Materials for electronic devices

Abstract

The present invention relates to compounds of a formula (I) or (II), processes for preparing compounds of this type, electronic devices, in particular OLEDs, containing one or more of these compounds, and the use of these compounds in electronic devices, in particular in OLEDs.

Description

[0001] Materials for electronic devices This application relates to aromatic amines that contain certain aromatic or heteroaromatic ring systems on the amine nitrogen atom. The compounds are suitable for use in electronic devices. Electronic devices within the meaning of this application are understood to be so-called organic electronic devices that contain organic semiconductor materials as functional materials. In particular, this refers to OLEDs (organic electroluminescent devices). The term OLEDs refers to electronic devices that have one or more layers containing organic compounds and emit light when an electrical voltage is applied. The structure and general operating principle of OLEDs are known to those skilled in the art.There is great interest in improving the performance of electronic devices, particularly OLEDs. A completely satisfactory solution has not yet been found in these areas. Emission layers and layers with hole-transporting functions have a significant influence on the performance of electronic devices. New compounds are still being sought for use in these layers, particularly hole-transporting compounds and compounds that can serve as hole-transporting matrix materials, particularly for phosphorescent emitters, in an emitting layer. For this purpose, compounds are particularly sought that exhibit a high glass transition temperature, high stability, and high hole conductivity. High compound stability is a prerequisite for achieving a long service life of the electronic device.Furthermore, compounds are sought whose use in electronic devices leads to improved device performance, in particular high efficiency, long service life, and low operating voltage. In the prior art, triarylamine compounds such as spirobifluorenamines and fluorenamines are known in particular as hole-transport materials and hole-transporting matrix materials for electronic devices. However, there is still a need for improvement with regard to the above-mentioned properties. It has now been found that aromatic amines according to the formulas below, which are characterized by having certain aromatic or heteroaromatic ring systems on the amine nitrogen atom, are outstandingly suitable for use in electronic devices.They are particularly suitable for use in OLEDs, particularly therein as hole-transport materials and for use as hole-transporting matrix materials, especially for phosphorescent emitters. The compounds lead to long lifetimes, high efficiency, and low operating voltage of the devices. Furthermore, the compounds found preferably have a high glass transition temperature, high stability, a low sublimation temperature, good solubility, good synthetic accessibility, and high hole conductivity. The present application thus relates to a compound according to one of the following formulas: where: W is the same or different at each occurrence and is selected from O and S, preferably O; Z is the same or different at each occurrence and is selected from CR 1 and N, preferably CR 1; i is equal to 0 or 1, where for i=0 the group Y is omitted; for i = 0 Z is 1 chosen the same or different at each occurrence from CR 1 and N; for i = 1, Z 1 for C; Y is, at each occurrence, the same or different, selected from a bond, C(R 1 )2, O or S; Ar L is selected at each occurrence, identically or differently, from aromatic ring systems with 6 to 40 aromatic ring atoms, which are substituted by radicals R 2 are substituted, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which are substituted with residues R 2 are substituted; k is equal to 0, 1, 2 or 3, where for k=0 the group Ar L is omitted and the two at Ar L bonding groups in formula (I) and (II) are directly connected to each other, where for k=2 two groups Ar L are bound in a chain one after the other, and where for k=3 three groups Ar L are bound one after the other in a chain; Ar 1is selected at each occurrence, identically or differently, from aromatic ring systems with 6 to 40 aromatic ring atoms, which are substituted by radicals R 4 are substituted, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which are substituted with residues R 4 are substituted; Ar 2 is selected at each occurrence, identically or differently, from aromatic ring systems with 6 to 40 aromatic ring atoms, which are substituted by radicals R 5 are substituted, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which are substituted with residues R 5 are substituted, wherein the aromatic or heteroaromatic ring systems are linked in the ortho position to the group V and the nitrogen atom; V is, identically or differently, selected at each occurrence from a bond, O, S, Si(R 5 )2and C(R 5 )2; R 1 is selected at each occurrence, the same or different, from H, D, F, Cl, Br, I, C(=O)R 6 , CN, Si(R 6)3, N(R 6 )2, P(=O)(R 6 )2, OR 6 , S(=O)R 6 , S(=O)2R 6 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 1 may be linked to one another and form a ring; wherein the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems are each linked to radicals R 6 are substituted; and wherein one or more CH2 groups in said alkyl, alkoxy, alkenyl and alkynyl groups are substituted by -R 6 C=CR 6 -, -C≡C-, Si(R 6 )2, C=O, C=NR 6 , -C(=O)O-, -C(=O)NR 6 -, NR 6 , P(=O)(R6 ), -O-, -S-, SO or SO2; R 2 is selected at each occurrence, the same or different, from H, D, F, Cl, Br, I, C(=O)R 6 , CN, Si(R 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 , S(=O)R 6 , S(=O)2R 6 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 2 may be linked to one another and form a ring; wherein the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems are each linked to radicals R 6are substituted; and wherein one or more CH2 groups in said alkyl, alkoxy, alkenyl and alkynyl groups are substituted by -R 6 C=CR 6 -, -C≡C-, Si(R 6 )2, C=O, C=NR 6 , -C(=O)O-, -C(=O)NR 6 -, NR 6 , P(=O)(R 6 ), -O-, -S-, SO or SO2; R 3 is selected at each occurrence, the same or different, from H, D, F, Cl, Br, I, C(=O)R 6 , CN, Si(R 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 , S(=O)R 6 , S(=O)2R 6 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 3may be linked to one another and form a ring; wherein the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems are each linked to radicals R 6 are substituted; and wherein one or more CH2 groups in said alkyl, alkoxy, alkenyl and alkynyl groups are substituted by -R 6 C=CR 6 -, -C≡C-, Si(R 6 )2, C=O, C=NR 6 , -C(=O)O-, -C(=O)NR 6 -, NR 6 , P(=O)(R 6 ), -O-, -S-, SO or SO2; R 4 is selected at each occurrence, the same or different, from H, D, F, Cl, Br, I, C(=O)R 6 , CN, Si(R 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 , S(=O)R 6 , S(=O)2R 6, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 4 may be linked to one another and form a ring; wherein the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems are each linked to radicals R 6 are substituted; and wherein one or more CH2 groups in said alkyl, alkoxy, alkenyl and alkynyl groups are substituted by -R 6 C=CR 6 -, -C≡C-, Si(R 6 )2, C=O, C=NR 6 , -C(=O)O-, -C(=O)NR 6 -, NR 6 , P(=O)(R 6 ), -O-, -S-, SO or SO2; R 5is selected at each occurrence, the same or different, from H, D, F, Cl, Br, I, C(=O)R 6 , CN, Si(R 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 , S(=O)R 6 , S(=O)2R 6 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 5 may be linked to one another and form a ring; wherein the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems are each linked to radicals R 6 are substituted; and wherein one or more CH2 groups in said alkyl, alkoxy, alkenyl and alkynyl groups are substituted by -R 6 C=CR 6-, -C≡C-, Si(R 6 )2, C=O, C=NR 6 , -C(=O)O-, -C(=O)NR 6 -, NR 6 , P(=O)(R 6 ), -O-, -S-, SO or SO2; R 6 is selected at each occurrence, the same or different, from H, D, F, Cl, Br, I, C(=O)R 7 , CN, Si(R 7 )3, N(R 7 )2, P(=O)(R 7 )2, OR 7 , S(=O)R 7 , S(=O)2R 7 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 6may be linked to one another and form a ring; wherein the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems are each linked to radicals R 7 are substituted; and wherein one or more CH2 groups in said alkyl, alkoxy, alkenyl and alkynyl groups are substituted by -R 7 C=CR 7 -, -C≡C-, Si(R 7 )2, C=O, C=NR 7 , -C(=O)O-, -C(=O)NR 7 -, NR 7 , P(=O)(R 7 ), -O-, -S-, SO or SO2; R 7 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 7may be linked together to form a ring; and wherein said alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems may be substituted by one or more radicals selected from F and CN. , drawn in a ring, it is to be understood that at each of the four free positions on the ring a residue R 3 is bound, where the residues R 3 can be the same or different at each occurrence. For similar representations, such as or corresponding definitions apply, where the remainder R 1is bonded to the corresponding ring and four or five free positions are present to which the residues are bonded, which may be the same or different at each occurrence. The following definitions apply to the chemical groups used in the present application. They apply unless more specific definitions are given. An aryl group in the sense of this invention is understood to be either a single aromatic cycle, i.e. benzene, or a condensed aromatic polycycle, for example naphthalene, phenanthrene or anthracene. A condensed aromatic polycycle in the sense of the present application consists of two or more individual aromatic cycles condensed together. Condensation between cycles is understood to meanthat the cycles share at least one edge. An aryl group within the meaning of this invention contains 6 to 40 aromatic ring atoms. Furthermore, an aryl group does not contain a heteroatom as the aromatic ring atom, but only carbon atoms. A heteroaryl group within the meaning of this invention is understood to be either a single heteroaromatic cycle, for example pyridine, pyrimidine, or thiophene, or a fused heteroaromatic polycycle, for example quinoline or carbazole. A fused heteroaromatic polycycle within the meaning of the present application consists of two or more fused individual aromatic or heteroaromatic cycles, where at least one of the aromatic and heteroaromatic cycles is a heteroaromatic cycle. Condensation between cycles is understood to meanthat the rings share at least one edge. A heteroaryl group within the meaning of this invention contains 5 to 40 aromatic ring atoms, of which at least one is a heteroatom. The heteroatoms of the heteroaryl group are preferably selected from N, O and S. An aryl or heteroaryl group, which may in each case be substituted with the above-mentioned radicals, is understood to mean, in particular, groups which are derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, triphenylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, Imidazole, benzimidazole, benzimidazolo[1,2-a]benzimidazole,Naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazinimidazole, quinoxalinimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, Pyrazine, phenazine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine, and benzothiadiazole. An aromatic ring system within the meaning of this invention is a system that does not necessarily contain only aryl groups, but may additionally contain one or more non-aromatic rings.which are condensed with at least one aryl group. These non-aromatic rings contain exclusively carbon atoms as ring atoms. Examples of groups encompassed by this definition are tetrahydronaphthalene, fluorene, and spirobifluorene. Furthermore, the term aromatic ring system encompasses systems consisting of two or more aromatic ring systems linked to one another via single bonds, for example biphenyl, terphenyl, 7-phenyl-2-fluorenyl, quaterphenyl, and 3,5-diphenyl-1-phenyl. An aromatic ring system within the meaning of this invention contains 6 to 40 C atoms and no heteroatoms in the ring system. The definition of "aromatic ring system" does not include heteroaryl groups. A heteroaromatic ring system corresponds to the above definition of an aromatic ring system, with the difference that it must contain at least one heteroatom as a ring atom. As is the case with the aromatic ring system,The heteroaromatic ring system need not contain exclusively aryl groups and heteroaryl groups, but may additionally contain one or more non-aromatic rings fused with at least one aryl or heteroaryl group. The non-aromatic rings may contain exclusively C atoms as ring atoms, or they may additionally contain one or more heteroatoms, wherein the heteroatoms are preferably selected from N, O, and S. An example of such a heteroaromatic ring system is benzopyranyl. Furthermore, the term "heteroaromatic ring system" refers to systems consisting of two or more aromatic or heteroaromatic ring systems linked to one another via single bonds, such as, for example, 4,6-diphenyl-2-triazinyl. A heteroaromatic ring system within the meaning of this invention contains 5 to 40 ring atoms selected from carbon and heteroatoms.wherein at least one of the ring atoms is a heteroatom. The heteroatoms of the heteroaromatic ring system are preferably selected from N, O, and S. The terms “heteroaromatic ring system” and “aromatic ring system” as defined in the present application thus differ from one another in that an aromatic ring system cannot have a heteroatom as a ring atom, whereas a heteroaromatic ring system must have at least one heteroatom as a ring atom. This heteroatom can be present as a ring atom of a non-aromatic heterocyclic ring or as a ring atom of an aromatic heterocyclic ring. According to the above definitions, any aryl group is encompassed by the term “aromatic ring system,” and any heteroaryl group is encompassed by the term “heteroaromatic ring system.” An aromatic ring system with 6 to 40 aromatic ring atoms or a heteroaromatic ring system with 5 to 40 aromatic ring atoms,are understood in particular to mean groups derived from the groups mentioned above under aryl groups and heteroaryl groups as well as from biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, indenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, indenocarbazole, or from combinations of these groups. In the context of the present invention, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, in which individual H atoms or CH2 groups can also be substituted by the groups mentioned above in the definition of the radicals, preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neo-pentyl, n-hexyl, cyclohexyl, neo-hexyl, 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 or octynyl. An alkoxy or thioalkyl group having 1 to 20 C atoms, in which individual H atoms or CH2 groups may also be substituted by the groups mentioned above in the definition of the radicals, is preferably methoxy, trifluoromethoxy, 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, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-Butylthio, n-Pentylthio, s-Pentylthio, n-Hexylthio, Cyclohexylthio, n-Heptylthio, Cycloheptylthio, n-Octylthio, Cyclooctylthio, 2-Ethylhexylthio, Trifluoromethylthio, Pentafluoroethylthio,2,2,2-Trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio, or octynylthio. The phrase "two or more radicals can form a ring with each other" is understood, in the context of the present application, to mean, among other things, that the two radicals are linked by a chemical bond. Furthermore, the above-mentioned phrase also means that if one of the two radicals represents hydrogen, the second radical binds to the position to which the hydrogen atom was bonded, forming a ring. According to a preferred embodiment, Z is CR. 1 . According to an alternative preferred embodiment, Z is selected at each occurrence, identically or differently, from CR1 and N, where at most one group Z per ring is equal to N. The index i is equal to 0 or 1, where for i=0 the group Y is omitted and the group Z 1 is chosen the same or different at each occurrence from CR 1 and N. Z is preferred 1 for i = 0 CR 1 . In the case where i = 1, the group Y is present and is chosen at each occurrence, the same or different, from a bond, C(R 1 )2, O or S, preferably a bond or C(R 1 )2, particularly preferably a bond. In a particularly preferred embodiment, i = 1 and Y represents a bond. In this embodiment, a spirobifluorene framework is formed. Furthermore, preferred over other embodiments in which i = 1 is that i = 0 and Z 1 for CR 1 However, the embodiment in which i = 1 and Y represents a bond is preferred over the embodiment in which i = 0 and Z 1for CR 1 According to a preferred embodiment, W is O at each occurrence. Ar L is selected at each occurrence, identically or differently, from aromatic ring systems having 6 to 25 aromatic ring atoms, which are substituted by radicals R 2 are substituted, and heteroaromatic ring systems with 5 to 25 aromatic ring atoms, which are substituted with radicals R 2 are substituted; and particularly preferably at each occurrence, identically or differently selected from phenyl, biphenyl, naphthyl and fluorenyl, each substituted by radicals R 2 are substituted; and most preferably selected from phenyl which is substituted with radicals R 2 is substituted. Ar L is preferably selected at each occurrence, identically or differently, from groups of the following formulas:

