Materials for organic light-emitting devices

Abstract

The present invention relates to specific diazadibenzofuran and diazadibenzothiophene derivatives as OLED materials, to mixtures and formulations containing them and to electronic devices containing these compounds, in particular organic light-emitting devices containing these compounds as matrix materials, electron-transport materials or hole-blocking materials.

Description

[0001] Materials for organic light-emitting devices Technical field The present invention relates to specific diazadibenzofuran and diazadibenzothiophene derivatives, mixtures and formulations containing them, and electronic devices containing these compounds, in particular organic electroluminescent devices containing these compounds as matrix materials, electron-transport materials, or hole-blocking materials. State of the art Phosphorescent organometallic complexes are frequently used in organic electroluminescent devices (OLEDs). In general, there is still room for improvement in OLEDs, for example with regard to efficiency, operating voltage, and lifetime. The properties of phosphorescent OLEDs are determined not only by the triplet emitters used. The other materials used, such as matrix materials, are also of particular importance here.Improvements to these materials can therefore also lead to significant improvements in OLED properties. WO2018060307 A1, WO2018074881 A1, WO2021112303 A1, US2021036244 A, KR20210144979 A, ​​WO22173203 A1, KR2022042658 A, WO2019027189 A1, WO2019013526 A1, CN102786508 A, and CN113861171 A describe specific diazadibenzofuran derivatives and diazadibenzothiophene derivatives, respectively, and their suitability for organic electronic devices. In general, these materials still require improvement, particularly for use as matrix materials. The object of the present invention is to provide compounds that are particularly suitable for use as matrix materials, electron transport materials, electron injection materials, or hole blocking materials 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%, especially 3 to 15%, since the device lifetime is particularly limited here. In particular, the object of the present invention is to provide electron-transport materials that lead to an improved lifetime. It has now been found that electroluminescent devices containing compounds according to the following formula (1) exhibit improvements over the prior art, particularly 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, solves this problem and eliminates the disadvantages of the prior art. Summary of the invention The present invention firstly provides a compound of the formula (1). Formula (1), where the symbols and indices used are: Y is a bond, O or S; o is 0 or 1; (D) a ,(D) b , (D) c, (D) drepresent a monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution or no substitution with deuterium; R 0 is, identically or differently at each occurrence, CN, a straight-chain alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms or an aromatic ring system having 5 to 40 ring atoms which is substituted by one or more radicals R 1 may be substituted, where two substituents R 0 can form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system which can be substituted with one or more radicals R 1 may be substituted; a1, a2 are, identically or differently at each occurrence, 0, 1, 2, 3 or 4; n, m are 0 or 1, where n+m=1; Rx is CN or Ar2; L1 is, identically or differently at each occurrence, a single bond or a linker selected from the groups L-1 to L-30, L -13

