Materials for organic electroluminescent devices

Abstract

To provide materials for organic electroluminescent devices.SOLUTION: Provided are amine compounds having dibenzofuran, dibenzothiophene and fluorene groups for use as triplet matrix materials in organic electroluminescent devices. Further provided are electronic devices comprising the compounds.SELECTED DRAWING: None

Description

Summary of the Invention

[0001] The present invention describes amines bearing dibenzofuran, dibenzothiophene and fluorene groups, in particular for use as triplet matrix materials in organic electroluminescent devices. The present invention further relates to methods for preparing the compounds of the invention and to electronic devices comprising these compounds.

[0002] The structure of organic electroluminescent device (OLED) that uses organic semiconductor as functional material is described in, for example, US4539507, US5151629, EP0676461 and WO98 / 27136.The luminescent material used is often an organometallic complex that exhibits phosphorescence.For quantum mechanical reasons, the use of organometallic compounds as phosphorescent emitters can achieve up to four times the energy efficiency and power efficiency.In general, OLED, especially in OLED that exhibits phosphorescence, still needs to be improved, for example, in terms of efficiency, operating voltage and lifespan.

[0003] The properties of phosphorescent OLEDs are not solely determined by the triplet emitters used. More specifically, other materials used, such as matrix materials, are also particularly important in this regard. Therefore, improvements in these materials can also lead to significant improvements in the properties of the OLED.

[0004] In the prior art, amines containing fluorene and dibenzofuran groups are known from US 2014 / 0284578. Compounds containing carbazole are also known from EP 2421064. US 2013 / 0234118 discloses amines containing fused aromatic groups, for example amines containing fused aromatic groups such as pyrene.

[0005] In general, for these materials used as matrix materials, improvements are still required, especially with regard to lifetime and oxidation sensitivity, but also with regard to device efficiency and operating voltage.

[0006] It is an object of the present invention to provide compounds suitable for use in phosphorescent or fluorescent OLEDs, especially as matrix materials. More particularly, it is an object of the present invention to provide matrix materials suitable for red, yellow, and green phosphorescent OLEDs, and possibly also for blue phosphorescent OLEDs, which lead to long lifetimes, good efficiency, and low operating voltages. In particular, the properties of the matrix material also have a significant impact on the lifetime and efficiency of organic electroluminescent devices.

[0007] It has surprisingly been found that electroluminescent devices comprising compounds of formula (1) below have improvements over the prior art, particularly when used as matrix materials for phosphorescent dopants.

[0008] Therefore, the present invention provides a compound of the following formula (1):

[0009] [ka]

[0010] [where the symbols used are as follows: X is O or S; Y is O, S, or CR2; Ar, in each occurrence, is the same or different and is an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, optionally substituted by one or more R radicals, where Ar contains only aryl or heteroaryl groups having up to 15 aromatic ring atoms, does not contain a carbazolyl group as a heteroaryl group, and does not contain a 9,9'-spirobifluorene group; R, in each occurrence, is the same or different and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO, N(Ar 1 )2, N(R 4 )2, C(=O)Ar 1 , C(=O)R 4 , P(=O)(Ar 1 )2, P(Ar 1)2, B(Ar 1 )2, a linear alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms (each of which may be selected from the group consisting of one or more R 4 radical, and one or more non-adjacent CH groups may be substituted by R 4 C=CR 4 , C=O, C=S, C=NR 4 , P(=O)(R 4 ), SO, SO2, NR 4 , O, S or CONR 4 and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2), having 5 to 40 aromatic ring atoms, in each case one or more R 4 Aromatic or heteroaromatic ring systems, optionally substituted by radicals, having 5 to 40 aromatic ring atoms and one or more R 1 an aryloxy or heteroaryloxy group, optionally substituted by a radical, or a group having 5 to 40 aromatic ring atoms and one or more R 4 and wherein two R substituents attached to the same carbon atom or adjacent carbon atoms are selected from the group consisting of aralkyl or heteroaralkyl groups, optionally substituted by a radical; and wherein two R substituents attached to the same carbon atom or adjacent carbon atoms are selected from the group consisting of one or more R 4 optionally forming a monocyclic or polycyclic aliphatic ring system, optionally substituted by radicals; R 1 are in each case the same or different and are H, D, F, Cl, Br, I, CN, NO2, N(Ar 1 )2, N(R 4 )2, C(=O)Ar 1 , C(=O)R 4 , P(=O)(Ar 1 )2, P(Ar 1 )2, B(Ar 1)2, a linear alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms (each of which may be selected from the group consisting of one or more R 4 radical, and one or more non-adjacent CH groups may be substituted by R 4 C=CR 4 , C=O, C=S, C=NR 4 , P(=O)(R 4 ), SO, SO2, NR 4 , O, S or CONR 4 and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2), having 5 to 40 aromatic ring atoms, in each case one or more R 4 Aromatic or heteroaromatic ring systems, optionally substituted by radicals, having 5 to 40 aromatic ring atoms and one or more R 4 an aryloxy or heteroaryloxy group, optionally substituted by a radical, or a group having 5 to 40 aromatic ring atoms and one or more R 4 and at the same time, two R bonded to adjacent carbon atoms are selected from the group consisting of aralkyl and heteroaralkyl groups, optionally substituted by a radical; 1 Substituent or two R 1 and R 3 The substituent is one or more R 4 optionally forming a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, optionally substituted by radicals; R 2 are in each case the same or different and are H, D, F, Cl, Br, I, CN, NO2, N(Ar 1 )2, N(R 4 )2, C(=O)Ar 1 , C(=O)R 4 , P(=O)(Ar 1 )2, P(Ar 1 )2, B(Ar 1)2, a linear alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms (each of which may be selected from the group consisting of one or more R 4 radical, and one or more non-adjacent CH groups may be substituted by R 4 C=CR 4 , C=O, C=S, C=NR 4 , P(=O)(R 4 ), SO, SO2, NR 4 , O, S or CONR 4 and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2), having 5 to 40 aromatic ring atoms, in each case one or more R 4 Aromatic or heteroaromatic ring systems, optionally substituted by radicals, having 5 to 40 aromatic ring atoms and one or more R 4 an aryloxy or heteroaryloxy group, optionally substituted by a radical, or a group having 5 to 40 aromatic ring atoms and one or more R 4 and at the same time, two R bonded to adjacent carbon atoms are selected from the group consisting of aralkyl and heteroaralkyl groups, optionally substituted by a radical; 2 The substituent is one or more R 4 optionally forming a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, optionally substituted by radicals; R 3 are in each case the same or different and are H, D, F, Cl, Br, I, CN, NO2, N(Ar 1 )2, N(R 4 )2, C(=O)Ar 1 , C(=O)R 4 , P(=O)(Ar 1 )2, P(Ar 1 )2, B(Ar 1)2, a linear alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms (each of which may be selected from the group consisting of one or more R 4 radical, and one or more non-adjacent CH groups may be substituted by R 4 C=CR 4 , C=O, C=S, C=NR 4 , P(=O)(R 4 ), SO, SO2, NR 4 , O, S or CONR 4 and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2), having 5 to 40 aromatic ring atoms, in each case one or more R 4 Aromatic or heteroaromatic ring systems, optionally substituted by radicals, having 5 to 40 aromatic ring atoms and one or more R 4 an aryloxy or heteroaryloxy group, optionally substituted by a radical, or a group having 5 to 40 aromatic ring atoms and one or more R 4 and at the same time, two R bonded to adjacent carbon atoms are selected from the group consisting of aralkyl and heteroaralkyl groups, optionally substituted by a radical; 3 and R 1 The substituent is one or more R 4 optionally forming a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, optionally substituted by radicals; Ar 1 are, in each occurrence, the same or different, have 5 to 30 aromatic ring atoms, and one or more non-aromatic R 4 an aromatic or heteroaromatic ring system optionally substituted by a radical; and at the same time, two Ar 1 The radical is a single bond or N(R 4 ), C(R 4) 2, may be crosslinked to each other by bridges selected from O and S, R 4 are in each case the same or different and are H, D, F, Cl, Br, I, CN, NO2, N(R 5 )2, C(=O)R 5 a linear alkyl, alkoxy, or thioalkyl group having 1 to 20 carbon atoms, a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms (each of which may be selected from the group consisting of one or more R 5 radical, and one or more non-adjacent CH groups may be substituted by R 5 C=CR 5 , C=O, C=S, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2), having 5 to 40 aromatic ring atoms, in each case one or more R 5 Aromatic or heteroaromatic ring systems, optionally substituted by radicals, having 5 to 40 aromatic ring atoms and one or more R 5 an aryloxy or heteroaryloxy group, optionally substituted by a radical, or a group having 5 to 40 aromatic ring atoms and one or more R 5 and at the same time, two R attached to the same carbon atom or adjacent carbon atoms are selected from the group consisting of aralkyl or heteroaralkyl groups, optionally substituted by a radical; 4 The substituent is one or more R 5 optionally forming a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, optionally substituted by radicals; R 5are the same or different in each occurrence and are selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, or CN, and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; and at the same time, two or more adjacent R 5 The substituents together may form a monocyclic or polycyclic aliphatic ring system; Here, as an example, the nitrogen atom is represented by R 1 or R 3 is attached to the corresponding carbon atom instead of 3 In this case, Y is not CR2. The present invention provides a compound of the formula:

