Materials for organic light-emitting devices

Abstract

The invention relates to specifically substituted indolocarbazoles as OLED material, to mixtures containing them, to the use thereof in organic electronic devices and to organic electronic devices containing these compounds, in particular organic light-emitting devices or OLEDs containing these compounds as matrix materials, hole-transport materials, hole-injection materials or electron-blocking materials.

Description

[0001] P24-132 SC - 1 - Materials for Organic Light-Emitting Devices Technical Field The present invention relates specifically to substituted indolocarbazoles, mixtures containing these 5, the use of which in organic electronic devices, as well as organic electronic devices containing these compounds, in particular organic electroluminescent devices or OLEDs containing these compounds, as matrix materials, hole transport materials, hole injection materials, or electron blocking materials. 10 Prior Art Phosphorescent metal-organic 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 not solely determined by the triplet emitters used.Here, the other materials used, such as matrix materials or hole transport materials, are of particular importance. Improvements to these materials can therefore also lead to significant improvements in the OLED properties. According to the prior art, carbazole derivatives, dibenzofuran derivatives, indenocarbazole derivatives, indolocarbazole derivatives, benzofurocarbazole derivatives, and benzothienocarbazole derivatives are used, among others, as matrix materials for phosphorescent emitters. WO2013151297 A1 describes specific organic electroluminescent materials. WO2019017618 A1 and US2022399517 A1 describe specific combinations of OLED materials and their use in organic layers of organic optoelectronic devices. US2018130954 and US20160064041 A1 describe specific indolocarbazole compounds and their use as OLED material.In general, there is still room for improvement with these materials, especially for use in light-emitting devices. The object of the present invention is to provide compounds that are particularly suitable for use as matrix materials, hole transport materials, hole injection materials, or electron blocking materials in a phosphorescent OLED. In particular, it is the object of the present invention to provide matrix materials that have high temperature stability, so that they can be evaporated without decomposition in a high vacuum. This property is a fundamental requirement for the reproducible fabrication of organic electronic devices and has a particularly positive effect on the operational lifetime of these devices. This object applies especially to the use of matrix materials in combination with a low to medium emitter concentration, i.e.,Emitter concentrations in the range of 3 to 25%, particularly 3 to 15%, and especially preferably 4 to 8%, are required, as the device lifetime is particularly limited at these concentrations. This objective applies especially to the use of matrix materials in combination 10 with special hole injection materials, hole transport materials, or electron blocking materials. It has now been found that electroluminescent devices containing compounds according to formula (1) exhibit improvements over the prior art 15, particularly when the compounds are used as matrix materials for phosphorescent dopants. By using the compounds of formula (1), the operating voltage can be significantly reduced.It was further found that the combination of at least one compound of formula (1) as the first host material and at least one electron-transporting compound, for example in combination with one or more compounds of formulas (A), (B), (C), (D) and / or (E), as the further host material(s) in a light-emitting layer of an organic electronic device, in particular an organic light-emitting device, solves this problem and eliminates the disadvantages of the prior art.It was further found that an organic electronic device, in particular an organic light-emitting device, solves the problem which contains in the light-emitting layer of the organic layer a combination of at least one compound of formula (1) as the first host material and at least one electron-transporting compound, for example in combination with one or more compounds of formulas (A), (B), (C), (D) and / or (E), as a further host material(s) and in the hole-injecting layer and / or hole-transporting layer and / or electron-blocking layer of the organic layer contains a hole-injecting material or hole-transporting material or electron-blocking material belonging to the class of arylamines, which contains at least one fluorenyl unit or spirobifluorenyl unit and no carbazole unit.P24-132 SC - 3 - Summary of the invention A first object of the present invention are compounds of formula (1), 5 10. where the symbols and indices used are defined as follows: (R)a, (R)b each independently represent a monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution, or no substitution with the substituent R; R, in each instance, is independently D or unsubstituted, partially or completely deuterated phenyl; R 0 is H or D; 20Y is O or S regardless of occurrence; Ar* is an aryl group with 6 to 30 C atoms, linked to one or more R groups 1 can be substituted; R 1is selected, in each occurrence, as the same or different from the group consisting of D, F, CN, Si(aryl)3, a straight-chain alkyl group with 1 to 25 or 20 C atoms, or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein one or more non-adjacent CH2 groups may be replaced by O or S, and wherein one or more H atoms may be replaced by D, F, or CN, or a non-deuterated or partially or completely deuterated aryl group with 6 to 30 C atoms; 30 Aryl is, in each occurrence independently, as the same or different from the group consisting of D, F, CN, Si(aryl)3, a straight-chain alkyl group with 1 to 25 or 20 C atoms, or a heteroaryl group with 5 to 40 ring atoms, which may be partially or completely deuterated. Another object of the invention is a mixture comprising at least one compound of formula (1) as previously described or preferably described later, and at least one further compound selected from the group of matrix materials.the phosphorescent emitter, the fluorescent emitter and / or the emitter exhibiting TADF (thermally activated delayed fluorescence). P24-132 SC - 4 - Another object of the invention is the use of at least one compound according to formula (1) in an organic electronic device. 5 Another object of the invention is an organic electronic, preferably electroluminescent, device comprising an anode, a cathode and at least one organic layer, containing at least one compound according to formula (1), wherein the organic layer is at least a light-emitting layer, a hole-transporting layer, a hole-injecting layer or an electron-blocking layer. Description of the invention In the present patent application, “D” or “D atom” denotes deuterium. The degree of deuteration, expressed in mol%, denotes the proportion of H atoms,which are replaced by 15 deuterium. Since the deuterated compounds are often a mixture of compounds that differ in the exact position and proportion of the D atoms, the degree of deuteration denotes the average proportion of the H atoms that are replaced by D. At a degree of deuteration of 50 mol%, on average 50 mol% of the H atoms in the 20 compound are replaced by D, so that the degree of deuteration is average. An aryl group according to this invention contains 6 to 40 ring atoms, or preferably 6 to 30 ring atoms, or preferably 6 to 18 ring atoms, wherein the ring atoms are C atoms. A heteroaryl group according to this invention contains 5 to 40 ring atoms, wherein 25 the ring atoms comprise C atoms and at least one heteroatom, provided 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 is understood to be a simple aromatic cycle, for example phenyl derived from benzene, or a fused aryl group, for example derived from naphthalene, anthracene, 30 phenanthrene, or triphenylene. However, for the purposes of the invention, the term aryl group also includes biphenyl, terphenyl, quaterphenyl, fluorenyl, 9,9-dialkylfluorenyl, 9,9-diarylfluorenyl, or spirobifluorenyl. A preferred 9,9-dialkylfluorenyl group is 9,9-dimethylfluorenyl. A preferred 9,9-diarylfluorenyl group is 9,9-diphenylfluorenyl. An aryl group with 6 to 18 carbon atoms is therefore preferably phenyl, naphthyl, 35 phenanthryl, or triphenylenyl, the attachment of the aryl group as a substituent being unrestricted. The aryl group according to this invention can carry one or more residues, the suitable residue being described below. Deuterium is preferred as the residue. If no such residue is described,The aryl group or heteroaryl group is not substituted. P24-132 SC - 5 - A heteroaryl group is understood to be either a simple heteroaromatic cycle, for example derived from pyridine, pyrimidine, or thiophene, or a fused heteroaryl group, for example derived from quinoline, isoquinoline, 5 benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, or carbazole, but the term heteroaryl group, as used in this invention, also includes a heteroaryl group that is bonded by a single bond to an aryl group or to another heteroaryl group, for example phenyl-bipyridyl or bipyridyl. The heteroaryl group as used in this invention may bear one or more substituents, 10 wherein the suitable substituent is described below. Preferably, the substituent is deuterium. If no such substituent is described,The heteroaryl group is unsubstituted. An aromatic ring system according to this invention contains 6 to 40 carbon atoms in the ring system. The aromatic ring system comprises aryl groups as previously described, and the term is used synonymously below. An aromatic ring system with 6 to 18 carbon atoms, or the aryl group with 6 to 18 carbon atoms, is preferably selected from phenyl, biphenyl, naphthyl, phenanthryl, and triphenylenyl, which may bear one or more substituents, the suitable substituent being described below. Deuterium is preferred. If no such substituent is described, the aromatic ring system / aryl group is unsubstituted. A heteroaromatic ring system according to 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 comprises heteroaryl groups,as described above, and the term will be used synonymously in the following. 30 An aromatic or heteroaromatic ring system with 5 to 40 ring atoms or a heteroaryl group with 5 to 40 ring atoms, which may be linked via any position on the aromatic or heteroaromatic compound and which may bear one or more substituents, as described below, preferably includes the following groups, which are derived from benzene, naphthalene, anthracene, 35 benzanthracene, phenanthrene, triphenylene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzfluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, terphenyl, quaterphenyl, fluorene, 9,9-dimeethylfluorene, 9,9-diphenylfluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-monobenzoindenofluorene, cis- or trans-dibenzoindenofluorene, truxene, P24-132 SC - 6 - isotruxene, spirotruxene, spiroisotruxene, 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, 5 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-Diaza- 10 pyren, 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-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, 15-pteridine, indolizine, benzothiadiazole, phenylpyridine, and bipyridine. The abbreviation Ar* stands for an aryl group with 6 to 30 carbon atoms, which is linked to one or more R groups. 1 can be substituted, with the remainder being R 1 has a meaning as described above or below. 20 The abbreviation "aryl" is, in each occurrence independently, the same or different: an aryl group with 6 to 30 carbon atoms or a heteroaryl group with 5 to 40 ring atoms, which may be partially or completely deuterated. The abbreviation "aryl" preferably refers to phenyl, which may be partially or completely deuterated. 25 The abbreviation Ar 5 In each instance, the term represents, in the same or different ways, an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which is coupled with one or more R groups.7 may be substituted or synonymous with an aryl group with 6 to 40 carbon atoms or a heteroaryl group with 5 to 40 ring atoms, which is coupled with one or more R groups 7 can be substituted, where the substituent R 7 or the 30 substituents R 7 has / have a meaning as described before or below. A preferred meaning of Ar*, "Aryl" and Ar 5This is described below. An electron-rich heteroaromatic is a heterocyclic aromatic compound with an excess of electrons, i.e., a lone pair of electrons of the heteroatom forms the cyclically delocalized electrons with the p-35 electrons of the carbon atoms. This definition also applies accordingly to an electron-rich heteroaromatic ring system. A cyclic alkyl, alkoxy, or thioalkyl group within the meaning of this invention is understood to be a monocyclic, bicyclic, or polycyclic group. P24-132 SC - 7 - Within the scope of the present invention, for example the following residues are found under a straight-chain, branched or cyclic C1 to C20 alkyl group: 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, 3-5-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- 10 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-15-Decyl)-cyclohex-1-yl- are understood. The compounds of formula (1) and their preferred embodiments are described below. The preferred embodiments also apply to the mixture and the organic electronic or electroluminescent device according to the invention. Preferred embodiments of the compounds of formula (1) are compounds in which YO is represented by formula (1a), 25 30, Formula (1a), where Ar*, (R) a , (R) b , R 0and R have a meaning preferably specified above or below. 35 Another object of the invention is therefore compounds of formula (1a), as described above or preferably below. In compounds of formulas (1) or (1a), the linkage sites are not limited. P24-132 SC - 8 - Particularly preferred compounds of formula (1) are compounds of formulas (1b) or (1c), 5 10 15 20 where Ar*, (R)a, (R)b, R, R 0 and Y have a previously specified or a preferably specified meaning. 25 The attachment of the respective dibenzofuran units or of the dibenzofuran or of the dibenzothiophene unit to the indolocarbazole backbone is possible independently of one another at positions 1, 2, 3 or 4, as shown in the following illustration as representative of dibenzofuran: 30 Particularly preferred compounds of formula (1) are therefore compounds 35 of formulas (1d) to (1k), P24-132 SC - 9 - 5 10 15 20 25 30 35 Formula (1j) Formula (1k) where Ar*, (R) a , (R) b , R, R 0and Y have a meaning preferably specified before or after. P24-132 SC - 10 - Particularly preferred embodiments of the compounds of formula (1) correspond to formulas (1d) to (1g). Preferred embodiments of the compounds of formula (1) correspond to formulas (1h) to (1k). 5 In compounds of formulas (1), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k), the dibenzofuran or dibenzothiophene unit is preferably bound in position 1. In compounds of formulas (1), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k), the dibenzofuran or dibenzothiophene unit is preferably bound in position 2. 10 In compounds of formulas (1), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k) the dibenzofuran or dibenzothiophene unit is preferentially bound in the 3-position.In compounds of formulas (1), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k), the dibenzofuran or dibenzothiophene unit is preferably bound in the 4-position. 15 In a preferred embodiment of the compounds of formulas (1), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k), the symbol Y denotes O. A particularly preferred embodiment of the compounds of formula (1) are compounds of formulas (1d) or (1h), as described above. 20 Accordingly, a further object of the invention is compounds of formulas (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k), as described above or preferably below, in which Y denotes O in each instance. In combinations of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and 25 (1k) represent (R). a and (R) ba monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution, or no substitution with substituent R. It is preferred if at most one substituent R represents unsubstituted, partially or completely deuterated phenyl, and the other substituents R represent D when present. It is particularly preferred if the substituent R represents D when present. 30 In the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k), Ar* is preferentially selected from the group Ar-1 to Ar-17. 35

