Materials for organic electroluminescent devices

Abstract

The present invention relates to diazadibenzofuran derivatives and diazadibenzothiophene derivatives and to electronic devices containing said compounds, in particular organic electroluminescent devices containing said compounds in the form of triplet matrix materials, optionally combined with another triplet matrix material and suitable phosphorescent emitters, and to suitable mixtures and formulations.

Description

[0001] Materials for organic electroluminescent devices Technical field The present invention relates to diazadibenzofuran or diazadibenzothiophene derivatives and to electronic devices comprising these compounds, in particular to organic electroluminescent devices comprising these compounds as triplet matrix materials, optionally in combination with another triplet matrix material and suitable phosphorescent emitters, and to suitable mixtures and formulations. State of the art Phosphorescent organometallic complexes are frequently used in organic electroluminescent devices (OLEDs). In general, there is still room for improvement in OLEDs, for example with regard to efficiency, operating voltage, and lifetime. The properties of phosphorescent OLEDs are determined not only by the triplet emitters used.The other materials used, such as matrix materials, are also of particular importance here. Improvements to these materials can therefore also lead to significant improvements in OLED properties. According to the prior art, carbazole derivatives, dibenzofuran derivatives, indenocarbazole derivatives, indolocarbazole derivatives, benzofurocarbazole derivatives, and benzothienocarbazole derivatives are used as matrix materials for phosphorescent emitters. WO2019 / 190239 A1, WO2019 / 190241 A1, KR20200136072 A, and KR20220063428 A describe specific diazadibenzofuran and diazadibenzothiophene derivatives as matrix materials. CN114560864 A describes specific diazadibenzofuran and diazadibenzothiophene derivatives as electron-transport materials. In general, there is still room for improvement in these materials for use as matrix materials.The object of the present invention is to provide compounds which are particularly suitable for use as matrix material in a phosphorescent OLED. In particular, the object of the present invention is to provide matrix materials which lead to an improved lifetime. This applies in particular to the use of a low to medium emitter concentration, ie emitter concentrations in the order of magnitude of 3 to 20%, in particular of 3 to 15%, since the device lifetime is particularly limited here. It has now been found that electroluminescent devices which contain compounds according to the following formula (1) have improvements over the prior art, in particular when the compounds are used as matrix material for phosphorescent dopants. It has furthermore been found that the combination of at least one compound of the formula (1) as the first host material and at least one hole transport. ing compound, for example in combination with one or more compounds of formulas (6), (7), (8), (9), (10) or (11) as further host material(s) in a light-emitting layer of an organic electronic device, in particular an organic electroluminescent device, this object can be achieved and the disadvantages of the prior art can be eliminated. Summary of the Invention A first subject of the present invention is a compound according to formula (1) where the following applies to the symbols and indices used: Y is N, C-[L]b-Ar2 or C-[L]b1-Ar3 at each occurrence, independently of one another, where exactly two Y's stand for N, which are separated by a group C-[L]b-Ar2 or C-[L]b1-Ar3; V is O or S; Het corresponds to one of the formulas (1-2), (1-3), (1-4) or (1-5), * denotes the connection to the rest of formula (1), R 1is at each occurrence, independently of one another, H, D, or non-deuterated or partially or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl; Ar, Ar1 are at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms which is substituted by one or more radicals R 2 may be substituted; Ar2, Ar3 are at each occurrence, identically or differently, an aromatic ring system having 6 to 40 ring atoms or a heteroaromatic ring system having 9 to 40 ring atoms, which can be substituted with one or more radicals R 2 may be substituted; R 2is selected, identically or differently at each occurrence, from the group consisting of D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms may be replaced by D, F, or CN; R# is, at each occurrence, D, or non-deuterated or partially or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl; [L] is an aromatic ring system having 6 to 40 ring atoms or a heteroaromatic ring system having 9 to 40 ring atoms, which may be unsubstituted or partially or fully substituted by D; b, b1, b2 are each independently 0 or 1. The invention further relates to a mixture,containing at least one compound of formula (1) as described above or preferably described later, and at least one further compound selected from the group of matrix materials, phosphorescent emitters, fluorescent emitters, and / or emitters exhibiting TADF (thermally activated delayed fluorescence). The invention further provides a formulation containing at least one compound of formula (1), as described above or preferably described later, or a mixture as described above, and at least one solvent. The invention further provides an organic electronic, preferably electroluminescent, device comprising an anode, a cathode, and at least one organic layer containing at least one compound of formula (1),as described above or preferably described later. The invention further provides a process for producing an organic electronic, preferably electroluminescent, device, as described above or preferably described below, characterized in that the organic layer is applied by vapor deposition or from solution. Description of the invention In the present patent application, "D" or "D atom" denotes deuterium. An aryl group in the sense of this invention contains 6 to 40 ring atoms, preferably C atoms. A heteroaryl group in the sense of this invention contains 5 to 40 ring atoms, where the ring atoms comprise C atoms and at least one heteroatom, with the proviso that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aryl group or heteroaryl group is defined as either a simple aromatic cycle, i.e. phenyl,derived from benzene, or a simple heteroaromatic cycle, for example derived from pyridine, pyrimidine or thiophene, or a condensed aryl or heteroaryl group, for example derived from naphthalene, anthracene, phenanthrene, quinoline or isoquinoline. An aryl group with 6 to 18 C atoms is therefore preferably phenyl, naphthyl, phenanthryl or triphenylenyl, whereby the attachment of the aryl group as a substituent is not restricted. The aryl or heteroaryl group within the meaning of this invention can carry one or more radicals, whereby the suitable radical is described below. If no such radical is described, the aryl group or heteroaryl group is not substituted. An aromatic ring system within the meaning of this invention contains 6 to 40 C atoms in the ring system. The aromatic ring system also includes aryl groups, as described above. An aromatic ring system with 6 to 18 C atoms is preferably made of phenyl,fully deuterated phenyl, biphenyl, naphthyl, phenanthryl and triphenylenyl. A heteroaromatic ring system within the meaning of this invention contains 5 to 40 ring atoms and at least one heteroatom. A preferred heteroaromatic ring system has 9 to 40 ring atoms and at least one heteroatom. The heteroaromatic ring system also includes heteroaryl groups, as described above. The heteroatoms in the heteroaromatic ring system are preferably selected from N, O and / or S. An aromatic or heteroaromatic ring system within the meaning of this invention is understood to mean a system that does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups can also be interrupted by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as a C or O atom or a carbonyl group. For example, systems such as 9,9'-spirobifluorene, 9,9-Dialkylfluorene, 9,9-diarylfluorene, diaryl ethers, stilbene, etc. are understood as aromatic or heteroaromatic 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 encompassed by the definition of aromatic or heteroaromatic ring systems. An aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which can be linked to the aromatic or heteroaromatic ring via any position, is understood to mean, for example, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzfluoranthene, naphthacene, pentacene, benzopyrene,Biphenyl, Biphenylen, Terphenyl, Terphenylen, Fluoren, Spirobifluoren, Dihydrophenanthren, Dihydropyren, Tetrahydropyren, cis- oder trans-Indenofluoren, cis- oder trans-Monobenzoindenofluoren, cis- oder trans-Dibenzoindenofluoren, Truxen, Isotruxen, Spirotruxen, Spiroisotruxen, Furan, Benzofuran, Isobenzofuran, Dibenzofuran, Thiophen, Benzothiophen, Isobenzothiophen, Dibenzothiophen, Pyrrol, Indol, Isoindol, Carbazol, Indolocarbazol, Indenocarbazol, Pyridin, Chinolin, Isochinolin, Acridin, Phenan- thridin, Benzo-5,6-chinolin, Benzo-6,7-chinolin, Benzo-7,8-chinolin, Phenothiazin, Phenoxazin, Pyrazol, Indazol, Imidazol, Benzimidazol, Naphthimidazol, Phenan- thrimidazol, Pyridimidazol, Pyrazinimidazol, Chinoxalinimidazol, Oxazol, Benzoxazol, Naphthoxazol, Anthroxazol, Phenanthroxazol, Isoxazol, 1,2-Thiazol, 1,3-Thiazol, Benzo- thiazol, Pyridazin, Benzopyridazin, Pyrimidin, Benzpyrimidin, Chinoxalin, 1,5-Diaza- anthracen, 2,7-Diazapyren, 2,3-Diazapyren, 1,6-Diazapyren, 1,8-Diazapyren, 4,5-diazapyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorubin, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine, and benzothiadiazole. The abbreviations Ar and Ar1, identically or differently at each occurrence, mean an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which is substituted by one or more radicals R, 2 may be substituted, where the radical R 2 or the substituents R 2has / have a meaning as described above or below. A preferred meaning of Ar and Ar1 is described below. The abbreviations Ar2 and Ar3, identically or differently, at each occurrence mean an aromatic ring system having 6 to 40 ring atoms or a heteroaromatic ring system having 9 to 40 ring atoms, which is