[0011] Adjacent carbon atoms in the context of the present invention are carbon atoms that are directly bonded to one another.

[0012] The expression that two or more radicals may together form a ring is understood in the context of the present description to mean, inter alia, that the two radicals are connected to one another by a chemical bond, with the formal elimination of two hydrogen atoms, as exemplified by the following scheme:

[0013] [ka]

[0014] However, it should be further understood that the above expression also means that when one of the two radicals is hydrogen, the second radical is attached to the position where the hydrogen atom was attached, forming a ring, as exemplified by the following scheme:

[0015] [ka]

[0016] A fused aryl group in the context of the present invention is a group in which two or more aromatic groups are fused, i.e., fused to each other along a common edge, as in, for example, naphthalene. In contrast, for example, fluorene is not a fused aryl group in the context of the present invention, because the two aromatic groups in fluorene do not share a common edge.

[0017] An aryl group in the context of the present invention contains 6 to 40 carbon atoms; a heteroaryl group in the context of the present invention contains 2 to 40 carbon atoms and at least one heteroatom, provided that the total number of carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aryl or heteroaryl group is understood here to mean either a single aromatic ring, i.e., benzene, or a single heteroaromatic ring, such as, for example, pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl group, such as, for example, naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc.

[0018] An aromatic ring system in the context of the present invention comprises 6 to 40 carbon atoms in the ring system. A heteroaromatic ring system in the context of the present invention comprises 1 to 40 carbon atoms and at least one heteroatom in the ring system, provided that the total number of carbon atoms and heteroatoms is at least 5. The heteroatom is preferably selected from N, O, and / or S. An aromatic or heteroaromatic ring system in the context of the present invention is understood to mean a system that does not necessarily contain only aryl or heteroaryl groups, but also in which two or more aryl or heteroaryl groups can be interrupted by non-aromatic units (preferably less than 10% of atoms other than H), such as carbon, nitrogen, or oxygen atoms, or carbonyl groups. Thus, for example, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc., as well as systems in which two or more aryl groups are interrupted by, for example, linear or cyclic alkyl or silyl groups, are also considered to be aromatic ring systems in the context of the present invention. In addition, systems in which two or more aryl or heteroaryl groups are directly bonded to one another, such as biphenyl, terphenyl, quaterphenyl, or bipyridine, are also properly considered to be aromatic or heteroaromatic ring systems.

[0019] In the context of this invention, a cyclic alkyl, alkoxy or thioalkoxy group is understood to mean a mono-, bi- or polycyclic group.

[0020] In the context of the present invention, C1 to C 20-Alkyl groups (in which individual hydrogen atoms or CH groups may also be replaced by the above groups) are, for example, methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neohexyl, cyclohexyl, 1-methylbutyl, 2 ... -Methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2.2.2]octyl, 2-bicyclo[2.2.2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hexyl thi-1-yl, 1,1-dimethyl-n-hept-1-yl, 1,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n-dec-1-yl, 1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl, 1,1-dimethyl-n-hexadec-1-yl, 1,1-dimethyl-n-octadec-1-yl, 1,1-diethyl-n-hex-1-yl, 1,1-diethyl-n-hept-1-yl, 1,1-diethyl-n-oct-1-yl, 1,1-diethyl-n- It is understood to mean the dec-1-yl, 1,1-diethyl-n-dodec-1-yl, 1,1-diethyl-n-tetradec-1-yl, 1,1-diethyl-n-hexadec-1-yl, 1,1-diethyl-n-octadec-1-yl, 1-(n-propyl)cyclohex-1-yl, 1-(n-butyl)cyclohex-1-yl, 1-(n-hexyl)cyclohex-1-yl, 1-(n-octyl)cyclohex-1-yl and 1-(n-decyl)cyclohex-1-yl radicals.Alkynyl groups are understood to mean, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl. Alkynyl groups are understood to mean, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. C1-C. 40 An -alkoxy group is understood to mean, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy.

[0021] Aromatic or heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and which may in each case be substituted by the above-mentioned radicals and which may be connected to the aromatic or heteroaromatic ring system in any desired position are, for example, benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzofluoranthene, nephthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, spirobifluorene, Dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-monobenzoindenofluorene, cis- or trans-dibenzoindenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, indolocarbazole, indenocarbazole pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3 -thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1,5-diazaanthracene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazapyrylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorubine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,It is understood to mean groups derived from 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.

[0022] Preferably, in formula (1), when Y is CR2, the nitrogen atom is R 1 and when Y is O or S, the nitrogen atom is bonded to the corresponding carbon atom instead of R 1 or R 3 is bonded to the corresponding carbon atom instead of

[0023] In a preferred embodiment, X is O.

[0024] In a further preferred embodiment, Y is CR2.

[0025] In a further preferred embodiment, X is O and Y is CR2.

[0026] In a further preferred embodiment of the present invention, the compound of formula (1) is optionally substituted carbazole, R 1 or R 2 When it has a substituent, the carbazole is not bonded through the two positions.

[0027] In a further embodiment of the invention, the compound has formula (1-1) or formula (1-2):

[0028] [ka]

[0029] (where the symbols correspond to those in equation (1)) The compound is selected from the group consisting of:

[0030] In a further preferred embodiment of the invention, Ar in each occurrence is the same or different and is an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably 6 to 18 aromatic ring atoms, more preferably an aromatic ring system having 6 to 12 aromatic ring atoms or a heteroaromatic ring system having 6 to 13 aromatic ring atoms, each of which may be substituted by one or more R radicals, but is preferably unsubstituted, and wherein Ar contains only aryl or heteroaryl groups having up to 15 aromatic ring atoms, does not contain carbazolyl groups, and does not contain 9,9'-spirobifluorene groups. Examples of suitable Ar groups are selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, especially branched terphenyl, quaterphenyl, especially branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, and 1-, 2-, 3- or 4-dibenzothienyl, each of which may be substituted by one or more R radicals, but is preferably unsubstituted.

[0031] In a preferred embodiment of the present invention, Ar is represented by any one of the formulae (Ar-1) to (Ar-16):

[0032] [ka]

[0033] [ka]

[0034] is selected from the structure where the symbols correspond to those in equation (1), and in addition Q may be the same or different in each case, and CR 4 or N, with not more than three Q symbols per ring being N; E is in each case the same or different, and C(R 4 )2, O, S or C=O; where two R 4 does not form an aromatic or heteroaromatic ring system; G is NR in each case 4 , C(R 4 )2, O, S or C=O; and * indicates a bond to a nitrogen atom.

