Compounds that can be used as active compounds in an organic electronic device

Description

[0001] The present invention describes compounds, in particular for use in electronic devices. The invention further relates to a process for preparing the compounds according to the invention and to electronic devices containing these compounds.

[0002] The structure of organic electroluminescent devices (OLEDs), in which organic semiconductors are used as functional materials, is described, for example, in US 4539507, US 5151629, EP 0676461, and WO 98 / 27136. Organometallic complexes that exhibit phosphorescence are often used as emitting materials. For quantum mechanical reasons, up to four times the energy and power efficiency is possible when using organometallic compounds as phosphorescence emitters. In general, there is still room for improvement with OLEDs, and especially with OLEDs that exhibit phosphorescence, for example with regard to efficiency, operating voltage, and lifetime. Furthermore, organic electroluminescent devices are known that comprise fluorescent emitters or emitters that exhibit TADF (thermally activated delayed fluorescence).

[0003] The properties of organic electroluminescent devices are not only determined by the emitters used. The other materials used, such as host / matrix materials, hole-blocking materials, electron-transport materials, hole-transport materials, and electron- or exciton-blocking materials, are also of particular importance. Improvements to these materials can lead to significant improvements in electroluminescent devices.

[0004] According to the prior art, compounds with bi- or tricyclic ring systems are used, in particular, to produce metal complexes that exhibit phosphorescence. These compounds serve, in particular, as ligands in the corresponding complexes. This prior art includes, in particular, the publications WO 2014 / 094960 A1, WO 2014 / 094961 A1, WO 2015 / 104045 A1, WO 2015 / 117718 A1, WO 2016 / 124304, and WO 2018 / 069197 A1. Matrix materials, electron-transport materials, hole-transport materials, fluorescent emitters, or emitters that exhibit TADF (thermally activated delayed fluorescence) are not described in these documents.

[0005] Furthermore, WO 2015 / 036078 discloses heterocyclic compounds that can be used, among other things, as matrix materials, electron-transport materials, or hole-transport materials. Most of these compounds comprise a bicyclic ring system fused to a pyridine or pyridazine structure, to which, in turn, an aromatic or heteroaromatic ring system is fused. WO 2018 / 087346 A1 lists compounds with an acceptor and a donor group that can be used as TADF materials, host materials, electron-transport materials, or hole-transport materials.

[0006] Furthermore, G. Li et al., Tetrahedron Letters, Vol. 45, No. 45, pp. 8399–8402, November 1, 2004, describe the synthesis, structural characterization, and rearrangement of dibenzotricyclo[3.3.0.02,6]-1,2,5,6-tetrasubstituted octanes.

[0007] In general, these materials, for example, for use as matrix materials, hole-conducting materials, or electron-transport materials, still require improvement, particularly in terms of lifetime, but also in terms of device efficiency and operating voltage. Furthermore, the compounds should exhibit high color purity.

[0008] A further object of the present invention is to provide compounds which are suitable for use in an organic electronic device, in particular in an organic electroluminescent device, as fluorescent emitters or emitters which exhibit TADF (thermally activated delayed fluorescence) and which, when used in this device, lead to good device properties, and to provide the corresponding electronic device.

[0009] The object of the present invention is therefore to provide compounds which are suitable for use in an organic electronic device, in particular in an organic electroluminescent device, and which, when used in this device, lead to good device properties, as well as to provide the corresponding electronic device.

[0010] In particular, the object of the present invention is to provide compounds that result in a long lifetime, good efficiency, and low operating voltage. The properties of the matrix materials, the hole-conducting materials, or the electron-transport materials have a significant influence on the lifetime and efficiency of the organic electroluminescent device.

[0011] A further object of the present invention can be seen in providing compounds suitable for use in a phosphorescent or fluorescent OLED, in particular as a matrix material. In particular, it is an object of the present invention to provide matrix materials suitable for red, yellow, and green phosphorescent OLEDs.

[0012] Furthermore, the compounds should lead to devices with excellent color purity, especially when used as matrix materials, as hole-transport materials or as electron-transport materials in organic electroluminescent devices.

[0013] Furthermore, the compounds should be as easy to process as possible, particularly exhibiting good solubility and film formation. For example, the compounds should exhibit increased oxidation stability and an improved glass transition temperature.

[0014] Another task can be seen in providing electronic devices with excellent performance as cost-effectively as possible and in consistent quality

[0015] Furthermore, the electronic devices should be able to be used or adapted for a variety of purposes. In particular, the performance of the electronic devices should be maintained over a wide temperature range.

[0016] Surprisingly, it has been found that certain compounds, described in more detail below, achieve these objects and eliminate the disadvantage of the prior art. The use of these compounds leads to very good properties of organic electronic devices, in particular 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.

[0017] The present invention therefore relates to a compound which can be used as an active compound in an organic electronic device, characterized in that the compound has at least one aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, which is condensed to an aliphatic polycyclic ring system having at least 3 rings, characterized in that the aliphatic polycyclic ring system having at least 3 rings, which is condensed to an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, forms a partial structure of the formulas (N-1) to (N-6), where the dashed lines represent the links of the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, to which the aliphatic polycyclic ring system having at least 3 rings is condensed, and where the following applies to the symbols R 1< , v, t and s: R 1< is on each occurrence, identically or differently, H, D, OH, F, Cl, Br, I, CN, NO 2 , 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(OR 2< ) 2 , Si(Ar 1< ) 3 , Si(R 2< ) 3 , a straight-chain alkyl, Alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which may be substituted by one or more radicals R 2<, where one or more non-adjacent CH 2 groups are substituted by -R 2< C=CR 2< -, -C=C-, Si(R 2< ) 2 , Ge(R 2< ) 2 , Sn(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 SO 2 and where one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO 2, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which can be substituted by one or more radicals R 2<, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which can be substituted by one or more radicals R 2<, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which can be substituted by one or more radicals R 2<, or a combination of these systems; two or more, preferably adjacent radicals R 1< can form with one another a mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system; Ar 1< is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms,which may be substituted by one or more, preferably non-aromatic, radicals R 2<, two radicals Ar 1< which bond to the same Si atom, N atom, P atom or B atom may also be bridged to one another 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, SO 2 , N(R 2< ), P(R 2< ) and P(=O)R 2< ; R 2< is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CN, B(OR 3< ) 2 , NO 2 , C(=O)R 3< , CR 3< =C(R 3< ) 2, C(=O)OR 3, C(=O)N(R 3< ) 2 , Si(R 3< ) 3 , P(R 3< ) 2 , B(R 3< ) 2, N(R 3< ) 2, NO 2 , P(=O)(R 3< ) 2 , OSO 2 R 3< , OR 3< , S(=O)R 3< , S(=O) 2 R 3< , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 3<,where one or more non-adjacent CH 2 groups may be replaced by -R 3< C=CR 3< -, -C=C-, Si(R 3< ) 2 , Ge(R 3< ) 2 , Sn(R 3< ) 2 , C=O, C=S, C=NR 3< , -C(=O)O-, -C(=O)NR 3< -, NR 3< , P(=O)(R 3< ), -O-, -S-, SO or SO 2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more radicals R 3<, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 3<, or a combination of these systems; two or more, preferably adjacent substituents R 2< may also form a mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system; R 3< is, at each occurrence, identical or different, selected from the group consisting of H, D, F, CN,an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; two or more, preferably adjacent, substituents R 3< may also form a mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system with one another; the index s is 0, 1 or 2; the index t is 0, 1, 2, 3, 4, 5, 6, 7 or 8, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2; the index v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1 or 2, and characterized in that the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms,to which an aliphatic polycyclic ring system with at least 3 rings is condensed, forming a partial structure of the formulas (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and (Ar-55) to (Ar-66), , where X' is N or CR 1< , preferably CR 1<, where R 1< has the meaning set out above and the aliphatic polycyclic ring system having at least 3 rings bonds to the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms at the positions marked by o to form a ring.

[0018] Furthermore, it can be provided that the ring via which the aliphatic polycyclic ring system with at least 3 rings is condensed to the aromatic or heteroaromatic ring system with 5 to 60 carbon atoms comprises six ring atoms and at least two non-adjacent nitrogen atoms.

[0019] Furthermore, it can be provided that the ring via which the aliphatic polycyclic ring system with at least 3 rings is condensed to the aromatic or heteroaromatic ring system with 5 to 60 carbon atoms comprises six ring atoms and no nitrogen atom.

[0020] Furthermore, it can be provided that the ring via which the aliphatic polycyclic ring system with at least 3 rings is condensed to the aromatic or heteroaromatic ring system with 5 to 60 carbon atoms comprises six ring atoms and at least one nitrogen atom and no further ring system is condensed to this ring.

[0021] Active compounds are generally the organic or inorganic materials which are introduced, for example, in an organic electronic device, in particular in an organic electroluminescent device between the anode and the cathode, for example charge injection, charge transport or charge blocking materials, but in particular emission materials and matrix materials.

[0022] The compound that can be used as an active compound in an organic electronic device can 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-conducting materials, hole-injecting materials, n-dopants, p-dopants, 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-conducting materials, hole-injecting materials, n-dopants, p-dopants, wide-band-gap materials, electron-blocking materials, and / or hole-blocking materials are preferred.

[0023] For the purposes of the present invention, adjacent carbon atoms are carbon atoms that are directly linked to one another. Furthermore, "adjacent radicals" in the definition of radicals means that these radicals are bonded to the same carbon atom or to adjacent carbon atoms. These definitions apply accordingly, among other things, to the terms "adjacent groups" and "adjacent substituents."

[0024] For the purposes of this description, the phrase "two or more residues can form a ring" is understood to mean, among other things, that the two residues are linked by a chemical bond with the formal elimination of two hydrogen atoms. This is illustrated by the following scheme.

[0025] Furthermore, the above formulation should also be understood to mean that if one of the two residues represents hydrogen, the second residue binds to the position to which the hydrogen atom was bonded, forming a ring. This is illustrated by the following scheme:

[0026] A fused aryl group, a fused aromatic ring system, or a fused 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, so that, for example, two C atoms belong to the at least two aromatic or heteroaromatic rings, as in naphthalene, for example. In contrast, fluorene, for example, is not a fused aryl group within the meaning of the present invention, since in fluorene the two aromatic groups do not have a common edge. Corresponding definitions apply to heteroaryl groups and to fused ring systems, which may or may not also contain heteroatoms.

[0027] If two or more, preferably adjacent, radicals R, R 1< , R 2< and / or R 3< form a ring system with one another, a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system can be formed.

[0028] An aryl group within the meaning of this invention contains 6 to 60 C atoms, preferably 6 to 40 C atoms, particularly preferably 6 to 30 C atoms; a heteroaryl group within the meaning of this invention contains 2 to 60 C atoms, preferably 2 to 40 C atoms, particularly preferably 2 to 30 C atoms and at least one heteroatom, with the proviso that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aryl group or heteroaryl group is understood to be either a simple aromatic cycle, i.e. benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a condensed aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc.

[0029] An aromatic ring system within the meaning of this invention contains 6 to 60 C atoms, preferably 6 to 40 C atoms, particularly preferably 6 to 30 C atoms in the ring system. A heteroaromatic ring system within the meaning of this invention contains 1 to 60 C, preferably 1 to 40 C atoms, particularly preferably 1 to 30 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aromatic or heteroaromatic ring system within the meaning of this invention is to be understood as a system which does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups can also be replaced by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as, for example, B. a C, N or O atom or a carbonyl group.For example, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc., are 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 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.

[0030] A cyclic alkyl, alkoxy or thioalkoxy group in the sense of this invention is understood to mean a monocyclic, a bicyclic or a polycyclic group.

[0031] In the context of the present invention, a C 1 - to C 20 -alkyl group, in which individual H atoms or CH 2 groups can also be substituted by the above-mentioned groups, is understood to mean, for example, the radicals methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, Cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, trifluoromethyl, pentafluoroethyl, 2,2,2-Trifluoroethyl, 1,1-Dimethyl-n-hex-1-yl-, 1,1-Dimethyl-n-hept-1-yl-, 1,1-Dimethyl-n-oct-1-yl-, 1,1-Dimethyl-n-dec-1-yl-, 1,1-Dimethyl-n-dodec-1-yl-, 1,1-Dimethyl-n-tetradec-1-yl-, 1,1-Dimethyl-n-hexadec-1-yl-, 1,1-Dimethyl-n-octadec-1-yl-, 1,1-Diethyl-n-hex-1-yl-, 1,1-Diethyl-n-hept-1-yl-, 1,1-Diethyl-n-oct-1-yl-, 1,1-Diethyl-n-dec-1-yl-, 1,1-Diethyl-n-dodec-1-yl-, 1,1-Diethyl-n-tetradec-1-yl-, 1,1-Diethyln-n-hexadec-1-yl-, 1,1-Diethyl-n-octadec-1-yl-, 1-(n-propyl)-cyclohex-1-yl-, 1-(n-butyl)-cyclohex-1-yl-, 1-(n-hexyl)-cyclohex-1-yl-, 1-(n-Octyl)-cyclohex-1-yl- and 1-(n-Decyl)-cyclohex-1-yl- An alkenyl group is understood to mean, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, or cyclooctadienyl. An alkynyl group is understood to mean, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, or octynyl. A C 1 - to C 40 -alkoxy group is understood to mean, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, or 2-methylbutoxy.

[0032] An aromatic or heteroaromatic ring system having 5 to 60, preferably 5-40 aromatic ring atoms, particularly preferably 5 to 30 aromatic ring atoms, which may also be substituted by the above-mentioned radicals and which may be linked to the aromatic or heteroaromatic ring via any desired positions, is understood to mean, for example, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzfluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-monobenzoindenofluorene, cis- or trans-dibenzoindenofluorene, truxene, isotruxene, Spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole,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, Azacarbazol, Benzocarbolin, Phenanthrolin, 1,2,3-Triazol, 1,2,4-Triazol, Benzotriazol, 1,2,3-Oxadiazol, 1,2,4-Oxadiazol, 1,2,5-Oxadiazol, 1,3,4-Oxadiazol, 1,2,3-Thiadiazol, 1,2,4-Thiadiazol, 1,2,5-Thiadiazol, 1,3,4-Thiadiazol, 1,3,5-Triazin, 1,2,4-Triazin, 1,2,3-Triazin, Tetrazol, 1,2,4,5-Tetrazin, 1,2,3,4-Tetrazin, 1,2,3,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole.

[0033] According to the present invention, the aliphatic polycyclic ring system having at least 3 rings which is condensed to an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms forms a partial structure of the formulas (N-1) to (N-6) where the symbols R 1< , v, t and s have the meaning given above and the dashed lines represent the links of the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms to which the aliphatic polycyclic ring system having at least 3 rings is fused. The double bond shown in the structures according to formulas (N-1) to (N-6) can be regarded as part of the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms to which the structure according to one of the formulas (N-1) to (N-6) is fused.

[0034] Furthermore, the invention provides that the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, which is fused to an aliphatic polycyclic ring system having at least 3 rings, forms a partial structure of the formulas (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and (Ar-55) to (Ar-66): where X' is N or CR 1< , preferably CR 1<, where R 1< has the meaning given above and the aliphatic polycyclic ring system having at least 3 rings bonds at the positions marked by o to the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms to form a ring.

[0035] Furthermore, compounds with partial structures of the formulas (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and (Ar-55) to (Ar-66) are preferred, in which at most two groups X' per ring are N, preferably all groups X' per ring are CR 1<, and preferably at least one, particularly preferably at least two of the groups X' per ring are selected from CH and CD.

[0036] Furthermore, compounds with partial structures of the formulae (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and (Ar-55) to (Ar-66) are preferred, in which no more than four, preferably no more than two groups X' stand for N, and particularly preferably all groups X' stand for CR 1<, where preferably at most four, particularly preferably at most three and especially preferably at most two of the groups CR 1<, which X' stands for, are not equal to the group CH.

[0037] In a further embodiment, compounds with partial structures of the formulas (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and (Ar-55) to (Ar-66) are preferred, in which two groups X' stand for N, these groups X being not adjacent.

[0038] In yet another embodiment, compounds with partial structures of the formulas (Ar-55) to (Ar-66) are preferred, in which preferably a maximum of two groups X' stand for N.

