Materials for organic electroluminescent devices

Abstract

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

Description

[0001] Foreign filing text P25-055.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 aliphatic

[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.The electron transport layer typically uses heteroaromatic compounds with electron-deficient heteroaryl groups, such as triazine or benzimidazole, whose refractive index is also typically in the range of 1.7 to 1.9. While a reduction in the refractive index of the layers improves the extraction of electrons,

[0008] -2 -

[0009] While this is desirable, it cannot be achieved with currently used charge 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, a requirement for these materials is that they are inert to charge transport within the layer and thus do not negatively affect the electronic properties of the OLED when doped into the layer at a moderate level. Furthermore, these materials must be sublimable and sufficiently thermally stable when processed from the gas phase.

[0010] 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 objective 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.

[0011] Another object of the present invention is the provision of 25 materials suitable for hydrophobizing surfaces, for example for cathode structuring.

[0012] 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 addition to the hole and / or electron transport layer, as well as the emitting layer. The resulting improved extraction leads to an improvement in the Foreignfiling text P25-055.docx

[0013] - 3 -

[0014] Efficiency is improved compared to OLEDs that do not contain these materials, while the other properties of the OLED, in particular operating voltage and lifetime, remain unaffected. These compounds, as well as electronic devices, especially organic electroluminescent devices containing such compounds, are therefore the subject of the present invention.

[0015] The subject of the present invention is a compound according to the following formula (1),

[0016] 10

[0017] 15

[0018]

[0019] Formula 1)

[0020] where the compound may also be partially or completely deuterated, and the following applies to the symbols and indices used:

[0021] 20 M is the same or different Si or Ge in each occurrence;

[0022] R 1In each occurrence, the alkyl group is either 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 partially or completely deuterated and / or with one or more fluorine atoms and / or Si(R) groups. 7 )3 may be substituted, or 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 3 can be substituted 30, with a maximum of two groups R 1 represent an aromatic ring system; this can involve two or three substituents R 1 also form a ring with each other;

[0023] R 2In each occurrence, the alkyl group is either a straight-chain alkyl group with 1 to 20 carbon atoms or a branched or cyclic alkyl group with 3 to 20 carbon atoms, the alkyl group being partially or completely different.

[0024] - 4 -

[0025] wisely or completely deuterated and / or with one or more fluorine atoms and / or groups Si(R 7 )3 can be substituted, an aromatic ring system with 6 to 30 aromatic ring atoms, which can also be partially or completely deuterated and / or 5 which can also be modified by one or more substituents R 4 may 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 4may be substituted, or an aralkyl group with 6 to 30 aromatic ring atoms, which may also be partially or completely deuterated and / or which may also be modified by one or more substituents R 4 It can be substituted; this can involve two or three substituents R 2 , which bind to the same Si or Ge atom, also form a ring together;

[0026] 15 L stands for -[Ar]0-[Alk] p -[Ar] q -;

[0027] Ar is, in each occurrence, 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 may be substituted, or 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;

[0028] 25 Alk is a straight-chain, branched or cyclic alkylene group with 1 to 20 carbon atoms, which may also be partially or completely deuterated and / or which may also be modified by one or more substituents R 6 may be substituted;

[0029] 30 R 3 , R 4 , R 5 , R 6 is the same or different in each occurrence F, CN,

[0030] Si(R 7 )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 and / or substituted with one or more fluorine atoms, an aromatic ring system with 6 to 24 aromatic ring atoms, which may also be partially or completely deuterated and / or Foreignfiling text P25-055.docx

[0031] - 5 -

[0032] which also includes one or more groups Si(R) 7)3 and / or alkyl groups with 1 to 10 C atoms, wherein two or more of these alkyl groups can also form a ring together, or an aralkyl group with 6 to 24 aromatic ring5 atoms, which can also be partially or completely deuterated and / or which can also be substituted with one or more Si(R) groups 7 )3 and / or alkyl groups with 1 to 10 carbon atoms, wherein two or more of these alkyl groups can also form a ring together; in this case, two or more R groups can be substituted 3 , two 10 or more remainders R 4 , two or more residues R 5 and / or two or more residues R 6 also form a mono-, oligo- or polycyclic ring with each other;

[0033] R 7In 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 30 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, wherein two or more of these alkyl groups may also form a ring together; in this case, two or more substituents R may also be present. 7 together form a mono-, oligo- or polycyclic ring 25;

[0034] n, o, p, q is either the same or different from 0 or 1 in each occurrence, with the proviso that o + p + q ≥ 1;

[0035] 30, provided that the compound has a molecular weight of at least 500 g / mol,

[0036] and furthermore with the proviso that the following compound is excluded from the invention: Foreignfiling text P25-055.docx

[0037] 5

[0038]

[0039] 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 understood to be either a simple aromatic cycle, i.e., benzene, or a 15-fold heteroaromatic cycle, for example, pyridine, pyrimidine, thiophene, etc., or a fused (fused) aryl or heteroaryl group, for example, naphthalene, anthracene, phenanthrene, quinoline, dibenzofuran, etc. Aromatic compounds linked together by single bonds, such as biphenyl or bipyridine, are referred to not as aryl or heteroaryl groups, but as aromatic or heteroaromatic ring systems.

[0040] An aromatic ring system according to the present invention contains 6 to 30 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 30 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 systems in which two or more aryl groups are linked to each other 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, 9,9-diarylfluorene, tetraphenylmethane, xanthene, and spiroxanthene.Accordingly, a heteroaromatic ring system comprises Foreignfiling text P25-055.docx.

[0041] -7 -

[0042] For the purposes of the present invention, 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 -0 or the corresponding partially or completely deuterated groups, for example bipyridine or phenylpyridine. Preferably, the aromatic ring system is selected from an aryl group, fluorene, 9,9'-spirobifluorene, xanthene, spiroxanthene, or a group in which two or more aryl groups are linked to one another by single bonds, in particular phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, or 9,9'-spirobifluorene.

[0043] An aralkyl group within the meaning of the present invention is understood to be an alkyl group substituted with an aromatic ring system, 15 which is bonded via the alkyl group, such as, for example, in the simplest case, a benzyl group.

[0044] Within the scope of the present invention, the following are preferably incorporated 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, adamantyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, and corresponding partially or completely fluorinated groups.

[0045] 25 deuterated groups are understood. In general, according to the present invention, the term alkyl group is understood to be a straight-chain, branched, or cyclic group. A cyclic alkyl group is understood to be a monocyclic, bicyclic, or oligocyclic group, whereby not all carbon atoms of the cyclic alkyl group need to be bonded within the cycle itself, but can also be bonded exocyclically, as is the case, for example, in 1-methylcyclohexyl or 4-tert-butylcyclohexyl.

[0046] An aromatic ring system with 6 to 30 aromatic ring atoms, which may be further substituted with the aforementioned residues and which may be linked via any positions on the aromatic ring, is understood in particular to be groups that are derived from Foreignfiling text P25-055.docx

[0047] - 8 -

[0048] understood from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, xanthene and spiroxanthene. A heteroaromatic ring system with 5 to 30 aromatic ring atoms is understood to include, in particular, groups derived from cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazinimidazole, quinoxalineimidazole, oxazole, benzoxazole, naphthoxazole.

[0049] 15 Anthroxazol, Phenanthroxazol, Isoxazol, 1,2-Thiazol, 1,3-Thiazol, Benzo- thiazol, Pyridazin, Hexaazatriphenylen, Benzopyridazin, Pyrimidin, Benzpyrimidin, Chinazolin, Chinoxalin, 1,5-Diazaanthracen, 2,7-Diazapyren, 2,3- Diazapyren, 1,6-Diazapyren, 1,8-Diazapyren, 4,5-Diazapyren, 4,5,9,10- Tetraazaperylen, Pyrazin, Phenazin, Phenoxazin, Phenothiazin, Fluorubin, 20 Naphthyridin, Azacarbazol, Benzocarbolin, Phenanthrolin, 1,2,3-Triazol,

[0050] 1.2.4-Triazol, Benzotriazol, 1,2,3-Oxadiazol, 1,2,4-Oxadiazol, 1,2,5-Oxa- diazol, 1,3,4-Oxadiazol, 1,2,3-Thiadiazol, 1,2,4-Thiadiazol, 1,2,5-Thiadiazol, 1.3.4-Thiadiazol, 1,3,5-Triazin, 1,2,4-Triazin, 1,2,3-Triazin, Tetrazol, 1,2,4,5-Tetrazin, 1,2,3,4-Tetrazin, 1,2,3,5-Tetrazin, Purin, Pteridin, Indolizin 25 und Benzothiadiazol.

[0051] The phrase "two or more residues can form a ring" in the context of this description means, among other things, that the two residues are linked to each other by a chemical bond 30, with the formal elimination of two hydrogen atoms. This is illustrated by the following scheme.

[0052] Ring formation

[0053]

[0054] the remains R

[0055] 35 R

[0056]

[0057] R H3C C2H5H2C S X CH2

[0058]

[0059] H2Foreignfiling text P25-055.docx

[0060] - 9 -

[0061] 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:

[0062] Ring formation of the residues R

[0063] 1 CH

[0064]

[0065] 02

[0066] Similarly, residues bonded to the same silicon atom can also form a ring together.

[0067] 15

[0068] Preferred embodiments of the connection according to the invention are described below.

[0069] In a preferred embodiment of the invention, M stands for Si, so that it is a compound of the following formula (2), 20

[0070]

[0071] 25 Formula (2)

[0072] the symbols and indices used have the meanings mentioned above.

[0073] 30 In another preferred embodiment of the invention, R 1 In each occurrence, the alkyl group is either the same or different: 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 with one or more Si(R) groups. 7 )3substituted35, 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 3 substi-Foreignfiling text P25-055.docx

[0074] - 10 -

[0075] can be tutored, with a maximum of two groups R 1 represent an aromatic ring system; this can involve two or three substituents R 1they can also form a ring together. R is particularly favored. 1 In each occurrence, the alkyl group may be the same or different: a straight-chain alkyl group with 1 to 5 carbon atoms, in particular methyl, ethyl, n-propyl or n-butyl; a branched alkyl group with 3 to 6 carbon atoms, in particular isopropyl, isobutyl, sec-butyl or tert-butyl; or a cyclic alkyl group with 5 to 10 carbon atoms, in particular cyclopentyl, cyclohexyl, biscyclo[2.2.2]octanyl or adamantanyl, wherein the alkyl group may be partially or completely deuterated; or a phenyl group, which may also be partially or completely deuterated and / or which may also be modified by one or more substituents. 3 can be substituted, with a maximum of two groups R 1 R represents a phenyl group; two or three substituents are possible. 1 also form a ring together. R is particularly favored in 15 cases. 1Whether the same or different in each occurrence, methyl or ethyl, or a group R 1 stands for methyl and the other two groups R 1 Together they form a cyclopentane or cyclohexane ring, or the three groups together form an adamantyl group.

[0076] 20 Preferred groups of the following formula, which are bonded to M according to the invention,

[0077] 25

[0078]

[0079] where dashed lines represent the bond to M, the groups are those of the following formulas (a) to (f), where the groups may also be partially or completely deuterated and groups (a) to (e) are particularly preferred.

[0080] 35Foreignfiling text P25-055.docx

[0081] - 11 -

[0082] 5

[0083]

[0084]

[0085] 10

[0086] In a further preferred embodiment of the invention, R 2 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 is in each case partially or completely 15

[0087] deuterated and / or with one or more groups Si(R) 7 )3 can be substituted, an aromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, which can also be partially or completely deuterated and / or which can also be modified by one or more substituents R 4 may be substituted, a dibenzo- 20

[0088] furan group, which may also be partially or completely deuterated and / or which may also be modified by one or more substituents R 4may be substituted, or an aralkyl group with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, which may also be partially or completely deuterated and / or which may also be modified by 25

[0089] one or more substituents R 4 It can be substituted; this can involve two or three substituents R 2 , which bond to the same Si or Ge atom, also form a ring with each other. R is particularly preferred. 2 In each occurrence, a straight-chain alkyl group with 1 to 5 carbon atoms, in particular methyl, ethyl, n-propyl or n-butyl, a ver30

[0090] branched alkyl group with 3 to 6 C atoms, in particular iso-propyl, iso-butyl, sec-butyl, tert-butyl, tert-pentyl or neo-pentyl, or a cyclic alkyl group with 5 to 10 C atoms, in particular cyclopentyl, cyclohexyl, bicyclo[2.2.2]octanyl or adamantanyl, wherein the alkyl group is in each case partially or completely deuterated and / or with one or more

[0091] 35

[0092] Groups Si(R 7 )3-substituted, or an aromatic ring system with 6 to 12 aromatic ring atoms, preferably a phenyl group, Foreignfiling text P25-055.docx

[0093] - 12 -

[0094] where these groups may also be partially or completely deuterated and / or contain one or more substituents R 4 They can be substituted; two or three substituents can be used. 2 , which bind to the same Si or Ge atom, also form a ring together.

[0095] 5

[0096] In a further preferred embodiment of the invention, Ar is, in each occurrence, 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 modified by one or more sub10 stituents R. 5 may be substituted, or 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 Ar may be substituted. Particularly preferred is, in each occurrence, 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. 5Ar can be substituted, and most preferably Ar is a phenyl group, which can also be partially or completely deuterated and / or which can also be modified by one or more substituents R. 5 may be substituted.

[0097] 20

[0098] In a further preferred embodiment of the invention, Alk is a linear alkylene group with 1 to 10 C atoms or a branched or cyclic alkylene group with 3 to 10 C atoms, wherein the alkylene group may also be partially or completely deuterated and / or also 25 by one or more substituents R 6The alkyl group may be substituted. Particularly preferred is a linear alkylene group with 1 to 5 carbon atoms, in particular methylene, ethylene, n-propylene or n-butylene, a branched alkylene group with 3 to 5 carbon atoms, in particular isopropylene, isobutylene, sec-butylene, tert-butylene, or a cyclic alkylene group with 6 to 30 to 10 carbon atoms, wherein the alkylene group may also be partially or completely deuterated and / or modified by one or more substituents R. 6 may be substituted. Particularly preferred is a methylene group or a cyclic alkylene group with 6 to 10 carbon atoms, especially groups derived from cyclohexane, bicyclo[2.2.2]octane or 35 adamantane, wherein the alkylene group may also be partially or fully substituted.

[0099] - 13 -

[0100] may be constantly deuterated and / or also by one or more substituents R 6 may be substituted.

[0101] The following combinations of the indices o, p and 5 are still preferred.

[0102] q:

[0103] - o = 1, p = 0 and q = 0, so that L = -Ar- is;

[0104] - o = 0, p = 1 and q = 0, so that L = -Alk- is;

[0105] - o = 1, p = 1 and q = 1, so that L = -Ar-Alk-Ar.

[0106] Ten examples of preferred left-handed L structures are listed below.

[0107] 15

[0108] 20

[0109] 25

[0110] 30

[0111]

[0112] 35-14-

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120] Foreignfiling text P25-055.docxForeignfiling text P25-055.docx

[0121] - 15 -

[0122] 5

[0123] 10

[0124]

[0125] 15

[0126] where these structures may also be partially or completely deuterated, R 7 which has the meanings mentioned above, and where the dashed bond represents the bond to M. Preferred groups -Si(R 7 )3 are explained in more detail below.

[0127] 20

[0128] Preferred substituents R 3 , which act as optional substituents on R 1 They may be bound if R 1 for an aromatic ring system, are the same or different at each occurrence Si(R) 7 )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 25

[0129] or can be completely deuterated and substituted; in this case, two or more residues R can be involved. 3 they can also form a mono-, oligo- or polycyclic ring together. R is particularly preferred. 3 same or different at each occurrence Si(R 7 )3, a straight-chain alkyl group with 1 to 5 carbon atoms, in particular methyl, ethyl, n-propyl or n-butyl, or a 30

[0130] branched or cyclic alkyl group with 3 to 6 carbon atoms, in particular iso-propyl, iso-butyl, sec-butyl, tert-butyl, cyclopentyl or cyclohexyl, wherein the alkyl group may be partially or completely deuterated; in each case, two or more R groups may be present. 3 also form a mono-, oligo- or polycyclic ring with each other. 35 is particularly preferred.

[0131] is R 3 not present, i.e., if R 1 For an aromatic ring system, this is particularly preferred in its unsubstituted form. Foreignfiling text P25-055.docx

[0132] - 16 -

[0133] Preferred substituents R 4 , which act as optional substituents on R 2 They may be bound if R 4 for an aromatic ring system, dibenzofuran or an aralkyl group, are the same or different in each case Si(R) occur 7 )3, 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 fully deuterated; in each case, two or more R groups may be 4 they can also form a mono-, oligo- or polycyclic ring together. R is particularly preferred. 4 10 same or different at each occurrence Si(R 7)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 isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl or cyclohexyl, wherein the alkyl group may in each case be partially or fully deuterated; in each case two or more R groups may be 4 They can also form a mono-, oligo- or polycyclic ring together.