[0002] P24-132 SC - 12 - 5 , where R 3 H or R 1 means that 10 the dashed bond represents the bond to the rest of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k), where R 1 has a previously mentioned or a previously preferred meaning. In Ar*, the substituent R 1Preferably, in each occurrence, the same or different 15 is selected from the group consisting of D, F, CN or a non-deuterated, partially deuterated or fully deuterated aryl group with 6 to 30 carbon atoms. In Ar*, the substituent is R 1 Particularly preferred, in each occurrence, are selected from the group consisting of D, non-deuterated, or partially or fully deuterated phenyl, whether the same or different. In Ar*, the substituent R 1 20 D is particularly favored. In structures Ar-1 to Ar-17, the substituent R 3 Preferably, in each occurrence, the substituent is selected from the group consisting of H, D, F, CN, or a non-deuterated, partially deuterated, or fully deuterated aryl group with 6 to 30 C-25 atoms. In structures Ar-1 to Ar-17, the substituent is R 3Particularly preferred in each occurrence, the substituent is selected from the group consisting of H, D, non-deuterated, or partially or completely deuterated phenyl, either the same or different. In structures Ar-1 to Ar-17, the substituent is R. 3 Ar* is particularly preferentially selected from the group consisting of H or D, whether the same or different, in each occurrence. 30 In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k), Ar* is particularly preferentially selected from the group Ar-1 to Ar-4, where R 3 has a previously specified or preferentially specified meaning. 35 In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k), Ar* is particularly preferentially selected from the group Ar-2 to Ar-4, wherein R 3has a previously specified or preferably specified meaning. P24-132 SC - 13 - In a preferred embodiment of the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k), as previously or preferably described, these are partially or completely deuterated.5 If the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k) are deuterated compounds, it is possible in their preparation, provided that the preparation is carried out by reacting a non-deuterated compound of one of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k) with a deuterating source, or provided that 10 deuterated starting compounds are chosen in the preparation which are a mixture of deuterated starting compounds, that a mixture of deuterated products of the same basic chemical structure is obtained which differ only in the degree of deuteration and / or the deuteration patterns.15 Such mixtures of deuterated compounds of the same basic chemical structure of formula (1) or of the basic structure of the preferred embodiments, which differ only in the degree of deuteration and / or the deuteration patterns, are understood to be “at least one compound of formula (1)” within the meaning of the invention. 20 In a preferred embodiment of the at least one compound of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k), as previously or preferably described, the average degree of deuteration is 5 mol% to 100 mol%, preferably 30 mol% to 95 mol%, and particularly preferably 50 mol% to 90 mol%.Suitable deuteration methods are known to those 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 hydrogen atoms for dium atoms is to treat the compound to be deuterated in the presence of a platinum or palladium catalyst and a deuterium source. The term "deuterium source" means any compound that contains one or more dium atoms and can release 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 P24-132 SC - 14 deuterium source is D₂O, benzene-d₆, chloroform-d₆, 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, the fully deuterated solvent not being 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 under heating, more preferably under heating to temperatures between 100 °C and 10,200 °C.Furthermore, the reaction is preferably carried out under pressure. Examples of suitable compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k) are the structures listed below in Table 1. 15 Table 1: 20 25 30. 35 P24-132 SC - 29 - 5 10 Particularly suitable compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k) are compounds H1 to H33 of Table 2. Table 2: 20 25 30 35 P24-132 SC - 30 - 5 10 15 20 25 30 35 P24-132 SC - 31 - 5 10 15 20 25 30 35 P24-132 SC - 32 - 5 10 For the sake of simplicity, the compounds in Tables 1 and 2 are partially represented as fully deuterated compounds, which generally refers to compounds having an average degree of deuteration of at least 50 mol%. The average degree of deuteration for the fully deuterated compounds in Tables 1 and 2 is therefore between 50 mol% and 100 mol%, or has a preferred degree of deuteration as described herein. For partially deuterated compounds, a D atom signifies that the corresponding position in the molecule has a degree of deuteration of at least 40 mol%. 20 The compounds according to 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. In the following synthetic schemes, the compounds are shown with a small number of substituents to simplify the structures.This does not preclude the presence of any further 25 substituents in the processes. The methods shown for the synthesis of the compounds according to the invention are to be understood as examples. The person skilled in the art can develop alternative synthetic routes within the scope of their general technical knowledge. 30 35 P24-132 SC - 33 - Scheme 1: 5 10 15 20 25 30. 35 Detailed reaction conditions are known from the prior art or are described in the example section. P24-132 SC - 34 - 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 15. 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 or of mixtures of compounds according to the invention with further functional materials, such as matrix materials, fluorescent emitters, phosphorescent emitters and / or emitters exhibiting TADF 10, 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 3-15-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, 20 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, 1-25-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, diethyl sebacic acid ester, octyl octanoate, heptylbenzene, menthyl isovalerate, cyclohexylhexanoate, or mixtures of these solvents. A suitable formulation is a formulation containing at least one compound according to the invention, as described above.or a mixture according to the invention, as described below, and at least one solvent. The solvent may be one of the solvents mentioned above or a mixture of these solvents. The compounds according to the invention of formula(s) (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) and (1k), as previously described or preferably described, are suitable for use in an organic electroluminescent device, in particular as a hole transport material, as a hole injection material, as an electron blocking material or as a matrix material. P24-132 SC - 35 - When the compound according to the invention is used as a matrix material or, synonymously, host material in an emitting layer, it is preferably used in combination with another compound. 5 A further object of the invention is therefore a mixture containing at least one compound of formula (1) or at least one preferred compound of one of formulas (1), (1a), (1b),(1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) or (1k), or a compound from Table 1 or one of compounds H1 to H33 and at least one further compound selected from the group consisting 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 are described below. 15 Another object of the present invention is an organic electronic device comprising an anode, a cathode and at least one organic layer, containing at least one compound of formula (1) or at least one preferred compound of one of formulas (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) or (1k), or a compound of Table 1 or one of compounds H1 to H33.wherein the organic layer is at least a light-emitting layer, a hole-transporting layer, a hole-injecting layer, or an electron-blocking layer. Particularly suitable matrix materials, which are advantageously combined with the 25 compounds according to the invention in a mixed-matrix system, can be selected from the compounds of formulas (A), (B), (C), (D), or (E), as described below. The organic electronic device can be, for example, composed of the 30 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 are selected. 35 Preferably, the organic electronic device is an organic electroluminescent or organic light-emitting device. The organic electroluminescent device according to the invention (synonymously organic electroluminescence device or organic light-emitting device) P24-132 SC - 36 - 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 comprises, 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 may also include several layers of this group, preferably selected from EML, HIL, HTL, ETL, EIL, and HBL.The system may contain multiple emitting layers. Interlayers, which may, for example, have an exciton-blocking function, may also be introduced between two emitting layers. If multiple emission layers are present, they preferably exhibit multiple emission maxima between 380 nm and 750 nm, resulting in overall white emission. This means that different emitting compounds, which can fluoresce or phosphoresce, are used in the emitting layers. Multiple fluorescent and / or phosphorescent compounds may also be contained in a single emitting layer. Systems with three emitting layers, wherein the three layers exhibit blue, green, and orange or red emission, are particularly preferred. Alternatively to the combination described above,An emitting layer can also exhibit yellow emission. Such combinations are known to those skilled in the art. The organic electroluminescent device according to the invention can also be a tandem electroluminescent device, particularly for white-emitting OLEDs. The device can also contain inorganic materials or layers that are composed entirely of inorganic materials. A large number of materials known in the prior art are suitable for use in the layers of the organic electroluminescent device described above. When selecting materials, common considerations regarding their chemical and physical properties must be taken into account, since the materials in an organic electroluminescent device are in interaction with each other. This relates, for example, to the energy levels of the orbitals (HOMO,LUMO) or the position of triplet and singlet energies, as well as other material properties. 5 The compound of formula (1) according to the invention, as previously described or preferably described, can be used in different layers, depending on the exact structure. Preferably, an organic electroluminescent device is used, 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 emitters exhibiting TADF (thermally activated delayed fluorescence).especially for phosphorescent emitters. Furthermore, the compound according to the invention can also be used in a hole-transporting layer, a hole-injecting layer, or an electron-blocking layer. The compound according to the invention is particularly preferably used as a matrix material in an emitting layer or as a hole-transporting, hole-injecting, or electron-blocking material in a hole-transporting, hole-injecting, or electron-blocking layer. Another object of the present invention is an organic electronic device as described above, wherein the organic layer contains at least one light-emitting layer comprising at least one compound of formula (1) or at least one preferred compound of one of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j), or (1k).or a compound of Table 1 or one of compounds H1 to H33. 25 In one embodiment of the invention, at least one further matrix material is selected for the light-emitting layer of the device according to the invention, which is used with compounds of formula (1), as previously described or preferably described, or with the compounds of Table 1 or compounds H1 to H33. 