Silicon compounds for organic electroluminescent devices

Abstract

The invention relates to organic light-emitting materials, in particular silicon compounds and germanium compounds having aromatic substituents, which are suitable for use in electronic devices; and also to electronic devices, in particular organic electroluminescent devices containing these OLED materials.

Description

[0001] Silicon compounds for organic electroluminescence devices

[0002] The present invention relates to organic light-emitting materials, in particular silicon compounds with aromatic substituents, for use in electronic devices, in particular in organic electroluminescent devices, and to electronic devices, in particular organic electroluminescent devices, containing these OLED materials.

[0003] Electroluminescent devices often comprise additional layers besides an emission layer, such as one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, and / or charge generation layers. These layers have a significant influence on the performance of electroluminescent devices.

[0004] In general, there is still room for improvement in the materials used, especially with regard to efficiency, but also with regard to the lifespan of the device.

[0005] The object of the present invention is therefore to provide compounds which are suitable for use in an organic electronic device, in particular in an organic electroluminescence device, and which lead to good device properties when used in this device, as well as to provide the corresponding electronic device.

[0006] In particular, the object of the present invention is to provide compounds that lead to good efficiency and a long lifetime. Besides the emitters, hole transport materials, hole injection materials, electron blocking materials, electron injection materials, electron transport materials, and hole blocking materials contribute to these properties. Furthermore, the properties of the matrix materials, also referred to herein as host materials, have a significant influence on the lifetime and efficiency of the organic electroluminescence device.

[0007] Furthermore, it is an object of the present invention to provide compounds which are characterized by a low refractive index (RI).

[0008] Another task can be seen as providing electronic devices with excellent performance as cost-effectively as possible and in consistent quality.

[0009] Furthermore, the electronic devices should be usable or adaptable for many purposes. In particular, the performance of the electronic devices should be maintained over a wide temperature range.

[0010] Surprisingly, it was found that certain compounds, described in more detail below, solve this problem, are well suited for use in electroluminescent devices, and lead to organic electroluminescent devices that exhibit very good properties, particularly with regard to lifetime, color purity, efficiency, and refractive index. These compounds, as well as electronic devices, especially organic electroluminescent devices containing such compounds, are therefore the subject of the present invention.

[0011] The present invention relates to a compound according to formula (I), formula (I) where the following applies to the symbols and indices: M stands for Si or Ge;

[0012] R 1 , R 2 , R 3 and R 4In each occurrence, the compound may be a straight-chain alkyl group with 1 to 40 carbon atoms, a branched or cyclic alkyl group with 3 to 40 carbon atoms, each of which may be substituted with one or more R groups other than H, a non-condensed or condensed aromatic ring system with 6 to 60 aromatic ring atoms, preferably a non-condensed aromatic ring system, or a non-condensed or condensed heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably a non-condensed heteroaromatic ring system containing at least one heteroatom selected from O and S, preferably one heteroatom selected from O and S, particularly preferably an O atom, wherein the aromatic and heteroaromatic ring systems may be substituted with one or more R groups other than H; at least one of the R groups may be 1 , R 2 , R 3 and R 4with at least one other of the residues R 1 , R 2 , R 3 and R 4 form a ring; provided that at least one of the residues R 1 , R 2 , R 3 and R 4 corresponds to the following formula (1a),

[0013] R is the same or different in each occurrence H, D, F, C(Ar')3, C(R')3, Si(Ar')3, Si(R')3, Ge(Ar')3, Ge(R')3, a straight-chain alkyl group with 1 to 40 C atoms or an alkenyl or alkynyl group with 2 to 40 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group may each be substituted with one or more R' groups other than H, wherein one or more non-adjacent CH2 groups may be replaced by Si(R')2, an aromatic ring system with 6 to 60 aromatic ring atoms, or a heteroaromatic ring system with 5 to 60 aromatic ring atoms, which includes at least one heteroatom selected from O and S, preferably one heteroatom selected from O and S, particularly preferably an O atom, contains, wherein the aromatic and hetero-aromatic ring systems can each be substituted by one or more R' groups, an aryloxy group with 6 to 60 aromatic ring atoms,or a heteroaryloxy group with 5 to 60 aromatic ring atoms, which contains at least one heteroatom selected from O and S, preferably one heteroatom selected from O and S, particularly preferably one O atom, wherein the aryloxy or heteroaryloxy group can be substituted by one or more R' groups, wherein two R' groups can also be linked to each other or one R' group can be linked to another group, in particular one R' group, a , R b , R c and R d form a ring system;

[0014] Ar' is, in each occurrence, either the same or different, an aromatic ring system with 6 to 60 aromatic ring atoms, or a hetero-aromatic ring system with 5 to 60 aromatic ring atoms, which includes at least one heteroatom selected from O and S, preferably one heteroatom selected from O and S, particularly preferably one O atom, wherein the aromatic and heteroaromatic ring system may be substituted with one or more R' substituents other than H, wherein two Ar' substituents bonding to the same C atom or Si atom may also be bridged by a single bond or a bridge selected from C(R')2, Si(R')2, C=O, C=C(R')2, O, S, S=O and SO2;

[0015] R' is selected in each occurrence, either the same or differently, from the group consisting of H, D, F, an aliphatic hydrocarbon residue with 1 to 20 C atoms, an aromatic ring system with 6 to 30 aromatic ring atoms, or a hetero-aromatic ring system with 5 to 30 aromatic ring atoms, in which at least one heteroatom is selected from O and S, preferably a heteroatom is selected from O and S, particularly preferably an O atom, wherein in the aromatic and heteroaromatic ring system one or more H atoms may be replaced by D, F and which may be substituted by one or more alkyl groups with 1 to 4 carbon atoms each, whereby two or more substituents R' may together form a ring system;

[0016] R a , R b , R c and R dF is the same or different in each occurrence, a straight-chain alkyl group with 1 to 40 C atoms or a branched or cyclic alkyl group with 3 to 40 C atoms, each of which may be substituted with one or more R' groups other than H, where one R group may be a with a remainder R b , a remainder R c with a remainder R d , or one of the remainders R a or R b with one of the remaining R c or R d form a ring; n is the same or different (1, 2, or 3) in each occurrence;

[0017] R e and R f is the same or different H, D, F in each occurrence, a straight-chain alkyl group with 1 to 40 C atoms or a branched or cyclic alkyl group with 3 to 40 C atoms, each of which may be substituted with one or more R' groups other than H, where one R group may be e with a remainder R fform a ring and / or at least one of the residues R e and R f with at least one of the residues R a , R b , R c and R d form a ring.

[0018] An aryl group according to the present invention contains 6 to 40 carbon atoms; a heteroaryl group according to this invention contains 3 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 selected from oxygen and / or sulfur. An aryl group or heteroaryl group is understood to be either a simple aromatic cycle, i.e., benzene, or a simple heteroaromatic cycle, for example, furan, thiophene, etc., or a fused (fused) aryl or heteroaryl group, for example, naphthalene, anthracene, phenanthrene, dibenzofuran, dibenzothiophene, etc. Aromatics linked together by single bonds, such as biphenyl, are not referred to as aryl or heteroaryl groups, but rather as aromatic ring systems.

[0019] An aromatic ring system according to the present invention contains 6 to 60 carbon atoms in the ring system, preferably 6 to 40 carbon atoms in the ring system. A heteroaromatic ring system according to this invention contains 3 to 60 carbon atoms, 3 to 40 carbon atoms, and at least one heteroatom in the ring system, provided that the sum of carbon atoms and heteroatoms is at least 5. The heteroatoms are selected from oxygen and / or sulfur. An aromatic or heteroaromatic ring system according to the present invention is understood to be a system that does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups may also be linked by a non-aromatic unit, such as a carbon, sulfur, or oxygen atom. For example, systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, diaryl ethers, stilbene, etc., are also considered to be aromatic or heteroaromatic ring systems according to the present invention.These are understood to be aromatic ring systems within the meaning of the present invention, and also systems in which two or more aryl groups are connected, for example, by a short alkyl group. Preferably, the aromatic ring system is selected from fluorene, 9,9'-spirobifluorene, or groups in which two or more aryl and / or heteroaryl groups are linked to one another by single bonds.

[0020] Within the scope of the present invention, the following are preferably used as the groupings of an aliphatic hydrocarbon residue or an alkyl group or an alkenyl or alkynyl group, which may contain 1 to 20 carbon atoms and in which individual hydrogen atoms or CH2 groups may also be substituted by the groups mentioned above: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, neo-pentyl, cyclopentyl, n-hexyl, neo-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, Cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentinyl, hexynyl, heptynyl or octynyl.Unter einer Alkoxygruppe mit 1 bis 40 C-Atomen werden bevor- zugt Methoxy, Trifluormethoxy, Ethoxy, n-Propoxy, i-Propoxy, n-Butoxy, i-Butoxy, s-Butoxy, t-Butoxy, n-Pentoxy, s-Pentoxy, 2-Methylbutoxy, n- Hexoxy, Cyclohexyloxy, n-Heptoxy, Cycloheptyloxy, n-Octyloxy, Cyclo- octyloxy, 2-Ethylhexyloxy, Pentafluorethoxy und 2,2,2-Trifluorethoxy ver- standen. Unter einer Thioalkylgruppe mit 1 bis 40 C-Atomen werden ins- besondere Methylthio, Ethylthio, n-Propylthio, i-Propylthio, n-Butylthio,.

[0021] 1-Butylthio, s-Butylthio, t-Butylthio, n-Pentylthio, s-Pentylthio, n-Hexylthio, Cyclohexylthio, n-Heptylthio, Cycloheptylthio, n-Octylthio, Cyclooctylthio,

[0022] 2-Ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethinylthio, propynylthio, butynylthio, pentinylthio, hexinylthio, heptinylthio, or octinylthio. In general, alkyl, alkoxy, or thioalkyl groups according to the present invention can be straight-chain, branched, or cyclic, wherein one or more non-adjacent CH₂ groups can be replaced by the groups mentioned above; furthermore, one or more H atoms can also be replaced by D or F, preferably F.

[0023] An aromatic or heteroaromatic ring system with 5 to 60 or 5 to 40 aromatic ring atoms, respectively, which may be further substituted with the aforementioned substituents and which may be linked via any positions on the aromatic or heteroaromatic compound, is understood to include, in particular, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, preferably dibenzofuran and dibenzothiophene, particularly preferably Dibenzofuran, or groups derived from combinations of these systems.The phrase "two or more residues can form a ring" in this description means, among other things, that the two residues are linked to each other by a chemical bond involving the formal elimination of two hydrogen atoms. This is illustrated by the following scheme.

[0024] 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:

[0025] Furthermore, it may be provided that the compound has exactly one Si atom or exactly one Ge atom, or that the compound has exactly two Si atoms, exactly two Ge atoms, or exactly one Si atom and exactly one Ge atom.

[0026] In a preferred embodiment, the compounds of formula (I) are characterized in that two, three or four, particularly preferably three or four of the residues R 1 , R 2 , R 3 and R 4 correspond to formula (1a).

[0027] In a further preferred embodiment of the present invention, formula (1a) corresponds to the following formula (1b),

[0028] where the symbols have the meanings mentioned above in relation to formula (1a).

[0029] In yet another preferred embodiment of the present invention, formula (1a) corresponds to the following formula (1c), where the symbols have the meanings mentioned above in relation to formula (1a).

[0030] In a particularly preferred embodiment of the present invention, the compound of formula (I) corresponds to one of the following formulas (IIa) to (I Id),

[0031]

[0032] Formula (lId) where the symbols and indices have the meanings mentioned above in relation to formula (I) and (la).

[0033] In a preferred embodiment of the present invention, n in formulas (1a), (1b), (2a), (2b), (2c) and (2d) is 1 in each case.

[0034] In a further preferred embodiment of the present invention, n in formulas (1a), (1b), (Ha), (Hb), (Hc) and (2d) is 2 in each case.

[0035] In yet another preferred embodiment of the present invention, formulas (Hb), (Hc) and (IId) include at least one n = 1 and at least one n = 2.