[0002] where the dashed lines represent the bonds to the rest of the formula, and where the formulas Ar L -1, Ar L -2 and Ar L -3 are particularly preferred. Furthermore, it can be provided that Ar L is selected at each occurrence, identically or differently, from phenyl, biphenyl, naphthyl and fluorenyl, each of which is substituted by radicals R 2 are substituted, preferably phenyl and biphenyl, particularly preferably phenyl. Ar 1 is selected at each occurrence, identically or differently, from aromatic ring systems with 6 to 40 aromatic ring atoms, which are substituted by radicals R 4 are substituted, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which are substituted with residues R 4 are substituted. Preferably, Ar 1 at each occurrence, identically or differently selected from aromatic ring systems having 6 to 25 aromatic ring atoms, which are substituted by radicals R 4are substituted, and heteroaromatic ring systems with 5 to 25 aromatic ring atoms, which are substituted with radicals R 4 are substituted. Preferred groups Ar 1 are, at each occurrence, identically or differently selected from monovalent groups derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, 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, where each of the monovalent groups is substituted with radicals R 4 is substituted. Preferred groups are Ar 1furthermore, at each occurrence, identically or differently selected from combinations of 2 to 4 groups derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, 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, where each of the monovalent groups is substituted with radicals R 4 is substituted. Particularly preferred are the groups Ar 1 at each occurrence, identically or differently selected from monovalent groups derived from benzene, biphenyl, terphenyl, quaterphenyl, fluorene, benzofluorene, spirobifluorene, particularly preferably biphenyl, terphenyl, fluorene, spirobifluorene, where each of the monovalent groups is substituted with radicals R 4 is substituted. Ar 1is preferably selected at each occurrence, identically or differently, from groups of the following formulas: where the dashed line represents the bond to the nitrogen atom and where the groups at the unsubstituted positions are bonded to residues R 4 may be substituted, and preferably have only H in the unsubstituted positions shown. Preferred among the above-mentioned groups are the groups Ar 1 -1 to Ar 1 -106 and Ar 1 -139 to Ar 1 -271, especially preferred are the groups Ar 1 -2 to Ar 1 -106 and Ar 1 -139 to Ar 1 -271. It is particularly preferred if one or both of the groups Ar 1 , prefers both of the groups Ar 1, are selected from groups Ar 1 -2, Ar 1 -5, Ar 1 -48, Ar 1 - 50, Ar 1 -74, Ar 1 -78, Ar 1 -140, Ar 1 -141, Ar 1 -144, Ar 1 -149, Ar 1 -193, Ar 1 -195, Ar 1 -257 to Ar 1 -264, Ar 1 -265, Ar 1 -266 ares 1 -268 and Ar 1 -271. Both groups are preferred 1 chosen from groups of formulas (Ar 1 - 1) to (Ar 1 -10) and (Ar 1 -139) to (Ar 1 -171), as defined above. Preferred among the formulas (Ar 1 -1) to (Ar 1 -10) are the formulas (Ar 1 -1), (Ar 1 -2), (Ar 1 -3), (Ar 1 -6), (Ar 1 -7), (Ar 1 -8) and (Ar 1 -9). In an alternative embodiment, it can preferably be provided that one or both of the groups Ar 1 , prefers both of the groups Ar 1, are selected from groups Ar 1 -2, Ar 1 -5, Ar 1 -48, Ar 1 -50, Ar 1 -78, Ar 1 -140, Ar 1 - 141, Ar 1 -149, Ar1-139 to Ar 1 -171, Ar 1 -193, Ar 1 -265, Ar 1 -266, Ar 1 -268 and Ar 1 -271, especially preferred Ar 1 -2, Ar 1 -139 and Ar 1 -141. According to a preferred embodiment, the groups Ar 1 no carbazole group as substituent R 4 , R 6 or R 7 . Preferably, it can be provided that the two groups Ar 1 only via the nitrogen atom to which both groups Ar 1 bind, are connected, but not via substituents R 4 , R 6 or R 7 that can form a ring system. Ar 2is selected at each occurrence, identically or differently, from aromatic ring systems with 6 to 40 aromatic ring atoms, which are substituted by radicals R 5 are substituted, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which are substituted with residues R 5 are substituted. Preferably, Ar 2 at each occurrence, identically or differently selected from aromatic ring systems having 6 to 25 aromatic ring atoms, which are substituted by radicals R 5 are substituted, and heteroaromatic ring systems with 5 to 25 aromatic ring atoms, which are substituted with radicals R 5 are substituted. Preferred groups Ar 2are, at each occurrence, identically or differently selected from groups which are divalent in the ortho position and are derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, 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, where each of the divalent groups is substituted with radicals R 5 is substituted. Preference is also given to the groups Ar 2at each occurrence, identically or differently selected from combinations of 2 to 4 groups derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, 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, where each of the groups is 5 is substituted. Particularly preferred are the groups Ar 2 at each occurrence, identically or differently selected from groups which are divalent in the ortho position and are derived from benzene, biphenyl, terphenyl, quaterphenyl, fluorene, benzofluorene, spirobifluorene, particularly preferably biphenyl, terphenyl, fluorene, spirobifluorene, where each of the divalent groups is substituted by radicals R 5 is substituted. Ar 2is preferably selected at each occurrence, identically or differently, from groups of the following formulas:

[0003] where the dashed lines represent the bond to the nitrogen atom or the bond to group V, respectively, and where the groups at the unsubstituted positions are substituted by residues R 5 may be substituted, and preferably have only H in the unsubstituted positions shown. Preferred among the above-mentioned groups are the groups Ar 2 -1 to Ar 2 -79 and Ar 2 -104 to Ar 2 -220, especially preferred groups Ar 2 -2 to Ar 2 -47 and Ar 2 -104 to Ar 1-220. It is particularly preferred if one or both of the groups Ar 2 , prefers both of the groups Ar 2 , are selected from groups Ar 2 -2, Ar 2 -4, Ar 2 -35, Ar 2 - 37, Ar 2 -107, Ar 2 -109, Ar 2 -110, Ar 2 -111, Ar 2 -125, Ar 2 -126, Ar 2 -213, Ar 2 -214, Ar 2 -215 and Ar 2 -220. Both groups are preferred 2 chosen from groups of formulas (Ar 2 - 1) to (Ar 2 -7) and (Ar 2 -104) to (Ar 2 -151), as defined above. Preferred among the formulas (Ar 2 -1) to (Ar 2 -7) are the formulas (Ar 2 -1), (Ar 2 -2), (Ar 2 -3), (Ar 2 -4) and (Ar 2 -5). In an alternative embodiment, it can preferably be provided that one or both of the groups Ar 2 , prefers both of the groups Ar 2, are selected from groups Ar 2 -2, Ar 2 -4, Ar 2 -35, Ar 2 -37, Ar 2 -107, Ar 2 -109, Ar 2 -110, Ar 2 -111, Ar 2 -125, Ar 2 -126, Ar 2 -213, Ar 2 -214, Ar 2 -215 and Ar 2 -220, especially preferred Ar 2 -2, Ar 2 -104 and Ar 2 -105. According to a preferred embodiment, the groups Ar 2 no carbazole group as substituent R 5 , R 6 or R 7 . According to a preferred embodiment, V is selected from a bond, O, Si(R 5 )2and C(R 5 )2, preferably a bond, Si(R 5 )2and C(R 5 )2. V is particularly preferably a bond. In this case, together with the groups Ar 2 and the nitrogen atom, a carbazole-like structure is formed. R 1is preferably selected at each occurrence, identically or differently, from H, D, F, CN, Si(R 6 )3, N(R 6 )2, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl and alkoxy groups, the said aromatic ring systems and the said heteroaromatic ring systems are each substituted by radicals R 6 are substituted; and wherein in said alkyl or alkoxy groups one or more CH2 groups are substituted by -C≡C-, -R 6 C=CR 6 -, Si(R 6 )2, C=O, C=NR 6 , -NR 6 -, -O-, -S-, -C(=O)O- or -C(=O)NR 6 - may be replaced. R is particularly preferred 1 at each occurrence, the same or different, selected from H, D, F, CN, Si(R 6)3, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aryl groups having 6 to 25, preferably 6 to 14 aromatic ring atoms, and heteroaryl groups having 5 to 40 aromatic ring atoms, wherein the said alkyl groups, the said aryl groups and the said heteroaryl groups are each substituted by radicals R 6 are substituted. Preferably, in the compounds according to one of the formulas (I) and (II) there are no, one, two or three groups R 1 each formula not equal to H and D. Preferably, these groups, which are not equal to H and D, are selected from F, CN, Si(R 6)3, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aryl groups having 6 to 25, preferably 6 to 14 aromatic ring atoms, and heteroaryl groups having 5 to 40 aromatic ring atoms, preferably 5 to 25 aromatic ring atoms, particularly preferably 6 to 14 aromatic ring atoms, wherein the said alkyl groups, the said aryl groups and the said heteroaryl groups are each substituted by radicals R 6 are substituted. Preferably none or one of the groups R 1 each formula not equal to H and D and particularly preferably none of the groups R 1 each formula not equal to H and D. Particularly preferred are all radicals R 1 in formulas (I) and (II) is H or D, particularly preferably H. In an alternative embodiment, it can preferably be provided that the compounds according to one of the formulas (I) and (II) contain at least one group R 1which is selected from aromatic ring systems with 6 to 40 aromatic ring atoms, which are bonded to residues R 6 are substituted; particularly preferably, the compounds according to one of the formulas (I) and (II) have at least one group R 1 which is selected from aryl groups having 6 to 25, preferably 6 to 14 aromatic ring atoms, which are reacted with radicals R 6 are substituted. In an alternative embodiment, it can be particularly preferably provided that the compounds according to one of the formulas (I) and (II) contain at least one group R 1 which is a phenyl group which is reacted with residues R 6 is substituted. R 2 is preferably selected at each occurrence, identically or differently, from H, D, F, CN, Si(R 6 )3, N(R 6)2, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl and alkoxy groups, the said aromatic ring systems and the said heteroaromatic ring systems are each substituted by radicals R 6 are substituted; and wherein in said alkyl or alkoxy groups one or more CH2 groups are substituted by -C≡C-, -R 6 C=CR 6 -, Si(R 6 )2, C=O, C=NR 6 , -NR 6 -, -O-, -S-, -C(=O)O- or -C(=O)NR 6 - may be replaced. R is particularly preferred 2 at each occurrence, the same or different, selected from H, D, F, CN, Si(R 6)3, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aryl groups having 6 to 25, preferably 6 to 14 aromatic ring atoms, and heteroaryl groups having 5 to 40 aromatic ring atoms, preferably 5 to 25 aromatic ring atoms, particularly preferably 6 to 14 aromatic ring atoms, wherein the said alkyl groups, the said aryl groups and the said heteroaryl groups are each substituted by radicals R 6 are substituted. Preferably, in the compounds according to one of the formulas (I) and (II) there are no, one, two or three groups R 2 each formula not equal to H and D. Preferably, these groups, which are not equal to H and D, are selected from F, CN, Si(R 6)3, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aryl groups having 6 to 25, preferably 6 to 14 aromatic ring atoms, and heteroaryl groups having 5 to 40 aromatic ring atoms, preferably 5 to 25 aromatic ring atoms, particularly preferably 6 to 14 aromatic ring atoms, wherein the said alkyl groups, the said aryl groups and the said heteroaryl groups are each substituted by radicals R 6 are substituted. Preferably none or one of the groups R 2 each formula not equal to H and D and particularly preferably none of the groups R 2 each formula not equal to H and D. R 3 is preferably selected at each occurrence, identically or differently, from H, D, F, CN, Si(R 6 )3, N(R 6)2, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl and alkoxy groups, the said aromatic ring systems and the said heteroaromatic ring systems are each substituted by radicals R 6 are substituted; and wherein in said alkyl or alkoxy groups one or more CH2 groups are substituted by -C≡C-, -R 6 C=CR 6 -, Si(R 6 )2, C=O, C=NR 6 , -NR 6 -, -O-, -S-, -C(=O)O- or -C(=O)NR 6 - may be replaced. Preferably, in the compounds according to one of the formulas (I) and (II) there are no, one, two or three groups R 3 each formula not equal to H and D. Preferably, these groups, which are not equal to H and D, are selected from F, CN, Si(R 6)3, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aryl groups having 6 to 25, preferably 6 to 14 aromatic ring atoms, and heteroaryl groups having 5 to 40 aromatic ring atoms, preferably 5 to 25 aromatic ring atoms, particularly preferably 6 to 14 aromatic ring atoms, wherein the said alkyl groups, the said aryl groups and the said heteroaryl groups are each substituted by radicals R 6 are substituted. Preferably none or one of the groups R 3 each formula not equal to H and D and particularly preferably none of the groups R 3 each formula not equal to H and D. Particularly preferred are all radicals R 3 in formulas (I) and (II) is H or D, particularly preferably H. In an alternative embodiment, it can preferably be provided that the compounds according to one of the formulas (I) and (II) contain at least one group R 3which is selected from aromatic ring systems with 6 to 40 aromatic ring atoms, which are bonded to residues R 6 are substituted; particularly preferably, the compounds according to one of the formulas (I) and (II) have at least one group R 3 which is selected from aryl groups having 6 to 25, preferably 6 to 14 aromatic ring atoms, which are reacted with radicals R 6 are substituted. In an alternative embodiment, it can be particularly preferably provided that the compounds according to one of the formulas (I) and (II) contain at least one group R 3 which is a phenyl group which is reacted with residues R 6 Preferably, all radicals R 1 and R 3 in formulas (I) and (II) are H or D. R 4 is preferably selected at each occurrence, identically or differently, from H, D, F, CN, Si(R 6 )3, N(R 6)2, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl and alkoxy groups, the said aromatic ring systems and the said heteroaromatic ring systems are each substituted by radicals R 6 are substituted; and wherein in said alkyl or alkoxy groups one or more CH2 groups are substituted by -C≡C-, -R 6 C=CR 6 -, Si(R 6 )2, C=O, C=NR 6 , -NR 6 -, -O-, -S-, -C(=O)O- or -C(=O)NR 6 - may be replaced. Preferably, in the compounds according to one of the formulas (I) and (II) none, one, two, three or four of the groups R 4 per remaining area 1 not equal to H and D. Preferably, these groups, which are not equal to H and D, are selected from F, CN, Si(R 6)3, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aryl groups having 6 to 25, preferably 6 to 14 aromatic ring atoms and heteroaryl groups having 5 to 40 aromatic ring atoms, preferably 5 to 25 aromatic ring atoms, particularly preferably 6 to 14 aromatic ring atoms, wherein the said alkyl groups, the said aryl groups and the said heteroaryl groups are each substituted by radicals R 6 are substituted. Preferably none, one or two of the groups R 4 each formula is not equal to H and D and particularly preferably none or one of the groups R 4 each formula not equal to H and D. R 5 is preferably selected at each occurrence, identically or differently, from H, D, F, CN, Si(R 6 )3, N(R 6)2, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl and alkoxy groups, the said aromatic ring systems and the said heteroaromatic ring systems are each substituted by radicals R 6 are substituted; and wherein in said alkyl or alkoxy groups one or more CH2 groups are substituted by -C≡C-, -R 6 C=CR 6 -, Si(R 6 )2, C=O, C=NR 6 , -NR 6 -, -O-, -S-, -C(=O)O- or -C(=O)NR 6 - may be replaced. Preferably, in the compounds according to one of the formulas (I) and (II) none, one, two, three or four of the groups R 5 per remaining area 2 not equal to H and D. Preferably, these groups, which are not equal to H and D, are selected from F, CN, Si(R6 )3, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aryl groups having 6 to 25, preferably 6 to 14 aromatic ring atoms and heteroaryl groups having 5 to 40 aromatic ring atoms, preferably 5 to 25 aromatic ring atoms, particularly preferably 6 to 14 aromatic ring atoms, wherein the said alkyl groups, the said aryl groups and the said heteroaryl groups are each substituted by radicals R 6 are substituted. Preferably none, one or two of the groups R 5 each formula is not equal to H and D and particularly preferably none or one of the groups R 5 each formula not equal to H and D. R 6 is preferably selected at each occurrence, identically or differently, from H, D, F, CN, Si(R 7 )3, N(R 7)2, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl and alkoxy groups, the said aromatic ring systems and the said heteroaromatic ring systems are each substituted by radicals R 7 are substituted; and wherein in said alkyl or alkoxy groups one or more CH2 groups are substituted by -C≡C-, -R 7 C=CR 7 -, Si(R 7 )2, C=O, C=NR 7 , -NR 7 -, -O-, -S-, -C(=O)O- or -C(=O)NR 7 - may be replaced. Formula (I) preferably corresponds to one of the following formulas: where the groups appearing are defined as above. Preferred embodiments of the above formulas correspond to the following formulas: where the groups occurring are defined as above. Formula (II) preferably corresponds to one of the following formulas:

[0004] where the groups appearing are defined as above. Preferred embodiments of the above formulas correspond to the following formulas:

[0005] where the groups appearing are defined as above. Preferred compounds according to the present application are shown below:

[0006] The compounds according to the present application can be prepared using the synthetic methods described below. According to the process shown in Scheme 1, a Hartwig-Buchwald coupling can be carried out starting from an indenodibenzofuran derivative, introducing an amino group into the molecule. This yields a compound according to the present application with index k=0. Alternatively, as shown in Schemes 2 and 3, a Suzuki coupling can be performed, introducing an aromatic ring system into the molecule. This yields a compound according to the present application in which index k is >0. Scheme 2

[0007] The definitions of the variable groups in the schemes shown above are as previously defined, where for the other groups: R = H or organic residue Q = reactive group Ar = optionally substituted aromatic or heteroaromatic, corresponding to the previously defined groups Ar L , Ar 1 , Ar 2and V The present application thus relates to a process for preparing a compound according to the present application, characterized in that an indenodibenzofuran derivative substituted by a reactive group is a) reacted in a coupling reaction with a secondary amine, or b) reacted in a coupling reaction with an aromatic or heteroaromatic compound carrying a reactive group. In variant b), the reactive group on the indenodibenzofuran derivative preferably contains boron, and the reactive group on the aromatic or heteroaromatic compound is preferably selected from Cl, Br, and I. Alternatively, the reactive group on the indenodibenzofuran derivative is selected from Cl, Br, and I, and the reactive group on the aromatic or heteroaromatic compound preferably contains boron.In a first embodiment of variant b), an indenodibenzofuran derivative substituted with a reactive group is reacted in a coupling reaction with an aromatic or heteroaromatic compound bearing a boron-containing group. In a second embodiment of variant b), an indenodibenzofuran derivative substituted with a boron-containing group is reacted in a coupling reaction with an aromatic or heteroaromatic compound bearing a reactive group. Reactive groups are known to the person skilled in the art for the specific reaction. One of the reactive groups is preferably selected from Cl, Br, and I, particularly preferably from Br and I. The coupling reaction in the reaction under a) is preferably a Hartwig-Buchwald coupling reaction. The coupling reaction under b) is preferably a Suzuki coupling reaction.In a Suzuki coupling reaction, one reactive group is preferably selected as previously outlined, and another reactive group is preferably a boron atom-containing group, preferably a boric acid or boric acid ester group. The indenodibenzofuran derivative substituted with one reactive group is preferably prepared starting from a dibenzofuran derivative substituted with two reactive groups, which is reacted with a carbonyl compound in an organometallic addition reaction. Compounds containing a boron atom-containing group, preferably a boric acid or boric acid ester group, can preferably be obtained by reaction with organometallic compounds, preferably organometallic lithium compounds. Unsubstituted indenodibenzofuran derivatives can also be used.Furthermore, indenodibenzofuran derivatives having a reactive group selected from Cl, Br, and I, particularly preferably Br and I, can also be obtained from unsubstituted indenodibenzofuran derivatives by reaction with organometallic compounds, preferably organometallic lithium compounds. The process instructions and synthesis steps outlined above are disclosed, inter alia, in the publications WO 2015 / 090504 and WO 2015 / 022051 A1. These publications are hereby explicitly incorporated by reference. The compounds according to the invention described above, in particular compounds substituted by reactive leaving groups, such as bromine, iodine, chlorine, boronic acid, or boronic acid esters, can be used as monomers for producing corresponding oligomers, dendrimers, or polymers.Suitable reactive leaving groups are, for example, bromine, iodine, chlorine, boronic acids, boronic acid esters, amines, alkenyl or alkynyl groups with a terminal CC double bond or CC triple bond, oxiranes, oxetanes, groups that undergo cycloaddition, for example a 1,3-dipolar cycloaddition, such as dienes or azides, carboxylic acid derivatives, alcohols, and silanes. The invention therefore further relates to oligomers, polymers, or dendrimers comprising one or more compounds of the formula (I) or (II), wherein the bond(s) to the polymer, oligomer, or dendrimer are formed at any desired linkage designated by R in formula (I) or (II). 1 , R 2 , R 3 , R 4 or R 5substituted positions. Depending on the linkage of the compound according to formula (I) or (II), the compound is part of a side chain of the oligomer or polymer or part of the main chain. An oligomer in the sense of this invention is understood to be a compound composed of at least three monomer units. A polymer in the sense of the invention is understood to be a compound composed of at least ten monomer units. The polymers, oligomers or dendrimers according to the invention can be conjugated, partially conjugated or non-conjugated. The oligomers or polymers according to the invention can be linear, branched or dendritic. In the linearly linked structures, the units according to formula (I) or (II) can be linked directly to one another or they can be linked via a bivalent group, for example via a substituted or unsubstituted alkylene group.be linked to one another via a heteroatom or via a bivalent aromatic or heteroaromatic group. In branched and dendritic structures, for example, three or more units according to formula (I) or (II) can be linked to form a branched or dendritic oligomer or polymer via a trivalent or higher-valent group, for example via a trivalent or higher-valent aromatic or heteroaromatic group. For the repeating units according to formula (I) or (II) in oligomers, dendrimers, and polymers, the same preferences apply as described above for compounds according to formula (I) or (II). To prepare the oligomers or polymers, the monomers according to the invention are homopolymerized or copolymerized with other monomers. Suitable and preferred comonomers are selected from fluorenes, spirobifluorenes, paraphenylenes, carbazoles, thiophenes, dihydrophenanthrenes, cis- and trans-indenofluorenes, ketones,Phenanthrenes or several of these units. The polymers, oligomers, and dendrimers typically contain further units, for example emitting (fluorescent or phosphorescent) units, such as vinyltriarylamines or phosphorescent metal complexes, and / or charge transport units, in particular those based on triarylamines. The polymers, oligomers, and dendrimers according to the invention have advantageous properties, in particular long lifetimes, high efficiencies, and good color coordinates. The polymers and oligomers according to the invention are generally prepared by polymerizing one or more types of monomers, of which at least one monomer in the polymer leads to repeating units of the formula (I) or (II). Suitable polymerization reactions are known to the person skilled in the art and are described in the literature. Particularly suitable and preferred polymerization reactions that lead to CC or CN linkages,are the following: (A) SUZUKI polymerization; (B) YAMAMOTO polymerization; (C) STILLE polymerization; and (D) HARTWIG-BUCHWALD polymerization. How the polymerization can be carried out by these methods and how the polymers can then be separated from the reaction medium and purified is known to the person skilled in the art and is described in detail in the literature. For processing the compounds of the invention from the liquid phase, for example by spin coating or by printing processes, formulations of the compounds of 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 are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, alpha-terpineol, Benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, NMP, p-cymene, phenetol, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, Diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, Tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane or mixtures of these solvents. The invention therefore further relates to a formulation, in particular a solution, dispersion or emulsion,containing at least one compound of formula (I) or (II) or at least one polymer, oligomer, or dendrimer containing at least one unit of formula (I) or (II), and at least one solvent, preferably an organic solvent. How such solutions can be prepared is known to the person skilled in the art. The compound of formula (I) or (II) is suitable for use in an electronic device, in particular an organic electroluminescent device (OLED). Depending on the substitution, the compound of formula (I) or (II) can be used in different functions and layers. Preference is given to use as a hole-transporting material in a hole-transporting layer and / or as a matrix material in an emitting layer.particularly preferably in combination with a phosphorescent emitter. The invention therefore further relates to the use of a compound according to formula (I) or (II) in an electronic device. The electronic device is preferably selected from the group consisting of organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic light-emitting transistors (OLETs), organic solar cells (OSCs), organic optical detectors, organic photoreceptors, organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers), and particularly preferably organic electroluminescent devices (OLEDs). The invention further relates to an electronic device,containing at least one compound according to formula (I) or (II). The electronic device is preferably selected from the above-mentioned devices. Particular preference is given to an organic electroluminescent device containing an anode, a cathode, and at least one emitting layer, characterized in that at least one organic layer is contained in the device which contains at least one compound according to formula (I) or (II). Preferred is an organic electroluminescent device containing an anode, a cathode, and at least one emitting layer, characterized in that at least one organic layer in the device, selected from hole-transporting and emitting layers, contains at least one compound according to formula (I) or (II). A hole-transporting layer is understood to mean all layers arranged between the anode and the emitting layer, preferably a hole-injection layer.Hole transport layer, and