[0002] which may be partially or fully deuterated; V1 is O or S; the dashed lines indicate the bond to the corresponding radical of formula (1); X is, at each occurrence, independently of one another, N, C-Ar1 or C, bonded to L1, where exactly two Y are N, separated by C-Ar1 or C bonded to L1; W is O or S; R# is, at each occurrence, independently of one another, D, F, CN or phenyl which is substituted with one or more radicals R 2 may be substituted; [R#]a3 represents a monosubstitution, a disubstitution, the maximum allowed substitution or no substitution with R#; R 1 is selected at each occurrence, identically or differently, from the group consisting of D, F, Cl, Br, I, CN, NO2, C(=O)R 2 , P(=O)(Ar)2, P(Ar)2, B(Ar)2, Si(Ar)3, Si(R 2)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 C atoms, each of which is substituted by one or more radicals R 2 may be substituted, with one or more non-adjacent CH2 groups being substituted by R 2 C=CR 2 , Si(R 2 )2, C=O, C=S, C=NR 2 , P(=O)(R 2 ), SO, SO2, NR 2 , O, S or CONR 2 and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which is substituted by one or more radicals R 2 may be substituted, an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 2may 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 is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms which is substituted by one or more radicals R 2 may be substituted; Ar1 ​​is an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which may be substituted with one or more radicals R 1 may be substituted; Ar2 is an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which can be substituted with one or more radicals R 1 may be substituted, excluding heteroaromatic ring systems containing a C=O bond; 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 the formula (1) as described above or preferably described later and at least one further compound selected from the group of matrix materials, phosphorescent emitters, fluorescent emitters and / or emitters exhibiting TADF (thermally activated delayed fluorescence) and / or a solvent. The invention further provides a mixture,containing at least one compound of formula (1) as described above or preferably described later, and at least one further compound selected from the group of electron-transport materials, electron-injection materials, hole-blocking materials, materials having a high dielectric constant, and / or a solvent. The invention further provides an organic electronic, preferably electroluminescent, device comprising an anode, a cathode, and at least one organic layer containing at least one compound of formula (1), as described above or preferably described later. The invention further provides a process for producing an organic electronic, preferably electroluminescent, device, as described above or preferably described below, characterized in thatthat the organic layer is applied by vapor deposition or from solution. Description of the invention In the present patent application, "D" or "D atom" denotes deuterium. An aryl group within the meaning of this invention contains 6 to 40 ring atoms, preferably C atoms. A heteroaryl group within the meaning of this invention contains 5 to 40 ring atoms, wherein the ring atoms comprise C atoms and at least one heteroatom, with the proviso that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aryl group or heteroaryl group is defined as either a simple aromatic cycle, i.e. phenyl, derived from benzene, or a simple heteroaromatic cycle, for example derived from pyridine, pyrimidine or thiophene, or a condensed aryl or heteroaryl group, for example derived from naphthalene, anthracene, phenanthrene, quinoline or isoquinoline.understood. An aryl group with 6 to 18 C atoms is therefore preferably phenyl, naphthyl, phenanthryl or triphenylenyl, whereby the attachment of the aryl group as a substituent is not restricted. The aryl or heteroaryl group within the meaning of this invention can carry one or more radicals, whereby the suitable radical is described below. If no such radical is described, the aryl group or heteroaryl group is not substituted. An aromatic ring system within the meaning of this invention contains 6 to 40 C atoms in the ring system. The aromatic ring system also includes aryl groups, as described above. An aromatic ring system with 6 to 18 C atoms is preferably formed from phenyl, fully deuterated phenyl, biphenyl, naphthyl,Phenanthryl and triphenylenyl are selected. A heteroaromatic ring system within the meaning of this invention contains 5 to 40 ring atoms and at least one heteroatom. A preferred heteroaromatic ring system has 9 to 40 ring atoms and at least one heteroatom. The heteroaromatic ring system also includes heteroaryl groups, as described above. The heteroatoms in the heteroaromatic ring system are preferably selected from N, O and / or S. An aromatic or heteroaromatic ring system within the meaning of this invention is understood to mean a system that does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups can also be interrupted by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as a C or O atom or a carbonyl group. For example, systems such as 9,9'-spirobifluorene, 9,9-dialkylfluorene, 9,9-diarylfluorene, diaryl ether, stilbene,etc. are understood as aromatic or heteroaromatic ring systems within the meaning of this invention, as are systems in which two or more aryl groups are interrupted, for example, by a linear or cyclic alkyl group or by a silyl group. Furthermore, systems in which two or more aryl or heteroaryl groups are directly bonded to one another, such as biphenyl, terphenyl, quaterphenyl or bipyridine, are also encompassed by the definition of the aromatic or heteroaromatic ring system. An aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which can be linked via any positions to the aromatic or heteroaromatic ring, is understood to mean, for example, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzfluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene,Spirobifluoren, Dihydrophenanthren, Dihydropyren, Tetrahydropyren, cis- oder trans-Indenofluoren, cis- oder trans-Monobenzoindenofluoren, cis- oder trans-Dibenzoindenofluoren, Truxen, Isotruxen, Spirotruxen, Spiroisotruxen, Furan, Benzofuran, Isobenzofuran, Dibenzofuran, Thiophen, Benzothiophen, Isobenzothiophen, Dibenzothiophen, Pyrrol, Indol, Isoindol, Carbazol, Indolocarbazol, Indenocarbazol, Pyridin, Chinolin, Isochinolin, Acridin, Phenan- thridin, Benzo-5,6-chinolin, Benzo-6,7-chinolin, Benzo-7,8-chinolin, Phenothiazin, Phenoxazin, Pyrazol, Indazol, Imidazol, Benzimidazol, Naphthimidazol, Phenan- thrimidazol, Pyridimidazol, Pyrazinimidazol, Chinoxalinimidazol, Oxazol, Benzoxazol, Naphthoxazol, Anthroxazol, Phenanthroxazol, Isoxazol, 1,2-Thiazol, 1,3-Thiazol, Benzo- thiazol, Pyridazin, Benzopyridazin, Pyrimidin, Benzpyrimidin, Chinoxalin, 1,5-Diaza- anthracen, 2,7-Diazapyren, 2,3-Diazapyren, 1,6-Diazapyren, 1,8-Diazapyren, 4,5-Diaza- pyren, 4,5,9,10-Tetraazaperylen, Pyrazin,Phenazine, phenoxazine, phenothiazine, fluorubin, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, Purine, pteridine, indolizine and benzothiadiazole. The abbreviations Ar and Ar1, identically or differently at each occurrence, mean an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which is substituted by one or more radicals R, 1 may be substituted, where the radical R 1 or the substituents R 1 has / have a meaning as described above or below. The abbreviation Ar2 stands for aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which is substituted by one or more radicals R 1may be substituted, excluding heteroaromatic ring systems containing a C=O bond, and wherein the radical R 1 or the substituents R 1 has / have a meaning as described above or below. The abbreviation Ar5, identically or differently at each occurrence, stands for an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which is substituted by one or more radicals R 7 may be substituted, where the radical R 7 or the substituents R 7has / have a meaning as described above or below. A preferred meaning of Ar5 is described below. The phrase "two or more residues can form a ring" is understood, in the context of the present description, to mean, among other things, that the two residues are linked to one another 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, the formulation according to the invention, and the organic electronic or electroluminescent device according to the invention. Preferred compounds of formula (1) with the condition n+m = 1 and n and m = 0 or 1, are compounds of formula (1a) in which Y is a bond, o = 1, n = 1 and m = 0, compounds of formula (1b) in which Y is o = 1, n = 1 and m = 0, compounds of formula (1c) in which Y is o = 1, n = 0 and m = 1, compounds of formula (1d) in which Y is o = 1, n = 1 and m = 0, compounds of formula (1e) in which Y is o = 1,n = 0 and m = 1, compounds of formula (1f) where o = 0, n = 1 and m = 0 and compounds of formula (1g) where o = 0, n = 0 and m = 1, orme ( b),

[0003] , where R 0 , (D) a , (D) b , (D) c , (D) d , a1, a2, L, X, W, R#, [R#] a3 , n, m, n+m and Ar2 have a meaning mentioned above or mentioned below with preference. The index a1 or a2 each independently represents 0, 1, 2, 3 or 4, where the position of the substituents R 0are not restricted upon occurrence. In compounds of the formula (1a), a1 is preferably 0, 1 or 2 and a2 is preferably 0 or a2 is preferably 0 or 2 and a1 is preferably 0. In compounds of the formula (1b), a1 is preferably 0 or 1 and a2 is preferably 0. In compounds of the formula (1c), a2 is preferably 0 or 1 and a1 is preferably 0. In compounds of the formula (1g), a2 is preferably 0 or 1 and a1 is preferably 0. The radical R 0 is, identically or differently at each occurrence, preferably CN, a branched or cyclic alkyl group having 3 to 20 C atoms or an aromatic ring system having 5 to 40 ring atoms which is substituted by one or more radicals R 1 may be substituted, where two substituents R 0 can form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system which can be substituted with one or more radicals R 1 may be substituted, where R 1has a meaning mentioned above or preferred below. The radical R 0 is, on each occurrence, identically or differently, particularly preferably CN, tert-butyl, 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 1 For compounds of formula (1a) it is preferred that the radical R 0 at each occurrence, identically or differently, preferably a branched or cyclic alkyl group having 3 to 20 C atoms or an aromatic ring system having 5 to 40 ring atoms which is substituted by one or more radicals R 1 may be substituted, where two substituents R 0 can form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system which can be substituted with one or more radicals R 1 may be substituted, where R 1has a meaning mentioned above or mentioned below with preference. For compounds of formula (1a), it is particularly preferred that the radical R 0 at each occurrence, identically or differently, denotes tert-butyl, 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 1 Particularly preferred compounds of formula (1) are the compounds of formulas (1a), (1b), (1c) and (1f), where R 0 , (D) a , (D) b , (D) c , (D) d , a1, a2, L, X, W, R#, [R#] a3, n, m, n+m and Ar2 have a meaning mentioned above or mentioned with preference below. In one embodiment of the invention, Rx is preferably Ar2. In one embodiment of the invention, Rx is preferably CN. In the linkers L-18 to L-30, V1 is preferably O. In one embodiment of the invention, the linker L1 in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) is a single bond or a linker selected from the group L-1 to L-17, which may be partially or fully deuterated. In a preferred embodiment of the invention, the linker L1 in compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) represents a single bond or a linker selected from the group L-2, L-3, L-4, L-5 or L-7, which may be partially or completely deuterated.In a preferred embodiment of the invention, L1 in compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) is a single bond. In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), formula (1-1) preferably corresponds to one of formulas (1-2), (1-3), (1-4) or (1-5). where * means the connection to the linker L1 and Rx, Ar1, [R#], [R#] a3 and W have a meaning previously mentioned or preferably mentioned below. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), the formula (1-1) preferably corresponds to one of the formulas (1-2) or (1-3) as described above. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) and the formulas (1-1), (1-2), (1-3), (1-4) and (1-5), W is preferably O. The substituent R 1is, when identical or different, preferably selected from the group D, F, CN, Si(Ar)3, a branched or cyclic alkyl group having 3 to 20 C atoms or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, each of which is substituted by one or more radicals R 2 may be substituted, where Ar and R 2 have a meaning previously mentioned. The substituent R 1 is preferably D, CN, phenyl, 1,3-biphenyl or 1,4-biphenyl, each of which is substituted with one or more radicals R 2 can be substituted. R 2 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 1is particularly preferably CN, D or tert-butyl, particularly preferably D. The invention accordingly further provides compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g), as described above or preferably described, in which WO is In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) or preferred compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), R# is preferably, independently of one another, on each occurrence D, F, CN or a non-deuterated, partially deuterated or fully deuterated phenyl. In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) or preferred compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), R# is preferably D at each occurrence. If R# is D, then [R#] a3 preferred for the maximum permissible substitution. If R# stands for F or CN, [R#] a3preferably for monosubstitution or disubstitution. If R# represents a non-deuterated, partially deuterated, or fully deuterated phenyl, then [R#] a3 preferably for monosubstitution. In one embodiment of the invention, [R#] a3 in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) or in preferred compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) do not represent a substitution. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) or preferred compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), Ar1 and Ar2, on each occurrence, are the same or different, preferably represent an aromatic or heteroaromatic ring system having 5 to 40 ring atoms from the group Ar-1 to Ar-28,

