MATERIALS FOR ORGANIC LIGHT-EMITTING DEVICES

Abstract

The present invention relates to OLED materials containing triphenyleno[1,12-bcd]furan or triphenyleno[1,12-bdc]thiophene, their use in organic electronic devices, mixtures containing these materials and electronic devices containing these compounds, in particular organic electroluminescent devices containing these compounds as matrix materials, electron transport materials or hole blocking materials.

Description

Technical area

[0001] The present invention relates to triphenyleno[1,12-bcd]furans or triphenyleno[1,12-bdc]thiophenes, mixtures containing them, their use in organic electronic devices and electronic devices containing these compounds, in particular organic light-emitting devices containing these compounds as matrix materials, electron transport materials or hole blocking materials. State of the art

[0002] Phosphorescent organometallic complexes are frequently used in organic electroluminescent devices (OLEDs). In general, there is still room for improvement in OLEDs, for example, with regard to efficiency, operating voltage, and lifetime. The properties of phosphorescent OLEDs are determined not only by the triplet emitters used. The other materials used, such as matrix materials, are also particularly important. Improvements to these materials can therefore also lead to significant improvements in OLED properties.

[0003] According to the state of the art, carbazole derivatives, dibenzofuran derivatives, indenocarbazole derivatives, indolocarbazole derivatives, triphenylene derivatives, triphenyleno[1,12-bcd]furans or triphenyleno[1,12-bdc]thiophenes are used as matrix materials for phosphorescent emitters.

[0004] In WO11137157A1, WO12048781 A1, WO22038066 A1, CN112225727 A, WO22148717 A1, CN112961144 A, CN112961145 A, CN113429334 A, CN114409589 A, special triphenyleno[1,12-bcd]furans or triphenyleno[1,12-bdc]thiophenes are described, among other things, as matrix materials.

[0005] In general, there is still room for improvement with these materials, particularly for use as matrix materials. The object of the present invention is to provide compounds which are particularly suitable for use as matrix material, electron transport material or hole blocking material in a phosphorescent OLED. In particular, the object of the present invention is to provide matrix materials which, when used in an OLED, lead to an improved lifetime and a lower capacity of the device. The desire for an improved lifetime applies in particular when using a low to medium emitter concentration in the light-emitting layer, i.e. at emitter concentrations in the order of 3 to 20%, in particular 3 to 15%, since the device lifetime is limited in particular in this case.

[0006] The capacitance of a device is an important parameter with regard to the achievable switching times of the device. Since modern OLED displays operate at ever-increasing refresh rates (from 60 Hz in the past to 120 Hz or even 240 Hz today), short switching times of OLED devices are essential. A key prerequisite for this is the lowest possible capacitance, both with regard to the threshold voltage of the rise in the capacitance curve (beyond the level of geometric capacitance) and with regard to the maximum capacitance signal.

[0007] It has now been found that electroluminescent devices containing compounds according to the following formula (1) exhibit improvements over the prior art, in particular when using the compounds as matrix material for phosphorescent dopants.

[0008] It has further been found that the combination of at least one compound of the formula (1) as the first host material and at least one hole-transporting compound, for example in combination with one or more compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6), as a further host material or further host materials in a light-emitting layer of an organic electronic device, in particular an organic electroluminescent device, solves this problem and eliminates the disadvantages of the prior art. Summary of the invention

[0009] A first object of the present invention is a compound of formula (1), ABC Formula (1), where B represents a structure of formula (2), A represents a structure of formulas (3) or (4) and C represents a structure of formulas (5), (6), (7) or (8), where the symbols and indices used are: Z is O or S; a, b, c, d, e and f represent the respective linking points to formulas (3), (4), (5), (6), (7) or (8); X is independently CH, CR 1 or N, where at least one X N means; V is O or S; Y is independently N, C, CH or CR 1 , where at least one Y stands for N and it is excluded that two adjacent Y simultaneously stand for N; R# is at each occurrence independently an aryl group with 6 to 20 C atoms which is reacted with one or more radicals R 0 can be substituted; m is 0, 1 or 2 independently at each occurrence; * is the point of attachment to a, b, c, d or f of formula (2); # is the point of attachment to a, b, c, d or f of formula (2); R a , Rb , R c and R d represent a monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution or no substitution; R a , R b , R c and R d are D at every occurrence; Ar1, Ar2 and Ar3 are each independently at each occurrence an aryl or heteroaryl group having 5 to 40 ring atoms which can be substituted with one or more radicals R 0 can be substituted; R 1 is at each occurrence independently D, CN, F or an aryl or heteroaryl group having 5 to 40 ring atoms which can be substituted by one or more radicals R 0 can be substituted; R 0 is selected at each occurrence, identically or differently, from the group consisting of D, F, Cl, Br, I, CN, NO2, C(=O)R 2 , P(=O)(Ar)2, P(Ar)2, B(Ar)2, Si(Ar)3, Si(R 2)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 C atoms, each of which is substituted by one or more radicals R 2 may be substituted, with one or more non-adjacent CH2 groups being substituted by R 2 C=CR 2 , Si(R 2 )2, C=O, C=S, C=NR 2 , P(=O)(R 2 ), SO, SO2, NR 2 , O, S or CONR 2 and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aryl or heteroaryl group having 5 to 40 ring atoms which may be substituted with one or more radicals R 2 may be substituted, an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, which may be substituted with one or more radicals R 2may be substituted, or an aralkyl or heteroaralkyl group having 5 to 40 ring atoms which may be substituted with one or more radicals R 2 can be substituted; R 2 is selected, identically or differently at each occurrence, from the group consisting of D, F, CN, Si(Aryl)3, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms may be replaced by D, F, or CN, Aryl is an unsubstituted, partially or fully deuterated aryl group with 6 to 40 C atoms, with the condition that the structure of formulas (3) or (4) with the linking point * and the structure of formulas (5), (6), (7) or (8) with the linking point # in formula (2) are directly adjacent.

[0010] The direct proximity of structure A next to structure C leads to special properties of the compounds of formula (1), in particular with regard to their solubility and with regard to evaporation temperatures, which are suitable for combination with hole-transporting host materials.

[0011] The invention further relates to a mixture comprising at least one compound of formula (1) as described above or preferably described later and at least one further compound selected from the group of matrix materials, phosphorescent emitters, fluorescent emitters and / or emitters which exhibit TADF (thermally activated delayed fluorescence).

[0012] Another object of the invention is the use of a compound according to formula (1) in an organic electronic device.

[0013] A further subject matter of the invention is an organic electronic, preferably electroluminescent or light-emitting, device comprising an anode, a cathode and at least one organic layer containing at least one compound of formula (1), as described above or preferably described later.

[0014] A further subject of the invention is a process for producing an organic electronic, preferably electroluminescent or light-emitting, device, as described above or preferably described below, characterized in that the organic layer is applied by vapor deposition or from solution. Description of the invention

[0015] In this patent application, "D" or "D atom" refers to deuterium. The degree of deuteration, expressed in mol%, indicates the proportion of H atoms replaced by deuterium. Since deuterated compounds are often a mixture of compounds that differ in the exact position and proportion of D atoms, the degree of deuteration indicates the average proportion of H atoms replaced by D. With an average degree of deuteration of 50 mol%, an average of 50 mol% of the H atoms in the compound are replaced by D.

[0016] An aryl group within the meaning of this invention contains 6 to 40 ring atoms or preferably 6 to 30 ring atoms or preferably 6 to 18 ring atoms, where the ring atoms are C atoms. A heteroaryl group within the meaning of this invention contains 5 to 40 ring atoms, where the ring atoms comprise C atoms and at least one heteroatom, with the proviso that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aryl group is understood to be a simple aromatic ring, for example phenyl derived from benzene, or a condensed aryl group, for example derived from naphthalene, anthracene, phenanthrene, triphenylene, but the term aryl group within the meaning of the invention also includes biphenyl, terphenyl, quaterphenyl, fluorenyl, 9,9-dialkylfluorenyl, 9,9-diarylfluorenyl or spirobifluorenyl. A preferred 9,9-dialkylfluorenyl group is 9,9-dimethylfluorenyl.A preferred 9,9-diarylfluorenyl group is 9,9-diphenylfluorenyl. An aryl group with 6 to 18 carbon atoms is therefore preferably phenyl, naphthyl, phenanthryl, or triphenylenyl, whereby the attachment of the aryl group as a substituent is not restricted. The aryl group within the meaning of this invention can bear one or more radicals, with the suitable radical being described below. The radical is preferably deuterium. If no such radical is described, the aryl group or heteroaryl group is unsubstituted.

[0017] A heteroaryl group is understood to be either a simple heteroaromatic cycle, for example derived from pyridine, pyrimidine or thiophene, or a condensed heteroaryl group, for example derived from quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene or carbazole. However, the term heteroaryl group in the sense of the invention also includes a heteroaryl group which is bonded to an aryl group or another heteroaryl group by a single bond, for example phenylbipyridyl or bipyridyl. The heteroaryl group in the sense of this invention can carry one or more radicals, the suitable radical being described below. The radical is preferably deuterium. If no such radical is described, the heteroaryl group is unsubstituted.

[0018] An aromatic ring system within the meaning of this invention contains 6 to 40 carbon atoms in the ring system. The aromatic ring system includes aryl groups, as described above, and the term is used synonymously below.

[0019] An aromatic ring system with 6 to 18 carbon atoms is preferably selected from phenyl, biphenyl, naphthyl, phenanthryl, and triphenylenyl, which may carry one or more radicals, the suitable radical being described below. Preferably, the radical is deuterium. If no such radical is described, the aromatic ring system is unsubstituted.

[0020] A heteroaromatic ring system within the meaning of this invention contains 5 to 40 ring atoms and at least one heteroatom. A preferred heteroaromatic ring system has 9 to 40 ring atoms and at least one heteroatom. The heteroaromatic ring system comprises heteroaryl groups, as described above, and the term is used synonymously below.

[0021] An aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which can be linked to the aromatic or heteroaromatic ring via any position and which can carry one or more radicals, as described below, is preferably understood to mean the following groups, which are derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, triphenylene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzfluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, terphenyl, quaterphenyl, fluorene, 9,9-dimehtylfluorene, 9,9-diphenylfluorene, 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,Isochinolin, Acridin, Phenanthridin, Benzo-5,6-chinolin, Benzo-6,7-chinolin, Benzo-7,8-chinolin, Phenothiazin, Phenoxazin, Pyrazol, Indazol, Imidazol, Benzimidazol, Naphthimidazol, Phenanthrimidazol, Pyridimidazol, Pyrazinimidazol, Chinoxalinimidazol, Oxazol, Benzoxazol, Naphthoxazol, Anthroxazol, Phenanthroxazol, Isoxazol, 1,2-Thiazol, 1,3-Thiazol, Benzothiazol, Pyridazin, Benzopyridazin, Pyrimidin, Benzpyrimidin, Chinoxalin, 1,5-Diazaanthracen, 2,7-Diazapyren, 2,3-Diazapyren, 1,6-Diazapyren, 1,8-Diazapyren, 4,5-Diazapyren, 4,5,9,10-Tetraazaperylen, Pyrazin, Phenazin, Phenoxazin, Phenothiazin, Fluorubin, Naphthyridin, Azacarbazol, Benzocarbolin, Phenanthrolin, 1,2,3-Triazol, 1,2,4-Triazol, Benzotriazol, 1,2,3-Oxadiazol, 1,2,4-Oxadiazol, 1,2,5-Oxadiazol, 1,3,4-Oxadiazol, 1,2,3-Thiadiazol, 1,2,4-Thiadiazol, 1,2,5-Thiadiazol, 1,3,4-Thiadiazol, 1,3,5-Triazin, 1,2,4-Triazin, 1,2,3-Triazin, Tetrazol, 1,2,4,5-Tetrazin, 1,2,3,4-Tetrazin, 1,2,3,5-Tetrazin, Purin, Pteridin, Indolizin,Benzothiadiazole, phenylpyridine and bipyridine.

[0022] The abbreviations Ar1, Ar2 and Ar3 each independently represent an aryl or heteroaryl group with 5 to 40 ring atoms, which can be substituted with one or more radicals R 0 may be substituted, where the radical R 0 has a meaning as described above or below.

[0023] The abbreviation "aryl" refers, independently of one another and identically or differently, to an unsubstituted, partially or fully deuterated aryl group containing 6 to 40 carbon atoms. The abbreviation "aryl" is preferably phenyl, 1,2-biphenyl, 1,3-biphenyl, or 1,4-biphenyl, which may be partially or fully deuterated.

[0024] The abbreviation Ar5 stands, identically or differently at each occurrence, for an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which is substituted by one or more radicals R 7can be substituted or is synonymous with an aryl group with 6 to 40 C atoms or a heteroaryl group with 5 to 40 ring atoms, which can be substituted with one or more radicals R 7 may be substituted, where R 7 or the substituents R 7 has / have a meaning as described above or below.

[0025] A preferred meaning of Ar1, Ar2, Ar3, “aryl” and Ar5 is described below.

[0026] An electron-rich heteroaromatic compound is a heterocyclic aromatic compound with a π excess, i.e., a lone pair of electrons on the heteroatom forms the cyclically delocalized electrons with the p electrons of the carbon atoms. This definition also applies to an electron-rich heteroaromatic ring system.