[0134] Preferred substituents R 5 , which can be bonded to Ar as optional substituents, are the same or different at each occurrence Si(R) 7 )3, 20 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 be partially or completely deuterated; in each case two or more R groups may be 5they can also form a mono-, oligo- or polycyclic ring together. R is particularly preferred. 5 same or different 25 at each occurrence Si(R 7 )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 isopropyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl or cyclohexyl, wherein the alkyl group may be partially or completely deuterated 30; wherein two or more R groups may be 5 They can also form a mono-, oligo- or polycyclic ring together.

[0135] Preferred substituents R 6 , which can be bonded to Alk as optional substituents, are the same or different at each occurrence Si(R 7)335 or an aromatic ring system with 6 to 12 aromatic ring atoms, which may also be partially or completely deuterated and / or Foreignfiling text P25-055.docx

[0136] - 17 -

[0137] which also includes one or more groups Si(R) 7 )3 and / or may be substituted with one or more alkyl groups having 1 to 10 carbon atoms, wherein two or more of these alkyl groups may also form a ring together. Particularly preferred substituents R 6 are the same or 5 different at each occurrence Si(R) 7 )3 or a phenyl group, which may also be partially or completely deuterated and / or which may also be joined with one or more Si(R) groups 7 )3 and / or may be substituted with one or more alkyl groups with 1 to 10 C atoms, wherein two or more of these alkyl groups may also form a ring together 10.

[0138] Preferred substituents R 7The following are identical or different 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, 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 substituted with one or more alkyl groups with 1 to 10 carbon atoms, wherein two or more of these alkyl groups may also form a ring together; in this case, two or more R groups may be present. 7 , which bond to the same Si atom, also form a mono-, oligo- or polycyclic ring with each other. R is particularly preferred. 7same or different in each occurrence, a straight-chain alkyl group with 1 to 5 C atoms, in particular methyl, ethyl, n-propyl or n-butyl, a branched alkyl group with 3 to 6 C atoms, in particular isopropyl, isobutyl, sec-butyl, tert-butyl, tert-pentyl or neo-pentyl, or a cyclic alkyl group with 5 to 10 C atoms, in particular cyclopentyl, cyclohexyl, bicyclo[2.2.2]octanyl or adamantanyl, wherein the alkyl group may in each case be partially or completely deuterated, or 30 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 10 C atoms, wherein two or more of these alkyl groups may also form a ring with each other; This can involve two or three substituents R 7 , which bind to the same silicon atom, also form a ring together. Foreignfiling text P25-055.docx

[0139] - 18 -

[0140] Preferred groups -Si(R 7 )3 are the structures shown below:

[0141] 5

[0142] 10

[0143] 15

[0144] 20

[0145] 25

[0146]

[0147] If one or more of the groups R 1 to R 7 If Ar represents an aromatic ring system, then this aromatic ring system preferably contains no fused aryl groups. Furthermore, Ar preferably contains no 30

[0148] condensed aryl groups. A condensed aryl group is defined as a group in which two or more aryl groups are directly fused to one another via a common edge of their respective six-membered rings, as in naphthalene. Preferably, the aromatic ring system is the same or different in each occurrence. 35

[0149] from the group consisting of phenyl, biphenyl, terphenyl, quaterphenyl, fluorenyl or spirobifluorenyl, each of which is partially or completely Foreignfiling text P25-055.docx

[0150] - 19 -

[0151] The aromatic ring system may be deuterated and / or substituted as described above. Particularly preferred is the aromatic ring system selected from phenyl and biphenyl, either differently in each occurrence, which may each be partially or completely deuterated and / or substituted as described above.

[0152] Preferred aromatic ring systems R 1 to R 7 The groups of the following formulas are Ar-1 to Ar-58, with groups Ar-1 to Ar-4 being preferred.

[0153] 10

[0154] 15

[0155] 20

[0156] 25

[0157] 30

[0158]

[0159] 35Foreignfiling text P25-055.docx

[0160] -20 -

[0161] 5

[0162] 10

[0163] 15

[0164] 20

[0165] 25

[0166] 30

[0167] 35

[0168]

[0169] Foreign filing text P25-055.docx

[0170] 5

[0171] 10

[0172] Ar-55

[0173] 15

[0174]

[0175] 20

[0176] where the dashed bond represents the position of the bond of this group. Furthermore, these structures can also be partially or completely deuterated and / or substituted by substituents, as defined above, i.e.

[0177] - if the structures Ar-1 to Ar-58 form a group R 1 represent, can 25

[0178] they through R 3 be substituted;

[0179] - if the structures Ar-1 to Ar-58 form a group R 2 They can be represented by R 4 be substituted;

[0180] - if the structures Ar-1 to Ar-58 form a group R 3 , R 4 , R 5 or R 6 They can be represented by one or more Si(R) each 7 )s and / or 30

[0181] Alkyl groups may be substituted with 1 to 10 carbon atoms; and

[0182] - if the structures Ar-1 to Ar-58 form a group R 7 They can be represented by one or more alkyl groups with 1 to 10 carbon atoms.

[0183] 35Foreignfiling text P25-055.docx

[0184] -22 -

[0185] In one embodiment of the invention, two substituents bonded to an aromatic ring system form a ring together. Preferably, the following structures are formed:

[0186] 5

[0187] 10

[0188] 15

[0189] 20

[0190]

[0191] where the dashed line represents the connection point of the respective group and the structures may also be partially or completely deuterated.

[0192] 25

[0193] 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 layer. Since the production of deuterated

[0194] Since the materials used are 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.

[0195] 35 The preferred embodiments mentioned above can be combined arbitrarily within the limitations defined in claim 1. Foreignfiling text P25-055.docx

[0196] - 23 -

[0197] can be combined. In a particularly preferred embodiment of the invention, the aforementioned advantages occur simultaneously.

[0198] Therefore, compounds of formula (1) are preferred, for which the following holds:

[0199] 5 M is Si;

[0200] R 1 In 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 is in each case partially or completely deuterated and / or with one or more Si(R) groups. 7)3 may be substituted, 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 3 can be substituted, with a maximum of two groups R 1 for an aromatic ring system; 15 where two or three substituents R can be present 1 also form a ring with each other;

[0201] R 2 In 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 is in each case partially or completely deuterated and / or with one or more Si(R) groups. 7)3 can be substituted, an aromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, which can also be partially or completely deuterated and / or which can also be modified by one or more substitutions. 4 may 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 4 may be substituted, or an aralkyl group with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, which may also be partially or fully deuterated and / or which may also be modified by one or more substituents R 4 It can be substituted; this can involve two or three substituents R 2 , which bind to the same Si atom, also form a ring together;

[0202] Ar is, in each occurrence, an aromatic ring35 system with 6 to 18 aromatic ring atoms, which may also be partially or completely deuterated and / or which may also be characterized by Foreignfiling text P25-055.docx

[0203] -24 -

[0204] one or more substituents R 5 may be substituted, or 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;

[0205] 5. Alk is a linear alkylene group with 1 to 10 carbon atoms or a branched or cyclic alkylene group with 3 to 10 carbon atoms, whereby the alkylene group may also be partially or completely deuterated and / or modified by one or more substituents R. 6 may be substituted;

[0206] 10 for o, p and q:

[0207] - o = 1, p = 0 and q = 0; or

[0208] - o = 0, p = 1 and q = 0; or

[0209] - o = 1, p = 1 and q = 1;

[0210] R 3 is the same or different at each occurrence Si(R 7 )3, 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; in each case, two or more R groups may be 3 also form a mono-, oligo- or polycyclic ring with each other;

[0211] 20 R 4 is the same or different at each occurrence Si(R 7 )3, 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 fully deuterated; in each case, two or more R groups may be 4also together form a mono-, oligo- or polycyclic ring;

[0212] R 5 is the same or different at each occurrence Si(R 7 )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 may be partially or completely deuterated; wherein 30 two or more R groups may be 5 also form a mono-, oligo- or polycyclic ring with each other;

[0213] R 6 is the same or different at each occurrence Si(R 7 )3 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 35 with one or more Si(R) groups 7 )3 and / or may be substituted with one or more alkyl groups with 1 to 10 carbon atoms, Foreignfiling text P25-055.docx

[0214] - 25 -

[0215] where two or more of these alkyl groups can also form a ring together;

[0216] R 7 In 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, 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 substituted with one or more alkyl groups with 1 to 10 carbon atoms, wherein two or more of these alkyl groups may also form a ring together; in this case, two or more R groups may be present. 7 , which bind to the same Si atom, also form a mono-, oligo- or polycyclic ring with each other;

[0217] with the proviso that R 1 to R 7and Ar do not contain a condensed aryl group 15.

[0218] Compounds of formula (1) are particularly preferred, for which the following applies:

[0219] M is Si;

[0220] R 1 In each occurrence, the alkyl group may be a straight-chain alkyl group with 1 to 5 carbon atoms, in particular methyl, ethyl, n-propyl or n-butyl; a branched alkyl group with 3 to 6 carbon atoms, in particular isopropyl, isobutyl, sec-butyl or tert-butyl; or a cyclic alkyl group with 5 to 10 carbon atoms, in particular cyclopentyl, cyclohexyl, biscyclo[2.2.2]octanyl or adamantanyl, wherein the alkyl group may be partially or completely deuterated; or a phenyl group, which may also be partially or completely deuterated and / or which may also be modified by one or more substituents. 3 can be substituted, with a maximum of two groups R 1stand for a phenyl group; two or three substituents are possible 30 R 1 also form a ring with each other;

[0221] R 2 is, in each occurrence, the same or different, a straight-chain alkyl group with 1 to 5 carbon atoms, a branched alkyl group with 3 to 6 carbon atoms, or a cyclic alkyl group with 5 to 10 carbon atoms, wherein the alkyl group is in each case partially or completely deuterated 35 and / or with one or more Si(R) groups 7 )3 may be substituted, or an aromatic ring system with 6 to 12 aromatic Foreignfiling text P25-055.docx

[0222] - 26 -

[0223] Ring atoms, whereby these groups may also be partially or completely deuterated and / or also by one or more substituents R 4 They can be substituted; two or three substituents can be used. 2 , which bind to the same Si atom, also form a ring together;

[0224] Ar, whether identical or different in each occurrence, is 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 may be substituted;

[0225] 10 Alk is a linear alkylene group with 1 to 5 carbon atoms, in particular methylene, ethylene, n-propylene or n-butylene, a branched alkylene group with 3 to 5 carbon atoms, in particular isopropylene, isobutylene, sec-butylene, tert-butylene, or a cyclic alkylene group with 6 to 10 carbon atoms, wherein the alkylene group may also be partially or completely deuterated and / or modified by one or more substituents R 6 may be substituted;

[0226] The following applies to the indices o, p and q:

[0227] - o = 1, p = 0 and q = 0; or

[0228] - o = 0, p = 1 and q = 0; or

[0229] 20 - o = 1, p = 1 and q = 1;

[0230] R 3 is the same or different at each occurrence Si(R 7 )s, 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 be partially or completely deuterated; in each case, two or more R groups may be 3 also form a mono-, oligo- or polycyclic ring with each other;

[0231] R 4 is the same or different at each occurrence Si(R 7 )3, an even-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 more R groups may be present 4also form a mono-, oligo- or polycyclic ring with each other;

[0232] 35 R 5 is the same or different at each occurrence Si(R 7 )3, a straight-chain alkyl group with 1 to 5 carbon atoms or a branched or Foreignfiling text P25-055.docx

[0233] - 27 -

[0234] Cyclic alkyl group with 3 to 6 carbon atoms, wherein the alkyl group may be partially or completely deuterated; two or more R groups may be present. 5 also form a mono-, oligo- or polycyclic ring with each other;

[0235] 5 R 6 is the same or different at each occurrence Si(R 7 )3 or a phenyl group, which may also be partially or completely deuterated and / or which may also be joined with one or more Si(R) groups 7)3 and / or may be substituted with one or more alkyl groups with 1 to 5 carbon atoms, wherein two or more of these alkyl groups may also form a ring together;

[0236] R 7 is the same or different in each occurrence a straight-chain alkyl group with 1 to 5 carbon atoms, a branched alkyl group with 3 to 6 carbon atoms, or a cyclic alkyl group with 5 to 10 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 which may also be substituted with one or more alkyl groups with 1 to 5 carbon atoms, wherein two or more of these alkyl groups may also form a ring with each other; in this case, two or three substituents R 7 , which bind to the same 20 Si atom, also form a ring with each other;

[0237] with the proviso that R 1 to R 7and Ar do not contain a fused aryl group.

[0238] Compounds of formula (1) for which 25 holds are therefore particularly preferred:

[0239] M is Si;

[0240] R 1 is the same or different in each occurrence: methyl or ethyl, or a group R 1 stands for methyl and the other two groups R 1 together they form a cyclopentane or cyclohexane ring, or the 30 three groups together form an adamantyl group;

[0241] R 2 is the same or different in each occurrence methyl, ethyl, n-propyl, n-butyl, iso-propyl, iso-butyl, sec-butyl, tert-butyl, tert-pentyl, neo-pentyl, cyclopentyl, cyclohexyl, bicyclo[2.2.2]octanyl or adamantanyl, wherein the alkyl group is in each case partially or completely deuterated and / or with one or more Si(R) groups 7)3 may be substituted, or a phenyl group, which may also be partially or fully substituted-Foreignfiling text P25-055.docx

[0242] - 28 -

[0243] may be constantly deuterated and / or also by one or more substituents R 4 It can be substituted; this can involve two or three substituents R 2 , which bind to the same Si atom, also form a ring together;

[0244] 5Ar is a phenyl 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;

[0245] Alk is a methylene group or a cyclic alkylene group with 6 to 10 carbon atoms, especially groups derived from cyclohexane.

[0246] 10 Bicyclo[2.2.2]octane or adamantane, wherein the alkylene group may also be partially or completely deuterated and / or modified by one or more substituents R 6can be substituted; for the indices o, p and q:

[0247] - o = 1, p = 0 and q = 0; or

[0248] 15 - o = 0, p = 1 and q = 0; or

[0249] - o = 1, p = 1 and q = 1;

[0250] R 3 is the same or different at each occurrence Si(R 7 )3, Methyl, Ethyl, n-Propyl, n-Butyl, iso-Propyl, iso-Butyl, sec-Butyl, tert-Butyl, Cyclopentyl or Cyclohexyl, wherein the alkyl group may be partially or fully deuterated20; in each case two or more R groups may be 3 also form a mono-, oligo- or polycyclic ring with each other; R 4 is the same or different at each occurrence Si(R 7 )3, Methyl, Ethyl, n-Propyl, n-Butyl, iso-Propyl, iso-Butyl, sec-Butyl, tert-Butyl, Cyclopentyl or Cyclohexyl, wherein the alkyl group may be partially or fully deuterated25; in each case two or more R groups may be 4also form a mono-, oligo- or polycyclic ring with each other; R 5 is the same or different at each occurrence Si(R 7 )3, Methyl, Ethyl, n-Propyl, n-Butyl, iso-Propyl, iso-Butyl, sec-Butyl, tert-Butyl, Cyclopentyl or Cyclohexyl, wherein the alkyl group may be partially or fully deuterated; two or more R groups may be 5 also form a mono-, oligo- or polycyclic ring with each other; R 6 is the same or different at each occurrence Si(R 7 )3 or a phenyl group, which may also be partially or completely deuterated and / or which may also be combined with one or more groups 35 Si(R 7 )3 and / or with one or more alkyl groups with 1, 2, 3, 4 Foreignfiling text P25-055.docx

[0251] - 29 -

[0252] or can be substituted with 5 carbon atoms, whereby two or more of these alkyl groups can also form a ring together;

[0253] R 7 is the same or different in each occurrence methyl, ethyl, n-propyl, n-butyl, iso-propyl, iso-butyl, sec-butyl, tert-butyl, tert-pentyl, neo-pentyl, cyclopentyl, cyclohexyl, bicyclo[2.2.2]octanyl or adamantanyl, wherein the alkyl group 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 with one or more alkyl groups having 1, 2, 3, 4 or 5 carbon atoms, wherein two or more of these alkyl groups may also form a ring with each other; in this case, two or three substituents R 7 , which bind to the same Si atom, also form a ring together.

[0254] 15 The ordinary refractive index of the compounds according to the invention, measured via ellipsometry at 620 nm, is preferably < 1.6, particularly preferably < 1.55 and most preferably < 1.5.

[0255] According to the invention, the compound has a molecular weight of at least 500 g / mol. In a preferred embodiment of the invention, the compound has a molecular weight ≤ 4000 g / mol, preferably ≤ 3000 g / mol, particularly preferably ≤ 2000 g / mol, and most preferably ≤ 1500 g / mol. Particularly preferably, the compound has a molecular weight of 500 to 2000 g / mol, and most preferably 800 to 1500 g / mol. When processed from solution, higher molecular weights may also be suitable and preferred.

[0256] Furthermore, preferred compounds according to the invention are characterized by the fact that they are sublimable.

