Materials for organic electroluminescent devices

Abstract

The present invention relates to 4H-naphtho[1,2,3,4-def] carbazoles as OLED materials, to mixtures and formulations containing them, 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] P23-216 Sc - 1 - Materials for organic electroluminescent devices Technical field The present invention relates to 4H-naphtho[1,2,3,4-def]carbazoles, mixtures and formulations comprising them, and electronic devices comprising these compounds, in particular organic electroluminescent 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 a need 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 state of the art, carbazole derivatives, dibenzofuran derivatives, indenocarbazole derivatives, indolocarbazole derivatives, benzofurocarbazole derivatives, and benzothienocarbazole derivatives are used as matrix materials for phosphorescent emitters. 25 WO2012048781 A1 and CN115626914 A describe, among other things, special 4H-naphtho[1,2,3,4-def]carbazole derivatives as matrix materials. KR20210036304 A, KR20210034528 A, WO22038065 A1, CN115073356 A, CN112062753 A, and US2022263031 A1 describe, among other things, complex carbazole derivatives as matrix materials. KR2014141337 A, WO2013165192 A1, WO2017115608 A1, US20200079735 A, KR2020078254 A, KR2023111045 A, and WO2023136696 A1 describe, among other things, specific carbazole derivatives as matrix materials.35 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 that 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 that lead to an improved lifetime. This applies in particular to the use of a low to medium emitter concentration, i.e., emitter concentrations in the range of 3 to 20%, in particular 3 to 15%, since the device lifetime is particularly limited in this case.It has now been found that electroluminescent devices containing compounds of the following formula (1) exhibit improvements over the prior art, in particular when the compounds are used as matrix material for phosphorescent dopants. It has further been found that the combination of at least one compound of the formula (1) as the first host material and at least one hole-transporting compound, for example in combination with one or more compounds of the 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, achieves this object and eliminates the disadvantages of the prior art. Summary of the Invention A first subject of the present invention is a compound of the formula (1). Formula (1), where the symbols and indices used are: X is each independently N, CH, CD or CR 0 , where a maximum of three Xs can stand for N; it is excluded that adjacent Xs simultaneously represent N; X1 is each independently N, CH, CD or CR 0 , where at least one X1 is N; L1, L2 are each independently a single bond or an arylene or heteroarylene group having 5 to 40 ring atoms which is reacted with one or more radicals R 1 may be substituted; R 0 is selected at each occurrence, identically or differently, from the group consisting of 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, Cl, Br, I, CN or NO2, an aryl group having 6 to 40 C atoms, each of which is substituted by one or more radicals R 2 may be substituted, a heteroaryl group having 5 to 40 ring atoms, each substituted by one or more radicals R 2 may be substituted, an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, which may be substituted with one or more radicals R2 may be substituted, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms which may be substituted by one or more radicals R 2 may be substituted; R 1 is selected at each occurrence, identically or differently, from the group consisting of D, F, CN, NO2, Si(Ar)3, Si(R 2 )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 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, where one or more non-adjacent CH2 groups are represented by R 2 C=CR 2 , Si(R 2 )2, NR 2 , O or S and where one or more H atoms can be replaced by D, F, CN or NO2, an aryl group with 6 to 40 C atoms, each of which can be substituted with one or more radicals R 2may be substituted, a heteroaryl group having 5 to 40 ring atoms, each substituted by one or more radicals R 2 may be substituted, an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, which may be substituted with one or more radicals R 2 may be substituted, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms which may be substituted by one or more radicals R 2 may be substituted; Ar, Ar1, Ar2 are independently an aryl group having 6 to 40 C atoms, each substituted by one or more radicals R 2 may be substituted, or a heteroaryl group having 5 to 40 ring atoms, each substituted by one or more radicals R 2 may be substituted; R 2is selected, identically or differently at each occurrence, from the group consisting of D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms may be replaced by D, F, or CN. The invention further provides a mixture comprising at least one compound of formula (1) as described above or preferably described later and at least one further compound selected from the group of matrix materials, phosphorescent emitters, fluorescent emitters and / or emitters,which exhibit TADF (thermally activated delayed fluorescence). The invention further relates to the use of a compound of formula (1) in an organic electronic device. The invention further relates to an organic electronic, preferably electroluminescent, device comprising an anode, a cathode, and at least one organic layer containing at least one compound of formula (1), as described above or preferably described below. The invention further relates to a process for producing an organic electronic, preferably electroluminescent, device, as described above or preferably described below, characterized in that the organic layer is applied by vapor deposition or from solution. Description of the invention In the present patent application, "D" or "D atom" refers to deuterium. The degree of deuteration, expressed in mol%,means the proportion of H atoms replaced by deuterium. Since the deuterated compounds are often a mixture of compounds that differ in the exact position and the exact proportion of the D atoms, the degree of deuteration refers to the average proportion of H atoms replaced by D. With a degree of deuteration of 50 mol%, on average 50 mol% of the H atoms in the compound are replaced by D, so that this is a medium degree of deuteration. An aryl group within the meaning of this invention contains 6 to 40 ring atoms or preferably 6 to 30 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 ring, for example phenyl, derived from benzene, or a condensed aryl group, for example derived from naphthalene, anthracene, phenanthrene, triphenylene. However, the term aryl group also encompasses biphenyl, terphenyl, quaterphenyl, fluorenyl, 9,9-dialkylfluorenyl, 9,9-diarylfluorenyl, or spirobifluorenyl within the meaning of the invention. 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 C atoms is therefore preferably phenyl, naphthyl, phenanthryl, or triphenylenyl, whereby the attachment of the aryl group as a substituent is not restricted. The aryl group in the sense of this invention can carry 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 is unsubstituted. A heteroaryl group is understood to be either a simple heteroaromatic ring, for example derived from pyridine, pyrimidine, or thiophene, or a fused heteroaryl group, for example derived from quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, or carbazole. However, the term heteroaryl group within the meaning of the invention also encompasses a heteroaryl group bonded to an aryl group or another heteroaryl group by a single bond, for example phenylbipyridyl or bipyridyl. The heteroaryl group within the meaning of this invention may carry one or more radicals, with the suitable radical being described below. The radical is preferably deuterium. If no such radical is described,the heteroaryl group is unsubstituted. An aromatic ring system within the meaning of this invention contains 6 to 40 C atoms in the ring system. The aromatic ring system also includes aryl groups, as described above, and the term is used synonymously below. An aryl group having 6 to 18 C atoms is preferably selected from phenyl, biphenyl, naphthyl, phenanthryl, and triphenylenyl, which may carry one or more radicals, the suitable radical being described below. The radical is preferably deuterium. A heteroaromatic ring system within the meaning of this invention contains 5 to 40 ring atoms and at least one heteroatom. A preferred heteroaromatic ring system has 9 to 40 ring atoms and at least one heteroatom. The heteroaromatic ring system also includes heteroaryl groups, as described above, and the term is used synonymously below. An aryl group with 6 to 40 C atoms or a heteroaryl group with 5 to 40 ring atoms,which can be linked to the aromatic or heteroaromatic ring via any position, are understood to mean, for example, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, triphenylene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzfluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, terphenyl, quaterphenyl, fluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-monobenzoindenofluorene, cis- or trans-dibenzoindenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, Isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole,Benzimidazol, Naphthimidazol, Phenanthrimidazol, Pyridimidazol, Pyrazinimidazol, Chinoxalinimidazol, Oxazol, Benzoxazol, Naphthoxazol, Anthroxazol, Phenanthroxazol, Isoxazol, 1,2-Thiazol, 1,3-Thiazol, Benzothiazol, Pyridazin, Benzopyridazin, Pyrimidin, Benzpyrimidin, Chinoxalin, 1,5-Diazaanthracen, 2,7-Diazapyren, 2,3-Diazapyren, 1,6-Diazapyren, 1,8-Diazapyren, 4,5-Diazapyren, 4,5,9,10-Tetraazaperylen, Pyrazin, Phenazin, Phenoxazin, Phenothiazin, Fluorubin, Naphthyridin, Azacarbazol, Benzocarbolin, Phenan- throlin, 1,2,3-Triazol, 1,2,4-Triazol, Benzotriazol, 1,2,3-Oxadiazol, 1,2,4-Oxadiazol, 1,2,5-Oxadiazol, 1,3,4-Oxadiazol, 1,2,3-Thiadiazol, 1,2,4-Thiadiazol, 1,2,5-Thiadiazol, 1,3,4-Thiadiazol, 1,3,5-Triazin, 1,2,4-Triazin, 1,2,3-Triazin, Tetrazol, 1,2,4,5-Tetrazin, 1,2,3,4-Tetrazin, 1,2,3,5-Tetrazin, Purin, Pteridin, Indolizin, Benzothiadiazol, Phenyl- pyridin und Bipyridin. Die Abkürzungen Ar,Ar1 and Ar2, identically or differently, represent at each occurrence an aryl group having 6 to 40 C atoms, each of which is substituted by one or more radicals R, 2 may be substituted, or a heteroaryl group having 5 to 40 ring atoms, each substituted by one or more radicals R 2 may be substituted; where the radical R 2 or the substituents R 2 has / have a meaning as described above or below. A preferred meaning of Ar and Ar1 and Ar2 is described below. The abbreviation Ar5, identically or differently at each occurrence, independently stands for an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which is substituted by one or more radicals R 7 may be substituted or is synonymous, identically or differently on each occurrence, an aryl group having 6 to 40 C atoms, each substituted with one or more radicals R 7may be substituted, or a heteroaryl group having 5 to 40 ring atoms, each substituted by one or more radicals R 7 may be substituted, where the radical R 7 or the substituents R 7 has / have a meaning as described above or below. A preferred meaning of Ar5 is described below. The phrase that two or more radicals can form a ring with each other is understood, in the context of the present description, to mean, among other things, that the two radicals are linked to each other by a chemical bond with formal elimination of two hydrogen atoms. This is illustrated by the following scheme: Rin bild n Furthermore, the above formulation should also be understood to mean that if one of the two residues represents hydrogen, the second residue binds to the position to which the hydrogen atom was bonded, forming a ring. This is illustrated by the following scheme: . A cyclic alkyl, alkoxy or thioalkyl group in the sense of this invention is understood to mean a monocyclic, a bicyclic or a polycyclic group. In the context of the present invention, a straight-chain, branched or cyclic C1 to C 20-Alkylgruppe beispielsweise die Reste Methyl, Ethyl, n-Propyl, i-Propyl, Cyclopropyl, n-Butyl, i-Butyl, s-Butyl, t-Butyl, Cyclobutyl, 2-Methylbutyl, n-Pentyl, s-Pentyl, t-Pentyl, 2-Pentyl, neo-Pentyl, Cyclopentyl, n-Hexyl, s-Hexyl, t-Hexyl, 2-Hexyl, 3- Hexyl, neo-Hexyl, Cyclohexyl, 1-Methylcyclopentyl, 2-Methylpentyl, n-Heptyl, 2-Heptyl, 3- Heptyl, 4-Heptyl, Cycloheptyl, 1-Methylcyclohexyl, n-Octyl, 2-Ethylhexyl, Cyclooctyl, 1- Bicyclo[2,2,2]octyl, 2-Bicyclo[2,2,2]octyl, 2-(2,6-Dimethyl)octyl, 3-(3,7-Dimethyl)octyl, Adamantyl, Trifluormethyl, Pentafluorethyl, 2,2,2-Trifluorethyl, 1,1-Dimethyl-n-hex-1-yl-, 1,1-Dimethyl-n-hept-1-yl-, 1,1-Dimethyl-n-oct-1-yl-, 1,1-Dimethyl-n-dec-1-yl-, 1,1-Dimethyl- n-dodec-1-yl-, 1,1-Dimethyl-n-tetradec-1-yl-, 1,1-Dimethyl-n-hexadec-1-yl-, 1,1-Dimethyl- n-octadec-1-yl-, 1,1-Diethyl-n-hex-1-yl-, 1,1-Diethyl-n-hept-1-yl-, 1,1-Diethyl-n-oct-1-yl-, 1,1-Diethyl-n-dec-1-yl-, 1,1-Diethyl-n-dodec-1-yl-, 1,1-Diethyl-n-tetradec-1-yl-, 1,1- Diethyln-n-hexadec-1-yl-,1,1-Diethyl-n-octadec-1-yl-, 1-(n-propyl)-cyclohex-1-yl-, 1-(n-butyl)-cyclohex-1-yl-, 1-(n-hexyl)-cyclohex-1-yl-, 1-(n-octyl)-cyclohex-1-yl- and 1-(n-decyl)-cyclohex-1-yl- are understood as meanings. 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 or electroluminescent device according to the invention. In a preferred embodiment of the invention, the compounds of formula (1) correspond to a compound of formula (1a), Formula (1a), where Ar1, Ar2, X1, L1, L2 and R0 have a previously given meaning and(D) a ,(D) b , (D) c, (D) d, (D) erepresent a monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution or no substitution with deuterium and a1, a2, a3 each independently represent 0, 1, 2 or 3. Preferred embodiments of the compounds of formulas (1) or (1a) are compounds of formulas (1b), (1c), (1d) and (1e),