[0027] A cyclic alkyl, alkoxy or thioalkyl group in the sense of this invention is understood to mean a monocyclic, a bicyclic or a polycyclic group.

[0028] In the context of the present invention, a straight-chain, branched or cyclic C1 to C 20-Alkylgruppe beispielsweise die Reste 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, neo-Pentyl, Cyclopentyl, n-Hexyl, s-Hexyl, t-Hexyl, 2-Hexyl, 3-Hexyl, neo-Hexyl, Cyclohexyl, 1-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, Trifluormethyl, Pentafluorethyl, 2,2,2-Trifluorethyl, 1,1-Dimethyl-n-hex-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-dec-1-yl-, 1,1-Diethyl-n-dodec-1-yl-, 1,1-Diethyl-n-tetradec-1-yl-, 1,1-Diethyln-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- understood.,

[0029] An alkenyl group is understood to mean, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.

[0030] An alkynyl group is understood to mean, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

[0031] Under a C1 to C 20 -Alkoxy group means, for example, methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy.

[0032] Under a C1 to C 20-Thioalkyl group means, for example, S-alkyl groups, for example thiomethyl, 1-thioethyl, 1-thio-i-propyl, 1-thio-n-propoyl, 1-thio-i-butyl, 1-thio-n-butyl or 1-thio-t-butyl.

[0033] An aryloxy or heteroaryloxy group with 5 to 40 aromatic ring atoms means O-aryl or O-heteroaryl and means that the aryl or heteroaryl group is bonded via an oxygen atom.

[0034] An aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms means that an alkyl group, as previously described, is substituted with an aryl group or heteroaryl group, respectively.

[0035] The compounds of formula (1) and their preferred embodiments are described below. The preferred embodiments also apply to the mixture according to the invention and the organic electronic device according to the invention, the organic electroluminescent or light-emitting device.

[0036] Preferred embodiments of the compounds of formula (1) are compounds of formulas (1a), (1b), (1c), (1d), (1e), (1f) or (1g), where A, C, Z, R a , R b and R c have a meaning previously mentioned or preferred below.

[0037] Particularly preferred embodiments of the compounds of formula (1) are compounds of formulas (1a), (1b), (1c), (1f) and (1g), where A, C, Z, R a , R b and R c have a meaning previously mentioned or preferred below.

[0038] Very particularly preferred embodiments of the compounds of formula (1) are compounds of formula (1g), wherein A, C, Z, R a , R b and R c have a meaning previously mentioned or preferred below.

[0039] In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), the symbol Z preferably represents O.

[0040] A further subject matter is accordingly a compound of one of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g), where Z is O and A, C, Z, R a , R b and R c have a meaning previously mentioned or preferred below.

[0041] In a preferred embodiment of A according to formula (3), two X stand for N and one X stands for CH or CR 1 or all three X stand for N, this embodiment being described by the formulas (3-1), (3-2), (3-3), (3-4), (3-5), (3-6) and (3-7), where R 1 , Ar1 and Ar2 have a meaning mentioned above or preferred below.

[0042] A particularly preferred embodiment of A according to formula (3) are embodiments of formulas (3-1), (3-3), (3-5) and (3-7), where R1 , Ar1 and Ar2 have a meaning mentioned above or preferred below.

[0043] In embodiments of A according to formulas (3), (3-3), (3-5) and (3-7), R 1 preferably selected from the group D, CN, F or an aryl or heteroaryl group having 5 to 40 ring atoms, wherein the aryl or heteroaryl group may be substituted by one or more D.

[0044] R 1 In embodiments of A according to formulas (3), (3-3), (3-5) and (3-7), is preferably selected from the group D, CN, phenyl, biphenyl, terphenyl, quaterphenyl, dibenzofuranyl or dibenzothiophenyl, where said aryl or heteroaryl groups may be substituted by one or more D. R is particularly preferably 1 for D.

[0045] In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) or preferred compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), it is preferred if A represents the formula (3) and the symbol X represents N, where Ar1 and Ar2 have a meaning mentioned above or mentioned below with preference.

[0046] In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) or preferred compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), it is preferred if A represents the formula (3-1), where Ar1 and Ar2 have a meaning mentioned above or mentioned below with preference.

[0047] Preferred embodiments of A according to formula (4) are described in formulas (4-1) to (4-12), where V, R 1 , R#, m and R d have a meaning previously mentioned or preferred below.

[0048] In embodiments of A according to formulas (4), (4-1), (4-2), (4-3), (4-4), (4-5), (4-6), (4-7), (4-8), (4-9), (4-10), (4-11) and (4-12), R 1 at each occurrence independently of one another are preferably selected from the group D, CN, F or an aryl or heteroaryl group having 5 to 40 ring atoms, where the aryl or heteroaryl group may be substituted by one or more D.

[0049] R 1 In embodiments of A according to the formulas (4), (4-1), (4-2), (4-3), (4-4), (4-5), (4-6), (4-7), (4-8), (4-9), (4-10), (4-11) and (4-12), at each occurrence, independently of one another, is preferably selected from the group D, CN, phenyl, biphenyl, terphenyl, quaterphenyl, dibenzofuranyl or dibenzothiophenyl, where the aryl or heteroaryl groups mentioned may be substituted by one or more D. R is particularly preferably 1for phenyl, biphenyl, terphenyl, quaterphenyl, dibenzofuranyl or dibenzothiophenyl, where the aryl or heteroaryl groups mentioned may be substituted by one or more D.

[0050] In embodiments of A according to formulas (4), (4-1), (4-2), (4-3), (4-4), (4-5), (4-6), (4-7), (4-8), (4-9), (4-10), (4-11) and (4-12), m is preferably 0 or 1. In embodiments of A according to formulas (4), (4-1), (4-2), (4-5), (4-6), (4-7) and (4-8), m is particularly preferably 1.

[0051] In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) or preferred compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), it is preferred if A represents the formula (4), where two Y represent N, the remaining Y represent CH or CR 1 stand and V, R d , R# and R 1 have a meaning previously mentioned or subsequently or previously preferred.

[0052] In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) or preferred compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), it is preferred if A represents one of formulas (4-1), (4-2), (4-3) or (4-4), where V, R d , R# and R 1 have a meaning previously mentioned or subsequently or previously preferred.

[0053] In embodiments of A according to formulas (4), (4-1), (4-2), (4-3), (4-4), (4-5), (4-6), (4-7), (4-8), (4-9), (4-10), (4-11) and (4-12), V is preferably O.

[0054] In the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), where A corresponds to one of formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6), (3-7), (4), (4-1), (4-2), (4-3), (4-4), (4-5), (4-6), (4-7), (4-8), (4-9), (4-10), (4-11) or (4-12), Ar1, Ar2 and R#, when occurring independently of one another, are preferably selected from the group Ar-1 to Ar-42, where Y 2 O, S or Se means Y 3 O, S, NAr4 or C(R*)2, R 3 H or R 0 means, the dashed bond represents the bond to the remainder of formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6), (3-7), (4), (4-1), (4-2), (4-3), (4-4), (4-5), (4-6), (4-7), (4-8), (4-9), (4-10), (4-11) and (4-12), Ar4 represents an aryl group having 6 to 30 ring atoms or a heteroaryl group having 5 to 40 ring atoms which is reacted with one or more radicals R 0 may be substituted, R* at each occurrence, identically or differently, represents a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, each of which is substituted by one or more radicals R 0may be substituted, where one or more H atoms may be replaced by D, F or CN or represents an aryl group having 6 to 30 ring atoms or a heteroaryl group having 5 to 40 ring atoms, which may be substituted with one or more radicals R 0 can be substituted, and where R 0 has a meaning previously mentioned or a meaning preferred below.

[0055] The substituent R 0 Ar4 in N-Ar4 is preferably D, F or CN, particularly preferably D. In the formulas Ar-15 to Ar-18 and Ar-23 to Ar-26, Ar4, when occurring in N-Ar4, is Y 3 particularly preferably selected from non-deuterated, partially deuterated or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl.

[0056] The symbol Y 3 in the formulas Ar-15 to Ar-18 and Ar-23 to Ar-26 preferably denotes N-Ar4, C(CH3)2, O or S, particularly preferably O or S, very particularly preferably O.

[0057] R 0 in R* is preferably D, F or CN, particularly preferably D.

[0058] Y 2 in the formulas Ar-31 to Ar-35 is preferably S or O, particularly preferably O.

[0059] In Ar1, Ar2 or R# the substituent R 0 preferably selected, identically or differently at each occurrence, from the group consisting of D, F, CN or a non-deuterated, partially deuterated or fully deuterated aryl group having 6 to 30 ring atoms or a non-deuterated, partially deuterated or fully deuterated electron-rich heteroaryl group having 9 to 40 ring atoms. In Ar1, Ar2 or R#, the substituent R 0 particularly preferably, at each occurrence, identically or differently selected from the group consisting of D, non-deuterated or partially or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl. In Ar1, Ar2 or R#, the substituent R 0especially preferred D.

[0060] In the structures Ar-1 to Ar-42 the substituent R 3 preferably selected, identically or differently at each occurrence, from the group consisting of H, D, F, CN or a non-deuterated, partially deuterated or fully deuterated aryl group having 6 to 30 ring atoms or a non-deuterated, partially deuterated or fully deuterated electron-rich heteroaryl group having 9 to 40 ring atoms. In the structures Ar-1 to Ar-42, the substituent R 3 particularly preferably, at each occurrence, identically or differently selected from the group consisting of H, D, non-deuterated or partially or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl. In the structures Ar-1 to Ar-42, the substituent R 3 most preferably selected, identically or differently at each occurrence, from the group consisting of H or D.

[0061] Ar1 in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), where A corresponds to one of the formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6) or (3-7) is particularly preferably selected from the group Ar-1 to Ar-18 and Ar-23 to Ar-30, where R 3 has a previously specified or preferred meaning.

[0062] Ar1 in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), where A corresponds to one of the formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6) or (3-7) is very particularly preferably selected from the group Ar-1 to Ar-10, Ar-15 to Ar-18 and Ar-23 to Ar-28, where R 3 has a previously specified or preferred meaning.

[0063] Ar2 in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), where A corresponds to one of the formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6) or (3-7) is particularly preferably selected from the group Ar-1 to Ar-18 and Ar-23 to Ar-30, where R 3 has a previously specified or preferred meaning.

[0064] Ar2 in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), where A corresponds to one of the formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6) or (3-7) is very particularly preferably selected from the group Ar-1 to Ar-10, Ar-15 to Ar-18 and Ar-23 to Ar-28, where R 3 has a meaning previously indicated or preferably indicated. In one embodiment, Ar2 is preferably phenyl, 1,4-biphenyl, 1,3-biphenyl, or 1,2-biphenyl, which are partially deuterated or fully deuterated.

[0065] R# in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), where A corresponds to one of the formulas (4), (4-1), (4-2), (4-3), (4-4), (4-5), (4-6), (4-7), (4-8), (4-9), (4-10), (4-11) or (4-12) is particularly preferably selected from the group Ar-1 to Ar-18 and Ar-23 to Ar-30, where R 3 has a meaning previously indicated or preferably indicated. In one embodiment, R# is preferably phenyl, 1,4-biphenyl, 1,3-biphenyl, 1,2-biphenyl, or dibenzofuranyl, which are partially deuterated or fully deuterated.

[0066] R# in compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), where C corresponds to one of formulas (5), (6), (7) or (8), is particularly preferably selected from the group Ar-1 to Ar-18 and Ar-23 to Ar-30, where R 3has a meaning previously indicated or preferably indicated. In one embodiment, R# is preferably phenyl, 1,4-biphenyl, 1,3-biphenyl, 1,2-biphenyl, or dibenzofuranyl, which are partially deuterated or fully deuterated.

[0067] In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), C is preferably selected from formula (5) or (6).

[0068] In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), where A has a meaning given above or preferred and C corresponds to formula (5), m is 0, 1 or 2, preferably 1 or 2, particularly preferably 1 and R# has a meaning given above or preferred.

[0069] In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), where A has a meaning given above or preferably and C corresponds to formula (6), m is 0, 1 or 2, preferably 0 or 1, particularly preferably 1, and R# has a meaning given above or preferably. Ar3 in formula (6) is preferably selected from the group Ar-1 to Ar-42, as described above. Ar3 in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), where A has a meaning given above or preferably and C corresponds to formula (6), is very particularly preferably selected from the group Ar-1 to Ar-10, Ar-15 to Ar-18 and Ar-23 to Ar-28, where R 3 has a meaning previously indicated or preferably indicated. In one embodiment, Ar3 is preferably phenyl, 1,4-biphenyl, 1,3-biphenyl, or 1,2-biphenyl, which are partially deuterated or fully deuterated.

[0070] In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), where A has a meaning given above or preferred and C corresponds to formula (7), m is 0, 1 or 2, preferably 0 or 1, particularly preferably 0, and R# has a meaning given above or preferred.

[0071] In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), where A has a meaning given above or preferred and C corresponds to formula (8), m is 0, 1 or 2, preferably 0 or 1, particularly preferably 0, and R# has a meaning given above or preferred.