[0257] 30

[0258] 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 according to the embodiments are particularly preferred, which have a glass transition temperature of at least 70 °C, and especially preferably of at least

[0259] 110 °C, most preferably at least 125 °C and especially-Foreignfiling text P25-055.docx

[0260] - 30 -

[0261] which preferably have a temperature of at least 150 °C, determined according to DIN 51005 (version 2005-08).

[0262] Examples of preferred connections according to the 5 embodiments listed above are the connections listed in the following table.

[0263] 10

[0264] 15

[0265] 20

[0266] 25

[0267] 30

[0268] 35

[0269]

[0270] 9£

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278] Foreignfiling text P25-055.docx9£

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286] Foreignfiling text P25-055.docxForeignfiling text P25-055.docx

[0287] - 33 -

[0288] 5

[0289] 10

[0290] 15

[0291]

[0292] The compounds 4 according to the invention, containing an aromatic compound bound to M, can be prepared starting from aryl halides 1 known from the literature and the halosilanes 3, containing a residue -CH2-C(R) 1 )3 20 or a corresponding deuterated group, hereinafter referred to as R N The aryl halides 1 are prepared by salt metathesis reaction, as shown in Scheme 1. First, the aryl halides 1 are transmetallated to the compounds 2 by reaction with a reactive metal, such as Li, Mg, or Zn, or with an organometallic compound, such as an organolithium compound, 25 preferably n-butyllithium, n-hexyllithium, tert-butyllithium, or a Grignard reagent, preferably isopropyl-MgCl₂*LiCl₂ (Knöchel Turbo-Grignard). The intermediate aryl-metal compounds 2 thus obtained are then transmetallated with a mono-, di-, tri-, or tetra-halosilane or -german 3, containing a -CH₂-C(R₂) group. 1 )3- 30 Rest R NThe reaction is carried out. X is preferentially Br and Y is preferentially CI. For clarity, optional substituents have not been shown in Scheme 1.

[0293] Scheme 1:

[0294] 35Foreignfiling text P25-055.docx

[0295] -34 -

[0296] Y 4-m M(R 2 ) m R N RM* or M 3 M: Si, Ge Y = CI, Br R 2 : Alkyl, Aryl X: CI, Br, IM': Li, MgX R N : -CH2-C(R 1 )3

[0297] 1 2 m: 0,1,2

[0298]

[0299] Alternatively, compounds 8 according to the invention can be prepared from the alkyl halogenides 5 and the halosilanes 7, wherein at least 10

[0300] one of the residues R or R N a residue -CH2-C(R 1)3 must be as shown in Scheme 2. For this purpose, the alkyl halides 5 are first reacted with a reactive metal, such as Li, Mg or Zn, or with an organometallic compound, such as an organolithium compound, preferably n-butyllithium, n-hexyllithium, tert-butyllithium, or a

[0301] 15

[0302] Grignard reagent, preferably iso-propyl-MgCl*LiCl (Knöchel Turbo-Grignard), is transmetallated to give compounds 6. The intermediate alkyl-metal compounds 6 obtained in this way are then reacted with a mono-, di-, tri-, or tetra-halosilane or -german 7. X is preferably Br and Y is preferably CI. For clarity, 20

[0303] Optional substituents are not shown in Scheme 1.

[0304] Scheme 2:

[0305] Y4-m-nMR 2 m R N n R RM* or M* I

[0306] 25

[0307] XR: Alkyl, R N M* M: Si, Ge X: CI, Br, IM*: Li, MgX Y = Cl, Br 4-mn

[0308]

[0309] 56R 2 : Alkyl, Aryl 8

[0310] R N : -CH2-C(R 1 )3

[0311] m+n: 1,2,3

[0312] m: 0, 1, 2, 3

[0313] n: 0.1

[0314] 30

[0315] Preferred reaction media in both processes are dipolar aprotic solvents such as ethers or cyclic ethers, in particular diethyl di-n-butyl ether, tert-butyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, or dioxane, or mixtures thereof. The exothermic salt metathesis is 35

[0316] The reaction is preferably carried out at cryogenic temperatures or under refrigeration if necessary; however, it can also be carried out at elevated temperatures to complete the reaction. Foreignfiling text P25-055.docx

[0317] - 35 -

[0318] The work is carried out at a specific temperature. The processing and purification of the compounds 4 and 8 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 in high vacuum.

[0319] Another object of the present invention is therefore a process for producing a compound according to the invention, wherein first an aryl halide or alkyl halide is reacted to form an aryl or alkyl metal compound and the aryl or alkyl metal compound is then reacted with a halogenated silicon compound or a halogenated germanium compound by salt metathesis.

[0320] These processes, possibly followed by purification, such as...

[0321] 15. By recrystallization or sublimation, the compounds according to the invention can be obtained in high purity, preferably more than 99% (determined by means of 1H-NMR, HPLC and / or GC).

[0322] Particularly for the use of the compounds according to the invention in 20 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.

[0323] 25

[0324] 30

[0325]

[0326] Formula (T)

[0327] wherein the symbols and indices have the meanings mentioned above, characterized in that the compound consists of one or more of the substituents R instead of R 1 to R 7 contains a networkable group 35. Foreignfiling text P25-055.docx

[0328] - 36 -

[0329] In the present invention, a crosslinkable group 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 is thus a reactive group. The reaction of the crosslinkable group results in a correspondingly crosslinked compound. The chemical reaction can also be carried out within a layer, forming 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.“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 that 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.

[0330] 20

[0331] The compound according to the invention can comprise one, two, three or more crosslinkable groups, with two, three or more crosslinkable groups being preferred.

[0332] 25

[0333] Suitable and preferred networkable groups are listed below:

[0334] a) Terminal or cyclic alkenyl or terminal dienyl and alkynyl groups:

[0335] 30

[0336] 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 alkenyl, terminal dienyl or terminal alkynyl groups with 2 to 20 carbon atoms, preferably with 2 to 10 carbon atoms, wherein individual 35

[0337] CH2 groups and / or individual H atoms may be replaced by the above-mentioned R groups, and the groups may be partially or fully replaced. - Foreignfiling text P25-055.docx

[0338] - 37 -

[0339] They can be constantly deuterated. Furthermore, groups that can be considered precursors and that are capable of forming a double or triple bond in situ are also suitable.

[0340] 5 b) Alkenyloxy, dienyloxy or alkynyloxy groups:

[0341] Alkenyloxy, dienyloxy or alkynyloxy groups are also suitable, preferably alkenyloxy groups.

[0342] c) Acrylic acid groups:

[0343] 10. 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.

[0344] The crosslinking reaction of the groups mentioned above under a) to c) can proceed via a radical, cationic, or anionic mechanism, as well as via cycloaddition. It can be advantageous to add a suitable initiator for the crosslinking reaction. Suitable initiators for radical crosslinking include, for example, dibenzoyl peroxide, AIBN, or TEMPO. Suitable initiators for cationic crosslinking include, for example, AIDS, BF3, triphenyl methyl perchlorate, or tropylium hexachloroantimonate. Suitable initiators for anionic crosslinking are bases, particularly butyllithium. In a preferred embodiment of the present invention, however, the crosslinking is carried out without the addition of an initiator and is ultimately initiated 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.

[0345] 30 d) Oxetanes and oxiranes:

[0346] Another suitable class of crosslinkable groups are oxetanes and oxiranes, which crosslink cationically via ring opening. Here, too, it can be advantageous to add an initiator for the crosslinking reaction. Suitable initiators include, for example, AICI3, BF3, triphenylmethylper35 chlorate, or tropylium hexachloroantimonate. Photoacids can also be added as initiators.

[0347] - 38 -

[0348] e) Silanes:

[0349] Silane groups SiRs are also suitable as a class of crosslinkable groups, where at least two groups R, preferably all three groups R5, 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.

[0350] f) Cyclobutane groups

[0351] 10

[0352] The crosslinkable groups mentioned above under a) to f) are generally known to those skilled in the art, as are the suitable reaction conditions used to crosslink these groups.

[0353] 15 Preferred crosslinkable groups include alkenyl groups of the following formula Q1, dienyl groups of the following formula Q2, alkynyl groups of the following formula Q3, alkenyloxy groups of the following formula Q4, dienyloxy groups of the following formula Q5, alkynyloxy groups of the following formula Q6, acrylic acid groups of the following formulas Q7 and Q8, oxetane groups of the following formulas Q9 and Q10, oxirane groups of the following formula Q11, and cyclobutane groups of the following formulas Q12, Q13, and Q14:

[0354] 25

[0355] 30

[0356] 35

[0357]

[0358] Foreign filing text P25-055.docx

[0359] - 39 -

[0360] 5

[0361] 10

[0362] 15

[0363] 20

[0364]

[0365] The symbols and indices used have the following meanings:

[0366] 25

[0367] R 11 , R 12 , R 13 , R 14 are, in each occurrence, the same or different alkyl group H, D, a straight-chain group with 1 to 6 C atoms, preferably with 1 to 4 C atoms, or a branched or cyclic alkyl group with 3 to 6 C atoms, preferably H, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, sec-Butyl or tert-Butyl and particularly preferably H or Methyl;

[0368] m is 0 to 8;

[0369] n is 1 to 8;

[0370] Ar 10 In each occurrence, the aromatic ring system is either the same or different, with 6 to 40 aromatic ring atoms or a hetero35 aromatic ring system with 5 to 40 aromatic ring atoms, wherein the aromatic or heteroaromatic ring system is connected to a Foreignfiling text P25-055.docx

[0371] - 40 -

[0372] or can be substituted by several residues other than H, the residues preferably being the same.

[0373] The dashed bonds in formulas Q1 to Q11 and Q14, as well as the 5 dashed bonds in formulas Q12 and Q13, represent the connection of the crosslinkable group to the repeating units.

[0374] The crosslinkable groups of formulas Q1 to Q14 can be directly linked to the repeating unit, or indirectly, via a further mono- or polycyclic aromatic or heteroaromatic ring system Ar. 10 , as shown in the following formulas Q15 to Q28:

[0375] 15

[0376] 20

[0377] 25

[0378] 30

[0379]

[0380] 35Foreignfiling_text P25-055.docx

[0381] -41 -

[0382] 5

[0383] 10

[0384] 15

[0385]

[0386] 20

[0387] where the symbols and indices have the same meanings as described above.

[0388] The following groups are particularly favored for networking: 25 H

[0389] H

[0390] H _> H -(CH2) m ^

[0391] Q1a Q2a

[0392] 30

[0393] 0

[0394] R 11

[0395] H

[0396] / k H

[0397] -(CH2) m -O-(CH2) n ^ H

[0398] 35....... (CH2) m

[0399]

[0400] Q4a Q7aForeignfiling text P25-055.docx

[0401] -42 -

[0402] 5

[0403] 10

[0404] 15

[0405] 20

[0406] 25

[0407] 30

[0408] 35

[0409]

[0410] Foreign filing text P25-055.docx

[0411] -43 -

[0412] 5

[0413]

[0414] the symbols and indices used have the 10 meanings mentioned above.

[0415] The following groups are particularly favored for networking:

[0416] 15

[0417] 20

[0418] 25

[0419] 30

[0420]

[0421] 35Foreignfiling_text P25-055.docx

[0422] -44 - HH

[0423] H / HT / T — O'

[0424] Q13a Q14b

[0425] H

[0426] H — H Q15b Q15c

[0427] HHHH

[0428] Q15d Q15e

[0429] H

[0430] Q15f Q15g

[0431] HH

[0432] \ H \ — H Q16b Q16c

[0433] Hz H

[0434] — H

[0435]

[0436] Q16d Q16e

[0437] 35Foreignfiling text P25-055.docx

[0438] 5

[0439] 10

[0440] 15

[0441]

[0442] 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 20

[0443] especially if the compounds are to be used in a capping layer. Covalent incorporation into polymers is possible, in addition to the crosslinkable groups defined above, particularly with compounds substituted with reactive leaving groups such as bromine, iodine, chlorine, boronic acid, or boronic acid esters. These can be used as monomers for the 25

[0444] The invention can be used to produce corresponding oligomers, dendrimers, or polymers. The oligomerization or polymerization preferably occurs via the halogen functionality or the boronic acid functionality, respectively. It is also possible to crosslink the polymers via such groups. The compounds and polymers according to the invention can be described as 30

[0445] A networked or non-networked layer can be used.

[0446] Further subject matter 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 listed above.35

[0447] forms, wherein one or more bonds of the compounds according to the invention to the polymer, oligomer or dendrimer are present. JeForeignfiling text P25-055.docx

[0448] -46 -

[0449] After linking the structures of formula (1) or the preferred embodiments, these therefore form a side chain of the oligomer or polymer or are linked in the main chain. The polymers, oligomers, 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 according to the invention.

[0450] 10

[0451] 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, 25 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, sebacic acid diethyl ester, octyl octanoate, heptylbenzene, menthyl isovalerate, cyclohexylhexanoate or mixtures of these solvents.

[0452] 35 Another object of the present invention is therefore a formulation or a composition containing at least one Foreignfiling text P25-055.docx

[0453] -47 -

[0454] The compound according to formula (1) or according to the preferred embodiments and at least one further compound. Formulations or compositions containing oligomers, dendrimers, or polymers of the present invention are included herein. The further compound 5 can, 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 hereby referred to as a formulation.The further compound can also be at least one further organic or inorganic compound that is also used in the electronic device, 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 that is also used in the electronic device is here referred to as a composition or mixture.

[0455] Another object of the present invention is a mixture comprising at least one compound according to formula (1) or according to 20 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,

[0456] 25 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.

[0457] 30 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 electroluminescent device. This makes it easy to adapt and match the refractive indices of different 35 functional layers, thereby enabling a significant increase in the efficiency of the devices. This yields the Foreignfiling text P25-055.docx

[0458] -48 -

[0459] Refractive index of the layer approximately as the arithmetic mean of the refractive indices of the functional materials in the layer and the compound of formula (1) or the preferred embodiments as a function of the respective concentration.

[0460] 5

[0461] 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, ten, 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.

[0462] 15 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 10 vol.% to 70 vol.%, most preferably in the range of 15 vol.% to 60 vol.% and particularly in the range of 15 vol.% to 50 vol.%.

[0463] 20 This proportion has proven to be particularly suitable for reducing the refractive index without negatively affecting the electronic properties of the layer.

[0464] Preferably, it can be provided that the composition

[0465] 25 comprising at least one compound according to formula (1) or the preferred embodiments and at least one hole transport material.

[0466] 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.

[0467] -49 -

[0468] Preferred compounds exhibiting hole injection and / or hole transport properties include, for example, triarylamine, benzidine, tetraaryl-para-phenylenediamine, triarylphosphine, phenothiazine, 5-phenoxazine, dihydrophenazine, thianthrene, dibenzo-para-dioxine, phenoxathiine, carbazole, azulene, thiophene, pyrrole, and furan derivatives, and other 0-, S-, or N-containing heterocycles with a high-lying HOMO (HOMO = highest occupied molecular orbital).

[0469] Ten compounds exhibiting hole injection and / or hole transport properties are preferably selected from triarylamines, in particular mono-triarylamines, bis-triarylamines, and carbazolamines. A mono-triarylamine is understood to be a compound containing a single amine group, wherein three groups selected from aromatic and heteroaromatic ring systems are bonded to the nitrogen atom of the amine group. A bis-triarylamine is understood to be a compound comprising two and no further amine groups, wherein three groups selected from aromatic and heteroaromatic ring systems are bonded to each of the nitrogen atoms of the two amine groups. A carbazolamine is understood to be 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 heteroaroma25 tic ring systems are bonded to the nitrogen atom of the amine group.

[0470] 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)

[0471] 30

[0472] Ar 15

[0473] Ar 15 Ar 15

[0474] \ /

[0475] ''N-- Ar 15 N-Ar 16 — N

[0476] Ar 15 'Ar 15 Ar 15

[0477]

[0478] _ (L-1) _ _ (k2) _

[0479] 35Foreignfiling text P25-055.docx

[0480] - 50 -

[0481] where the connections may be partially or completely deuterated and the following applies to the symbols used:

[0482] Ar 15 is chosen the same or differently in each occurrence 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 They may be substituted;

[0483] 10

[0484] 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 sub15 may be situated;

[0485] R 15 is 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 -, -C≡C-, Si(R 16 )2, C=O,

[0486] C=NR 16 , -C(=O)O-, -C(=O)NR 16 -, NR 16, P(=O)(R 16 ), -O-, -S-, SO or SO2; wherein two or more, preferably adjacent, residues R 15 together form a ring system;

[0487] 35 R 16 is chosen from H, D, in every occurrence, whether the same or different,

[0488] 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 ,Foreign filing text P25-055.docx

[0489] - 51 -

[0490] 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 10 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 -,

[0491] -C≡C-, Si(R 17 )2, C=O, C=NR 17 , -C(=O)O-, -C(=O)NR 17 -, NR 17 , P(=O)(R 17 ), -O-, -S-, SO or SO2; where two or

[0492] 15 several, preferably adjacent residues R 16 together form a ring system;

[0493] R 17 The group consists of the same or different elements in each occurrence, selected 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.