[0035] Preferably, no Q is N.

[0036] In further preferred embodiments, the Ar group in each case is selected from groups having the structure of formulae (Ar-1) to (Ar-16), where these general formulae are replaced by the particularly preferred respective embodiments of the following formulae (Ar-1-1) to (Ar-16-6) (e.g., formula (Ar-1) is replaced by one of the formulae (Ar-1-1) to (Ar-1-9)),

[0037] [ka]

[0038] [ka]

[0039] [ka]

[0040] [ka]

[0041] [ka]

[0042] [ka]

[0043] Here, the symbols correspond to the symbols in formulae (Ar-1) to (Ar-16). 4 may be substituted by

[0044] In a further embodiment of the present invention, R 2 are in each case the same or different, and in the case of aromatic or heteroaromatic ring systems, the structures of the formulae (Ar-1) to (Ar-16), or preferred embodiments thereof, as well as the formulae (Ar-17) and (Ar-18):

[0045] [ka]

[0046] is selected from the structure where the symbols correspond to those in formula (1), and furthermore, in formulas (Ar-17) and (Ar-18): Q may be the same or different in each case, and CR 4 or N, with not more than three Q symbols per ring being N; E in each case may be the same or different, and NR 4 , C(R 4 )2, O, S or C=O, where two R 4 does not form an aromatic or heteroaromatic ring system; G is, in each case, NR 4 , C(R 4 )2, O, S or C=O; and * indicates attachment to an aromatic ring system.

[0047] Preferably, no Q is N.

[0048] In a further preferred embodiment, in each instance of R 2In the case of an aromatic or heteroaromatic ring system, the group is selected from groups having the structure of formulae (Ar-1) to (Ar-18), where these general formulae are replaced by the particularly preferred respective embodiments of the following formulae (Ar-1-1) to (Ar-16-6) (for example, formula (Ar-1) is replaced by one of the formulae (Ar-1-1) to (Ar-1-9)), and furthermore, groups having the following formulae:

[0049] [ka]

[0050] is preferred, Here, the symbols correspond to those in equation (1).

[0051] In one embodiment of the invention, the compound has formula (2) or formula (3):

[0052] [ka]

[0053] The structure is where the symbols correspond to those in formula (1), where one R bonded to a carbon atom 2 and one R 4 is replaced by a single bond, and in formula (2), R 2 In this case, it is preferably in a six-membered ring that is not bonded to a nitrogen atom.

[0054] In a preferred embodiment of the invention, the carbazole is not linked through its two positions.

[0055] In a further preferred embodiment of the present invention, the compound has the formula (2-1) and (2-2):

[0056] [ka]

[0057] where the symbols correspond to the symbols in formula (2), and where one R in formula (2-1) 2 and one R bonded to a carbon atom in formula (2-2) 4 is replaced by a single bond (in the case of formula (2-2), on the six-membered ring that is not bonded to the nitrogen atom).

[0058] In a further preferred embodiment of the present invention, the compound has the formula (2-3):

[0059] [ka]

[0060] is a compound of Here, the symbols correspond to those in equation (2).

[0061] In a further preferred embodiment of the present invention, the compound has the formula (3-1) and (3-2):

[0062] [ka]

[0063] is a compound of the structure where the symbols correspond to those in formula (3), where one R in formula (3-1) 2 and one R bonded to a carbon atom in formula (3-2) 4 is replaced by a single bond (in the case of formula (3-2), on the six-membered ring bonded to the nitrogen atom).

[0064] In a further preferred embodiment of the present invention, the compound has the formula (3-3):

[0065] [ka]

[0066] is a compound of Here, the symbols correspond to those in equation (3).

[0067] In a further embodiment of the present invention, the compound has the formula (2-1a), (2-1b), (2-2a), (2-2b):

[0068] [ka]

[0069] [ka]

[0070] is a compound of Here, the symbols correspond to those in equation (2).

[0071] In a further embodiment of the invention, the compound has the formula (3-1a), (3-1b), (3-2a) or (3-2b):

[0072] [ka]

[0073] [ka]

[0074] is a compound of Here, the symbols correspond to those in equation (3).

[0075] In a further preferred embodiment of the present invention, the compound has formula (2-3a) or (2-3b):

[0076] [ka]

[0077] is a compound of Here, the symbols correspond to those in equation (2-3).

[0078] In a further preferred embodiment of the present invention, the compound has formula (3-3a) or (3-3b):

[0079] [ka]

[0080] is a compound of Here, the symbols correspond to those in equation (3-3).

[0081] In a further embodiment of the present invention, R 1 and R 3 are in each case the same or different and, in the case of an aromatic or heteroaromatic ring system, are selected from one of the formulae (Ar-1) to (Ar-16), in which the definitions of the symbols correspond to those defining Ar, * is a bond to an aromatic ring system.

[0082] Preferably, the R substituent attached to Ar is H, D, F, CN, N(Ar 1 ) 2, a linear alkyl group having 1 to 8 carbon atoms, preferably having 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group having 3 to 8 carbon atoms, preferably having 3, 4, 5 or 6 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, preferably having 2, 3 or 4 carbon atoms (an alkyl or alkenyl group may in each case be represented by one or more R 4 or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, more preferably having 6 to 13 aromatic ring atoms (each of which may be substituted by one or more R 4 at the same time, two R substituents attached to adjacent carbon atoms are selected from the group consisting of one or more R 4It is optionally possible to form a monocyclic or polycyclic aliphatic ring system which may be substituted by radicals, but is preferably unsubstituted.

[0083] When Y is CR2, the R radicals attached to this carbon atom are in each case the same or different and are straight-chain alkyl groups having 1 to 8 carbon atoms, preferably having 1, 2, 3 or 4 carbon atoms, or branched or cyclic alkyl groups having 3 to 8 carbon atoms, preferably having 3, 4, 5 or 6 carbon atoms, or alkenyl groups having 2 to 8 carbon atoms, preferably having 2, 3 or 4 carbon atoms (each alkyl or alkenyl group being a group consisting of one or more R 4 radicals, wherein one or more non-adjacent CH groups may be replaced by O and one or more hydrogen atoms may be replaced by D or F), or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, more preferably having 6 to 13 aromatic ring atoms (each of which may be substituted by one or more R 4 and at the same time, two R substituents are preferably substituted by one or more R 4 Optionally, the radicals may form a monocyclic or polycyclic aliphatic ring system, optionally substituted. The ring formation between two R substituents forms a spiro system.

[0084] Preferably, R 1 The substituents are H, D, F, CN, N(Ar 1 ) 2, a linear alkyl group having 1 to 8 carbon atoms, preferably having 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group having 3 to 8 carbon atoms, preferably having 3, 4, 5 or 6 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, preferably having 2, 3 or 4 carbon atoms (an alkyl or alkenyl group may in each case be represented by one or more R 4or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, more preferably having 6 to 13 aromatic ring atoms (each of which may be substituted by one or more R 4 at the same time, two R 1 Substituent or two R 1 and R 3 The substituent is one or more R 4 It is optionally possible to form a monocyclic or polycyclic aliphatic ring system which may be substituted by radicals, but is preferably unsubstituted.

[0085] Preferably, R 2 The substituents are H, D, F, CN, N(Ar 1 ) 2, a linear alkyl group having 1 to 8 carbon atoms, preferably having 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group having 3 to 8 carbon atoms, preferably having 3, 4, 5 or 6 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, preferably having 2, 3 or 4 carbon atoms (an alkyl or alkenyl group may in each case be represented by one or more R 4 or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, more preferably having 6 to 13 aromatic ring atoms (each of which may be substituted by one or more R 4 at the same time, two R 2 The substituent is one or more R 4 It is optionally possible to form a monocyclic or polycyclic aliphatic ring system which may be substituted by radicals, but is preferably unsubstituted.

