CONNECTIONS USABLE IN AN ORGANIC ELECTRONIC DEVICE

Description

[0001] The present invention describes compounds according to claims 12 and 13, in particular for use in electronic devices. The invention further relates to a method for producing the compounds according to the invention according to claim 18. The present invention describes an electronic device according to claim 1.

[0002] The design of organic electroluminescent devices, in which organic semiconductors are used as functional materials, is described, for example, in US 4539507, US 5151629, EP 0676461, WO 98 / 27136, and WO 2010 / 151006 A1. Organometallic complexes exhibiting phosphorescence are frequently used as emitting materials. For quantum mechanical reasons, up to four times the energy and power efficiency is possible when using organometallic compounds as phosphorescent emitters. In general, there is still room for improvement in electroluminescent devices, especially those exhibiting phosphorescence, for example, with regard to efficiency, operating voltage, and lifetime. Furthermore, organic electroluminescent devices are known that include fluorescent emitters or emitters exhibiting TADF (thermally activated delayed fluorescence).

[0003] Specific cyclic compounds are described in Nataliya N Karaush-Karmazin et al, New Journal of Chemistry, Vol. 43, No. 30, 2019 and Carlos A. Manzano et al, Environmental Science & Technology Vol. 51, No. 10, 2017.

[0004] The properties of organic electroluminescent devices are not solely determined by the emitters used. The other materials employed, such as host / matrix materials, hole-blocking materials, electron transport materials, and electron / exciton blocking materials, are also of particular importance. Improvements to these materials can lead to significant enhancements in electroluminescent devices.

[0005] In general, there is still room for improvement with these materials, for example, for use as matrix materials, hole transport materials, or electron transport materials, particularly with regard to their lifespan, but also with regard to the efficiency and operating voltage of the device. Furthermore, the compounds should exhibit high color purity.

[0006] A further object of the present invention is the provision of compounds which are suitable for use in an organic electronic device, in particular in an organic electroluminescence device, as fluorescent emitters or emitters which exhibit TADF (thermally activated delayed fluorescence), and which lead to good device properties when used in this device, as well as the provision of the corresponding electronic device.

[0007] 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 electroluminescence device, and which lead to good device properties when used in this device, as well as to provide the corresponding electronic device.

[0008] In particular, the object of the present invention is to provide compounds that lead to a long service life, good efficiency, and low operating voltage. The properties of the matrix materials, the hole transport materials, and the electron transport materials also have a significant influence on the service life and efficiency of the organic electroluminescence device.

[0009] A further object of the present invention can be seen as providing compounds suitable for use in phosphorescent or fluorescent electroluminescent devices, in particular as matrix materials. In particular, it is an object of the present invention to provide matrix materials suitable for red and yellow phosphorescent electroluminescent devices.

[0010] Furthermore, the compounds, especially when used as matrix materials, hole transport materials or electron transport materials in organic electroluminescence devices, should lead to devices that exhibit excellent color purity.

[0011] Furthermore, the compounds should be as easy to process as possible, exhibiting in particular good solubility and film formation. For example, the compounds should show increased oxidation stability and an improved glass transition temperature.

[0012] Another task can be seen as providing electronic devices with excellent performance as cost-effectively as possible and in consistent quality.

[0013] Furthermore, the electronic devices should be usable or adaptable for many purposes. In particular, the performance of the electronic devices should be maintained over a wide temperature range.

[0014] Surprisingly, it was found that certain electronic devices and connections, described in more detail below, solve these problems and eliminate the disadvantage of the prior art. The use of these connections leads to very good properties of organic electronic devices, especially organic electroluminescent devices, particularly with regard to lifetime, efficiency, and operating voltage. Electronic devices, especially organic electroluminescent devices, and the corresponding preferred embodiments are therefore the subject of the present invention.

[0015] The present invention therefore relates to an electronic device comprising at least one connection comprising at least one structure of formula (1a), preferably (1b), (1c), (1d), (1e) and / or (1f), where the following applies in formulas (1a) to (If): X is the same or different from CR in each occurrence, where at most 2 of the groups CR, for which X stands, are different from the group CH; Y is the same or different from each occurrence a bridge selected from O, S, B(R), C=O, N(R) and N(Ar), especially preferred O, S, N(Ar); Rist, whether the same or different at each occurrence, is H, D, F, CN, N(Ar) 2 , N(R 1< ) 2 , Si(Ar) 3 , Si(R 1< ) 3 , B(Ar) 2 , B(R 1< ) 2 , a straight-chain alkyl or alkoxy group with 1 to 40 C atoms, or a branched or cyclic alkyl or alkoxy group with 3 to 20 C atoms, wherein the alkyl or alkoxy group may be substituted with one or more R 1< residues, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 1< residues; two R residues may also form a ring system together;Arist, in each occurrence the same or different, is an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which may be substituted with one or more R 1< residues, whereby two Ar residues bonding to the same Si atom, N atom or B atom may also be bridged by a single bond or a bridge selected from B(R 1< ), C(R 1< ) 2 , Si(R 1< ) 2 , C=O, C=NR 1< , C=C(R 1< ) 2 , O, N(R 1< ), P(R 1< ) and P(=O)R 1< , to each other;R 1< is the same or different in each occurrence: H, D, F, CN, N(Ar 1< ) 2 , N(R 2< ) 2 , B(Ar 1< ) 2 , B(R 2< ) 2 , Si(Ar 1< ) 3 , Si(R 2< ) 3 , a straight-chain alkyl or alkoxy group with 1 to 40 C atoms, or a branched or cyclic alkyl or alkoxy group with 3 to 40 C atoms, each of which may be substituted with one or more R 2< residues, where one or more H atoms may be replaced by D, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 2< residues; Two or more, preferably adjacent, residues R 1< can form a ring system together; one or more residues R 1< can form a ring system with another part of the compound;Ar 1< is, in each occurrence, the same or different, an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which may be substituted with one or more non-aromatic residues R 2<, whereby two residues Ar 1<, which bond to the same Si atom, N atom or B atom, may also be bridged to each other 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, N(R 2< ), P(R 2< ) and P(=O)R 2< ; R 2< is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbon residue with 1 to 20 C atoms or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D and which may be substituted by one or more alkyl groups with 1 to 4 carbon atoms each;Two or more, preferably adjacent, substituents R 2< can form a ring system together.

[0016] The present invention also relates to connections according to claim 12 and claim 13.

[0017] Preferably, the aforementioned compounds can be used as active compounds in electronic devices. Active compounds are generally the organic or inorganic materials that are introduced, for example, in an organic electronic device, particularly in an organic electroluminescent device, between the anode and cathode; for example, charge injection, charge transport, or charge blocking materials, but especially emission materials and matrix materials. Organic materials are preferred.

[0018] Preferably, a compound according to claim 12 or 13 is a purely organic compound. A purely organic compound is a compound that is not bonded to a metal atom, i.e., it neither forms a coordination bond with a metal atom nor a covalent bond with a metal atom. In this context, a purely organic compound preferably does not include any metal atom used in phosphorescent emitters. These metals, such as copper, molybdenum, etc., and in particular rhenium, ruthenium, osmium, rhodium, iridium, and palladium, will be described in detail later.

[0019] The compound that can be used as an active compound in an organic electronic device may preferably be selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF (thermally activated delayed fluorescence), host materials, electron transport materials, exciton blocking materials, electron injection materials, hole transport materials, hole injection materials, n-dopeds, p-dopeds, wide-band-gap materials, electron blocking materials, and / or hole blocking materials. Fluorescent emitters, emitters exhibiting TADF (thermally activated delayed fluorescence), host materials, electron transport materials, exciton blocking materials, electron injection materials, hole transport materials, hole injection materials, n-dopeds, p-dopeds, wide-band-gap materials, electron blocking materials, and / or hole blocking materials are preferred.

[0020] Adjacent carbon atoms within the meaning of the present invention are carbon atoms that are directly linked to one another. Furthermore, "adjacent residues" in the definition of residues means that these residues are bonded to the same carbon atom or to neighboring carbon atoms. These definitions apply accordingly, inter alia, to the terms "adjacent groups" and "adjacent substituents".

[0021] In the context of this description, the phrase "two or more residues can form a ring" means, among other things, that the two residues are linked to each other by a chemical bond involving the formal elimination of two hydrogen atoms. This is illustrated by the following scheme.

[0022] Furthermore, the above formulation should also be understood to mean that if one of the two residues represents hydrogen, the second residue binds to the position to which the hydrogen atom was bonded, forming a ring. This is illustrated by the following diagram:

[0023] A condensed aryl group, a condensed aromatic ring system, or a condensed heteroaromatic ring system within the meaning of the present invention is a group in which two or more aromatic groups are fused, i.e., fused, to one another via a common edge, such that, for example, two carbon atoms belong to at least two aromatic or heteroaromatic rings, as in naphthalene. In contrast, fluorene, for example, is not a condensed aryl group within the meaning of the present invention, since in fluorene the two aromatic groups do not share a common edge. Corresponding definitions apply to heteroaryl groups and to condensed ring systems, which may, but need not, also contain heteroatoms.

[0024] If two or more, preferably adjacent, residues R, R 1< and / or R 2< form a ring system together, a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system can be formed.

[0025] An aryl group according to this invention contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, and particularly preferably 6 to 30 carbon atoms; a heteroaryl group according to this invention contains 2 to 60 carbon atoms, preferably 2 to 40 carbon atoms, and particularly preferably 2 to 30 carbon atoms, and at least one heteroatom, provided that the sum of the carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from nitrogen, oxygen, and / or sulfur. An aryl group or heteroaryl group is understood to be either a simple aromatic cycle, i.e., benzene, or a simple heteroaromatic cycle, for example, pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl group, for example, naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc.

[0026] An aromatic ring system according to this invention contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, and particularly preferably 6 to 30 carbon atoms in the ring system. A heteroaromatic ring system according to this invention contains 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms, and particularly preferably 1 to 30 carbon atoms, and at least one heteroatom in the ring system, provided that the sum of the carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from nitrogen, oxygen, and / or sulfur. An aromatic or heteroaromatic ring system according to this invention is understood to be a system that does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups may also be interrupted by a non-aromatic unit (preferably less than 10% of the atoms other than hydrogen), such as a carbon, nitrogen, or oxygen atom or a carbonyl group.For example, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc., are to be understood as aromatic ring systems within the meaning of this invention, as are systems in which two or more aryl groups are interrupted, for example, by a linear or cyclic alkyl group or by a silyl group. Furthermore, systems in which two or more aryl or heteroaryl groups are directly bonded to one another, such as biphenyl, terphenyl, quaterphenyl, or bipyridine, are also to be understood as aromatic or heteroaromatic ring systems.

[0027] For the purposes of this invention, a cyclic alkyl, alkoxy or thioalkoxy group is understood to be a monocyclic, a bicyclic or a polycyclic group.

[0028] Within the scope of the present invention, the following groups, for example, are formed under a C1 to C20 alkyl group, in which individual hydrogen atoms or CH2 groups may also be substituted by the groups mentioned above: 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- understood. Examples of alkenyl groups include ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, and cyclooctadienyl. Examples of alkynyl groups include ethinyl, propynyl, butynyl, pentinyl, hexinyl, heptinyl, and octynyl. Examples of C1 to C40 alkoxy groups include methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, and 2-methylbutoxy.

[0029] An aromatic or heteroaromatic ring system with 5 to 60, preferably 5 to 40, aromatic ring atoms, particularly preferably 5 to 30 aromatic ring atoms, which may each be further substituted with the aforementioned substituents and which may be linked via any positions on the aromatic or heteroaromatic compound, includes, for example, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzfluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-monobenzoindenofluorene, cis- or trans-dibenzoindenofluorene, truxene, isotruxene, spirotruxene, 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.

[0030] In a preferred embodiment, the electronic device according to the invention can include at least one connection comprising a structure of formulas (IIa), (IIb), (IIc), (IId), (IIe) and / or (IIf), preferably the connection has a structure of the aforementioned formulas, wherein the remainders X, Y and R have the aforementioned meaning, the index m is equal to or different from 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, more preferably 0 or 1, and the index o is equal to or different from 0, 1 or 2, more preferably 0 or 1, wherein the sum of the indices o and m is preferably 1 or 2, more preferably 1.

[0031] Preferably, the electronic device may include at least one connection comprising a structure of formulas (IIIa), (IIIb), (IIIc), (IIId), (IIIe) and / or (IIIf), preferably the connection has a structure of the aforementioned formulas. wherein the remainders X, Y and R have the aforementioned meaning, the index m is equal to or different from 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, more preferably 0 or 1, and the index n is equal to or different from 0, 1, 2 or 3, more preferably 0, 1 or 2, more preferably 0 or 1, wherein the sum of the indices n and m is preferably 1 or 2, more preferably 1.

[0032] It is intended that in formulas (1a) to (If), (IIa) to (IIf) and / or (IIIa) to (IIIf) at most 2 of the groups CR, for which X stands, are not equal to the group CH.

[0033] In a further embodiment of the electronic device, it is provided that the electronic device contains at least one connection comprising at least one structure of formulas (IVa), (IVb), (IVc), (IVd), (IVe) and / or (IVf), preferably the connection has a structure of the aforementioned formulas, wherein the remainders Y and R have the meaning previously mentioned, in particular for formulas (1a) to (If), the index k is equal to or different from 0 or 1, preferably 0, the index o is equal to or different from 0, 1 or 2, preferably 0 or 1, the index n is equal to or different from 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably 0 or 1 and the index m is equal to or different from 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably 0 or 1, wherein the sum of the indices k, m, n and o is preferably 1 or 2, particularly preferably 1.

[0034] Preferably, the sum of the indices k, m, n, and o in formulas (IIa) to (IIf), (IIIa) to (IIIf), and / or (IVa) to (IVf) is at most 6, preferably at most 4, and particularly preferably at most 2. It is further preferred that the sum of the indices o and n in formulas (IIa) to (IIf), (IIIa) to (IIIf), and / or (IVa) to (IVf) is at least 1. Particularly preferably, the sum of the indices o and n in formulas (IIa) to (IIf), (IIIa) to (IIIf), and / or (IVa) to (IVf) is 1 or 2, and especially preferably exactly 1.

[0035] Furthermore, it may be provided that the electronic device comprises at least one connection comprising a structure of the formulas (Va), (Vb), (Vc), (Vd), (Ve), (Vf), (Vg), (Vh), (Vi), (Vj) and / or (Vk), preferably the connection has a structure of the aforementioned formulas, where the remainders Y and R have the previously mentioned meaning and the following also applies: R a< is the same or different in each occurrence F, CN, N(Ar) 2 , N(R 1< ) 2 , Si(Ar) 3 , Si(R 1< ) 3 , B(Ar) 2 , B(R 1< ) 2 , a straight-chain alkyl or alkoxy group with 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group with 3 to 40 C atoms, wherein the alkyl or alkoxy group may each be substituted with one or more R 1< residues, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 1< residues; in this respect, R a< residues may also form a ring system with a residue R, wherein the residues Ar and R 1< have the aforementioned meaning; kist equal to or different from 0 or 1, preferably 0; oist equal to or different from 0, 1 or 2, preferably 0 or 1; nist equal to or different from 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably 0 or 1;and the number of particles is the same or different: 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1.