[0036] In a particularly preferred embodiment of the present invention, the compound of formula (I) corresponds to one of the following formulas (Ha1 ) to (IId2),

[0037]

[0038] Formula (Ild2) wherein the symbols and indices have the meanings mentioned above in relation to formula (I) and (1a).

[0039] In formulas (Ila), (IlIb), (IIe), (IlId) as well as in formulas (Ila1), (Ila2), (Ilb1), (Ilb2), (Ilc1), (Ilc2), (Ild1) and (Ild2), the residues R e and R f In a preferred embodiment, all are equal to H, in a further preferred embodiment, all are equal to D, and in yet another preferred embodiment, all are equal to a straight-chain alkyl group with 1 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms.

[0040] In a preferred embodiment of the present invention, the two residues R form a and R b together with the C atom to which the two R groups are attached a and R b bind the two remaining R c and R d together with the C atom to which the two R groups are attached c and R dbind, and / or the two residues R e and R f together with the C atom to which the two R groups are attached e and R f bind a ring of formulas (RC-1 ) to (RC-14) or R 1 , R 2 , R 3 and / or R 4 is selected from the structures of formulas (RC-1 ) to (RC-14),

[0041] Formula (RC-1 ) Formula (RC-2) Formula (RC-3)

[0042] Formula (RC-4) Formula (RC-5) Formula (RC-6)

[0043] Formula (RC-10) Formula (RC-11 ) Formula (RC-12)

[0044] Formula (RC-13) Formula (RC-14) wherein R' has the meaning set out above, in particular for formula (I), the dashed bonds represent the attachment points to the respective group, and the other symbols have the following meanings: r is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1 or 2; s is 0, 1, 2, 3, 4, 5, 6, 7 or 8, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1 or 2; t is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1 or 2; v is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1 or 2; z is the same or different 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 13, 14, 15 or 16, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1 or 2.

[0045] Structures of formulas (RC-1 ), (RC-2), (RC-6), (RC-7), (RC- 10) and (RC-11 ) are preferred.

[0046] Furthermore, it may be provided that a remainder R a and a remainder R b , a remainder R c and a remainder R d , and / or a remainder R e and a remainder R f form a ring and together constitute a group of the formula -(C(R')2)m-, where m is an integer in the range of 1 to 6, preferably 1 to 5, particularly preferably 1 to 4 and R' has the meaning mentioned in relation to formula (I).

[0047] Preferably, a remainder R a and a remainder R b , a remainder R c and a remainder R d , and / or a remainder R e and a remainder R f The group may be a straight-chain alkyl group with 1 to 40 carbon atoms, preferably 1 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 40 carbon atoms, preferably 3 to 20 carbon atoms, which may be substituted with one or more R' groups other than H.

[0048] In a further preferred embodiment, it can be provided that two adjacent residues R, two adjacent residues selected from R 1 , R 2 , R 3 and R 4 as well as R a and R b , R c and R d or R e and R f together form a group of the formula (Cy-1 ),

[0049] where the dashed bonds represent the connection points, R and R' have the meaning mentioned above, especially for formula (I), and the following applies to the other symbols:

[0050] V 1represents a bond, a straight-chain alkylene group with 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms, or a branched or cyclic alkylene group with 3 to 40 carbon atoms, preferably 3 to 20 carbon atoms, each of which may be substituted with one or more R' groups other than H, or an ortho-linked aromatic or heteroaromatic ring system with 6 to 60, preferably 6 to 40 aromatic ring atoms, which may be substituted with one or more R' groups other than H. Preferably, V represents a bond, a group -C(R')2-, -C(R')2-C(R')2-, -C(R')2-C(R')2-, -C(R')=C(R')- or an ortho-linked phenylene group, which may be substituted with one or more R' groups other than H. R' can be substituted;

[0051] W° represents a group -C(R e)2- or an ortho-linked aromatic or heteroaromatic ring system with 6 to 60, preferably 6 to 40 aromatic ring atoms, which may be substituted with one or more R-non-H substituents; represents a group -C(R f )2- or an ortho-linked aromatic or heteroaromatic ring system with 6 to 60, preferably 6 to 40 aromatic ring atoms, which may be substituted with one or more R substituents other than H;

[0052] R e The element H, D, is the same or different in each occurrence; it is a straight-chain alkyl group with 1 to 40 carbon atoms, preferably 1 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 40 carbon atoms, preferably 3 to 20 carbon atoms, which may be substituted with one or more R' groups other than H, wherein two R' groups may be e together or a remainder R e with a remainder R f form a ring, where in the case that a group R eFor H or D stands, the group W c preferably binds directly to the benzene ring;

[0053] R f The element H, D, is the same or different in each occurrence; it is a straight-chain alkyl group with 1 to 40 carbon atoms, preferably 1 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 40 carbon atoms, preferably 3 to 20 carbon atoms, which may be substituted with one or more R' groups other than H, wherein two R' groups may be f together or a remainder R f with a remainder R e form a ring, where in the case that a group R f For H or D stands, the group W d preferably binds directly to the benzene ring.

[0054] In a preferred embodiment of the invention, two adjacent residues R preferably form a group of formulas (CyC-1 ) to (CyC-4) where the dashed bonds represent the attachment points to the benzene ring, the symbols R and R 1 the meanings previously set out, in particular for formula (I), and the symbols R e and R f the meanings mentioned above, especially for formula (Cy-1 ).

[0055] Furthermore, it may be provided that at least one remainder R 1 , R 2 , R 3 and / or R 4 The derivative R is selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or triphenylene, each of which may be substituted with one or more R groups other than H. Preferably, R is... 1 , R 2 , R 3 and R 4 structures that do not have a condensed aromatic or heteroaromatic ring system.

[0056] Furthermore, it may be provided that at least one residue R is selected from the group consisting of H, D, an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which may be substituted with one or more residues R', preferably at least one substituent R is selected from the group consisting of an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which may be substituted with one or more residues R'.

[0057] Furthermore, it may be provided that the substituents R and R' according to the formulas above do not form a condensed aromatic or heteroaromatic ring system with the ring atoms of the ring system to which the substituents R and R' bind. This includes the formation of a condensed aromatic or heteroaromatic ring system with possible substituents that may be bonded to the substituents R and R'.

[0058] If the compound according to the invention is substituted with aromatic or heteroaromatic groups R or R', it is preferred in one embodiment if these groups do not have aryl or heteroaryl groups with more than two directly fused aromatic six-membered rings. Particularly preferred are the substituents not having any aryl or heteroaryl groups with directly fused aromatic or heteroaromatic six-membered rings at all. This preference is due to the low triplet energy of such structures. Condensed aryl groups with more than two directly fused aromatic six-membered rings that are nevertheless suitable according to the invention are phenanthrene and triphenylene, since these also exhibit a high triplet energy level.

[0059] Furthermore, it can be provided that the residue R or R' does not comprise an aromatic or heteroaromatic ring system having three linearly condensed aromatic six-membered rings, wherein preferably none of the residues R comprises an aromatic or heteroaromatic ring system having three linearly condensed aromatic six-membered rings.

[0060] Furthermore, it can be provided that the substituents R and R' according to the above formulas do not form a condensed aromatic or heteroaromatic ring system with the ring atoms of the ring system, preferably not a condensed ring system. This includes the formation of a condensed ring system with possible substituents that can be bonded to the R and R' groups.

[0061] When two substituents, which may be selected from R and / or R', form a ring system, this system can be monocyclic or polycyclic, aliphatic, heteroaliphatic, aromatic, or heteroaromatic. The substituents forming the ring system can be adjacent, meaning they are bonded to the same carbon atom or to carbon atoms that are directly bonded to each other, or they can be further apart. Furthermore, the ring systems containing the substituents R and / or R' can also be linked by a bond, thus resulting in ring closure.

[0062] If a remainder R a and a remainder R b , a remainder R c and a remainder R d , and / or a remainder R e and a remainder R fWhen two R groups form a ring, it can be monocyclic or polycyclic, in particular bicyclic, tricyclic, tetracyclic, or pentacyclic. e together or two residues R f When they form a ring together, it can be mono- or polycyclic, in particular bicyclic, tricyclic, tetracyclic or pentacyclic.

[0063] Furthermore, it may be provided that at least one residue R is selected, either the same or different in each occurrence, from the group consisting of an aromatic or heteroaromatic ring system selected from the groups of the following formulas Ar-1 to Ar-41, and / or the group Ar' is selected, either the same or different in each occurrence, from the groups of the following formulas Ar-1 to Ar-41.

[0064] where R' has the meanings mentioned above, the dashed line represents the connection to the corresponding group, and furthermore: Ar 1 In each occurrence, the system is either the same or different: a bivalent aromatic ring system with 6 to 18 aromatic ring atoms or a heteroaromatic ring system with 5 to 18 aromatic ring atoms, which contains at least one heteroatom selected from O and S, preferably one heteroatom selected from O and S, particularly preferably an O atom, wherein the aromatic and heteroaromatic ring systems can each be substituted with one or more R' groups;

[0065] A is either the same or different from C(R')2, 0 or S for each occurrence; p is 0 or 1 , where p = 0 means that the group Ar 1 is not present and that the corresponding aromatic or heteroaromatic group is directly bound to the corresponding residue.

[0066] The structures of formulas (Ar-1) to (Ar-41) presented above represent preferred configurations of aromatic or heteroaromatic ring systems, such as those for R 1 , R 2 , R 3 and R 4 in structures of formula (I), where in this case the substituents R' in formulas (Ar-1) to (Ar-41) are to be replaced by R, where R has the meaning previously explained, in particular for formula (I). Furthermore, some of the aromatic or heteroaromatic ring systems are ortho-linked and in this case include an additional binding site in the ortho position, where here in formulas (Ar-1) to (Ar-41) a residue R' can represent a binding site.

[0067] Furthermore, it may be provided that at least one remainder R a , R b , R c and / or R dselected from structures of the groups shown in formulas (Ar-1) to (Ar-41), wherein the substituents R shown in formulas (Ar-1) to (Ar-41) 1 to be replaced by R.

[0068] Structures of formulas (Ar-1), (Ar-2), (Ar-3), and (Ar-4) are preferred. If the aforementioned groups for structures of formulas (Ar-1) to (Ar-41) have multiple groups A, then all combinations from the definition of A are possible.

[0069] If A stands for C(R')2, then the substituents R 1, which are bonded to this carbon atom, preferably identical or different in each occurrence for a linear alkyl group with 1 to 10 carbon atoms, or for a branched or cyclic alkyl group with 3 to 10 carbon atoms, or for an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms. Most preferably, R' represents a methyl group or a phenyl group. The R' groups can also form a ring system with each other, leading to a spiro system.

[0070] Preferably, it can be provided that at least one of the remainder R a , R b , R c and / or R d , preferably all remaining R a , R b , R c and R dThe alkyl group, whether the same or different at each occurrence, is selected from a straight-chain alkyl group with 1 to 20 C atoms, preferably 1 to 10 C atoms, a branched or cyclic alkyl group with 3 to 25 C atoms, preferably 3 to 18 C atoms, each of which may be substituted with one or more R' groups other than H.

[0071] Furthermore, it may be provided that the two remainders R a and R b or R c and R d do not form a ring.

[0072] Preferably, it can be provided that the groups R are bonded to the cyclopentyl group a and R b , R c and R d and / or R e and R f are the same or the groups R bonded to the cyclopentyl group a and R b , R c and R d and / or R e and R f form a ring.

[0073] Preferred substituents R are described below.

[0074] In a preferred embodiment of the present invention, R is selected, either the same or different at each occurrence, from the group consisting of H, D, F, Si(R')s, a straight-chain alkyl group with 1 to 20 C atoms, or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl group may be substituted with one or more R' groups, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, which may be substituted by one or more R' groups.

[0075] In a further preferred embodiment of the present invention, the substituent R is selected, either the same or different at each occurrence, from the group consisting of H, D, F, a straight-chain alkyl group with 1 to 20 C atoms, or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl group may be substituted with one or more R' groups, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, which may each be substituted by one or more R' groups.