[0494] Preferred Groups Ar 15are identical or different at each occurrence 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, pyrimidine, pyrazine, pyridazine and triazine, each of the groups being partially or completely deuterated and / or with one or more R groups 15 can be substituted. Foreignfiling text P25-055.docx

[0495] - 52 -

[0496] 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, ter5 phenyl, 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 10 being partially or completely deuterated and / or with one or more R groups 15 may be substituted.

[0497] Particularly preferred groups Ar 15are, the same or different at each occurrence, chosen from monovalent groups derived from benzene, 15-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 20, which is substituted with a group consisting of naphthyl,

[0498] Phenanthrenyl, fluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidyl and triazinyl are selected, each of the above groups being partially or completely deuterated and / or with one or more R groups. 15 may be substituted.

[0499] 25

[0500] Preferred Groups Ar 16are selected from divalent groups, which differ from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, 30 dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene,

[0501] Derive indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, each of the groups being partially or completely deuterated and / or having one or more R residues. 15 may be substituted.

[0502] 35 Preferably the groups Ar 16 selected from divalent groups, which represent combinations of 2 to 4 groups, which are selected from Foreignfiling text P25-055.docx

[0503] - 53 -

[0504] 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, 5-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.

[0505] Particularly preferred groups Ar 16are selected from divalent groups, 10 which are derived 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 15 dibenzothienyl, each of the above groups being partially or completely deuterated and / or with R groups 15 may be substituted.

[0506] Preferably R 15 Equal or different choices made from H, D, F, CN, Si(R) 16 )3, N(R 16)2, straight-chain alkyl or alkoxy groups with 1 to 20 C-20 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 25 and / or modified by R groups 16 may be substituted.

[0507] 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 carbon atoms, branched or cyclic alkyl or alkoxy groups with 3 to 30 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 and alkoxy groups and the aromatic and heteroaromatic ring systems are partially or completely deuterated and / or modified by one or more R groups 17 may be substituted.

[0508] 35Foreignfiling text P25-055.docx

[0509] - 54 -

[0510] Preferably R 17 The elements chosen for each occurrence are the same or different 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.

[0511] 5

[0512] Particularly preferred executions of the connections of the formula (L-1) correspond to the following formulas,

[0513] (R 15 )5^^ / R 15\ ( R15 )3

[0514] 10

[0515] Ar15 [f I || -j- (Ar 17 )nN Ar 15 [LXX JJ~-(R 15 L (R 15 )5\=X (R 15 )4V^ X A^

[0516] 15

[0517] (L-1-1) (L-1 -2)

[0518] R 15 R 15 Ar 15 R15 The 15 (The^

[0519] , R is> f \\_ / / -5 Ar f L / V Ar 15 — \= / (R?3

[0520] 20

[0521] (L-1 -3) (L-1 -4)

[0522] R 1 5 R 15 (R 15 )2 The 15 D15

[0523] R 15 R 15 pR 15 The 15 / / \ ^(The 17 )nN ^_(Ar 17 )n—N (R 15)4V_ / \ / \— 5? Ar15

[0524] — — X (R 15 )3(R 15 )4< \=_ / / \ \=_\\=V / V \=Ö / X^ (R I 5) AR15 R15^ R

[0525] 25 15 (R 15 )2

[0526] (L-1 -5) (L-1 -6) f^X(R 15 )4

[0527] R 15 YAJ Ar \ ^Ar 15 30 1 X Ar15

[0528] t ^(Ar 17 )n R T ~tr~ (Ar )n " N \

[0529] AX, R 1 5. Ar 15

[0530] / 3 (R' S )4Ä= /

[0531]

[0532] _ (L-1-7) _ _ (L-1-8) _

[0533] 35Foreignfiling text P25-055.docx

[0534] - 55 -

[0535] 5

[0536]

[0537] where the compounds may be partially or completely deuterated, 10

[0538] the symbols Ar15 and R 15 the meanings mentioned above, especially for formula (L-1), and the following applies to the other symbols:

[0539] Ar 17 is selected from aromatic ring systems with 6 to 13 aromatic ring atoms, separated by one or more R groups 15 15

[0540] can be substituted, and heteroaromatic ring systems with 5 to 13 aromatic ring atoms separated by one or more R groups 15 can be substituted with something other than H;

[0541] X is chosen from a pool of 20, either the same or different in each instance.

[0542] Binding, 0, S, NR 15 and C(R 15 )2;

[0543] Y 1 is chosen from 0 or S;

[0544] n is either 0 or 1, where n = 0 means that the group with index 25

[0545] n is not present and that the groups bound to the group with index n are directly connected to each other, provided that n is not 0 in the case of the formula (L-1 -9).

[0546] The preferred group is Ar 17 selected from divalent groups, which differed from 30

[0547] Benzene, biphenyl, naphthalene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, are derived, each of the groups having R substituents. 15 may be substituted.

[0548] The compounds of formulas (L-1-2) and 35 are particularly preferred.

[0549] (L-1-3), wherein compounds of the following formula (L-1-2-1) are particularly preferred as embodiments of formula (L-1-2), Foreignfiling text P25-055.docx

[0550] - 56 -

[0551] 5

[0552]

[0553] 10

[0554] wherein the compounds may be partially or completely deuterated and the symbols and indices have the aforementioned meanings and preferably correspond to the preferred embodiments mentioned above.

[0555] 15

[0556] Particularly preferred embodiments of the compounds of formula (L-2) correspond to the following formulas (L-2-1) and / or (L-2-2),

[0557] 20

[0558] 25

[0559] 30

[0560]

[0561] where the compounds may be partially or completely deuterated, the symbols Ar 15 and R 15 the aforementioned meanings and 35 preferably correspond to the preferred embodiments mentioned above, and the following applies to the further symbols: Foreignfiling text P25-055.docx

[0562] - 57 -

[0563] Y 2is chosen the same or differently from a bond, 0, S, NR, in each occurrence. 15 and C(R 15 )2;

[0564] 5k is 1, 2, 3 or 4, preferably 1 or 2;

[0565] i is 1, 2 or 3, preferably 1 or 2, particularly preferably 1.

[0566] 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:

[0567] 15

[0568] 20

[0569] 25

[0570] 30

[0571] 35

[0572]

[0573] 35

[0574] 30

[0575] 25 20 15 10 5

[0576]

[0577] - 89 - Foreign filing text P25-055.docx35

[0578] 30

[0579] 25 20 15 10 5

[0580]

[0581] - 69 - Foreignfiling text P25-055.docx35

[0582] 30

[0583] 25 20 15 10 5

[0584]

[0585] Foreignfiling text P25-055.docx35

[0586] 30

[0587] 25 20 15 10 5

[0588]

[0589] Foreignfiling text P25-055.docx35

[0590] 30

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[1351] F Fy MX n ^YCFFXCC- M^ Ou ^r C / J Fz XXrX^) FW~~ _ _ _ CM!) Cx JxC) OF

[1352] X. F-#

[1353] v3 / W^XXFX FJ

[1354] O

[1355] MX\X CXM} r\M \=FF tF A < FMF XA / XFM) CM A

[1356]

[1357] MM M 0

[1358] - 86 -

[1359] Foreignfiling text P25-055.docxForeignfiling text P25-055.docx

[1360] - 99 -

[1361] 5

[1362] 10

[1363] 15

[1364] 20

[1365] 25

[1366] 30

[1367]

[1368] 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 (vs. vacuum level), especially Foreignfiling text P25-055.docx

[1369] - 100 -

[1370] preferably from more than −5.5 eV, as defined by quantum mechanical calculations.

[1371] 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.

[1372] 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.

[1373] This design provides sublimable compositions that can be used particularly reliably in a plant for the production of high-quality electronic devices.

[1374] 30

[1375] 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.

[1376] 35 compounds exhibiting electron injection and / or electron transport properties, also referred to herein as electron transport materials. Foreignfiling text P25-055.docx

[1377] - 101 -

[1378] 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).

[1379] Particularly suitable compounds for electron-transporting and electron-injecting layers are metal chelates of 8-hydroxyquinoline 10 (e.g., LiQ, AlQ3, 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).

[1380] 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),

[1381] 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).

[1382] Examples of electron transport materials are the compounds shown below, which may also be partially or completely deuterated:

[1383] 30

[1384] 35Foreignfiling text P25-055.docx

[1385] - 102 -

[1386] 5

[1387] 10

[1388]

[1389] 15

[1390] Formula ET-4

[1391]

[1392] 20 Formula ET-5

[1393] 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.

[1394] 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 P25-055.docx

[1395] - 103 -

[1396] 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).

[1397] 5

[1398] O1

[1399] <7= _

[1400] Hx

[1401] >

[1402] CO

[1403] 10

[1404]

[1405] 15

[1406]

[1407]

[1408] In a preferred embodiment, the composition may include at least one electron transport material selected from compounds of formulas (E-1) to (E-4).

[1409] , N.

[1410] fl '-?-Ar 18

[1411] 25 X (R 15 )3

[1412] (E-1) (E-2)

[1413] (R 15 )4_rr yy

[1414] f lr Ar18

[1415] ^^^NT ^R 15 30 ^\R 15 )4

[1416]

[1417] _ (E-3) _ _ (E-4) _

[1418] where the compounds may be partially or completely deuterated, R 15 the meaning previously mentioned for formula (L-1) and furthermore 35

[1419] applies:Foreignfiling text P25-055.docx

[1420] - 104 -

[1421] 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.

[1422] Compounds according to formulas (E-1) to (E-3) are preferred, in particular compounds according to formula (E-1).

[1423] 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)

[1424] 15

[1425] 20

[1426] 25

[1427]

[1428] where the compounds can also be partially or completely deuterated, the symbols R 15 which has the aforementioned meanings and preferably corresponds to the preferred embodiments 30 mentioned above, and for the further symbols the following applies:

[1429] 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 separated by one or more R groups 15 can be substituted; Foreignfiling text P25-055.docx

[1430] - 105 -

[1431] 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.

[1432] 5

[1433] 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:

[1434] 10

[1435] 15

[1436] 20

[1437] 25

[1438] 30

[1439]

[1440] 3535

[1441] 30

[1442] 25 20 15 10 5

[1443]

[1444] - 90k - Foreignfiling text P25-055.docx35

[1445] 30

[1446] 25 20 15 10 5

[1447]

[1448] - ZOk - Foreignfiling text P25-055.docx

[1449]

[1450]

[1451]

[1452]

[1453]

[1454]

[1455]

[1456]

[1457] Foreignfiling text P25-055.docx35

[1458] 30

[1459] 25 20 15 10 5

[1460]

[1461] - 60 k - Foreignfiling text P25-055.docx35

[1462] 30

[1463] 25 20 15 10 5

[1464]

[1465] - Ok k - Foreignfiling text P25-055.docxForeignfiling text P25-055.docx

[1466] - 111 -

[1467] 5

[1468] 10

[1469]

[1470] 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.

[1471] 25

[1472] 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.

[1473] 35 This design provides sublimable compositions that can be reliably used in a plant to manufacture high-quality electronic devices. Foreignfiling text P25-055.docx

[1474] - 112 -

[1475] 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.

[1476] Furthermore, the compositions according to the invention can comprise at least one hole blocking material (HBM).

[1477] 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.

[1478] 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.

[1479] 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, adjacent to an emission layer on the anode side.

[1480] - 113 -

[1481] 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.

[1482] 10 Organic functional materials, as described above and below, are often characterized by the properties of their frontier orbitals, which are explained in more detail below. The energy levels of molecular orbitals (highest occupied molecular orbital HOMO, lowest unoccupied molecular orbital LUMO, lowest triplet state T1, lowest excited singlet state S1) are determined by quantum mechanical calculations. The Gaussian16 (Rev. B.01) software package is used in all quantum chemical calculations. The neutral singlet ground state is optimized at the B3LYP / 6-31G(d) level. 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.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:

[1483] HOMO_corr = 0.90603 * HOMO (in eV) - 0.84836

[1484] LUMO_corr = 0.99687 * LUMO (in eV) - 0.72445

[1485] For the purposes of this application, these values ​​are to be regarded as HOMO or LUMO-30 energy levels of the materials.

[1486] The lowest triplet state T1 is defined as the energy of the lowest-energy triplet state resulting from the described quantum chemical calculation. The lowest excited singlet state Si is defined as the energy of the excited singlet state. Foreignfiling text P25-055.docx

[1487] - 114 -

[1488] with the lowest energy, which results from the described quantum chemical calculation.

[1489] A further object of the present invention is the use 5 of a compound according to formula (1) or of the preferred embodiments mentioned above, or of corresponding crosslinkable or crosslinked compounds or oligomers, polymers, or dendrimers in an electronic device, in particular in an organic electroluminescent device. Preferably, it may be provided that the compounds according to the invention 10 are used to vary the refractive index, in particular to reduce the refractive index.

[1490] 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.

[1491] An electronic device within the meaning of the present invention is a device comprising at least one layer containing at least one organic compound. The component may also contain inorganic materials or layers composed entirely of inorganic materials. A particularly preferred electronic device is 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), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), and 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.

[1492] (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs) and organic electrical sensors, preferably organic Foreignfiling text P25-055.docx

[1493] - 115 -

[1494] Electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), particularly preferably organic light-emitting diodes (OLEDs), small molecule-based organic light-emitting diodes (sOLEDs) and organic light-emitting diodes based on

[1495] 5 polymers (PLEDs).

[1496] The organic electroluminescent device contains a cathode, anode, and at least one emitting layer. In addition to these layers, it may contain further 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. Interlayers, which may, for example, have an exciton blocking function, may also be introduced between two emitting layers. It should be noted, however, that not every one of these layers is necessarily present. The organic electroluminescent device may contain one or more emitting layers.If multiple emission layers are present, these preferably exhibit a total of 20 emission maxima between 380 nm and 750 nm, resulting in overall white emission. This means that different emitting compounds capable of fluorescence or phosphorescence are used in the emitting layers. Systems with three emitting layers are particularly preferred, wherein the three layers exhibit blue, green, and orange or red emission. The organic electroluminescence device according to the invention can also be a tandem electroluminescence device, especially for white-emitting OLEDs.

[1497] 30 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 and / or in a hole-blocking layer, each in combination with an electron transport or hole-blocking material, is preferred. A further preferred organic electroluminescent device containing the compound is [Foreignfiling text P25-055.docx].

[1498] - 116 -

[1499] The compound can be used in a hole transport layer and / or electron blocking layer, each in combination with a hole transport or electron blocking material. It can also be used in an emission layer. Furthermore, 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 high concentrations and preferably as a pure layer.

[1500] 10

[1501] 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). Suitable emitters for the emission layer include...

[1502] 15. In principle, all commonly used emitters (dotandes) can be used. The emitter (dotande) is usually used in combination with one or more matrix materials, and all commonly used matrix materials are suitable for this purpose.

[1503] 20 Preferably, the fluorescent emitter in the composition has a peak emission wavelength between 420 - 550 nm, preferably between 420 - 470 nm.

[1504] 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 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, aromatic anthracenediamine, aromatic pyrene, aromatic pyrenediamine, aromatic chrysene, or aromatic chrysenediamine. An aromatic anthracene is understood to be a compound in which a diarylamine group is directly bonded to the nitrogen.

[1505] - 117 -

[1506] An aromatic anthracene group is defined as a compound in which two diarylamine groups are directly bonded to an anthracene group, preferably at the 9 and 10 positions. Similarly, aromatic 5-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. Pyrenarylamines disclosed in WO 2012 / 048780 and WO 2013 / 185871 are also preferred.Eben15 if 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 fluorine derivatives bound to 20 furan units or to thiophene units disclosed in WO 2016 / 150544.

[1507] 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, KR 2018046851, WO 2019 / 009052, WO 2020 / 101001, US 2020 / 0207787, 25 WO 2020 / 138874, KR 2020081978, JP 2020-147563, US 2020 / 0335705 or KR 2022041028 can be used.

[1508] Preferably, the at least one fluorescent emitter has a full width at half maximum (FWHM) ≤ 50–30 nm, preferably FWHM ≤ 40 nm, more preferably FWHM ≤ 30 nm.

[1509] 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.

[1510] - 118 -

[1511] preferably from -4.9 eV to -5.1 eV, as defined by quantum chemical calculations.

[1512] Preferably, the energy of the lowest singlet state S1 of the 5 fluorescent emitters 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.

[1513] In a preferred embodiment of the invention, the fluorescent 10 emitter is selected from structures of the following formula (F-1),

[1514] 15

[1515]

[1516] Formula (F-1)

[1517] where R has the meanings mentioned above and the following applies to the other 20 symbols and indices used:

[1518] 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

[1519] 25 heteroaromatic ring system may contain nitrogen, boron and / or phosphorus atoms;

[1520] Y 30 is B or N;

[1521] 30 Y 31 , Y 32 , Y 33 is the same or different in each occurrence and represents 0

[1522]

[1523] , S, C(R°)2, C=O, C=S, C=NR°, C=C(R°)2, Si(R°)2, BR°, NR°, PR°, SO2, SeO2 or a chemical bond, with the proviso 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 P25-055.docx

[1524] - 119 -

[1525] 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;

[1526] q is either 0 or 1.