[0039] According to a preferred embodiment, the combinations according to the following table are preferred, among others: Partial structure of the formula Partial structure of the formula Number of groups X' that represent N, where these groups X are not adjacent Number of groups X' that represent CR 1<, where the group CR 1< is not equal to the group CH N-1 Ar-2 0 0 to 4, preferably 1 or 2, preferably 1 N-3 Ar-2 0 0 to 4, preferably 1 or 2, preferably 1 N-5 Ar-2 0 0 to 4, preferably 1 or 2, preferably 1 N-6 Ar-2 0 0 to 4, preferably 1 or 2, preferably 1 N-1 Ar-2 2 0 to 2, preferably 1 or 2, preferably 1 N-3 Ar-2 2 0 to 2, preferably 1 or 2, preferably 1 N-5 Ar-2 2 0 to 2, preferably 1 or 2, preferably 1 N-6 Ar-2 2 0 to 2, preferably 1 or 2, preferably 1 N-1 Ar-3 0 0 to 4, preferably 1 or 2, preferably 1 N-3 Ar-3 0 0 to 4, preferably 1 or 2, preferably 1 N-5 Ar-3 0 0 to 4, preferably 1 or 2, preferably 1 N-6 Ar-3 0 0 to 4, preferably 1 or 2, preferably 1 N-1 Ar-3 2 0 to 2, preferably 1 or 2, preferably 1 N-3 Ar-3 2 0 to 2, preferably 1 or 2, preferably 1 N-5 Ar-3 2 0 to 2, preferably 1 or 2, preferably 1 N-6 Ar-3 2 0 to 2, preferably 1 or 2, preferably 1 2 * N-1 Ar-16 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-3 Ar-16 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-5 Ar-16 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-6 Ar-16 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-1 Ar-17 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-3 Ar-17 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-5 Ar-17 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-6 Ar-17 0 0 to 2, preferably 1 or 2, preferably 1 3 * N-1 Ar-18 0 0 3 * N-3 Ar-18 0 0 3 * N-5 Ar-18 0 0 3 * N-6 Ar-18 0 0 2 * N-1 Ar-19 0 0 to 4, preferably 1 or 2, preferably 1 2 * N-3 Ar-19 0 0 to 4, preferably 1 or 2, preferably 1 2 * N-5 Ar-19 0 0 to 4, preferably 1 or 2, preferably 1 2 * N-6 Ar-19 0 0 to 4, preferably 1 or 2, preferably 1 2 * N-1 Ar-19 2 0 to 4, preferably 1 or 2, preferably 1 2 * N-3 Ar-19 2 0 to 4, preferably 1 or 2, preferably 1 2 * N-5 Ar-19 2 0 to 4, preferably 1 or 2, preferably 1 2 * N-6 Ar-19 2 0 to 4, preferably 1 or 2, preferably 1 2 * N-1 Ar-20 0 0 to 4, preferably 1 or 2, preferably 1 2 * N-3 Ar-20 0 0 to 4, preferably 1 or 2, preferably 1 2 * N-5 Ar-20 0 0 to 4, preferably 1 or 2, preferably 1 2 * N-6 Ar-20 0 0 to 4, preferably 1 or 2, preferably 1 2 * N-1 Ar-20 2 0 to 4, preferably 1 or 2, preferably 1 2 * N-3 Ar-20 2 0 to 4, preferably 1 or 2, preferably 1 2 * N-5 Ar-20 2 0 to 4, preferably 1 or 2, preferably 1 2 * N-6 Ar-20 2 0 to 4, preferably 1 or 2, preferably 1 2 * N-1 Ar-21 0 0 to 4, preferably 1 or 2, preferably 1 2 * N-3 Ar-21 0 0 to 4, preferably 1 or 2, preferably 1 2 * N-5 Ar-21 0 0 to 4, preferably 1 or 2, preferably 1 2 * N-6 Ar-21 0 0 to 4, preferably 1 or 2, preferably 1 2 * N-1 Ar-21 2 0 to 4, preferably 1 or 2, preferably 1 2 * N-3 Ar-21 2 0 to 4, preferably 1 or 2, preferably 1 2 * N-5 Ar-21 2 0 to 4, preferably 1 or 2, preferably 1 2 * N-6 Ar-21 2 0 to 4, preferably 1 or 2, preferably 1 2 * N-1 Ar-22 0 0 to 4, preferably 1 or 2, preferably 1 2 * N-3 Ar-22 0 0 to 4, preferably 1 or 2, preferably 1 2 * N-5 Ar-22 0 0 to 4, preferably 1 or 2, preferably 1 2 * N-6 Ar-22 0 0 to 4, preferably 1 or 2, preferably 1 2 * N-1 Ar-22 2 0 to 4, preferably 1 or 2, preferably 1 2 * N-3 Ar-22 2 0 to 4, preferably 1 or 2, preferably 1 2 * N-5 Ar-22 2 0 to 4, preferably 1 or 2, preferably 1 2 * N-6 Ar-22 2 0 to 4, preferably 1 or 2, preferably 1 N-2 Ar-45 0 0 to 4, preferably 1 or 2, preferably 1 N-4 Ar-45 0 0 to 4, preferably 1 or 2, preferably 1 N-2 Ar-45 2 0 to 2, preferably 1 or 2, preferably 1 N-4 Ar-45 2 0 to 2, preferably 1 or 2, preferably 1

[0040] The groups X', which represent CR 1<, where the group CR 1< is not the same as the group CH, are preferably selected from hole-conducting groups and / or electron-conducting groups, where the electron-conducting groups preferably comprise at least two nitrogen atoms in a six-membered ring or in two fused six-membered rings, and are particularly preferably selected from triazines or pyrimidines. Groups that promote TADF (thermally activated delayed fluorescence) are also preferred, depending on the intended use of the compounds of the invention.

[0041] Of the compounds presented above, particular preference is given to compounds which have condensed, particularly preferably areally condensed, aromatic or heteroaromatic ring systems, such as, for example, compounds having partial structures of the formulas (Ar-2), (Ar-3), (Ar-19) to (Ar-22) and (Ar-45).

[0042] For clarity regarding the above combinations, it should be noted that, for example, the combination of a partial structure N-1 with a partial structure Ar-2 results in a compound according to the invention. The same applies to the other combinations.

[0043] Furthermore, it can be provided that the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, to which an aliphatic polycyclic ring system having at least 3 rings is condensed, forms a partial structure of the formulas (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22), (Ar'-45), (Ar'-55) to (Ar'-65): where R 1< has the meaning given above, the index o is 0, 1 or 2, preferably 0 or 1, the index n is 0, 1, 2 or 3, preferably 0, 1 or 2 and the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and the index I is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1 or 2, and the aliphatic polycyclic ring system having at least 3 rings bonds to the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms at each of the positions marked by o to form a ring. Structures of the formula (Ar'-22) are preferred.

[0044] Furthermore, in the partial structures according to the formulas (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22), (Ar'-45) and (Ar'-55) to (Ar'-65) it can be provided that the sum of the indices o, n, m and I is at most 6, preferably at most 4 and particularly preferably at most 2.

[0045] Further preferred are the partial structures according to the formulas (Ar'-55) to (Ar'-65).

[0046] According to a preferred embodiment, the combinations according to the following table are preferred, among others: Partial structure of the formula Partial structure of the formula Index v, t and s in the substructures according to formulas (N-1) to (N-6) Sum of the indices o, n, m and l in the substructures according to the formulas (Ar'-1) to (Ar'-53) N-1 Ar'-2 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 N-3 Ar'-2 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 N-5 Ar'-2 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 N-6 Ar'-2 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 N-1 Ar'-2 0 0 to 2, preferably 1 or 2, preferably 1 N-3 Ar'-2 0 0 to 2, preferably 1 or 2, preferably 1 N-5 Ar'-2 0 0 to 2, preferably 1 or 2, preferably 1 N-6 Ar'-2 0 0 to 2, preferably 1 or 2, preferably 1 N-1 Ar'-3 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 N-3 Ar'-3 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 N-5 Ar'-3 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 N-6 Ar'-3 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 N-1 Ar'-3 0 0 to 2, preferably 1 or 2, preferably 1 N-3 Ar'-3 0 0 to 2, preferably 1 or 2, preferably 1 N-5 Ar'-3 0 0 to 2, preferably 1 or 2, preferably 1 N-6 Ar'-3 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-1 Ar'-16 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 2, preferably 1 or 2, preferably 1 2 * N-3 Ar'-16 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 2, preferably 1 or 2, preferably 1 2 * N-5 Ar'-16 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 2, preferably 1 or 2, preferably 1 2 * N-6 Ar'-16 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 2, preferably 1 or 2, preferably 1 2 * N-1 Ar'-16 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-3 Ar'-16 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-5 Ar'-16 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-6 Ar'-16 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-1 Ar'-17 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 2, preferably 1 or 2, preferably 1 2 * N-3 Ar'-17 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 2, preferably 1 or 2, preferably 1 2 * N-5 Ar'-17 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 2, preferably 1 or 2, preferably 1 2 * N-6 Ar'-17 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 2, preferably 1 or 2, preferably 1 2 * N-1 Ar'-17 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-3 Ar'-17 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-5 Ar'-17 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-6 Ar'-17 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-1 Ar'-18 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 2 * N-3 Ar'-18 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 2 * N-5 Ar'-18 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 2 * N-6 Ar'-18 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 2 * N-1 Ar'-18 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-3 Ar'-18 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-5 Ar'-18 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-6 Ar'-18 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-1 Ar'-19 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 2 * N-3 Ar'-19 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 2 * N-5 Ar'-19 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 2 * N-6 Ar'-19 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 2 * N-1 Ar'-19 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-3 Ar'-19 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-5 Ar'-19 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-6 Ar'-19 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-1 Ar'-20 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 2 * N-3 Ar'-20 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 2 * N-5 Ar'-20 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 2 * N-6 Ar'-20 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 2 * N-1 Ar'-20 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-3 Ar'-20 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-5 Ar'-20 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-6 Ar'-20 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-1 Ar'-21 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 2 * N-3 Ar'-21 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 2 * N-5 Ar'-21 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 2 * N-6 Ar'-21 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 2 * N-1 Ar'-21 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-3 Ar'-21 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-5 Ar'-21 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-6 Ar'-21 0 0 to 2, preferably 1 or 2, preferably 1 2 * N-1 Ar'-22 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 to 3, preferably 2 2 * N-3 Ar'-22 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 to 3, preferably 2 2 * N-5 Ar'-22 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 to 3, preferably 2 2 * N-6 Ar'-22 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 to 3, preferably 2 2 * N-1 Ar'-22 0 0 to 3, preferably 1, 2 or 3, preferably 2 2 * N-3 Ar'-22 0 0 to 3, preferably 1, 2 or 3, preferably 2 2 * N-5 Ar'-22 0 0 to 3, preferably 1, 2 or 3, preferably 2 2 * N-6 Ar'-22 0 0 to 3, preferably 1, 2 or 3, preferably 2 N-2 Ar'-45 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 N-4 Ar'-45 0 to 6, preferably 0 to 3, preferably 0 or 1 0 to 4, preferably 1 or 2, preferably 1 N-2 Ar'-45 0 0 to 2, preferably 1 or 2, preferably 1 N-4 Ar'-45 0 0 to 2, preferably 1 or 2, preferably 1

[0047] The group R 1< in the above combinations, where the group R 1< is not the group H, is preferably selected from hole-conducting groups and / or electron-conducting groups, wherein the electron-conducting groups preferably comprise at least two nitrogen atoms in a six-membered ring or in two fused six-membered rings, and are particularly preferably selected from triazines or pyrimidines. Groups that promote TADF (thermally activated delayed fluorescence) are also preferred, depending on the intended use of the compounds of the invention.

[0048] Of the compounds presented above, particular preference is given to compounds which have condensed, particularly preferably areally condensed, aromatic or heteroaromatic ring systems, such as, for example, compounds having partial structures of the formulae (Ar'-2), (Ar'-3), (Ar'-18) to (Ar'-22) and (Ar'-45), particularly preferably (Ar'-22 and (Ar'-45).

[0049] According to a further embodiment of the present invention, compounds comprising fluorene, dibenzofuran, dibenzothiofuran, carbazole, spirobifluorene and similar structures are preferred.

[0050] In a further embodiment, it can be provided that the compound which can be used as an active compound in an organic electronic device comprises a condensed aromatic or heteroaromatic ring system with at least 2, preferably three condensed rings, which may optionally be substituted.

[0051] According to a further embodiment, it can be provided that the compound which can be used as an active compound in an organic electronic device comprises a hole-transport group, wherein preferably in a structure according to the formulas (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and / or (Ar'-1), (Ar'-2), (Ar'-16) to (Ar'-22) and (Ar'-45) a group R 1< comprises, preferably represents, a hole-transport group. Hole-transport groups are known in the art, and these preferably comprise triarylamine or carbazole groups.

[0052] Preferably, it can be provided that the hole transport group comprises a group, preferably represents a group selected from the formulas (H-1) to (H-3), where the dashed bond marks the attachment position and Ar 2< , Ar 3< , Ar 4< are each independently an aryl group having 6 to 40 C atoms or a heteroaryl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 1<; p is 0 or 1, and Z is 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, SO 2 , Se, O or S, preferably a bond or C(R 1< ) 2 , NR 1< , O or S, where the symbols Ar 1< and R 1< have the meaning given above. In this case, the substituents R 1< in the structures of formulae (H-1) to (H-3) in structures according to formulae (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22) and (Ar'-45) are to be replaced by substituents R 2<. Furthermore, the presence of an N-N bond is preferably excluded.

[0053] Furthermore, it can be provided that the hole transport group comprises a group, preferably represents a group selected from the formulas (H-4) to (H-26), where Y 1< represents O, S, C(R 1< ) 2 , NR 1< or NAr 1<, the dashed bond marks the attachment position, e is 0, 1 or 2, j is 0, 1, 2 or 3, h is the same or different on each occurrence and is 0, 1, 2, 3 or 4, p is 0 or 1, Ar 1< and R 1< have the meanings given above and Ar 2< have the meanings given above, in particular for formula (H-1) or (H-2). In this case, the substituents R 1< in the structures of formulae (H-3) to (H-26) in structures according to formulae (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and (Ar-55) to (Ar-66) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22) and (Ar'-45) are to be replaced by substituents R 2<. Furthermore, the presence of an N-N bond is preferably excluded.

[0054] From the above formulation it can be seen that if the index p = 0, the corresponding group Ar 2< is not present and a bond is formed.

[0055] Preferably, the group Ar 2< can form a continuous conjugation with the aromatic or heteroaromatic radical or the nitrogen atom to which the group Ar 2< can be bonded according to the formulas (H-1) to (H-26).

[0056] In a further preferred embodiment of the invention, Ar 2< represents an aromatic or heteroaromatic ring system having 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system having 6 to 12 carbon atoms, which may be substituted by one or more radicals R 1<, but is preferably unsubstituted, where R 1< may have the meaning given above. Particularly preferably, Ar 2< represents an aromatic ring system having 6 to 10 aromatic ring atoms or a heteroaromatic ring system having 6 to 13 heteroaromatic ring atoms, each of which may be substituted by one or more radicals R 1<, but is preferably unsubstituted, where R 1< may have the meaning given above.

[0057] Furthermore, the symbol Ar 2< shown inter alia in formulae (H-1) to (H-26) preferably represents an aryl or heteroaryl radical having 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 ring atoms, so that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is bonded directly, ie via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group.

[0058] Furthermore, it can be provided that the group Ar 2< shown in formulas (H-1) to (H-26) comprises an aromatic ring system with at most two fused aromatic and / or heteroaromatic 6-membered rings, preferably not a fused aromatic or heteroaromatic ring system with fused 6-membered rings. Accordingly, naphthyl structures are preferred over anthracene structures. Furthermore, fluorenyl, spirobifluorenyl, dibenzofuranyl, and / or dibenzothienyl structures are preferred over naphthyl structures. Particular preference is given to structures that do not exhibit condensation, such as, for example, phenyl, biphenyl, terphenyl, and / or quaterphenyl structures.

[0059] Furthermore, it can be provided that the group Ar 2< set out inter alia in formulas (H-1) to (H-26) has at most 1 nitrogen atom, preferably at most 2 heteroatoms, particularly preferably at most one heteroatom and particularly preferably no heteroatom.

[0060] In a further preferred embodiment of the invention, Ar 3< and / or Ar 4<, identically or differently on each occurrence, represents an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, particularly preferably an aromatic ring system having 6 to 12 aromatic ring atoms or a heteroaromatic ring system having 6 to 13 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1<, but is preferably unsubstituted, where R 1< may have the meaning shown above.