[0036] Preferably, it can be provided that in formulas (Va) to (Vk) the sum of the indices k, m, n and o is at most 6, preferably at most 4, particularly preferably at most 2, especially preferably at most 1 and most particularly preferably 0.

[0037] In a preferred embodiment, the two residues Y in the formulas presented above and below may be identical. Furthermore, in another preferred embodiment, the two residues Y in the formulas presented above and below may be different.

[0038] Preferably, at least one of the residues R and / or R a< is selected from the group consisting of fluorenes, indenofluorenes, spirobifluorenes, carbazoles, indenocarbazoles, indolocarbazoles, spirocarbazoles, pyrimidines, triazines, lactams, triarylamines, dibenzofurans, dibenzothienes, imidazoles, benzimidazoles, benzoxazoles, benzthiazoles, 5-aryl-phenanthridin-6-ones, 9,10-dehydrophenanthrenes, fluoranthenes, anthracenes, benzanthracenes, and fluoradenes.

[0039] It can preferably be provided that a residue R directly bonded to a nitrogen atom does not represent a group selected from F, CN, N(Ar)₂, N(R₁<)₂, where R₁< has the meaning given above, particularly for formulas (1a) to (If). Accordingly, in formulas (Vf) to (Vk), the group R₁< preferably does not represent an F, CN, N(Ar)₂, N(R₁<)₂ residue, where R₁< has the meaning given above, particularly for formulas (1a) to (If). In a further preferred embodiment, the structures of formulas (1a) to (If) and the preferred embodiments of these structures described above and below do not have a nitrogen-narrowing bond.

[0040] Furthermore, it may be provided that at least one of the residues R and / or R a< 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, 9,9'-diaryl-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, pyrenyl, triazinyl, imidazolyl, benzimidazolyl, benzoxazolyl, benzthiazolyl, 1-, 2-, 3- or 4-carbazolyl, 1- or 2-napthyl, anthracenyl, preferably 9-anthracenyl, trans- and cis-indenofluorenyl, indenocarbazolyl, indolocarbazolyl, spirocarbazolyl, 5-aryl-phenanthridin-6-on-yl, 9,10-dehydrophenanthrenyl, fluoranthenyl, tolyl, mesityl, phenoxytolulyl, anisolyl, triarylaminyl, bis-triarylaminyl, tristriarylaminyl, Hexamethylindanyl, tetralinyl, monocycloalkyl, biscycloalkyl, tricycloalkyl, alkyl, such astert-Butyl, Methyl, Propyl, Alkoxyl, Alkylsulfanyl, Alkylaryl, Triarylsilyl, Trialkylsilyl, Xanthenyl, 10-Aryl-Phenoxazinyl, Phenanthrenyl and / or Triphenylenyl, each of which may be substituted by one or more substituents, but preferably are unsubstituted, wherein Phenyl, Spirobifluorene, Fluorene, Dibenzofuran, Dibenzothiophene, Anthracene, Phenanthrene, Triphenylene groups are particularly preferred.

[0041] If the structures described above and below are substituted by substituents R and / or R a<, then these substituents R and / or R a< are preferably chosen from the group consisting of H, D, F, CN, N(Ar) 2 , a straight-chain alkyl or alkoxy group with 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group with 3 to 10 C atoms, each of which may be substituted with one or more R 1< groups, an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, each of which may be substituted with one or more R 1< groups, but is preferably unsubstituted;Optionally, two substituents R and / or R a<, which are preferably bonded to adjacent carbon atoms, can form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted with one or more R 1< groups, wherein the group Ar has the meaning given above, in particular for formulas (1a) to (If).

[0042] Particularly preferred are these substituents R and / or R a< selected from the group consisting of H, D, F, CN, N(Ar) 2 , a straight-chain alkyl group with 1 to 8 C atoms, preferably with 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group with 3 to 8 C atoms, preferably with 3 or 4 C atoms, each of which may be substituted with one or more R 1< groups, but preferably is unsubstituted, or an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably with 6 to 13 aromatic ring atoms, each of which may be substituted with one or more non-aromatic R 1< groups, but preferably is unsubstituted; Optionally, two substituents R 1< , preferably bonded to adjacent carbon atoms, can form a monocyclic or polycyclic aliphatic ring system, where Ar can have the meaning set out above.

[0043] Particularly preferred are the substituents R selected from the group consisting of H or an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, each of which may be substituted with one or more non-aromatic residues R 1<, but is preferably unsubstituted. Examples of suitable substituents R are selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, triazinyl, quinazolinyl, quinoxalinyl, quinolinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, 1-, 2-, 3- or 4-carbazolyl and indenocarbazolyl, each of which may be substituted by one or more residues R 1<, but are preferably unsubstituted.

[0044] Particularly preferred are the substituents R a< selected from the group consisting of an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, each of which may be substituted with one or more non-aromatic residues R 1<, but preferably is unsubstituted. Examples of suitable substituents R a< are selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, triazinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, 1-, 2-, 3- or 4-carbazolyl and indenocarbazolyl, each of which may be substituted by one or more residues R 1<, but are preferably unsubstituted.

[0045] Furthermore, it may be provided that the substitutes R and / or R a< of the structures set out above and below, preferably structures according to formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) do not form a condensed aromatic or heteroaromatic ring system, preferably not a condensed ring system, among themselves.

[0046] According to a further embodiment, the electronic device may contain at least one connection comprising a hole transport group, wherein preferably at least one of the previously described groups R and / or R a<, which may be contained, inter alia, in a structure according to formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk), comprises, preferably represents, a hole transport group. Hole transport groups are known in the art, preferably comprising triarylamine or carbazole groups.

[0047] Preferably, the hole transport group may comprise a group, preferably a group selected from formulas (H-1) to (H-3), wherein the dashed bond marks the bonding position and the symbols have the following meanings; Ar 2< , Ar 3< , Ar 4< is each independently an aromatic ring system with 6 to 40 C atoms or a heteroaromatic ring system with 3 to 40 C atoms, each of which may be substituted by one or more R 1< groups; p is 0 or 1; Z stands for 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 for a bond or C(R 1< ) 2 , N-Ar 1< , O or S; wherein the symbols Ar 1< and R 1< have the meanings given above, in particular for formulas (1a) to (1f). The presence of a non-binary bond is preferably excluded.

[0048] Furthermore, it may be provided that the hole transport group includes a group, preferably a group, which is selected from formulas (H-4) to (H-26), where Y< 1< represents O, S, C(R< 1< ) 2 , NR< 1< or NAr< 1<, the dashed line marks the bonding position, e is 0, 1 or 2, j is 0, 1, 2 or 3, h is the same or different at each occurrence 0, 1, 2, 3 or 4, p is 0 or 1, Ar< and R< have the meanings given above, in particular for formulas (1a) to (1f) and Ar< have the meanings given above, in particular for formulas (H-1) or (H-2). The presence of an NN bond is preferably excluded.

[0049] From the above formulation it is evident that if the index p = 0, the corresponding group Ar 2< is not present and a bond is formed.

[0050] Preferably, the group Ar 2< can form a continuous conjugation with the aromatic or heteroaromatic residue or the nitrogen atom to which the group Ar 2< can be bonded according to formulas (H-1) to (H-26).

[0051] In a further preferred embodiment, Ar 2< represents an aromatic or heteroaromatic ring system with 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system with 6 to 12 carbon atoms, which may be substituted by one or more substituents R 1<, but is preferably unsubstituted, wherein R 1< may have the meaning given above, particularly for formulas (1a) to (if). Particularly preferably, Ar 2< represents an aromatic ring system with 6 to 10 aromatic ring atoms or a heteroaromatic ring system with 6 to 13 heteroaromatic ring atoms, each of which may be substituted by one or more substituents R 1<, but is preferably unsubstituted, wherein R 1< may have the meaning given above, particularly for formulas (1a) to (if).

[0052] Furthermore preferably, the symbol Ar 2< shown in formulas (H-1) to (H-26) represents an aryl or heteroaryl residue with 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 ring atoms, such that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is directly bonded to the respective atom of the further group, i.e. via an atom of the aromatic or heteroaromatic group.

[0053] Furthermore, the group Ar 2< set out in formulas (H-1) to (H-26) may comprise an aromatic ring system with at most two fused aromatic and / or heteroaromatic six-membered rings, preferably no fused aromatic or heteroaromatic ring system with fused six-membered rings. Accordingly, naphthyl structures are preferred over anthracene structures. Fluorenyl, spirobifluorenyl, dibenzofuranyl, and / or dibenzothienyl structures are also preferred over naphthyl structures. Structures that do not exhibit condensation, such as phenyl, biphenyl, terphenyl, and / or quaterphenyl structures, are particularly preferred.

[0054] Furthermore, it may be provided that the group Ar 2< set out in formulas (H-1) to (H-26) includes at most 1 nitrogen atom, preferably at most 2 heteroatoms, in particular preferably at most one heteroatom and in particular preferably no heteroatom.

[0055] In a further preferred embodiment of the invention, Ar 3< and / or Ar 4<, whether identical or different, represent an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably an aromatic ring system with 6 to 12 aromatic ring atoms or a heteroaromatic ring system with 6 to 13 aromatic ring atoms, each of which may be substituted by one or more residues R 1<, but preferably is unsubstituted, wherein R 1< may have the meaning previously described, in particular in formulas (1a) to (1f).

[0056] According to a further embodiment, the device according to the invention may comprise at least one compound comprising an electron transport group-containing residue, wherein preferably at least one of the previously described groups R and / or R a<, which may be contained, inter alia, in a structure according to formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk), comprises, preferably represents, an electron transport group-containing residue. Electron transport groups are widely known in the art and enhance the ability of compounds to transport and / or conduct electrons.

[0057] Furthermore, devices according to the invention, comprising at least one compound, exhibit surprising advantages if this compound comprises 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.

[0058] In a preferred embodiment of the present invention, it can be provided that the electron transport group-comprising residue represents a group that can be represented by the formula (QL), wherein L' represents a bond or an aromatic or heteroaromatic ring system with 5 to 40, preferably 5 to 30 aromatic ring atoms, which may be substituted by one or more substituents R 1<, Q is an electron transport group, wherein R 1< has the meaning given above, in particular for formulas (1a) to (If), and the dashed bond marks the bonding position.

[0059] Preferably, group L< can form a continuous conjugation with group Q and the atom, preferably the carbon or nitrogen atom, to which group L< is bonded according to formula (QL). A continuous conjugation of the aromatic or heteroaromatic systems is formed as soon as direct bonds are formed between adjacent aromatic or heteroaromatic rings. Further linkage between the aforementioned conjugated groups, for example via an S, N, or O atom or a carbonyl group, does not impair conjugation.In a fluorene system, the two aromatic rings are directly bonded. The sp³-hybridized carbon atom at position 9 prevents condensation of these rings, but conjugation is still possible because this sp³-hybridized carbon atom at position 9 is not necessarily located between the electron-transporting group Q and the atom through which the group of formula (QL) bonds to other structural elements of a compound according to the invention. In contrast, in a second spirobifluorene structure, continuous conjugation can occur if the bond between group Q and the aromatic or heteroaromatic residue to which group L' according to formula (QL) is bonded is formed via the same phenyl group of the spirobifluorene structure or via phenyl groups of the spirobifluorene structure that are directly bonded to each other and lie in the same plane.If the connection between group Q and the aromatic or heteroaromatic residue to which group L' is bonded according to formula (QL) occurs via different phenyl groups of the second spirobifluorene structure, which are connected via the sp 3< hybridized carbon atom at position 9, the conjugation is interrupted.

[0060] In a further preferred embodiment of the invention, L 1< represents a bond or an aromatic or heteroaromatic ring system with 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system with 6 to 12 carbon atoms, which may be substituted by one or more substituents R 1<, but preferably is unsubstituted, wherein R 1< may have the meaning mentioned above, in particular for formulas (1a) to (If).

[0061] Particularly preferably, L' represents an aromatic ring system with 6 to 10 aromatic ring atoms or a heteroaromatic ring system with 6 to 13 heteroaromatic ring atoms, each of which may be substituted by one or more substituents R 2<, but preferably is unsubstituted, wherein R 2< can have the meaning mentioned above, in particular for formulas (1a) to (If).

[0062] Furthermore preferably, the symbol L' shown, among other things, in formula (QL), whether the same or different, represents a bond or an aryl or heteroaryl residue with 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 ring atoms, such that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is directly bonded, i.e. via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group.

[0063] Furthermore, it may be provided that the group L1< shown in formula (QL) comprises an aromatic ring system with at most two fused aromatic and / or heteroaromatic six-membered rings, preferably no fused aromatic or heteroaromatic ring system. Accordingly, naphthyl structures are preferred over anthracene structures. Furthermore, fluorenyl, spirobifluorenyl, dibenzofuranyl, and / or dibenzothienyl structures are preferred over naphthyl structures.

[0064] Structures that do not exhibit condensation, such as phenyl, biphenyl, terphenyl and / or quaterphenyl structures, are particularly preferred.

[0065] Examples of suitable aromatic or heteroaromatic ring systems L 1< are selected from the group consisting of ortho-, meta- or para-phenylenes, ortho-, meta- or para-biphenylenes, terphenylenes, in particular branched terphenylene, quaterphenylenes, in particular branched quaterphenylene, fluorenylenes, spirobifluorenylenes, dibenzofuranyles, dibenzothienylenes and carbazolylenes, each of which may be substituted by one or more residues R 1<, but are preferably unsubstituted.

[0066] Furthermore, it may be provided that the group L 1< set out in formula (QL) has at most 1 nitrogen atom, preferably at most 2 heteroatoms, in particular preferably at most one heteroatom and in particular preferably no heteroatom.

[0067] Preferably, the group Q or the electron transport group shown in formula (QL) can be selected from structures of formulas (Q-1), (Q-2), (Q-4), (Q-4), (Q-5), (Q-6), (Q-7), (Q-8), (Q-9) and / or (Q-10), wherein the dashed bond marks the bonding position, Q' represents CR 1< or N at each occurrence, and Q"NR 1< , O or S; wherein at least one Q' is equal to N and R 1< as defined above, in particular in formulas (1a) to (If).

[0068] Furthermore, the group Q or the electron transport group, which is represented, among other things, in formula (QL), may preferably be selected from a structure of formulas (Q-11), (Q-12), (Q-13), (Q-14) and / or (Q-15), wherein the symbol R 1< has the meaning previously given for formulas (1a) to (If), X' is N or CR 1< and the dashed bond marks the bonding position, wherein X' preferably represents a nitrogen atom.

[0069] In another embodiment, the group Q or the electron transport group set out in formula (QL) can be selected from structures of formulas (Q-16), (Q-17), (Q-18), (Q-19), (Q-20), (Q-21) and / or (Q-22), wherein the symbol R 1< has the meaning previously set out for formulas (1a) to (1b), the dashed line marks the connection position, and m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, n is 0, 1, 2 or 3, preferably 0, 1 or 2, and o is 0, 1 or 2, preferably 1 or 2. The structures of formulas (Q-16), (Q-17), (Q-18) and (Q-19) are preferred.

