Materials for organic light-emitting devices

Abstract

The present invention relates to OLED materials for use in electronic devices, in particular in organic light-emitting devices, and to electronic devices, in particular organic light-emitting devices, which contain these OLED materials.

Description

[0001] Foreignfiling_text P24-134.doc - 1 - Materials for Organic Light-Emitting Devices The present invention relates to OLED materials for use in electronic devices, in particular in organic light-emitting devices, as well as electronic devices, in particular organic light-emitting devices, containing these OLED materials. In organic electroluminescent devices (OLEDs), phosphorescent metal-organic complexes are frequently used as emitting materials. In general, there is still room for improvement in OLEDs, especially in OLEDs that exhibit triplet emission (phosphorescence), for example with regard to efficiency, operating voltage, and lifetime. The properties of phosphorescent OLEDs are not solely determined by the triplet emitters used.15 Here, the other materials used, such as matrix materials or charge transport materials, are also of particular importance. Improvements to these materials can therefore also lead to improvements in the OLED properties. 20 In addition, many electroluminescent devices include, besides an emission layer, other layers, such as one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, and / or charge generation layers. These layers have a significant influence on the performance of electroluminescent devices. For charge transport materials, such as electron transport materials, there is a particular need for materials with a low refractive index (RI).A reduced refractive index of the electron transport layer leads to improved light extraction and thus to improved external quantum efficiency. The object of the present invention is to provide compounds suitable for use in an OLED, in particular as a matrix material for phosphorescent emitters or as an electron transport material, and which exhibit good properties there. In particular, it is an object of the present invention to provide materials with a low refractive index for use in an electron transport layer, which thereby lead to improved extraction. Compounds of the general formula [RSiO3 / 2]n with n = 6, 8, 10 or 12 are generally known under the generic term silsesquioxanes.Surprisingly, it was found that certain silsesquioxane derivatives, described in more detail below, solve the problem described above and are well suited for use in OLEDs. In particular, the OLEDs exhibit a long lifetime, high efficiency, and low operating voltage. Furthermore, the materials have a lower refractive index than materials commonly used in electron transport layers. These compounds, as well as electronic devices, especially organic electroluminescent devices containing these compounds, are therefore the subject of the present invention. The use of silsesquioxane derivatives in the hole transport layer of an OLED is known from US 9,755,165. Silsesquioxane derivatives suitable for use in an electron transport layer are not disclosed.25 US 11,183,649 describes an OLED which includes a performance enhancement layer with a refractive index ≤ 1.6 at a wavelength of 1200 nm as an additional layer between the electron transport layer and the cathode, and discloses, among other materials for use in this layer, alkyl- or aryl-substituted silsesquioxane derivatives, in particular compounds substituted with fluorinated alkyl or aralkyl groups. This layer also contains an n-doped element. Compared to the standard OLED structure, this design has the disadvantage that the use of an additional layer results in a significantly more complex device structure. Furthermore, the use of fluorinated alkyl or aryl groups is disadvantageous from an environmental perspective, and a ban on certain fluorine-substituted alkyl groups (PFAS) is currently under discussion.The present invention therefore relates to a compound according to the following formula (1), 5 (R')7Si8O12-Ar-ETU Formula (1) wherein the symbols used are defined as follows: 10 ETU is an electron-transporting unit selected from the group consisting of triazine, pyrimidine, quinoxaline, quinazoline, benzoquinazoline, benzoquinoxaline, benzimidazole, diazadibenzofuran, diazadibenzothiophene and diazacarbazole, wherein these groups may each be partially or completely deuterated 15 and / or substituted by one or more R groups; Ar is a bivalent aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, each of which may be partially or completely deuterated and / or substituted by one or more 20 R groups. 1 may be substituted; R' is the same or different in each occurrence F, OR 1, a straight-chain alkyl group with 1 to 20 carbon atoms or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein the alkyl group 25 may in each case be partially or completely deuterated and / or with one or more R groups 1 can be substituted, with one or more non-adjacent CH2 groups being replaced by Si(R 1 )2, C=O, NR 1 , O, S or CONR 1 can be replaced, or an aromatic ring system with 6 to 12 aromatic ring atoms, 30 each of which can be partially or completely deuterated and / or with one of the several R groups 1 may be substituted; R is the same or different in each occurrence H, D, F, N(R 1 )2, CN, NO2, OR 1 , SR 1 , COOR 1 , C(=O)N(R 1 )2, Si(R 1 )3, B(OR 1 )2, C(=O)R 1 , 35 P(=O)(R 1 )2, S(=O)R 1 , S(=O)2R 1 , OSO2R 1, a straight-chain alkyl group with 1 to 20 carbon atoms, or an alkenyl or alkynyl group with 2 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein the alkyl, alkenyl, or alkynyl group is each linked to one or more R groups 1 can be substituted, with one or more non-adjacent CH2 groups 5 being replaced by Si(R 1 )2, C=O, NR 1 , O, S or CONR 1 can be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, which is coupled with one of the several R groups 1 can be substituted; two residues R can also form an aliphatic, heteroaliphatic, aromatic or 10 heteroaromatic ring system together; R 1 is the same or different in each occurrence H, D, F, Cl, Br, I, N(R 2 )2, CN, NO2, OR 2 , SR 2 , Si(R 2 )3, B(OR 2)2, C(=O)R 2 , P(=O)(R 2 )2, S(=O)R 2 , S(=O)2R 2 , OSO2R 2 , a straight-chain alkyl group with 1 to 15-20 carbon atoms, or an alkenyl or alkynyl group with 2 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein the alkyl, alkenyl, or alkynyl group is each linked to one or more R groups 2 can be substituted, with one or more non-adjacent CH2 groups being replaced by Si(R 2 )2, C=O, 20 NR 2 , O, S or CONR 2 can be replaced and wherein one or more H atoms in the alkyl, alkenyl or alkynyl group can be replaced by D, F, Cl, Br, I or CN, or an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, each of which is replaced by one or more R groups 2 can be substituted 25; in this case, two or more residues R can be involved. 1together form an aliphatic, aromatic, or heteroaromatic ring system; R 2is, in each occurrence, the same or different H, D, F, CN, or an aliphatic, aromatic, or heteroaromatic organic residue, in particular a hydrocarbon residue, with 1 to 20 C atoms, in which one or more H atoms may also be replaced by F. 35 Foreignfiling_text P24-134.doc - 5 - The unit (R')7Si8O12- in the compound according to the invention is a silsesquioxane with eight silicon atoms and has the following structure: 5 . 10 Here, the dashed bond describes the bond to the unit -Ar-ETU in formula (1), and R' has the meanings listed above. An aryl group within the meaning of this invention contains 6 to 40 C atoms; a 15 heteroaryl group within the meaning of this invention contains 2 to 40 C atoms and at least one heteroatom, provided that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aryl group is used as the basis for this.A heteroaryl group is understood to be either a simple aromatic cycle, i.e., benzene, or a simple heteroaromatic cycle, for example, pyridine, pyrimidine, thiophene, etc., or a fused (fused) aryl or heteroaryl group, for example, naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic compounds linked to each other by single bonds, such as biphenyl, are not referred to as aryl or heteroaryl groups, but rather as aromatic ring systems. An aromatic ring system within the meaning of this invention contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, in the ring system. A heteroaromatic ring system according to this invention contains 2 to 60 carbon atoms, preferably 2 to 40 carbon atoms, and at least one heteroatom in the ring system, provided that the sum of carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from nitrogen, oxygen, and / or sulfur.An aromatic or heteroaromatic ring system within the meaning of this invention is understood to be a system that does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups may also be linked by a non-aromatic unit, such as a carbon, nitrogen, or oxygen atom. Likewise, systems in which two or more aryl or heteroaryl groups are directly linked to one another are understood to be aromatic ring systems within the meaning of this invention, as are systems in which two or more aryl or heteroaryl groups may be linked by a non-aromatic unit, such as a carbon, nitrogen, or oxygen atom. Preferred aromatic or heteroaromatic ring systems are simple aryl or...Heteroaryl groups, as well as groups in which two or more aryl or heteroaryl groups are directly linked to one another, for example biphenyl or bipyridine, as well as fluorene or spirobifluorene. 15 Within the scope of the present invention, the term alkyl group includes both linear and branched and / or cyclic alkyl groups, wherein cyclic alkyl groups can be monocyclic, bicyclic, tricyclic or oligocyclic. The same applies to alkenyl and alkynyl groups. 20 Within the scope of the present invention, an aliphatic hydrocarbon residue or an alkyl group oran alkenyl or alkynyl group, which may contain 1 to 40 carbon atoms, and in which individual hydrogen atoms or CH2 groups may also be substituted by the groups 25 mentioned above, preferably the residues methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, neo-pentyl, cyclopentyl, n-hexyl, neo-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, 30 hexenyl, cyclohexenyl, heptenyl, Cycloheptenyl, Octenyl, Cyclooctenyl, Ethinyl, Propynyl, Butynyl, Pentinyl, Hexinyl, Heptinyl, or Octinyl are understood. Under an alkoxy group OR. 1mit 1 bis 40 C-Atomen werden bevorzugt Methoxy, Trifluormethoxy, Ethoxy, n-Propoxy, i-Propoxy, n-Butoxy, i-Butoxy, s-Butoxy, t-Butoxy, n-Pentoxy, s-Pentoxy, 2-Methyl- 35 butoxy, n-Hexoxy, Cyclohexyloxy, n-Heptoxy, Cycloheptyloxy, n-Octyloxy, Foreignfiling_text P24-134.doc - 7 - Cyclooctyloxy, 2-Ethylhexyloxy, Pentafluorethoxy und 2,2,2-Trifluorethoxy verstanden. Unter einer Thioalkylgruppe SR 1mit 1 bis 40 C-Atomen werden insbesondere Methylthio, Ethylthio, n-Propylthio, i-Propylthio, n- Butylthio, i-Butylthio, s-Butylthio, t-Butylthio, n-Pentylthio, s-Pentylthio, n- Hexylthio, Cyclohexylthio, n-Heptylthio, Cycloheptylthio, n-Octylthio, Cyclo- 5 octylthio, 2-Ethylhexylthio, Trifluormethylthio, Pentafluorethylthio, 2,2,2- Trifluorethylthio, Ethenylthio, Propenylthio, Butenylthio, Pentenylthio, Cyclopentenylthio, Hexenylthio, Cyclohexenylthio, Heptenylthio, Cyclo- heptenylthio, Octenylthio, Cyclooctenylthio, Ethinylthio, Propinylthio, Butinylthio, Pentinylthio, Hexinylthio, Heptinylthio oder Octinylthio ver- 10 standen.In general, alkyl, alkenyl, alkynyl, alkoxy, or thioalkyl groups according to the present invention can be straight-chain, branched, or cyclic, wherein one or more non-adjacent CH₂ groups can be replaced by the aforementioned groups; furthermore, one or more H atoms can also be replaced by D, F, Cl, Br, I, CN₁₅, or NO₂, preferably by D, F, or CN. An aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each further compounded with the aforementioned R groups, is further described. 1Substitutions may include, in particular, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, Acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, 30 pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazinimidazole, quinoxalinimidazole, oxazole, benz- oxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzo-pyridazine, pyrimidine, benzopyrimidine, quinazoline, quinoxaline, 1,5-diaza-35anthracene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-Diaza- Foreignfiling_text P24-134.doc - 8 - pyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorubin, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3- Oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-5-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, or groups derived from combinations of these systems. The formulation states that two or more residues can combine to form a 10-membered ring.Within the context of this description, it should be understood, among other things, that the two residues are linked to each other by a chemical bond with the formal elimination of two hydrogen atoms. This is illustrated by the following scheme: 15 Ring formation = of the residues RR, R H3 C C2H5 H2 C CH2C H2. 20 Analogously, the formation of a condensed aromatic ring is possible if two substituents R, each representing an alkenyl group, are linked together by a chemical bond with the formal elimination of two hydrogen atoms. 