[0061] In a further preferred embodiment, it can be provided that the compound which can be used as an active compound in an organic electronic device comprises a radical comprising an electron transport group, wherein preferably in a structure according to the formulas (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) ) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22) and (Ar'-45) a group R 1< comprises, preferably represents, a radical comprising an electron transport group. Electron transport groups are widely known in the art and promote the ability of compounds to transport and / or conduct electrons.

[0062] Furthermore, compounds that can be used as active compounds in an organic electronic device 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.

[0063] In a preferred embodiment of the present invention, it can be provided that the electron transport group-comprising radical represents a group which can be represented by the formula (QL), wherein L 1< represents a bond or an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 1<, Q is an electron transport group, where R 1< has the meaning given above, and the bond marks the attachment position. In this case, the substituents R 1< in the structure of formula (QL) in structures according to formulae (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22) and (Ar'-45) are to be replaced by substituents R 2<.

[0064] Preferably, the group L 1< can form a continuous conjugation with the group Q and the atom, preferably the carbon or nitrogen atom, to which the group L 1< is bonded according to formula (QL). Continuous conjugation of the aromatic or heteroaromatic systems is formed as soon as direct bonds are formed between adjacent aromatic or heteroaromatic rings. A further linkage between the aforementioned conjugated groups, for example, via an S, N, or O atom or a carbonyl group, does not harm the conjugation.In a fluorene system, the two aromatic rings are directly bonded, whereby the sp 3< hybridized carbon atom in position 9 prevents condensation of these rings, but conjugation can occur because this sp 3< 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 other structural elements of a compound according to the invention. In contrast, in a second spirobifluorene structure, continuous conjugation can be formed if the connection between the group Q and the aromatic or heteroaromatic radical to which the group L 1< according to formula (QL) is bonded occurs via the same phenyl group of the spirobifluorene structure or via phenyl groups of the spirobifluorene structure that are directly bonded to one another and lie in one plane.If the connection between the group Q and the aromatic or heteroaromatic residue to which the group L 1< is bonded according to formula (QL) is made via different phenyl groups of the second spirobifluorene structure, which are connected via the sp 3< hybridized carbon atom in position 9, the conjugation is interrupted.

[0065] In a further preferred embodiment of the invention, L 1< represents a bond or an aromatic or heteroaromatic ring system having 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system having 6 to 12 carbon atoms, which may be substituted by one or more radicals R 1<, but is preferably unsubstituted, where R 1< may have the meaning given above. Particularly preferably, L 1< represents an aromatic ring system having 6 to 10 aromatic ring atoms or a heteroaromatic ring system having 6 to 13 heteroaromatic ring atoms, each of which may be substituted by one or more radicals R 2<, but is preferably unsubstituted, where R 2< may have the meaning given above.

[0066] Furthermore, the symbol L 1< shown inter alia in formula (QL) preferably represents, identically or differently on each occurrence, a bond or an aryl or heteroaryl radical having 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 ring atoms, so that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is bonded directly, ie via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group.

[0067] Furthermore, it can be provided that the group L 1< shown in formula (QL) comprises an aromatic ring system with at most two fused aromatic and / or heteroaromatic 6-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.

[0068] Particularly preferred are structures that do not exhibit condensation, such as phenyl, biphenyl, terphenyl and / or quaterphenyl structures.

[0069] Examples of suitable aromatic or heteroaromatic ring systems L 1< are selected from the group consisting of ortho-, meta- or para-phenylene, ortho-, meta- or para-biphenylene, terphenylene, in particular branched terphenylene, quaterphenylene, in particular branched quaterphenylene, fluorenylene, spirobifluorenylene, dibenzofuranylene, dibenzothienylene and carbazolylene, which may each be substituted by one or more radicals R 1<, but are preferably unsubstituted.

[0070] Furthermore, it can be provided that the group L 1< set out inter alia in formula (QL) has at most 1 nitrogen atom, preferably at most 2 heteroatoms, particularly preferably at most one heteroatom and particularly preferably no heteroatom.

[0071] Preferably, the group Q shown inter alia in the formula (QL) or the electron transport group can be selected from structures of the formulas (Q-1), (Q-2), (Q-4), (Q-4), (Q-5), (Q-6), (Q-7), (Q-8), (Q-9) and / or (Q-10) where the dashed bond marks the attachment position, Q' at each occurrence, identically or differently, represents CR 1< or N, and Q" represents NR 1< , O or S; where at least one Q' is equal to N and R 1< as defined previously.

[0072] The substituents R 1< in the structures of formulae (Q-1) to (Q-10) are to be replaced by substituents R 2< in structures according to formulae (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22) and (Ar'-45).

[0073] Furthermore, the group Q shown inter alia in the formula (QL) or the electron transport group can preferably be selected from a structure of the formulas (Q-11), (Q-12), (Q-13), (Q-14) and / or (Q-15) where the symbol R 1< has the meaning given above, X' is N or CR 1< and the dashed bond marks the attachment position, where X' preferably represents a nitrogen atom. The substituents R 1< in the structures of formulae (Q-11) to (Q-15) are to be replaced by substituents R 2< in structures according to formulae (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22) and (Ar'-45).

[0074] In a further embodiment, the group Q shown inter alia in the formula (QL) or the electron transport group can be selected from structures of the formulas (Q-16), (Q-17), (Q-18), (Q-19), (Q-20), (Q-21) and / or (Q-22) wherein the symbol R 1< has the meaning set out above, the dashed bond marks the attachment 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 the formulas (Q-16), (Q-17), (Q-18) and (Q-19) are preferred. Furthermore, the substituents R 1< in the structures of the formulas (Q-16) to (Q-22) in structures according to formulas (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22) and (Ar'-45) are to be replaced by substituents R 2<.

[0075] In a further embodiment, the group Q shown inter alia in the formula (QL) or the electron transport group can be selected from structures of the formulas (Q-23), (Q-24) and / or (Q-25), wherein the symbol R 1< has the meaning previously defined and the dashed bond marks the attachment position. Furthermore, the substituents R 1< in the structures of formulas (Q-23) to (Q-25) in structures according to formulas (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22) and (Ar'-45) are to be replaced by substituents R 2<.

[0076] In a further embodiment, the group Q shown inter alia in the formula (QL) or the electron transport group can be selected from structures of the formulas (Q-26), (Q-27), (Q-28), (Q-29) and / or (Q-30), where symbols Ar 1< and R 1< have the meaning given above, X' is N or CR 1< and the dashed bond marks the attachment position. Preferably, in the structures of formulae (Q-26), (Q-27) and (Q-28) exactly one X' represents a nitrogen atom. Furthermore, the substituents R 1< in the structures of formulae (Q-26) to (Q-30) in structures according to formulae (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22) and (Ar'-45) are to be replaced by substituents R 2<.

[0077] Preferably, the group Q shown inter alia in the formula (QL) or the electron transport group can be selected from structures of the 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), wherein the symbols Ar 1< and R 1< have the meaning set out above, the dashed bond marks the attachment 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 this case, the substituents R 1< in the structures of formulae (Q-31) to (Q-44) in structures according to formulae (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22) and (Ar'-45) are to be replaced by substituents R 2<.

[0078] In a further preferred embodiment of the invention, Ar 1< is identical or different on each occurrence and represents an aromatic or heteroaromatic ring system, preferably an aryl or heteroaryl radical having 5 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, particularly preferably an aromatic ring system, preferably an aryl radical having 6 to 12 aromatic ring atoms or a heteroaromatic ring system, preferably a heteroaryl group having 5 to 13 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2<, but is preferably unsubstituted, where R 2< may have the meaning shown above.

[0079] Preferably, the symbol Ar 1< represents an aryl or heteroaryl radical, so that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is bonded directly, ie 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 represented groups (H-1) to (H-26) or (Q-26) to (Q-44).

[0080] Advantageously, Ar 1< in the formulas (H-1) to (H-26) or (Q-26) to (Q-44) represents an aromatic ring system having 6 to 12 aromatic ring atoms, which may be substituted by one or more radicals R 2<, but is preferably unsubstituted, where R 2< may have the meaning shown above.

[0081] Preferably, the radicals R 1< or R 2< in formulas (H-1) to (H-26) or (Q-1) to (Q-44) do not form a fused ring system with the ring atoms of the aryl group or heteroaryl group Ar 1< , Ar 2< , Ar 3< and / or Ar 4< to which the radicals R 1< or R 2< are bonded. This includes the formation of a fused ring system with possible substituents R 2< , R 3< that may be bonded to the radicals R 1< or R 2<.

[0082] Furthermore, it can be provided that the group Ar, Ar 1< , Ar 2< , Ar 3< and / or Ar 4< is 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, imimidazolyl, benzimidazolyl, benzoxazolyl, benzthiazolyl, 1-, 2-, 3- or 4-carbazolyl, indenocarbazolyl, 1- or 2-naphthyl, Anthracenyl, preferably 9-anthracenyl, phenanthrenyl and / or triphenylenyl, each of which may be substituted by one or more radicals R 1< and / or R 2<, but is preferably unsubstituted, with phenyl, spirobifluorene, fluorene, dibenzofuran, dibenzothiophene, anthracene, phenanthrene, triphenylene groups being particularly preferred.

[0083] If X or X 1< stands for CR 1< or if the aromatic and / or heteroaromatic groups are substituted by substituents R 1<, then these substituents R 1< are preferably selected 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 having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms or an alkenyl group having 2 to 10 C atoms, each of which may be substituted by one or more radicals R 2<, where one or more non-adjacent CH 2 groups may be replaced by O and where 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 of which may be substituted by one or more radicals R 2<, but is preferably unsubstituted, or an aralkyl or heteroaralkyl group with 5 to 25 aromatic ring atoms,which may be substituted by one or more radicals R 2<; optionally two substituents R 1<, which are preferably bonded to adjacent carbon atoms, may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more radicals R 1<, where the group Ar 1< has the meaning given above.,

[0084] These substituents R 1< are particularly preferably selected from the group consisting of H, D, F, CN, N(Ar 1< ) 2 , a straight-chain alkyl group having 1 to 8 C atoms, preferably having 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group having 3 to 8 C atoms, preferably having 3 or 4 C atoms, or an alkenyl group having 2 to 8 C atoms, preferably having 2, 3 or 4 C atoms, each of which may be substituted by one or more radicals R 2<, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, particularly preferably having 6 to 13 aromatic ring atoms, each of which may be substituted by one or more non-aromatic radicals R 1< may be substituted, but is preferably unsubstituted;optionally two substituents R 1<, preferably which are bonded to adjacent carbon atoms, can form a monocyclic or polycyclic, aliphatic ring system which can be substituted by one or more radicals R 2<, but is preferably unsubstituted, where Ar 1< can have the meaning set out above.;

[0085] Most preferably, the substituents R 1< are selected from the group consisting of H or an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, preferably having 6 to 13 aromatic ring atoms, which may each be substituted by one or more non-aromatic radicals R 2<, but is preferably unsubstituted. Examples of suitable substituents R 1< 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, 1-, 2-, 3- or 4-dibenzothienyl, 1-, 2-, 3- or 4-carbazolyl and indenocarbazolyl, which may each be substituted by one or more radicals R 2<, but are preferably unsubstituted.

[0086] Furthermore, it can be provided that the substituents R 1< of the heteroaromatic ring system according to the formulas (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22) and (Ar'-45) do not form a fused aromatic or heteroaromatic ring system, preferably not a fused ring system, with the ring atoms of the aromatic or heteroaromatic ring system. This includes the formation of a fused ring system with possible substituents R 2< , R 3<, which can be bonded to the radicals R 1<.

[0087] Furthermore, it can be provided that in a structure according to formula (I) to (XVIII), (Ia) to (XVIIIa), (N-1) to (N-6), (Ar-2) (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22) and (Ar'-45) at least one radical R 1< or Ar 1< represents a group selected from the formulas (R 1< -1) to (R 1< - 92), or in a structure according to formula (H-1) to (H-26), (Q-1) to (Q-44) at least one radical Ar 1< or R 1< represents a group selected from the formulas (R 1< -1) to (R 1< - 92): where the symbols used are: Y 1< is O, S or NR 2< , preferably O or S; k is independently 0 or 1 at each occurrence; i is independently 0, 1 or 2 at each occurrence; j is independently 0, 1, 2 or 3 at each occurrence; h is independently 0, 1, 2, 3 or 4 at each occurrence; g is independently 0, 1, 2, 3, 4 or 5 at each occurrence; R 2< can have the meaning given above and the dashed bond marks the attachment position.

[0088] The groups of the formulae R 1< -1 to R 1< -54 are preferred, with the groups R 1< -1, R'-3, R 1< -5, R'-6, R'-15, R 1< -29, R'-30, R 1< -31, R'-32, R 1< -33, R 1< -38, R'-39, R 1< -40, R 1< -41, R 1< -42, R 1< -43, R 1< -44 and / or R 1< -45 being particularly preferred.

[0089] 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< -92) is in each case at most 3, preferably at most 2 and particularly preferably at most 1.

[0090] Preferably, the R 2< radicals in the formulas (R 1< -1) to (R 1< -92) do not form a fused aromatic or heteroaromatic ring system with the ring atoms of the aryl group or heteroaryl group to which the R 2< radicals are bonded, preferably not a fused ring system. This includes the formation of a fused ring system with possible R 3< substituents that may be bonded to the R 2< radicals.

[0091] The previously presented radicals of the formulas (R 1< -1) to (R 1< -92) represent preferred radicals Ar 3< , Ar 4< according to formulas (H-1) to (H-3) or preferred embodiments of these formulas, in which case the groups R 2< presented in the formulas (R 1< -1) to (R 1< -92) are to be replaced by radicals R 1<. The previously presented preferences with regard to the formulas (R 1< -1) to (R 1< -92) apply accordingly.

[0092] Preferred are compounds comprising at least one structure of the formulae (H-1) to (H-26) in which the group Ar 2< represents a group selected from the formulae (L 1< -1) to (L 1< -108), and / or compounds comprising structures of the formula (QL) in which the group L 1< represents a bond or a group selected from the formulae (L 1< -1) to (L 1< -108) where the dashed bonds each mark the attachment positions, the index k is 0 or 1, the index I is 0, 1 or 2, the index j is independently 0, 1, 2 or 3 at each occurrence; the index h is independently 0, 1, 2, 3 or 4 at each occurrence, the index g is 0, 1, 2, 3, 4 or 5; the symbol Y 1< is O, S or NR 1< , preferably O or S; and the symbol R 1< has the meaning given above.

[0093] Preferably, it can be provided that the sum of the indices k, l, g, h and j in the structures of the formula (L 1< -1) to (L 1< -108) is in each case at most 3, preferably at most 2 and particularly preferably at most 1.

[0094] Preferred compounds according to the invention having a group of the 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< -78) and / or (L 1< -92) to (L 1< -108), preferably of the formula (L 1< -1) to (L 1< -54) and / or (L 1< -92) to (L 1< -108), especially preferably of the formula (L 1< -1) to (L 1< -29) and / or (L 1< -92) to (L 1< -103). Advantageously, the sum of the indices k, l, g, h and j in the structures of the formulas (L 1< -1) to (L 1< -78) and / or (L 1< -92) to (L 1< -108), preferably of the formula (L 1< -1) to (L 1< -54) and / or (L 1< -92) to (L 1< -108), especially preferably of the formula (L 1< -1) to (L 1< -29) and / or (L 1< -92) to (L 1< -103) can each be at most 3, preferably at most 2 and particularly preferably at most 1.

[0095] Preferred compounds according to the invention having a group of the formula (QL) comprise a group L 1< which represents a bond or which is selected from one of the formulae (L 1< -1) to (L 1< -78) and / or (L 1< -92) to (L 1< -108), preferably of the formula (L 1< -1) to (L 1< -54) and / or (L 1< -92) to (L 1< -108), especially preferably of the formula (L 1< -1) to (L 1< -29) and / or (L 1< -92) to (L 1< -103). Advantageously, the sum of the indices k, l, g, h and j in the structures of the formulas (L 1< -1) to (L 1< -78) and / or (L 1< -92) to (L 1< -108), preferably of the formula (L 1< -1) to (L 1< -54) and / or (L 1< -92) to (L 1< -108), especially preferably of the formula (L 1< -1) to (L 1< -29) and / or (L 1< -92) to (L 1< -103) can each be at most 3, preferably at most 2 and particularly preferably at most 1.

[0096] Preferably, the R 2< radicals in the formulas (L 1< -1) to (L 1< -108) do not form a fused aromatic or heteroaromatic ring system with the ring atoms of the aryl group or heteroaryl group to which the R 2< radicals are bonded, preferably not a fused ring system. This includes the formation of a fused ring system with possible R 3< substituents that may be bonded to the R 2< radicals.

