Materials for organic light-emitting devices

Abstract

The present invention relates to OLED materials containing aza-dibenzofuran or aza-dibenzothiophene; to the use thereof in organic electronic devices; to mixtures containing these materials; and to electronic devices containing these compounds, in particular organic electroluminescent devices containing these compounds as matrix materials, electron-transport materials or hole-blocking materials.

Description

[0001] P24072 Sc - 1 - Materials for organic light-emitting devices Technical field The present invention relates to azadibenzofurans or azadibenzothiophenes, 5 mixtures comprising them, their use in organic electronic devices, and electronic devices comprising these compounds, in particular organic light-emitting devices comprising these compounds as matrix materials, electron-transport materials, or hole-blocking materials. 10 State of the art Phosphorescent organometallic complexes are frequently used in organic electroluminescent devices (OLEDs). In general, there is still room for improvement in OLEDs, for example with regard to efficiency, operating voltage, and lifetime. The properties of phosphorescent OLEDs are not only determined by the triplet emitters used.The other materials used, such as matrix materials, are also of particular importance here. Improvements to these materials can therefore also lead to significant improvements in OLED properties. 20 According to the prior art, carbazole derivatives, dibenzofuran derivatives, indenocarbazole derivatives, indolocarbazole derivatives, or triphenylene derivatives are used, among others, as matrix materials for phosphorescent emitters. US2015336937 A1, WO18060218 A1, WO19066282 A1, and WO2020111602 A1 25 describe special diazadibenzofurans or diazadibenzothiophenes, among others, as matrix materials. In general, there is still room for improvement with these materials, particularly for use as matrix materials.The object of the present invention is to provide compounds which are particularly suitable for use as matrix material, electron transport material or hole blocking material in a phosphorescent OLED. In particular, the object of the present invention is to provide matrix materials which, when used in an OLED, lead to an improved lifetime and a lower capacitance of the device. The desire for an improved lifetime applies in particular when using a low to medium emitter concentration in the light-emitting layer, ie at emitter concentrations in the order of magnitude of 3 to 20%, in particular 3 to 15%, since the device lifetime is limited in particular here. P24072 Sc - 2 - The capacitance of a device is an important parameter with regard to achievable switching times of the device.Since modern OLED screens are operated at ever-increasing refresh rates (from 60 Hz to 120 Hz or even 240 Hz today), short switching times for OLED devices are essential. An important prerequisite for this is the lowest possible capacitance, both with regard to the threshold voltage of the rise in the capacitance curve (beyond the level of geometric capacitance) and with regard to the maximum capacitance signal. It has now been found that electroluminescent devices containing compounds 10 according to the following formula (1) exhibit improvements over the prior art, particularly when using the compounds as matrix material for phosphorescent dopants.It has further been found that the combination of at least one compound of formula (1) as the first host material and at least one hole-transporting compound, for example in combination with one or more compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6), as a further host material or further host materials in a light-emitting layer of an organic electronic device, in particular an organic electroluminescent device, solves this problem and eliminates the disadvantages of the prior art. Summary of the Invention The present invention firstly provides a compound of formula (1), ABC formula (1), where B denotes a structure of formula (2), A denotes a structure of formula (3) and C denotes a structure of formulas (4), (5) or (6). Formula (2), P24072 Sc - 3 - 5 10 15 where the symbols and indices used are: a, b and c represent the respective linking points to formulas (3), (4), (5) or (6); 20 V is O or S; Y is each independently N, C, CH or CR 1 , where at least one Y is N and where it is excluded that two adjacent Ys simultaneously represent N; R# is at each occurrence independently an aryl group having 6 to 20 25 C atoms which is reacted with one or more radicals R 0 may be substituted; m is independently 0, 1 or 2 at each occurrence; * is the linkage point to a, b or c of formula (2); # is the linkage point to a, b or c of formula (2); R a , R b , R c and R d represent a monosubstitution, a disubstitution, a 30 trisubstitution, the maximum permissible substitution or no substitution; R a , R b , R c and R dare D at each occurrence; Ar3 is an aryl or heteroaryl group with 5 to 40 ring atoms which can be substituted with one or more radicals R 0 can be substituted; 35 R 1 is at each occurrence independently D, CN, F or an aryl or heteroaryl group having 5 to 40 ring atoms which can be substituted by one or more radicals R 0 may be substituted; R 0 is selected at each occurrence, identically or differently, from the group consisting of D, F, Cl, Br, I, CN, NO2, C(=O)R 2 , P(=O)(Ar)2, P(Ar)2, B(Ar)2, P24072 Sc - 4 - Si(Ar)3, Si(R 2 )3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 C atoms, each of which is substituted by one or more radicals R 2 may be substituted 5, where one or more non-adjacent CH2 groups are substituted by R 2 C=CR 2, Si(R 2 )2, C=O, C=S, C=NR 2 , P(=O)(R 2 ), SO, SO2, NR 2 , O, S or CONR 2 and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aryl or heteroaryl group having 5 to 40 ring atoms which may be substituted with one or more radicals R 2 may be substituted 10, an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, which may be substituted with one or more radicals R 2 may be substituted, or an aralkyl or heteroaralkyl group having 5 to 40 ring atoms which may be substituted with one or more radicals R 2 may be substituted; R 2is selected, identically or differently at each occurrence, from the group 15 consisting of D, F, CN, Si(Aryl)3, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms may be replaced by D, F or CN, 20 Aryl is an unsubstituted, partially or fully deuterated aryl group having 6 to 40 C atoms, with the condition that the structure of the formula (3) with the linkage point * and the structure of the formulas (4), (5) or (6) with the linkage point # in the formula (2) are directly adjacent. 25 The direct proximity of structure A next to structure C leads to special properties of the compounds of formula (1), in particular with regard to their solubility and evaporation temperatures,which are suitable for combination with hole-transporting host materials. 30 The invention further relates to a mixture comprising at least one compound of the formula (1) as described above or preferably described later and at least one further compound selected from the group of matrix materials, phosphorescent emitters, fluorescent emitters 35 and / or emitters exhibiting TADF (thermally activated delayed fluorescence). The invention further relates to the use of a compound of the formula (1) in an organic electronic device. P24072 Sc - 5 - The invention further relates to an organic electronic, preferably electroluminescent or light-emitting, device comprising an anode, a cathode and at least one organic layer comprising at least one compound of the formula (1),as described above or preferably described later. 5 The invention further provides a process for producing an organic electronic, preferably electroluminescent or light-emitting, device, as described above or preferably described below, characterized in that the organic layer is applied by vapor deposition or from solution. Description of the invention In the present patent application, "D" or "D atom" refers to deuterium. The degree of deuteration, expressed in mol%, indicates the proportion of H atoms replaced by deuterium. Since deuterated compounds are often a mixture of compounds that differ in the exact position and proportion of the D atoms, the degree of deuteration indicates the average proportion of H atoms.which are replaced by D. With an average degree of deuteration of 50 mol%, on average 50 mol% of the H atoms in the compound are replaced by D. 20 An aryl group within the meaning of this invention contains 6 to 40 ring atoms or preferably 6 to 30 ring atoms or preferably 6 to 18 ring atoms, where the ring atoms are C atoms. A heteroaryl group within the meaning of this invention contains 5 to 40 ring atoms, where the ring atoms comprise C atoms and at least one heteroatom, with the proviso that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aryl group is understood to mean a simple aromatic cycle, for example phenyl, derived from benzene, or a condensed aryl group, for example derived from naphthalene, anthracene, phenanthrene, triphenylene, but 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, phenanthryl, or triphenylenyl, whereby the attachment of the aryl group as substituent 35 is not restricted. The aryl group within the meaning of this invention can bear one or more radicals, with the suitable radical being described below. The radical is preferably deuterium. If no such radical is described, the aryl group or heteroaryl group is unsubstituted. P24072 Sc - 6 - A heteroaryl group is defined as either a simple heteroaromatic cycle, for example derived from pyridine, pyrimidine or thiophene, or a condensed heteroaryl group, for example derived from quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran,Dibenzothiophene or carbazole is understood, 5 but the term heteroaryl group in the sense of the invention also includes a heteroaryl group which is bonded by a single bond to an aryl group or another heteroaryl group, for example phenyl-bipyridyl or bipyridyl. The heteroaryl group in the sense of this invention can carry one or more radicals, the suitable radical being described below. Preferably, the radical 10 is deuterium. If no such radical is described, the heteroaryl group is unsubstituted. An aromatic ring system in the sense of this invention contains 6 to 40 C atoms in the ring system. The aromatic ring system comprises aryl groups, as described above 15 and the term is used synonymously below. An aromatic ring system with 6 to 18 C atoms is preferably selected from phenyl, biphenyl, naphthyl, phenanthryl and triphenylenyl, which can carry one or more radicals,where the suitable radical is described below. Preferably, the radical is deuterium. If no such radical is described, the aromatic 20 ring system is unsubstituted. A heteroaromatic ring system within the meaning of this invention contains 5 to 40 ring atoms and at least one heteroatom. A preferred heteroaromatic ring system has 9 to 40 ring atoms and at least one heteroatom. The heteroaromatic ring system 25 comprises heteroaryl groups, as described above, and the term is used synonymously below. An aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which can be linked via any positions to the aromatic or heteroaromatic 30 and which can carry one or more radicals, as described below, is preferably understood to mean the following groups, which are derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, triphenylene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene,Benzfluoranthen, Naphthacen, Pentacen, Benzpyren, Biphenyl, Terphenyl, Quaterphenyl, Fluoren, 9,9-Dimehtylfluoren, 35 9,9-Diphenylfluoren, Spirobifluoren, Dihydrophenanthren, Dihydropyren, Tetrahydropyren, cis- oder trans-Indenofluoren, cis- oder trans-Monobenzoindenofluoren, cis- oder trans- Dibenzoindenofluoren, Truxen, Isotruxen, Spirotruxen, Spiroisotruxen, Furan, Benzofuran, Isobenzofuran, Dibenzofuran, Thiophen, Benzothiophen, Isobenzothiophen, Dibenzo- thiophen, Pyrrol, Indol, Isoindol, Carbazol, Indolocarbazol, Indenocarbazol, Pyridin, P24072 Sc - 7 - Chinolin, Isochinolin, Acridin, Phenanthridin, Benzo-5,6-chinolin, Benzo-6,7-chinolin, Benzo-7,8-chinolin, Phenothiazin, Phenoxazin, Pyrazol, Indazol, Imidazol, Benzimidazol, Naphthimidazol, Phenanthrimidazol, Pyridimidazol, Pyrazinimidazol, Chinoxalinimidazol, Oxazol, Benzoxazol, Naphthoxazol, Anthroxazol, Phenanthroxazol, Isoxazol, 1,2-Thiazol, 5 1,3-Thiazol, Benzothiazol, Pyridazin, Benzopyridazin, Pyrimidin, Benzpyrimidin,Quinoxaline, 1,5-diazaanthracene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorubin, Naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 10 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine, benzothiadiazole, phenylpyridine, and bipyridine. 15 The abbreviation Ar3 stands, independently at each occurrence, for an aryl or heteroaryl group having 5 to 40 ring atoms which can be substituted by one or more radicals R, 0 may be substituted, where the radical R 0has a meaning as described above or below. 20 The abbreviation "aryl" is at each occurrence, independently of one another, identically or differently, an unsubstituted, partially or fully deuterated aryl group having 6 to 40 C atoms. The abbreviation "aryl" is preferably phenyl, 1,2-biphenyl, 1,3-biphenyl or 1,4-biphenyl, which may be partially or fully deuterated. 25 The abbreviation Ar5 is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which is substituted by one or more radicals R 7 can be substituted or is synonymous with an aryl group with 6 to 40 C atoms or a heteroaryl group with 5 to 40 ring atoms, which can be substituted with one or more radicals R 7 may be substituted, where R 7 or the substituents R 7has / have a 30 meaning as described above or below. A preferred meaning of Ar1, Ar2, Ar3, "aryl" and Ar5 is described below. An electron-rich heteroaromatic compound is a heterocyclic aromatic compound with 35 a ^-excess, ie a free electron pair of the heteroatom forms the cyclically delocalized electrons with the p-electrons of the carbon atoms. This definition also applies accordingly to an electron-rich heteroaromatic ring system. P24072 Sc - 8 - A cyclic alkyl, alkoxy or thioalkyl group in the sense of this invention is understood to mean a monocyclic, bicyclic or polycyclic group. In the context of the present invention, a straight-chain, branched or cyclic C1 to C20 alkyl group is understood to mean, for example, the radicals methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl,neo-Pentyl, Cyclopentyl, n-Hexyl, s-Hexyl, t-Hexyl, 2-Hexyl, 3- Hexyl, neo-Hexyl, Cyclohexyl, 1-Methylcyclopentyl, 2-Methylpentyl, n-Heptyl, 2-Heptyl, 3- Heptyl, 4-Heptyl, Cycloheptyl, 1-Methylcyclohexyl, n-Octyl, 2-Ethylhexyl, Cyclooctyl, 1- 10 Bicyclo[2,2,2]octyl, 2-Bicyclo[2,2,2]octyl, 2-(2,6-Dimethyl)octyl, 3-(3,7-Dimethyl)octyl, Adamantyl, Trifluormethyl, Pentafluorethyl, 2,2,2-Trifluorethyl, 1,1-Dimethyl-n-hex-1-yl-, 1,1-Dimethyl-n-hept-1-yl-, 1,1-Dimethyl-n-oct-1-yl-, 1,1-Dimethyl-n-dec-1-yl-, 1,1-Dimethyl- n-dodec-1-yl-, 1,1-Dimethyl-n-tetradec-1-yl-, 1,1-Dimethyl-n-hexadec-1-yl-, 1,1-Dimethyl- n-octadec-1-yl-, 1,1-Diethyl-n-hex-1-yl-, 1,1-Diethyl-n-hept-1-yl-, 1,1-Diethyl-n-oct-1-yl-, 15 1,1-Diethyl-n-dec-1-yl-, 1,1-Diethyl-n-dodec-1-yl-, 1,1-Diethyl-n-tetradec-1-yl-, 1,1- Diethyln-n-hexadec-1-yl-, 1,1-Diethyl-n-octadec-1-yl-, 1-(n-Propyl)-cyclohex-1-yl-, 1-(n- Butyl)-cyclohex-1-yl-, 1-(n-Hexyl)-cyclohex-1-yl-,1-(n-octyl)-cyclohex-1-yl- and 1-(n-decyl)-cyclohex-1-yl- are understood. 