Materials for electronic devices

Abstract

The present invention relates to compounds that are suitable for use in electronic devices, and to electronic devices, more particularly organic electroluminescent devices, containing these compounds.

Description

[0001] Materials for electronic devices The present invention relates to materials for use in electronic devices, in particular in organic electroluminescent devices, and to electronic devices, in particular organic electroluminescent devices containing these materials. Electronic devices containing organic, organometallic and / or polymeric semiconductors are becoming increasingly important, and are used in many commercial products for reasons of cost and due to their performance. Examples include organic-based charge transport materials (e.g., triarylamine-based hole transporters) in copiers, organic or polymeric light-emitting diodes (OLEDs or PLEDs) in indicators and display devices, or organic photoreceptors in copiers.Organic solar cells (O-SCs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic switching elements (O-ICs), organic optical amplifiers, and organic laser diodes (O-lasers) are at an advanced stage of development and may become very important in the future. Electronic devices within the meaning of this invention are understood to be organic electronic devices that contain organic semiconductor materials as functional materials. In particular, the electronic devices represent electroluminescent devices such as OLEDs. The structure of OLEDs, in which organic compounds are used as functional materials, is known to those skilled in the art. In general, OLEDs are understood to be electronic devices that have one or more layers comprising organic compounds and that emit light when a voltage is applied.In electronic devices, especially OLEDs, there is a great need to improve performance, particularly lifetime, efficiency, and operating voltage. No satisfactory solution has yet been found for these aspects. Electronic devices typically comprise a cathode, an anode, and at least one functional, preferably emitting layer. In addition to these layers, they may contain further layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, and / or charge generation layers. The hole transport layers and electron transport layers have a major influence on the performance of electronic devices.The object of the present invention is to provide compounds which are suitable for use in an electronic device, in particular an OLED, in particular as material for hole-transport layers or material for electron-transport layers, and which lead to good properties there. Surprisingly, it has been found that certain triptycenes, described in more detail below, achieve this object and are well suited for use in electronic devices, in particular OLEDs. The OLEDs in particular have a long lifetime, high efficiency and a low operating voltage. These compounds and electronic devices, in particular organic electroluminescent devices, which contain these compounds, therefore form the subject matter of the present invention. The subject matter of the present invention is a compound according to one of the formulas (1) or (2).