[0097] According to a preferred embodiment, compounds according to the invention which can be used as an active compound in an organic electronic device are selected from the group of phenyls, 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, fluoradenes.

[0098] According to a preferred embodiment, compounds according to the invention can be prepared by a combination of the partial structures according to the formulas (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22) and (Ar'-45). Preferably, compounds which can be used as an active compound in an organic electronic device, preferably compounds which can be obtained by a combination of the partial structures according to the formulas (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22) and (Ar'-45), 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 very particularly preferably less than or equal to 1200 g / mol.

[0099] Furthermore, preferred compounds according to the invention are characterized by their sublimability. These compounds generally have a molecular weight of less than approximately 1200 g / mol.

[0100] If the compound according to the invention is substituted with aromatic or heteroaromatic groups R 1< or R 2<, it is preferred if these do not contain any aryl or heteroaryl groups with more than two directly fused aromatic six-membered rings. Particularly preferably, the substituents do not contain any aryl or heteroaryl groups with directly fused aromatic six-membered rings. 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 also suitable according to the invention are phenanthrene and triphenylene, since these also have a high triplet level.

[0101] When designing the compounds according to the invention which can be used as an active compound in an organic electronic device, for use as a fluorescent emitter or as blue OLED materials, preferred compounds can contain corresponding groups, for example fluorene, anthracene and / or pyrene groups, which can be substituted by groups R 1< or R 2< or which are formed by corresponding substitution of the groups (R 1< -1) to (R 1< -95), preferably (R 1< -33) to (R 1< -57) and (R 1< -76) to (R'-86), or (L 1< -1) to (L 1< -109), preferably (L 1< -30) to (L 1< -60) and (L 1< -71) to (L 1< -91), with the substituents R 2<.

[0102] In a further preferred embodiment of the invention, R 2< , for example in the structures in which reference is made to these formulas, is selected on each occurrence, identically or differently, from the group consisting of H, D, an aliphatic hydrocarbon radical having 1 to 10 C atoms, preferably having 1, 2, 3 or 4 C atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, preferably having 5 to 24 aromatic ring atoms, particularly preferably having 5 to 13 aromatic ring atoms, which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms, but is preferably unsubstituted.

[0103] Preferably, the R 2< radicals do not form a fused aromatic or heteroaromatic ring system with the ring atoms of the aryl group or heteroaryl group to which the R 2< radicals are bonded, preferably not a fused ring system. This includes the formation of a fused ring system with possible R 3< substituents that may be bonded to the R 2< radicals.

[0104] In a further preferred embodiment of the invention, R 3< , for example in the structures in which reference is made to these formulas, is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 10 C atoms, preferably having 1, 2, 3 or 4 C atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, preferably having 5 to 24 aromatic ring atoms, particularly preferably having 5 to 13 aromatic ring atoms, which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms, but is preferably unsubstituted.

[0105] In a further embodiment of the present invention, compounds are preferred which are obtained by a combination of two partial structures N-1 and one partial structure Ar-23, wherein a total of at most 6, preferably at most 4 and especially preferably at most 2 radicals of the formula X' are not CH or CD, which have the following properties: R 1< , not equal to H or D preferably At least one R 1< preferably R 1< -1 to R 1< -95 R 1< -1 to R 1< -54 H-1 to H-26 H1 R 1< -1 to R 1< -95 R 1< -1 to R 1< -54 H-1 to H-26 H4 or H-5 R 1< -1 to R 1< -4 R 1< -1 R 1< -1 to R 1< -54 H1 R 1< -1 to R 1< -4 R 1< -1 H-1 to H-26 H4 or H-5 R 1< -1 to R 1< -95 R 1< -1 to R 1< -54 QL Q-11 to Q-19, Q-23 to Q-28, Q-31 to Q-42 R 1< -1 to R 1< -4 R 1< -1 QL Q-11 to Q-19

[0106] In a further embodiment of the present invention, compounds are preferred which are obtained by a combination of two partial structures N-1 and one partial structure Ar-22', wherein the sum of the indices v, o and m is at most 5, preferably at most 3 and especially preferably 2, wherein the index v is especially preferably 0, which have the following properties: R 1< , not equal to H or D preferably At least one R 1< preferably R 1< -1 to R 1< -95 R 1< -1 to R 1< -54 H-1 to H-26 H1 R 1< -1 to R 1< -95 R 1< -1 to R 1< -54 H-1 to H-26 H4 or H-5 R 1< -1 to R 1< -4 R 1< -1 R 1< -1 to R 1< -54 H1 R 1< -1 to R 1< -4 R 1< -1 H-1 to H-26 H4 or H-5 R 1< -1 to R 1< -95 R 1< -1 to R 1< -54 QL Q-11 to Q-19, Q-23 to Q-28, Q-31 to Q-42 R 1< -1 to R 1< -4 R 1< -1 QL Q-11 to Q-19

[0107] Furthermore, it can be provided that the compound which can be used as an active compound in an organic electronic device is not in direct contact with a metal atom, preferably does not represent a ligand for a metal complex.

[0108] Examples of suitable compounds according to the invention are the structures shown below according to the following formulas 1 to 108: Formula 1* Formula 2* Formula 3* Formula 4* Formula 5* Formula 6* Formula 7* Formula 8* Formula 9* Formula 10* Formula 11* Formula 12* Formula 13* Formula 14* Formula 15* Formula 16* Formula 17* Formula 18* Formula 19* Formula 20* Formula 21* Formula 22* Formula 23* Formula 24* Formula 25* Formula 26* Formula 27* Formula 28* Formula 29* Formula 30* Formula 31* Formula 32* Formula 33* Formula 34* Formula 35* Formula 36* Formula 37* Formula 38* Formula 39* Formula 40 Formula 41 Formula 42 Formula 43* Formula 44* Formula 45* Formula 46* Formula 47* Formula 48* Formula 49* Formula 50* Formula 51* Formula 52* Formula 53* Shapes 54* Formula 55* Formula 56* Formula 57* Formula 58* Formula 59* Formula 60 Formula 61* Formula 62* Formula 63 Formula 64 Formula 65* Formula 66* Formula 67* Formula 68* Formula 69* Formula 70* Formula 71* Formula 72 Formula 73* Formula 74* Formula 75* Formula 76* Formula 77* Formula 78* Formula 79 Formula 80 Formula 81 Formula 82 Formula 83 Formula 84 Formula 85 Formula 86 Formula 87 Formula 88 Formula 89 Formula 90 Formula 91 Formula 92 Formula 93 Formula 94* Formula 95* Formula 96* Formula 97* Formula 98* Formula 99* Formula 100 Formula 101 Formula 102 Formula 103 Formula 104 Formula 105 Formula 106 Formula 107 Formula 108 *non-inventive examples

[0109] The structures of formulas 1 to 18 are suitable, among other things, as hole-transport materials (HTM) and, optionally, as electron-blocking materials (EMB). The structures of formulas 1 to 33 are suitable, among other things, as triplet matrix materials (TMMs), in particular for phosphorescent emitters, and as matrix materials for TADF compounds. The structures of formulas 34 to 45 are particularly suitable as wide-band gap materials. The structures of formulas 46 to 60 are particularly suitable as electron-transport materials (ETMs) and as electron-conducting triplet matrix materials (eTMMs). The structures of formulas 61 to 67 are particularly suitable as matrix materials for fluorescent emitters (SMBs). The structures of formulas 67 to 93 are particularly suitable as fluorescent emitters (SEBs). The structures of formulas 94 to 105 are particularly suitable as emitters that exhibit TADF (thermally activated delayed fluorescence) and as TADF compounds in hyperfluorescences

[0110] Preferred embodiments of compounds according to the invention are explained 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.

[0111] Provided that the conditions stated in claim 1 are met, the above-mentioned preferred embodiments can be combined with one another as desired. In a particularly preferred embodiment of the invention, the above-mentioned preferred embodiments apply simultaneously.

[0112] The compounds of the invention can, in principle, be prepared by various methods. However, the methods described below have proven particularly suitable.

[0113] Therefore, a further subject of the present invention is a process for preparing the compounds according to the invention, in which a compound comprising at least one aliphatic polycyclic ring system having at least 3 rings is combined with a compound comprising at least one aromatic or heteroaromatic group in a coupling reaction.

[0114] Suitable compounds comprising at least one aliphatic polycyclic ring system having at least 3 rings can often be obtained commercially, the starting compounds presented in the examples being obtainable by known processes, so that reference is made thereto.

[0115] These compounds can be reacted with other compounds comprising at least one aromatic or heteroaromatic group by known coupling reactions, the necessary conditions for this being known to the person skilled in the art and detailed information in the examples assisting the person skilled in the art in carrying out these reactions.

[0116] Particularly suitable and preferred coupling reactions, all of which lead to CC and / or CN bond formations, are those according to BUCHWALD, SUZUKI, YAMAMOTO, STILLE, HECK, NEGISHI, SONOGASHIRA, and HIYAMA. These reactions are widely known, and the examples provide further guidance to the skilled person.

[0117] The principles of the preparation processes described above are, in principle, known from the literature for similar compounds and can be easily adapted by a person skilled in the art to prepare the compounds of the invention. Further information can be found in the examples.

[0118] By these processes, optionally followed by purification, such as recrystallization or sublimation, the compounds according to the invention can be obtained in high purity, preferably more than 99% (determined by 1< H-NMR and / or HPLC).

[0119] The compounds according to the invention can also have suitable substituents, for example, longer alkyl groups (approx. 4 to 20 C atoms), in particular branched alkyl groups, or optionally substituted aryl groups, for example xylyl, mesityl, or branched terphenyl or quaterphenyl groups, which impart solubility in common organic solvents, so that the compounds are soluble, for example, in toluene or xylene at room temperature in sufficient concentration to enable processing from solution. These soluble compounds are particularly suitable for processing from solution, for example by printing processes. Furthermore, it should be noted that the compounds according to the invention already possess increased solubility in these solvents.

[0120] The compounds according to the invention can also be mixed with a polymer. It is also possible to incorporate these compounds covalently into a polymer. This is particularly possible with compounds substituted by reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic acid esters, or by 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 takes place 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.

[0121] The invention therefore further provides oligomers, polymers, or dendrimers comprising one or more compounds according to the invention, wherein one or more bonds of the compounds according to the invention to the polymer, oligomer, or dendrimer are present. Depending on the linkage 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. The same preferences apply to the repeating units of the compounds according to the invention in oligomers, dendrimers, and polymers as described above.

[0122] To prepare the oligomers or polymers, the monomers of the invention are homopolymerized or copolymerized with other monomers. Copolymers are preferred, with the preferred embodiments described above and below being present in amounts of 0.01 to 99.9 mol%, preferably 5 to 90 mol%, 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.

[0123] Of particular interest are also compounds according to the invention which are characterized by a high glass transition temperature. In this context, compounds according to the invention which can be used as an active compound in an organic electronic device are particularly preferred, preferably compounds which are obtainable by a combination of the partial structures according to the formulas (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22) and (Ar'-45) or the preferred embodiments described above and below, which have a glass transition temperature of at least 70°C, more preferably of at least 110°C, most preferably of at least 125°C, and especially preferably of at least 150°C, determined according to DIN 51005 (version 2005-08).

[0124] For processing the compounds of the invention from the liquid phase, for example by spin coating or printing processes, formulations of the compounds of the invention are required. These formulations can be, for example, solutions, dispersions, or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, 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, methyl benzoate, NMP,p-Cymene, phenetole, 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, hexamethylindane or mixtures of these solvents.

[0125] The present invention therefore further provides a formulation comprising a compound according to the invention and at least one further compound. The further compound can, for example, be a solvent, in particular one of the abovementioned solvents or a mixture of these solvents. However, the further compound can also be at least one further organic or inorganic compound which is also used in the electronic device, for example an emitting compound, for example a fluorescent dopant, a phosphorescent dopant or a compound which exhibits TADF (thermally activated delayed fluorescence), in particular a phosphorescent dopant, and / or a further matrix material. This further compound can also be polymeric.

[0126] The present invention therefore further provides a composition comprising a compound according to the invention and at least one further organic functional material. Functional materials are generally the organic or inorganic materials introduced between the anode and cathode. The organic functional material is preferably 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 conductor materials, hole injection materials, electron blocking materials, hole blocking materials, wide-band gap materials, and n-dopants.

[0127] The present invention therefore also relates to a composition comprising at least one compound according to the invention, preferably a compound of the preferred embodiments described above and below, and at least one further matrix material. According to a particular aspect of the present invention, the further matrix material has hole-transporting properties.

[0128] The present invention further provides a composition comprising at least one compound according to the invention, preferably a compound of the preferred embodiments described above and below, and at least one wide-band gap material, wherein wide-band gap material is understood to mean a material within the meaning of the disclosure of US Pat. No. 7,294,849. These systems exhibit particularly advantageous performance data in electroluminescent devices.

[0129] Preferably, the additional compound can have a band gap of 2.5 eV or more, preferably 3.0 eV or more, most preferably 3.5 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).

[0130] Molecular orbitals, in particular the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), their energy levels, and the energy of the lowest triplet state T1 and the lowest excited singlet state S1 of the materials are determined using quantum chemical calculations. For the calculation of organic substances without metals, a geometry optimization is first performed using the "Ground State / Semi-empirical / Default Spin / AM1 / Charge 0 / Spin Singlet" method. Subsequently, an energy calculation is performed based on the optimized geometry. The "TD-SCF / DFT / Default Spin / B3PW91" method with the "6-31G(d)" basis set is used (Charge 0, Spin Singlet). For metal-containing compounds, the geometry is optimized using the "Ground State / Hartree-Fock / Default Spin / LanL2MB / Charge 0 / Spin Singlet" method.The energy calculation is performed analogously 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. The energy calculation yields the HOMO energy level HEh and the LUMO energy level LEh in Hartree units. From this, the HOMO and LUMO energy levels, calibrated using cyclic voltammetry measurements, are determined in electronvolts as follows: . HOMO(eV) = ((HEh*27.212)-0.9899) / 1.1206 LUMO(eV) = ((LEh*27.212)-2.0041) / 1.385

[0131] For the purposes of this application, these values ​​are to be regarded as HOMO or LUMO energy levels of the materials.

[0132] The lowest triplet state T 1 is defined as the energy of the triplet state with the lowest energy resulting from the quantum chemical calculation described.

[0133] The lowest excited singlet state S 1 is defined as the energy of the excited singlet state with the lowest energy resulting from the described quantum chemical calculation.

[0134] The method described here is independent of the software package used and always produces the same results. Examples of commonly used programs for this purpose are "Gaussian09W" (Gaussian Inc.) and Q-Chem 4.1 (Q-Chem, Inc.).

[0135] The present invention also relates to a composition comprising at least one compound comprising structures according to formulas (I) to (XVIII) or the preferred embodiments described above and below, and at least one phosphorescent emitter, wherein the term phosphorescent emitter is also understood to include phosphorescent dopants.

[0136] In a system containing a matrix material and a dopant, a dopant is understood to be the component whose proportion in the mixture is the smaller. Similarly, in a system containing a matrix material and a dopant, a matrix material is understood to be the component whose proportion in the mixture is the larger.

[0137] Preferred phosphorescent dopants for use in matrix systems, preferably mixed matrix systems, are the preferred phosphorescent dopants listed below.

[0138] The term phosphorescent dopants typically includes compounds in which light emission occurs through 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.

[0139] Particularly suitable phosphorescent compounds (= triplet emitters) are compounds which, upon suitable excitation, emit light, preferably in the visible range, and which also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80, in particular a metal with this atomic number. Preferably, compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are used as phosphorescence emitters, in particular compounds containing iridium or platinum. For the purposes of the present invention, all luminescent compounds containing the above-mentioned metals are regarded as phosphorescent compounds.

[0140] Examples of the emitters described above can be found in applications WO 00 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 05 / 033244, WO 05 / 019373, US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, WO 2010 / 102709, WO 2011 / 032626, WO 2011 / 066898, WO 2011 / 157339, WO 2012 / 007086, WO 2014 / 008982, WO 2014 / 023377, WO 2014 / 094961, WO 2014 / 094960, WO 2015 / 036074, WO 2015 / 104045, WO 2015 / 117718, WO 2016 / 015815, WO 2016 / 124304, WO 2016124304, WO 2017032439, WO 2018019687, WO 2018019688, WO 2018041769, WO 2018054798, WO 2018069196, WO 2018069197, WO 2018069273.In general, all phosphorescent complexes as used according to the prior art for phosphorescent OLEDs and as known to the person skilled in the art in the field of organic electroluminescence are suitable, and the person skilled in the art can use further phosphorescent complexes without inventive step.