[0070] In another embodiment, the group Q or the electron transport group set out in formula (QL) can be selected from structures of formulas (Q-23), (Q-24) and / or (Q-25), wherein the symbol R 1< has the meaning previously set out for formula (1a) to (If) and the dashed bond marks the bonding position.

[0071] In another embodiment, the group Q or the electron transport group set out in formula (QL) can be selected from structures of formulas (Q-26), (Q-27), (Q-28), (Q-29) and / or (Q-30), where the symbols Ar< and R< have the meaning previously given for formulas (1a) to (1f), X' is N or CR<, and the dashed bond marks the bonding position. Preferably, in the structures of formulas (Q-26), (Q-27), and (Q-28), exactly one X' represents a nitrogen atom.

[0072] Preferably, the group Q or the electron transport group shown in formula (QL) can be selected from structures of formulas (Q-31), (Q-32), (Q-33), (Q-34), (Q-35), (Q-36), (Q-37), (Q-38), (Q-39), (Q-40), (Q-41), (Q-42), (Q-43) and / or (Q-44), wherein the symbols Ar 1< and R 1< have the meaning previously set out for formulas (1a) to (1f), the dashed line 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 I is 1, 2, 3, 4 or 5, preferably 0, 1 or 2.

[0073] In a further preferred embodiment of the invention, Ar 1< represents, in each instance, an aromatic or heteroaromatic ring system, preferably an aryl or heteroaryl residue with 5 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably an aromatic ring system, preferably an aryl residue with 6 to 12 aromatic ring atoms, or a heteroaromatic ring system, preferably a heteroaryl group with 5 to 13 aromatic ring atoms, each of which may be substituted by one or more residues R 2<, but preferably is unsubstituted, wherein R 2< may have the meaning previously described, in particular in formulas (1a) to (1f).

[0074] Preferably, the symbol Ar 1< represents an aryl or heteroaryl residue, such that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is directly, i.e. via an atom of the aromatic or heteroaromatic group, bonded 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).

[0075] Advantageously, Ar 1< in formulas (H-1) to (H-26) or (Q-26) to (Q-44) represents an aromatic ring system with 6 to 12 aromatic ring atoms, which may be substituted with one or more substituents R 2<, but is preferably unsubstituted, wherein R 2< can have the meaning previously described, in particular for formulas (1a) to (If).

[0076] Preferably, the residues R1< or R2< 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 or heteroaryl group Ar1<, Ar2<, Ar3< and / or Ar4< to which the residues R1< or R2< are bonded. This excludes the formation of a fused ring system with possible substituents R2< that may be bonded to the residues R1<.

[0077] Furthermore, it may 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, imidazolyl, benzimidazolyl, benzoxazolyl, benzthiazolyl, 1-, 2-, 3- or 4-carbazolyl, indenocarbazolyl, 1- or 2-napthyl, anthracenyl, preferably 9-Anthracenyl, phenanthrenyl and / or triphenylenyl, each of which may be substituted by one or more R 1< and / or R 2< groups, but preferably are unsubstituted, wherein phenyl, spirobifluorene, fluorene, dibenzofuran, dibenzothiophene, anthracene, phenanthrene, and triphenylene groups are particularly preferred.

[0078] In a preferred embodiment, it can be provided that at least two residues R and / or R a< in a structure according to formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) each comprise, preferably represent, a hole transport group.

[0079] Furthermore, it may be provided that at least one of the residues R and / or R a< in a structure according to formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) comprises two hole transport groups. In this case, one hole transport group can be considered as residue R 1<, whereby the substituents R 1< shown in the structures of formulas (H-1) to (H-26) are to be replaced by residues R 2<.

[0080] Furthermore, it may be provided that at least one of the residues R 1< in a structure according to one of the formulas (Vg) to (Vk) comprises a hole transport group, in which case the substituents R 1< shown in the structures of formulas (H-1) to (H-26) are to be replaced by residues R 2<.

[0081] In a preferred embodiment, it can be provided that at least two residues R and / or R a< in a structure according to formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) each comprise an electron transport group-comprising residue, preferably represent.

[0082] Furthermore, it may be provided that at least one of the residues R and / or R a< in a structure according to formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) comprises two electron-transport group-containing residues. In this case, one electron-transport group-containing residue can be considered as residue R 1<, in which case the substituents R 1< shown in the structures of formulas (QL) and / or (Q-1) to (Q-44) are to be replaced by residues R 2<.

[0083] Furthermore, it may be provided that at least one of the residues R 1< in a structure according to one of the formulas (Vg) to (Vk) comprises an electron transport group-containing residue, in which case the substituents R 1< shown in the structures of formulas (H-1) to (H-26) are to be replaced by residues R 2<, in which case the substituents R 1< shown in the structures of formulas (QL) and / or (Q-1) to (Q-44) are to be replaced by residues R 2<.

[0084] In a further embodiment, it can be provided that at least one of the residues R and / or R a< in a structure according to formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) comprises a hole transport group, preferably represents, and at least one of the residues R and / or R a< comprises an electron transport group-comprising residue, preferably represents.

[0085] Furthermore, it may be provided that at least one of the residues R and / or R a< in a structure according to formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) comprises both an electron-transporting residue and a hole-transporting residue. In this case, an electron-transporting residue or a hole-transporting residue can be considered as residue R 1<, in which case the substituents R 1< shown in the structures of formulas (QL), (Q-1) to (Q-44) or (H-1) to (H-26) are to be replaced by residues R 2<.

[0086] In a further embodiment, it can be provided that at least one of the residues R and / or R< a< comprises at least one group that leads to wide-band-gap materials. The term "group that leads to wide-band-gap materials" indicates that the compounds can be used as wide-band-gap materials, so that the compounds have corresponding groups. Wide-band-gap materials will be explained in more detail later.

[0087] Furthermore, it may be provided that at least one of the residues R and / or R< a< comprises at least one group leading to materials that can be used as host materials. The term "group leading to materials that can be used as host materials" indicates that the compounds can be used as host materials, such that the compounds contain corresponding groups. Host materials are explained in more detail later.

[0088] In a further embodiment, the compound may comprise a condensed aromatic or heteroaromatic ring system with at least 2, preferably three condensed rings, which may optionally be substituted.

[0089] Preferably, at least one of the residues R and / or R a< in structures of formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) comprises at least one aromatic or heteroaromatic ring system with two, preferably three, condensed aromatic or heteroaromatic rings.

[0090] Preferably, the aromatic or heteroaromatic ring system with two, preferably three, condensed aromatic or heteroaromatic rings may be selected from the groups of formulas (Ar-1) to (Ar-11). wherein X' is N or CR 1< , preferably CR 1< , L' represents a bond or an aromatic or heteroaromatic ring system with 5 to 40, preferably 5 to 30 aromatic ring atoms, which may be substituted by one or more substituents R 1< , wherein R 1< has the meaning set forth above, in particular for formulas (1a) to (If) and the dashed bond marks the bonding position.

[0091] It is particularly preferred that the aromatic or heteroaromatic ring system with two, preferably with three condensed aromatic or heteroaromatic rings is selected from the groups of formulas (Ar'-1) to (Ar'-11), where L' represents a bond or an aromatic or heteroaromatic ring system with 5 to 40, preferably 5 to 30 aromatic ring atoms, which may be substituted by one or more substituents R 1<, where R 1< has the meaning set out above, in particular for formulas (1a) to (If), the dashed bond marks the bonding position and the following applies to the indices: pist 0 or 1; eist 0, 1 or 2, preferably 0 or 1; jist, in each occurrence independently 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably 0 or 1; hist, in each occurrence independently 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1; iist, in each occurrence independently 0, 1 or 2; mist an integer in the range of 0 to 7, preferably 0, 1, 2, 3, 4, 5 or 6, particularly preferably 0, 1, 2, 3 or 4, especially preferably 0, 1 or 2.

[0092] Preferably, the sum of the indices p, e, i, j, h and m in the structures of formula (Ar'-1) to (Ar'-11) is at most 3, preferably at most 2 and particularly preferably at most 1.

[0093] The structures of formulas (Ar-1) to (Ar-11) and / or (Ar'-1) to (Ar'-11) presented above are particularly preferred residues for compounds suitable for use as fluorescent emitters or as blue OLED materials.

[0094] In a preferred embodiment of the present invention, one of the previously described structures of formulas (Ar-1) to (Ar-11) and / or (Ar'-1) to (Ar'-11) represents a residue Ra< in a structure of formulas (Vb) to (Vk), preferably (Vc) to (Ve).

[0095] In a further preferred embodiment of the present invention, the group L' in the previously described structures of formulas (Ar-1) to (Ar-11) and / or (Ar'-1) to (Ar'-11) represents an aromatic or heteroaromatic ring system with 5 to 40, preferably 5 to 30 aromatic ring atoms, which may be substituted by one or more residues R 1<, wherein R 1< has the meaning previously described, in particular for formulas (1a) to (If).

[0096] If X 1< stands for CR 1< or if the aromatic and / or heteroaromatic group is substituted by substituents R 1<, then these substituents R 1< are preferably chosen from the group consisting of H, D, F, CN, N(Ar 1< ) 2 , a straight-chain alkyl or alkoxy group with 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group with 3 to 10 C atoms, each of which may be substituted with one or more substituents R 2<, wherein one or more H atoms may be replaced by D , an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, each of which may be substituted with one or more substituents R 2<, but is preferably unsubstituted, ;Optionally, two substituents R 1<, which are preferably bonded to adjacent carbon atoms, can form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, wherein the group Ar 1< has the meaning previously mentioned, in particular for formulas (1a) to (If).

[0097] Particularly preferred are these substituents R 1< selected from the group consisting of H, D, F, CN, N(Ar 1< ) 2 , a straight-chain alkyl group with 1 to 8 C atoms, preferably with 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group with 3 to 8 C atoms, preferably with 3 or 4 C atoms, each of which may be substituted with one or more R 2< groups, but preferably is unsubstituted, or an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably with 6 to 13 aromatic ring atoms, each of which may be substituted with one or more non-aromatic R 2< groups, but preferably is unsubstituted; Optionally, two substituents R 1< , preferably bonded to adjacent carbon atoms, can form a monocyclic or polycyclic aliphatic ring system, where Ar 1< can have the meaning set out above.

[0098] Particularly preferred are the substituents R 1< selected from the group consisting of H or an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, each of which may be substituted with one or more non-aromatic residues 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, each of which may be substituted by one or more residues R 2<, but are preferably unsubstituted.

[0099] Furthermore, it can be provided that the substituents R 1< of an aromatic or heteroaromatic ring system do not form a condensed aromatic or heteroaromatic ring system with other ring atoms of the aromatic or heteroaromatic ring system, preferably not a condensed ring system. This includes the formation of a condensed ring system with possible substituents R 2<, which may be bonded to the R 1< groups.

[0100] Furthermore, it may be provided that in a structure according to formula (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) at least one remainder R 1< or Ar 1< represents a group selected from the formulas (R 1< -1) to (R 1< - 43), or in a structure according to formula (H-1) to (H-26), (QL), (Q-1) to (Q-44), (Ar-1) to (Ar-11) and / or (Ar'-1) to (Ar'-11) at least one remainder Ar 1< or R 1< represents a group selected from the formulas (R 1< -1) to (R 1< - 43). where the following applies to the symbols used: Y 1< is O, S or NR 2< , preferably O or S; kist is 0 or 1 regardless of occurrence; iist is 0, 1 or 2 regardless of occurrence; jist is 0, 1, 2 or 3 regardless of occurrence; hist is 0, 1, 2, 3 or 4 regardless of occurrence; gist is 0, 1, 2, 3, 4 or 5 regardless of occurrence; R 2< can have the meaning mentioned above, in particular for formulas (1a) to (If) and the dashed line marks the tie position.

[0101] The groups of formulas R 1< -1 to R 1< -28 are preferred, with groups R'-1, R 1< -3, R 1< -4, R'-10, R'-11, R'-12, R'-13, R'-14, R'-16, R'-17, R'-18, R 1< -19, R 1< -20, R 1< -21 and / or R 1< -22 being particularly preferred.

[0102] Preferably, the sum of the indices k, i, j, h and g in the structures of the formula (R 1< -1) to (R 1< -43) may be at most 3, preferably at most 2 and particularly preferably at most 1.

[0103] Preferably, the R 2< residues in the formulas (R 1< -1) to (R 1< -43) do not form a condensed aromatic or heteroaromatic ring system with the ring atoms of the aryl group or heteroaryl group to which the R 2< residues are bonded, preferably not a condensed ring system.

[0104] The previously set forth residues of formulas (R 1< -1) to (R 1< -43) represent preferred residues Ar according to formulas (1a) to (1f) or Ar 3< , Ar 4< according to formulas (H-1) to (H-3) or preferred embodiments of these formulas, wherein in this case the groups R 2< set forth in formulas (R 1< -1) to (R 1< -43) are to be replaced by residues R 1< . The previously set forth preferences with regard to formulas (R 1< -1) to (R 1< -43) apply accordingly.

[0105] Preferably, the compound may comprise at least one connecting group selected from formulas (L 1< -1) to (L 1< -73), preferably in the structure according to formulas (H-1) to (H-26), the group Ar 2< selected from formulas (L 1< -1) to (L 1< -73), or the electron transport group is connected to further structural elements via a connecting group selected from formulas (L 1< -1) to (L 1< -73), or the residue L 1< in formulas (QL), (Ar-1) to (Ar-11) and / or (Ar'-1) to (Ar'-11) represents a group selected from formulas (L 1< -1) to (L 1< -73). wherein the dashed lines mark the attachment positions, the index k is 0 or 1, the index I is 0, 1 or 2, the index j is 0, 1, 2 or 3 regardless of occurrence; the index h is 0, 1, 2, 3 or 4 regardless of occurrence, the index g is 0, 1, 2, 3, 4 or 5; the symbol Y 2< is O, S or NR 1< , preferably O or S; and the symbol R 1< has the meaning given above, in particular for formulas (1a) to (if).

[0106] Preferably, the sum of the indices k, l, g, h, and j in the structures of formula (L1 < -1) to (L1 < -73) is at most 3, preferably at most 2, and particularly preferably at most 1. Preferred compounds according to the invention with a group of formulas (H-1) to (H-26) comprise a group Ar2< selected from one of the formulas (L1 < -1) to (L1 < -46) and / or (L1 < -57) to (L1 < -73), preferably the formula (L1 < -1) to (L1 < -32) and / or (L1 < -57) to (L1 < -73), and particularly preferably the formula (L1 < -1) to (L1 < -10) and / or (L1 < -57) to (L1 < -68).Advantageously, the sum of the indices k, l, g, h and j in the structures of the formulas (L 1< -1) to (L 1< -46) and / or (L 1< -57) to (L 1< -73), preferably the formula (L 1< -1) to (L 1< -32) and / or (L 1< -57) to (L 1< -73), especially preferably the formula (L 1< -1) to (L 1< -10) and / or (L 1< -57) to (L 1< -68) can each be at most 3, preferably at most 2 and particularly preferably at most 1.