substituted by one or more radicals R 2 may be substituted, where the radical R 2 or the substituents R 2 has / have a meaning as described above or below. A preferred meaning of Ar2 and Ar3 is described below. The abbreviation Ar5, identical or different at each occurrence, stands for an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which is substituted by one or more radicals R 7 may be substituted, where the radical R 7 or the substituents R 7has / have a meaning as described above or below. A preferred meaning of Ar5 is described below. A cyclic alkyl, alkoxy or thioalkyl group in the sense of this invention is understood to mean a monocyclic, bicyclic or polycyclic group. In the context of the present invention, a straight-chain, branched or cyclic C1 to C 20-Alkylgruppe beispielsweise die Reste Methyl, Ethyl, n-Propyl, i-Propyl, Cyclopropyl, n-Butyl, i-Butyl, s-Butyl, t-Butyl, Cyclobutyl, 2-Methylbutyl, n-Pentyl, s-Pentyl, t-Pentyl, 2-Pentyl, neo-Pentyl, Cyclopentyl, n-Hexyl, s-Hexyl, t-Hexyl, 2-Hexyl, 3- Hexyl, neo-Hexyl, Cyclohexyl, 1-Methylcyclopentyl, 2-Methylpentyl, n-Heptyl, 2-Heptyl, 3- Heptyl, 4-Heptyl, Cycloheptyl, 1-Methylcyclohexyl, n-Octyl, 2-Ethylhexyl, Cyclooctyl, 1- Bicyclo[2,2,2]octyl, 2-Bicyclo[2,2,2]octyl, 2-(2,6-Dimethyl)octyl, 3-(3,7-Dimethyl)octyl, Adamantyl, Trifluormethyl, Pentafluorethyl, 2,2,2-Trifluorethyl, 1,1-Dimethyl-n-hex-1-yl-, 1,1-Dimethyl-n-hept-1-yl-, 1,1-Dimethyl-n-oct-1-yl-, 1,1-Dimethyl-n-dec-1-yl-, 1,1-Dimethyl- n-dodec-1-yl-, 1,1-Dimethyl-n-tetradec-1-yl-, 1,1-Dimethyl-n-hexadec-1-yl-, 1,1-Dimethyl- n-octadec-1-yl-, 1,1-Diethyl-n-hex-1-yl-, 1,1-Diethyl-n-hept-1-yl-, 1,1-Diethyl-n-oct-1-yl-, 1,1-Diethyl-n-dec-1-yl-, 1,1-Diethyl-n-dodec-1-yl-, 1,1-Diethyl-n-tetradec-1-yl-, 1,1- Diethyln-n-hexadec-1-yl-,1,1-Diethyl-n-octadec-1-yl-, 1-(n-propyl)-cyclohex-1-yl-, 1-(n-butyl)-cyclohex-1-yl-, 1-(n-hexyl)-cyclohex-1-yl-, 1-(n-octyl)-cyclohex-1-yl-, and 1-(n-decyl)-cyclohex-1-yl- are understood. The phrase "two or more radicals can form a ring system with each other" refers to the formation of an aliphatic, heteroaliphatic, aromatic, or heteroaromatic ring system, and in the context of the present description, it is understood, among other things, that the two radicals are linked to each other by a chemical bond with the formal elimination of two hydrogen atoms. This is illustrated by the following scheme: Furthermore, the above formulation should also be understood to mean that if one of the two residues represents hydrogen, the second residue binds to the position to which the hydrogen atom was bonded, forming a ring. This is illustrated by the following scheme: The compounds of formula (1) and their preferred embodiments are described below. The preferred embodiments also apply to the mixture according to the invention, the formulation according to the invention, and the organic electroluminescent device according to the invention. In compounds of formula (1), Y is, independently of one another, N, C- [L] b -Ar2or C-[L] b1 -Ar3, where exactly two Y stand for N, which are replaced by a group C-[L] b - Ar2or C-[L] b1 -Ar3 are separated. Preferred embodiments of the compounds of formula (1) are compounds of formula (1a) or (1b) in which the position of the two N atoms is described in more detail, the remaining Y C-[L] b -Ar2 and C-[L] b1 -Ar3, and the symbols used are V, [L], Ar2, Ar3, b, b1, Het, R 1 , R# and b2 have a meaning given above or preferred below, The invention accordingly further relates to compounds of formulas (1a) or (1b), as described above or preferably described below. In compounds of formulas (1), (1a) and (1b), Het preferably represents formula (1-2). In formulas (1-2) to (1-5), R represents 1 preferably represents H or D. In compounds of formula (1a), Het is preferably bonded in position 9 of the diazadibenzofuran or diazadibenzothiophene. In compounds of formula (1b), Het is preferably bonded in position 5 of the diazadibenzofuran or diazadibenzothiophene. The numbering of the positions is shown below using the example of the diazadibenzofuran skeleton: In compounds of formulas (1), (1a) and (1b), V is preferably O. In compounds of formulas (1), (1a) and (1b), R 1preferably H or D, particularly preferably H. In compounds of the formulas (1), (1a) and (1b), R# preferably represents D or non-deuterated or partially or fully deuterated phenyl, particularly preferably D. In compounds of the formulas (1), (1a) and (1b), b2 preferably represents 0. In compounds of the formulas (1), (1a) and (1b) or preferred compounds of the formulas (1), (1a) and (1b), the symbol [L] as a linker represents an aromatic ring system having 6 to 40 ring atoms or a heteroaromatic ring system having 9 to 40 ring atoms, which may be unsubstituted or partially or fully substituted by D. In compounds of formulas (1), (1a) and (1b) or preferred compounds of formulas (1), (1a) and (1b), the symbol [L], when occurring, independently preferably represents a linker selected from the group L-1 to L-34, which may be unsubstituted or partially or fully substituted by D where V1 each independently represents O, S or N-aryl, the dashed lines represent the bond to Ar2 or Ar3 and to the radical of formulas (1), (1a) or (1b) and where the abbreviation “aryl” represents an aromatic or heteroaromatic ring system having 5 to 30 ring atoms which is bonded to one or more radicals R 2may be substituted. “Aryl” is preferably phenyl, 1,3-biphenyl, 1,4-biphenyl, dibenzofuranyl or dibenzothiophenyl, where these radicals may be unsubstituted or partially or fully substituted by D. Preference is given to V1O or N-aryl. Particular preference is given to V1O. In compounds of the formulas (1), (1a) and (1b) or preferred compounds of the formulas (1), (1a) and (1b), the symbol [L], when it occurs, in each case independently, particularly preferably represents linkers selected from the group L-2, L-3, L-4, L-5, L-21 to L-34, as described above or preferably described, which may be partially or fully substituted by D. In compounds of formulas (1), (1a) and (1b) or preferred compounds of formulas (1), (1a) and (1b), b is preferably 0. In compounds of formulas (1), (1a) and (1b) or preferred compounds of formulas (1), (1a) and (1b), b1 is preferably 0.In compounds of formulas (1), (1a) and (1b) or preferred compounds of formulas (1), (1a) and (1b), Ar and Ar1 are preferably different from one another. Ar and Ar1 are each independently preferably selected from the following groups Ar1 to Ar17:. where R' is selected at each occurrence, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(Ar0)2, NH2, N(R 2 )2, C(=O)Ar0, C(=O)H, C(=O)R 2 , P(=O)(Ar0)2, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is substituted by one or more radicals R 2 may be substituted, where one or more non-adjacent CH2 groups are substituted by HC=CH, R 2 C=CR 2 , C≡C, Si(R 2 )2, Ge(R 2 )2, Sn(R 2)2, C=O, C=S, C=Se, C=NR 2 , P(=O)(R 2 ), SO, SO2, NH, NR 2 , O, S, CONH or CONR 2 and wherein one or more H atoms may be replaced by F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which is substituted by one or more radicals R 2 may be substituted, an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, which may be substituted with one or more radicals R 2 may be substituted, or a combination of these systems, where optionally two or more adjacent substituents R' may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted with one or more radicals R 2 may be substituted; and Ar0 is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms which is substituted by one or more radicals R 2may be substituted; one or more R' may also be directly bonded to a C atom of Ar0. The dashed line indicates the bonding site to the radical of formulas (1-2), (1-3), (1-4) and (1-5). Particularly preferably, Ar or Ar1 each independently represent Ar-1, Ar-2, Ar-6, Ar-11 and Ar-17, where R' has a meaning given above or given below with preference. R' in substituents of formulas Ar-1 to Ar-17, as described above, is preferably selected from the group H, D, CN, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which is bonded to one or more radicals R 2may be substituted. Ar0 in substituents of the formulas Ar-13 to Ar-16, as described above, is preferably phenyl, 1,2-biphenyl, 1,3-biphenyl or 1,4-biphenyl, which may optionally be partially or fully deuterated. In compounds of the formulas (1), (1a) and (1b) or preferably described compounds of the formulas (1), (1a) and (1b), Ar2 and Ar3 each independently represent an aromatic ring system having 6 to 40 ring atoms or a heteroaromatic ring system having 9 to 40 ring atoms, which is substituted with one or more radicals R 2may be substituted. In compounds of formulas (1), (1a) and (1b) or preferred compounds of formulas (1), (1a) and (1b), Ar2 and Ar3 are preferably different from one another. Ar2 and Ar3 are each independently selected from the groups Ar-1 to Ar-17, as previously described or preferably described, wherein the dashed line indicates the bonding site to [L] or the radical of formulas (1), (1a) and (1b). In compounds of formulas (1), (1a) and (1b) or preferably described compounds of formulas (1), (1a) and (1b), Ar2 and Ar3 each independently of one another particularly preferably denote phenyl, 1,2-biphenyl, 1,3-biphenyl, 1,4-biphenyl, triphenylenyl, fluoranthenyl, dibenzofuranyl, indenocarbazol-N-yl, N-aryl-indolocarbazol-N-yl, carbazol-N-yl or aryl-N-carbazolyl, which are reacted with one or more radicals R 2 may be substituted, where aryl has a meaning mentioned above and R 2has a meaning given above or below. If the substituent Ar2 or Ar3, as described above, is substituted with one or more radicals R 2 substituted, R 2 preferably each independently selected from the group D, F or CN, particularly preferably as D. In compounds of formulas (1), (1a) and (1b) or preferably described compounds of formulas (1), (1a) and (1b), Ar2 and Ar3 each independently very particularly preferably denote phenyl, 1-4-biphenyl or dibenzofuranyl, which may be partially or fully deuterated. In a preferred embodiment of the compounds of formulas (1), (1a) and (1b), these compounds are partially or fully deuterated, particularly preferably fully deuterated. Examples of suitable host materials of formulas (1), (1a) and (1b), as previously described or preferably described, are the structures listed below in Table 1. Table 1:

[0002]

[0003] -02-

[0004] Particularly suitable compounds of formulas (1), (1a) and (1b), as previously described or preferably described, are the compounds E1 to E27 of Table 2. Table 2:

[0005] The compounds of the invention can be prepared by synthetic steps known to those skilled in the art, such as bromination, Suzuki coupling, Ullmann coupling, Hartwig-Buchwald coupling, etc. Suitable compounds containing a diazadibenzofuran or diazadibenzothiophene group can often be obtained commercially; the starting compounds presented in the examples are obtainable by known processes, so reference is made thereto. In the following synthesis schemes, the compounds are shown with a small number of substituents to simplify the structures. This does not exclude the presence of any other substituents in the processes. The processes shown for synthesizing the compounds of the invention are to be understood as examples. The skilled person can develop alternative synthesis routes within the scope of their general specialist knowledge. Scheme 3: Ar and Ar' correspond to Ar2 and Ar3 in compounds of formula (1) Scheme 4: Ar and Ar' correspond to Ar2 and Ar3 in compounds of formula (1) Scheme 5: Scheme 6: Representative of all Schemes 1 to 5, Scheme 6 shows the reaction with Het-B(OH)2 Detailed reaction conditions are known from the prior art or are described in the examples. By these processes, optionally followed by purification, such as recrystallization or sublimation, the compounds of formula (1) can be obtained in high purity, preferably more than 99% (determined by 1H-NMR and / or HPLC). For processing the compounds of the invention from the liquid phase, for example by spin coating or printing processes, formulations of the compounds of the invention or mixtures of compounds of the invention with other functional materials, such as matrix materials, fluorescent emitters, phosphorescent emitters, and / or emitters exhibiting TADF, are required. These formulations can be, for example, solutions, dispersions, or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone,3-Methylanisole, 4-Methylanisole, 3,4-Dimethylanisole, 3,5-Dimethylanisole, Acetophenone, α-Terpineol, Benzothiazole, Butyl Benzoate, Cumene, Cyclohexanol, Cyclohexanone, Cyclohexylbenzene, Decalin, Dodecylbenzene, Ethyl Benzoate, Indane, 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 sebacate, octyl octanoate, heptylbenzene, menthyl isovalerate, cyclohexylhexanoate or mixtures of these solvents. The compounds of formula (1) according to the invention, as described above or preferably described,are suitable for use in an organic electroluminescent device, in particular as a matrix material. If the compound according to the invention is used as a matrix material or synonymously as a host material in an emitting layer, it is preferably used in combination with another compound. The invention therefore further provides a mixture comprising at least one compound of formula (1) or at least one preferred compound of one of the formulas (1), (1a) and (1b) or a compound of Table 1 or one of the compounds E1 to E27 and at least one other compound selected from the group of matrix materials, phosphorescent emitters, fluorescent emitters and / or emitters exhibiting TADF (thermally activated delayed fluorescence). Suitable matrix materials and emitters that can be used in this mixture according to the invention areare described below. The present invention further provides a formulation comprising at least one compound according to the invention, as described above, or a mixture according to the invention, as described above, and at least one solvent. The solvent can be an above-mentioned solvent or a mixture of these solvents. The present invention further provides an organic electronic device comprising an anode, a cathode, and at least one organic layer, comprising at least one compound of formula (1) or at least one preferred compound of one of the formulas (1), (1a), and (1b), or a compound of Table 1, or one of the compounds E1 to E27. The organic electronic device can, for example, consist of organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs),organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors, organic photoreceptors. The organic electronic device is preferably an organic electroluminescent device. The organic electroluminescent device according to the invention (synonymously organic electroluminescent device) is, for example, an organic light-emitting transistor (OLET), an organic field quench device (OFQD), an organic light-emitting electrochemical cell (OLEC),an organic laser diode (O-laser) or an organic light-emitting diode (OLED). The organic electroluminescent device according to the invention is in particular an organic light-emitting diode or an organic light-emitting electrochemical cell. The device according to the invention is particularly preferably an OLED. The organic layer of the device according to the invention preferably contains, in addition to a light-emitting layer (EML), a hole injection layer (HIL), a hole transport layer (HTL), a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), an exciton blocking layer, an electron blocking layer and / or charge generation layers. The device according to the invention can also contain several layers from this group, preferably selected from EML, HIL, HTL, ETL, EIL and HBL.Interlayers can also be introduced between two emitting layers, which, for example, have an exciton-blocking function. If multiple emitting layers are present, they preferably have a total of several emission maxima between 380 nm and 750 nm, resulting in an overall white emission, i.e., different emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. One emitting layer can also contain several fluorescent and / or phosphorescent compounds. Systems with three emitting layers are particularly preferred, with the three layers exhibiting blue, green, and orange or red emission. As an alternative to the combination as described above,An emitting layer can also exhibit yellow emission. Such combinations are known to the person skilled in the art. The organic electroluminescent device according to the invention can also be a tandem electroluminescent device, in particular for white-emitting OLEDs. The device can also contain inorganic materials or layers composed entirely of inorganic materials. It is not difficult for the person skilled in the art to resort to a large number of materials known in the prior art in order to select suitable materials for use in the previously described layers of the organic electroluminescent device. In doing so, the person skilled in the art makes common considerations regarding the chemical and physical properties of the materials, since it is known to himthat the materials in an organic electroluminescent device interact with one another. This applies, for example, to the energy positions of the orbitals (HOMO, LUMO) or the position of triplet and singlet energies, but also to other material properties. The compound of formula (1) according to the invention, as described above or preferably described, can be used in different layers, depending on the precise structure. An organic electroluminescent device containing a compound according to formula (1) or the preferred embodiments described above in an emitting layer as a matrix material for fluorescent emitters, phosphorescent emitters, or for emitters exhibiting TADF (thermally activated delayed fluorescence) is preferred.in particular for phosphorescent emitters. Furthermore, the compound according to the invention can also be used in an electron-transport layer and / or in a hole-transport layer and / or in an exciton-blocking layer and / or in a hole-blocking layer. The compound according to the invention is particularly preferably used as a matrix material in an emitting layer or as an electron-transport or hole-blocking material in an electron-transport or hole-blocking layer. The present invention further provides an organic electronic device as described above, wherein the organic layer contains at least one light-emitting layer which comprises at least one compound of the formula (1) or the at least one preferred compound of one of the formulas ((1),(1a) and (1b) or a compound of Table 1 or one of the compounds E1 to E27. In one embodiment of the invention, a further matrix material is selected for the device according to the invention in the light-emitting layer, which is used with compounds of formula (1), as described above or preferably described, or with the compounds of Table 1 or the compounds E1 to E27. The present invention accordingly further provides an organic electronic device as described above, wherein the organic layer contains at least one light-emitting layer containing at least one compound of formula (1) or the at least one preferred compound of one of the formulas (1), (1a) and (1b) or a compound of Table 1 or one of the compounds E1 to E27 and a further matrix material. Suitable matrix materials that can be used in combination with the compounds according to the invention,are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, triarylamines, carbazole derivatives, biscarbazoles, indolocarbazole derivatives, indenocarbazole derivatives, azacarbazole derivatives, bipolar matrix materials, azaboroles or boronic esters, triazine derivatives, zinc complexes, diazasilole or tetraazasilole derivatives, diazaphosphole derivatives, bridged carbazole derivatives, triphenylene derivatives, or dibenzofuran derivatives. Likewise, another phosphorescent emitter, which emits at a shorter wavelength than the actual emitter, can be present in the mixture as a co-host, or a compound that does not participate, or only participates to a limited extent, in charge transport, such as a wide-band-gap compound. Wide-band-gap material is understood herein to mean a material as disclosed in US 7,294,849, which is characterized by a band gap of at least 3.5 eV,where the band gap is understood to be the distance between the HOMO and LUMO energy of a material. Particularly suitable matrix materials, which are advantageously combined with compounds of formula (1), as described above or as preferred, in a mixed matrix system, can be selected from the compounds of formulas (6), (7), (8), (9), (10) or (11), as described below. Accordingly, a further subject of the invention is an organic electronic device comprising an anode, a cathode, and at least one organic layer containing at least one light-emitting layer, wherein the at least one light-emitting layer contains at least one compound of formula (1) as matrix material 1, as described above or as preferred, and at least one compound of formulas (6), (7), (8), (9), (10) or (11) as matrix material 2.