25 Furthermore, the above formulation should also be understood to mean that if one of the two substituents represents hydrogen, the second substituent bonds to the position to which the hydrogen atom was bonded, forming a ring. This is illustrated by the following scheme: 30 Ring formation = of the substituents RR R H CHCH 32.35 Foreignfiling_text P24-134.doc - 9 - The compounds according to the invention can also be partially or completely deuterated. According to the invention, the compounds have an electron transporting unit (ETU) 5 which is linked to the silsesquioxane (R')7Si8O12- via an aromatic or heteroaromatic linker Ar and which is selected from the group consisting of triazine, pyrimidine, quinoxaline, quinazoline, benzoquinazoline, benzoquinoxaline, benzimidazole, diazadibenzofuran, diazadibenzothiophene, and diazacarbazole, wherein these groups can each be partially 10 or completely deuterated and / or substituted by one or more R groups. In a preferred embodiment of the invention, the ETU unit is selected from the structures of the following formulas (ETU-1) to (ETU-13), 15 RRR N R RR R N R N N N N N N NR R R20(ETU-1) (ETU-2) (ETU-3)(ETU-4) RRRRRRRRNRRNRRNNR 25 N N RR (ETU-5) (ETU-6)(ETU-7) RRRRRRRR 30 RNRRRRRRRNN N RRRN N(ETU-10) (ETU-8) (ETU-9) 35 Foreignfiling_text P24-134.doc - 10 - 5 where R has the meanings mentioned above, E stands for O, S or NR, and the dashed line indicates the bond to Ar. Preferably, a maximum of two of the explicitly drawn residues R represent a residue other than H or D. 10 Preferred structures ETU are the structures of the following formulas (ETU-1a) to (ETU-13a), 15 20 25 30 35 Foreignfiling_text P24-134.doc - 11 - where the symbols used have the meanings mentioned above and the structures may also be partially or completely deuterated. The explicitly drawn residues R preferably represent, in each occurrence the same or different, an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, each of which is also partially or completely deuterated and / or contains one or more residues R 1may be substituted. If E stands for NR, then the residue R, which bonds to the N atom, preferably represents an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, each of which is also partially or completely deuterated and / or contains one or more residues R 1 can be substituted. In a preferred embodiment of the invention, R is selected from the group consisting of 15 H, D, F, CN, OR, either the same or different, for each occurrence. 1 , a straight-chain alkyl group with 1 to 10 carbon atoms or an alkenyl group with 2 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl or alkenyl group is each linked to one or more R groups 1 may be substituted, but is preferably unsubstituted, or an aromatic 20 or heteroaromatic ring system with 6 to 30 aromatic ring atoms, coupled with one or more R groups 1may be substituted; two adjacent R groups may also form an aliphatic, aromatic, or heteroaromatic ring system. Particularly preferably, R is selected from the group consisting of H, D, a straight-chain alkyl group with 1 to 6 carbon atoms, in particular with 1, 2, 3, or 4 carbon atoms, a straight-chain alkenyl group with 2 to 4 carbon atoms, in particular with 2 carbon atoms, or a branched or cyclic alkyl group with 3 to 6 carbon atoms, wherein the alkyl or alkenyl group is each 30 linked to one or more R groups. 1 may be substituted, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, coupled with one or more R groups 1may be substituted. R is particularly preferred in each occurrence, whether selected the same or different from the group 35 consisting of H, D or an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, in particular with 6 to 13 aromatic ring atoms, each of which is coupled with one or more R groups. 1may be substituted. Suitable aromatic or heteroaromatic ring systems R are 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, fluorene, which may be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which may be linked via the 1-, 2-, 3- or 4-position, naphthalene, which may be linked via the 1- or 2-position, 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, dibenzothiophene, which may be linked via the 1-, 2-, 3- or 4-position linked 15 may be, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline, quinoxaline, benzimidazole, phenanthrene,Triphenylene or a combination of two or three of these groups, each of which may be partially or completely deuterated and / or have one or more R groups, 1 Substitutions can be made. Aromatic ring systems or carbazole are preferred. The aromatic or heteroaromatic groups R are preferably chosen from the groups of the following formulas R-1 to R-83, 25 30 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R1 R1 R1 R1 R1 R1 R1 R1 R 1 R 1 R 1 R1 R 1 R 1 R 1 1 R 1 R 1 R 1 R 1 35 R R -5 R-6 R-7 Foreignfiling_text P24-134.doc - 14 - 5 10 R 1 R 1 R 1 A 1 Ar 1 R 1 R 1 R 1 R 1 R 1 R 1 A 1 R 1 R 1 m N A 1 R 1 R 1 R 1 R 1 R 1 R 1 15 R 1 1 1 R 1 R 1 A R1 1 1 R 1 A R1 1 R1 R 1 R R R R-29 R-31 R-30 A r 1 1 1 1 1 1 1 m R R 1 1 1 R R R R 1 R R R R N A 1 A1 R 1 R 1 R 1 R 1 R 1 A 1 1 A 1 R1 R1 1 A 1 20 R1 R1 R1 R R1 R1 R R 1 R -32 R-33 R 1 R 1 R 1 R-34 25 30 35 Foreignfiling_text P24-134.doc - 16 - 5 10 15 20 25 R 1 R 1 R 1 R 1 R 1 R 1 30 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R-69 R-70 R-71 R-7235 Foreignfiling_text P24-134.doc - 17 - 5 10 15 20 wobei R 1the above-mentioned meanings, the dashed line represents the group's connection to ETU and furthermore: 25 Ar 1 In each occurrence, it is either the same or different: a bivalent aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, each with one or more R groups. 1 may be substituted; 30 A 1 is the same or different in each occurrence C(R) 1 )2, NR 1 , O or S; or in formulas R-40, R-41 and R-42, a single bond is the same or different at each occurrence, C(R 1 )2, NR 1 , O or S; n is 0 or 1, where n = 0 means that there is no 35 Group A at this position. 1 is bound and instead of carbon atoms, residues R 1 are bound; Foreignfiling_text P24-134.doc - 18 - m is 0 or 1. If the above-mentioned groups R-1 to R-83 are multiple groups A 1If they exhibit, then all combinations from the definition of 5 A are suitable. 1 in question. Preferred embodiments are then those in which a group A 1 for NR 1 and the other group A 1 for C(R 1 )2 stands or in which both groups A 1 for NR 1 stand or in which both groups A 1 for O. In a particularly preferred embodiment of the invention, groups R, which are several groups A, represent 1 exhibit at least 10 members of a group A 1 for C(R 1 )2 or for NR 1 If A 1 for NR 1 The substituent R stands. 1 , which is bonded to the nitrogen atom, preferably for an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, which may also be extended by 15 one or more R groups 2 can be substituted. In a particularly preferred embodiment, this substituent R 1same or different in each occurrence for an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 12 aromatic ring atoms, which does not have any fused aryl groups or heteroaryl groups in which two or more aromatic or heteroaromatic 6-ring groups are directly fused to one another, and which is also modified by one or more R groups. 2 can be substituted. Particularly preferred are phenyl, biphenyl, terphenyl and quaterphenyl with linkage patterns as listed above for R-1 25 to R-11, wherein these structures are modified by one or more R groups. 2 They can be substituted, but are preferably unsubstituted. If A 1 for C(R 1 )2, the substituents R are present 1, which are bonded to this carbon atom, preferably the same or different in each occurrence for a linear alkyl group with 1 to 10 C atoms or for a branched or cyclic alkyl group with 3 to 10 C atoms or for an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, which may also be further divided by one or more R groups 2 It can be substituted. R is particularly preferred. 1 for a methyl group or for a phenyl group. The R groups can be used in this context. 1 They can also form a ring system together, leading to a spiro system. Preferred embodiments for the Ar group are described below. In a preferred embodiment of the invention, Ar 5 is a bivalent aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, each of which may be partially or completely deuterated and / or modified by one or more R groups.1 Ar may be substituted. Particularly preferably, Ar represents an aromatic ring system with 6 to 12 aromatic ring atoms or a heteroaromatic ring system with 6 to 13 aromatic ring atoms, each of which may be partially or completely deuterated and / or modified by one or more R groups. 1 may be substituted, preferably with non-aromatic residues R 1 15 Preferred bivalent aromatic or heteroaromatic ring systems Ar are selected from phenylene, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, fluorene, spirobifluorene, carbazole, dibenzofuran or dibenzothiophene, wherein these groups may each be partially or completely deuterated and / or with one or more R groups 1 can be substituted, preferably with non-aromatic residues R 1This concerns Ar. Particularly preferably, Ar represents phenylene or biphenyl, whereby these groups may each be partially or completely deuterated and / or contain one or more R groups. 1 substituted 25 can be, preferably non-aromatic residues R 1 This concerns [the topic]. Ar is particularly preferred for phenylene or biphenyl, which may also be partially or completely deuterated. Preferred Ar groups are therefore the groups of the following formulas 30 (Ar-1) to (Ar-12), 35 Foreignfiling_text P24-134.doc - 20 - R 1 R 1 R 1 R 1 R 1 R 1 * # * R 1 * R 1 R 1 R 1 R 1 # # R 1 (Ar-1) (Ar-2) (Ar-3) 5 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 * # * R 1 R 1 R 1 R 1 R 1 R 1 R1 R 1 # (On-4) (On-5) 10 R 1 R 1 R 1 R 1 R 1 R 1 R 1 R 1 * R 1 * R 1 * R 1 R 1 R 1 R 1 R 1 1 1 # R 1 RR (Ar-6) R 1 R 1 R 1 R 1 15 R 1 # R 1 # (On-7) (On-8) R 1 R 1 R 1 R 1 R 1 R 1 *R 1 *R 1 *R 1 R 1 R 1 R 1 20 R 1 R 1 R 1 # R 1 R 1 R 1 R 1 R 1 R 1 R 1 # R 1 R 1# (Ar-9) (Ar-10) (Ar-11) 25 30 where the symbols used have the meanings mentioned above, the dashed bond marked with * represents the bond to silicon and the dashed bond marked with # represents the bond to ETU. Preferably, a maximum of two R groups are used. 1 for 35 residues other than H or D. A maximum of one residue R is particularly preferred. 1 Foreignfiling_text P24-134.doc - 21 - for a remainder other than H or D, and especially preferred are all remainders R 1 The values ​​for H and D are either the same or different for each occurrence. Ar is therefore particularly preferred for a group according to one of the following formulas (Ar-1a) to (Ar-12a), 5 * # * * # # (Ar-1a) (Ar-2a) (Ar-3a) 10 * # * (Ar-4a) (Ar-5a) # * * * 15 # (Ar-6a) (Ar-7a) # # (Ar-8a)20 * * * * # # (Ar-9a)# (Ar-10a)# (Ar-12a) (Ar-11a) 25 where the symbols used have the meanings mentioned above and the structures may be partially or completely deuterated. 30 Preferred embodiments of the substituents R' bonded to the silicon atoms of the silsesquioxane are described below. Preferably, R' is chosen to be the same or different from OR at each occurrence. 1 , where R 1 in the OR group 1for a straight-chain alkyl group with 1 to 4 C atoms or a branched or cyclic alkyl group with 3 to 35 C atoms, wherein the alkyl group may also be partially or completely deuterated, or a straight-chain alkyl group with 1 to 6 C atoms or a branched or cyclic alkyl group with 3 to 6 C atoms, wherein the alkyl group may also be partially or completely deuterated. Particularly preferably, R' represents, in each instance, a straight-chain alkyl group with 1, 2, 3, 5, or 4 carbon atoms, in particular methyl, or a branched alkyl group with 3, 4, or 5 carbon atoms, in particular isopropyl, tert-butyl, or neopentyl, wherein the alkyl group may in each case be partially or completely deuterated. In a further preferred embodiment of the invention, R 1 same or different, selected from the group consisting of H, D, F, CN, OR for each occurrence2 , a straight-chain alkyl group with 1 to 10 carbon atoms or an alkenyl group with 2 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl or alkenyl group is each linked to one or more R groups 2 may be substituted and wherein one or more non-adjacent CH2 groups may be replaced by O, or an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, each of which is separated by one or more R groups 2 can be substituted; 20 where two or more residues R can be involved 1 together form an aliphatic ring system. In a particularly preferred embodiment of the invention, R 1same or different at each occurrence selected from the group consisting of H, a straight-chain alkyl group with 1 to 6 C atoms, in particular with 1, 2, 3 or 4 C atoms, or a 25 branched or cyclic alkyl group with 3 to 6 C atoms, wherein the alkyl group is joined with one or more R groups 2 may be substituted, but preferably is unsubstituted, or an aromatic or hetero-aromatic ring system with 6 to 24 aromatic ring atoms, each of which is separated by one or more R groups 2 can be substituted, but is preferably unsubstituted. In a further preferred embodiment of the invention, R 2The alkyl