[0086] Preferably, R 3 The substituents are H, D, F, CN, N(Ar 1 ) 2, a linear alkyl group having 1 to 8 carbon atoms, preferably having 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group having 3 to 8 carbon atoms, preferably having 3, 4, 5 or 6 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, preferably having 2, 3 or 4 carbon atoms (an alkyl or alkenyl group may in each case be represented by one or more R 4 or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, more preferably having 6 to 13 aromatic ring atoms (each of which may be substituted by one or more R 4 at the same time, two R 3 and R 1 The substituent is one or more R 4 It is optionally possible to form a monocyclic or polycyclic aliphatic ring system which may be substituted by radicals, but is preferably unsubstituted.

[0087] Preferably, R 4 The substituents are H, D, F, CN, N(Ar 1 )2, N(R 5 ) 2, a linear alkyl group having 1 to 8 carbon atoms, preferably having 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group having 3 to 8 carbon atoms, preferably having 3, 4, 5 or 6 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, preferably having 2, 3 or 4 carbon atoms (an alkyl or alkenyl group may in each case be represented by one or more R 4or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, more preferably having 6 to 13 aromatic ring atoms (each of which may be substituted by one or more non-aromatic R radicals, but is preferably unsubstituted); 5 at the same time, two R 4 The substituent is one or more R 5 It is optionally possible to form a monocyclic or polycyclic aliphatic ring system which may be substituted by radicals, but is preferably unsubstituted.

[0088] E or G is NR 4 If R is bonded to this nitrogen atom, 4 The radicals are in each case the same or different and have 5 to 24 aromatic ring atoms and in each case one or more R 5 An aromatic or heteroaromatic ring system, preferably having 6 to 18 aromatic ring atoms, optionally substituted by a radical, and one or more R 5 Preferably, the ring system is an aromatic or heteroaromatic ring system, optionally substituted by a suitable radical. 4 Examples of substituents are selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, especially branched terphenyl, quaterphenyl, especially branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1,3,5-triazinyl, 4,6-diphenyl-1,3,5-triazinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, and 1-, 2-, 3- or 4-carbazolyl, where the carbazolyl group is selected from the group consisting of a nitrogen atom and an R other than H or D. 5 Each of these groups is substituted by one or more R 5 It may be substituted by a radical, but is preferably unsubstituted.

[0089] In a further embodiment of the invention, the compound does not contain any additional non-bridging amines, except for the central nitrogen atom. This means, for example, that none of the radicals are N(Ar 1 )2 or N(R 4 )2.

[0090] In a further embodiment of the present invention, at least one of R, R in formula (1) 1 , R 2 or R 3 is a heteroaryl group.

[0091] In a further embodiment of the invention, Ar is not a group of formula (Ar-10-2), such as a 2-fluoroenyl group.

[0092] The above preferences can be expressed individually or together. It is preferred when the above preferences are expressed together.

[0093] Examples of suitable compounds of the present invention are those structures shown below.

[0094] [Table 1-1]

[0095] [Table 1-2]

[0096] [Table 1-3]

[0097] [Table 1-4]

[0098] [Table 1-5]

[0099]

Table 1-6

[0100]

Table 1-7

[0101]

Table 1-8

[0102]

Table 1-9

[0103]

Table 1-10

[0104]

Table 1-11

[0105]

Table 1-12

[0106]

Table 1-13

[0107]

Table 1-14

[0108]

Table 1-15

[0109] [Table 1-16]

[0110] The compounds of the present invention can be prepared by synthetic steps known to those skilled in the art, such as bromination, Suzuki coupling, Ullmann coupling, Hartwig-Buchwald coupling, etc. A suitable synthetic method is generally depicted in Scheme 1 below.

[0111] [ka]

[0112] The compound of formula (2) can be prepared according to the following scheme (2):

[0113] [ka]

[0114] can be obtained by

[0115] In this scheme, R is a group of R, R according to formula (1) or (2). 1 , R 2 or R 3 Rather than fluorene derivatives, it is also possible to use corresponding dibenzofuran or dibenzothiophene derivatives.

[0116] For example, by spin coating or printing method, the compound of the present invention is processed from the liquid phase, and the compound of the present invention is required to be prepared.These preparations can be, for example, solutions, dispersions or emulsions.For this purpose, it may be preferable to use a mixture of two or more solvents. 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, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone ... Examples of suitable solvents include xylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, NMP, p-cymene, phenetole, 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, hexamethylindane, and mixtures of these solvents.

[0117] Therefore, the present invention further provides a formulation comprising the compound of the present invention and at least one additional compound.The additional compound can be, for example, a solvent, particularly one of the above-mentioned solvents, or a mixture of these solvents.Alternatively, the additional compound can be at least one additional organic or inorganic compound, such as a light-emitting compound, particularly a phosphorescent dopant, and / or an additional matrix material, which are also used in electronic devices.Suitable light-emitting compounds and additional matrix materials are listed at the end of this document in relation to organic electroluminescent devices.This additional compound can also be a polymer.

[0118] The compounds and mixtures of the present invention are suitable for use in electronic devices.Electronic devices are understood to mean devices that comprise at least one layer that comprises at least one organic compound.This component can also comprise inorganic material, or else the layer that is entirely made of inorganic material.

[0119] The present invention therefore further provides the use of the compounds or mixtures of the invention in electronic devices, in particular in organic electroluminescent devices.

[0120] The present invention further provides an electronic device comprising at least one compound or mixture of the invention as detailed above, in which case the preferences detailed above for the compound also apply to the electronic device.

[0121] The electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs, PLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic dye-sensitized solar cells, organic optical detectors, organic photoreceptors, organic field-quenched devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), and organic plasmonic light-emitting devices, preferably organic electroluminescent devices (OLEDs, PLEDs), in particular phosphorescent OLEDs.

[0122] An organic electroluminescent device comprises a cathode, an anode, and at least one emissive layer. In addition to these layers, it may also comprise additional layers, such as, in each case, one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, and / or charge generation layers. Similarly, an interlayer with exciton blocking functionality may be introduced, for example, between two emissive layers. However, it should be noted that the presence of any of these layers is not necessarily required. In this case, the organic electroluminescent device may comprise one emissive layer or multiple emissive layers. When multiple emissive layers are present, they preferably have several emission maxima in the range of 380 nm to 750 nm, so that the overall result is white light emission. In other words, various emissive compounds capable of emitting fluorescence or phosphorescence are used in the emissive layers. One embodiment of the present invention relates to a system having three emissive layers, where the three layers exhibit blue, green, and orange or red emission. These may be fluorescent or phosphorescent layers, or hybrid systems in which fluorescent and phosphorescent layers are combined with each other. A further aspect of the invention relates to tandem OLEDs. White-emitting electroluminescent devices can be used, for example, for lighting applications, but can also be used in combination with color filters for full-color displays.

[0123] The compounds of the present invention according to the above-described embodiments can be used in various layers depending on the exact structure.Preferred organic electroluminescent devices include the compounds of formula (1) or preferred embodiments as the matrix material for fluorescent or phosphorescent emitters, or for emitters that exhibit TADF (thermally activated delayed fluorescence), especially for phosphorescent emitters, and / or in electron transport layer and / or electron blocking layer or exciton blocking layer and / or hole transport layer and / or hole injection layer, depending on the exact substitution.In this regard, the preferred embodiments described above also apply to the use of materials in organic electronic devices.