[0006] where the symbols and indices used are: A 1 is C(R 7 )2, NR 7 , O or S; L is a bond, O, S, C(R 7 )2or NR 7 ; A is at each occurrence independently a group of formula (3) or (4), X2is the same or different at each occurrence CH, CR 6 or N, where a maximum of 2 symbols can represent X2N; * indicates the binding site to the formula (9); U 1 , U 2 are a bond, O, S, C(R 7 )2 or NR 7 ; R 6 is, identically or differently at each occurrence, D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 7may be substituted and wherein one or more non-adjacent CH2 groups are substituted by Si(R 7 )2, C=O, NR 7 , O, S or CONR 7 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, each of which is substituted by one or more radicals R 7 can be substituted; two radicals R 6 also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar5, identically or differently at each occurrence, independently represents an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which is reacted with one or more radicals R 7 may be substituted; R 7 is the same or different at each occurrence D, F, Cl, Br, I, N(R 8 )2, CN, NO2, OR 8 , SR 8 , Si(R 8 )3, B(OR 8 )2, C(=O)R 8 , P(=O)(R 8 )2, S(=O)R 8 , S(=O)2R 8 , OSO2R8 , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 8 may be substituted, with one or more non-adjacent CH2 groups being substituted by Si(R 8 )2, C=O, NR 8 , O, S or CONR 8 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which is substituted by one or more radicals R 8 may be substituted; two or more radicals R 7 together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system, preferably the radicals R 7 no such ring system; R 8is, on each occurrence, the same or different, H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, in particular a hydrocarbon radical, having 1 to 20 C atoms, in which one or more H atoms may also be replaced by F; c, c1, c2 each independently denote 0 or 1 on each occurrence, where the sum of the indices on each occurrence is c+c1+c2 = 1; d, d1, d2 each independently denote 0 or 1 on each occurrence, where the sum of the indices on each occurrence is d+d1+d2 = 1; q, q1, q2 each independently denote 0 or 1 on each occurrence; s is, on each occurrence, the same or different, 0, 1, 2, 3 or 4; t is, on each occurrence, the same or different, 0, 1, 2 or 3; u is, on each occurrence, the same or different, 0, 1 or 2; u1, u2 each independently represent 0 or 1 on each occurrence, where the sum u1 + u2 = 1; and v is 0 or 1.In compounds of formulas (6), (7), (8), (10) or (11), s is preferably 0 or 1 when the radical R. 6 is different from D, or particularly preferably 0. In compounds of formula (6), (7) or (8), t is preferably 0 or 1 if the radical R 6 is different from D, or particularly preferably 0. In compounds of formulas (6), (7), (8) or (10), u is preferably 0 or 1 if the radical R 6 is different from D, or particularly preferably 0. The sum of the indices s, t and u in compounds of the formulas (6), (7), (8), (10) or (11) is preferably at most 6, particularly preferably at most 4 and particularly preferably at most 2. This preferably applies when R 6is different from D. In compounds of the formula (9), c, c1, c2 each independently denote 0 or 1 at each occurrence, where the sum of the indices at each occurrence denotes c+c1+c21. Preferably, c2 has the meaning 1. In compounds of the formula (9), L is preferably a single bond or C(R 7 )2, where R 7 has a meaning mentioned above, particularly preferably L is a single bond. In formula (4), U 1 or U 2 when occurring, preferably a single bond or C(R 7 )2, where R 7 has a meaning mentioned above, particularly preferred are U 1 or U 2 when occurring, a single bond. In a preferred embodiment of the compounds of formulas (6), (7), (8), (9), (10) or (11), which can be combined according to the invention with compounds of formula (1), as described above, R 6identically or differently on each occurrence selected from the group consisting of D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl group is in each case substituted with one or more radicals R 7 may be substituted, or an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, preferably having 5 to 40 ring atoms, each substituted by one or more radicals R 7 may be substituted. In a preferred embodiment of the compounds of formulas (6), (7), (8), (9), (10) or (11), which can be combined according to the invention with compounds of formula (1), as described above, R 6 identically or differently on each occurrence selected from the group consisting of D or an aromatic or heteroaromatic ring system having 6 to 30 ring atoms, which is reacted with one or more radicals R 7can be substituted. Preferably, Ar5 in compounds of formulas (6), (7), (8), (10) or (11) is selected from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorenyl, which may be linked via the 1-, 2-, 3- or 4-position, spirobifluorenyl, which may be linked via the 1-, 2-, 3- or 4-position, naphthyl, in particular 1- or 2-linked naphthyl, or residues derived from indole, benzofuran, benzothiophene, carbazole, which may be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, which may be linked via the 1-, 2-, 3- or 4-position can be, dibenzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline,Phenanthrene or triphenylene, each of which is substituted with one or more radicals R, 7 may be substituted. Preferably, Ar5 is unsubstituted. If A 1 in formula (7) or (8) or (11) for NR 7 the substituent R 7 which is bonded to the nitrogen atom, preferably represents an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which can also be substituted by one or more radicals R 8 In a particularly preferred embodiment, this substituent R 7 identical or different on each occurrence, represents an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, in particular having 6 to 18 aromatic ring atoms. Preferred embodiments for R 7are phenyl, biphenyl, terphenyl and quaterphenyl, which are preferably unsubstituted, as well as radicals derived from triazine, pyrimidine and quinazoline, which are substituted by one or more radicals R 8 can be substituted. If A 1 in formula (7) or (8) or (11) for C(R 7 )2, the substituents R 7 which are bonded to this carbon atom, preferably identically or differently on each occurrence, represent a linear alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which can also be substituted by one or more radicals R 8 R is particularly preferably 7 represents a methyl group or a phenyl group. The radicals R 7also form a ring system with each other, resulting in a spiro system. In a preferred embodiment of the compounds of formulas (6), (7), (8), (9), (10) and (11), these compounds are partially or fully deuterated, particularly preferably fully deuterated. The preparation of the compounds of formulas (6), (7), (8), (9), (10) and (11) is generally known, and some of the compounds are commercially available. Compounds of formula (9) are disclosed, for example, in WO2021 / 180614, pages 110 to 119, in particular as examples on pages 120 to 127. Their preparation is disclosed in WO2021 / 180614 on page 128 and in the synthesis examples on pages 214 to 218. The preparation of the triarylamines of formula (11) is known to the person skilled in the art, and some of the compounds are commercially available.If the additional matrix material is a deuterated compound, it is possible for the additional matrix material to be a mixture of deuterated compounds of the same basic chemical structure, differing only in the degree of deuteration. In a preferred embodiment of the additional matrix material, this is a mixture of deuterated compounds of the formulas (6), (7), (8), (9), (10), or (11), as described above, wherein the degree of deuteration of these compounds is at least 50% to 90%, preferably 70% to 100%. Corresponding deuteration methods are known to the person skilled in the art and are described, for example, in KR2016041014, WO2017 / 122988, KR202005282, KR101978651 and WO2018 / 110887 or in Bulletin of the Chemical Society of Japan, 2021, 94(2), 600-605 or Asian Journal of Organic Chemistry, 2017, 6(8), 1063-1071.A suitable method for deuterating a compound by exchanging one or more H atoms for D atoms is to treat the compound to be deuterated in the presence of a platinum catalyst or palladium catalyst and a deuterium source. The term "deuterium source" refers to any compound containing one or more D atoms and capable of releasing them under suitable conditions. The platinum catalyst is preferably dry platinum on carbon, preferably 5% dry platinum on carbon. The palladium catalyst is preferably dry palladium on carbon, preferably 5% dry palladium on carbon. A suitable deuterium source is D2O, benzene-d6, chloroform-d3, acetonitrile-d3, acetone-d6, acetic acid-d4, methanol-d4, or toluene-d8. A preferred deuterium source is D2O or a combination of D2O and a fully deuterated organic solvent.A particularly preferred deuterium source is the combination of D2O with a fully deuterated organic solvent, whereby the fully deuterated solvent is not restricted here. Particularly suitable fully deuterated solvents are benzene-d6 and toluene-d8. A particularly preferred deuterium source is a combination of D2O and toluene-d8. The reaction is preferably carried out with heating, more preferably with heating to temperatures between 100°C and 200°C. Furthermore, the reaction is preferably carried out under pressure. Examples of suitable further matrix materials for a combination with compounds of formula (1), as described above or preferably described, are the compounds described in WO2019 / 229011, Table 3, pages 137 to 203, which may also be partially or fully deuterated.Examples of suitable further matrix materials for a combination with compounds of the formula (1), as described above or preferably described, are the compounds described in WO2021 / 180625, Table 3, pages 131 to 127 and in Table 4, pages 137 to 139, which may also be partially or fully deuterated. Examples of suitable further matrix materials for a combination with compounds of the formula (1), as described above or preferably described, are the compounds described in WO2011 / 088877, Table page 30, compounds 1 to 166, which may also be partially or fully deuterated. Examples of suitable further matrix materials for a combination with compounds of the formula (1), as described above or preferably described, are the compounds described in WO2011 / 128017, Table page 23, compounds 1 to 151, which may also be partially or fully deuterated.For a combination with a compound of formula (1), as described above or preferably described, compounds of formula (6) are particularly suitable in which at least one group Ar5 represents a heteroaromatic ring system having 5 to 40 ring atoms which is substituted by one or more radicals R. 7may be substituted or compounds of formula (9) or (10). For a combination with a compound of formula (1), as described above or preferably described, very particularly preferred compounds of formula (9) or (10) are suitable. For a combination with a compound of formula (1), as described above or preferably described, very particularly preferred compounds of formula (10) are suitable. Further examples of suitable host materials of formulas (6), (7), (8), (9), (10) and (11) for a combination with compounds of formula (1), as described above or preferably described, are the structures listed below in Table 3 and Table 4. Table 3:

[0007] Particularly suitable compounds of formulas (6), (7), (8), (9), (10) or (11), which are selected according to the invention and are preferably used in combination with at least one compound of formula (1) in the electroluminescent device according to the invention, are the compounds of Table 4. Table 4:

[0008] The above-mentioned host materials of formula (1) and their preferred embodiments, or the compounds of Table 1 and compounds E1 to E27, can be combined in any way in the device according to the invention with the aforementioned matrix materials / host materials, the matrix materials / host materials of formulas (6), (7), (8), (9), (10), or (11), and their preferred embodiments in Table 3, or compounds H1 to H27. Very particularly preferred mixtures of the compounds of formula (1) with the host materials of formulas (6), (7), (8), (9), (10), or (11) for the device according to the invention are obtained by combining compounds E1 to E27 with compounds H1 to H27, as shown below in Table 5. The first mixture M1, for example, is a combination of compound E1 with H1. Table 5:

[0009] The concentration of the host material of formula (1), as described above or described as preferred, in the mixture according to the invention or in the light-emitting layer of the device according to the invention is usually in the range from 5 wt.% to 90 wt.%, preferably in the range from 10 wt.% to 85 wt.%, more preferably in the range from 20 wt.% to 85 wt.%, even more preferably in the range from 30 wt.% to 80 wt.%, very particularly preferably in the range from 20 wt.% to 60 wt.% and most preferably in the range from 30 wt.% to 50 wt.%, based on the entire mixture or based on the entire composition of the light-emitting layer. The concentration of the host material of one of the formulas (6), (7), (8), (9), (10) or (11), as described above or described as preferred, in the mixture according to the invention or in the light-emitting layer of the device according to the invention is usually in the range from 10 wt.% to 95 wt.-%, preferably in the range from 15 wt.% to 90 wt.%, more preferably in the range from 15 wt.% to 80 wt.%, even more preferably in the range from 20 wt.% to 70 wt.%, very particularly preferably in the range from 40 wt.% to 80 wt.% and most preferably in the range from 50 wt.% to 70 wt.%, based on the entire mixture or based on the entire composition of the light-emitting layer. The present invention also relates to a mixture which, in addition to the above-mentioned host materials of the formula (1), referred to as host material 1 in the future, and the host material of one of the formulas (6), (7), (8), (9), (10) or (11), referred to as host material 2 in the future, as described above or preferably described, in particular mixtures M1 to M729, contains at least one phosphorescent emitter.The present invention also relates to an organic electroluminescent device, as described above or preferably described, wherein the light-emitting layer, in addition to the aforementioned host materials of formula (1) and one of formulas (6), (7), (8), (9), (10) or (11), as described above or preferably described, in particular the material combinations M1 to M729, contains at least one phosphorescent emitter. The term phosphorescent emitters typically encompasses compounds in which light emission occurs through a spin-forbidden transition from an excited state with higher spin multiplicity, i.e., a spin state > 1, for example, through a transition from a triplet state or a state with an even higher spin quantum number, for example, a quintet state. Preferably, this refers to a transition from a triplet state.Particularly suitable phosphorescent emitters (= triplet emitters) are compounds that emit light upon suitable excitation, preferably in the visible range, and also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80, in particular a metal with this atomic number. Preferably, compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are used as phosphorescent emitters, in particular compounds containing iridium or platinum. For the purposes of the present invention, all luminescent compounds containing the above-mentioned metals are considered phosphorescent emitters.In general, all phosphorescent complexes as used in the prior art for phosphorescent OLEDs and as known to those skilled in the art in the field of organic electroluminescent devices are suitable. Preferred phosphorescent emitters according to the present invention correspond to formula (IIIa). where the symbols and indices for this formula (IIIa) have the meaning: n+m is 3, n is 1 or 2, m is 2 or 1, X is, identically or differently on each occurrence, N or CR, R is, identically or differently on each occurrence, H, D, F, CN or a branched or linear alkyl group having 1 to 10 C atoms or a partially or fully deuterated branched or linear alkyl group having 1 to 10 C atoms or a cycloalkyl group having 4 to 7 C atoms which may be partially or fully substituted with deuterium or an aromatic or heteroaromatic ring system having 5 to 60 ring atoms which may be partially or fully substituted with deuterium.The invention accordingly further provides an organic electroluminescent device as described above or preferably described, characterized in that the light-emitting layer, in addition to the host materials 1 and 2, contains at least one phosphorescent emitter which corresponds to the formula (IIIa), as described above. In emitters of the formula (IIIa), n is preferably 1 and m is preferably 2. In emitters of the formula (IIIa), one X is preferably selected from N and the other Xs are CR or all Xs, identical or different on each occurrence, are CR. In emitters of the formula (IIIa), at least one R is preferably different from H. In emitters of the formula (IIIa), two Rs are preferably different from H and have one of the meanings otherwise given above for the emitters of the formula (IIIa). Preferred phosphorescent emitters according to the present invention correspond to the formulas (I), (II), (III), (IV) or (V).

[0010] where the symbols and indices for these formulas (I), (II), (III), (IV) and (V) have the meaning: R1 is H or D, R2 is H, D, F, CN or a branched or linear alkyl group having 1 to 10 C atoms or a partially or fully deuterated branched or linear alkyl group having 1 to 10 C atoms or a cycloalkyl group having 4 to 10 C atoms, which may be partially or fully substituted with deuterium. Preferred phosphorescent emitters according to the present invention correspond to the formulas (VI), (VII) or (VIII),