[0076] Furthermore, it can be provided that at least one residue R, preferably a substituent R, is selected in the same or different ways at each occurrence from the group consisting of H, D, an aromatic or hetero-aromatic ring system with 6 to 30 aromatic ring atoms, which may be substituted with one or more residues R'.

[0077] Particularly preferably, the residue R is preferably the same or different from the substituent R in each occurrence selected from the group consisting of H, D or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably with 6 to 13 aromatic ring atoms, each of which may be substituted with one or more residues R'.

[0078] Furthermore, it may be provided that at least one residue R represents an aromatic or heteroaromatic ring system with 5 to 13 aromatic ring atoms, which may be substituted with one or more residues R'.

[0079] Preferably, at least one residue, preferably a substituent R, may be selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene, each of which may be substituted with one or more residues R'.

[0080] Here, the term substituent means, in particular, that R is not equal to H. Furthermore, the substituents R can be the same or different if two or more substituents are present that are selected from the aforementioned aromatic or heteroaromatic groups.

[0081] Preferably, it can be provided that the groups R a , R b , R c , R d , R eand R f The groups, whether the same or different, are selected from straight-chain alkyl groups with 1 to 20 carbon atoms or branched or cyclic alkyl groups with 3 to 20 carbon atoms, each of which may be substituted with one or more R' groups, preferably deuterated, wherein the R' groups bonded to a carbon atom may be a and R b , R c and R d , and / or R e and R f together form a ring system.

[0082] In a further preferred embodiment of the present invention, R a , R b , R c , R d , R e and R f same or different, selected 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 may be substituted with one or more R' groups; the R groups bonded to a carbon atom may bea and R b , R c and R d , and / or R e and R f together form a ring system.

[0083] R is particularly preferred a , R b , R c , R d , R e and R f same or different, in each occurrence selected from a straight-chain alkyl group with 1 to 5 C atoms or a branched or cyclic alkyl group with 3 to 5 C atoms, wherein the alkyl group may in each case be substituted with one or more R' substituents, the R groups bonded to a C atom a and R b , R c and R d , and / or R e and R f together form a ring system. Furthermore, it may preferably be provided that the groups R a , R b , R c , R d , R e and R f for methyl, ethyl, propyl or phenyl, or two groups R a and R b, R c and R d , as well as R e and R f , which bind to a carbon atom of the cycloalkyl group to form a cycloalkyl residue with 5 or 6, preferably 5, carbon atoms, wherein these groups may be deuterated. Preferably the groups R a , R b , R c , R d , R e and R f unsubstituted, apart from D.

[0084] Preferred aromatic or heteroaromatic ring systems for groups W c or W dor the substituents R or Ar' are selected from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, which may be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which may be linked via the 1-, 2-, 3- or 4-position, naphthalene, in particular 1- or 2-linked naphthalene, benzofuran, benzothiophene, dibenzofuran, which may be linked via the 1-, 2-, 3- or 4-position, dibenzothiophene, which may be linked via the 1-, 2-, 3- or 4-position, anthracene, pyrene, perylene, chrysene, phenanthrene or triphenylene, each of which may be linked with one or more The remains R' can be substituted.

[0085] The structures Ar-1 to Ar-41 listed above are particularly preferred, with structures of formulas (Ar-1), (Ar-2), (Ar-3), and (Ar-4) being favored. It should be noted that structures Ar-1 to Ar-41 are represented with a substituent R'. In the case of groups W c or W d These substituents R' are to be replaced by R, where one substituent R' represents a bond, since the groups W c or W d are ortho-linked.

[0086] In a further preferred embodiment of the invention, R 1 , R 2 , R 3 and R 4Selected from the group consisting of 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 substituted with one or more R groups, or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, each of which may be substituted by one or more R groups, provided that at least one of the R groups 1 , R 2 , R 3 or R 4 for a group of formula (1a) or the preferred embodiments.

[0087] In a particularly preferred embodiment of the invention, R 1 , R 2 , R 3 and R 4The group consisting of a straight-chain alkyl group with 1 to 6 carbon atoms, in particular with 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group with 3 to 6 carbon atoms, wherein the alkyl group may be substituted with one or more R groups, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system with 6 to 13 aromatic ring atoms, each of which may be substituted by one or more R groups, but is preferably unsubstituted, provided that at least one of the R groups 1 , R 2 , R 3 or R 4 for a group of formula (1a) or the preferred embodiments.

[0088] In compounds according to the invention that are processed by vacuum evaporation, the alkyl groups preferably have no more than ten carbon atoms, particularly preferably no more than six carbon atoms, and most preferably no more than four carbon atoms. For compounds processed from solution, compounds substituted with alkyl groups, in particular branched alkyl groups, with up to 10 carbon atoms, or substituted with oligoarylene groups, for example ortho-, meta-, para- or branched terphenyl or quaterphenyl groups, are also suitable.

[0089] Furthermore, the compounds may include crosslinkable groups Q. A crosslinkable group Q, as used in the present invention, is a functional group capable of undergoing a reaction to form an insoluble compound. This reaction can occur with another identical group Q, another different group Q, 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 the layer, forming an insoluble layer. Crosslinking can typically be accelerated by heat 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 according to the invention, 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.

[0090] The compound according to formula (I) or preferred embodiments of this formula may comprise one, two, three or more crosslinkable groups Q, wherein the compound according to formula (I) or preferred embodiments of this formula preferably comprises two, three or more crosslinkable groups Q.

[0091] According to the invention, preferred crosslinkable groups Q are the following groups: a) Terminal or cyclic alkenyl or terminal dienyl and alkynyl groups:

[0092] Suitable units include 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 40 carbon atoms, preferably with 2 to 10 carbon atoms, wherein individual CH₂ groups and / or individual hydrogen atoms may also be replaced by the aforementioned groups R. Furthermore, groups that can be considered precursors and that are capable of forming a double or triple bond in situ are also suitable. b) Alkenyloxy, dienyloxy, or alkynyloxy groups: Alkenyloxy, dienyloxy, or alkynyloxy groups are also suitable, preferably alkenyloxy groups. c) Acrylic acid groups:

[0093] Acrylic acid units in the broadest sense are also suitable, preferably acrylic esters, acrylamides, methacrylic esters and methacrylamides. Ci-w-alkyl acrylate and Ci-10-alkyl methacrylate are particularly preferred.

[0094] The crosslinking reaction of the groups mentioned above under a) to c) can occur via a radical, a cationic or anionic mechanism, but also via cycloaddition.

[0095] It can be beneficial to add a suitable initiator for the crosslinking reaction. Suitable initiators for radical crosslinking include dibenzoyl peroxide, AIBN, or TEMPO. Suitable initiators for cationic crosslinking include AICI3, BF3, triphenyl methyl perchlorate, or tropylium hexachloroantimonate. Suitable initiators for anionic crosslinking are bases, especially butyllithium.

[0096] In a preferred embodiment of the present invention, however, the crosslinking is carried out without the addition of an initiator and is initiated exclusively thermally. This preference is justified by the fact that the absence of the initiator prevents impurities in the layer that could lead to a deterioration of the device properties. d) Oxetanes and oxiranes:

[0097] Another suitable class of crosslinkable groups Q are oxetanes and oxiranes, which crosslink cationically by ring opening.

[0098] It can be useful to add a suitable initiator for the crosslinking reaction. Suitable initiators include, for example, AICI3, BF3, triphenylmethyl perchlorate, or tropylium hexachloroantimonate. Photoacids can also be added as initiators. e) Silanes:

[0099] Silane groups SiR3 are also suitable as a class of crosslinkable groups, where at least two R groups, preferably all three R groups, 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. f) Cyclobutane groups

[0100] The crosslinkable groups Q mentioned above under a) to f) are generally known to those skilled in the art, as are the suitable reaction conditions used to react these groups.

[0101] Preferred crosslinkable groups Q 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:

[0102] The remains R 11 , R 12 , R 13 and R 14 In formulas Q1 to Q8, Q11, Q13 and Q14, H, a straight-chain or branched alkyl group with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, is present in each instance, whether identical or different. The R 11 , R 12 , R 13 and R 14H, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, sec-Butyl or tert-Butyl I and especially preferably H or Methyl. The indices used have the following meanings: m = 0 to 8; and n = 1 to 8.

[0103] Ar 10 In formula Q14, the same meaning can be assumed as Ar' in formula (I). The dashed bonds in formulas Q1 to Q11 and Q14, as well as the dashed bonds in formulas Q12 and Q13, represent the connection of the crosslinkable group to the repeating units.

[0104] The crosslinkable groups of formulas Q1 to Q14 can be directly linked to the repeating unit, or indirectly, via another mono- or polycyclic aromatic or heteroaromatic ring system Ar 10 , as shown in the following formulas Q15 to Q28:

[0105] where Ar 10in formulas Q15 to Q28, Ar' can take on the same meanings as in formula (I).

[0106] The following are particularly preferred networkable groups Q: The remains R 11 , R 12 ,R 13 and R 14 In each occurrence, whether identical or different, H or a straight-chain or branched alkyl group with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, are present. The R groups are particularly preferred. 11 , R 12 ,R 13 and R 14 Methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl or tert-butyl, and especially methyl.

[0107] The indices used have the following meaning: m = 0 to 8 and n = 1 to 8.

[0108] The following are particularly preferred networkable groups Q:

[0109] When the compounds of formula (I) or the preferred embodiments are used as matrix material for a phosphorescent emitter or in a layer directly adjacent to a phosphorescent layer, it is further preferred that the compound does not contain fused aryl or heteroaryl groups in which more than two six-membered rings are directly fused to one another. Phenanthrene and triphenylene are exceptions to this, as they may be preferred despite the presence of fused aromatic six-membered rings due to their high triplet energy.

[0110] Preferably, in one embodiment, the compound may not comprise an aromatic or heteroaromatic ring system having three aromatic rings condensed together.

[0111] In a preferred embodiment, the compounds according to the invention have a high degree of deuteration. Preferably, the degree of deuteration is at least 50%, more preferably at least 80%, more preferably at least 90%, and most preferably at least 95%. The degree of deuteration is determined by the numerical ratio of deuterium to the sum of deuterium and 1 Hydrogen (D / (D+H)*100). The compounds are particularly preferred if they are fully deuterated.

[0112] The ordinary refractive indices of the compounds according to the invention, measured via ellipsometry at 450 nm, are preferably < 1.7, more preferably < 1.6, particularly preferably < 1.55 and especially preferably < 1.45. Preferably, the compound according to the invention may have a molecular weight of < 5000 g / mol, more preferably < 4000 g / mol, more preferably < 3000 g / mol, more preferably < 2000 g / mol, more preferably < 1500 g / mol and most preferably < 1000 g / mol.

[0113] Furthermore, preferred compounds according to the invention are characterized by being sublimable. These compounds generally have a molar mass of less than approximately 1500 g / mol.

[0114] Furthermore, it may be provided that the compound according to formula (I) or a preferred embodiment of these compounds is not in direct contact with a metal atom, preferably does not represent a ligand for a metal complex.

[0115] The preferred embodiments mentioned above can be combined with one another as desired within the limitations defined in claim 1. In a particularly preferred embodiment of the invention, the preferences mentioned above occur simultaneously.

[0116] Examples of preferred connections according to the embodiments listed above are the connections listed in the following table.