30 A further object of the present invention is therefore an organic electronic device as previously described, wherein the organic layer contains at least one light-emitting layer which contains at least one compound of formula (1) or at least one preferred compound of one of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) or (1k),or a compound of Table 1 or one of compounds H1 to H33 and at least one further matrix material. P24-132 SC - 38 - A further object of the present invention is therefore an organic electronic device as described above, wherein the organic layer contains at least one light-emitting layer comprising at least one compound of formula (1) or at least one preferred compound of one of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) or (1k), or a compound of Table 1 or one of compounds H1 to H33 and at least two further matrix materials. Suitable matrix materials which can be used in combination with the 10 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, azaborols or boron esters, triazine derivatives, zinc complexes, diazasilol or tetraazasilol derivatives, diazaphosphole derivatives, bridged carbazole derivatives, triphenylene derivatives, or dibenzofuran derivatives. Likewise, another phosphorescent emitter emitting at a shorter wavelength than the primary emitter may be present in the mixture as a co-host, or a compound that does not participate, or does not participate to a significant extent, in charge transport, such as a wide-bandgap compound. Herein, a wide-bandgap material is understood to be a material as defined in US 7,294,849, characterized by a band gap of at least 3.5 eV, where band gap is defined as the difference between the HOMO and LUMO energies of a material. 25 Particularly suitable matrix materials advantageously combined with compounds of formula(s) (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) or (1k),As previously described or preferably described, combined in a mixed-matrix system, the compounds can be selected from the compounds of formulas (A), (B), (C), (D) or (E), as described below. A further object of the invention is therefore a mixture comprising at least one compound according to the invention of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) or (1k) and at least one compound of formulas (A), (B), (C), (D) and / or (E), P24-132 SC - 39 - 5 10 15 20 25 30. where the following applies to the symbols and indices used: X is the same or different in each occurrence N or CR 6 , preferably N; L 2 In each occurrence, it is either the same or different: a single bond or an aromatic or heteroaromatic ring system with 5 to 24 ring atoms, each with one or more R groups. 7may be substituted; R## is the same or different in each occurrence D, F, CN or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which is coupled with one or more R substituents 6 can be substituted and two adjacent substituents R## can together form an aromatic, heteroaromatic, aliphatic or P24-132 SC - 40 - heteroaliphatic ring system, which is coupled with one or more R groups 7 It may be substituted; Y is the same or different in each occurrence N or CR 9 , where it is excluded that two adjacent Ys simultaneously represent N; 5 V 2 is O or S; R 6is the same or different in each occurrence D, F, CN, a straight-chain alkyl group with 1 to 20 C atoms or an alkenyl or alkynyl group with 2 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each linked to one or more R groups 7 can be substituted and where one or more non-adjacent CH2 groups are replaced by Si(R 7 )2, C=O, NR 7 , O, S or CONR 7 can be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, each of which can be partially or completely deuterated; in which case two residues R 6 also together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar 5In each instance, the term represents, in the same or different ways, an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which is coupled with one or more R groups. 7 may be substituted; R 7 is the same or different in each occurrence D, F, Cl, Br, I, N(R 8 )2, CN, NO2, 20 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 with 1 to 20 carbon atoms, or an alkenyl or alkynyl group with 2 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein one or more non-adjacent CH2 groups are fused by Si(R 8 )2, C=O, NR 8 , O, S or CONR 8can be replaced, or a 25 aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which can be partially or completely deuterated; in which case two or more R groups can be 7 together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; R 8 is the same or different H, D, F or an aliphatic, aromatic or heteroaromatic organic residue, in particular a hydrocarbon residue, with 1 to 20 C atoms, in which one or more H atoms may also be replaced by D or F; R 9 is the same or different in each occurrence H, 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, 35 a straight-chain alkyl group with 1 to 20 C atoms or an alkenyl or alkynyl group with 2 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each linked to one or more R groups 6 can be substituted, with one or more non-adjacent CH2 groups being replaced by Si(R 8 )2, C=O, NR 8 , O, S or CONR 8 replaced P24-132 SC - 41 - may be, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each separated by one or more R groups 6 It can be substituted; in this case, two or more residues R can be involved. 9together form an aromatic, heteroaromatic, aliphatic, or heteroaliphatic ring system; 5 b1 is 0, 1, 2, 3, or 4; b2 is 0, 1, 2, or 3. A further object of the invention is an organic electronic device, in particular an organic electroluminescent device comprising an anode, cathode 10, and at least one organic layer, containing at least one light-emitting layer, wherein the at least one light-emitting layer comprises at least one compound of formula (1) as matrix material 1, as previously or preferably described, and at least one compound of formulas (A), (B), (C), (D), and / or (E) as matrix material 2, as previously or subsequently preferably described. 15 Preferred compounds of formula (A) are the compounds of formulas (Aa), (Ab), (Ac), (Ad), (Ae), and (Af), 20 25 30 35 Ab) P24-132 SC - 42 - 5 10 15 20 25 30 35 , P24-132 SC - 43 - where the symbols and indices for these formulas have the following meaning: W, W 1 O, S, C(R) mean the same or different in each occurrence. W )2 or N-Ar 5 ; 5 R W In each instance, the alkyl group may be the same or different: a straight-chain alkyl group with 1 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein one or more hydrogen atoms may be replaced by D, F, or CN; or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which may be replaced by one or more substituents selected from D, F, CN, or a straight-chain alkyl group with 1 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein one or more hydrogen atoms of the alkyl group on the aromatic or heteroaromatic ring system may be replaced by D, F, or CN; the two R groups may be W, which bond to the same carbon atom, also form a 15-ring system together; A is the same or different in each occurrence CR 7 or N, where a maximum of two groups A per cycle stand for N and where A stands for C if L is placed at this position 2 is bound; a3 is the same or different 0, 1, 2, 3 or 4 in each occurrence; b3 is the same or different 0, 1, 2 or 3 in each occurrence; Ring B is derived from an aryl group with 6 to 20 ring atoms, which may be substituted with one or more substituents R##; 25 L 3 is an aromatic ring system with 6 to 40 ring atoms or a 30 heteroaromatic ring system with 5 to 40 ring atoms, which is coupled with one or more R groups 7 can be substituted; and where L 2 , X, Ar 5 , R 7and R## have the meanings given above. 35 In one embodiment of the invention, compounds of formula (Aa) are combined with at least one compound of formula (1) or preferred embodiments wherein W N-Ar 5 means. In this embodiment, L 2 preferably selected from the linkers L-1 to L13, each with one or more residues R 7 may be substituted, P24-132 SC - 44 - 5 10 15 20 , where the dashed lines denote the connection to the rest of the formula (Aa) and where R 7 has a previously stated or subsequently stated meaning. 25 Particularly preferred compounds of formulas (A) and (Aa) are the compounds of formulas (Aa-1) to (Aa-7), 30 35 Formula (Aa-1), P24-132 SC - 45 - 5 10 15 20 25 30 35 - , P24-132 SC - 46 - 5 10 15 - , where the following applies to the symbols and indices used: Ar** is equal to or different from an aromatic ring system with 6 to 40 ring atoms, 20 that with one or more substituents R 7 may be substituted; L 5 is a bond or an aromatic ring system with 6 to 40 ring atoms, which includes one or more substituents R 7 may be substituted, (R 7 ) x , (R 7 ) y , (R 7 ) x1 , (R 7 ) y1 represent a monosubstitution, a disubstitution, a trisubstitution, or the maximum permissible substitution with the substituent R. 7 25 dar, R 18 The group consists of a straight-chain alkyl group with 1 to 10 carbon atoms or an aryl group with 6 to 12 carbon atoms, either the same or different in each occurrence, with two substituents R. 18together they can form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, 30 which with one or more substituents R 7 can be substituted; where X, L 2 , Ar 5 and R 7 have a previously mentioned or a previously and subsequently preferred meaning. In compounds of formulas (Aa-1) to (Aa-7), X is preferably N. 35 In compounds of formulas (Aa-1) to (Aa-4), the linkers are L 2 and L 5 preferentially one bond. In compounds of the formula (Aa-5), the linker is L. 2 prefers one bond. P24-132 SC - 47 - In compounds of formulas (Aa-6) and (Aa-7), one of the linkers is L 2 preferably selected from the linkers L-1 to L-13, which contain one or more substituents R 7 They can be substituted, as described previously. In compounds of formulas (Aa-6) and (Aa-7), one of the linkers is L. 2The linker L-12, which has one or more 5 substituents R, is preferred. 7 It can be substituted, as previously described. This one left L 2 It is preferentially bound to the diazadibenzofuran or diazadibenzothiophene unit. The further links L 2 In compounds of formulas (Aa-6) and (Aa-7), there is preferably one bond. 10 In compounds of formulas (Aa-1), (Aa-2), (Aa-3), (Aa-4) and (Aa-5), the substituents R 7 in (R 7 ) x , (R 7 ) y , (R 7 ) x1 , (R 7 ) y1 When occurring, they are preferably as indicated above or below, and are most preferably D. In compounds of formulas (Aa-6) and (Aa-7), the substituents R 7 in (R 7 ) x When occurring, they are preferably as previously stated, and are especially preferred D. In 15 compounds of formulas (Aa-6) and (Aa-7), the substituents R 7 in (R 7 )y When occurring, preferably as previously stated, and are particularly preferably a non-deuterated, partially or fully deuterated aryl group with 6 to 18 carbon atoms. Compounds of formula (Aa-4), as previously or preferably described, 20 are also preferred embodiments of the compound of formula (Ac). In one embodiment of the invention, compounds of formula (Ad) are combined with at least one compound of formula (1) or preferred embodiments in which one of the linker L 2 an aromatic or heteroaromatic 25-ring system with 5 to 24 ring atoms, each with one or more R substituents 7 can be substituted means. In this embodiment, one of the links L 2 preferably selected from the linkers L-1 to L13, each with one or more residues R 7can be substituted as previously described, where the dashed lines denote the connection to the rest of the formula (Ad) and where R 7 has a meaning previously specified or subsequently specified. In one embodiment of the invention, compounds of formula (Ad) are combined with at least one compound of formula (1) or preferred embodiments in which one of the linker L 2 selected from the linkers L-1, L-2, L-3, L-8, L-9, L-12 and L-13, each with one or more remainders R 7 can be substituted 35. In this embodiment, one of the links L 2 preferably selected from the linker L-12, each with one or more residues R 7 It can be substituted, as previously described. In this embodiment, one of the links L 2 preferably selected from the linker L-9, each with one or more residues R 7It can be substituted, as previously described. This one left L 2 The 4H-naphtho[1,2,3,4-def]carbazole unit of the compounds of formula (Ad) is preferably bound to P24-132 SC - 48 -. The further linker L 2 are preferably a bond. In an alternative embodiment of the compounds of formula (Ad), all linkers are L 2 preferably