[0107] Preferred compounds according to the invention with a group of formula (QL) comprise a group L 1< , which represents a bond or which is selected from one of the formulas (L 1< -1) to (L 1< -46) and / or (L 1< -57) to (L 1< -73), preferably the formula (L 1< -1) to (L 1< -32) and / or (L 1< -57) to (L 1< -73), particularly preferably the formula (L 1< -1) to (L 1< -10) and / or (L 1< -57) to (L 1< -68). Advantageously, the sum of the indices k, l, g, h and j in the structures of the formulas (L 1< -1) to (L 1< -46) and / or (L 1< -57) to (L 1< -73), preferably the formula (L 1< -1) to (L 1< -32) and / or (L 1< -57) to (L 1< -73), especially preferably the formula (L 1< -1) to (L 1< -10) and / or (L 1< -57) to (L 1< -68) can each be at most 3, preferably at most 2 and particularly preferably at most 1.

[0108] Preferred compounds according to the invention with a group of formulas (Ar-1) to (Ar-11) and / or (Ar'-1) to (Ar'-11) comprise a group L 1< , which represents a bond or which is selected from one of the formulas (L 1< -1) to (L 1< -46) and / or (L 1< -57) to (L 1< -73), preferably the formula (L 1< -1) to (L 1< -32) and / or (L 1< -57) to (L 1< -73), particularly preferably the formula (L 1< -1) to (L 1< -10) and / or (L 1< -57) to (L 1< -68). Advantageously, the sum of the indices k, l, g, h and j in the structures of the formulas (L 1< -1) to (L 1< -46) and / or (L 1< -57) to (L 1< -73), preferably the formula (L 1< -1) to (L 1< -32) and / or (L 1< -57) to (L 1< -73), especially preferably the formula (L 1< -1) to (L 1< -10) and / or (L 1< -57) to (L 1< -68) can each be at most 3, preferably at most 2 and particularly preferably at most 1.

[0109] Preferably, the R 2< residues in the formulas (L 1< -1) to (L 1< -73) do not form a condensed aromatic or heteroaromatic ring system with the ring atoms of the aryl group or heteroaryl group to which the R 2< residues are bonded, preferably not a condensed ring system.

[0110] According to a preferred embodiment, a compound according to claim 12 or 13 can be represented by at least one of the structures according to formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk). Preferably, compounds comprising structures according to formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) have a molecular weight of less than or equal to 5000 g / mol, preferably less than or equal to 4000 g / mol, particularly preferably less than or equal to 3000 g / mol, especially preferably less than or equal to 2000 g / mol and most preferably less than or equal to 1200 g / mol.

[0111] Furthermore, preferred compounds according to the invention are characterized by being sublimable. These compounds generally have a molar mass of less than approximately 1200 g / mol.

[0112] If the compound according to the invention is substituted with aromatic or heteroaromatic groups R1< or R2<, respectively, it is preferred that these groups do not have aryl or heteroaryl groups with more than two directly fused aromatic six-membered rings. Particularly preferred are the substituents that have no aryl or heteroaryl groups with directly fused six-membered rings at all. This preference is due to the low triplet energy of such structures. Condensed aryl groups with more than two directly fused aromatic six-membered rings that are nevertheless suitable according to the invention are phenanthrene and triphenylene, since these also exhibit a high triplet energy level.

[0113] In the embodiment of the compounds according to the invention for use as fluorescent emitters or as blue OLED materials, preferred compounds may contain corresponding groups, for example fluorene, anthracene and / or pyrene groups, which may be substituted with groups R 1< or R 2< or which are formed by corresponding substitution of the groups (L 1< -1) to (L 1< -73) or (R 1< -1) to (R 1< -43) with the substituents R 1< or R 2<.

[0114] In a further preferred embodiment of the invention, R 2< , for example in a structure according to formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) as well as preferred embodiments of this structure or the structures to which reference is made, is selected in each occurrence, in the same or different ways, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon residue with 1 to 10 C atoms, preferably with 1, 2, 3 or 4 C atoms, or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, preferably with 5 to 24 aromatic ring atoms, particularly preferably with 5 to 13 aromatic ring atoms, which may be substituted by one or more alkyl groups, each with 1 to 4 carbon atoms, but is preferably unsubstituted.

[0115] Preferably, the residues R 2< do not form a condensed aromatic or heteroaromatic ring system with the ring atoms of the aryl group or heteroaryl group to which the residues R 2< are bonded, preferably not a condensed ring system.

[0116] Furthermore, it can be provided that the compound according to the invention is not in direct contact with a metal atom, preferably does not represent a ligand for a metal complex.

[0117] Compounds with structures of formula (Va) which have the following properties are particularly preferred: Rest R a< comprises one of the groups preferably especially preferred especially preferred H-1 to H-26 H-1 - H-11 and H-15 to H-17 H-1 to H-11 H-1 H-1 to H-26 H-4 to H-26 H-4 to H-11 and H-15 to H-17 H4, H5 QL Q-11 to Q-25, Q-16 to 19 and Q-23 to Q-25 Q-23 QL Q-26 to Q44 Q-33 to Q-42 Q-35 Ar-1 to Ar-11 Ar-3 to Ar-11 Ar-3 to Ar-5 Ar-5 Ar'-1 to Ar'-11 Ar'-3 to Ar'-11 Ar'-3 to Ar'-5 Ar'-5

[0118] Compounds with structures of formula (Vb) which have the following properties are particularly preferred: Rest R a< comprises one of the groups preferably especially preferred especially preferred H-1 to H-26 H-1 - H-11 and H-15 to H-17 H-1 to H-11 H-1 H-1 to H-26 H-4 to H-26 H-4 to H-11 and H-15 to H-17 H4, H5 QL Q-11 to Q-25, Q-16 to 19 and Q-23 to Q-25 Q-23 QL Q-26 to Q44 Q-33 to Q-42 Q-35 Ar-1 to Ar-11 Ar-3 to Ar-11 Ar-3 to Ar-5 Ar-5 Ar'-1 to Ar'-11 Ar'-3 to Ar'-11 Ar'-3 to Ar'-5 Ar'-5

[0119] Connections with structures of the Formula (Vc), which has the following properties: Rest R a< comprises one of the groups preferably especially preferred especially preferred H-1 to H-26 H-1 - H-11 and H-15 to H-17 H-1 to H-11 H-1 H-1 to H-26 H-4 to H-26 H-4 to H-11 and H-15 to H-17 H4, H5 QL Q-11 to Q-25, Q-16 to 19 and Q-23 to Q-25 Q-23 QL Q-26 to Q44 Q-33 to Q-42 Q-35 Ar-1 to Ar-11 Ar-3 to Ar-11 Ar-3 to Ar-5 Ar-5 Ar'-1 to Ar'-11 Ar'-3 to Ar'-11 Ar'-3 to Ar'-5 Ar'-5

[0120] Compounds with structures of formula (Vd) which have the following properties are particularly preferred: Rest R a< comprises one of the groups preferably especially preferred especially preferred H-1 to H-26 H-1 - H-11 and H-15 to H-17 H-1 to H-11 H-1 H-1 to H-26 H-4 to H-26 H-4 to H-11 and H-15 to H-17 H4, H5 QL Q-11 to Q-25, Q-16 to 19 and Q-23 to Q-25 Q-23 QL Q-26 to Q44 Q-33 to Q-42 Q-35 Ar-1 to Ar-11 Ar-3 to Ar-11 Ar-3 to Ar-5 Ar-5 Ar'-1 to Ar'-11 Ar'-3 to Ar'-11 Ar'-3 to Ar'-5 Ar'-5

[0121] Compounds with structures of the formula (Ve) which have the following properties are particularly preferred: Rest R a< comprises one of the groups preferably especially preferred especially preferred H-1 to H-26 H-1 - H-11 and H-15 to H-17 H-1 to H-11 H-1 H-1 to H-26 H-4 to H-26 H-4 to H-11 and H-15 to H-17 H4, H5 QL Q-11 to Q-25, Q-16 to 19 and Q-23 to Q-25 Q-23 QL Q-26 to Q44 Q-33 to Q-42 Q-35 Ar-1 to Ar-11 Ar-3 to Ar-11 Ar-3 to Ar-5 Ar-5 Ar'-1 to Ar'-11 Ar'-3 to Ar'-11 Ar'-3 to Ar'-5 Ar'-5

[0122] Connections with structures of the Formula (Vf) which has the following properties: Rest R a< comprises one of the groups preferably especially preferred especially preferred H-1 to H-26 H-1 - H-11 and H-15 to H-17 H-1 to H-11 H-1 H-1 to H-26 H-4 to H-26 H-4 to H-11 and H-15 to H-17 H4, H5 QL Q-11 to Q-25, Q-16 to 19 and Q-23 to Q-25 Q-23 QL Q-26 to Q44 Q-33 to Q-42 Q-35 Ar-1 to Ar-11 Ar-3 to Ar-11 Ar-3 to Ar-5 Ar-5 Ar'-1 to Ar'-11 Ar'-3 to Ar'-11 Ar'-3 to Ar'-5 Ar'-5

[0123] Connections with structures of the Formula (Vk) which has the following properties: Rest R a< comprises one of the groups preferably especially preferred especially preferred H-1 to H-26 H-1 - H-11 and H-15 to H-17 H-1 to H-11 H-1 H-1 to H-26 H-4 to H-26 H-4 to H-11 and H-15 to H-17 H4, H5 QL Q-11 to Q-25, Q-16 to 19 and Q-23 to Q-25 Q-23 QL Q-26 to Q44 Q-33 to Q-42 Q-35 Ar-1 to Ar-11 Ar-3 to Ar-11 Ar-3 to Ar-5 Ar-5 Ar'-1 to Ar'-11 Ar'-3 to Ar'-11 Ar'-3 to Ar'-5 Ar'-5

[0124] The remainders of formulas H-1 to H-26 in the tables presented above are preferably selected according to the following criteria: Ar 1< (if available) Ar 2< (if available) Ar 3< , Ar 4< R 1< -1 to R 1< -43 L 1< -1 to L 1< -73 R 1< -1 to R 1< -43 R 1< -1 to R 1< -28 L 1< -1 to L 1< -46 or L 1< -57 to L 1< -73 R 1< -1 to R 1< -28 R 1< -1 to R 1< -43 L1 < -1 to L1 < -4 R 1< -1 to R 1< -43

[0125] The remainders of the formula QL in the tables presented above are preferably selected according to the following criteria: L 1< preferably Q preferably A bond or L 1< -1 to L 1< -73 A bond or L 1< -1 to L 1< -46 or L 1< -57 to L 1< -73 Q-11 to Q-25 Q-16 to 19 and Q-23 to Q-25 A bond or L 1< -1 to L 1< -73 A bond or L 1< -1 to L 1< -46 or L 1< -57 to L 1< -73 Q-26 to Q44 Q-33 to Q-42

[0126] Examples of suitable connections according to the embodiments listed above are the connections listed in the following table:

[0127] Preferred embodiments of the compounds according to the invention are described in more detail in the examples, wherein these compounds can be used alone or in combination with others for all uses according to the invention.

[0128] Provided that the conditions specified in claim 1 are met, the preferred embodiments mentioned above can be combined with one another as desired. In a particularly preferred embodiment of the invention, the preferred embodiments mentioned above apply simultaneously.

[0129] The compounds according to the invention can in principle be produced by various methods. However, the methods described below have proven to be particularly suitable.

[0130] Therefore, a further object of the present invention is a method for production according to claim 18, in which a compound comprising a heterocyclic structure is coupled in a coupling reaction with a compound comprising at least one aromatic or heteroaromatic group.

[0131] Suitable compounds, comprising at least one heterocyclic structure, can often be obtained commercially, with the starting compounds presented in the examples being obtainable by known methods, which are therefore referenced here.

[0132] These compounds can be reacted with other compounds comprising at least one aromatic or heteroaromatic group by known coupling reactions, the necessary conditions for which are known to the person skilled in the art and detailed information in the examples assists the person skilled in the art in carrying out these reactions.

[0133] Particularly suitable and preferred coupling reactions, all leading to CC couplings and / or CN couplings, are those according to BUCHWALD, SUZUKI, YAMAMOTO, STILLE, HECK, NEGISHI, SONOGASHIRA and HIYAMA. These reactions are widely known, and the examples provided offer further guidance to those skilled in the art.

[0134] The principles of the manufacturing processes described above are known from the literature for similar compounds and can be easily adapted by a person skilled in the art to produce the compounds according to the invention. Further information can be found in the examples.

[0135] By these methods, possibly followed by purification, such as recrystallization or sublimation, the compounds comprising structures according to formula (1a) to (1f) can be obtained in high purity, preferably more than 99% (determined by <1H-NMR and / or HPLC).

[0136] The compounds may also possess suitable substituents, for example, longer alkyl groups (approximately 4 to 20 carbon atoms), particularly branched alkyl groups, or optionally substituted aryl groups, such as xylyl, mesityl, or branched terphenyl or quaterphenyl groups, which ensure solubility in common organic solvents, so that the compounds are soluble in toluene or xylene at room temperature at sufficient concentrations to allow processing from solution. These soluble compounds are particularly well-suited for processing from solution, for example, by printing processes. Furthermore, it should be noted that the compounds comprising at least one structure of formulas (1a) to (1f), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf), and / or (Va) to (Vk) already exhibit increased solubility in these solvents.

[0137] Furthermore, the compounds can contain one or more crosslinkable groups. A "crosslinkable group" is a functional group capable of irreversible reaction, resulting in the formation of a crosslinked material that is insoluble. Crosslinking can typically be accelerated by heat or by UV, microwave, X-ray, or electron radiation. This process produces very little byproduct. Moreover, the crosslinkable groups present in these functional compounds crosslink very readily, requiring lower energy levels for crosslinking (e.g., < 200°C for thermal crosslinking).

[0138] Examples of crosslinkable groups are units containing a heterocyclic, addition-polymerizable residue. Crosslinkable groups include, among others, di(hydrocarbyl)amino, cyclobutylphenyl, and tri(C1-4)-alkylsilyl. Cyclobutylphenyl is particularly preferred.

[0139] The compounds according to the invention can also be mixed with a polymer. It is also possible to covalently incorporate these compounds into a polymer. This is particularly possible with compounds substituted with reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic acid esters, or with reactive, polymerizable groups, such as olefins or oxetanes. These can be used as monomers for the production of corresponding oligomers, dendrimers, or polymers. The oligomerization or polymerization preferably proceeds 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.

[0140] A further aspect of the invention is therefore oligomers, polymers, or dendrimers according to claim 14, comprising one or more of the structures of formulas (1a) to (1f), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf), and / or (Va) to (Vk), wherein one or more bonds of the compounds according to the invention or of the structures of formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf), and / or (Va) to (Vk) are present to the polymer, oligomer, or dendrimer. Depending on the linkage of the structures, 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.