[0141] Explicit examples of phosphorescent dopants are listed in the following table.

[0142] The compounds described above, including the preferred embodiments listed above, can preferably be used as an active component in an electronic device. An electronic device is understood to be a device that contains an anode, a cathode, and at least one layer located between the anode and the cathode, wherein this layer contains at least one organic or organometallic compound. The electronic device according to the invention thus contains an anode, a cathode, and at least one layer located between them, which contains at least one compound according to the invention.Preferred electronic devices are selected from the group consisting of organic electroluminescent devices (OLEDs, PLEDs), 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), organic electrical sensors, light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), and organic plasmon-emitting devices (DM Koller et al., Nature Photonics 2008, 1-4), preferably organic electroluminescent devices (OLEDs, PLEDs), in particular phosphorescent OLEDs, containing at least one compound according to the invention in at least one layer. Particular preference is given to organic electroluminescent devices.Active components are generally the organic or inorganic materials that are introduced between the anode and cathode, for example charge injection, charge transport or charge blocking materials, but in particular emission materials and matrix materials.

[0143] A preferred embodiment of the invention is organic electroluminescent devices. The organic electroluminescent device contains a cathode, an anode, and at least one emitting layer. In addition to these layers, it may contain further layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, charge generation layers, and / or organic or inorganic p / n junctions. It is possible for one or more hole transport layers to be p-doped, for example with metal oxides such as MoO 2 or WO 3 , or with (per)fluorinated electron-deficient aromatics, and / or for one or more electron transport layers to be n-doped.Interlayers can also be inserted between two emitting layers, which, for example, have an exciton-blocking function and / or control the charge balance in the electroluminescent device. However, it should be noted that not all of these layers are necessarily present.

[0144] The organic electroluminescent device can contain one emitting layer or it can contain several emitting layers. If several emitting layers are present, these preferably have a total of several emission maxima between 380 nm and 750 nm, so that overall white emission results, i.e. different emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. Particular preference is given to three-layer systems, wherein the three layers exhibit blue, green and orange or red emission (for the basic structure see, for example, WO 2005 / 011013) or systems which have more than three emitting layers. Tandem OLEDs are also preferred. It can also be a hybrid system, wherein one or more layers fluoresce and one or more other layers phosphoresce.

[0145] In a preferred embodiment of the invention, the organic electroluminescent device contains the compound according to the invention, preferably a compound of the preferred embodiments listed above, as matrix material, preferably as electron-conducting matrix material 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 compound with a wide band gap that is not involved, or not involved to a significant extent, in hole and electron transport in the layer. An emitting layer comprises at least one emitting compound.

[0146] In a further particularly preferred embodiment of the present invention, an organic electroluminescent device according to the invention comprises the compound according to the invention, preferably a compound of the preferred embodiments listed above, in a hole-conducting layer or an electron-conducting layer.

[0147] Suitable matrix materials which can be used in combination with the compounds according to the invention 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, in particular monoamines, e.g. according to WO 2014 / 015935, carbazole derivatives, e.g. B. CBP (N,N-biscarbazolylbiphenyl) or the carbazole derivatives disclosed in WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527 or WO 2008 / 086851, indolocarbazole derivatives, e.g. according to WO 2007 / 063754 or WO 2008 / 056746, indenocarbazole derivatives, e.g. according to WO 2010 / 136109 and WO 2011 / 000455, azacarbazole derivatives, e.g. according to EP 1617710, EP 1617711, EP 1731584, JP 2005 / 347160, bipolar matrix materials, e.g. B. according to WO 2007 / 137725, silanes, e.g. according to WO 005 / 111172, azaboroles or boronate esters, e.g. according to WO 2006 / 117052, triazine derivatives, e.g.according to WO 2010 / 015306, WO 2007 / 063754 or WO 2008 / 056746, zinc complexes, e.g. according to EP 652273 or WO 2009 / 062578, diazasilole or tetraazasilole derivatives, e.g. according to WO 2010 / 054729, diazaphosphole derivatives, e.g. according to WO 2010 / 054730, bridged carbazole derivatives, e.g. according to US 2009 / 0136779, WO 2010 / 050778, WO 2011 / 042107, WO 2011 / 088877 or WO 2012 / 143080, triphenylene derivatives, e.g. B. according to WO 2012 / 048781, lactams, e.g. 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, or dibenzofuran derivatives, e.g. according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608 or the not yet published applications EP 16158460.2 and EP 16159829.7. Likewise, a further phosphorescent emitter, which emits at a shorter wavelength than the actual emitter, can be present in the mixture as a co-host.

[0148] Preferred co-host materials are triarylamine derivatives, especially monoamines, indenocarbazole derivatives, 4-spirocarbazole derivatives, lactams and carbazole derivatives.

[0149] Preferred triarylamine derivatives used as co-host materials together with the compounds of the invention are selected from the compounds of the following formula (TA-1), where Ar 5<, identical or different on each occurrence, represents an aromatic or heteroaromatic ring system having 6 to 40 C atoms, each of which may be substituted by one or more radicals R 2<, where optionally two or more adjacent substituents R 2< may form a mono- or polycyclic, aliphatic ring system which may be substituted by one or more radicals R 3<, where the symbol R 2< has the meaning given above, in particular for formulas (I) to (XVIII). Preferably, Ar 5<, identical or different on each occurrence, represents an aryl or heteroaryl group having 5 to 24, preferably 5 to 12 aromatic ring atoms, each of which may be substituted by one or more radicals R 2<, but is preferably unsubstituted.

[0150] 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, which may each be substituted by one or more radicals R 2<, but are preferably unsubstituted.

[0151] Preferably, the groups Ar 5< are selected, identically or differently at each occurrence, from the abovementioned groups R 1< -1 to R'-92, particularly preferably R 1< -1 to R 1< -54.

[0152] In a preferred embodiment of the compounds of formula (TA-1), at least one Ar 5< group is 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 Ar 5< group is selected from a fluorene group or spirobifluorene group, which 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 5< is selected from a phenylene or biphenyl group, which is an ortho-, meta- or para-linked group which is substituted by 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.biphenyl group 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.

[0153] In a particularly preferred embodiment of the compounds of formula (TA-1), one group Ar 5< is selected from a fluorene or spirobifluorene group, in particular a 4-fluorene or 4-spirobifluorene group, and one 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 5< is selected from a para-phenylene group or a para-biphenyl group substituted by a dibenzofuran group, in particular a 4-dibenzofuran group, or a carbazole group, in particular an N-carbazole group or a 3-carbazole group.

[0154] Preferred indenocarbazole derivatives used as co-host materials together with the compounds of the invention are selected from the compounds of the following formula (TA-2), where Ar 5< and R 1< have the meanings listed above, in particular for formulas (I) and / or (TA-1). Preferred embodiments of the group Ar 5< are the structures R 1< -1 to R'-92 listed above, particularly preferably R 1< -1 to R'-54.

[0155] A preferred embodiment of the compounds of formula (TA-2) are the compounds of the following formula (TA-2a), where Ar 5< and R 1< have the meanings listed above, in particular for formulas (I) and / or (TA-1). The two groups R 1< which are bonded to the indenocarbon atom are preferably identical or different and represent an alkyl group having 1 to 4 C atoms, in particular methyl groups, or an aromatic ring system having 6 to 12 C atoms, in particular phenyl groups. The two groups R 1< which are bonded to the indenocarbon atom are particularly preferably methyl groups. Furthermore, the substituent R 1< which is bonded to the indenocarbazole parent structure in formula (TA-2a) is preferably H or a carbazole group which can be bonded to the indenocarbazole parent structure via the 1-, 2-, 3- or 4-position or via the N atom, in particular via the 3-position.

[0156] Preferred 4-spirocarbazole derivatives used as co-host materials together with the compounds of the invention are selected from the compounds of the following formula (TA-3), where Ar 5< and R 1< have the meanings listed above, in particular for formula (TA-1). Preferred embodiments of the group Ar 5< are the structures R 1< -1 to R'-92 listed above, particularly preferably R 1< -1 to R 1< -54.

[0157] A preferred embodiment of the compounds of formula (TA-3) are the compounds of the following formula (TA-3a), where Ar 5< and R 1< have the meanings listed above, in particular for formula (TA-1). Preferred embodiments of the group Ar 5< are the structures R 1< -1 to R'-92 listed above, particularly preferably R 1< -1 to R'-54.

[0158] Preferred lactams used as co-host materials together with the compounds of the invention are selected from the compounds of the following formula (LAC-1), where R 1< has the meaning given above.

[0159] A preferred embodiment of the compounds of formula (LAC-1) are the compounds of the following formula (LAC-1a), where R 1< has the meaning given above. R 1< is preferably the same or different on each occurrence and is H or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 2<, where R 2< may have the meaning given above. The substituents R 1< are very particularly preferably selected from the group consisting of H or an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, preferably having 6 to 13 aromatic ring atoms, each of which may be substituted by one or more non-aromatic radicals R 2<, but is preferably unsubstituted.Examples of suitable substituents R 1< 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, 1-, 2-, 3- or 4-dibenzothienyl and 1-, 2-, 3- or 4-carbazolyl, which may each be substituted by one or more radicals R 2<, but are preferably unsubstituted. Suitable structures R 1< are the same structures as previously shown for R-1 to R-79, particularly preferably R 1< -1 to R 1< -51.

[0160] It may also be preferable to use several different matrix materials as a mixture, in particular at least one electron-conducting matrix material and at least one hole-conducting matrix material. Likewise preferred is the use of a mixture of a charge-transporting matrix material and an electrically inert matrix material that is not involved, or not significantly involved, in charge transport, as described, for example, in WO 2010 / 108579.

[0161] 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.

[0162] Particularly preferably, a compound according to the invention 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 a compound of the preferred embodiments described above and below is present in the electronic device in combination with one or more dopants, preferably phosphorescent dopants.

[0163] In this case, the proportion of the 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 for fluorescent emitting layers between 92.0 and 99.5 vol.% and for phosphorescent emitting layers between 85.0 and 97.0 vol.%.

[0164] Accordingly, the proportion of the dopant is between 0.1 and 50.0 vol.%, preferably between 0.5 and 20.0 vol.% and particularly preferably for fluorescent emitting layers between 0.5 and 8.0 vol.% and for phosphorescent emitting layers between 3.0 and 15.0 vol.%.

[0165] An emitting layer of an organic electroluminescent device can also contain systems comprising multiple matrix materials (mixed-matrix systems) and / or multiple dopants. In this case, too, the dopants are generally the materials whose proportion is the smaller in the system, and the matrix materials are the materials whose proportion is the larger in the system. In individual cases, however, the proportion of a single matrix material in the system may be smaller than the proportion of a single dopant.

[0166] In a further preferred embodiment of the invention, the compounds according to the invention of 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, particularly preferably two different matrix materials. Preferably, one of the two materials is a material with hole-transporting properties and the other material 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 further mixed-matrix component(s) fulfilling 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, particularly 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. More detailed information on mixed-matrix systems can be found, among other things, in the application WO 2010 / 108579.

[0167] Furthermore, an electronic device, preferably an organic electroluminescent device, is the subject of the present invention, which comprises 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 electron-conducting compound.

[0168] Metals with a low work function, metal alloys, or multilayer structures made of different metals are preferred as the cathode, such as alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Alloys made of an alkali or alkaline earth metal and silver, for example, an alloy of magnesium and silver, are also suitable. In multilayer structures, other metals with a relatively high work function, such as Ag, can also be used in addition to the metals mentioned, in which case combinations of the metals, such as Mg / Ag, Ca / Ag, or Ba / Ag, are generally used. It may also be preferable to introduce a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor.Suitable materials for this purpose include alkali metal or alkaline earth metal fluorides, as well as the corresponding oxides or carbonates (e.g., LiF, Li 2 O, BaF 2 , MgO, NaF, CsF, Cs 2 CO 3 , etc.). Organic alkali metal complexes, such as Liq (lithium quinolinate), are also suitable. The thickness of this layer is preferably between 0.5 and 5 nm.

[0169] Materials with a high work function are preferred as the anode. The anode preferably has a work function greater than 4.5 eV vs. vacuum. Metals with a high redox potential, such as Ag, Pt, or Au, are suitable for this purpose. Metal / metal oxide electrodes (e.g., Al / Ni / NiO x , Al / PtO x ) may also be preferred. For some applications, at least one of the electrodes must be transparent or partially transparent to enable either the irradiation of the organic material (O-SC) or the coupling out of light (OLED / PLED, O-LASER). Preferred anode materials here are conductive mixed metal oxides. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred. Also preferred are conductive, doped organic materials, in particular conductive doped polymers, e.g., PEDOT, PANI, or derivatives of these polymers.It is also preferred if a p-doped hole-transport material is applied to the anode as a hole-injection layer. Suitable p-dopants are metal oxides, for example, MoOs or WO 3 , or (per)fluorinated electron-deficient aromatics. Other suitable p-dopants are HAT-CN (hexacyanohexaazatriphenylene) or the compound NPD9 from Novaled. Such a layer simplifies hole injection in materials with a deep HOMO, i.e., a large HOMO.

[0170] In the further layers, it is generally possible to use all materials as used for the layers according to the prior art, and the person skilled in the art can combine any of these materials with the materials according to the invention in an electronic device without inventive step.

[0171] The device is structured accordingly (depending on the application), contacted and finally hermetically sealed, since the lifetime of such devices is drastically reduced in the presence of water and / or air.

[0172] Also preferred is an electronic device, in particular an organic electroluminescent device, characterized in that one or more layers are coated using a sublimation process. The materials are vapor-deposited in vacuum sublimation systems at an initial pressure of typically less than 10 -5 mbar, preferably less than 10 -6 mbar. It is also possible for the initial pressure to be even lower or even higher, for example, less than 10 -7 mbar.

[0173] Also preferred is an electronic device, in particular an organic electroluminescent device, characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or by means of carrier gas sublimation. The materials are applied at a pressure between 10 -5 mbar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured (e.g., BMS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

[0174] Also preferred is an electronic device, in particular an organic electroluminescent device, which is characterized in that one or more layers are produced from solution, such as by spin coating, or by any printing process, such as screen printing, flexographic printing, offset printing, or nozzle printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing. Soluble compounds are required for this, which are obtained, for example, by suitable substitution.

[0175] The electronic device, in particular the organic electroluminescent device, can also be manufactured as a hybrid system by applying one or more layers from solution and vapor-depositing one or more other layers. For example, it is possible to apply an emitting layer containing a compound according to the invention and a matrix material from solution and then vacuum-deposit a hole-blocking layer and / or an electron-transport layer thereon.

[0176] These processes are generally known to the person skilled in the art and can be applied by him without problems to electronic devices, in particular organic electroluminescent devices containing compounds according to the invention of the preferred embodiments listed above.

[0177] 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 comprising compounds, oligomers, polymers, or dendrimers according to the invention that can be used as an active compound in an organic electronic device, or the preferred embodiments described above and below, in particular as electron-conducting materials and / or hole-conducting materials or as matrix materials, have a very good lifetime. 2. Electronic devices, in particular organic electroluminescent devices comprising compounds, oligomers, polymers, or dendrimers according to the invention that can be used as an active compound in an organic electronic device, or the preferred embodiments described above and below, in particular as electron-transport materials, hole-conducting materials, and / or as host materials, have excellent efficiency.In particular, the efficiency is significantly higher compared to analogous compounds that do not contain an aliphatic polycyclic ring system with at least 3 rings fused to an aromatic or heteroaromatic ring system with 5 to 60 carbon atoms. The compounds, oligomers, polymers, or dendrimers according to the invention, which can be used as an active compound in an organic electronic device, or the preferred embodiments described above and below, result in a low operating voltage when used in electronic devices. In particular, these compounds result in low roll-off, i.e., a low drop in the power efficiency of the device at high luminance levels. 3.Electronic devices, in particular organic electroluminescent devices containing compounds, oligomers, polymers or dendrimers which can be used as an active compound in an organic electronic device, or the preferred embodiments described above and below as electron-transport materials, hole-conductor materials and / or as host materials, have excellent color purity. 4. The compounds, oligomers, polymers or dendrimers according to the invention which can be used as an active compound in an organic electronic device, or the preferred embodiments described above and below, display very high thermal and photochemical stability and lead to compounds with a very long lifetime. 5. Compounds, oligomers, polymers or dendrimers which can be used as an active compound in an organic electronic device, orThe preferred embodiments described above and below can prevent the formation of optical loss channels in electronic devices, in particular organic electroluminescent devices. As a result, these devices are characterized by high PL and thus high EL efficiency of emitters and excellent energy transfer from the matrices to dopants. 6. Compounds, oligomers, polymers or dendrimers that can be used as an active compound in an organic electronic device, or the preferred embodiments described above and below, have excellent glass film formation. 7. Compounds, oligomers, polymers or dendrimers that can be used as an active compound in an organic electronic device, or the preferred embodiments described above and below, form very good films from solutions.