a bond. 5 In one embodiment of the invention, compounds of formula (Ae) are combined with at least one compound of formula (1) or preferred embodiments, wherein W 1 O or C(R W )2 means, where R W has a previously specified meaning. In this embodiment, it is preferred that the remainder R W Methyl 10 means or the two R groups W , which bond to the same carbon atom and together form a ring system. In this embodiment, it is preferred if one of the linkers L 2an aromatic or heteroaromatic ring system with 5 to 24 ring atoms, each with one or more R groups 7 It can be substituted. In this embodiment, one of the left L 2 preferably selected from the linkers L-1 to L13, 15 as previously described, each with one or more residues R 7 can be substituted, where the dashed lines denote the connection to the rest of the formula (Ae) and where R 7 has a previously stated or subsequently stated meaning. This one left L 2 is preferentially bound to the carbazole unit of the compounds of formula (Ae). The further linker L 2 are preferably a 20 bond. In an alternative embodiment of the compounds of formula (Ae), all linkers are L 2 A bond is preferred. Particularly preferred compounds of formulas (A) and (Af) are the compounds of formulas (Af-1) to (Af-3), 25 30 35 Formula (Af-1), P24-132 SC - 49 - 5 10 15 20 where the following applies to the symbols and indices used: 25 (R 7 ) x , (R 7 ) y represent a monosubstitution, a disubstitution, a trisubstitution, or the maximum permissible substitution with the substituent R. 7 dar, R 18 The group consists of a straight-chain alkyl group with 1 to 10 carbon atoms or an aryl group with 6 to 12 carbon atoms, either the same or different in each occurrence, with two substituents R. 18 together they can form a monocyclic or polycyclic, aliphatic, aromatic or 30 heteroaromatic ring system, which can be combined with one or more substituents R 7 can be substituted; where X, L 2 , Ar 5 and R 7have a previously mentioned meaning or a meaning preferably mentioned previously and subsequently. 35 In compounds of formulas (Af-1), (Af-2) and (Af-3), all X preferably stand for N. In compounds of formulas (Af-1), (Af-2) and (Af-3), the substituents R 7 in (R 7 ) x , (R 7 ) y When occurring, preferably as indicated below, most preferably D. P24-132 SC - 50 - Preferred compounds of formula (B) are the compounds of formula (Ba), 5 Formula (Ba), where Y, V 2 , L 2 , R 7 , R 9 and a3 have a previously specified meaning, D corresponds to deuterium and a40 means 1 or 2. 10 Preferred compounds of formula (C) are the compounds of formula (Ca), 15 20 Formula (Ca) where the symbols and indices for this formula (Ca) have the following meaning: W 1 is the same or different in each occurrence O, S, C(R W )2 or N-Ar5 ; #X is CR or NAr 5 , preferably NAr 5 ; 25 R W is, in each occurrence, the same or different: a straight-chain alkyl group with 1 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein one or more H atoms may be replaced by D, F, or CN; or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which may be replaced by one or more substituents selected from D, F, CN; 30 a straight-chain alkyl group with 1 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein one or more H atoms of the alkyl group on the aromatic or heteroaromatic ring system may be replaced by D, F, or CN; a3 is, in each occurrence, the same or different: 0, 1, 2, 3, or 4; 35 R ing B is derived from an aryl group with 6 to 20 ring atoms, which may be substituted with one or more substituents R##; P24-132 SC - 51 - where L 2 , Ar 5 and R## have the meanings given above. 5 In compounds of formula (Aa), W is preferably O or N-Ar. 5 In compounds of formula (Aa), A is preferably the same or different from CH or CR in each occurrence. 7 , where A stands for C when L is placed at that position 2 is bound. 10 In compounds of the formulas (Ae) or (Ca), W 1 preferably O, C(R W )2 or N-Ar 5 , especially preferred N-Ar 5 In compounds of the formula (Af), L 3 preferably a heteroaromatic ring system with 159 to 30 ring atoms, coupled with one or more R substituents 7may be substituted. In compounds of formulas (A), (Aa), (Ab), (Ac), (Ad), (Ae), (Af), (B), (Ba), (C), (Ca), (D) or (E), which can be combined according to the invention with the above-mentioned compounds as described above, Ar 5 In every 20 occurrences, independently of each other, preferred from the groups Ar 5 -1 to Ar 5 -21 selected, 25 30 35 P24-132 SC - 52 - 5 10 15 20 25 30 where the symbols and indices have the following meaning: 35 Y 3 is O, S, NAr 4 or C(R 5 )2, the dashed line is the bond that links to the rest of the formulas (A), (Aa), (Ab), (Ac), (Ad), (Ae), (Af), (B), (Ba), (C), (Ca), (D) or (E); P24-132 SC - 53 - R 5 is methyl or phenyl, which can be partially or completely deuterated and wherein two substituents R 5together they can form a spirobifluorenyl, which may be partially or completely deuterated; Ar represents phenylene, which may be partially or completely deuterated; 5m is 0 or 1 and Ar 4 is phenyl, biphenyl or terphenyl, which may be partially or completely deuterated and where R 8 has a meaning as previously described or preferably described. 10 In Y 3 is R 5 Prefers methyl. In Ar 5 -16 to Ar 5 -19 is Y 3 preferably O or NAr 4 In Ar 5 -16 to Ar 5 -19 is preferably 0. In Ar 5 -1 to Ar 5 -21 is R 8 preferably H or D. 15 In a preferred embodiment of the compounds of formulas (A), (Aa), (Ab), (Ac), (Ad), (Ae), (Af), (B), (Ba), (C), (Ca), (D) or (E), which can be combined according to the invention with the above-mentioned compounds as described above, R 7The compounds selected from the group consisting of D, F, CN, a straight-chain alkyl group with 1 to 20 carbon atoms, a branched or cyclic alkyl group with 3 to 20 carbon atoms, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which may be partially or completely deuterated, are either the same or different at each occurrence. In a particularly preferred embodiment of the compounds of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (C), (Ca), (D), or (E), which can be combined according to the invention with the aforementioned compounds as described above, R 7The matrix material, whether identical or different at each occurrence, is selected from the group consisting of D or an aromatic or heteroaromatic ring system with 6 to 30 ring atoms, each of which may be partially or completely deuterated. The preparation of the compounds of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (C), (Ca), (D), or (E) 35 is generally known, and some of the compounds are commercially available. If the at least one other matrix material is a deuterated compound, it is possible that this at least one matrix material is a mixture of deuterated compounds of the same basic chemical structure, differing only in the degree and / or deuteration pattern. The explanations regarding deuterated mixtures and the production of deuterated materials,As previously described for compounds of formula (1), the following applies accordingly. 5 In a preferred embodiment of the at least one further matrix material, this is a mixture of deuterated compounds of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (C), (Ca), (D) or (E), as previously described, wherein the average degree of deuteration 10 of these compounds is at least 10 mol% to 100 mol%, preferably 50 mol% to 95 mol%, and particularly preferably 70 mol% to 90 mol%. Suitable compounds of formula (A) are known, for example, from the following publications: WO2007 / 077810A1, WO2008 / 056746A1, WO2010 / 136109A1, WO2011 / 057706A2, WO2011 / 160757A1, WO2012 / 023947A1, WO2012 / 048781A1, WO2013 / 077352A1, WO2013147205A1, WO2013 / 083216A1, WO2014 / 094963A1, WO2014 / 007564A1, WO2014 / 015931A1, WO2015 / 090504A2, WO2015 / 105251A1, WO2015 / 169412A1, WO2016 / 015810A1, WO2016 / 013875A1,WO2016 / 010402A1, WO2016 / 033167A1, WO2017 / 178311A1, WO2017 / 076485A1, WO2017 / 186760A1, 20 WO2018 / 004096A1, WO2018 / 016742A1, WO2018 / 123783A1, WO2018 / 159964A1, WO2018 / 174678A1, WO2018 / 174679A1, WO2018 / 174681A1, WO2018 / 174682A1, WO2019 / 177407A1, WO2019 / 245164A1, WO2019 / 240473A1, WO2019 / 017730A1, WO2019 / 017731A1, WO2019 / 017734A1, WO2019 / 145316A1, WO2019 / 121458A1,WO2020 / 130381A1, WO2020 / 130509A1, WO2020 / 169241A1, 25 WO2020 / 141949A1, WO2021 / 066623A1, WO2021 / 101220A1, WO2021 / 037401A1, WO2021 / 180614A1, WO2021 / 239772A1, WO2022 / 015084A1, WO2022 / 025714A1, WO2022 / 055169A1, EP3575296A1, EP3591728A1, US2014 / 0361254A1, US2014 / 0361268A1, KR20210036304A, KR20210036857A, KR2021147993A, JP2011 / 160367A2 and JP2017 / 107992A2. 30 Particularly suitable compounds of formula (A) are compounds of WO2015 / 169412A1, described on pages 28 to 63, 93 and 110 to 114, compounds of WO2019 / 007866A1, described in Tables 1 to 8 on pages 37 to 100, compounds of WO2019 / 096717A2,described in Table 1 on pages 35, 27 to 33 and the compounds described on pages 96 to 102, compounds from WO2019 / 229011A1, described in Tables 1 and 2 on pages 31 to 117 and compounds described on pages 251 to 254, compounds from WO2021 / 037401A1, described on pages 31 to 64 and compounds P1 to P110 of pages 132 to 144, compounds from WO2020 / 169241A1, described in P24-132 SC - 55 - Table 1 on pages 30 to 73 and compounds 1 to 36 and 67 to 81 on pages 74 to 78 as well as compounds described on pages 223 to 231, compounds from WO2023247662A1, described in Tables 1 and 2 on pages 18 to 23 and compounds described on pages 100 to 102, 5 compounds from WO2023247663A1, described in Tables 1 and 2 on pages 43 to 58 and compounds described on pages 151 to 173, compounds from US2023172065 A,described on pages 6 to 413 and 435 to 498, connections from WO2016 / 015810A1, described on pages 27 to 34, 51 to 56 and 61 to 64, connections from WO18174678 A1, described on pages 20 to 10, 32 and 38 to 50, connections from WO18174681 A1, described on pages 20 to 32 and 42 to 61, connections from WO2021 / 052921A1, described in Table 1 on pages 20 to 27, connections 1 to 11 and 29 to 44 on pages 27 to 31 and connections described on pages 122 to 125, connections from WO2017 / 178311A1, described on pages 37 to 44 and connections 15 described on pages 97 to 105, compounds from WO2010 / 136109A1, described on pages 32 to 54 and the compounds of examples 1 to 54 described on pages 74 to 139, compounds from WO2011 / 000455A1, described on pages 19 to 32 and the compounds of examples 1 to 7a described on pages 51 to 59, compounds from WO2021 / 239772A1,20 described in Table 1 on pages 27 to 120 and compounds E55 to E60 on pages 223 to 224 and E61 on page 227. Suitable compounds of formula (B) are known, for example, from the following publications: WO2015 / 182872A1, WO2015 / 105316A1, WO2017 / 109637A1, WO2018 / 060307A1, WO2018 / 151479A2, WO2018 / 088665A2, WO2018 / 060218A1, WO2018 / 234932A1, WO2019 / 058200A1, WO2019 / 017730A1, WO2019 / 017731A1, WO2019 / 066282A1, WO2019 / 059577A1, WO2020 / 141949A1, WO2020 / 067657A1, WO2022063744A1, WO2022 / 090108A1, WO2022 / 207678A1, WO2023061998A1, KR20170139443A, KR20190036867A, KR2019035308A, KR2021147993A, 30 CN110294753A, CN110437241A, US2016 / 072078A1, US2019 / 148646A1. Suitable compounds of formula (C) are known, for example, from the following publications: WO2017 / 160089A1, WO2019 / 017730A1, WO2019 / 017731A1, WO2020 / 032424A1. Suitable compounds of formula (E) are known, for example, from the following publications: WO2015 / 093878A1, WO2016 / 033167A1, WO2017 / 183859A1.WO2017 / 188655A1, WO2018 / 159964A1. P24-132 SC - 56 - For combination with the compounds according to the invention, as previously described or preferably described, compounds of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B) and / or (Ba) are particularly suitable, as previously described or preferably described, or 5 corresponding compounds from the following tables which fall under these formulas. Compounds of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2) and / or (Af-3) are particularly preferred. Further examples of suitable host materials of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (C), (Ca), (D) or (E), which can be combined according to the invention with the aforementioned compounds as described above, are:The structures listed below are shown in Tables 3 and 4. Table 3: 20 25 30 35