group H, F, or an aryl group with 1 to 4 carbon atoms, which may be substituted with an alkyl group with 1 to 4 carbon atoms, but is preferably unsubstituted, is identical or different in each occurrence. In compounds according to the invention that are processed by vacuum evaporation, the alkyl groups preferably have no more than 5 carbon atoms, particularly preferably no more than 4 carbon atoms, and most preferably no more than 1 carbon atom. For compounds processed from solution, compounds substituted with alkyl groups, in particular branched alkyl groups, with up to 10 carbon atoms, or substituted with oligoarylene groups, for example ortho-, meta-, para- or branched terphenyl or quaterphenyl groups, are also suitable.When the compounds according to the invention are used as a matrix material for a phosphorescent emitter or as a matrix material in hyperphosphorescent OLEDs or in a layer directly adjacent to a phosphorescent layer, it is further preferred that the compound does not contain any fused aryl or heteroaryl groups Ar or R in which more than two six-membered rings are directly fused to one another. Phenanthrene and triphenylene are exceptions to this, as they may be preferred despite the presence of fused aromatic six-membered rings due to their high triplet energy. The preferred embodiments mentioned above can be combined with one another as desired within the limitations defined in claim 1. In a particularly preferred embodiment of the invention, the preferences mentioned above occur simultaneously.Examples of suitable connections according to the above-mentioned design forms are the connections listed in Table 1 below. Table 1 35 Foreignfiling_text P24-134.doc - 24 - 5 1 2 10 3 4 15 20 5 6 25 7 8 30 35 9 10 Foreignfiling_text P24-134.doc - 25 - 5 11 12 10 15 13 14 20 15 16 25 30 17 18 35 Foreignfiling_text P24-134.doc - 26 - 5 19 20 10 15 21 22 20 23 24 25 30 25 26 The compounds (5) according to the invention can be obtained according to the reaction sequence shown in Scheme 35 1. Starting from the alkyl- or aryl-functionalized triols (1) known from the literature, a base-mediated reaction with a halogenaryl-functionalized trichlorosilane (2) according to S. Morimoto et al., Bull. Chem. Soc. Jpn., 2018, 91, 1390 or with a halogenaryl-functionalized trialkoxysilane (2) according to I. Blanco et al., Journal of Thermal Analysis and Calorimetry (2012), 5 108(2), 807 can be carried out in step 1 in a so-calledThe halogenaryl-functionalized polyhedral octasilsesquioxane POSS (3) can be prepared via a corner capping reaction. The halogenaryl-functionalized POSS (3) can be converted to the boranylaryl-functionalized POSS (4) in a borylation reaction (step 2). The borylation of POSS (3) to POSS (4) can be carried out either by lithiation followed by reaction with a boric acid ester or by palladium-catalyzed reaction of POSS (3) with an alkyldiborane, preferably B₂Pin₂, in the presence of a base, preferably potassium acetate. The POSS (3) and the POSS (4) can be converted into the POSS (5) according to the invention in step 3 and 4 respectively by CC- 15 coupling reactions known to the skilled person, preferably the Suzuki coupling, with aryl or heteroaryl boronic acids or halides or triflates known from the literature in the presence of a base, a palladium compound, a phosphine and a solvent or solvent mixture.20 Scheme 1: 25 30 35 Foreignfiling_text P24-134.doc - 28 - For processing the compounds according to the invention from the liquid phase, for example by spin coating or by printing processes, formulations of the compounds according to the invention are required. These formulations can be, for example, solutions, dispersions 5 or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose. A further object of the present invention is therefore a formulation containing at least one compound according to the invention and at least one further compound. The further compound can be, for example, another matrix material 10 and / or a phosphorescent emitter and / or a fluorescent emitter and / or an emitter exhibiting TADF (thermally activated delayed fluorescence), and / or a solvent.Another object of the invention is the use of the compounds 15 according to the invention in an electronic device, in particular in an organic electroluminescent device. An electronic device within the meaning of the present invention is a device which contains at least one layer which contains at least one organic compound. The component may also contain inorganic materials 20 or layers which are composed entirely of inorganic materials. Yet another object of the invention is an electronic device, in particular an organic electroluminescent device 25, containing one or more compounds according to the invention.The electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), dye-sensitized organic solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-Lasers) and “organic plasmon emitting devices”, but preferably organic electroluminescent devices (OLEDs), particularly preferably phosphorescent or hyperphosphorescent OLEDs. The organic electroluminescent device contains a cathode, anode 5 and at least one emitting layer.In addition to these layers, it can contain further layers, for example, one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, and / or charge generation layers. Interlayers, which may, for example, have an exciton-blocking function, can also be introduced between two emitting layers. It should be noted, however, that not every one of these layers is necessarily present. The organic electroluminescence device can contain one emitting layer, or it can contain several emitting layers. If several emission layers are present, they preferably exhibit several emission maxima between 380 nm and 750 nm, resulting in overall white emission.Twenty different emitting compounds, capable of fluorescence or phosphorescence, are used in the emitting layers. Systems with three emitting layers are particularly preferred, wherein the three layers exhibit blue, green, and orange or red emission. The organic electroluminescent device according to the invention can also be a tandem OLED, particularly for white-emitting OLEDs. The compound according to the invention can be used in different layers, depending on the precise structure. In a preferred embodiment of the invention, the compound according to the invention can be used as an electron transport material in an electron transport layer and / or a hole-blocking layer of an organic electroluminescent device.Due to the low refractive index of the compounds according to the invention, they are particularly suitable for use in an electron transport layer 35, as they lead to improved light extraction there. A hole-blocking layer is typically used as a pure layer of a material. An electron transport layer is typically used either as a pure layer of a material or as a mixture with another electron transport material, for example, as a mixture with 5 a triaryltriazine or LiQ (lithium quinolinate). As an electron injection layer, a pure layer of the electron injection material, for example LiQ or LiF, is typically used as a very thin layer, for example, with a layer thickness in the range of 1 to 5 nm, in direct contact with the cathode.10 In a further embodiment of the invention, the compound according to the invention can be used in an emitting layer of an organic electroluminescent device as a matrix material for phosphorescent emitters, fluorescent emitters, or emitters exhibiting TADF (thermally activated delayed fluorescence), particularly for phosphorescent emitters. The large shielding (R')7Si8O12 group largely or completely suppresses the formation of exciplexes between the host and emitter in phosphorescent OLEDs or between the host and phosphorescent sensitizer in hyperphosphorescent OLEDs, which is particularly important for blue and green emitting OLEDs. The organic electroluminescent device can contain one emitting layer, or it can contain several emitting layers, wherein at least one emitting layer contains at least one compound according to the invention as a matrix material.Depending on the group ETU, the compounds according to the invention are suitable not only as matrix materials for green, yellow, orange, or red phosphorescent emitters, but also for blue phosphorescent emitters or for blue hyperphosphorescent emission layers. When the compound according to the invention is used as a matrix material for a phosphorescent compound in an emitting layer, it is preferably used in combination with one or more phosphorescent materials (triplet emitters). Phosphorescence 35 within the meaning of this invention is understood to mean luminescence from an excited state with a higher spin multiplicity, i.e., a spin state > 1, in particular from an excited triplet state.For the purposes of this application, all luminescent complexes with transition metals or lanthanides, in particular all iridium, platinum, and copper complexes, are to be considered phosphorescent compounds. The mixture of the compound according to the invention and the emitting compound contains between 99 and 1 vol%, preferably between 98 and 10 vol%, particularly preferably between 97 and 60 vol%, and in particular between 95 and 80 vol% of the compound according to the invention, based on the total mixture of emitter and matrix material. Correspondingly, the mixture contains between 1 and 99 vol%, preferably between 2 and 90 vol%, and in particular between 3 and 40 vol%, and in particular between 5 and 20 vol% of the emitter, based on the total mixture of emitter and matrix material.15 Another preferred embodiment of the present invention is the use of the compound according to the invention as a matrix material for a phosphorescent emitter in combination with another matrix material. Suitable matrix materials which can be used in combination with the compounds according to the invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680, triarylamines, carbazole derivatives, etc. B. CBP (N,N-Biscarbazolylbiphenyl) or those in WO 2005 / 039246, US 25 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or WO 2013 / 041176, indolocarbazole derivatives, e.g. according to WO 2007 / 063754 or WO 2008 / 056746, indenocarbazole derivatives, e.g. according to WO 2010 / 136109, WO 2011 / 000455, WO 2013 / 041176 or WO 2013 / 056776, azacarbazole derivatives, e.g. B. according to EP 1617710, EP 30 1617711, EP 1731584, JP 2005 / 347160, bipolar matrix materials, e.g.according to WO 2007 / 137725, silanes, e.g. according to WO 2005 / 111172, azaboroles or boron esters, e.g. according to WO 2006 / 117052, triazine derivatives, e.g. according to WO 2007 / 063754, WO 2008 / 056746, WO 2010 / 015306, WO 2011 / 057706, WO 2011 / 060859 or WO 2011 / 060877, pyrimidine 35 derivatives, zinc complexes, e.g. according to EP 652273 or WO 2009 / 062578, Foreignfiling_text P24-134.doc - 32 - diazasilol or tetraazasilol derivatives, e.g. B. according to WO 2010 / 054729, diazaphosphole derivatives, e.g. according to WO 2010 / 054730, bridged carbazole derivatives, e.g. according to WO 2011 / 042107, WO 2011 / 060867, WO 2011 / 088877 and WO 2012 / 143080, triphenylene derivatives, e.g. according to WO 2012 / 048781, or dibenzofuran derivatives, e.g. according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO 2017 / 148565.Likewise, another phosphorescent emitter, which emits at a shorter wavelength than the actual emitter, can be present as a co-host in the mixture, or a compound that does not participate in charge transport or does not participate to a significant extent, as described, for example, in WO 2010 / 108579. The compounds according to the invention are electron-deficient or electron-transporting compounds. Preferred co-matrix materials are therefore selected from the group of hole-transporting compounds, preferably carbazole, indenocarbazole, indolocarbazole, or triarylamine derivatives.A further object of the invention is therefore a mixture containing at least one compound of formula (1) or at least 20 a corresponding preferred compound and at least one further compound selected from the group consisting of matrix materials, phosphorescent emitters, fluorescent emitters and / or emitters exhibiting TADF (thermally activated delayed fluorescence). Suitable matrix materials and emitters that can be used in this mixture according to the invention are described below. Particularly suitable hole-transporting matrix materials, which are advantageously combined with compounds of formula (1) as previously described or preferably described, in a mixed-matrix system, 30 can be selected from the compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-6), (HH-7) or (HH-8) described below.A further object of the invention is therefore an organic 35 electronic device comprising an anode, a cathode and Foreignfiling_text P24-134.doc - 33 - 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 according to the invention as a first matrix material and at least one compound according to one of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-6) or (HH-7) as a second matrix material 5, 10 formula (HH-1) Ar5[R. 6 ] t [R 6 ] N u 15 1 [R 6 ] t A 6 [R 6 ] s [R ] s N Ar5Formula (HH-2) 20 25 Formula (HH-3) 30 Formula (HH-4) 35 Foreignfiling_text P24-134.doc - 34 - 5 Formula (HH-5) 10 Formula (HH-6) Ar5N R 6 t R 6 s 15 NR 6 s R 6 s formula (HH-7) where the following applies to the symbols and indices used: 20 A1 is C(R 7 )2, NR 7 , O or S; L is a bond, O, S, C(R 7 )2 or NR 7 ; A is, independently of each other, a group of formula (HH-4-1) or (HH-4-2), 25 30 formula (HH-4-1) formula (HH-4-2); X2 is the same or different from CH, CR, depending on each occurrence 6 or N, where a maximum of 2 symbols can represent X2 N; * indicates the binding site to the formula (HH-4); U 1 , U 2 are, when they occur, a bond, O, S, C(R 7 )2 or NR 7 ; 35 Foreignfiling_text P24-134.doc - 35 - R 6 is the same or different in each occurrence D, F, CN, a straight-chain alkyl group with 1 to 20 C atoms or an alkenyl or alkynyl group with 2 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each linked to one or more 5R substituents 7can be substituted and where one or more non-adjacent CH2 groups are replaced by Si(R 7 )2, C=O, NR 7 , O, S or CONR 7 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, each of which is replaced by one or more R groups 7 can be substituted; in this case, two residues 10 R can be used. 6 also together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar5, in each occurrence, stands independently for an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which is coupled with one or more R groups. 