methylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethinylthio, propynylthio, butynylthio, pentinylthio, hexinylthio, heptinylthio, or octinylthio is understood to mean methylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propynylthio, butynylthio, pentinylthio, hexinylthio, heptinylthio, or octinylthio. In general, alkyl, alkoxy, or thioalkyl groups according to the present invention can be straight-chain, branched, or cyclic, wherein one or more non-adjacent CH₂ groups can be replaced by the groups mentioned above; furthermore, one or more H atoms can also be replaced by D, F, CI, Br, I, CN, or NO₂, preferably F, CI, or CN, and particularly preferably F or CN. An aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, which may be further substituted with the aforementioned residues or a hydrocarbon residue and which may be linked via any positions on the aromatic or heteroaromatic compound, is understood to include, in particular, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indocarbazole, cis- or trans-monobenzoindenofluorene, cis- or trans- Dibenzoindenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole,Indol, Isoindol, Carba- zol, Pyridin, Chinolin, Isochinolin, Acridin, Phenanthridin, Benzo-5,6-chino- lin, Benzo-6,7-chinolin, Benzo-7,8-chinolin, Phenothiazin, Phenoxazin, Pyrazol, Indazol, Imidazol, Benzimidazol, Naphthimidazol, Phenanthrimi- dazol, Pyridimidazol, Pyrazinimidazol, Chinoxalinimidazol, Oxazol, Benz- oxazol, Naphthoxazol, Anthroxazol, Phenanthroxazol, Isoxazol, 1 ,2- Thiazol, 1 ,3-Thiazol, Benzothiazol, Pyridazin, Hexaazatriphenylen, Benzo- pyridazin, Pyrimidin, Benzpyrimidin, Chinoxalin, 1 ,5-Diazaanthracen, 2,7- Diazapyren, 2,3-Diazapyren, 1 ,6-Diazapyren, 1 ,8-Diazapyren, 4,5-Diaza- pyren, 4,5,9, 10-Tetraazaperylen, Pyrazin, Phenazin, Phenoxazin, Pheno-, thiazine, fluorubin, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 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 or groups derived from combinations of these systems. The phrase "two or more residues can form a ring system" 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: Further preferred embodiments are shown in the following formulas (3) to (6): where the symbols used have the meanings mentioned above for formula (1 ). In a preferred embodiment of the invention, a maximum of two symbols X per cycle represent N, particularly preferably a maximum of one symbol X. In a preferred embodiment of the invention, X represents CR. In a preferred embodiment, all X represent CR, where R represents H, D, F or CN. In a preferred embodiment of the invention, Y is the same or different at each occurrence CR' or N, with the proviso that 2 or 3 groups Y per cycle represent N, wherein if two or more adjacent Y, which represent CR', together form a condensed aromatic or heteroaromatic ring system, 1, 2, or 3 groups Y represent N. The two CR' form, for example, a condensed five-membered ring, whereby the system may also include further aromatic or heteroaromatic rings. Preferred embodiments of the compounds of formulas (3), (4), (5) and (6) are the following compounds of formulas (3-1 ) to (6-1 ): where the symbols, where present, have the meanings given for formulas (3) to (6). The compounds of formulas (1), (3), (4), (5) or (6) or their preferred embodiments can form an enantiomeric pair depending on the substitution. Preferably, the compound according to the invention exists as a racemate, but it can also exist as a pure enantiomer. In a preferred embodiment, the group of formula (2) is selected from one of the formulas (2-1 ) to (2-9): where the symbols, where present, have the meanings given for formula (2) and additionally, Y 1 The same or different for BR in every occurrence 1 , C(R 1 )2, NR 1 , O or S stands, preferably for 0 or S, most preferably for O. In a preferred embodiment, the group of formulas (2) represents one of the formulas (2-1), (2-2), (2-3), (2-4) or (2-5). In a preferred embodiment, the compound according to the invention is selected from one of the following compounds: In a preferred embodiment, the compound according to the invention is selected from the compounds in the preceding table, where Z represents one of the formulas (2-1 ), (2-2), (2-3), (2-4) or (2-5). The following are preferred substituents R, Ar', R', R 1 and R 2 described. In a particularly preferred embodiment of the invention, the following preferences apply to R, Ar', R', R. 1 and R 2 simultaneously and apply to the structures of formula (1) as well as to all preferred embodiments listed above. Additionally, for R and R', if R, or R', and associated residues comprise at least one heteroaromatic ring system including at least one nitrogen atom with three single bonds, then for each of these heteroaromatic ring systems, at least two of the residues bonded to the respective nitrogen atom via single bonds are always connected to the respective nitrogen atom and, independently of it, to the core structure. This means that in the case of a heteroaromatic ring system with a nitrogen atom of the formula N(R")3, where the residues R" can also form a ring with each other and one R" comprises the core structure, at least two residues R" are always connected to the core structure via one or more covalent bonds, independent of the nitrogen atom. In a carbazole, for example, two residues R" are connected to each other by a single bond.If the basic structure is part of the third residue R, then the two other interconnected residues do not have a nitrogen-independent bond with the basic structure. If the basic structure is part of one of the connected residues, then each of these residues has a bond with the nitrogen and an independent bond with the basic structure. The bond with the basic structure is a covalent bond. An independent bond means that the respective nitrogen is not part of the bond with the basic structure. The residues R, or R', and dependent residues, therefore, from the perspective of the backbone, do not contain any nitrogen atoms, particularly as part of a heteroaromatic ring system, which are connected to the backbone via only a single bond. These are In particular, carbazoles and derivatives thereof linked via the nitrogen atom. The term "backbone" refers to the condensed structure, e.g., triptycene, in formula (1) with formula (2), without R and R' substituents. Thus, starting from the backbone, no heteroaromatics are linked to it via only one nitrogen atom. In a preferred embodiment of the invention, R or R' is selected from the group consisting of H, D, F, CN, OR, either the same or different, for each occurrence. 1 , a straight-chain alkyl group with 1 to 10 carbon atoms or an alkenyl group with 2 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl or alkenyl group is each linked to one or more R groups 1may be substituted, but preferably is unsubstituted, and wherein one or more non-adjacent CH2 groups may be replaced by O, or an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, each of which is separated by one or more R groups 1 The substitution can be carried out by two R or R' substituents; in this case, two R or R' substituents can also form an aliphatic, aromatic, or heteroaromatic ring system. Particularly preferably, R or R' is selected, in each instance, from the group consisting of H, F, CN, a straight-chain alkyl group with 1 to 6 carbon atoms, in particular with 1, 2, 3, or 4 carbon atoms, or a branched or cyclic alkyl group with 3 to 6 carbon atoms, wherein the alkyl group is in each case linked to one or more R substituents. 