[0003] P24-132 SC - 64 - 5 10 15 20 25 30 35 P24-132 SC - 80 - Particularly suitable compounds of formulas (A), (Aa), (Ab), (Ac), (Ad), (Ae), (Af) and / or (B), which can be combined according to the invention with the aforementioned compounds as described above and used in the electroluminescent device or mixture according to the invention, are compounds E1 to E36 of Table 4. Table 4: 10 15 20 25 30 35 P24-132 SC - 81 - 5 10 15 20 25 30 35 P24-132 SC - 82 - 5 10 15 20 25 30 For simplicity, the compounds in Tables 3 and 4 are partially represented as fully deuterated compounds, generally referring to 35 compounds that have an average degree of deuteration of at least 50 mol%. The average degree of deuteration for the fully deuterated compounds in Tables 3 and 4 is therefore between 50 mol% and 100 mol%, or has a preferred degree of deuteration as described here. For partially deuterated compounds, a D atom indicates that the P24-132 SC-83- corresponding position in the molecule has a degree of deuteration of at least 40 mol%.The host materials mentioned above according to the invention, as well as their preferably described embodiments, can be combined in the device according to the invention as desired with the aforementioned matrix materials / host materials, the matrix materials / host materials of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (C), (Ca), (D) or (E), as well as their preferably described embodiments of Table 3 or the compounds E1 to E36 of Table 4. Particularly preferred mixtures of the compounds of formula (1) with the host materials of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (C), (Ca), (D) or (E) for the device according to the invention are obtained by combining compounds H1 to H33 with compounds E1 to E36. Table 5 below shows particularly preferred mixtures.The first mixture M1, for example, is a combination of compound E1 with H1. Table 5: 20 25 30 35. P24-132 SC - 84 - 5 10 15 20 25 30 35 P24-132 SC - 85 - 5 10 15 20 25 30 35 P24-132 SC - 86 - 5 10 15 20 25 30 35 P24-132 SC - 87 - 5 10 15 20 25 30 35 P24-132 SC - 88 - 5 10 15 20 25 30 35 P24-132 SC - 89 - 5 10 15 20 25 30 35 P24-132 SC - 90 - 5 10 15 20 25 30 35 P24-132 SC - 91 - 5 10 15 20 25 30 35 P24-132 SC - 92 - 5 10 15 20 25 The concentration of the host material of formula (1), as previously described or preferably described, in the mixture according to the invention or in the light-emitting layer of the device according to the invention is typically in the range of 10 wt.% to 95 wt.%, preferably in the range of 15 wt.% to 90 wt.%, more preferably in the range of 15 wt.% to 80 wt.%, even more preferably in the range of 20 wt.% to 70 wt.%, most preferably in the range of 40 wt.% to 80 wt.% and most preferably in the range of 50 wt.% to 70 wt.%, based on the entire mixture or based on the entire composition of the light-emitting layer.P24-132 SC - 93 - The concentration of the sum of all host materials of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (C), (Ca), (D) or (E), as previously or preferably described, in the mixture according to the invention or in the light-emitting layer of the device according to the invention is typically in the range of 5 wt.% to 90 wt.%, preferably in the range of 10 wt.% to 85 wt.%, more preferably in the range of 20 wt.% to 85 wt.%, even more preferably in the range of 30 wt.% to 80 wt.%, most preferably in the range of 20 wt.% to 60 wt.% and most preferably in the range of 30 wt.% to 50 wt.% wt.%, based on the entire mixture 10 or based on the entire composition of the light-emitting layer.The present invention also relates to a mixture which, in addition to the host materials of formula (1), hereinafter referred to as host material 1, mentioned above, and the host material of at least one of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (C), (Ca), (D), or (E), as previously or preferably described, contains at least one further phosphorescent emitter. The present invention also relates to a mixture selected from a combination 20 of compounds H1 to H33 with compounds E1 to E36 or mixtures M1 to M1188, which contains at least one further phosphorescent emitter.The present invention also relates to an organic electroluminescent device as previously described or preferably described, wherein the 25 light-emitting layer, in addition to the aforementioned host materials of formula (1) and at least one of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (C), (Ca), (D) and (E), as previously described or preferably described, in particular the material combinations M1 to M1188, contains at least one phosphorescent emitter. 30 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, such as a quintet state.A transition from a triplet state is preferred. Suitable phosphorescent emitters (= triplet emitters) are compounds that, upon suitable excitation, emit light, 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, especially 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 phosphorescent emitters, especially compounds containing iridium or platinum. For the purposes of the present invention, all luminescent compounds containing the aforementioned metals are considered phosphorescent emitters.10 In general, all phosphorescent complexes suitable are those used in the prior art for phosphorescent OLEDs and those known to those skilled in the art in the field of organic electroluminescence devices. Preferred phosphorescent emitters according to the present invention correspond to formulas (I), (II), (III), (IV) or (V), 20 25 30. , 35 P24-132 SC - 95 - 5 10 15 20 25 where the symbols and indices for these formulas (I), (II), (III), (IV) and (V) have the following meanings: R1 is H or D, R2 is H, D, F, CN or a branched or linear alkyl group with 1 to 10 C atoms or a partially or completely deuterated branched or linear alkyl group with 1 to 10 C atoms or a cycloalkyl group with 4 to 10 C atoms, which may be partially or completely substituted with deuterium. Preferred phosphorescent emitters according to the present invention correspond to formula (VI), P24-132 SC - 96 - 5Formula (VI), where the symbols and indices for this formula (VI) have the following meanings: 10 n+m is 3, n is 1 or 2, m is 2 or 1, X is the same or different as N or CR in each occurrence, R is the same or different as H, D, F, CN or a branched or linear alkyl group with 1 to 10 C atoms or a partially or completely deuterated branched or linear alkyl group with 1 to 10 C atoms or a cycloalkyl group 15 with 4 to 7 C atoms which may be partially or completely substituted with deuterium or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms which may be partially or completely substituted with deuterium. In emitters of formula (VI), n is preferably 1 and m is preferably 2. 20 In emitters of formula (VI), preferably one X is selected from N and the other X represent CR, or all X represent CR, either the same or different, at each occurrence.In emitters of formula (VI), at least one R is preferably different from H. In emitters of formula (VI), two Rs are preferably different from H and have one of the meanings previously specified for the emitters of formula (VI). 25 A further object of the invention is therefore an organic electroluminescent device, as previously described or preferably described, characterized in that the light-emitting layer contains, in addition to the host materials 1 and 2, at least one phosphorescent emitter corresponding to one of formulas (I) 30 to (VI), as previously described, preferably to formula (VI). 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 included in the description by reference.35 Particularly preferred examples of phosphorescent emitters are listed in Table 6 below. P24-132 SC - 97 - Table 6: 5 10 15 20 25 30 35. P24-132 SC - 99 - 5 10 15 20 25 In the mixtures according to the invention or in the light-emitting layer of the device according to the invention, preferably each mixture of compounds H1 to H33 is combined with E1 to E36, and more preferably each mixture selected from the sum of the mixtures M1 to M1188 is combined with a compound of formulas (I) to (VI) 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, more preferably a yellow or green-emitting layer, and most preferably a green-emitting layer. A yellow-emitting layer is understood to be a layer whose photoluminescence maximum lies in the range of 540 to 570 nm.An orange P24-132 SC-100 emitting layer is defined as a layer whose photoluminescence maximum lies in the range of 570 to 600 nm. A red emitting layer is defined as a layer whose photoluminescence maximum lies in the range of 600 to 750 nm. A green emitting layer is defined as a layer whose photoluminescence maximum lies in the range of 490 to 540 nm. A blue emitting layer is defined as a layer whose photoluminescence maximum lies in the range of 440 to 490 nm.The photoluminescence maximum of the layer is determined by measuring the photoluminescence spectrum of the layer with a thickness of 50 nm at room temperature, wherein the layer comprises the inventive combination of the host material 1 of formulas (1), (1a), (1b), (1c), (1d), (1e) or (1f) and the host material 2, consisting of at least one of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (C), (Ca), (D) and (E), 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 obtained in oxygen-free solution, 10. -5The triplet energy T1 in eV is measured at room temperature using any solvent in which the chosen emitter dissolves at the specified concentration. Particularly suitable solvents are typically toluene or 2-methyl-THF, but also dichloromethane. The measurement is performed 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 formulas (I) to (VI) or from Table 6, whose triplet energy T1 is preferably at ~2.3 eV to ~2.1 eV.Preferred phosphorescent emitters are therefore green emitters, preferably of formulas (I) to (VI) or from Table 6, whose triplet energy T1 is preferably between ~2.5 eV and ~2.3 eV. Particularly preferred phosphorescent emitters are therefore green emitters, preferably of formulas (I) to (VI) or from Table 6, as described above, whose triplet energy T1 is preferably between ~2.5 eV and ~2.3 eV. P24-132 SC - 101 - Green emitters, preferably of formulas (I) to (VI) or from Table 6, as described above, are most preferably selected for the mixture or emitting layer according to the invention. 5 Fluorescent emitters may also be included 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, wherein preferably at least one of the aromatic or hetero-aromatic ring systems of the arylamine is a fused ring system, particularly preferably with at least 14 ring atoms. Preferred examples are aromatic anthracene amines, aromatic anthracenediamines, aromatic pyrene amines, aromatic pyrenediamines, aromatic chrysene amines, or aromatic chrysenediamines. An aromatic anthracene amine is understood to be a compound in which a diarylamine group is directly bonded to an anthracene group, preferably at position 9. An aromatic anthracenediamine is understood to be a compound in which two diarylamine groups are directly bonded to an anthracene group, preferably at positions 9 and 10.Aromatic pyrenamines, pyrenediamines, chrysenamines, and chrysenediamines are defined analogously, wherein the 20 diarylamine groups on the pyrene are preferably bonded at the 1-position or the 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. Benzoindenofluorene amines, 25 benzofluorene amines, extended benzoindenofluorenes, phenoxazines, and fluorene derivatives linked to furan or thiophene units are also preferred. Furthermore, the light-emitting device or the mixture according to the invention can also contain materials exhibiting TADF (thermally activated delayed fluorescence).30 In a further preferred embodiment of the invention, the at least one light-emitting layer of the organic electroluminescent device can have three or four different matrix materials, preferably three different matrix materials. These corresponding mixed-matrix systems can consist of the matrix materials described for host material 1 and host material 2; however, they can 35 also include, as a third or fourth matrix material, for example, wide-band-gap materials, bipolar host materials, electron transport materials (ETMs), or hole transport materials (HTMs), in addition to host material 1 or host material 2. Preferably, the mixed-matrix system is optimized for an emitter of formulas (I) to (VI) or for an emitter from Table 6.P24-132 SC - 102 - According to one embodiment of the present invention, the mixture contains, in addition to the components of the host material 1 and the host material 2 as previously or preferably described, no further components, i.e., functional materials. These are material mixtures that are used as such for the production of the light-emitting layer. These mixtures are also referred to as premix systems, which are used as the sole material source in the deposition of the host materials for the light-emitting layer and which have a constant mixing ratio during deposition. This allows the deposition of a layer with a uniform distribution of the components to be achieved in a simple and rapid manner, without the need for precise control of a multitude of material sources.According to an alternative embodiment of the present invention, the mixture 15 contains, in addition to the components of host material 1 and host material 2 as previously or preferably described, a phosphorescent emitter as previously described. With a suitable mixing ratio during evaporation, this mixture can also be used as the sole material source. 20 Premix systems consisting of two matrix materials are preferred, namely a compound of formulas (1), (1a), (1b), (1c), (1d), (1e) or (1f) and a compound of one of the formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (C), (Ca), (D) or (E).Preferred are premix systems consisting of three matrix materials, namely one compound of formulas (1), (1a), (1b), (1c), (1d), (1e) or (1f) and two compounds of one of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), (Ba), (C), (Ca), (D) or (E). The components 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 previously or preferably described, optionally with the phosphorescent emitter, as previously or preferably described, is provided in a formulation containing at least one solvent. Suitable formulations have been previously described.The light-emitting layer in the device according to the invention, in the preferred embodiments, and the emitting compound preferably contains between 99.9 and 1 vol.%, more preferably between 99 and 10 vol.%, particularly P24-132 SC - 103 - preferably between 98 and 60 vol.%, most preferably between 97 and 80 vol.% of matrix material consisting of at least one compound of formulas (1), (1a), (1b), (1c), (1d), (1e) or (1f) and at least one compound of one of formulas (A), (Aa), (Aa-1), (Aa-2), (Aa-3), (Aa-4), (Aa-5), (Ab), (Ac), (Ad), (Ae), (Af), (Af-1), (Af-2), (Af-3), (B), 5 (Ba), (C), (Ca), (D) or (E) 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.%, and particularly preferably between 2 and 40 vol.%.-%, most preferably between 3 and 20 vol% of the 10 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 amounts in vol% specified above. 15 The present invention also relates to an organic electroluminescent device as previously or preferably described, wherein the organic layer comprises a hole injection layer (HIL) and / or a hole transport layer (HTL) and / or an electron blocking layer (EBL), the hole-injecting material or hole-transporting material or electron blocking material of which belongs to the class of 20 arylamines, which contains at least one fluorenyl unit, azafluorenyl unit, azaspirobifluorenyl unit or spirobifluorenyl unit and no carbazole unit.The present invention also relates to an organic electronic device, preferably an organic light-emitting device, as previously described or 25 more preferably described, wherein the layer containing the arylamine has at least one fluorenyl unit, azafluorenyl unit, azaspirobifluorenyl unit or spirobifluorenyl unit and no carbazole unit, and is directly adjacent to the emitting layer. 