[0141] To produce the oligomers or polymers, the monomers are homopolymerized or copolymerized with further monomers. Copolymers are preferred, wherein the units according to formulas (1a) to (1f), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) or the previously and subsequently described preferred embodiments are present in amounts of 0.01 to 99.9 mol%, preferably 5 to 90 mol%, and particularly preferably 20 to 80 mol%. Suitable and preferred comonomers forming the polymer backbone are selected from fluorenes (e.g., according to EP 842208 or WO 2000 / 022026), spirobifluorenes (e.g., according to EP 707020, EP 894107 or WO 2006 / 061181), para-phenylenes (e.g., according to WO 92 / 18552), carbazoles (e.g., according to WO 2004 / 070772 or WO 2004 / 113468), thiophenes (e.g., according to EP 1028136), dihydrophenanthrenes (e.g., according to WO 2005 / 014689), cis- and trans-indenofluorenes (e.g., according to WO 2004 / 041901 or WO 2004 / 113412). Ketones (e.g. according to WO 2005 / 040302), phenanthrenes (e.g.B. 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.

[0142] Of particular interest are compounds according to the invention which are characterized by a high glass transition temperature. In this context, compounds according to the invention comprising structures according to formulas (1a) to (1f), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) or the previously and subsequently described preferred embodiments are particularly preferred, which have a glass transition temperature of at least 70 °C, particularly preferably at least 110 °C, most preferably at least 125 °C and most preferably at least 150 °C, as determined according to DIN 51005 (version 2005-08).

[0143] For processing the compounds according to the invention from the liquid phase, for example by spin coating or by printing processes, formulations of the compounds according to the invention are required. These formulations can be, for example, solutions, dispersions, or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents include, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrol, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin. Dodecylbenzene, ethyl benzoate, indane, NMP, p-cymene, phenetol,1,4-Diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, 2-methylbiphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, diethyl sebacic acid ester, octyl octanoate, heptylbenzene, menthyrosevalerate, cyclohexylhexanoate or mixtures of these solvents.

[0144] A further object of the present invention is therefore a formulation according to claim 16 or a composition comprising at least one compound according to the invention and at least one further compound. The further compound may, for example, be a solvent, in particular one of the solvents mentioned above or a mixture of these solvents. If the further compound comprises a solvent, this mixture is referred to herein as the formulation. The further compound may also be at least one further organic or inorganic compound that is also used in the electronic device, for example, an emitting compound and / or a further matrix material. Suitable emitting compounds and further matrix materials are listed later in connection with the organic electroluminescent device. The further compound may also be a polymer.

[0145] Another object of the present invention is therefore a composition comprising a compound according to claim 15. Functional materials are generally the organic or inorganic materials introduced between the anode and cathode. Preferably, the organic functional material is selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF (thermally activated delayed fluorescence), host materials, electron transport materials, electron injection materials, hole transport materials, hole injection materials, electron blocking materials, hole blocking materials, wide-band-gap materials, and n-dopeds.

[0146] Claim 15 also comprises a composition containing at least one compound according to the invention, preferably a compound according to formulas (1a) to (1b), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk), or the preferred embodiments described above and below, as well as at least one wide-band-gap material, wherein a wide-band-gap material is understood to be a material as defined in US 7,294,849. These systems exhibit particularly advantageous performance characteristics in electroluminescent devices.

[0147] Preferably, the additional compound can have a band gap of 2.5 eV or more, more preferably 3.0 eV or more, and most preferably 3.3 eV or more. The band gap can be calculated, among other methods, from the energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO).

[0148] 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 via quantum chemical calculations. For organic substances without metals, geometry optimization is first performed using the method "Ground State / Semi-empirical / Default Spin / AM1 / Charge 0 / Spin Singlet". Subsequently, an energy calculation is performed based on the optimized geometry. Here, the method "TD-SCF / DFT / Default Spin / B3PW91" with the basis set "6-31G(d)" (Charge 0, Spin Singlet) is used. For metal-containing compounds, the geometry is optimized using the method "Ground State / Hartree-Fock / Default Spin / LanL2MB / Charge 0 / Spin Singlet".The energy calculation is 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 these, the HOMO and LUMO energy levels, calibrated using cyclic voltammetry measurements, are determined in electron volts as follows: HOMO eV = HEh * 27.212 − 0.9899 / 1.1206 LUMO eV = LEh * 27.212 − 2.0041 / 1.385

[0149] For the purposes of this application, these values ​​are to be regarded as HOMO or LUMO energy levels of the materials.

[0150] The lowest triplet state T 1 is defined as the energy of the triplet state with the lowest energy, which results from the described quantum chemical calculation.

[0151] The lowest excited singlet state S 1 is defined as the energy of the lowest excited singlet state resulting from the described quantum chemical calculation.

[0152] The method described herein is independent of the software package used and always yields the same results. Examples of commonly used programs for this purpose are "Gaussian09W" (Gaussian Inc.) and Q-Chem 4.1 (Q-Chem, Inc.).

[0153] Claim 15 also comprises a composition comprising at least one compound according to the invention according to formulas (1a) to (1b), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) or the previously and subsequently described preferred embodiments, as well as at least one phosphorescent emitter, wherein the term phosphorescent emitter also includes phosphorescent dopants.

[0154] In a system containing a matrix material and a dopant, a dopant is understood to be the component whose proportion in the mixture is 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 larger.

[0155] Preferred phosphorescent dopants for use in matrix systems, preferably mixed matrix systems, are the preferred phosphorescent dopants listed below.

[0156] The term phosphorescent dopants typically encompasses 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, such as a quintet state.

[0157] Suitable phosphorescent compounds (= triplet emitters) are, in particular, compounds that emit light, preferably in the visible range, upon suitable excitation and also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, and especially preferably greater than 56 and less than 80, particularly a metal with this atomic number. Compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are preferred as phosphor emitters, especially compounds containing iridium or platinum.

[0158] Examples of the issuers described above can be found in applications WO 00 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 05 / 033244, WO 05 / 019373, US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, WO 2010 / 102709, WO 2011 / 032626, WO 2011 / 066898, WO 2011 / 157339, WO 2012 / 007086, WO 2014 / 008982, WO 2014 / 023377, WO 2014 / 094961, WO 2014 / 094960, WO 2015 / 036074, WO 2015 / 104045, WO 2015 / 117718, WO 2016 / 015815, WO 2016 / 124304, WO 2017 / 032439, WO 2018 / 011186, WO 2018 / 001990, WO 2018 / 019687, WO 2018 / 019688, WO 2018 / 041769, WO 2018 / 054798, WO 2018 / 069196, WO 2018 / 069197, WO 2018 / 069273, WO 2018 / 178001, WO 2018 / 177981, WO 2019 / 020538, WO 2019 / 115423, WO 2019 / 158453 and WO 2019 / 179909.In general, all phosphorescent complexes as used in phosphorescent electroluminescence devices according to the prior art and as known to the skilled person in the field of organic electroluminescence are suitable, and the skilled person can use further phosphorescent complexes without inventive effort.

[0159] Examples of phosphorescent dopants are listed in the following table.

[0160] When the compound is used as a matrix material for a phosphorescent compound in an emitting layer, it is preferably used in combination with one or more phosphorescent materials (triplet emitters). For the purposes of this invention, phosphorescence is understood to mean luminescence from an excited state with a higher spin multiplicity, i.e., a spin state > 1, in particular from an excited triplet state. For the purposes of this application, all luminescent complexes with transition metals or lanthanides, in particular all iridium, platinum, and copper complexes, are to be considered phosphorescent compounds.

[0161] The mixture of the compound and the emitting compound contains between 99 and 1 vol%, preferably between 98 and 10 vol%, particularly preferably between 97 and 60 vol%, and especially between 95 and 80 vol% of the compound, based on the total mixture of emitter and matrix material. Similarly, the mixture contains between 1 and 99 vol%, preferably between 2 and 90 vol%, and especially between 3 and 40 vol%, and particularly between 5 and 20 vol% of the emitter, based on the total mixture of emitter and matrix material.

[0162] In one embodiment of the invention, the compound according to the invention is used as the single matrix material ("single host") for the phosphorescent emitter.

[0163] In a preferred embodiment of the invention, the organic electroluminescent device according to the invention comprises the compound comprising structures according to formulas (1a) to (1f), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) or the preferred embodiments listed above as a matrix material, preferably as an 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 large-bandgap compound that is not involved, or not to a significant extent, in hole and electron transport in the layer. An emitting layer comprises at least one emitting compound.

[0164] In a further particularly preferred embodiment of the present invention, an organic electroluminescence device according to the invention comprises the compound comprising structures according to formulas (1a) to (1f), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) or the preferred embodiments listed above in a hole transport layer or an electron transport layer.

[0165] The present invention therefore also relates to a composition according to claim 15 comprising at least one compound according to the invention, preferably a compound according to formulas (1a) to (1f), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) or the previously and subsequently described preferred embodiments as well as at least one further matrix material.

[0166] Suitable matrix materials which can be used in combination with the compounds according to formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) or according to the preferred embodiments are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680, triarylamines, carbazole derivatives, etc. B. CBP (N,N-Biscarbazolylbiphenyl) or those in WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or WO 2013 / 041176, indolocarbazole derivatives, e.g. according to WO 2007 / 063754 or WO 2008 / 056746, indenocarbazole derivatives, e.g. according to WO 2010 / 136109, WO 2011 / 000455, WO 2013 / 041176 or WO 2013 / 056776, azacarbazole derivatives, e.g. B. according to EP 1617710, EP 1617711, EP 1731584, JP 2005 / 347160, bipolar matrix materials, e.g. according to WO 2007 / 137725, silanes, e.g. according to WO 2005 / 111172, azaborols or boron esters, e.g.according to WO 2006 / 117052, triazine derivatives, e.g. according to WO 2007 / 063754, WO 2008 / 056746, WO 2010 / 015306, WO 2011 / 057706, WO 2011 / 060859 or WO 2011 / 060877, zinc complexes, e.g. according to EP 652273 or WO 2009 / 062578, diazasilol or tetraazasilol derivatives, e.g. according to WO 2010 / 054729, diazaphosphol derivatives, e.g. according to WO 2010 / 054730, bridged carbazole derivatives, e.g. B. according to WO 2011 / 042107, WO 2011 / 060867, WO 2011 / 088877 and WO 2012 / 143080, triphenylene derivatives, e.g. according to WO 2012 / 048781, dibenzofuran derivatives, e.g. according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO 2017 / 148565 or biscarbazoles, e.g. according to JP 3139321 B2, lactams, e.g. B. according to WO 2011 / 116865, WO 2011 / 137951 or WO 2013 / 064206, 4-spirocarbazole derivatives, e.g. according to WO 2014 / 094963 or WO 2015 / 192939. Likewise, another phosphorescent emitter, which emits at a shorter wavelength than the actual emitter, may be present as a co-host in the mixture.

[0167] Preferred co-host materials are triazines, quinazolines, quinoxalines, triarylamine derivatives, especially monoamines, indenocarbazole derivatives, 4-spirocarbazole derivatives, lactams and carbazole derivatives.

[0168] Preferred triarylamine derivatives used as co-host materials together with the compounds according to the invention are selected from the compounds of the following formula (TA-1), where Ar 5<, whether identical or different in each occurrence, represents an aromatic or heteroaromatic ring system with 6 to 40 carbon atoms, each of which may be substituted with one or more R 1< groups, wherein optionally two or more adjacent R 1< substituents may form a mono- or polycyclic aliphatic ring system, which may be substituted with one or more R 2< groups, wherein the symbols R 1< and R 2< have the meanings given above, particularly for formulas (1a) to (if). Preferably, Ar 5<, whether identical or different in each occurrence, represents an aryl or heteroaryl group with 5 to 24, preferably 5 to 12, aromatic ring atoms, each of which may be substituted with one or more R 1< groups, but is preferably unsubstituted.

[0169] Examples of suitable groups Ar 5< are selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, indenocarbazolyl, 1-, 2-, 3- or 4-dibenzothienyl and 1-, 2-, 3- or 4-carbazolyl, each of which may be substituted by one or more residues R 1<, but are preferably unsubstituted.

[0170] The groups Ar 5< are preferably selected from the above-mentioned groups R 1< -1 to R 1< -43, either the same or different at each occurrence, and R 1< -1 to R 1< -28 are particularly preferred.

[0171] In a preferred embodiment of the compounds of formula (TA-1), at least one group Ar 5< 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 group Ar 5< is selected from a fluorene group or spirobifluorene group, wherein these groups may each be bonded to the nitrogen atom at 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 substituted with a dibenzofuran group, a dibenzothiophene group, or a carbazole group, in particular a dibenzofuran group, wherein the dibenzofuran or dibenzothiophene group is linked to the phenylene or biphenyl group, respectively, via the 1-, 2-, 3-, or 4-position.biphenyl group is linked and the carbazole group is linked to the phenylene or biphenyl group via the 1-, 2-, 3- or 4-position or via the nitrogen atom.

[0172] In a particularly preferred embodiment of the compounds of formula (TA-1), a group Ar 5< is selected from a fluorene or spirobifluorene group, in particular a 4-fluorene or 4-spirobifluorene group, and a group Ar 5< is selected from a biphenyl group, in particular a para-biphenyl group, or a fluorene group, in particular a 2-fluorene group, and the third group Ar 5< is selected from a para-phenylene group or a para-biphenyl group substituted with a dibenzofuran group, in particular a 4-dibenzofuran group, or a carbazole group, in particular an N-carbazole group or a 3-carbazole group.

[0173] Preferred indenocarbazole derivatives used as co-host materials together with the compounds according to the invention are selected from the compounds of the following formula (TA-2), where Ar 5< and R 1< have the meanings listed above, particularly for formulas (I) and / or (TA-1). Preferred embodiments of the group Ar 5< are the structures R 1< -1 to R 1< -43 listed above, and particularly preferably R 1< -1 to R 1< -28.

[0174] A preferred embodiment of the compounds of formula (TA-2) are the compounds of the following formula (TA-2a), where Ar< and R< have the meanings given above, particularly for formulas (I) and / or (TA-1). The two groups R< bonded to the indenocarbazole carbon atom preferably represent, either identically or differently, an alkyl group with 1 to 4 carbon atoms, particularly methyl groups, or an aromatic ring system with 6 to 12 carbon atoms, particularly phenyl groups. Particularly preferably, the two groups R< bonded to the indenocarbazole carbon atom represent methyl groups. Furthermore preferably, the substituent R< bonded to the indenocarbazole core in formula (TA-2a) represents H or a carbazole group, which may be bonded to the indenocarbazole core via the 1, 2, 3, or 4 position or via the N atom, particularly via the 3 position.

[0175] Preferred 4-spirocarbazole derivatives, which are used as co-host materials together with the compounds according to the invention, are selected from the compounds of the following formula (TA-3), where Ar 5< and R 1< 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 1< -43 listed above, and particularly preferably R 1< -1 to R 1< -28.

[0176] 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 1< -43 listed above, and particularly preferably R 1< -1 to R 1< -28.

[0177] Preferred lactams used as co-host materials together with the compounds according to the invention are selected from the compounds of the following formula (LAC-1), where R 1< has the meaning listed above.