1may be substituted, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, each separated by one or more R groups 1 , preferably non-aromatic residues R 1 , may be substituted. Most preferably, R or R' is selected, in each occurrence the same or differently, from the group consisting of H or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, each of which is modified by one or more R groups. 2 , preferably non-aromatic residues R 2 , can be substituted. Suitable aromatic or heteroaromatic ring systems R or R' are selected from phenyl, biphenyl, in particular ortho-, meta- or para-Biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, which may be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which may be linked via the 1-, 2-, 3- or 4-position, naphthalene, which may be linked via the 1- or 2-position, indole, benzofuran, benzothiophene, which may be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, carbazole, which may be linked via the 1-, 2-, 3- or 4-position, dibenzothiophene, which may be linked via the 1-, 2-, 3- or 4-position, indenocarbazole, indolocarbazole, pyridine, pyrimidine, Pyrazine, pyridazine, triazine, quinoline, quinazoline, benzimidazole, phenanthrene, triphenylene or a combination of two or three of these groups, each with one or more R groups 1They can be substituted. If R stands for a heteroaryl group, especially for triazine, pyrimidine, or quinazoline, aromatic or heteroaromatic residues can also be substituted. 1 be favored at this heteroaryl group. The groups R or R', when they represent an aromatic or heteroaromatic ring system respectively, are preferably chosen from the groups of the following formulas R-1 to R-147, where R 1 the above-mentioned meanings, the dashed line represents the connection to formula (1) and furthermore: Ar 3In each occurrence, it is either the same or different: a bivalent aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, each with one or more R groups. 1 may be substituted; A 1 Is it the same or different in every occurrence? BR 1 , C(R 1 )2, NR 1 , 0 or S, preferably C(R 1 )2, 0 or S; A 2 is the same or different in each occurrence C(R) 1 )2, NR 1 , 0 or S; p is 0 or 1 , where p = 0 means that the group Ar 3 is not present and that the corresponding aromatic or heteroaromatic group is directly bonded to the associated atom, for example a carbon atom or to a heteroatom such as a nitrogen atom. r is 0 or 1, where r = 0 means that no group A is present at this position. 1 is bound and instead of carbon atoms, residues R 1are bound. In a preferred embodiment, Ar comprises 3 Bivalent aromatic or heteroaromatic ring systems based on groups R-1 to R-147, where p equals 0 and the dashed bond and an R 1 for the bond to the aromatic or heteroaromatic group is located according to R-1 to R-147. If the above-mentioned groups R-1 to R-147 for R multiple groups A 1 If A exhibits such characteristics, then all combinations from the definition of A are suitable. 1 in question. Preferred embodiments are then those in which a group A 1 for C(R 1 )2, NR 1 , O or S and the other group A 1 for C(R 1 )2 stands or in which both groups A 1 for S or O, or in which both groups A 1 stand for 0 or S. If A 1 for NR 1 The substituent R stands. 1, which is bonded to the nitrogen atom, preferably for an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, which may also be further modified by one or more R groups 2 can be substituted. In a particularly preferred embodiment, this substituent R 1 same or different in each occurrence for an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 12 aromatic ring atoms, which does not have any fused aryl groups or heteroaryl groups in which two or more aromatic or heteroaromatic 6-ring groups are directly fused to one another, and which is also characterized by one or more R groups. 2 can be substituted. Particularly preferred are phenyl, biphenyl, terphenyl and quaterphenyl with linkage patterns as listed above for R-1 to R-35, wherein these structures are modified by one or more R groups. 1They may be substituted, but are preferably unsubstituted. If A 1 for C(R 1 )2, the substituents R are present 1 , which are bonded to this carbon atom, preferably the same or different in each occurrence for a linear alkyl group with 1 to 10 C atoms or for a branched or cyclic alkyl group with 3 to 10 C atoms or for an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, which may also be further divided by one or more R groups 2 It can be substituted. R is particularly preferred. 1 for a methyl group or for a phenyl group. The R groups can be used in this process. 1 They can also form a ring system together, resulting in a spiro system. In a preferred embodiment of the invention, R' is selected from the group consisting of D, F, CN, OR, either the same or different for each occurrence. 1or an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, each separated by one or more R groups 1 may be substituted. Particularly preferably, R' is selected in each occurrence, either the same or differently, from the group consisting of D, F, CN or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, particularly preferably with 6 to 12 aromatic ring atoms, each of which is separated by one or more R groups. 1 , preferably non-aromatic residues R 1 , can be substituted. Suitable aromatic or heteroaromatic ring systems R' are selected from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, which may be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which may be linked via the 1-, 2-, 3- or 4-position, naphthalene, which may be linked via the 1- or 2-position, indole, benzofuran, benzothiophene, which may be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, carbazole, which may be linked via the 1-, 2-, 3- or 4-position, dibenzothiophene, which may be linked via the 1-, 2-, 3- or 4-position linked, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline, benzimidazole, phenanthrene,Triphenylene or a combination of two or three of these groups, each with one or more R groups, 1 They can be substituted. If R' stands for a heteroaryl group, especially for triazine, pyrimidine, or quinazoline, aromatic or heteroaromatic residues can also be substituted. 1 be favored at this heteroaryl group. The groups R', when they represent an aromatic or heteroaromatic ring system, are preferably selected from the groups of the preceding formulas R-1 to R-147, and particularly preferably from the groups of the above formulas R-1 to R-147, wherein A 1 for C(R 1 )2, O or S. In a further preferred embodiment of the invention, R 1 , which is not bonded to the quaternary carbon atom of the framework, the same or different at each occurrence, selected from the group consisting of H, D, F, CN, OR 2, a straight-chain alkyl group with 1 to 10 carbon atoms or an alkenyl group with 2 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl or alkenyl group is each linked to one or more R groups 2 may be substituted and wherein one or more non-adjacent CH2 groups may be replaced by O, or an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, each of which is separated by one or more R groups 2 can be substituted; in this case, two or more residues R can be involved. 1 together form an aliphatic ring system. In a particularly preferred embodiment of the invention, R 1Selected from the group consisting of H, a straight-chain alkyl group with 1 to 6 C atoms, in particular with 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group with 3 to 6 C atoms, wherein the alkyl group is joined with one or more R groups, either the same or different at each occurrence. 