[0072] Particularly preferred embodiments of the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) are compounds in which A corresponds to formula (3-1) and C corresponds to one of formulas (5), (6), (7) or (8), where Ar1, Ar2, Ar3, R# and m have a meaning mentioned above or preferably mentioned.

[0073] Particularly preferred embodiments of the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) are compounds in which A corresponds to formula (3-1) and C corresponds to formula (5), where Ar1, Ar2, R# and m have a meaning mentioned above or preferably mentioned.

[0074] In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), where A corresponds to one of formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6), (3-7), (4), (4-1), (4-2), (4-3), (4-4), (4-5), (4-6), (4-7), (4-8), (4-9), (4-10), (4-11) or (4-12) and C corresponds to one of formulas (5), (6), (7) or (8), R a , R b , R c and R d a monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution or no substitution and R a , R b , R c and R d are D at every occurrence.

[0075] Compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), where A corresponds to one of the formulas (3), (3-1), (3-2), (3-3), (3-4), (3-5), (3-6), (3-7), (4), (4-1), (4-2), (4-3), (4-4), (4-5), (4-6), (4-7), (4-8), (4-9), (4-10), (4-11) or (4-12) and C corresponds to one of the formulas (5), (6), (7) or (8) are preferably partially or fully deuterated, ie at least one R a , R b , R c or R d corresponds to a monosubstitution with D.

[0076] A further subject matter accordingly are compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g), as previously described or preferably described, which are partially or completely deuterated.

[0077] If the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) are deuterated compounds, it is possible during their preparation, provided that the preparation is chosen by reacting a non-deuterated compound of one of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g) with a deuteration source or provided that deuterated starting compounds are chosen during the preparation which are a mixture of deuterated starting compounds, that a mixture of deuterated products of the same basic chemical structure is formed which only differ in the degree of deuteration and / or the deuteration patterns.

[0078] Such mixtures of deuterated compounds of the same basic chemical structure of formula (1) or the basic structure of the preferred embodiments, which differ only in the degree of deuteration and / or the deuteration patterns, are understood by the term at least one compound of formula (1) in the sense of the invention.

[0079] In a preferred embodiment of the at least one compound of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) and (1g), as described above or preferably described, the average degree of deuteration is at least 10 mol% to 100 mol%, preferably 50 mol% to 95 mol%, particularly preferably 70 mol% to 90 mol%.

[0080] Corresponding deuteration methods are known to the person skilled in the art and are described, for example, in KR2016041014, WO2017 / 122988, KR202005282, KR101978651 and WO2018 / 110887 or in Bulletin of the Chemical Society of Japan, 2021, 94(2), 600-605 or Asian Journal of Organic Chemistry, 2017, 6(8), 1063-1071.

[0081] A suitable method for deuterating a compound by exchanging one or more hydrogen atoms for diatoms is to treat the compound to be deuterated in the presence of a platinum or palladium catalyst and a deuterium source. The term "deuterium source" refers to any compound containing one or more diatoms and capable of releasing them under suitable conditions.

[0082] The platinum catalyst is preferably dry platinum on carbon, preferably 5% dry platinum on carbon. The palladium catalyst is preferably dry palladium on carbon, preferably 5% dry palladium on carbon. A suitable deuterium source is D2O, benzene-d6, chloroform-d, acetonitrile-d3, acetone-d6, acetic acid-d4, methanol-d4, or toluene-d8. A preferred deuterium source is D2O or a combination of D2O and a fully deuterated organic solvent. A particularly preferred deuterium source is the combination of D2O with a fully deuterated organic solvent, whereby the fully deuterated solvent is not limited here. Particularly suitable fully deuterated solvents are benzene-d6 and toluene-d8. A particularly preferred deuterium source is a combination of D2O and toluene-d8.The reaction is preferably carried out with heating, more preferably with heating to temperatures between 100 °C and 200 °C. Furthermore, the reaction is preferably carried out under pressure.

[0083] Examples of suitable host materials of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) are the structures listed below in Table 1.

[0084] Particularly suitable compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) are compounds E1 to E30 of Table 2.

[0085] For simplicity, the compounds in Tables 1 and 2 are partially depicted as fully deuterated compounds, which generally refers to compounds that have a degree of deuteration of at least 50 mol%. The degree of deuteration for the fully deuterated compounds in Tables 1 and 2 is therefore between 50 and 100 mol% or has a preferred degree of deuteration, as previously described. For partially deuterated compounds, a D atom means that the corresponding position in the molecule has a degree of deuteration of at least 40 mol%.

[0086] The compounds according to the invention can be prepared by synthesis steps known to the person skilled in the art, such as bromination, Suzuki coupling, Ullmann coupling, Hartwig-Buchwald coupling, etc.

[0087] By these processes, optionally followed by purification, such as recrystallization or sublimation, the compounds of formula (1) can be obtained in high purity, preferably more than 99% (determined by 1 H-NMR and / or HPLC).

[0088] For processing the compounds of the invention from the liquid phase, for example by spin coating or printing processes, formulations of the compounds of the invention or mixtures of compounds of the invention with other functional materials, such as matrix materials, fluorescent emitters, phosphorescent emitters, and / or emitters exhibiting TADF, 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-Dimethylanisol, 3,5-Dimethylanisol, Acetophenon, α-Terpineol, Benzothiazol, Butylbenzoat, Cumol, Cyclohexanol, Cyclohexanon, Cyclohexylbenzol, Decalin, Dodecylbenzol, Ethylbenzoat, Indan, NMP, p-Cymol, Phenetol, 1,4-Diisopropylbenzol, Dibenzylether, Diethylenglycolbutylmethylether, Triethylenglycolbutylmethylether, Diethylenglycoldibutylether, Triethylenglycoldimethylether, Diethylenglycolmonobutylether, Tripropyleneglycoldimethylether, Tetraethylenglycoldimethylether, 2-Isopropylnaphthalin, Pentylbenzol, Hexylbenzol, Heptylbenzol, Octylbenzol, 1,1-Bis(3,4-dimethylphenyl)ethan, 2-Methylbiphenyl, 3-Methylbiphenyl, 1-Methylnaphthalin, 1-Ethylnaphthalin, Ethyloctanoat, Sebacinsäure-diethylester, Octyloctanoat, Heptylbenzol, Menthyl-isovalerat, Cyclohexylhexanoat oder Mischungen dieser Lösemittel.,

[0089] A suitable formulation is a formulation comprising at least one compound according to the invention, as described above, or a mixture according to the invention, as described below, and at least one solvent. The solvent can be one of the solvents mentioned above or a mixture of these solvents.

[0090] The compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) according to the invention, as described above or preferably described, are suitable for use in an organic electroluminescent device, in particular as matrix material.

[0091] If the compound according to the invention is used as matrix material or synonymously host material in an emitting layer, it is preferably used in combination with another compound.

[0092] The invention therefore further provides a mixture comprising at least one compound of formula (1) or at least one preferred compound of one of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) or a compound of Table 1 or one of the compounds E1 to E30 and at least one further compound selected from the group of matrix materials, phosphorescent emitters, fluorescent emitters and / or emitters exhibiting TADF (thermally activated delayed fluorescence). Suitable matrix materials and emitters that can be used in this mixture according to the invention are described below.

[0093] The present invention further provides an organic electronic device comprising an anode, a cathode and at least one organic layer containing at least one compound of formula (1) or at least one preferred compound of one of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g), or a compound of Table 1 or one of the compounds E1 to E30.

[0094] The organic electronic device can be selected, for example, from organic integrated circuits (OLCs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors, organic photoreceptors. Preferably, the organic electronic device is an organic electroluminescent device.

[0095] The organic electroluminescent device according to the invention (synonymously referred to as organic electroluminescent device) is, for example, an organic light-emitting transistor (OLET), an organic field quench device (OFQD), an organic light-emitting electrochemical cell (OLEC), an organic laser diode (O-laser), or an organic light-emitting diode (OLED). The organic electroluminescent device according to the invention is, in particular, an organic light-emitting diode or an organic light-emitting electrochemical cell. The device according to the invention is particularly preferably an OLED.

[0096] The organic layer of the device according to the invention preferably contains, in addition to a light-emitting layer (EML), a hole-injection layer (HIL), a hole-transport layer (HTL), a hole-blocking layer (HBL), an electron-transport layer (ETL), an electron-injection layer (EIL), an exciton-blocking layer, an electron-blocking layer, and / or charge-generation layers. The device according to the invention can also contain several layers from this group, preferably selected from EML, HIL, HTL, ETL, EIL, and HBL. Interlayers, which, for example, have an exciton-blocking function, can also be introduced between two emitting layers.

[0097] If a plurality of emission layers are present, these preferably have a total of a plurality of emission maxima between 380 nm and 750 nm, resulting in an overall white emission, i.e. different emitting compounds which can fluoresce or phosphoresce are used in the emitting layers. A plurality of fluorescent and / or phosphorescent compounds can also be present in one emitting layer. Systems with three emitting layers are particularly preferred, wherein the three layers exhibit blue, green and orange or red emission. As an alternative to the combination as described above, an emitting layer can also exhibit yellow emission. Such combinations are known to the person skilled in the art. The organic electroluminescent device according to the invention can also be a tandem electroluminescent device, in particular for white-emitting OLEDs.

[0098] The device may also contain inorganic materials or layers made entirely of inorganic materials.

[0099] A variety of materials known in the prior art are suitable for use in the layers of the organic electroluminescent device described above. When selecting materials, common considerations regarding their chemical and physical properties must be taken into account, as the materials in an organic electroluminescent device are interrelated. This applies, for example, to the energy positions of the orbitals (HOMO, LUMO) or the position of triplet and singlet energies, as well as other material properties.

[0100] The compound of the formula (1) according to the invention, as described above or preferably described, can be used in different layers, depending on the precise structure. Preference is given to an organic electroluminescent device comprising a compound of the formula (1) or the preferred embodiments described above in an emitting layer as a matrix material for fluorescent emitters, phosphorescent emitters or for emitters which display TADF (thermally activated delayed fluorescence), in particular for phosphorescent emitters. Furthermore, the compound of the invention can also be used in an electron transport layer and / or an electron injection layer and / or in a hole blocking layer. The compound of the invention is particularly preferably used as a matrix material in an emitting layer or as an electron transport or electron injection orHole blocking material used in an electron transport, electron injection or hole blocking layer.

[0101] A further subject matter of the present invention is an organic electronic device as described above, wherein the organic layer contains at least one light-emitting layer which contains at least one compound of the formula (1) or the at least one preferred compound of one of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) or a compound of Table 1 or one of the compounds E1 to E30.

[0102] In one embodiment of the invention, at least one further matrix material is selected for the device according to the invention in the light-emitting layer, which is used with compounds of the formula (1), as described above or preferably described, or with the compounds of Table 1 or the compounds E1 to E30.

[0103] A further subject matter of the present invention is accordingly an organic electronic device as described above, wherein the organic layer contains at least one light-emitting layer which contains at least one compound of the formula (1) or the at least one preferred compound of one of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) or a compound of Table 1 or one of the compounds E1 to E30 and at least one further matrix material. A further subject matter of the present invention is accordingly an organic electronic device as described above, wherein the organic layer contains at least one light-emitting layer which contains at least one compound of the formula (1) or the at least one preferred compound of one of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) or a compound of Table 1 or one of the compounds E1 to E30 and two further matrix materials.

[0104] Suitable matrix materials that can be used in combination with the compounds according to the invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, triarylamines, carbazole derivatives, biscarbazoles, indolocarbazole derivatives, indenocarbazole derivatives, azacarbazole derivatives, bipolar matrix materials, azaboroles or boronic esters, triazine derivatives, zinc complexes, diazasilole or tetraazasilole derivatives, diazaphosphole derivatives, bridged carbazole derivatives, triphenylene derivatives, or dibenzofuran derivatives. Likewise, another phosphorescent emitter that emits at a shorter wavelength than the actual emitter can be present in the mixture as a co-host, or a compound that does not participate, or does not participate to a significant extent, in charge transport, such as a wide-band-gap compound.

[0105] A wide-band-gap material is understood herein to mean a material within the meaning of the disclosure of US 7,294,849, which is characterized by a band gap of at least 3.5 eV, where the band gap is understood to be the distance between the HOMO and LUMO energy of a material.

[0106] Particularly suitable hole-transporting matrix materials which are advantageously combined with compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g), as previously described or preferably described, in a mixed matrix system can be selected from the compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6), as described below.