electron blocking layer. A hole injection layer is understood to be a layer that directly borders the anode. A hole transport layer is understood to be a layer that is present between the anode and the emitting layer, but not directly bordering the anode, and preferably not directly bordering the emitting layer either. An electron blocking layer is understood to be a layer that is present between the anode and the emitting layer and directly bordering the emitting layer. An electron blocking layer preferably has a high-energy LUMO and thus prevents electrons from escaping from the emitting layer. In addition to the cathode, anode, and emitting layer, the electronic device can contain further layers. These are selected, for example, from one or more hole injection layers, hole transport layers, hole blocking layers,Electron-transport layers, electron-injection layers, electron-blocking layers, exciton-blocking layers, interlayers, charge-generation layers, and / or organic or inorganic p / n junctions. It should be noted, however, that not all of these layers necessarily need to be present, and the choice of layers always depends on the compounds used and, in particular, on whether the device is fluorescent or phosphorescent. The sequence of layers in the electronic device is preferably as follows: -anode- -hole-injection layer- -hole-transport layer- -optional further hole-transport layers- -emitting layer- -optional hole-blocking layer- -electron-transport layer- -electron-injection layer- -cathode-. It should be noted again that not all of the aforementioned layers need to be present.and / or that additional layers may be present. The organic electroluminescent device according to the invention can contain a plurality of emitting layers. Particularly preferably, these emitting layers have a total of several emission maxima between 380 nm and 750 nm, resulting in overall white emission, i.e., various emitting compounds that can fluoresce or phosphoresce and that emit blue, green, yellow, orange, or red light are used in the emitting layers. Particular preference is given to three-layer systems, i.e., systems with three emitting layers, wherein one of the three layers exhibits blue emission, one of the three layers exhibits green emission, and one of the three layers exhibits orange or red emission. The compounds according to the invention are preferably present in a hole-transporting layer or in the emitting layer. It should be noted thatthat for the generation of white light, instead of several color-emitting emitter compounds, a single emitter compound which emits in a broad wavelength range can also be suitable. It is preferred that the compound of formula (I) or (II) is used as the hole-transport material. The emitting layer can be a fluorescent emitting layer or it can be a phosphorescent emitting layer. The emitting layer is preferably a blue fluorescent layer or a green phosphorescent layer. If the device comprising the compound of formula (I) or (II) contains a phosphorescent emitting layer, it is preferred that this layer has two or more, preferably exactly two,contains various matrix materials (mixed matrix system). Preferred embodiments of mixed matrix systems are described in more detail below. If the compound according to formula (I) or (II) is used as a hole-transport material in a hole-transport layer, a hole-injection layer, or an electron-blocking layer, the compound can be used as pure material, i.e., in a proportion of 100%, in the hole-transport layer, or it can be used in combination with one or more further compounds. According to a preferred embodiment, a hole-transporting layer comprising the compound of formula (I) or (II) additionally contains one or more further hole-transporting compounds. These further hole-transporting compounds are preferably selected from triarylamine compounds,particularly preferably from mono-triarylamine compounds. They are most preferably selected from the preferred embodiments of hole-transport materials specified below. In the preferred embodiment described, the compound of formula (I) or (II) and the one or more further hole-transporting compounds are preferably each present in a proportion of at least 10%, particularly preferably each present in a proportion of at least 20%. According to a preferred embodiment, a hole-transporting layer comprising the compound of formula (I) or (II) additionally contains one or more p-dopants. According to the present invention, p-dopants are preferably those organic electron acceptor compounds which can oxidize one or more of the other compounds of the mixture. Particularly preferred p-dopants are quinodimethane compounds, azaindenofluorenediones, azaphenalenes, azatriphenylenes, I2,Metal halides, preferably transition metal halides, metal oxides, preferably metal oxides containing at least one transition metal or a metal of main group 3, and transition metal complexes, preferably complexes of Cu, Co, Ni, Pd, and Pt with ligands containing at least one oxygen atom as a bonding site. Also preferred are transition metal oxides as dopants, preferably oxides of rhenium, molybdenum, and tungsten, particularly preferably Re2O7, MoO3, WO3, and ReO3. Complexes of bismuth in oxidation state (III), in particular bismuth(III) complexes with electron-deficient ligands, are also preferred.in particular carboxylate ligands. The p-dopants are preferably largely uniformly distributed in the p-doped layers. This can be achieved, for example, by co-evaporation of the p-dopant and the hole-transport material matrix. The p-dopant is preferably present in a proportion of 1 to 10% in the p-doped layer. The following compounds are particularly preferred as p-dopants: N NC CN, ( ) ( ) ( )

[0008] According to a preferred embodiment, the device contains a hole-injection layer that corresponds to one of the following embodiments: a) it contains a triarylamine and a p-dopant; or b) it contains a single electron-deficient material (electron acceptor). According to a preferred embodiment of embodiment a), the triarylamine is a mono-triarylamine, in particular one of the preferred triarylamine derivatives mentioned below. According to a preferred embodiment of embodiment b), the electron-deficient material is a hexaazatriphenylene derivative, as described in US 2007 / 0092755. The compound of formula (I) or (II) can be present in a hole-injection layer, in a hole-transport layer, and / or in an electron-blocking layer of the device.If the compound is present in a hole injection layer or in a hole transport layer, it is preferably p-doped, i.e. it is present in the layer mixed with a p-dopant, as described above. The compound of formula (I) or (II) is preferably present in an electron blocking layer. In this case, it is preferably not p-doped. Furthermore, in this case, it is preferably present as a single compound in the layer, without the admixture of any further compound. According to an alternative preferred embodiment, the compound of formula (I) or (II) is used in an emitting layer as a matrix material in combination with one or more emitting compounds, preferably phosphorescent emitting compounds. The phosphorescent emitting compounds are preferably selected from red phosphorescent and green phosphorescent compounds.The proportion of matrix material in the emitting layer in this case is between 50.0 and 99.9 vol.%, preferably between 80.0 and 99.5 vol.%, and particularly preferably between 85.0 and 97.0 vol.%. Accordingly, 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 3.0 and 15.0 vol.%. An emitting layer of an organic electroluminescent device can also contain systems comprising multiple matrix materials (mixed matrix systems) and / or multiple emitting compounds. In this case, too, the emitting compounds are generally those compounds whose proportion is the smaller in the system, and the matrix materials are those compounds whose proportion is the larger in the system. In individual cases, however, the proportion of an individual matrix material in the system can be smaller than the proportion of an individual emitting compound.It is preferred that the compounds of formula (I) or (II) are used as a component of mixed-matrix systems, preferably for phosphorescent emitters. The mixed-matrix systems preferably comprise two or three different matrix materials, particularly preferably two different matrix materials. Preferably, one of the two materials is a material with hole-transporting properties and the other material is a material with electron-transporting properties. It is further preferred if one of the materials is selected from compounds with a large energy difference between HOMO and LUMO (wide-bandgap materials). In a mixed-matrix system, the compound of formula (I) or (II) preferably represents the matrix material with hole-transporting properties.Accordingly, when the compound of formula (I) or (II) is used as a matrix material for a phosphorescent emitter in the emitting layer of an OLED, a second matrix compound having electron-transporting properties is present in the emitting layer. The two different matrix materials can be present in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, particularly preferably 1:10 to 1:1, and most preferably 1:4 to 1:1. However, the desired electron-transporting and hole-transporting properties of the mixed-matrix components can also be combined primarily or entirely in a single mixed-matrix component, with the additional mixed-matrix component(s) fulfilling other functions.The following material classes are preferably used in the above-mentioned layers of the device: Phosphorescent emitters: The term "phosphorescent emitters" typically encompasses compounds in which light emission occurs through a spin-forbidden transition, for example, a transition from an excited triplet state or a state with a higher spin quantum number, such as a quintet state. Particularly suitable as phosphorescent emitters are compounds that emit light upon suitable excitation, preferably in the visible range, and also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, and particularly preferably greater than 56 and less than 80.Preferably, compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are used as phosphorescent emitters, in particular compounds containing iridium, platinum, or copper. For the purposes of the present invention, all luminescent iridium, platinum, or copper complexes are regarded as phosphorescent compounds. In general, all phosphorescent complexes as used in the prior art for phosphorescent OLEDs and as known to those skilled in the art in the field of organic electroluminescent devices are suitable for use in the devices according to the invention. Further examples of suitable phosphorescent emitters are shown in the following table:.