2 may be substituted, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, each of which is separated by one or more R groups 2 It can be substituted, but is preferably unsubstituted. In a further preferred embodiment of the invention, R 2 the same or different at each occurrence H, F, an alkyl group with 1 to 4 C atoms or an aryl group with 6 to 10 C atoms, which may be substituted with an alkyl group with 1 to 4 C atoms, but is preferably unsubstituted. In another preferred embodiment of the invention, all residues R 1 , insofar as they are for an aromatic or heteroaromatic ring system, or R 2 insofar as they represent aromatic or heteroaromatic groups, selected from groups R-1 to R-147, which however, each time with R accordingly 2 , or rather the one at R 2 the aforementioned groups are substituted. In a preferred embodiment of the invention, all aromatic or heteroaromatic groups of the residues R, R', R 1 or R 2 selected from the relevant groups R-1 to R-147, preferably selected from groups R-1 to R-147, wherein A 1 for 0, S or C(R 1 )2 or the corresponding remainder C(R 2 )2 or C(R 3 )2stands. In a preferred embodiment, the R groups do not form any further aromatic or heteroaromatic groups fused to the basic structure of formula (1). In a preferred embodiment of the invention, R represents, in each instance, H, D, F, CN or a group selected from groups R-1 to R-147 and R, either the same or different. 1 For these groups, H, D, F or CN stands for, the preferred groups are R-1 to R-47, R-104 to R-110. In a preferred embodiment, R is the same or different for each occurrence in all cycles of the compound of formula (1 ) for H, D, F or CN, preferably H or D. In a preferred embodiment, the cycle with the Y and optionally with the residues R' forms a group selected from the groups R-70, R-71, R-72, R-73, R-74, R-75, R-76, R-80, R-81, R-113, R-133, R-134, R-135, R-136, R-145, R-146, R-147, where p equals 0. In a further embodiment of the invention, the group R 1 , which is bonded to the quaternary carbon atom of the framework, H, D, F, CN, OR 2 , a straight-chain alkyl group with 1 to 10 carbon atoms or an alkenyl group with 2 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl or alkenyl group is each linked to one or more R groups 2 may be substituted and in which one or more non-adjacent CH2 groups may be replaced by O, or a heteroaromatic ring system with 5 to 30 aromatic ring atoms, each separated by one or more R groups 2 can be substituted, with two or more residues R 1 together they can form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system. This R is preferred 1selected from groups R-1 to R-147 at the bridge, with the stipulation that they are compatible with R 2 are substituted, especially preferably selected from groups R-1 to R-147, provided that they are compatible with R 2 are substituted and A 1 for C(R 2 )2, 0 or S. In a preferred embodiment, R' in the groups of formulas (2-1) to (2-9) represents, in each occurrence, an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, each of which is further divided by one or more R groups. 1 can be substituted, wherein two or more residues R preferentially bound to the same cycle can form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system, which can be combined with one or more residues R 1The substitution can be, preferably with each occurrence the same or different group selected from R-1 to R-147. Preferably the residues R 1 in this case then for H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic residue with 1 to 20 C atoms, in which one or more H atoms may also be replaced by D or F; in this case two or more substituents R 1 be linked together and form a ring. In one embodiment of the invention, R' in formula (2) or one of formulas (2-1) to (2-9) represents, in each instance, the same or different group selected from R-1, R-2, R-3, R-44, R-45, R-46, R-47, R-112, R-114. In a preferred embodiment, in the case of multiple groups R', at least one group represents R-1, while at least one further group R' is selected from R-2, R-3, R-44, R-45, R-46, R-47, R-112, R-114. In the case of three groups R', one group may also represent CN. In compounds according to the invention, which are processed by vacuum evaporation, the alkyl groups preferably have no more than five carbon atoms, particularly preferably no more than four carbon atoms, and most preferably no more than one carbon atom. For compounds processed from solution, compounds substituted with alkyl groups, in particular branched alkyl groups, with up to 10 carbon atoms, or substituted with oligoarylene groups, for example ortho-, meta-, para- or branched terphenyl or quaterphenyl groups, are also suitable. The preferred embodiments mentioned above can be combined with one another as desired within the limitations defined in claim 1. In a particularly preferred embodiment of the invention, the preferences mentioned above occur simultaneously. Examples of preferred connections according to the embodiments listed above are the connections listed in the following table. The compounds according to the invention can be prepared according to synthesis steps known to those skilled in the art, such as bromination, Suzuki coupling, Ullmann coupling, Heck reaction, Hartwig-Buchwald coupling, etc. Another object of the present invention is therefore a method for producing the compounds according to the invention, characterized by the following steps: (A) Synthesis of the condensed skeleton according to formula (1); (B) Introducing aromatic or heteroaromatic groups to the bridging atoms by coupling reactions. The compounds according to the invention can therefore be prepared starting from bicyclics known from the literature, brominated or iodinated at the bridgehead carbon atom according to M. Oi et al., Chem. Sei., 2019, 10, 6107. This is shown in Schemes 1 and 2 using triptycene as an example. In step 1, the bridgehead carbon atom is first lithiated by reacting the bromide with n-butyllithium, followed by transmetallation with a copper(I) halide, preferably CuCl, and subsequent palladium-catalyzed CC coupling with a halogen heteroaromatic, such as 2-chlorotriazine, 2- or 4-chloropyrimidine, 2-chloropyrazine, 2-quinazoline, 2-quinoxaline, 2-chlorobenzofuro[2,3-d]pyrimidine, 2-chlorobenzofuro[3,2-d]pyrimidine, 2-chloro

[0001] Benzothieno-[2,3-d]pyrimidine, 2-chloro[1]benzothieno-[3,2-d]pyrimidine, etc. The heteroaromatic compound corresponds to the group containing Y in formula (1). Analogously, the corresponding bromo- or iodo-heteroaromatic compounds can be used. Electron-rich phosphines such as Tis(o-tolyl)-, Tris(o-methoxyphenyl)-, Tricyclohexyl-, Tri-tert-butyl-phosphine or S-Phos, X-Phos, RuPhos, Amphos, etc., are preferably used. When using less reactive chloro-heteroaromatic compounds, activation can be achieved by adding stoichiometric amounts of anhydrous lithium bromide or lithium iodide. 9,10-Dibromotriptycene can be selectively monolithiated (see G. Märkl et al., Tetrahedron Lett., 1974, 20, 1817) and subsequently coupled with a first Hal-HetAr as described above. Here, HetAr corresponds to the group containing Y in formula (1). In a second step, the remaining Br group can be coupled with another halogen aromatic Hal-Ar or halogen heteroaromatic Hal-HetAr, so that symmetrically and asymmetrically 9,10-substituted triptycenes can be obtained, see Scheme 2. 