[0002] Formula (1e), where Ar1, Ar2, X1, L1, L2, R 0 , (D) a ,(D) b , (D) c, (D) d, (D) e, a1, a2 and a3 have a meaning given above or given below as preferred. Particularly preferred compounds of formula (1) or (1a) are compounds of formula (1b). In a preferred embodiment of the compounds of formula (1), (1a), (1b), (1c), (1d) or (1e), at least two X1 are N and the third X is CD or CR 0 , where R 0has a meaning preferably given above or below. In a particularly preferred embodiment of the compounds of the formulas (1), (1a), (1b), (1c), (1d) or (1e), all three X1s are N. The invention accordingly further provides compounds of the formulas (1), (1a), (1b), (1c), (1d) or (1e), as described above, in which all X1s are N. Particularly preferred compounds of the formulas (1), (1a) or (1b) are compounds of the formula (1f), Formula (1f), where Ar1, Ar2, L1, L2, R 0 , (D) a ,(D) b , (D) c, (D) d, (D) e, a1, a2 and a3 have a meaning given above or given below as a preferred meaning. In a preferred embodiment of the compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e) or (1f), the linkers L1 and L2 each independently represent a single bond or an arylene or heteroarylene group having 5 to 40 ring atoms of the formulas L-1 to L-34, which are linked to one or more radicals R 1 can be substituted:

[0003] , where the dashed lines indicate the bond to the residue of formula (1) or the residue of formulas (1a), (1b), (1c), (1d), (1e) or (1f); V1O, S or Se and where R 1has a meaning given above or given below. V1 is particularly preferably O. From the group of linkers of the formulas L-1 to L-34, the linkers L-1 to L-7 are preferably selected. From the group of linkers of the formulas L-1 to L-34, the linkers L-1, L-2 and L-3 are particularly preferably selected. In a particularly preferred embodiment of the compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e) or (1f), the linker L1 represents a single bond and the linker L2 has a meaning given above or given with preference. In a particularly preferred embodiment of the compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e) or (1f), the linker L2 represents a single bond and the linker L1 has a meaning given above or given with preference. The invention accordingly further relates to compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e) or (1f), as described above, in which L2 represents a single bond.In a particularly preferred embodiment of the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e) or (1f), the linkers L1 and L2 represent a single bond. The index a1 represents 0, 1, 2 or 3, where the position of the substituents R. 0 are not restricted upon occurrence. Preferred compounds of formulas (1), (1a), (1b), (1c), (1d), (1e) or (1f) are compounds in which a1 = 0 or 1. The index a2 means 0, 1, 2 or 3, where the position of the substituents R 0 are not restricted upon occurrence. Preferred compounds of formulas (1), (1a), (1b), (1c), (1d), (1e) or (1f) are compounds in which a2 = 0 or 1. The index a3 means 0, 1, 2 or 3, where the position of the substituents R 0are not restricted upon occurrence. Preferred compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e) or (1f) are compounds in which a3 = 0 or 1. In one embodiment of the invention, it is preferred if the sum of the indices (a2 + a3) is 0 or 1. The radical R 0 is, identically or differently at each occurrence, preferably 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 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, an aryl group having 6 to 40 C atoms, each substituted with one or more radicals R 2 may be substituted or a heteroaryl group having 5 to 40 ring atoms, each substituted by one or more radicals R 2 may be substituted, where R 2 has a meaning given above or below. The residue R 0is, identically or differently at each occurrence, particularly preferably F, CN, phenyl, 1,2-biphenyl, 1,3-biphenyl or 1,4-biphenyl, where phenyl, 1,2-biphenyl, 1,3-biphenyl or 1,4-biphenyl are substituted with one or more radicals R 2 can be substituted. The residue R 0 is, at each occurrence, identically or differently, particularly preferably CN or phenyl which is substituted with one or more radicals R 2 can be substituted. The substituent R 1 when identical or different, is preferably selected from the group D, F, CN, Si(Ar)3, Si(R 2 )3or an aryl group having 6 to 40 C atoms, each of which is substituted by one or more radicals R 2 may be substituted or a heteroaryl group having 5 to 40 ring atoms, each substituted by one or more radicals R 2 may be substituted, where R 2 and Ar have a meaning given above or below. The substituent R 1is preferably D, phenyl or dibenzofuranyl. Ar in Si(Ar)3 is preferably the same and is an aryl group having 6 to 18 carbon atoms which can be substituted with one or more radicals R 2 can be substituted. R 2 in Ar is preferably D, F or CN, particularly preferably D. In Si(Ar)3, Ar is particularly preferably selected from non-deuterated, partially deuterated or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl. The substituent R 1 is particularly preferred when occurring D. The substituent R 2 is in each case independently upon occurrence preferably D or CN, particularly preferably D. In the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f), Ar, Ar1 and Ar2 are each independently preferably selected from the group Ar-1 to Ar-42,