[0009] Fluorescent emitters: Preferred fluorescent emitting compounds are selected from the class of arylamines. An arylamine or an aromatic amine within the meaning of this invention is understood to be a compound containing three substituted or unsubstituted aromatic or heteroaromatic ring systems directly bonded to the nitrogen. Preferably, at least one of these aromatic or heteroaromatic ring systems is a fused ring system, particularly preferably with at least 14 aromatic ring atoms. Preferred examples are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic chryseneamines, or aromatic chrysenediamines. An aromatic anthraceneamine is understood to be a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9-position.An aromatic anthracenediamine is understood to be a compound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 9,10-position. Aromatic pyrenamines, pyrenediamines, chrysenamines, and chrysenediamines are defined analogously, with the diarylamino groups on the pyrene preferably being bonded in the 1-position or 1,6-position, respectively. Further preferred emitting compounds are indenofluorenamines and diamines, benzoindenofluorenamines and diamines, and dibenzoindenofluorenamines and diamines, as well as indenofluorene derivatives with fused aryl groups. Pyrene-arylamines are also preferred. Also preferred are benzoindenofluoreneamines, benzofluoreneamines, extended benzoindenofluorenes, phenoxazines, and fluorene derivatives bonded to furan units or thiophene units.Matrix materials for fluorescent emitters: Preferred matrix materials for fluorescent emitters are selected from the classes of oligoarylenes (e.g., 2,2',7,7'-tetraphenylspirobifluorene), in particular oligoarylenes containing condensed aromatic groups, oligoarylenevinylenes, polypodal metal complexes, hole-conducting compounds, electron-conducting compounds, in particular ketones, phosphine oxides, and sulfoxides; atropisomers, boronic acid derivatives, or benzanthracenes. Particularly preferred matrix materials are selected from the classes of oligoarylenes containing naphthalene, anthracene, benzanthracene, and / or pyrene or atropisomers of these compounds, oligoarylenevinylenes, ketones, phosphine oxides, and sulfoxides. Very particularly preferred matrix materials are selected from the classes of oligoarylenes containing anthracene, benzanthracene, benzphenanthrene and / or pyrene or atropisomers of these compounds.An oligoarylene, within the meaning of this invention, is understood to mean a compound in which at least three aryl or arylene groups are bonded to one another. Matrix materials for phosphorescent emitters: In addition to the compounds of formula (I) or (II), preferred matrix materials for phosphorescent emitters are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, triarylamines, carbazole derivatives, e.g., CBP (N,N-biscarbazolylbiphenyl) or carbazole derivatives, indolocarbazole derivatives, indenocarbazole derivatives, azacarbazole derivatives, bipolar matrix materials, silanes, azaboroles or boronic esters, triazine derivatives, zinc complexes, diazasilole or tetraazasilole derivatives, diazaphosphole derivatives, bridged carbazole derivatives, triphenylene derivatives, or lactams. Electron-transporting materials: Suitable electron-transporting materials include those described in Y. Shirota et al., Chem. Rev.2007, 107(4), 953-1010, or other materials as used in these layers according to the prior art. All materials that are used in the prior art as electron-transport materials in the electron-transport layer can be used as materials for the electron-transport layer. Particularly suitable are aluminum complexes, for example Alq3; zirconium complexes, for example Zrq4; lithium complexes, for example Liq; benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives, and phosphine oxide derivatives. Preferred electron-transport and electron-injection materials are shown in the table on pages 73-75 of WO2020 / 109434A1.Hole-transporting materials: Further compounds which, in addition to the compounds of formula (I) or (II), are preferably used in hole-transporting layers of the OLEDs according to the invention are indenofluorenamine derivatives, amine derivatives, hexaazatriphenylene derivatives, amine derivatives with condensed aromatics, monobenzoindenofluorenamines, dibenzoindenofluorenamines, spirobifluorene amines, fluorene amines, spiro-dibenzopyran amines, dihydroacridine derivatives, spirodibenzofurans and spirodibenzothiophenes, phenanthrene diarylamines, spiro-tribenzotropolones, spirobifluorenes with meta-phenyldiamine groups, spiro-bisacridines, xanthene diarylamines, and 9,10-dihydroanthracene spiro compounds with diarylamino groups. Preferred hole-transporting compounds are shown in the table on pages 76-80 of WO2020 / 109434A1. The following compounds HT-1 to HT-35 are particularly well suited for use in a layer with a hole-transport function of an OLED.This applies not only to OLEDs according to the definitions and claims of the present application, but to OLEDs in general:.