[0117] The compounds 4 according to the invention can be prepared from aryl halides 1 known from the literature and the halosilanes 3 by salt metathetic reaction. For this purpose, the aryl halides 1 are first transmetallated to the compounds 2 by reaction with a reactive metal, such as Li, Mg, or zinc, or a metal-organic compound, such as an organo-lithium compound, preferably n-butyllithium, n-hexyllithium, tert-butyllithium, or a Grignard reagent, preferably iso-propyl-MgCl*LiCl (Knöchel Turbo-Grignard). The aryl-metal compounds 2 thus obtained as intermediates are then reacted with a mono-, di-, tri-, or tetra-halogenated silane or germane 3. Preferred reaction media are dipolar aprotic solvents such as ethers or cyclic ethers, in particular diethyl, di-n-butyl, tert-butyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran or dioxane or mixtures thereof.The exothermic salt metathesis is preferably carried out initially at cryogenic temperatures or under cooling; however, if necessary, the reaction can also be performed at elevated temperatures to complete the reaction. The work-up and purification of the compounds 4 according to the invention are carried out according to steps known to those skilled in the art, such as quenching, extraction, chromatography, recrystallization, and fractional distillation or sublimation under high vacuum.

[0118] The meaning of the symbols used in the scheme set out above is essentially the same as that defined for formula (I), although for the sake of clarity, numbering and a full representation of all symbols have been omitted.

[0119] The scheme above specifically depicts aromatic groups with substituents that represent a preferred embodiment. The above descriptions are therefore specific and can be easily generalized by those skilled in the art.

[0120] Another object of the present invention is therefore a process for producing a compound according to the invention, wherein first an aryl halide is converted to an aryl metal compound and the aryl metal compound is then reacted with a halogen-silicon compound or a halogen-germanium compound by salt metathesis.

[0121] By these processes, optionally followed by purification, such as recrystallization or sublimation, the compounds according to the invention can be obtained in high purity, preferably more than 99% (determined by 1H-NMR, HPLC and / or GC).

[0122] The compounds according to the invention can also be mixed with a polymer. It is also possible to covalently incorporate these compounds into a polymer. This is particularly possible with compounds substituted with reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic esters, or with reactive, polymerizable groups, such as olefins or oxetanes. These can be used as monomers to produce corresponding oligomers, dendrimers, or polymers. The oligomerization or polymerization preferably proceeds via the halogen functionality or the boronic acid functionality, or via the polymerizable group. It is also possible to crosslink the polymers via such groups. The compounds and polymers according to the invention can be used as crosslinked or uncrosslinked layers.

[0123] A further object of the present invention is therefore oligomers, polymers, or dendrimers containing one or more of the structures of formula (I) and preferred embodiments of this formula listed above, or compounds according to the invention, wherein one or more bonds of the compounds according to the invention or of the structures of formula (I) and preferred embodiments of this formula are present with the polymer, oligomer, or dendrimer. Depending on the linkage of the structures of formula (I) and preferred embodiments of this formula or of the compounds, 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.

[0124] To produce the oligomers or polymers, the monomers according to the invention are homopolymerized or copolymerized with further monomers. Copolymers are preferred, wherein the units according to formula (I) or the preferred embodiments described above and below are present in amounts of 0.01 to 99.9 mol%, preferably 5 to 90 mol%, and particularly preferably 20 to 80 mol%. Suitable and preferred comonomers forming the polymer backbone are selected from fluorenes (e.g., according to EP 842208 or WO 2000 / 022026), spirobifluorenes (e.g., according to EP 707020, EP 894107, or WO 2006 / 061181), para-phenylenes (e.g., according to WO 92 / 18552), carbazoles (e.g., according to WO 2004 / 070772 or WO 2004 / 113468), thiophenes (e.g., according to EP 1028136), dihydrophenanthrenes (e.g., according to WO 2005 / 014689), cis- and trans-indenofluorenes (e.g., according to WO 2004 / 041901 or WO 2004 / 113412), and ketones (e.g., according to WO 2005 / 040302), phenanthrenes (e.g.(according to WO 2005 / 104264 or WO 2007 / 017066) or several of these units. The polymers, oligomers and dendrimers may contain further units, for example hole transport units, in particular those based on triarylamines, and / or electron transport units.

[0125] Of particular interest are also compounds according to the invention which are characterized by a high glass transition temperature. In this context, compounds according to formula (I) or according to the preferred embodiments described above and below are particularly preferred, which have a glass transition temperature of at least 70 °C, particularly preferably at least 110 °C, most preferably at least 125 °C and most preferably at least 150 °C, as determined according to DIN 51005 (version 2005-08).

[0126] 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, butylbenzoate, cumene, cyclohexanol, cyclohexanone, cyclo- hexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, NMP,p-cymene, phenetol, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropyl naphthalene, 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, octyloctanoate, heptylbenzene, Menthyl isovalerate, cyclohexyl hexanoate or mixtures of these solvents.

[0127] Another object of the present invention is therefore a formulation or a composition containing at least one compound according to formula (I), formula (I) wherein the symbols have the aforementioned meanings, and at least one further compound. Formulations or compositions containing oligomers, dendrimers, or polymers of the present invention are included herein. The further compound may, for example, be a solvent, in particular one of the solvents mentioned above or a mixture of these solvents. If the further compound comprises a solvent, 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 conductor material, an emitting compound, and / or a matrix material, wherein a mixture of a compound according to formula (I) and an organic or inorganic compound that is also used in the electronic device is referred to herein as a composition. A further object of the present invention is therefore a

[0128] Composition containing at least one compound according to formula (I), formula (I) wherein the symbols have the aforementioned meanings 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, electron blocking materials and hole blocking materials, preferably electron injection materials, electron transport materials, hole injection materials or hole conductor materials, particularly preferably electron transport materials or hole conductor materials.

[0129] 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 electroluminescent device, as described in more detail below. This makes it very easy to adapt and match the refractive indices of different functional layers, thereby enabling an unexpected increase in the efficiency of these devices.

[0130] The compound according to the invention can be used in combination with fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF, and / or host materials to modify their refractive index. Since the emission layer often already comprises at least two, three, or more components, and finding a power maximum is therefore complex, surprising advantages can arise from using the compounds according to the invention in an electron transport layer and / or a hole transport layer.

[0131] It should be noted that the compounds presented above and below, in combination with the compounds according to formula (I) and preferred embodiments of these compounds, such as hole transport materials and / or electron transport materials, often contain nitrogen atoms. Therefore, the previously presented definitions of heteroaryl groups and / or heteroaromatic ring systems must be extended to include compounds containing nitrogen, boron, or phosphorus atoms. This is often indicated here by clarifying that the heteroaromatic ring systems may contain nitrogen atoms.

[0132] Preferably, the proportion of compounds according to formula (I) or preferred embodiments of this formula in a composition may be in the range of 5 volume % to 90 volume %, particularly preferably in the range of 10 volume % to 80 volume % and especially preferably in the range of 30 volume % to 70 volume %.

[0133] Preferably, the composition may therefore comprise at least one compound according to formula (I) or preferred embodiments of this formula and at least one hole transport material.

[0134] Compounds with hole transport properties, also referred to herein as hole conductor materials 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 an electronic device, a hole transport material can also be used as a hole injection material.Preferred compounds exhibiting hole injection and / or hole transport properties include, for example, triarylamine, benzidine, tetraaryl-para-phenylenediamine, triarylphosphine, phenothiazine, phenoxazine, dihydrophenazine, thianthrene, dibenzo-para-dioxin, phenoxathiin, carbazole, azulene, thiophene, pyrrole and furan derivatives and other 0-, S- or N-containing heterocycles with a high-lying HOMO (HOMO = highest occupied molecular orbital).

[0135] Compounds exhibiting hole injection and / or hole transport properties are preferably selected from triarylamines, in particular mono-triarylamines and bis-triarylamines, and carbazolamines. A mono-triarylamine is defined as 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 defined as 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 defined as a compound containing a carbazole group and an amine group, wherein the amine group is preferably a triarylamine group.A triarylamine group is an amine group in which three groups, selected from aromatic and heteroaromatic ring systems, are bonded to the nitrogen atom of the amine group.

[0136] 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) where the following applies to the symbols:

[0137] Ar 15 In each occurrence, whether the same or different, it is selected from aromatic ring systems with 6 to 50 aromatic ring atoms, separated by R groups. 15 which can be substituted with non-H atoms, and heteroaromatic ring systems which can contain N atoms, with 5 to 40 aromatic ring atoms separated by R groups 15 can be substituted with something other than H;

[0138] Ar 16In each occurrence, whether the same or different, it is selected from aromatic ring systems with 6 to 50 aromatic ring atoms, separated by R groups. 15 which can be substituted with non-H atoms, and heteroaromatic ring systems which can contain N atoms, with 5 to 40 aromatic ring atoms separated by R groups 15 can be substituted with something other than H;

[0139] 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, which may contain nitrogen atoms, with 5 to 40 aromatic ring atoms; wherein the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic and heteroaromatic ring systems are enclosed by R groups 16 can be substituted with non-H and where 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, 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;

[0140] R 16is chosen from H, D, F, C(=O)R for each occurrence, whether the same or different. 17 , CN, Si(R 17 )3, N(R 17 )2, P(=O)(R 17 )2, OR 17 , S(=O)R 17 , S(=O)2R 17 , straight-chain alkyl or alkoxy groups with 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups with 3 to 20 carbon atoms, alkenyl or alkynyl groups with 2 to 20 carbon atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems, which may contain nitrogen atoms, with 5 to 40 aromatic ring atoms; wherein the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic and heteroaromatic ring systems are enclosed by R groups 17 can be substituted with non-H and where one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups can each be replaced by -R 17 C=CR 17 -, -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; wherein two or more, preferably adjacent, residues R 16 together form a ring system;

[0141] R 17 The group is selected in each occurrence, either the same or different, from H, D, F, CI, Br, I, CN, alkyl groups with 1 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems, which may contain N atoms, with 5 to 40 aromatic ring atoms; wherein the alkyl groups, the aromatic and the heteroaromatic ring systems may be substituted by residues F and CN, with two or more, preferably adjacent, residues R 17 together form a ring system.

[0142] 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 with R substituents 15 may be substituted.

[0143] Preferably the groups Ar 15the same or different at each occurrence chosen from monovalent groups representing combinations of 2 to 4 groups selected from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, each of the groups with R groups 15 may be substituted.

[0144] Particularly preferred groups Ar 15are, the same 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, carbazole, benzofuran, benzothiophene, benzo-condensed dibenzofuranyl, benzo-condensed dibenzothiophenyl, and phenyl, which is substituted with a group selected from naphthyl, phenanthrenyl, fluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, pyrimidyl, and triazinyl, each of the above groups with R substituents 15 may be substituted.

[0145] Preferred Groups Ar 16are, the same or different at each occurrence, selected from divalent groups derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, each of the groups with R substituents 15 may be substituted.

[0146] Preferably the groups Ar 16the same or different at each occurrence chosen from monovalent groups representing combinations of 2 to 4 groups selected from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenanthrene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, each of the groups with R groups 15 may be substituted.

[0147] Particularly preferred groups Ar 16are, the same or different at each occurrence, chosen from divalent groups consisting of 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 dibenzothiophenyl, each of the above groups with R substituents 15 may be substituted.

[0148] 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 carbon atoms, branched or cyclic alkyl or alkoxy groups with 3 to 20 carbon atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems, which may contain nitrogen atoms, with 5 to 40 aromatic ring atoms; wherein the aforementioned alkyl and alkoxy groups and the aforementioned aromatic and heteroaromatic ring systems are hyphenated by R groups 16 can be substituted with something other than H.

[0149] 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 20 carbon atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems, which may contain nitrogen atoms, with 5 to 40 aromatic ring atoms; wherein the aforementioned alkyl and alkoxy groups and the aforementioned aromatic and heteroaromatic ring systems are hyphenated by R groups 17 can be substituted with something other than H.

[0150] Preferably R 17 The elements, whether the same or different at each occurrence, are selected from H, D, F, CN, alkyl groups with 1 to 20 carbon atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems, which may contain nitrogen atoms, with 5 to 40 aromatic ring atoms. Particularly preferred embodiments of the compounds of formula (L-1) correspond to the following formulas. where the symbols Ar 15 and R 15, which have the meanings previously mentioned especially for formula (L-1) and for the other symbols:

[0151] Ar 17 is selected from aromatic ring systems with 6 to 13 aromatic ring atoms, separated by R groups 15 which may be substituted with non-H atoms, and heteroaromatic ring systems which may contain N atoms, with 5 to 13 aromatic ring atoms separated by R groups 15 can be substituted with something other than H;

[0152] X is chosen from a pair, 0, S, NR, in each occurrence, whether the same or different. 15 and (C(R) 15 )2;

[0153] Y 1 is chosen from 0 or S; n is 0 or 1 , where n = 0 means that the group with index n is not present and that the groups bound to the group with index n are directly connected to each other, with the proviso that n is not 0 in the case of formula (L-1 -9).