[0004] Ar-14

[0005] where Y 3at each occurrence, identically or differently, is O, S, NAr or C(R)2, R is methyl or phenyl, R 3 H, R 2 or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which with one or more radicals R 2 may be substituted; the dashed bond represents the bond to the remainder of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g); p is 0 or 1, where p = 0 means that the group Ar is not present and R 2 and Ar have a meaning mentioned above or a preferred meaning. Y 3 is preferably O, S, NAr or C(CH3)2. Y 3 is particularly preferably O or S. Y 3 is very particularly preferably O. Ar is preferably phenyl, 1,2-biphenyl, 1,3-biphenyl, 1,4-biphenyl, triphenylenyl, dibenzofuranyl or dibenzothiophenyl, which is substituted with one or more radicals R 2 may be substituted, where R 2has a meaning mentioned above or mentioned with preference. Ar is particularly preferably phenyl, 1,2-biphenyl, 1,3-biphenyl or 1,4-biphenyl. The substituent R 2 in Ar-1 to Ar-28, when identical or different, is preferably selected from the group consisting of D, F, CN or a straight-chain or branched alkyl group having 1 to 10 C atoms, where one or more H atoms of the alkyl group may be replaced by D, F, or CN. The substituent R 2 is preferably D or F, particularly preferably D. R 2 in Ar is preferably D, F or CN, particularly preferably D. In the structures Ar-1 to Ar-28 the substituent R 3 preferably selected, identically or differently at each occurrence, from the group consisting of H, D, F, CN or an aromatic ring system having 6 to 30 ring atoms, each of which is substituted by one or more radicals R 2 can be substituted. In the structures Ar-1 to Ar-28, the substituent R 3particularly preferably, on each occurrence, identically or differently selected from the group consisting of H, D, non-deuterated or partially or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) or preferred compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), Ar1 and Ar2, on each occurrence, identically or differently, preferably represent a group selected from Ar-1 to Ar-4, Ar-12 to Ar-16, Ar-21 to Ar-27, as described above. In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), or preferred compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), (D) a , (D) b , (D) c and (D) da 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), (1f) and (1g) are deuterated, wherein the degree of deuteration of the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) is preferably at least 10% to 100%, particularly preferably 30% to 90% and most particularly preferably 50% to 70%. The degree of deuteration is given in mol%. In one embodiment of the invention, (D) a , (D) b , (D) c and (D) d for no substitution. In one embodiment of the invention, (D) a , (D) b , (D) c and (D) dfor maximum substitution. Examples of suitable compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), and (1g) are the structures listed below in Table 1. Table 1:

[0006] Particularly suitable compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) are compounds E1 to E21 of Table 2. Table 2:

[0007] The compounds of the invention can be prepared by synthetic steps known to those skilled in the art, such as bromination, Suzuki coupling, Ullmann coupling, Hartwig-Buchwald coupling, etc. 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 the synthesis of the compounds of the invention are to be understood as examples. The skilled person can develop alternative synthesis routes within the scope of their general technical knowledge. Scheme 1: Scheme 2: Scheme 6: Detailed reaction conditions are known from the prior art or are described in the examples. By these processes, optionally followed by purification, such as recrystallization or sublimation, the compounds of formula (1) can be obtained in high purity, preferably more than 99% (determined by 1H-NMR and / or HPLC). For processing the compounds of the invention from the liquid phase, for example by spin coating or printing processes, formulations of the compounds of the invention or mixtures of compounds of the invention with other functional materials, such as matrix materials, fluorescent emitters, phosphorescent emitters, and / or emitters exhibiting TADF, are required. These formulations can be, for example, solutions, dispersions, or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone,3-Methylanisole, 4-Methylanisole, 3,4-Dimethylanisole, 3,5-Dimethylanisole, Acetophenone, α-Terpineol, Benzothiazole, Butyl Benzoate, Cumene, Cyclohexanol, Cyclohexanone, Cyclohexylbenzene, Decalin, Dodecylbenzene, Ethyl Benzoate, Indane, NMP, p-Cymene, Phenetol, 1,4-Diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, Heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, 2-Methylbiphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, diethyl sebacate, octyl octanoate, heptylbenzene, menthyl isovalerate, cyclohexylhexanoate, or mixtures of these solvents. The compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), and (1g) according to the invention, as described above or preferably described,are suitable for use in an organic electroluminescent device, in particular as a matrix material. If the compound according to the invention is used as a matrix material or synonymously as a host material in an emitting layer, it is preferably used in combination with another compound. The invention therefore further provides a mixture comprising at least one compound of formula (1) or at least one preferred compound of one of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), or a compound of Table 1 or one of the compounds E1 to E21 and at least one further compound selected from the group of matrix materials, phosphorescent emitters, fluorescent emitters, emitters exhibiting TADF (thermally activated delayed fluorescence) and / or a solvent. Suitable matrix materials and emitters that can be used in this mixture according to the invention,are described below. If the further material is a solvent, the mixture is synonymously a formulation comprising at least one compound according to the invention, as described above, and at least one solvent. The solvent can be an above-mentioned solvent or a mixture of these solvents. The present invention further provides an organic electronic device comprising an anode, a cathode, and at least one organic layer comprising at least one compound of formula (1) or at least one preferred compound of one of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), and (1g), or a compound of Table 1 or one of the compounds E1 to E21. The organic electronic device can, for example, consist of organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices,organic solar cells (OSCs), organic optical detectors, organic photoreceptors. The organic electronic device is preferably an organic electroluminescent device. The organic electroluminescent device according to the invention (synonymously organic electroluminescent device) is, for example, an organic light-emitting transistor (OLET), an organic field quench device (OFQD), an organic light-emitting electrochemical cell (OLEC),an organic laser diode (O-laser) or an organic light-emitting diode (OLED). The organic electroluminescent device according to the invention is in particular an organic light-emitting diode or an organic light-emitting electrochemical cell. The device according to the invention is particularly preferably an OLED. The organic layer of the device according to the invention preferably contains, in addition to a light-emitting layer (EML), a hole injection layer (HIL), a hole transport layer (HTL), a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), an exciton blocking layer, an electron blocking layer and / or charge generation layers. The device according to the invention can also contain several layers from this group, preferably selected from EML, HIL, HTL, ETL, EIL and HBL.Interlayers can also be introduced between two emitting layers, which, for example, have an exciton-blocking function. If multiple emitting layers are present, they preferably have a total of several emission maxima between 380 nm and 750 nm, resulting in an overall white emission, i.e., different emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. One emitting layer can also contain several fluorescent and / or phosphorescent compounds. Systems with three emitting layers are particularly preferred, with the three layers exhibiting blue, green, and orange or red emission. As an alternative to the combination as described above,An emitting layer can also exhibit yellow emission. Such combinations are known to the person skilled in the art. The organic electroluminescent device according to the invention can also be a tandem electroluminescent device, in particular for white-emitting OLEDs. The device can also contain inorganic materials or layers composed entirely of inorganic materials. It is not difficult for the person skilled in the art to resort to a large number of materials known in the prior art in order to select suitable materials for use in the previously described layers of the organic electroluminescent device. In doing so, the person skilled in the art makes common considerations regarding the chemical and physical properties of the materials, since it is known to himthat the materials in an organic electroluminescent device interact with one another. This applies, for example, to the energy positions of the orbitals (HOMO, LUMO) or the position of triplet and singlet energies, but also to other material properties. The compound of formula (1) according to the invention, as described above or preferably described, can be used in different layers, depending on the precise structure. An organic electroluminescent device containing a compound according to formula (1) or the preferred embodiments described above in an emitting layer as a matrix material for fluorescent emitters, phosphorescent emitters, or for emitters exhibiting TADF (thermally activated delayed fluorescence) is preferred.in particular for phosphorescent emitters. Furthermore, the compound according to the invention can also be used in an electron-transport layer and / or in a hole-transport layer and / or in an exciton-blocking layer and / or in a hole-blocking layer. The compound according to the invention is particularly preferably used as a matrix material in an emitting layer or in an electron-transport layer. The present invention further provides an organic electronic device as described above, wherein the organic layer contains at least one light-emitting layer which comprises at least one compound of the formula (1) or the at least one preferred compound of one of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g),or a compound of Table 1 or one of the compounds E1 to E21. 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 E21. 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 (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g),or a compound of Table 1 or one of the compounds E1 to E21 and at least one further matrix material. Accordingly, the present invention further provides an organic electronic device as described above, wherein the organic layer contains at least one light-emitting layer containing at least one compound of formula (1) or at least one preferred compound of one of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), or a compound of Table 1 or one of the compounds E1 to E21 and two further matrix materials. Suitable matrix materials that can be used in combination with the compounds according to the invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, triarylamines, carbazole derivatives, biscarbazoles, indolocarbazole derivatives, indenocarbazole derivatives, azacarbazole derivatives, bipolar matrix materials, azaboroles or boronic esters.Triazine derivatives, zinc complexes, diazasilole or tetraazasilole derivatives, diazaphosphole derivatives, bridged carbazole derivatives, triphenylene derivatives, or dibenzofuran derivatives. Likewise, another phosphorescent emitter 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 advantageously react with compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), 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,