[0124] In a preferred embodiment of the present invention, the compound of formula (1) or a preferred embodiment thereof is used as a matrix material for fluorescent or phosphorescent compounds, especially for phosphorescent compounds, in the light-emitting layer. In this case, the organic electroluminescent device may comprise one light-emitting layer, or it may comprise multiple light-emitting layers, in which case at least one light-emitting layer comprises at least one compound of the present invention as a matrix material.

[0125] When the compound of formula (1) or preferred embodiment is used as a matrix material for a light-emitting compound in the light-emitting layer, it is preferably used in combination with one or more phosphorescent materials (triplet emitters).Phosphorescence in the context of the present invention is understood to mean luminescence from an excited state with a spin multiplicity of >1, in particular from an excited triplet state.In the context of this application, all luminescent transition metal complexes and luminescent lanthanide complexes, in particular all complexes of iridium, platinum and copper, are considered to be phosphorescent compounds.

[0126] The mixture of a compound according to formula (1) or a preferred embodiment with a light-emitting compound comprises from 99% to 1% by volume, preferably from 98% to 10% by volume, more preferably from 97% to 60% by volume, and in particular from 95% to 80% by volume, of the compound according to formula (1) or a preferred embodiment, based on the total mixture of light-emitting material and matrix material. Correspondingly, the mixture comprises from 1% to 99% by volume, preferably from 2% to 90% by volume, more preferably from 3% to 40% by volume, and in particular from 5% to 20% by volume of the light-emitting material, based on the total mixture of light-emitting material and matrix material. When the compounds are processed from a solution, it is preferable to use the corresponding amounts in weight percent rather than the amounts in volume percent specified above.

[0127] Suitable phosphorescent compounds (= triplet emitters) are in particular compounds that emit light, preferably in the visible range, when appropriately excited, and contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, more preferably greater than 56 and less than 80, in particular a metal with this atomic number. Preferred phosphorescent emitters used are compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, in particular compounds containing iridium or platinum. In the context of the present invention, all luminescent compounds containing the above metals are considered phosphorescent compounds.

[0128] Examples of such luminescent materials are disclosed in applications WO00 / 70655, WO2001 / 41512, WO2002 / 02714, WO2002 / 15645, EP1191613, EP1191612, EP1191614, WO05 / 033244, WO05 / 019373, US2005 / 0258742, WO2009 / 146770, WO2010 / 015307, WO2010 / 031485, WO2010 / 054731, WO2010 / 054728, WO2010 / 086089, WO2011 / 016094, WO2012 / 016096, WO2013 / 016098, WO2014 / 016099, WO2015 / 016099, WO2016 / 016099, WO2017 / 016099, WO2018 / 016099, WO2019 / 017099, WO2019 / 018099, WO2019 / 018099, WO2019 / 019 ... WO2015 / 036074, WO2015 / 104045, WO2015 / 117718, WO2016 / 015815, and WO2016 / 124304. Generally, all phosphorescent complexes used in phosphorescent OLEDs according to the prior art and known to those skilled in the art of organic electroluminescence are suitable, and those skilled in the art will be able to use further phosphorescent complexes without exerting an effort commensurate with the invention.

[0129] A further preferred embodiment of the present invention is the use of a compound according to formula (1) or a preferred embodiment as a matrix material for a phosphorescent emitter in combination with a further matrix material. In a preferred embodiment of the present invention, the further matrix material is a hole-transporting compound. In a further preferred embodiment of the present invention, the further matrix material is an electron-transporting compound. In a further preferred embodiment, the further matrix material is a compound with a large band gap that participates, if at all, insignificantly in the transport of holes and electrons in the layer.

[0130] Suitable matrix materials which can be used in combination with the compounds of formula (1) or preferred embodiments are, for example, aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or 2010 / 006680, triarylamines, in particular monoamines, carbazole derivatives, such as CBP(N,N-biscarbazolylbiphenyl) or carbazole derivatives as disclosed in WO2005 / 039246, US2005 / 0069729, JP2004 / 288381, EP1205527 or WO2008 / 086851, for example according to WO2007 / 063754 or WO2008 / 056746, indolocarbazole derivatives as disclosed in WO2010 / 136109 and WO2011 / 000455, for example indenocarbazole derivatives as disclosed in WO2010 / 136109 and WO2011 / 000455, carbazole derivatives, for example according to EP 1617710, EP 1617711, EP 1731584, JP 2005 / 347160; azacarbazole derivatives, for example according to WO 2007 / 137725; bipolar matrix materials, for example according to WO 2005 / 111172; silanes, for example according to WO 2006 / 117052; azaboroles or boronic acid esters, for example according to WO 2010 / 015306, WO 2007 triazine derivatives, for example, according to EP 652273 or WO 2009 / 062578, zinc complexes, for example, according to WO 2010 / 054729, diazasilole or tetrazasilole derivatives, for example, according to WO 2010 / 054730, diazaphosphole derivatives, for example, according to US 2009 / 0136779, WO 2010 / 050778, WO 2011 Bridged carbazole derivatives, for example, according to WO 2012 / 048781, triphenylene derivatives, for example, according to WO 2011 / 116865, WO 2011 / 137951 or WO 2013 / 064206, or 4-spirocarbazole derivatives, for example, according to WO 2014 / 094963 or WO 2015 / 192939. In addition, a further phosphorescent emitter, which emits at a shorter wavelength than the actual emitter, can be present in the mixture as a co-host.

[0131] Preferred co-host materials are triarylamine derivatives, especially monoamines, indenocarbazole derivatives, 4-spirocarbazole derivatives, lactams and carbazole derivatives.

[0132] In a further embodiment of the present invention, the organic electroluminescent device of the present invention does not include any separate hole injection layer and / or hole transport layer and / or hole blocker layer and / or electron transport layer, which means that the light-emitting layer is directly in contact with the hole injection layer or anode and / or the light-emitting layer is directly in contact with the electron transport layer or electron injection layer or cathode, as described, for example, in WO 2005 / 053051. Furthermore, as described, for example, in WO 2009 / 030981, a metal complex identical to or similar to the metal complex in the light-emitting layer can be used as the hole transport or hole injection material directly in contact with the light-emitting layer.

[0133] Additionally, the compounds of the present invention can be used in hole transport or electron blocker layers.

[0134] In the further layer of the organic electroluminescent device of the present invention, any material commonly used in the prior art can be used.Therefore, those skilled in the art can use any material known in organic electroluminescent devices in combination with the compound of formula (1) or preferred embodiment of the present invention without exerting the skill equivalent to the invention.

[0135] Additionally preferred is an organic electroluminescent device characterized in that one or more layers are coated by sublimation. In this case, the material is evaporated in a vacuum sublimation apparatus at 10 -5 less than mbar, preferably 10 -6 It is applied by evaporation at an initial pressure of less than 10 mbar. Lower or higher initial pressures may also be used, e.g. -7 It is also possible for it to be less than mbar.

[0136] Likewise preferred are organic electroluminescent devices characterized in that one or more layers are coated by the OVPD (organic vapor phase deposition) method or with the aid of carrier gas sublimation. In this case, the materials are -5 It is applied at pressures between mbar and 1 bar. A special case of this method is the OVJP (organic vapor jet printing) method, in which the material is applied directly by a nozzle, thus providing structure (e.g., MS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301). In addition, organic electroluminescent devices are preferred, characterized in that one or more layers are produced from solution, for example by spin coating or by some printing method, for example inkjet printing, LITI (light-induced thermal imaging, thermal transfer printing), screen printing, flexographic printing, offset printing or nozzle printing. For this purpose, soluble compounds are required, which can be obtained, for example, by suitable substitution.

[0137] The compounds of the present invention have improved oxidation stability, especially in solution, compared with commonly used diamines.This is particularly important in printing processes.The compounds of the present invention also feature high thermal stability, so they can be deposited under high vacuum without decomposition.Thermal stability also extends the working life of the compounds.

[0138] Additionally, hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition, for example, it is possible to apply an emissive layer from solution and an electron transport layer by vapor deposition.