20 An alkenyl group is understood to mean, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl. An alkynyl group is understood to mean, for example, ethynyl, propynyl, butynyl, pentynyl, 25 hexynyl, heptynyl or octynyl. A C1- to C20-alkoxy group is understood to mean, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy. 30 A C1- to C20-thioalkyl group is understood to mean, for example, S-alkyl groups, for example thiomethyl, 1-thioethyl, 1-thio-i-propyl, 1-thio-n-propoyl, 1-thio-i-butyl, 1-thio-n-butyl or 1-thio-t-butyl. 35 An aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms means O-aryl or O-heteroaryl and means,that the aryl or heteroaryl group is bonded via an oxygen atom. P24072 Sc - 9 - An aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms means that an alkyl group, as described above, is substituted with an aryl group or heteroaryl group. 5 The compounds of formula (1) and their preferred embodiments are described below. The preferred embodiments also apply to the mixture according to the invention and the organic electronic device according to the invention, the organic electroluminescent or light-emitting device. 10 Preferred embodiments of the compounds of formula (1) are compounds of 15 20 25, where A, C, R a , R b and R c have a meaning mentioned above or mentioned with preference below. 30 Particularly preferred embodiments of the compounds of formula (1) are compounds of formulas (1a) and (1b), where A, C, R a , Rb and R c have a meaning mentioned above or mentioned with preference below. 35 Very particularly preferred embodiments of the compounds of formula (1) are compounds of formula (1a), where A, C, R a , R b and R c have a meaning previously mentioned or preferred below. P24072 Sc - 10 - Preferred embodiments of A according to formula (3) are described in formulas (3-1) to (3-12), 5 10 15 20 25 30 , where V, R 1 , R#, m and R d have a meaning mentioned above or mentioned below with preference. 35 In embodiments of A according to the formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6), (3-7), (3-8), (3-9), (3-10), (3-11) and (3-12), R 1at each occurrence, independently of one another, is preferably selected from the group D, CN, F or an aryl or heteroaryl group P24072 Sc - 11 - having 5 to 40 ring atoms, where the aryl or heteroaryl group may be substituted by one or more D. R 1 is in embodiments of A according to the formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6), (3-7), (3-8), (3-9), (3-10), (3-11) and (3-12) at each occurrence independently of one another preferably selected from the group D, CN, phenyl, biphenyl, terphenyl, quaterphenyl, triphenylenyl, dibenzofuranyl or dibenzothiophenyl, where the aryl or heteroaryl groups mentioned may be substituted by one D or more D. R is particularly preferably 1for phenyl, biphenyl, terphenyl, quaterphenyl, dibenzofuranyl or dibenzothiophenyl, where the aryl or heteroaryl groups mentioned may be substituted by one or more D. In embodiments of A according to the formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6), (3-7), (3-8), (3-9), (3-10), (3-11) and (3-12), m is preferably 0 or 1. 15 In embodiments of A according to the formulas (3), (3-1), (3-2), (3-5), (3-6), (3-7) and (3-8), m is particularly preferably 1. In compounds of the formulas (1), (1a), (1b) and (1c) or preferred compounds of the formulas (1), (1a), (1b) and (1c), it is preferred if A represents the formula 20 (3), where two Y represent N, the remaining Y represent CH or CR 1 stand and V, R d , R# and R 1have a meaning mentioned above or below or previously preferred. In compounds of the formulas (1), (1a), (1b) and (1c) or preferred compounds of the formulas (1), (1a), (1b) and (1c), it is preferred if A represents one of the formulas (3-1), (3-2), (3-3) or (3-4), where V, R d , R# and R 1 have a meaning mentioned above or below or previously preferred. In compounds of the formulas (1), (1a), (1b) and (1c) or preferred compounds of the formulas (1), (1a), (1b) and (1c), it is particularly preferred if A represents one of the formulas (3-1) or (3-2), where V, R d , R# and R 1have a meaning previously mentioned or subsequently or previously preferred. In embodiments of A according to the formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6), (3-7), (3-8), (3-9), (3-10), (3-11) and (3-12), V is preferably O. In the compounds of the formulas (1), (1a), (1b) and (1c), where A corresponds to one of the formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6), (3-7), (3-8), (3-9), (3-10), (3-11) or (3-12), R#, when occurring, is preferably selected independently from the group Ar-1 to Ar-42, 5 10 15 20 25 30 35 P24072 Sc - 14 - P24072 Sc - 15 - 5 , Y 2 O, S or Se means 10 Y 3 O, S, NAr4 or C(R*)2, R 3 H or R 0means, the dashed bond represents the bond to the rest of the formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6), (3-7), (3-8), (3-9), (3-10), (3-11) and (3-12), Ar4 represents an aryl group having 6 to 30 ring atoms or a heteroaryl group having 5 to 40 ring atoms, which is reacted with one or more radicals R 0 may be substituted, R* at each occurrence, identically or differently, represents a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, each of which is substituted by one or more radicals R 0 may be substituted, where one or more H atoms may be replaced by D, F or CN or an aryl group with 20 6 to 30 ring atoms or a heteroaryl group with 5 to 40 ring atoms, which with one or more radicals R 0 may be substituted, and where R 0 has a meaning mentioned above or a meaning preferred below. 25 The substituent R0 Ar4 in N-Ar4 is preferably D, F or CN, particularly preferably D. In the formulas Ar-15 to Ar-18 and Ar-23 to Ar-26, Ar4, when occurring in N-Ar4, is Y 3 particularly preferably selected from non-deuterated, partially deuterated or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl. 30 The symbol Y 3 in the formulas Ar-15 to Ar-18 and Ar-23 to Ar-26, N is preferably Ar4, C(CH3)2, O or S, particularly preferably O or S, very particularly preferably O. R 0 in R* is preferably D, F or CN, particularly preferably D. 35 Y 2 in the formulas Ar-31 to Ar-35 is preferably S or O, particularly preferably O. In R# the substituent R 0preferably selected, identically or differently at each occurrence, from the group consisting of D, F, CN or a non-deuterated, partially deuterated or fully deuterated aryl group having 6 to 30 ring atoms or a non-deuterated, partially deuterated or fully deuterated electron-rich heteroaryl group having 9 to 40 ring atoms. In R#, the substituent R 0 particularly preferably selected, identically or differently at each occurrence, from group 5 consisting of D, non-deuterated or partially or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl. In R#, the substituent R 0 most preferably D. In the structures Ar-1 to Ar-42 the substituent R 3preferably at each occurrence 10 are selected, identically or differently, from the group consisting of H, D, F, CN or a non-deuterated, partially deuterated or fully deuterated aryl group having 6 to 30 ring atoms or a non-deuterated, partially deuterated or fully deuterated electron-rich heteroaryl group having 9 to 40 ring atoms. In the structures Ar-1 to Ar-42, the substituent R 3 particularly preferably at each occurrence 15 is selected, identically or differently, from the group consisting of H, D, non-deuterated or partially or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl. In the structures Ar-1 to Ar-42, the substituent R 3very particularly preferably on each occurrence, identically or differently selected from the group consisting of H or D. 20 R# in compounds of the formulas (1), (1a), (1b) and (1c), where A corresponds to one of the formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6), (3-7), (3-8), (3-9), (3-10), (3-11) or (3-12) is particularly preferably selected from the group Ar-1 to Ar-18 and Ar-23 to Ar-30, where R 3 has a meaning previously given or preferably given. In one embodiment, R# is preferably phenyl, 1,4-biphenyl, 1,3-biphenyl, 1,2-biphenyl or dibenzofuranyl, which are partially deuterated or fully deuterated. R# in compounds of the formulas (1), (1a), (1b) and (1c), where C corresponds to one of the formulas (4), (5) or (6), is particularly preferably selected from the group Ar-1 to Ar-18 and Ar-23 to Ar-30, where R 3has a meaning given above or with preference. In one embodiment, R# is preferably phenyl, 1,4-biphenyl, 1,3-biphenyl, 1,2-biphenyl or dibenzofuranyl, which are partially deuterated or fully deuterated. 35 In compounds of the formulas (1), (1a), (1b) and (1c), C is preferably selected from the formula (4) or (5). In compounds of the formulas (1), (1a), (1b) and (1c), where A has a meaning given above or with preference and C corresponds to the formula (4), m is 0, 1 or 2, preferably 1 or 2, particularly preferably 1 and R# has a meaning given above or with preference. In compounds of formulas (1), (1a), (1b) and (1c), where A has a meaning given above or preferably given above and C corresponds to formula (5), m is 0, 1 or 2, preferably 0 or 1, particularly preferably 1, and R# has a meaning given above or preferably given above.Ar3 in formula (5) is preferably selected from the group Ar-1 to Ar-42, as described above. Ar3 in compounds of formulas (1), (1a), (1b) and (1c), where A has a previously mentioned or preferred meaning and C corresponds to formula (5), is very particularly preferably selected from the group Ar-1 to Ar-10, Ar-15 to Ar-18 and Ar-23 to Ar-28, where R. 3has a meaning given above or with preference. In one embodiment, Ar3 is preferably phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl, which are partially deuterated or fully deuterated. 15 In compounds of the formulas (1), (1a), (1b) and (1c), where A has a meaning given above or with preference and C corresponds to the formula (6), m is 0, 1 or 2, preferably 0 or 1, particularly preferably 0, and R# has a meaning given above or with preference. 20 Particularly preferred embodiments of the compounds of the formulas (1), (1a), (1b) and (1c) are compounds in which A corresponds to the formula (3-1) and C corresponds to one of the formulas (4), (5) or (6), where Ar3, R# and m have a meaning given above or with preference.25 Particularly preferred embodiments of the compounds of the formulas (1), (1a), (1b) and (1c) are compounds in which A corresponds to the formula (3-2) and C corresponds to one of the formulas (4), (5) or (6), where Ar3, R# and m have a meaning given above or given with preference. 30 Particularly preferred embodiments of the compounds of the formulas (1), (1a), (1b) and (1c) are compounds in which A corresponds to the formula (3-3) and C corresponds to one of the formulas (4), (5) or (6), where Ar3, R# and m have a meaning given above or given with preference. 35 Particularly preferred embodiments of the compounds of the formulas (1), (1a), (1b) and (1c) are compounds in which A corresponds to the formula (3-4) and C corresponds to one of the formulas (4), (5) or (6), where Ar3, R# and m have a meaning given above or given with preference.P24072 Sc - 18 - Particularly preferred embodiments of the compounds of the formulas (1), (1a), (1b) and (1c) are compounds in which A corresponds to the formula (3-1) and C corresponds to the formula (4), where Ar3, R# and m have a meaning given above or with preference. 5 Particularly preferred embodiments of the compounds of the formulas (1), (1a), (1b) and (1c) are compounds in which A corresponds to the formula (3-2) and C corresponds to the formula (4), where Ar3, R# and m have a meaning given above or with preference. 10 Particularly preferred embodiments of the compounds of the formulas (1), (1a), (1b) and (1c) are compounds in which A corresponds to the formula (3-3) and C corresponds to the formula (4), where Ar3, R# and m have a meaning given above or with preference.15 Particularly preferred embodiments of the compounds of the formulas (1), (1a), (1b) and (1c) are compounds in which A corresponds to the formula (3-4) and C corresponds to the formula (4), where Ar3, R# and m have a meaning given above or preferably. 20 In compounds of the formulas (1), (1a), (1b) and (1c), where A corresponds to one of the formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6), (3-7), (3-8), (3-9), (3-10), (3-11) or (3-12) and C corresponds to one of the formulas (4), (5) or (6), R a , R b , R c and R d a monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution or no substitution and R a , R b , R c and R dare 25 D at each occurrence. Compounds of the formulas (1), (1a), (1b) and (1c), where A corresponds to one of the formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6), (3-7), (3-8), (3-9), (3-10), (3-11) or (3-12) and C corresponds to one of the formulas (4), (5) or (6) are preferably partially or completely deuterated, ie at least one R a , R b , R c or R d corresponds to a monosubstitution with D .A further subject matter accordingly relates to compounds of the formulas (1), (1a), (1b) and (1c), as described above or preferably described, which are partially or fully deuterated. 35 If the compounds of the formulas (1), (1a), (1b) and (1c) are deuterated compounds, it is possible during their preparation, provided that the preparation is chosen by reacting a non-deuterated compound of one of the formulas (1), (1a), (1b) and (1c) with a deuteration source or provided that deuterated starting compounds are chosen during the preparation P24072 Sc - 19 - which are a mixture of deuterated starting compounds, that a mixture of deuterated products of the same basic chemical structure is formed which differ only in the degree of deuteration and / or the deuteration patterns.5 Such mixtures of deuterated compounds having the same basic chemical structure of formula (1) or the basic structure of the preferred embodiments, which differ only in the degree of deuteration and / or the deuteration patterns, are understood by the term "at least one compound of formula (1)" within the meaning of the invention. In a preferred embodiment of the at least one compound of formulas (1), (1a), (1b) and (1c), as described above or preferably described, the average degree of deuteration is at least 10 mol% to 100 mol%, preferably 15 mol% to 50 mol% to 95 mol%, particularly preferably 70 mol% to 90 mol%. Corresponding deuteration methods are known to the person skilled in the art and are described, for example, in KR2016041014, WO2017 / 122988, KR202005282, KR101978651 and WO2018 / 110887 or in Bulletin of the Chemical Society of Japan, 2021, 94(2), 600-605 or Asian 20 Journal of Organic Chemistry, 2017, 6(8), 1063-1071.A suitable method for deuterating a compound by exchanging one or more H atoms for D atoms is treatment of 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 containing one or more D atoms and capable of releasing them under suitable conditions. The platinum catalyst is preferably dry platinum on carbon, preferably 5% dry platinum on carbon. The palladium catalyst is preferably dry palladium on carbon, preferably 5% dry palladium on carbon. A suitable deuterium source is D2O, benzene-d6, chloroform-d3, acetonitrile-d3, acetone-d6, acetic acid-d4, methanol-d4, or toluene-d8. A preferred deuterium source is D2O or a combination of D2O and a fully deuterated organic solvent.A particularly preferred deuterium source is the combination of D2O with a fully deuterated organic solvent, whereby the fully deuterated solvent 35 is not limited here. Particularly suitable fully deuterated solvents are benzene-d6 and toluene-d8. A particularly preferred deuterium source is a combination of D2O and toluene-d8. The reaction is preferably carried out with heating, more preferably with heating to temperatures between 100°C and 200°C. Furthermore, the reaction is preferably carried out under pressure. P24072 Sc - 20 - Examples of suitable host materials of formulas (1), (1a), (1b), and (1c) are the structures listed below in Table 1.