7 can be substituted; R 7 is the same or different in 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 with 1 to 20 carbon atoms, or an alkenyl or alkynyl group with 2 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein the alkyl, alkenyl, or alkynyl group is each linked to one or more R groups 8 can be substituted, with one or more non-adjacent CH2 groups being replaced by Si(R 8 )2, C=O, NR 8 , O, S or CONR 8 may be replaced, or an aromatic 25 or heteroaromatic ring system with 5 to 40 ring atoms, each of which is replaced by one or more R groups 8 can be substituted, where R 8 does not mean H; in this case, two or more residues R can be present. 7 together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system, preferably the 30 residues R 7 no such ring system; R 8is the same or different H, D, F or an aliphatic, aromatic or heteroaromatic organic residue, in particular a hydrocarbon residue, with 1 to 20 C atoms, in which one or more H atoms may also be replaced by D or F 35; Foreignfiling_text P24-134.doc - 36 - c, c1, c2 each independently mean 0 or 1 for each occurrence, where the sum of the indices for each occurrence c+c1+c2 = 1; d, d1, d2 each independently mean 0 or 1 for each occurrence, where the sum of the indices for each occurrence d+d1+d2 = 1; q, q1, q2 each independently mean 0, 1, 2, 3 or 4 for each occurrence; s is equal to or different from 0, 1, 2, 3 or 4 for each occurrence; t is equal to or different from 0, 1, 2, or 3 for each occurrence; u is equal to or different from 0, 1 or 2 for each occurrence; u1, u2 each independently mean 0 or 1 for each occurrence, where the sum u1 + u2 = 1; and v is 0, 1, 2 or 3. 15 Preferred compounds of formula (HH-5) are compounds of formulas (HH-5-A) to (HH-5-E), 20 Formula (HH-5-A) 25 30 Formula (HH-5-B) 35 Foreignfiling_text P24-134.doc - 37 - 5 Formula (HH-5-C) 10 Formula (HH-5-D) 15 Formula (HH-5-E) where Ar5, R. 6, s and u have a previously specified or preferably specified meaning. 20 Preferred compounds of formula (HH-7) are the compounds of the following formula (HH-7-A), 25 30 formula (HH-7-A) where the symbols used have the meanings given above. 35 In compounds of formulas (HH-1), (HH-2), (HH-3), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), (HH-6), (HH-7) or (HH-7-A), s is preferably 0 or 1 if the remainder R 6 is different from D, and is particularly preferably 0. In compounds of formulas (HH-1), (HH-2), (HH-3), (HH-7) or (HH-7-A), t is preferably 0 or 1 if the remainder R 6 is different from D, and 5 is particularly preferably 0. In compounds of formulas (HH-1), (HH-2), (HH-3), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D) or (HH-5-E), u is preferably 0 or 1 if the residue R 6is different from D, or particularly preferably 0. 10 The sum of the indices s, t and u in compounds of formulas (HH-1), (HH-2), (HH-3), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), (HH-6), (HH-7) or (HH-7-A) is preferably at most 6, more preferably at most 4 and most preferably at most 2. This is particularly true if R 6 different from D. 15 In compounds of formula (HH-4), c, c1, c2 each independently mean 0 or 1 at each occurrence, where the sum of the indices means c+c1+c21 at each occurrence. Preferably, c2 has the meaning 1. 20 In compounds of formula (HH-4), L is preferably a single bond or C(R 7 )2, where R 7 L has a previously mentioned meaning, and is particularly preferred as a single bond. In formula (HH-4-1), v is preferably 0 or 1 if the residue R 6 is different from D. 25 In formula (HH-4-2) U 1 or U 2When occurring, a single bond or C(R) is preferred 7 )2, where R 7 has a previously mentioned meaning, especially preferred are U 1 or U 2 A single bond occurs when this is present. In formula (HH-4-2), q, q1, q2 are preferably 0 or 1 if the remainder R 6 30 of D is different. In a preferred embodiment of the compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), (HH-6), (HH-7) or (HH-7-A), which according to the invention 35 can be combined with compounds of formula (1) or the preferred embodiments, R 6 same or different at each occurrence selected from the group consisting of D, F, CN, a straight-chain alkyl group with 1 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl group is in each case linked to one or more R groups 7may be substituted, or 5 an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, preferably with 5 to 40 ring atoms, each of which is separated by one or more R groups 7 may be substituted. In a preferred embodiment of the compounds of formulas 10 (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), (HH-6), (HH-7) or (HH-7-A), which can be combined according to the invention with compounds of formula (1) or preferred compounds of formula (1) as described above, R 6 same or different at each occurrence selected from group 15 consisting of D or an aromatic or heteroaromatic ring system with 6 to 30 ring atoms, which is joined with one or more R groups 7may be substituted. Ar5 is preferably selected in compounds of formulas (HH-1), (HH-2), (HH-3), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), (HH-6), (HH-7) or (HH-7-A) from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorenyl, which may be linked via the 1-, 2-, 3- or 4-position, 9,9-dimethylfluorenyl, which may be linked via the 1-, 2-, 3- or 4-position, spirobifluorenyl, which may be linked via the 1-, 2-, 3- or 4-position, naphthyl, in particular 1- or 2-linked naphthyl, or residues derived from indole, benzofuran, benzothiophene, carbazole, which may be linked via the 1-, 2-, 3-, 3- or 4-position, dibenzofuran, which may be linked via the 1-, 2-, 3- or 4-position, dibenzothiophene, which may be linked via the 1-, 2-,3- or 4-position linked, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene, which 35 Foreignfiling_text P24-134.doc - 40 - each with one or more R groups, 7 Ar5 can be substituted. Preferably, Ar5 is deuterated, but not further substituted. If A 1 in formula (HH-2) or (HH-3) or (HH-6) for NR 7 The substituent R stands. 7 , which is bonded to the nitrogen atom, preferably for 5 an aromatic or heteroaromatic ring system with 5 to 24 ring atoms, which may also be further divided by one or more R groups 8 can be substituted. In a particularly preferred embodiment, this substituent R 7the same or different in each occurrence for an aromatic or heteroaromatic ring system with 6 to 24 ring atoms, 10 in particular with 6 to 18 ring atoms. Preferred embodiments for R 7 are phenyl, biphenyl, terphenyl and quaterphenyl, which are preferably deuterated, as well as residues derived from triazine, pyrimidine and quinazoline, which are joined by one or more R residues 8 can be substituted, where R 8 does not mean H. 15 If A 1 in formula (HH-2) or (HH-3) or (HH-6) for C(R 7 )2, the substituents R are present 7 , which are bonded to this carbon atom, preferably the same or different in each occurrence for a linear alkyl group with 1 to 10 C atoms or for a branched or cyclic alkyl group with 3 to 10 C atoms or for an aromatic or heteroaromatic ring system with 5 to 24 ring atoms, which may also be further modified by one or more R groups 8can be substituted, where R 8 It does not mean H. R is especially preferred. 7 for a methyl group or for a phenyl group. The R groups can be used in this process. 7 25 also form a ring system together, leading to a spiro system. Other suitable hole-transporting host materials, which are particularly suitable for use in combination with blue phosphorescent emitters, are the structures of the following formula (HH-8), 30 R N1 XNR M1 XMXNR M2 X m 35 RN2 Formula (HH-8) Foreignfiling_text P24-134.doc - 41 - where the following applies to the symbols and indices used: M is Si or Ge, preferably Si; 5 X is the same or different CR or N in each occurrence, with the proviso that no more than two X per cycle stand for N; R M1 , R M2are, in each occurrence, either the same or different, a straight-chain alkyl group with 1 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms in which one or more hydrogen atoms may be replaced by fluorine or fluorine, or an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, which may be substituted with one of the several substituents R, where R has the meanings mentioned above; in this case, R M1 and R M2 also form an aliphatic, aromatic or heteroaromatic ring system together; R N1 , R N2In each occurrence, the following are, in the same or different ways, an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, which may be substituted with one of the several substituents R 20, where R has the meanings mentioned above; n is 1 or 2; 25m is (2−n). In a preferred embodiment of the compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), (HH-6), (HH-7), (HH-7-A) and (HH-8), these 30 compounds are partially or completely deuterated, particularly preferably completely deuterated. The preparation of the compounds with formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), (HH-35-6), (HH-7), (HH-7-A), and (HH-8) is generally known, and some of the compounds are commercially available. Foreignfiling_text P24-134.doc - 42 - Compounds of formula (HH-4) are disclosed, for example, in WO2021 / 180614, pages 110 to 119, in particular as examples on pages 120 to 127. Their preparation is disclosed in WO2021 / 180614 A1 on page 128 and in the synthesis examples on pages 214 to 218. 5 The preparation of the triarylamines of formula (HH-6) is known to those skilled in the art, and some of the compounds are commercially available. If the at least one other matrix material is a deuterated compound, it is possible that a mixture of deuterated compounds with the same basic chemical structure may be obtained, differing only in the degree of deuteration and / or the deuteration pattern.15 In a preferred embodiment of the at least one further matrix material, it is a mixture of deuterated compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), (HH-6), (HH-7), (HH-7-A) or (HH-8), as previously described, wherein the average degree of deuteration of these 20 compounds is at least 50 mol% to 90 mol%, preferably 70 mol% to 100 mol%. Examples of suitable further matrix materials for combination with compounds of formula (1), as previously described or preferably described in 25, are the compounds described in WO 2019 / 229011 A1, Table 3, pages 137 to 203, which may also be partially or completely deuterated.Examples of suitable additional matrix materials for combination with 30 compounds of formula (1) or preferred compounds of formula (1), as previously or preferably described, are the compounds described in WO 2021 / 180625 A1, Table 3, pages 131 to 137 and in Table 4, pages 137 to 139, which may also be partially or completely deuterated. Examples of suitable additional matrix materials for combination with compounds of formula (1) or preferred compounds of formula (1), as previously or preferably described, are the compounds described in KR 20230034896 A, on pages 42 to 47, compounds [2-1] to [2-110], or on pages 49 to 51, compounds [3-1] to [3-26].Examples of suitable additional matrix materials for combination with compounds of formula (1) or preferred compounds of formula (1), as previously or preferably described, are the compounds described in KR 20230154750 A, on pages 39 to 49, compounds [B-1] to [B-243], or on pages 49 to 53, compounds [C-1] to [C-102], or on pages 54 to 57, compounds [D-1] to [D-120]. Examples of suitable additional matrix materials for combination with compounds of formula (1) or preferred compounds of formula (1), as previously or preferably described, are the compounds described in US 2023 / 0172065 A, on pages 413 to 434.20 Further examples of suitable host materials of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) and (HH-6) for 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 25 and Table 3. Table 2: 30 35.