[0010] The compounds HT-1 to HT-35 can generally be used in any hole-transport layer of OLEDs. The term "hole-transport layer" here refers to any layer of an OLED located between the anode and the emitting layer. The term "OLED" is not specifically restricted and applies to all OLEDs, in particular to the OLED structures common at the time of filing this application. The compounds HT-1 to HT-35 can be prepared by processes disclosed in the application texts listed in the table above under the respective compounds HT-1 to HT-35. The teachings regarding the use of the compounds and the processes for preparing the compounds contained in the above-mentioned application texts are hereby expressly incorporated into the present disclosure by reference.The compounds HT-1 to HT-35 exhibit excellent properties when used in OLEDs, particularly excellent lifetime and efficiency. This is especially the case when used in a hole-transport layer of the OLED. Metals with low work functions, metal alloys, or multilayer structures composed of different metals are preferred as the cathode of the electronic device, such as alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Alloys composed of an alkali or alkaline earth metal and silver, for example, an alloy of magnesium and silver, are also suitable. In multilayer structures, other metals with a relatively high work function, such as Ag or Al, can also be used in addition to the metals mentioned. Combinations of these metals, such as Ca / Ag, Mg / Ag, or Ba / Ag, are then generally used.It may also be preferable to introduce a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor. Examples of suitable materials include alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates (e.g., LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.). Lithium quinolinate (LiQ) can also be used for this purpose. The thickness of this layer is preferably between 0.5 and 5 nm. Materials with a high work function are preferred as the anode. The anode preferably has a work function greater than 4.5 eV vs. vacuum. Metals with a high redox potential, such as Ag, Pt, or Au, are suitable for this purpose. Metal / metal oxide electrodes (e.g., Al / Ni / NiOx, Al / PtOx) may also be preferred.For some applications, at least one of the electrodes must be transparent or partially transparent to enable either the irradiation of the organic material (organic solar cell) or the coupling out of light (OLED, O-LASER). Preferred anode materials here are conductive mixed metal oxides. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred. Also preferred are conductive, doped organic materials, in particular conductive doped polymers. Furthermore, the anode can also consist of several layers, for example an inner layer of ITO and an outer layer of a metal oxide, preferably tungsten oxide, molybdenum oxide, or vanadium oxide. In a preferred embodiment, the electronic device is characterized in that one or more layers are coated using a sublimation process. The materials are sublimated in vacuum sublimation systems at an initial pressure of less than 10.-5 mbar, preferably less than 10 -6 mbar. However, it is also possible that the initial pressure is even lower, for example less than 10 -7 mbar. Also preferred is an electronic device characterized in that one or more layers are coated using the OVPD (Organic Vapour Phase Deposition) process or by means of carrier gas sublimation. The materials are deposited at a pressure between 10 -5mbar and 1 bar. A special case of this process is the OVJP (Organic Vapour Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured (e.g. BMS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301). Also preferred is an electronic device, characterized in that one or more layers are produced from solution, for example by spin coating, or using any printing process, such as screen printing, flexographic printing, nozzle printing or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing. For this purpose, soluble compounds according to formula (I) or (II) are required. High solubility can be achieved by suitable substitution of the compounds.It is further preferred that, to produce an electronic device according to the invention, one or more layers are applied from solution and one or more layers are applied by a sublimation process. After application of the layers, the device is structured, contacted, and finally sealed, depending on the application, to exclude the damaging effects of water and air. According to the invention, the electronic devices comprising one or more compounds of the formula (I) or (II) can be used in displays, as light sources in lighting applications, and as light sources in medical and / or cosmetic applications. Examples A) Synthesis Examples 1) Synthesis of Compound 1a. 33.4 g (63 mmol) CAS 1799406-63-5, 32.4 g (63 mmol), 21.1 g (94 mmol) potassium phosphate monohydrate and 1.6 g (1.9 mmol) XPhos Palladacylce Gen.3 are dissolved in 60 ml THF / water (4:1) and stirred for 16 hours at 60°C. The reaction mixture is then concentrated on a rotary evaporator and the residue is dissolved with dichloromethane. The organic phase is washed twice with water and the aqueous phases are extracted twice with dichloromethane. The organic phases are combined, dried over sodium sulfate, filtered and concentrated to dryness on a rotary evaporator. The residue is extracted several times over hot aluminum oxide (toluene / heptane 1:1) and crystallized to an HPLC purity of >99.9%. Finally, the product is isolated after sublimation (10 -6 bar, 325 °C) as a solid. Yield: 25.9 g (30.7 mmol; 49%). The following compounds are prepared analogously: 2) Synthesis of Int-2 The synthesis of Int-1 is analogous to the synthesis of CAS 2459761-30-7 described in WO 2020 / 159333 A1. 3) Synthesis of Int-3a The synthesis of Int-3a is analogous to the two-step synthesis of Int-7, described in WO 2015 / 022051 A1 (see page 85ff.). The following compounds are prepared analogously: *This reaction produces a mixture of isomers that can be separated chromatographically. 4) Synthesis of Int-4a The boronic acid is prepared analogously to the synthesis of compound CAS 1799406-63-5, described in WO 2015 / 090504, starting from Int-3c. The following compounds are synthesized in an analogous manner: 5) Synthesis of reference compound 2a 15.4 g (35 mmol) of Int-4, 8.3 g (35 mmol) of CAS 952431-30-0, and 10.6 g (70 mmol) of cesium fluoride are suspended in 400 ml of dioxane. 1.02 g (1.40 mmol) of palladium dichloride bis(tricyclohexylphosphine) are added to this suspension, and the reaction mixture is refluxed for 18 hours. The reaction mixture is then allowed to cool to room temperature. The organic phase is washed three times with 100 mL of water and evaporated to dryness in a rotary evaporator. The residue is taken up in toluene and filtered through silica gel. The residue is purified by recrystallization from toluene / heptane to an HPLC purity of >99.9% and finally sublimed under high vacuum. Yield: 10.4 g (13 mmol; 37% of theory). The following compound is prepared analogously: 6) Synthesis of compound 3a 13.4 g (26 mmol) of Int-1a, 8.83 g (26 mmol) of CAS 1879963-55-9, 3.5 g (37 mmol) of sodium tert-butoxide, and 616 mg (0.73 mmol) of XPhos Pd Gen3 are suspended in 400 ml of toluene and stirred at 100°C for 16 hours. After complete conversion, the reaction mixture is allowed to cool to room temperature, filtered through aluminum oxide, and rinsed with toluene. After removal of the solvents, the crude product is dissolved in toluene / heptane 1:1 and filtered through silica gel. Further purification is carried out by repeated crystallization from heptane / toluene to an HPLC purity of >99.9%. Finally, the product is obtained as a solid after two sublimations under high vacuum. Yield: 6.7 g (9 mmol; 35%). the following connections are made: B) Device examples 1) General manufacturing process for the OLEDs and characterization of the OLEDs Glass plates coated with structured ITO (indium tin oxide) with a thickness of 50 nm form the substrates onto which the OLEDs are applied. The OLEDs basically have the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL1) / optional second hole transport layer (HTL2) / electron blocking layer (EBL) / emission layer (EML) / optional hole blocking layer (HBL) / electron transport layer (ETL1) / optional second electron transport layer (ETL2) / electron injection layer (EIL) and finally a cathode. The cathode is formed by a 100 nm thick aluminum layer. The exact structure of the OLEDs can be found in the following tables. The materials required to manufacture the OLEDs are shown in the following table. All materials are thermally vapor deposited in a vacuum chamber.The emission layer consists of at least one matrix material (host material) and an emitting dopant (emitter), which is mixed into the matrix material(s) by co-evaporation in a specific volume fraction. A specification such as H:SEB (95%:5%) means that the H material is present in a volume fraction of 95% and SEB in a volume fraction of 5% in the layer. Similarly, the electron transport layer and the hole injection layer also consist of a mixture of two materials. The structures of the materials used in the OLEDs are shown in Table 7. The compound HTM-B, which is also used, is a 2-aminofluorene bearing a substituent on one of the aromatic six-membered rings of the fluorene. The compound EBM-B, which is also used, contains an amino group and a 1-spirobifluorenyl group. The OLEDs are characterized as standard.For this purpose, the electroluminescence spectra, the external quantum efficiency (EQE, measured in %) as a function of luminance, calculated from current-voltage-luminance curves assuming a Lambertian radiation pattern, and the lifetime are determined. The specification EQE @ 10 mA / cm² refers to the external quantum efficiency achieved at 10 mA / cm². The lifetime LT is defined as the time after which the luminance drops from the starting luminance to a certain percentage when operated at a constant current density. A specification LT90 means that the specified lifetime corresponds to the time after which the luminance has dropped to 90% of its initial value. The specification @60 mA / cm. 2 means that the lifetime in question is 60 mA / cm 2 is measured. 2) Use as an electron blocker in a blue fluorescent OLED: OLEDs with the following structure are manufactured: OLEDs 1 to 4 demonstrate that the compounds of the invention are excellently suited as materials in OLEDs. The OLEDs exhibit very good properties as hole-transport materials, especially in an EBL layer, where they lead primarily to very high external quantum efficiencies, low operating voltage, and very good lifetime. The OLEDs exhibit good results for lifetime, efficiency, and operating voltage, as shown in the following table: 3) Examples for use in the electron blocking layer of a green phosphorescent OLED OLEDs with the following structure are manufactured: OLEDs 5 and 6 demonstrate that the compounds of the invention are excellently suited as electron blockers for green phosphorescent OLEDs. The OLEDs exhibit very good properties as hole-transport and electron-blocking materials, respectively, and, above all, exhibit low operating voltages with good external quantum efficiencies and outstanding lifetimes. The OLEDs exhibit good results for lifetime, efficiency, and operating voltage, as shown in the following table:

[0011] 4) Example for use as a hole transport layer of a blue fluorescent OLED An OLED with the following structure is manufactured: The example (OLED 7) demonstrates that the compound HTM-1 according to the invention is ideally suited as a hole-transport material for blue-fluorescent OLEDs. The OLED exhibits excellent hole-transport properties and low operating voltage with good external quantum efficiencies and an outstanding lifetime. The OLED exhibits good results for lifetime, efficiency, and operating voltage, as shown in the following table: HTM-2 can also be used in a stack as shown in Table 5, with good OLED performance. 5) Furthermore, the following blue fluorescent OLEDs containing a compound according to the invention were produced in the EBL:

[0012] OLEDs 8 and 9 demonstrate that the compounds of the invention are excellently suited as electron-blocking materials for blue-fluorescent OLEDs. The OLEDs achieve a low operating voltage with good external quantum efficiency and long lifetime: 6) Furthermore, the following green phosphorescent OLEDs containing a compound according to the invention HTM-1, HTM-2 or HTM-3 are produced in the EBL: OLEDs 10-12 demonstrate that the compounds of the invention are excellently suited as materials in the electron-blocking layer of green phosphorescent OLEDs. The OLEDs achieve a low operating voltage with good external quantum efficiency and outstanding lifetime: 7) Furthermore, the following blue fluorescent OLED containing the compound HTM-3 according to the invention is produced in the HTL: This OLED (Example 13) demonstrates that the compound HTM-3 according to the invention is suitable as a hole-transport material for blue fluorescent OLEDs. The OLED is characterized by very good efficiency, as well as good voltage and lifetime: 8) Furthermore, the compounds HTM-1 and HTM-2 are used as hole transport material for a blue fluorescent OLED and are compared with the compounds CE-1 and CE-2 in an otherwise identical stack structure: Examples 14 and 15 demonstrate that the compounds of the invention are outstandingly suitable as hole-transport materials for blue-fluorescent OLEDs. The OLEDs achieve a low operating voltage with good external quantum efficiency and an outstanding lifetime (see below). Example 14 shows, in comparison with Experiment Comp. 1, that the compound HTM-1 of the invention leads to a lower operating voltage, higher efficiency, and longer lifetime of the OLED than the comparative compound CE-1. Example 15 shows, in comparison with Experiment Comp. 2, that the compound HTM-2 of the invention also leads to a lower operating voltage, higher efficiency, and longer lifetime of the OLED than the compound CE-2.