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, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone. Cyclohexylbenzene, decalin, dodecylbenzene, 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, diethyl sebacic acid ester, octyl octanoate, heptylbenzene, menthyl isovalerate, cyclohexylhexanoate or mixtures of these solvents. A further object of the present invention is therefore a formulation, in particular a solution, dispersion, or emulsion, 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. The preparation of such solutions is known to those skilled in the art and is described, for example, in WO 2002 / 072714, WO 2003 / 019694, and the literature cited therein. However, 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 a matrix material. This further compound may also be polymeric. The compounds according to the invention are suitable for use in an electronic device, in particular in an organic electroluminescent device (OLED). Depending on the substitution, the compounds can be used in different functions and layers. Another object of the present invention is therefore the use of a connection according to the invention in an electronic device. A further object of the present invention is an electronic device comprising at least one connection according to the invention. The compounds according to the invention can exist particularly when used as a racemate or as a pure enantiomer. An electronic device within the meaning of the present invention is a device which contains at least one layer containing at least one organic compound. The component may also contain inorganic materials or layers which are composed entirely of inorganic materials. The electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs), 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), dye-sensitized organic solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-Lasers) and organic plasmon-emitting devices, but preferably organic electroluminescent devices (OLEDs). The device is particularly preferably an organic electroluminescence device comprising a cathode, anode, and at least one emitting layer, wherein at least one organic layer, which may be an emitting layer, hole transport layer, electron transport layer, hole blocking layer, electron blocking layer, or another functional layer, comprises at least one compound according to the invention. The layer depends on the substitution of the compound. In addition to these layers, the organic electroluminescent device can contain further layers, for example, one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, charge generation layers, and / or organic or inorganic p / n junctions. Interlayers, which may, for example, have an exciton-blocking function, can also be introduced between two emitting layers. but pointed out that not every one of these layers necessarily has to be present. 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 are particularly preferred, wherein the three layers exhibit blue, green, and orange or red emission (the basic structure is described, for example, in WO 2005 / 011013). The organic electroluminescent device according to the invention can also be a tandem OLED, particularly for white-emitting OLEDs. The compound according to formula (1) is preferably used in an organic electroluminescent device comprising one or more phosphorescent emitters. The compound according to the embodiments described above can be used in different layers, depending on the precise structure. The organic electroluminescent device can contain one emitting layer, or it can contain several emitting layers, wherein at least one layer contains at least one compound according to the invention. Furthermore, the compound according to the invention can also be used in an electron transport layer and / or in a hole-blocking layer and / or in an exciton-blocking layer. The term "phosphorescent compound" typically refers to compounds in which the emission of light occurs through a spin-forbidden transition, e.g., a transition from an excited triplet state or a state with a higher spin quantum number, e.g., 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 particularly preferably greater than 56 and less than 80. Preferably, all luminescent complexes with transition metals or lanthanides are considered phosphorescent compounds, especially those containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, indium, palladium, platinum, silver, gold, or europium, and especially compounds containing indium, platinum, or copper. Within the scope of the present invention, all luminescent indium, platinum, or copper complexes are considered phosphorescent emitting compounds. 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 / 041769, WO 2019 / 020538, WO This can be taken from 2018 / 178001, WO 2019 / 115423 and WO 2019 / 158453. In general, all phosphorescent complexes such as those used for phosphorescent OLEDs according to the prior art and as 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.Even without inventive step, it is possible for a person skilled in the art to use further phosphorescent complexes in combination with the compounds of formula (1) in organic electroluminescent devices. Further examples are listed in the table below. According to the invention, it is also possible to use the compound of formula (1) in an electronic device containing one or more fluorescent emitting compounds. In a preferred embodiment of the invention, the compounds of formula (1) are used as an electron-transporting material. In this case, the compounds are preferably contained in an electron transport layer, a hole-blocking layer, or an electron-conducting or bipolar host material. Use in an electron transport layer is particularly preferred. An electron transport layer within the meaning of the present application is a layer with an electron-transporting function between the cathode and the emitting layer. Within the scope of this application, electron injection layers and hole-blocking layers are understood to be specific embodiments of electron transport layers. In the case of multiple electron transport layers between the cathode and the emitting layer, an electron injection layer is an electron transport layer that is directly adjacent to the cathode or separated from it only by a single coating of the cathode. In the case of multiple electron transport layers between the cathode and the emitting layer, a hole-blocking layer is the electron transport layer that is directly adjacent to the emitting layer on the cathode side. Preferably, the OLED according to the invention comprises two, three, or four electron transport layers between the cathode and the emitting layer, of which preferably at least one, and more preferably exactly one or two, contain a compound of formula (1). If the compound of formula (1) is used as an electron transport material in an electron transport layer, an electron injection layer or a hole blocking layer, the compound can be used as pure material, i.e. in a proportion of 100%, in the electron transport layer It can be used on its own, or it can be used in combination with one or more other compounds. Hole transport layers or electron blocking layers of the electronic devices according to the invention can additionally comprise one or more p-doping agents. The p-doping agents used according to the present invention are preferably organic electron acceptor compounds capable of oxidizing one or more of the other compounds in the mixture. Particularly preferred embodiments of p-doping agents are the compounds disclosed in WO 2011 / 073149, EP 1968131, EP 2276085, EP 2213662, EP 1722602, EP 2045848, DE 102007031220, US 8044390, US 8057712, WO 2009 / 003455, WO 2010 / 094378, WO 2011 / 120709, US 2010 / 0096600, WO 2012 / 095143 and DE 102012209523. Particularly preferred p-doping agents are quinodimethane compounds, azaindenofluorenediones, azaphenylenes, azatriphenylenes, iodine (I₂), metal halides, preferably transition metal halides, metal oxides, preferably metal oxides containing at least one transition metal or a metal of group 3, and