[0011] where the symbols and indices for these formulas (VI), (VII), and (VIII) have the following meaning: R1 is H or D, R2 is H, D, F, CN, or a branched or linear alkyl group having 1 to 10 C atoms, or a partially or fully deuterated branched or linear alkyl group having 1 to 10 C atoms, or a cycloalkyl group having 4 to 10 C atoms, which may be partially or fully substituted with deuterium. Preferred examples of phosphorescent emitters are described in WO2019 / 007867 on pages 120 to 126 in Table 5 and on pages 127 to 129 in Table 6. The emitters are incorporated into the description by this reference. Particularly preferred examples of phosphorescent emitters are listed in Table 6 below. Table 6: In the mixtures according to the invention or in the light-emitting layer of the device according to the invention, each mixture selected from the sum of the mixtures M1 to M729 is preferably combined with a compound of the formula (IIIa) or a compound of the formulas (I) to (VIII) or a compound from Table 6. The light-emitting layer in the organic electroluminescent device according to the invention comprising at least one phosphorescent emitter is preferably an infrared-emitting, yellow-, orange-, red-, green-, blue-, or ultraviolet-emitting layer, particularly preferably a yellow- or green-emitting layer, and very particularly preferably a green-emitting layer. A yellow-emitting layer is understood to mean a layer whose photoluminescence maximum is in the range from 540 to 570 nm.An orange-emitting layer is understood to be a layer whose photoluminescence maximum lies in the range from 570 to 600 nm. A red-emitting layer is understood to be a layer whose photoluminescence maximum lies in the range from 600 to 750 nm. A green-emitting layer is understood to be a layer whose photoluminescence maximum lies in the range from 490 to 540 nm. A blue-emitting layer is understood to be a layer whose photoluminescence maximum lies in the range from 440 to 490 nm. The photoluminescence maximum of the layer is determined by measuring the photoluminescence spectrum of the layer with a layer thickness of 50 nm at room temperature, wherein the layer contains the inventive combination of the host materials of formula (1) and one of the formulas (6), (7), (8), (9), (10) or (11) and the corresponding emitter.The photoluminescence spectrum of the layer is recorded, for example, using a commercially available photoluminescence spectrometer. The photoluminescence spectrum of the selected emitter is usually measured in an oxygen-free solution, 10. -5molar, measured at room temperature, and any solvent in which the selected emitter dissolves at the specified concentration is suitable. Particularly suitable solvents are usually toluene or 2-methyl-THF, but also dichloromethane. The measurement is carried out using a commercially available photoluminescence spectrometer. The triplet energy T1 in eV is determined from the photoluminescence spectra of the emitters. First, the peak maximum Plmax. (in nm) of the photoluminescence spectrum is determined. The peak maximum Plmax. (in nm) is then converted to eV according to: E(T1 in eV) = 1240 / E(T1 in nm) = 1240 / PLmax. (in nm). Preferred phosphorescent emitters are therefore yellow emitters, preferably of formula (IIIa), formulas (I) to (VIII) or from Table 6, whose triplet energy T1 is preferably between ~2.3 eV and ~2.1 eV.Preferred phosphorescent emitters are accordingly green emitters, preferably of formula (IIIa), formulas (I) to (VIII), or from Table 6, whose triplet energy T1 is preferably between ~2.5 eV and ~2.3 eV. Particularly preferred phosphorescent emitters are accordingly green emitters, preferably of formula (IIIa), formulas (I) to (VIII), or from Table 6, as described above, whose triplet energy T1 is preferably between ~2.5 eV and ~2.3 eV. Very particular preference is given to selecting green emitters, preferably of formula (IIIa), formulas (I) to (VIII), or from Table 6, as described above, for the mixture according to the invention or the emitting layer according to the invention. Fluorescent emitters can also be present in the light-emitting layer of the device according to the invention or in the mixture according to the invention.Preferred fluorescent-emitting compounds are selected from the class of arylamines, where preferably at least one of the aromatic or heteroaromatic ring systems of the arylamine is a fused ring system, particularly preferably having at least 14 ring atoms. Preferred examples of these are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic chryseneamines, or aromatic chrysenediamines. An aromatic anthraceneamine is understood to be a compound in which one diarylamino group is bonded directly to one anthracene group, preferably in the 9-position. An aromatic anthracenediamine is understood to be a compound in which two diarylamino groups are bonded directly to one anthracene group, preferably in the 9,10-position.Aromatic pyrenamines, pyrenediamines, chrysenamines, and chrysenediamines are defined analogously, with the diarylamino groups on the pyrene preferably being bonded in the 1-position or 1,6-position. Further preferred emitting compounds are indenofluorenamines or diamines, benzoindenofluorenamines or diamines, and dibenzoindenofluorenamines or diamines, as well as indenofluorene derivatives with fused aryl groups. Pyrene-arylamines are also preferred. Also preferred are benzoindenofluorene amines, benzofluorene amines, extended benzoindenofluorenes, phenoxazines, and fluorene derivatives linked to furan units or thiophene units. Furthermore, the light-emitting device or the mixture according to the invention can also contain materials that exhibit TADF (thermally activated delayed fluorescence).In a further preferred embodiment of the invention, the at least one light-emitting layer of the organic electroluminescent device can comprise, in addition to the host materials 1 and 2, as described above or described as preferred, further host materials or matrix materials, so-called mixed-matrix systems. The mixed-matrix systems preferably comprise three or four different matrix materials, particularly preferably three different matrix materials (i.e., a further matrix component in addition to the host materials 1 and 2, as described above). Particularly suitable matrix materials, which can be used in combination as a matrix component of a mixed-matrix system, are selected from wide-band gap materials, bipolar host materials, electron transport materials (ETMs), and hole transport materials (HTMs).The mixed-matrix system is preferably optimized for an emitter of formula (IIIa), formulas (I) to (VIII), or from Table 6. According to one embodiment of the present invention, the mixture contains no further components, i.e., functional materials, besides the constituents of the host material of formula (1) and host material 2, as described above. These are material mixtures used as such to produce the light-emitting layer. These mixtures are also referred to as premix systems, which are used as the sole material source during the vapor deposition of the host materials for the light-emitting layer and which have a constant mixing ratio during vapor deposition. This allows for the simple and rapid vapor deposition of a layer with a uniform distribution of the components, without the need for precise control of a large number of material sources.According to an alternative embodiment of the present invention, in addition to the constituents of the host material of formula (1) and the host material 2, as described above, the mixture also contains a phosphorescent emitter, as described above. With a suitable mixing ratio during vapor deposition, this mixture can also be used as the sole material source, as described above. The components or constituents of the light-emitting layer of the device according to the invention can thus be processed by vapor deposition or from solution. The material combination of the host materials 1 and 2, as described above or preferably described, optionally with the phosphorescent emitter, as described above or preferably described, is provided for this purpose in a formulation containing at least one solvent. Suitable formulations have been described above.The light-emitting layer in the device according to the invention according to the preferred embodiments and the emitting compound preferably contains between 99.9 and 1 vol.%, more preferably between 99 and 10 vol.%, particularly preferably between 98 and 60 vol.%, very particularly preferably between 97 and 80 vol.% of matrix material composed of at least one compound of formula (1) and at least one compound of one of formulas (6), (7), (8), (9), (10) or (11) according to the preferred embodiments, based on the total composition of emitter and matrix material. Accordingly, the light-emitting layer in the device according to the invention preferably contains between 0.1 and 99 vol.%, more preferably between 1 and 90 vol.%, particularly preferably between 2 and 40 vol.%, very particularly preferably between 3 and 20 vol.% of the emitter, based on the total composition of the light-emitting layer consisting of emitter and matrix material.If the compounds are processed from solution, the corresponding amounts in wt. % are preferably used instead of the above-specified amounts in vol. %. The present invention also relates to an organic electroluminescent device as described above or preferably described, wherein the organic layer contains a hole-injection layer (HIL) and / or a hole-transport layer (HTL), the hole-injecting material and hole-transporting material of which belong to the class of arylamines. The sequence of layers in the organic electroluminescent device according to the invention is preferably the following: anode / hole-injection layer / hole-transport layer / emitting layer / hole-blocking layer / electron-transport layer / electron-injection layer / cathode. This sequence of layers is a preferred sequence.It should be noted again that not all of the layers mentioned need to be present and / or that additional layers may be present. All materials that are used according to the prior art as electron transport materials in the electron transport layer can be used as materials for the electron transport layer. In particular, aluminum complexes, for example Alq3, zirconium complexes, for example Zrq4, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives and phosphine oxide derivatives are suitable as the cathode of the device according to the invention. Metals with a low work function, metal alloys or multilayer structures made of different metals, such as alkaline earth metals, alkali metals, main group metals or lanthanides (e.g.Alloys of an alkali or alkaline earth metal and silver are also suitable, for example an alloy of magnesium and silver. In multilayer structures, in addition to the metals mentioned, other metals with a relatively high work function can be used, such as Ag or Al, in which case combinations of the metals, such as Ca / Ag, Mg / Ag, or Ba / Ag, are generally used. It may also be preferable to insert a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor. Examples of suitable materials for this include alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates (e.g. LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.). Lithium quinolinate (LiQ) can also be used for this purpose. The layer thickness of this layer is preferably between 0.5 and 5 nm.Materials with a high work function are preferred as anodes. The anode preferably has a work function greater than 4.5 eV vs. vacuum. Metals with a high redox potential, such as Ag, Pt, or Au, are suitable for this purpose. Metal / metal oxide electrodes (e.g., Al / Ni / NiO) can also be used. x , Al / PtO x) may be preferred. For some applications, at least one of the electrodes must be transparent or partially transparent in order to enable either the irradiation of the organic material (organic solar cell) or the coupling out of light (OLED, O-LASER). Preferred anode materials here are conductive mixed metal oxides. Particular preference is given to indium tin oxide (ITO) or indium zinc oxide (IZO). Also preferred are conductive, doped organic materials, in particular conductive doped polymers. Furthermore, the anode can also consist of several layers, for example an inner layer made of ITO and an outer layer made of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.The organic electroluminescent device according to the invention is structured, contacted, and finally sealed during production (depending on the application), since the lifetime of the devices according to the invention is shortened in the presence of water and / or air. The production of the device according to the invention is not restricted by this. It is possible to coat one or more organic layers, including the light-emitting layer, using a sublimation process. The materials are heated in vacuum sublimation systems at an initial pressure of less