[0178] These advantages mentioned above are not accompanied by a deterioration of the other electronic properties.

[0179] The compounds and mixtures according to the invention are suitable for use in an electronic device. An electronic device is understood to be a device that contains at least one layer containing at least one organic compound. However, the component can also contain inorganic materials or layers composed entirely of inorganic materials.

[0180] A further object of the present invention is therefore the use of the compounds or mixtures according to the invention in an electronic device, in particular in an organic electroluminescent device.

[0181] Yet another object of the present invention is the use of a compound according to the invention and / or an oligomer, polymer or dendrimer according to the invention in an electronic device as a fluorescent emitter, emitter that exhibits TADF (thermally activated delayed fluorescence), host material, electron transport material, electron injection material, hole conductor material, hole injection material, electron blocking material, hole blocking material and / or wide band gap material, preferably as a fluorescent emitter (singulet emitter), host material, hole conductor material and / or electron transport material.

[0182] The present invention further provides an electronic device comprising at least one of the compounds or mixtures according to the invention described above. The preferences described above for the compound also apply to the electronic devices. Particularly preferred electronic devices are selected from the group consisting of organic electroluminescent devices (OLEDs, PLEDs), 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), organic electrical sensors, light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), and organic plasmon-emitting devices (DM Koller et al.)., Nature Photonics 2008, 1-4), preferably organic electroluminescent devices (OLEDs, PLEDs), especially phosphorescent OLEDs.

[0183] 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 the same as or similar to the metal complex in the emitting layer as a hole transport or hole injection material directly adjacent to the emitting layer, as described, for example, in WO 2009 / 030981.

[0184] In the further layers of the organic electroluminescent device according to the invention, all materials can be used as are customarily used according to the prior art. Therefore, without inventive step, the person skilled in the art can use all materials known for organic electroluminescent devices in combination with the compounds according to the invention that can be used as an active compound in an organic electronic device, preferably compounds obtainable by combining the partial structures according to the formulas (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-22) and (Ar'-45) or according to the preferred embodiments.

[0185] The compounds of the invention generally exhibit very good properties when used in organic electroluminescent devices. In particular, when the compounds of the invention are used in organic electroluminescent devices, their lifetime is significantly improved compared to similar compounds according to the prior art. The other properties of the organic electroluminescent device, in particular the efficiency and voltage, are also improved or at least comparable.

[0186] It should be understood that variations of the embodiments described in the present invention are within the scope of this invention. Unless explicitly excluded, any feature disclosed in the present invention may be replaced by alternative features serving the same, equivalent, or similar purpose. Thus, unless otherwise stated, any feature disclosed in the present invention is to be considered as an example of a generic series or as an equivalent or similar feature.

[0187] All features of the present invention may be combined with each other 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 may be used separately (and not in combination).

[0188] It should further be noted that many of the features, and particularly those of the preferred embodiments of the present invention, are inventive in their own right and should not be considered merely part of the embodiments of the present invention. Independent protection may be sought for these features in addition to or as an alternative to any presently claimed invention.

[0189] The teaching of technical action disclosed by the present invention can be abstracted and combined with other examples.

[0190] The invention is explained in more detail by the following examples, without intending to limit it thereby.

[0191] The person skilled in the art can produce further electronic devices according to the invention from the descriptions without inventive step and thus carry out the invention in the entire claimed scope. Examples

[0192] Unless otherwise stated, the following syntheses are carried out under a protective gas atmosphere in dried solvents. The metal complexes are also handled in the absence of light or under yellow light. The solvents and reagents can be obtained from Sigma-ALDRICH or ABCR, for example. The respective information in square brackets or the numbers given for individual compounds refer to the CAS numbers of the compounds known from the literature. For compounds that can exhibit multiple tautomeric forms, one tautomeric form is shown as a representative example. 1) Synthesis of synthons S: Example S1:

[0193]

[0194] A well-stirred mixture of 27.2 g (100 mmol) of 2-bromo-6,7,8,9,10,11-hexahydro-5,9:7,11-dimethano-5 H -benzocyclononene [1801624-97-4], 32.4 g (100 mmol) 2-(6,7,8,9,10,11-hexahydro-5,9:7,11-dimethano-5 H-benzocyclononen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [1801624-63-4], 63.7 g (300 mmol) tripotassium phosphate, 1.83 g (6 mmol) tri-o-tolylphosphine, 225 mg (1 mmol) palladium(II) acetate, 350 ml toluene, 80 ml dioxane, and 300 ml water are heated under reflux for 16 h. After cooling, the aqueous phase is separated, the organic phase is washed once with 300 ml water, once with 300 ml saturated sodium chloride solution, and then dried over magnesium sulfate. The drying agent is filtered off through a bed of silica gel pre-slurried with toluene, and the filtrate is concentrated to dryness. The glassy residue is recrystallized from isopropanol. Yield: 30.8 g (78 mmol) 78%. Purity according to 1< H-NMR approx. 97%.

[0195] The following connections can be represented analogously: e.g. Educts bromide ketone / electrophile product yield S10 81 % [1801624-97-4] [195062-57-8] S11 78 % [1801624-97-4] [24388-23-6] Example S2:

[0196]

[0197] A mixture of 3.1 ml (120 mmol) of bromine and 100 ml of dichloromethane is added dropwise over 3 h to a well-stirred solution of 39.5 g (100 mmol) of S1 in 500 ml of dichloromethane under exclusion of light. After the addition is complete, the mixture is stirred for 4 h under reflux and for 8 h at room temperature. 200 ml of saturated sodium sulfite solution is added to destroy excess bromine, the organic phase is separated, and it is washed with 500 ml of water and 300 ml of saturated sodium sulfite solution.

[0198] Sodium bicarbonate solution and dried over magnesium sulfate. The desiccant is removed by filtration, the filtrate is concentrated to dryness, and the viscous red residue is recrystallized from approximately 500 ml of isopropanol. Yield: 32.7 g (69 mmol), 69%. Purity according to 1< H-NMR: approximately 95%.

[0199] The following connection can be represented analogously: e.g. Educts bromide ketone / electrophile product yield S12 S10 46 % Example S3:

[0200]

[0201] Preparation analogous to S2, except that 6.4 ml (240 mmol) of bromine is used. Additionally, 100 mg of iron powder is added to the solution of S1 in dichloromethane. Yield: 33.7 g (61 mmol), 61%. Purity according to 1< H-NMR: approximately 97%.

[0202] The following connection can be represented analogously: e.g. Educts bromide ketone / electrophile product yield S13 S11 43 % Example S4:

[0203]

[0204] A well-stirred solution of 27.6 g (50 mmol) of S3 in 500 mL of THF, cooled to -78 °C, is treated dropwise with 65.6 mL (105 mmol) of n-BuLi in hexane, 1.6 M, and stirred for 30 min. A mixture of 5.1 mL (55 mmol) of dimethylcarbamoyl chloride [79-44-7] (Caution: Toxic, carcinogenic) and 50 mL of THF is then slowly added dropwise, stirred for 30 min, and then allowed to warm slowly to room temperature. After 2 h at room temperature, 200 mL of saturated ammonium chloride solution is added, diluted with 300 mL of ethyl acetate, the aqueous phase is separated, and the organic phase is evaporated to dryness. The residue is taken up in 250 ml of dichloromethane (DCM), washed three times with 300 ml of water and once with 300 ml of saturated sodium chloride solution, and dried over magnesium sulfate. The drying agent is removed by filtration, the filtrate is concentrated to dryness in vacuo, and the residue is recrystallized from acetonitrile. Yield: 18.1 g (43 mmol), 85%. Purity according to 1< H-NMR: approximately 97%. Example S5:

[0205]

[0206] A well-stirred solution of 47.4 g (100 mmol) of S2 in 500 ml of THF, cooled to -78 °C, is treated dropwise with 65.6 ml (105 mmol) of n-BuLi in hexane, 1.6 M, and stirred for 3 h. A solution of 27.2 g (105 mmol) of 2-bromo-9-fluorenone [3096-56-3] in 300 ml of THF is then slowly added dropwise, stirred for 30 min, and then allowed to warm slowly to room temperature. After 2 h at room temperature, the THF is removed under vacuum, the residue is taken up in 500 ml of glacial acetic acid, 30 ml of concentrated hydrochloric acid is added, and the mixture is heated under reflux for 3 h. The mixture is allowed to cool to 80 °C, 500 ml of water is slowly added dropwise, and the precipitated product is filtered off while still warm. The mixture is washed with 100 ml of water and then three times with 100 ml of methanol, and dried in vacuo. Yield: 56.6 g (89 mmol), 89%. Purity according to 1< H-NMR: approximately 97%.

[0207] The following connections can be represented analogously. e.g. Educts bromide ketone / electrophile product yield S6 S2 86 % [14348-75-5] S7 79 % [13029-09-9] S4 S8 S3 83 % [486-25-9] S9 S3 80 % S4 S15 S12 78 % [3096-56-3] Example S20:

[0208]

[0209] A well-stirred mixture of 28.3 g (100 mmol) of (2-bromo-4-chlorophenyl)phenylamine [2149611-39-0], 32.4 g (100 mmol) of 2-(6,7,8,9,10,11-hexahydro-5,9:7,11-dimethano-5 H-benzocyclononen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [1801624-63-4], 63.7 g (300 mmol) of tripotassium phosphate, 1.83 g (6 mmol) of tri-o-tolylphosphine, 225 mg (1 mmol) of palladium(II) acetate, 350 ml of toluene, 60 ml of dioxane, and 300 ml of water are heated under reflux for 16 h. After cooling, the aqueous phase is separated, the organic phase is washed once with 300 ml of water, once with 300 ml of saturated sodium chloride solution, and then dried over magnesium sulfate. The drying agent is filtered off through a bed of silica gel pre-slurried with toluene, and the filtrate is concentrated to dryness. The residue is recrystallized from acetonitrile with the addition of a little ethyl acetate. The resulting sec. amine is dissolved in 300 ml of DMF, treated with 45.4 g (250 mmol) of copper(II) acetate and 2.24 g (10 mmol) of palladium(II) acetate and stirred for 4 h at 140 °C. The DMF is largely removed under vacuum, the residue is taken up in 500 ml of DCM and treated with 300 ml of conc.Ammonia solution, stirred for 1 h at room temperature, separated the organic phase, washed three times with 100 ml of concentrated ammonia solution, once with saturated sodium chloride solution, and dried over magnesium sulfate. The magnesium sulfate was filtered off through a silica gel bed pre-slurried with DCM, the filtrate was concentrated to dryness, and the residue was recrystallized from acetonitrile / ethyl acetate. Yield: 18.7 g (47 mmol), 47%. Purity according to 1< H-NMR: approximately 95%. Example S25:

[0210]

[0211] A well-stirred mixture of 27.2 g (100 mmol) of 2-bromo-6,7,8,9,10,11-hexahydro-5,9:7,11-dimethano-5 H-benzocyclononene [1801624-97-4], 18.4 g (110 mmol) of carbazole [86-74-8], 41.5 g (300 mmol) of potassium carbonate, 1.9 g (10 mmol) of copper(I) iodide [7681-65-4], 100 g of glass beads (3 mm diameter), and 300 ml of dimethylacetamide are heated under reflux for 30 h. While still warm, the salts are filtered off with suction through a bed of Celite pre-slurried with dimethylacetamide, the filtrate is concentrated to dryness, the residue is taken up in 300 ml of DCM, filtered through a silica gel column (10 x 30 cm), and the nuclear fraction is removed. The eluate is freed from DCM in vacuo, and the residue is recrystallized from acetonitrile. Yield: 33.4 g (88 mmol) 88%. Purity according to 1< H-NMR approx. 99%. Example S26:

[0212]

[0213] A well-stirred solution of 38.0 g (100 mmol) of S25 in 500 ml of DCM, cooled to 0 °C, is treated dropwise with a solution of 17.8 g (100 mmol) of N-bromosuccinimide in 300 ml of dichloromethane under exclusion of light. The mixture is then stirred at room temperature for 12 h. The reaction solution is washed once with 200 ml of saturated sodium bicarbonate solution, three times with 200 ml of water each time, and once with 200 ml of saturated sodium chloride solution, and then dried over magnesium sulfate. The drying agent is filtered off, the filtrate is concentrated, and the residue is subjected to flash chromatography (Combi-Flash Torrent from A. Semrau). Yield: 33.0 g (72 mmol), 72%. Purity according to 1< H NMR: approximately 95%. Example S30:

[0214]

[0215] A well-stirred mixture of 17.3 g (100 mmol) 2-bromophenol [95-96-7], 32.4 g (100 mmol) 2-(6,7,8,9,10,11-hexahydro-5,9:7,11-dimethano-5 H-benzocyclononen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [1801624-63-4], 63.7 g (300 mmol) tripotassium phosphate, 1.83 g (6 mmol) tri-o-tolylphosphine, 225 mg (1 mmol) palladium(II) acetate, 350 ml toluene, 60 ml ethanol, and 300 ml water are heated under reflux for 16 h. After cooling, 60 ml 10N aqueous HCl is added, the aqueous phase is separated, and the organic phase is washed once with 300 ml water, once with 300 ml saturated sodium chloride solution, and then dried over magnesium sulfate. The drying agent is filtered off through a silica gel bed pre-slurried with toluene, and the filtrate is concentrated to dryness. The residue is recrystallized from isopropanol with the addition of a small amount of ethyl acetate. The resulting phenol is dissolved in 800 ml of mesitylene, and the well-stirred solution is treated with 27.6 g (200 mmol) of potassium carbonate, 100 g of molecular sieve 3A, 9.3 g (50 mmol) of sodium 2,4,6-trimethylbenzoate [32642-28-7], 1.82 g (10 mmol) of 4,5-diazafluoren-9-one [50890-67-0], and 4.26 g (10 mmol) of 1,3-bis[2,6-bis(1-methylethyl)phenyl]-1H-imidazolium chloride [250285-32-6] and 1.12 g (5 mmol) of palladium(II) acetate were added, and the mixture was then heated to 120 °C for 16 h while passing a gentle stream of air. While still warm, the mixture was filtered with suction through a bed of silica gel pre-slurried with mesitylene, the mesitylene was removed in vacuo, and the residue was recrystallized from acetonitrile. Yield: 15.6 g (54 mmol), 54%. Purity according to 1< H-NMR: approximately 95%. Example S31:

[0216]

[0217] A well-stirred mixture of 33.2 g (100 mmol) of S30 and 500 ml of THF, cooled to -78 °C, is treated dropwise with 65.6 ml (105 mmol) of n-BuLi in hexane, 1.6 M, and stirred for 60 min at -78 °C and then for 30 min at -40 °C. After cooling again to -78 °C, a mixture of 20.7 g (110 mmol) of tri-isopropyl borate [5419-55-6] and 50 ml of THF is quickly added with thorough stirring and stirred for a further 30 min. The reaction mixture is allowed to warm to room temperature, 100 ml of saturated ammonium chloride solution is added, the mixture is stirred for a further 15 min, and the org. The organic phase was separated, the residue was diluted with 500 ml of ethyl acetate, and washed three times with 300 ml of water each time and once with 200 ml of saturated sodium chloride solution. The organic phase was concentrated to dryness in vacuo, and the residue was recrystallized from acetonitrile with the addition of a little water. Yield: 18.9 g (57 mmol), 57%. Purity according to 1< H-NMR: approximately 95%. Example S35:

[0218]

[0219] A well-stirred mixture of 35.6 g (100 mmol) of 2,3-dibromo-6,7,8,9,10, 11-hexahydro-5,9:7,11-dimethano-5 H -benzocyclononene [1801624-66-7], 26.9 g (300 mmol) of copper(I) cyanide, 50 g of glass beads (3 mm diameter), and 300 ml of NMP are heated to 170 °C for 18 h. While still warm, the mixture is filtered with suction through a bed of Celite pre-suspended with NMP, the filtrate is concentrated to dryness in vacuo, and the residue is stirred in 300 ml of boiling MeOH. The crude product is extracted twice with hot acetonitrile. Yield: 15.0 g (60 mmol), 60%. Purity according to 1< H-NMR: approximately 95%. Example S36:

[0220]

[0221] A well-stirred solution of 35.6 g (100 mmol) of 2,3-dibromo-6,7,8,9,10,11-hexahydro-5,9:7,11-dimethano-5H-benzocyclononene [1801624-66-7] in 1000 ml of THF, cooled to -100 °C, is treated dropwise with 235 ml (400 mmol) of t-BuLi, 1.7 M in pentane and stirred for 30 min. Then a solution of 24.8 g (100 mmol) of S35 in 300 ml of THF is slowly added dropwise, stirred for 1 h, allowed to warm to room temperature and quenched by adding 50 ml of methanol. The THF is removed in vacuo, the residue is taken up in 300 ml of NMP and treated with 30 ml of conc. aqueous hydrochloric acid and heated to approximately 150 °C for 4 h. After cooling, the mixture is diluted with 500 ml of ethyl acetate, the organic phase is washed three times with 500 ml of water each time, once with 300 ml of saturated sodium chloride solution, and dried over magnesium sulfate. The drying agent is removed by filtration, the filtrate is concentrated to dryness in vacuo, and the yellow residue is recrystallized twice from acetonitrile. Yield: 19.4 g (43 mmol), 43%. Purity according to 1< H-NMR: approximately 95%.

