Materials for organic electroluminescent devices

Abstract

The invention relates to OLED materials and in particular silicon and germanium compounds having specific aromatic substituents for use in electronic devices, and also relates to electronic devices, in particular organic light-emitting devices, containing said materials.

Description

[0001] Foreign filing text P25-001 .docx

[0002] - 1 -

[0003] Materials for organic electroluminescence devices

[0004] The present invention relates to OLED materials and in particular silicon and germanium compounds with special aromatic

[0005] 5 Substituents for use in electronic devices, and electronic devices, in particular organic light-emitting devices, containing these materials.

[0006] Organic electroluminescent devices comprise one or more emission layers, as well as additional 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 15 layers significantly influence the performance of organic electroluminescent devices. Generally, there is still room for improvement in the materials used, particularly regarding efficiency, but also regarding the device's lifetime.

[0007] 20 The object of the present invention is therefore to provide compounds suitable for use in an organic electronic device, in particular in an organic electroluminescent device. In particular, it is an object of the present invention to provide compounds characterized by a low refractive index (RI). Reducing the refractive index of an OLED layer leads to improved light extraction and thus to improved efficiency. This applies in particular to reducing the refractive index of the hole or electron transport layer. Triarylamine derivatives, whose refractive index is typically in the range of 1.7 to 1.9, are commonly used in the hole transport layer.Aromatic compounds with electron-deficient heteroaromatics, such as triazine or benzimidazole, are typically used in the electron transport layer, with refractive indices typically in the range of 1.7 to 1.9. While a reduction in the refractive index of the layers is desirable for improved extraction, this is Foreignfiling text P25-001 .docx.

[0008] -2 -

[0009] This cannot be achieved with currently used cargo transport materials. A reduction in the refractive index can also be achieved by adding materials with a low refractive index. Besides their low refractive index, one requirement for these materials is...

[0010] 5. Refractive index, that these are inert to charge transport in the layer and therefore do not negatively affect the electronic properties of the OLED if they are doped into the layer at a not too high doping level.

[0011] 10 A further object of the present invention is the provision of materials suitable for use in a capping layer (cover layer, output layer) of an OLED. Here, too, the aim is improved output through a low refractive index of the materials. Such a capping layer is a transparent, colorless layer that does not absorb visible light and is arranged above the (semi-)transparent electrode, thus modulating the light output in such a way that the amount of output light increases and / or the viewing angle dependence of brightness and / or color is optimized. Furthermore, such a layer is used to improve the mechanical stability of the display.

[0012] Another object of the present invention is the provision of materials suitable for hydrophobizing surfaces, for example for cathode structuring.

[0013] 25

[0014] Surprisingly, it was found that certain compounds, described in more detail below, solve this problem and, when used in organic electroluminescent devices, lead to devices that exhibit very good properties, particularly with regard to lifetime, color purity, and efficiency. In particular, these materials have a low refractive index and are inert to charge transport, making them suitable for inclusion in the hole and / or electron transport layer, as well as the emitting layer. The resulting improved extraction leads to an increase in efficiency compared to OLEDs that do not contain these materials, while the other properties of the OLED, especially Foreignfiling text P25-001 .docx

[0015] - 3 -

[0016] Operating voltage and service life should not deteriorate. These compounds, as well as electronic devices, in particular organic electroluminescent devices containing such compounds, are therefore the subject of the present invention.

[0017] 5

[0018] The subject of the present invention is a compound according to the following formula (1),

[0019]

[0020] Formula 1)

[0021] where the compound may also be partially or completely deuterated, and the following applies to the symbols and indices used:

[0022] 20

[0023] M is the same or different Si or Ge in each occurrence;

[0024] R 1 In each occurrence, the alkyl group is 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, wherein the alkyl group is in each case part25

[0025] an aromatic ring system with 6 to 40 aromatic ring atoms, which may also be partially or completely deuterated and / or substituted with one or more fluorine atoms, an aromatic ring system with 6 to 40 aromatic ring atoms, which may also be partially or completely deuterated and / or which may also be substituted with one or more substituents R 5 may be substituted, a dibenzofuran- 30

[0026] group, which may also be partially or completely deuterated and / or which may also be modified by one or more substituents R 5 may be substituted, or an aralkyl group, which may also be partially or completely deuterated and / or which may also be modified by one or more substituents R 5 It may be substituted; in this case, 35

[0027] two or three substituents R 1 , which are related to the same Si or Ge atom. Foreignfiling text P25-001 .docx

[0028] - 4 -

[0029] to bind, also to form a ring together, whereby the linking occurs via a direct bond or via an O atom;

[0030] R 2 is M(R 1 )3, H, D, F, CN, a straight-chain alkyl group with 1 to 20 C- 5 atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl group may be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 40 aromatic ring atoms, which may also be partially or completely deuterated 10 and / or which may also be substituted by one or more substituents R 5 may be substituted;

[0031] R 3is the same or different in each occurrence F, 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 may be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 40 aromatic ring atoms, which may also be partially or completely deuterated and / or which may also be substituted by one or more substituents R 5 can be substituted; in this case, two residues R can be involved. 3 , which are bonded to the same carbon atom, or which are bonded to different carbon atoms in the same cycle, or a residue R 3 and a remainder R 4 , which are bonded in the same cycle and preferably to neighboring carbon atoms, also form a ring together;

[0032] R 4is the same or different in each occurrence H, D, F, 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 30 may be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 40 aromatic ring atoms, which may also be partially or completely deuterated and / or which may also be substituted by one or more substituents R 5 may be substituted;

[0033] 35 where two remainders R 4 , which are bonded to the same carbon atom, or a residue R 4 and a remainder R 3 , which are in the same cycle and Foreignfiling text P25-001 .docx

[0034] - 5 -

[0035] preferentially bonded to neighboring carbon atoms, they also form a ring with each other;

[0036] R 5is the same or different at each occurrence H, D, F, CN, Si(R) 6 )s, 5 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 may be partially or completely deuterated and / or substituted with one or more fluorine atoms; wherein two or more R groups may be 5 , which are bonded to neighboring carbon atoms, also form a mono-, oligo- or polycyclic ring with each other;

[0037] R 6In each occurrence, the alkyl group may be a straight-chain alkyl group with 1 to 10 carbon atoms, or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl group may be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 40 aromatic ring atoms, which may also be partially or completely deuterated and / or substituted with one or more alkyl groups with 1 to 10 carbon atoms, preferably with 1 to 6 carbon atoms, wherein two or more of these alkyl groups may also form a ring together;

[0038] n is either the same or different (1 or 2) in each occurrence;

[0039] 25

[0040] p is 1, 2, 3 or 4.

[0041] An aryl group according to the present invention contains 6 to 40 carbon atoms and no heteroatoms. A heteroaryl group according to this invention contains 2 to 40 carbon atoms and at least one heteroatom, provided that the sum of the carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from nitrogen, oxygen, and / or sulfur. An aryl group or heteroaryl group is defined as either a simple aromatic cycle, i.e., benzene, or a heteroaromatic cycle, for example, pyridine, pyrimidine, thiophene, etc., or a fused (fused) aryl or heteroaryl group.

[0042] - 6 -

[0043] Aromatic groups, for example naphthalene, anthracene, phenanthrene, quinoline, dibenzofuran, etc., are understood as such. Aromatic compounds linked together by single bonds, such as biphenyl or bipyridine, are not referred to as aryl or heteroaryl groups, but as aromatic five-ring systems.

[0044] An aromatic ring system according to the present invention contains 6 to 40 carbon atoms in the ring system and contains no heteroatoms in the aromatic cycle. A heteroaromatic ring system according to the present invention contains 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 N, O, and / or S. An aromatic ring system according to the present invention comprises both aryl groups and

[0045] 15 Systems in which two or more aryl groups are linked to one another via single bonds or via a group -CH2-, -C(CH3)2-, or O, or the corresponding partially or completely deuterated groups, for example biphenyl or terphenyl, and further comprises fluorene, 9,9'-spirobifluorene, and 9,9-diarylfluorene. Accordingly, a hetero20 aromatic ring system according to the present invention comprises both heteroaryl groups and systems in which two or more heteroaryl or aryl groups, at least one of which is a heteroaryl group, are linked to one another via single bonds or via a group -CH2-, -C(CH3)2-, or O, or the corresponding partially or completely deuterated 25 groups, for example bipyridine or phenylpyridine. Preferably, the aromatic ring system is selected from an aryl group, fluorene, 9,9'-spirobifluorene, or a group in which two or more aryl groups are linked to one another by single bonds.

[0046] 30

[0047] Within the scope of the present invention, the following are preferably used as groups under an alkyl group which may contain 1 to 20 carbon atoms and which may also be partially or completely fluorinated: 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-tri-foreignfiling text P25-001 .docx

[0048] - 7 -

[0049] Fluoroethyl, as well as corresponding partially or completely deuterated groups, are understood to be alkyl groups. In general, alkyl groups according to the present invention can be straight-chain, branched, or cyclic. Cyclic alkyl groups can be mono-, bi-, or polycyclic.

[0050] 5

[0051] An aromatic ring system with 6 to 40 aromatic ring atoms, which may each be substituted with the aforementioned substituents and which may be linked via any positions on the aromatic compound, is understood to include in particular groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenyl, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene.A heteroaromatic ring system with 5 to 40 aromatic ring atoms includes, in particular, groups derived from cis- or trans-indenocarbazole, cis- or trans-indenocarbazole, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-20 quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine.

[0052] Pyrazol, Indazol, Imidazol, Benzimidazol, Naphthimidazol, Phenanthrimida- zol, Pyridimidazol, Pyrazinimidazol, Chinoxalinimidazol, Oxazol, Benz- oxazol, Naphthoxazol, Anthroxazol, Phenanthroxazol, Isoxazol, 1,2-Thiazol, 1.3-Thiazol, Benzothiazol, Pyridazin, Hexaazatriphenylen, Benzopyridazin, 25 Pyrimidin, Benzpyrimidin, Chinazolin, Chinoxalin, 1 ,5-Diazaanthracen, 2,7- Diazapyren, 2,3-Diazapyren, 1 ,6-Diazapyren, 1 ,8-Diazapyren, 4,5-Diaza- pyren, 4,5,9,10-Tetraazaperylen, Pyrazin, Phenazin, Phenoxazin, Pheno- thiazin, Fluorubin, Naphthyridin, Azacarbazol, Benzocarbolin, Phenan- throlin, 1 ,2,3-Triazol, 1 ,2,4-Triazol, Benzotriazol, 1 ,2,3-Oxadiazol, 1,2,4- 30 Oxadiazol, 1 ,2,5-Oxadiazol, 1 ,3,4-Oxadiazol, 1 ,2,3-Thiadiazol, 1 ,2,4-Thia- diazol, 1 ,2,5-Thiadiazol, 1 ,3,4-Thiadiazol, 1 ,3,5-Triazin, 1 ,2,4-Triazin, 1.2.3-Triazin, Tetrazol, 1 ,2,4,5-Tetrazin, 1 ,2,3,4-Tetrazin, 1 ,2,3,5-Tetrazin, Purin, Pteridin, Indolizin und Benzothiadiazol.

[0053] 35 The phrase "two or more residues can form a ring" is used in the present description under Foreignfiling text P25-001 .docx

[0054] - 8 -

[0055] This can also be understood as the two residues being linked together by a chemical bond involving the formal elimination of two hydrogen atoms. This is illustrated by the following scheme.

[0056] 5 Ring formation

[0057]

[0058] 10

[0059] Furthermore, the above formulation should also be understood to mean that if one of the two residues represents hydrogen, the second residue binds to the position to which the hydrogen atom was bonded, forming a ring. This is illustrated by the following diagram:

[0060] 15

[0061]

[0062] 20

[0063] Preferred embodiments of the connection according to the invention are described below.

[0064] In a preferred embodiment, compound of formula (1) contains exactly one Si atom, exactly one Ge atom, exactly two Si atoms, exactly two 25

[0065] Ge atoms or exactly one Si atom and exactly one Ge atom.

[0066] In a preferred embodiment of the invention, M represents Si and the compound contains, depending on the choice of R 2 and R 5 , exactly one, two or three Si atoms, especially preferably exactly one or two Si atoms.

[0067] 30

[0068] In another preferred embodiment of the invention, R 1 , the same or different at each occurrence, for a straight-chain alkyl group with 1 to 10 C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, wherein the alkyl group is in each case partially or 35

[0069] may be completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 24 aroma-Foreignfiling text P25-001 .docx

[0070] - 9 -

[0071] tic ring atoms, which may also be partially or completely deuterated and / or which may also be modified by one or more substituents R 5 It can be substituted; there can be two or three substituents R 1 , which bond to the same Si or Ge atom also form a ring with each other. 5 R is particularly favorably 1, the same or different in each occurrence, for a straight-chain alkyl group with 1 to 5 carbon atoms, in particular methyl, ethyl, n-propyl or n-butyl, or a branched or cyclic alkyl group with 3 to 6 carbon atoms, in particular isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl or cyclohexyl, wherein the alkyl group may in each case be partially or completely deuterated, or an aromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 12 aromatic ring atoms and particularly preferably phenyl, wherein the aromatic ring system does not contain any fused aryl groups and may also be partially or completely deuterated and / or also by one or more substituents R 5 It can be substituted; there can be two or three substituents R 1 , which bind to the same Si or Ge atom, also form a ring together.

[0072] In another preferred embodiment of the invention, R2 , 20 same or different at each occurrence, for H, D, F, CN, a straight-chain alkyl group with 1 to 10 C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, wherein the alkyl group may in each case be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 25 6 to 24 aromatic ring atoms, which may also be partially or completely deuterated and / or which may also be substituted by one or more substituents R 5 It can be substituted. R is particularly preferred. 2 , the same or different in each occurrence, for H, D, F, CN, a straight-chain alkyl group with 1, 2 or 3 C atoms or a branched or cyclic alkyl group with 3, 4, 5 or 6 C atoms, wherein the alkyl group may in each case be partially or completely deuterated. R is particularly preferred 2 for H or D, especially for H.

[0073] In another preferred embodiment of the invention, R 3 , 35 same or different at each occurrence, for a straight-chain alkyl group with 1 to 10 C atoms or a branched or cyclic alkyl foreign filing text P25-001 .docx

[0074] - 10 -

[0075] group with 3 to 10 C atoms, wherein the alkyl group may be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 12 aromatic ring atoms, which may also be partially or completely deuterated and / or substituted with one or more fluorine atoms 5 can be substituted; in this case, two residues R can be involved. 3 , which are bonded to the same carbon atom, or which are bonded to different carbon atoms in the same cycle, or a residue R 3 and a remainder R 4, which are bonded to neighboring carbon atoms, also form a ring with each other. R is particularly favorably bound. 3 , the same or different in each occurrence, for a straight-chain alkyl group with 1, 2, 3 or 4 carbon atoms, in particular for methyl or ethyl, or a branched or cyclic alkyl group with 3, 4, 5 or 6 carbon atoms, wherein the alkyl group may in each case be partially or completely deuterated, or a phenyl group, which may also be partially or completely deuterated and / or by one or more R groups 5 can be substituted, but is preferably unsubstituted; in this case, two residues R can exist. 3 , which bond to the same carbon atom, also form a 5- or 6-membered ring together. R is particularly favored. 3 , the same or different at each occurrence, for 20 methyl or ethyl, each of which may also be partially or completely deuterated; where two residues R 3, which bind to the same carbon atom, also form a 5-membered ring together.