30 Preferred arylamines that can be used according to the invention are compounds of formula (IA), 35. Formula (IA), where the symbols and indices used in these compounds of formula (IA) are as follows: P24-132 SC - 104 - Ar 10 , Ar 11 When they occur, they are either identical or different, independently of each other: an aromatic ring system with 6 to 40 ring atoms or a heteroaromatic ring system with 5 to 40 ring atoms, which are equipped with one or more substituents R 12can be substituted, with two substituents Ar 10 5 and Ar 11 together they can form an aliphatic, aromatic or heteroaromatic ring, which may contain one or more substituents R 12 may be substituted; L 12 In cases where the elements occur independently of each other, whether identical or different, a single bond or an aromatic or heteroaromatic ring system with 5, 10, or 30 ring atoms, containing one or more substituents R, is present. 13 can be substituted; k12 means 1, 2 or 3; Ar 12 will be made up of the groups Ar 12 -1 or Ar 12 -2 selected, 15 20 25 Z and Z 1 are each independent of each other C, CH or N, excluding the possibility that two adjacent groups Z or two adjacent groups Z 1 30 simultaneously mean N; a is 1, 2 or 3; b, c, d are each independently 1, 2, 3 or 4; R 12 or R 13H, D, F, Cl, Br, I, CHO, CN, NH2, N(R) mean, when they occur, independently of each other, either the same or different. 19 )2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, 35 NO2, Si(R 19 )3, B(OH)2, B(OR 19 )2, OSO2R 19 , a straight-chain alkyl, alkoxy or thioalkyl group with 1 to 40 C atoms or a branched or cyclic alkyl group with 3 to 40 C atoms, wherein one or more H atoms are replaced by R 19 can be replaced, with one or more non-adjacent CH2 groups being replaced by R 19 C=CR 19 , HC=CH, C≡C, Si(R 19 )2, Ge(R 19 )2, Sn(R 19 )2, C=O, C=S, C=Se, P24-132 SC - 105 - P(=O)(R 19 ), may be replaced by SO, SO2, O or S, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which is modified by one or more substituents R 19 may be substituted; R 19is selected, in each occurrence, as the same or different from group 5 consisting of D, F, CN, Si(Ar)3, a straight-chain alkyl group with 1 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein one or more non-adjacent CH2 groups may be replaced by O or S and wherein one or more H atoms may be replaced by D, F, or CN, or a non-deuterated or partially or completely deuterated aryl group with 6 to 30 C atoms; Ar is, in each occurrence independently, as the same or different from each other, an aryl group with 6 to 30 C atoms or a heteroaryl group with 5 to 40 ring atoms, which may be partially or completely deuterated; * indicates the connection to the remainder of formula (IA); 15 and wherein the compounds of formula (IA) do not contain a carbazole unit. A preferred embodiment of group Ar 12 -1 are the groups Ar 12 -1-1 or Ar 12 - 20 25 30 35 , where R 12 , a, b, c, d and * have a previously specified meaning. P24-132 SC - 106 - A preferred embodiment of group Ar 12 -2 are the groups Ar 12 -2-1 or Ar 12 - 5 10 where R 12 , Z 1 , a, b, c, d and * have a previously specified meaning. 15 In a preferred embodiment of the compounds of formula (IA), these are selected from compounds of formulas (IA-1) to (IA-4), 20 25 30 Formula (IA-3) Formula (IA-4), where R 12 , Ar 10 , Ar 11 and L 12 have a previously specified meaning, where H represents R 12 35 is excluded and where R 12*In each occurrence, independently of one another, a straight-chain or branched alkyl group with 1 to 10 carbon atoms or phenyl is represented, wherein the alkyl or phenyl group may contain one or more d atoms, and with the condition that no carbazole unit is present in the compounds. P24-132 SC - 107 - In compounds of formulas (IA), (IA-1), (IA-2), (IA-3) and (IA-4), the linker L 12 preferably a single bond or selected from phenylenes, biphenyls, terphenyls, naphthylene, fluorenylenes, indenofluorenylenes, spirobifluorenylenes, dibenzofuranyles or 5 dibenzothiophenylenes, which have one or more substituents R 13 They can be substituted. L is particularly preferred. 12 a bond or phenyls, biphenyls, terphenyls, naphthylenes, dibenzofuranyles or dibenzothiophenyls, which have one or more substituents R 13 They can be substituted. L is particularly preferred. 12a bond, phenyls or biphenyls, which has one or more 10 substituents R 13 They can be substituted. R 13 D is preferred. In combinations of formulas (IA-1), (IA-2), (IA-3) and (IA-4), R is preferred. 12* preferably methyl or phenyl, which may be substituted with one or more D atoms. In compounds of formulas (IA-1), (IA-2), (IA-3) and (IA-4) R 12 Preferably 15 independently of one another, a straight-chain or branched alkyl group with 1 to 10 carbon atoms, an aryl group with 6 to 18 carbon atoms, or an arylalkyl group with 6 to 30 carbon atoms, wherein these groups may be substituted with one or more d atoms. In compounds of formulas (IA-1), (IA-2), (IA-3), and (IA-4), R 12Particularly 20, preferably independently of one another, tert-butyl, phenyl, or phenyl substituted by tert-butyl, wherein these groups may be substituted with one or more D atoms. In one embodiment of the compounds of formulas (IA), (IA-1), (IA-2), (IA-3) and 25 (IA-4), the group 30 selected from groups (A-1) to (A-39), where these groups may also be partially or completely deuterated, 35 A-1 A-2 P24-132 SC - 108 - 5 10 15 20 25 30 35 P24-132 SC - 109 - 5 10 15 20 25 30 35 P24-132 SC - 110 - 5 10 15 20 25 30 35 P24-132 SC - 111 - P24-132 SC - 112 - 5 10 15 20 where the dashed line signifies the connection to the rest of the formulas (IA), (IA-1), (IA-2), (IA-3) and (IA-4) and where R 4In each occurrence, independently the same or 25 different, a straight-chain or branched alkyl group with 1 to 10 carbon atoms or a phenyl group is meant, wherein the alkyl group or phenyl group may be partially or completely deuterated and wherein two substituents R 4 together they can form an aliphatic, aromatic, or heteroaromatic ring, preferably a spiro system, which may be partially or completely deuterated. 30 Compounds of formulas (IA), (IA-1), (IA-2), (IA-3), and (IA-4) are preferably partially or completely deuterated. Preferred compounds with hole transport functionality for the hole injection layer (HIL) / hole transport layer (HTL) and / or electron blocking layer (EBL) are shown in Table 7 below, which may be partially or completely deuterated. Table 7: The following compounds in this table may also be partially or completely deuterated. P24-132 SC - 121 - 5 10 15 20 25 Methods for synthesizing the compounds of formulas (IA), (IA-1), (IA-2), (IA-3) and (IA-4), the preferred embodiments of these compounds and the compounds of Table 7 are known in the prior art, in particular from the following publications of the table below: 30 35 P24-132 SC - 122 - 5 10 The sequence of layers in the organic electroluminescence 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 aforementioned layers need to be present and / or that additional layers may be present. All materials used as electron transport materials in electron transport layers according to the prior art can be used as materials for the electron transport layer.Particularly suitable are aluminium 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, 30 boranes, diazaphosphol derivatives and phosphine oxide derivatives. The present invention also relates to an organic electroluminescent device as previously or preferably described, wherein the organic layer comprises a hole injection layer (HIL) and / or a hole transport layer (HTL) 35 and / or an electron blocking layer, the hole-injecting material and hole-transporting material of which is selected from the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) or (1k), as previously or preferably described.P24-132 SC - 123 - Suitable cathodes for the device according to the invention include metals with 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., Ca, Ba, Mg, Al, In, Yb, Sm, etc.). Alloys 5 of an alkali or alkaline earth metal and silver are also suitable, for example, an alloy of magnesium and silver. In multilayer structures, additional metals with relatively high work functions, such as Ag or Al, can also be used, in which case combinations of the metals, such as Ca / Ag, Mg / Ag, or Ba / Ag, are generally employed. It may also be preferred 10 to introduce a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor.Suitable materials for this purpose include alkali metal or alkaline earth metal fluorides, as well as the corresponding oxides or carbonates (e.g., LiF, Li₂O, BaF₂, MgO, NaF, CsF, Cs₂CO₃, etc.). Lithium quinolinate 15 (LiQ) can also be used. The thickness of this layer is preferably between 0.5 and 5 nm. Materials with a high work function are preferred as the anode. Preferably, the anode 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. Alternatively, metal / metal oxide electrodes (e.g., Al / Ni / NiO) can also be used. x , Al / PtO x) is preferred. For some applications, at least one of the electrodes must be transparent or semi-transparent to allow either the irradiation of the organic material (organic solar cell) or the extraction of light (OLED, O-LASER). 25 Preferred anode materials are conductive mixed metal oxides. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred. Conductive, doped organic materials, especially conductive doped polymers, are also preferred. Furthermore, the anode can also consist of several layers, for example, an inner layer of ITO and an outer layer of a 30 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 its manufacture (depending on the application), since the lifetime of the devices according to the invention is reduced in the presence of water and / or air. The manufacture of the device according to the invention is not limited in this respect. It is possible to coat one or more organic layers, including the light-emitting layer, using a sublimation process. In this process, the P24-132 SC-124 materials are sublimated in vacuum sublimation systems at an initial pressure of less than 10. -5 mbar, preferably less than 10 -6 The initial pressure is vapor-deposited at mbar. However, it is also possible that the initial pressure is even lower, for example less than 10 mbar. -7mbar. 5 The organic electroluminescence device according to the invention is preferably characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or with the aid of carrier gas sublimation. The materials are applied 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 containing the composition according to the invention are produced from solution, e.g., by spin coating, or by 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. Soluble host materials 1 and 2 and phosphorescent emitters are required for this purpose.The 20 solution-based processing method 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. 25 Furthermore, hybrid processes are possible in which, for example, one or more layers are applied from solution and one or more additional layers are vapor-deposited. These processes are generally known to those skilled in the art and can be applied to organic 30 electroluminescent devices.A further object of the invention is therefore a method for producing the organic electroluminescent device according to the invention, as previously or preferably described, characterized in that the organic layer 35, preferably the light-emitting layer, the hole injection layer and / or hole transport layer, is applied by vapor deposition, in particular by a sublimation process and / or by an OVPD (Organic Vapor Phase Deposition) process and / or by means of carrier gas sublimation, or from solution, in particular by spin coating or by a printing process. P24-132 SC - 125 - In the production by means of vapor deposition, there are basically two possibilities as to how the organic layer according to the invention, preferably the light-emitting layer, can be applied or vapor-deposited onto any substrate or the previous layer 5.Firstly, the materials used can each be placed in a separate material source and then evaporated from the various material sources ("co-evaporation"). Secondly, the different materials can be premixed ("premix 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 numerous material sources.15 The following methods are possible: A method for producing the organic electroluminescent device according to the invention, as previously described or preferably described, characterized in that the organic layer, preferably the light-emitting layer, the electron transport layer and / or hole-blocking layer, is applied by 20 gas phase deposition, in particular with a sublimation process and / or with 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 with a printing process.25 A method for producing the organic electroluminescent device according to the invention, as previously described or preferably described, characterized in that the light-emitting layer of the organic layer is applied by gas phase deposition, wherein the at least one compound of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) or (1k) together 30 with the further materials forming the light-emitting layer are deposited successively or simultaneously from at least two material sources from the gas phase.A method for producing the device according to the invention, characterized in that the light-emitting layer of the organic layer is applied by gas phase deposition, wherein the at least one compound of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j) or (1k) together with at least one further matrix material as a premix, is deposited from the gas phase successively or simultaneously with the light-emitting materials selected from the group consisting of P24-132 SC - 126 - phosphorescent emitters, fluorescent emitters and / or emitters exhibiting TADF (thermally activated delayed fluorescence).5 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: The electronic devices according to the invention, in particular organic electroluminescent devices, are characterized by one or more of the following surprising advantages over the prior art: 1. Electronic devices, in particular organic electroluminescent devices, containing compounds according to formula (1) or 15 the previously and subsequently described preferred embodiments, in particular as matrix material or as hole-conducting materials, have a very low operating voltage. In this respect, these compounds in particular result in a low roll-off, i.e., a low drop in the power efficiency of the device at high luminances.Compounds according to the invention containing a biphenyl group instead of a phenyl group exhibit, in particular, an increased lifetime. With deuterated derivatives, the lifetime is further increased. Thus, it is unexpectedly shown that the compounds according to the invention of formula (1) or the previously described embodiments, preferably with two dibenzofuran units in position 3 or 4 of the indolocarbazole backbone in an OLED, lead to a significantly improved voltage and / or lifetime of the OLED. 2. The compounds according to the invention according to formula (1) or the previously and subsequently described preferred embodiments exhibit very high stability and lifetime. 3. With compounds according to formula (1) or the previously and subsequently described preferred embodiments, the formation of optical loss channels can be avoided in electronic devices, in particular organic electroluminescent devices.These devices are characterized by high PL and thus high EL efficiency of emitters, or excellent energy transfer from the matrices to the dopants. P24-132 SC - 127 - 4. The compounds according to formula (1) and the preferred embodiments described before and after exhibit a low triplet level T1, which can be in the range of 2.40 eV to 2.90 eV. 5 These advantages mentioned above are not accompanied by an unduly high 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 section 10 of 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 considered as an example of a generic series or as an equivalent or similar feature to