[0004]

[0005]

[0006] Ar-37 Ar-38 Ar-39

[0007] , where Y 2 O, S, Se or NAr3 means Y 3 O, S, NAr3 or C(R # )2means R 3 H, R 2 , a non-deuterated, partially deuterated or fully deuterated aryl group having 6 to 30 C atoms or a non-deuterated, partially deuterated or fully deuterated heteroaryl group having 5 to 40 ring atoms, the dashed bond represents the bond to the radical of formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f), Ar3 represents an aryl group having 6 to 30 C atoms or a heteroaryl group having 5 to 40 ring atoms which is bonded to one or more radicals R 2 can be substituted, R # at each occurrence, identically or differently, denotes 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 2may be substituted, where one or more H atoms may be replaced by D, F or CN or represents an aryl group having 6 to 30 C atoms or a heteroaryl group having 5 to 40 ring atoms, which may be substituted with one or more radicals R 2 may be substituted, and where R 2 has a meaning previously mentioned or a previously preferred meaning. In the formulas Ar-31 to Ar-35, Y is 2 preferably O or NAr3. The substituent R 2 when Ar3in N-Ar3is preferably D, F or CN, particularly preferably D. In the formulas Ar-15 to Ar-18 and Ar-23 to Ar-26, Ar3when occurring in N-Ar3is Y 3 particularly preferably selected from non-deuterated, partially deuterated or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl. The symbol Y 3 in the formulas Ar-15 to Ar-18 and Ar-23 to Ar-26, N is preferably Ar3, C(CH3)2, O or S, particularly preferably O or S, very particularly preferably O. R 2in R# is preferably D, F or CN, particularly preferably D. Y 2 in the formulas Ar-31 to Ar-35 is preferably N-Ar3, S or O, particularly preferably O. In the structures Ar-1 to Ar-42 the substituent R 3 preferably selected, identically or differently at each occurrence, from the group consisting of H, D, F, CN or a non-deuterated, partially deuterated or fully deuterated aryl group having 6 to 30 C atoms and a non-deuterated, partially deuterated or fully deuterated heteroaryl group having 5 to 40 ring atoms. In the structures Ar-1 to Ar-42, the substituent R 3 particularly preferably, at each occurrence, selected identically or differently from 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, the same or different is selected from the group consisting of H, D or non-deuterated, partially or fully deuterated phenyl. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f), Ar, on each occurrence, the same or different is particularly preferably selected from the group Ar-1 to Ar-10, Ar-15 to Ar-18, Ar-23 to Ar-26, Ar-29 and Ar-30, where R 3 has a meaning previously indicated or preferably indicated. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f), Ar1 and Ar2, identically or differently, are particularly preferably selected at each occurrence from the group Ar-1 to Ar-10, Ar-15 to Ar-18, Ar-23 to Ar-26, Ar-29 and Ar-30, where R 3has a meaning previously indicated or preferably indicated. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f), Ar1 and Ar2, identically or differently, are particularly preferably selected at each occurrence from the group Ar-1 to Ar-7, Ar-10, Ar-15 to Ar-18, Ar-29 and Ar-30, where R 3 has a meaning previously given or preferably given. In a preferred embodiment of the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f), Ar1 and Ar2 are identical. In a preferred embodiment of the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f), Ar1 and Ar2 are different from one another, whereby this difference can also lie in the position of the linkage, for example, Ar1 could be dibenzofuran-1-yl and Ar2 could be dibenzofuran-3-yl. In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f) or preferred compounds of formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f), (D)a , (D) b , (D) c , (D) d and (D) ea monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution or no substitution with deuterium. In a preferred embodiment of the invention, the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f) are partially or completely deuterated. If the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f) are deuterated compounds, it is possible during their preparation, provided that the preparation is chosen by reacting a non-deuterated compound of one of formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f) with a deuteration source or provided that deuterated starting compounds are chosen during the preparation which are a mixture of deuterated starting compounds, that a mixture of deuterated products of the same basic chemical structure is formed which only differ in the degree of deuteration and / or the deuteration patterns.Such mixtures of deuterated compounds with 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 one embodiment of the invention, (D) are used. a , (D) b , (D) c , (D) d and (D) e for no substitution. In one embodiment of the invention, (D) a , (D) b , (D) c , (D) d and (D) efor maximum substitution. In a preferred embodiment of the at least one compound of formulas (1), (1a), (1b), (1c), (1d), (1e), and (1f), as described above or preferably described, the average degree of deuteration is at least 10 mol% to 100 mol%, preferably 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 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 catalyst 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, although the fully deuterated solvent 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. Examples of suitable compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), and (1f) are the structures listed below in Table 1. Table 1:. ro ro cn o

[0008]

[0009]

[0010] m co

[0011]

[0012] Particularly suitable compounds of formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f) are compounds E1 to E39 of Table 2. Table 2:

[0013] For the sake of simplicity, some of the compounds in Tables 1 and 2 are shown as fully deuterated compounds. These compounds generally refer to compounds having an average degree of deuteration of at least 50 mol%. The average degree of deuteration for these fully deuterated compounds in Tables 1 and 2 is preferably between 50 mol% and 100 mol%, or it has a preferred value as described above. The compounds according to the invention can be prepared by synthesis steps known to those skilled in the art, such as bromination, Suzuki coupling, Ullmann coupling, Hartwig-Buchwald coupling, etc. In the following synthesis schemes, the compounds are shown with a small number of substituents to simplify the structures. This does not exclude the presence of any other substituents in the processes.The processes shown for synthesizing the compounds of the invention are to be understood as examples. Those skilled in the art can develop alternative synthesis routes within the scope of their general technical knowledge.