[0076] In another preferred embodiment of the invention, R 4 , 25 same or different at each occurrence, for H, D, F, a straight-chain alkyl group with 1 to 10 C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, wherein the alkyl group may in each case be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 18 aromatic ring atoms, which may also be partially or completely deuterated and / or which may also be substituted by one or more substituents R 5 can be substituted; in this case, two residues R can be involved. 4 , which are bonded to the same carbon atom, or a residue R 4 and a remainder R 3, which are bonded to neighboring carbon atoms, also form a ring together. R is particularly favorably positioned. 4 , same or different at each occurrence, for H, D, F, a straight-chain alkyl group with 1, 2, 3Foreignfiling text P25-001 .docx

[0077] - 11 -

[0078] or 4 carbon atoms or a branched or cyclic alkyl group with 3, 4, 5 or 6 carbon atoms, wherein the alkyl group may be partially or completely deuterated. R is particularly preferred 4 the same or different in each occurrence for H or D, especially for H.

[0079] 5

[0080] If one or more of the groups R 1 to R 4 or R 6If an aromatic ring system is to be represented, then this aromatic ring system preferably does not contain any fused aryl groups. A fused aryl group is understood to be a group in which two or more aryl groups are directly fused to one another via a common edge of the respective six-membered rings, as, for example, in naphthalene. Preferably, the aromatic ring system is selected from the group consisting of phenyl, biphenyl, terphenyl, quaterphenyl, fluorenyl, or spirobifluorenyl, each of which may be partially or completely deuterated and / or, in the case of R, 1 to R 4 by one or more substituents R 5 may be substituted or, in the case of R 6can be substituted by one or more alkyl groups, as defined above, wherein two or more alkyl groups can also form a ring together. Particularly preferred is the aromatic ring system selected from phenyl and biphenyl, either the same or different in each occurrence, which can each be partially or completely deuterated and / or in the case of R 1 to R 4 by one or more substituents R 5 may be substituted or, in the case of R 6 can be substituted by one or more alkyl groups, as defined above, 25 wherein two or more alkyl groups can also form a ring together. Most preferably, the aromatic ring system is a phenyl group, which can be partially or completely deuterated and / or, in the case of R 1 to R 4 by one or more substituents R 5 may be substituted or in the case of R 6 through one or

[0081] 30 several alkyl groups, as defined above, can be substituted, whereby two or more alkyl groups can also form a ring together.

[0082] Preferred aromatic ring systems R 1 to R 4 The groups of the following 35 formulas are Ar-1 to Ar-58, with groups Ar-1 to Ar-4 being preferred. Foreignfiling_text P25-001.docx

[0083] - 12 -

[0084]

[0085] 35Foreignfilingjext P25-001 .docx

[0086] - 13 -

[0087]

[0088] 35Foreignfiling text P25-001 .docx

[0089] - 14 -

[0090]

[0091] 35Foreignfiling text P25-001 .docx

[0092] - 15 -

[0093]

[0094] where R 5the above-mentioned meanings, the dashed line represents the position of the binding of this group, and furthermore: 35Foreignfiling text P25-001 .docx

[0095] - 16 -

[0096] Ar* is an optionally partially or fully deuterated aromatic ring system with 6 to 12 aromatic ring atoms, which is separated by one or more R groups. 5 may be substituted;

[0097] 5q is either 0 or 1.

[0098] In another preferred embodiment of the invention, R 5 , same or different at each occurrence, for H, D, F, CN, Si(R 6 )s, a straight-chain alkyl group with 1 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl group may be partially or completely deuterated and / or substituted with one or more fluorine atoms; in each case, two or three substituents R 5, which bond to neighboring carbon atoms, also form a ring with each other. R is particularly favored. 5 , same or different at 15 each occurrence, for H, D, Si(R 6 )3, a straight-chain alkyl group with 1 to 5 carbon atoms, in particular methyl, ethyl, n-propyl or n-butyl, or a branched or cyclic alkyl group with 3 to 6 carbon atoms, in particular iso-propyl, iso-butyl, sec-butyl, tert-butyl, neo-pentyl, cyclopentyl or cyclohexyl, wherein the alkyl group is in each case partially or completely

[0099] 20 can be deuterated; in this case, two or three substituents R can be used. 5 Substituents that bond to adjacent carbon atoms also form a ring with each other. If the substituents R 5 If they form a ring together, it can be monocyclic, oligocyclic, or polycyclic.

[0100] 25 In another preferred embodiment of the invention, R 6, the same or different in each occurrence, for a straight-chain alkyl group with 1 to 5 carbon atoms, in particular methyl, ethyl, n-propyl or n-butyl, or a branched or cyclic alkyl group with 3 to 6 carbon atoms, in particular isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl or cyclohexyl, wherein the alkyl group may in each case be partially or completely deuterated, or for a phenyl group, which may also be partially or completely deuterated and / or which may also be substituted with one or more alkyl groups with 1 to 5 carbon atoms, wherein two or more adjacent alkyl groups may also form a ring 35 together. Foreignfiling text P25-001 .docx

[0101] - 17 -

[0102] In another preferred embodiment of the invention, n = 1.

[0103] In another preferred embodiment of the invention, p = 1 or 2.

[0104] 5

[0105] In a particularly preferred embodiment of the invention, the above-mentioned advantages occur simultaneously.

[0106] Therefore, compounds of formula (1) are preferred, for which the following holds:

[0107] 10

[0108] M is Si;

[0109] R 1 The symbol R represents, in each case differently, a straight-chain alkyl group with 1 to 10 carbon atoms, or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl group may be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 24 aromatic ring atoms, which may also be partially or completely deuterated and / or substituted with one or more fluorine atoms. 5 It can be substituted; there can be two or three substituents R 1 , which bind to the same Si atom, also form a ring with each other;

[0110] R 2 The represents H, D, F, CN, a straight-chain alkyl group with 1 to 10 carbon atoms, or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl group may be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 24 aromatic ring atoms, which may also be partially or completely deuterated and / or substituted with one or more fluorine atoms. 5 may be substituted;

[0111] R 3 Whether the term "parallel" or "different" in each instance represents a straight-chain alkyl group with 1 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl group is in each case partially or completely deuterated and / or has one or more foreign filing text P25-001.docx

[0112] - 18 -

[0113] may be substituted with fluorine atoms, or an aromatic ring system with 6 to 12 aromatic ring atoms, which may also be partially or completely deuterated and / or which may also be modified by one or more substituents R 5 can be substituted; in this case, 5 can be two residues R 3 , which are bonded to the same carbon atom, or which are bonded to different carbon atoms in the same cycle, or a residue R 3 and a remainder R 4 , which are bonded to neighboring carbon atoms, also form a ring with each other;

[0114] 10 R 4The symbol R represents, in the same or different ways, H, D, F, a straight-chain alkyl group with 1 to 10 carbon atoms, or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl group may be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 18 aromatic ring atoms, which may also be partially or completely deuterated and / or substituted with one or more fluorine atoms. 5 can be substituted; in this case, two residues R can be involved. 4 , which are bonded to the same carbon atom, or a residue R 4 and a remainder R 3 , which are bonded to neighboring carbon atoms, also form a ring with each other;

[0115] R 5 The symbol represents H, D, F, CN, Si(R) in each instance, either the same or different. 6)3, a straight-chain alkyl group with 1 to 10 C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, wherein 25 the alkyl group may be partially or completely deuterated and / or substituted with one or more fluorine atoms; in each case two or three substituents R 5 , which bind to neighboring C atoms, also form a ring with each other;

[0116] 30 R 6 The term "equal or different" in each instance represents a straight-chain alkyl group with 1 to 5 carbon atoms or a branched or cyclic alkyl group with 3 to 6 carbon atoms, the alkyl group being partially or completely deuterated, or a phenyl group, which may also be partially or completely deuterated, and / or which may also be represented by one or more alkyl groups.

[0117] - 19 -

[0118] can be substituted by up to 5 carbon atoms, whereby two or more adjacent alkyl groups can also form a ring together;

[0119] n is 1 ;

[0120] 5

[0121] p is either 1 or 2.

[0122] Compounds of formula (1) are particularly preferred, for which the following applies:

[0123] 10 M is Si;

[0124] R 1 In each instance, R represents a straight-chain alkyl group with 1 to 5 carbon atoms, or a branched or cyclic alkyl group with 3 to 6 carbon atoms, wherein the alkyl group may be partially or completely deuterated, or an aromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 12 aromatic ring atoms, wherein the aromatic ring system does not contain any fused aryl groups and may also be partially or completely deuterated and / or also be modified by one or more substituents. 5It can be substituted; there can be two or three substituents R 1 , which bind to the same Si atom, also form a ring with each other;

[0125] R 2 The represents, in each case the same or different, H, D, F, CN, a 25 straight-chain alkyl group with 1, 2 or 3 C atoms or a branched or cyclic alkyl group with 3, 4, 5 or 6 C atoms, wherein the alkyl group may be partially or completely deuterated;

[0126] R 3 The symbol R represents, in each case the same or different, a straight-chain alkyl group with 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group with 3, 4, 5 or 6 carbon atoms, the alkyl group being either partially or completely deuterated, or a phenyl group, which may also be partially or completely deuterated and / or modified by one or more R groups. 5can be substituted, but 35 is preferably unsubstituted; in this case, two residues R can be present. 3 , the foreign filing text P25-001.docx

[0127] - 20 -

[0128] The same carbon atom can also form a ring with each other, preferably forming a 5-ring or 6-ring;

[0129] R 4 The symbol represents, in each case the same or different, H, D, F, a 5 straight-chain alkyl group with 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group with 3, 4, 5 or 6 C atoms, wherein the alkyl group may be partially or completely deuterated;

[0130] R 5 stands equal or different for H, D, Si(R) in each occurrence. 6 )s, a 10 straight-chain alkyl group with 1 to 5 carbon atoms or a branched or cyclic alkyl group with 3 to 6 carbon atoms, wherein the alkyl group may be partially or completely deuterated; in each case, two or three substituents R may be present5 , which bind to neighboring C atoms, also form a ring with each other;

[0131] 15

[0132] R 6 The represents, in each case differently, a straight-chain alkyl group with 1 to 5 carbon atoms or a branched or cyclic alkyl group with 3 to 6 carbon atoms, wherein the alkyl group may be partially or completely deuterated, or a 20 phenyl group, which may also be partially or completely deuterated and / or may also be substituted by one or more alkyl groups with 1 to 5 carbon atoms, wherein two or more adjacent alkyl groups may also form a ring with each other;

[0133] 25 n is 1 ;

[0134] p is either 1 or 2.

[0135] Compounds of formula (1) are particularly preferred, for which the following applies: 30

[0136] M is Si;

[0137] R 1The abbreviation, whether the same or different, represents methyl, ethyl, n-propyl, n-butyl, iso-propyl, iso-butyl, sec-butyl, tert-butyl, cyclopentyl 35, or cyclohexyl, where each of these groups may be partially or completely deuterated, or a phenyl group, which may also be Foreignfiling text P25-001 .docx

[0138] -21 -

[0139] may be partially or completely deuterated and / or may be modified by one or more substituents R 5 It can be substituted; there can be two or three substituents R 1 , which bind to the same Si atom, also form a ring with each other;

[0140] 5

[0141] R 2 The term "same" or "different" in each occurrence represents H or D, especially H;

[0142] R 3The group represents methyl, ethyl, or phenyl, either the same or different, in each occurrence, whereby these groups may also be partially or completely deuterated, with methyl and ethyl being particularly preferred; where two R groups may be present. 3 , which bind to the same carbon atom, also form a 5-membered ring together;

[0143] 15 R 4 The term "same" or "different" in each occurrence represents H or D, especially H;

[0144] R 5 stands equal or different for H, D, Si(R) in each occurrence. 6 )s, Methyl, Ethyl, n-Propyl, n-Butyl, iso-Propyl, iso-Butyl, sec-Butyl, tert-Butyl, neo-Pentyl, Cyclopentyl or Cyclohexyl, wherein these groups may each be partially or completely deuterated; in which case two or three substituents R 5 , which bind to neighboring C atoms, also form a ring with each other;

[0145] 25 R 6The symbol represents, in the same or different ways, methyl, ethyl, n-propyl, n-butyl, iso-propyl, iso-butyl, sec-butyl, tert-butyl, cyclopentyl or cyclohexyl, each of which may be partially or completely deuterated, or a phenyl group, which may also be partially or completely deuterated and / or may also be substituted by 30 with one or more alkyl groups having 1 to 5 carbon atoms, wherein two or more adjacent alkyl groups may also form a ring with each other;

[0146] n is 1 ;

[0147] 35

[0148] p is 1 or 2. Foreignfiling text P25-001 .docx

[0149] In one embodiment of the present invention, the two residues R form 3 together with the C atom to which the two R groups are attached 3 bind, 5 and / or the two remainders R 4 together with the C atom to which the two R groups are attached 4bind, a ring of formulas (RC-1) to (RC-7), wherein the structures (RC-1), (RC-2) and (RC-6) are preferred,

[0150] 10

[0151]

[0152]

[0153] Formula (RC-3) 15

[0154]

[0155] Formula (RC-4) Formula (RC-5) Formula (RC-6) 20

[0156]

[0157] Formula 25 (RC-7)

[0158] where the dashed lines represent the connection points to the respective group and the other symbols have the following meaning:

[0159] 30 R' is the same or different at each occurrence H, D or Methyl, which may also be partially or completely deuterated;

[0160] v is O to 14;

[0161] z is O to 18.

[0162] 35 In the compounds according to the invention, which are processed by vacuum evaporation, the alkyl groups preferably have no more than Foreignfiling text P25-001 .docx

[0163] -23 -

[0164] Ten carbon atoms, particularly preferably no more than six carbon atoms, most preferably no more than four carbon atoms. For compounds processed from solution, compounds substituted with alkyl groups, especially branched alkyl groups, with up to 10⁵ carbon atoms and / or substituted with oligoarylene groups, for example ortho-, meta-, para- or branched terphenyl or quaterphenyl groups, are also suitable.

[0165] Particularly for the use of the compounds according to the invention in 10 of a capping layer, i.e., a layer outside the active stack of the OLED, it may be preferred if the compounds contain one or more crosslinkable groups. A further object of the present invention is therefore a compound according to formula (1') or according to the preferred embodiments described above.

[0166] 15

[0167]

[0168] Formula (T)

[0169] wherein the symbols and indices have the meanings mentioned above,25 characterized in that the compound consists of one or more of the substituents R 1 to R 6 contains a networkable group.

[0170] In the present invention, a crosslinkable group 30 is a functional group capable of undergoing a reaction to form an insoluble compound. This reaction can occur with another identical crosslinkable group, another different crosslinkable group, or any other part of the same or a different compound. The crosslinkable group 35 is therefore a reactive group. The result of the reaction of the crosslinkable group is a correspondingly crosslinked compound.