[0139] These methods are generally known to those skilled in the art and can be applied by those skilled in the art to organic electroluminescent devices containing the compounds of the present invention without exerting a skill equivalent to the invention.

[0140] When the compound of the present invention is used in organic electroluminescence device, it generally has very good properties.In particular, when the compound of the present invention is used in organic electroluminescence device, the lifetime is significantly better than that of the similar compound of the prior art.At the same time, the other properties of organic electroluminescence device, especially efficiency and voltage, are also better or at least equal.

[0141] The present invention will now be illustrated in detail by the following examples, without any intention of limiting the invention thereto.

[0142] [Example] The following syntheses are carried out in dry solvents under a protective gas atmosphere unless otherwise stated. Solvents and reagents can be purchased, for example, from Sigma-ALDRICH or ABCR. For compounds known from the literature, the corresponding CAS numbers are also reported in each case.

[0143] Synthesis Example a) 4-bromo-9-methyl-9-phenyl-9H-fluorene

[0144] [ka]

[0145] 30 g (94 mmol) of 2,2'-dibromobiphenyl is dissolved in 200 ml of dry THF in a baked-out flask. The reaction mixture is cooled to -78 °C. At this temperature, n-butyllithium (94 mmol) in 2.5 M hexane (37.7 ml) is slowly added dropwise (over approximately 1 hour). The mixture is stirred at -70 °C for an additional hour. Next, 11.1 ml of acetophenone (94 mmol) is dissolved in 100 ml of THF and added dropwise at -70 °C. After the addition is complete, the reaction mixture is gradually warmed to room temperature, quenched with NH4Cl, and then concentrated on a rotary evaporator. 300 ml of acetic acid is carefully added to the concentrated solution, followed by 50 ml of fuming HCl. The mixture is heated to 75 °C for 6 hours, during which time a white solid precipitates. The mixture is cooled to room temperature, the precipitated solid is filtered off with suction and washed with methanol, and the residue is dried under reduced pressure at 40° C. The yield is 25.3 g (75 mmol) (80% of theory).

[0146] b) 4-bromo-9,9-diphenyl-9H-fluorene

[0147] [ka]

[0148] 37 g (152 mml) of 2,2'-dibromobiphenyl is dissolved in 300 ml of dry THF in a baked-out flask. The reaction mixture is cooled to -78°C. At this temperature, n-butyllithium (119 mmol) in a 15% hexane solution (75 ml) is slowly added dropwise (over approximately 1 hour). The mixture is stirred at -70°C for an additional hour. Next, 21.8 g of benzophenone (119 mmol) is dissolved in 100 ml of THF and added dropwise at -70°C. After the addition is complete, the reaction mixture is gradually warmed to room temperature, quenched with NH4Cl, and then concentrated on a rotary evaporator. 510 ml of acetic acid is carefully added to the concentrated solution, followed by 100 ml of fuming HCl. The mixture is heated to 75°C for 4 hours, during which time a white solid precipitates. The mixture is cooled to room temperature, the precipitated solid is filtered off with suction and washed with methanol, and the residue is dried under reduced pressure at 40° C. The yield is 33.2 g (83 mmol) (70% of theory).

[0149] The following brominated compounds are prepared in a similar manner:

[0150] [Table 2]

[0151] c) 6-bromo-2-fluoro-2'-methoxybiphenyl

[0152] [ka]

[0153] 200 g (664 mmol) of 1-bromo-3-fluoro-2-iodobenzene, 101 g (664 mmol) of 2-methoxyphenylboronic acid, and 137.5 g (997 mmol) of sodium tetraborate were dissolved in 1000 ml of THF and 600 ml of water, degassed, and 9.3 g (13.3 mmol) of bis(triphenylphosphino)palladium(II) chloride and 1 g (20 mmol) of hydrazinium hydroxide were added. The reaction mixture was then stirred at 70 °C for 48 hours under a protective gas atmosphere. The cooled solution was supplemented with toluene, washed repeatedly with water, dried, and concentrated. The product was purified by column chromatography on silica gel with toluene / heptane (1:2). Yield: 155 g (553 mmol), 83% of theory.

[0154] The following compounds are prepared in a similar manner:

[0155] [Table 3]

[0156] d) 6'-Bromo-2'-fluorobiphenyl-2-ol

[0157] [ka]

[0158] 112 g (418 mmol) of 6-bromo-2-fluoro-2'-methoxybiphenyl is dissolved in 2 L of dichloromethane and cooled to 5 °C. 41.0 ml (431 mmol) of boron tribromide is added dropwise to this solution within 90 minutes, and stirring of the mixture is continued overnight. The mixture is then slowly mixed with water, and the organic phase is washed three times with water, dried over Na2SO4, concentrated by rotary evaporation, and purified by chromatography. Yield: 104 g (397 mmol), 98% of theory.

[0159] The following compounds are prepared in a similar manner:

[0160] [Table 4]

[0161] e) 1-Bromodibenzofuran

[0162] [ka]

[0163] 111 g (416 mmol) of 6'-bromo-2'-fluorobiphenyl-2-ol is dissolved in 2 L of DMF (max. HO 0.003%) SeccoSolv® and cooled to 5°C. 20 g (449 ml) of sodium hydride (60% suspension in paraffin) is added in portions to this solution, and once the addition is complete, the mixture is stirred for 20 minutes, and then the mixture is heated to 100°C for 45 minutes. After cooling, 500 ml of ethanol is slowly added to the mixture, which is concentrated by rotary evaporation and then purified by chromatography. Yield: 90 g (367 mmol), 88.5% of theory.

[0164] The following compounds are prepared in a similar manner:

[0165] [Table 5]

[0166] f) Biphenyl-4-yldibenzofuran-1-ylamine

[0167] [ka]

[0168] 30.0 g (177 mmol, 1.0 eq) of 4-aminobiphenyl, together with 43.7 g (177 mmol, 1.0 eq) of 1-bromodibenzofuran and 2.4 g (212 mmol, 1.20 eq) of sodium tert-pentoxide [14593-46-5], were first added to 600 ml of anhydrous toluene and degassed for 30 minutes. Next, 398 mg (1.77 mmol, 0.01 eq) of palladium(II) acetate [3375-31-3] and 1.46 g (3.56 mmol, 0.02 eq) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPHOS) [657408-07-6] were added, and the mixture was heated to reflux overnight. After the reaction was complete, the mixture was cooled to room temperature and extracted with 500 ml of water. The aqueous phase is then washed three times with toluene, the combined organic layers are dried over sodium sulfate, and the solvent is removed on a rotary evaporator. The brown residue is dissolved in about 200 ml of toluene and filtered through silica gel. For further purification, recrystallization from toluene / heptane is carried out. Yield: 44 g (133 mmol), 76% of theory.

[0169] The following compounds are prepared in a similar manner:

[0170] [Table 6-1]

[0171] [Table 6-2]

[0172] [Table 6-3]

[0173] [Table 6-4]

[0174] g) Dibenzofuran-1-yl-(4-dibenzofuran-4-ylphenyl)-(9,9-dimethyl-9H-fluoren-4-yl)amine

[0175] [ka]

[0176] A mixture of 13.6 g (50 mmol) of 4-bromo-9,9-dimethyl-9H-fluorene, 25.5 g (60 mmol) of dibenzofuran-1-yl-(4-dibenzofuran-4-ylphenyl)amine, 7.7 g (80 mmol) of sodium tert-butoxide, 1.4 g (5 mmol) of tricyclohexylamine, 561 mg (2.5 mmol) of palladium(II) acetate, and 300 ml of mesitylene is heated under reflux for 24 hours. After cooling, 200 ml of water is added, the mixture is stirred for another 30 minutes, the organic phase is removed, the organic phase is filtered through a short Celite bed, and the solvent is then removed under reduced pressure. The residue is recrystallized five times from DMF and finally fractionally sublimed twice (p approximately 10 -6 mbar, T=340-350°C). Yield: 23 g (37 mmol), 75% of theory; 99.9% by HPLC.