[0002] where the symbols used are: Ar 1 , Ar 2 are, identically or differently at each occurrence, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R, where Ar 1 and / or Ar 2 can each be linked to R' via a radical R or a single bond; A 1 , A 2 are, identically or differently at each occurrence, a bivalent alkylene group having 1 to 4 carbon atoms, a bivalent alkenylene group having 2 to 4 carbon atoms or a bivalent arylene or heteroarylene group having 5 to 60 ring atoms, where the alkylene, alkenylene, arylene or heteroarylene groups may be substituted by one or more groups R. R' is, identically or differently at each occurrence, H, D, F, Cl, Br, I, OAr', SAr', B(R 1 )2, B(OR 1)2, CHO, C(=O)R, CR=C(R)2, CN, C(=O)OR, C(=O)NR, Si(R)3, NO2, P(=O)(R)2, OSO2R, OR, S(=O)R, S(=O)2R, SR, 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 may each be substituted by one or more radicals R, where one or more non-adjacent CH2 groups are substituted by -RC=CR-, -C≡C-, Si(R)2, NR, CONR, C=O, C=S, -C(=O)O-, P(=O)(R), -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more radicals R, where two or more radicals R may together form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more radicals R 1may be substituted; R is, identically or differently at each occurrence, H, D, F, Cl, Br, I, N(Ar')2, N(R 1 )2, OAr', SAr', B(R 1 )2, B(OR 1 )2, CHO, C(=O)R 1 , CR 1 =C(R 1 )2, CN, C(=O)OR 1 , C(=O)NR 1 , Si(R 1 )3, NO2, P(R 1 )2, P(=O)(R 1 )2, OSO2R 1 , OR 1 , S(=O)R 1 , S(=O)2R 1 , SR 1 , 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 1 may be substituted, with one or more non-adjacent CH2 groups being replaced by -R 1 C=CR 1 -, -C≡C-, Si(R 1 )2, NR 1 , CONR 1 , C=O, C=S, -C(=O)O-, P(=O)(R 1), -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, each substituted by one or more radicals R 1 may be substituted, where two or more radicals R bonded to the same cycle or the same carbon atom can form with each other and / or with R' an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system which can be substituted with one or more radicals R 1 may be substituted; Ar' is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is substituted by one or more radicals R 1 may be substituted; R 1 is the same or different at each occurrence H, D, F, I, B(R 2 )2, B(OR 2 )2, N(R 2 )2, CHO, C(=O)R 2 , CR 2 =C(R 2)2, CN, C(=O)OR 2 , Si(R 2 )3, NO2, P(R 2 )2, P(=O)(R 2 )2, OSO2R 2 , SR 2 , OR 2 , S(=O)R 2 , S(=O)2R 2 , 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 2 and wherein one or more CH2 groups in the above-mentioned groups are substituted by -R 2 C=CR 2 -, -C≡C-, Si(R 2 )2, C=O, C=S, -C(=O)O-, NR 2 , CONR 2 , P(=O)(R 2), -O-, -S-, SO or SO2 and wherein one or more H atoms in the above-mentioned groups may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, each substituted by one or more radicals R 2 may be substituted, where two or more radicals R 1 can form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R 2 is, identically or differently at each occurrence, H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which one or more H atoms may be replaced by D or F; two or more substituents R 2be linked together to form a ring. An aryl group within the meaning of this invention contains 6 to 40 C atoms; a heteroaryl group within the meaning of this invention contains 5 to 40 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 or heteroaryl group is understood to be either a simple aromatic cycle, i.e. benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a condensed (fused) aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatics linked to one another by a single bond, such as biphenyl, are not referred to as aryl or heteroaryl groups, but as an aromatic ring system.An aromatic ring system within the meaning of this invention contains 6 to 60 C atoms, preferably 6 to 40 C atoms in the ring system. A heteroaromatic ring system within the meaning of this invention contains 1 to 60 C atoms, preferably 1 to 40 C atoms and at least one heteroatom in the ring system, 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 aromatic or heteroaromatic ring system within the meaning of this invention is to be understood as a system which does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups can also be linked by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as a C, N or O atom or carbonyl group. This also includes systems in which two or more aryl orHeteroaryl groups are directly linked to one another, such as, for example, biphenyl, terphenyl, bipyridine, or phenylpyridine. For example, systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc. are also to be understood as aromatic ring systems within the meaning of this invention, as are systems in which two or more aryl groups are linked, for example, by a linear or cyclic alkyl group or by a silyl group. Preferred aromatic or heteroaromatic ring systems are simple aryl or heteroaryl groups, as well as groups in which two or more aryl or heteroaryl groups are directly linked to one another, for example biphenyl, terphenyl, quaterphenyl, or bipyridine, as well as fluorene or spirobifluorene. An electron-rich heteroaromatic ring system is characterized by the fact that it is a heteroaromatic ring system that does not contain any electron-poor heteroaryl groups.An electron-poor heteroaryl group is a six-membered ring heteroaryl group with at least one nitrogen atom or a five-membered ring heteroaryl group with at least two heteroatoms, one of which is a nitrogen atom and the other oxygen, sulfur, or a substituted nitrogen atom, to which further aryl or heteroaryl groups may be fused. In contrast, electron-rich heteroaryl