[0171] -24 -

[0172] The chemical reaction can also be carried out within the layer, resulting in an insoluble layer. Crosslinking can be accelerated by heat and / or by UV, microwave, X-ray, or electron radiation, optionally in the presence of an initiator.

[0173] 5 “Insoluble” within the meaning of the present invention preferably means that the compound, after the crosslinking reaction, i.e., after the reaction of the crosslinkable groups, has a solubility at room temperature in an organic solvent which is at least a factor of 3, preferably at least a factor of 10, lower than that of the corresponding non-crosslinked compound according to the invention in the same organic solvent.

[0174] The compound according to the invention can comprise one, two, three or more crosslinkable groups, with two, three or more crosslinkable groups being preferred.

[0175] Suitable and preferred networkable groups are listed below:

[0176] 20

[0177] a) Terminal or cyclic alkenyl or terminal dienyl and alkynyl groups:

[0178] Suitable units are those containing a terminal or cyclic double bond, a terminal dienyl group or a terminal triple bond, in particular terminal or cyclic 25

[0179] Alkenyl, terminal dienyl, or terminal alkynyl groups with 2 to 20 carbon atoms, preferably with 2 to 10 carbon atoms, wherein individual CH2 groups and / or individual hydrogen atoms may also be replaced by the aforementioned groups R, and the groups may be partially or completely deuterated. Furthermore, groups comprising 30

[0180] are to be regarded as precursors and are capable of forming a double or triple bond in situ.

[0181] b) Alkenyloxy, dienyloxy or alkynyloxy groups:

[0182] Alkenyloxy, dienyloxy and alkynyloxy are also suitable.35

[0183] groups, preferably alkenyloxy groups. Foreignfiling text P25-001 .docx

[0184] - 25 -

[0185] c) Acrylic acid groups:

[0186] Acrylic acid units in the broadest sense are also suitable, preferably acrylic esters, acrylamides, methacryl esters and methacrylamides. Ci-w-alkyl acrylate and Ci-io-alkyl methacrylate are particularly preferred.

[0187] 5

[0188] The crosslinking reaction of the groups mentioned above under a) to c) can proceed via a radical, a cationic, or anionic mechanism, as well as via cycloaddition. It can be advantageous to add a suitable initiator for the crosslinking reaction.10 Suitable initiators for radical crosslinking are, for example, dibenzoyl peroxide, AIBN, or TEMPO. Suitable initiators for cationic crosslinking are, for example, AIDS, BF3, triphenyl methyl perchlorate, or tropylium hexachloroantimonate. Suitable initiators for anionic crosslinking are bases, in particular butyllithium. In a 15 preferred embodiment of the present invention, however, the crosslinking is carried out without the addition of an initiator and is initiated exclusively thermally.This preference is justified by the fact that the absence of the initiator prevents contamination of the layer, which could lead to a deterioration of the device properties 20.

[0189] d) Oxetanes and oxiranes:

[0190] Another suitable class of crosslinkable groups are oxetanes and oxiranes, which crosslink cationically via ring opening. Here, too, it can be useful to add an initiator for the crosslinking reaction.

[0191] Suitable initiators include, for example, AICI3, BF3, triphenylmethyl perchlorate, or tropylium hexachloroantimonate. Photoacids can also be added as initiators.

[0192] 30 e) Silanes:

[0193] Silane groups SiRs are also suitable as a class of crosslinkable groups, where at least two groups R, preferably all three groups R, represent CI or an alkoxy group with 1 to 20 carbon atoms. This group reacts in the presence of water to form an oligo- or polysiloxane. Foreignfiling text P25-001 .docx

[0194] f) Cyclobutane groups

[0195] The crosslinkable groups mentioned above under a) to f) are generally known to the person skilled in the art, as are the suitable reaction5 conditions used to crosslink these groups.

[0196] Preferred crosslinkable groups include alkenyl groups of formula Q1, dienyl groups of formula Q2, alkynyl groups of formula Q3, alkenyloxy groups of formula Q4, dienyloxy groups of formula Q5, alkynyloxy groups of formula Q6, acrylic acid groups of formulas Q7 and Q8, oxetane groups of formulas Q9 and Q10, oxirane groups of formula Q11, and cyclobutane groups of formulas Q12, Q13, and Q14.

[0197] 15

[0198] 20

[0199] 25

[0200] 30

[0201]

[0202] 35Foreignfiling text P25-001 .docx

[0203] - 27 -

[0204] 5

[0205] 10

[0206]

[0207] 15

[0208] where the symbols and indices used have the following meanings:

[0209] R 11, R 12 , R 13 , R 14 are the same or different in each occurrence H, D, 20

[0210] a straight-chain alkyl group with 1 to 6 carbon atoms, preferably with 1 to 4 carbon atoms, or a branched or cyclic alkyl group with 3 to 6 carbon atoms, preferably H, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl or tert-butyl and particularly preferably H or methyl;

[0211] m is 0 to 8;

[0212] 25

[0213] n is 1 to 8;

[0214] Ar 10 In each occurrence, the aromatic ring system is either the same or different, consisting of 6 to 40 aromatic ring atoms or a heteroaromatic ring system with 5 to 40 aromatic ring atoms, wherein the aromatic or heteroaromatic ring system is connected to a 30

[0215] or can be substituted by several residues other than H, wherein the residues preferably have the same .

[0216] The dashed bonds in formulas Q1 to Q11 and Q14, as well as the dashed bonds in formulas Q12 and Q13, represent the

[0217] 35

[0218] Linking the networkable group to the repetition units. Foreignfiling text P25-001 .docx

[0219] - 28 -

[0220] The crosslinkable groups of formulas Q1 to Q14 can be directly linked to the repeating unit, or indirectly, via another mono- or polycyclic, aromatic or heteroaromatic ring system Ar 10 , as shown in the following formulas Q15 to Q28:

[0221] 10

[0222] 15

[0223] 20

[0224] 25

[0225] 30

[0226] 35

[0227]

[0228] Foreignfiling_text P25-001.docx

[0229] -29 -

[0230] "

[0231] <

[0232] >

[0233]

[0234] where the symbols and indices have the same meanings as described above.

[0235] The following groups are particularly favored for networking:

[0236] 15

[0237] >

[0238] 20

[0239] 25

[0240] 30

[0241] 35

[0242]

[0243] Foreign filing text P25-001 .docx

[0244] - 30 -

[0245] 5

[0246] 10

[0247] 15"

[0248] 20

[0249] 25

[0250] 30

[0251]

[0252] the symbols and indices used have the meanings mentioned above.

[0253] 35

[0254] The following groups are particularly favored for networking: Foreignfiling text P25-001 .docx

[0255] - 31 -

[0256] 5

[0257] 10

[0258] 15

[0259] 20

[0260] 25

[0261] 30

[0262]

[0263] 35Foreignfiling text P25-001 .docx

[0264] - 32 -

[0265] 5

[0266] 10

[0267] 15

[0268] 20

[0269] 25

[0270] 30

[0271]

[0272] 35Foreignfiling text P25-001 .docx

[0273] - 33 -

[0274] 5

[0275]

[0276] As described above, the compounds according to the invention can also be partially or completely deuterated. However, no advantage of deuterated materials is to be expected when used to reduce the refractive index of the 10 layer. Since the production of deuterated materials is complex and expensive, it is therefore preferred if the compounds according to the invention are not deuterated, i.e., if they contain deuterium in its natural isotopic distribution, as deuteration does not lead to any particular technical effect.

[0277] 15

[0278] The ordinary refractive index of the compounds according to the invention, measured via ellipsometry at 620 nm, is preferably < 1.7, particularly preferably < 1.6 and most preferably < 1.55.

[0279] 20 Preferably, the compound according to the invention may have a molecular weight of < 4000 g / mol, preferably < 3000 g / mol, particularly preferably < 2000 g / mol, and most preferably < 1500 g / mol. Higher molecular weights may also be suitable and preferred when processed from solution.

[0280] 25

[0281] Furthermore, preferred compounds according to the invention are characterized by the fact that they are sublimable.

[0282] The preferred embodiments mentioned above can be combined arbitrarily within the limitations defined in claim 1. In a particularly preferred embodiment of the invention, the above-mentioned preferences occur simultaneously.

[0283] Examples of preferred compounds according to the 35 embodiments listed above are those listed in the following table. Foreignfiling text P25-001 .docx

[0284] 5

[0285] >

[0286] 10

[0287] 15

[0288] 20

[0289] 25

[0290] 30

[0291] 35

[0292]

[0293] Foreignfiling text P25-001 .docx

[0294] - 35 -

[0295] 5

[0296] 10

[0297] 15

[0298] 20

[0299] 25

[0300] 30

[0301]

[0302] Foreignfiling text P25-001 .docx

[0303] - 36 -

[0304] 5

[0305] 10

[0306] 15

[0307] 20

[0308] 25

[0309]

[0310] 30

[0311] As shown in Scheme 1, the compounds 4 according to the invention can be prepared from aryl halides 1 known from the literature and the halosilanes 3 by salt metathetic reaction. For this purpose, the aryl halides 1 are first reacted with a 35 reactive metal M* such as Li, Mg or Zn, or with a metal-organic compound such as an organolithium compound, preferably n-butyllithium, n-hexyllithium, tert-butyllithium, or a Grignard reagent.

[0312] - 37 -

[0313] Preferably iso-propyl-MgCl*LiCl (Knöchel Turbo-Grignard) is transmetallated to give the compounds 2. The intermediately obtained arylmetal compounds 2 are then reacted with a mono-, di-, tri- or tetra-halo-silane or -german 3, preferably with a mono- or di-halo-silane or -german 5 3.

[0314] Scheme 1 :

[0315]

[0316]

[0317]

[0318] The symbols and indices used in Scheme 1 have the meanings given above, M* stands for a reactive metal, for example Li or Mg, and X stands for a halogen, for example Chlorine.

[0319] 25

[0320] Alternatively, the halosilanes 5 known from the literature can be reacted with the organolithium, organomagnesium or organozinc compounds 6 known from the literature to form compounds 7 according to the invention, as shown in Scheme 2.

[0321] 30

[0322] Scheme 2: Foreign filing text P25-001 .docx

[0323] - 38 -

[0324]

[0325] 10

[0326] Preferred reaction media in both cases are dipolar aprotic solvents, such as ethers or cyclic ethers, in particular diethyl, di-n-butyl, tert-butyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, or dioxane, or mixtures thereof. The exothermic salt metathesis is preferably carried out first at cryogenic temperatures or under refrigeration. If necessary, 15

[0327] The reaction is flexible and can also be carried out at elevated temperatures to complete the reaction. The work-up and purification of the compounds according to the invention is carried out according to steps known to those skilled in the art, such as quenching, extraction, chromatography, recrystallization, and fractional distillation or sublimation under high vacuum.

[0328] 20

[0329] Another object of the present invention is therefore a method for producing a compound according to the invention, wherein first an aryl halide is converted to an aryl metal compound, in particular a lithium or magnesium compound, and the aryl25

[0330] The metal compound is then reacted with a halogen-silicon compound or a halogen-germanium compound by salt metathesis.

[0331] These processes, optionally followed by purification, such as recrystallization or sublimation, allow the 30 compounds according to the invention to be obtained.

[0332] Compounds of high purity, preferably more than 99% (determined by 1 H-NMR, HPLC and / or GC).

[0333] The compounds according to the invention can also be mixed with a polymer and / or covalently incorporated into a polymer. This applies in particular to 35

[0334] especially if the compounds are to be used in a capping layer. Covalent incorporation into polymers is particularly possible with Ver-Foreignfiling text P25-001 .docx

[0335] - 39 -

[0336] Bonds which are substituted with reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic acid esters, or with reactive, polymerizable groups, such as olefins or oxetanes. These can be used as monomers to generate corresponding oligomers, dendrimers, or polymers. The oligomerization or polymerization preferably occurs via the halogen functionality, the boronic acid functionality, or via the polymerizable group. It is also possible to crosslink the polymers via such groups. The compounds and polymers according to the invention can be used as a crosslinked or uncrosslinked layer.

[0337] A further object of the present invention is therefore oligomers, polymers, or dendrimers containing one or more of the structures of formula (1) or of the preferred embodiment 15 listed above, wherein one or more bonds of the compounds according to the invention are present with the polymer, oligomer, or dendrimer. Depending on the linkage of the structures of formula (1) or of the preferred embodiments, these therefore form a side chain of the oligomer or polymer or are linked in the main chain. The polymers, oligomers 20, or dendrimers can be conjugated, partially conjugated, or non-conjugated. The oligomers or polymers can be linear, branched, or dendritic. The same preferences apply to the repeating units of the compounds according to the invention in oligomers, dendrimers, and polymers as described above for the compounds 25 according to the invention.

[0338] Of particular interest are compounds according to the invention which are characterized by a high glass transition temperature. In this context, compounds according to formula (1) or (2) are particularly relevant.

[0339] 30 according to the embodiments preferably having a glass transition temperature of at least 70 °C, particularly preferably at least 110 °C, most preferably at least 125 °C and particularly preferably at least 150 °C, determined according to DIN 51005 (version 2005-08).

[0340] 35Foreignfiling text P25-001 .docx

[0341] -40 -

[0342] 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, or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents include, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrol, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin. Dodecyl benzene, ethyl benzoate, indane, 15 NMP,p-Cymene, Phenetol, 1,4-Diisopropylbenzene, Dibenzyl ether, Diethylene glycol butyl ether, Triethylene glycol butyl ether, Diethylene glycol dibutyl ether, Triethylene glycol dimethyl ether, Diethylene glycol monobutyl ether, Tripropylene glycol dimethyl ether, Tetraethylene glycol dimethyl ether, 2-Isopropylnaphthalene, Pentylbenzene, Hexylbenzene, Heptylbenzene, Octylbenzene, 1,1-Bis(3,4-dimethylphenyl)ethane, 2-Methylbiphenyl, 3-Methylbiphenyl, 1-Methylnaphthalene, 1-Ethylnaphthalene, Ethyl octanoate, Sebacia diethyl ester, Octyl octanoate, Heptylbenzene, Menthyl isovalerate, Cyclohexylhexanoate or mixtures of these solvents.

[0343] 25 Another object of the present invention is therefore a formulation or composition comprising at least one compound according to formula (1) or according to the preferred embodiments and at least one further compound. Formulations or compositions comprising oligomers, dendrimers, or polymers 30 of the present invention are included here. The further compound may, for example, be a solvent, in particular one of the solvents mentioned above, or a mixture of these solvents. If the further compound comprises one or more solvents, this mixture is referred to here as the formulation. The further compound 35 may also be at least one further organic or inorganic compound that is also used in the electronic device.

[0344] - 41 -

[0345] for example an electron transport material, a hole transport material, an emitting compound and / or a matrix material, wherein a mixture of a compound according to formula (1) and another organic or inorganic compound also used in the electronic device is hereby referred to as the composition or mixture.

[0346] Another object of the present invention is therefore a mixture containing at least one compound according to formula (1) or

[0347] 10 according to the preferred embodiments and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF, host materials, electron transport materials, electron injection materials, hole transport materials, hole injection materials, exciton- 15 blocking materials, electron blocking materials and hole blocking materials, preferably electron injection materials, electron transport materials, hole injection materials or hole transport materials, particularly preferably electron transport materials or hole transport materials.