[0002]  Foreignfiling_text P24-134.doc - 48 - 5 10 15 NN 20 NN n n 25 30 35 Foreignfiling_text P24-134.doc - 49 - NNN 5 N nn 10 NN n 15 20 25 30 35 Foreignfiling_text P24-134.doc - 50 - NN 5 n 10 15 20 25 30 NN 35 n Foreignfiling_text P24-134.doc - 51 - NNN 5 n 10 15 NN 20 N n 25 30 35 Foreignfiling_text P24-134.doc - 52 - 5 10 15 ON 20 N n 25 30 35

[0003] 30

[0004] 35 

[0005] 

[0006]

[0007] -09- Foreignfiling_text P24-134.doc - 61 - 5 10 15 20 25 In the table above, n represents the number of D atoms in the respective compound and is 0 or D1 to Dmax, preferably D1 to Dmax. If n = 0, this means that it is a non-deuterated compound. n = D1 means that in the respective compound, one H atom is replaced by one D atom. Dmax means the maximum number of D atoms possible in the respective compound. The maximum number Dmax can vary from compound to compound. Foreignfiling_text P24-134.doc - 62 - Depending on the connection, Dmax can take on the following values: 20, 24, 26, 28, 30, 31, 32, 34, 35, 36, 37, 38 and 40.Particularly suitable compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6), which are selected according to the invention and are preferably used in combination with at least one compound of formula (1) in the electroluminescent device according to the invention, are the compounds of Table 3. Table 3: 15 20 H1 H2 H3 25 30 H4 H5 H6 35 Foreignfiling_text P24-134.doc - 63 - 5 H7 H8 H9 10 15 20 H10 H11 H12 25 30 H13 H14 H15 35 Foreignfiling_text P24-134.doc - 64 - 5 H16 H17 H18 10 15 H19 H20 H21 20 25 30 H22 H23 H24 35 Foreignfiling_text P24-134.doc - 65 - 5 10 H25 H26 H27 15 20 H28 H29 H30 25 30 H31 H32 H33 35 Foreignfiling_text P24-134.doc - 66 - 5 H34 H35 H36 10 15 H37 H38 H39 20 25 H40 H41 H42 30 35 Foreignfiling_text P24-134.doc - 67 - 5 H43 H44 H45 10 15 H46 H47 H48 20 25 H49 H50 H51 Examples of host materials of formula (HH-7) or(HH-7-A), which are particularly suitable for use in combination with blue phosphorescent emitters, are the structures shown in Table 4 below: Table 4: 35 Foreignfiling_text P24-134.doc - 68 - 5 10 15 20 25 The host materials of formula (1) mentioned above, as well as their preferably described embodiments, can be combined in the device according to the invention as desired with the matrix materials mentioned above, the matrix materials of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), (HH-6), (HH-7), (HH-7-30 A) or (HH-8) as well as their preferably described embodiments of Table 2, 3 or 4. The concentration of the host material of formula (1), as previously described or preferably described, in the inventive mixture 35 or in the light-emitting layer of the inventive device Foreignfiling_text P24-134.doc - 69 - is typically in the range of 5 wt.% to 90 wt.%, preferably in the range of 10 wt.% to 85 wt.%, more preferably in the range of 20 wt.% to 85 wt.%, even more preferably in the range of 30 wt.% to 80 wt.%, most preferably in the range of 20 wt.% to 60 wt.% and most preferably in the range of 30 wt.% to 550 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), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), (HH-6), (HH-7), (HH-7-A) or (HH-8), as previously described or preferably described, in the inventive mixture or in the light-emitting layer of the inventive device is typically in the range of 10 wt.% to 95 wt.%, preferably in the range of 15 wt.% to 90 wt.%, more preferably in the range of 15 wt.% to 80 wt.%.-%, more preferably in the range of 20 wt.% to 70 wt.%, most preferably in the range of 40 wt.% to 80 wt.% and most preferably in the range of 50 wt.% to 70 wt.%, based on the entire mixture or based on the entire composition of the light-emitting layer. 20 The present invention also relates to a mixture which, in addition to the host materials of formula (1) mentioned above, hereinafter referred to as host material 1, and the host material of at least one of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), (HH-6), (HH-7), (HH-7-A) and (HH-8), hereinafter referred to as host material 2, as previously described or preferably described, 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 a higher spin multiplicity, i.e., a spin state > 1, for example, through a transition from a triplet state or a state with an even higher spin quantum number, such as a quintet state. Preferably, a transition from a triplet state is understood here. 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, especially a metal with this atomic number.Compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are preferred as phosphor emitters, particularly compounds containing iridium or platinum. For the purposes of the present invention, all luminescent compounds containing the aforementioned metals are considered phosphor emitters. In general, all phosphorescent complexes such as those used in phosphorescent OLEDs according to the prior art and known to those skilled in the art in the field of organic electroluminescence devices are suitable.Examples can be found in applications WO 00 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 2005 / 033244, WO 2005 / 019373, US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, WO 2010 / 102709, WO 2011 / 032626, WO 2011 / 066898, WO 2011 / 157339, WO 2012 / 007086, WO 2014 / 008982, WO 2014 / 023377, WO 2014 / 094961, WO 2014 / 094960, WO 2015 / 036074, WO 2015 / 104045, WO 25 2015 / 117718, WO 2016 / 015815, WO 2016 / 124304, WO 2017 / 032439, WO 2018 / 011186 and WO 2018 / 041769, WO 2019 / 020538, WO 2018 / 178001, WO 2019 / 115423 and WO 2019 / 158453. 30 Preferred phosphorescent emitters correspond to the following formula (I), 35 Foreignfiling_text P24-134.doc - 71 - 5 Formula (I) where the symbols and indices for this formula (I) have the following meanings: 10 n+m is 3, n is 1 or 2, m is 2 or 1, X is the same or different N or CR in each occurrence, R is the same or different H, D, F, CN or a branched or linear alkyl group with 1 to 10 C atoms or a partially or completely deuterated branched or linear alkyl group with 15 1 to 10 C atoms or a cycloalkyl group with 4 to 7 C atoms, which may be partially or completely substituted with deuterium or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, which may be partially or completely substituted with deuterium. 20 In emitters of formula (I) n is preferably 1 and m is preferably 2. In emitters of formula (I) one X is preferably selected from N and the other X represent CR or all X are the same or different at each occurrence representing CR.25 In emitters of formula (I), at least one R is preferably different from H. In emitters of formula (I), two R are preferably different from H and have one of the meanings previously given. 30 Platinum complexes of the following formula (II) are also preferred, 35 Foreignfiling_text P24-134.doc - 72 - 5 Formula (II) where R has the meaning given above and furthermore: 10 Y. 1 , Y 2 , Y 3 , Y 4 , Y 5 The same or different for each occurrence for a group CR Y or N; or Y 1 -Y 2 and / or Y 3 -Y 4 or Y 4 -Y 5 can form a condensed aryl or heteroaryl ring with 5 to 18 aromatic ring atoms, each of which can also be substituted by one or more R groups; E 50 the same or different for C(R) in each occurrence C0 )2, NR N0 , O or S is shown; 20 ares 50In each occurrence, whether the same or different, it is an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, each of which may also be substituted by one or more R groups; 25 Ar 51 , Ar 52 , Ar 53 the same or different represent a fused aryl or heteroaryl ring with 5 to 18 aromatic ring atoms, each of which may also be substituted by one or more R groups; 30 R YThe residue is selected from H, D, F, Cl, Br, I, CHO, CN, C(=O)R, P(=O)(R)2, S(=O)R, S(=O)2Ar, N(R)2, NO2, Si(R)3, B(OR)2, OSO2R, a straight-chain alkyl, alkoxy or thioalkyl group with 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group with 3 to 35 to 40 C atoms, each of which is the same or different for a residue R Foreignfiling_text P24-134.doc - 73 - may be substituted, wherein one or more non-adjacent CH2 groups may be replaced by RC=CR, C≡C, Si(R)2, Ge(R)2, Sn(R)2, C=O, C=S, C=Se, P(=O)(R), SO, SO2, O, S or CONR and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or 5 heteroaromatic ring system with 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R groups, and an aryloxy group with 5 to 40 aromatic ring atoms, which may be substituted by one or more R groups, wherein two R groups. Y together they can form an aliphatic, aromatic 10 or heteroaromatic ring system, which may be substituted by one or more R' residues; R C0in each occurrence the same or different for a residue selected from H, D, a straight-chain alkyl group with 1 to 40 C-15 atoms, which may be substituted by one or more residues R, an aryl or heteroaryl group with 6 to 18 aromatic ring atoms, each of which may be substituted by one or more residues R, where two residues R C together they can form an aliphatic, aromatic or heteroaromatic ring system substituted by one or more R residues; R N0In each occurrence, the residue is selected from H, D, F, a straight-chain alkyl group with 1 to 40 C atoms, or a branched or cyclic alkyl group with 3 to 25 or 40 C atoms, each of which is substituted by one or more residues R, wherein one or more H atoms may be replaced by D, F, or CN, or an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, each of which may be substituted by one or more residues R. 30 Preferably, Ar 50 In each occurrence, the aromatic or heteroaromatic ring system has the same or different components, with 5 to 30, particularly preferably 6 to 24, and most preferably 6 to 18 aromatic ring atoms, each of which may also be substituted by one or more R groups. Foreignfiling_text P24-134.doc - 74 - Preferably Ar 51 , Ar 52 , Ar 53same or different for a fused aryl or heteroaryl ring with 6 aromatic ring atoms, each of which may also be substituted by one or more R groups. 5 Preferably, R YIn each occurrence, the following may be the same or different for H, D, F: a straight-chain alkyl, alkoxy, or thioalkyl group with 1 to 40, preferably 1 to 20, and more preferably 1 to 10 carbon atoms; or a branched or cyclic alkyl, alkoxy, or thioalkyl group with 3 to 40, preferably 3 to 20, and more preferably 3 to 10 carbon atoms, each of which may be substituted by one or more R groups, wherein one or more non-adjacent CH2 groups may be replaced by RC=CR, C≡C, O, or S, and wherein one or more H atoms may be replaced by D or F; an aromatic or heteroaromatic ring system with 5 to 30, particularly preferably 5 to 18, aromatic ring atoms, each of which may be substituted by one or more R groups. Preferably, R C0The residue is selected from H, D, a straight-chain alkyl group with 1 to 20, preferably 1 to 6 and further preferably 1 to 3 carbon atoms, which may be substituted by one or more residues R, or an aryl or heteroaryl group with 6 to 18 and preferably 6 to 12 aromatic ring atoms, each of which may be substituted by one or more residues R, in each occurrence being the same or different. C0 together they can form an aliphatic, aromatic, or heteroaromatic ring system substituted by one or more R groups. Preferably, R N0The residue is selected from an aromatic or heteroaromatic ring system with 5 to 40, particularly preferably 5 to 30, and even more preferably 5 to 18 aromatic ring atoms, each of which may be substituted by one or more residues R. A further object of the invention is therefore an organic electroluminescent device, as previously described or preferably described, characterized in that the light-emitting layer contains, in addition to the host material(s), at least one phosphorescent emitter corresponding to one of formulas (I) or (II). Preferred examples of phosphorescent emitters are described in WO 5 2019 / 007867 on pages 120 to 126 in Table 5 and on pages 127 to 129 in Table 6. The emitters are included in the description by reference.Particularly favored examples of phosphorescent emitters are listed in Table 5 below. Table 5: NONO 15 Ir Ir OO 2. F 2 20 NN N N N Pt NN Ir Pt 3 25 CD3CD N N3Ir N N NN Ir Ir N 30 3 2 3 35 Foreignfiling_text P24-134.doc - 76 - 5 10 15 20 25 DD D D DDD D C D 3 CD3 D D NN Ir DDNN CD 30 Ir 30 NDDOND 2 CD DDD 3 2 35 Foreignfiling_text P24-134.doc - 77 - 5 10 15 N Ir NN 20 ONC D 2 3 DDNDDN Ir 25 DNDD D 30 35 Foreignfiling_text P24-134.doc - 78 - 5 10 Examples of suitable blue phosphorescent platinum and iridium complexes are shown in Table 6 below: 15 Table 6: 20 25 30 35 Foreignfiling_text P24-134.doc - 79 - F F Pt N DN N ND D D D D 5 D D D D 2417635-93-710 15 20 25 30 35 Foreignfiling_text P24-134.doc - 82 - O N Pt N N N N N D D D D DDD 5 DDD 10 15 20 25 30 35 Foreignfiling_text P24-134.doc - 83 - 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 include, for example, wide-band-gap materials, bipolar host materials, electron transport materials (ETMs), or hole transport materials (HTMs) as a third or fourth matrix material, in addition to host material 1 or host material 2.10 According to one embodiment of the present invention, the mixture contains, in addition to the components of the host material 1 and the host material 2 as previously or preferably described, no further components, i.e., functional materials. 15 These are material mixtures that are used as such for the production of the light-emitting layer. These mixtures are also referred to as premix systems, which are used as the sole material source in the deposition of the host materials for the light-emitting layer and which have a constant mixing ratio during deposition. 20 This allows the deposition of a layer with a uniform distribution of the components to be achieved in a simple and rapid manner, without the need for precise control of a multitude of material sources.25 According to an alternative embodiment of the present invention, the mixture contains, in addition to the components of host material 1 and host material 2 as previously or preferably described, a phosphorescent emitter as previously described. With a suitable mixing ratio during evaporation, this mixture 30 can also be used as the sole material source. Premix systems consisting of two matrix materials are preferred, namely a compound of formula (1) and a compound of one of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), (HH-6), (HH-7), (HH-7-A), or (HH-8). Foreignfiling_text P24-134.doc - 84 - Premix systems consisting of three matrix materials are also preferred, namely a compound of formula (1) and two compounds of one of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), (HH-6), (HH-7), (HH-7-A) or (HH-8). 