[0178] A preferred embodiment of the compounds of formula (LAC-1) are the compounds of the following formula (LAC-1a), where R1< has the meaning given above, in particular for formulas (1a) to (1f). In each instance, R1< preferably represents H or an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, which may be substituted with one or more substituents R2<, where R2< may have the meaning given above. Most preferably, the substituents R1< are selected from the group consisting of H or an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, each of which may be substituted with one or more non-aromatic substituents R2<, but is preferably unsubstituted.Examples of suitable substituents R1< 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, each of which may be substituted by one or more substituents R2<, but are preferably unsubstituted. Suitable structures R1< are the same structures as those previously shown for R-1 to R-79, particularly preferably R1< -1 to R1< -51.

[0179] It may also be preferred to use several different matrix materials as a mixture, in particular at least one electron-conducting matrix material and at least one hole-conducting matrix material. Equally preferred is the use of a mixture of a charge-transporting matrix material and an electrically inert matrix material that does not participate, or does not participate to a significant extent, in charge transport, as described, for example, in WO 2010 / 108579. In particular, compounds with a large band gap that do not participate, or at least do not participate to a significant extent, in charge transport of the emitting layer are suitable as co-matrix materials in combination with the compound according to the invention. Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009 / 124627 or in WO 2010 / 006680.

[0180] It is also 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.

[0181] Particularly preferably, a compound according to the invention according to formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) can be used in a preferred embodiment as a matrix material in an emission layer of an organic electronic device, in particular in an organic electroluminescent device, for example in an OLED or OLEC. The matrix material, comprising a compound according to formulas (1a) to (If), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk) or the previously and subsequently described preferred embodiments, is present in the electronic device in combination with one or more dopants, preferably phosphorescent dopants.

[0182] In this case, the proportion of matrix material in the emitting layer is between 50.0 and 99.9 vol.%, preferably between 80.0 and 99.5 vol.%, and particularly preferably between 92.0 and 99.5 vol.% for fluorescent emitting layers and between 85.0 and 97.0 vol.% for phosphorescent emitting layers.

[0183] 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 between 0.5 and 8.0 vol.% for fluorescent emitting layers and between 3.0 and 15.0 vol.% for phosphorescent emitting layers.

[0184] 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 those materials with the smaller proportion in the system, and the matrix materials are those materials with the larger proportion. In some cases, however, the proportion of a single matrix material in the system may be smaller than the proportion of a single dopant.

[0185] In a further preferred embodiment of the invention, the compounds comprising structures according to formulas (1a) to (1f), (IIa) to (IIf), (IIIa) to (IIIf), (IVa) to (IVf) and / or (Va) to (Vk), or the preferred embodiments described above and below, are used as a component of mixed-matrix systems. The mixed-matrix systems preferably comprise two or three different matrix materials, 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 is contained, inter alia, in application WO 2010 / 108579.

[0186] Another object of the present invention is the use of a compound according to the invention in an electronic device, in particular in an organic electroluminescence device.

[0187] A further object of the present invention is the use of a compound according to claim 12 or 13 and / or an oligomer, polymer or dendrimer according to claim 14 in an electronic device as a fluorescent emitter, emitter exhibiting TADF (thermally activated delayed fluorescence), host material, electron transport material, electron injection material, hole transport material, hole injection material, electron blocking material, hole blocking material and / or wide-band gap material, preferably as a fluorescent emitter (singulet emitter), host material, hole transport material and / or electron transport material.

[0188] A further object of the present invention is an electronic device comprising at least one compound according to claim 19. An electronic device within the meaning of the present invention is a device comprising an anode, a cathode, and at least one intermediate layer containing at least one organic compound. The component may also contain inorganic materials or layers composed entirely of inorganic materials.

[0189] The electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes based on small molecules (sOLEDs), organic light-emitting diodes based on polymers (PLEDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), "organic plasmon emitting devices" (DM Koller et al., Nature Photonics 2008, 1-4); organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs) and organic electrical sensors, preferably organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.).), particularly preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes based on small molecules (sOLEDs), organic light-emitting diodes based on polymers (PLEDs), especially phosphorescent OLEDs.

[0190] 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, such as one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, and / or charge generation layers. Interlayers, which may, for example, have an exciton-blocking function, may also be introduced between two emitting layers. It should be noted, however, that not every one of these layers is necessarily present. The organic electroluminescent device may contain a single emitting layer, or it may contain multiple emitting layers.If multiple emission layers are present, these preferably exhibit several emission maxima between 380 nm and 750 nm, resulting in overall white emission. This means that different emitting compounds capable of fluorescence or phosphorescence are used in the emitting layers. Systems with three emitting layers exhibiting blue, green, and orange or red emission are particularly preferred. The organic electroluminescence device according to the invention can also be a tandem electroluminescence device, especially for white-emitting OLEDs.

[0191] In a further embodiment of the invention, the organic electroluminescent device according to the invention does not contain a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer; i.e., the emitting layer is directly adjacent to the hole injection layer or the anode, and / or the emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode, as described, for example, in WO 2005 / 053051. Furthermore, it is possible to use a metal complex that is identical or similar to the metal complex in the emitting layer directly adjacent to the emitting layer as a hole transport or hole injection material, as described, for example, in WO 2009 / 030981.

[0192] The compound according to the invention can be used in different layers, depending on the precise structure. A preferred application is an organic electroluminescent device containing a compound according to formulas (1a) to (1b) or the preferred embodiments described above in an emitting layer as a matrix material for phosphorescent emitters, for emitters exhibiting TADF (thermally activated delayed fluorescence), in particular for fluorescent or phosphorescent emitters. Furthermore, the compound according to the invention can also be used in an electron transport layer and / or in a hole transport layer and / or in an exciton blocking layer and / or in a hole blocking layer. The compound according to the invention is particularly preferred as a matrix material for red, orange, or yellow phosphorescent emitters, in particular for red phosphorescent emitters, in an emitting layer or as an electron transport or hole blocking layer.Hole-blocking material is used in an electron transport or hole-blocking layer.

[0193] Furthermore, an electronic device, preferably an organic electroluminescence device, is preferred, comprising one or more compounds according to the invention and / or at least one oligomer, polymer or dendrimer according to the invention in one or more electron-conducting layers, as the electron-conducting compound.

[0194] In the subsequent layers, all materials can generally be used as they are used for the layers according to the prior art, and the person skilled in the art can combine any of these materials in an electronic device with the materials according to the invention without inventive effort.

[0195] The device is structured accordingly (depending on the application), contacted, and finally hermetically sealed, as the lifespan of such devices is drastically reduced in the presence of water and / or air.

[0196] A further preferred option 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 deposited in vacuum sublimation systems at an initial pressure typically less than 10⁻⁵ mbar, preferably less than 10⁻⁶ mbar. It is also possible for the initial pressure to be even lower or higher, for example, less than 10⁻⁷ mbar.

[0197] A preferred electronic device, in particular an organic electroluminescence device, is 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).

[0198] A further preferred electronic device, in particular an organic electroluminescent device, is characterized in that one or more layers are produced from a solution, e.g. by spin coating, or by any printing process, e.g. 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 can be obtained, for example, by suitable substitution.

[0199] Hybrid processes are also possible, in which, for example, one or more layers of solution are applied and one or more further layers are vapor-deposited.

[0200] These methods are generally known to those skilled in the art and can be applied by them without inventive effort to organic electroluminescent devices containing the compounds according to the invention.

[0201] The electronic devices according to the invention, in particular organic electroluminescence devices, are characterized by one or more of the following surprising advantages over the prior art: 1. Electronic devices, in particular organic electroluminescent devices containing compounds, oligomers, polymers, or dendrimers according to the invention, or the preferred embodiments described above and below, especially as electron-conducting materials and / or hole transport materials or as matrix materials, exhibit a very good lifetime. 2. Electronic devices, in particular organic electroluminescent devices containing compounds, oligomers, polymers, or dendrimers according to the invention, or the preferred embodiments described above and below, especially as electron transport materials, hole transport materials, and / or as host materials, exhibit excellent efficiency. In particular, the efficiency is significantly higher compared to analogous compounds that do not contain a structure according to the invention. The compounds, oligomers, polymers, or dendrimers according to the invention, or theThe preferred embodiments described above and below exhibit a low operating voltage when used in electronic devices. In particular, these compounds result in a low roll-off, i.e., a low drop in the power efficiency of the device at high luminance levels. 3. Electronic devices, especially organic electroluminescent devices containing compounds, oligomers, polymers, or dendrimers, or the preferred embodiments described above and below, as electron transport materials, hole transport materials, and / or host materials, exhibit excellent color purity. 4. The compounds, oligomers, polymers, or dendrimers according to the invention, or the preferred embodiments described above and below, exhibit very high thermal and photochemical stability and result in compounds with a very long lifetime. 5.With compounds, oligomers, polymers, or dendrimers, or the preferred embodiments described above and below, the formation of optical loss channels can be avoided in electronic devices, particularly organic electroluminescent devices. This results in these devices exhibiting high PL and thus high EL efficiency of emitters, or excellent energy transfer from the matrices to the dopants. 6. Compounds, oligomers, polymers, or dendrimers, or the preferred embodiments described above and below, exhibit excellent glass film formation. 7. Compounds, oligomers, polymers, or dendrimers, or the preferred embodiments described above and below, form very good films from solutions.

[0202] These advantages mentioned above generally do not come at the expense of other electronic properties.

[0203] In the further layers of the organic electroluminescence device according to the invention, all materials can be used as they are commonly used according to the prior art.

[0204] The compounds according to the invention generally exhibit very good properties when used in organic electroluminescent devices. In particular, when the compounds according to the invention are used in organic electroluminescent devices, the lifetime is significantly better compared to similar compounds according to the prior art. Furthermore, the other properties of the organic electroluminescent device, especially the efficiency and the voltage, are also better or at least comparable.

[0205] It should be noted that variations of the embodiments described in the present invention fall within the scope of this invention. Unless explicitly excluded, each feature disclosed in the present invention may be replaced by alternative features serving the same, an equivalent, or a similar purpose. Thus, unless otherwise stated, each feature disclosed in the present invention is to be considered as an example of a generic series or as an equivalent or similar feature.

[0206] All features of the present invention can be combined with one another in any way, unless certain features and / or steps are mutually exclusive. This applies in particular to preferred features of the present invention. Likewise, features of non-essential combinations can be used separately (and not in combination).

[0207] The invention is further explained by the following examples, without thereby limiting it. Examples

[0208] Unless otherwise stated, the following syntheses are carried out under a protective gas atmosphere in dried solvents. The metal complexes are additionally handled in the absence of light or under yellow light. The solvents and reagents can be obtained, for example, from Sigma-Aldrich or ABCR. The information in square brackets and the numbers given for individual compounds refer to the CAS numbers of the compounds known from the literature. For compounds that can have several enantiomeric, diastereomeric, or tautomeric forms, one form is shown as a representative example.

[0209] The following diagram serves to better understand the synthesis route described in more detail below.

[0210] Reaktionsbedingungen: a) XPhos Pd G3, K 3 PO 4 , RF, THF, H 2 O, RF, 24 h, 62 %; b) NBS, DCM, RT, 2 h, 95 %; c) Pd(PPh 3 ) 2 Cl 2 , Trimethylsilylacetylen, TEA, RF, 24 h, 66 %; d) K 2 CO 3 , MeOH, RT, 0.5 h, 93 %; e) Au(SPhos)(NTf 2 ), meta-Xylol, RF, 20 h, 48 %; f) Pd(PCy 3 ) 2 Cl 2 , K 2 CO 3 , DMF, RF, 50 h, 70 %. Synthesis of synthons S: Example S1:

[0211]

[0212] A well-stirred mixture of 22.7 g (100 mmol) 3-bromo-5-methoxybenzofuran [333385-25-4], 27.9 g (110 mmol) bis(pinacolato)diborane [73183-34-3], 29.5 g (300 mmol) anhydrous potassium acetate, 50 g glass beads (3 mm diameter), and 500 ml THF is treated with 841 mg (3 mmol) tricyclohexylphosphine and then with 224 mg (1 mmol) palladium(II) acetate and heated under reflux for 16 h. While still warm, the mixture is filtered through a Celite bed pre-flourished with THF, the solvent is removed under vacuum, and the residue is dissolved in 100 ml of hot methanol. Allow to cool to room temperature while stirring, filter off the precipitated product, wash it once with 30 ml of methanol, and dry under vacuum. Yield: 19.3 g (70 mmol) 70%; Purity: approx. 95% n.l. < ¹H NMR.

[0213] The following connections can be represented analogously: Example. Educt product yield S2 1822631-86-6 74 % S3 487021-62-5 66 % G40 G30 72 % G41 G22 69 % Example G1: Synthesis of base material G1, see reaction scheme Stage a): Connection 1

[0214]

[0215] A mixture of 28.1 g (100 mmol) 1-bromo-9-chlorodibenzofuran [2179279-83-3], 16.3 g (100 mmol) 3-benzofuranylboronic acid [317830-83-4], 53.1 g (250 mmol) tripotassium phosphate, 3.4 g (4 mmol) XPhos Pd G3 [1445058-55-1], 800 ml of THF and 200 ml of water are heated under reflux for 24 hours. The reaction mixture is then concentrated under vacuum, and the residue is dissolved in 800 ml of ethyl acetate. The organic phase is washed three times with 200 ml of water each time, once with 300 ml of saturated saline solution, and then concentrated under vacuum to dryness.

[0216] The black, oily residue is dissolved in 500 ml of n-heptane and fractionally filtered over silica gel. After removal of the n-heptane under vacuum, the product is obtained as a colorless oil. Yield: 19.8 g (62 mmol) 62%; Purity: approx. 95% n.1 < H-NMR. Stage b): Connection 2

[0217]

[0218] A well-stirred solution of 33.9 g (100 mmol) of compound 1 in 300 ml of dichloromethane (DCM) is mixed with 18.0 g (100 mmol) of NBS at room temperature and stirred for 2 h. The solvent is then removed under vacuum, the oily residue is dissolved in 500 ml of n-heptane, and filtered through silica gel. After removal of the n-heptane under vacuum, the product is obtained as a colorless oil: yield: 37.8 g (95 mmol) 95%; purity: approx. 95%. 1 < ¹H NMR. Stage c): Connection 3

[0219]

[0220] A well-degassed mixture of 39.7 g (100 mmol) of compound 2, 42.4 ml (300 mmol) of trimethylsilylacetylene, 1000 ml of DMF, and 500 ml of triethylamine is treated with 1.2 g (6 mmol) of copper iodide and then with 4.0 g (4 mmol) of tetrakistriphenylphosphinopalladium(0) and stirred at 80°C for 24 h. After cooling, the reaction mixture is filtered through a Celite bed suspended with DMF. The filtrate is removed from the solvent under vacuum at 30°C, the residue is drawn up with 500 ml of DCM onto ISOLUTE® and chromatographed with n-heptane / ethyl acetate using an automated column chromatograph (Torrent, A. Semrau). Yield: 25.3 g, (66 mmol) 66%, Purity: approx. 95% y n. 1< H-NMR. Stage d): Connection 4

[0221]

[0222] A well-stirred solution of 41.7 g (100 mmol) of compound 3 in 500 ml of MeOH is mixed with 27.6 g (200 mmol) of potassium carbonate at room temperature and stirred for 30 min. The potassium carbonate is filtered off, the MeOH is removed under vacuum at 30 °C, the residue is dissolved in 300 ml of DCM, washed three times with 100 ml of water, once with 100 ml of saturated saline, dried over sodium sulfate, filtered off the drying agent, and the filtrate is concentrated under vacuum to dryness. Yield: 32.1 g (93 mmol), 93%; Purity: approx. 95%, < 1H NMR. Level e): Connection 5

[0223]

[0224] A well-stirred solution of 17.2 g (50 mmol) of compound 4 in 1000 ml m-xylene is heated under reflux, then a solution of 4.4 g (5 mmol) of SPhosAuNTf 2 [1121960-90-4] in 200 ml m-xylene is added dropwise for 8 h, and finally heated under reflux for a further 12 h. After cooling, the solvent is removed under vacuum. The oily residue is dissolved in 300 ml DCM and drawn onto ISOLUTE® and chromatographed with n-heptane using an automated column chromatograph (Torrent, A. Semrau). Yield: 8.3 g (48 mmol), 48%; purity: approx. 95%. 1H NMR. Stage f): Basic body G1

[0225]

[0226] A well-stirred mixture of 17.2 g (50 mmol) of compound 5, 27.6 g (200 mmol) of potassium carbonate, 1.9 g (2.5 mmol) of Pd(PCy3)2Cl2 [29934-17-6], 50 g of glass beads, and 1000 ml of DMF is heated under gentle reflux for 50 h. After cooling, the DMF is removed under vacuum, the residue is dissolved in 1000 ml of hot chlorobenzene, filtered through a pre-flourished aloxic acid bed, concentrated under vacuum to dryness, and the beige residue is stirred twice with 300 ml of hot n-heptane. Yield: 10.9 g (35 mmol), 70%; purity: approx. 95%. < 1H NMR.