transition metal complexes, preferably complexes of Cu, Co, Ni, Pd, and Pt with ligands containing at least one oxygen atom as a bonding site. Transition metal oxides are also preferred as dopants, preferably oxides of rhenium, molybdenum, and tungsten, particularly preferably Re₂O₇, MoO₃, WO₃, and ReO₃. The p-doping agents are preferably present in a substantially homogeneous distribution within the p-doped layers. This can be achieved, for example, by co-evaporation of the p-doping agent and the hole transport material matrix. Preferred p-doping agents include, in particular, the following compounds: J II N d " / ill d d NO^^ON N -09- The hole transport materials used can be employed in combination with a hexaazatriphenylene derivative, as described in US 2007 / 0092755. The hexaazatriphenylene derivative is particularly preferred when used in a separate layer. In a further embodiment of the present invention, the compound of formula (1) is used in an emitting layer as a matrix material in combination with one or more emitting compounds, preferably phosphorescent compounds. The proportion of matrix material in the emitting layer is, in this case, 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. Accordingly, the proportion of the emitting compound is between 0.1 and 50.0 vol.%, preferably between 0.5 and 20.0 vol.%, 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 comprise systems containing a variety of matrix materials (mixed matrix systems) and / or a variety of emitting compounds. In this case, too, the emitting compounds are usually the ones that constitute the smaller fraction in the system, and the matrix materials are the ones that constitute the larger fraction. In some cases, however, the fraction of a single matrix material in the system may be smaller than the fraction of a single emitting compound. Preferably, the compounds of formula (1) are used as components of mixed matrix systems. The mixed matrix systems preferably consist of two or three different matrix materials. Particularly preferably, the compound consists of 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. The compound of formula (1) is preferably the matrix material with electron-transporting properties. However, the desired electron-transporting and hole-transporting properties of the mixed matrix components can also be predominantly or completely combined in a single mixed matrix component, wherein the further mixed matrix component(s) fulfills other functions. The two different matrix materials can be present in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, even more preferably 1:10 to 1:1, and most preferably 1:4 to 1:1.Mixed matrix systems are preferably used in phosphorescent organic electroluminescent devices. A source for more detailed information on mixed matrix systems is application WO 2010 / 108579. The mixed matrix systems can contain one or more emitting compounds, preferably one or more phosphorescent compounds. In general, mixed matrix systems are preferably used in phosphorescent organic electroluminescence devices. Particularly suitable matrix materials, which can be used in combination with the compounds according to the invention as matrix components of a mixed matrix system, are selected from the preferred matrix materials for phosphorescent compounds or the preferred matrix materials for fluorescent compounds mentioned below, depending on which type of emitting compound is used in the mixed matrix system. Preferred phosphorescent compounds for use in mixed matrix systems are the same as those described above as generally preferred phosphorescent emitter materials. Preferred embodiments of the various functional materials in the electronic device are listed below. Examples of phosphorescent compounds are listed below. Preferred fluorescent-emitting compounds are selected from the class of arylamines. For the purposes of this invention, an arylamine or aromatic amine is understood to be a compound containing three substituted or unsubstituted aromatic or heteroaromatic ring systems directly bonded to the nitrogen atom. Preferably, at least one of these aromatic or heteroaromatic ring systems is a condensed ring system, particularly preferably with at least 14 aromatic ring atoms. Preferred examples include aromatic anthracene amines, aromatic anthracenediamines, aromatic pyrene amines, aromatic pyrenediamines, aromatic chrysene amines, or aromatic chrysenediamines. An aromatic anthracene amine is understood to be a compound in which a diarylamine group is directly bonded to an anthracene group, preferably at position 9.An aromatic anthracenediamine is understood to be a compound in which two diarylamine groups are directly bonded to an anthracene group, preferably at positions 9 and 10. Similarly, aromatic pyrenamines, pyrendiamines, chrysenamines, and chrysendiamines are defined, in which the diarylamine groups are preferably bonded to the pyrene at position 1 or 1,6. Other preferred emitting compounds are indenofluorenamines or fluorendiamines, for example according to WO 2006 / 108497 or WO 2006 / 122630, benzoindenofluorenamines, or benzofluorendiamines. For example, according to WO 2008 / 006449, and dibenzoindenofluorenamines or diamines, for example according to WO 2007 / 140847, as well as the indenofluorene derivatives with fused aryl groups disclosed in WO 2010 / 012328. Pyrenearylamines disclosed in WO 2012 / 048780 and WO 2013 / 185871 are also preferred. Also preferred are the benzoindenofluorenamines disclosed in WO 2014 / 037077, the benzofluorenamines disclosed in WO 2014 / 106522, the extended benzoindenofluorenes disclosed in WO 2014 / 111269 and WO 2017 / 036574, the phenoxazines disclosed in WO 2017 / 028940 and WO 2017 / 028941 and the furan or thiophene-bound fluorine derivatives disclosed in WO 2016 / 150544. Furthermore, boron compounds according to W02020208051 , W02015102118, WO2016152418 , WO201 8095397, WO2019004248 , WO2019132040, US20200161552 , WO2021 089450 can be used. Useful matrix materials, preferably for fluorescent compounds, include materials from various classes of substances. Preferred matrix materials are selected from the classes of oligoaryls (e.g., 2,2',7,7'-tetraphenylspirobifluorene according to EP 676461 or dinaphthylanthracene), in particular oligoaryls with fused aromatic groups, oligoarylene vinylenes (e.g., DPVBi or Spiro-DPVBi according to EP 676461), polypodal metal complexes (e.g., according to WO 2004 / 081017), hole-conducting compounds (e.g., according to WO 2004 / 058911), electron-conducting compounds, in particular ketones, phosphine oxides, sulfoxides, etc. (e.g., according to WO 2005 / 084081 and WO 2005 / 084082), atropisomers (e.g., according to WO 2006 / 048268), and boronic acid derivatives (e.g., according to WO 2006 / 048268). WO 2006 / 117052) or the benzanthracenes (for example according to WO 2008 / 145239).Particularly preferred matrix materials are selected from the classes of oligoarylenes containing naphthalene, anthracene, benzanthracene and / or pyrene or atropisomers of these compounds, the oligoarylene vinylenes, the ketones, the phosphine oxides and the sulfoxides. Most particularly preferred matrix materials are selected from the classes of oligoarylenes comprising anthracene, benzanthracene, benzophenanthrene and / or pyrene or atropisomers of these compounds. An oligoarylene is defined within the scope of... The present invention is understood to be a compound in which at least three aryl or arylene groups are linked together. Further preferred are the anthracene derivatives disclosed in WO 2006 / 097208, WO 2006 / 131192, WO 2007 / 065550, WO 2007 / 110129, WO 2007 / 065678, WO 2008 / 145239, WO 2009 / 100925, WO 2011 / 054442 and EP 1553154, the pyrene compounds disclosed in EP 1749809, EP 1905754 and US 2012 / 0187826, the benzanthracenylanthracene compounds disclosed in WO 2015 / 158409, the indenobenzofurans disclosed in WO 2017 / 025165 and those disclosed in WO 2017 / 036573 revealed phenanthrylanthracenes. Preferred matrix materials for phosphorescent compounds are, as well as compounds according to formula (1), 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, e.g. CBP (N,N-biscarbazolylbiphenyl) or WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or WO 2013 / 041176, indolocarbazole derivatives, e.g. B. 