[0002]

[0003]

[0004] P24072 Sc - 28 - 5 10 15 20 25 Particularly suitable compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) are the compounds E1 to E30 of Table 2. 30 Table 2: 35 P24072 Sc - 29 - 5 10 15 20 25 30 35 P24072 Sc - 30 - 5 10 15 20 25 30 35 P24072 Sc - 31 - 5 10 For the sake of simplicity, the compounds in Tables 1 and 2 are partially shown as fully deuterated compounds, which generally means compounds that have a degree of deuteration of at least 50 mol%. The degree of deuteration for the fully deuterated compounds in Tables 1 and 2 is therefore between 50 and 100 mol% or has a preferred degree of deuteration, as described above. In partially deuterated compounds, a D atom means 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 the person skilled in the art, such as bromination, Suzuki coupling, Ullmann coupling, Hartwig-Buchwald coupling, etc. 25 30 35 P24072 Sc - 32 - By these processes, optionally followed by purification, such as recrystallization or sublimation, the compounds of formula (1) can be obtained in high purity, preferably more than 99% (determined by 1H-NMR and / or HPLC). 5 For processing the compounds of the invention from the liquid phase, for example by spin coating or by printing processes, formulations of the compounds of the invention or mixtures of compounds of the invention with other functional materials, such as matrix materials, fluorescent emitters, phosphorescent emitters, and / or emitters exhibiting TADF 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 are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-15 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-Methylnaphthalene, 1-Ethylnaphthalene, ethyl octanoate, diethyl sebacate, 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 can be an above-mentioned solvent or a mixture of these solvents. The compounds according to the invention of the formulas (1), (1a), (1b) or (1c), as described above or preferably described, are suitable for use in an organic electroluminescent device, in particular as matrix material. P24072 Sc - 33 - If the compound according to the invention is used as matrix material or synonymously host material in an emitting layer, it is preferably used in combination with another compound. 5 The invention therefore further provides a mixture comprising at least one compound of the formula (1) or at least one preferred compound of one of the formulas (1), (1a), (1b) or (1c) or a compound of Table 1 or one of the compounds E1 to E30 and at least one other compound,selected from the group of matrix materials, phosphorescent emitters, fluorescent emitters, and / or emitters exhibiting TADF (thermally activated delayed fluorescence). Suitable matrix materials and emitters that can be used in this mixture according to the invention are described below. The present invention further provides 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 the formulas (1), (1a), (1b), or (1c), or a compound of Table 1 or one of the compounds E1 to E30. The organic electronic device can, for example, consist of organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices,organic solar cells (OSCs), organic optical detectors, organic photoreceptors. 25 Preferably, the organic electronic device is an organic electroluminescent device. The organic electroluminescent device according to the invention (synonymous with 30 organic electroluminescent device) is, for example, an organic light-emitting transistor (OLET), an organic field quench device (OFQD), an organic light-emitting electrochemical cell (OLEC),an organic laser diode (O-laser) or an organic light-emitting diode (OLED). The organic electroluminescent device according to the invention is in particular an organic light-emitting diode or an organic light-emitting electrochemical cell. The device according to the invention is particularly preferably an OLED. The organic layer of the device according to the invention preferably contains, in addition to a light-emitting layer (EML), a hole injection layer (HIL), a hole transport layer (HTL), a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), an exciton blocking layer, an electron blocking layer, and / or charge generation layers. The device according to the invention can also contain several layers from this group, preferably selected from EML, HIL, HTL, ETL, EIL, and HBL.Interlayers can also be introduced between two emitting layers, which, for example, have an exciton-blocking function. If multiple emitting layers are present, they preferably have a total of 10 multiple emission maxima between 380 nm and 750 nm, resulting in overall white emission, i.e., different emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. One emitting layer can also contain several fluorescent and / or phosphorescent compounds. Systems 15 with three emitting layers are particularly preferred, wherein the three layers exhibit blue, green, and orange or red emission. As an alternative to the combination as described above,An emitting layer can also exhibit yellow emission. Such combinations are known to the person skilled in the art. The organic electroluminescent device according to the invention can also be a tandem electroluminescent device 20, in particular for white-emitting OLEDs. The device can also contain inorganic materials or layers composed entirely of inorganic materials. A large number of materials known in the prior art are suitable for use in the previously described layers of the organic electroluminescent device. 25 When selecting, common considerations regarding the chemical and physical properties of the materials must be taken into account, since the materials in an organic electroluminescent device are interrelated. This concerns, for example, the energy positions of the orbitals (HOMO, LUMO) or the position of triplet and singlet energies.but also other 30 material properties. The compound of formula (1) according to the invention, as described above or preferably described, can be used in different layers, depending on the precise structure. An organic electroluminescent device containing a compound according to formula (1) or the preferred embodiments described above in an emitting layer as a matrix material for fluorescent emitters, phosphorescent emitters, or for emitters exhibiting TADF (thermally activated delayed fluorescence) is preferred.in particular for phosphorescent emitters. Furthermore, the compound according to the invention can also be used in an electron transport layer P24072 Sc - 35 - and / or an electron injection layer and / or in a hole blocking layer. The compound according to the invention is particularly preferably used as a matrix material in an emitting layer or as an electron transport or electron injection or hole blocking material in an electron transport, electron injection or hole blocking layer. The present invention further provides an organic electronic device as described above, wherein the organic layer contains at least one light-emitting layer which comprises at least one compound of the formula (1) or at least one preferred compound of one of the formulas (1), (1a),(1b) or (1c) or a compound of Table 1 or one of the compounds E1 to E30. In one embodiment of the invention, at least one further matrix material is selected for the device according to the invention in the light-emitting layer, which is used with 15 compounds of the formula (1), as described above or preferably described, or with the compounds of Table 1 or the compounds E1 to E30. The present invention accordingly further provides an organic electronic device as described above, wherein the organic layer 20 contains at least one light-emitting layer which contains at least one compound of the formula (1) or the at least one preferred compound of one of the formulas (1), (1a),(1b) or (1c) or a compound of Table 1 or one of the compounds E1 to E30 and at least one further matrix material. 25 The present invention accordingly further provides an organic electronic device as described above, wherein the organic layer contains at least one light-emitting layer which contains at least one compound of formula (1) or the at least one preferred compound of one of the formulas (1), (1a), (1b) or (1c) or a compound of Table 1 or one of the compounds E1 to E30 30 and two further matrix materials. Suitable matrix materials which can be used in combination with the compounds according to the invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, triarylamines, carbazole derivatives, 35 biscarbazoles, indolocarbazole derivatives, indenocarbazole derivatives, azacarbazole derivatives, bipolar matrix materials, azaboroles or boronic esters.Triazine derivatives, zinc complexes, diazasilole or tetraazasilole derivatives, diazaphosphole derivatives, bridged carbazole derivatives, triphenylene derivatives, or dibenzofuran derivatives. Likewise, another phosphorescent emitter, which emits at a shorter wavelength than the actual emitter, can be present in the mixture as a co-P24072 Sc - 36 - host, or a compound that does not participate, or does not participate significantly, in charge transport, such as a wide-band-gap compound. 5 A wide-band-gap material is understood herein to mean a material within the meaning of the disclosure of US Pat. No. 7,294,849, which is characterized by a band gap of at least 3.5 eV, where the band gap is understood to be the difference between the HOMO and LUMO energy of a material. 10 Particularly suitable hole-transporting matrix materials which advantageously react with compounds of the formulas (1), (1a), (1b) or (1c), as described above or preferably described,in a mixed matrix system can be selected from the compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6), as described below. 