[0154] The preferred group is Ar17 selected from divalent groups derived from benzene, biphenyl, naphthalene, fluorene, in particular 9,9'-dimethyl-fluorene and 9,9'-diphenylfluorene, each of the groups with R substituents 15 may be substituted.

[0155] Particularly preferred are the compounds of formulas (L-1-2) and (L-1-3), wherein compounds of the following formula (L-1-2-1) as an embodiment of formula (L-1-2) are especially preferred: wherein the symbols and indices have the meaning set forth above and preferably correspond to the preferred embodiments mentioned above.

[0156] Particularly preferred embodiments of the compounds of formula (L-2) correspond to the following formulas (L-2-1 ) and / or (L-2-2) where the symbols Ar 15 and R 15, which have the aforementioned meanings and preferably correspond to the preferred embodiments mentioned above, and the following applies to the other symbols:

[0157] Y 2 is chosen from a bond, 0, S, NR, in every occurrence, whether the same or different. 15 and (C(R) 15 )2; k is 1, 2, 3 or 4, preferably 1 or 2; i is 1, 2 or 3, preferably 1 or 2, particularly preferably 1. Preferred specific compounds that can be used as hole conductor material according to the present invention are listed in the following table:

[0158] Preferably, these arylamines and heterocycles, which are generally used as hole injection and / or hole transport materials, lead to a HOMO of more than -5.8 eV (relative to vacuum level), particularly preferably more than -5.5 eV, as defined by quantum mechanical calculations. According to a preferred embodiment of the present invention, the composition (hereinafter also referred to as the mixture) contains, in addition to the components of the compound according to formula (I) and the hole transport material as previously or preferably described, no further components, i.e., functional materials. These are thus material mixtures that are used as such for the production of the hole transport layer. These mixtures are also referred to as premix systems, which are used as the sole material source in the evaporation of the materials for the hole transport layer and which have a constant mixing ratio during evaporation.This makes it possible to achieve the vapor deposition of a layer with a uniform distribution of components in a simple and quick way, without the need for precise control of a large number of material sources.

[0159] Preferred are premix systems consisting of two materials, namely a compound of formulas (11-a), (11-b), (11-c) or (11-d) and a compound of formulas (L-1 ) or (L-2), particularly preferably a compound of formulas (11-a1 ), (11-a2), (11-b1 ), (11-b2), (11-c1 ), (11-c2), (11-d1 ) or (11-d2) and a compound of formulas (L-1-1 ), (L-1 -2), (L-1 -3), (L-1 -4), (L-1 -5), (L-1 -6), (L-1 -7), (L-1 -8) or (L-1 -9).

[0160] Preferably, the composition may further include at least one hole transport material and at least one compound according to formula (I), wherein the hole transport material and the compound according to formula (I) are sublimable and the difference in the sublimation temperature is at most 5 °C, preferably at most 2 °C, wherein the sublimation temperature is determined e.g. by vacuum TGA measurement.

[0161] This design provides easily and safely sublimable compositions that can be used with particular reliability in a plant for the production of very high-quality electronic devices. Preferably, the composition may therefore comprise at least one compound according to formula (I) or preferred embodiments of this formula and at least one electron transport material.

[0162] Compounds exhibiting electron injection and / or electron transport properties, hereinafter referred to as electron transport materials, include, for example, 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 heterocycles with a low-lying LUMO (LUMO = lowest unoccupied molecular orbital).

[0163] Particularly suitable compounds for electron-transporting and electron-injecting layers are metal chelates of 8-hydroxyquinoline (e.g., LiQ, AIQ3, GaQ3, MgQt2, ZnQ2, InQ3, ZrQ4), BAIQ, Ga-oxinoid complexes, 4-azaphenanthrene-5-ol-Be complexes (US 5529853 A, see formula ET-1), butadiene derivatives (US 4356429), heterocyclic optical brighteners (US 4539507), 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). 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), silacyclopentadiene derivatives (EP 1480280, EP 1478032, EP 1469533), borane derivatives such as triarylborane derivatives with Si (US 2007 / 0087219 A1, cf.Formula ET-3), pyridine derivatives (JP 2004-200162), 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 anthracene-linked phenanthrolines (US 2007-0122656 A1, see formulas ET-4 and ET-5).

[0164]

[0165] 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 1,3,4-oxadiazoles, 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.

[0166] Organic compounds such as derivatives of fluorenone, fluorenylidenemethane, perylenetetracarbonic acid, anthraquinone dimethane, diphenoquinone, anthrone, and anthraquinone diethylenediamine can also be used. 2,9,10-substituted anthracenes (with 1- or 2-naphthyl and 4- or 3-biphenyl) or molecules containing two anthracene units are preferred (US 2008 / 0193796 A1, see formula ET-6). The combination of 9,10-substituted anthracene units with benzimidazole derivatives is also very advantageous (US 2006 147747 A and EP 1551206 A1, see formulas ET-7 and ET-8).

[0167] Formula ET-6

[0168] Formula ET-8

[0169] In a preferred embodiment, the composition may include at least one electron transport material selected from compounds of formulas (E-1) to (E-4). where the symbol R 15, which has the meaning previously mentioned especially for formula (L-1 ) and which applies to the further symbol:

[0170] Ar 18 is selected from aromatic ring systems with 6 to 50 aromatic ring atoms, separated by R groups 15 which can be substituted with non-H atoms, and heteroaromatic ring systems which can contain N atoms, with 5 to 50 aromatic ring atoms separated by R groups 15 can be substituted with something other than H.

[0171] Compounds according to formulas (E-1 ) to (E-3) are preferred.

[0172] 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) where the symbols R 15 , which has the meaning previously mentioned in particular for formula (L-1) and preferably corresponds to the preferred embodiments mentioned above, and for the further symbols the following applies:

[0173] Ar 19 is selected from aromatic ring systems with 6 to 20 aromatic ring atoms, separated by R groups 15 which can be substituted with non-H atoms, and heteroaromatic ring systems which can contain N atoms, with 5 to 20 aromatic ring atoms separated by R groups 15 can be substituted with values ​​other than H; m is 0 or 1, where m = 0 means that the group with index m does not exist and that the elements attached to the group (Ar 19 ) m Bound groups are directly connected to each other.

[0174] Preferred specific compounds that can be used as electron transport materials according to the present invention are listed in the following table:

[0175] According to a preferred embodiment of the present invention, the composition (hereinafter also referred to as the mixture) contains, in addition to the components of the compound according to formula (I) and the electron transport material as previously or preferably described, no further components, i.e., functional materials. It is therefore a material mixture that is used as such for the fabrication 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 multitude of material sources.Preferred are premix systems consisting of two materials, namely a compound of formulas (11-a), (11-b), (11-c) or (11-d) and a compound of formulas (E-1), (E-2), (E-3) or (E-4), particularly preferably a compound of formulas (11-a1), (11-a2), (11-b1), (11-b2), (11-c1), (11-c2), (11-d1) or (11-d2) and a compound of formulas (E-1-1) or (E-1-2).

[0176] Preferably, the composition may further include at least one electron transport material and at least one compound according to formula (I), wherein the electron transport material and the compound according to formula (I) are sublimable and the difference in the sublimation temperature is at most 5 °C, preferably at most 2 °C, wherein the sublimation temperature is determined e.g. by vacuum TGA measurement.

[0177] This design provides easily and safely sublimable compositions that can be used particularly reliably in a plant for the production of very high-quality electronic devices.

[0178] 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 (relative to vacuum level), particularly preferably less than -2.7 eV, as defined by quantum mechanical calculations.

[0179] Preferably, the composition may further include at least one electron transport material and at least one compound according to formula (I), wherein the electron transport material and the compound according to formula (I) are sublimable and the difference in the sublimation temperature is at most 5 °C, preferably at most 2 °C, wherein the sublimation temperature is determined e.g. by vacuum TGA measurement.

[0180] Furthermore, the compositions according to the invention can comprise at least one hole-blocking material (HBM). A hole-blocking material is a material which, in a multilayer composite, prevents or minimizes the transmission of holes (positive charges), particularly if this material is arranged in the form of a layer adjacent to an emission layer or a hole-conducting layer. In general, a hole-blocking material has a lower HOMO level than the hole-transporting material in the adjacent layer. Hole-blocking layers are frequently arranged between the light-emitting layer and the electron transport layer in OLEDs.

[0181] In principle, any known hole-blocking material can be used. In addition to other hole-blocking materials described elsewhere in this 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 this purpose (US 2003 / 0175553 A1). Phenanthroline derivatives, such as BCP, or phthalimides, such as TMPP, can also be used.

[0182] Furthermore, suitable hole-blocking materials are described in WO 00 / 70655 A2, WO 01 / 41512 and WO 01 / 93642 A1.

[0183] 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, particularly if this material is arranged in the form of a layer adjacent to an emission layer or an electron-conducting layer. In general, an electron blocking material has a higher LUMO level than the electron transport material in the adjacent layer.

[0184] In principle, any known electron-blocking material can be used. In addition to other electron-blocking materials described elsewhere in this application, suitable electron-blocking materials include transition metal complexes such as lr(ppz)3(US 2003 / 0175553).

[0185] Preferably, the electron blocking material can be selected from amines, triarylamines and their derivatives.

[0186] Organically functional materials, such as those described above and below, are often described by the properties of the frontier orbitals, which will be explained in more detail below.

[0187] The energy levels of molecular orbitals (highest occupied molecular orbital HOMO, lowest unoccupied molecular orbital LUMO, lowest triplet state Ti, lowest excited singlet state Si) are determined via quantum mechanical calculations. The Gaussian16 (Rev. B.01) software package is used in all quantum chemical calculations. The neutral singlet ground state is optimized at the B3LYP / 6-31 G(d) level. HOMO and LUMO values ​​are determined at the B3LYP / 6-31 G(d) level for the ground state energy optimized with B3LYP / 6-31 G(d). Subsequently, TD-DFT singlet and triplet excitations (vertical excitations) are calculated using the same method (B3LYP / 6-31 G(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 calculations, are additionally scaled by the following factors:

[0188] HOMO_corr = 0.90603 * HOMO (in eV) - 0.84836 LUMO_corr = 0.99687 * LUMO (in eV) - 0.72445 These values ​​are to be regarded as HOMO and LUMO energy levels of the materials for the purposes of this application.

[0189] The lowest triplet state Ti 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 lowest-energy excited singlet state resulting from the described quantum chemical calculation. A further aspect of the present invention is the use of a compound according to formula (I) or the preferred embodiments described above, formula (I). wherein the symbols have the aforementioned meanings, in an electronic device, in particular in an organic electroluminescent device. Oligomers, dendrimers or polymers of the present invention can be used accordingly.

[0190] Preferably, the compounds according to formula (I) may be used in an electronic device for varying the refractive index.

[0191] A further object of the present invention is an electronic device comprising at least one connection according to formula (I) or the preferred embodiments described above, formula (I) wherein the symbols have the aforementioned meanings. Electronic devices containing oligomers, dendrimers, or polymers of the present invention are included herein. An electronic device within the meaning of the present invention is a device which contains at least one layer which contains at least one organic compound. The component may also contain inorganic materials or layers which are composed entirely of inorganic materials. Particularly preferred is an electronic device selected from the group consisting of organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.).), preferably organic light-emitting diodes (OLEDs), small molecule organic light-emitting diodes (sOLEDs), polymer-based organic light-emitting diodes (PLEDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-Lasers), “organic plasmon emitting devices” (DM Koller et al., Nature Photonics 2008, 1-4); organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs) and organic electrical sensors, preferably organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.).), particularly preferably organic light-emitting diodes (OLEDs), small molecule organic light-emitting diodes (sOLEDs), polymer-based organic light-emitting diodes (PLEDs), especially phosphorescent or fluorescent OLEDs.