[0227] The following connections can be represented analogously: Example. Starting materials product Yield over 6 stages G2 S1 10 % G3 S2 15 % G4 675876-98-9 21 % G5 1569089-52-6 17 % G6 1869141-62-7 15 % G7 S3 13 % TMM30 1869140-80-6 15 % TMM31 1869140-91-9 14 % Example G10:

[0228]

[0229] A mixture of 16.8 g (50 mmol) of G2 and 115.6 g (1 mol) of pyridinium hydrochloride [628-13-7] is melted and heated with good stirring in a water separator for 3 h at 230 °C (heating bowl temperature), with the pyridine formed being removed periodically. The reaction mixture is allowed to cool to about 100 °C and 500 ml of water is carefully added dropwise. After cooling, the precipitated solid is filtered off, washed three times with 100 ml of warm water and once with 50 ml of cold methanol, and dried under vacuum. Yield: 16.1 g (48 mmol), 96%; Purity: about 95% n.l. < ¹H NMR.

[0230] The following connections can be represented analogously: Example. Educt product yield G11 G3 95 % G12 G4 93 % G13 G7 91 % Example G20:

[0231]

[0232] A well-stirred suspension of 16.1 g (50 mmol) of G10 in 300 ml DCM, cooled to 0 °C, is treated with 12 ml of pyridine and then dropwise with 16.8 ml (100 mmol) of trifluoromethanesulfonic anhydride [358-23-6] and stirred for 2 h at 0 °C. The reaction mixture is allowed to warm to room temperature, stirred for 2 h, then poured onto 500 g of ice and stirred for 30 min. The organic phase is separated, washed twice with 100 ml saturated sodium chloride solution, and the solvent is removed under vacuum. Yield: 21.7 g (47.5 mmol), 95%; Purity: approx. 95% n. 1< H-NMR.

[0233] The following connections can be represented analogously: Example. Educt product yield G21 G11 93 % G22 95 % G23 G13 90 % Example G30:

[0234]

[0235] A suspension of 3.06 g (10.0 mmol) of G1 in 100 ml of chloroform is treated with 3.53 g (11 mmol) of pyridinium perbromide under exclusion of light and then stirred for 24 h at 60 °C. After cooling, 30 ml of 10 wt% sodium sulfite solution is added, the mixture is stirred for 30 min, the organic phase is separated, the mixture is concentrated to dryness under vacuum, the residue is stirred twice with 25 ml of hot methanol, and recrystallizes from a small amount of chlorobenzene. Yield: 3.05 g (7.8 mmol), 78%; purity: approx. 95%, < 1H NMR. Example TMM1:

[0236]

[0237] A mixture of 4.54 g (10 mmol) G20, 3.83 g (12 mmol) 3,6-diphenylcarbazole [56525-79-2], 5.31 g (25 mmol) tripotassium phosphate, 20 g glass beads (3 mm diameter), and 100 ml o-xylene is stirred at room temperature with 289 mg (0.5 mmol) XantPhos and 112 mg (0.5 mmol) palladium(II) acetate and then stirred under reflux for 36 h. The solvent is largely removed under vacuum, the solid is stirred twice with 200 ml of hot water each time, the precipitated product is filtered by suction, washed three times with 100 ml of water each time, three times with 30 ml of methanol, and dried under vacuum. The crude product is dissolved in 300 ml of DCM and filtered through a keel gel bed pre-floured with DCM. The filtrate is treated with 100 ml of methanol, the DCM is removed under vacuum, the precipitated solid is collected by filtration and dried under vacuum. Purification is carried out by repeated hot extraction with toluene, using a feed volume of 150 ml, and Whatman cellulose extraction pods.Alternatively, other solvents can be used. Finally, the product is fractionally sublimed under high vacuum (p ~ 10⁻⁵ < mbar). Yield: 3.93 g (6.3 mmol), 63%; Purity: > 99.9% n. HPLC.

[0238] The following connections can be represented analogously: Example. Starting materials product yield TMM2 1060735-14-9 72 % TMM3 G22 68 % 1257220-47-5 TMM4 G23 44 % 1374446-05-5 TMM5 G30 61 % 1338919-70-2 Example TMM10:

[0239]

[0240] A mixture of 4.54 g (10 mmol) G20, 5.34 g (12 mmol) 9-[1,1'-Biphenyl]-3-yl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole [1533406-38-0], 6.9 g (30 mmol) tripotassium phosphate monohydrate [27176-10-9], 20 g glass beads (3 mm diameter), 347 mg (0.3 mmol) tetrakis-triphenylphosphinopalladium(0) and 100 ml DMSO is stirred for 24 h at 100 °C. The warm reaction mixture is poured into 300 ml of hot water, stirred for 20 minutes, and the precipitated product is filtered off. This product is washed three times with 50 ml of water and three times with 30 ml of methanol, and then dried under vacuum. The crude product is dissolved in 300 ml of DCM and filtered through a keel gel bed pre-floured with DCM. The filtrate is mixed with 100 ml of methanol, the DCM is removed under vacuum, the precipitated solid is filtered off, and the product is dried under vacuum. Purification is carried out by repeated hot extraction with toluene, using a feed volume of 150 ml and Whatman cellulose extraction pods.Alternatively, other solvents can be used. Finally, the product is fractionally sublimed under high vacuum (p ~ 10⁻⁵ < mbar). Yield: 2.8 g (4.5 mmol), 45%; Purity: > 99.9% n. HPLC.

[0241] The following connections can be represented analogously: Example. Starting materials product yield TMM 11 G21 57 % 2088364-11-6 TMM12 G22 63 % ETM1 2032365-30-1 TMM13 G23 38 % 1852465-33-8 TMM14 G30 71 % 1115639-92-3 TMM20:

[0242] Stage a)

[0243]

[0244] A well-stirred mixture of 4.32 g (10 mmol) G30, 2.22 g (11 mmol) 2-bromonitrobenzene [577-19-5], 4.15 g (30 mmol) potassium carbonate, 116 mg (0.1 mmol) tetrakistriphenylphosphinopalladium(0), 150 ml THF, and 30 ml water is heated under reflux for 16 h. The still-warm reaction mixture is treated with 200 ml water, concentrated under vacuum to approximately 100 ml, filtered off the precipitated solid, washed three times with 50 ml water, twice with 30 ml methanol, and dried under vacuum. Yield: 3.99 g (9.3 mmol), 93%; purity: approximately 95%. < 1H NMR. Level b):

[0245]

[0246] Analogous to SH Smitrovich et al., Org. Lett, 2004, 6, 4, 533. A mixture of 4.27 g (10 mmol) TMM20 step a), 72 mg (0.4 mmol) 1,10-phenanthroline, 45 mg (0.2 mmol) palladium(II) acetate, and 50 ml DMF is stirred in an autoclave under 5 bar CO pressure for 16 h at 140 °C. After cooling, the DMF is removed under vacuum, the residue is dissolved in 100 ml of boiling chlorobenzene, and while still hot, filtered through a silica gel bed pre-flourished with chlorobenzene. The filtrate is then concentrated under vacuum at 80 °C until crystallization begins and stirred at room temperature to complete crystallization. The product is filtered by suction, washed three times with 30 ml of methanol, and dried under vacuum. Yield: 3.44 g (8.7 mmol), 87%; Purity: approx. 95% y n. 1< H-NMR. Level c): TMM20

[0247] A mixture of 3.95 g (10 mmol) TMM20 stage b), 3.27 g (14 mmol) 3-bromobiphenyl [2113-57-7], 1.44 g (15 mmol) sodium tert-butanoate, 41.0 mg (0.1 mmol) S-Phos, 22.5 mg (0.1 mmol) palladium(II) acetate, and 100 ml o-xylene is stirred under reflux for 24 h. After cooling, the o-xylene is removed under vacuum, and the residue is stirred with 100 ml of a 1:2 mixture of water and methanol while hot. The solid is filtered by suction, washed three times with 30 ml of methanol each time, and dried under vacuum. The residue is dissolved in 100 ml of boiling chlorobenzene and filtered while still hot through a silica gel bed pre-flourished with chlorobenzene. The filtrate is then concentrated under vacuum at 80 °C until crystallization begins, and stirred at room temperature to complete crystallization. The product is filtered by suction, washed three times with 30 ml of methanol, and dried under vacuum. Purification is carried out by repeated hot extraction with toluene, using a feed volume of 150 ml and cellulose extraction pods from [Company Name].Whatman solvent. Alternatively, other solvents can be used. Finally, the product is fractionally sublimed under high vacuum (p ~ 10⁻⁵ < mbar). Yield: 3.84 g (7.0 mmol), 70%; Purity: > 99.9% n. HPLC.

[0248] The following connections can be represented analogously: Example. Starting materials product yield TMM21 1955546-91-4 48 % TMM22 1413367-86-9 45 % Example SMM1:

[0249]

[0250] A well-stirred mixture of 4.32 g (10 mmol) G30, 5.05 g (11 mmol) 10-(4-(1-Naphthenyl)phenyl)-9-bromoanthracene [1092390-01-6], 6.37 g (30 mmol) tripotassium phosphate, 183 mg (0.6 mmol) tri-o-tolylphosphine, 22.5 mg (0.1 mmol) palladium(II) acetate, 100 ml toluene, 50 ml dioxane, and 100 ml water is heated under reflux for 16 h. After cooling, the precipitated solid is filtered off, washed three times with 50 ml of water, three times with 30 ml of methanol, and dried under vacuum. The solid is taken up in 200 ml of DCM, filtered through a silica gel bed pre-flourished with DCM, the filtrate is mixed with 100 ml of methanol, and concentrated under vacuum until crystallization begins. The crystallizate is filtered off, washed twice with 30 ml of methanol, and dried under vacuum. Purification is carried out by repeated hot extraction with toluene, using a feed volume of 150 ml and Whatman cellulose extraction hulls. Alternatively, other solvents can be used.Finally, the product is fractionally sublimed under high vacuum (p ~ 10⁻⁵ < mbar). Yield: 4.60 g (6.7 mmol), 67%; Purity: > 99.9% n. HPLC.

[0251] The following connections can be represented analogously: Example. Starting materials product yield SMM2 G41 60 % Vacuum-processed devices:

[0252] The production of OLEDs according to the invention as well as OLEDs according to the prior art is carried out according to a general method according to WO 2004 / 058911, which is adapted to the conditions described here (layer thickness variation, materials used).

[0253] The following examples present the results for various OLEDs. Cleaned glass plates (cleaned in a Miele laboratory dishwasher using Merck Extran detergent) 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), sourced as CLEVIOS™< P VP AI 4083 from Heraeus Precious Metals GmbH Germany, centrifugally applied from aqueous solution) for improved processing. These coated glass plates are then baked out at 180°C for 10 minutes. These coated glass plates form the substrates onto which the OLEDs are applied.

[0254] The OLEDs have the following basic layer structure: Substrate / Hole injection layer 1 (HIL1) consisting of Ref-HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm / Hole transport layer 1 (HTL1) consisting of 200 nm Ref-HTM1 / Hole transport layer 2 (HTL2) consisting of 10 nm Ref-HTM2 / Emission layer (EML) 30 nm / Hole blocking layer (HBL) 10 nm / Electron transport layer (ETL) 30 nm / Optional electron injection layer (EIL) and finally a cathode. The cathode is formed by a 100 nm thick aluminum layer.

[0255] First, vacuum-processed OLEDs are described. For this process, all materials are thermally vapor-deposited in a vacuum chamber. The emission layer always consists of at least one matrix material (host material) and an emitting dopant, which is added to the matrix material(s) by co-evaporation in a specific volume fraction. A specification such as Ref-TMM1:Ref-TMM2:Ir1 (55%:35%:10%) means that Ref-TMM1 is present in the layer at a volume fraction of 55%, Ref-TMM2 at a fraction of 35%, and IrL1 at a fraction of 10%. Similarly, the electron transport layer can also consist of a mixture of two materials. The exact structure of the OLEDs can be found in Table 1. The materials used to fabricate the OLEDs are shown in Table 3.

[0256] The OLEDs are characterized according to standard procedures. This includes determining the electroluminescence spectra, current efficiency (measured in cd / A), power efficiency (measured in lm / W), and external quantum efficiency (EQE, measured in percent) as a function of luminance, calculated from current-voltage-luminance curves (IUL curves) assuming a Lambertian emission characteristic, 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 a starting brightness of <10000 cd / m².