15 A further subject of the invention is therefore an organic electronic device comprising an anode, a cathode and at least one organic layer containing at least one light-emitting layer, wherein the at least one light-emitting layer contains at least one compound of the formula (1) as matrix material 1, 20 as described above or as preferred, and at least one compound of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6) as matrix material 2, 25 30 35, ormel (HH-2), P24072 Sc - 37 - 5 10 15 20 25 - , where the symbols and indices used are: 30 A 1 is C(R 7 )2, NR 7 , O or S; L is a bond, O, S, C(R 7 )2 or NR 7; A is at each occurrence independently a group of the formula (HH-4-1) or (HH-4-2), 35 P24072 Sc - 38 - 5 10 X2is the same or different at each occurrence CH, CR 6 or N, where a maximum of 2 symbols can represent X2N; * indicates the binding site to the formula (HH-4); U 1 , U 2 are a bond, O, S, C(R 7 )2 or NR 7 ; R 6 is at each occurrence, identically or differently, D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 7 may be substituted and wherein one or more non-adjacent CH2 groups are substituted by Si(R 7 )2, C=O, NR 7 , O, S or CONR 7may be replaced by 20, or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, each of which is substituted by one or more radicals R 7 can be substituted; two radicals R 6 also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar5, identical or different at each occurrence, independently represents an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which with one or more radicals R 7 may be substituted; R 7 is the same or different at each occurrence D, F, Cl, Br, I, N(R 8 )2, CN, NO2, OR 8 , SR 8 , Si(R 8 )3, B(OR 8 )2, C(=O)R 8 , P(=O)(R 8 )2, S(=O)R 8 , S(=O)2R 8 , OSO2R 8, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 8 may be substituted, with one or more non-adjacent CH2 groups being substituted by Si(R 8 )2, C=O, NR 8 , O, S or CONR 8 or an aromatic or hetero- 35 aromatic ring system with 5 to 40 ring atoms, each of which is substituted by one or more radicals R 8 may be substituted, where R 8 does not denote H; two or more radicals R 7 together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system, preferably the radicals R 7 no such ring system; P24072 Sc - 39 - R 8is, on each occurrence, the same or different, H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, in particular a hydrocarbon radical, having 1 to 20 C atoms, in which one or more H atoms may also be replaced by D or F; 5 c, c1, c2 each independently denote 0 or 1 on each occurrence, where the sum of the indices c+c1+c2 = 1 on each occurrence; d, d1, d2 each independently denote 0 or 1 on each occurrence, where the sum of the indices d+d1+d2 = 1 on each occurrence; q, q1, q2 each independently denote 0, 1, 2, 3 or 4 on each occurrence; 10 s is, on each occurrence, the same or different, 0, 1, 2, 3 or 4; t is, on each occurrence, the same or different, 0, 1, 2, or 3; u is, at each occurrence, the same or different: 0, 1, or 2; u1, u2 each independently mean 0 or 1 at each occurrence, where the sum u1 + u2 = 1; and v is 0, 1, 2, or 3.Preferred compounds of formula (HH-5) are compounds of formulas (HH-5-A) to (HH-5-E), 20 25 30. , 35 P24072 Sc - 40 - 5 10 15 20 , where Ar5, R 6 , s and u have a meaning given above or given preferably. In compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6), s is preferably 0 or 1 if the radical R 6 is different from D, or particularly preferably 0. In compounds of the formulas (HH-1), (HH-2) or (HH-3), t is preferably 0 or 1 if the radical R 6 is different from D, or particularly preferably 0. In compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D) or (HH-5-E), u is preferably 0 or 1 when the radical R 6is different from D, or particularly preferably 0. The sum of the indices s, t and u in compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6) is preferably at most 6, particularly preferably at most 4 and particularly preferably at most 2. This preferably applies when R 6 is different from D. In compounds of the formula (HH-4), c, c1, c2 each independently of one another at each occurrence is 0 or 1, where the sum of the indices at each occurrence c+c1+c2 is 1. Preferably, c2 is 1. P24072 Sc - 41 - In compounds of the formula (HH-4), L is preferably a single bond or C(R 7 )2, where R 7 has a meaning mentioned above, particularly preferably L is a single bond. In formula (HH-4-1), v is preferably 0 or 1 when the radical R 6 is different from D. 5 In formula (HH-4-2) U 1 or U 2when occurring, preferably a single bond or C(R 7 )2, where R 7 has a meaning mentioned above, particularly preferred are U 1 or U 2 a single bond when occurring. In formula (HH-4-2), q, q1, q2 are preferably 0 or 1 when the radical R 6 is different from D. 10 In a preferred embodiment of the compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6), which can be combined according to the invention with compounds of formula (1) or preferred compounds of formula (1), as described above, R 6 identically or differently on each occurrence selected from the group consisting of D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl group is in each case substituted with one or more radicals R 7may be substituted, or an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, preferably having 5 to 40 ring atoms, 20 each substituted by one or more radicals R 7 may be substituted. In a preferred embodiment of the compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6), which can be combined according to the invention with compounds of formula (1) or preferred compounds of formula (1), as described above, R 6 identically or differently on each occurrence selected from the group consisting of D or an aromatic or heteroaromatic ring system having 6 to 30 ring atoms, which is reacted with one or more radicals R 7can be substituted. 30 Preferably, Ar5 in compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6) is selected from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorenyl, which may be linked via the 1-, 2-, 3- or 4-position, 9,9-dimethylfluorenyl, which may be linked via the 1-, 2-, 3- or 4-position, spirobifluorenyl, which may be linked via the 1-, 2-, 3- or 4-position, naphthyl, in particular 1- or 2-linked naphthyl, or residues derived from indole, benzofuran, benzothiophene, carbazole, which can be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, which can be linked via the 1-, 2-, 3- or 4- P24072 Sc - 42 - position, dibenzothiophene, which can be linked via the 1-, 2-,3- or 4-position, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene, each of which is linked to one or more radicals R, 7 may be substituted. 5 Preferably, Ar5 is deuterated, but not further substituted. If A 1 in formula (HH-2) or (HH-3) or (HH-6) for NR 7 the substituent R 7 which is bonded to the nitrogen atom, preferably represents an aromatic or heteroaromatic ring system having 5 to 24 ring atoms, which can also be substituted by one or more radicals R 8 In a particularly preferred embodiment, this substituent R 7 identically or differently on each occurrence represents an aromatic or heteroaromatic ring system having 6 to 24 ring atoms, in particular having 6 to 18 ring atoms. Preferred embodiments for R7 are phenyl, biphenyl, terphenyl and quaterphenyl, which are preferably deuterated, as well as residues 15 derived from triazine, pyrimidine and quinazoline, which are substituted by one or more residues R 8 may be substituted, where R 8 does not mean H. If A 1 in formula (HH-2) or (HH-3) or (HH-6) for C(R 7 )2, the substituents R 7 which are bonded to this carbon atom, preferably identically or differently on each occurrence, represent a linear alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms or an aromatic or heteroaromatic ring system having 5 to 24 ring atoms, which can also be substituted by one or more radicals R 8 may be substituted, where R 8 does not represent H. Most preferably, R 7 represents a methyl group or a 25 phenyl group. The radicals R 7also form a ring system with each other, resulting in a spiro system. In a preferred embodiment of the compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) and (HH-6), these compounds are partially or fully deuterated, particularly preferably fully deuterated. The preparation of the compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) and (HH-6) is generally known, and some of the compounds are commercially available. Compounds of formula (HH-4) are disclosed, for example, in WO2021 / 180614, pages 110 to 119, in particular as examples on pages 120 to 127. Their preparation P24072 Sc - 43 - is disclosed in WO2021 / 180614 A1 on page 128 and in the synthesis examples on pages 214 to 218. The preparation of the triarylamines of formula (HH-6) is known to the person skilled in the art, and some of the compounds are commercially available.If the at least one further matrix material is a deuterated compound, it is possible for this at least one matrix material to be a mixture of deuterated compounds of the same basic chemical structure, which differ only in the degree of deuteration and / or the deuteration pattern. The statements regarding deuterated mixtures and the preparation of deuterated materials, as described above for compounds of formula (1), apply here accordingly. In a preferred embodiment of the at least one further matrix material, this is a mixture of deuterated compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6), as described above, wherein the average degree of deuteration of these compounds is at least 50 mol% to 90 mol%, preferably 70 mol% to 100 mol%.20 Examples of suitable further matrix materials for a combination with compounds of formula (1), as described above or preferably described, are the compounds described in WO2019 / 229011 A1, Table 3, pages 137 to 203, which may also be partially or fully deuterated. 25 Examples of suitable further matrix materials for a combination with compounds of formula (1) or preferred compounds of formula (1), as described above or preferably described, are the compounds described in WO2021 / 180625 A1, Table 3, pages 131 to 137 and in Table 4, pages 137 to 139, which may also be partially or fully deuterated.30 Examples of suitable further matrix materials for combination with compounds of formula (1) or preferred compounds of formula (1) as previously described or preferably described are the compounds described in KR20230034896 A, on pages 42 to 47, compounds [2-1] to [2-110], or on pages 49 to 51, 35 compounds [3-1] to [3-26]. Examples of suitable further matrix materials for combination with compounds of formula (1) or preferred compounds of formula (1) as previously described or preferably described are the compounds described in KR20230154750 A, P24072 Sc - 44 - on pages 39 to 49, compounds [B-1] to [B-243], or on pages 49 to 53, compounds [C-1] to [C-102] or on pages 54 to 57, compounds [D-1] to [D-120].5 Examples of suitable further matrix materials for a combination with compounds of the formula (1) or preferred compounds of the formula (1), as described above or preferably described, are the compounds described in US2023172065 A, on pages 413 to 434. 10 For a combination with compounds of the formulas (1), (1a), (1b) or (1c), as described above or preferably described, compounds of the formula (HH-1) and / or the formula (HH-4) and / or the formulas (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D) and (HH-5-E) are particularly suitable, as described above or preferably described. In the subgroup of compounds of formula (HH-5), selected from 15 compounds of formulas (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), compounds of formulas (HH-5A, (HH-5-B) and (HH-5-D) are preferred, with compounds of formula (HH-5-A) being particularly preferred.For a combination with compounds of the formulas (1), (1a), (1b) or (1c), as described above or preferably described, compounds of the formula (HH-1), (HH-4) and / or compounds of the formula (HH-5) are particularly suitable. For a combination with a compound of the formulas (1), (1a), (1b) or (1c), as described above or preferably described, compounds of the formula (HH-4) or (HH-5) or (HH-5-A) are very particularly suitable. Further examples of suitable host materials of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) and (HH-6) for combination with compounds of the formula (1) or preferred compounds of the formula (1), as previously described or preferably described, are the structures of Table 3 and Table 4 mentioned below. 35 Table 3:.