[1527] Connections are particularly preferred where the following applies:

[1528] 20

[1529] - q = 0; Y 30 = B; and Y 31 , Y 32 = NR°; or

[1530] - q = 0; Y 30 = B; and Y 31 , Y 32 = NR°; or

[1531] - q = 1; Y 30 = N; and Y 31 , Y 32 = BR°; Y 33 = chemical bond.

[1532] 25 examples of suitable fluorescent emitters are shown in the table below:

[1533] 30

[1534] 35

[1535]

[1536]

[1537]

[1538]

[1539]

[1540]

[1541]

[1542]

[1543]

[1544] Foreignfiling text P25-055.docx35

[1545] 30

[1546] 25 20 15 10 5

[1547]

[1548] - kZk - Foreignfiling text P25-055.docx35

[1549] 30

[1550] 25 20 15 10 5

[1551]

[1552] - 33k - Foreignfiling text P25-055.docx

[1553]

[1554] Q

[1555] _N. QX>

[1556] M CbO -v> C 3

[1557] QT0 0.0^0 N

[1558] N

[1559] o^ XfJ^Lo o xS

[1560]

[1561] qW qqq qPP O^-'P^O 0 N p o V'XJ M

[1562]

[1563] p QQ a QQQQ ap npq aip®öqrci ax) dro q?

[1564]

[1565] p Q 9 p cP QQ o Ap oO7ö apppp

[1566] ax 6x q / p ir\p

[1567]

[1568] yes yes

[1569] QQQQQQQQ OWW ^ typXö?^

[1570]

[1571] q / pa\ p at) (Jx'o

[1572] oo 0-0 (TO QoQoQoQ QJ?.

[1573]

[1574] aXt^Ä 'O ' / CX J7V:

[1575]

[1576] a'-ö • tiro (kt!) ckö

[1577] - 123 - Foreignfiling text P25-055.docxForeignfiling text P25-055.docx

[1578] - 124 -

[1579] 5

[1580] 10

[1581] 15

[1582]

[1583] The following are examples of preferred compounds that can serve as phosphorescent emitters. The term "phosphorescent compound" (or "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 higher spin quantum number, e.g., a quintet state. Luminescent complexes with transition metals or lanthanides are preferred as phosphorescent compounds. Within the scope of the present invention, all luminescent indium, platinum, or copper complexes are considered phosphorescent emitting compounds. Iridium or platinum complexes are particularly preferred.

[1584] 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 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 P25-055.docx

[1585] - 125 -

[1586] 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 for phosphorescent OLEDs according to the prior art and as known to those skilled in the art in the field of organic electroluminescence are suitable, and those skilled in the art can use further 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.

[1587] 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.

[1588] 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

[1589] 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.

[1590] 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.

[1591] - 126 -

[1592] 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.

[1593] 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.

[1594] 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, 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.

[1595] Examples of phosphorescent compounds are listed below.

[1596] 3535

[1597] 30

[1598] 25 20 15 10 5

[1599]

[1600] - ZZk - Foreign filing text P25-055.docx98

[1601] OS

[1602] 92 03 9 k O k 9

[1603]

[1604] - 83k - Foreign filing text P25-055.docx35

[1605] 30

[1606] 25 20 15 10 5

[1607]

[1608] - 63k - Foreignfiling text P25-055.docxForeignfiling text P25-055.docx

[1609] - 130 -

[1610] 5

[1611] 10

[1612]

[1613] In one embodiment of the invention, a hyperfluorescence and / or hyperphosphorescence system is formed by a suitable combination of compounds.

[1614] 15

[1615] 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.

[1616] 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.

[1617] 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 P25-055.docx

[1618] - 131 -

[1619] 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 singlet-triplet distance ΔE(S1–T1) of, for example, less than about 2000 cm' is required in the emitter. 1 necessary. In order to open the spin-forbidden transition T1→S1, another compound can be provided in the matrix next to the emitter, which has strong spin-orbit coupling, so that inter-system crossing is enabled via the spatial proximity and the thus possible interaction between the molecules, or the spin-orbit coupling is generated via a metal atom contained in the emitter.

[1620] 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.

[1621] 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.

[1622] 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.

[1623] 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 condensed aromatic groups such as e.g.

[1624] Anthracene, Benzanthracene, Benzphenanthrene (DE 102009005746, WO 35 09 / 069566), Phenanthrene, Tetracene, Coronene, Chrysene, Fluorene, Spirobifluorene, Perylene, Phthaloperylene, Naphthaloperylene, Decacycles, Rubrene, Foreignfiling text P25-055.docx

[1625] - 132 -

[1626] 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. B. AlQ3(= Aluminium(III)tris(8-hydroxyquinoline)) or 5 Bis(2-methyl-8-quinolinolato)-4-(phenylphenolinolato)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, spirocarbazoles, 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.

[1627] 20

[1628] Preferred host materials are in particular selected from compounds of the formula (H-100),

[1629] Ar 5 -(Ar 6 ) P -Ar 7 (H-100)

[1630] 25

[1631] 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.

[1632] 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 P25-055.docx

[1633] - 133 -

[1634] and / or Ar 7a fused aryl group selected from 1- or 2-naphthyl, 2-, 3- or 9-phenanthrenyl, or 2-, 3-, 4-, 5-, 6- or 7-benzanthracenyl. Anthracene-based compounds are described in US 2007 / 0092753 A1 and US 2007 / 0252517 A1, e.g. B. 2-(4-methylphenyl)- 5,10-di-(2-naphthyl)anthracene, 9-(2-naphthyl)-10-(1,1'-biphenyl)anthracene and 9,10-bis[4-(2,2-diphenylethenyl)phenyl]anthracene, 9,10-diphenyl-anthracene, 9,10-bis(phenylethynyl)anthracene and 1,4-bis(9'-ethynyl-anthracene)benzene. Compounds with two anthracene units are also preferred (US 2008 / 0193796 A1), e.g., 10,10'-bis[1,1',4',

[1635] 10 1”]terphenyl-2-yl-9,9'-bisanthracenyl.

[1636] Other preferred compounds are derivatives of arylamine, styrylamine, fluorescein, diphenylbutadiene, tetraphenylbutadiene, cyclopentadiene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, and coumarin.

[1637] 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.

[1638] 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 AlQ3 can be used as co-hosts.

[1639] 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.

[1640] 35Foreignfiling text P25-055.docx

[1641] - 134 -

[1642] 5

[1643]

[1644] Formula H-102 Formula H-103

[1645] 10

[1646]

[1647] 15

[1648]

[1649] Formula H-104 Formula H-105

[1650] 20

[1651]

[1652] Formula H-106 Formula H-107

[1653] 25

[1654]

[1655] Formula H-108

[1656] 30 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, 35 aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g.

[1657] according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WOForeignfiling text P25-055.docx

[1658] - 135 -

[1659] 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 derivatives, e.g. according to WO 2007 / 063754 or WO 2008 / 056746, indeno-5 carbazole derivatives, e.g. B. 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 2005 / 111172, azaborols or boron esters, e.g. according to WO 2006 / 117052, 10 triazine derivatives, e.g. B. 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 derivatives, e.g. according to WO 2010 / 054730, bridged carbazole derivatives, e.g.

[1660] 15 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 20 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 as a co-host in the mixture, or a compound that does not participate in charge transport or does not participate to a significant extent, as described for example in WO 25 2010 / 108579.

[1661] 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.

[1662] Furthermore, it can be provided that the electronic device is an organic electroluminescent device and that the electroluminescent device comprises an electron transport layer, wherein the

[1663] 35 Electron transport layer comprising at least one electron transport material and a compound according to formula (1). Preferably the Elek-Foreignfiling text P25-055.docx

[1664] - 136 -

[1665] electron transport layer comprising 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).

[1666] 5. 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 according to formula (1). Preferably, the hole transport layer 10 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).

[1667] The ordinary refractive indices 15 of the layers of an electronic device, preferably an organic electroluminescence 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.

[1668] 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 compounds according to formula (1) or according to the preferred embodiments described above.

[1669] In addition to the layers described above, the electronic device, preferably the organic electroluminescence device, can comprise 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 an electronic device, preferably an organic electroluminescence device.

[1670] - 137 -

[1671] cenz device comprising at least one outcoupling layer, capping layer or covering layer and / or matching layer, which contains at least one connection according to formula (1) or according to the preferred embodiments and preferably consists of one or more of these connections.

[1672] Preferred electroluminescent devices (OLEDs) according to the invention comprise the following layer structure, whereby it is not excluded that further layers are present:

[1673] 10 - Anode

[1674] - Hole injection layer (HIL)

[1675] - Hole transport layer (HTL)

[1676] - Electron blocking layer (EBL)

[1677] - Emission layer (EML) containing a fluorescent or phosphor dopant

[1678] - Hole-blocking layer (HBL)

[1679] - Electron transport layer (ETL)

[1680] - Electron injection layer

[1681] - Cathode.

[1682] 20

[1683] Various embodiments of the invention are summarized in the following table: _

[1684] EML compound of formula (I) or preferred embodiments in

[1685] 25 following shift

[1686] 1 fluorescent HIL

[1687] 2 fluorescent HTL

[1688] 3 fluorescent EBL

[1689] 4 fluorescent HBL

[1690] 30

[1691] 5 fluorescent ETL

[1692] 6 fluorescent HIL + HTL

[1693] 7 fluorescent HIL + EBL

[1694] 8 fluorescent HIL + HBL

[1695] 9 fluorescent HIL + ETL

[1696] 35

[1697] 10 fluorescent HTL + EBL

[1698]

[1699] 11 fluorescent HTL + HBLForeignfiling text P25-055.docx

[1700] - 138 -

[1701] 12 fluoreszent HTL + ETL

[1702] 13 fluoreszent EBL + HBL

[1703] 14 fluoreszent EBL + ETL

[1704] 15 fluoreszent HBL + ETL

[1705] 5

[1706] 16 fluoreszent HIL + HTL + EBL

[1707] 17 fluoreszent HIL + HTL + HBL

[1708] 18 fluoreszent HIL + HTL + ETL

[1709] 19 fluoreszent HIL + EBL + HBL

[1710] 20 fluoreszent HIL + EBL + ETL

[1711] 10

[1712] 21 fluoreszent HIL + HBL + ETL

[1713] 22 fluoreszent HTL + EBL + HBL

[1714] 23 fluoreszent HTL + EBL + ETL

[1715] 24 fluoreszent HTL + HBL + ETL

[1716] 25 fluoreszent EBL + HBL + ETL

[1717] 15

[1718] 26 fluoreszent HIL + HTL + EBL + HBL 27 fluoreszent HIL + HTL + HBL + ETL 28 fluoreszent HTL + EBL + HBL + ETL 29 fluoreszent HIL + HTL + EBL + HBL + ETL 20 30 phosphoreszent HIL

[1719] 31 phosphoreszent HTL

[1720] 32 phosphoreszent EBL

[1721] 33 phosphoreszent HBL

[1722] 34 phosphoreszent ETL

[1723] 25 35 phosphoreszent HIL + HTL

[1724] 36 phosphoreszent HIL + EBL

[1725] 37 phosphoreszent HIL + HBL

[1726] 38 phosphoreszent HIL + ETL

[1727] 39 phosphoreszent HTL + EBL

[1728] 30 40 phosphoreszent HTL + HBL

[1729] 41 phosphoreszent HTL + ETL

[1730] 42 phosphoreszent EBL + HBL

[1731] 43 phosphoreszent EBL + ETL

[1732] 44 phosphoreszent HBL + ETL

[1733] 35 41 phosphoreszent HIL + HTL + EBL

[1734]

[1735] 42 phosphoreszent HIL + HTL + HBLForeignfiling text P25-055.docx

[1736] - 139 -

[1737] 43 phosphoreszent HIL + HTL + ETL

[1738] 44 phosphoreszent HIL + EBL + HBL

[1739] 45 phosphoreszent HIL + EBL + ETL

[1740] 46 phosphoreszent HIL + HBL + ETL

[1741] 5

[1742] 47 phosphoreszent HTL + EBL + HBL

[1743] 48 phosphoreszent HTL + EBL + ETL

[1744] 49 phosphoreszent HTL + HBL + ETL

[1745] 50 phosphoreszent EBL + HBL + ETL

[1746] 51 phosphoreszent HIL + HTL + EBL + HBL

[1747] 10

[1748] 52 phosphoreszent HIL + HTL + HBL + ETL

[1749] 53 phosphoreszent HTL + EBL + HBL + ETL

[1750]

[1751] 54 phosphoreszent HIL + HTL + EBL + HBL + ETL

[1752] A further preferred option is an organic electroluminescence device, 15

[1753] characterized in that one or more layers are coated using a sublimation process. The materials are subjected to this process in vacuum sublimation systems at an initial pressure of less than 10⁻⁶. 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.

[1754] 20

[1755] A preferred organic electroluminescence device is also 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 25

[1756] at a pressure between 10' 5Pressures of mbar and 1 bar are applied. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured.

[1757] 30

[1758] A further preferred organic electroluminescence device is characterized in that one or more layers of solution, 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 35

[1759] Nozzle printing is used to produce these materials. Soluble compounds are required for this process, which can be obtained, for example, through suitable substitution. Foreignfiling text P25-055.docx

[1760] - 140 -

[1761] 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.

[1762] 5

[1763] 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 containing the compounds according to formula (1) or according to the preferred embodiments.

[1764] 10

[1765] 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:

[1766] 15

[1767] 1. Electronic devices, in particular organic electroluminescent devices containing compounds according to formula (1) or according to the preferred embodiments, especially in combination with an emitter, with a matrix material, with a 20-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 according to the invention.

[1768] 25 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.

[1769] 3. The compounds according to formula (1) or according to the preferred embodiments exhibit very high stability.

[1770] 35 4. Layers containing compounds according to formula (1) or according to the preferred embodiments exhibit lower refractive index. Foreignfiling text P25-055.docx

[1771] - 141 -

[1772] indices on layers that do not contain these compounds, resulting in improved light extraction and thus improved efficiency of the electronic device, in particular the organic electroluminescent device, containing these 5 layers.

[1773] 5. Compounds according to formula (1) or according to the preferred embodiments exhibit excellent glass film formation and form very good 10 films both when vapor-deposited and from solution.

[1774] These aforementioned advantages are not accompanied by a significant deterioration of other electronic properties.

[1775] 15 All features of the present invention can be combined with one another in any way, unless certain features and / or steps are mutually exclusive. This applies in particular to preferred features of the present invention. Likewise, features of non-essential combinations can be used separately 20 (and not in combination).

[1776] The invention is further explained by the following examples, without thereby limiting it. The person skilled in the art can implement the invention in its entire disclosed scope from the descriptions 25 and, without inventive effort, produce further connections according to the invention and use them in electronic devices or apply the method according to the invention.

[1777] Examples:

[1778] 30 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-Aldrich or ABCR. The information in square brackets or the numbers given for individual compounds 35 refer to the CAS numbers of the compounds known from the literature.

[1779] For compounds that have several isomers, enantiomers, diastereomers or Foreignfiling text P25-055.docx

[1780] - 142 -

[1781] Since tautomeric forms can be present, one form is shown as a representative example.