[15] . All features of the present invention may 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.

[20] Likewise, features of non-essential combinations may be used separately (and not in combination). The teaching on technical action disclosed with the present invention may be abstracted and combined with other examples.

[25] The invention is further explained by the following examples without being intended to limit it.Examples Synthesis Examples 30 The following syntheses are carried out under a protective gas atmosphere in dried solvents, unless otherwise stated. The compounds according to the invention can be prepared using synthesis methods known to those skilled in the art. 35 a) 4-(2-Bromo-6-nitrophenyl)-9-phenyl-9H-carbazole P24-132 SC - 128 -. 5. A well-stirred, degassed suspension of 53 g (184 mmol) (9-phenyl-9H-carbazol-4-yl)boronic acid, 60 g (184 mmol) 1-bromo-2-iodo-3-nitrobenzene, and 66.5 g (212.7 mmol) potassium carbonate in a mixture of 250 mL water and 250 mL THF is treated with 1.7 g (1.49 mmol) Pd(PPh3)4 and heated under reflux for 17 h. After cooling, the organic phase is separated, washed three times with 200 mL water and once with 200 mL saturated aqueous sodium chloride solution, dried over magnesium sulfate, and rotated to dryness. The gray residue is recrystallized from hexane. The precipitated crystals are filtered off, washed with a little methanol, and dried under vacuum. Yield: 64 g (144 mmol), 79% of theory. 15 20 25 30 35 P24-132 SC - 129 - 5 10 15 20 25 b) 1-Bromo-8-phenyl-5,8-dihydroindolo[2,3-c]carbazole 30 A mixture of 53 g (120 mmol) of 4-(2-bromo-6-nitrophenyl)-9-phenyl-9H-carbazole and 35,145 ml (800 mmol) of triethyl phosphite is heated under reflux for 12 h. The remaining triethyl phosphite is then distilled off (72–76 °C / 9 mm Hg). The residue is treated with water / methanol (1:1), the solid is filtered off, and recrystallized. Yield: 36 g (87 mmol), 73% of theory. P24-132 SC - 130 - The following compounds are prepared analogously: 5 10 15 20 25 30 35 P24-132 SC - 131 - 5 10 c) 1-(Dibenzo[b,d]furan-1-yl)-8-phenyl-5,8-dihydroindolo[2,3-c]carbazole 15 6.7 g (32 mmol) of (dibenzofuran-1-yl)boronic acid, 13.3 g (32 mmol) of 1-bromo-8-phenyl-5,8-dihydroindolo[2,3-c]carbazole, and 31 mL (63 mmol) of Na₂CO₃ (2 M solution) are suspended in 120 mL of toluene and 120 mL of ethanol. To this suspension, 0.73 g (0.63 mmol) of Pd(PPh₃)₄ is added, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated, filtered over silica gel, washed three times with 200 mL of water, and then concentrated to dryness. The residue is recrystallized from toluene. The yield is 10 g (20 mmol), corresponding to 63% of theory. The following compounds are prepared analogously: 35 P24-132 SC - 132 - 5 P24-132 SC - 133 - 5 10 15 20 25 30 35 P24-132 SC - 134 - 5 10 15 20 25 30 35 P24-132 SC - 135 - 5 10 15 20 d) 1,5-Bis(dibenzo[b,d]furan-1-yl)-8-phenyl-5,8-dihydroindolo[2,3-c]carbazole 25 30 A degassed solution of 36.1 g (147 mmol) of 1-bromodibenzofuran and 73.2 g (147 mmol) of 1-(dibenzo[b,d]furan-1-yl)-8-phenyl-5,8-dihydroindolo[2,3-c]carbazolein in 600 mL of toluene is saturated with nitrogen for 1 h. The solution is then treated first with 2.09 mL (8.6 mmol) of P(tBu)3,35, then with 1.38 g (6.1 mmol) of palladium(II) acetate, and finally with 17.7 g (185 mmol) of solid NaOtBu. The reaction mixture is heated under reflux for 1 h. After cooling to room temperature, 500 mL of water are carefully added. The aqueous phase is washed with 3 x 50 mL toluene, dried over P24-132 SC - 136 - MgSO4, and the solvent is removed under vacuum. The crude product is then purified chromatographically over silica gel with heptane / acetic acid ester (20 / 1). The residue is recrystallized from toluene and finally evaporated under high vacuum (p = 5 x 10⁻⁶). 6The solution sublimes at a pressure of 10 mbar. The yield is 81 g (121 mmol), corresponding to 83% of the theoretical yield. The following compounds are prepared analogously: 10 15 20 25 30 35 P24-132 SC - 137 - 5 10 15 20 25 30 35 P24-132 SC - 138 - 5 10 15 20 25 30 35 P24-132 SC - 139 - 5 10 15 20 25 30 35 P24-132 SC - 140 - 5 10 15 20 25 30 35 P24-132 SC - 141 - 5 10 15 20 25 30 35 P24-132 SC - 142 - 5 10 15 20 25 30 35 P24-132 SC - 143 - 5 10 15 20 25 30 35 P24-132 SC - 144 - 5 e) 1,5-Bis(dibenzo[b,d]furan-1-yl-d7)-8-(phenyl-d5)-5,8-dihydroindolo[2,3-c]carbazole- 10 2,3,4,6,7,9,10,11,12-d9 15 20 30.5 g (46.0 mmol; 1.00 eq) of 1,5-bis(dibenzo[b,d]furan-1-yl)-8-phenyl-5,8-dihydroindolo[2,3-c]carbazole is suspended in 640 mL (120 eq) of toluene-d8 [CAS 2037-26-5]. 16.6 mL (6.00 eq) of trifluoromethanesulfonic acid is added to this mixture while cooling. The reaction mixture is stirred at ambient temperature (25°C) for 6 hours. Subsequently, 120 mL (130 eq) of deuterium oxide [CAS 7789-20-0] is added dropwise at 0°C. After neutralization with a potassium sulfate solution, the mixture is extracted with toluene, and the combined organic phases are washed with sodium chloride and dried over sodium sulfate. After filtration, the solvent is removed under reduced pressure. 18.1 g (26 mmol, 57% of theory) of the product shown above, in mixture with portions of H / D isotopomers and H / D isotopologues, are obtained after chromatographic purification and finally evaporated under high vacuum (p = 5 x 10⁻⁵). -7(mbar) sublimed (purity 99.9%). 35 P24-132 SC - 145 - The following compounds are prepared analogously: 5 10 15 20 25 30 35 P24-132 SC - 146 - 5 10 15 20 25 30 35 P24-132 SC - 147 - 5 10 15 20 25 30 35 P24-132 SC - 148 - 5 10 Fabrication of the OLEDs The following examples V1-1 and Ex1-1 to Ex7 (see Tables 8 and 9) present the data for various OLEDs. Examples Ex1-1 to Ex7 show data for 15 OLEDs according to the invention; example V1-1 is a comparative example according to the prior art. Glass platelets coated with structured ITO (indium tin oxide) with a thickness of 50 nm are used as the substrate for the OLEDs in Table 8. The exact structure of the OLEDs is given in Table 8. The materials required for fabricating the OLEDs are shown in Table 10, unless described earlier. All materials are thermally deposited in a vacuum chamber. The emission layer always consists of at least one matrix material (also called host material 25) and an emitting dopant (doping agent, emitter), which is added to the matrix material(s) by cover evaporation in a specific volume fraction.A specification like E8:SdT1:TEG3 (42%:50%:8%) 40nm means that material E8 is present in a volume fraction of 42% as host material 1, the compound SdT1 as host material 2 in a fraction of 50%, and TEG3 in a fraction of 8% in a 40nm thick layer. Similarly, the hole injection layer (HIL) and the electron transport layer (ETL) can also consist of a mixture of two materials. OLEDs are characterized using standard methods. For this, the 35 electroluminescence spectra and current-voltage-luminance (IUL) characteristics are measured, and the EQE is calculated from these measurements. The calculation assumes a Lambertian emission characteristic. The voltage required for a current density of 10 mA / cm² is denoted here as U10. EQE10 denotes the external quantum efficiency at a current density of 10 mA / cm².P24-132 SC - 149 - For each example (Ex) according to the invention, the relative EQE and the relative voltage are calculated in comparison to the respective reference example (V): rel. U (Ex) = 100 * (U10(Ex) / U10(V)) rel. EQE (Ex) = 100 * (EQE10(Ex) / EQE10(V)). 5 The lifetime LT90 is defined as the time after which the luminance decreases from a starting luminance L0 (in cd / m²) to 90% of this starting luminance when operating with a constant current density j0 in mA / cm². In the examples shown here, the current density used is 60 mA / cm². 10 For each example (Ex) according to the invention, the relative LT is calculated in comparison to the respective reference example (V): rel. LT (Ex) = 100 * (LT90(Ex) / LT90(V)) 15 Use of mixtures according to the invention in OLEDs The compounds or material combinations according to the invention can be used in the emission layer in phosphorescent green OLEDs.The examples according to the invention show, in particular, a significant advantage in the lifetime and operating voltage of the device compared to the prior art. With deuterated derivatives, the lifetime is further increased. Table 8: Structure of the OLEDs 25 30 35. P24-132 SC - 150 - 5 10 15 Table 9: 20 25 30 Table 10: Materials used, unless described above 35 P24-132 SC - 151 - 5 10 15 20 25 30 35