[0107] A further subject matter of the invention is accordingly an organic electronic device comprising an anode, a cathode and at least one organic layer containing at least one light-emitting layer, wherein the at least one light-emitting layer contains at least one compound of the formula (1) as matrix material 1, as described above or described as preferred, and at least one compound of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6) as matrix material 2, where the symbols and indices used are: A 1 is C(R 7 )2, NR 7 , O or S; L is a bond, O, S, C(R 7 )2 or NR 7 ; A is at each occurrence independently a group of the formula (HH-4-1) or (HH-4-2), X2 is the same or different at each occurrence CH, CR 6 or N, where a maximum of 2 symbols X2 can mean N; * indicates the binding site to the formula (HH-4); U 1 , U 2 are a bond, O, S, C(R 7 )2 or NR 7 ; R 6 is at each occurrence, identically or differently, D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 7 may be substituted and wherein one or more non-adjacent CH2 groups are substituted by Si(R 7 )2, C=O, NR 7 , O, S or CONR 7 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, each of which is substituted by one or more radicals R 7 can be substituted; two radicals R 6also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system with each other; Ar5, identically or differently at each occurrence, independently represents an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which is substituted by one or more radicals R 7 can be substituted; R 7 is the same or different at each occurrence D, F, Cl, Br, I, N(R 8 )2, CN, NO2, OR 8, SR 8 , Si(R 8 )3, B(OR 8 )2, C(=O)R 8 , P(=O)(R 8 )2, S(=O)R 8 , S(=O)2R 8 , OSO2R 8 , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 8may be substituted, with one or more non-adjacent CH2 groups being substituted by Si(R 8 )2, C=O, NR 8 , O, S or CONR 8 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which is substituted by one or more radicals R 8 may be substituted, where R 8 does not denote H; two or more radicals R 7 together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system, preferably the radicals R 7 no such ring system; R 8 is, at each occurrence, identically or differently, H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, in particular a hydrocarbon radical, having 1 to 20 C atoms, in which one or more H atoms may be replaced by D or F; c, c1, c2 each independently represent 0 or 1 at each occurrence, where the sum of the indices at each occurrence is c+c1+c2 = 1; d, d1, d2 each independently represent 0 or 1 at each occurrence, where the sum of the indices at each occurrence is d+d1+d2 = 1; q, q1, q2 each independently represent 0, 1, 2, 3 or 4 at each occurrence; s is the same or different at each occurrence: 0, 1, 2, 3 or 4; t is the same or different at each occurrence: 0, 1, 2, or 3; u is the same or different at each occurrence: 0, 1 or 2; u1, u2 each independently represent 0 or 1 on each occurrence, where the sum u1 + u2 = 1; and v is 0, 1, 2 or 3.

[0108] Preferred compounds of formula (HH-5) are compounds of formulas (HH-5-A) to (HH-5-E), where Ar5, R 6, s and u have a previously specified or preferred meaning.

[0109] In compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6), s is preferably 0 or 1 if the radical R 6 is different from D, or more preferably 0.

[0110] In compounds of the formulas (HH-1), (HH-2) or (HH-3), t is preferably 0 or 1 if the radical R 6 is different from D, or more preferably 0.

[0111] In compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D) or (HH-5-E), u is preferably 0 or 1 if the radical R 6 is different from D, or more preferably 0.

[0112] The sum of the indices s, t and u in compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6) is preferably at most 6, particularly preferably at most 4 and particularly preferably at most 2. This preferably applies when R 6 is different from D.

[0113] In compounds of formula (HH-4), c, c1, c2 each independently represent 0 or 1 at each occurrence, where the sum of the indices c+c1+c2 represents 1 at each occurrence. Preferably, c2 represents 1.

[0114] In compounds of formula (HH-4), L is preferably a single bond or C(R 7 )2, where R 7 has a meaning mentioned above, particularly preferably L is a single bond.

[0115] In formula (HH-4-1), v is preferably 0 or 1 if the radical R 6 is different from D.

[0116] In formula (HH-4-2) U 1 or U 2when occurring, preferably a single bond or C(R 7 )2, where R 7 has a meaning mentioned above, particularly preferred are U 1 or U 2 when a single bond occurs.

[0117] In formula (HH-4-2), q, q1, q2 are preferably 0 or 1 when the radical R 6 is different from D.

[0118] In a preferred embodiment of the compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6), which can be combined according to the invention with compounds of formula (1) or preferred compounds of formula (1), as described above, R 6 identically or differently on each occurrence selected from the group consisting of D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl group is in each case substituted with one or more radicals R7 may be substituted, or an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, preferably having 5 to 40 ring atoms, each substituted by one or more radicals R 7 can be substituted.

[0119] In a preferred embodiment of the compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6), which can be combined according to the invention with compounds of formula (1) or preferred compounds of formula (1), as described above, R 6 identically or differently on each occurrence selected from the group consisting of D or an aromatic or heteroaromatic ring system having 6 to 30 ring atoms, which is reacted with one or more radicals R 7 can be substituted.

[0120] Preferably, Ar5 in compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6) is selected from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorenyl, which may be linked via the 1-, 2-, 3- or 4-position, 9,9-dimethylfluorenyl, which may be linked via the 1-, 2-, 3- or 4-position, spirobifluorenyl, which may be linked via the 1-, 2-, 3- or 4-position, naphthyl, in particular 1- or 2-linked naphthyl, or residues derived from indole, benzofuran, benzothiophene, carbazole, which may be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, which may be linked via the 1-, 2-, 3- or 4-position, dibenzothiophene, which may be linked via the 1-, 2-, 3- or 4-position, indenocarbazole,Indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene, each of which is substituted with one or more radicals R, 7 may be substituted. Ar5 is preferably deuterated, but not further substituted.

[0121] If A 1 in formula (HH-2) or (HH-3) or (HH-6) for NR 7 the substituent R 7 which is bonded to the nitrogen atom, preferably represents an aromatic or heteroaromatic ring system having 5 to 24 ring atoms, which may also be substituted by one or more radicals R 8 In a particularly preferred embodiment, this substituent R 7 identically or differently on each occurrence represents an aromatic or heteroaromatic ring system having 6 to 24 ring atoms, in particular having 6 to 18 ring atoms. Preferred embodiments for R 7are phenyl, biphenyl, terphenyl and quaterphenyl, which are preferably deuterated, as well as residues derived from triazine, pyrimidine and quinazoline, which are substituted by one or more residues R 8 may be substituted, where R 8 does not mean H.

[0122] If A 1 in formula (HH-2) or (HH-3) or (HH-6) for C(R 7 )2, the substituents R 7 which are bonded to this carbon atom, preferably identically or differently on each occurrence, represent a linear alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms or an aromatic or heteroaromatic ring system having 5 to 24 ring atoms, which can also be substituted by one or more radicals R 8 may be substituted, where R 8 does not represent H. Most preferably, R 7 represents a methyl group or a phenyl group. The radicals R 7also form a ring system with each other, which leads to a spiro system.

[0123] In a preferred embodiment of the compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) and (HH-6), these compounds are partially or completely deuterated, particularly preferably completely deuterated.

[0124] The preparation of the compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) and (HH-6) are generally known and some of the compounds are commercially available.

[0125] Compounds of formula (HH-4) are disclosed, for example, in WO2021 / 180614, pages 110 to 119, in particular as examples on pages 120 to 127. Their preparation is disclosed in WO2021 / 180614 A1 on page 128 and in the synthesis examples on pages 214 to 218.

[0126] The preparation of the triarylamines of formula (HH-6) is known to the person skilled in the art and some of the compounds are commercially available.

[0127] If the at least one further matrix material is a deuterated compound, it is possible that this at least one matrix material is a mixture of deuterated compounds with the same basic chemical structure, differing only in the degree of deuteration and / or the deuteration pattern. The statements regarding deuterated mixtures and the preparation of deuterated materials, as previously described for compounds of formula (1), apply here accordingly.

[0128] In a preferred embodiment of the at least one further matrix material, this is a mixture of deuterated compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6), as described above, wherein the average degree of deuteration of these compounds is at least 50 mol% to 90 mol%, preferably 70 mol% to 100 mol%.

[0129] Examples of suitable further matrix materials for a combination with compounds of formula (1), as previously described or preferably described, are the compounds described in WO2019 / 229011 A1, Table 3, pages 137 to 203, which may also be partially or completely deuterated.

[0130] Examples of suitable further matrix materials for combination with compounds of formula (1) or preferred compounds of formula (1) as previously described or preferably described are the compounds described in WO2021 / 180625 A1, Table 3, pages 131 to 137 and in Table 4, pages 137 to 139, which may also be partially or completely deuterated.

[0131] Examples of suitable further matrix materials for combination with compounds of formula (1) or preferred compounds of formula (1) as previously described or preferably described are the compounds described in KR20230034896 A, on pages 42 to 47, compounds [2-1] to [2-110], or on pages 49 to 51, compounds [3-1] to [3-26].

[0132] Examples of suitable further matrix materials for combination with compounds of formula (1) or preferred compounds of formula (1) as previously described or preferably described are the compounds described in KR20230154750 A, on pages 39 to 49, compounds [B-1] to [B-243], or on pages 49 to 53, compounds [C-1] to [C-102] or on pages 54 to 57, compounds [D-1] to [D-120].

[0133] Examples of suitable further matrix materials for combination with compounds of formula (1) or preferred compounds of formula (1) as previously described or preferably described are the compounds described in US2023172065 A, on pages 413 to 434.

[0134] For a combination with compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g), as described above or preferably described, compounds of the formula (HH-1) and / or the formula (HH-4) and / or the formulas (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D) and (HH-5-E) are particularly suitable, as described above or preferably described. In the subgroup of compounds of the formula (HH-5), selected from compounds of the formulas (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E), compounds of the formulas (HH-5A, (HH-5-B) and (HH-5-D) are preferred, with compounds of the formula (HH-5-A) being particularly preferred.

[0135] For a combination with compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g), as described above or preferably described, compounds of formula (HH-1), (HH-4) and / or compounds of formula (HH-5) are particularly suitable.

[0136] For a combination with a compound of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g), as previously described or preferably described, compounds of formula (HH-4) or (HH-5) or (HH-5-A) are very particularly suitable.

[0137] Further examples of suitable host materials of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) and (HH-6) for combination with compounds of the formula (1) or preferred compounds of the formula (1), as previously described or preferably described, are the structures of Table 3 and Table 4 mentioned below.

[0138] n in Table 3 above means the number of D atoms in the respective compound and is 0 or D1 to D max , preferably D1 to D maxIf n = 0, this means that the compound is non-deuterated. n = D1 means that in the respective compound, one H atom is replaced by a D atom. D max means the maximum number of D atoms possible in the respective compound. The maximum number of D max can vary from connection to connection. D max Depending on the connection, this can take the following values: 20, 24, 26, 28, 30, 31, 32, 34, 35, 36, 37, 38 and 40.

[0139] Particularly suitable compounds of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6), which are selected according to the invention and are preferably used in combination with at least one compound of the formula (1) in the electroluminescent device according to the invention, are the compounds of Table 4.

[0140] For simplicity, the compounds in Tables 3 and 4 are partially presented as fully deuterated compounds, which generally refers to compounds that have a degree of deuteration of at least 50 mol%. The degree of deuteration for the fully deuterated compounds in Tables 3 and 4 is therefore between 50 and 100 mol% or has a preferred degree of deuteration as previously described. For partially deuterated compounds, a D atom means that the corresponding position in the molecule has a degree of deuteration of at least 40 mol%.

[0141] The above-mentioned host materials of formula (1) and their preferred embodiments or the compounds of Table 1 and the compounds E1 to E30 can be combined as desired in the device according to the invention with the above-mentioned matrix materials / host materials, the matrix materials / host materials of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6) and their preferred embodiments of Table 3 or the compounds H1 to H51.