[0005] P24072 Sc - 62 - 5 10 15 20 25 30 n in Table 3 above represents the number of D atoms in the respective compound and is 0 or D1 to Dmax, preferably D1 to Dmax. If n = 0, this means that the compound is non-deuterated. n = D1 means that in 35% of the respective compound, one H atom is replaced by a D atom. Dmax represents the maximum number of D atoms possible in the respective compound. The maximum number Dmax can vary from compound to compound. Depending on the compound, Dmax can assume the following values: 20, 24, 26, 28, 30, 31, 32, 34, 35, 36, 37, 38, and 40.P24072 Sc - 63 - Particularly suitable compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6), which are selected according to the invention and are preferably used in combination with at least one compound of the formula (1) in the electroluminescent device according to the invention, are the compounds of Table 4. Table 4: 10 15 20 25 30. 35 P24072 Sc - 65 - 5 10 15 20 25 30 35 P24072 Sc - 66 - 5 10 15 20 25 30 35 P24072 Sc - 67 - 5 10 15 20 25 30 35 P24072 Sc - 68 - 5 10 15 20 25 30 For simplicity, the compounds in Tables 3 and 4 are partially presented as fully deuterated compounds, which generally refers to compounds that have a degree of deuteration of at least 50 mol%. The degree of deuteration for the fully deuterated compounds in Tables 3 and 4 is therefore between 50 and 100 mol% or has a preferred degree of deuteration as previously described. For partially deuterated compounds, a D atom indicates that the corresponding position in the molecule has a degree of deuteration of at least 40 mol%.The above-mentioned host materials of formula (1) and their preferred embodiments 5 described or the compounds of Table 1 and the compounds E1 to E30 can be combined as desired in the device according to the invention with the above-mentioned matrix materials / host materials, the matrix materials / host materials of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6) and their preferred embodiments 10 described in Table 3 or the compounds H1 to H51. Very particularly preferred mixtures of the compounds of formula (1) with the host materials of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6) for the device according to the invention are obtained by combining the compounds E1 to E30 with the compounds H1 to H51. Very preferred mixtures are shown in Table 5 below.The first mixture M1, for example, is a combination of compound E1 with H1. Table 5: 20 25 30 35. P24072 Sc - 70 - 5 10 15 20 25 30 35 P24072 Sc - 71 - 5 10 15 20 25 30 35 P24072 Sc - 72 - 5 10 15 20 25 30 35 P24072 Sc - 73 - 5 10 15 20 25 30 35 P24072 Sc - 74 - 5 The concentration of the host material of formula (1), as described above or preferably described, in the mixture according to the invention or in the light-emitting layer of the device according to the invention is usually in the range from 5 wt.% to 90 wt.%, preferably in the range from 10 wt.% to 85 wt.%, more preferably in the range from 20 wt.% to 85 wt.%, even more preferably in the range from 30 wt.% to 80 wt.%, very particularly preferably in the range from 20 wt.% to 60 wt.% and most preferably in the range from 30 wt.% to 50 wt.%, based on the total mixture or based on the total composition of the light-emitting layer.The concentration of the sum of all host materials of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) and (HH-6), as described above or described as preferred, in the mixture according to the invention or in the light-emitting layer of the device according to the invention is usually in the range from 10 wt.% to 95 wt.%, preferably in the range from 15 wt.% to 90 wt.%, more preferably in the range from 15 wt.% to 80 wt.%, even more preferably in the range from 20 wt.% to 70 wt.%, very particularly preferably in the range from 40 wt.% to 80 wt.% and most preferably in the range from 25 wt.% to 50 wt.% to 70 wt.%, based on the entire mixture or based on the entire composition of the light-emitting layer.The present invention also relates to a mixture which, in addition to the abovementioned host materials of the formula (1), hereinafter referred to as host material 1, and the host material of at least one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) and (HH-6), hereinafter referred to as host material 2, as described above or preferably described, contains at least one phosphorescent emitter. 35 The present invention also relates to a mixture selected from a combination of the compounds E1 to E30 with the compounds H1 to H51 or the mixtures M1 to M600, which contains at least one phosphorescent emitter.P24072 Sc - 75 - The present invention also relates to an organic electroluminescent device as described above or preferably described, wherein the light-emitting layer contains at least one phosphorescent emitter in addition to the abovementioned host materials of the formula (1) and at least one of the formulae (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) and (HH-6), as described above or preferably described, in particular the material combinations M1 to M600. The term phosphorescent emitters typically includes compounds in which the light emission occurs through a spin-forbidden transition from an excited state with higher spin multiplicity, i.e. a spin state > 1, for example through a transition from a triplet state or a state with an even higher spin quantum number, for example a quintet state.Preferably, this refers to a transition from a triplet state. 15 Particularly suitable phosphorescent emitters (= triplet emitters) are compounds which, upon suitable excitation, emit light, preferably in the visible range, and which also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80, 20 in particular a metal with this atomic number. Preferably, compounds which contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium are used as phosphorescent emitters, in particular compounds which contain iridium or platinum. For the purposes of the present invention, all luminescent compounds which contain the above-mentioned metals 25 are regarded as phosphorescent emitters.In general, all phosphorescent complexes as used in the prior art for phosphorescent OLEDs and as known to those skilled in the art in the field of organic electroluminescent devices are suitable. 30 Preferred phosphorescent emitters according to the present invention correspond to the formulas (I), (II), (III), (IV) or (V), 35 P24072 Sc - 76 - 5 10 15 20 25 30 35. , P24072 Sc - 77 - 5 , 10 where the symbols and indices for these formulas (I), (II), (III), (IV) and (V) have the meaning: R1 is H or D, R2 is H, D, F, CN or a branched or linear alkyl group having 1 to 10 C atoms or a partially or fully deuterated branched or linear alkyl group having 1 to 10 C atoms or a cycloalkyl group having 4 to 10 C atoms, which may be partially or fully substituted with deuterium. Preferred phosphorescent emitters according to the present invention correspond to the formula (VI), 20 25 Formula (VI), where the symbols and indices for this formula (VI) have the meaning: n+m is 3, n is 1 or 2, m is 2 or 1, X is, identically or differently on each occurrence, N or CR, R is, identically or differently on each occurrence, H, D, F, CN or a branched or linear alkyl group having 1 to 10 C atoms or a partially or fully deuterated branched or linear alkyl group having 1 to 10 C atoms or a cycloalkyl group having 4 to 7 C atoms which may be partially or fully substituted with deuterium or an aromatic or heteroaromatic ring system having 5 to 60 ring atoms which may be partially or fully substituted with deuterium and / or a partially or fully deuterated, branched or linear alkyl group having 1 to 10 C atoms. In emitters of formula (VI), n is preferably 1 and m is preferably 2.P24072 Sc - 78 - In emitters of the formula (VI), one X is preferably selected from N and the other Xs are CR or all Xs, identically or differently on each occurrence, are CR. In emitters of the formula (VI), at least one R is preferably different from H. In emitters of the formula (VI), two Rs are preferably different from H and have one of the 5 meanings otherwise given above for the emitters of the formula (VI). The invention accordingly further provides an organic electroluminescent device as described above or preferably described, characterized in that the light-emitting layer contains, in addition to the host materials 1, 10 and 2, at least one phosphorescent emitter which corresponds to one of the formulas (I) to (VI), as described above, preferably corresponds 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. 15 The emitters are incorporated into the description by this reference. Particularly preferred examples of phosphorescent emitters are listed in Table 6 below. Table 6: 20 25 30 35 P24072 Sc - 80 - 5 10 15 20 25 30 35 P24072 Sc - 81 - In the mixtures according to the invention or in the light-emitting layer of the device according to the invention, preferably each mixture selected from the sum of the mixtures M1 to M600 is combined with a compound of the formulas (I) to (VI) or with a compound from Table 6. The light-emitting layer in the organic electroluminescent device according to the invention comprising at least one phosphorescent emitter is preferably an infrared-emitting, yellow, orange, red, green, blue or ultraviolet-emitting layer, particularly preferably a yellow or green-emitting layer and very particularly preferably a green-emitting layer. A yellow-emitting layer is understood to mean a layer whose photoluminescence maximum is in the range from 540 to 570 nm. An orange-emitting layer is understood to mean a layer whose photoluminescence maximum is in the range from 570 to 600 nm.A red-emitting layer is defined as a layer whose photoluminescence maximum lies in the range from 600 to 750 nm. A green-emitting layer is defined as a layer whose photoluminescence maximum lies in the range from 490 to 540 nm. A blue-emitting layer is defined as a layer whose photoluminescence maximum lies in the range from 440 to 490 nm. The photoluminescence maximum of the layer is determined by measuring the photoluminescence spectrum of the layer with a layer thickness of 50 nm at room temperature, wherein the layer contains the inventive combination of the host material 1 of the formulas (1), (1a), (1b) or (1c) and the 25 host material 2, consisting of at least one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) and (HH-6), and the corresponding emitter.The photoluminescence spectrum of the layer is recorded, for example, using a commercially available photoluminescence spectrometer. The photoluminescence spectrum of the selected emitter is usually measured in an oxygen-free solution. -5The measurement is carried out at room temperature, and any solvent in which the selected emitter dissolves at the specified concentration is suitable. Particularly suitable solvents are usually toluene or 2-methyl-THF, but also dichloromethane. The measurement is carried out using a commercially available photoluminescence spectrometer. The triplet energy T1 in eV is determined from the photoluminescence spectra of the emitters. First, the peak maximum Plmax. (in nm) of the photoluminescence spectrum is determined. The peak maximum Plmax. (in P24072 Sc - 82 - 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 the 5 formulas (I) to (VI) or from Table 6, whose triplet energy T1 is preferably between ~2.3 eV and ~2.1 eV.Preferred phosphorescent emitters are accordingly green emitters, preferably of the 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 accordingly green emitters, preferably of the 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. 15 Green emitters, preferably of the formulas (I) to (VI) or from Table 6, as described above, are very particularly preferably selected for the mixture according to the invention or the emitting layer according to the invention. 20 Fluorescent emitters can also be present in the light-emitting layer of the device according to the invention or in the mixture according to the invention.Preferred fluorescent-emitting compounds are selected from the class of arylamines, where preferably at least one of the aromatic or heteroaromatic ring systems of the arylamine is a fused ring system, particularly preferably with at least 14 ring atoms. Preferred examples of these are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic chryseneamines, or aromatic chrysenediamines. An aromatic anthraceneamine is understood to be a compound in which one diarylamino group is bonded directly to one anthracene group, preferably in the 9-position. An aromatic anthracenediamine is understood to be a compound in which two diarylamino groups are bonded directly to one anthracene group, preferably in the 9,10-position.Aromatic pyrenamines, pyrenediamines, chrysenamines, and chrysenediamines are defined analogously, with the diarylamino groups on the pyrene preferably being bonded in the 1-position or 1,6-position. Further preferred emitting compounds are indenofluorenamines or diamines, benzoindenofluorenamines or diamines, and dibenzoindenofluorenamines or diamines, as well as indenofluorene derivatives with fused aryl groups. Pyrene-arylamines are also preferred. Benzoindenofluorene amines, benzofluorene amines, extended benzoindenofluorenes, phenoxazines, and fluorene derivatives linked to furan units or thiophene units are also preferred. Furthermore, the light-emitting device or the mixture according to the invention can also contain materials that exhibit TADF (thermally activated delayed fluorescence).5 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, but they can also contain, as a third or fourth matrix material, for example, in addition to a host material 1 or host material 2, wide-band-gap materials, bipolar host materials, electron-transport materials (ETM), or hole-transport materials (HTM). The mixed-matrix system is preferably optimized for an emitter of the formulas (I) to (VI) or for an emitter of Table 6.15 According to one embodiment of the present invention, the mixture contains no further components, i.e., functional materials, apart from the constituents of host material 1 and host material 2, as previously described or preferably described. These are material mixtures that are used as such to produce the 20 light-emitting layer. These mixtures are also referred to as premix systems, which are used as the sole material source during the vapor deposition of the host materials for the light-emitting layer and which have a constant mixing ratio during vapor deposition. This allows the vapor deposition of a layer with a uniform distribution of the 25 components to be achieved in a simple and rapid manner, without the need for precise control of a large number of material sources.According to an alternative embodiment of the present invention, the mixture contains, in addition to the constituents of host material 1 and host material 2, as described above or preferably described, a phosphorescent emitter as described above. With a suitable mixing ratio during vapor deposition, this mixture can also be used as the sole material source. Preference is given to premix systems consisting of two matrix materials, namely a compound of formulas (1), (1a), (1b) or (1c) and a compound of one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6). Preferred are premix systems consisting of three matrix materials, namely a compound of formulas (1), (1a), (1b) or (1c) and two compounds of one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6). The components orComponents of the light-emitting layer of the device according to the invention can thus be processed by vapor deposition or from solution. The material combination of the host materials 1 and 2, as described above or preferably described, optionally with the phosphorescent emitter, as described above or preferably described, are provided for this purpose in a formulation which contains at least one solvent. Suitable formulations have been described above. The light-emitting layer in the device according to the invention according to the preferred embodiments and the emitting compound preferably contains between 99.9 and 1 vol.