[0014] Scheme 1: Detailed reaction conditions are known from the prior art or are described in the examples. By these processes, optionally followed by purification, such as recrystallization or sublimation, the compounds of formula (1) can be obtained in high purity, preferably more than 99% (determined by 1H-NMR and / or HPLC). For processing the compounds of the invention from the liquid phase, for example by spin coating or printing processes, formulations of the compounds of the invention or mixtures of compounds of the invention with other functional materials, such as matrix materials, fluorescent emitters, phosphorescent emitters, and / or emitters exhibiting TADF, are required. These formulations can be, for example, solutions, dispersions, or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone,3-Methylanisole, 4-Methylanisole, 3,4-Dimethylanisole, 3,5-Dimethylanisole, Acetophenone, α-Terpineol, Benzothiazole, Butyl Benzoate, Cumene, Cyclohexanol, Cyclohexanone, Cyclohexylbenzene, Decalin, Dodecylbenzene, Ethyl Benzoate, Indane, NMP, p-Cymene, Phenetol, 1,4-Diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, Heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, 2-Methylbiphenyl, 3-Methylbiphenyl, 1-Methylnaphthalene, 1-Ethylnaphthalene, ethyl octanoate, diethyl sebacate, octyl octanoate, heptylbenzene, menthyl isovalerate, cyclohexylhexanoate or mixtures of these solvents. 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), (1c), (1d), (1e) and (1f), as described above or preferably described, are suitable for use in an organic electronic device, preferably in an organic electroluminescent device, in particular as a matrix material. If the compound according to the invention is used as a matrix material or synonymously as a host material in an emitting layer, it is preferably used in combination with another compound. The invention therefore further provides a mixture comprising at least one compound of the formula (1) or at least one preferred compound of one of the formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f),or a compound of Table 1 or one of the compounds E1 to E39 and at least one further compound selected from the group of matrix materials, phosphorescent emitters, fluorescent emitters and / or emitters exhibiting TADF (thermally activated delayed fluorescence). 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 (1a), (1b), (1c), (1d), (1e) and (1f), or a compound of Table 1 or one of the compounds E1 to E39. The organic electronic device can, for example, consist of the organic integrated circuits (OICs),organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors, or organic photoreceptors. The organic electronic device is preferably an organic electroluminescent device. The organic electroluminescent device according to the invention (synonymously organic electroluminescent device) is, for example, an organic light-emitting transistor (OLET), an organic field quench device (OFQD), an organic light-emitting electrochemical cell (OLEC),an organic laser diode (O-laser) or an organic light-emitting diode (OLED). The organic electroluminescent device according to the invention is in particular an organic light-emitting diode or an organic light-emitting electrochemical cell. The device according to the invention is particularly preferably an OLED. The organic layer of the device according to the invention preferably contains, in addition to a light-emitting layer (EML), a hole injection layer (HIL), a hole transport layer (HTL), a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), an exciton blocking layer, an electron blocking layer and / or charge generation layers. The device according to the invention can also contain several layers from this group, preferably selected from EML, HIL, HTL, ETL, EIL and HBL.Interlayers can also be introduced between two emitting layers, which, for example, have an exciton-blocking function. If multiple emitting layers are present, they preferably have a total of several emission maxima between 380 nm and 750 nm, resulting in an overall white emission, i.e., different emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. One emitting layer can also contain several fluorescent and / or phosphorescent compounds. Systems with three emitting layers are particularly preferred, with the three layers exhibiting blue, green, and orange or red emission. As an alternative to the combination as described above,An emitting layer can also exhibit yellow emission. Such combinations are known to the person skilled in the art. The organic electroluminescent device according to the invention can also be a tandem electroluminescent device, in particular for white-emitting OLEDs. The device can also contain inorganic materials or layers composed entirely of inorganic materials. A large number of materials known in the prior art are suitable for use in the previously described layers of the organic electroluminescent device. When selecting materials, 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 applies, for example, to the energy positions of the orbitals (HOMO, LUMO) or the position of triplet and singlet energies.but also other material properties. The compound of formula (1) according to the invention, as described above or preferably described, can be used in different layers, depending on the precise structure. An organic electroluminescent device comprising a compound according to formula (1) or the preferred embodiments described above in an emitting layer as a matrix material for fluorescent emitters, phosphorescent emitters, or for emitters exhibiting TADF (thermally activated delayed fluorescence) is preferred.in particular for phosphorescent emitters. Furthermore, the compound according to the invention can also be used in an electron-transport layer and / or in 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, 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 comprising at least one compound of formula (1) or at least one preferred compound of one of formulas (1a), (1b), (1c), (1d), (1e), and (1f),or a compound of Table 1 or one of the compounds E1 to E39. 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 compounds of the formula (1), as described above or preferably described, or with the compounds of Table 1 or the compounds E1 to E39. 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 the formula (1) or the at least one preferred compound of one of the formulas (1a), (1b), (1c), (1d), (1e) and (1f),or a compound of Table 1 or one of the compounds E1 to E39 and at least one further matrix material. 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 at least one preferred compound of one of the formulas (1a), (1b), (1c), (1d), (1e) and (1f), or a compound of Table 1 or one of the compounds E1 to E39 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, 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 that emits at shorter wavelengths than the actual emitter can be present in the mixture as a co-host, or a compound that does not participate, or does not participate significantly, in charge transport, such as a wide-band-gap compound. 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. Particularly suitable hole-transporting matrix materials which are advantageously combined with compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f), as described above or preferably described, in a mixed matrix system,can be selected from the compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6), as described below. Accordingly, a further subject of the invention is an organic electronic device comprising an anode, a cathode and at least one organic layer containing at least one light-emitting layer, wherein the at least one light-emitting layer contains at least one compound of formula (1) as matrix material 1, as described above or as preferred, and at least one compound of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6) as matrix material 2, Formula (HH-1),

[0015] - , where the symbols and indices used are: A 1 is C(R 7 )2, NR 7 , O or S; L is a bond, O, S, C(R 7 )2or NR 7; A is at each occurrence independently a group of the formula (HH-4-1) or (HH-4-2), , Formula (HH-4-1) Formula (HH-4-2); 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 )2or NR 7 ; R 6 is, identically or differently at each occurrence, D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 7 may be substituted and wherein one or more non-adjacent CH2 groups are substituted by Si(R 7 )2, C=O, NR 7 , O, S or CONR 7may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, each of which is substituted by one or more radicals R 7 can be substituted; two radicals R 6 also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar5, identically or differently at each occurrence, independently represents an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which is reacted with one or more radicals R 7 may be substituted; R 7 is the same or different at each occurrence D, F, Cl, Br, I, N(R 8 )2, CN, NO2, OR 8 , SR 8 , Si(R 8 )3, B(OR 8 )2, C(=O)R 8 , P(=O)(R 8 )2, S(=O)R 8 , S(=O)2R 8 , 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 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which is substituted by one or more radicals R 8 may be substituted; two or more radicals R 7 together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system, preferably the radicals R 7 no such ring system; R 8is, on each occurrence, the same or different, H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, in particular a hydrocarbon radical, having 1 to 20 C atoms, in which one or more H atoms may also be replaced by D or F; 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; 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 the same or different at each occurrence: 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-4) are compounds of formula (HH-4-A). , where X2 is independently CH or CR 6 means and Ar5, R 6 , q, q1, q2 and v have a previously indicated or preferred meaning. Preferred compounds of formula (HH-5) are compounds of formulas (HH-5-A) to (HH-5-E),

[0016] where Ar5, R 6 , s and u have a previously indicated or preferred meaning. 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 6is 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 6 is 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 has the meaning 1. In compounds of the formula (HH-4), L is preferably a single bond or C(R 7 )2, where R 7has 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. In formula (HH-4-2) U 1 or U 2 when occurring, preferably a single bond or C(R 7 )2, where R 7 has a meaning mentioned above, particularly preferred are U 1 or U 2 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. In formula (HH-4-A), q, q1, q2 are preferably 0 or 1 when the radical R 6 is different from D. In a preferred embodiment of the compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-4-A), (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, R6 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 7 may be substituted, or an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, preferably having 5 to 40 ring atoms, each substituted by one or more radicals R 7 may be substituted. In a preferred embodiment of the compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-4-A), (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 6identically or differently on each occurrence selected from the group consisting of D or an aromatic or heteroaromatic ring system having 6 to 30 ring atoms, which is reacted with one or more radicals R 7can be substituted. Preferably, Ar5 in compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4-A), (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-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. 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 aromatic ring atoms, which may also be substituted by one or more radicals R 8 In a particularly preferred embodiment, this substituent R 7identical or different on each occurrence, represents an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, in particular having 6 to 18 aromatic ring atoms. Preferred embodiments for R 7 are phenyl, biphenyl, terphenyl and quaterphenyl, which are preferably deuterated, as well as residues derived from triazine, pyrimidine and quinazoline, which are substituted by one or more residues R 8 can be substituted. 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 aromatic ring atoms, which can also be substituted by one or more radicals R 8R is particularly preferably 7 for a methyl group or for a phenyl group, which may be deuterated. 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-4-A), (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-4-A), (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 the formula (HH-4) or (HH-4-A) are disclosed, for example, in WO2021 / 180614, pages 110 to 119, in particular as examples on pages 120 to 127. Their preparation is disclosed in WO2021 / 180614 A1 on page 128 and in the synthesis examples on pages 214 to 218.The preparation of triarylamines of formula (HH-6) is generally known, and some of the compounds are commercially available. If the at least one additional matrix material is a deuterated compound, it is possible that this at least one matrix material is a mixture of deuterated compounds with the same basic chemical structure, differing only in the degree of deuteration and / or the deuteration pattern. The statements regarding deuterated mixtures and the preparation of deuterated materials, as previously described 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-4-A), (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%. Examples of suitable further matrix materials for a combination with compounds of the formula (1), as described above or preferably described, are the compounds described in WO2019 / 229011 A1, Table 3, pages 137 to 203, which may also be partially or fully deuterated.Examples of suitable further matrix materials for a combination with compounds of formula (1) or preferred compounds of formula (1), as previously described 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. Examples of suitable further matrix materials for a 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, 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, 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]. For a combination with compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f), as described above or preferably described, compounds of the formula (HH-1) and / or the formulas (HH-4) and (HH-4-A) 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 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 a compound of formulas (1), (1a), (1b), (1c), (1d), (1e) and (1f), as previously described or preferably described, very particularly preferred compounds of formula (HH-1) or (HH-4-A) or (HH-5) or (HH-5-A) are suitable. Further examples of suitable host materials of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-4-A), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) and (HH-6) for a combination with compounds of formula (1) or preferred compounds of formula (1) as previously described or preferably described are the structures of Table 3 and Table 4 mentioned below. Table 3:.