Claims

1. P24-132 SC - 152 - Claims 5 10 , where the following applies to the symbols and indices used: 15 (R) a , (R) b Each term independently represents monosubstitution, disubstitution, trisubstitution, the maximum permissible substitution, or no substitution with substituent R; R, in each instance, is independently D or unsubstituted, partially or completely deuterated phenyl; 20 R 0 is H or D; Y is O or S regardless of occurrence; Ar* is an aryl group with 6 to 30 C atoms, linked to one or more R groups 1 can be substituted; R 1is selected, in each occurrence, as the same or different from group 25, consisting of D, F, CN, Si(aryl)3, a straight-chain alkyl group with 1 to 20 C atoms, or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein one or more non-adjacent CH2 groups may be replaced by O or S, and wherein one or more H atoms may be replaced by D, F, or CN, or a non-deuterated or partially or completely deuterated aryl group with 6 to 30 C atoms; the aryl group, in each occurrence independently, is either an aryl group with 6 to 30 C atoms or a heteroaryl group with 5 to 40 ring atoms, which may be partially or completely deuterated. 35 2. Compounds according to claim 1, wherein in compounds of formula (1) YO means.

3. Compounds according to claim 1 or 2, wherein the average degree of deuteration is 5 mol% to 100 mol%. P24-132 SC - 153 - 4.Compound according to one or more of claims 1 to 3, selected from compounds H1 to H33: 5 10 15 20 25 30 35. P24-132 SC - 154 - 5 10 15 20 25 30 35 P24-132 SC - 155 - 5 10 15 20 25 5. A mixture comprising at least one compound of formula (1) according to one or more of claims 1 to 4 and at least one further compound, 30 selected from the group consisting of matrix materials, phosphorescent emitters, fluorescent emitters and / or emitters exhibiting TADF (thermally activated delayed fluorescence).

6. Use of at least one compound of formula (1) according to one or 35 several of claims 1 to 4 in an organic electronic device.

7. An organic electronic device comprising an anode, a cathode and at least one organic layer, comprising at least one compound of formula (1) according to one or more of claims 1 to 4, wherein the organic P24-132 SC - 156 layer is at least a light-emitting layer, a hole-transporting layer, a hole-injecting layer or an electron-blocking layer. 8.Organic electronic device according to claim 7, wherein the electronic device is an organic integrated circuit (OIC), an organic field-effect transistor (OFET), an organic thin-film transistor (OTFT), an organic electroluminescent device, an organic solar cell (OSC), an organic optical detector, or an organic photoreceptor. Organic electronic device according to claim 7 or 8, characterized in that the light-emitting layer contains the at least one compound of formula (1) according to any one of claims 1 to 4. Organic electronic device according to one or more of claims 7 to 9, characterized in that the light-emitting layer, in addition to the compound of formula (1) according to any one of claims 1 to 4, contains at least one further matrix material selected from the compounds of formulas (A), (B), (C), (D), (C), (A), (D), (C), (D), (C), (C), (C), (C), (C), (C), (C), (C), (C), (C), (C), (C), (C), (C), (C, ..., (C), (C), (C), (C), (C), (C, (C), (C), (C), (C), (C), (C, (C), (C), (C), (C), (C), (C, (C), (C), (C), (C), (C), (C), (C), (C, (C , P24-132 SC - 157 - 5 10 , where the following applies to the symbols and indices used: X is the same or different from N or CR in each occurrence 6 , preferably N; L 2 is the same or different in each occurrence a single bond or 15 an aromatic or heteroaromatic ring system with 5 to 24 ring atoms, each with one or more R groups 7 may be substituted; R## is the same or different in each occurrence D, F, CN or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which is joined with one or more R substituents 6 can be substituted and two adjacent substituents R## can together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system, which is joined with one or more R groups 7 It may be substituted; Y is the same or different in each occurrence N or CR 9 , where it is excluded that two adjacent Ys simultaneously mean N; V2 is O or S; R 6 is the same or different in each occurrence D, F, CN, a straight-chain alkyl group with 1 to 20 C atoms or an alkenyl or alkynyl group with 2 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each linked to one or more R groups 7 can be substituted and where one or more non-adjacent CH2 groups are replaced by Si(R 7 )2, C=O, NR 7 , O, S or CONR 7 can be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, each of which can be partially or completely deuterated; in which case two residues R 6 also together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; P24-132 SC - 158 - Ar 5In each instance, the term represents, in the same or different ways, an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which is coupled with one or more R groups. 7 may be substituted; R 7 is the same or different in each occurrence D, F, Cl, Br, I, N(R 8 )2, CN, 5 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 with 1 to 20 carbon atoms, or an alkenyl or alkynyl group with 2 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein one or more non-adjacent CH2 groups are truncated by Si(R 8 )2, C=O, NR 8 , O, 10 S or CONR 8can be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which can be partially or completely deuterated; in this case, two or more R groups can be present. 7 together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; 15 R 8 is, in each occurrence, the same or different H, D, F or an aliphatic, aromatic or heteroaromatic organic residue, in particular a hydrocarbon residue, with 1 to 20 C atoms, in which one or more H atoms may also be replaced by D or F; R 9 is the same or different in each occurrence H, D, F, Cl, Br, I, N(R 8 )2, 20 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 with 1 to 20 carbon atoms, or an alkenyl or alkynyl group with 2 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein the alkyl, alkenyl or alkynyl group is each linked to one or more 25R substituents 6 can be substituted, where one or more non-adjacent CH2 groups are replaced by Si(R) 8 )2, C=O, NR 8 , O, S or CONR 8 can be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which is replaced by one or more R groups 6 It can be substituted; in this case, two or more residues R can be involved. 9together form a 30 aromatic, heteroaromatic, aliphatic, or heteroaliphatic ring system; b1 is 0, 1, 2, 3, or 4; b2 is 0, 1, 2, or 3. 35 11. Organic electronic device according to one or more of claims 7 to 10, wherein the light-emitting layer contains a phosphorescent emitter. P24-132 SC - 159 - 12. Organic electronic device according to one or more of claims 7 to 11, wherein the organic layer contains a hole injection layer and / or a hole transport layer and / or an electron blocking layer, the hole-injecting material or hole-transporting material or electron blocking material belonging to the class of arylamines, which contains at least one fluorenyl unit, azafluorenyl unit, azaspirobifluorenyl unit, or spirobifluorenyl unit. 13.Organic electronic device according to claim 12, wherein the layer containing the 10 arylamine and containing at least one fluorenyl unit or spirobifluorenyl unit is directly adjacent to the emitting layer.

14. Organic electronic device according to one or more of claims 7 to 13, characterized in that it is an 15 electroluminescent device selected from the organic light-emitting transistors (OLETs), organic field-quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers), and organic light-emitting diodes (OLEDs). 20 25 30 35.

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