%, further preferably between 99 and 10 vol.%, particularly preferably between 98 and 60 vol.%, very particularly preferably between 97 and 80 vol.-% of matrix material comprising at least one compound of the formulas (1), (1a), (1b) or (1c) and at least one compound of one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6) according to the preferred embodiments, based on the total composition of emitter and matrix material. Accordingly, the light-emitting layer in the device according to the invention preferably contains between 0.1 and 99 vol.%, more preferably between 1 and 90 vol.%, particularly preferably between 2 and 40 vol.%, very particularly preferably between 3 and 20 vol.% of the emitter, based on the total composition of the light-emitting layer consisting of emitter and matrix material. If the compounds are processed from solution, the corresponding amounts in wt.% are preferably used instead of the above-specified amounts in vol.%.The present invention also relates to an organic electroluminescent device, as described above or preferably described, wherein the organic layer contains a hole-injection layer (HIL) and / or a hole-transport layer (HTL), whose hole-injecting material and hole-transporting material belong to the class of arylamines. The sequence of layers in the organic electroluminescent device according to the invention is preferably the following: anode / hole-injection layer / hole-transport layer / emitting layer / hole-blocking layer / electron-transport layer / electron-injection layer / cathode. P24072 Sc - 85 - This sequence of layers is a preferred sequence. It should be noted again that not all of the mentioned layers need to be present and / or that additional layers may be present.5 All materials used in the prior art as electron-transport materials in the electron-transport layer can be used as materials for the electron-transport layer. Particularly suitable are aluminum complexes, for example Alq3, zirconium complexes, for example Zrq4, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives, and phosphine oxide derivatives.The present invention also relates to an organic electroluminescent 15 device, as described above or preferably described, wherein the organic layer contains an electron injection layer (EIL) and / or an electron transport layer (ETL) and / or a hole blocking layer, whose electron-injecting material and electron-transporting material are selected from the compounds of the formulas (1), (1a), (1b) or (1c), as described above or preferably described. 20 Suitable as the cathode of the device according to the invention are metals with a low work function, metal alloys or multilayer structures made of different metals, such as alkaline earth metals, alkali metals, main group metals or lanthanides (e.g. Ca, Ba, Mg, Al, In, Yb, Sm, etc.). Alloys 25 made of an alkali or alkaline earth metal and silver, for example an alloy of magnesium and silver, are also suitable.In multilayer structures, in addition to the metals mentioned, other metals with a relatively high work function can be used, such as Ag or Al, in which case combinations of metals such as Ca / Ag, Mg / Ag, or Ba / Ag are generally used. It may also be preferable to introduce a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor. Examples of suitable materials for this include alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates (e.g., LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.). Lithium quinolinate (LiQ) can also be used. The thickness of this layer is preferably between 0.5 and 5 nm. Materials with a high work function are preferred as the anode. The anode preferably has a work function greater than 4.5 eV vs. vacuum.On the one hand, metals with a high redox potential, such as Ag, Pt, or Au, are suitable for this purpose. On the other hand, metal / metal oxide electrodes (e.g., Al / Ni / NiO) can also be used. x , Al / PtO x) may be preferred. For some applications, at least one of the electrodes must be transparent or partially transparent to enable either the irradiation of the organic material (organic solar cell) or the coupling out of light (OLED, O-LASER). Preferred anode materials here are conductive mixed metal oxides. Particular preference is given to indium tin oxide (ITO) or indium zinc oxide (IZO). Also preferred are conductive, doped organic materials, in particular conductive doped polymers. Furthermore, the anode can also consist of several layers, 10 for example of an inner layer of ITO and an outer layer of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.The organic electroluminescent device according to the invention is structured, contacted, and finally sealed during production (depending on the application), since the lifetime of the devices according to the invention is shortened in the presence of water and / or air. The production of the device according to the invention is not restricted by this. It is possible for one or more organic layers, including the light-emitting layer, to be coated using a sublimation process. The materials are sublimated in vacuum sublimation systems at an initial pressure of less than 10. -5 mbar, preferably less than 10 -6 mbar. However, it is also possible that the initial pressure is even lower, for example less than 10 -7mbar. 25 The organic electroluminescent device according to the invention is preferably characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) method or by means of carrier gas sublimation. In this case, the materials are heated to a pressure of between 10 -5mbar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) 30 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 35 composition according to the invention are produced from solution, such as 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.P24072 Sc - 87 - Solution processing 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. 5 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. 10 These processes are generally known to those skilled in the art and can be applied to organic electroluminescent devices.The invention therefore further provides a process for producing the organic electroluminescent device according to the invention, as described above or preferably described, characterized in that the organic layer, preferably the light-emitting layer, the hole-injection layer, and / or hole-transport layer, is applied by vapor deposition, in particular using a sublimation process and / or an OVPD (Organic Vapor Phase Deposition) process and / or with the aid of carrier gas sublimation, or from solution, in particular by spin coating or a printing process. When produced by vapor deposition, there are basically two ways in which the organic layer according to the invention, preferably the light-emitting layer, can be applied or vapor-deposited onto any desired substrate or the previous layer.On the one hand, the materials used can each be placed in a single material source and then evaporated from the different material sources ("co-evaporation"). On the other hand, the different materials can be premixed ("premixed systems") and the mixture placed in a single material source, from which it is then evaporated ("premix evaporation"). This allows for the simple and rapid deposition of the light-emitting layer with a uniform distribution of the components, without the need for precise control of a large number of material sources.35 The following processes are possible: A process for producing the organic electroluminescent device according to the invention, as described above or preferably described, characterized in that the organic layer, preferably the light-emitting layer, the electron transport layer and / or hole blocking layer, is applied by P24072 Sc - 88 - vapor phase deposition, in particular using a sublimation process and / or using an OVPD (Organic Vapor Phase Deposition) process and / or with the aid of carrier gas sublimation, or from solution, in particular by spin coating or using a printing process.5 A process for producing the organic electroluminescent device according to the invention, as described above 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 10 of the formulas (1), (1a), (1b) or (1c) together with the further materials which form 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 the formulas (1), (1a), (1b) or (1c) is deposited from the gas phase together with at least one further matrix material as a premix, one after the other or simultaneously with the light-emitting materials selected from the group of phosphorescent emitters, fluorescent emitters and / or emitters which exhibit TADF (thermally activated delayed fluorescence). The electronic devices according to the invention, in particular organic electroluminescent devices, are distinguished by one or more of the following surprising advantages over the prior art: 1. Electronic devices, in particular organic electroluminescent devices comprising compounds according to formula (1) orThe preferred embodiments described above and below, in particular as matrix material or as electron-conducting materials, have a very good lifetime. These compounds particularly result in low roll-off, i.e., a low drop in the power efficiency of the device at high luminance levels. 2. Electronic devices, in particular organic electroluminescent devices comprising compounds of the formula (1) or the preferred embodiments described above and below as electron-conducting materials and / or matrix materials, have excellent efficiency. Compounds according to the invention P24072 Sc - 89 - according to the formula (1) or the preferred embodiments described above and below result in a low operating voltage when used in electronic devices. 3.Electronic devices, in particular organic electroluminescent devices comprising compounds of formula (1) or the preferred embodiments described above and below as electron-conducting materials and / or matrix materials, have a low capacitance. This is advantageous for achieving high switching times when used as electroluminescent devices in display screens. 4. The compounds of formula (1) according to the invention or the preferred embodiments described above and below exhibit very high stability and lifetime. 5. The compounds of formula (1) according to the invention or the preferred embodiments described above and below exhibit very good solubility and evaporation temperatures suitable for premix development (<350°C, p = 10). -6mbar), particularly due to the direct proximity of the 20 partial structures A and C. 6. Using compounds according to formula (1) or the preferred embodiments outlined above and below, the formation of 25 optical loss channels can be avoided in electronic devices, in particular organic electroluminescent devices. As a result, these devices are characterized by high PL and thus high EL efficiency of emitters and excellent energy transfer from the matrices to dopants. 7. The use of compounds according to formula (1) or the preferred embodiments outlined above and below in layers of electronic devices, in particular organic electroluminescent devices, leads to high mobility of the electron-conductor structures. 8. Compounds according to formula (1) or the preferred embodiments outlined above and below exhibit excellent glass film formation. 9.Compounds according to formula (1) or the preferred embodiments described above and below form very good films from solutions. P24072 Sc - 90 - 10. The compounds according to formula (1) or the preferred embodiments described above and below have a deep triplet level T1, which can be in the range of 2.50 eV - 2.90 eV. 5 These above-mentioned advantages 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 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 can be combined with one another in any way, unless certain features and / or steps are mutually exclusive. This applies in particular to preferred features of the present 20 invention. Likewise, features of non-essential combinations can be used separately (and not in combination). The teaching of technical practice disclosed with the present invention can be abstracted and combined with other examples. 25 The invention is explained in more detail by the following examples, without intending to limit it thereby.30 35 P24072 Sc - 91 - Examples Synthesis Examples The following syntheses are carried out under a protective gas atmosphere in dried solvents, unless otherwise stated. 5 a) (3-Amino-4-chloro-2-benzofuranyl)phenylmethanone 10. 319 g (979 mmol) of cesium carbonate are added portionwise under argon at room temperature to a solution of 99 g (489 mmol) of 2-bromo-6-hydroxybenzonitrile and 99.5 g (489 mmol) of bromoacetophenone in 790 ml of acetone. The reaction mixture is heated to 60°C for 2 hours. The mixture is then cooled to room temperature, filtered, and finally concentrated to dryness under reduced pressure and recrystallized from heptane. The yield is 107 g (316 mmol), corresponding to 69% of theory. 