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. 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. B.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, diazaphosphol 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, lactams, e.g. according to WO 2011 / 116865 or WO 2011 / 137951, or dibenzofuran derivatives, e.g. according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO 2017 / 148565. Likewise, another phosphorescent emitter, which has a shorter wavelength than the actual emitter, may be used. emitted, present as a co-host in the mixture, or a compound that does not participate in the cargo transport or does not participate to a significant extent, as described for example in WO 2010 / 108579. Suitable charge transport materials, such as those that can be used in the hole injection or hole transport layer or in the electron barrier layer or in the electron transport layer of the electronic device according to the invention, are, in addition to the compounds of formula (1), for example those described in Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010, or other materials such as are used in these layers according to the prior art. Any materials used as hole transport materials in hole transport layers according to the prior art can be used as materials for the hole transport layer. Aromatic amine compounds can be used. Other compounds that are preferably used in hole transport layers of the OLEDs according to the invention are, in particular, indenofluorenamine derivatives (e.g., according to WO 06 / 122630 or WO 06 / 100896), the amine derivatives disclosed in EP 1661888, and hexaazatriphenylene derivatives (e.g.,according to WO 01 / 049806), amine derivatives with fused aromatics (for example, according to US 5,061,569), the amine derivatives disclosed in WO 95 / 09147, monobenzoindenofluorenamines (for example, according to WO 08 / 006449), dibenzoindenofluorenamines (for example, according to WO 07 / 140847), spirobifluorenamines (for example, according to WO 2012 / 034627 or WO 2013 / 120577), fluorenamines (for example, according to WO 2014 / 015937, WO 2014 / 015938, WO 2014 / 015935 and WO 2015 / 082056), spirodibenzopyranamines (for example, according to WO 2013 / 083216), dihydroacridine derivatives (to Example according to WO 2012 / 150001), spirodibenzofurans and spirodibenzothiophenes (for example according to WO 2015 / 022051, WO 2016 / 102048 and WO 2016 / 131521), phenanthrene diarylamines (for example according to WO 2015 / 131976), spirotribenzotropolones (for example according to WO 2016 / 087017), spirobifluorenes with meta-phenyldiamine groups (for example according to WO 2016 / 078738), spirobisacridines (for example according to WO 2015 / 158411), xanthene diarylamines (for example according to WO. 2014 / 072017), and 9,10-dihydroanthracene spiro compounds with diarylamino groups according to WO 2015 / 086108. Particularly preferred is the use of spirobifluorenes substituted by diarylamine groups in the 4-position as hole-transporting compounds, in particular the use of those compounds claimed and disclosed in WO 2013 / 120577, and the use of spirobifluorenes substituted by diarylamine groups in the 2-position as hole-transporting compounds, in particular the use of those compounds claimed and disclosed in WO 2012 / 034627. Preferably, the OLED according to the invention comprises two or more different electron-transporting layers. The compound of formula (1) can be used in one, more, or all of the electron-transporting layers. In a preferred embodiment, the compound of formula (1) is used in exactly one or exactly two electron-transporting layers, and other compounds are used in the other electron-transporting layers. Other compounds that can be used besides the compounds of formula (1) are all materials that are used as electron-transporting materials in the electron-transporting layer according to the prior art. Aluminum complexes, e.g., Alq3, zirconium complexes, e.g., Zrq4, and lithium complexes, e.g.,Liquid, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives, and phosphine oxide derivatives. Other suitable materials are derivatives of the aforementioned compounds as disclosed in JP 2000 / 053957, WO 2003 / 060956, WO 2004 / 028217, WO 2004 / 080975, and WO 2010 / 072300. Preferred cathodes for the electronic component are metals with low work function, metal alloys, or multilayer structures made of different metals, e.g., alkaline earth metals, alkali metals, Main group metals or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.) are suitable. Alloys of an alkali or alkaline earth metal and silver are also suitable, e.g., a magnesium-silver alloy. In multilayer structures, in addition to the aforementioned metals, other metals with a relatively high work function can be used, e.g., Ag or Al, with combinations of the metals, such as Ca / Ag, Mg / Ag, or Ba / Ag, typically employed. It can also be advantageous to introduce a thin interlayer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor. Examples of suitable materials include alkali or alkaline earth metal fluorides, as well as the corresponding oxides or carbonates (e.g., LiF, Li₂Ü, BaF₂, MgO, NaF, CsF, CS₂CO₃, etc.). Lithium quinolinate (LiQ) can also be used for this purpose.The thickness of this layer is preferably between 0.5 and 5 nm. Preferred anodes are materials with a high work function. Preferably, the anode has a work function of more than 4.5 eV against a vacuum. Firstly, metals with a high redox potential, e.g., Ag, Pt, or Au, are suitable. Secondly, metal / metal oxide electrodes (e.g., Al / Ni / NiOx, Al / PtOx) can also be preferred. For some applications, at least one of the electrodes must be transparent or semi-transparent to allow irradiation of the organic material (organic solar cell) or emission of light (OLED, O-laser). Preferred anode materials in this case are conductive mixed metal oxides. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred. Conductively doped organic materials, especially conductively doped polymers, are also preferred.Furthermore, the anode can also consist of two or more layers, for example an inner layer of ITO and an outer layer of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide. The device is structured, contacted, and finally sealed according to the application to prevent harmful influences from water and air. 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 formula (1) or the preferred embodiments described above. A further preferred organic electroluminescence device is characterized in that one or more layers are coated using a sublimation process. The materials are applied in vacuum sublimation systems at an initial pressure of less than 10⁻⁵ m. 5 mbar, preferably less than 10 6 mbar vapor deposition. However, it is also possible that the initial pressure is even lower, for example less than 10⁻⁶ mbar. 7 mbar. A preferred option is an organic electroluminescence device, 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 -5 Pressures of mbar and 1 bar are applied. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured. A further preferred organic electroluminescent device is characterized in that one or more layers are produced from solution, e.g., by spin coating, or by any printing process, e.g., screen printing, flexographic printing, offset printing, LITI (light-induced thermal imaging, thermal transfer printing), inkjet printing, or nozzle printing. Soluble compounds are required for this purpose, 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 methods 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. According to the invention, the electronic devices containing one or more compounds of formula (1) can be used in displays, as light sources in lighting applications and as light sources in medical and / or cosmetic applications (e.g. light therapy). The compounds and organic electroluminescent devices according to the invention are characterized by one or more of the following properties: 1. The connections according to the invention lead to long service lives. 2. The compounds according to the invention lead to high efficiencies, in particular to a high EQE. 3. The connections according to the invention result in low operating stresses. The invention is further explained by the following examples, without being intended to limit it. A person skilled in the art can implement the invention in its entire disclosed scope from the descriptions and, without inventive effort, create further connections according to the invention and use them in electronic devices or apply the method according to the invention. 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. Solvents and reagents can be obtained, for example, from Sigma-Aldrich or ABCR. The information in square brackets or 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. A) Synthesis of compounds B and synthons S according to the invention: Example B1: Variant A: via organo-lithium compound A solution of 3.3 g (10 mmol) of LS1 in a mixture of 100 ml THF and 150 ml toluene, cooled to -78 °C, is treated dropwise with 4.0 ml (10.5 mmol) of n-BuLi (2.6 molar in n-hexane) for 30 min and stirred for 1.5 h. A solution of 2.8 g (10.5 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine [3842-55-5] in 100 ml THF is added dropwise, stirred for 30 min, the reaction mixture is then slowly warmed to room temperature and stirred for 2 h. With thorough stirring, 2 ml of water are added, the reaction mixture is concentrated to dryness, the residue is stirred with 30 ml of methanol, and chromatography is performed (Torrent, column chromatography system by A. Semrau). Further purification is carried out by repeated hot extraction crystallization (using common organic solvents or combinations thereof, preferably acetonitrile-DCM, 1:3 to 3:1 vv) and fractional sublimation or annealing under high vacuum. Yield: 1.7 g (3.4 mmol) 34%; Purity: approx. 99.9% by HPLC. Variant B: via organo-copper compound Procedure according to M. Oi et al., Chem. Sei., 2019, 10, 6107, Example 16. Preparation: 33.3 g (100 mmol) LS1, 39.5 g (110 mmol) 2-iodo-4,6-diphenyl-1,3,5-triazine [83819-97-0], in a stirred autoclave, 140 °C, 35 h. Further purification is carried out by chromatography and / or repeated hot extraction crystallization (common organic solvents or combinations thereof, preferably acetonitrile DCM, 1:3 to 3:1 vv) and fractional extraction. Sublimation or annealing under high vacuum. Yield: 34.3 g (71 mmol) 71%; Purity: approx. 99.9% n. HPLC. The following compounds can be prepared analogously. Unless otherwise noted, variant B is used below. The yields for chlorides are typically in the range of 30–70%, those for bromides in the range of 50–80%, and those for iodides in the range of 60–90%.  Example: Manufacturing of OLEDs 1) Vacuum-processed devices: The production 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 of various OLEDs. Cleaned glass plates (cleaned in a Miele laboratory dishwasher using Merck Extran cleaner), coated with a 50 nm thick structured ITO (indium tin oxide), are pretreated with UV ozone for 25 minutes (UV ozone generator PR-100, UVP). These coated glass plates form the substrates onto which the OLEDs are applied. 1a) Blue Fluorescent OLED Components - BF: The compounds B according to the invention can be used in the electron transport layer (ETL) and the hole-blocking layer (HBL). All materials are thermally vapor-deposited in a vacuum chamber. The emission layer (EML) always consists of at least one matrix material (host material) SMB (see Table 1) and an emitting dopant D, which is added to the matrix material(s) by co-evaporation in a specific volume fraction. A specification such as SMB:D (97:3%) means that the material SMB is present in a volume fraction of 97% and the dopant D in a fraction of 3% in the layer. Similarly, the electron transport layer also consists of a mixture of two materials, see Table 1. The materials used to produce the OLEDs are shown in Table 5. The OLEDs are characterized according to standard procedures. This includes determining the electroluminescence spectra, current efficiency (measured in cd / A), power efficiency (measured in µm / W), and external quantum efficiency (EQE, measured in percent) as a function of luminance, calculated from current-voltage-luminance curves (IUL curves) assuming a Lambertian emission characteristic. The lifetime is also determined. EQE (%) and voltage (V) are specified at a luminance of 1000 cd / m². 2 The lifespan is calculated at a starting luminance of 1000 cd / m². 2 The time it takes for the brightness of the reference to drop to 90% of its initial brightness is determined. The lifetime of the OLED components containing the compounds B according to the invention is expressed as a percentage of the reference. The OLEDs have the following layer structure: Substrat HIL hole injection layer made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm Hole transport layer (HTL) made of HTM1, 160 nm Electron blocking layer (EBL) made of EBM1, 10 nm Emission layer (EML), see Table 1 Hole blocker layer (HBL), see Table 1 Electron transport layer (ETL), see Table 1 Electron injection layer (EIL) made of ETM2, 1 nm Aluminum cathode, 100 nm Table 1: Structure of Blue Fluorescent OLED Components Table 2: Results for Blue Fluorescent OLED Components 1 b) Phosphorescent OLED components: The compounds B according to the invention can be used as matrix materials (host materials) in the electron transport layer (ETL), the hole-blocking layer (HBL), and the emission layer (EML). For this purpose, all materials are thermally vapor-deposited in a vacuum chamber. The emission layer always consists of at least one or more matrix materials M and a phosphorescent dopant Ir, which is added to the matrix material(s) by co-evaporation in a specific volume fraction. A specification such as M1 :M2:Ir (55%:35%:10%) means that material M1 is present in the layer in a volume fraction of 55%, M2 in a volume fraction of 35%, and Ir in a volume fraction of 10%. Similarly, the electron transport layer can also be composed of a mixture of two materials. The exact structure of the OLEDs can be found in Table 3. The materials used to manufacture the OLEDs are shown in Table 5. The OLEDs are characterized according to standard procedures. This includes determining the electroluminescence spectra, current efficiency (measured in cd / A), power efficiency (measured in µm / W), and external quantum efficiency (EQE, measured in percent) as a function of luminance, calculated from current-voltage-luminance curves (IUL curves) assuming a Lambertian emission characteristic. The lifetime