[0142] Very particularly preferred mixtures of the compounds of formula (1) with the host materials of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6) for the device according to the invention are obtained by combining the compounds E1 to E30 with the compounds H1 to H51. Very preferred mixtures are shown in Table 5 below. The first mixture M1, for example, is a combination of the compound E1 with H1. Table 5: M1 E1 H1 M2 E2 H1 M3 E3 H1 M4 E4 H1 M5 E5 H1 M6 E6 H1 M7 E7 H1 M8 E8 H1 M9 E9 H1 M10 E10 H1 M11 E11 H1 M12 E12 H1 M13 E13 H1 M14 E14 H1 M15 E15 H1 M16 E16 H1 M17 E17 H1 M18 E18 H1 M19 E19 H1 M20 E20 H1 M21 E21 H1 M22 E22 H1 M23 E23 H1 M24 E24 H1 M25 E25 H1 M26 E26 H1 M27 E27 H1 M28 E28 H1 M29 E29 H1 M30 E30 H1 M31 E1 H2 M32 E2 H2 M33 E3 H2 M34 E4 H2 M35 E5 H2 M36 E6 H2 M37 E7 H2 M38 E8 H2 M39 E9 H2 M40 E10 H2 M41 E11 H2 M42 E12 H2 M43 E13 H2 M44 E14 H2 M45 E15 H2 M46 E16 H2 M47 E17 H2 M48 E18 H2 M49 E19 H2 M50 E20 H2 M51 E21 H2 M52 E22 H2 M53 E23 H2 M54 E24 H2 M55 E25 H2 M56 E26 H2 M57 E27 H2 M58 E28 H2 M59 E29 H2 M60 E30 H2 M61 E1 H3 M62 E2 H3 M63 E3 H3 M64 E4 H3 M65 E5 H3 M66 E6 H3 M67 E7 H3 M68 E8 H3 M69 E9 H3 M70 E10 H3 M71 E11 H3 M72 E12 H3 M73 E13 H3 M74 E14 H3 M75 E15 H3 M76 E16 H3 M77 E17 H3 M78 E18 H3 M79 E19 H3 M80 E20 H3 M81 E21 H3 M82 E22 H3 M83 E23 H3 M84 E24 H3 M85 E25 H3 M86 E26 H3 M87 E27 H3 M88 E28 H3 M89 E29 H3 M90 E30 H3 M91 E1 H4 M92 E2 H4 M93 E3 H4 M94 E4 H4 M95 E5 H4 M96 E6 H4 M97 E7 H4 M98 E8 H4 M99 E9 H4 M100 E10 H4 M101 E11 H4 M102 E12 H4 M103 E13 H4 M104 E14 H4 M105 E15 H4 M106 E16 H4 M107 E17 H4 M108 E18 H4 M109 E19 H4 M110 E20 H4 M111 E21 H4 M112 E22 H4 M113 E23 H4 M114 E24 H4 M115 E25 H4 M116 E26 H4 M117 E27 H4 M118 E28 H4 M119 E29 H4 M120 E30 H4 M121 E1 H5 M122 E2 H5 M123 E3 H5 M124 E4 H5 M125 E5 H5 M126 E6 H5 M127 E7 H5 M128 E8 H5 M129 E9 H5 M130 E10 H5 M131 E11 H5 M132 E12 H5 M133 E13 H5 M134 E14 H5 M135 E15 H5 M136 E16 H5 M137 E17 H5 M138 E18 H5 M139 E19 H5 M140 E20 H5 M141 E21 H5 M142 E22 H5 M143 E23 H5 M144 E24 H5 M145 E25 H5 M146 E26 H5 M147 E27 H5 M148 E28 H5 M149 E29 H5 M150 E30 H5 M151 E1 H6 M152 E2 H6 M153 E3 H6 M154 E4 H6 M155 E5 H6 M156 E6 H6 M157 E7 H6 M158 E8 H6 M159 E9 H6 M160 E10 H6 M161 E11 H6 M162 E12 H6 M163 E13 H6 M164 E14 H6 M165 E15 H6 M166 E16 H6 M167 E17 H6 M168 E18 H6 M169 E19 H6 M170 E20 H6 M171 E21 H6 M172 E22 H6 M173 E23 H6 M174 E24 H6 M175 E25 H6 M176 E26 H6 M177 E27 H6 M178 E28 H6 M179 E29 H6 M180 E30 H6 M181 E1 H7 M182 E2 H7 M183 E3 H7 M184 E4 H7 M185 E5 H7 M186 E6 H7 M187 E7 H7 M188 E8 H7 M189 E9 H7 M190 E10 H7 M191 E11 H7 M192 E12 H7 M193 E13 H7 M194 E14 H7 M195 E15 H7 M196 E16 H7 M197 E17 H7 M198 E18 H7 M199 E19 H7 M200 E20 H7 M201 E21 H7 M202 E22 H7 M203 E23 H7 M204 E24 H7 M205 E25 H7 M206 E26 H7 M207 E27 H7 M208 E28 H7 M209 E29 H7 M210 E30 H7 M211 E1 H8 M212 E2 H8 M213 E3 H8 M214 E4 H8 M215 E5 H8 M216 E6 H8 M217 E7 H8 M218 E8 H8 M219 E9 H8 M220 E10 H8 M221 E11 H8 M222 E12 H8 M223 E13 H8 M224 E14 H8 M225 E15 H8 M226 E16 H8 M227 E17 H8 M228 E18 H8 M229 E19 H8 M230 E20 H8 M231 E21 H8 M232 E22 H8 M233 E23 H8 M234 E24 H8 M235 E25 H8 M236 E26 H8 M237 E27 H8 M238 E28 H8 M239 E29 H8 M240 E30 H8 M241 E1 H9 M242 E2 H9 M243 E3 H9 M244 E4 H9 M245 E5 H9 M246 E6 H9 M247 E7 H9 M248 E8 H9 M249 E9 H9 M250 E10 H9 M251 E11 H9 M252 E12 H9 M253 E13 H9 M254 E14 H9 M255 E15 H9 M256 E16 H9 M257 E17 H9 M258 E18 H9 M259 E19 H9 M260 E20 H9 M261 E21 H9 M262 E22 H9 M263 E23 H9 M264 E24 H9 M265 E25 H9 M266 E26 H9 M267 E27 H9 M268 E28 H9 M269 E29 H9 M270 E30 H9 M271 E1 H10 M272 E2 H10 M273 E3 H10 M274 E4 H10 M275 E5 H10 M276 E6 H10 M277 E7 H10 M278 E8 H10 M279 E9 H10 M280 E10 H10 M281 E11 H10 M282 E12 H10 M283 E13 H10 M284 E14 H10 M285 E15 H10 M286 E16 H10 M287 E17 H10 M288 E18 H10 M289 E19 H10 M290 E20 H10 M291 E21 H10 M292 E22 H10 M293 E23 H10 M294 E24 H10 M295 E25 H10 M296 E26 H10 M297 E27 H10 M298 E28 H10 M299 E29 H10 M300 E30 H10 M301 E1 H11 M302 E2 H11 M303 E3 H11 M304 E4 H11 M305 E5 H11 M306 E6 H11 M307 E7 H11 M308 E8 H11 M309 E9 H11 M310 E10 H11 M311 E11 H11 M312 E12 H11 M313 E13 H11 M314 E14 H11 M315 E15 H11 M316 E16 H11 M317 E17 H11 M318 E18 H11 M319 E19 H11 M320 E20 H11 M321 E21 H11 M322 E22 H11 M323 E23 H11 M324 E24 H11 M325 E25 H11 M326 E26 H11 M327 E27 H11 M328 E28 H11 M329 E29 H11 M330 E30 H11 M331 E1 H12 M332 E2 H12 M333 E3 H12 M334 E4 H12 M335 E5 H12 M336 E6 H12 M337 E7 H12 M338 E8 H12 M339 E9 H12 M340 E10 H12 M341 E11 H12 M342 E12 H12 M343 E13 H12 M344 E14 H12 M345 E15 H12 M346 E16 H12 M347 E17 H12 M348 E18 H12 M349 E19 H12 M350 E20 H12 M351 E21 H12 M352 E22 H12 M353 E23 H12 M354 E24 H12 M355 E25 H12 M356 E26 H12 M357 E27 H12 M358 E28 H12 M359 E29 H12 M360 E30 H12 M361 E1 H13 M362 E2 H13 M363 E3 H13 M364 E4 H13 M365 E5 H13 M366 E6 H13 M367 E7 H13 M368 E8 H13 M369 E9 H13 M370 E10 H13 M371 E11 H13 M372 E12 H13 M373 E13 H13 M374 E14 H13 M375 E15 H13 M376 E16 H13 M377 E17 H13 M378 E18 H13 M379 E19 H13 M380 E20 H13 M381 E21 H13 M382 E22 H13 M383 E23 H13 M384 E24 H13 M385 E25 H13 M386 E26 H13 M387 E27 H13 M388 E28 H13 M389 E29 H13 M390 E30 H13 M391 E1 H14 M392 E2 H14 M393 E3 H14 M394 E4 H14 M395 E5 H14 M396 E6 H14 M397 E7 H14 M398 E8 H14 M399 E9 H14 M400 E10 H14 M401 E11 H14 M402 E12 H14 M403 E13 H14 M404 E14 H14 M405 E15 H14 M406 E16 H14 M407 E17 H14 M408 E18 H14 M409 E19 H14 M410 E20 H14 M411 E21 H14 M412 E22 H14 M413 E23 H14 M414 E24 H14 M415 E25 H14 M416 E26 H14 M417 E27 H14 M418 E28 H14 M419 E29 H14 M420 E30 H14 M421 E1 H15 M422 E2 H15 M423 E3 H15 M424 E4 H15 M425 E5 H15 M426 E6 H15 M427 E7 H15 M428 E8 H15 M429 E9 H15 M430 E10 H15 M431 E11 H15 M432 E12 H15 M433 E13 H15 M434 E14 H15 M435 E15 H15 M436 E16 H15 M437 E17 H15 M438 E18 H15 M439 E19 H15 M440 E20 H15 M441 E21 H15 M442 E22 H15 M443 E23 H15 M444 E24 H15 M445 E25 H15 M446 E26 H15 M447 E27 H15 M448 E28 H15 M449 E29 H15 M450 E30 H15 M451 E1 H16 M452 E2 H16 M453 E3 H16 M454 E4 H16 M455 E5 H16 M456 E6 H16 M457 E7 H16 M458 E8 H16 M459 E9 H16 M460 E10 H16 M461 E11 H16 M462 E12 H16 M463 E13 H16 M464 E14 H16 M465 E15 H16 M466 E16 H16 M467 E17 H16 M468 E18 H16 M469 E19 H16 M470 E20 H16 M471 E21 H16 M472 E22 H16 M473 E23 H16 M474 E24 H16 M475 E25 H16 M476 E26 H16 M477 E27 H16 M478 E28 H16 M479 E29 H16 M480 E30 H16 M481 E1 H17 M482 E2 H17 M483 E3 H17 M484 E4 H17 M485 E5 H17 M486 E6 H17 M487 E7 H17 M488 E8 H17 M489 E9 H17 M490 E10 H17 M491 E11 H17 M492 E12 H17 M493 E13 H17 M494 E14 H17 M495 E15 H17 M496 E16 H17 M497 E17 H17 M498 E18 H17 M499 E19 H17 M500 E20 H17 M501 E21 H17 M502 E22 H17 M503 E23 H17 M504 E24 H17 M505 E25 H17 M506 E26 H17 M507 E27 H17 M508 E28 H17 M509 E29 H17 M510 E30 H17 M511 E1 H18 M512 E2 H18 M513 E3 H18 M514 E4 H18 M515 E5 H18 M516 E6 H18 M517 E7 H18 M518 E8 H18 M519 E9 H18 M520 E10 H18 M521 E11 H18 M522 E12 H18 M523 E13 H18 M524 E14 H18 M525 E15 H18 M526 E16 H18 M527 E17 H18 M528 E18 H18 M529 E19 H18 M530 E20 H18 M531 E21 H18 M532 E22 H18 M533 E23 H18 M534 E24 H18 M535 E25 H18 M536 E26 H18 M537 E27 H18 M538 E28 H18 M539 E29 H18 M540 E30 H18 M541 E1 H19 M542 E2 H19 M543 E3 H19 M544 E4 H19 M545 E5 H19 M546 E6 H19 M547 E7 H19 M548 E8 H19 M549 E9 H19 M550 E10 H19 M551 E11 H19 M552 E12 H19 M553 E13 H19 M554 E14 H19 M555 E15 H19 M556 E16 H19 M557 E17 H19 M558 E18 H19 M559 E19 H19 M560 E20 H19 M561 E21 H19 M562 E22 H19 M563 E23 H19 M564 E24 H19 M565 E25 H19 M566 E26 H19 M567 E27 H19 M568 E28 H19 M569 E29 H19 M570 E30 H19 M571 E1 H20 M572 E2 H20 M573 E3 H20 M574 E4 H20 M575 E5 H20 M576 E6 H20 M577 E7 H20 M578 E8 H20 M579 E9 H20 M580 E10 H20 M581 E11 H20 M582 E12 H20 M583 E13 H20 M584 E14 H20 M585 E15 H20 M586 E16 H20 M587 E17 H20 M588 E18 H20 M589 E19 H20 M590 E20 H20 M591 E21 H20 M592 E22 H20 M593 E23 H20 M594 E24 H20 M595 E25 H20 M596 E26 H20 M597 E27 H20 M598 E28 H20 M599 E29 H20 M600 E30 H20

[0143] The concentration of the host material of formula (1), as described above or preferably described, in the mixture according to the invention or in the light-emitting layer of the device according to the invention is usually in the range from 5 wt.% to 90 wt.%, preferably in the range from 10 wt.% to 85 wt.%, more preferably in the range from 20 wt.% to 85 wt.%, even more preferably in the range from 30 wt.% to 80 wt.%, very particularly preferably in the range from 20 wt.% to 60 wt.% and most preferably in the range from 30 wt.% to 50 wt.%, based on the total mixture or based on the total composition of the light-emitting layer.

[0144] The concentration of the sum of all host materials of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) and (HH-6), as described above or described as preferred, in the mixture according to the invention or in the light-emitting layer of the device according to the invention is usually in the range from 10 wt.% to 95 wt.%, preferably in the range from 15 wt.% to 90 wt.%, more preferably in the range from 15 wt.% to 80 wt.%, even more preferably in the range from 20 wt.% to 70 wt.%, very particularly preferably in the range from 40 wt.% to 80 wt.% and most preferably in the range from 50 wt.% to 70 wt.%, based on the entire mixture or based on the entire composition of the light-emitting layer.

[0145] The present invention also relates to a mixture which, in addition to the above-mentioned host materials of the formula (1), hereinafter referred to as host material 1, and the host material of at least one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) and (HH-6), hereinafter referred to as host material 2, as described above or preferably described, contains at least one phosphorescent emitter.

[0146] The present invention also relates to a mixture selected from a combination of the compounds E1 to E30 with the compounds H1 to H51 or the mixtures M1 to M600, which also contains at least one phosphorescent emitter.

[0147] The present invention also relates to an organic electroluminescent device as described above or preferably described, wherein the light-emitting layer contains at least one phosphorescent emitter in addition to the above-mentioned host materials of the formula (1) and at least one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) and (HH-6), as described above or preferably described, in particular the material combinations M1 to M600.