[0348] 20

[0349] The compounds according to the invention can be used in particular to vary and especially to reduce the refractive index of functional layers in an electronic device, preferably an organic electroluminescence device. This makes it easy to adapt and match the refractive indices of different functional layers, thereby enabling a significant increase in the efficiency of these devices.

[0350] The compound according to the invention can be used in combination with fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF, and / or host materials to modify their refractive index. Since the emission layer often already comprises at least two, three, or more components, and finding a power maximum is therefore complex, surprising advantages can arise from using the compounds according to the invention in an electron transport layer and / or a hole transport layer.

[0351] - 42 -

[0352] Preferably, the proportion of compounds according to formula (1) or preferred embodiments in a mixture may be in the range of 5 vol.% to 90 vol.%, particularly preferably in the range of 5 to 10 vol.% to 70 vol.%, and most preferably in the range of 15 vol.% to 50 vol.%. This proportion has proven to be particularly suitable for reducing the refractive index without a negative impact on the electronic properties of the layer.

[0353] 10 Preferably, the composition may comprise at least one compound according to formula (1) or the preferred embodiments and at least one hole transport material.

[0354] Compounds with hole transport properties, also referred to herein as hole conductor or hole transport materials, are capable of transporting holes, i.e., positive charges, which are generally injected from the anode or an adjacent layer, for example, a hole injection layer. A hole transport material generally exhibits a high HOMO level, preferably at least -5.4 eV, as defined by quantum mechanical calculations. Depending on the design of the electronic device, a hole transport material can also be used as a hole injection material.

[0355] Preferred compounds exhibiting hole injection and / or hole transport properties include, for example, triarylamine, benzidine, tetraaryl-para-phenylenediamine, triarylphosphine, phenothiazine, phenoxazine, dihydrophenazine, thianthrene, dibenzo-para-dioxin, phenoxathiin, carbazole, azulene, thiophene, pyrrole and furan derivatives and other 0-, S- or N-containing heterocycles with a high HOMO 30 (HOMO = highest occupied molecular orbital).

[0356] Compounds exhibiting hole injection and / or hole transport properties are preferably selected from triarylamines, in particular mono-triarylamines and bis-triarylamines and carbazolamines. A mono-triarylamine is understood to be a compound containing a single amine group, wherein the nitrogen atom of the amine group is... Foreignfiling text P25-001 .docx

[0357] -43 -

[0358] Three groups selected from aromatic and heteroaromatic ring systems are bonded to each nitrogen atom of the two amine groups. A bis-triarylamine is a compound comprising two and no further amine groups, wherein three groups selected from aromatic and heteroaromatic ring systems are bonded to each nitrogen atom of the two amine groups. A carbazolamine is a compound containing a carbazole group and an amine group, wherein the amine group is preferably a triarylamine group. A triarylamine group is an amine group in which three groups selected from aromatic and heteroaromatic ring systems are bonded to the nitrogen atom of the amine group.

[0359] In a preferred embodiment, the composition may comprise at least one hole conductor material selected from compounds of formulas (L-1) and / or (L-2).

[0360] 20

[0361]

[0362] where the connections may be partially or completely deuterated and the following applies to the symbols used:

[0363] 25 ares 15 The composition is chosen in each instance, either the same or different, from aromatic ring systems with 6 to 40 aromatic ring atoms, separated by one or more R groups. 15 can be substituted, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, separated by one or more R groups 15 can be substituted 30;

[0364] Ar 16 is an aromatic ring system with 6 to 40 aromatic ring atoms, separated by one or more R groups 15 may be substituted, or a heteroaromatic ring system with 5 to 40 aromatic ring atoms, which is modified by one or more R groups 15 may be substituted; Foreignfiling text P25-001 .docx

[0365] - 44 -

[0366] R 15is chosen from H, D, F, C(=O)R for each occurrence, whether the same or different. 16 , CN, Si(R 16 )3, N(R 16 )2, P(=O)(R 16 )2, OR 16 , S(=O)R 16 , S(=O)2R 16 , straight-chain alkyl or alkoxy groups with 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups with 3 to 20 carbon atoms, alkenyl or alkynyl groups with 2 to 20 carbon atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic and heteroaromatic ring systems may be partially or completely deuterated and / or modified by one or more R groups 16 can be substituted and wherein one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups can each be replaced by -R 16 C=CR 16 -, -CEC-, Si(R 16 )2, C=O,

[0367] C=NR 16 , -C(=O)O-, -C(=O)NR 16 -, NR 16 , P(=O)(R 16 ), -0-, -S-, SO or SO2; wherein two or more, preferably adjacent, residues R 15 together form a ring system;

[0368] 20 R 16 is chosen from H, D, in every occurrence, whether the same or different,

[0369] F, C(=O)R 17 , CN, Si(R 17 )3, N(R 17 )2, P(=O)(R 17 )2, OR 17 , S(=O)R 17 , S(=O)2R 17, straight-chain alkyl or alkoxy groups with 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups with 3 to 20 carbon atoms, alkenyl or alkynyl groups with 2 to 20 carbon atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein the alkyl, alkoxy, alkenyl, and alkynyl groups and the aromatic and heteroaromatic ring systems may each be partially or completely deuterated and / or modified by one or more R groups 17 can be substituted and wherein one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups can each be replaced by -R 17 C=CR 17 -,

[0370] -C=C-, Si(R 17 )2, C=O, C=NR 17 , -C(=O)O-, -C(=O)NR 17 -, NR 17 , 35 P(=O)(R 17 ), -0-, -S-, SO or SO2; where two or Foreignfiling text P25-001 .docx

[0371] -45 -

[0372] several, preferably adjacent residues R 16 together form a ring system;

[0373] R 17 The ring system is selected in each occurrence from H, D, F, CI, Br, I, CN, alkyl groups with 1 to 20 carbon atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein the alkyl groups, the aromatic and the heteroaromatic ring systems may each be partially or completely deuterated and / or substituted by F and / or CN groups; in this case, two or more, preferably adjacent, R groups may be used. 17 together form a ring system.

[0374] Preferred Groups Ar 15are the same or different at each occurrence 15 selected from monovalent groups derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, 20 pyrimidine, pyrazine, pyridazine and triazine, each of the groups being partially or completely deuterated and / or having one or more R groups 15 may be substituted.

[0375] Preferably the groups Ar 15the same or different at each occurrence, selected from monovalent groups representing combinations of 2 to 4 groups selected from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, 30 benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, each of the groups being partially or completely deuterated and / or with one or more R groups 15 may be substituted.

[0376] 35 Particularly preferred groups Ar 15 are, the same or different at each occurrence, chosen from monovalent groups that differ from benzene, Foreignfiling text P25-001 .docx

[0377] -46 -

[0378] Biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, carbazole, benzofuran, benzothiophene, benzo-condensed dibenzofuranyl, benzo-condensed dibenzothiophenyl and phenyl, which is substituted with a group selected from naphthyl, phenanthrenyl, fluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidyl and triazinyl, each of the above groups being partially or completely deuterated and / or modified with one or more R groups. 15 may be substituted.

[0379] Preferred Groups Ar 16are selected from divalent groups derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, each of the groups being partially or completely deuterated and / or having one or more R groups 15 may be substituted.

[0380] 20

[0381] Preferably the groups Ar 16 selected from divalent groups representing combinations of 2 to 4 groups selected from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, 25 benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran,

[0382] Dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, each of the groups being partially or completely deuterated and / or with one or more R groups 15 may be substituted.

[0383] 30

[0384] Particularly preferred groups Ar 16 are selected from divalent groups that differ from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, carbazole, benzofuran, benzothiophene, benzo-condensed dibenzofuranyl and benzo-condensed Foreignfiling text P25-001 .docx

[0385] - 47 -

[0386] derive dibenzothienyl, wherein each of the above groups is partially or completely deuterated and / or combined with R groups. 15 may be substituted.

[0387] Preferably R 15 same or different chosen from H, D, F, CN, 5 Si(R 16 )3, N(R 16 )2, straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, wherein the alkyl and alkoxy groups and the aromatic and heteroaromatic ring systems are partially or completely deuterated and / or modified by R groups 16 may be substituted.

[0388] Preferably R 16 Equal or different choices made from H, D, F, CN, Si(R) 17 )3, N(R 17)2, straight-chain alkyl or alkoxy groups with 1 to 20 C-15 atoms, branched or cyclic alkyl or alkoxy groups with 3 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, wherein the alkyl and alkoxy groups and the aromatic and heteroaromatic ring systems are partially or completely deuterated 20 and / or by one or more R groups 17 may be substituted.

[0389] Preferably R 17 The same or different elements are chosen for each occurrence from H, D, F, CN, alkyl groups with 1 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms and heteroaromatic ring systems with 5 to 40 aromatic ring atoms.

[0390] Particularly preferred embodiments of the compounds of formula (L-1) correspond to the following formulas,

[0391] 30

[0392] 35

[0393]

[0394] Foreign filing text P25-001 .docx

[0395] - 48 -

[0396] >

[0397] 5

[0398] < "

[0399] 10

[0400] >

[0401] 15

[0402] 20

[0403] 25

[0404]

[0405] where the compounds may be partially or completely deuterated, the symbols Ar 15 and R 15 the meanings mentioned above, especially for formula (L-1), and the following applies to the other symbols:

[0406] 30

[0407] Ar 17 is selected from aromatic ring systems with 6 to 13 aromatic ring atoms, separated by one or more R groups 15 can be substituted, and heteroaromatic ring systems with 5 to 13 aromatic ring atoms, separated by one or

[0408] 35 several remainders R 15 can be substituted with something other than H; Foreignfiling text P25-001 .docx

[0409] -49 -

[0410] X is chosen from a bond, 0, S, NR, either the same or different in each occurrence. 15 and C(R 15 )2;

[0411] Y 1 is selected from 0 or S;

[0412] 5

[0413] n is 0 or 1 , where n = 0 means that the group with index n does not exist and that the groups bound to the group with index n are directly connected to each other, with the proviso that n is not 0 in the case of formula (L-1-9).

[0414] 10

[0415] The preferred group is Ar 17 selected from divalent groups derived from benzene, biphenyl, naphthalene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, each of the groups with R substituents 15 may be substituted.

[0416] 15

[0417] Particularly preferred are the compounds of formulas (L-1-2) and (L-1-3), wherein compounds of the following formula (L-1-2-1) as an embodiment of formula (L-1-2) are especially preferred,

[0418] 20

[0419] 25

[0420]

[0421] where the compounds may be partially or completely deuterated 30

[0422] and the symbols and indices have the aforementioned meanings and preferably correspond to the preferred embodiments mentioned above.

[0423] Particularly preferred embodiments of the compounds of formula 35

[0424] (L-2) correspond to the following formulas (L-2-1) and / or (L-2-2), Foreignfiling text P25-001 .docx

[0425] - 50 -

[0426]

[0427] 15 where the compounds may be partially or completely deuterated, the symbols Ar15 and R 15 the aforementioned meanings and preferably correspond to the preferred embodiments mentioned above, and the following applies to the other symbols:

[0428] 20 Y 2 is chosen the same or differently from a bond, 0, S, NR, in each occurrence. 15 and C(R 15 )2;

[0429] k is 1, 2, 3 or 4, preferably 1 or 2;

[0430] 25 i is 1, 2 or 3, preferably 1 or 2, particularly preferably 1.

[0431] Preferred specific compounds that can be used as hole conductor material according to the present invention are listed in the following table, wherein these compounds can also be partially or completely deuterated:

[0432] 35

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[0802]

[0803] 35 Preferably, these arylamines and heterocycles, which are generally used as hole injection and / or hole transport materials, have a HOMO of more than -5.8 eV (relative to vacuum level), especially Foreignfiling text P25-001 .docx

[0804] - 94 -

[0805] preferably from more than -5.5 eV, as defined by quantum mechanical calculations.

[0806] According to a preferred embodiment of the present invention 5, the mixture contains, in addition to the compound according to the invention and the hole transport material as described above, no further components, i.e., no further functional materials. These are therefore material mixtures that are used as such for the production of the hole transport layer. These mixtures 10 are also referred to as premix systems, which are used as the sole material source for the deposition of the materials for the hole transport layer and which have a constant mixing ratio during deposition. This allows the deposition of a layer with a uniform distribution of the components 15 to be achieved in a simple and rapid manner, without the need for precise control of a multitude of material sources.

[0807] For the use of such a premix system, which is evaporated as a mixture, it is preferred if the composition comprises at least one hole transport material and at least one compound according to the invention, wherein the hole transport material and the compound according to the invention are sublimable and the difference in the sublimation temperature of the individual compounds is a maximum of 5 °C, preferably a maximum of 2 °C, wherein the sublimation temperature is determined e.g. by means of vacuum TGA measurement.

[0808] This design provides sublimable compositions that can be used particularly reliably in a plant for the production of high-quality electronic devices.

[0809] 30

[0810] Furthermore, it may be provided that the composition comprises at least one compound according to formula (1) or according to the preferred embodiments and at least one electron transport material.

[0811] 35 compounds exhibiting electron injection and / or electron transport properties, hereafter also referred to as electron transport materials. Foreignfiling text P25-001 .docx

[0812] - 95 -

[0813] Examples of such derivatives include pyridine, pyrimidine, pyridazine, pyrazine, oxadiazole, quinoline, quinoxaline, anthracene, benzanthracene, pyrene, perylene, benzimidazole, triazine, ketone, phosphine oxide and phenazine derivatives, but also triarylboranes and other 0-, S- or N-containing 5 heterocycles with a low LUMO (LUMO = lowest unoccupied molecular orbital).

[0814] Particularly suitable compounds for electron-transporting and electron-injecting layers are metal chelates of 8-hydroxyquinoline 10 (e.g., LiQ, AIQ3, GaQs, MgCte, ZnCte, InQs, ZrCU), BAIQ, Ga-oxinoid complexes, 4-azaphenanthrene-5-ol-Be complexes (US 5529853 A, see formula ET-1), butadiene derivatives (US 4356429), benzimidazole derivatives (US 2007 / 0273272 A1), such as TPBI (US 5766779, see formula ET-2), 1,3,5-triazines, e.g., spirobifluorene-triazine derivatives (e.g., according to the DE).

[0815] 15 102008064200), pyrenes, anthracenes, tetracenes, fluorenes, spirofluorenes, dendrimers, tetracenes (e.g. rubrene derivatives), 1,10-phenanthroline derivatives (JP 2003-115387, JP 2004-311184, JP-2001 -267080, WO 2002 / 043449), sila-cyclopentadiene derivatives (EP 1480280, EP 1478032, EP 1469533), borane derivatives, such as. B. triarylborane derivatives with Si (US 20 2007 / 0087219 A1, see formula ET-3), pyridine derivatives (JP 2004-200162),

[0816] Phenanthrolines, especially 1,10-phenanthroline derivatives, such as BCP and Bphen, also several phenanthrolines linked via biphenyl or other aromatic groups (US-2007-0252517 A1) or phenanthrolines linked with anthracene (US 2007-0122656 A1, see formulas ET-4 and 25 ET-5).