[0008] - ), 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), 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 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.In compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-5) or (HH-6), s is preferably 0 or 1 when the radical R. 6 is different from D, or particularly preferably 0. In compounds of the formulas (HH-1), (HH-2) or (HH-3), t is preferably 0 or 1 if the radical R 6 is different from D, or particularly preferably 0. In compounds of the formulas (HH-1), (HH-2), (HH-3) or (HH-5), u is preferably 0 or 1 if the radical R 6 is different from D, or particularly preferably 0. The sum of the indices s, t and u in compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-5) or (HH-6) is preferably at most 6, particularly preferably at most 4 and particularly preferably at most 2. This preferably applies when R 6is different from D. In compounds of the formula (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 7 has a meaning mentioned above, particularly preferably L is a single bond. In formula (HH-4-1), v is preferably 0 or 1 when the radical R 6 is different from D. 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 6is different from D. In a preferred embodiment of the compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6), which can be combined according to the invention with compounds of formula (1) or preferred compounds of formula (1), as described above, R 6 identically or differently on each occurrence selected from the group consisting of D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl group is in each case substituted with one or more radicals R 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 7may be substituted. In a preferred embodiment of the compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6), which can be combined according to the invention with compounds of formula (1) or preferred compounds of formula (1), as described above, R 6 identically or differently on each occurrence selected from the group consisting of D or an aromatic or heteroaromatic ring system having 6 to 30 ring atoms, which is reacted with one or more radicals R 7can be substituted. Preferably, Ar5 in compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-5) 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, spirobifluorenyl, which may be linked via the 1-, 2-, 3- or 4-position, naphthyl, in particular 1- or 2-linked naphthyl, or residues derived from indole, benzofuran, benzothiophene, carbazole, which may be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, which may be linked via the 1-, 2-, 3- or 4-position can, dibenzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline,Phenanthrene or triphenylene, each of which is substituted with one or more radicals R, 7 may be substituted. Preferably, Ar5 is not 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 7 identical or different on each occurrence, represents an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, in particular having 6 to 18 aromatic ring atoms. Preferred embodiments for R 7are phenyl, biphenyl, terphenyl and quaterphenyl, which are preferably unsubstituted, as well as radicals derived from triazine, pyrimidine and quinazoline, which are substituted by one or more radicals R 8 can be substituted. If A 1 in formula (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 8 R is particularly preferably 7 represents a methyl group or a phenyl group. The radicals R 7also form a ring system with each other, resulting in a spiro system. In a preferred embodiment of the compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) and (HH-6), these compounds are partially or fully deuterated, particularly preferably fully deuterated. The preparation of the compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) and (HH-6) is generally known and some of the compounds are commercially available. Compounds of the formula (HH-4) are disclosed, for example, in WO2021 / 180614, pages 110 to 119, in particular as examples on pages 120 to 127. Their preparation is disclosed in WO2021 / 180614 A1 on page 128 and in the synthesis examples on pages 214 to 218. The preparation of the triarylamines of formula (HH-6) is known to the person skilled in the art and some of the compounds are commercially available.If the at least one further matrix material is a deuterated compound, it is possible for this at least one matrix material to be a mixture of deuterated compounds of the same basic chemical structure, which differ only in the degree of deuteration. In a preferred embodiment of the at least one further matrix material, this is a mixture of deuterated compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6), as described above, wherein the degree of deuteration of these compounds is at least 50% to 90%, preferably 70% to 100%. In a preferred embodiment of the at least one further matrix material, this is a mixture of deuterated compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) and / or (HH-6), as described above, wherein the degree of deuteration of these compounds is at least 50% to 90%, preferably 70% to 100%.Corresponding deuteration methods are known to the person skilled in the art and are described, for example, in KR2016041014 A, WO2017 / 122988 A1, KR2020052820 A, KR101978651 B1, and WO2018 / 110887 A1 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 or palladium catalyst and a deuterium source. The term "deuterium source" refers to any compound containing one or more D atoms and capable of releasing them under suitable conditions. The platinum catalyst is preferably dry platinum on carbon, preferably 5% dry platinum on carbon. The palladium catalyst is preferably dry palladium on carbon, preferably 5% dry palladium on carbon.A suitable deuterium source is D2O, benzene-d6, chloroform-d8, acetonitrile-d3, acetone-d6, acetic acid-d4, methanol-d4, or toluene-d8. A preferred deuterium source is D2O or a combination of D2O and a fully deuterated organic solvent. A particularly preferred deuterium source is the combination of D2O with a fully deuterated organic solvent, whereby the fully deuterated solvent is not 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 further matrix materials for a combination with compounds of formula (1), as described above or preferably described, are the compounds described in WO2019 / 229011 A1, Table 3, pages 137 to 203, which may also be partially or fully deuterated. Examples of suitable further matrix materials for a combination with compounds of formula (1) or preferred compounds of formula (1), as described above or preferably described, are the compounds described in WO2021 / 180625 A1, Table 3, pages 131 to 137 and in Table 4, pages 137 to 139, which may also be partially or fully deuterated.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]. For a combination with compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), as previously described or preferably described, compounds of formula (HH-1) and / or formula (HH-4) and / or formula (HH-5) are particularly suitable, as previously described or preferably described.For a combination with compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), as described above or preferably described, compounds of the formula (HH-1) are particularly suitable in which at least one group Ar5 represents a heteroaromatic ring system having 5 to 40 ring atoms which is reacted with one or more radicals R. 7may be substituted and / or compounds of formula (HH-4) and / or compounds of formula (HH-5). For a combination with a compound of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), as previously described or preferably described, very particularly preferred compounds of formula (HH-4) or (HH-5) are suitable.] Further examples of suitable host materials of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) 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 listed below in Table 3 and Table 4. Table 3: DDDDD D DDDDD

[0009] The abbreviation D1-D32 indicates the number of D atoms in the molecule. D1 means one H atom is exchanged for one D atom. D32 means that 32 H atoms are replaced by 32 D atoms. Particularly suitable compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6), which are selected according to the invention and are preferably used in combination with at least one compound of formula (1) in the electroluminescent device according to the invention, are the compounds in Table 4. Table 4:

[0010] The aforementioned host materials of formula (1) and their preferred embodiments, or the compounds of Table 1 and compounds E1 to E21, can be combined in any desired manner in the device according to the invention with the aforementioned matrix materials / host materials, the matrix materials / host materials of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), or (HH-6), as well as their preferred embodiments in Table 3, or compounds H1 to H33. Particularly preferred mixtures of the compounds of formula (1) with the host materials of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), or (HH-6) for the device according to the invention are obtained by combining compounds E1 to E21 with compounds H1 to H33, 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 described as preferred, in the mixture according to the invention or in the light-emitting layer of the device according to the invention is usually in the range from 5 wt. % to 90 wt. %, preferably in the range from 10 wt. % to 85 wt. %, more preferably in the range from 20 wt. % to 85 wt. %, even more preferably in the range from 30 wt. % to 80 wt. %, very particularly preferably in the range from 20 wt. % to 60 wt. % and most preferably in the range from 30 wt. % to 50 wt. %, based on the entire mixture or based on the entire composition of the light-emitting layer. The concentration of the sum of all host materials of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) 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 above-mentioned host materials of the formula (1), referred to as host material 1 in the future, and the host material of at least one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) and (HH-6), referred to as host material 2 in the future, as described above or preferably described, contains at least one phosphorescent emitter. The present invention also relates to a mixture selected from M1 to M693, which contains at least one phosphorescent emitter.It is further preferred to use a mixture of two or more triplet emitters together with a matrix of host material 1 and host material 2. The triplet emitter with the shorter-wavelength emission spectrum serves as a co-matrix for the triplet emitter with the longer-wavelength emission spectrum. The present invention also relates to an organic electroluminescent device, as described above or preferably described, wherein the light-emitting layer, in addition to the aforementioned host materials of the formula (1) and at least one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) and (HH-6), as described above or preferably described, in particular the material combinations M1 to M693, contains at least one phosphorescent emitter.The term phosphorescent emitters typically encompasses compounds in which light emission occurs through a spin-forbidden transition from an excited state with higher spin multiplicity, i.e., a spin state > 1, for example, through a transition from a triplet state or a state with an even higher spin quantum number, e.g., a quintet state. Preferably, this refers to a transition from a triplet state. Particularly suitable as phosphorescent emitters (= triplet emitters) are compounds that, upon suitable excitation, emit light, preferably in the visible range, and also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80, in particular a metal with this atomic number.Compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are preferably 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 regarded as phosphorescent emitters. In general, all phosphorescent complexes as used according to the prior art for phosphorescent OLEDs and as known to the person 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).