[0148] The term "phosphorescent emitters" typically encompasses compounds in which light emission occurs through a spin-forbidden transition from an excited state with higher spin multiplicity, i.e., a spin state > 1, for example, through a transition from a triplet state or a state with an even higher spin quantum number, such as a quintet state. Preferably, this refers to a transition from a triplet state.

[0149] Particularly suitable phosphorescent emitters (= triplet emitters) are compounds that, upon suitable excitation, emit light, 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, particularly preferably greater than 56 and less than 80, in particular a metal with this atomic number. 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 or platinum. For the purposes of the present invention, all luminescent compounds containing the above-mentioned metals are considered phosphorescent emitters.

[0150] In general, all phosphorescent complexes as used in the prior art for phosphorescent OLEDs and as known to the person skilled in the art in the field of organic electroluminescent devices are suitable.

[0151] Preferred phosphorescent emitters according to the present invention correspond to the formulas (I), (II), (III), (IV) or (V), where the symbols and indices for these formulas (I), (II), (III), (IV) and (V) have the meaning: R 1 is H or D, R 2 is H, D, F, CN or a branched or linear alkyl group having 1 to 10 C atoms or a partially or fully deuterated branched or linear alkyl group having 1 to 10 C atoms or a cycloalkyl group having 4 to 10 C atoms, which may be partially or fully substituted with deuterium.

[0152] Preferred phosphorescent emitters according to the present invention correspond to the formula (VI), where the symbols and indices for this formula (VI) have the meaning: n+m is 3, n is 1 or 2, m is 2 or 1, X is the same or different at each occurrence, N or CR, R is, on each occurrence, identically or differently, H, D, F, CN or a branched or linear alkyl group having 1 to 10 C atoms or a partially or fully deuterated branched or linear alkyl group having 1 to 10 C atoms or a cycloalkyl group having 4 to 7 C atoms which may be partially or fully substituted with deuterium or an aromatic or heteroaromatic ring system having 5 to 60 ring atoms which may be partially or fully substituted with deuterium and / or a partially or fully deuterated, branched or linear alkyl group having 1 to 10 C atoms.

[0153] In emitters of formula (VI), n is preferably 1 and m is preferably 2.

[0154] In emitters of the formula (VI), one X is preferably selected from N and the other Xs are CR or all Xs, identical or different at each occurrence, are CR.

[0155] In emitters of formula (VI), at least one R is preferably different from H. In emitters of formula (VI), two R are preferably different from H and have one of the meanings otherwise previously given for the emitters of formula (VI).

[0156] A further subject matter of the invention is accordingly an organic electroluminescent device as described above or preferably described, characterized in that the light-emitting layer contains, in addition to the host materials 1 and 2, at least one phosphorescent emitter which corresponds to one of the formulas (I) to (VI), as described above, preferably to the formula (VI).

[0157] Preferred examples of phosphorescent emitters are described in WO2019 / 007867 on pages 120 to 126 in Table 5 and on pages 127 to 129 in Table 6. The emitters are incorporated into the description by this reference.

[0158] Particularly preferred examples of phosphorescent emitters are listed in Table 6 below.

[0159] In the mixtures according to the invention or in the light-emitting layer of the device according to the invention, each mixture selected from the sum of the mixtures M1 to M600 is preferably combined with a compound of the formulas (I) to (VI) or a compound from Table 6.

[0160] The light-emitting layer in the organic electroluminescent device according to the invention containing at least one phosphorescent emitter is preferably an infrared-emitting, yellow, orange, red, green, blue or ultraviolet-emitting layer, particularly preferably a yellow or green-emitting layer and very particularly preferably a green-emitting layer.

[0161] A yellow-emitting layer is understood to be a layer whose photoluminescence maximum lies in the range from 540 to 570 nm. An orange-emitting layer is understood to be a layer whose photoluminescence maximum lies in the range from 570 to 600 nm. A red-emitting layer is understood to be a layer whose photoluminescence maximum lies in the range from 600 to 750 nm. A green-emitting layer is understood to be a layer whose photoluminescence maximum lies in the range from 490 to 540 nm. A blue-emitting layer is understood to be a layer whose photoluminescence maximum lies in the range from 440 to 490 nm.The photoluminescence maximum of the layer is determined by measuring the photoluminescence spectrum of the layer with a layer thickness of 50 nm at room temperature, wherein the layer contains the inventive combination of the host material 1 of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) and the host material 2, consisting of at least one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) and (HH-6), and the corresponding emitter.

[0162] The photoluminescence spectrum of the layer is recorded, for example, using a commercially available photoluminescence spectrometer.

[0163] The photoluminescence spectrum of the selected emitter is usually measured in oxygen-free solution, 10 -5molar, measured at room temperature, and any solvent in which the selected emitter dissolves at the specified concentration is suitable. Particularly suitable solvents are usually toluene or 2-methyl-THF, but also dichloromethane. The measurement is carried out using a commercially available photoluminescence spectrometer. The triplet energy T1 in eV is determined from the photoluminescence spectra of the emitters. First, the peak maximum Plmax. (in nm) of the photoluminescence spectrum is determined. The peak maximum Plmax. (in nm) is then converted to eV according to: E(T1 in eV) = 1240 / E(T1 in nm) = 1240 / PLmax. (in nm).

[0164] Preferred phosphorescent emitters are therefore yellow emitters, preferably of the formulas (I) to (VI) or from Table 6, whose triplet energy T1 is preferably between ~2.3 eV and ~2.1 eV.

[0165] Preferred phosphorescent emitters are therefore green emitters, preferably of the formulas (I) to (VI) or from Table 6, whose triplet energy T1 is preferably between -2.5 eV and -2.3 eV.

[0166] Particularly preferred phosphorescent emitters are accordingly green emitters, preferably of the formulas (I) to (VI) or from Table 6, as described above, whose triplet energy T1 is preferably between -2.5 eV and -2.3 eV.

[0167] Green emitters, preferably of the formulas (I) to (VI) or from Table 6, as described above, are very particularly preferably selected for the mixture according to the invention or the emitting layer according to the invention.

[0168] Fluorescent emitters can also be present in the light-emitting layer of the device according to the invention or in the mixture according to the invention. Preferred fluorescent emitting compounds are selected from the class of arylamines, wherein preferably at least one of the aromatic or heteroaromatic ring systems of the arylamine is a fused ring system, particularly preferably with at least 14 ring atoms. Preferred examples thereof 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 one diarylamino group is bonded directly to one 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 one 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. Further preferred emitting compounds are indenofluorenamines or diamines, benzoindenofluorenamines or diamines, and dibenzoindenofluorenamines or diamines, as well as indenofluorene derivatives with fused aryl groups. Pyrene-arylamines are also preferred. Also preferred are benzoindenofluorene amines, benzofluorene amines, extended benzoindenofluorenes, phenoxazines, and fluorene derivatives linked to furan units or thiophene units. Furthermore, the light-emitting device or the mixture according to the invention can also contain materials that exhibit TADF (thermally activated delayed fluorescence).

[0169] In a further preferred embodiment of the invention, the at least one light-emitting layer of the organic electroluminescent device can have three or four different matrix materials, preferably three different matrix materials. These corresponding mixed-matrix systems can consist of the matrix materials described for host material 1 and host material 2, but they can also contain, as a third or fourth matrix material, for example, in addition to a host material 1 or host material 2, wide-band-gap materials, bipolar host materials, electron-transport materials (ETM), or hole-transport materials (HTM). The mixed-matrix system is preferably optimized for an emitter of the formulas (I) to (VI) or for an emitter of Table 6.

[0170] According to one embodiment of the present invention, the mixture contains no further components, i.e., functional materials, apart from the components of host material 1 and host material 2, as previously described or preferably described. These are material mixtures that are used as such to produce the light-emitting layer. These mixtures are also referred to as premix systems, which are used as the sole material source during the vapor deposition of the host materials for the light-emitting layer and which have a constant mixing ratio during vapor deposition. This allows for the simple and rapid vapor deposition of a layer with a uniform distribution of the components, without the need for precise control of a large number of material sources.

[0171] According to an alternative embodiment of the present invention, the mixture contains, in addition to the components of host material 1 and host material 2, as described above or preferably described, a phosphorescent emitter as described above. With a suitable mixing ratio during vapor deposition, this mixture can also be used as the sole material source.

[0172] Preferred are premix systems consisting of two matrix materials, namely a compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) and a compound of one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6).

[0173] Preferred are premix systems consisting of three matrix materials, namely a compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) and two compounds of one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6).

[0174] The components or constituents of the light-emitting layer of the device according to the invention can thus be processed by vapor deposition or from solution. The material combination of host materials 1 and 2, as described above or preferably described, optionally with the phosphorescent emitter, as described above or preferably described, is provided for this purpose in a formulation containing at least one solvent. Suitable formulations have been described previously.

[0175] The light-emitting layer in the device according to the invention according to the preferred embodiments and the emitting compound preferably contains between 99.9 and 1 vol.%, further preferably between 99 and 10 vol.%, particularly preferably between 98 and 60 vol.%, very particularly preferably between 97 and 80 vol.% of matrix material made of at least one compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) and at least one compound of one of the formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5), (HH-5-A), (HH-5-B), (HH-5-C), (HH-5-D), (HH-5-E) or (HH-6) according to the preferred embodiments, based on the total composition of emitter and matrix material. Accordingly, the light-emitting layer in the device according to the invention preferably contains between 0.1 and 99 vol.%, more preferably between 1 and 90 vol.%, particularly preferably between 2 and 40 vol.%, most preferably between 3 and 20 vol.-% of the emitter based on the total composition of the light-emitting layer consisting of emitter and matrix material. If the compounds are processed from solution, the corresponding amounts in wt.% are preferred instead of the above-mentioned amounts in vol.%.

[0176] The present invention also relates to an organic electroluminescent device as described above or preferably described, wherein the organic layer contains a hole injection layer (HIL) and / or a hole transport layer (HTL), whose hole injecting material and hole transporting material belong to the class of arylamines.

[0177] The sequence of layers in the organic electroluminescent device according to the invention is preferably as follows: Anode / hole injection layer / hole transport layer / emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode.

[0178] This sequence of layers is a preferred sequence.

[0179] It should be noted again that not all of the layers mentioned need to be present and / or that additional layers may be present.

[0180] All materials used in the electron transport layer according to the state of the art can be used as electron transport materials. Particularly suitable are aluminum complexes, for example, Alq3; zirconium complexes, for example, Zrq4; 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.

[0181] The present invention also relates to an organic electroluminescent device as described above or preferably described, wherein the organic layer contains an electron injection layer (EIL) and / or an electron transport layer (ETL) and / or a hole blocking layer, whose electron injecting material and electron transporting material are selected from the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g), as described above or preferably described.

[0182] Suitable cathodes for the device according to the invention include metals with low work functions, metal alloys, or multilayer structures made of different metals, such as alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Yb, Sm, etc.). Alloys made of an alkali or alkaline earth metal and silver, for example, an alloy of magnesium and silver, are also suitable. In multilayer structures, in addition to the metals mentioned, other metals with a relatively high work function, such as Ag or Al, can also be used. Combinations of the 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.Suitable materials for this purpose include alkali metal or alkaline earth metal fluorides, as well as the corresponding oxides or carbonates (e.g., LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.). Lithium quinolinate (LiQ) can also be used. The thickness of this layer is preferably between 0.5 and 5 nm.

[0183] Materials with a high work function are preferred as anodes. 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 / PtO) can also be used. x) may be preferred. For some applications, at least one of the electrodes must be transparent or partially transparent in order 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. Particular preference is given to indium tin oxide (ITO) or indium zinc oxide (IZO). 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 made of ITO and an outer layer made of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.

[0184] The organic electroluminescent device according to the invention is structured, contacted and finally sealed accordingly (depending on the application) during production, since the lifetime of the devices according to the invention is shortened in the presence of water and / or air.

[0185] The manufacture of the device according to the invention is not restricted in this respect. It is possible to coat one or more organic layers, including the light-emitting layer, 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.

[0186] The organic electroluminescent device according to the invention is preferably characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) method or by means of carrier gas sublimation. The materials are then sublimated at a pressure between 10 -5 mbar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured (e.g., BMS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

[0187] Furthermore, the organic electroluminescent device according to the invention is preferably characterized in that one or more organic layers comprising the composition according to the invention are produced from solution, for example by spin coating, or by 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. Soluble host materials 1 and 2 and phosphorescent emitters are required for this purpose. Processing from solution has the advantage that, for example, the light-emitting layer can be applied very easily and cost-effectively. This technique is particularly suitable for the mass production of organic electroluminescent devices.

[0188] Furthermore, hybrid processes are possible, in which, for example, one or more layers are applied from solution and one or more further layers are vapor-deposited.

[0189] These methods are generally known to the person skilled in the art and can be applied to organic electroluminescent devices.

[0190] A further subject of the invention is therefore a method for producing the organic electroluminescent device according to the invention, as described above or preferably described, characterized in that the organic layer, preferably the light-emitting layer, the hole injection layer and / or hole transport layer, is applied by vapor phase deposition, in particular with a sublimation process and / or with an OVPD (Organic Vapor Phase Deposition) process and / or with the aid of carrier gas sublimation, or from solution, in particular by spin coating or with a printing process.