[0177] The following compounds are obtained in a similar manner:

[0178] [Table 7-1]

[0179] [Table 7-2]

[0180] [Table 7-3]

[0181] [Table 7-4]

[0182] [Table 7-5]

[0183] h) 1-Bromo-8-iododibenzofuran

[0184] [ka]

[0185] 20 g (80 mmol) of dibenzofuran-1-boronic acid, 2.06 g (40.1 mmol) of iodine, 3.13 g (17.8 mmol) of iodic acid, 80 ml of acetic acid, 5 ml of sulfuric acid, 5 ml of water, and 2 ml of chloroform are stirred at 65 °C for 3 hours. After cooling, the mixture is mixed with water, and the precipitated solid is filtered off with suction and washed three times with water. The residue is recrystallized from toluene and from dichloromethane / heptane. The yield is 25.6 g (68 mmol), which corresponds to 85% of theory.

[0186] The following compounds are prepared in a similar manner:

[0187] [Table 8]

[0188] i) 3-(9-bromodibenzofuran-2-yl)-9-phenyl-9H-carbazole

[0189] [ka]

[0190] 58 g (156 mmol) of 1-bromo-8-iododibenzofuran, 50 g (172 mmol) of N-phenylcarbazole-3-boronic acid, and 36 g (340 mmol) of sodium carbonate were suspended in 1000 ml of ethylene glycol dimethyl ether and 280 ml of water. 1.8 g (1.5 mmol) of tetrakis(triphenylphosphine)palladium(0) was added to the suspension, and the reaction mixture was heated to reflux for 16 hours. After cooling, the organic layer was removed, filtered through silica gel, washed three times with 200 ml of water, and then concentrated to dryness. The yield was 48 g (89 mmol), corresponding to 64% of theory.

[0191] The following compounds are prepared in a similar manner:

[0192] [Table 9-1]

[0193] [Table 9-2]

[0194] [Table 9-3]

[0195] [Table 9-4]

[0196] j) biphenyl-4-yl-(9,9-dimethyl-9H-fluoren-4-yl)-[8-(9-phenyl-9H-carbazol-3-yl)dibenzofuran-1-yl]amine

[0197] [ka]

[0198] A mixture of 9.3 g (26 mmol) of biphenyl-4-yl-(9,9-dimethyl-9H-fluoren-4-yl)amine, 12 g (26 mmol) of 3-(9-bromodibenzofuran-2-yl)-9-phenyl-9H-carbazole, 7.7 g (80 mmol) of sodium tert-butoxide, 2.6 ml (78 mmol) of tri-tert-butylphosphine (1 M, toluene), 224 mg (2.6 mmol) of palladium(II) acetate, and 300 ml of mesitylene is heated under reflux for 24 hours. After cooling, 200 ml of water is added, the mixture is stirred for another 30 minutes, the organic phase is removed, the organic phase is filtered through a short Celite bed, and the solvent is then removed under reduced pressure. The residue is recrystallized five times from DMF and finally fractionally sublimed twice (p approximately 10 -6 mbar, T=340-350°C). Yield: 13 g (17 mmol), 68% of theory; 99.9% by HPLC.

[0199] The following compounds are prepared in a similar manner:

[0200] [Table 10-1]

[0201] [Table 10-2]

[0202] [Table 10-3]

[0203] [Table 10-4]

[0204] [Table 10-5]

[0205] [Table 10-6]

[0206] [Table 10-7]

[0207] [Table 10-8]

[0208] OLED manufacturing In the following Examples C1-I9 (see Tables 1 and 2), data for various OLEDs is shown.

[0209] Pretreatment for Examples C1-I9: Glass plates coated with 50 nm thick structured ITO (indium tin oxide) are coated with 20 nm of PEDOT:PSS (poly(3,4-ethylenedioxythiophene) poly(styrenesulfonic acid) purchased from Heraeus Precious Metals GmbH, Germany as CLEVIOS™ P VP AI 4083 and spun on from an aqueous solution) for improved processing. These coated glass plates form the substrates onto which the OLEDs are attached.

[0210] An OLED basically has the following layer structure: substrate / transport layer (HTL) / optional interlayer (IL) / electron blocker layer (EBL) / emissive layer (EML) / optional hole blocker layer (HBL) / electron transport layer (ETL) / optional electron injection layer (EIL), and finally a cathode. The cathode is formed by a 100 nm thick aluminum layer. The exact structure of the OLED can be found in Table 1. The materials required for the fabrication of the OLED are shown in Table 3.

[0211] All materials are applied by thermal evaporation in a vacuum chamber. In this case, the light-emitting layer always consists of at least one matrix material (host material) and a light-emitting dopant (emitter), which is added to the matrix material(s) by co-evaporation in a specific volume ratio. A description such as IC5:IC3:TEG1 (45%:45%:10%) 30 nm means that the layer contains the materials IC5 in a volume ratio of 45%, IC3 in a volume ratio of 45%, and TEG1 in a volume ratio of 10%. Similarly, the electron-transporting layer also consists of a mixture of two materials.

[0212] OLEDs are characterized in the standard way. For this purpose, the electroluminescence spectrum, voltage, and external quantum efficiency (EQE, measured as a percentage) are determined as a function of luminance, calculated from the current-voltage-luminance characteristic (IUL characteristic) assuming Lambertian emission characteristics, and lifetime. The electroluminescence spectrum is measured at 1000 cd / m 2 The parameter U1000 in Table 2 is determined here by the luminance of 1000 cd / m 2 EQE1000 represents the voltage required for a brightness of 1000cd / m 2 The lifetime LT is defined as the time it takes for the luminance to drop to a certain ratio L1 from the starting luminance during operation at a constant current. In Table 2, L0; j0 = 4000 cd / m 2 and L1=70% are the values ​​reported for the LT series, starting at 4000 cd / m 2 ~2800cd / m 2 Similarly, L0;j0=20mA / cm 2 , L1=80% is 20mA / cm 2 This means that the brightness in the operating process at 100° C. drops to 80% of its starting value after time LT.

[0213] Data for various OLEDs are collected in Table 2. Examples C1-C8 are comparative examples according to the prior art; Examples I1-I9 show data for OLEDs of the present invention.

[0214] Some of the examples are detailed below to illustrate the advantages of the OLED of the present invention.

[0215] Use of the mixtures of the present invention in the light-emitting layer of phosphorescent OLEDs When used in the light-emitting layer (EML) and electron-blocking layer (EBL) of phosphorescent OLEDs, the materials of the present invention provide significant improvements over the prior art, particularly with regard to the lifetime of the OLED components. By using the compounds INV-1 to INV-3 of the present invention in combination with IC5 and the green dopant TEG1, a lifetime increase of more than 40% can be observed compared to the prior art VG-1 to VG-4 (compare with I1 to I3 in Examples C1 to C4). By using the compounds INV-1 to INV-3 of the present invention in the EBL, a lifetime increase of more than 25% can be observed compared to the prior art VG-1 to VG-4 (compare with I4 to I6 in Examples C5 to C8).