[0192] 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 emitting layer, or it may contain several emitting layers.If multiple emission layers are present, these preferably exhibit several 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 exhibiting blue, green, and orange or red emission are particularly preferred. The organic electroluminescence device according to the invention can also be a tandem electroluminescence device, especially for white-emitting OLEDs.

[0193] The compound according to formula (I) or the preferred embodiments described above can be used in different layers, depending on the precise structure. An organic electroluminescent device containing a compound according to formula (I) or the preferred embodiments described above in an electron transport layer and / or in a hole-blocking layer is preferred. Furthermore, an organic electroluminescent device containing a compound according to formula (I) or the preferred embodiments described above in a hole transport layer and / or electron-blocking layer is preferred. The compound according to formula (I) or the preferred embodiments described above can also be used in an emission layer.

[0194] Emission layers generally comprise emitters. The term emitter refers to a material which, after excitation (which can be achieved by the transfer of any type of energy), undergoes a radiative transition to a ground state, emitting light. Generally, two classes of emitters are known: fluorescent and phosphorescent emitters. The term fluorescent emitter refers to materials or compounds in which a radiative transition from an excited singlet state to the ground state occurs. The term phosphorescent emitter preferably refers to luminescent materials or compounds comprising transition metals.

[0195] Emitters are often also referred to as dopants if the dopants impart the properties described above to a system. In a system containing a matrix material and a dopant, a dopant is understood to be the component whose proportion in the mixture is smaller. Similarly, in a system containing a matrix material and a dopant, a matrix material is understood to be the component whose proportion in the mixture is larger. Therefore, the term phosphorescent emitters can also refer to phosphorescent dopants.

[0196] Preferably, the fluorescent emitter in the composition has a peak emission wavelength between 420 and 550 nm, preferably between 420 and 470 nm.

[0197] Preferred fluorescent-emitting compounds are selected from the class of arylamines. For the purposes of this 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 atom. 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 include aromatic anthracene amines, aromatic anthracene diamines, aromatic pyrene amines, aromatic pyrenediamines, aromatic chrysene amines, or aromatic chrysenediamines. An aromatic anthracene amine is understood to be a compound in which a diarylamine group is directly bonded to an anthracene group, preferably at the 9-position.An aromatic anthracene diamine 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 pyrenamines, pyrenediamines, chrysenamines, and chrysenediamines 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.Also preferred are the benzoindenofluorenamines disclosed in WO 2014 / 037077, the benzofluorenamines disclosed in WO 2014 / 106522, the extended benzoindenofluorenes disclosed in WO 2014 / 111269 and WO 2017 / 036574, the phenoxazines disclosed in WO 2017 / 028940 and WO 2017 / 028941 and the furan or thiophene unit-linked fluorine derivatives disclosed in WO 2016 / 150544. Furthermore, boron compounds can be used in accordance with WO 2020 / 208051, WO 2015 / 102118, WO 2016 / 152418, WO 2018 / 095397, WO 2019 / 004248, WO 2019 / 132040, US 2020 / 0161552 and WO 2021 / 089450, WO 2015 / 102118, KR 2018046851, WO 2019 / 009052, WO 2020 / 101001, US 2020 / 0207787, WO 2020 / 138874, KR 2020081978, JP 2020-147563, US 2020 / 0335705 or KR 2022041028 can be used.

[0198] Preferably, the at least one fluorescent emitter has a full width at half maximum (FWHM) < 50 nm, preferably FWHM < 40 nm, more preferably FWHM < 30 nm.

[0199] 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, more preferably of -4.9 eV to -5.1 eV, as defined by quantum chemical calculations.

[0200] Preferably, the energy of the lowest singlet state Si of the fluorescent emitter is between 2.65 eV and 2.9 eV, more preferably between 2.7 and 2.8 eV, and more preferably between 2.7 and 2.75 eV, as defined by quantum mechanical calculations.

[0201] In a preferred embodiment of the invention, the fluorescent emitter is selected from structures of the following formula (F-1 ), formula (F-1) where R has the meanings mentioned above and the following applies to the other symbols and indices used:

[0202] Ar 30 , Ar 31 , Ar 32is 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 heteroaromatic ring system may contain nitrogen, boron and / or phosphorus atoms;

[0203] Y 30 is B or N;

[0204] Y 31 , Y 32 , Y 33 is the same or different in each occurrence and stands for

[0205] 20 0, S, C(R°)2, C=O, C=S, C=NR°, C=C(R°)2, Si(R°)2, BR°, NR°, PR°, SO2, SeÜ2 or a chemical bond, provided that if Y 30 for B stands, at least one of the groups Y 31 , Y 32 , Y 33 NR° stands for, and if Y 30 N stands for at least one of the group Y 31 , Y 32 , Y 33 BR° stands for;

[0206] 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 R substituents, 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 R substituents, 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;q is either 0 or 1.;

[0207] Connections are particularly preferred where the following applies:

[0208] - q = 0; Y 30 = B; and Y 31 , Y 32 = NR°; or

[0209] - q = 0; Y 30 = B; and Y 31 , Y 32 = NR°; or

[0210] - q = 1 ; Y 30 = N; and Y 31 , Y 32 = BR°; Y 33 = chemical bond.

[0211] Examples of suitable fluorescent emitters are shown below.

[0212] Table shown:

[0213] The following are examples of preferred compounds that can serve as phosphorescent emitters. The term "phosphorescent compound" (triplet emitter) typically refers to compounds in which the emission of light occurs through a spin-forbidden transition, e.g., a transition from an excited triplet state or a state with a higher spin quantum number, e.g., a quintet state. Luminescent complexes with transition metals or lanthanides are preferred as phosphorescent compounds, particularly when they contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, indium, palladium, platinum, silver, gold, or europium, especially compounds containing indium, platinum, or copper. 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.

[0214] 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, US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, WO 2010 / 102709, WO 2011 / 032626, WO 2011 / 066898, WO 2011 / 157339, WO 2012 / 007086, WO 2014 / 008982, WO 2014 / 023377, WO 2014 / 094961, WO 2014 / 094960, WO 2015 / 036074, WO 2015 / 104045, WO 2015 / 117718, WO 2016 / 015815, WO 2016 / 124304, WO 2017 / 032439, WO 2018 / 011186, WO 2018 / 041769, WO 2019 / 020538, WO This can be taken from 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 other phosphorescent complexes without inventive effort.Since the compounds to be used according to the invention can also have a high triplet energy depending on the substitution, it is particularly possible to use them as a matrix material for blue phosphorescent emitters.

[0215] Suitable phosphorescent metal complexes that can be used in phosphorescent OLEDs or as sensitizers in hyperphosphorescent OLEDs are further disclosed, inter alia, in Sungho Nam et al., Adv. 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, and in US 2020 / 0140471, in particular the compounds on pages 166 to 175. in KR 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 and US 2022 / 0271236.

[0216] The proportion of matrix material in the emitting layer is, in this case, 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. Correspondingly, the proportion of the emitting compound is between 0.1 and 50.0 vol%, preferably between 0.5 and 20.0 vol%, and 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.

[0217] 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 may be smaller than the proportion of a single emitting compound.

[0218] Preferably, mixed matrix systems can be used. These systems preferably consist of two or three different matrix materials, and more preferably of two different matrix materials. Preferably, one of the two materials has hole-transporting properties, and the other has 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 according to the invention as matrix components of a mixed matrix system are described in more detail below.

[0219] Examples of phosphorescent compounds are listed below.

[0220]

[0221] In one embodiment, a hyperfluorescence and / or hyperphosphorescence system is preferably formed by a suitable combination of compounds.

[0222] Preferably, a fluorescent emitter is used in combination with one or more phosphorescent materials (triplet emitter) and / or a compound that represents a TADF (thermally activated delayed fluorescence) host material.

[0223] 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, with the energy being transferred from the phosphorescent compound to the fluorescent emitter (hyperphosphorescence). In this context, the phosphorescent compound behaves like a host material. As those skilled in the art know, 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. The systems disclosed in the prior art exhibit precisely such an energy ratio.

[0224] A fluorescent emitter can preferably be used in combination with a TADF host material and / or a TADF emitter, as previously described. The process, known as thermally activated delayed fluorescence (TADF), is described, for example, by BH Uoyama et al., Nature 2012, Vol. 492, 234. To enable this process, a comparatively small singlet-triplet distance AE(Si-Ti) of, for example, less than approximately 2000 cm⁻¹ is required in the emitter. -1 necessary. In order to open the inherently spin-forbidden Ti -> Si transition, another compound can be provided in the matrix next to the emitter, which exhibits strong spin-orbit coupling, so that inter-system crossing is enabled via the spatial proximity and the resulting possible interaction between the molecules, or the spin-orbit coupling is generated via a metal atom contained in the emitter.

[0225] 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.

[0226] Host materials generally exhibit larger band gaps between the HOMO and LUMO than the emitter materials used. Additionally, preferred host materials display either hole-transport or electron-transport properties. Furthermore, host materials can exhibit both electron- and hole-transport properties.

[0227] 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.

[0228] Preferred host materials or co-host materials, which are used particularly together with fluorescent dopants, are selected from the classes of oligoarylenes (e.g., 2,2',7,7'-tetraphenylspirobifluorene according to EP 676461 or dinaphthylanthracene), in particular oligoarylenes containing fused aromatic groups such as anthracene, benzanthracene, benzphenanthrene (DE 102009 005746, WO 09 / 069566), phenanthrene, tetracene, coronene, chrysene, fluorene, spirofluorene, perylene, phthaloperylene, naphthaloperylene, decacycles, rubrene, and oligoarylene vinylenes (e.g., DPVBi = 4,4'-bis(2,2-diphenyl-ethenyl)-1,T-biphenyl). or Spiro-DPVBi according to EP 676461), the polypodal metal complexes (e.g. according to WO 04 / 081017), in particular metal complexes of 8-hydroxyquinoline, e.g.AIQ3 (= Aluminium(III)tris(8-hydroxyquinoline)) or 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, 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 Benzanthracene (e.g. according to WO 08 / 145239).

[0229] Particularly preferred compounds that can serve as host materials or co-host materials are selected from the classes of oligoarylenes containing anthracene, benzanthracene and / or pyrene or atropisomers of these compounds. For the purposes of this invention, an oligoarylene is understood to be a compound in which at least three aryl or arylene groups are bonded to one another.

[0230] Preferred host materials are in particular selected from compounds of the formula (H-100), (H-100) where Ar 5 , Ar 6 , Ar 7 where, 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 ir electrons in Ar 5 , Ar 6 and Ar 7at least 30 if p = 1, and at least 36 if p = 2, and at least 42 if p = 3.

[0231] 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, whereby these groups may be substituted. At least one of the groups Ar is particularly preferred. 5 and / or Ar 7a condensed aryl group selected from 1- or 2-naphthyl, 2-, 3- or 9-phenanthrenyl or 2-, 3-, 4-, 5-, 6- or 7-benz-anthracenyl. Anthracene-based compounds are described in US 2007 / 0092753 A1 and US 2007 / 0252517 A1, e.g., 2-(4-methylphenyl)-9,10-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-anthracenyl)benzene. Compounds with two anthracene units are also preferred (US 2008 / 0193796 A1), e.g. 10,10'-Bis[1 ,1 ',4',1 ”]-terphenyl-2-yl-9,9'-bisanthracenyl.

[0232] Other preferred compounds are derivatives of arylamine, styrylamine, fluorescein, diphenylbutadiene, tetraphenylbutadiene, cyclopentadiene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, coumarin, 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, diaminocarbazole, pyran, thiopyran. Diketopyrrolopyrrole, polymethin, cinnamic acid esters and fluorescent dyes.