groups are five-membered ring heteroaryl groups with exactly one heteroatom selected from oxygen, sulfur, or substituted nitrogen, to which further aryl groups and / or further electron-rich five-membered ring heteroaryl groups may be fused. Examples of electron-rich heteroaryl groups are pyrrole, furan, thiophene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, or indenocarbazole. An electron-rich heteroaryl group is also referred to as an electron-rich heteroaromatic radical.An electron-poor heteroaromatic ring system is characterized in that it contains at least one electron-poor heteroaryl group, and particularly preferably no electron-rich heteroaryl groups. In the context of the present invention, the term alkyl group is used as a generic term for both linear or branched alkyl groups and cyclic alkyl groups. Analogously, the terms alkenyl group and alkynyl group are used as generic terms for both linear or branched alkenyl or alkynyl groups, as well as for cyclic alkenyl or alkynyl groups. A cyclic alkyl, alkoxy or thioalkoxy group in the sense of this invention is understood to mean a monocyclic, bicyclic or polycyclic group. The term “bivalent” in a bivalent alkylene, alkenylene, arylene or heteroarylene group, as used for A. 1 and A 2are defined, is intended to clarify that these groups are each bonded to the two explicitly drawn carbon atoms in formula (1) and formula (2), respectively. As in the definition of A 1 or A 2listed, these groups may still be substituted by one or more radicals R. Even if such substitution with R is present, these groups are still referred to as bivalent groups in the sense of the present invention. In the context of the present invention, an aliphatic hydrocarbon radical or an alkyl group or an alkenyl or alkynyl group which may contain 1 to 40 C atoms and in which individual H atoms or CH2 groups may be substituted by the above-mentioned groups, preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 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, cyclooctyl, 2-ethylhexyl, 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 und 1-(n-Decyl)-cyclohex-1-yl, Ethenyl, Propenyl, Butenyl, Pentenyl, Cyclopentenyl, Hexenyl, Cyclohexenyl, Heptenyl, Cycloheptenyl, Octenyl, Cyclooctenyl, Cyclooctadienyl, Ethinyl, Propinyl, Butinyl, Pentinyl, Hexinyl, Heptinyl oder Octinyl verstanden. Unter einer Alkoxygruppe OR, 1mit 1 bis 40 C-Atomen werden bevorzugt Methoxy, Trifluormethoxy, Ethoxy, n-Propoxy, i-Propoxy, n-Butoxy, i-Butoxy, s-Butoxy, t-Butoxy, n- Pentoxy, s-Pentoxy, 2-Methylbutoxy, n-Hexoxy, Cyclohexyloxy, n-Heptoxy, Cycloheptyloxy, n-Octyloxy, Cyclooctyloxy, 2-Ethylhexyloxy, Pentafluor- ethoxy und 2,2,2-Trifluorethoxy verstanden. Unter einer Thioalkylgruppe SR 1with 1 to 40 carbon atoms are in particular methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, n-pentylthio, s-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, Cyclo-heptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, Cycloheptenylthio, Octenylthio, Cyclooctenylthio, Ethynylthio, Propynylthio, Butynylthio, Pentinylthio, Hexynylthio, heptynylthio, or octynylthio. In general, alkyl, alkoxy, or thioalkyl groups according to the present invention can be straight-chain, branched, or cyclic, where one or more non-adjacent CH2 groups can be replaced by the above-mentioned groups; furthermore, one or more H atoms can be replaced by D, F, Cl, Br, I, CN, or NO2, preferably F, Cl, or CN.particularly preferably F or CN. An aromatic or heteroaromatic ring system with 5 - 60 aromatic ring atoms, preferably 5 - 40 aromatic ring atoms, which may also be substituted by the above-mentioned radicals or a hydrocarbon radical and which may be linked to the aromatic or heteroaromatic ring via any desired positions, is understood to mean, in particular, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, cis- or trans-monobenzoindenofluorene, cis- or trans- Dibenzoindenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene,Isobenzothiophen, Dibenzothiophen, Pyrrol, Indol, Isoindol, Carba- zol, Pyridin, Chinolin, Isochinolin, Acridin, Phenanthridin, Benzo-5,6-chino- lin, Benzo-6,7-chinolin, Benzo-7,8-chinolin, Phenothiazin, Phenoxazin, Pyrazol, Indazol, Imidazol, Benzimidazol, Naphthimidazol, Phenanthrimi- dazol, Pyridimidazol, Pyrazinimidazol, Chinoxalinimidazol, Oxazol, Benz- oxazol, Naphthoxazol, Anthroxazol, Phenanthroxazol, Isoxazol, 1,2- Thiazol, 1,3-Thiazol, Benzothiazol, Pyridazin, Hexaazatriphenylen, Benzo- pyridazin, Pyrimidin, Benzpyrimidin, Chinoxalin, 1,5-Diazaanthracen, 2,7- Diazapyren, 2,3-Diazapyren, 1,6-Diazapyren, 1,8-Diazapyren, 4,5-Diaza- pyren, 4,5,9,10-Tetraazaperylen, Pyrazin, Phenazin, Phenoxazin, Pheno- thiazin, Fluorubin, Naphthyridin, Azacarbazol, Benzocarbolin, Phenan- throlin, 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-Thia- diazol, 1,2,5-Thiadiazol, 1,3,4-Thiadiazol, 1,3,5-Triazin,1,2,4-Triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine, and benzothiadiazole, or groups derived from combinations of these systems. The phrase "two or more residues can form a ring system" is understood, for the purposes of this description, to mean, among other things, that the two residues are linked by a chemical bond with the formal elimination of two hydrogen atoms. This is illustrated by the following scheme: Furthermore, the above formulation should also be understood to mean that if one of the two residues represents hydrogen, the second residue binds to the position to which the hydrogen atom was bonded, forming a ring. This is illustrated by the following scheme: In a preferred embodiment, the compound is a compound of formula (3) or (4):