Claims

Claims 1. A compound according to one of the following formulas: where: W is the same or different at each occurrence selected from O and S; Z is the same or different at each occurrence selected from CR 1 and N; i is equal to 0 or 1, where for i=0 the group Y is omitted; for i = 0, Z is 1 chosen the same or different at each occurrence from CR 1 and N; for i = 1, Z 1 for C; Y is, at each occurrence, the same or different, selected from a bond, C(R 1 )2, O or S; Ar L is selected at each occurrence, identically or differently, from aromatic ring systems with 6 to 40 aromatic ring atoms, which are substituted by radicals R 2 are substituted, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which are substituted with residues R 2 are substituted; k is equal to 0, 1, 2 or 3, where for k=0 the group Ar L is omitted and the two at Ar Lbonding groups in formula (I) and (II) are directly connected to each other, where for k=2 two groups Ar L are bound in a chain one after the other, and where for k=3 three groups Ar L are bound one after the other in a chain; Ar 1 is selected at each occurrence, identically or differently, from aromatic ring systems with 6 to 40 aromatic ring atoms, which are substituted by radicals R 4 are substituted, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which are substituted with residues R 4 are substituted; Ar 2 is selected at each occurrence, identically or differently, from aromatic ring systems with 6 to 40 aromatic ring atoms, which are substituted by radicals R 5 are substituted, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which are substituted with residues R 5are substituted, wherein the aromatic or heteroaromatic ring systems are linked in the ortho position to the group V and the nitrogen atom; V is, at each occurrence, the same or different, selected from a bond, O, S, Si(R 5 )2and C(R 5 )2; R 1 is selected at each occurrence, the same or different, from H, D, F, Cl, Br, I, C(=O)R 6 , CN, Si(R 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 , S(=O)R 6 , S(=O)2R 6 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 1may be linked to one another and form a ring; wherein the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems are each linked to radicals R 6 are substituted; and wherein one or more CH2 groups in said alkyl, alkoxy, alkenyl and alkynyl groups are substituted by -R 6 C=CR 6 -, -C≡C-, Si(R 6 )2, C=O, C=NR 6 , -C(=O)O-, -C(=O)NR 6 -, NR 6 , P(=O)(R 6 ), -O-, -S-, SO or SO2; R 2 is selected at each occurrence, the same or different, from H, D, F, Cl, Br, I, C(=O)R 6 , CN, Si(R 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 , S(=O)R 6 , S(=O)2R 6, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 2 may be linked to one another and form a ring; wherein the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems are each linked to radicals R 6 are substituted; and wherein one or more CH2 groups in said alkyl, alkoxy, alkenyl and alkynyl groups are substituted by -R 6 C=CR 6 -, -C≡C-, Si(R 6 )2, C=O, C=NR 6 , -C(=O)O-, -C(=O)NR 6 -, NR 6 , P(=O)(R 6 ), -O-, -S-, SO or SO2; R 3is selected at each occurrence, the same or different, from H, D, F, Cl, Br, I, C(=O)R 6 , CN, Si(R 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 , S(=O)R 6 , S(=O)2R 6 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 3 may be linked to one another and form a ring; wherein the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems are each linked to radicals R 6 are substituted; and wherein one or more CH2 groups in said alkyl, alkoxy, alkenyl and alkynyl groups are substituted by -R 6 C=CR 6-, -C≡C-, Si(R 6 )2, C=O, C=NR 6 , -C(=O)O-, -C(=O)NR 6 -, NR 6 , P(=O)(R 6 ), -O-, -S-, SO or SO2; R 4 is selected at each occurrence, the same or different, from H, D, F, Cl, Br, I, C(=O)R 6 , CN, Si(R 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 , S(=O)R 6 , S(=O)2R 6 , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 4may be linked to one another and form a ring; wherein the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems are each linked to radicals R 6 are substituted; and wherein one or more CH2 groups in said alkyl, alkoxy, alkenyl and alkynyl groups are substituted by -R 6 C=CR 6 -, -C≡C-, Si(R 6 )2, C=O, C=NR 6 , -C(=O)O-, -C(=O)NR 6 -, NR 6 , P(=O)(R 6 ), -O-, -S-, SO or SO2; R 5 is selected at each occurrence, the same or different, from H, D, F, Cl, Br, I, C(=O)R 6 , CN, Si(R 6 )3, N(R 6 )2, P(=O)(R 6 )2, OR 6 , S(=O)R 6 , S(=O)2R 6, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 5 may be linked to one another and form a ring; wherein the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems are each linked to radicals R 6 are substituted; and wherein one or more CH2 groups in said alkyl, alkoxy, alkenyl and alkynyl groups are substituted by -R 6 C=CR 6 -, -C≡C-, Si(R 6 )2, C=O, C=NR 6 , -C(=O)O-, -C(=O)NR 6 -, NR 6 , P(=O)(R 6 ), -O-, -S-, SO or SO2; R 6is selected at each occurrence, the same or different, from H, D, F, Cl, Br, I, C(=O)R 7 , CN, Si(R 7 )3, N(R 7 )2, P(=O)(R 7 )2, OR 7 , S(=O)R 7 , S(=O)2R 7 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more residues R 6 may be linked to one another and form a ring; wherein the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic ring systems and heteroaromatic ring systems are each linked to radicals R 7 are substituted; and wherein one or more CH2 groups in said alkyl, alkoxy, alkenyl and alkynyl groups are substituted by -R 7 C=CR7 -, -C≡C-, Si(R 7 )2, C=O, C=NR 7 , -C(=O)O-, -C(=O)NR 7 -, NR 7 , P(=O)(R 7 ), -O-, -S-, SO or SO2; R 7 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 7 may be linked together to form a ring; and wherein said alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems may be substituted by one or more radicals selected from F and CN.

2. A compound according to claim 1, characterized in that Z is CR 1 3. A compound according to claim 1 or 2, characterized in that ArL is selected at each occurrence, identically or differently, from phenyl, biphenyl, naphthyl and fluorenyl, each of which is substituted by radicals R 2 are substituted.

4. A compound according to one or more of claims 1 to 3, characterized in that i is 1 and Y is a bond.

5. A compound according to one or more of claims 1 to 4, characterized in that Ar 1 is selected, identically or differently at each occurrence, from monovalent groups derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, 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, where each of the monovalent groups is linked to residues R 46. A compound according to one or more of claims 1 to 5, characterized in that Ar 2 is selected at each occurrence, identically or differently, from groups which are divalent in the ortho position and are derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, 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 and pyridazine, where each of the monovalent groups is substituted with radicals R 5 7. A compound according to one or more of claims 1 to 6, characterized in that in the compounds according to one of the formulas (I) and (II) none, one, two or three of the groups R 1 in each formula other than H and D, and that these groups other than H and D are selected at each occurrence, the same or different, from F, CN, Si(R6 )3, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aryl groups having 6 to 25, preferably 6 to 14 aromatic ring atoms, and heteroaryl groups having 5 to 40 aromatic ring atoms, wherein the said alkyl groups, the said aryl groups and the said heteroaryl groups are each substituted by radicals R 6 are substituted.

8. Compound according to one or more of claims 1 to 7, characterized in that in the compounds according to one of the formulas (I) and (II) no, one, two or three groups R 3 in each formula other than H and D, and that these groups other than H and D are selected at each occurrence, the same or different, from F, CN, Si(R 6)3, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aryl groups having 6 to 25, preferably 6 to 14 aromatic ring atoms, and heteroaryl groups having 5 to 40 aromatic ring atoms, where the alkyl groups mentioned, the mentioned aryl groups and the mentioned heteroaryl groups each with radicals R 6 9. A compound according to one or more of claims 1 to 8, characterized in that all radicals R 1 and R 3 in formulas (I) and (II) are H or D.

10. A compound according to one or more of claims 1 to 9, characterized in that no, one, two, three or four groups R 4 per remaining area 1 not equal to H and D, and that these groups not equal to H and D are chosen at each occurrence, the same or different, from F, CN, Si(R 6)3, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aryl groups having 6 to 25, preferably 6 to 14 aromatic ring atoms, and heteroaryl groups having 5 to 40 aromatic ring atoms, wherein the said alkyl groups, the said aryl groups and the said heteroaryl groups are each substituted by radicals R 6 11. A compound according to one or more of claims 1 to 10, characterized in that no, one, two, three or four groups R 5 per remaining area 2 not equal to H and D, and that these groups not equal to H and D are chosen at each occurrence, the same or different, from F, CN, Si(R 6)3, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aryl groups having 6 to 25, preferably 6 to 14 aromatic ring atoms, and heteroaryl groups having 5 to 40 aromatic ring atoms, wherein the said alkyl groups, the said aryl groups and the said heteroaryl groups are each substituted by radicals R 6 are substituted.

12. A compound according to one or more of claims 1 to 11, characterized in that the compound corresponds to one of the following formulas: wherein the groups occurring are defined as in one or more of the preceding claims; or that the compound corresponds to one of the following formulas wherein the groups occurring are defined as in one or more of the preceding claims.

13. A compound according to any one of claims 1 to 12, characterized in that the compound corresponds to one of the following formulas: wherein the groups occurring are defined as in one or more of the preceding claims; or that the compound corresponds to one of the following formulas wherein the groups occurring are defined as in one or more of the preceding claims.

14. A process for preparing a compound according to one or more of claims 1 to 13, characterized in that an indenodibenzofuran derivative substituted by a reactive group is reacted a) in a coupling reaction with a secondary amine, or b) in a coupling reaction with an aromatic or heteroaromatic compound carrying a reactive group.

15. An oligomer, polymer or dendrimer comprising one or more compounds according to one or more of claims 1 to 13, wherein the bond(s) to the polymer, oligomer or dendrimer are at any desired positions denoted by R in formula (I) and (II). 1 , R 2 , R 3 , R 4 or R 5substituted positions.

16. A formulation comprising at least one compound according to one or more of claims 1 to 13 or at least one polymer, oligomer, or dendrimer according to claim 15, and at least one solvent.

17. An electronic device comprising at least one compound according to one or more of claims 1 to 13, or at least one polymer, oligomer, or dendrimer according to claim 15.

18. The electronic device according to claim 17, characterized in that it is an organic electroluminescent device and contains an anode, a cathode, and at least one emitting layer, and in that the compound is contained in a hole-transporting layer or in an emitting layer of the device.

19. Use of a compound according to one or more of claims 1 to 13 in an electronic device.

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