[0191] When manufactured by vapor deposition, there are basically two ways in which the organic layer according to the invention, preferably the light-emitting layer, can be applied or vapor-deposited onto any substrate or the previous layer. Firstly, the materials used can each be placed in a material source and then evaporated from the various material sources ("co-evaporation"). Secondly, the various materials can be premixed ("premixed" systems) and the mixture placed in a single material source, from which it is then vaporized ("premix evaporation"). This allows for the vapor deposition of the light-emitting layer with a uniform distribution of the components in a simple and rapid manner, without the need for precise control of a large number of material sources.

[0192] The following procedures are possible: A method for producing the organic electroluminescent device according to the invention, as described above or preferably described, characterized in that the organic layer, preferably the light-emitting layer, the electron transport layer and / or hole blocking layer, is applied by vapor phase deposition, in particular with a sublimation process and / or with an OVPD (Organic Vapor Phase Deposition) process and / or with the aid of carrier gas sublimation, or from solution, in particular by spin coating or with a printing process.

[0193] A method for producing the organic electroluminescent device according to the invention, as described above or preferably described, characterized in that the light-emitting layer of the organic layer is applied by gas phase deposition, wherein the at least one compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) together with the further materials which form the light-emitting layer are deposited successively or simultaneously from at least two material sources from the gas phase.

[0194] A method for producing the device according to the invention, characterized in that the light-emitting layer of the organic layer is applied by vapor deposition, wherein the at least one compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f) or (1g) is deposited from the vapor phase together with at least one further matrix material as a premix, sequentially or simultaneously with the light-emitting materials selected from the group of phosphorescent emitters, fluorescent emitters and / or emitters which exhibit TADF (thermally activated delayed fluorescence).

[0195] The electronic devices according to the invention, in particular organic electroluminescent devices, are characterized by one or more of the following surprising advantages over the prior art: 1. Electronic devices, in particular organic electroluminescent devices containing compounds according to formula (1) or the preferred embodiments described above and below, in particular as matrix material or as electron-conducting materials, exhibit a very long lifetime. These compounds, in particular, result in low roll-off, i.e., a low drop in the power efficiency of the device at high luminance levels. 2. Electronic devices, in particular organic electroluminescent devices containing compounds of formula (1) or the preferred embodiments described above and below as electron-conducting materials and / or matrix materials, exhibit excellent efficiency. Compounds of the invention according to formula (1) or the preferred embodiments described above and below result in a low operating voltage when used in electronic devices. 3. Electronic devices, in particular organic electroluminescent devices containing compounds according to formula (1) or the preferred embodiments described above and below as electron-conducting materials and / or matrix materials, exhibit low capacitance. This is advantageous for achieving high switching times when used as electroluminescent devices in display screens. 4. The compounds according to the invention according to formula (1) or the preferred embodiments described above and below show a very high stability and lifetime. 5. The compounds according to the invention according to formula (1) or the preferred embodiments described above and below, in particular where A is a structure of formula (3), show very good solubility and evaporation temperatures suitable for premix development (< 350°C, p = 10 -6 mbar), particularly due to the direct proximity of substructures A and C. 6. Using compounds according to formula (1) or the preferred embodiments described above and below, the formation of optical loss channels can be avoided in electronic devices, particularly organic electroluminescent devices. As a result, these devices are characterized by high PL and thus high EL efficiency of emitters and excellent energy transfer from the matrices to dopants. 7. The use of compounds according to formula (1) or the preferred embodiments described above and below in layers of electronic devices, in particular organic electroluminescent devices, leads to a high mobility of the electron conductor structures. 8. Compounds according to formula (1) or the preferred embodiments described above and below have excellent glass film formation. 9. Compounds according to formula (1) or the preferred embodiments described above and below form very good films from solutions. 10. The compounds according to formula (1) or the preferred embodiments described above and below have a deep triplet level T1, which can be in the range of 2.50 eV - 2.90 eV.

[0196] These advantages mentioned above are not accompanied by an excessive deterioration of the other electronic properties.

[0197] It should be noted that variations of the embodiments described in the present invention fall within the scope of this invention. Any feature disclosed in the present invention may, unless explicitly excluded, be replaced by alternative features serving the same, equivalent, or similar purpose. Thus, unless otherwise stated, any feature disclosed in the present invention is to be considered an example of a generic series or an equivalent or similar feature.

[0198] All features of the present invention may be combined with each other in any way, unless certain features and / or steps are mutually exclusive. This applies in particular to preferred features of the present invention. Likewise, features of non-essential combinations may be used separately (and not in combination).

[0199] The teaching of technical action disclosed in the present invention can be abstracted and combined with other examples.

[0200] The invention is explained in more detail by the following examples, without intending to limit it thereby. ExamplesSynthesis examples

[0201] Unless otherwise stated, the following syntheses are carried out under a protective gas atmosphere in dried solvents. a) 2-(Dibenzo[b,d]furan-1-yl)-5-fluoroaniline: 5.7 g (26.9 mmol) of 1-dibenzofuranylboronic acid, 2.4 g (2.07 mmol) of Pd(PPh3)4, and 11.5 g (82.8 mmol) of K2CO3 are dissolved in 250 ml of toluene, 100 ml of H2O, and 20 ml of EtOH. 3.9 g (20.7 mmol) of 2-bromo-5-fluoroaniline is added, and the resulting mixture is heated to 95 °C for 16 hours. After cooling, the solution is treated with 500 ml of saturated aqueous NH4Cl solution and 500 ml of CH2Cl2, and the phases are separated. The organic phase is dried over Na2SO4 and filtered. The filtrate is concentrated in vacuo and then recrystallized. Yield 6.8 g, (24.7 mmol, 92%).

[0202] Analogously, the following connections are made: Educt 1 Educt 2 product yield 1a 72% 2a 80% 3a 77% b) 4-Bromo-2-(dibenzo[b,d]furan-1-yl)-5-fluoroaniline

[0203] A solution of 41 g (150 mmol) of 2-(dibenzo[b,d]furan-1-yl)-5-fluoroaniline in 1000 mL of chloroform was treated portionwise with N-bromosuccinimide (24.7 g, 139 mmol) at 0 °C under exclusion of light and stirred at this temperature for 2 h. The reaction was terminated by adding sodium sulfite solution, and the mixture was stirred for a further 30 min at room temperature. After phase separation, the organic phase was washed with water, and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in toluene and filtered through silica gel. The crude product was then recrystallized from toluene / heptane.

[0204] Yield: 47 g (134 mmol, 91%).

[0205] Analogously, the following connections are made: Educt 1 product yield 54% c) 9-Bromo-10-fluorotriphenyleno[1,12-bcd]furan: 3.5 g (10 mmol) of 4-bromo-2-(dibenzo[b,d]furan-1-yl)-5-fluoroaniline is suspended in 10 mL of distilled water and 10 mL of concentrated HCl (36.5%). The mixture is stirred for 30 minutes under ice-cooling. Then, NaNO2 solution (15 mL, 15 mmol) is added dropwise, and the resulting mixture is stirred at 0 °C for 1 h. The resulting solution is then heated to 95 °C and stirred for a further 1 hour. After cooling to room temperature, the solution is diluted with 400 mL of saturated aqueous Na2CO3 solution and 300 mL of ethyl acetate. The aqueous phase is extracted with ethyl acetate (3 × 200 mL) and combined. The organic phases were washed with brine (400 ml), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography. Yield: 2.9 g (9.4 mmol, 89%).

[0206] Analogously, the following connections are made: Educt 1 product yield 1c 62% 2c 56% 3c 52% d) 2-(10-Fluorotriphenyleno[1,12-bcd]furan-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. 43.8 g (130 mmol) of 9-bromo-10-fluorotriphenyleno[1,12-bcd]furan, 60 g (236 mmol) of bis(pinacolato)diboron, and 35 g of 1,4-dioxane are placed in 800 ml of 1,4-dioxane and inertized with argon for 30 min. Subsequently, 3.5 g (3.8 mmol) of tris(dibenzylideneacetone)dipalladium (97%) and 4 g (14 mmol) of tricyclohexylphosphine are added, and the mixture is stirred under reflux for 24 h. After cooling, the solvent is removed on a rotary evaporator, and the residue is extracted with dichloromethane and water. The combined organic phases are dried over Na2SO4, ethanol (150 ml) is added, and the dichloromethane is removed on a rotary evaporator. The precipitated solid is filtered off with suction and dried in a vacuum drying oven. The crude product is used in the next step without further purification.

[0207] Yield: 31 (80 mmol, 62%), purity 95 % according to 1 H-NMR.

[0208] Analogously, the following connections are made: Educt 1 product yield 1d 59% 2d 51% e) 2-(10-Fluorotriphenyleno[1,12-bcd]furan-9-yl)-4,6-diphenyl-1,3,5-triazine10.4 g (27 mmol) of 2-(10-Fluorotriphenyleno[1,12-bcd]furan-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 7.3 g (27 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 14.14 g (66.61 mmol) of K2CO3 are placed in 200 mL of toluene and 40 ml of water and inertized with argon for 30 min. Then, 301 mg (0.33 mmol) of tris(dibezylideneacetone)dipalladium and 206 mg (0.13 mmol) of triphenylphosphine are added successively, and the reaction mixture is heated to reflux for 18 h. After cooling, the precipitated solid is filtered off with suction and washed with water and ethanol. The crude product is extracted once with toluene and three times with o-xylene under hot conditions, and finally sublimed under high vacuum. Yield: 9.4 g (19.1 mmol, 71%).

[0209] The following compounds can be prepared analogously. S-Phos or P(o-tol)3 with Pd2(dba)3 or Pd(OAc)2 can also be used as a catalyst system. Column chromatography, hot extraction, or recrystallization can be used for purification. Common solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, and 1,4-dioxane can be used for recrystallization or hot extraction. High-boiling solvents such as dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, etc., can be used for recrystallization. Educt 1 Educt 2 product yield 1e 63% 2e 70% 3e 76% 4e 62% 5e 64% 6e 60% 7e 61% 8e 63% 9e 54% 10e 64% 11e 65% 12e 67% 13e 56% 14e 59% 15e 57% 16e 53% 17e 54% f) 9-(10-(4,6-diphenyl-1,3,5-triazin-2-yl)triphenyleno[1,12-bcd]furan-9-yl)-9H-carbazole. 47 g (96 mmol) of 2-(10-fluorotriphenyleno[1,12-bcd]furan-9-yl)-4,6-diphenyl-1,3,5-triazine, 30 g (179 mmol) of carbazole, and 54 g (166 mmol) of cesium carbonate are suspended in 1500 mL of N,N-dimethylformamide under argenic suspension, and the reaction mixture is heated under reflux at 150°C for 40 h. The reaction mixture is cooled to room temperature, and 1500 mL of water is added. The precipitated solid is filtered off, washed with 300 mL of ethanol, and recrystallized several times from xylene. After hot filtration through Alox and final sublimation in high vacuum (p = 5 × 10 -7 mbar), the purified product (purity 99.9%) is obtained as a colorless solid; 49.6 g (77.7 mmol; 81%).

[0210] Analogously, the following connections are made: Educt 1 Educt 2 product yield 1f 72% 2f 77% 3f 73% 4f 72% 5f 79% 6f 78% 7f 72%% 8f 67% 9f 65% 10f 71% 11f 70% 12f 67% 13f 74%% 14f 61% 15f 68% 16f 70% 17f 64% 18f 61% 19f 62% 20f 62% 21f 63% 22f 61% 23f 62% 24f 61% 25f g) 9-(10-(4,6-diphenyl-1,3,5-triazin-2-yl)triphenyleno[1,12-bcd]furan-9-yl)-9H-carbazole-d26 33.6 g (48.0 mmol, 1.00 eq) of 9-(10-(4,6-diphenyl-1,3,5-triazin-2-yl)triphenyleno[1,12-bcd]furan-9-yl)-9H-carbazole is suspended in 640 mL (120 eq) of toluene-d8. 16.6 mL (6.00 eq) of trifluoromethanesulfonic acid is added to this mixture while cooling. The reaction mixture is stirred at ambient temperature for 6 hours. Subsequently, 120 mL (130 eq) of deuterium oxide [CAS 7789-20-0] is added dropwise at 0°C. After neutralization with a potassium sulfate solution, the mixture is extracted with toluene, and the combined organic phases are washed with brine and dried over sodium sulfate. After filtration, the solvent is removed under reduced pressure. 24 g (36 mmol, 70% of theory) of the product shown above in a mixture with portions of H / D isotopomers and H / D isotopologues are obtained after chromatographic purification and finally concentrated under high vacuum (p = 5 × 10 -7 mbar) sublimated (purity 99.9%).

[0211] Analogously, the following connections are made: Educt 1 product yield 1e 67% Production of OLEDs

[0212] The following examples Ex1 to Ex9 (see Tables 7 and 8) present various OLEDs. Examples Ex1 to Ex9 describe OLEDs according to the invention.

[0213] The substrates used for the OLEDs shown in Table 7 are glass plates coated with 50 nm thick structured ITO (indium tin oxide). The exact structure of the OLEDs can be found in Table 7. The materials required for the fabrication of the OLEDs are shown in Table 8, unless previously described.