5 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.%, and most preferably between 97 and 80 vol.%.-% of matrix material from at least one compound according to the invention and at least one compound of one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), (HH-6), (HH-7), (HH-7-A) or (HH-8) 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%, and most preferably between 20.3 and 20 vol% of the emitter based on the total composition of the light-emitting layer consisting of emitter and matrix material. If the compounds are processed from solution, the corresponding amounts in wt.% are preferably used instead of the amounts given above in vol.%.25 The light-emitting layer of the device according to the invention or the mixture according to the invention may also contain fluorescent emitters. 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 with at least 14 ring atoms. Preferred examples are aromatic anthracene amines, aromatic anthracene diamines, aromatic pyrene amines, aromatic pyrenediamines, aromatic chrysene amines, or aromatic chrysenediamines. An aromatic anthracene amine is understood to be a compound in which a diarylamine group is directly bonded to an anthracene group, preferably in the 9-position.An aromatic anthracenediamine is defined as a compound in which two diarylamine groups are directly bonded to an anthracene group, preferably at the 9, 10 position. Aromatic pyrenamines, pyren-5 diamines, chrysenamines, and chrysendiamines are defined analogously, wherein the diarylamine groups are preferably bonded to the pyrene at the 1 position or the 1, 6 position, respectively. Other preferred emitting compounds are indenofluorenamines or diamines, benzoindenofluorenamines or diamines, and dibenzoindenofluorenamines or diamines, as well as indenofluorene derivatives with fused aryl groups. Pyrene arylamines are also preferred. Benzoindenofluorene amines, benzofluorene amines, extended benzoindenofluorenes, phenoxazines, and fluorene derivatives linked to furan or thiophene units are also preferred. Furthermore, the light-emitting device 15 can be...The mixture according to the invention also contains materials exhibiting TADF (thermally activated delayed fluorescence). In a preferred embodiment of the invention, the fluorescent emitter is selected from structures of the following formula (F-1), 20 Ar. 30 Y 31 Y32 Y 30 A r 31 Ar 32 25 Y 33 Formula (F-1) where R has the meanings mentioned above and the following applies to the other symbols and indices used: 30 Ar 30 , Ar 31 , Ar 32 is the same or different in each occurrence a substituted or unsubstituted aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms; 35 Y 30 is B or N; Foreignfiling_text P24-134.doc - 86 - Y 31 , Y 32 , Y 33 is the same or different in each occurrence and stands for O, S, C(R 0 )2, C=O, C=S, C=NR 0 , C=C(R 0 )2, Si(R 0 )2, BR 0 , NR 0, PR 0 , SO2, SeO2 or a chemical bond, provided that if Y 30 for B stands, at least one of the groups Y 31 , Y 32 , Y 33 for 5 NR 0 stands, and if Y 30 N stands for at least one of the group Y 31 , Y 32 , Y 33 for BR 0 stands; R 0is the same or different in each occurrence, H, D, F, a straight-chain alkyl group with 1 to 20, preferably with 1 to 10 C atoms, or 10 a branched or cyclic alkyl group with 3 to 20, preferably with 3 to 10 C atoms, each of which may be substituted with one or more substituents R, wherein one or more non-adjacent CH2 groups may be replaced by O or S and wherein one or more H atoms may be replaced by D or F, 15 or an aromatic or heteroaromatic ring system with 5 to 40, preferably with 5 to 30, particularly preferably with 6 to 18 aromatic ring atoms, each of which may be substituted with one or more substituents R; in this case, two adjacent substituents R 0together form an aliphatic or aromatic ring system, which may be substituted with one or more substituents R; q is 0 or 1. Compounds in which the following holds are particularly preferred: - q = 0; Y 30 = B; and Y 31 , Y 32 = NR 0 ; or - q = 0; Y 30 = B; and Y 31 , Y 32 = NR 0 ; or - q = 1; Y 30 = N; and Y 31 , Y 32 = BR 0 ; Y 33 = chemical bond. 30 examples of suitable fluorescent emitters are shown in the table below: 35 Foreignfiling_text P24-134.doc - 91 - 5 10 BO ON 15 NN 20 25 30 35 Foreignfiling_text P24-134.doc - 92 - 5 10 The present invention also relates to an organic electroluminescent device as previously or preferably described, wherein the organic layer comprises a hole injection layer (HIL) and / or a hole transport layer (HTL), the hole-injecting material and hole-transporting material of which belong to the class of arylamines. 15 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 / 20 cathode. This sequence of layers is a preferred sequence, but not all of the aforementioned layers need to be present and / or additional layers may be present.All materials 25 used as electron transport materials in electron transport layers according to the prior art can be used as materials for the electron transport layer. In particular, aluminum complexes, for example Alq3, zirconium complexes, for example Zrq4, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline 30 derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives, and phosphine oxide derivatives are suitable. In the further layers of the organic electroluminescent device according to the invention, all materials 35 commonly used according to the prior art can be used. The person skilled in the art can therefore use all materials known for organic electroluminescent devices in combination with the compounds according to the invention without any inventive effort.A further preferred organic electroluminescence device is characterized in that one or more layers are coated using a sublimation process. The materials are applied in vacuum sublimation systems at an initial pressure of less than 10. -5 mbar, preferably less than 10 -6 The initial pressure is vapor-deposited at mbar. However, it is also possible that the initial pressure is even lower, for example less than 10 mbar. -7 mbar. 10 An organic electroluminescence device is also preferred, characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or with the aid of carrier gas sublimation. The materials 15 are applied at a pressure between 10 -5mbar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured. 20 A further preferred organic electroluminescent device is characterized in that one or more layers are produced from solution, e.g., by spin coating, or with any printing process, such as screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), ink-jet printing, or 25 nozzle printing. Soluble compounds are required for this, which can be obtained, for example, by suitable substitution. Hybrid processes are also possible, in which, for example, one or more layers of solution are applied and one or more further layers are vapor-deposited.In the production process using vapor deposition, there are basically two ways in which the organic layer 35 according to the invention, preferably the light-emitting layer, can be applied or evaporated onto any substrate or the previous layer. Firstly, the materials used can each be placed in a separate material source and then evaporated from the different material sources (co-evaporation). Secondly, the different materials can be premixed (premix systems) and the mixture placed in a single material source from which it is then evaporated (premix evaporation). This allows the deposition of the light-emitting layer with a uniform distribution of the components to be achieved simply and quickly, without the need for precise control of a large number of material sources.These methods are generally known to those skilled in the art and can be applied by them without inventive effort to electronic devices, in particular organic electroluminescent devices containing the compounds according to formula (1). 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 compounds and electronic devices according to the invention, in particular the organic electroluminescent devices, are characterized by one or more of the following surprising advantages over the prior art: 1.The materials according to the invention have a low refractive index of 30. OLEDs containing these compounds as electron transport material in an electron transport layer and / or hole-blocking layer therefore exhibit improved light extraction, leading to improved external quantum efficiency (EQE) of the OLED. 35 Foreignfiling_text P24-134.doc - 95 - 2. The use of the compounds according to the invention as a matrix material for phosphorescent emitters or hyperphosphorescent emission layers leads to OLEDs with improved color purity by suppressing the formation of exciplexes (LUMO of the compound according to the invention and HOMO of the phosphorescent emitter or sensitizer). This also prevents a loss of efficiency. 3.OLEDs containing the compounds according to the invention as matrix material for phosphorescent emitters or hyperphosphorescent emission layers lead to long lifetimes, high efficiencies, and low operating voltages. The invention is further explained by the following examples, without thereby limiting it. A person skilled in the art can implement the invention in its entirety from the descriptions and produce further electronic devices according to the invention without inventive effort. Examples: Unless otherwise specified, the following syntheses are carried out under a protective gas atmosphere in dried solvents. The solvents and reagents can be obtained, for example, from Sigma-Aldrich or ABCR. The respective information in square brackets or the numbers given for individual compounds refer to the CAS numbers of the compounds known from the literature.For compounds that can have several isomeric, enantiomeric, diastereomeric, or tautomeric forms, one form is shown as a representative example. 30 A: Synthons known from the literature LS*: 1) 1,3,5,7,9,11,14-Heptakis(alkyl / aryl)tricyclo[7.3.3.1. 5,11 ]heptasiloxane- 3,7,14-triol 35 Foreignfiling_text P24-134.doc - 96 - 5 Rest R` CAS Synthon 326621-23-2 LS*1 10 Methyl 326621-07-2 LS*2 Ethyl 1046051-91-5 LS*3 15 n-Propyl 2800920-41-4 LS*4 iso-Propyl CH320 CH3307531-92-6 LS*5 2-Methyl-propyl 183387-28-2 LS*6 Cyclopentyl 25 47904-22-3 LS*7 Cyclohexyl 444315-26-8 LS*8 30 Phenyl 2) Aryl-trialkoxy-silane 35 Foreignfiling_text P24-134.doc - 97 - NI Br OO Si S OO O i O5 18036-94-7 81095-62-7 18954-74-0 18052-81-8 LS101 LS102 LS100 LS103 Alternatively, the trimethoxysilanes or trichlorosilanes known from the literature 10 can be used. B: Preparation of the synthons S: Example S1a: 15 20 Preparation by “corner capping reaction” according to I. Blanco et al., Journal of Thermal Analysis and Calorimetry (2012), 108(2), 807. Starting material: 4.97 g (10.0 mmol) LS*1 and 3.32 g (10.4 mmol) LS100. Yield: 5.85 g (8.6 mmol); 86%; Purity: 98% n.a. 1H-NMR. 25 The symbol “LS” in the symbolic representations of the following synthons S and examples B refers to the respective literature-known synthons LS*, which reacted with the aryl-triethoxysilanes via a condensation reaction and elimination of three equivalents of ethanol. Accordingly, the symbol “LS” in the symbolic representation 30 has three fewer hydrogen atoms, namely those of the three OH groups, than the LS* in the literature-known synthon. The following compounds can be represented analogously: Example: Reactants Product 35 Foreignfiling_text P24-134.doc - 98 - LS*2 S2a LS100 5 LS*3 S3a LS100 LS*4 S4a LS100 10 LS*5 S5a LS100 15 LS*6 S6a LS100 O LS*7 O S7a Si 20 LS100 LS7 Br O LS*8 S8a LS100 25 LS*1 S1b LS101 30 LS*2 S2b LS101 LS*3 S3b LS101 35 Foreignfiling_text P24-134.doc - 99 - LS*4 S4b LS101 5 LS*5 S5b LS101 LS*6 S6b LS101 10 LS*7 S7b LS101 15 LS*8 S8b LS101 LS*1 20 S1c LS102 LS*2 S2c LS102 25 LS*3 S3c LS102 30 LS*4 S4c LS104 35 Foreignfiling_text P24-134.doc - 100 - LS*5 S5c LS102 5 LS*6 S6c LS102 10 LS*7 S7c LS102 LS*8 15 S8c LS102 LS*1 S1d 20 LS103 Example S101a: 25 30 A well stirred mixture of 6.78 g (10.0 mmol) S1a, 5.08 g (20.0 mmol) Bis(pinacolato)diborane [73183-34-3], 2.95 g (30.0 mmol) Potassium acetate, anhydrous [127-08-2], 30 g glass beads (3 mm diameter), 222 mg (0.3 mmol) Bis(tricyclohexylphosphino)palladium(II) chloride [29934-17-6] and 100 ml dioxane are stirred for 18 h at 100 °C. The filtrate is filtered while still warm over a Celite bed pre-flourished with dioxane, Foreignfiling_text P24-134.doc - 101 - the filtrate is concentrated under vacuum, the residue is taken up in 200 ml DCM, the organic phase is washed twice with 50 ml water and once with 50 ml saturated saline solution and dried over magnesium sulfate.The filtrate is filtered through a silica gel bed pre-flourished with DCM, concentrated to dryness, and crystallized by adding 30 ml of tetrahydro-5-furan (THF) and 30 ml of acetonitrile. The filtrate is then filtered and dried under vacuum. Yield: 5.92 g (8.2 mmol); 82%; Purity: approx. 98% by 1H-NMR. The following connections can be represented analogously: 10 Example: Starting Material Product S102a S2a 15 S103a S3a S104a S4a 20 S105a S5a 25 S106a S6a S107a S7a 30 S108a S8a 35 Foreignfiling_text P24-134.doc - 102 - S101b S1b 5 S102b S2b 10 S103b S3b S104b S4b 15 S105b S5b 20 S106b S6b 25 S107b S7b 30 S108b S8b 35 Foreignfiling_text P24-134.doc - 103 - LS1S101c S1c 5 L. S 2S102c S2c 10 S103c S3c 15 L S 4 O OO Si S104c S4c O B O 20 S105c S5c 25 LS6 O OO Si S106c S6c O B O 30 35 Foreignfiling_text P24-134.doc - 104 - LS7 O OO Si S107c S7c O B O 5 L S8S108c S8c 10 S101d S1d 15 Example B1: 20 25 A well stirred mixture of 7.25 g (10.0 mmol) S101a, 2.68 g (10.0 mmol) 2-chloro-4,6-diphenyl-1,3,5-triazine [3842-55-5], tripotassium phosphate monohydrate [27176-10-9], 231 mg (0.2 mmol) tetrakis-triphenyl-30 phosphinopalladium(0), 30 g glass beads (3 mm diameter) and 120 ml DMSO is stirred for 24 h at 100 °C. After complete conversion, allow to cool, pour the reaction mixture into 200 ml of a water / methanol mixture (1:1 vv), stir briefly, filter off the precipitated solid, wash it three times with 50 ml of a water / methanol mixture 35 (1:1 vv) and five times with 30 ml of methanol, and dry under vacuum. Alternatively, dissolve the solid in 300 ml of dichloromethane (DCM), filter through a silica gel bed pre-flourished with DCM, concentrate the filtrate under vacuum at 40 °C with stirring, and replace the distilled-off DCM with methanol.The crystallized solid is filtered, washed three times with 30 ml of methanol each time, and dried under vacuum. Further purification is carried out by repeated hot extraction crystallization (common organic solvents or combinations thereof, preferably acetonitrile DCM, 1:3 to 3:1 vv) or chromatography and fractional sublimation or annealing under high vacuum. Yield: 5.49 g (6.6 mmol); 66%. Purity: 99.9% n. HPLC. Alternatively, analogous to MF Roll, ACS Nano, 2008, 2, 2, 320, silver(I) oxide in THF can be used as a base. The following compounds can be prepared analogously. 