[0233] Particularly preferred are derivatives of arylamine and styrylamine, e.g., TNB (= 4,4'-bis[N-(1-naphthyl)-N-(2-naphthyl)amino]biphenyl). Metal I oxinoid complexes such as LiQ or AIQ3 can be used as co-hosts.

[0234] 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 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 .

[0235]

[0236] Furthermore, compounds that can be used as a host or matrix include materials that are used together with phosphorescent emitters. Preferred matrix materials for phosphorescent compounds, which can also be used in combination with the compounds according to the invention, are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680, triarylamines, carbazole derivatives, e.g. CBP (N,N-biscarbazolylbiphenyl) 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, indenocarbazole derivatives, e.g. according to WO 2010 / 136109, WO 2011 / 000455, WO 2013 / 041176 or WO 2013 / 056776, azacarbazole derivatives, e.g. according to EP 1617710, EP 1617711, EP 1731584, JP 2005 / 347160, bipolar matrix materials, e.g. according to WO 2007 / 137725, silanes, e.g.according to WO 2005 / 111172, azaboroles or boron esters, e.g. according to WO 2006 / 117052, triazine derivatives, e.g. according to WO 2007 / 063754, WO 2008 / 056746, WO 2010 / 015306, WO 2011 / 057706, WO 2011 / 060859 or WO 2011 / 060877, zinc complexes, e.g. according to EP 652273 or WO 2009 / 062578, diazasilol or tetraazasilol derivatives, e.g. according to WO 2010 / 054729, diazaphosphole derivatives, e.g. according to WO 2010 / 054730, bridged carbazole derivatives, e.g. according to WO 2011 / 042107, WO 2011 / 060867, WO 2011 / 088877 and WO 2012 / 143080, triphenylene derivatives, e.g. according to WO 2012 / 048781, lactams, e.g. according to WO 2011 / 116865 or WO 2011 / 137951, dibenzofuran derivatives, e.g. according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO 2017 / 148565 or bridged triarylbor compounds, for example according to US 2021 / 0122765.Similarly, another phosphorescent emitter, which emits at a shorter wavelength than the actual emitter, may be present in the mixture as a co-host, or a compound that does not participate in charge transport or does not participate to a significant extent, as described, for example, in WO 2010 / 108579.

[0237] The previously cited publications describing the functional materials which can be used to manufacture functional layers of electronic devices are incorporated into the present application for disclosure purposes by reference thereto.

[0238] Furthermore, the electronic device may be an organic electroluminescent device comprising an electron transport layer, wherein the electron transport layer comprises at least one electron transport material and a compound according to formula (I). Preferably, the electron transport layer may contain a composition according to the invention, preferably consisting of a composition according to the invention, wherein this composition comprises an electron transport material.

[0239] Furthermore, it may be provided that the electronic device is an organic electroluminescent device and that the electroluminescent device comprises a hole transport layer, wherein the hole transport layer comprises at least a hole conductor material and a compound according to formula (I).

[0240] Preferably, the hole transport layer can contain a composition according to the invention, preferably consisting of a composition according to the invention, wherein this composition comprises a hole conductor material.

[0241] The ordinary refractive indices of the layers of an electronic device, preferably an organic electroluminescent device, measured via ellipsometry at 450 nm, are preferably less than 1.8, more preferably less than 1.7, more preferably less than 1.6 and particularly preferably less than 1.5.

[0242] In the further layers of the organic electroluminescent device according to the invention, all materials commonly used in the prior art can be employed. Therefore, without any inventive effort, a person skilled in the art can use all materials known for organic electroluminescent devices in combination with the compounds according to formula (I) or the preferred embodiments described above.

[0243] In addition to the layers described above, an electronic device, preferably an organic electroluminescent device, may comprise further layers. In particular, a compound according to formula (I) or preferred embodiments of this formula may be used to produce an outcoupling layer, a capping layer, or a matching layer. A further preferred aspect of the present invention is therefore an electronic device, preferably an organic electroluminescent device, with an outcoupling layer, a capping layer, or a matching layer comprising a compound according to formula (I) or preferred embodiments of this formula, preferably consisting of one or more of these compounds.

[0244] Preferred electroluminescent devices (OLEDs) according to the invention comprise the following layer structure, whereby it is not excluded that further layers are present:

[0245] - Anode

[0246] - Bone Injectable Layer (HIL)

[0247] - Hole transport layer (HTL)

[0248] - Electron blocking layer (EBL)

[0249] - Emission layer (EML) containing a fluorescent or phosphorescent dopant

[0250] - Hole-blocking layer (HBL)

[0251] - Electron transport layer (ETL)

[0252] - Electron injection layer

[0253] - Cathode.

[0254] Various embodiments of the invention are summarized in the following table:

[0255] The fluorescent or phosphorescent EML can emit blue, green, yellow, or red light, respectively. In a preferred embodiment, the fluorescent EML is a blue-emitting layer. The fluorescent EML can also be a hyperfluorescent EML containing a TADF compound as a sensitizer, or a hyperphosphorescent EML containing a phosphorescent compound as a sensitizer. In another preferred embodiment, the phosphorescent EML is a green, yellow, or red-emitting layer.

[0256] A further preferred organic electroluminescence device is characterized in that one or more layers are coated using a sublimation process. The materials are applied in vacuum sublimation systems at an initial pressure of less than 10⁻⁵ m. 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.

[0257] 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 are coated at a pressure between 10° 5 Pressures 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.

[0258] A further preferred organic electroluminescent device is characterized in that one or more layers are produced from solution, e.g., by spin coating, or by any printing process, e.g., screen printing, flexographic printing, offset printing, LITI (light-induced thermal imaging, thermal transfer printing), inkjet printing, or nozzle printing. Soluble compounds are required for this purpose, which can be obtained, for example, by suitable substitution.

[0259] Formulations for applying a compound according to formula (I) or its previously described preferred embodiments are novel. A further object of the present invention is therefore a formulation comprising at least one solvent and a compound according to formula (I) or its previously described preferred embodiments.

[0260] 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.

[0261] 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 (I) or the preferred embodiments described above and below.

[0262] Depending on their specific embodiment, the compounds and organic electroluminescent devices according to the invention can be characterized by a low refractive index (RI). Furthermore, these compounds and the organic electroluminescent devices obtained therefrom exhibit an improved lifetime. The other electronic properties of the electroluminescent devices, such as efficiency, remain at least as good. In a further embodiment, the compounds and organic electroluminescent devices according to the invention are distinguished from the prior art, in particular, by improved efficiency and / or a longer lifetime.

[0263] 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:

[0264] 1. Electronic devices, in particular organic electroluminescent devices containing compounds according to formula (I) or the preferred embodiments described above and below, especially in combination with an emitter, with a matrix material, with a hole-conducting material or with an electron-conducting material, exhibit excellent efficiency.

[0265] 2. Electronic devices, in particular organic electroluminescent devices containing compounds according to formula (I) or the preferred embodiments described above and below, especially in combination with an emitter, with a matrix material, with a hole-conducting material or with an electron-conducting material, have a very good lifetime.

[0266] 3. The compounds according to formula (I) or the preferred embodiments described above and below exhibit very high stability.

[0267] 4. Electronic devices, in particular organic electroluminescent devices containing compounds according to formula (I) or the preferred embodiments described above and below, exhibit very low refractive indices. 5. With compounds according to formula (I) or the preferred embodiments described above and below, the formation of losses due to optical reflection can be avoided in electronic devices, in particular organic electroluminescent devices.

[0268] 6. Compounds according to formula (I) or the preferred embodiments described above and below exhibit excellent glass film formation.

[0269] 7. Compounds according to formula (I) or the preferred embodiments described above and below form very good films from solutions.

[0270] These aforementioned advantages do not come at the cost of an excessively high deterioration of other electronic properties.

[0271] It should be noted that variations of the embodiments described in the present invention fall within the scope of this invention. Unless explicitly excluded, each feature disclosed in the present invention may be replaced by alternative features serving the same, an equivalent, or a similar purpose. Thus, unless otherwise stated, each feature disclosed in the present invention is to be considered as an example of a generic series or as an equivalent or similar feature.

[0272] All features of the present invention can be combined with one another in any way, unless certain features and / or steps are mutually exclusive. This applies in particular to preferred features of the present invention. Likewise, features of non-essential combinations can be used separately (and not in combination).

[0273] It should further be noted that many of the features, and in particular those of the preferred embodiments of the present invention, are themselves inventive and not merely to be considered part of the embodiments of the present invention. Independent protection for these features may be sought in addition to or as an alternative to any currently claimed invention.

[0274] The teaching on technical action disclosed in the present invention can be abstracted and combined with other examples.

[0275] The invention is further explained by the following examples, without being intended to limit it. A person skilled in the art can implement the invention in its entire disclosed scope from the descriptions and, without inventive effort, create further connections according to the invention and use them in electronic devices or apply the method according to the invention.

[0276] Examples:

[0277] 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 and the numbers given for individual compounds refer to the CAS numbers of the compounds known from the literature. For compounds that can have several isomeric, enantiomeric, diastereomeric, or tautomeric forms, one form is shown as a representative example.

[0278] A: Synthons known in literature:

[0279] 2) MonoHalogenSilane MHS, MonoHalogenGermane MHS:

[0280] 3) DiHalogenSilane DHS, DiHalogenGermane DHG:

[0281] 4) TriHalogenSilane THS, TriHalogenGermane THG

[0282] 5) TetraHalogenDiSilane, TetraHalogenDiGermane, HexaHalogenDiSilane, HexaHalogenDiGermane:

[0283] B Representation of the synthons S:

[0284] Example S1

[0285] 800 ml n-heptane are mixed with 3.3 g (5 mmol) B is[( 1 ,2, 5,6-r|)-1 ,5-cyclo-octadiene]di-p-methoxydi-iridium(l) [12148-71-9], then with 2.7 g (10 mmol) 4,4'-Di-tert-butyl-[2,2']bipyridinyl [72914-19-3] and then with 5.1 g (10 mmol) Bis(pinkolato)diborane and stirred for 15 minutes at room temperature. Then, 127.0 g (500 mmol) of bis(pinacolato)diborane and then 113.2 g (500 mmol) of dispiro[cyclopentane-1,1'-[1H]indene-3'(2'H),1"-cyclopentane] [405281-78-9] are added, and the mixture is heated to 80 °C for 12 hours (TLC control: heptane:ethyl acetate 5:1). After cooling, the reaction mixture is treated with 300 ml of ethyl acetate, filtered through a silica gel bed, and the filtrate is completely concentrated under vacuum. The crude product is recrystallized twice from acetone (approx. 800 ml). Yield: 158.8 g (450 mmol), 90%; purity: approx. 99%. 1 H-NMR. b) S1

[0286] 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% after 1 H-NMR.

[0287] C: Representation of the compounds according to the invention:

[0288] Example B1:

[0289] Representation according to DE4229086, example 2.

[0290] A well-stirred mixture of 102.3 g (404 mmol) AB1 and 1000 ml diethyl ether, cooled to -78 °C, is treated dropwise with 475.3 ml (808 mmol) tert-butyllithium, 1.7 M in n-hexane. After stirring for 15 minutes, the mixture is allowed to warm to 10 °C, and then a mixture of 11.5 ml (100 mmol) silicon tetrachloride [10026-04-7] and 100 ml diethyl ether is slowly added dropwise. After the exothermic reaction has subsided, the mixture is heated under reflux for 2 hours. After cooling, slowly pour into 2 L of ice-cold 2 N hydrochloric acid with good stirring, stir briefly, separate the organic phase, wash it twice with 300 mL of water each time, once with 300 mL of saturated sodium chloride solution, and dry over a mixture of magnesium sulfate and potassium carbonate. Filter from the drying agent over a silica gel bed and concentrate under vacuum to dryness. Further purification is carried out by repeated hot extraction crystallization (using common organic solvents or...).whose combinations, preferably acetonitrile-DCM, 1:3 to 3:1 vv) or chromatography and fractional sublimation or annealing under high vacuum. Yield: 55.3 g (77 mmol), 77%; Purity: approx. 99.9% by HPLC.