[0011] formula , 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), ,

[0012] formula , 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 the 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:. FFFNFNNF Ir Ir FNFNDDDNDNDDDDN Ir N Ir NNDDDDDDDD

[0013] 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 M693 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), (1f) or (1g) and the host material 2, consisting of at least one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) 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 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 one of the formulas (I) to (IX) or for an emitter of Table 6. According to one embodiment of the present invention, the mixture contains no further components, 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.Premix systems consisting of two matrix materials are preferred, namely a compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) and a compound of one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6). Premix systems consisting of three matrix materials are preferred, namely a compound of (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) and two compounds of one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) 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 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.%, very particularly preferably between 97 and 80 vol.% of matrix material made of at least one compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) and at least one compound of one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6) according to the preferred embodiments, based on the total composition of emitter and matrix material. Accordingly, the light-emitting layer in the device according to the invention preferably contains between 0.1 and 99 vol.%, more preferably between 1 and 90 vol.%, particularly preferably between 2 and 40 vol.%, very particularly preferably between 3 and 20 vol.-% of the emitter based on the total composition of the light-emitting layer consisting of emitter and matrix material. If the compounds are processed from solution, the corresponding amounts in wt.% are preferably used instead of the above-specified amounts in vol.%. The present invention also relates to an organic electroluminescent device as described above or preferably described, wherein the organic layer contains a hole-injection layer (HIL) and / or a hole-transport layer (HTL), the hole-injecting material and hole-transporting material of which belong to the class of arylamines. The sequence of layers in the organic electroluminescent device according to the invention is preferably the following: anode / hole-injection layer / hole-transport layer / emitting layer / hole-blocking layer / electron-transport layer / electron-injection layer / cathode. This sequence of layers is a preferred sequence.It should be noted again that not all of the layers mentioned need to be present and / or that additional layers may be present. All materials used as electron-transport materials in the electron-transport layer according to the state of the art 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, whose electron-injecting material and electron-transporting material are selected from the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g), as described above or preferably described. Furthermore, an electronic device, preferably an organic electroluminescent device, is preferred, which comprises one or more compounds according to the invention in one or more electron transport layers in combination with a material having a high dielectric constant.Materials that have a high dielectric constant include, for example, alkali metal or alkaline earth metal fluorides, alkali metal or alkaline earth metal oxides, alkali metal or alkaline earth metal carbonates, lanthanide compounds, or organic alkali metal complexes. A combination of organic alkali metal complexes, preferably with lithium quinolate = LiQ, with a compound according to the invention is particularly preferred. Suitable materials that have a high dielectric constant include, for example, LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, Yb2O3, or lithium quinolate. Examples of organic alkali metal complexes are compounds 179 to 223. The two different materials of the electron-transport layer can be present in a ratio of 1:50 to 50:1, preferably 1:10 to 10:1, particularly preferably 1:4 to 4:1, and most preferably 1:2 to 2:1. It is also possible to introduce an electron-injection layer between the electron-transport layer according to the invention and the cathode. Suitable materials for the electron-injection layer are, for example, LiF, lithium quinolinate, CsF, Cs2CO3, Li2O, LiBO2, K2SiO3, Cs2O, or Al2O3. Metals with a low work function, metal alloys, or multilayer structures made of different metals, such as alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Yb, Sm), are suitable as the cathode of the device according to the invention. Alloys made from an alkali or alkaline earth metal and silver are also suitable, for example an alloy made from magnesium and silver.In multilayer structures, in addition to the metals mentioned, other metals with a relatively high work function can be used, such as Ag or Al. In this case, combinations of metals such as Ca / Ag, Mg / Ag, or Ba / Ag are generally used. It may also be preferable to insert a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor. Examples of suitable materials for this include alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates (e.g., LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3). Lithium quinolinate (LiQ) can also be used. The thickness of this layer is preferably between 0.5 and 5 nm. Materials with a high work function are preferred as the anode. The anode preferably has a work function greater than 4.5 eV vs. vacuum.On the one hand, metals with a high redox potential, such as Ag, Pt, or Au, are suitable for this purpose. On the other hand, metal / metal oxide electrodes (e.g., Al / Ni / NiO) can also be used. x , Al / PtO x) may be preferred. For some applications, at least one of the electrodes must be transparent or partially transparent in order to enable either the irradiation of the organic material (organic solar cell) or the coupling out of light (OLED, O-LASER). Preferred anode materials here are conductive mixed metal oxides. Particular preference is given to indium tin oxide (ITO) or indium zinc oxide (IZO). Also preferred are conductive, doped organic materials, in particular conductive doped polymers. Furthermore, the anode can also consist of several layers, for example an inner layer made of ITO and an outer layer made of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.The organic electroluminescent device according to the invention is structured, contacted, and finally sealed during production (depending on the application), since the lifetime of the devices according to the invention is shortened in the presence of water and / or air. The production of the device according to the invention is not restricted by this. It is possible to coat one or more organic layers, including the light-emitting layer, using a sublimation process. The materials are heated in vacuum sublimation systems at an initial pressure of less than 10. -5 mbar, preferably less than 10 -6 mbar. However, it is also possible that the initial pressure is even lower, for example less than 10 -7mbar. The organic electroluminescent device according to the invention is preferably characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) method or by means of carrier gas sublimation. The materials are then sublimated at a pressure between 10 -5mbar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured (e.g. BMS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301). Furthermore, the organic electroluminescent device according to the invention is preferably characterized in that one or more organic layers comprising the composition according to the invention are produced from solution, for example by spin coating, or using any printing process, such as screen printing, flexographic printing, nozzle printing or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing. This requires soluble host materials 1 and 2 and phosphorescent emitters. Processing from solution has the advantage that, for example, the light-emitting layer can be applied very easily and cost-effectively.This technique is particularly suitable for the mass production of organic electroluminescent devices. Hybrid processes are also possible, in which, for example, one or more layers are applied from solution and one or more additional layers are deposited by vapor deposition. These processes are generally known to those skilled in the art and can be applied to organic electroluminescent devices.The invention therefore further provides a process for producing the organic electroluminescent device according to the invention, as described above or preferably described, characterized in that the organic layer, preferably the light-emitting layer, the hole-injection layer and / or hole-transport layer, is applied by vapor deposition, in particular using a sublimation process and / or an OVPD (Organic Vapor Phase Deposition) process and / or with the aid of carrier gas sublimation, or from solution, in particular by spin coating or using a printing process. When produced by vapor deposition, there are basically two ways in which the organic layer according to the invention, preferably the light-emitting layer, can be applied or vapor-deposited onto any desired substrate or the previous layer.On the one hand, the materials used can each be placed in a single material source and then evaporated from the different material sources ("co-evaporation"). On the other hand, the different materials can be premixed ("premixed systems") and the mixture placed in a single material source, from which it is then evaporated ("premix evaporation"). This allows for the simple and rapid deposition of the light-emitting layer with a uniform distribution of the components, without the need for precise control of a large number of material sources.The following methods are possible: A method for producing the organic electroluminescent device according to the invention, as described above or preferably described, characterized in that the organic layer, preferably the light-emitting layer, the electron transport layer and / or hole blocking layer, is applied by 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 electroluminescent device according to the invention, as described above or preferably described, characterized in that the light-emitting layer of the organic layer is applied by gas phase deposition, wherein the at least one compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) 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 vapor deposition, wherein the at least one compound of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), or (1g) is deposited from the vapor phase together with at least one further matrix material as a premix, sequentially or simultaneously with the light-emitting materials selected from the group of phosphorescent emitters, fluorescent emitters, and / or emitters exhibiting TADF (thermally activated delayed fluorescence). The electronic devices according to the invention, in particular organic electroluminescent devices, are characterized by one or more of the following surprising advantages over the prior art: 1.Electronic devices, in particular organic electroluminescent devices comprising compounds of the formula (1) or the preferred embodiments set out above and below, in particular as matrix material or as electron-conducting materials, have a very long service life. In particular, these compounds bring about low roll-off, i.e. a low drop in the power efficiency of the device at high luminance levels. 2. Electronic devices, in particular organic electroluminescent devices comprising compounds of the formula (1) or the preferred embodiments set out above and below as electron-conducting materials, and / or matrix materials, have excellent efficiency. In particular, compounds of the formula (1) according to the invention or the preferred embodiments set out above and below bring about a low operating voltage when used in electronic devices.3. The compounds of the invention according to formula (1) or the preferred embodiments set out above and below display very high stability and lifetime. 4. Using compounds of the formula (1) or the preferred embodiments set out above and below, the formation of optical loss channels can be avoided in electronic devices, in particular organic electroluminescent devices. As a result, these devices are distinguished by high PL and thus high EL efficiency of emitters and excellent energy transfer from the matrices to dopants. 5. The use of compounds of the formula (1) or the preferred embodiments set out above and below in layers of electronic devices, in particular organic electroluminescent devices, leads to high mobility of the electron conductor structures. 6. Compounds of the formula (1) orThe preferred embodiments described above and below exhibit excellent glass film formation. 7. Compounds according to formula (1) or the preferred embodiments described above and below form very good films from solutions. 8. The compounds according to formula (1) or the preferred embodiments described above and below exhibit a triplet level T1, which can, for example, be in the range of 2.50 eV - 2.90 eV. These aforementioned advantages are not accompanied by an unduly high deterioration of the other electronic properties. It should be noted that variations of the embodiments described in the present invention fall within the scope of this invention. Any feature disclosed in 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) 2-chloro-4,8-diphenylbenzofuro[3,2-d]pyrimidine. 31.4 g (100 mmol) of 2,4-dichloro-8-phenyl-benzofuro[3,2-d]pyrimidine, 12.2 g (100 mmol) of phenylboronic acid, and 11.8 g (111 mmol) of sodium carbonate were dissolved in 800 mL of 1,4-dioxane, 800 mL of water, and 250 mL of toluene, and stirred under an argon atmosphere. 1.2 g (1 mmol) of tetrakis(triphenylphosphine)palladium was added to the flask. The reaction mixture was stirred under reflux overnight. After cooling, the mixture was quenched. The organic phase was separated, washed three times with 300 mL of water, dried over MgSO4, filtered, and the solvent was removed in vacuo. The residue is purified by column chromatography on silica gel (eluent: DCM / heptane (1:10). The yield is 28 g (80 mmol), corresponding to 80% of theory. The following compounds are prepared analogously:

[0014] b) 4,8-Diphenyl-2-(9,9'-spirobi[fluorene]-2'-yl)benzofuro[3,2-d]pyrimidin 35.6 g (100 mmol) of 2-chloro-4,8-diphenylbenzofuro[3,2-d]pyrimidine, 36 g (100 mmol) of 9,9'-spirobi[fluorene]-2'-boronic acid, and 11.8 g (111 mmol) of sodium carbonate were dissolved in 800 ml of 1,4-dioxane, 800 ml of water, and 250 ml of toluene, and stirred under an argon atmosphere. 1.2 g (1 mmol) of tetrakis(triphenylphosphine)palladium was added. The reaction mixture was stirred under reflux overnight. After cooling, the mixture was quenched. The organic phase was separated, washed three times with 300 ml of water, dried over MgSO4, filtered, and the solvent was removed in vacuo. The residue is purified by column chromatography on silica gel (eluent: DCM / heptane (1:10)) and finally sublimed under high vacuum. The yield is 51 g (79 mmol), corresponding to 79% of theory. The following compounds are prepared analogously:

[0015] c) B-[4-(9,9′-Spirobi[9H- fluoren-9,9′-[9H]xanthen -2-yl)phenyl] boronsäure 46 g (95 mmol) of 2-(4-bromophenyl)spiro[9H-fluorene-9,9′-[9H]xanthene was dissolved in 500 mL of THF under an argon atmosphere and then cooled to -78 °C. 10 mL (104 mmol / 2.5 M in hexane) of butyllithium was added dropwise at -78 °C, and the mixture was stirred for two hours. 15 g (144 mmol) of trimethyl borate was then added dropwise at -78 °C, and the mixture was stirred overnight at room temperature. 200 mL of 2N hydrochloric acid was added and stirred for one hour. The organic phase was separated, washed three times with 300 mL of water, dried over MgSO4, filtered, and the solvent was removed in vacuo. The residue was washed with 500 mL of heptane, filtered, and dried. The yield is 32.6 g (72 mmol), corresponding to 76% of theory. Preparation of the OLEDs (Example A): The following examples (V1 to V12 and B1 to B34) (see Tables 7 and 8) present the data for various OLEDs.Examples B1 to B34 show data from OLEDs according to the invention. Glass plates coated with structured ITO (indium tin oxide) with a thickness of 50 nm are used as the substrate for the OLEDs in Table 7. The exact structure of the OLEDs can be found in Table 7. The materials required to produce the OLEDs are shown in Table 9, unless previously described. All materials are thermally vapor-deposited in a vacuum chamber. The emission layer always consists of at least one matrix material (also called host material) and an emitting dopant (dopant, emitter), which is admixed to the matrix material(s) in a specific volume fraction by co-evaporation.A specification such as VG1:H2:TEG1 (33%:60%:7%) 30nm means that the material VG1 is present in a volume fraction of 33% as host material 1, the compound H2 as host material 2 in a fraction of 60%, and TEG1 in a fraction of 7% in a 30nm thick layer. Analogously, the hole injection layer (HIL) and the electron transport layer (ETL), for example, can 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 electroluminescence spectra are determined at a luminance of 1000 cd / m², and the CIE 1931 x and y color coordinates are calculated from this. The value U1000 in Table 8 refers to the voltage required for a luminance of 1000 cd / m².EQE1000 refers to the external quantum efficiency at a luminance of 1000 cd / m². The lifetime LT is defined as the time after which the luminance drops from an initial luminance L0 (in cd / m²) to a certain proportion L1 (in cd / m²) when operated at a constant current density of 20 mA / cm². A value of L1 / L0 = 80% in Table 8 means that the lifetime specified in column LT corresponds to the time (in hours) after which the luminance drops to 80% of its initial value (L0). Use of mixtures according to the invention in OLEDs The compounds or material combinations according to the invention can be used in the emission layer in phosphorescent green OLEDs. The examples according to the invention demonstrate, in particular, a significant advantage in the current efficiency and / or lifetime of the device. Table 7: Structure of the OLEDs.