15 Example educt product S101a Cl NNN B2 N 20 1268244-56-9 S101b Cl 25 NNN B3 N 1268244-56-9 30 S101c Cl NNN B4 N 35 1268244-56-9 Foreignfiling_text P24-134.doc - 106 - S102a Cl NNN B5 N 5 2361416-42-2S101a Cl NNN 10 B6 1472062-94-4 S101b 15 Cl NNN B7 20 1472062-94-4 S101c Cl NNN 25 B8 1472062-94-4 S102b 30 Cl NN B9. NN 35 Foreignfiling_text P24-134.doc - 107 - 2260688-83-1 S106a Cl N N N B10 5 O 2142681-84-1S104c Cl 10 N N N N B11 15 2260688-93-3 S101a Cl N N 20 B12 N 1689576-03-1 S101b Cl 25 N N N N B13 O 30 2260688-95-5 B14 S102c 35 Foreignfiling_text P24-134.doc - 108 - Cl N N N O 5 1472729-25-1 S101b Cl N N N 10 B15 182918-13-4 S101b 15 Cl N N N N B16 20 2260688-92-2 S101c Cl N B17 N N 25 N 2447065-52- S101b Cl 30 N N N B18 N N C 2570228-27-0 35 Foreignfiling_text P24-134.doc - 109 - S101b Cl N N N N B19 5 2567920-24-3 S107b Cl N N B20 N 10 O 1883265-32-4 S104a Cl 15 N N B21 N 3842-55-5 20 S107a S N B22 N Cl N 25 1476735-48-4 S108c Cl N N N 30 B23 1621467-35-3 35 Foreignfiling_text P24-134.doc - 110 - S101b N Cl N B24 N N 5 2172944-00-0 S101b D D D Cl 10 D N B25 N N D N D D D 2574571-56-3 15 S101c D D Cl N D N N D B26 D D D D 20 D D1300115-09-6 S101b Cl N N B27 N 25 N 2173555-83-2 S101b O 30 B28 N N Cl N 35 2226747-67-5 Foreignfiling_text P24-134.doc - 111 - S108b Cl N F N B29 N 5 2098852-73-2 S101a Cl N N 10 B30 N N N 877615-05-9 S101b Cl 15 N N B31 N N N 877615-05-9 20 S101c Cl N N B32 N N N 25 877615-05-9S101a Cl N B33 N N 30 N 1476785-42-8 35 Foreignfiling_text P24-134.doc - 112 - S101b Cl N NC N B34 N 5 2054155-13-2 S101b Cl N N N 10 B35 N 2348384-34-7 S101b 15 O Cl B36 N N N 20 2305720-32-3 S101b N Cl N N25 B37 Si 1788911-46-5 30 S101c Cl N N N B38 O 35 Foreignfiling_text P24-134.doc - 113 - 1883265-36-8 S101c Cl N B39 N 5 N 1835683-69-6 S101b Cl N 10 N N B40 O 15 2305348-66-5 S101b Cl N N N O B41 20 O 2437221-69-5 S101c 25 B42 30 1788911-46-5 35 Foreignfiling_text P24-134.doc - 114 - S101b B43 5 1788911-46-5 S103a 10 B100 2915-16-4 S107a 15 B101 20 2286234-09-9 S103b 25 B102 2305895-68-3 30 S108a B103 35 1528738-48-8 Foreignfiling_text P24-134.doc - 115 - S108b B104 5 1421599-30-5 S106b 10 B105 1592541-57-5S101a 15 B106 20 2041800-09-1 S105b 25 B200 1628819-30-6 30 B201 S101b 35 Foreignfiling_text P24-134.doc - 116 - 5 1628819-30-6 S104b 10 B202 1398394-27-8 15 S101b B203 20 1973473-88-9 S103c B300 25 1801325-93-8 S105c 30 B301 35 1821152-54-8 Foreignfiling_text P24-134.doc - 117 - S101a B302 5 2363033-70-7 S101b B303 10 1821152-34-4 S101c 15 B304 1821152-68-420 Beispiel B400: 25 30 Ein Gemisch aus 6.78 g (10.0 mmol) S1a, 4.79 g (11.0 mmol) 4,6-Diphenyl- 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine 35 [1313018-07-3], 2.76 g (12.0 mmol) Tripotassium phosphate monohydrate Foreignfiling_text P24-134.doc - 118 - [27176-10-9], 231 mg (0.2 mmol) Tetrakis-triphenylphosphinopalladium(0), 30 g glass beads (3 mm diameter) and 120 ml DMSO are stirred for 24 h at 100 °C. After complete conversion, allow to cool, pour the reaction mixture into 200 ml of a 1:1 water / methanol mixture, stir briefly, filter off the precipitated solid, wash it five times with 50 ml of a 1:1 water / methanol mixture and five times with 30 ml of methanol, and dry under vacuum. Reabsorb the solid in 300 ml of dichloromethane (DCM), filter through a silica gel bed pre-flourished with DCM, and concentrate the filtrate under vacuum at 40 °C with stirring, replacing the distilled DCM with methanol.One filters off the crystallized solid, washes it three times with 30 ml of methanol each time, and dries it under vacuum. Further purification is carried out by repeated hot extraction crystallization (common organic solvents or combinations thereof, preferably acetonitrile-DCM, 1:3 to 3:1 vv) or chromatography and fractional sublimation or annealing under high vacuum. Yield: 5.87 g (6.5 mmol); 65%; Purity: approx. 99.9% n. HPLC. Alternatively, analogous to MF Roll, ACS Nano, 2008, 2, 2, 320, silver(I) oxide in THF can be used as a base. The following compounds can be prepared analogously: Example: Starting materials Product S1a HO OH B 25 B401 NNNN 30 2378846-09-2 N. 402 S1b 35 Foreignfiling_text P24-134.doc - 119 - HO OH BNNNN 5 2378846-09-2 S1c HO OH B 10 B403 NNNN 15 2378846-09-2 S1b HO OH B 20 B404 NNNC N2259756-08-4 S6b 25 HO OH B B405 N N N 30 B52382780-04-5 35 Foreignfiling_text P24-134.doc - 120 - S6b HO OH B B406 N N 5 N 2308565-18-4 S1b OH B 10 OH B407 N N N 15 1612243-82-9 S2a O O B 20 B408 N N N O O 25 1835206-79-5 S3c H O B OH N 30 B409 N N 35 1987895-22-6 Foreignfiling_text P24-134.doc - 121 - S6a H O B OH N B N 5 410 N 2348302-22-5 10 S1b HO OH B B4 N N 15 11 N O 2378846-11-6 20 S1b H O B OH B412 N N 25 N 1821675-76-6 S2b 30 HO OH B B413 N N N 35 Foreignfiling_text P24-134.doc - 122 - 2408940-94-1 S1b O O B 5 B414 D N N D D D N D D D D D D 10 2588144-81-2 S2b O B O 15 N B415 N N N 20 2305366-95-2 S1c O O B 25 B416 N N N 30 1312412-10-4 35 Foreignfiling_text P24-134.doc - 123 - S7a HO OH B B417 N N 5 N O 2378846-11-6 10 S1b H O O B OH B418 N N N 15 2396739-37-8 S1c 20 O O B B419 N N N 25 C N2226916-97-6 LS7b HO OH B 30 B420 N N N N 35 2378846-09-2 Foreignfiling_text P24-134.doc - 124 - LS1a B421 5 1820037-43-1 LS1b 10 B422 15 1820037-43-1 LS1c 20 B423 25 1820037-43-1 LS1c O O B 30 B424 D N N D D D N D D D D 35 D D Foreignfiling_text P24-134.doc - 125 - 2588144-81-2 LS1b O O B O 5 B425 N N N 2265924-57-8 10 LS8b O B O N 15 B426 N N N 20 2305366-95-2 LS1b H O B OH 25 N B427 N N O 30 B4282305626-41-7 35 Foreignfiling_text P24-134.doc - 126 - LS1b O B O N 5 N B428 N O 10 2287210-68-6 LS8b O B O O 15 N N B429 N 20 2417057-68-0 LS3a OH B OH N B430 N 25 N 1612243-82-9 30 B 431 LS1c 35 Foreignfiling_text P24-134.doc - 127 - H O B OH N N N 5 O 2259346-74-0 10 LS8c O 15 O B432 B O N N N 20 2375521-29-0 LS7c O O B 25 O B433 N N N 30 2441038-37-3 B 434 LS1b35 Foreignfiling_text P24-134.doc - 128 - OBOONNN 5 2265924-61-4 LS1b NC OH B OH 10 B435 NNN 2140928-48-7 15 LS1a OBO B436 NN 20 NN 1971914-46-1 LS1b 25 OBO B437 NN 30 NN 1971914-46-1 35 Foreignfiling_text P24-134.doc - 129 - LS1c OBO B438 5 NNNN 1971914-46-1 10 S8a B500 15 1260393-76-7 S4b 20 B501 25 1689538-49-5 S4c 30 B502 2263909-91-5 35 Foreignfiling_text P24-134.doc - 130 - LS1b B503 5 2376611-44-6 10 S5b B504 15 1835206-54-6 LS1b 20 B505 2092371-64-5 25 LS1b B600 30 2245332-73-2 35 Foreignfiling_text P24-134.doc - 131 - LS1b B601 5 1821395-31-6 S1b 10 B700 15 2403814-83-3 LS1b 20 B701 2660012-61-1 25 LS1b 30 B800 2822550-66-1 35 Foreignfiling_text P24-134.doc - 132 - Example: Production of OLEDs The production of OLEDs according to the invention as well as OLEDs according to the prior art is carried out according to a general method according to WO 2004 / 058911, which is adapted to the conditions described here (layer thickness variation, materials used).5 The following examples present the results for various OLEDs. Cleaned glass plates (cleaned in a Miele laboratory dishwasher, using Merck Extran cleaner) coated with structured ITO (indium tin oxide) of 50 nm thickness are pretreated with UV-Ozone 10 for 25 minutes (UV-Ozone generator PR-100, UVP). These coated glass plates form the substrates onto which the OLEDs are applied. a) Blue Fluorescent OLED Components – BF: 15 The compounds E according to the invention can be used in the hole-blocking layer (HBL) and / or the electron transport layer (ETL). All materials are thermally vapor-deposited in a vacuum chamber. The emission layer (EML) always consists of at least one matrix material (host material) SMB (see Table 1, 20) and an emitting dopant D, which corresponds to the matrix material orThe matrix materials are added in a specific volume fraction by co-evaporation. A specification such as SMB:D (95%:5%) means that the material SMB is present in a volume fraction of 95% and the dopant D in a volume fraction of 5% in the layer. Similarly, the electron transport layer can also consist of a mixture of two materials, see Table 1. The materials used to manufacture the OLEDs are shown in Table 5. The OLEDs are characterized according to standard procedures. For this purpose, the electroluminescence spectra, the current efficiency (measured in cd / A), the power efficiency (measured in lm / W), and the external quantum efficiency (EQE, measured in percent) are determined as a function of luminance, calculated from current-voltage-luminance characteristics (IUL characteristics) assuming a Lambertian emission characteristic.doc - 133 - The EQE in (%) and the voltage in (V) are specified at a luminance of 1000 cd / m. 2. The OLEDs have the following layer structure: - Substrate 5 - Hole injection layer (HIL) made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm - Hole transport layer (HTL), made of HTM1, 180 nm - Electron blocking layer (EBL), see Table 1 - Emission layer (EML), see Table 1 10 - Hole blocking layer (HBL), see Table 1 - Electron transport layer (ETL), see Table 1 - Electron injection layer (EIL) made of ETM2, 1 nm - Cathode made of aluminum, 100 nm 15 Table 1: Structure of Blue Fluorescent OLED Devices Example EBL EML HBL ETL Thickness Thickness Thickness SMB1:D1 B1 EBM1 BF1 (95%:5%) --- 30 nm 10 nm 20 20 nm EBM1 SMB1:D1 B7 BF2 (95%:5%) 10 nm --- 30 nm 20 nm SMB2:D1 B26 EBM1 BF3 (95%:5%) --- 30 nm 25 10 nm 20 nm SMB3:D1 B414 EBM1 BF4 (95%:5%) --- 30 nm 10 nm 20 nm SMB3:D1 ETM1:ETM2 EBM1 (95%: B10 30 BF5 5%) (50%:50%) 10 nm 20 nm 5 nm 30 nm Table 2: Results Blue Fluorescent OLED Devices 35 Foreignfiling_text P24-134.doc - 134 - B sp. EQE (%) Voltage (V)BF1 9.1 4.3BF2 8.5 4.2 BF3 9.3 4.5 5 BF4 8.8 4.4 BF5 8.7 4.6 b) Phosphorescent OLED components: 10 The compounds E according to the invention can be used, in particular, in the hole-blocking layer (HBL), the electron transport layer (ETL) and / or in the emission layer (EML) as an electron-conducting matrix material (host material) (hTMM or eTMM, respectively). For this purpose, all materials are thermally vapor-deposited in a vacuum chamber. The emission layer always consists of at least one or more matrix materials M and a phosphorescent dopant Ir, which is added to the matrix material(s) by co-evaporation in a specific volume fraction. A specification such as M1:M2:Ir (55%:35%:10%) means that the material M1 is present in a volume fraction of 55%, M2 in a volume fraction of 35% and Ir in a volume fraction of 10% in the layer.Similarly, the electron transport layer can also consist of a mixture of two materials. The exact structure of the OLEDs can be found in Table 3. The 25 materials used to manufacture the OLEDs are shown in Table 5. The OLEDs are characterized according to standard procedures. For this purpose, the electroluminescence spectra, the current efficiency (measured in cd / A), the power efficiency (measured in lm / W), and the external quantum efficiency (EQE, measured in percent) are determined as a function of the luminance, calculated from current-voltage-luminance curves (IUL curves) assuming a Lambertian emission characteristic. The EQE is given in percent and the voltage in volts at a luminance of 1000 cd / m². 2. 35 Foreignfiling_text P24-134.doc - 135 - The OLEDs have the following layer structure: - Substrate - Hole injection layer (HIL) made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm - Hole transport layer (HTL) made of HTM1, 180 nm for blue, 50 nm for green, yellow and red - Electron blocking layer (EBL), see Table 3 - Emission layer (EML), see Table 3 - Hole blocking layer (HBL), see Table 3 - Electron transport layer (ETL), see Table 3 - Electron injection layer (EIL) made of ETM2, 1 nm - Cathode made of aluminum, 100 nm Table 3: Structure of phosphorescent OLED components EML EBL HBL ETL 15 ExampleDicke Dicke Dicke Dicke Blau B30:M4:IrB1 EBM2 HBM2 ETM1:ETM2 BP1 20 (40% (50%:50%) 20 nm :60%:5%) 5 nm 25 nm 30 nm B31:M4:IrB1 ETM1:ETM2 EBM2 HBM2 BP2 20 nm (40%:60%:5%) 5 nm (50%:50%) 25 nm 30 nm B31:M4:IrB1 ETM1:ETM2 EBM2 B31 25 BP3 20 nm (40%:60%:5%) 5 nm (50%:50%) 25 nm 30 nm Grün M1:M2:IrG1 EBM1 HBM1 GP1 (30 B14 30 20 nm %:60%:10%) 5 nm 40 nm 30 nm EBM1 M1:M2:IrG1 HBM1 GP2 (30%:60%:10%) B20 20 nm 5 nm 40 nm 30 nm M1:M2:IrG1 ETM1:ETM2 EBM1 B430 GP3 20 (30%:60%:10%) (50%:50%) 35 nm 5 nm 40 nm 30 nm Foreignfiling_text P24-134.doc - 136 - Yellow M1:M2:IrG2 GP50 EBM1 (30%:60%:10%) HBM1 B12 20 nm 5 nm 40 nm 30 nm 5 M1:M2:IrG2 EBM1 HBM1 GP50 (30%:60%:10%) B13 20 nm 40 nm 5 nm 30 nm Red EBM1 B100:IrR1 HBM1 ETM1:ETM2 10 RP1 (92%:8%) (50%:50%) 20 nm 5 nm 35 nm 30 nm B201:IrR1 ETM1:ETM2 EBM1 HBM1 RP2 20 nm (90%:10%) 5 nm (50%:50%) 35 nm 30 nm EBM1 B303:IrR1 HBM1 ETM1:ETM2 15 RP3 (90%:10%) (50%:50%) 20 nm 5 nm 35 nm 30 nm B600:IrR1 B31 EBM1 B7 RP4 20 nm (90%:10%) 5 nm (50%:50%) 35 nm 30 nm 20 Table 4: Results Phosphorescent OLED Devices 25 30 35 Foreignfiling_text P24-134.doc - 137 - Blue Example EQE (%) Voltage (V) BP1 22.0 4.3 BP2 22.5 4.4 5 BP2 22.6 4.2 Green GP1 24.1 3.5 10 GP2 23.8 3.4 GP3 24.4 3.6 Yellow GP50 32.3 3.3 15 GP51 33.0 3.2 Rot RP1 16.7 3.5 RP2 16.4 3.3 20 RP3 16.6 3.5 RP4 17.4 3.4 Table 5: Structural formulas of the materials used 25 NN 30 HTM1 136463-07-5 EBM1 1450933-44-4 35 Foreignfiling_text P24-134.doc - 138 - 5 EBM2 1206465-62-4 M1 1822310-86-0 10 NNNNN 15 M2 M3 = HBM2 1643479-47-31201800-83-0 20 M4 25 342638 HBM-154 1955543-57-3 N Li 30 O ETM2 25387-93-3 ETM1 35 1819335-36-8 Foreignfiling_text P24-134.doc - 139 - 5 SMB1 1087346-88-0 SMB2 6363 Blaoreszu Fluorescence 10 ON SMB3 D1 15 1627916-48-6 1182175-27-4 Phosphorescent Blue Phosphorescent Green NN 20. N N Ir Ir N 3 N IrB1 IrG1 25 1541114-98-0 2245866-06-0 Phosphoreszent Tiefrot N Ir 30 Phosphoreszent Gelb 3 IrR1 35 1562420-79-4 Foreignfiling -te P24-14. NN Ir 5 N 10 IrG2 2245945-28-0 15 20 25 30 35