[0817] Examples of electron transport materials are the compounds shown below, which may also be partially or completely deuterated:

[0818] 30

[0819] 35Foreignfiling text P25-001 .docx

[0820] - 96 -

[0821]

[0822] 15

[0823] Formula ET-4

[0824]

[0825] 20 Formula ET-5

[0826] Heterocyclic organic compounds such as thiopyran dioxides, oxazoles, triazoles, imidazoles, or oxadiazoles are also suitable. Examples of the use of five-membered rings with N such as oxazoles, preferably 25 1,3,4-oxadiazoles, which are set out, among others, in US 2007 / 0273272 A1; thiazoles, oxadiazoles, thiadiazoles, triazoles, etc., see US 2008 / 0102311 A1 and YA Levin, MS Skorobogatova, Khimiya Geterotsiklicheskikh Soedinenii 1967 (2), 339-341 silacyclopentadiene derivatives. Organic compounds such as derivatives of fluorenone, 30-fluorenylidene methane, perylenetetracarbonic acid, anthraquinone dimethane, diphenoquinone, anthrone and anthraquinone diethylenediamine can also be used.

[0827] Preferred are 2,9,10-substituted anthracenes (with 1- or 2-35 naphthyl and 4- or 3-biphenyl) or molecules containing two anthracene units (US2008 / 0193796 A1, see formula ET-6). Advantageous is Foreignfiling text P25-001 .docx

[0828] - 97 -

[0829] also the combination of 9,10-substituted anthracene units with benzimidazole derivatives (US 2006 147747 A and EP 1551206 A1, see formulas ET-7 and ET-8).

[0830] 5

[0831] 10

[0832]

[0833]

[0834]

[0835] In a preferred embodiment, the composition 20 may comprise at least one electron transport material selected from compounds of formulas (E-1) to (E-4)

[0836] 25

[0837] >

[0838] <

[0839] 30

[0840]

[0841] where the compounds may be partially or completely deuterated, R 15 the meaning previously mentioned for formula (L-1) and which also applies to 35: Foreignfiling text P25-001 .docx

[0842] - 98 -

[0843] Ar 18 is selected from aromatic ring systems with 6 to 40 aromatic ring atoms, separated by one or more R groups 15 can be substituted, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, separated by one or more R groups 15 can be substi5 tuiert.

[0844] Compounds according to formulas (E-1) to (E-3) are preferred, in particular compounds according to formula (E-1).

[0845] 10 Particularly preferred embodiments of compounds that can be used as electron transport materials correspond to the following formulas (E-1-1) and / or (E-1-2)

[0846] 15

[0847] 20

[0848] 25

[0849]

[0850] where the compounds can also be partially or completely deuterated, the symbols R 15which has the aforementioned meanings and preferably corresponds to the preferred embodiments 30 mentioned above, and for the further symbols the following applies:

[0851] Ar 19 is selected from aromatic ring systems with 6 to 20 aromatic ring atoms, separated by one or more R groups 15 can be substituted, and heteroaromatic ring systems 35 with 5 to 20 aromatic ring atoms, which are separated by one or more R groups 15 can be substituted; Foreignfiling text P25-001 .docx

[0852] - 99 -

[0853] m is 0 or 1, where m = 0 means that the group with index m does not exist and that the values ​​attached to the group (Ar 19 ) m bound groups are directly connected to each other.

[0854] 5

[0855] Preferred specific compounds that can be used as electron transport materials according to the present invention are listed in the following table, wherein these compounds may also be partially or completely deuterated:

[0856] 10

[0857] 15

[0858] 20

[0859] 25

[0860] 30

[0861]

[0862] 35Foreignfiling text P25-001 .docx

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[0907]

[0908] According to a preferred embodiment of the present invention, the mixture contains no further components besides the components of the compound according to formula (1) or the preferred embodiments and the electron transport material, i.e., no further functional materials. These are therefore material mixtures that are used as such for the production of the electron transport layer. These mixtures are also referred to as premix systems, which are used as the sole material source for the deposition of the materials for the electron transport layer and which have a constant mixing ratio during deposition. This allows for the simple and rapid deposition of a layer with a uniform distribution of the components without the need for precise control of a large number of material sources.

[0909] 25

[0910] For the use of such a premix system, which is evaporated as a mixture, it is preferred if the composition comprises at least one electron transport material and at least one compound according to the invention, wherein the electron transport material and the compound according to the invention are sublimable and the difference in the sublimation temperature is a maximum of 5 °C, preferably a maximum of 2 °C, wherein the sublimation temperature is determined e.g. by means of vacuum TGA measurement.

[0911] 35 This design provides sublimable compositions that can be reliably used in a plant to manufacture high-quality electronic devices. Foreignfiling text P25-001 .docx

[0912] - 106 -

[0913] Preferably, the compounds that can generate the electron injection and / or electron transport properties lead to a LUMO of less than -2.3 eV, preferably less than -2.5 eV (vs. 5 vacuum levels), particularly preferably less than -2.7 eV, as defined by quantum mechanical calculations.

[0914] Furthermore, the compositions according to the invention can comprise at least one hole blocking material (HBM).

[0915] 10 A hole-blocking material is a material which, in a multilayer composite, prevents or minimizes the passage of holes (positive charges), wherein the hole-blocking layer containing the hole-blocking material is usually arranged adjacent to an emission layer on the cathode side. Hole-blocking layers are frequently placed 15 between the light-emitting layer and the electron transport layer in OLEDs.

[0916] In principle, any known hole-blocking material can be used. In addition to further hole-blocking materials described at 20 other locations in the present application, suitable hole-blocking materials include metal complexes (US 2003 / 0068528), such as bis(2-methyl-8-quinolinolato)(4-phenylphenolato)-aluminum(III) (BAIQ). Fac-tris(1-phenylpyrazolato-N,C2)iridium(III) (Ir(ppz)3) is also used for these purposes (US 2003 / 0175553 25 A1). Phenanthroline derivatives, such as BCP, or phthalimides, such as TMPP, can also be used. Further suitable hole-blocking materials are described in WO 00 / 70655 A2, WO 01 / 41512, and WO 01 / 93642 A1.

[0917] 30 Furthermore, the compositions according to the invention can comprise at least one electron blocking material (EBM). An electron blocking material is a material which, in a multilayer composite, prevents or minimizes the conduction of electrons, wherein the electron blocking layer containing the EBM is arranged, in particular, on the anode side adjacent to an emission layer.

[0918] - 107 -

[0919] In principle, any known electron-blocking material can be used. In addition to other electron-blocking materials described elsewhere in this application, five suitable electron-blocking materials are transition metal complexes, such as lr(ppz)3 (US 2003 / 0175553). Preferably, the electron-blocking material can further be selected from amines, triaryl amines, and their derivatives.

[0920] 10 Organic functional materials, such as those described above and below, are often described by the properties of the frontier orbitals, which are explained in more detail below.

[0921] The energy levels of molecular orbitals (highest occupied molecular orbital HOMO, lowest unoccupied molecular orbital LUMO, lowest triplet state Ti, lowest excited singlet state Si) are determined via quantum mechanical calculations. The Gaussian16 (Rev. B.01) software package is used in all quantum chemical calculations. The neutral singlet ground state is based on the

[0922] 20 B3LYP / 6-31G(d)-level optimizations are performed. HOMO and LUMO values ​​are determined at the B3LYP / 6-31G(d) level for the ground state energy optimized with B3LYP / 6-31G(d). Subsequently, TD-DFT singlet and triplet excitations (vertical excitations) are calculated using the same method (B3LYP / 6-31G(d)) and the optimized ground state geometry.

[0923] 25. The default settings for SCF and gradient convergence are used. The HOMO and LUMO values ​​in eV, derived from the quantum chemical calculation, are additionally scaled by the following factors:

[0924] HOMO_corr = 0.90603 * HOMO (in eV) - 0.84836

[0925] 30 LUMO_corr = 0.99687 * LUMO (in eV) - 0.72445

[0926] For the purposes of this application, these values ​​are to be regarded as HOMO or LUMO energy levels of the materials.

[0927] The lowest triplet state Ti is defined as the energy of the lowest-energy triplet35 state resulting from the described quantum chemical calculation. The lowest excited singlet foreign filing text P25-001 .docx

[0928] - 108 -

[0929] state Si is defined as the energy of the excited singlet state with the lowest energy, which results from the described quantum chemical calculation.

[0930] 5. A further object of the present invention is the use of a compound according to formula (1) or of the preferred embodiments mentioned above, or corresponding crosslinkable or crosslinked compounds or oligomers, polymers, or dendrimers, in an electronic device, in particular in an organic electroluminescence device. Preferably, the compounds according to the invention may be used to vary the refractive index, in particular to reduce the refractive index.

[0931] A further object of the present invention is an electronic device comprising at least one compound according to formula (1) or according to the above-mentioned preferred embodiments or corresponding crosslinkable or crosslinked compounds or oligomers, polymers or dendrimers.

[0932] 20 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 or layers which are composed entirely of inorganic materials. Particularly preferred is an electronic 25 device selected from the group consisting of organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), preferably organic light-emitting diodes (OLEDs), small-molecule organic light-emitting diodes (sOLEDs), polymer-based organic light-emitting diodes (PLEDs), 30 light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), “organic plasmon emitting devices” (DM Koller et al., Nature Photonics 2008, 1-4); organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors.

[0933] 35 (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quench devices Foreignfiling text P25-001 .docx

[0934] - 109 -

[0935] (O-FQDs) and organic electrical sensors, preferably organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), particularly preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes based on small molecules 5 (sOLEDs) and organic light-emitting diodes based on polymers (PLEDs).

[0936] The organic electroluminescent device contains a cathode, anode, and at least one emitting layer. In addition to these layers, it may contain 10 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. Likewise,

[0937] 15 Interlayers may be introduced between two emitting layers, which, for example, have an exciton-blocking function. However, it should be noted that not every one of these layers is necessarily required. The organic electroluminescent device may contain one or more emitting layers. 20 If several emission layers are present, they preferably exhibit several emission maxima between 380 nm and 750 nm, resulting in overall white emission; that is, different emitting compounds capable of fluorescence or phosphorescence are used in the emitting layers. 25 Systems with three emitting layers are particularly preferred, wherein the three layers exhibit blue, green, and orange or red emission.The organic electroluminescence device according to the invention can also be a tandem electroluminescence device, in particular for white emitting OLEDs.

[0938] 30

[0939] The compound according to formula (1) or according to the preferred embodiments described above can be used in different layers. An organic electroluminescent device containing the compound in an electron transport layer 35 and / or in a hole-blocking layer, each in combination with an electron transport or hole-blocking material, is preferred. Further preferred is Foreignfiling text P25-001 .docx

[0940] - 110 -

[0941] An organic electroluminescent device containing the compound in a hole transport layer and / or electron blocking layer, each in combination with a hole transport or electron blocking material, respectively. Furthermore, the compound can be used in an emission layer. Additionally, the compound can be used in a so-called capping layer, i.e., outside the active stack, of an organic electroluminescent device. Such a layer is frequently used to improve light extraction from the electroluminescent device. For this purpose, the material is typically used in a high concentration and preferably as a pure layer.

[0942] The emission layer of the organic electroluminescent device according to the invention can be fluorescent or phosphorescent, with fluorescence also including the special case of TADF (thermally activated delayed fluorescence). In principle, all commonly used emitters (dopeds) can be used as emitters for the emission layer. The emitter (doped) is usually used in combination with one or more matrix materials, and all commonly used matrix materials are suitable for this purpose.

[0943] 20

[0944] Preferably, the fluorescent emitter in the composition has a peak emission wavelength between 420 and 550 nm, preferably between 420 and 470 nm.

[0945] 25 Preferred fluorescent emitting compounds for hyperphosphorescent OLEDs are selected from the class of arylamines. For the purposes of the present invention, an arylamine or an aromatic amine is understood to be a compound containing three substituted or unsubstituted aromatic or heteroaromatic ring systems 30 directly bonded to the nitrogen. Preferably, at least one of these aromatic or heteroaromatic ring systems is a condensed ring system, particularly preferably with at least 14 aromatic ring atoms. Preferred examples are aromatic anthracene amines, aromatic anthracene diamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic chrysenamines, or aromatic chrysenediamines. An aromatic anthracene amine is defined as...

[0946] - 111 -

[0947] An aromatic anthracene diamine is a compound in which a diarylamine group is directly bonded to an anthracene group, preferably at the 9-position. An aromatic anthracene diamine is a compound in which two diarylamine groups are directly bonded to an anthracene group, preferably at the 9- and 10-positions. Similarly, aromatic pyrenamines, pyrendiamines, chrysenamines, and chrysendiamines are defined in which the diarylamine groups are preferably bonded to the pyrene at the 1- or 1,6-position. Other preferred emitting compounds are indenofluorenamines or fluorendiamines, for example according to WO 2006 / 108497 or WO 2006 / 122630, benzoindenofluorenamines or fluorendiamines, for example according to WO 2008 / 006449, and dibenzoindenofluorenamines or didiamines, for example according to WO 2007 / 140847, as well as the indenofluorene derivatives with fused aryl groups disclosed in WO 2010 / 012328.Equally preferred are the pyrenarylamines disclosed in WO 15 2012 / 048780 and in WO 2013 / 185871. Also preferred are the benzoindenofluorenamines disclosed in WO 2014 / 037077, the benzofluorenamines disclosed in WO 2014 / 106522, the extended benzoindenofluorenes disclosed in WO 2014 / 111269 and in WO 2017 / 036574, the phenoxazines disclosed in WO 2017 / 028940 and in WO 2017 / 028941, and the furan- or thiophene-linked fluorine derivatives disclosed in WO 2016 / 150544. Furthermore, boron compounds can be used in accordance with WO 2020 / 208051, WO 2015 / 102118, WO 2016 / 152418, WO 2018 / 095397, WO 2019 / 004248, WO 2019 / 132040, US 2020 / 0161552 and WO 2021 / 089450, WO 2015 / 102118, 25 KR 2018046851, WO 2019 / 009052, WO 2020 / 101001, US 2020 / 0207787, WO 2020 / 138874, KR 2020081978, JP 2020-147563, US 2020 / 0335705 or KR 2022041028 can be used.

[0948] Preferably, the at least one fluorescent emitter has a full width at half maximum (FWHM) < 50 nm, preferably FWHM < 40 nm, more preferably FWHM < 30 nm.

[0949] Preferably, the at least one fluorescent emitter has a LUMO of -2.1 eV to -2.5 eV, more preferably of -2.2 eV to -2.4 eV, as defined by quantum chemical calculations. Preferably, the at least one fluorescent emitter has a HOMO of -4.8 eV to -5.2 eV.

[0950] - 112 -

[0951] preferably from -4.9 eV to -5.1 eV, as defined by quantum chemical calculations.

[0952] Preferably, the energy of the lowest singlet state Si of the 5 fluorescent emitter is between 2.65 eV and 2.9 eV, more preferably between 2.7 and 2.8 eV, and more preferably between 2.7 and 2.75 eV, as defined by quantum mechanical calculations.