[1782] A: Synthons known in literature:

[1783] 5 1) Aryl bromides AB:

[1784] Co Co Br '^ C 5tx o / \< 169695-24-3 1562418-82-9 1562418-80-7 10 AB1 AB2 AB3

[1785] D

[1786] D3 V CD3

[1787] X JCK Br' x ^ / / \ CD 3

[1788] DC CD B r C^r 3 3 / \y F D

[1789] 15 1562418-83-0 1562418-81-8 1562418-85-2

[1790] AB4 AB5 AB6

[1791] OO v 20 XXx ^ JCLA 1562418-94-3 3006054-57-2

[1792] 3006050-34-3 AB7 AB8

[1793] AB9

[1794] 25

[1795] With C< K ^ J Br / ^ sx O > \ ^ CLX Br '^JC 5sx OO > \

[1796] 27452-17-1

[1797] 2835450-70-7 3006050-35-4 AB11

[1798] AB12 30 AB10

[1799] ' UL^< cc XYn BC Br OO 16499-72-2

[1800] 35 1562418-87-4

[1801] 2559731-19-8 AB50

[1802] AB51

[1803]

[1804] AB13Foreignfiling text P25-055.docx

[1805] – 143 –

[1806] 5 1801624-95-2

[1807] AB52 1801624-96-3

[1808] AB53 2649510-09-6 AB54

[1809] 10

[1810] Br ^ " Xy

[1811] Br ^^^ 1801624-97-4

[1812] AB70

[1813] 2413719-28-3 15 2649510-10-9

[1814] AB55 AB71

[1815] — Br Br "^ — /

[1816] 20 B / JOQX> 1935965-17-5 2245-43-4 Br

[1817] AB100 AB101 2413719-30-7

[1818] AB72

[1819] 25

[1820] Br

[1821] 1459-53-6 Br Br 22385-77- 120173-44-6 AB 102 9

[1822] AB103 AB 104 30

[1823] 0 i Xy iQ

[1824] Br Br

[1825] 2910924-12-6 1421058-75-4 Br 35 AB 105 AB 106 57244-77-6

[1826]

[1827] AB 107Foreignfiling text P25-055.docx

[1828] - 144 -

[1829] / Br

[1830] / =: ^ / Br Br / B / O > F 16400-51-4 28396-42-1

[1831] 92160-12-8

[1832] 5 AB 108 AB110

[1833] AB109

[1834] F Br o 0O B / " z vV' Br

[1835] Br^— Br \ r 57186-90-0

[1836] 79990

[1837] 10 2414088-08-5 -92-4 AB112

[1838] AB111 AB113 Br Br Br. Ck^^^Br

[1839] 617 Br OOJ Br 15 201138-91-2 707-33-2

[1840] 2407761-48-0 AB114 AB115

[1841] AB116

[1842] 0-0

[1843] 20 Br^— Jr Br Br 0-0

[1844] Br Br 13974-85-1 28139-76-6

[1845] 2393951-38-5 AB117 AB118

[1846] AB119

[1847] 25

[1848] -0

[1849] Br Br Br Br 0-0

[1850] Br Br 607731-60-2 2393951-63-6

[1851] 2830000-47-6 AB120

[1852] 30 AB121

[1853] AB 122 / == \ QrO

[1854] — Br 0-0 Br^^-^ X _ / 35 Br Br

[1855] 727730-32-7 128406-10-0 1418299-83-8

[1856]

[1857] AB 123 AB124 AB 125Foreignfiling text P25-055.docx

[1858] - 145 -

[1859] 5

[1860] 10

[1861] 15

[1862] 20

[1863] 25

[1864] 30

[1865] 35

[1866]

[1867] Foreignfiling text P25-055.docx

[1868] - 146 -

[1869] 5

[1870] 661464-84-2 AB301 AB302

[1871]

[1872] AB300

[1873] 10

[1874] 2) Monohalocensile MHS, Monohalocene MHG:

[1875] 15

[1876] 76814-99-8 MHS1 MHS3

[1877] 20

[1878] F3C CF3—Si— -Si- 427-32-7

[1879] 1401585-12-3 MHS4 MHS5

[1880] MHS6 25

[1881] 30

[1882] 1401573-63-4

[1883] 1401585-15-6

[1884] MHS8 MHS9

[1885] 35

[1886]

[1887] Foreignfiling text P25-055.docx

[1888] - 147 -

[1889]

[1890] 5

[1891] 10

[1892] 15

[1893] 20

[1894] 25

[1895] 30

[1896]

[1897] 35Foreignfiling text P25-055.docx

[1898] - 148 -

[1899] 5

[1900] 10

[1901]

[1902] 4) Trihaloqensilane THS,

[1903]

[1904] ane THG

[1905] 15 ci— s >i— Cl

[1906] Cl— Si-CI Cl— Si-CI (?l I I Cl Cl 18171 -74-9

[1907] 98-12-4 2407777-16-4 TH S1

[1908] THS2 THS3 20

[1909] Si^

[1910] Cl— Si— Cl Cl— Si-CI Cl— Si -Cl

[1911] I I I

[1912] Cl Cl C

[1913] 18245-29-9 16538-62-8

[1914] 60812-91-1

[1915] 25 THS4 THS6 THS5

[1916] F

[1917] Qi o Qil\ r T II - I1 / F^ y jS ^F ci— s >i— Cl Cl— Si-CI

[1918] 30 I Cl— Si-CI c:i Cl 1 72190-63-7 98-13-5 Cl THS8 20083-38-9 TH S7

[1919]

[1920]

[1921] THS9

[1922] 35Foreignfiling text P25-055.docx

[1923] - 149 -

[1924] Q

[1925] 5 Cl— Si— Cl

[1926] I I ci— s >i— Cl Cl Cl

[1927] c:i 17902-75-9 107742-40-5

[1928] 17886-89-4 THS10 THS11

[1929] THS12 10

[1930] - K Cl i Cl— Si-CI < / y-si-ci T I

[1931] 15 Cl— Si— Cl Cl x= / Cl I

[1932] Cl 841313-84-6 70402-93-6 70402-92-5 THS14 THS15 THS13

[1933] Si

[1934] 20

[1935] Cl— Si-CI

[1936] I ^ Cl— jCci ^ Cl— Si-CI Cl I

[1937] I Cl Cl 18030-62-1

[1938] 1401573-62-3 25 2832113-54-7 THS17

[1939] THS16 THS8

[1940] 30

[1941] Cl— Si-CI

[1942] I

[1943] Cl

[1944] 70402-94-7

[1945]

[1946] THS19

[1947] 35Foreignfiling text P25-055.docx

[1948] - 150 -

[1949] 5

[1950]

[1951] 5) Chlorosilanes containing substituted Alkyl groups ECS:

[1952] 10 ci r , — S Ii— / / \ 2 \ Cl \ Cl

[1953] 15942-84-4 157223-29-5

[1954] 176248-02-5 ECS1 ECS2

[1955] 15 ECS3 _ _ / ~\. Si,c\ \ / Cl tj r MF 4— sV 54 Cl / \

[1956] 473456-63-2 20 153306-40-2

[1957] 90753-10-9 ECS6 ECS4

[1958] ECS5

[1959] ^ / cl ci Cl \ A V-Az^ s A ^V^s / i^ ( / ^\ I ci z c\ c\

[1960] 25 88652-69-1 157223-30-8 1101139-82-7

[1961] ECS7 ECS8 ECS9 ci \ Cl, /

[1962] VPM si / \ CI XX / Cl there X I c / SL / Cl 30 128530-61-0 18293-42-0

[1963] ECS10 473456-53-0 ECS12 ESC11

[1964] then then

[1965] SL

[1966] c z l cK X CI A Ci

[1967] I and C z Cl

[1968] 35

[1969] 6838-86-4 1808105-05-6

[1970]

[1971] ECS13 ECS14Foreignfiling_text P25-055.docx

[1972] - 151 -

[1973] 6) Organolithium compounds containing inventively sized Alkyl groups EL:

[1974] 5

[1975] A, ^-3^^ Lj —

[1976] 7412-67-1 134628-22-1

[1977] 942600-71-7

[1978] EL1 EL3

[1979] EL2

[1980] 10

[1981] \i Li 145576-27-8 857856-46-3 29904-33-4

[1982] EL5 EL6 EL4

[1983] F — — \

[1984] 15 ' - ' The \i

[1985] 857856-50-9 76270-42-3

[1986]

[1987] EL7 EL8

[1988] B) Representation of the synthons S:

[1989] 20 Example S1

[1990] a) S1a:

[1991] 25

[1992]

[1993] 800 ml n-heptane are reacted with 3.3 g (5 mmol) Bis[(1,2,5,6-η)-1,5-cyclo-octadiene]di-μ-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

[1994] (10 mmol) Bis(pinacolato)diborane added and left to stand for 15 min at room temperature 30

[1995] The mixture was stirred. Then, 127.0 g (500 mmol) of bis(pinacolato)diborane and then 113.2 g (500 mmol) of dispiro[cyclopentane-1,1'-[1H]indene-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 mixture was treated with 300 ml of ethyl acetate and filtered through a silica gel bed.

[1996] and completely concentrates the filtrate under vacuum. The raw product becomes Foreignfiling_text P25-055.docx

[1997] - 152 -

[1998] Recrystallized twice from acetone (approx. 800 ml). Yield: 158.8 g (450 mmol), 90%; Purity: approx. 99% according to [method not specified]. 1 H-NMR.

[1999] 5

[2000]

[2001] 10. Procedure analogous to C. Reus et al., J. Org. Chem. 2012, 77, 3518, Verb. 5, 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.

[2002] 15

[2003] 20

[2004] 2

[2005]

[2006] 5

[2007] C: Representation of the compounds according to the invention:

[2008] 30

[2009]

[2010] Preparation according to Journal of Organometallic Chemistry 620 (2001), 287-35, 295, Compound 12. A well stirred mixture of 32.1 g (105 mmol) S1 and 500 ml diethyl ether, cooled to -78 °C, is added dropwise with Foreignfiling_text P25-055.docx

[2011] - 153 -

[2012] 123.5 ml (210 mmol) of tert-butyllithium, 1.7 M, were dissolved in n-hexane. The mixture was stirred for 15 minutes, heated to 10 °C, and then a mixture of 27.7 g (100 mmol) of ECS4 and 300 ml of diethyl ether was slowly added dropwise. After the exothermic reaction subsided, the mixture was heated under reflux for 5 hours.

[2013] 5. After cooling, slowly pour into 1 L of ice-cold 2 N hydrochloric acid while stirring well, stir briefly, separate the organic phase, wash it twice with 300 ml of water each time, once with 300 ml of saturated saline solution, and dry over a mixture of magnesium sulfate and potassium carbonate. Filter off the drying agent through a silica gel bed and concentrate in the

[2014] 10. Vacuum to dryness. Further purification is carried out by repeated hot extraction crystallization (usual organic solvents or combinations thereof, preferably alcohols such as ethanol, isopropanol, sec-butanol, optionally in combination with dichloromethane, ethyl acetate or toluene) or chromatography and fractional sublimation / distillation or...

[2015] 15 annealing cycles under high vacuum. Yield: 37.2 g (79 mmol) 79%; Purity: approx.

[2016] 99.9% after HPLC or high-temperature GC.

[2017] Instead of the aryl bromides, which are first converted into the corresponding organolithium compounds, other compounds known from the literature can be used.

[2018] 20 commercially available organolithium compounds or Grignard compounds are used.

[2019] The following compounds can be represented analogously, possibly with adjustments to the stoichiometry.

[2020] 25 examples: reactants, product

[2021] S2

[2022] B2

[2023] ECS5

[2024] 30

[2025]

[2026] 04^

[2027] 35Foreignfiling_text P25-055.docx

[2028] - 154 -

[2029] S3

[2030] B3

[2031] ECS5

[2032] 5 04^

[2033] AB8

[2034] B4

[2035] 10 ECS1

[2036] O Pix

[2037] AN71

[2038] 15 B5

[2039] ECS2 J LM — w X _' '

[2040] EL8

[2041] B6

[2042] 20 ECS3

[2043] AB13

[2044] B7 t> A ECS6

[2045] 25 7^ 7

[2046] AB54

[2047] B8

[2048] 30 ECS7

[2049]

[2050] 35Foreignfiling_text P25-055.docx

[2051] - 155 -

[2052] AB55

[2053] B9

[2054] ECS8

[2055] 5

[2056] AB72

[2057] B10

[2058] ECS9

[2059] 10

[2060] AB72

[2061] B11

[2062] 15 ECS10

[2063] EL6 / b X 20 B12

[2064] ECS11 ZH y

[2065] 25 AB9

[2066] B13

[2067] ECS3

[2068] 30

[2069] AB7

[2070] B14 (yxo

[2071] ECS5

[2072]

[2073] 35Foreignfiling_text P25-055.docx

[2074] - 156 -

[2075] AB1

[2076] B15

[2077] ECS10 5

[2078] W d

[2079] Q I A A AB2

[2080] B16

[2081] ECS8 LXD '

[2082] 10

[2083] AB3

[2084] 15 B17

[2085] ECS11

[2086] 20

[2087] AB4

[2088] B18

[2089] ECS11

[2090] 25 CD3 CD3

[2091] D3CJJL CD3n p D3C- —

[2092] D3C 3 V CD3 / y X

[2093] AB5 V( D 3 C \ JA B19

[2094] ECS11 D3C A # 1 1 / 30

[2095] “ 7 A

[2096] AB6

[2097] B20 E \ /

[2098] 35 ECS10

[2099] / C F

[2100]

[2101] X / C F Foreignfiling_text P25-055.docx

[2102] - 157 -

[2103] 5

[2104] 10

[2105] 15

[2106] 20

[2107] 25

[2108] 30

[2109] 35

[2110]

[2111] Foreignfiling_text P25-055.docx

[2112] - 158 -

[2113] AB70

[2114] B27

[2115] 5 ECS12

[2116] 10 AB100

[2117] B28

[2118] ECS12 o 0 / ^\

[2119] 15 0

[2120] AB100

[2121] B29 O _ ECS12

[2122] 20

[2123] AB101

[2124] B30

[2125] ECS12

[2126] 25

[2127] 30 AB 102

[2128] B31

[2129] ECS12

[2130] X' X^s^Si / \

[2131]

[2132] x / 35Foreignfiling_text P25-055.docx

[2133] - 159 -

[2134] AB103

[2135] B32

[2136] ECS12

[2137] 5

[2138] Q AB 104 Xi ( jO< 10 B33

[2139] ECS12

[2140] A

[2141] 15

[2142] AB105

[2143] B34 X / ^7^ s '

[2144] ECS7

[2145] 20

[2146] AB 106

[2147] B35

[2148] ECS3

[2149] 25 A

[2150] 0

[2151] AB107

[2152] B36

[2153] 30 ECS12

[2154] 35 AB108

[2155] B37

[2156] ECS3

[2157]

[2158] Foreignfiling_text P25-055.docx

[2159] - 160 -

[2160] AB109

[2161] B38

[2162] ECS3 SorQy- 'Ö -^O A'-O AB110 0

[2163] B39

[2164] ECS3

[2165] B z Q

[2166] K

[2167] The 111

[2168] B40 THERE / T \Z—

[2169] \ ^-Si x | ^ Si , ECS4 J ] Y / ( \ AB112 X o

[2170] B41

[2171] The ECS3

[2172] X \A / O. o / \ AB113 AQ B42

[2173] ECS5

[2174] AB114

[2175] B43

[2176] ECS5 '^ocxS

[2177] AB115

[2178] B44

[2179] ECS3

[2180]

[2181] 35Foreignfiling_text P25-055.docx

[2182] - 161 -

[2183] AB116

[2184] B45

[2185] ECS4 V 0^0 v 5

[2186] XJ AB117

[2187] B46

[2188] ECS3 X U- 10 dl

[2189] AB118

[2190] B47

[2191] ECS3 QC^QO 15

[2192] AB119

[2193] B48

[2194] ECS3 Q0XXP 20

[2195] AB120

[2196] B49

[2197] 25 ECS3 O£> QP

[2198] 30 AB121

[2199] B50

[2200] ECS4

[2201]

[2202] 35Foreignfiling_text P25-055.docx

[2203] - 162 -

[2204] AB122

[2205] B51

[2206] 5 ECS4 j A r A

[2207] 10

[2208] AB123

[2209] B52

[2210] ECS4 / / _ J - /

[2211] 15

[2212] AB124

[2213] B53

[2214] ECS4

[2215] 20

[2216] AB125

[2217] B54

[2218] ECS4

[2219] V ICJ V

[2220] 25

[2221] CGO i AB126

[2222] B55

[2223] ECS4 i (XYiX / u 30

[2224] ll IJ AB127

[2225] B56

[2226] ECS4

[2227] 35

[2228]

[2229] Foreignfiling_text P25-055.docx

[2230] – 163 –

[2231] AB128 000

[2232] B57

[2233] ECS4

[2234] 5 and bXjOOZV U

[2235] 10 AB129 OCX>

[2236] B58

[2237] ECS4 \ Oo^bozV L /

[2238] 15 AB130

[2239] B59

[2240] ECS4 and bojOocV

[2241] 20

[2242] AB131 Or JO

[2243] B60

[2244] ECS4\bxj TxV 25

[2245] AB 132

[2246] B61

[2247] ECS4 STATEMENTS 30

[2248] AB133

[2249] B62

[2250] ECS4

[2251] 35

[2252]

[2253] Foreignfiling_text P25-055.docx

[2254] - 164 -

[2255] AB 134 XX- B63

[2256] ECS4 S A- 7 5

[2257] AB135

[2258] B64

[2259] ECS4

[2260] 10

[2261] AB200

[2262] 15 B65

[2263] ECS4

[2264] 20

[2265] AB201

[2266] B66

[2267] ECS4

[2268] 25

[2269] 30

[2270] AB202

[2271] B67

[2272] ECS4

[2273] 35 x^J Y-__ /

[2274]

[2275] Foreignfiling_text P25-055.docx

[2276] - 165 -

[2277] AB203

[2278] 5 B68

[2279] ECS4

[2280] 10

[2281] AB204

[2282] B69

[2283] ECS4

[2284] 15 i ir UOA \pnco p

[2285] 20

[2286] AB300

[2287] B70

[2288] ECS4 i qxxozV u 25

[2289] AB301

[2290] B71

[2291] 30 ECS4

[2292]

[2293] 35Foreignfiling_text P25-055.docx

[2294] - 166 -

[2295] AB301

[2296] B72

[2297] ECS4

[2298] MHS1

[2299] B73

[2300] EL8

[2301] MHS2

[2302] B74

[2303] EL8

[2304] o

[2305] MHS3

[2306] B75

[2307] EL8

[2308] MHS4

[2309] B76 v> 0^ EL8

[2310] C , F 3 F3C F3C^4 / \ MHS5 > X^CF3B77. Si

[2311] EL8 ^^ CF3

[2312]

[2313] ^\z F3C

[2314] 35 Foreign filing_text P25-055.docx

[2315] - 167 -

[2316] — Si

[2317] MHS6

[2318] B78

[2319] EL8

[2320] 5

[2321] J, 's.-

[2322] MHS7

[2323] 10 B79

[2324] EL6

[2325] Si Si— 1 /

[2326] 15

[2327] MHS8 \z —

[2328] B80

[2329] EL4

[2330] 20

[2331] _

[2332] MHS9

[2333] B81

[2334] EL8

[2335] 25

[2336] MHS10 Qo B82. — si EL8

[2337] 30

[2338] DHS1

[2339] B83

[2340] EL8

[2341]

[2342] 35Foreignfiling_text P25-055.docx

[2343] - 168 -

[2344] / \ \ F

[2345] DHS2

[2346] B84

[2347] EL8

[2348] DHS3

[2349] B85

[2350] EL2

[2351] CPO

[2352] DHS3

[2353] B86

[2354] EL8

[2355] / s;i —Si— —Si— DHS5

[2356] B87

[2357] EL8

[2358] ) <x

[2359] DHS6

[2360] B88

[2361] EL8

[2362] So>

[2363] OV DHS7

[2364] B89 Si / — j.