is also determined. EQE (%) and voltage (V) are specified at a luminance of 1000 cd / m². 2 The lifespan is calculated at a starting luminance of 1000 cd / m². 2 (Blue and Red Devices) or 10000 cd / m² 2(Yellow and Green Devices) determined. The measured time in which the brightness of the reference has decreased to 80% of the initial brightness is set to 100%. The lifetime of the OLED components containing the compounds B according to the invention is given as a percentage of the reference. The OLEDs have the following layer structure: substrate HIL hole injection layer made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm Hole transport layer (HTL) made of HTM1, 180 nm for blue, 50 nm for green, 40 nm for yellow, 90 nm for red Electron blocking layer (EBL): 20 nm made of EBM2 for blue, 20 nm made of EBM1 for green and yellow, 10 nm for red Emission layer (EML), see Table 3 Hole blocker layer (HBL), see Table 3 Electron transport layer (ETL), see Table 3 Electron injection layer (EIL) made of ETM2, 1 nm Aluminum cathode, 100 nm Table 3: Structure of phosphorescent OLED components Table 5: Structural formulas of the materials used

Claims

Patent claims 1 . Compound according to formula (1 ) and formula (2), Formula (1 ) Formula (2) where the symbols used are: X is the same or different at each occurrence CR or N with the proviso that a maximum of two groups X per cycle represent N; Z represents a group of formula (2), where the dashed bond in formula (2) represents the bond to the quaternary carbon; Y is the same or different on each occurrence and is CR' or N, with the proviso that 2 or 3 Y groups per cycle are N or that 1, 2 or 3 Y groups are N, and two or more Y which are CR' together form an aromatic or heteroaromatic ring system, preferably in each case 2 or 3 Y groups are N; Q represents a bivalent alkylene group having 1 to 4 carbon atoms, a bivalent alkenylene group having 2 to 4 carbon atoms or a bivalent aryl or heteroaryl group having 5 to 60 ring atoms, where the alkylene, alkenylene, aryl or heteroaryl groups may be substituted by one or more groups R; R is the same or different at each occurrence and is H, D, F, CI, Br, I, OAr', SAr', B(OR 1 )2, CHO, C(=O)R 1 , CR 1 =C(R 1 )2, CN, C(=O)OR 1 , C(=O)NR 1 , Si(R 1 )3, NO2, P(=O)(R 1 )2, OSO2R 1 , OR 1 , S(=O)R 1 , S(=O)2R 1 , SR 1 , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 1may be substituted, with one or more non-adjacent CH2 groups being replaced by -R 1 C=CR 1 -, -C=C-, Si(R 1 )2, CONR 1 , C=O, C=S, -C(=O)O-, P(=O)(R 1 ), -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, each substituted by one or more radicals R 1 may be substituted, where two or more R radicals preferably bound to the same cycle may form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system which may be substituted with one or more R radicals 1may be substituted, wherein if R and associated radicals comprise at least one heteroaromatic ring system comprising at least one nitrogen atom with three single bonds, for each of these heteroaromatic ring systems, at least two of the radicals bonded to the respective nitrogen atom via single bonds are always bonded to the respective nitrogen atom and independently thereof to the basic structure; R' is the same or different at each occurrence and is H, D, F, CI, Br, I, OAr', SAr', B(OR 1 )2, CHO, C(=O)R 1 , CR 1 =C(R 1 )2, CN, C(=O)OR 1 , C(=O)NR 1 , Si(R 1 )3, NO2, P(=O)(R 1 )2, OSO2R 1 , OR 1 , S(=O)R 1 , S(=O)2R 1 , SR 1, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 1 may be substituted, with one or more non-adjacent CH2 groups being replaced by -R 1 C=CR 1 -, -C=C-, Si(R 1 )2, CONR 1 , C=O, C=S, -C(=O)O-, P(=O)(R 1 ), -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, each of which is substituted by one or more radicals R 1 may be substituted, where two or more R radicals preferably bound to the same cycle can form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system which can be reacted with one or more R radicals1 may be substituted, wherein if R' and associated radicals comprise at least one heteroaromatic ring system comprising at least one nitrogen atom with three single bonds, for each of these heteroaromatic ring systems, at least two of the radicals bonded to the respective nitrogen atom via single bonds are always bonded to the respective nitrogen atom and independently thereof to the basic structure; Ar' is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is substituted by one or more radicals R 1 may be substituted, where two or more R 1 can form an aromatic or heteroaromatic ring system with each other; R 1 is the same or different at each occurrence H, D, F, I, B(OR 2 )2, CHO, C(=O)R 2 , CR 2 =C(R 2 )2, CN, C(=O)OR 2 , Si(R 2 )3, NO2, P(=O)(R2 )2, OSO2R 2 , SR 2 , OR 2 , S(=O)R 2 , S(=O)2R 2 , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 2 and wherein one or more CH2 groups in the above-mentioned groups are substituted by -R 2 C=CR 2 -, -C=C-, Si(R 2 )2, C=O, C=S, -C(=O)O-, CONR 2 , P(=O)(R 2 ), -O-, -S-, SO or SO2 and where one or more H atoms in the above-mentioned groups can be replaced by D, F, CI, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, each of which is substituted by one or more radicals R 2 may be substituted, where two or more radicals R 1can form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R 2 is, identically or differently at each occurrence, H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which one or more H atoms may be replaced by D or F; two or more substituents R 2 be linked together and form a ring.

2. A compound according to claim 1, selected from the compounds of formulas (3), (4), (5) or (6), wherein the symbols used have the meanings given in claim 1.

3. A compound according to one or more of claims 1 or 2, selected from the compounds of formulas (3-1), (4-1), (5-1) or (6-1), wherein the symbols used have the meanings given in claim 2.

4. A compound according to one or more of claims 1 or 3, wherein the group of formula (2) is selected from one of the formulas (2-1) to (2-9): where the symbols used have the meanings given in claim 1 and additionally, Y 1 same or different for each occurrence for BR 1 , C(R 1 )2, NR 1 , O or S.

5. A process for preparing a compound according to one or more of claims 1 to 4, characterized by the following steps: (A) Synthesis of the condensed skeleton according to formula (1 ); (B) introducing the aromatic or heteroaromatic groups at the bridge atoms by coupling reactions.

6. An oligomer, polymer or dendrimer comprising one or more compounds of the formula (1) according to one or more of claims 1 to 4, where the bond(s) to the oligomer, polymer or dendrimer can be made at any position in formula (1).

7. A formulation comprising at least one compound according to one or more of claims 1 to 4 and at least one further compound and / or at least one solvent.

8. Use of a compound according to one or more of claims 1 to 4 and / or a formulation according to claim 7 in an electronic device.

9. Electronic device comprising at least one compound according to one or more of claims 1 to 4 and / or at least one oligomer, polymer or dendrimer according to claim 6.

10. Electronic device according to claim 9, which is an organic electroluminescent device, characterized in that the device comprises an anode, a cathode and at least one emitting layer, wherein at least one organic layer, which can be an emitting layer, hole transport layer, electron transport layer, hole blocking layer, electron blocking layer or another functional layer, comprises at least one compound according to formula (1).

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