than 10. -5 mbar, preferably less than 10 -6 mbar. However, it is also possible that the initial pressure is even lower, for example less than 10 -7mbar. The organic electroluminescent device according to the invention is preferably characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) method or by means of carrier gas sublimation. The materials are then sublimated at a pressure between 10 -5mbar 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). Furthermore, the organic electroluminescent device according to the invention is preferably characterized in that one or more organic layers comprising the composition according to the invention are produced from solution, for example by spin coating, or using any printing process, such as screen printing, flexographic printing, nozzle printing or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing. This requires soluble host materials 1 and 2 and phosphorescent emitters. Processing from solution has the advantage that, for example, the light-emitting layer can be applied very easily and cost-effectively.This technique is particularly suitable for the mass production of organic electroluminescent devices. Hybrid processes are also possible, in which, for example, one or more layers are applied from solution and one or more additional layers are deposited by vapor deposition. These processes are generally known to those skilled in the art and can be applied to organic electroluminescent devices.The invention therefore further provides a process for producing the organic electroluminescent device according to the invention, as described above or preferably described, characterized in that the organic layer, preferably the light-emitting layer, the hole-injection layer and / or hole-transport layer, is applied by vapor deposition, in particular using a sublimation process and / or an OVPD (Organic Vapor Phase Deposition) process and / or with the aid of carrier gas sublimation, or from solution, in particular by spin coating or using a printing process. When produced by vapor deposition, there are basically two ways in which the organic layer according to the invention, preferably the light-emitting layer, can be applied or vapor-deposited onto any desired substrate or the previous layer.On the one hand, the materials used can each be placed in a single material source and then evaporated from the different material sources ("co-evaporation"). On the other hand, the different materials can be premixed ("premixed systems") and the mixture placed in a single material source, from which it is then evaporated ("premix evaporation"). This allows for the simple and rapid deposition of the light-emitting layer with a uniform distribution of the components, without the need for precise control of a large number of material sources.The invention accordingly further provides a method for producing the device according to the invention, characterized in that the light-emitting layer of the organic layer is applied by vapor deposition, wherein the at least one compound of formula (1) together with the other materials forming the light-emitting layer are deposited successively or simultaneously from the vapor phase from at least two material sources. In a preferred embodiment of the present invention, the light-emitting layer is applied by vapor deposition, wherein the components of the composition are premixed and evaporated from a single material source.The invention accordingly further provides a method for producing the device according to the invention, characterized in that the light-emitting layer of the organic layer is applied by vapor deposition, wherein the at least one compound of formula (1) is deposited from the vapor phase together with at least one further matrix material as a premix, sequentially or simultaneously with the light-emitting materials selected from the group of phosphorescent emitters, fluorescent emitters, and / or emitters exhibiting TADF (thermally activated delayed fluorescence). The electronic devices according to the invention, in particular organic electroluminescent devices, are characterized by one or more of the following surprising advantages over the prior art: 1.Electronic devices, in particular organic electroluminescent devices comprising compounds of the formula (1) or the preferred embodiments set out above and below, in particular as matrix material or as electron-conducting materials, have a very long service life. In particular, these compounds bring about low roll-off, i.e. a low drop in the power efficiency of the device at high luminance levels. 2. Electronic devices, in particular organic electroluminescent devices comprising compounds of the formula (1) or the preferred embodiments set out above and below as electron-conducting materials, and / or matrix materials, have excellent efficiency. In particular, compounds of the formula (1) according to the invention or the preferred embodiments set out above and below bring about a low operating voltage when used in electronic devices.3. The compounds of the invention according to formula (1) or the preferred embodiments set out above and below display very high stability and lifetime. 4. Using compounds of the formula (1) or the preferred embodiments set out above and below, the formation of optical loss channels can be avoided in electronic devices, in particular organic electroluminescent devices. As a result, these devices are distinguished by high PL and thus high EL efficiency of emitters and excellent energy transfer from the matrices to dopants. 5. The use of compounds of the formula (1) or the preferred embodiments set out above and below in layers of electronic devices, in particular organic electroluminescent devices, leads to high mobility of the electron conductor structures. 6. Compounds of the formula (1) orThe preferred embodiments described above and below exhibit excellent glass film formation. 7. Compounds according to formula (1) or the preferred embodiments described above and below form very good films from solutions. 8. The compounds according to formula (1) or the preferred embodiments described above and below exhibit a low triplet level T1, which can, for example, be in the range of 2.50 eV - 2.90 eV. These aforementioned advantages are not accompanied by an undue deterioration of the other electronic properties. It should be noted that variations of the embodiments described in the present invention fall within the scope of this invention. Any feature disclosed in the present invention may, unless explicitly excluded, 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 regarded as an example of a generic series or as an equivalent or similar feature. All features of the present invention can be combined with one another in any way, unless certain features and / or steps are mutually exclusive. This applies in particular to preferred features of the present invention. Likewise, features of non-essential combinations can be used separately (and not in combination). The teaching of technical practice disclosed in the present invention can be abstracted and combined with other examples. The invention is explained in more detail by the following examples, without intending to limit it thereby. Examples General methods: The Gaussian16 program package (Rev. B.01) is used in all quantum chemical calculations.The neutral singlet ground state is optimized at the B3LYP / 6-31G(d) level. HOMO and LUMO values ​​are determined at the B3LYP / 6-31G(d) level for the ground-state energy optimized with B3LYP / 6-31G(d). TD-DFT singlet and triplet excitations (vertical excitations) are then calculated using the same method (B3LYP / 6-31G(d)) and the optimized ground-state geometry. The default settings for SCF and gradient convergence are used. From the energy calculation, the HOMO is determined as the last orbital occupied by two electrons (alpha occupancy eigenvalues) and the LUMO as the first unoccupied orbital (alpha virtual eigenvalues) in Hartree units, where HEh and LEh represent the HOMO energy in Hartree units and the LUMO energy in Hartree units, respectively. From this, the HOMO and LUMO values ​​in electronvolts, calibrated using cyclic voltammetry measurements, are determined as follows: HOMOcorr = 0.90603 * HOMO - 0.84836 LUMOcorr = 0.99687 * LUMO - 0.72445 The triplet level T1 of a material is defined as the relative excitation energy (in eV) of the triplet state with the lowest energy, which results from the quantum chemical energy calculation. The singlet level S1 of a material is defined as the relative excitation energy (in eV) of the singlet state with the second lowest energy, which results from the quantum chemical energy calculation. The lowest energetic singlet state is referred to as S0. The method described here is independent of the software package used and always delivers the same results. Examples of frequently used programs for this purpose are "Gaussian09" (Gaussian Inc.) and Q-Chem 4.1 (Q-Chem, Inc.). In this case, the program package "Gaussian16 (Rev. B.01)" is used to calculate the energies. Synthesis examples The following syntheses are carried out under a protective gas atmosphere in dried solvents, unless otherwise stated.The compounds of the invention can be prepared by synthetic methods known to those skilled in the art. a) (3-Amino-4-chloro-2-benzofuranyl)phenylmethanone. To a solution of 99 g (489 mmol) of 2-bromo-6-hydroxybenzonitrile and 99.5 g (489 mmol) of bromoacetophenone in 790 ml of acetone, 319 g (979 mmol) of cesium carbonate are added portionwise at room temperature under argon. The reaction mixture is heated to 60°C for 2 hours. The mixture is then cooled to room temperature, filtered, and finally concentrated to dryness under reduced pressure and recrystallized from heptane. The yield is 107 g (316 mmol), corresponding to 69% of theory. The following brominated compounds are prepared analogously: b) 6-Bromo-2-cyanophenyl benzoate A solution of 10 g (50 mmol) of 2-bromo-6-hydroxybenzonitrile, 10.4 ml (75 mmol) of triethylamine, and 61 mg (0.5 mmol) of 4-N,N-dimethylaminopyridine in 200 ml of CH2Cl2 is initially charged, cooled to 0°C, and then 10.5 g (75 mmol) of benzoyl chloride is added. The mixture is stirred at room temperature for 3 h. The reaction mixture is poured into 20 ml of sodium chloride solution and extracted three times with Et2O. The combined organic phase is dried over MgSO4. The organic solvent is removed under reduced pressure, and the residue is subjected to flash column chromatography on silica gel (hexane / AcOEt = 20 / 1–7 / 1). Yield: 10.4 g (33 mmol), 70% of theory. c) S-(2-cyano-3-bromo-phenyl)-benzene carbothionate In a baked flask under argon, 8 g (25 mmol) of 2-bromo-6-iodobenzonitrile, 0.47 g (10 mol%, 2.5 mmol) of CuI, 0.9 g (20 mol%, 5 mmol) of 1,10-phenanthroline, and 5.1 g (37.5 mmol) of thiobenzoic acid were added to 20 ml of degassed toluene under nitrogen and stirred at 100 °C for 24 h. The reaction mixture was cooled to room temperature. Diethyl ether (1000 ml) and saturated sodium chloride solution (1000 ml) were added, and the mixture was stirred. The organic phase was separated, and the aqueous phase was extracted with diethyl ether (2 × 1000 ml). The combined organic phases were dried over Na2SO4, and the product was isolated by column chromatography. Yield: 5.3 g (16.2 mmol), 65% of theory d) 2-Amino-4-Bromo-3-benzofuranyl)phenylmethanone In a heated flask under argon, 0.67 g (30 mmol) of Pd(OAc)2, 1.69 g (6 mmol) of PCy3 (tricyclohexylphosphine), 1.96 g (30 mmol) of zinc powder, and 3 g of 4 Å molecular sieves (MS4A) were placed in 1200 mL of DMF. After stirring at room temperature for 20 min, 9.4 g (30 mmol) of bromo-2-cyanophenyl benzoate were added, and the mixture was stirred overnight at 100°C. Saturated NaCl solution was added to the mixture, and the aqueous phase was extracted with Et2O (100 mL x 3). The combined organic phases were dried over MgSO4 and filtered. The organic solvent was removed in vacuo, and the residue was purified by flash column chromatography on silica gel (hexane / AcOEt = 7 / 1 - 2 / 1). Yield: 6.2 g (20 mmol), 67% of theory. The following brominated compounds are prepared analogously: e) 9-Bromo-2,4-diphenylbenzofuro[3,2-d]pyrimidine Under argon, 107 g (316 mmol) of (3-amino-4-chloro-2-benzofuranyl)phenylmethanone and 104 g (1015 mmol) of benzonitrile are placed in 1000 ml of o-xylene, and 56 g (677 mmol) of sodium 2-methylpropan-2-olate are added. The mixture is stirred for 5 hours at 140°C. 30 ml of water is drained off using a water separator, then a little acetone is added, and stirring is continued for another hour. After cooling, the mixture is quenched with one liter of water. The organic phase is separated, washed three times with 300 ml of water, dried over MgSO4, filtered, and the solvent removed in vacuo. The residue is purified by column chromatography. The yield is 64 g (160 mmol), corresponding to 48% of theory. The following compounds are prepared analogously:

[0012] f) 2,9-Drichloro-4-phenyl-benzofuro[3,2-d]pyrimidine 13 g (110.0 mmol) of phenylboronic acid, 15.1 g (56 mmol) of 2,4,9-trichlorobenzofuro[3,2-d]pyrimidine, and 21 g (210.0 mmol) of sodium carbonate were suspended in 500 ml of ethylene glycol diamine ether and 500 ml of water. 913 mg (3.0 mmol) of tri-o-tolylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate were added to this suspension, and the reaction mixture was heated under reflux for 16 h. After cooling, the organic phase was separated, filtered through silica gel, and then evaporated to dryness. The residue was recrystallized from toluene and dichloromethane / heptane. Yield: 13.1 g (42 mmol), 75% of theory. The following compounds were prepared analogously:

[0013] Production of the OLEDs The following examples V1 to V7 and B1 to B34 (see Tables 7 and 8) present the data for various OLEDs. Examples B1 to B34 show data from OLEDs according to the invention. The substrate for the OLEDs in Table 7 is glass flakes coated with structured ITO (indium tin oxide) with a thickness of 50 nm. The exact structure of the OLEDs can be found in Table 7. The materials required to produce the OLEDs are shown in Table 9, unless previously described. All materials are thermally vapor-deposited in a vacuum chamber. The emission layer always consists of at least one matrix material (also called host material) and an emitting dopant (dopant, emitter), which is admixed with the matrix material(s) in a specific volume fraction by co-evaporation.A specification such as 7f:H2:TEG1 (33%:60%:7%) 30nm means that the material 7f is present in a volume fraction of 33% as host material 1, the compound H2 as host material 2 in a fraction of 60%, and TEG1 in a fraction of 7% in a 30nm thick layer. Analogously, the electron-transport layer can also consist of a mixture of two materials. OLEDs are characterized as standard. For this purpose, the electroluminescence spectra and current-voltage-luminance characteristics (IUL characteristics) are measured. EQE and the current efficiency SE (in cd / A) are calculated from these. The SE is calculated assuming a Lambertian radiation pattern. The electroluminescence spectra are determined at a luminance of 1000 cd / m², and the CIE 1931 x and y color coordinates are calculated from these. The value U1000 in Table 8 refers to the voltage required for a luminance of 1000 cd / m².SE1000 refers to the power efficiency at 1000 cd / m. 2is achieved. Finally, EQE1000 refers to the external quantum efficiency at an operating luminance of 1000 cd / m². The lifetime LT is defined as the time after which the luminance drops from an initial luminance L0 (in cd / m²) to a certain proportion L1 (in cd / m²) when operated at a constant current density j0 in mA / cm². A value of L1 = 80% in Table 8 means that the lifetime specified in column LT corresponds to the time (in hours) after which the luminance drops to 80% of its initial value (L0). Use of mixtures according to the invention in OLEDs The material combinations according to the invention can be used in the emission layer in phosphorescent green OLEDs. The data for the various OLEDs are summarized in Table 8. Examples V1 to V7 are comparative examples according to the prior art, examples B1 to B34 show data for OLEDs according to the invention.The examples according to the invention demonstrate a significant advantage in the lifetime of the device. Table 7: Structure of the OLEDs.

[0014] Table 8: Table 9: Materials used, unless previously described

Claims

Patent claims 1. Compound according to formula (1), where the symbols and indices used are: Y is at each occurrence independently N, C-[L]b-Ar2 or C-[L]b1- Ar3, where exactly two Y stand for N, which are linked by a group C-[L]b-Ar2or C-[L]b1-Ar3 are separated; V is O or S; Het corresponds to one of the formulas (1-2), (1-3), (1-4) or (1-5), denotes the connection to the rest of formula (1), R 1 is at each occurrence independently H, D or non-deuterated or partially or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl; Ar, Ar1 are at each occurrence, identically or differently, an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which is substituted with one or more radicals R 2 can be substituted; Ar2, Ar3 are, at each occurrence, identically or differently, an aromatic Ring system with 6 to 40 ring atoms or a heteroaromatic ring system with 9 to 40 ring atoms, which is substituted by one or more radicals R 2 can be substituted; R 2is selected, identically or differently at each occurrence, from the group consisting of D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms may be replaced by D, F, or CN; R# is, at each occurrence, D, or non-deuterated or partially or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl; [L] is an aromatic ring system having 6 to 40 ring atoms or a heteroaromatic ring system having 9 to 40 ring atoms, which may be unsubstituted or partially or fully substituted by D; b, b1, and b2 are each independently 0 or 1.

2. A compound according to claim 1, wherein Het corresponds to formula (1-2).

3. A compound according to claim 1, wherein VO is 4.A mixture comprising at least one compound according to one or more of claims 1 to 3 and at least one further compound selected from the group of matrix materials, phosphorescent emitters, fluorescent emitters, and / or emitters exhibiting TADF (thermally activated delayed fluorescence).

5. A formulation comprising at least one compound according to one or more of claims 1 to 3 or a mixture according to claim 4 and at least one solvent.

6. An organic electronic device comprising an anode, a cathode, and at least one organic layer comprising at least one compound according to one or more of claims 1 to 3.

7. The organic electronic device according to claim 6, wherein the electronic device is an electroluminescent device. 8.An organic electronic device according to claim 6 or 7, wherein the organic layer contains at least one light-emitting layer containing the compounds according to any one of claims 1 to 3.

9. The organic electronic device according to one or more of claims 6 to 8, characterized in that the light-emitting layer contains a further matrix material.

10. The organic electronic device according to claim 9, characterized in that the second matrix material corresponds to a compound of the formulas (6), (7), (8), (9), (10) or (11), where the symbols and indices used are: A 1 is C(R 7 )2, NR 7 , O or S; L is a bond, O, S, C(R 7 )2or NR 7 ; A is at each occurrence independently a group of formula (3) or (4), X2is the same or different at each occurrence CH, CR6 or N, where a maximum of 2 symbols can represent X2N; * indicates the binding site to the formula (9); U 1 , U 2 are a bond, O, S, C(R 7 )2or NR 7 ; R 6 is, identically or differently at each occurrence, D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 7 may be substituted and wherein one or more non-adjacent CH2 groups are substituted by Si(R 7 )2, C=O, NR 7 , O, S or CONR 7 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, each of which is substituted by one or more radicals R 7 can be substituted; two radicals R 6also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar5, identical or different at each occurrence, independently represents an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which is reacted with one or more radicals R 7 may be substituted; R 7 is the same or different at each occurrence D, F, Cl, Br, I, N(R 8 )2, CN, NO2, OR 8 , SR 8 , Si(R 8 )3, B(OR 8 )2, C(=O)R 8 , P(=O)(R 8 )2, S(=O)R 8 , S(=O)2R 8 , OSO2R 8 , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 8 may be substituted, with one or more non-adjacent CH2 groups being substituted by Si(R8 )2, C=O, NR 8 , O, S or CONR 8 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which is substituted by one or more radicals R 8 may be substituted; two or more radicals R 7 together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system, preferably the radicals R 7 no such ring system; R 8 is, at each occurrence, identically or differently, H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, in particular a hydrocarbon radical, having 1 to 20 C atoms, in which one or more H atoms may be replaced by F; c, c1, c2 each independently mean 0 or 1 on each occurrence, where the sum of the indices on each occurrence is c+c1+c2 = 1; d, d1, d2 each independently mean 0 or 1 on each occurrence, where the sum of the indices on each occurrence is d+d1+d2 = 1; q, q1, q2 each independently mean 0 or 1 on each occurrence; s is the same or different 0, 1, 2, 3 or 4 on each occurrence; t is the same or different 0, 1, 2 or 3 on each occurrence; u is the same or different 0, 1 or 2 on each occurrence; u1, u2 each independently mean 0 or 1 on each occurrence, where the sum u1 + u2 = 1; and v is 0 or 1.

11. The organic electronic device according to one or more of claims 6 to 10, characterized in that the light-emitting layer contains a phosphorescent emitter. 12.The organic electronic device according to one or more of claims 6 to 11, characterized in that it is an electroluminescent device selected from the group consisting of organic light-emitting transistors (OLETs), organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O-lasers), and organic light-emitting diodes (OLEDs).

13. The method for producing a device according to one or more of claims 6 to 12, characterized in that the organic layer is applied by vapor deposition or from solution. 14.A method according to claim 13, characterized in that the light-emitting layer of the organic layer is applied by vapor deposition, wherein the at least one compound of formula (1) together with the further materials forming the light-emitting layer are deposited successively or simultaneously from the gas phase from at least two material sources.

15. A method according to claim 13 or 14, characterized in that the light-emitting layer of the organic layer is applied by vapor deposition, wherein the at least one compound of formula (1) together with at least one further matrix material is deposited as a premix. deposited from the gas phase sequentially or simultaneously with the light-emitting materials selected from the group of phosphorescent emitters, fluorescent emitters and / or emitters exhibiting TADF (thermally activated delayed fluorescence).

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