[2365] EL8

[2366] x-ö ^y?

[2367]

[2368] 35Foreignfiling_text P25-055.docx

[2369] - 169 -

[2370] DHS8

[2371] B90

[2372] EL8

[2373] 5

[2374] DHG1

[2375] B91

[2376] EL8

[2377] 10

[2378] DHG2

[2379] B82 / Ge J EL8

[2380] 15

[2381] I \

[2382] DHG3

[2383] B93 | Ge T EL7

[2384] 20

[2385] THS1

[2386] B94 EL8

[2387] 25

[2388] THS2

[2389] B95 EL3

[2390] 30

[2391] A >

[2392] THS3

[2393] B96

[2394] 35 EL8

[2395]

[2396] Foreignfiling_text P25-055.docx

[2397] - 170 -

[2398] THS4

[2399] B97

[2400] EL8

[2401] THS5

[2402] B98

[2403] EL8

[2404] THS6

[2405] B99

[2406] EL6

[2407] THS7

[2408] B100

[2409] EL3

[2410] I S THS8

[2411] B101

[2412] EL8

[2413] F F

[2414] F — 4 y { jy? THS9

[2415] B102

[2416] EL8

[2417]

[2418] 35Foreignfiling text P25-055.docx

[2419] - 171 -

[2420] THS10

[2421] B103

[2422] EL8

[2423] 5

[2424] THS11

[2425] 10 B104

[2426] EL8

[2427] 15

[2428] THS12

[2429] B105

[2430] EL8 / —

[2431] 20

[2432] THS13

[2433] B106

[2434] EL8

[2435] 25

[2436] THS14

[2437] B107

[2438] EL8

[2439] 30

[2440] THS15

[2441] B108

[2442] EL8

[2443] 35

[2444]

[2445] Foreignfiling text P25-055.docx

[2446] - 172 -

[2447] THS16

[2448] B109

[2449] EL8

[2450] 5 O

[2451] THS17

[2452] 10 B110

[2453] EL4 •

[2454] 0^0 15

[2455] THS18

[2456] B111

[2457] EL8

[2458] 20

[2459] THS19

[2460] B112

[2461] EL1 \ / — Si — ' 25 T y.

[2462] THG1

[2463] B113

[2464] EL8 ^0^ 30

[2465] THG2

[2466] B114 Q<» 35 EL8

[2467]

[2468] Foreign filing text P25-055.docx

[2469] - 173 -

[2470] 5

[2471]

[2472] D: Production of mixtures: PreMix

[2473] 10 Example: PreMixl

[2474] A mixture of 7.5 g HTM [136463-07-5], vacuum temperature TGA (5 wt% loss): 211 °C, see Table 4, and 2.5 g B45, vacuum temperature TGA (5 wt% loss): 209 °C, is carefully melted in a Schlenk tube under argon without overheating the melt. After homogenizing the melt, this

[2475] 15. The organic glass obtained in this way is cooled and pulverized; in this form it is used as PreMixl for the production of OLED components, see example E2b.

[2476] E: Device examples for blue fluorescent OLEDs

[2477] 20 In the following three examples, OLEDs according to the invention (examples bE1a to bE1e, bE2a to bE2e and bE3a) and one OLED according to the prior art (comparative examples bC1, bC2 and bC3) are produced. The exact structure of the OLEDs can be found in Tables 1, 2 and 3. The materials used to produce the OLEDs are shown in Table 4. 25 The properties of the OLEDs according to the invention of examples bE1a to bE1e, bE2a to bE2e and bE3a and the properties of the OLEDs according to the prior art are listed in Tables 5, 6 and 7.

[2478] Manufacturing of blue OLEDs

[2479] 30. Glass platelets coated with structured ITO (indium tin oxide) with a thickness of 50 nm are used as substrates 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 35 (doped, emitter), which is added to the matrix material(s) by cover vapor deposition in a specific volume fraction. [Foreignfiling text P25-055.docx]

[2480] - 174 -

[2481] The specification 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 is present in a volume fraction of 3% in a 20 nm thick layer. Similarly, the hole injection layer (HIL), the hole transport layer 5 (HTL), and / or 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.

[2482] Table 1: Structure of blue OLEDs

[2483] 10 HIL HTL EBL EML HBL ETL EIL Example 1

[2484] Thickness Thickness Thickness Thickness Thickness Thickness HTM1: PD BH: BD ETM1: LiQ HTM1 EBM HBM LiQ bC1 (95:5) (97:3) (50:50)

[2485] 175nm 5nm 5nm 2nm 10nm 20nm 33nm HTM1: PD BH: BD ETM1:B31

[2486] 15 HTM1 EBM HBM LiQ bE1a (95:5) (97:3) (50:50)

[2487] 175 nm 5 nm 5 nm 2 nm 10 nm 20 nm 33 nm HTM1: PD BH: BD ETM1: B31: LiQ HTM1 EBM HBM LiQ bE1b (95:5) (97:3) (50:30:20)

[2488] 175 nm 5 nm 5 nm 2 nm 10 nm 20 nm 33 nm HTM1: PD BH: BD ETM2: B2

[2489] HTM1 EBM HBM LiQ 20 bE1c (95:5) (97:3) (50:50)

[2490] 175 nm 5 nm 5 nm 2 nm 10 nm 20 nm 33 nm HTM1: PD BH: BD ETM3: B27

[2491] HTM1 EBM HBM LiQ bE1d (95:5) (97:3) (45:55)

[2492] 175 nm 5 nm 5 nm 2 nm 10 nm 20 nm 33 nm HTM1: PD BH: BD ETM4: B114

[2493] HTM1 EBM HBM LiQ 25 bE1e (95:5) (97:3) (45:55)

[2494] 175 nm 5 nm 5 nm 2 nm

[2495]

[2496] 10 nm 20 nm 33 nm

[2497] Tabelle 2: Aufbau der blue OLEDs

[2498] HIL HTL EBL EML HBL ETL EIL

[2499] Example 2

[2500] Dicke Dicke Dicke Dicke Dicke Dicke Dicke 30 HTM1: PD BH: BD ETM1: LiQ HTM1 EBM HBM LiQ C2 (95:5) (97:3) (50:50)

[2501] 180 nm 5 nm 5 nm 2 nm 10 nm 20 nm 30 nm HTM1: PD HTM1:B31BH: BD ETM1: LiQEBM HBM LiQ bE2a (95:5) (70:30) (97:3) (50:50)

[2502] 5 nm 5 nm 2 nm 10 nm 180 nm 20 nm 30 nm

[2503] 35 HTM1: PD BH: BD ETM1: LiQ PreMixI EBM HBM LiQ bE2b (95:5) (97:3) (50:50)

[2504] 180 nm 5 nm 5 nm 2 nm

[2505]

[2506] 10 nm 20 nm 30 nmForeignfiling text P25-055.docx

[2507] - 175 -

[2508] HTM1: PD HTM1:B98 BH: BD ETM1: LiQ EBM HBM LiQ bE2c (95:5) (80:20) (97:3) (50:50)

[2509] 5 nm 5 nm 2 nm 10 nm 180 nm 20 nm 30 nm HTM1: PD HTM2: B11 BH: BD ETM1: LiQ EBM HBM LiQ bE2d (95:5) (75:25) (97:3) (50:50)

[2510] 5 nm 5 nm 2 nm 5 10 nm 180 nm 20 nm 30 nm HTM1: PD HTM3: B25 BH: BD ETM1: LiQ EBM HBM LiQ bE2e (95:5) (85:15) (97:3) (50:50)

[2511] 5 nm 5 nm 2 nm

[2512]

[2513] 10 nm 180 nm 20 nm 30 nm

[2514] Table 3: Structure of blue OLEDs

[2515] 10 HIL HTL EBL EML HBL ETL EIL Example 3

[2516] Thickness Thickness Thickness Thickness Thickness Thickness HTM1: PD BH: BD ETM1: LiQ HTM1 EBM HBM LiQ bC3 (95:5) (97%: 3%) (50:50)

[2517] 183nm 5nm 5nm 2nm 10nm 20nm 34nm HTM1: PD HTMTB31 BH: BD ETM1:B31

[2518] EBM HBM LiQ 15 bE3a (95:5) (70:30) (97%: 3%) (50:50)

[2519] 5 nm 5 nm 2 nm

[2520]

[2521] 10 nm 183 nm 20 nm 34 nm

[2522] Table 4: OLED materials

[2523] 20

[2524] 25

[2525] 30

[2526]

[2527] 35Foreignfiling text P25-055.docx

[2528] - 176 -

[2529] 5

[2530] LJ EBM LiQ [25387-93-3]

[2531] 10 CuO

[2532] CCCOOo

[2533] o

[2534] BH [1087346-88-0] BD [1182175-27-4] $

[2535] 15 _1 11 Oh

[2536] v UO z

[2537] J ( Oh

[2538] rvfYv N= <

[2539] Yes

[2540] 20 O et al <rP0 rn\

[2541] Q HBM [1955543-57-3] ETM1 [1233200-52-6] o

[2542] 25 N=<.? 2.

[2543] oo-'^ -oo QUQ ETM2 [2173328-31-7] ETM3

[2544] 30 Q

[2545] ^ the J >

[2546] yes 7

[2547] rvxY Oh

[2548] fYA / A jT

[2549] < / \ z°^<

[2550] 35 CFO

[2551]

[2552] ETM435

[2553] 30

[2554] 25 20 15 10 5

[2555]

[2556] - ZZk - Foreignfiling text P25-055.docxForeignfiling text P25-055.docx

[2557] - 178 -

[2558] 5

[2559]

[2560] Characterization of blue OLEDs

[2561] 10. The OLEDs are characterized according to standard procedures. For this purpose, the electroluminescence spectra and current-voltage-luminance characteristics (IUL characteristics) are measured, and the EQE 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 determined and from this the CIE 1931 x and y color coordinates calculated.

[2562] The voltage required for a current density of 10 mA / cm² 2The required value is denoted here as U10. EQE10 denotes the external quantum efficiency 20 at a current density of 10 mA / cm². 2 .

[2563] For each example, the relative EQE and the relative voltage are calculated in comparison to the respective reference example:

[2564] rel. U (Ex) = (U10(Ex) / U10(V))

[2565] 25 rel. E

[2566]

[2567] QE (Ex) = (EQE10(Ex) / EQE10(V))

[2568] 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.

[2569] The samples for determining the refractive index (RI) are produced on SiO2 substrates with three different layer thicknesses. The respective material is thermally vapor-deposited. From these 35 measurements, the mean refractive index value for each material is calculated.

[2570] Material mixture determined. Foreignfiling text P25-055.docx

[2571] - 179 -

[2572] The results are shown in Tables 5, 6 and 7 below.

[2573] Properties of blue OLEDs

[2574] 5

[2575] Table 5: Properties of blue OLEDs

[2576] relative relative CIE x / y at RI ETL* Example 1

[2577] U10 (%) EQE10 (%) 1000 cd / m 2 @ 620 nm bC1 1.00 1.00 0.14 / 0.13 1.71 10

[2578] bE1a 1.02 1.08 0.14 / 0.14 1.63 bE1b 1.01 1.06 0.14 / 0.14 1.65 bE1c 1.02 1.05 0.14 / 0.13 1.65 bE1d 1.01 1.07 0.14 / 0.13 1.64 15 bE1e 1.02 1.08 0.14 / 0.13 1.63

[2579]

[2580] (* of the complete ETL layer of the OLED)

[2581] Table 6: Properties of blue OLEDs

[2582] relative relative CIE x / y at RI HTL* 20 Example 2

[2583] U10 (%) EQE10 (%) 1000 cd / m 2 @ 620 nm bC2 1.00 1.00 0.14 / 0.14 1.73 bE2a 1.02 1.09 0.14 / 0.13 1.67 bE2b 1.01 1.05 0.14 / 0.13 1.69 25 bE2c 1.02 1.10 0.14 / 0.13 1.67 bE2d 1.01 1.06 0.14 / 0.13 1.69 bE2e 1.01 1.07 0.14 / 0.13 1.68

[2584]

[2585] (* of the complete HTL layer of the OLED)

[2586] 30 Table 7: Properties of blue OLEDs

[2587] relative relative

[2588] CIE x / y at RI HTL* RI ETL* Example 3 U10 EQE10

[2589] 1000 cd / m 2 @ 620 nm @ 620 nm (%) (%)

[2590] bC3 1.00 1.00 0.13 / 0.14 1.73 1.71 35 bE3a 1.03 1.11 0.14 / 0.14 1.67 1.63

[2591]

[2592] (* of the complete layer of the OLED – ETL or HTL) Foreignfiling text P25-055.docx

[2593] - 180 -

[2594] When comparing the inventive examples E1a-E1e, E2a-E2e, and E3a with the corresponding comparative examples C1, C2, and C3, it is clearly evident that the inventive OLEDs exhibit a significant advantage in device efficiency, without negatively affecting lifetime, voltage, or color. This can be attributed to the lower refractive index of 1.54 for the inventive material B13, 1.56 for the inventive material B45, and 1.52 for the inventive material B98, with the other 10 inventive materials exhibiting comparably low refractive indices. In comparison, LiQ in comparative examples C1 and C3 has a refractive index of 1.65, and HTM1 in comparative examples C2 and C3 has a refractive index of 1.73.

[2595] 15 F: Device examples for green phosphorescent OLEDs

[2596] In the following three examples, OLEDs according to the invention (examples gE1a-c, gE2a-b, gE3a and gE4a-gE4c) and one OLED according to the prior art (comparative examples gCV1, gC2, gC3 and gC4) are produced. The exact structure of the OLEDs is shown in Table 8.

[2597] See Figure 20. Table 9 shows the materials used to manufacture the OLEDs, in addition to those already shown. The properties of the OLEDs according to the invention, as well as the examples and comparative examples, are summarized in Table 10.

[2598] 25 Production of green OLEDs

[2599] 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 8%. Similarly, for example, the hole injection foreign filing text P25-055.docx

[2600] - 181 -

[2601] layer (H IL), the hole transport layer (HTL), the electron blocking layer (EBL), the hole blocking layer (HBL) and / or the electron transport layer (ETL) made from a mixture of two or more materials

[2602] The structure of the respective OLEDs is shown in Table 8, and materials 5 for green OLEDs are shown in Table 9. After the electron injection layer (EIL) is deposited, a 100 nm thick aluminum cathode is deposited onto each component.

[2603] Table 8: Structure of green OLEDs

[2604] 10

[2605] HIL HTL EBL EML HBL ETL EIL

[2606] Example.