[0953] In a preferred embodiment of the invention, the fluorescent 10 emitter is selected from structures of the following formula (F-1),

[0954] 15

[0955]

[0956] Formula (F-1)

[0957] where R has the meanings mentioned above and the following applies to the other 20 symbols and indices used:

[0958] 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, wherein the

[0959] 25 heteroaromatic ring system may contain nitrogen, boron and / or phosphorus atoms;

[0960] Y 30 is B or N;

[0961] 30 Y 31 , Y 32 , Y 33 is the same or different in each occurrence and stands for

[0962]

[0963] SO2, SeÜ2 or a chemical bond, provided that if Y 30 for B stands, at least one of the groups Y 31 , Y 32 , Y 33 NR° stands for, and if Y 30 N stands for at least one of the group Y 31 , Y 32 , 35 Y 33 BR° stands for; Foreignfiling text P25-001 .docx

[0964] - 113 -

[0965] R° is 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 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, 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, wherein the heteroaromatic ring system may contain nitrogen, boron and / or phosphorus atoms; Two adjacent substituents R° can form an aliphatic or aromatic ring system, which can be substituted with one or more substituents R;

[0966] q is either 0 or 1.

[0967] Connections are particularly preferred where the following applies:

[0968] 20

[0969] - q = 0; Y 30 = B; and Y 31 , Y 32 = NR°; or

[0970] - q = 0; Y 30 = B; and Y 31 , Y 32 = NR°; or

[0971] - q = 1; Y 30 = N; and Y 31 , Y 32 = BR°; Y 33 = chemical bond.

[0972] 25 examples of suitable fluorescent emitters are shown in the table below:

[0973] 30

[0974]

[0975] 35 Foreignfiling_text P25-001.docx

[0976]

[0977] 35Foreignfiling_text P25-001 .docx

[0978] - 115 -

[0979] 5

[0980] 10

[0981] 15

[0982] 20

[0983] 25

[0984] 30

[0985] 35

[0986]

[0987] Foreignfiling text P25-001 .docx

[0988] - 116 -

[0989] 5

[0990] <

[0991] 10

[0992] 15

[0993] 20

[0994] 25

[0995] " 30

[0996] 35

[0997]

[0998] Foreignfiling text P25-001 .docx

[0999] - 117 -

[1000] 5

[1001] 10

[1002] 15

[1003] 20

[1004] 25

[1005] 30

[1006] 35

[1007]

[1008] Foreignfiling text P25-001 .docx

[1009] - 118 -

[1010] 5

[1011] 10

[1012] 15

[1013]

[1014] The following are examples of preferred compounds that meet the 20 criteria.

[1015] can serve as phosphorescent emitters. The term "phosphorescent compound" or "phosphorescent compound" (= triplet emitter) typically refers to compounds in which the emission of light occurs through a spin-forbidden transition, e.g., a transition from an excited triplet state or a state with a 25

[1016] higher spin quantum number, e.g., a quintet state. Luminescent complexes with transition metals or lanthanides are preferably considered as phosphorescent compounds. Within the scope of the present invention, all luminescent indium, platinum, or copper complexes are considered phosphorescent emitting compounds 30

[1017] considered. Iridium or platinum complexes are particularly favored.

[1018] Examples of phosphorescent emitters can be found in applications WO 00 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 05 / 033244, WO 05 / 019373, 35

[1019] US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, Foreignfiling text P25-001 .docx

[1020] - 119 -

[1021] 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 2015 / 117718, WO 2016 / 015815, WO 2016 / 124304, WO 2017 / 032439, WO 2018 / 011186, 5 WO 2018 / 041769, WO WO 2019 / 020538, WO 2018 / 178001, WO 2019 / 115423 and WO 2019 / 158453. In general, all phosphorescent complexes such as those used in the prior art for phosphorescent OLEDs and known to those skilled in the art in the field of organic electroluminescence are suitable, and those skilled in the art can use other phosphorescent complexes without inventive effort. Since the compounds according to the invention can generally also have a high triplet energy, it is particularly possible to use them as a matrix material for blue phosphorescent emitters or in combination with blue phosphorescent emitters.

[1022] Suitable phosphorescent metal complexes that can be used in phosphorescent OLEDs or as sensitizers in hyperphosphorescent OLEDs are disclosed, among others, in Sungho Nam et al., Adv.

[1023] 20 Sei. 2021, 2100586, Eungdo Kin et al., Sei. Adv. 2022, 8, 1641. Further compounds suitable as sensitizers are disclosed in EP 3435438 A2, in particular compounds 2 and 3 on page 21, in CN 109111487, in particular the compounds on pages 76 and 77, in US 2020 / 0140471, in particular the compounds on pages 166 to 175; in KR

[1024] 25 2020108705, in particular the compounds on pages 8 to 14, in US 2019 / 0119312, in particular the compounds on pages 114 to 121, and in US 2020 / 0411775, in particular the compounds on pages 123 to 128. Further suitable phosphorescent metal complexes are disclosed in US 2022 / 0115607, US 2022 / 0298193, US 2016 / 0072082 30 and US 2022 / 0271236.

[1025] The proportion of matrix material in the emitting layer is typically between 50.0 and 99.9 vol.%, preferably between 80.0 and 99.5 vol.%, and particularly preferably between 92.0 and 99.5 vol.% for fluorescent emitting layers and between 85.0 and 97.0 vol.% for phosphorescent emitting layers.

[1026] - 120 -

[1027] Accordingly, the proportion of the emitting compound is between 0.1 and 50.0 vol.%, preferably between 0.5 and 20.0 vol.%, particularly preferably between 0.5 and 8.0 vol.% for fluorescent emitting layers and between 3.0 and 15.0 vol.% for phosphorescent emitting layers.

[1028] An emitting layer can also comprise systems containing a variety of matrix materials (mixed matrix systems) and / or a variety of emitting compounds. In this case, too, the emitting compounds are usually the ones with the smaller proportion in the system, and the matrix materials are the ones with the larger proportion. In some cases, however, the proportion of a single matrix material in the system can be less than the proportion of a single emitting compound.

[1029] Preferably, mixed matrix systems are used. These systems preferably consist of two or three different matrix materials, and particularly preferably of two different matrix materials. Preferably, one of the two materials is a material with hole-transporting properties, and the other is a material with electron-transporting properties. Further mixed matrix components can also fulfill other functions. The two different matrix materials can be present in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, even more preferably 1:10 to 1:1, and most preferably 1:4 to 1:1. Mixed matrix systems are preferably used in phosphorescent or hyperphosphorescent organic electroluminescent devices.Particularly suitable matrix materials that can be used in combination with the compounds 30 according to the invention as matrix components of a mixed matrix system are described in more detail below.

[1030] Examples of phosphorescent compounds are listed below.

[1031] 35Foreignfiling_text P25-001 .docx

[1032] - 121 -

[1033] 5

[1034] 10

[1035] 15

[1036] 20

[1037] 25

[1038] 30

[1039] 35

[1040]

[1041] Foreignfiling_text P25-001 .docx

[1042] - 122 -

[1043] 5

[1044] 10

[1045] 15

[1046] 20

[1047] 25

[1048] 30

[1049]

[1050] 35Foreignfiling_text P25-001 .docx

[1051] - 123 -

[1052]

[1053] 35Foreignfiling text P25-001 .docx

[1054] - 124 -

[1055] 5

[1056] 10

[1057]

[1058] In one embodiment of the invention, a hyperfluorescence and / or hyperphosphorescence system is formed by a suitable combination of compounds.

[1059] 15

[1060] Preferably, a fluorescent emitter is used in combination with one or more phosphorescent materials (triplet emitter) in the case of hyperphosphorescence and / or in combination with a compound that represents a TADF-20 host material (thermally activated delayed fluorescence) in the case of hyperfluorescence.

[1061] In WO 2015 / 091716 A1 and WO 2016 / 193243 A1, OLEDs are disclosed which contain both a phosphorescent compound and a fluorescent emitter in the emission layer, wherein the energy is transferred from the phosphorescent compound to the fluorescent emitter (hyperphosphorescence). In this context, the phosphorescent compound thus behaves like a host material. As is known to those skilled in the art, host materials have higher singlet and triplet energies compared to the emitters, so that the energy of the host material is transferred to the emitter as efficiently as possible.

[1062] A fluorescent emitter can preferably be used in combination with a TADF host material and / or a TADF emitter, as previously described in 35. Foreignfiling text P25-001 .docx

[1063] - 125 -

[1064] The process known as thermally activated delayed fluorescence (TADF) is described, for example, by BH Uoyarna et al., Nature 2012, Vol. 492, 234. To enable this process, a comparatively small 5 singlet-triplet distance AE(Si - Ti) of, for example, less than about 2000 cm' is required in the emitter. 1 necessary. In order to open the inherently spin-forbidden Ti → Si transition, another compound can be provided in the matrix next to the emitter, which exhibits strong spin-orbit coupling, so that inter-system crossing is enabled via the spatial proximity and the resulting possible interaction between the molecules, or the spin-orbit coupling is generated via a metal atom contained in the emitter.

[1065] Besides emitters, emission layers often include host materials, which are also frequently referred to as matrix materials. Compounds used as host materials, especially together with emitting compounds, comprise materials from various classes of substances.

[1066] Host materials generally exhibit larger band gaps between 20 HOMO and LUMO than the emitter materials used. Additionally, preferred host materials exhibit either hole-transport or electron-transport material properties. Furthermore, host materials can exhibit both electron- and hole-transport properties.

[1067] 25 Host materials are sometimes also referred to as matrix materials, especially if the host material is used in combination with a phosphorescent emitter in an OLED.

[1068] Preferred host materials or co-host materials, which are used in particular together with fluorescent dopants, are selected from the classes of oligoarylenes (e.g. 2,2',7,7'-tetraphenyl-spirobi-fluorene according to EP 676461 or dinaphthylanthracene), in particular oligoarylenes containing fused aromatic groups such as e.g.

[1069] Anthracene, Benzanthracene, Benzphenanthrene (DE 102009005746, WO 35 09 / 069566), Phenanthrene, Tetracene, Coronene, Chrysene, Fluorene, Spirobifluorene, Perylene, Phthaloperylene, Naphthaloperylene, Decacycles, Rubrene, Foreignfiling text P25-001 .docx

[1070] - 126 -

[1071] the oligoarylene vinylenes (e.g., DPVBi = 4,4'-bis(2,2-diphenyl-ethenyl)-1,T-biphenyl) or spiro-DPVBi according to EP 676461), the polypodal metal complexes (e.g., according to WO 04 / 081017), in particular metal complexes of 8-hydroxyquinoline, e.g., AIQ3 (= aluminum(III)tris(8-hydroxyquinoline)) or 5-bis(2-methyl-8-quinolinolato)-4-(phenylphenolino-olato)aluminium, also with imidazole chelate (US 2007 / 0092753 A1), as well as the quinoline metal complexes, aminoquinoline metal complexes, benzoquinoline metal complexes, the hole-conducting compounds (e.g., according to WO 04 / 058911), the electron-conducting compounds, in particular ketones, phosphine oxides, Sulfoxides, 10-carbazoles, spiro-carbazoles, indenocarbazoles, etc. (e.g. according to WO 05 / 084081 and WO 05 / 084082), the atropisomers (e.g. according to WO 06 / 048268), the boronic acid derivatives (e.g. according to WO 06 / 117052) or the benzanthracenes (e.g. according to WO 08 / 145239).Particularly preferred compounds that can serve as host materials or co-host materials 15 are selected from the classes of oligoarylenes containing anthracene, benzanthracene and / or pyrene or atropisomers of these compounds. For the purposes of the present invention, an oligoarylene is understood to be a compound in which at least three aryl or arylene groups are bonded to one another.

[1072] 20

[1073] Preferred host materials are in particular selected from compounds of formula (H-100),

[1074] Ar 5 -(Ar 6 ) P -Ar 7 (H-100)

[1075] 25

[1076] where Ar 5 , Ar 6 , Ar 7where, in each occurrence, the aryl or heteroaryl group with 5 to 30 aromatic ring atoms is the same or different, and may optionally be substituted, and p represents an integer in the range of 1 to 5; the sum of the TT electrons in Ar 5 , 30 ares 6 and Ar 7 at least 30 if p = 1, and at least 36 if p = 2, and at least 42 if p = 3.

[1077] The Ar group is particularly favored in compounds of formula (H-100). 6 for Anthracenes and the Ar groups 5 and Ar 7 are bound in positions 9 and 10-35, whereby these groups may be substituted. At least one of the groups Ar is particularly preferred. 5 Foreign filing text P25-001 .docx

[1078] - 127 -

[1079] and / or Ar 7a condensed aryl group selected from 1- or 2-naphthyl, 2-, 3- or 9-phenanthrenyl or 2-, 3-, 4-, 5-, 6- or 7-benz-anthracenyl. Anthracene-based compounds are described in US 2007 / 0092753 A1 and US 2007 / 0252517 A1, e.g., 2-(4-methylphenyl)- 5,10-di-(2-naphthyl)anthracene, 9-(2-naphthyl)-10-(1,1'-biphenyl)anthracene and 9,1-O-bis[4-(2,2-diphenylethenyl)phenyl]anthracene, 9,10-diphenyl-anthracene, 9,10-bis(phenylethynyl)anthracene and 1,4-bis(9'-ethynyl-anthracenyl)benzene. Compounds with two anthracene units are also preferred (US 2008 / 0193796 A1), e.g. 10,10'-Bis[1 ,1',4',

[1080] 10 1”]terphenyl-2-yl-9,9'-bisanthracenyl.

[1081] Other preferred compounds are derivatives of arylamine, styrylamine, fluorescein, diphenylbutadiene, tetraphenylbutadiene, cyclopentadiene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, and coumarin.

[1082] 15 Oxadiazole, Bisbenzoxazoline, Oxazole, Pyridine, Pyrazine, Imine, Benzothiazole, Benzoxazole, Benzimidazole (US 2007 / 0092753 A1), e.g. 2,2',2”-(1,3,5-phenylene)tris[1-phenyl-1H-benzimidazole], Aldazine, Stilbene, Styrylarylene derivatives, e.g. 9,10-Bis[4-(2,2-diphenylethenyl)phenyl]anthracene and Distyrylarylene derivatives (US 5121029), Diphenylethylene, Vinylanthracene, 20 Diaminocarbazole, Pyran, Thiopyran, Diketopyrrolopyrrole, Polymethine, Cinnamic acid esters and Fluorescent dyes.

[1083] Particularly preferred are derivatives of arylamine and styrylamine, e.g., TNB (= 4,4'-bis[N-(1-naphthyl)-N-(2-naphthyl)amino]biphenyl). Metal I-oxinoid complexes such as LiQ or AIQ3 can be used as co-hosts.

[1084] Preferred compounds with oligoarylenes as a matrix are set out in US 2003 / 0027016 A1, US 7326371 B2, US 2006 / 043858 A, WO 2007 / 114358, WO 08 / 145239, JP 3148176 B2, EP 1009044, US 2004 / 018383, WO 30 2005 / 061656 A1, EP 0681019B1, WO 2004 / 013073A1 , US 5077142, WO 2007 / 065678 and DE 102009005746, with particularly preferred compounds being described by formulas H-102 to H-108.