[0222] The following connections can be represented analogously. e.g. reactants product yield S37 S35 47 % [583-53-9] Example S38:

[0223]

[0224] A suspension of 44.9 g (100 mmol) of S36 in 500 ml of glacial acetic acid is treated with 100 ml of aqueous hydriodic acid (57 wt%) and 200 ml of aqueous hypophosphorous acid (50 wt%) and heated under reflux for 18 h. The precipitated solid is filtered off with suction, washed with five 300 ml portions of hot water each, then stirred with 300 ml of hot ethanol, filtered off with suction, washed with 300 ml of hot ethanol, and dried in vacuo. Yield: 38.6 g (92 mmol), 92%. Purity according to 1< H-NMR: approximately 95%.

[0225] The following connections can be represented analogously. e.g. reactants product yield S39 S37 72 % Example S40:

[0226]

[0227] A solution of 41.9 g (100 mmol) of S38 in 500 ml of dichloromethane is treated portionwise with 19.6 g (110 mmol) of N-bromosuccinimide while stirring vigorously and in the absence of light. The reaction mixture is washed once with 300 ml of saturated sodium bicarbonate solution, three times with 300 ml of water each time, and once with 300 ml of saturated sodium chloride solution, and dried over magnesium sulfate. The drying agent is removed by filtration, the filtrate is concentrated to dryness, and recrystallized from acetonitrile / ethyl acetate. Yield: 50.2 g (87 mmol), 87%. Purity according to 1< H-NMR: approximately 98%.

[0228] The following connections can be represented analogously. e.g. reactants product yield S41 S37 84 % 2) Synthesis of amines A: Example A1 (not according to the invention)

[0229]

[0230] A solution of 63.6 g (100 mmol) of S5 and 38.6 g (120 mmol) of bis-p-biphenylamine [102113-98-4] in 500 mL of toluene was treated with 4.0 mL (4.0 mmol) of a 1.0 M tri-tert-butylphosphine solution in toluene, 449 mg (2 mmol) of palladium acetate, and 16.0 g of sodium tert-butoxide (166 mmol), and the mixture was heated under reflux for 3 h. The reaction mixture was cooled to room temperature, diluted with toluene, and filtered through a bed of Celite. The filtrate was concentrated in vacuo, and the residue was crystallized from ethyl acetate / n-heptane. The crude product was extracted three times with hot acetonitrile and purified by two zone sublimations under vacuum (p ∼ 10 -5 < mbar, T ∼ 310 °C). Yield: 63.1 g (72 mmol) 72%. Purity by HPLC >99.9%.

[0231] The following connections can be represented analogously: e.g. reactants product yield A2* S5 70 % [32228-99-2] A3* S5 68 % [1322090-81-2] A4* S5 75 % [1372775-52-4] A5* S5 73 % [897671-69-1] A6* S5 65 % [1421789-16-3] A7* S5 69 % [1644054-07-8] A8* S5 74 % [955959-89-4] A9* S5 74 % [90-30-2] A10* S5 70 % [1427556-44-2] A11* S6 66 % [620-93-9] A12* S6 61 % [1198395-24-2] A13* S7 78 % [102113-98-4] A14* S7 75 % [500717-23-7] A15* S7 71 % [1629995-09-0] A16* S7 72 % [897671-81-7] A17* S7 70 % [1372775-93-9] A18* S7 76 % [955959-91-8] A19* S8 44 % [1314527-06-4] A20* S8 41 % [1290037-87-0] A21* S9 48 % [1318338-47-4] A30* S15 67 % [897671-69-1] A31* S15 65 % [102113-98-4] A40* S13 (50 mmol) 56 % [102113-98-4] Example A22 (not according to the invention):

[0232]

[0233] A well-stirred mixture of 63.6 g (100 mmol) of S5, 57.6 g (110 mmol) of N-[1,1'-biphenyl]-2-yl-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-[1,1'-biphenyl]-4-amine [1608462-54-9], 63.7 g (300 mmol) of tripotassium phosphate, 1.83 g (6 mmol) of tri-o-tolylphosphine, 225 mg (1 mmol) of palladium(II) acetate, 500 ml of toluene, 100 ml of dioxane and 400 ml of water is heated under reflux for 16 h. After cooling, the aqueous phase is separated, the organic phase is washed once with 300 ml of water, once with 300 ml of saturated sodium chloride solution, and then dried over magnesium sulfate. The drying agent is filtered off through a bed of silica gel pre-slurried with toluene, and the filtrate is concentrated to dryness. The glassy residue is purified from ethyl acetate / iso- Recrystallized from propanol. The crude product was extracted three times with hot toluene and purified by two zone sublimations under vacuum (p ∼ 10 -5 < mbar, T ∼ 330 °C). Yield: 66.8 g (70 mmol) 70%. Purity by HPLC >99.9%.

[0234] The following connections can be represented analogously. e.g. reactants product yield A23 * S5 68 % [1959599-90-6] A24 * S5 71 % [1609381-12-5] A25 * S5 75 % [1942032-55-4] A26 * S8 73 % [943836-24-6] A27 * S15 69 % [1959599-90-6] A28 * S15 73 [1609381-12-5] *non-inventive examples 3) Synthesis of carbazoles C: Example C1 (not according to the invention):

[0235]

[0236] A well-stirred mixture of 44.2 g (100 mmol) of S26, 36.9 g (100 mmol) of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole [1126522-69-7], 63.7 g (300 mmol) of tripotassium phosphate, 1.83 g (6 mmol) of tri-o-tolylphosphine, 225 mg (1 mmol) of palladium(II) acetate, 350 ml of toluene, 80 ml of dioxane, and 300 ml of water was heated under reflux for 16 h. After cooling, the aqueous phase was separated, and the organic phase was evaporated to dryness. The residue is taken up in 500 ml of DCM, the organic phase is washed once with 300 ml of water and once with 300 ml of saturated sodium chloride solution, and then dried over magnesium sulfate. The drying agent is filtered off through a silica gel bed pre-slurried with DCM, and the filtrate is concentrated to dryness. The residue is stirred with hot butyl acetate / isopropanol, then hot extracted three times with toluene and purified by zone sublimation under vacuum (p ∼ 10 -5 < mbar, T ∼ 320 °C). Yield: 40.0 g (66 mmol) 66%. Purity by HPLC >99.9%.

[0237] The following connections can be represented analogously. e.g. reactants product yield C2* S26 64 % [1493715-55-1] C3* S26 70 % [1391729-66-0] C4* S26 65 % [1533406-38-0] C5* S26 73 % [1351870-14-8] C6* S26 71 % [1357150-79-8] C7* C8* S26 51 % [1846559-20-3] S20 57 % Use of 2 mmol S-Phos instead of tri-o-tolylphosphine [1622875-90-4] C9* S20 64 % Use of 2 mmol S-Phos instead of tri-o-tolylphosphine [1446005-91-9] C10* S20 70 % Use of 2 mmol S-Phos instead of tri-o-tolylphosphine [1338068-90-8] C11* S20 68 % Use of 2 mmol S-Phos instead of tri-o-tolylohosphine [1656982-71-6] C12* S20 59 % Use of 2 mmol S-Phos instead of tri-o-tolylphosphine S31 *non-inventive examples 4) Synthesis of triazines T: Example T1 (not according to the invention):

[0238]

[0239] A well-stirred mixture of 42.0 g (100 mmol) of 2,4-bis([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine [1205748-61-3], 32.4 g (100 mmol) of 2-(6,7,8,9,10, 11-hexahydro-5,9:7,11-dimethano-5H-benzocyclononen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [1801624-63-4], 31.9 g (150 mmol) of tripotassium phosphate, 821 mg (2 mmol) of S-Phos, 225 mg (1 mmol) of palladium(II) acetate, 400 ml of toluene, 80 ml of dioxane and 300 ml of water is heated under reflux for 16 h. After cooling, the aqueous phase is separated, the organic phase is washed once with 300 ml of water, once with 300 ml of saturated sodium chloride solution, and then dried over magnesium sulfate. The drying agent is filtered off through a bed of silica gel pre-slurried with toluene, and the filtrate is concentrated to dryness. The residue is washed with ISO -propanol, then extracted five times with hot acetonitrile and purified by zone sublimation in vacuo (p ∼ 10 -5 < mbar, T ~ 310 °C). Yield: 37.8 g (65 mmol) 65%. Purity by HPLC >99.9%.

[0240] The following connections can be represented analogously. e.g. reactants product yield T2* S26 64 % [2170382-97-3] T3* S26 55 % [1699739-82-6] T4* S26 57 % [2047632-07-6] T5* S26 49 % [1233200-61-7] 5) Synthesis of host materials for singlet emitter SH: Example SH1:

[0241]

[0242] A well-stirred mixture of 45.6 g (100 mmol) of S41, 37.8 g (220 mmol) of 1-naphthylboronic acid [13922-41-3], 63.7 g (300 mmol) of tripotassium phosphate, 1.83 g (6 mmol) of tri-o-tolylphosphine, 225 mg (1 mmol) of palladium(II) acetate, 400 ml of toluene, 80 ml of dioxane, and 300 ml of water was heated under reflux for 16 h. After cooling, the aqueous phase was separated, and the organic phase was evaporated to dryness. The residue was taken up in 500 ml of DCM, the organic phase was washed once with 300 ml of water and once with 300 ml of saturated sodium chloride solution, and then dried over magnesium sulfate. The drying agent is filtered through a silica gel bed pre-slurried with DCM, and the filtrate is concentrated to dryness. The residue is triturated with hot butyl acetate / isopropanol, then extracted five times with hot toluene and purified by zone sublimation under vacuum (p ∼ 10 -5 < mbar, T ~ 320 °C). Yield: 31.9 g (58 mmol) 58%, a mixture of Sny / Anti isomers. Purity by HPLC >99.9%. 6) Synthesis of the singlet emitter S: Example SE1:

[0243]

[0244] Procedure analogous to A1, using 28.8 g (50 mmol) of S40 and 31.0 g (110 mmol) of 4-(1,1-dimethylethyl)- N -[4-(1,1-dimethylethyl)phenyl]phenylamine [4627-22-9] can be used. Purification by five hot extractions with cyclohexane and zone sublimation under vacuum (p ∼ 10 -5 < mbar, T ∼ 330 °C). Yield: 26.0 g (53 mmol) 53%. Purity by HPLC >99.9%.

[0245] The following connections can be represented analogously. e.g. reactants product yield SE2 S40 48 % [37055-49-5] 7) Synthesis of spiromaterials H:

[0246] Analogous to S5, the following connections can be represented. e.g. Educts bromide ketone / electrophile product yield H1* S2 91 % S4 H2* S2 78 % 50 mmol [84-65-1] H3* S3, 25 mmol 54 % SiCl 4 , 12 mmol [10026-04-7] *non-inventive examples Production of OLED devices 1) Vacuum-processed devices:

[0247] The production of OLEDs according to the invention and OLEDs according to the prior art is carried out according to a general process according to WO 2004 / 058911, which is adapted to the conditions described here (layer thickness variation, materials used).

[0248] The following examples present the results of various OLEDs. Cleaned glass plates (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, within 30 minutes, coated with 20 nm PEDOT:PSS (poly(3,4-ethylenedioxythiophene) poly(styrenesulfonate), purchased as CLEVIOS™< P VP Al 4083 from Heraeus Precious Metals GmbH, Germany, spin-coated from aqueous solution) for improved processing. These coated glass plates are then baked at 180°C for 10 minutes. These coated glass plates form the substrates onto which the OLEDs are applied.

[0249] The OLEDs essentially have the following layer structure: substrate / hole injection layer 1 (HIL1) consisting of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm / hole transport layer 1 (HTL1) / hole transport layer 2 (HTL2) / emission layer (EML) / hole blocking layer (HBL) / electron transport layer (ETL) / optional electron injection layer (EIL), and finally a cathode. The cathode is formed by a 100 nm thick aluminum layer.

[0250] First, vacuum-processed OLEDs are described. For this, 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 (emitter), which is mixed with the matrix material(s) by co-evaporation in a specific volume fraction. A specification such as TMM1:TMM2:Ir(L1) (55%:35%:10%) means that the TMM1 material is present in the layer in a volume fraction of 55%, TMM2 in a volume fraction of 35%, and Ir(L1) in a volume fraction of 10%. Analogously, 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 manufacture the OLEDs are shown in Table 4.

[0251] OLEDs are characterized as standard. For this purpose, the electroluminescence spectra, current efficiency (measured in cd / A), power efficiency (measured in lm / W), and external quantum efficiency (EQE, measured in percent) are determined as a function of luminance, calculated from current-voltage-luminance curves (IUL curves) assuming a Lambertian radiation pattern, as well as the lifetime. 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 an initial brightness of 10000 cd / m².