[0017] n in Table 3 above means the number of D atoms in the respective compound and is 0 or D1 to D max , preferably D1 to D max If n = 0, this means that the compound is non-deuterated. n = D1 means that in the respective compound, one H atom is replaced by a D atom. D max means the maximum number of D atoms possible in the respective compound. The maximum number of D max can vary from connection to connection. D maxcan assume the following values ​​depending on the compound: 20, 24, 26, 28, 30, 31, 32, 34, 35, 36, 37, 38 and 40. Particularly suitable compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-4-A), (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:

[0018] For the sake of simplicity, some of the compounds in Tables 3 and 4 are shown as fully deuterated compounds. These compounds generally refer to compounds that have an average degree of deuteration of at least 50 mol%. The average degree of deuteration for these fully deuterated compounds in Tables 3 and 4 is preferably between 50 mol% and 100 mol% or has a preferred value as previously described.The above-mentioned host materials of formula (1) and their preferred embodiments or the compounds of Table 1 and the compounds E1 to E39 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 the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-4-A), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6) and their preferred embodiments of Table 3 or the compounds H1 to H39. 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-4-A), (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 E39 with the compounds H1 to H39 as shown below in Table 5.The first mixture M1, for example, is a combination of compound E1 with H1. Table 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-4-A), (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 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 aforementioned host materials of 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-4-A), (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, also contains at least one phosphorescent emitter. The present invention also relates to a mixture selected from M1 to M1089 and M1090 to M1521, which also contains at least one phosphorescent emitter.The present invention also relates to an organic electroluminescent device as described above or preferably described, wherein the light-emitting layer contains at least one phosphorescent emitter in addition to the above-mentioned host materials of the formula (1) and at least one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-4-A), (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 M1089 and M1090 to M1521. 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.This is preferably understood to mean a transition from a triplet state. Particularly suitable phosphorescent emitters (= triplet emitters) are compounds that emit light upon suitable excitation, preferably in the visible range, and also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80, in particular a metal with this atomic number. Preferably, compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are used as phosphorescent emitters, in particular compounds containing iridium or platinum. For the purposes of the present invention, all luminescent compounds containing the above-mentioned metals are considered phosphorescent emitters.In general, all phosphorescent complexes as used in the prior art for phosphorescent OLEDs and as known to those skilled in the art in the field of organic electroluminescent devices are suitable. Preferred phosphorescent emitters according to the present invention correspond to formulas (I), (II), (III), (IV) or (V). , where the symbols and indices for these formulas (I), (II), (III), (IV) and (V) have the meaning: R1 is H or D, R2 is H, D, F, CN or a branched or linear alkyl group having 1 to 10 C atoms or a partially or fully deuterated branched or linear alkyl group having 1 to 10 C atoms or a cycloalkyl group having 4 to 10 C atoms, which may be partially or fully substituted with deuterium. Preferred phosphorescent emitters according to the present invention correspond to the formulas (VI), (VII) or (VIII), where the symbols and indices for these formulas (VI), (VII) and (VIII) 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 formula (IX), Formula (IX), where the symbols and indices for this formula (IX) have the meaning: n+m is 3, n is 1 or 2, m is 2 or 1, X is, identically or differently on each occurrence, N or CR, R is, identically or differently on each occurrence, H, D, F, CN or a branched or linear alkyl group having 1 to 10 C atoms or a partially or fully deuterated branched or linear alkyl group having 1 to 10 C atoms or a cycloalkyl group having 4 to 7 C atoms which may be partially or fully substituted with deuterium or an aromatic or heteroaromatic ring system having 5 to 60 ring atoms which may be partially or fully substituted with deuterium.The invention accordingly further provides an organic electroluminescent device as described above or preferably described, characterized in that the light-emitting layer, in addition to the host materials 1 and 2, contains at least one phosphorescent emitter which corresponds to the formula (IX), as described above. In emitters of the formula (IX), n is preferably 1 and m is preferably 2. In emitters of the formula (IX), one X is preferably selected from N and the other Xs are CR or all Xs, identical or different on each occurrence, are CR. In emitters of the formula (IX), at least one R is preferably different from H. In emitters of the formula (IX), two Rs are preferably different from H and have one of the meanings otherwise given above for the emitters of the formula (IX).Preferred examples of phosphorescent emitters are described in WO2019 / 007867 on pages 120 to 126 in Table 5 and on pages 127 to 129 in Table 6. The emitters are incorporated into the description by this reference. Particularly preferred examples of phosphorescent emitters are listed in Table 6 below. Table 6:.

[0019] FNFNNN

[0020]

[0021] In the mixtures according to the invention or in the light-emitting layer of the device according to the invention, each mixture selected from the sum of the mixtures M1 to M1089 and M1090 to M1521 is preferably combined with a compound of the formulas (I) to (IX) or a compound from Table 6. The light-emitting layer in the organic electroluminescent device according to the invention comprising at least one phosphorescent emitter is preferably an infrared-emitting, yellow, orange, red, green, blue or ultraviolet-emitting layer, particularly preferably a yellow or green-emitting layer and very particularly preferably a green-emitting layer. A yellow-emitting layer is understood to mean a layer whose photoluminescence maximum is in the range from 540 to 570 nm. An orange-emitting layer is understood to 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), (1c), (1d), (1e) or (1f) and the host material 2, consisting of at least one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-4-A), (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, 10. -5molar, measured at room temperature, and any solvent in which the selected emitter dissolves at the specified concentration is suitable. Particularly suitable solvents are usually toluene or 2-methyl-THF, but also dichloromethane. The measurement is carried out using a commercially available photoluminescence spectrometer. The triplet energy T1 in eV is determined from the photoluminescence spectra of the emitters. First, the peak maximum Plmax. (in nm) of the photoluminescence spectrum is determined. The peak maximum Plmax. (in nm) is then converted to eV according to: E(T1 in eV) = 1240 / E(T1 in nm) = 1240 / PLmax. (in nm). Preferred phosphorescent emitters are therefore yellow emitters, preferably of formulas (I) to (IX) or from Table 6, whose triplet energy T1 is preferably between ~2.3 eV and ~2.1 eV. Preferred phosphorescent emitters are therefore green emitters, preferably of formulas (I) to (IX) or from Table 6, whose triplet energy T1 is preferably between ~2.5 eV to ~2.3 eV. Accordingly, particularly preferred phosphorescent emitters are green emitters, preferably of the formulas (I) to (IX) or from Table 6, as described above, whose triplet energy T1 is preferably ~2.5 eV to ~2.3 eV. Very particular preference is given to selecting green emitters, preferably of the formulas (I) to (IX) or from Table 6, as described above, for the mixture according to the invention or emitting layer according to the invention. Fluorescent emitters can also be present in the light-emitting layer of the device according to the invention or in the mixture according to the invention. Preferred fluorescent emitting compounds are selected from the class of arylamines, wherein preferably at least one of the aromatic or heteroaromatic ring systems of the arylamine is a condensed ring system, particularly preferably having at least 14 ring atoms.Preferred examples are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic chrysenamines, or aromatic chrysenediamines. An aromatic anthraceneamine is understood to be a compound in which a diarylamino group is bonded directly to an 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 an anthracene group, preferably in the 9,10-position. Aromatic pyreneamines, 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, respectively. Further preferred emitting compounds are indenofluorenamines or diamines, benzoindenofluorenamines or diamines, and dibenzoindenofluorenamines or diamines, as well as indenofluorene derivatives with condensed aryl groups.Pyrene-arylamines are also preferred. Also preferred are benzoindenofluorene amines, benzofluorene amines, extended benzoindenofluorenes, phenoxazines, and fluorene derivatives linked to furan units or thiophene units. Furthermore, the light-emitting device or the mixture according to the invention can also contain materials that exhibit TADF (thermally activated delayed fluorescence). In a further preferred embodiment of the invention, the at least one light-emitting layer of the organic electroluminescent device can 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 formulas (I) to (IX) or for an emitter of Table 6. According to one embodiment of the present invention, the mixture contains no further constituents, i.e., functional materials, in addition to the constituents of the host material of formula (1) and host material 2, as described above or preferably described. These are material mixtures that are used as such to produce the light-emitting layer.These mixtures are also referred to as premix systems, which are used as the sole material source during the vapor deposition of the host materials for the light-emitting layer and which have a constant mixing ratio during vapor deposition. This allows the vapor deposition of a layer with a uniform distribution of the components to be achieved in a simple and rapid manner, without the need for precise control of a large number of material sources. According to an alternative embodiment of the present invention, the mixture contains, in addition to the constituents of the host material of formula (1) and the 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.Preferred are premix systems consisting of two matrix materials, namely a compound of the formulas (1), (1a), (1b), (1c), (1d), (1e) or (1f) and a compound of one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-4-A), (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), (1c), (1d), (1e), or (1f) and two compounds of one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-4-A), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), or (HH-6). The components or constituents of the light-emitting layer of the device according to the invention can thus be processed by vapor deposition or from solution.The material combination of host materials 1 and 2, as described above or preferably described, optionally with the phosphorescent emitter, as described above or preferably described, is provided for this purpose in a formulation containing at least one solvent. Suitable formulations have been described previously. The light-emitting layer in the device according to the invention according to the preferred embodiments and the emitting compound preferably contains between 99.9 and 1 vol.%, more preferably between 99 and 10 vol.%, particularly preferably between 98 and 60 vol.%, most preferably between 97 and 80 vol.%.-% of matrix material comprising at least one compound of the formulas (1), (1a), (1b), (1c), (1d), (1e) or (1f) and at least one compound of one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-4-A), (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 amounts in vol.% given above.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. Preferred hole-injecting materials and / or hole-transporting materials are shown in the following table. The materials in this table can also be partially or fully deuterated. Table: The following compounds can also be partially or fully deuterated.