[1085] 35Foreignfiling text P25-001 .docx

[1086] - 128 -

[1087]

[1088]

[1089] 15

[1090]

[1091]

[1092]

[1093] Formula H-108

[1094] 30

[1095] Furthermore, compounds that can be used as a host or matrix include materials that are used together with phosphorescent emitters. Preferred matrix materials for phosphorescent compounds, which can also be used in combination with the compounds according to the invention, are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g., Foreignfiling text P25-001 .docx

[1096] - 129 -

[1097] according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680, triarylamines, carbazole derivatives, e.g. CBP (N,N-biscarbazolyl-biphenyl) or WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or WO 2013 / 041176, indolocarbazole-5 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. according to EP 1617710, EP 1617711, EP 1731584, JP 2005 / 347160, bipolar matrix materials, e.g. according to WO 2007 / 137725, silanes, e.g. according to WO

[1098] 10 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, zinc complexes, e.g. according to EP 652273 or WO 2009 / 062578, diazasilol or tetraazasilol derivatives, e.g. according to WO 2010 / 054729, diazaphosphol-15 derivatives, e.g. according to WO 2010 / 054730, bridged carbazole derivatives, e.g.

[1099] according to WO 2011 / 042107, WO 2011 / 060867, WO 2011 / 088877 and WO 2012 / 143080, triphenylene derivatives, e.g. according to WO 2012 / 048781, lactams, e.g. according to WO 2011 / 116865 or WO 2011 / 137951, dibenzofuran or dibenzothiophene derivatives, e.g. according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO 2017 / 148565 or bridged triarylboron compounds, for example according to US 2021 / 0122765. Similarly, another phosphorescent emitter, which emits at a shorter wavelength than the actual emitter, may be present in the mixture as a co-host, 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.

[1100] The previously cited publications describing the functional materials which can be used to produce functional layers of electronic devices are incorporated into the present application for disclosure purposes by reference thereto.

[1101] Furthermore, it may be provided that the electronic device is an organic electroluminescent device and the electroluminescent device comprises an electron transport layer, wherein the electron transport layer contains at least one electron transport material and Foreignfiling text P25-001 .docx

[1102] - 130 -

[1103] a compound according to formula (1). Preferably, the electron transport layer can contain a composition according to the invention, wherein this composition comprises at least one electron transport material and at least one compound according to formula (1).

[1104] 5

[1105] Furthermore, the electronic device may be an organic electroluminescent device comprising a hole transport layer, wherein the hole transport layer comprises at least one hole transport material and a compound 10 according to formula (1). Preferably, the hole transport layer may contain a composition according to the invention, wherein this composition comprises at least one hole transport material and at least one compound according to formula (1).

[1106] 15 The ordinary refractive indices of the layers of an electronic device, preferably an organic electroluminescent device, measured via ellipsometry at 620 nm, are preferably less than 1.8, more preferably less than 1.7 and particularly preferably less than 1.6.

[1107] 20 In the further layers of the organic electroluminescent device according to the invention, all materials commonly used in the prior art can be employed. The person skilled in the art can therefore, without any inventive effort, use all materials known for organic electroluminescent devices in combination with the 25 compounds according to formula (1) or according to the preferred embodiments described above.

[1108] In addition to the layers described above, the electronic device, preferably the organic electroluminescence device, can comprise 30 further layers. In particular, a compound according to formula (1) or according to the preferred embodiments can be used to produce an outcoupling layer, a capping layer, or an adaptation layer that can be used to adapt different layer thicknesses of the red, green, and blue pixels. A further preferred aspect of the present invention is therefore a Foreignfiling text P25-001 .docx

[1109] - 131 -

[1110] electronic device, preferably an organic electroluminescence device comprising at least one outcoupling layer, capping layer and / or matching layer, which contains at least one compound according to 5 formula (1) or according to the preferred embodiments and preferably consists of one or more of these compounds.

[1111] Preferred electroluminescent devices (OLEDs) according to the invention comprise the following layer structure, whereby it is not excluded that further layers are present:

[1112] - Anode

[1113] - Bone Injectable Layer (HIL)

[1114] - Hole transport layer (HTL)

[1115] - Electron blocking layer (EBL)

[1116] 15 - Emission layer (EML) containing a fluorescent or phosphor dopant

[1117] - Hole-blocking layer (HBL)

[1118] - Electron transport layer (ETL)

[1119] - Electron injection layer

[1120] 20 - Cathode.

[1121] Various embodiments of the invention are summarized in the following table:

[1122] 25

[1123] 30

[1124] 35

[1125]

[1126] Foreign filing text P25-001 .docx

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[1128] 5

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[1135]

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[1141]

[1142] A further preferred organic electroluminescence device is characterized in that one or more layers are coated using a sublimation process. The materials are sublimated in 20 vacuum sublimation units at an initial pressure of less than 10°C. 5 mbar, preferably less than 10 6 mbar vapor deposition. However, it is also possible that the initial pressure is even lower, for example less than 10⁻⁶ mbar. 7 mbar.

[1143] A preferred organic electroluminescence device is also 25, characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or with the aid of carrier gas sublimation. The materials are coated at a pressure between 10° 5mbar and 1 bar are applied. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, 30 in which the materials are applied directly through a nozzle and thus structured.

[1144] A further preferred organic electroluminescent device is characterized in that one or more layers of solution 35, e.g. by spin coating, or with any printing process, e.g. screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), ink-jet printing or Foreignfiling text P25-001 .docx

[1145] - 134 -

[1146] Nozzle printing is used to produce these materials. Soluble compounds are required for this process, which can be obtained, for example, through suitable substitution.

[1147] 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.

[1148] These methods are generally known to the person skilled in the art and can be applied by him without inventive effort to organic electroluminescent devices 10 containing the compounds according to formula (1) or according to the preferred embodiments.

[1149] The electronic devices according to the invention, in particular organic electroluminescence devices, are characterized by one or more of the following surprising advantages over the prior art:

[1150] 1. Electronic devices, in particular organic electroluminescent devices containing compounds according to formula (1) 20 or according to the preferred embodiments, especially in combination with an emitter, with a matrix material, with a hole-transporting material or with an electron-transporting material, exhibit excellent efficiency. This efficiency is better than that of a corresponding OLED that does not contain a compound 25 according to the invention.

[1151] 2. Electronic devices, in particular organic electroluminescent devices containing compounds according to formula (1) or according to the preferred embodiments, in particular in combination with an emitter, with a matrix material, with a hole-transporting material or with an electron-transporting material, have a very good lifetime.

[1152] 3. The compounds according to formula (1) or according to the 35 preferred embodiments exhibit very high stability. Foreignfiling text P25-001 .docx

[1153] - 135 -

[1154] 4. Layers containing compounds according to formula (1) or according to the preferred embodiments have lower refractive indices than layers that do not contain these compounds, which leads to improved light extraction and thus to 5 improved efficiency of the electronic device, in particular the organic electroluminescent device, containing these layers.

[1155] 5. Compounds according to formula (1) or according to the preferred formulations exhibit excellent glass film formation and form very good films both when vapor-deposited and when taken from solution.

[1156] These advantages mentioned above are not accompanied by a significant deterioration of the other electronic properties.

[1157] 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 the aforementioned features of the present invention. Likewise, features of non-essential combinations can be used separately (and not in combination).

[1158] The invention is further explained by the following examples, without thereby limiting it. The person skilled in the art can, from the descriptions, implement the invention in its entire disclosed scope and, without inventive effort, create further connections according to the invention and use them in electronic devices or apply the method according to the invention.

[1159] 30

[1160] Examples:

[1161] Unless otherwise stated, 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-35 ALDRICH or ABCR. The respective information in square brackets or the numbers given for individual compounds are [Foreignfiling text P25-001 .docx].

[1162] - 136 -

[1163] These refer to the CAS numbers of 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.

[1164] 5

[1165] A: Synthons known in literature:

[1166] 1) Aryl bromides with alkyl group substitution according to the invention (EAB):

[1167] 10

[1168] 15

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[1177]

[1178] 2) Arylbromide (AB):

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[1201]

[1202] 3) Halogenosilanes with alkyl group substitution according to the invention (dihalosilane EDHS, trihalosilane ETHS, tetrahalodisilane

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[1261]

[1262] B Representation of the synthons S:

[1263] 20

[1264] Example S1

[1265]

[1266] 800 ml n-heptane are reacted with 3.3 g (5 mmol) Bis[(1,2,5,6-r|)-1,5-cyclooctadiene]di-p-methoxydiiridium(l) [12148-71-9], then with 2.7 g (10 mmol) 4,4'- Di-tert-butyl-[2,2']bipyridinyl [72914-19-3] and then with 5.1 g (10 mmol) 30

[1267] Bis(pinacolato)diborane was added and stirred for 15 min at room temperature. Then, 127.0 g (500 mmol) of bis(pinacolato)diborane and then 113.2 g (500 mmol) of dispiro[cyclopentane-1,1'-[1H]inden-3'(2'H),1"-cyclopentane] [405281-78-9] were added and the mixture was heated to 80 °C for 12 h (TLC control: heptane:ethyl acetate 5:1). After cooling, the reaction was treated with 35

[1268] A ion mixture with 300 ml of ethyl acetate is filtered through a silica gel bed, and the filtrate is completely concentrated under vacuum. The crude product is extracted twice. Foreignfiling text P25-001 .docx

[1269] - 145 -

[1270] Acetone (approx. 800 ml) recrystallized. Yield: 158.8 g (450 mmol), 90%; Purity: approx. 99% according to [method not specified]. 1 H-NMR.

[1271] 5

[1272]

[1273] Procedure analogous to C. Reus et al., J. Org. Chem. 2012, 77, 3518, Verb. 5, 10

[1274] Method B. Starting material: 35.2 g (100 mmol) S1a. Yield: 26.1 g (85 mmol), 85%, after bulb distillation; purity 99% according to 1 H-NMR.

[1275]

[1276] 25

[1277] C: Representation of the compounds according to the invention:

[1278] Example B1:

[1279]

[1280] A well-stirred mixture of 51.2 g (202 mmol) AB1 and 1000 ml diethyl ether, cooled to -78 °C, is added dropwise to 237.6 ml (404 mmol) Foreignfiling text P25-001 .docx

[1281] - 146 -

[1282] tert-Butyllithium (1.7 M in n-hexane) is added. Stirring continues for 15 minutes, the mixture is heated to 10 °C, and then a solution of 83.9 g (100 mmol) of EDHS1 in 300 ml of diethyl ether is slowly added dropwise. After the exothermic reaction has subsided, the mixture is heated under reflux for 5 hours. After cooling, the mixture is slowly poured into 2 L of ice-cold 2 N hydrochloric acid with good stirring, stirred briefly, the organic phase is separated, washed twice with 300 ml of water each time and once with 300 ml of saturated sodium chloride solution, and dried over a mixture of magnesium sulfate and potassium carbonate. The evaporation is filtered off from the drying agent through a silica gel bed and concentrated in the

[1283] 10. Vacuum to dry. 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: 69.8 g (68 mmol), 68%; Purity: approx. 99.9% by HPLC or high-temperature GC.

[1284] Similarly, commercial organolithium compounds, such as methyllithium, isopropyllithium, phenyllithium, etc., can be used.

[1285] 20 The dihalosilanes DHS can be reacted consecutively first with one equivalent of lithiated aryl bromide with alkyl group substitution according to the invention EAB and then with one equivalent of lithiated aryl bromide AB or one equivalent of an alkyllithium compound.

[1286] 25. Similarly, the following compounds can be represented, if necessary by adjusting the stoichiometry:

[1287] 30

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[1460] D: Production of mixtures: PreMix

[1461] Example: PreMixl

[1462] A mixture of 7.5 g HTM [136463-07-5], vacuum TGA (5 wt% - actual): 211 °C, (see Table 4) and 2.5 g B93, vacuum TGA (5 wt% - actual): 213 °C, is carefully heated in a Schlenk tube under argon, without overheating the melt, to 30

[1463] The melt is melted. After homogenizing the melt, it is allowed to cool and the resulting organic glass is pulverized, which in this form is used as PreMixl for the production of OLED components (see example 2b).

[1464] 35

[1465] E: Device examples for blue fluorescent OLEDs Foreignfiling text P25-001 .docx

[1466] - 165 -

[1467] In the following examples, OLEDs according to the invention (examples E1a to E1d, E2a to E2m and E3a) and one OLED according to the prior art (comparative example C1, C2 or C3) are produced. The exact structure of the OLEDs can be found in Tables 1, 2 and 3. The materials used for the production of the OLEDs are shown in Table 4. The properties of the OLEDs according to the invention of examples E1a to E1d, E2a to E2m and E3a and the properties of the OLEDs according to the prior art are listed in Tables 5, 6 and 7.

[1468] 10. Manufacturing of OLEDs

[1469] Glass platelets coated with a 50 nm thick, structured ITO (indium tin oxide) serve as the substrate for the OLEDs. All materials are thermally vapor-deposited in a vacuum chamber. The emission layer always consists of at least one matrix material (also called host material) and an emitting dopant, which is added to the matrix material(s) by cover vapor deposition in a specific volume fraction. A specification such as BH:BD (97:3) 20 nm means that the material BH is present as the host material in a volume fraction of 97%, and the compound BD in a volume fraction of 3% in a 20 nm thick layer. Similarly, the hole injection layer (HIL), the hole transport layer (HTL), and the electron transport layer (ETL) can also consist of a mixture of two or more materials. The structure of the respective OLEDs is shown in Tables 1, 2, and 3.

[1470] 25

[1471] Table 1:

[1472] 30

[1473] 35

[1474]

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[1477]

[1478] Table 2:

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[1489] Table 3:

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[1492] 10 Table 4: OLED materials

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[1526] Characterization of OLEDs

[1527] The OLEDs are characterized according to standard procedures. For this, the electroluminescence spectra and current-voltage-luminance characteristic curves (IIIL curves) are measured, and the efficiency is calculated from these measurements. The calculation is performed assuming a Lambertian emission characteristic. The electroluminescence spectra are measured at a luminance of 1000 cd / m². 2 The CIE 1931 x and y color coordinates were determined and calculated from them. The voltage required for a current density of

[1528] 25 10 mA / cm 2 The required value is denoted here as U10. EQE10 denotes the external quantum efficiency at a current density of 10 mA / cm². 2 For each example, the relative EQE and the relative voltage are calculated in comparison to the respective reference example:

[1529] rel.

[1530] 30 rel.

[1531]

[1532] The refractive index (RI) of a layer at a wavelength of 620 nm is determined using ellipsometry (JA Wollam Inc., USA). The measurement covers the wavelength range from 250 nm to 1000 nm, and the respective refractive index is determined via the dispersion curve. The samples for determining the refractive index (RI) are produced on SiU2 substrates with three different layer thicknesses. [Foreignfiling text P25-001 .docx]

[1533] - 171 -

[1534] The respective material is thermally vapor-deposited. From these measurements, the average refractive index for each material or material mixture is determined.

[1535] 5 The results are presented in the following tables 5, 6 and 7.