[2607] Thickness Thickness Thickness Thickness Thickness Thickness HTM6: PD GH1: GH2: GE ETM4: LiQ HTM6 HTM6 HBM LiQ gci (95:5) (32:60:8) (50:50)

[2608] 50nm 30nm 5nm 3nm 10nm 35nm 30nm

[2609] 15 HTM6: PD HTM6: B31 GH1: GH2: GE ETM4: LiQ HTM6 HBM LiQ gE1a (95:5) (70:30) (32:60:8) (50:50)

[2610] 30 nm 5 nm 3 nm 10 nm 50 nm 35 nm 30 nm HTM6: PD HTM6: B31 GH1: GH2: GE ETM4: LiQ HTM6 HBM LiQ gEi b (95:5) (70:30) (32:60:8) (50:50)

[2611] 50 nm 5 nm 3 nm 10 nm 30 nm 35 nm 30 nm HTM6: PD HTM6: B31 HTM6: B31 GH1: GH2: GE ETM4: LiQ

[2612] 20 HBM LiQ gElc (95:5) 10 (70:30) (70:30) (32:60:8) (50:50)

[2613] 5 nm 3 nm nm 50 nm 30 nm 35 nm 30 nm HTM6: PD GH1: GH2: GE ETM2: LiQ HTM6 HTM 5 HBM LiQ gC2 (95:5) (32:60:8) (50:50)

[2614] 50 nm 30 nm 5 nm 3 nm 10 nm 35 nm 32 nm HTM6: PD GH1: GH2: GE ETM2: B52: LiQ HTM6 HTM 5 HBM LiQ 25 gE2a (95:5) (32:60:8) (50:45:5)

[2615] 50 nm 30 nm 5 nm 3 nm 10 nm 35 nm 32 nm HTM6: PD HTM5: B52 GH1: GH2: GE ETM2: B52: LiQ HTM6 HBM LiQ gE2b (95:5) (80:20) (32:60:8) (50:45:5)

[2616] 50 nm 5 nm 3 nm 10 nm 30 nm 35 nm 32 nm HTM6: PD GH1: GH2: GE ETM3: LiQ HTM6 HTM 5 HBM LiQ 30 gC3 (95:5) (32:60:8) (50:50)

[2617] 50 nm 30 nm 5 nm 3 nm 10 nm 35 nm 32 nm HTM6: PD GH1: GH2: GE ETM3: B56

[2618] HTM6 HTM 5 HBM LiQ gE3a (95:5) (32:60:8) (50:50)

[2619] 50 nm 30 nm 5 nm 3 nm 10 nm 35 nm 32 nm HTM2: PD GH1: GH2: GE ETM5: LiQ HTM2 HTM4 HBM LiQ gC4 (95:5) (32:60:8) (50:50)

[2620] 35 50 nm 30 nm 7 nm 3 nm

[2621]

[2622] 10 nm 35 nm 25 nmForeignfiling text P25-055.docx

[2623] - 182 -

[2624] HTM2: PD HTM2: B45 GH1: GH2: GE ETM5: LiQ HTM4 HBM LiQ gE4a (95:5) (80:20) (32:60:8) (50:50)

[2625] o 30 nm 7 nm 3 nm 10 nm 50 nm 35 nm xP 25 ° n HTM2: PD HTM2: B om

[2626] 70 GH1: GH2: GE ETM6: LiQ HTM4 HBM LiQ gE4b (95:5) (80:20) (32:60:8) (50:50)

[2627] 30 nm 7 nm 3 nm 5 10 nm 50 nm 35 nm 25 n HTM2: PD HTM XH m XO Ty]] 2: B89 GH1: GH2: GE ETM5: LiQ HTM4 nÜ C HBM LiQ gE4c (95:5) (70:30) (3 (50:50)

[2628]

[2629] O \ 2:60

[2630] 30 m / ]:8)

[2631] n 7 nm 3 nm 10 nm 5 u0 nm 3 C5rÖ nm 25 nm

[2632] Table 9: OLED materials - green OLEDs (in addition to the

[2633] 10

[2634] Materials blue OLEDs in Tables 4) _

[2635] THEIR

[2636] 15

[2637] J k

[2638] CrÖ HTM4 HTM5

[2639] 20

[2640] 25 HTM6 GH1

[2641] D. D

[2642] NA 1 °

[2643] oX 1

[2644] 30 \ / D

[2645] / =\ D Cr 7

[2646] w kJ

[2647] D

[2648] 35

[2649]

[2650] GH2 GEForeignfiling text P25-055.docx

[2651] - 183 -

[2652] 5

[2653]

[2654] Characterization of green OLEDs

[2655] 10

[2656] 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.

[2657] Table 10: Properties of OLEDs

[2658] 15

[2659] relative relative CIE x / y at

[2660] Example

[2661] U10 EQE10 1000 cd / m 2

[2662] gC1 1.00 1.00 0.34 / 0.64

[2663] gE1a 1.01 1.03 0.34 / 0.64

[2664] 20 gE1b 1.02 1.04 0.34 / 0.64

[2665] gElc 1.02 1.08 0.34 / 0.64

[2666] gC2 1.00 1.00 0.36 / 0.61

[2667] gE2a 1.01 1.03 0.36 / 0.61

[2668] gE2b 1.02 1.07 0.35 / 0.62

[2669] 25

[2670] gC3 1.00 1.00 0.37 / 0.61

[2671] gE3a 1.01 1.06 0.37 / 0.63

[2672] gC4 1.00 1.00 0.36 / 0.62

[2673] gE4a 1.01 1.06 0.36 / 0.62

[2674] 30

[2675] gE4b 1.03 1.07 0.36 / 0.62

[2676] gE4c 1.02 1.06 0.36 / 0.62

[2677]

[2678] When comparing the inventive examples gE1a-c, gE2a-b, gE3a 35 and gE4a-c with the corresponding comparative examples gC1, gC2, gC3 and gC4, it is evident that the inventive OLEDs have a Foreignfiling text P25-055.docx

[2679] - 184 -

[2680] demonstrate a significant advantage in device efficiency, without negatively affecting lifespan, voltage, and color.

[2681] 5

[2682] 10

[2683] 15

[2684] 20

[2685] 25

[2686] 30

[2687] 35

Claims

Foreign filing text P25-055.docx - 185 - Patent claims 1. Compound according to formula (1 ), 5 Formula 1) 10 where the compound may also be partially or completely deuterated, and the following applies to the symbols and indices used: M is the same or different Si or Ge in each occurrence; 15 R 1 In each occurrence, the alkyl group is either 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 partially or completely deuterated and / or has one or more fluorine atoms and / or Si(R) groups. 7 )3 may be substituted, or 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 R3 can be substituted, where 25 can be a maximum of two groups R 1 stand for an aromatic ring system; This can involve two or three substituents R 1 also form a ring with each other; R 2 In each occurrence, the alkyl group is either a straight-chain 30 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 partially or completely deuterated and / or with one or more fluorine atoms and / or Si(R) groups. 7 )3 can be substituted, an aromatic ring system with 6 to 30 35 aromatic ring atoms, which can also be partially or completely deuterated and / or which can also be modified by one or more substituents R 4 may be substituted, a Dibenzo-Foreignfiling text P25-055.docx - 186 - furan group, which may also be partially or completely deuterated and / or which may also be modified by one or more substituents R 4 may be substituted, or an aralkyl group with 6 to 30 aromatic ring atoms, which may also be partially or fully deuterated and / or which may also be modified by one or more substituents R 4 It can be substituted; this can involve two or three substituents R 2 , which bind to the same Si or Ge atom, also form a ring together; 10 L stands for -[Ar]0-[Alk] p -[Ar] q -; Ar is, in each occurrence, 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. 5may be substituted, or 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; 20 Alk is an alkylene group with 1 to 20 carbon atoms, which may also be partially or completely deuterated and / or which may also be modified by one or more substituents R 6 may be substituted; R 3 , R 4 , R 5 , R 6 is the same or different at each occurrence F, CN, 25 Si(R 7)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 and / or substituted with one or more fluorine atoms, 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 Si(R) groups 7 )3 and / or alkyl groups with 1 to 10 carbon atoms, wherein two or more of these alkyl groups may also form a ring together, or an aralkyl group with 6 to 24 aromatic ring atoms, which may also be partially or completely deuterated and / or which may also be substituted with a or Foreignfiling text P25-055.docx - 187 - several groups Si(R 7)s and / or alkyl groups with 1 to 10 carbon atoms, whereby two or more of these alkyl groups can also form a ring together; in this case, two or more R groups can be substituted 3 , two or more residues R 4 , 5 two or more residues R 5 and / or two or more residues R 6 also form a mono-, oligo- or polycyclic ring with each other; R 7In 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 30 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, wherein two or more of these alkyl groups may also form a ring together; in this case, two or more substituents R may also be 7 together form a mono-, oligo- or polycyclic ring; n, o, p, q is either the same or different from 0 or 1 in each occurrence, with the proviso that o + p + q ≥ 1; 25, provided that the compound has a molecular weight of at least 500 g / mol; and further provided that the following compound is excluded from the invention: 30 Foreign filing text P25-055.docx - 188 - 2. Compound according to claim 1, characterized in that R 1 The alkyl group is selected in the same or different ways for each occurrence from 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 with one or more Si(R) groups. 7 )s may be substituted, 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 3 can be substituted 10, where at most two groups R1 represent an aromatic ring system; this can involve two or three substituents R 1 also form a ring together.

3. Compound according to claim 1 or 2, characterized in that the 15 Group of the following formula, which is bound to M, 20 where dashed line represents the bond to M, selected from the groups of formulas (a) to (f), where the groups may also be partially or completely deuterated, 25 30 35 4. Compound according to one or more of claims 1 to 3, characterized in that R 2 same or different in each occurrence. Foreignfiling text P25-055.docx - 189 - 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 with one or more Si(R) groups 7 )s can be substituted, an aromatic ring system with 6 to 24 aromatic ring atoms, which can also be partially or completely deuterated and / or which can also be modified by one or more substituents R 4 may 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 4 may be substituted, or an aralkyl group 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 4 It can be substituted; this can involve two or three substituents R 2, which bond to the same Si or Ge atom at 15, also form a ring together.

5. Compound according to one or more of claims 1 to 4, characterized in that the following applies to L: 20 L stands for — [Ar]0-[Alk] p -[Ar] q -; Ar is the same or different at each occurrence, selected from an aromatic ring system with 6 to 18 aromatic rings.25 atoms, 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 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 30 may be substituted; Alk is selected from a linear alkylene group with 1 to 10 C atoms or a branched or cyclic alkylene group with 3 to 10 C atoms, wherein the alkylene group is also partially 35 or may be completely deuterated and / or may be modified by one or more substituents R 6 may be substituted; Foreignfiling text P25-055.docx - 190 - The following applies to the indices o, p and q: o = 1, p = 0 and q = 0; or o = 0, p = 1 and q = 0; or 5 o = 1, p = 1 and q = 1.

6. Compound according to one or more of claims 1 to 5, wherein: M is Si; 10 R 1 In 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 is in each case partially or completely deuterated and / or with one or more groups S i(R) 7)s may be substituted, or 15 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 3 can be substituted, with a maximum of two groups R 1 for an aromatic ring system; this can involve two or three 20 substituents R 1 also form a ring with each other; R 2 In each occurrence, the alkyl group is either the same or different: 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 with one or more Si(R) groups. 7)3 can be substituted, an aromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, which can also be partially or completely deuterated and / or which can also be modified by one or more substituents R 4 30 may be substituted, a dibenzofuran group, which may also be partially or completely deuterated and / or which may also be replaced by one or more substituents R 4 may be substituted, or an aralkyl group with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, which may also be partially or completely deuterated and / or which may also be modified by one or more substituents R 4 may be substituted; in this case, Foreignfiling text P25-055.docx - 191 - two or three substituents R 2 , which bind to the same Si atom, also form a ring together; Ar is, in each occurrence, 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 modified by one or more substituents R. 5 may be substituted, or 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; 10 Alk is a linear alkylene group with 1 to 10 carbon atoms or a branched or cyclic alkylene group with 3 to 10 carbon atoms, wherein the alkylene group may also be partially or completely deuterated and / or modified by one or more substituents R 6 may be substituted; 15 for o, p and q: - o = 1, p = 0 and q = 0; or - o = 0, p = 1 and q = 0; or - o = 1, p = 1 and q = 1; R 3is the same or different at each occurrence Si(R 7 )3, 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; in each case, two or more R groups may be 3 also form a mono-, oligo- or polycyclic ring with each other; 25 R 4 is the same or different at each occurrence Si(R 7 )3, 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 fully deuterated; in each case, two or more R groups may be 4 also form a mono-, oligo- or polycyclic ring with each other; R 5 is the same or different at each occurrence Si(R 7)3, 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; in each case, two or more R groups may be present 5 also form a mono-, oligo- or polycyclic ring with each other; Foreignfiling text P25-055.docx - 192 - R 6 is the same or different at each occurrence Si(R 7 )3 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 equipped with one or more Si(R) groups 7 )3 and / or may be substituted with one or more alkyl groups with 1 to 10 carbon atoms, wherein two or more of these alkyl groups may also form a ring together; R 7In 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, 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 substituted with one or more alkyl groups with 1 to 10 carbon atoms, wherein two or more of these alkyl groups may also form a ring together; in this case, two or more R groups may be present. 7 , which bind to the same Si atom, also form a mono-, oligo- or polycyclic ring with each other; 20, provided that R 1 to R 7 and Ar do not contain a fused aryl group.

7. Compound according to one or more of claims 1 to 6, wherein: 25 M is Si; R1 is the same or different in each occurrence: methyl or ethyl, or a group R 1 stands for methyl and the other two groups R 1 together they form a cyclopentane or cyclohexane ring, or the three groups together form a 30 Adamantyl group; R 2 is the same or different in each occurrence methyl, ethyl, n-propyl, n-butyl, iso-propyl, iso-butyl, sec-butyl, tert-butyl, tert-pentyl, neo-pentyl, cyclopentyl, cyclohexyl, bicyclo[2.2.2]octanyl or adamantanyl, wherein the alkyl group is in each case partially or completely deuterated and / or with one or more Si(R) groups 7 )3 may be substituted, or a phenyl group, which may also be Foreignfiling text P25-055.docx - 193 - may be partially or completely deuterated and / or may be modified by one or more substituents R 4 It can be substituted; this can involve two or three substituents R 2, which bind to the same Si atom, also form a ring together; 5Ar is a phenyl 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; Alk is a methylene group or a cyclic alkylene group with 6 to 10 carbon atoms, in particular groups derived from cyclo10 hexane, bicyclo[2.2.2]octane or adamantane, wherein the alkylene group may also be partially or completely deuterated and / or modified by one or more substituents R 6 may be substituted; The following applies to the indices o, p and q: 15 - o = 1, p = 0 and q = 0; or - o = 0, p = 1 and q = 0; or - o = 1, p = 1 and q = 1; R 3 is the same or different at each occurrence Si(R 7)3, Methyl, Ethyl, n-Propyl, n-Butyl, iso-Propyl, iso-Butyl, sec-Butyl, tert-Butyl, Cyclopentyl or Cyclohexyl, wherein the alkyl group may be partially or completely deuterated; wherein two or more R groups may be 3 also form a mono-, oligo- or polycyclic ring with each other; R 4 is the same or different at each occurrence Si(R 7 )3, methyl, ethyl, n-propyl, n-butyl, iso-propyl, iso-butyl, sec-butyl, tert-butyl, Cyclopentyl or cyclohexyl, wherein the alkyl group may be partially or completely deuterated; two or more R groups may be present. 4 also form a mono-, oligo- or polycyclic ring with each other; 30 R 5 is the same or different at each occurrence Si(R 7)3, Methyl, Ethyl, n-Propyl, n-Butyl, iso-Propyl, iso-Butyl, sec-Butyl, tert-Butyl, Cyclopentyl or Cyclohexyl, wherein the alkyl group may be partially or completely deuterated; wherein two or more R groups may be 5 also form a mono-, oligo- or polycyclic ring with each other; Foreignfiling text P25-055.docx - 194 - R 6 is the same or different at each occurrence Si(R 7 )3 or a phenyl group, which may also be partially or completely deuterated and / or which may also be joined with one or more Si(R) groups 7 )3 and / or may be substituted with one or more alkyl groups with 1, 2, 3, 4 or 5 carbon atoms, wherein two or more of these alkyl groups may also form a ring together; R 7is the same or different in each occurrence: methyl, ethyl, n-propyl, n-butyl, iso-propyl, iso-butyl, sec-butyl, tert-butyl, tert-pentyl, neo-pentyl, cyclopentyl, cyclohexyl, bicyclo[2.2.2]octanyl or adamantanyl, wherein the alkyl group 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 with one or more alkyl groups having 1, 2, 3, 4, 15 or 5 carbon atoms, wherein two or more of these alkyl groups may also form a ring with each other; in this case, two or three substituents R 7 , which bind to the same Si atom, also form a ring together. 20 8. Compound according to one or more of claims 1 to 7, characterized in that the compound has a molecular weight of 500 to 2000 g / mol, preferably of 800 to 1500 g / mol.

9. A process for producing a compound according to one or more of claims 1 to 8, wherein first an aryl halide or alkyl halide is reacted to form an aryl or alkyl metal compound and the aryl or alkyl metal compound is then reacted with a halogenated silicon compound or a halogenated germanium compound by salt metathesis. 30 10. Connection according to formula (1 '), 35Foreignfiling text P25-055.docx - 195 - R 1 5 Formula (1') 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 7 10 contains at least one networkable group.

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

13. Use of a compound according to one or more of the 25 Claims 1 to 8, of 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 8, at least one oligomer, polymer or dendrimer according to claim 11 and / or at least one mixture according to claim 12. 35Foreignfiling text P25-055.docx - 196 - 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 8, 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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