[0252] The OLEDs can also be initially operated at other starting luminances. The lifetime values ​​can then be converted to values ​​for other starting luminances using conversion formulas familiar to those skilled in the art. Use of compounds according to the invention as materials in phosphorescent OLEDs

[0253] The compounds of the invention can be used, among other things, as HTM (hole transport material), TMM (triplet matrix material), ETM (electron transport material), and as emitter materials in the emission layer of OLEDs. The compounds shown in Table 4 were used as a comparison according to the state of the art. The OLED results are summarized in Table 2. Table 1: Structure of the OLEDs e.g. HTL1 thickness HTL2 thickness EML thickness HBL thickness ETL thickness Ref.D1 HTM1 210 nm HTM2 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm Ref. D2 HTM1 210 nm HTM2 10 nm TMM1:TMM2:Ir-Ref.2 (40%:50%:10%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D1* HTM1 210 nm A1 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D2* HTM1 210 nm A2 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D3* HTM1 210 nm A3 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D4* HTM1 210 nm A4 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D5* HTM1 210 nm A5 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D6* HTM1 210 nm A6 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D7* HTM1 210 nm A7 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D8* HTM1 210 nm A8 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D9* HTM1 210 nm A10 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D10* HTM1 210 nm A13 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D11* HTM1 210 nm A14 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D12* HTM1 210 nm A16 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D13* HTM1 210 nm A17 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D14* HTM1 210 nm A19 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D15* HTM1 210 nm A20 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D16* HTM1 210 nm A30 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D17* HTM1 210 nm A31 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D18* A9 210 nm HTM2 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D19* A11 210 nm HTM2 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D20* A12 210 nm HTM2 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D21* A40 210 nm HTM2 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D22* HTM1 210 nm A22 10 nm TMM1:TMM2:Ir-Ref.2 (40%:50%:10%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D23* HTM1 210 nm A23 10 nm TMM1:TMM2:Ir-Ref.2 (40%:50%:10%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D24* HTM1 210 nm A24 10 nm TMM1:TMM2:Ir-Ref.2 (40%:50%:10%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D25* HTM1 210 nm A25 10 nm TMM1:TMM2:Ir-Ref.2 (40%:50%:10%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D26* HTM1 210 nm A26 10 nm TMM1:TMM2:Ir-Ref.2 (40%:50%:10%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D27* HTM1 210 nm A27 10 nm TMM1:TMM2:Ir-Ref.2 (40%:50%:10%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D28* HTM1 210 nm A28 10 nm TMM1:TMM2:Ir-Ref.2 (40%:50%:10%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D29* HTM1 210 nm HTM2 10 nm TMM1:C1:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D30* HTM1 210 nm HTM2 10 nm TMM1:C3:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D31* HTM1 210 nm HTM2 10 nm TMM1:C4:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D32* HTM1 210 nm HTM2 10 nm TMM1:C5:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D33* HTM1 210 nm A13 10 nm TMM1:C12:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm ETM1:ETM2 (50%:50%) 30 nm D34* HTM1 210 nm HTM2 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm T1 10nm T1:ETM2 (50%:50%) 30 nm D35* HTM1 210 nm HTM2 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm T2 10nm T2:ETM2 (50%:50%) 30 nm D36* HTM1 210 nm HTM2 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm T3 10nm T3: ETM2 (50%:50%) 30 nm D37* HTM1 210 nm HTM2 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm ETM1 10nm T4:ETM2 (50%:50%) 30 nm D38* HTM1 210 nm HTM2 10 nm TMM1:TMM2:Ir-Ref.1 (45%:40%:15%) 30 nm T5 10nm T5: ETM2 (50%:50%) 30 nm D39 HTM1 160 nm HTM2 10 nm SH1:BD-Ref.1 (94%:6%) 20 nm --- ETM1:ETM2 (50%:50%) 30 nm D40 HTM1 200 nm HTM2 10 nm SH1:SE1 (94%:6%) 25 nm --- ETM1:ETM2 (50%:50%) 30 nm Tabelle 2: Ergebnisse der Vakuum-prozessierten OLEDs Bsp. EQE (%) 1000 cd / m 2< Spannung (V) 1000 cd / m 2< CIE x / y 1000 cd / m 2< LD90 (h) 10000 cd / m 2< Grüne und Gelbe OLEDs Ref.D1 19.2 3.3 0.33 / 0.62 310 Ref. D2 18.1 3.2 0.41 / 0.58 440 D1* 19.4 3.3 0.33 / 0.62 330 D2* 20.0 3.2 0.32 / 0.62 310 D3* 19.5 3.2 0.33 / 0.62 340 D4* 19.0 3.1 0.33 / 0.63 330 D5* 19.4 3.3 0.33 / 0.62 350 D6* 20.3 3.3 0.33 / 0.62 300 D7* 18.7 3.1 0.32 / 0.61 360 D8* 19.7 3.1 0.33 / 0.62 330 D9* 19.5 3.3 0.33 / 0.62 340 D10* 20.0 3.1 0.32 / 0.62 330 D11* 19.2 3.0 0.33 / 0.62 350 D12* 19.4 3.2 0.33 / 0.62 340 D13* 19.2 3.3 0.33 / 0.62 370 D14* 19.7 3.2 0.32 / 0.61 320 D15* 18.9 3.3 0.33 / 0.62 350 D16* 20.1 2.9 0.33 / 0.62 380 D17* 19.7 3.0 0.33 / 0.62 390 D18* 19.3 3.5 0.33 / 0.62 320 D19* 20.0 2.8 0.33 / 0.62 310 D20* 20.4 2.9 0.33 / 0.62 380 D21* 20.2 2.8 0.32 / 0.62 370 D22* 18.2 3.0 0.41 / 0.58 450 D23* 18.0 2.8 0.41 / 0.58 470 D24* 19.1 2.9 0.41 / 0.58 510 D25* 18.7 2.9 0.41 / 0.58 470 D26* 19.0 3.0 0.41 / 0.58 450 D27* 19.3 2.8 0.41 / 0.58 460 D28* 19.2 2.9 0.41 / 0.58 500 D29* 19.7 3.1 0.33 / 0.62 390 D30* 19.6 3.1 0.33 / 0.62 380 D31* 19.7 3.1 0.33 / 0.62 370 D32* 20.0 3.2 0.32 / 0.62 420 D33* 19.3 3.1 0.32 / 0.62 360 D34* 19.4 3.2 0.33 / 0.62 340 D35* 19.3 3.1 0.33 / 0.62 350 D36* 19.4 3.2 0.33 / 0.62 340 D37* 19.5 3.4 0.33 / 0.62 360 D38* 19.7 3.2 0.33 / 0.62 370 Blaue und Grüne OLEDs Bsp. EQE (%) 1000 cd / m 2 Voltage (V) 1000 cd / m 2< CIE x / y 1000 cd / m 2 LD90 (h) 10000 cd / m 2 D39 7.2 4.2 0.15 / 0.09 300h D40 8.6 3.7 0.29 / 0.62 --- 2. Solution-processed devices: A: From low molecular weight soluble functional materials

[0254] The materials according to the invention can also be processed from solution, resulting in OLEDs that are significantly simpler in terms of process technology than vacuum-processed OLEDs, yet still retain good properties. The production of such components is based on the production of polymer light-emitting diodes (PLEDs), which has been described extensively in the literature (e.g., in WO 2004 / 037887). The structure consists of a substrate, ITO, hole-injection layer (60 nm), interlayer (20 nm), emission layer (60 nm), hole-blocking layer (10 nm), electron-transport layer (40 nm), and cathode. Substrates from Technoprint (sodium tin oxide) are used for this purpose, onto which the ITO structure (indium tin oxide, a transparent, conductive anode) is applied. The substrates are cleaned in the cleanroom with DI water and a detergent (Deconex 15 PF) and then activated by a UV / ozone plasma treatment.A 20 nm hole-injection layer is then applied by spin coating, also in a clean room. The required spin rate depends on the degree of dilution and the specific spin coater geometry. To remove residual water from the layer, the substrates are baked on a hot plate at 200 °C for 30 minutes. The interlayer used serves to transport the holes; in this case, HL-X from Merck is used. Alternatively, the interlayer can be replaced by one or more layers, which only have to meet the condition of not being removed again during the subsequent processing step of EML deposition from solution. To produce the emission layer, the triplet emitters according to the invention are dissolved together with the matrix materials in toluene or chlorobenzene. The typical solids content of such solutions is between 16 and 25 g / L if, as here, the layer thickness of 60 nm, typical for a device, is to be achieved by spin coating.The solution-processed devices contain an emission layer consisting of Matrix1:Matrix2:Ir-Ref.3 and optionally Ir-Ref.4. A Matrix3 is also used if necessary (see Table 3). The emission layer is spin-coated in an inert gas atmosphere, in this case argon, and annealed for 10 min at 160 °C. The hole-blocking layer (10 nm ETM1) and the electron-transport layer (40 nm ETM1 (50%) / ETM2 (50%)) are evaporated over it (evaporation systems from Lesker et al., typical deposition pressure 5 x 10 -6 < mbar). Finally, a cathode made of aluminum (100 nm) (high-purity metal from Aldrich) is evaporated. To protect the device from air and humidity, the device is finally encapsulated and then characterized. The OLED examples mentioned are not yet optimized; Table 3 summarizes the obtained data.The lifetime LD50 is defined as the time after which the luminance drops to 50% of the starting luminance when operated with an initial brightness of 1000 cd / m2. Table 3: Results with materials processed from solution e.g. Matrix1 EQE (%) 1000 cd / m 2 Voltage (V) 1000 cd / m 2< CIE x / y LD50 (h) 1000 cd / m 2 Matrix2 Matrix3 Ir-Ref.3 Sol-D1* TMM3 (20%) 21.0 4.3 0.34 / 0.62 310000 TMM4 (60%) --- Ir-Ref.3 (20%) Sol-D2* TMM3 (26%) 20.9 3.9 0.34 / 0.62 330000 TMM4 (50%) A15 (8%) Ir-Ref.3 (16%) Sol-D3* TMM3 (30%) 21.2 3.9 0.35 / 0.62 350000 TMM4 (48%) A18 (6%) Ir-Ref.3 (16%) Sol-D4* TMM3 (30%) 21.5 3.8 0.34 / 0.62 330000 TMM4 (48%) A21 (6%) Ir-Ref.3 (16%) Sol-D5* TMM3 (30%) 21.3 4.2 0.35 / 0.62 340000 TMM4 (48%) C6 (6%) Ir-Ref.3 (16%) Sol-D6* TMM3 (30%) 21.1 4.1 0.35 / 0.62 330000 TMM4 (48%) C7 (6%) Ir-Ref.3 (16%) Sol-D7* C8 (20%) 21.4 4.1 0.35 / 0.62 370000 TMM4 (56%) --- Ir-Ref.3 (24%) Sol-D8* C9 (20%) 21.0 4.0 0.34 / 0.62 350000 TMM4 (56%) --- Ir-Ref.3 (24%) Sol-D9* TMM3 (38%) 20.8 3.9 0.35 / 0.62 340000 TMM4 (40%) C10 (6%) Ir-Ref.3 (16%) Sol-D10* TMM3 (20%) 21.6 4.2 0.34 / 0.62 360000 TMM4 (52%) H1 (8%) Ir-Ref.3 (20%) Sol-D11* TMM3 (10%) 18.1 5.7 0.67 / 0.33 300000 C11 (20%) TMM4 (34%) Ir-Ref.3 (30%) Ir-Ref.4 (6%) Table 4: Structural formulas of the materials used HTM1 [136463-07-5] HTM2 [1450933-43-3] TMM1 [1257248-13-7] TMM2 [1357150-54-9] <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> TMM3 [1616231-60-7] TMM4 [1246496-85-4] ETM1 = M10 [1233200-52-6] <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ETM2 [25387-93-3] Ir-Ref.1 [1989606-01-0] Ir-Ref.2 [1989605-56-2] Ir-Ref.3 [2170173-12-1] BD-Ref.1 [1883835-29-7] Ir-Ref.4 [1989604-92-3]

[0255] The present invention describes compounds that can be used as active compounds in an organic electronic device, particularly for use in electronic devices. The invention further relates to a process for preparing the compounds according to the invention and to electronic devices containing them.

Claims

1. Compound which can preferably be employed as active compound in an organic electronic device, characterised in that the compound has at least one aromatic or heteroaromatic ring system having 5 to 60 carbon atoms which is condensed onto an aliphatic polycyclic ring system having at least 3 rings, characterised in that the aliphatic polycyclic ring system having at least 3 rings which is condensed onto an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms forms a substructure of the formulae (N-1) to (N-6), where the dashed lines represent the links of the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms onto which the aliphatic polycyclic ring system having at least 3 rings is condensed, and where the following applies to the symbols R1, v, t and s: R1 is on each occurrence, identically or differently, H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar1)2, N(R2)2, C(=O)Ar1, C(=O)R2, P(=O)(Ar1)2, P(Ar1)2, B(Ar1)2, B(OR2)2, Si(Ar1)3, Si(R2)3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, which may in each case be substituted by one or more radicals R2, where one or more non-adjacent CH2 groups may be replaced by -R2C=CR2-, -C=C-, Si(R2)2, Ge(R2)2, Sn(R2)2, C=O, C=S, C=Se, C=NR2, -C(=O)O-, -C(=O)NR2-, NR2, P(=O)(R2), -O-, -S-, SO or SO2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R2, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R2, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R2, or a combination of these systems; two or more, preferably adjacent radicals R1 may form a mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system with one another; Ar1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more, preferably non-aromatic radicals R2; two radicals Ar1 that are bonded to the same Si atom, N atom, P atom or B atom may also be bridged to one another by a single bond or a bridge selected from B(R2), C(R2)2, Si(R2)2, C=O, C=NR2, C=C(R2)2, O, S, S=O, SO2, N(R2), P(R2) and P(=O)R2; R2 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, B(OR3)2, NO2, C(=O)R3, CR3=C(R3)2, C(=O)OR3, C(=O)N(R3)2, Si(R3)3, P(R3)2, B(R3)2, N(R3)2, NO2, P(=O)(R3)2, OSO2R3, OR3, S(=O)R3, S(=O)2R3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may in each case be substituted by one or more radicals R3, where one or more non-adjacent CH2 groups may be replaced by -R3C=CR3-, -C=C-, Si(R3)2, Ge(R3)2, Sn(R3)2, C=O, C=S, C=NR3, -C(=O)O-, -C(=O)NR3-, NR3, P(=O)(R3), -O-, -S-, SO or SO2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R3, or an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R3, or a combination of these systems; two or more, preferably adjacent substituents R2 may also form a mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system with one another; R3 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups, in each case having 1 to 4 carbon atoms; two or more, preferably adjacent substituents R3 may also form a mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system with one another; the index s is 0, 1 or 2; the index t is 0, 1, 2, 3, 4, 5, 6, 7 or 8, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2; the index v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2, and characterised in that the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms onto which an aliphatic polycyclic ring system having at least 3 rings is condensed forms a substructure of the formulae (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45) and (Ar-55) to (Ar-66), where X' is N or CR1, preferably CR1, where R1 has the meaning described above and the aliphatic polycyclic ring system having at least 3 rings is bonded to the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms in each case at the positions denoted by o with formation of a ring.

2. Compound according to Claim 1, characterised in that the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms onto which an aliphatic polycyclic ring system having at least 3 rings is condensed forms a substructure of the formulae (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-21), (Ar'-44) and (Ar'-54) to (Ar'-65): where R1 has the meaning described in Claim 1, the index o is 0, 1 or 2, preferably 0 or 1, the index n is 0, 1, 2 or 3, preferably 0, 1 or 2, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, the index I is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1 or 2 and the aliphatic polycyclic ring system having at least 3 rings is bonded to the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms in each case at the positions denoted by o with formation of a ring.

3. Compound according to at least one of Claims 1 or 2, characterised in that the compound comprises a hole-transport group, where a group R1 preferably comprises a hole-transport group in a structure of the formulae (N-1) to (N-6).

4. Compound according to at least one of the preceding claims, characterised in that the compound comprises, preferably represents, an electron-transport group or, in a structure of the formulae (N-1) to (N-6), (Ar-2), (Ar-3), (Ar-16) to (Ar-22), (Ar-45), (Ar-55) to (Ar-66) and / or (Ar'-2), (Ar'-3), (Ar'-16) to (Ar'-21), (Ar'-44), a group R1 comprises an electron-transport group, where the electron-conductor groups preferably comprise at least 2 nitrogen atoms in one six-membered ring or in two condensed six-membered rings.

5. Compound according to at least one of the preceding Claims 1, 2 and 4, characterised in that the ring via which the aliphatic polycyclic ring system having at least 3 rings is condensed onto the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms comprises six ring atoms and at least two non-adjacent nitrogen atoms.

6. Compound according to at least one of the preceding Claims 1, 2 and 4, characterised in that the ring via which the aliphatic polycyclic ring system having at least 3 rings is condensed onto the aromatic or heteroaromatic ring system having 5 to 60 carbon atoms comprises six ring atoms and at least one nitrogen atom and no further ring system is condensed onto this ring.

7. Oligomer, polymer or dendrimer containing one or more compounds according to one of Claims 1 to 6, where, instead of a hydrogen atom or a substituent, one or more bonds are present from the compounds to the polymer, oligomer or dendrimer.

8. Composition comprising at least one compound according to one or more of Claims 1 to 6 or an oligomer, polymer or dendrimer according to Claim 7 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters which exhibit TADF (thermally activated delayed fluorescence), host materials, electron-transport materials, electron-injection materials, hole-conductor materials, hole-injection materials, electron-blocking materials and hole-blocking materials.

9. Formulation comprising at least one compound according to one or more of Claims 1 to 6 or an oligomer, polymer or dendrimer according to Claim 7 or a composition according to Claim 8 and at least one solvent.

10. Use of a compound according to one or more of Claims 1 to 6, an oligomer, polymer or dendrimer according to Claim 7 or a composition according to Claim 8 in an electronic device as fluorescent emitter, emitter which exhibits TADF (thermally activated delayed fluorescence), host material, electron-transport material, electron-injection material, hole-conductor material, hole-injection material, electron-blocking material, hole-blocking material and / or wide-band-gap material, preferably as fluorescent emitter (singlet emitter), host material, hole-conductor material and / or electron-transport material.

11. Process for the preparation of a compound according to one or more of Claims 1 to 6 or an oligomer, polymer and / or dendrimer according to Claim 7, characterised in that a compound comprising at least one aliphatic polycyclic ring system having at least 3 rings is connected to a compound comprising at least one aromatic or heteroaromatic group in a coupling reaction.

12. Electronic device containing at least one compound according to one or more of Claims 1 to 6, an oligomer, polymer or dendrimer according to Claim 7 or a composition according to Claim 8, where 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.