[0022] The sequence of layers in the organic electroluminescent device according to the invention is preferably as follows: anode / hole-injection layer / hole-transport layer / emitting layer / hole-blocking layer / electron-transport layer / electron-injection layer / cathode. This sequence of layers is a preferred sequence. It should be noted again that not all of the layers mentioned need to be present and / or that additional layers may be present. All materials 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 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, the electron-injecting material and electron-transporting material of which is selected from the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), or (1f), as described above or preferably described.Suitable cathodes for the device according to the invention include metals with low work functions, 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 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, such as Ag or Al, can also be used. Combinations of the metals, such as Ca / Ag, Mg / Ag, or Ba / Ag, are then 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.For this purpose, alkali metal or alkaline earth metal fluorides, as well as the corresponding oxides or carbonates (e.g., LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.) can be used. Lithium quinolinate (LiQ) can also be used. The layer 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. Metals with a high redox potential, such as Ag, Pt, or Au, are suitable for this purpose. Metal / metal oxide electrodes (e.g., Al / Ni / NiO) can also be used. x , Al / PtO x) may be preferred. For some applications, at least one of the electrodes must be transparent or partially transparent in order to enable either the irradiation of the organic material (organic solar cell) or the coupling out of light (OLED, O-LASER). Preferred anode materials here are conductive mixed metal oxides. Particular preference is given to indium tin oxide (ITO) or indium zinc oxide (IZO). Also preferred are conductive, doped organic materials, in particular conductive doped polymers. Furthermore, the anode can also consist of several layers, for example an inner layer made of ITO and an outer layer made of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.The organic electroluminescent device according to the invention is structured, contacted, and finally sealed during production (depending on the application), since the lifetime of the devices according to the invention is shortened in the presence of water and / or air. The production of the device according to the invention is not restricted by this. It is possible to coat one or more organic layers, including the light-emitting layer, using a sublimation process. The materials are heated in vacuum sublimation systems at an initial pressure of less than 10. -5 mbar, preferably less than 10 -6 mbar. However, it is also possible that the initial pressure is even lower, for example less than 10 -7mbar. The organic electroluminescent device according to the invention is preferably characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) method or by means of carrier gas sublimation. The materials are sublimated at a pressure between 10 -5mbar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured (e.g. BMS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301). Furthermore, the organic electroluminescent device according to the invention is preferably characterized in that one or more organic layers comprising the composition according to the invention are produced from solution, for example by spin coating, or using any printing process, such as screen printing, flexographic printing, nozzle printing or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing. This requires soluble host materials 1 and 2 and phosphorescent emitters. Processing from solution has the advantage that, for example, the light-emitting layer can be applied very easily and cost-effectively.This technique is particularly suitable for the mass production of organic electroluminescent devices. Furthermore, hybrid processes are possible in which, for example, one or more layers are applied from solution and one or more further layers are vapor-deposited. The invention therefore further provides a process for producing the organic electronic 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, the electron-injection layer and / or hole-blocking layer, is applied by vapor deposition, in particular using a sublimation process and / or an OVPD (Organic Vapor Phase Deposition) process and / or with the aid of carrier gas sublimation, or from solution, in particular by spin coating or using a printing process.When manufactured 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 substrate or the previous layer. Firstly, the materials used can each be placed in a material source and then evaporated from the various material sources ("co-evaporation"). Secondly, the various materials can be premixed ("premixed" systems) and the mixture placed in a single material source, from which it is then vaporized ("premix evaporation"). This allows for the vapor deposition of the light-emitting layer with a uniform distribution of the components in a simple and rapid manner, without the need for precise control of a large number of material sources.The following methods are possible: A method for producing the organic electronic 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, the electron injection layer and / or hole blocking layer, is applied by vapor phase deposition, in particular with a sublimation method and / or with an OVPD (Organic Vapor Phase Deposition) method and / or with the aid of carrier gas sublimation, or from solution, in particular by spin coating or with a printing method.A method for producing the organic electronic 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 of the formulas (1), (1a), (1b), (1c), (1d), (1e) or (1f) 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), (1c), (1d), (1e) or (1f) 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 of the formula (1) orthe preferred embodiments described above and below, in particular as matrix material or as electron-conducting materials, have a very long service life. In this case, these compounds bring about a 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. In this case, compounds according to the invention of the formula (1) or the preferred embodiments described above and below bring about a low operating voltage when used in electronic devices. 3. The compounds according to the invention of the formula (1) orthe preferred embodiments described above and below show very high stability and lifetime. 4. Using compounds according to formula (1) or the preferred embodiments described above and below, the formation of optical loss channels can be avoided in electronic devices, in particular organic electroluminescent devices. As a result, these devices are characterized by high PL and thus high EL efficiency of emitters and excellent energy transfer from the matrices to dopants. 5. The use of compounds according to formula (1) or the preferred embodiments described above and below in layers of electronic devices, in particular organic electroluminescent devices, leads to high mobility of the electron conductor structures. 6. Compounds according to formula (1) orThe preferred embodiments described above and below exhibit excellent glass film formation. 7. Compounds according to formula (1) or the preferred embodiments described above and below form very good films from solutions. 8. The compounds according to formula (1) or the preferred embodiments described above and below exhibit a triplet level T1, which can be in the range of 2.50 eV - 2.90 eV. These aforementioned advantages are not accompanied by an undue deterioration of the other electronic properties. It should be noted that variations of the embodiments described in the present invention fall within the scope of this invention. Any feature disclosed in the present invention may, unless explicitly excluded, be replaced by alternative features serving the same, an equivalent, or a similar purpose.Thus, unless otherwise stated, each feature disclosed in the present invention is to be regarded as an example of a generic series or as an equivalent or similar feature. All features of the present invention can be combined with one another in any way, unless certain features and / or steps are mutually exclusive. This applies in particular to preferred features of the present invention. Likewise, features of non-essential combinations can be used separately (and not in combination). The teaching of technical practice disclosed in the present invention can be abstracted and combined with other examples. The invention is explained in more detail by the following examples, without intending to limit it thereby. Examples Synthesis Examples Unless otherwise stated, the following syntheses are carried out under a protective gas atmosphere in dried solvents.The compounds of the invention can be prepared by synthetic methods known to those skilled in the art. a) 9-(4-[1,1′-biphenyl]-4-yl-6-phenyl-1,3,5-triazin-2-yl)-1-bromo-9H-carbazole. 17 g (69.4 mmol) of 1-bromo-9H-carbazole, 26.1 g (128 mmol, 75.8 mmol) of 2-[1,1′-biphenyl]-4-yl-4-chloro-6-phenyl-1,3,5-triazine, and 29.3 g (62 mmol) of K3PO4 were initially charged in 300 ml of dried DMSO and rendered inert with argon. The mixture was then heated at 100°C for 16 hours. After the reaction was complete, the reaction mixture was carefully concentrated using a rotary evaporator, the precipitated solid was filtered off with suction and washed with water and ethanol. The crude product was purified twice using a hot extractor (toluene / heptane 1:1), and the resulting solid was recrystallized from toluene. The yield after sublimation was 24.8 g (45 mmol), corresponding to 65% of theory. Analogously, the following connections are made:

[0023] b) 9-(3-(4-([1,1'-Biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-1-bromo-9H- carbazol Under an inert atmosphere, 24.5 g (100 mmol) of 1-bromo-9H-carbazole, 51.1 g (100 mmol) of 2-([1,1'-biphenyl]-4-yl)-4-(3-iodophenyl)-6-phenyl-1,3,5-triazine, 34.55 g (250 mmol) of potassium carbonate, and 1.27 g (20.0 mmol) of copper powder were placed in 400 mL of DMF, rendered inert with argon for a further 15 min, and then stirred at 130 °C for 32 h. The mixture was allowed to cool to room temperature, filtered through a bed of Celite, washed twice with 200 mL of DMF, and the DMF was removed to dryness using a rotary evaporator. The residue is extracted with dichloromethane / water, the organic phase is washed twice with water and once with saturated NaCl solution, and dried over Na2SO4. 150 mL of ethanol are added, the dichloromethane is removed using a rotary evaporator at 500 mbar, and the precipitated solid is filtered off with suction and washed with ethanol. The yield is 37 g (59 mmol), corresponding to 59% of theory. The following compounds are prepared analogously:

[0024] 5 c) 4-(9-(4-([1,1'-Biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazol-1-yl)-4H- naphtho[1,2,3,4-def]carbazol 29 g (42.7 mmol) 9-(4-[1,1′-biphenyl]-4-yl-6-phenyl-1,3,5-triazin-2-yl)-1-bromo-9H-carbazole, 9.6 g (40.7 mmol) 4H-naphtho[1,2,3,4-def]carbazole and 7.82 g (81.4 mmol; 2.00 eq.) sodium tert-butylate [CAS 865-47-4] are suspended in 500 mL ortho-xylene [CAS 95-47-6]. To this suspension, 1.50 g (3.66 mmol; 9 mol%) of dicyclohexyl-(2',6'-dimethoxy-biphenyl-2-yl)-phosphine (SPhos) [CAS 657408-07-6] and 1.12 g (1.22 mmol, 3 mol%) of tris(dibenzylideneacetone)dipalladium [CAS 51364-51-3] were added, and the reaction mixture was heated under reflux for 16 h. The reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. The resulting solid was washed with 300 mL of ethanol and recrystallized several times from a mixture of heptane and xylene. After hot filtration through Alox and final sublimation under high vacuum, the purified product was obtained as a colorless solid (27 g; 37.8 mmol; 72%).Analogously, the following connections are made:. d) 4H-Naphtho[1,2,3,4-def]carbazole-d 10 3.7 g (15.5 mmol; 1.00 eq) of 4H-naphtho[1,2,3,4-def]carbazole and 20.0 g of 5% Pt on activated carbon were suspended in 400 g (502 mmol; 1.00 eq) of deuterium oxide [CAS 7789-20-0] and 200 g (778 mmol; 1.55 eq) of toluene-d8 [CAS 2037-26-5]. The reaction mixture was stirred for 5 days at 165°C under elevated autogenous pressure. After cooling, the mixture was extracted twice with tetrahydrofuran, and the combined organic phases were washed with brine and dried over sodium sulfate. After filtration, the solvent was removed under reduced pressure. The product shown above, in a mixture with portions of H / D isotopomers and H / D isotopologues, is obtained after further purification by extraction, recrystallization, and sublimation. The yield is 1.7 g (6.9 mmol), corresponding to 47% of theory. e) Alternative preparation of 4-(9-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazol-1-yl)-4H-naphtho[1,2,3,4-def]carbazol-d31 34 g (48.0 mmol; 1.0) of 4-(9-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazol-1-yl)-4H-naphtho[1,2,3,4-def]carbazole is suspended in 640 mL (120 eq) of toluene-d8 [CAS 2037-26-5]. 16.6 mL (6.00 eq.) of trifluoromethanesulfonic acid is added to this mixture while cooling. The reaction mixture is stirred at ambient temperature 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. 28 g (37.6 mmol, 79% of theory) of the product shown above are obtained in a mixture with portions of H / D isotopomers and H / D isotopologues after chromatographic purification. Finally, the mixture is concentrated under high vacuum (p = 5 x 10 -7mbar) (purity 99.9%). The following compounds are prepared analogously: f) 9-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-8-fluoro-9H-carbazol-1-carbonitrile 14.7 g (70 mmol) of 8-fluoro-9H-carbazole-1-carbonitrile, 26.1 g (128 mmol, 75.8 mmol) of 2-[1,1′-biphenyl]-4-yl-4-chloro-6-phenyl-1,3,5-triazine, 37 g (114 mmol) of cesium carbonate, 170 mg (0.76 mmol) of palladium acetate, and 463 mg (1.5 mmol) of tri(o-tolyl)phosphine were placed in 200 ml of dried p-xylene and made inert with argon. The mixture was then heated to 100°C for 16 hours. After the reaction was complete, the reaction mixture was carefully concentrated using a rotary evaporator, the precipitated solid was filtered off with suction, and the residue was washed with water and ethanol. The crude product is purified twice using a hot extractor (toluene / heptane 1:1), and the resulting solid is recrystallized from toluene. The yield after sublimation is 21.7 g (42 mmol), 60% of theory. g) 9-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-8-(4H-naphtho[1,2,3,4-def]carbazol-4-yl)-9H-carbazole-1-carbonitrile

[0025] 20.6 g (40 mmol) of 9-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-8-fluoro-9H-carbazole-1-carbonitrile, 9.6 g (40 mmol) of 4H-naphtho[1,2,3,4-def]carbazole and 22.6 g (69.6 mmol; 2.00 eq.) of cesium carbonate [CAS 534-17-8] are suspended under argon in 160 mL of benzonitrile and the reaction mixture is heated to 150°C for 24 h. The reaction mixture is cooled to room temperature and the solvent is removed under reduced pressure. The obtained solid is washed with 300 mL of ethanol and recrystallized several times from a mixture of heptane and xylene. After hot filtration through Alox and final sublimation under high vacuum, the purified product is obtained as a colorless solid: 18.2 g (24 mmol; 62% of theory). Preparation of the OLEDs (Example A). The following examples C1 to C6 and Ex1 to Ex20 (see Tables 7 and 8) present the data for various OLEDs. Examples Ex1 to Ex20 show data for OLEDs according to the invention.The substrates used for the OLEDs in Table 7 are glass plates coated with 50 nm thick, structured ITO (indium tin oxide). The exact structure of the OLEDs can be found in Table 7. The materials required to manufacture the OLEDs are shown in Table 9, unless previously described. All materials are thermally vapor-deposited in a vacuum chamber. The emission layer always consists of at least one matrix material (also called host material) and an emitting dopant (dopant, emitter), which is mixed into the matrix material(s) by co-evaporation in a specific volume fraction. A specification such as E1:H10:TEG2 (32%:60%:8%) 40nm means that material E1 is present in a volume fraction of 32% as host material 1, compound H10 is present as host material 2 in a volume fraction of 60%, and TEG2 is present in a volume fraction of 8% in a 40nm thick layer. Analogously, for example,The hole injection layer (HIL) and the electron transport layer (ETL) consist of a mixture of two materials. OLEDs are characterized as standard. For this purpose, the electroluminescence spectra and current-voltage-luminance (IUL) curves are measured, from which the EQE is calculated. The calculation is performed assuming a Lambertian radiation pattern. The electroluminescence spectra are determined at a luminance of 1000 cd / m², and the CIE 1931 x and y color coordinates are calculated from them. The value U10 in Table 8 refers to the voltage required for a current density of 10 mA / cm². EQE10 refers to the external quantum efficiency at a current density of 10 mA / cm². The lifetime LT is defined as the time after which the luminance drops from an initial luminance L0 (in cd / m²) to a certain fraction L1 (in cd / m²) when operated with a constant current density j0 in mA / cm².A value of L1 / L0 = 90% in Table 8 means that the lifetime specified in column LT corresponds to the time (in hours) after which the luminance drops to 90% of its initial value (L0). Use of mixtures according to the invention in OLEDs The compounds or material combinations according to the invention can be used in the emission layer in phosphorescent green OLEDs. The data for the various OLEDs are summarized in Table 8. Examples C1 to C6 are comparative examples according to the prior art; examples Ex1 to Ex20 show data for OLEDs according to the invention. The examples according to the invention demonstrate, in particular, a significant advantage in the lifetime of the device. Table 7: Structure of the OLEDs. LiQ ) 1nm L Q ) 1nm LiQ ) 1nm L Q ) 1nm LiQ ) 1nm L iQ ) 1nm LiQ ) 1nm Example: U10 (V) EQE10 (%) j 0 (mA / cm²) L1 / L0 (%) LT (h) V1 3.9 28.7 80 90 61 Ex13 3.6 28.3 80 90 145