20 25 30 35 P24072 Sc - 92 - 5 10 15 b) 6-Bromo-2-cyanophenyl benzoate 20 25 A solution of 10 g (50 mmol) of 2-bromo-6-hydroxybenzonitrile, 10.4 ml (75 mmol) of triethylamine, and 61 mg (0.5 mmol) of 4-N,N-dimethylaminopyridine in 200 ml of CH2Cl2 is initially charged, cooled to 0°C, and then 10.5 g (75 mmol) of benzoyl chloride is added. The mixture is stirred at room temperature for 3 h. The reaction mixture 30 is poured into 20 ml of sodium chloride solution and extracted three times with Et2O. The combined organic phase is dried over MgSO4. The organic solvent is removed under reduced pressure, and the residue is subjected to flash column chromatography on silica gel (hexane / AcOEt = 20 / 1–7 / 1). Yield: 10.4 g (33 mmol), 70% of theory. 35 P24072 Sc - 93 - c) S-(2-cyano-3-bromo-phenyl)-benzene carbothionate 5 In a flask heated under argon, 8 g (25 mmol) of 2-bromo-6-iodobenzonitrile, 0.47 g (10 mol%, 2.5 mmol) of CuI, 0.9 g (20 mol%, 5 mmol) of 1,10-10 phenanthroline, and 5.1 g (37.5 mmol) of thiobenzoic acid were added to 20 ml of degassed toluene under nitrogen and stirred at 100 °C for 24 h. The reaction mixture was cooled to room temperature. Diethyl ether (1000 ml) and saturated sodium chloride solution (1000 ml) were added, and the mixture was stirred. The organic phase was separated, and the aqueous phase was extracted with diethyl ether (2 × 1000 ml). The combined organic phases were dried over Na2SO4, and the product was isolated by column chromatography. Yield: 5.3 g (16.2 mmol), 65% of theory. d) 2-Amino-4-Bromo-3-benzofuranyl)phenylmethanone 20 25 In a heated flask under argon, 0.67 g (30 mmol) of Pd(OAc)2, 1.69 g (6 mmol) of PCy3 (tricyclohexylphosphine), 1.96 g (30 mmol) of zinc powder, and 3 g of 4 Å molecular sieve (MS4A) are placed in 1200 ml of DMF. After stirring at room temperature for 20 min, 9.4 g (30 mmol) of bromo-2-cyanophenyl benzoate is added, and the mixture is stirred overnight at 100°C. The mixture is then treated with 30 ml of saturated NaCl solution, and the aqueous phase is extracted with Et2O (100 ml x 3). The combined organic phases are dried over MgSO4 and filtered. The organic solvent is removed in vacuo, and the residue is purified by flash column chromatography on silica gel (hexane / AcOEt = 7 / 1 - 2 / 1). Yield: 6.2 g (20 mmol), 67% of theory. 35 P24072 Sc - 94 - The following brominated compounds are prepared analogously: 5 10 9-Bromo-2,4-diphenylbenzofuro[3,2-d]pyrimidine 15 20 Under argon, 107 g (316 mmol) of (3-amino-4-chloro-2-benzofuranyl)phenylmethanone and 104 g (1015 mmol) of benzonitrile are placed in 1000 ml of o-xylene, and 56 g (677 mmol) of sodium 2-methylpropan-2-olate are added. The mixture is stirred for 5 hours at 140°C. 30 ml of water is drained off using a water separator, then a little acetone is added, and stirring is continued for another hour. After cooling, the mixture is quenched with one liter of water. The organic phase is separated, washed three times with 300 ml of water, dried over MgSO4, filtered, and the solvent removed in vacuo. The residue is purified by column chromatography. The yield is 64 g (160 mmol), corresponding to 48% of theory. 35 P24072 Sc - 95 - The following compounds are prepared analogously: 5 10 15 20 25 30 35 P24072 Sc - 96 - 5 10 15 20 25 30 35 P24072 Sc - 97 - 5 10 15 20 25 30 35 P24072 Sc - 98 - 5 10 15 f) 2,9-Drichloro-4-phenyl-benzofuro[3,2-d]pyrimidine 20 13 g (110.0 mmol) of phenylboronic acid, 15.1 g (56 mmol) of 2,4,9-trichlorobenzofuro[3,2-d]pyrimidine, and 21 g (210.0 mmol) of sodium carbonate were suspended in 500 ml of ethylene glycol diamine ether and 500 ml of water. 913 mg (3.0 mmol) of tri-o-tolylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate 25 were added to this suspension, and the reaction mixture was heated under reflux for 16 h. After cooling, the organic phase was separated, filtered through silica gel, and then evaporated to dryness. The residue was recrystallized from toluene and dichloromethane / heptane. Yield: 13.1 g (42 mmol), 75% of theory. 30 The following compounds are prepared analogously: 35 P24072 Sc - 99 - 5 10 15 20 25 g) 2-Chloro-4,8-diphenyl-benzofuro[3,2-d]pyrimidine 30 31.4 g (100 mmol) of 2,4-dichloro-8-phenyl-benzofuro[3,2-d]pyrimidine, 12.2 g (100 mmol) of phenylboronic acid, and 11.8 g (111 mmol) of sodium carbonate were dissolved in 800 ml of 1,4-dioxane, 800 ml of water, and 250 ml of toluene, and stirred under argon. 1.2 g (1 mmol) of tetrakis(triphenylphosphine)palladium was added. The reaction mixture was stirred under reflux overnight. After cooling, the mixture was quenched. The organic phase was separated, washed three times with 300 ml of water, dried over MgSO4, filtered, and the solvent was removed in vacuo. The residue is purified by column chromatography on silica gel (eluent: DCM / heptane (1:10). The yield is 28 g (80 mmol), corresponding to 80% of theory. 5 10 15 20 25 30 35 P24072 Sc - 101 - 5 10 15 20 25 30 35 P24072 Sc - 102 - 5 10 15 20 25 30 35 P24072 Sc - 103 - 5 10 15 20 25 h) 2-(3-Fluorotriphenylen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 30 35 40 g (123 mmol) of 2-bromo-3-fluorotriphenylene, 60 g (236 mmol) of bis(pinacolato)diboron, and 35 g of 1,4-dioxane are initially charged in 800 ml of 1,4-dioxane and rendered inert with argon for 30 min. Subsequently, 3.5 g (3.8 mmol) of tris(dibenzylideneacetone)dipalladium (97%) and 4 g (14 mmol) of tricyclohexylphosphine are added, and the mixture is stirred under reflux for 24 h. P24072 Sc - 104 - After cooling, the solvent is removed on a rotary evaporator, and the residue is extracted with dichloromethane and water. The combined organic phases are dried over Na2SO4, ethanol (150 ml) is added, and the dichloromethane is removed on a rotary evaporator. The precipitated solid is filtered off with suction and dried in a vacuum drying cabinet. The crude product is used in the next step without further purification. Yield: 30.7 g (82 mmol, 67%), purity 94% according to 1 H-NMR. 10 15 63 g (156 mmol) of 8-bromo-2,4-diphenylbenzofuro[3,2-d]pyrimidine, 50 g (170 mmol) of 2-(3-fluorotriphenylen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and 36 g (340 mmol) of sodium carbonate were suspended in 1000 mL of ethylene glycol diamine ether and 280 mL of water. 1.8 g (1.5 mmol) of tetrakis(triphenylphosphine)palladium(0) were added to this suspension, and the reaction mixture was heated under reflux for 16 h. After cooling, the organic phase was separated, filtered through silica gel, and then evaporated to dryness. The product is purified by column chromatography on 25 silica gel with toluene / heptane (1:2) and finally evaporated in high vacuum (p = 5 x 10 -7 mbar) (purity 99.9%). The yield is 68 g (120 mmol), corresponding to 71% of theory. The following compounds are prepared analogously: 30 35 P24072 Sc - 105 - 5 10 15 20 25 30 35 P24072 Sc - 106 - 5 10 15 20 25 30 35 P24072 Sc - 107 - 5 10 15 20 25 30 35 P24072 Sc - 108 - 5 10 15 20 25 30 35 P24072 Sc - 109 - 5 P24072 Sc - 110 - 5 10 15 20 25 30 35 P24072 Sc - 111 - 5 10 15 20 25 j) 2,4-Diphenyl-8-(3-(4a,4b,8a,9a-tetrahydro-9H-carbazol-9-yl)triphenylen-2- yl)benzofuro[3,2-d]pyrimidin 30 35 Under Argen, 54 g (96 mmol) of 8-(3-fluorotriphenylen-2-yl)-2,4-diphenylbenzofuro[3,2-d]pyrimidine, 30 g (179 mmol) of carbazole, and 54 g (166 mmol) of cesium carbonate are suspended in 1500 mL of N,N-dimethylformamide, and the reaction mixture is heated under reflux at 150°C for 40 h. The reaction mixture P24072 Sc - 112 - is cooled to room temperature, 1500 mL of water is added, and the precipitated solid is filtered off. The resulting solid is washed with 300 mL of ethanol and recrystallized several times from xylene. After hot filtration through Alox and subsequent sublimation under high vacuum, the purified product is obtained as a colorless solid (58 g, 81 mmol; 85%). Analogously, the following compounds are prepared: 10 15 20 25 30 35 P24072 Sc - 113 - 5 10 15 20 25 30 35 P24072 Sc - 114 - 5 10 15 20 25 30 35 P24072 Sc - 115 - 5 10 15 20 25 30 35 P24072 Sc - 116 - 5 10 15 20 25 30 35 P24072 Sc - 117 - 5 10 15 20 25 30 35 P24072 Sc - 118 - 5 10 15 20 25 30 35 P24072 Sc - 119 - 5 10 15 20 25 30 35 P24072 Sc - 120 - 5 P24072 Sc - 121 - 5 10 15 20 25 30 35 P24072 Sc - 122 - 5 k) 2,4-Diphenyl-8-(3-(4a,4b,8a,9a-tetrahydro-9H-carbazol-9-yl)triphenylen-2- yl)benzofuro[3,2-d]pyrimidin-d 31 10 15 20 34.2 g (48.0 mmol; 1.0 eq) of 2,4-diphenyl-8-(3-(4a,4b,8a,9a-tetrahydro-9H-carbazol-9-yl)triphenylen-2-yl)benzofuro[3,2-d]pyrimidine-d 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 25°C ambient temperature for 6 hours. Subsequently, 120 mL (130 eq.) of deuterium oxide [CAS 7789-20-0] is added dropwise at 0°C. After neutralization with potassium sulfate solution, the mixture is extracted with toluene, and the combined organic phases are washed with brine and dried over sodium sulfate. After filtration, the solvent is removed under reduced pressure. 25 g (33.5 mmol, 70% of theory) of the product shown above, mixed with portions of H / D isotopomers and H / D isotopologues, are obtained after chromatographic purification and finally concentrated under high vacuum (p = 5 x 10 -7mbar) (purity 99.9%). 35 P24072 Sc - 123 - The following compounds are prepared analogously: 5 10 15 20 25 30 35 P24072 Sc - 124 - Production of the OLEDs Example A) In the following examples Ex1 to Ex9 (see Tables 7 and 8), various OLEDs are presented. Examples Ex1 to Ex9 describe OLEDs according to the invention. 5 The substrate for the OLEDs in Table 7 is glass flakes coated with structured ITO (indium tin oxide) with a thickness of 50 nm. The exact structure of the OLEDs can be found in Table 7. The materials required to produce the OLEDs are shown in Table 8, unless previously described. 10 All materials are thermally vapor-deposited in a vacuum chamber. The emission layer always consists of at least one matrix material (also host material) and an emitting dopant (dopant, emitter), which is admixed to the matrix material(s) by co-evaporation in a specific 15 volume fraction.A specification such as E6:H36:TEG3 (42%:50%:8%) 40nm means that the material E6 is present in a volume fraction of 42% as host material 1, the compound H36 as host material 2 in a fraction of 50%, and TEG3 in a fraction of 8% in a 40nm-thick layer. Analogously, the hole injection layer (HIL) and the electron transport layer (ETL), for example, can also consist of a mixture of two materials. OLEDs are characterized as standard. For this purpose, the electroluminescence spectra and current-voltage-luminance characteristics (IUL characteristics) are measured, from which the EQE is calculated. The calculation is performed assuming a Lambertian radiation characteristic. The voltage required for a current density of 10 mA / cm² is referred to here as U10. EQE10 refers to the external quantum efficiency at a current density of 10 mA / cm².The lifetime LT90 is defined as the time after which the luminance drops from an initial luminance L0 (in cd / m²) to 90% of this initial luminance when operated at a constant current density j0 in mA / cm². 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. P24072 Sc - 125 - Table 7: 5 10 15 20 25 Table 8: Materials used, unless previously described 30 35 P24072 Sc - 126 - 5 10 15 20 25 The compounds according to the invention are suitable for use as matrix material, electron-transport material, or hole-blocking material, particularly in a phosphorescent OLED. The OLEDs described above exhibit a good lifetime and low capacity. 30 Example B) In the following examples Ex1-9 (see Tables 9 and 10), data for various OLEDs according to the invention are presented. Glass flakes coated with structured ITO (indium tin oxide) with a thickness of 50 nm are used as the substrate and anode of the OLEDs in Table 9. These coated glass flakes are pretreated with an oxygen plasma followed by an argon plasma in a high vacuum immediately before the thermal deposition of the organic layers.The OLEDs basically have the following layer structure: substrate / P24072 Sc - 127 - hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / emission layer (EML) / hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) and finally a cathode made of 100nm aluminum. The exact structure of the OLEDs can be found in Table 9. The corresponding Device 5 data is summarized in Table 10. The materials required to manufacture the OLEDs are shown in Table 11, unless previously described. All materials are thermally evaporated in a vacuum chamber. The emission layer always consists of at least one matrix material (also host material 10 or host material) and an emitting dopant (dopant, emitter), which is mixed into the matrix material(s) in a specific volume fraction by co-evaporation.A specification such as E6:H52:TEG2 (32%:60%:8%) 40nm means that the material E6 is present in a volume fraction of 32% as host material 1, the compound H52 as host material 2 in a fraction of 60%, and TEG2 in a fraction of 15% (8%) in a 40nm thick layer. Analogously, the hole injection layer (HIL) and the electron transport layer (ETL), for example, can also consist of a mixture of two materials. OLEDs are characterized as standard. For this purpose, the 20 electroluminescence spectra and current-voltage-luminance characteristics (IUL characteristics) are measured, from which the EQE is calculated. The calculation is performed assuming a Lambertian radiation characteristic. The voltage required for a current density of 10 mA / cm² is referred to here as U10. EQE10 refers to the external quantum efficiency at a current density of 10 mA / cm².25 The lifetime LT is defined as the time in hours (h) after which the luminance drops from an initial luminance L0 (in cd / m²) to a specific proportion L1 (in cd / m²) of this initial luminance when the OLED is operated at a constant current density j0 (in mA / cm²). A value L1 / L0=90% means, for example, that the lifetime specified in the LT column in 30 Table 10 corresponds to the time (in h) after which the initial luminance (L0) has dropped to 90% of its initial value. In the examples shown here, the current density used is, for example, 80 mA / cm². Use of mixtures according to the invention in OLEDs 35 The compounds or material combinations according to the invention can be used in the emission layer in phosphorescent green OLEDs. The compounds according to the invention surprisingly exhibit high efficiency and a long lifetime. P24072 Sc Tab Bs 5 Ex1 Ex2 10 Ex3 Ex4 15 Ex5 Ex6 20 Ex7 E x8 HT1:PD1 E9:H7:TEG2 ST1:LiQ HT1 HT2 AT1 LiQ 25 Ex9 (95%:5%) (32%:60%:8%) (50%:50%) 50nm 20nm 5nm 1nm 20nm 40nm 30nm Table 10: Example EQE (%) j0 (mA / cm²) L1 / L0 (%) LT (h) 30 Ex1 25 80 90 150 Ex2 28.5 80 90 65 Ex3 28.3 80 90 92 Ex4 28.4 80 90 97 Ex5 25.1 80 90 190 Ex6 28.3 80 90 123 Ex7 24.5 80 90 215 35 Ex8 26 80 90 115 Ex9 23 80 90 180 P24072 Sc - 129 - Table 11: Materials used, unless previously described 5 10 15 20 25 30 35