[0214] All materials are thermally evaporated in a vacuum chamber. The emission layer always consists of at least one matrix material (also called host material) and an emitting dopant (dopant, emitter), which is mixed into the matrix material(s) by co-evaporation in a specific volume fraction. A specification such as E6:H36:TEG3 (42%:50%:8%) 40nm means that the material E6 is present in a volume fraction of 42% as host material 1, the compound H36 is present as host material 2 in a volume fraction of 50%, and TEG3 is present in a volume fraction of 8% in a 40nm thick layer. Similarly, the hole injection layer (HIL) and the electron transport layer (ETL), for example, can also consist of a mixture of two materials.

[0215] The OLEDs are characterized as standard. For this purpose, the electroluminescence spectra and current-voltage-luminance (IUL) curves are measured, from which the EQE is calculated. The calculation assumes a Lambertian radiation pattern. The voltage required for a current density of 10 mA / cm 2 required is referred to here as U10. EQE10 denotes the external quantum efficiency at a current density of 10 mA / cm 2 .

[0216] The lifetime LT90 is defined as the time after which the luminance when operated at a constant current density j0 in mA / cm 2 from a starting luminance L0 (in cd / m 2 ) drops to 90% of this starting luminance. Use of mixtures according to the invention in OLEDs

[0217] The compounds or material combinations according to the invention can be used in the emission layer in phosphorescent green OLEDs. Table 7: Structure of the OLEDs e.g. HILDicke HTL thickness EBLThickness EML thickness HBLThickness ETL thickness EILThickness Ex1 SpMA1:PD1(95%:5%)20nm SpMA150nm SpMA220nm E6:H36:TEG3(42%:50%:8%)40nm AT15nm ST1:LiQ(50%:50%)30nm LiQ1nm Ex2 SpMA1:PD1(95%:5%)20nm SpMA150nm SpMA220nm E1:H38:TEG2(42%:50%:8%)40nm AT15nm ST1:LiQ(50%:50%)30nm LiQ1nm Ex3 SpMA1:PD1(95%:5%)20nm SpMA150nm SpMA220nm E9:H38:TEG2(42%:50%:8%)40nm AT15nm ST1:LiQ(50%:50%)30nm LiQ1nm Ex4 SpMA1:PD1(95%:5%)20nm SpMA150nm SpMA220nm E9:H11:TEG2(42%:50%:8%)40nm AT15nm ST1:LiQ(50%:50%)30nm LiQ1nm Ex5 SpMA1:PD1(95%:5%)20nm SpMA150nm SpMA220nm E9:H52:TEG2(27%:65%:8%)40nm AT15nm ST1:LiQ(50%:50%)30nm LiQ1nm Ex6 SpMA1:PD1(95%:5%)20nm SpMA150nm SpMA220nm E13:H38:TEG2(42%:50%:8%)40nm AT15nm ST1:LiQ(50%:50%)30nm LiQ1nm Ex7 SpMA1:PD1(95%:5%)20nm SpMA150nm SpMA220nm E13:H11:TEG2(42%:50%:8%)40nm AT15nm ST1:LiQ(50%:50%)30nm LiQ1nm Ex8 SpMA1:PD1(95%:5%)20nm SpMA150nm SpMA220nm E2:H38:TEG2(52%:40%:8%)40nm AT15nm ST1:LiQ(50%:50%)30nm LiQ1nm Ex9 SpMA1:PD1(95%:5%)20nm SpMA150nm SpMA220nm E2:H11:TEG2(42%:50%:8%)40nm AT15nm ST1:LiQ(50%:50%)30nm LiQ1nm Table 8: Materials used, unless previously described PD1 (CAS Reg. No. 1224447-88-4) SpMA1 SpMA2 AT1 ST1 LiQ TEG2 TEG3 H52

[0218] The compounds of the invention are suitable for use as matrix material, electron-transport material, or hole-blocking material, particularly in a phosphorescent OLED. The OLEDs described above exhibit a good lifetime and low capacitance. QUOTES CONTAINED IN THE DESCRIPTION

[0000] This list of documents submitted by the applicant was generated automatically and is included solely for the convenience of the reader. This list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions. Cited patent literature

[0000] WO 11137157A1

[0004] WO 12048781 A1

[0004] WO 22038066 A1

[0004] CN 112225727 A

[0004] WO 22148717 A1

[0004] CN 112961144 A

[0004] CN 112961145 A

[0004] CN 113429334 A

[0004] CN 114409589 A

[0004] KR 2016041014

[0080] WO 2017 / 122988

[0080] KR 202005282

[0080] KR 101978651

[0080] WO 2018 / 110887

[0080] US 7,294,849

[0105] WO 2021 / 180614

[0125] WO 2021 / 180614 A1

[0125] WO 2019 / 229011 A1

[0129] WO 2021 / 180625 A1

[0130] KR 20230034896 A

[0131] KR 20230154750 A

[0132] US 2023172065 A

[0133] Zitierte Nicht-Patentliteratur

[0000] Bulletin of the Chemical Society of Japan, 2021, 94(2), 600-605 oder Asian Journal of Organic Chemistry, 2017, 6(8), 1063-1071

[0080] M. S. Arnold et al., Appl. Phys. Lett. 2008, 92, 053301

[0186]

Claims

[1] Compounds of formula (1), ABC formula (1), where B means a structure of formula (2), A means a structure of formulas (3) or (4) and C means a structure of formulas (5), (6), (7) or (8), the following applies to the symbols and indices used: Z is O or S; a, b, c, d, e and f represent the respective linking points to formulas (3), (4), (5), (6), (7) or (8); X is independent of each other CH, CR 1 or N, where at least one means XN; V is O or S; Y is independently N, C, CH or CR in each case. 1 , where at least one Y represents N and where it is excluded that two adjacent Ys simultaneously represent N; In each instance, R# is independently an aryl group with 6 to 20 carbon atoms, linked to one or more R substituents. 0 may be substituted; m is independent in each instance of 0, 1 or 2; * is the linking point at a, b, c, d or f of formula (2); # is the linking point at a, b, c, d or f of formula (2); R a , R b , R c and R d represent a monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution, or no substitution; R a , R b , R c and R d are D at every occurrence; Ar1, Ar2 and Ar3 each independently form an aryl or heteroaryl group with 5 to 40 ring atoms, which is connected to one or more R substituents. 0 may be substituted; R 1 In each occurrence, independently of one another, D, CN, F, or an aryl or heteroaryl group with 5 to 40 ring atoms, which is connected to one or more R residues 0 may be substituted; R0 is selected from the group consisting of D, F, Cl, Br, I, CN, NO2, C(=O)R in each occurrence, either the same or different. 2 , P(=O)(Ar)2, P(Ar)2, B(Ar)2, Si(Ar)3, Si(R 2 )3, a straight-chain alkyl, alkoxy or thioalkyl group with 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy or thioalkyl group with 3 to 20 carbon atoms, or an alkenyl group with 2 to 20 R 2 C atoms, each with one or more R groups 2 can be substituted, with one or more non-adjacent CH2 groups being replaced by R 2 C=CR 2 , Si(R 2 )2, C=O, C=S, C=NR 2 , P(=O)(R 2 ), SO, SO2, NR 2 , O, S or CONR 2 can be replaced and wherein one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO2, an aryl or heteroaryl group with 5 to 40 ring atoms, which is joined with one or more R groups 2may be substituted, an aryloxy or heteroaryloxy group with 5 to 40 ring atoms, which is joined with one or more R residues 2 may be substituted, or an aralkyl or heteroaralkyl group with 5 to 40 ring atoms, which is joined with one or more R groups 2 may be substituted; is selected in each occurrence, either the same or different, from the group consisting of D, F, CN, Si(aryl)3, a straight-chain alkyl group with 1 to 20 C atoms, or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein one or more non-adjacent CH2 groups may be replaced by O or S, and wherein one or more H atoms may be replaced by D, F, or CN. Aryl is an unsubstituted, partially or completely deuterated aryl group with 6 to 40 carbon atoms. with the condition that the structure of formulas (3) or (4) with the linking point * and the structure of formulas (5), (6), (7) or (8) with the linking point # in formula (2) are directly adjacent. [2] Compounds according to claim 1, wherein the symbol ZO means. [3] Compounds according to claim 1 or 2, wherein X represents N in each case. [4] Compounds according to one or more of claims 1 to 3, wherein two Y represent N. [5] Compounds according to one or more of claims 1 to 4, which are partially or completely deuterated. [6] Mixture comprising at least one compound of formula (1) according to one or more of claims 1 to 5 and at least one further compound selected from the group consisting of matrix materials, phosphorescent emitters, fluorescent emitters and / or emitters exhibiting TADF (thermally activated delayed fluorescence). [7] Use of at least one compound of formula (1) according to one or more of claims 1 to 5 in an organic electronic device. [8] Organic electronic device comprising an anode, a cathode and at least one organic layer, containing at least one compound of formula (1) according to one or more of claims 1 to 5. [9] Organic electronic device according to claim 8, wherein the electronic device is an organic integrated circuit (OlCs), an organic field-effect transistor (OFET), an organic thin-film transistor (OTFT), an organic electroluminescent device, an organic solar cell (OSC), an organic optical detector or an organic photoreceptor. [10] Organic electronic device according to claim 8 or 9, wherein the organic layer contains at least one light-emitting layer, one hole-transporting layer, one hole-injecting layer or one electron-blocking layer, which contains at least one compound according to any one of claims 1 to 5. [11] Organic electronic device according to one or more of claims 8 to 10, characterized by , that the light-emitting layer contains at least one compound of formula (1) according to any one of claims 1 to 5. [12] Organic electronic device according to one or more of claims 8 to 11, characterized by , that the light-emitting layer contains at least one further matrix material in addition to the compound of formula (1) according to any one of claims 1 to 5. [13] Organic electroluminescent device according to claim 12, characterized by, that the further matrix material of a compound or several of the compounds of formulas (HH-1), (HH-2), (HH-3), (HH-4), (HH-5) or (HH-6) contains matrix material 2, the following applies to the symbols and indices used: A 1 is C(R 7 )2, NR 7 , O or S; L is a bond, O, S, C(R 7 )2 or NR 7 ; A is, independently of each other, a group of formula (HH-4-1) or (HH-4-2) in each occurrence, X2 is the same or different in each occurrence CH, CR 6 or N, where a maximum of 2 symbols can mean X2 N; * indicates the binding site to the formula (HH-4); U 1 , U 2 are, when they occur, a bond, O, S, C(R 7 )2 or NR 7 ; R 6is the same or different in each occurrence D, F, CN, a straight-chain alkyl group with 1 to 20 C atoms or an alkenyl or alkynyl group with 2 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each linked to one or more R groups 7 can be substituted and where one or more non-adjacent CH2 groups are replaced by Si(R 7 )2, C=O, NR 7 , O, S or CONR 7 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, each of which is replaced by one or more R groups 7 can be substituted; in this case, two residues R can be involved. 6 also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system together; Ar5, whether the same or different, independently represents an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which is coupled with one or more R groups. 7 may be substituted; R 7 is the same or different in each occurrence D, F, Cl, Br, I, N(R 8 )2, CN, NO2, OR 8, SR B , Si(R 1 )3, B(OR 8 )2, C(=O)R 8 , P(=O)(R 8 )2, S(=O)R 8 , S(=O)2R 8 , OSO2R 8 , a straight-chain alkyl group with 1 to 20 carbon atoms, or an alkenyl or alkynyl group with 2 to 20 carbon atoms, or a branched or cyclic alkyl group with 3 to 20 carbon atoms, wherein the alkyl, alkenyl, or alkynyl group is each linked to one or more R groups 8 can be substituted, with one or more non-adjacent CH2 groups being replaced by Si(R 8 )2, C=O, NR 8 , O, S or CONR 8can be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which is replaced by one or more R groups 8 can be substituted, where R 8 does not mean H; thereby R 8 Can two or more residues R 7 together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system, preferably the R residues form 7 no such ring system; is the same or different H, D, F or an aliphatic, aromatic or heteroaromatic organic residue, in particular a hydrocarbon residue, with 1 to 20 C atoms, in which one or more H atoms may also be replaced by D or F; c, c1, c2 each independently mean 0 or 1 for each occurrence, where the sum of the indices for each occurrence c+c1+c2 = 1; d, d1, d2 each independently mean 0 or 1 for each occurrence, where the sum of the indices for each occurrence d+d1+d2 = 1; q, q1, q2 each independently mean 0, 1, 2, 3 or 4 in every occurrence; s is either the same or different in each occurrence: 0, 1, 2, 3 or 4; t is either the same or different (0, 1, 2, or 3) for each occurrence; u is either the same or different (0, 1 or 2) in each occurrence; u1 and u2 each independently represent 0 or 1 on every occurrence, where the sum u1 + u2 = 1; and v is 0, 1, 2 or 3. [14] Organic electronic device according to one or more of claims 8 to 13, characterized by that the light-emitting layer contains a phosphorescent emitter. [15] Organic electronic device according to one or more of claims 8 to 14, characterized bythat it is an organic electroluminescent device selected from the organic light-emitting transistors (OLETs), organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers) and organic light-emitting diodes (OLEDs).