[0026] Table 9: Materials used, unless previously described

[0027] Example B) In the following examples C1 and Ex1 (see Tables 10 and 11), data for various OLEDs are presented. Example Ex1 shows data for an OLED according to the invention, while Example C1 shows the corresponding comparative example according to the prior art. The substrate used for the OLEDs in Table 10 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 10. The materials required to produce the OLEDs are shown in Table 9, unless previously described. All materials are thermally vapor-deposited in a vacuum chamber. The emission layer always consists of at least one matrix material (also called host material) and an emitting dopant (dopant, emitter), which is admixed with the matrix material(s) in a specific volume fraction by co-evaporation.A specification such as SdT1:H10:TEG2 (27%:65%:8%) 40nm means that the material SdT1 is present in a volume fraction of 27% as host material 1, the compound H10 as host material 2 in a fraction of 65%, and TEG2 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.For each example according to the invention (Ex), the relative EQE and the relative voltage are calculated in comparison to the respectively associated comparative example (V): rel. U (Ex) = 100 * (U10(Ex) / U10(V)) rel. EQE (Ex) = 100 * (EQE10(Ex) / EQE10(V)). The lifetime LT90 is defined as the time after which the luminance drops from a starting luminance L0 (in cd / m²) to 90% of this starting luminance when operated at a constant current density j0 in mA / cm². In the examples shown here, the current density used is 60mA / cm². For each example according to the invention (Ex), the relative LT is calculated in comparison to the respectively associated comparative example (V): rel. LT (Ex) = 100 * (LT90(Ex) / LT90(V)) Table 10: Structure of the OLEDs. Table 11: OLED performance data

Claims

Claims 1. Compound according to formula (1), Formula (1), where the symbols and indices used are: X is each independently N, CH, CD or CR 0 , where a maximum of three Xs can stand for N; it is excluded that adjacent Xs simultaneously represent N; X1 is each independently N, CH, CD or CR 0 , where at least one X1 is N; L1, L2 are each independently a single bond or an arylene or heteroarylene group having 5 to 40 ring atoms which is reacted with one or more radicals R 1 may be substituted; R 0 is selected at each occurrence, identically or differently, from the group consisting of 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, Cl, Br, I, CN or NO2, an aryl group having 6 to 40 C atoms, each of which is substituted by one or more radicals R 2 may be substituted, a heteroaryl group having 5 to 40 ring atoms, each substituted by one or more radicals R 2 may be substituted, an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, which may be substituted with one or more radicals R2 may be substituted, or an aralkyl or heteroaralkyl group with 5 to 40 aromatic ring atoms which are linked to one or more radicals R 2 may be substituted; R 1 is selected at each occurrence, identically or differently, from the group consisting of D, F, CN, NO2, Si(Ar)3, Si(R 2 )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 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, NR 2 , O or S and where one or more H atoms can be replaced by D, F, CN or NO2, an aryl group with 6 to 40 C atoms, each of which is substituted by one or more radicals R 2may be substituted, a heteroaryl group having 5 to 40 ring atoms, each substituted by one or more radicals R 2 may be substituted, an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, which may be substituted with one or more radicals R 2 may be substituted, or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms which may be substituted with one or more radicals R 2 may be substituted; Ar is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms which is substituted with one or more radicals R 2 may be substituted; Ar1, Ar2 are independently an aromatic or heteroaromatic ring system with 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 consisting of D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms may be replaced by D, F, or CN.

2. A compound according to claim 1, wherein the compound corresponds to formula (1a), Formula (1a), where Ar1, Ar2, X1, L1, L2 and R 0 eine in Anspruch 1 angegebene Bedeutung haben and (D) a ,(D) b , (D) c, (D) d, (D) erepresent a monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution or no substitution with deuterium and a1, a2, a3 each independently represent 0, 1, 2 or 3.

3. A compound according to claim 1 or 2, wherein X1 is N at each occurrence.

4. A compound according to one or more of claims 1 to 3, wherein L2 is a single bond.

5. A mixture comprising at least one compound according to one or more of claims 1 to 4 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).

6. Use of a compound according to one or more of claims 1 to 4 in an organic electronic device. 7.Organic electronic device comprising an anode, a cathode and at least one organic layer containing at least one compound according to one or more of claims 1 to 4.

8. The organic electronic device according to claim 7, wherein the electronic device is an organic integrated circuit (OIC), an organic field-effect transistor (OFET), an organic thin-film transistor (OTFT), an organic electroluminescent device, an organic solar cell (OSC), an organic optical detector, or an organic photoreceptor.

9. The organic electronic device according to claim 7 or 8, wherein the electronic device is an electroluminescent device.

10. The organic electronic device according to one or more of claims 7 to 9, wherein the organic layer contains at least one light-emitting layer containing the compounds according to any one of claims 1 to 4.

11. The organic electronic device according to one or more of claims 7 to 10, characterized in that the light-emitting layer contains a further matrix material. 12.Organic electroluminescent device according to claim 11, characterized in that the further matrix material corresponds to a compound of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6). ormel (HH-2), - , where the symbols and indices used are: A 1 is C(R 7 )2, NR 7 , O or S; L is a bond, O, S, C(R 7 )2or NR 7 ; A is at each occurrence independently a group of the formula (HH-4-1) or (HH-4-2), , Formula (HH-4-1) Formula (HH-4-2); X2 is 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 )2or NR 7 ; R 6is, identically or differently at each occurrence, D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 7 may be substituted and wherein one or more non-adjacent CH2 groups are substituted by Si(R 7 )2, C=O, NR 7 , O, S or CONR 7 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, each of which is substituted by one or more radicals R 7 can be substituted; two radicals R 6 also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar5, identically or differently at each occurrence, independently represents an aryl group having 6 to 40 C atoms, each of which is substituted by one or more radicals R 7may be substituted, or a heteroaryl group having 5 to 40 ring atoms, each substituted by 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 8may 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 can be substituted; two or more several 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 0 or 1 on each occurrence, where the sum of the indices on each occurrence is c+c1+c2 = 1; d, d1, d2 each independently denote 0 or 1 on each occurrence, where the sum of the indices on each occurrence is d+d1+d2 = 1; q, q1, q2 each independently denote 0, 1, 2, 3 or 4 on each occurrence; s is, on each occurrence, the same or different, 0, 1, 2, 3 or 4; t is, on each occurrence, the same or different, 0, 1, 2, or 3; u is, the same or different at each occurrence, 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. 13.Organic electronic device according to one or more of claims 7 to 12, characterized in that the light-emitting layer contains a phosphorescent emitter.

14. Organic electronic device according to one or more of claims 7 to 13, characterized in that it is an electroluminescent device selected from 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).

15. Method for producing a device according to one or more of claims 7 to 14, characterized in that the organic layer is applied by vapor deposition or from solution.

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