[0291] Similarly, the following compounds can be represented, if necessary by adjusting the stoichiometry.

[0292]

[0293] D: Preparation of Mixtures: PreMix Example: PreMixl A mixture of 7.5 g HTM [136463-07-5], vacuum TGA (5 wt% - condensed): 211 °C, see Table 4, and 2.5 g B4, vacuum TGA (5 wt% - condensed): 212 °C, is carefully melted in a Schlenk tube under argon without overheating the melt. After homogenizing the melt, it is allowed to cool, and the resulting organic glass is pulverized. In this form, it is used as PreMix I for the production of OLED components, see Example 2b.

[0294] E: Examples of devices

[0295] In the following examples, OLEDs according to the invention (examples E1a to E1g, E2a to E2r, E3a, E4a and E4b) and one OLED according to the prior art (comparative examples C1, C2, C3, C4a and C4b) 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. The properties of the OLEDs according to the invention of examples E1a to E1g, E2a to E2r, E3a, E4a and E4b and the properties of the OLEDs according to the prior art are listed in Tables 5, 6, 7 and 9.

[0296] Manufacturing of OLEDs

[0297] Glass platelets coated with a 50 nm thick, structured ITO (indium tin oxide) serve as the substrate for the OLEDs. All materials are thermally vapor-deposited in a vacuum chamber. The emission layer always consists of at least one matrix material (also called host material) and an emitting dopant, which is added to the matrix material(s) by cover vapor deposition in a specific volume fraction. A specification such as BH:BD (97:3) 20 nm means that the material BH is present as the host material in a volume fraction of 97%, and the compound BD in a volume fraction of 3% in a 20 nm thick layer. Similarly, the hole injection layer (HIL), the hole transport layer (HTL), and the electron transport layer (ETL) can also consist of a mixture of two or more materials. The structure of the respective OLEDs is shown in Tables 1, 2, 3, and 8.

[0298] Table 1: Table 2:

[0299] Table 3:

[0300] Table 8:

[0301] Table 4: OLED materials

[0302] Characterization of OLEDs

[0303] The OLEDs are characterized according to standard procedures. For this, the electroluminescence spectra and current-voltage-luminance (IIIL) curves are measured, and the EQE is calculated from these measurements. The calculation assumes 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.

[0304] 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 at a current density of 10 mA / cm². 2 .

[0305] For each example, the relative EQE and the relative voltage are calculated in comparison to the respective reference example: rel. U (Ex) = (U10(Ex) / U10(V)) rel. EQE (Ex) = (EQE10(Ex) / EQE10(V))

[0306] 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.

[0307] Samples for determining the refractive index (RI) are prepared on SiO2 substrates with three different layer thicknesses. The respective material is thermally vapor-deposited. From these measurements, the mean refractive index value for each material or material mixture is determined.

[0308] The results are shown in Tables 5, 6 and 7 below.

[0309] Properties of OLEDs

[0310] Table 5: Properties of OLEDs

[0311] (* of the complete ETL layer of the OLED)

[0312] Table 6: Properties of OLEDs

[0313] (* of the complete HTL layer of the OLED)

[0314] Table 7: Properties of OLEDs

[0315] Table 9: Properties of OLEDs

[0316] (* of the complete ETL layer of the OLED)

[0317] When comparing the inventive examples E1a to E1g, E2a to E2r, E3a, E4a and E4b with the corresponding comparative examples C1, C2, C3, C4a and C4b, 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 the inventive materials; for example, the refractive index of B4 is 1.53. The other compounds according to the invention have similar 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.

[0318] E: Device examples for green phosphorescent OLEDs

[0319] In the following three examples, OLEDs according to the invention (examples gE1a-c, gE2a-b, gE3a and gE4a) and one OLED according to the prior art (comparative examples gC1, gC2, gC3 and gC4) are produced. The exact structure of the OLEDs can be found in Table 10. The materials used to produce the OLEDs, in addition to those already shown, are shown in Table 11. The properties of the OLEDs according to the invention in the examples and comparative examples are summarized in Table 12.

[0320] Production of green OLEDs

[0321] 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 (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 layer (HIL), hole transport layer (HTL), electron blocking layer (EBL), hole blocking layer (HBL), and electron transport layer (ETL) consist of a mixture of two or more materials. The structure of the respective OLEDs is shown in Table 10, and materials for green OLEDs are shown in Table 11. After the electron injection layer (EIL) is deposited, a 100 nm aluminum cathode is deposited onto each component. Table 10: Structure of green OLEDs.

[0322] Table 11: OLED materials - green OLEDs (in addition to the materials of blue OLEDs in Table 4)

[0323] Characterization of the green phosphorescent OLEDs: The OLEDs are characterized using standard procedures. This is done analogously to the characterization of the blue OLEDs. The results are summarized in Table 12.

[0324] Table 12: Properties of OLEDs

[0325] When comparing the inventive examples gE1a-c, gE2a-b, gE3a and gE4a with the corresponding comparative examples gC1, gC2, gC3 and gC4, it is clearly evident that the inventive OLEDs show a significant advantage in device efficiency, without negatively affecting lifetime, voltage and color.

Claims

Patent claims 1. Compound according to formula (I), Formula (I) where the following applies to the symbols: M stands for Si or Ge; R 1 , R 2 , R 3 and R 4In each occurrence, the compound may be a straight-chain alkyl group with 1 to 40 carbon atoms, a branched or cyclic alkyl group with 3 to 40 carbon atoms, each of which may be substituted with one or more R groups other than H, a non-condensed or condensed aromatic ring system with 6 to 60 aromatic ring atoms, or a non-condensed or condensed heteroaromatic ring system with 5 to 60 aromatic ring atoms, which includes at least one heteroatom selected from O and S, preferably one heteroatom selected from O and S, and particularly preferably an O atom, wherein the aromatic or heteroaromatic ring system may be substituted with one or more R groups other than H, one of which may be R 1 , R 2 , R 3 and R 4 with another of the remains R 1 , R 2 , R 3 and R 4 form a ring; provided that at least one of the residues R1 , R 2 , R 3 and R 4 corresponds to the following formula (1a), R is the same or different from H, D, F, C(Ar')3, C(R')3, Si(Ar')3, Si(R')3, Ge(Ar')3, Ge(R')3, , a straight-chain alkyl group with 1 to 40 carbon atoms, or an alkenyl or alkynyl group with 2 to 40 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein the alkyl, alkenyl, or alkynyl group may each be substituted with one or more R' groups other than H, wherein one or more non-adjacent CH2 groups may be replaced by Si(R')2, an aromatic ring system with 6 to 60 aromatic ring atoms, or a heteroaromatic ring system with 5 to 60 aromatic ring atoms, which includes at least one heteroatom selected from O and S, preferably one heteroatom selected from O and S, particularly preferably an O atom, contains, wherein the aromatic and heteroaromatic ring systems can each be substituted by one or more R' groups,or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted by one or more residues R', wherein two residues R can also be linked to each other or one residue R to another group, in particular a residue R, a , R b , R c and R d form a ring system; Ar' is, in each occurrence, either the same or different, an aromatic ring system with 6 to 60 aromatic ring atoms, or a heteroaromatic ring system with 5 to 60 aromatic ring atoms, which includes at least one heteroatom selected from O and S, preferably one heteroatom selected from O and S, particularly preferably one O atom, wherein the aromatic and heteroaromatic ring system can be substituted with one or more R' substituents other than H, whereby two Ar' substituents bonding to the same C atom or Si atom can also be bridged by a single bond or a bridge selected from C(R')2, Si(R')2, C=O, C=C(R')2, O, S, S=O and SO2; R' is selected in each instance, either the same or differently, from the group consisting of H, D, F, an aliphatic hydrogen carbonate residue with 1 to 20 C atoms, an aromatic ring system with 6 to 30 aromatic ring atoms, or a heteroaromatic ring system with 5 to 30 aromatic ring atoms, in which at least one heteroatom is selected from O and S, preferably one heteroatom selected from O and S, particularly preferably one O atom, wherein in the aromatic and heteroaromatic ring system one or more H atoms may be replaced by D, F and which may be substituted by one or more alkyl groups with 1 to 4 carbon atoms each, wherein two or more substituents R' may form a ring system together; R a , R b , R c and R dF is the same or different in each occurrence, a straight-chain alkyl group with 1 to 40 C atoms or a branched or cyclic alkyl group with 3 to 40 C atoms, each of which may be substituted with one or more R' groups other than H, where one R group may be a with a remainder R b or one of the remains R a or R b with one of the remaining R c or R d form a ring; n is the same or different (1, 2, or 3) in each occurrence; R e and R f is the same or different H, D, F, a straight-chain alkyl group with 1 to 40 C atoms or a branched or cyclic alkyl group with 3 to 40 C atoms, each with one or more R' substituents not equal to H They can be substituted, and a residual R may remain. e with a remainder R f form a ring.

2. Compound according to claim 1, characterized in that one, two, three or four, preferably three or four of the residues R 1 , R 2 , R 3 and R 4 correspond to formula (1a).

3. Compound according to claim 1 or 2, characterized in that formula (1a) corresponds to the following formula (1b) or (1c), wherein the symbols have the meanings mentioned in claim 1.

4. Compound according to one or more of claims 1 to 3, characterized in that the compound corresponds to one of the following formulas (Ha) to (I Id), Formula (Ile) wherein the symbols and indices have the meanings mentioned in claim 1.

5. Compound according to claim 4, characterized in that all n = 1 or that all n = 2 or that in formulas (Hb) to (I Id) there is at least one n = 1 and at least one n = 2.

6. Compound according to one or more of claims 1 to 5, characterized in that the two residues R a and R b together with the C atom to which the two R groups are attached a and R b bind, and / or that the two residues R c and R d together with the C atom to which the two R groups are attached c and R d bind, form a ring of formulas (RC-1 ) to (RC-14), or R 2 , R 3 and / or R 4 The structure selected is from formulas (RC-1 ) to (RC-14) wherein R' has the meaning set out in claim 1, the dashed bonds represent the attachment points to the respective group, and the other symbols have the following meanings: r is 0, 1, 2, 3, 4, 5 or 6; s is 0, 1, 2, 3, 4, 5, 6, 7 or 8; t is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; v is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; z is either 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 13, 14, 15 or 16 in each instance.

7. Compound according to formula (Illa) and (lllb), formula (Illa) Formula (lllb) wherein the symbols have the meanings mentioned in claim 1 and the dashed line represents any group of connections.

8. Compound according to one or more of claims 1 to 7, characterized in that M in formulas (I), (Ha) to (I Id), (Illa) and (lllb) stands for Si.

9. Compound according to one or more of claims 1 to 8, characterized in that the compounds of formulas (I), (Ha) to (I Id), (Illa) and (lllb) are partially deuterated or fully deuterated.

10. Oligomer, polymer or dendrimer comprising one or more compounds according to any one of claims 1 to 9, wherein instead of a hydrogen atom or a substituent, one or more bonds of the compounds to the polymer, oligomer or dendrimer are present.

11. Formulation comprising at least one compound according to one or more of claims 1 to 9 or an oligomer, polymer or dendrimer according to claim 10 and at least one further compound, wherein the further compound is preferably selected from one or more solvents.

12. Composition comprising at least one compound according to one or more of claims 1 to 9 or an oligomer, polymer or dendrimer according to claim 13 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 conductor materials, hole injection materials, electron blocking materials and hole blocking materials.

13. Method for producing a compound according to one or more of claims 1 to 9, characterized in that first an aryl halide is reacted to form an aryl metal compound and the aryl metal compound is then reacted with a halogen-silicon compound or a halogen-germanium compound by salt metathesis.

14. Use of a compound according to one or more of claims 1 to 9 or an oligomer, polymer or dendrimer according to claim 10 in an electronic device.

15. Electronic device comprising at least one compound according to one or more of claims 1 to 9 or an oligomer, polymer or dendrimer according to claim 10.

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