Claims

P24072 Sc - 130 - Claims 1. Compounds of formula (1), ABC formula (1), 5 where B represents a structure of formula (2), A represents a structure of formula (3) and C represents a structure of formula (4), (5) or (6), 10 15 20 25 30 35 where the symbols and indices used are: P24072 Sc - 131 - a, b and c represent the respective linkage points to formulas (3), (4), (5) or (6); V is O or S; Y is each independently N, C, CH or CR 1 , where at least one 5 Y stands for N and where it is excluded that two adjacent Y simultaneously stand for N; R# is at each occurrence independently of one another an aryl group having 6 to 20 C atoms which is reacted with one or more radicals R 0 may be substituted; m is independently 0, 1 or 2 at each occurrence; 10 * is the linkage point at a, b or c of formula (2); # is the linkage point at a, b or c of formula (2); Ra , R b , R c and R d represent a monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution or no substitution; 15 R a , R b , R c and R d are D at each occurrence; Ar3 is an aryl or heteroaryl group with 5 to 40 ring atoms which can be substituted with one or more radicals R 0 may be substituted; R 1 is at each occurrence independently D, CN, F or an aryl or heteroaryl group having 5 to 40 ring atoms which can be substituted by one or more 20 radicals R 0 may be substituted; R 0 is selected at each occurrence, identically or differently, from the group consisting of D, F, Cl, Br, I, CN, NO2, C(=O)R 2 , P(=O)(Ar)2, P(Ar)2, B(Ar)2, Si(Ar)3, Si(R 2)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 C atoms, each of which is substituted by one or more radicals R 2 may be substituted, with one or more non-adjacent CH2 groups being substituted by R 2 C=CR 2 , Si(R 2 )2, C=O, C=S, C=NR 2 , P(=O)(R 2 ), SO, SO2, NR 2 , O, S or CONR 2 and wherein one or more H atoms may be replaced by D, F, 30 Cl, Br, I, CN or NO2, an aryl or heteroaryl group having 5 to 40 ring atoms which may be substituted with one or more radicals R 2 may be substituted, an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, which may be substituted with one or more radicals R 2may be substituted, or an aralkyl or heteroaralkyl group having 5 to 40 ring atoms which may be substituted with one or more radicals R 2 may be substituted; R 2 is selected, identically or differently at each occurrence, from the group consisting of D, F, CN, Si(Aryl)3, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where one or more non-adjacent CH2 groups are replaced by O P24072 Sc - 132 - or S and wherein one or more H atoms may be replaced by D, F, or CN, Aryl is an unsubstituted, partially or fully deuterated aryl group having 6 to 40 C atoms, 5 with the condition that the structure of formula (3) with the linkage point * and the structure of formulas (4), (5) or (6) with the linkage point # in formula (2) are directly adjacent.

2. Compounds according to claim 1, wherein at least two Y's are N. 10 3. Compounds according to claim 1 or 2, wherein formula (3) corresponds to one of formulas (3-1), (3-2), (3-3) or (3-4), 15 , 20 25 where V, R 1 , R#, R dand m have a meaning mentioned in claim 1.

4. Compounds according to one or more of claims 1 to 3, where V is O.

5. Compounds according to one or more of claims 1 to 4, which are partially or fully deuterated.

6. Mixture comprising at least one compound of the formula (1) according to one or more of claims 1 to 5 and at least one further compound selected from the group of matrix materials, phosphorescent emitters, fluorescent emitters and / or emitters which exhibit TADF (thermally activated delayed fluorescence). P24072 Sc - 133 - 7. Use of at least one compound of formula (1) according to one or more of claims 1 to 5 in an organic electronic device.

8. An organic electronic device comprising an anode, a cathode, and at least one organic layer containing at least one compound of formula (1) according to one or more of claims 1 to 5.

9. The organic electronic device according to claim 8, 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. 10.The organic electronic device according to claim 8 or 9, wherein the organic layer contains at least one light-emitting layer, a hole-transporting layer, a hole-injecting layer, or an electron-blocking layer containing at least one compound according to one of claims 1 to 5.

11. The organic electronic device according to one or more of claims 8 to 10, characterized in that the light-emitting layer contains the at least one compound of formula (1) according to one of claims 1 to 5.

12. The organic electronic device according to one or more of claims 8 to 11, characterized in that the light-emitting layer contains, in addition to the compound of formula (1) according to one of claims 1 to 5, at least one further matrix material.Organic electroluminescent device according to claim 12, characterized in that the further matrix material contains one or more of the compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6) as matrix material 2, 30 35. , P24072 Sc - 134 - 5 10 15 20 25 30 35 - , where the symbols and indices used are: A 1 is C(R 7 )2, NR 7 , O or S; P24072 Sc - 135 - L is a bond, O, S, C(R 7 )2 or NR 7 ; A is at each occurrence independently a group of the formula (HH-4-1) or (HH-4-2), 5 10 X2is the same or different at each occurrence CH, CR 6 or N, where a maximum of 2 symbols can represent X2N; 15 * denotes the binding site to the formula (HH-4); U 1 , U 2 are a bond, O, S, C(R 7 )2 or NR7 ; R 6 is, at each occurrence, identically or differently, D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 7 may be substituted and wherein one or more non-adjacent CH2 groups are substituted by Si(R 7 )2, C=O, NR 7 , O, S or CONR 7 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, each of which is substituted by one or more radicals R 7 substituted 25; two radicals R 6also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar5, identically or differently at each occurrence, independently represents an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which is reacted with one or more radicals R 7 can be substituted; 30 R 7 is the same or different at each occurrence D, F, Cl, Br, I, N(R 8 )2, CN, NO2, OR 8 , SR 8 , Si(R 8 )3, B(OR 8 )2, C(=O)R 8 , P(=O)(R 8 )2, S(=O)R 8 , S(=O)2R 8 , OSO2R 8 , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group 35 is each substituted with one or more radicals R 8may be substituted, with one or more non-adjacent CH2 groups being substituted by Si(R 8 )2, C=O, NR 8 , O, S or CONR 8 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which is substituted by one or more radicals R 8 may be substituted, where R 8 does not mean H; P24072 Sc - 136 - two or more residues R 7 together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system, preferably the radicals R 7 no such ring system; R 8is, on each occurrence, the same or different, H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, in particular a hydrocarbon radical, having 1 to 20 C atoms, in which one or more H atoms may also be replaced by D or F; c, c1, c2 each independently denote on each occurrence 0 or 1, where the sum of the indices on each occurrence c+c1+c2 = 1; d, d1, d2 each independently denote on each occurrence 0 or 1, where the sum of the indices on each occurrence d+d1+d2 = 1; q, q1, q2 each independently denote 0, 1, 2, 3 or 4; s is, on each occurrence, the same or different, 0, 1, 2, 3 or 4; t is, on each occurrence, the same or different, 0, 1, 2, or 3; 15 u is, at each occurrence, the same or different, 0, 1, or 2; u1, u2 each independently mean 0 or 1 at each occurrence, where the sum u1 + u2 = 1; and v is 0, 1, 2, or 3.20 14. The organic electronic device according to one or more of claims 8 to 13, characterized in that the light-emitting layer contains a phosphorescent emitter.

15. The organic electronic device according to one or more of claims 8 to 14, characterized in that it is an organic electroluminescent device selected from the group consisting of 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). 30 35.

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