[0216] [Table 11-1]

[0217] [Table 11-2]

[0218] [Table 11-3]

[0219] [Table 12]

[0220] [Table 13-1]

[0221] [Table 13-2]

[0222]

Table 13-3

Claims

1. Formula (1) 【Chemical 1】 [wherein the symbols used are as follows: X is O or S; Y is O, S or CR 2 and Ar in each occurrence is the same or different and is an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, optionally substituted by one or more R radicals, where Ar contains only aryl or heteroaryl groups having up to 15 aromatic ring atoms, and does not contain carbazolyl groups as heteroaryl groups, and does not contain 9,9'-spirobifluorene groups; R is the same or different in each case and is H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 4 ) 2 , C(=O)Ar 1 , C(=O)R 4 , P(=O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , a linear alkyl, alkoxy, or thioalkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms (each of which may be one or more R 4 may be substituted by a radical, and one or more non-adjacent CH 2 The group is R 4 C=CR 4 , C=O, C=S, C=NR 4 , P(=O)(R 4 ), SO, SO 2 , N.R. 4 , O, S or CONR 4 and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 and having 5 to 40 aromatic ring atoms, in each case one or more R 4 an aromatic or heteroaromatic ring system, optionally substituted by a radical, having 5 to 40 aromatic ring atoms and one or more R 1 an aryloxy or heteroaryloxy group, optionally substituted by a radical, or a aryloxy group having 5 to 40 aromatic ring atoms and one or more R 4 and at the same time, two R substituents attached to the same carbon atom or adjacent carbon atoms are selected from the group consisting of aralkyl or heteroaralkyl groups, optionally substituted by a radical; and 4 optionally forming a monocyclic or polycyclic aliphatic ring system, optionally substituted by radicals; R 1 are in each case the same or different and are H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 4 ) 2 , C(=O)Ar 1 , C(=O)R 4 , P(=O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , a linear alkyl, alkoxy, or thioalkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms (each of which may be one or more R 4 may be substituted by a radical, and one or more non-adjacent CH 2 The group is R 4 C=CR 4 , C=O, C=S, C=NR 4 , P(=O)(R 4 ), SO, SO 2 , N.R. 4 , O, S or CONR 4 and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 and having 5 to 40 aromatic ring atoms, in each case one or more R 4 an aromatic or heteroaromatic ring system, optionally substituted by a radical, having 5 to 40 aromatic ring atoms and one or more R 4 an aryloxy or heteroaryloxy group, optionally substituted by a radical, or a aryloxy group having 5 to 40 aromatic ring atoms and one or more R 4 and at the same time, two R bonded to adjacent carbon atoms are selected from the group consisting of aralkyl or heteroaralkyl groups, optionally substituted by a radical. 1 Substituent or two R 1 and R 3 The substituent is one or more R 4 optionally forming a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, optionally substituted by radicals; R 2 are in each case the same or different and are H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 4 ) 2 , C(=O)Ar 1 , C(=O)R 4 , P(=O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , a linear alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms (each of which may be one or more R 4 may be substituted by a radical, and one or more non-adjacent CH 2 The group is R 4 C=CR 4 , C=O, C=S, C=NR 4 , P(=O)(R 4 ), SO, SO 2 , N.R. 4 , O, S or CONR 4 and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 and having 5 to 40 aromatic ring atoms, in each case one or more R 4 an aromatic or heteroaromatic ring system, optionally substituted by a radical, having 5 to 40 aromatic ring atoms and one or more R 4 an aryloxy or heteroaryloxy group, optionally substituted by a radical, or a aryloxy group having 5 to 40 aromatic ring atoms and one or more R 4 and at the same time, two R bonded to adjacent carbon atoms are selected from the group consisting of aralkyl or heteroaralkyl groups, optionally substituted by a radical. 2 The substituent is one or more R 4 optionally forming a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, optionally substituted by radicals; R 3 are in each case the same or different and are H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 4 ) 2 , C(=O)Ar 1 , C(=O)R 4 , P(=O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , a linear alkyl, alkoxy, or thioalkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms (each of which may be one or more R 4 may be substituted by a radical, and one or more non-adjacent CH 2 The group is R 4 C=CR 4 , C=O, C=S, C=NR 4 , P(=O)(R 4 ), SO, SO 2 , N.R. 4 , O, S or CONR 4 and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 and having 5 to 40 aromatic ring atoms, in each case one or more R 4 an aromatic or heteroaromatic ring system, optionally substituted by a radical, having 5 to 40 aromatic ring atoms and one or more R 4 an aryloxy or heteroaryloxy group, optionally substituted by a radical, or a aryloxy group having 5 to 40 aromatic ring atoms and one or more R 4 and at the same time, two R bonded to adjacent carbon atoms are selected from the group consisting of aralkyl or heteroaralkyl groups, optionally substituted by a radical. 1 and R 3 The substituent is one or more R 4 optionally forming a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, optionally substituted by radicals; Ar 1 are the same or different in each occurrence and have 5 to 30 aromatic ring atoms and one or more non-aromatic R 4 and at the same time, two Ar bonded to the same phosphorus or boron atom are aromatic or heteroaromatic ring systems optionally substituted by Ar radicals. 1 The radical is a single bond or N(R 4 ), C(R 4 ) 2 , optionally cross-linked to each other by bridges selected from O and S; R 4 are in each case the same or different and are H, D, F, Cl, Br, I, CN, NO 2 , N(R 5 ) 2 , C(=O)R 5 , a linear alkyl, alkoxy, or thioalkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms (each of which may be one or more R 5 may be substituted by a radical, and one or more non-adjacent CH 2 The group is R 5 C=CR 5 , C=O, C=S, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 and one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 and having 5 to 40 aromatic ring atoms, in each case one or more R 5 an aromatic or heteroaromatic ring system, optionally substituted by a radical, having 5 to 40 aromatic ring atoms and one or more R 5 an aryloxy or heteroaryloxy group, optionally substituted by a radical, or a aryloxy group having 5 to 40 aromatic ring atoms and one or more R 5 and at the same time, two R bonded to the same carbon atom or adjacent carbon atoms are selected from the group consisting of aralkyl or heteroaralkyl groups, optionally substituted by a radical. 4 The substituent is one or more R 5 optionally forming a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, optionally substituted by radicals; R 5 are in each occurrence the same or different and are selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, or CN, and which ring system may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; 5 The substituents together may form a monocyclic or polycyclic aliphatic ring system; Here, as an example, the nitrogen atom is represented by R 1 or R 3 is attached to the corresponding carbon atom instead of R 3 In this case, Y is CR 2 It cannot be Compound.

2. 2. The compound of claim 1, wherein X is O.

3. Y is CR 2 3. The compound according to claim 1 or 2, characterized in that it is

4. The compound is represented by formula (1-1) or formula (1-2): 【Chemistry 2】 where the symbols have the definitions given in claim 1. The compound according to any one of claims 1 to 3, characterized in that it is a compound of the formula:

5. The compound is represented by formula (2) 【Chemistry 3】 wherein the symbols have the definitions given in claim 1, and wherein one R bonded to a carbon atom 2 and one R 4 is replaced by a single bond) The compound according to any one of claims 1 to 4, characterized in that it is a compound of the formula:

6. The compound is represented by the formula (2-1) and (2-2) 【Chemistry 4】 (wherein the symbols have the definitions given in claim 1, and where one R 2 and one R bonded to the carbon atom of formula (2-2) 4 is replaced by a single bond) 6. The compound according to claim 1, wherein the compound is one of the following compounds:

7. In formula (2-2), R replaced by a single bond 2 The compound according to claim 6, characterized in that is not located on a six-membered ring bonded to the nitrogen atom.

8. A mixture comprising at least one compound according to any one of claims 1 to 7 and at least one further compound and / or at least one solvent.

9. Use of a compound according to any one of claims 1 to 7 or a mixture according to claim 8 in an electronic device.

10. An electronic device comprising at least one compound according to any one of claims 1 to 7 or a mixture according to claim 8.

11. 11. The electronic device according to claim 10, which is an organic electroluminescent device.

12. 12. The electronic device according to claim 11, characterized in that a compound according to any one of claims 1 to 7 or a mixture according to claim 8 is used in an emitting layer, in a hole transport layer or in an electron blocker layer, preferably in combination with a phosphorescent dopant and optionally one or more further matrix materials.

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