[0257] The OLEDs can initially be operated at other starting luminances. The lifetime values ​​can then be converted to values ​​for other starting luminances using conversion formulas known to experts. Verwendung von erfindungsgemäßen Verbindungen als Materialien in phosphoreszierenden OLEDs

[0258] The compounds according to the invention can be used, among other things, as TMMs (triplet matrix materials), ETMs (electron transport materials), and as SMMs (singulet matrix materials) as host materials in the emission layer of OLEDs. For comparison with the prior art, compounds according to Table 3 are used. The results for the OLEDs are summarized in Table 2. Tabelle 1: Aufbau der OLEDs Bsp. EML HBL ETL Ref.D1 Ref-TMM1:Ref-TMM2:Ir1 (45%:40%:15%) Ref-ETM1 Ref-ETM1:Ref-ETM2 (50%:50%) Ref.D2 Ref-TMM1:Ref-TMM2:Ir2 (45%:40%:15%) Ref-ETM1 Ref-ETM1:Ref-ETM2 (50%:50%) Ref.D3 Ref-TMM1:Ref-TMM2:Ir3 (45%:50%:5%) Ref-ETM1 Ref-ETM1:Ref-ETM2 (50%:50%) D1 Ref-TMM1:TMM1:Ir1 (45%:40%:15%) Ref-ETM1 Ref-ETM 1: Ref-ETM2 (50%:50%) D2 TMM12:TMM2:Ir1 (45%:40%:15%) Ref-ETM1 Ref-ETM1:Ref-ETM2 (50%:50%) D3 TMM12:TMM2:Ir2 (40%:50%:10%) Ref-ETM1 Ref-ETM1:Ref-ETM2 (50%:50%) D4 TMM12:TMM3:Ir2 (40%:50%:10%) Ref-ETM1 Ref-ETM1:Ref-ETM2 (50%:50%) D5 Ref-TMM1:TMM4:Ir2 (30%:60%:10%) Ref-ETM1 Ref-ETM1:Ref-ETM2 (50%:50%) D6 Ref-TMM1:TMM5:Ir2 (30%:55%:15%) Ref-ETM1 Ref-ETM1:Ref-ETM2 (50%:50%) D7 Ref-TMM1:TMM10:Ir1 (30%:55%:15%) Ref-ETM1 Ref-ETM1:Ref-ETM2 (50%:50%) D8 TMM12:TMM11:Ir1 (30%:55%:15%) Ref-ETM1 Ref-ETM1:Ref-ETM2 (50%:50%) D9 TMM13:Ir3 (95%:5%) --- Ref-ETM1:Ref-ETM2 (50%:50%) D10 TMM12:TMM13: Ir1 (40%:40%:20%) Ref-ETM1 Ref-ETM1:Ref-ETM2 (50%:50%) D11 TMM21:TMM20:Ir1 (50%:40%:10%) Ref-ETM1 Ref-ETM1:Ref-ETM2 (50%:50%) D12 TMM22:Ir3 (95%:5%) --- Ref-ETM1:Ref-ETM2 (50%:50%) D13 TMM22:Ir3 (95%:5%) ETM1 Ref-ETM 1: Ref-ETM2 (50%:50%) D14 TMM22: Ir3 (95%:5%) ETM1 ETM1:Ref-ETM2 (50%:50%) D15 TMM21:TMM30: Ir3 (50%:45%:5%) --- Ref-ETM1:Ref-ETM2 (50%:50%) D16 TMM21:TMM31:Ir3 (50%:45%:5%) --- Ref-ETM1:Ref-ETM2 (50%:50%) D17 SMM1:GD1 (94%:6%) --- Ref-ETM1:Ref-ETM2 (50%:50%) D18 SMM2:GD1 (94%:6%) --- Ref-ETM1:Ref-ETM2 (50%:50%) Table 2: Results of vacuum-processed OLEDs Example. EQE (%) 1000 cd / m²< Voltage (V) 1000 cd / m²< CIE x / y 1000 cd / m²< LD90 (h) 10000 cd / m²< Yellow and Red OLEDs Ref. D1 27.4 3.2 0.49 / 0.51 1700 Ref. D2 27.0 3.1 0.51 / 0.48 1300 Ref. D3 25.1 3.4 0.67 / 0.33 300 D1 27.3 2.9 0.49 / 0.51 1800 D2 27.6 2.9 0.49 / 0.51 1700 D3 27.4 2.8 0.51 / 0.48 1100 D4 27.8 2.8 0.51 / 0.48 --- D5 27.6 2.8 0.51 / 0.48 --- D6 27.6 2.9 0.51 / 0.49 --- D7 27.9 3.0 0.49 / 0.51 --- D8 27.1 2.9 0.49 / 0.51 --- D9 25.5 3.2 0.67 / 0.33 700 D10 27.4 3.0 0.49 / 0.51 --- D11 28.1 3.0 0.49 / 0.51 --- D12 25.9 3.1 0.67 / 0.33 --- D13 26.2 3.0 0.67 / 0.33 --- D14 26.3 3.0 0.67 / 0.33 --- D15 26.1 3.0 0.67 / 0.33 --- D16 25.9 2.9 0.68 / 0.32 600 Green OLEDs Example. EQE (%) 1000 cd / m²< Voltage (V) 1000 cd / m²< CIE x / y 1000 cd / m²< D17 8.6 3.7 0.29 / 0.62 D18 8.8 3.5 0.29 / 0.62 Table 3: Structural formulas of the materials used HTM1 [136463-07-5] HTM2 [1450933-43-3] Ref-TMM1 [1257248-13-7] Ref-TMM2 [1357150-54-9] Ref-ETM1 [1233200-52-6] Ref-ETM2 [25387-93-3] [2245945-28-0] Ir2 [2245945-28-0] Ir3 [1388666-65-6] GD1 [1182175-24-1] Ref-TMM1 [1257248-13-7] Ref-TMM2 [1357150-54-9]

[0259] The examples and comparative examples presented above show that the compounds according to the invention achieve unexpected improvements with regard to lifetime, quantum efficiency (EQE) and the required operating voltage.

[0260] For example, a comparison of reference example Ref. D1 with examples D1, D2, D7, D8, D10, and D11, each featuring compound Ir1 as the emitter, shows that the examples according to the invention achieve significant improvements in the above-mentioned criteria without incurring any significant disadvantages. Example D11, in particular, demonstrates surprising advantages with regard to quantum efficiency. The advantages of structures according to formulas (Vf) to (Vk), especially (Vh), are confirmed by comparing example D12 with examples D15 and D16.

[0261] A similar result is obtained by comparing reference example Ref.D2 with examples D3, D4, D5, and D6, each of which uses the Ir2 compound as the emitter. The same applies to a comparison of reference example Ref.D3 with examples D9, D12, D13, D14, D15, and D16, each of which uses the Ir3 compound as the emitter. Here, example D9 shows that, compared to Ref.D3, the lifetime is more than doubled, while simultaneously improving the quantum efficiency (EQE) and the required operating voltage.

[0262] Furthermore, a comparison of Examples D12, D13, and D14 shows that unexpectedly strong improvements can be achieved by using materials according to the invention in a hole-blocking layer (HBL). The use of materials according to the invention in an electron transport layer (ETM) also leads to improvements.

Claims

1. An electronic device comprising at least one compound comprising at least one structure of formula (la), preferably (Ib), (Ic), (Id), (Ie) and / or (If), wherein formulae (la) to (If) are as follows X is equal to or different from CR at each occurrence; wherein at most 2 of the groups CR, for which X stands, are not equal to the group CH; Y is, at each occurrence, identical or different, a bridge selected from O, S, B(R), C=O, N(R) and N(Ar), particularly preferred O, S, N(Ar); R in each occurrence is the same or different H, D, F, CN, N(Ar)2, N(R1)2, Si(Ar)3, Si(R1)3, B(Ar)2, B(R1)2, a straight-chain alkyl or alkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, wherein the alkyl or alkoxy group may each be substituted by one or more radicals R1, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which may each be substituted by one or more radicals R1; two radicals R can also form a ring system with each other; Ar is in each occurrence the same or different an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R1, whereby two radicals Ar, which bind to the same Si atom, N atom or B atom can also be linked by a single bond or a bridge selected from B(R1), C(R1)2, Si(R1)2, C=O, C=NR1, C=C(R1)2, O, N(R1), P(R1) and P(=O)R1; R1 is the same or different for each occurrence H, D, F, CN, N(Ar1)2, N(R2)2, B(Ar1)2, B(R2)2, Si(Ar1)3, Si(R2)3, a straight-chain alkyl or alkoxy group with 1 to 40 carbon atoms or a branched or cyclic alkyl or alkoxy group with 3 to 40 carbon atoms, which may each be substituted by one or more radicals R2, wherein one or more H atoms may be replaced by D, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which may each be substituted by one or more radicals R2; two or more preferably neighbouring radicals R1 can form a ring system with one another; one or more radicals R1 can form a ring system with a further part of the communication; Ar1 is in each occurrence the same or different an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which can be substituted with one or more nonaromatic radicals R2, whereby two radicals Ar1, which bind to the same Si atom, N atom or B atom, can also be linked 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, N(R2), P(R2) and P(=O)R2; R2 in each occurrence is the same or different and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 carbon 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 and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms, two or more preferably neighbouring substituents R2 forming a ring system with one another.

2. Electronic device according to claim 1, characterised in that the compound comprises at least one structure of formulae (IIa), (IIb), (IIc), (IId), (IIe) and / or (IIf), wherein the radicals X, Y and R have the meaning given in claim 1, the index m is equal to or different from 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably 0 or 1, and the index o is equal to or different from 0, 1 or 2, preferably 0 or 1, wherein the sum of the indices o or 0 and m is preferably 1 or 2, particularly preferably 1.

3. Electronic device according to claim 1 or 2, characterised in that the compound comprises at least one structure of formulae (IIIa), (IIIb), (IIIc), (IIId), (IIIe) and / or (IIIf), wherein the radicals X, Y and R have the meaning given in claim 1, the index m is equal to or different from 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably 0 or 1, and the index n is equal to or different from 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably 0 or 1, wherein the sum of the indices n or n and m is preferably 1 or 2, particularly preferably 1.

4. Electronic device according to one or more of the preceding claims, characterised in that the compound comprises at least one structure of formulae (IVa), (IVb), (IVc), (IVd), (IVe) and / or (IVf), wherein the radicals Y and R are as defined in claim 1, the subscript k is equal to or different from 0 or 1, preferably 0, the subscript o is equal to or different from 0, 1 or 2, preferably 0 or 1, the subscript n is equal to or different from 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferred 0 or 1, and the index m is equal to or different from 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferred 0 or 1, wherein the sum of the indices k, m, n and o is preferably 1 or 2, particularly preferred 1.

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

6. Electronic device according to one or more of the preceding claims, characterised in that the compound comprises at least one structure of formulae (Va), (Vb), (Vc), (Vd), (Ve), (Vf), (Vg), (Vh), (Vi), (Vj) and / or (Vk), wherein the radicals Y and R are as defined in claim 1 and furthermore Ra in each occurrence is the same or different F, CN, N(Ar)2, N(R1)2, Si(Ar)3, Si(R1)3, B(Ar)2, B(R1)2, a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, wherein the alkyl or alkoxy group may each be substituted by one or more radicals R1, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which may each be substituted by one or more radicals R1; radicals Ra can also form a ring system with a radical R, wherein the radicals Ar and R1 have the meaning given in claim 1; k is equal to or different from 0 or 1, preferably 0, o is the same or different 0, 1 or 2, preferably 0 or 1; n is equal to or different from 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferred 0 or 1; and m is equal to or different from 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferred 0 or 1.

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

8. Electronic device according to at least one of the preceding claims, characterised in that at least one of the radicals R and / or Ra is selected from the group of fluorenes, indenofluorenes, spirobifluorenes, carbazoles, indenocarbazoles, indolocarbazoles, spirocarbazoles, pyrimidines, triazines, lactams, triarylamines, dibenzofurans, dibenzothienes, imidazoles, benzimidazoles, benzoxazoles, benzthiazoles, 5-aryl-phenanthridin-6-ones, 9,10-dehydrophenanthrenes, fluoranthenes, anthracenes, benzanthracenes, fluoradenes.

9. Electronic device according to at least one of the preceding claims, characterised in that the connection comprises a hole transport group, wherein preferably one of the groups R and / or Ra comprises a hole transport group.

10. Electronic device according to at least one of the preceding claims, characterised in that one of the groups R and / or Ra is a hole transport group.

11. Electronic device according to at least one of the preceding claims, characterised in that one of the groups R and / or Ra represents an electron transport group.

12. A compound according to formula (Ib), (Ic), (Id), (le) or (If), wherein the radicals X and Y are as defined in claim 1.

13. A compound according to formula (la), wherein X is identical to or different from CR at each occurrence, wherein at most 2 of the groups CR, for which X stands, are not identical to the group CH; Y is, at each occurrence, identical or different, a bridge selected from N(Ar), O, S, B(R) and C=O, particularly preferred N(Ar), O and S; R is the same or different at each occurrence H, D, F, CN, N(Ar)2, N(R1)2, Si(Ar)3, Si(R1)3, B(Ar)2, B(R1)2, a straight-chain alkyl or alkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, wherein the alkyl or alkoxy group may be substituted in each case by one or more radicals R1, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted in each case by one or more radicals R1; Ar is in each occurrence the same or different an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R1, whereby two radicals Ar, which bind to the same Si atom, N atom or B atom can also be linked by a single bond or a bridge selected from B(R1), C(R1)2, Si(R1)2, C=O, C=NR1, C=C(R1)2, O, N(R1), P(R1) and P(=O)R1; R1 is the same or different for each occurrence H, D, F, CN, N(Ar1)2, N(R2)2, B(Ar1)2, B(R2)2, Si(Ar1)3, Si(R2)3, a straight-chain alkyl or alkoxy group with 1 to 40 carbon atoms or a branched or cyclic alkyl or alkoxy group with 3 to 40 carbon atoms, which may each be substituted by one or more radicals R2, wherein one or more H atoms may be replaced by D, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which may each be substituted by one or more radicals R2; Ar1 is in each occurrence the same or different an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which can be substituted with one or more nonaromatic radicals R2, whereby two radicals Ar1, which bind to the same Si atom, N atom or B atom can also be linked 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, N(R2), P(R2) and P(=O)R2; R2 in each occurrence is the same or different and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 carbon 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 and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms.

14. An oligomer, polymer or dendrimer containing one or more compounds according to claim 12 or 13, wherein instead of a hydrogen atom or a substituent one or more bonds of the compounds to the polymer, oligomer or dendrimer are present.

15. A composition containing at least one compound according to claim 12 or 13 or an oligomer, polymer or dendrimer according to claim 14 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF (thermally activated delayed fluorescence), host materials, electron transport materials, electron injection materials, hole transport materials, hole injection materials, electron blocking materials and hole blocking materials, wide-band-gap materials and n-dotands.

16. A formulation containing at least one compound according to claim 12 or 13 or an oligomer, polymer or dendrimer according to claim 14 or a composition according to claim 15 and at least one solvent.

17. Use of a compound according to claim 12 or 13, an oligomer, polymer or dendrimer according to claim 14 or a composition according to claim 15 in an electronic device as emitter, preferably fluorescent emitter, emitter showing TADF (thermally activated delayed fluorescence), host material, electron transport material, electron injection material, hole transport material, hole injection material, electron blocking material, hole blocking material and / or wide-band-gap material, particularly preferred as fluorescent emitter (singlet emitter), host material, hole transport material and / or electron transport material.

18. A process for preparing a compound according to claim 12 or 13 or an oligomer, polymer and / or dendrimer according to claim 14, characterised in that a compound comprising a heterocyclic structure is combined in a coupling reaction with a compound comprising at least one aromatic or heteroaromatic group.

19. An electronic device according to one or more of claims 1 to 11, containing at least one compound according to claim 12 or 13, an oligomer, polymer or dendrimer according to claim 14 or a composition according to claim 15, wherein the electronic device is 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.