Claims

Foreignfiling_text P24-134.doc - 141 - Claims 1. Compound according to formula (1), (R')7Si8O12-Ar-ETU Formula (1) 5 wherein the following applies to the symbols used: ETU is an electron-transporting unit selected from the group consisting of triazine, pyrimidine, quinoxaline, 10 quinazoline, benzoquinazoline, benzoquinoxaline, benzimidazole, diazadibenzofuran, diazadibenzothiophene and diazacarbazole, wherein these groups may each be partially or completely deuterated and / or substituted by one or more R groups; 15 Ar is a bivalent aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, each of which may each be partially or completely deuterated and / or substituted by one or more R groups 1 may be substituted; 20 R' is the same or different in each occurrence F, OR 1, a straight-chain alkyl group with 1 to 20 carbon atoms or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein the alkyl group may in each case be partially or completely deuterated 25 and / or with one or more R groups 1 can be substituted, with one or more non-adjacent CH2 groups being replaced by Si(R) 1 )2, C=O, NR 1 , O, S or CONR 1 may be replaced, or an aromatic ring system with 6 to 12 aromatic ring atoms, each of which may be partially or completely deuterated and / or with one of the several R groups 1 may be substituted; R is the same or different in each occurrence H, D, F, N(R 1 )2, CN, NO2, OR 1 , SR 1 , COOR 1 , C(=O)N(R 1 )2, Si(R 1 )3, B(OR 1 )2, 35 C(=O)R 1 , P(=O)(R 1 )2, S(=O)R 1 , S(=O)2R 1 , OSO2R 1 , a straight- Foreignfiling_text P24-134.doc - 142 - chain alkyl group with 1 to 20 C atoms or an alkenyl or alkynyl group with 2 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each linked to one or more R groups 1 can be substituted, where one or more non-adjacent CH2 groups are replaced by Si(R) 1 )2, C=O, NR 1 , O, S or CONR 1 can be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, which is coupled with one of the several R groups 1 can be substituted; two residues R can also form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system with each other; R 1 is the same or different in each occurrence H, D, F, Cl, Br, I, N(R 2 )2, CN, NO2, OR 2 , SR 2 , Si(R 2 )3, B(OR 2)2, C(=O)R 2 , 15 P(=O)(R 2 )2, S(=O)R 2 , S(=O)2R 2 , OSO2R 2 , a straight-chain alkyl group with 1 to 20 carbon atoms, or an alkenyl or alkynyl group with 2 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein the alkyl, alkenyl, or alkynyl group is each linked to one or more R groups 2 can be substituted, where one or more non-adjacent CH2 groups are replaced by Si(R) 2 )2, C=O, NR 2 , O, S or CONR 2 can be replaced and wherein one or more H atoms in the alkyl, alkenyl or alkynyl group can be replaced by D, F, Cl, Br, I or CN, or an aromatic or heteroaromatic 25 ring system with 5 to 40 aromatic ring atoms, each of which is replaced by one or more R groups 2 It can be substituted; in this case, two or more residues R can be involved. 1together form an aliphatic, aromatic, or heteroaromatic ring system; 30 R 2 is the same or different H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic residue, in particular a hydrocarbon residue, with 1 to 20 C atoms, in which one or more H atoms may also be replaced by F 35. Foreignfiling_text P24-134.doc - 143 - 2. Compound according to claim 1, characterized in that the group ETU is selected from the structures of formulas (ETU-1) to (ETU-13), 5 10 15 RRRRRRRRRNRRRRRRRN 20 N N RRRN N(ETU-10) (ETU-8) (ETU-9) RRRREERNNRNR 25 RNNNRRRRRRR (ETU-11) (ETU-12) (ETU-13) wherein R has the meanings mentioned in claim 1, E stands for O, 30 S or NR and the dashed bond indicates the bond to Ar.

3. Compound according to claim 1 or 2, characterized in that the group ETU is selected from the structures of formulas (ETU-35 1a) to (ETU-13a), Foreignfiling_text P24-134.doc - 144 - 5 10 NRRRN 15 N N N N(ETU-10a) (ETU-8a) (ETU-9a) REENN 20 NNNNRR ( 11a) (ETU-13a) (ETU-12a) wherein the symbols used have the meanings specified in claims 1 and 2 and the structures may also be partially or completely deuterated.

4. Compound according to claim 3, characterized in that the R groups in structures (ETU-1a) to (ETU-13a) represent an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, each of which may also be partially or completely deuterated and / or with one or more R groups. 1 can be substituted, and that, if E stands for NR, the residue R, which bonds to the N atom, stands for an aromatic or heteroaromatic 35 ring system with 6 to 30 aromatic ring atoms, each Foreignfiling_text P24-134.doc - 145 - also partially or completely deuterated and / or with one or more residues R 1may be substituted.

5. Compound according to one or more of claims 1 to 4, characterized in that R is selected as the same or as different from the group consisting of H, D, F, CN, OR in each occurrence. 1 , a straight-chain alkyl group with 1 to 10 carbon atoms or an alkenyl group with 2 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl or alkenyl group is each linked to one or more R groups 1 sub- 10 may be substituted, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, coupled with one or more R substituents 1may be substituted; two adjacent R groups may also form an aliphatic, aromatic, or heteroaromatic ring system.

6. Compound according to one or more of claims 1 to 5, characterized in that the group Ar is selected from the group consisting of phenylene, biphenyl, terphenyl, fluorene, spirobifluorene, carbazole, dibenzofuran, or dibenzothiophene, wherein these groups may each be partially or completely deuterated and / or comprise one or more R groups. 1 may be substituted.

7. Compound according to one or more of claims 1 to 6, 25 characterized in that Ar is selected from the groups of formulas (Ar-1) to (Ar-12), R 1 R 1 R 1 R 1 R 1 R 1 30 * # * R 1 * R 1 R 1 R 1 R 1 # # R 1 (Ar-1) (Ar-2) (Ar-3) 35 Foreignfiling_text P24-134.doc - 146 - 5 10 15 20 25 wherein the symbols used have the meanings specified in claim 1, the dashed bond marked with * represents the bond to silicon and the dashed bond marked with # represents the bond to ETU. 30 8. Compound according to one or more of claims 1 to 7, characterized in that Ar is selected from the groups of formulas (Ar-1a) to (Ar-12a), 35 Foreignfiling_text P24-134.doc - 147 - * # * * # # (Ar-1a) (Ar-2a) (Ar-3a) * # * 5 (Ar-4a) (Ar-5a) # * * * 10 # (Ar-6a) (Ar-7a) # # (Ar-8a) * * * * 15 # # (Ar-9a)# (Ar-10a)# (Ar-12a) (Ar-11a) 20 wherein the symbols used have the meanings specified in claim 7 and the structures may be partially or completely deuterated.

9. Compound according to one or more of claims 1 to 8, 25 characterized in that R' is selected from OR in the same or different way at each occurrence.1 , where R 1 in the OR group 1 for a straight-chain alkyl group with 1 to 4 carbon atoms or a branched or cyclic alkyl group with 3 to 6 carbon atoms, wherein the alkyl group may also be partially or completely deuterated. 30 Foreignfiling_text P24-134.doc - 148 - 10. Compound according to one or more of claims 1 to 9, characterized in that R' is the same or different in each occurrence and represents a straight-chain alkyl group with 1, 2, 3 or 4 carbon atoms or a branched alkyl group with 3, 4 or 5 carbon atoms, wherein the alkyl group may be partially or completely deuterated.

11. Use of a compound according to one or more of claims 1 to 10 in an electronic device.

12. Electronic device comprising one or more compounds according to one or more of claims 1 to 10.

13. Electronic device according to claim 12, wherein it is an organic electroluminescent device, characterized in that the compound according to one or more of claims 1 to 10 is used as an electron transport material in an electron transport layer and / or a hole-blocking layer. 14.Electronic device according to claim 12 or 13, wherein it is an organic electroluminescent device, characterized in that the compound according to one or more of claims 1 to 10 is used in an emitting layer as a matrix material 25 for phosphorescent emitters, fluorescent emitters, or emitters exhibiting TADF (thermally activated delayed fluorescence). Electronic device according to claim 14, characterized in that the compound according to one or more of claims 1 to 10 is used in combination with a further matrix material selected from carbazole, indenocarbazole, indolocarbazole, or triarylamine derivatives.

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