[0016] Table 8:

[0017] Table 9: Materials used, unless previously described

[0018] Example B) Production of the OLEDs In the following examples nV1, nB1 and nB2 (see Tables 10 and 11), the data for various OLEDs are presented. Examples nB1 to nB2 show data from OLEDs according to the invention. The substrate 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. 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 to the matrix material(s) in a specific volume fraction by co-evaporation.A specification such as ST2:H1:TEG2 (33%:60%:7%) 30nm means that the material ST2 is present in a volume fraction of 33% as host material 1, the compound H1 as host material 2 in a fraction of 60%, and TEG2 in a fraction of 7% in a 30nm thick layer. Analogously, the hole injection layer (HIL) and the electron transport layer (ETL), for example, can 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 electroluminescence spectra are determined at a luminance of 1000 cd / m², and the CIE 1931 x and y color coordinates are calculated from this. The value U10 in Table 11 indicates 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 operating at a constant current density j0 in mA / cm². A value of L1 / L0 = 80% in Table 11 means that the lifetime specified in column LT corresponds to the time (in hours) after which the luminance drops to 80% of its initial value (L0). Table 10: Structure of OLEDs. Table 11:

Claims

Claims 1. Compound according to formula (1), Formula (1), where the symbols and indices used are: Y is a bond, O or S; o is 0 or 1; (D)a, (D)b, (D)c, (D)d represent a monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution or no substitution with deuterium; R 0 is, identically or differently at each occurrence, CN, a straight-chain alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms or an aromatic ring system having 5 to 40 ring atoms which is substituted by one or more radicals R 1 may be substituted, where two substituents R 0 can form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system which can be substituted with one or more radicals R 1may be substituted; a1, a2 are, identically or differently at each occurrence, 0, 1, 2, 3 or 4; n, m are 0 or 1, where n+m=1; Rx is CN or Ar2; L1 is, identically or differently at each occurrence, a single bond or a linker selected from the groups L-1 to L-30, L-1 L-2 L-3 L-4 which may be partially or fully deuterated; V1 is O or S; the dashed lines indicate the bond to the corresponding radical of formula (1); X is, at each occurrence, independently N, C-Ar1 or C, bonded to L1, where exactly two Ys are N separated by C-Ar1 or C bonded to L1; W is O or S; R# is, at each occurrence, independently D, F, CN or phenyl which is substituted with one or more radicals R 2may be substituted; [R#]a3 represents a monosubstitution, a disubstitution, the maximum allowed substitution or no substitution with R#; R 1 is selected at each occurrence, identically or differently, from the group consisting of D, F, Cl, Br, I, CN, NO2, C(=O)R 2 , P(=O)(Ar)2, P(Ar)2, B(Ar)2, Si(Ar)3, Si(R 2 )3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 C atoms, each of which is substituted by one or more radicals R 2 may be substituted, with one or more non-adjacent CH2 groups being substituted by R 2 C=CR 2 , Si(R 2 )2, C=O, C=S, C=NR 2 , P(=O)(R 2 ), SO, SO2, NR 2 , O, S or CONR 2and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, each of which is substituted by one or more radicals R 2 may be substituted, an aryloxy or heteroaryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by 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 can 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 by one or more radicals R 2 may be substituted; Ar1 ​​is an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which may be substituted with one or more radicals R 1may be substituted; Ar2 is an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which is substituted with one or more radicals R 1 may be substituted, excluding heteroaromatic ring systems containing a C=O bond; 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. Compound according to claim 1, where Y is a bond and o = 1.

3. Compound according to claim 1 or 2, where Y is Y and o = 1.

4. Compound according to one or more of claims 1 to 3, where WO is.

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 exhibiting TADF (thermally activated delayed fluorescence) and / or a solvent. 6.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 electron transport materials, electron injection materials, hole blocking materials, materials having a high dielectric constant, and / or a solvent.

7. An 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. An organic electronic device according to claim 7, wherein the electronic device is an electroluminescent device.

9. An organic electronic device according to claim 7 or 8, wherein the organic layer contains at least one light-emitting layer containing the compounds according to one of claims 1 to 4.

10. An organic electronic device according to one or more of claims 7 to 9, characterized in that the light-emitting layer contains a further matrix material.

11. An organic electroluminescent device according to claim 10, 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), oe - , 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 at each occurrence, identically or differently, D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 7may be substituted and wherein one or more non-adjacent CH2 groups are substituted by Si(R 7 )2, C=O, NR 7 , O, S or CONR 7 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, each of which is substituted by one or more radicals R 7 can be substituted; two radicals R 6 also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar5, identically or differently at each occurrence, independently represents an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which is reacted with one or more radicals R 7 may be substituted; R 7 is the same or different at each occurrence D, F, Cl, Br, I, N(R 8 )2, CN, NO2, OR 8 , SR 8 , Si(R 8 )3, B(OR 8 )2, C(=O)R 8 , P(=O)(R 8 )2, S(=O)R 8 , S(=O)2R 8 , OSO2R8 , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 8 may be substituted, with one or more non-adjacent CH2 groups being substituted by Si(R 8 )2, C=O, NR 8 , O, S or CONR 8 or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which can be replaced by one or more residues R 8 may be substituted; two or more radicals R 7 together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system, preferably the radicals R 7 no such ring system; R 8is, on each occurrence, the same or different, H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, in particular a hydrocarbon radical, having 1 to 20 C atoms, in which one or more H atoms may also be replaced by F; c, c1, c2 each independently denote 0 or 1 on each occurrence, where the sum of the indices on each occurrence is c+c1+c2 = 1; d, d1, d2 each independently denote 0 or 1 on each occurrence, where the sum of the indices on each occurrence is d+d1+d2 = 1; q, q1, q2 each independently denote 0, 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, at each occurrence, the same or different, 0, 1, or 2; u1, u2 each independently represent 0 or 1 at each occurrence, with the sum u1 + u2 = 1; and v is 0, 1, 2, or 3. 12.The organic electronic device according to one or more of claims 7 to 11, characterized in that the light-emitting layer contains a phosphorescent emitter.

13. The organic electronic device according to claim 7 or 8, wherein the organic layer contains at least one electron-transport layer, electron-injection layer, or hole-blocking layer containing the compounds according to any one of claims 1 to 4.

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

15. A 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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