[1536] 10

[1537]

[1538] 15 (* of the complete ETL layer of the OLED)

[1539] 20

[1540] 25

[1541] 30

[1542]

[1543] (* of the complete HTL layer of the OLED)

[1544] Table 7: Properties of OLEDs

[1545] 35

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[1549]

[1550] (* of the entire layer of the OLED - ETL or HTL)

[1551] 5. When comparing the inventive examples E1a to E1d, E2a to E2m, and E3a with the corresponding comparative examples C1, C2, or C3, it is clearly evident that the inventive OLED exhibits a significant advantage in device efficiency, without negatively affecting lifetime, voltage, or color. This can be attributed to the 10-fold lower refractive index of the materials according to the invention; for example, the refractive index of B1 is 1.54. The other compounds according to the invention have similar refractive indices. In comparison, LiQ in comparative example C1 has a refractive index of 1.65, and HTM1 in comparative example C2 has a refractive index of 1.73.

[1552] Q: Device examples for green phosphorescent OLEDs

[1553] In the following three examples, OLEDs according to the invention (examples gB1a-c, gB2a-b, gB3a and gB4a) and one OLED according to the prior art (comparative examples gV1, gV2, gV3 and gV4) are produced. The exact structure of the OLEDs can be found in Table 8. The materials used to produce the OLEDs, in addition to those already shown, are shown in Table 9. The properties of the OLEDs according to the invention in the examples and comparative examples are summarized in Table 25.

[1554] Glass platelets coated with a 50 nm thick, structured ITO (indium tin oxide) serve as the substrate for the OLEDs. All materials are thermally vapor-deposited in a vacuum chamber. The emission layer always consists of at least one matrix material (also called host material) and an emitting dopant (emitter), which is added to the matrix material(s) by cover vapor deposition in a specific volume fraction. A specification such as GH1:GH2:GE (32:60:8) means that material GH1 is present in a volume fraction of 32% as host material 1, GH2 in a volume fraction of 60% as host material 2, and the compound GE in a volume fraction of 10%.

[1555] - 173 -

[1556] a volume fraction of 8% is present. Similarly, the hole injection layer (HIL), the hole transport layer (HTL), the electron blocking layer (EBL), the hole blocking layer (HBL), and the electron transport layer (ETL) can also consist of a mixture of two or more materials.

[1557] The structure of the respective OLEDs is shown in Table 8 and the materials for green OLEDs in Table 9. After the electron injection layer (EIL) is deposited, a 100 nm aluminum cathode is deposited onto each component.

[1558] 10 Table 8: Structure of green OLEDs

[1559] 15

[1560] 20

[1561] 25

[1562] 30

[1563] 35

[1564]

[1565] Foreign filing text P25-001 .docx

[1566] - 174 -

[1567] Table 9: OLED materials - green OLEDs (in addition to the materials for blue OLEDs in Table 4)

[1568] 5

[1569] <

[1570] 10

[1571] 15

[1572] 20

[1573] 25

[1574] 30

[1575]

[1576] Characterization of green phosphorescent OLEDs

[1577] 35Foreignfiling text P25-001 .docx

[1578] - 175 -

[1579] The OLEDs are characterized using standard procedures. This is done analogously to the characterization of the blue OLEDs. The results are summarized in Table 10.

[1580] 5

[1581] 10

[1582] 15

[1583]

[1584] When comparing the inventive examples gB1a-c, gB2a-b, gB3a and gB4a with the corresponding comparison examples gV1, gV2, gV3 and gV4, it is evident that the inventive OLEDs show a significant advantage in device efficiency, without negatively affecting lifetime, voltage and color.

[1585] 25

[1586] 30

[1587] 35

Claims

Foreign filing text P25-001 .docx - 176 - Patent claims 1. Compound according to formula (1 ), Formula 1) where the compound may also be partially or completely deuterated 15 and the following applies to the symbols and indices used: M is the same or different Si or Ge in each occurrence; R 1 is, in each occurrence, the same or different, a straight-chain alkyl group with 1 to 20 carbon atoms or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein the alkyl group may in each case be partially or completely deuterated and / or substituted with one or more fluorine atoms, an aromatic ring system with 6 to 40 aromatic ring atoms, 25 which may also be partially or completely deuterated and / or which may also be substituted by one or more substituents R 5may be substituted, a dibenzofuran group, which may also be partially or completely deuterated and / or which may also be modified by one or more substituents R 5 may be substituted 30, or an aralkyl group, which may also be partially or completely deuterated and / or which may also be substituents R 5 It can be substituted; there can be two or three substituents R 1 , which bind to the same Si or Ge atom, also form a ring together, with the linkage 35 occurring via a direct bond or via an O atom; Foreignfiling text P25-001 .docx - 177 - R 2 is M(R 1)3, H, 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 may be partially or completely deuterated and / or substituted with one or more fluorine atoms 5, or an aromatic ring system with 6 to 40 aromatic ring atoms, which may also be partially or completely deuterated and / or substituted with one or more substituents R 5 may be substituted; 10 R 3F is the same or different in each occurrence, 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 may be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 40 aromatic ring atoms, which may also be partially or completely deuterated and / or substituted with one or more fluorine atoms. 5 can be substituted; in this case, two residues R can be involved. 3 , which are bonded to the same carbon atom or which are bonded to different 20 carbon atoms in the same cycle, or a residue R 3 and a remainder R 4 , which are bound in the same cycle, also form a ring together; R 4is the same or different in each occurrence H, D, F, an even-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 may in each case be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 40 aromatic ring atoms, which may also be partially or completely deuterated and / or which may also be substituted by one or more substituents R 5 can be substituted; in this case, two residues R can be involved. 4 , which are bonded to the same carbon atom, or a residue R 4 and a remainder R 3 , which are bound in the same cycle, also form a ring together; Foreignfiling text P25-001 .docx - 178 - R 5 is the same or different at each occurrence H, D, F, CN, Si(R) 6)3, 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 be partially or completely deuterated 5 and / or substituted with one or more fluorine atoms; wherein two or more R groups may be 5 , which are bonded to neighboring carbon atoms, also form a ring with each other; 10 R 6In each occurrence, the alkyl group is either a straight-chain alkyl group with 1 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl group may be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 40 aromatic ring atoms, which may also be partially or completely deuterated and / or substituted with one or more alkyl groups with 1 to 10 carbon atoms, preferably with 1 to 6 carbon atoms, wherein two or more of these alkyl groups may also be 20 can form a ring together; n is either the same or different (1 or 2) in each occurrence; p is 1, 2, 3 or 4. 25 2. Compound according to claim 1, characterized in that it contains exactly one Si atom, exactly one Ge atom, exactly two Si atoms, exactly two Ge atoms or exactly one Si atom and exactly one Ge atom. 30 3. Compound according to claim 1 or 2, characterized in that R 1 , the same or different at each occurrence, is selected from a straight-chain alkyl group with 1 to 10 C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, wherein 35 the alkyl group may in each case be partially or completely deuterated and / or substituted with one or more fluorine atoms, or Foreignfiling text P25-001 .docx - 179 - an aromatic ring system with 6 to 24 aromatic ring atoms, which may also be partially or completely deuterated and / or which may also be modified by one or more substituents R 5 It can be substituted; there can be two or three substituents R 1, 5 which bind to the same Si or Ge atom also form a ring together.

4. Compound according to one or more of claims 1 to 3, characterized in that R 2 , same or different at each occurrence, 10 is selected from H, D, F, CN, a straight-chain alkyl group with 1 to 10 C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, wherein the alkyl group may in each case be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 15 24 aromatic ring atoms, which may also be partially or completely deuterated and / or which may also be substituted by one or more substituents R 5 may be substituted.

5. Combination according to one or more of claims 1 to 4, wherein 20 characterized that R 3, same or different at each occurrence, is selected from a straight-chain alkyl group with 1 to 10 C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, wherein the alkyl group is in each case partially or completely deuterated and / or substituted with one or more fluorine atoms 25 may be, or an aromatic ring system with 6 to 12 aromatic ring atoms, which may also be partially or completely deuterated and / or which may also be modified by one or more substituents R 5 can be substituted; in this case, two residues R can be involved. 3 , which are bonded to the same carbon atom or which are bonded to different 30 Carbon atoms are bonded in the same cycle, or a residue R 3 and a remainder R 4 , which are bonded to neighboring carbon atoms, also form a ring together.

6. Combination according to one or more of claims 1 to 5, wherein 35 characterized that R 4 , same or different at each occurrence, selected from H, D, F, a straight-chain alkyl group with 1 to 10 Foreignfiling text P25-001 .docx - 180 - C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, wherein the alkyl group may be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 18 aromatic ring atoms, which may also be partially or completely deuterated and / or substituted with one or more fluorine atoms 5 can be substituted; in this case, two residues R can be involved. 4 , which are bonded to the same carbon atom, or a residue R 4 and a remainder R 3 , which are bonded to neighboring carbon atoms, also form a ring 10 together.

7. Compound according to one or more of claims 1 to 6, wherein: 15 M is Si; R 1 The 'equals' or 'different' in each occurrence represents a straight-chain alkyl group with 1 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl20 The group may be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 24 aromatic ring atoms, which may also be partially or completely deuterated and / or substituted with one or more substituents R 5 25 It can be substituted; there can be two or three substituents R 1 , which bind to the same Si atom, also form a ring with each other; R 2 "Same or different" represents H, D, F, CN, 30 in each occurrence. a straight-chain alkyl group with 1 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl group may be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 24 aromatic 35 Ring atoms, which is also partially or completely deuterated. Foreignfiling text P25-001 .docx - 181 - may be and / or which may also be formed by one or more substituents R 5 may be substituted; R 3In each instance, the represents an even-chain alkyl group with 1 to 10 carbon atoms, or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl group may be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 12 aromatic ring atoms, which may also be partially or completely deuterated and / or substituted with one or more fluorine atoms. 5 can be substituted; in this case, two residues R can be involved. 3 , which are bonded to the same carbon atom or which are bonded to different carbon atoms in the same cycle, or a residue 15 R 3 and a remainder R 4 , which are bonded to neighboring carbon atoms, also form a ring with each other; R 4The symbol R represents, in each case the same or different, H, D, F, a straight-chain alkyl group with 1 to 10 carbon atoms, or a branched or cyclic alkyl group with 3 to 10 carbon atoms, wherein the alkyl group may be partially or completely deuterated and / or substituted with one or more fluorine atoms, or an aromatic ring system with 6 to 18 aromatic ring atoms, which may also be partially or completely deuterated and / or substituted with one or more fluorine atoms. 5 can be substituted; in this case, two residues R can be involved. 4 , which are bonded to the same carbon atom, or a residue R 4 and a remainder R 3 , which are bonded to neighboring carbon atoms, also form a ring with each other; 30 R 5 The symbol represents H, D, F, CN, Si(R) in each instance, either the same or different. 6)3, a straight-chain alkyl group with 1 to 10 C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, wherein the alkyl group is in each case partially or completely deuterated 35 and / or substituted with one or more fluorine atoms. Foreignfiling text P25-001 .docx - 182 - can; in this case, two or three substituents R can be used. 5 , which bind to neighboring C atoms, also form a ring with each other; R 6 The term "equal or different" in each instance represents a straight-chain alkyl group with 1 to 5 carbon atoms or a branched or cyclic alkyl group with 3 to 6 carbon atoms, the alkyl group being either partially or completely deuterated, or a phenyl group, which may also be partially or completely deuterated and / or replaced by a phenyl group. 10 can be substituted with several alkyl groups with 1 to 5 C atoms, whereby two or more adjacent alkyl groups can also form a ring together; n is 1 ; 15 p is either 1 or 2.

8. Compound according to one or more of claims 1 to 7, wherein: 20 M is Si; R 1 The symbol R represents, in the same or different ways, methyl, ethyl, n-propyl, n-butyl, iso-propyl, iso-butyl, sec-butyl, tert-butyl, cyclopentyl, or cyclohexyl, where each of these groups may be partially or completely deuterated, or a phenyl group, which may also be partially or completely deuterated and / or modified by one or more substituents. 5 It can be substituted; there can be two or three substituents R 1 , which bind to the same Si-30 atom, also form a ring with each other; R 2The term "same" or "different" in each occurrence represents H or D, especially H; 35 R 3 The term "same" or "different" in each instance represents methyl, ethyl, or phenyl, whereby these groups may also be partially or completely represented. Foreignfiling text P25-001 .docx - 183 - They may be deuterated, with methyl and ethyl being particularly preferred; two R groups may be used. 3 , which bond to the same carbon atom also form a 5-membered ring together; 5 R 4 The term "same" or "different" in each occurrence represents H or D, especially H; R 5 stands equal or different for H, D, Si(R) in each occurrence. 6 )3, Methyl, Ethyl, n-Propyl, n-Butyl, iso-Propyl, iso-Butyl, sec-Butyl, 10 tert-Butyl, neo-Pentyl, Cyclopentyl or Cyclohexyl, wherein these groups may each be partially or completely deuterated; wherein two or three substituents R 5, which bind to neighboring C atoms, also form a ring with each other; 15 R 6 The symbol represents, in the same or different ways, methyl, ethyl, n-propyl, n-butyl, iso-propyl, iso-butyl, sec-butyl, tert-butyl, cyclopentyl or cyclohexyl, each of which may be partially or completely deuterated, or a phenyl group, which may also be partially or completely deuterated and / or which may also be substituted by one or more alkyl groups with 1 to 5 carbon atoms, where two or more adjacent alkyl groups may also form a ring with each other; n is 1 ; 25 p is either 1 or 2.

9. Connection according to formula (1'), Formula (1 ')Foreignfiling text P25-001 .docx - 184 - wherein the symbols and indices have the meanings mentioned in claim 1, characterized in that the compound consists of one or more of the substituents R instead of R 1 to R 6 5 contains at least one networkable group.

10. A method for producing a compound according to one or more of claims 1 to 8, wherein first an aryl halide is converted to an aryl metal compound and the aryl metal compound is then 10 reacted with a halogen-silicon compound or a halogen-germanium compound by salt metathesis.

11. Oligomer, polymer or dendrimer containing one or more of the compounds according to one or more of claims 1 to 8, wherein 15 one or more bonds of the compound to the polymer, oligomer or dendrimer are present.

12. Mixture comprising at least one compound according to one or more of claims 1 to 8 and at least one further compound.20 dung, wherein the further compound is preferably selected from the group consisting of one or more hole transport materials, electron transport materials, matrix materials, emitting compounds and / or solvents. 25 13. Use of a compound according to one or more of claims 1 to 9, an oligomer, polymer or dendrimer according to claim 11 and / or a mixture according to claim 12 in an electronic device, in particular in an organic electroluminescent device. 30 14. Electronic device, in particular an organic electroluminescent device, comprising at least one compound according to one or more of claims 1 to 9, at least one oligomer, polymer or dendrimer according to claim 11 and / or at least 35 a mixture according to claim 12. Foreignfiling text P25-001 .docx - 185 - 15. Electronic device according to claim 14, wherein it is an organic electroluminescent device, characterized in that the compound according to one or more of claims 1 to 9, the oligomer, polymer or dendrimer according to claim 11 or the mixture according to claim 12 is used in an emitting layer in combination with at least one fluorescent or phosphorescent emitter, in a hole transport, hole injection or electron blocking layer in combination with at least one hole transport material, in an electron transport, electron injection or hole blocking layer in combination with at least one electron transport material or in a capping layer outside the active OLED stack. 15 20 25 30 35

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