[0003] where the symbols used have the meanings given above for formula (1) and additionally: Ar 3 is, identically or differently at each occurrence, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R; m, n are, identically or differently at each occurrence, 0 or 1; Y, Z are, identically or differently at each occurrence, a single bond, BR, BAr', C=O, C(R)2, -RC=CR-, o-arylene, NR, NAr', PR, SO2, SiR2, SiAr'2, P(O)R, P(O)Ar', O or S. In a preferred embodiment, A 1 and A 2identical or different at each occurrence for CR2, -CR2CR2-, -CR2CR2CR2-, CR=CR-, o-arylene or o-heteroarylene, preferably for CR2, -CR2CR2-, o-arylene or o-heteroarylene, where the o-arylene or o-heteroarylene groups may be substituted by one or more radicals R. Further preferred embodiments of the invention are shown by formulas (5) and (6): where the symbols used have the meanings given above for formula (3) or formula (4) and additionally: X is identical or different at each occurrence and is C when Z or Y is bonded there, CR, CH, CD or N, with the proviso that a maximum of three groups X per cycle represent N; Preferred embodiments of formulas (5) and (6) are shown by formulas (5-1) to (5-4) and (6-1) to (6-4):

[0004] where the symbols used have the meanings given above for formula (5) or formula (6). Preferred embodiments of formula (5) or (6) are shown by formulas (7-1) to (7-4), (8-1) to (8-4), (9-1) to (9-4), (10-1) to (10-4), (11-1) to (11-4) and (12-1) to (12-4):

[0005]

[0006] where the symbols used have the meanings given above for formula (5) or formula (6) and additionally: X is identical or different on each occurrence and is CR, CH, CD or N, with the proviso that a maximum of three X groups per cycle represent N; Q is identical or different on each occurrence and is CH, CD or CR. Further preferred embodiments are shown by the following formulas (7-1-1) to (7-4-1), (7-1-2) to (7-4-2), (8-1-1) to (8-4-1), (8-1-2) to (8-4-2), (9-1-1) to (9-4-1), (9-1-2) to (9-4-2),

[0007]

[0008]

[0009]

[0010] where the symbols used have the meanings given above for formulas (7-1) to (7-4). In a preferred embodiment, X is, identically or differently at each occurrence, CH, CD, CF, or N, with the proviso that a maximum of three X groups per cycle represent N, where the N groups are not adjacent. Preferably, a maximum of two X groups represent N, more preferably a maximum of one X group represents N, and most preferably, no X group represents N.Further preferred embodiments show the following formulas (7-1-1-1) to (7-1-1-8), (7-1-2-1) to (7-1-2-8), (7-2-1-1) to (7-2-1-8), (7-2-2-1) to (7-2-2-8), (7-3-1-1) to (7-3-1-8), (7-3-2-1) to (7-3-2-8), (7-4-1-1) to (7-4-1-8), (7-4-2-1) to (7-4-2-8), (8-1-1-1) to (8-1-1-8), (8-1-2-1) to (8-1-2-8), (8-2-1-1) to (8-2-1-8), (8-2-2-1) to (8-2-2-8), (8-3-1-1) to (8-3-1-8), (8-3-2-1) to (8-3-2-8), (8-4-1-1) to (8-4-1-8), (8-4-2-1) to (8-4-2-8), (9-1-1-1) to (9-1-1-8), (9-1-2-1) to (9-1-2-8), (9-2-1-1) to (9-2-1-8), (9-2-2-1) to (9-2-2-8), (9-3-1-1) to (9-3-1-8), (9-3-2-1) to (9-3-2-8), (9-4-1-1) to (9-4-1-8), (9-4-2-1) to (9-4-2-8), (10-1-1) to (10-1-8), (10-2-1) to (10-2- 8), (10-3-1) to (10-3-8), (10-4-1) to (10-4-8), (11-1-1) to (11-1-8), (11-2- 1) to (11-2-8), (11-3-1) to (11-3-8), (11-4-1) to (11-4-8), (12-1-1) to (12- 1-8), (12-2-1) to (12-2-8), (12-3-1) to (12-3-8), (12-4-1) to (12-4-8):.

[0011]

[0012] where the symbols used have the meanings given above for formulas (7-1) to (7-4), with the additional following: X 1is, at each occurrence, the same or different CH, CD, CF or N, with the proviso that a maximum of three groups X 1 per cycle represents N; q, p are the same or different at each occurrence and, depending on the substitutable positions on the respective cycle, are 0, 1, 2, 3, 4 or 5; Y 1 is, at each occurrence, the same or different, BR, BAr', C=O, C(R)2, -RC=CR-, o-arylene, NR, NAr', PR, SO2, SiR2, SiAr'2, P(O)R, P(O)Ar', O or S; Ar 4 is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is substituted by one or more radicals R 1 may be substituted; In a preferred embodiment, X is 1 at each occurrence, the same or different CH, CD, CF or N, with the proviso that a maximum of three groups X 1per cycle represent N, where the N are not adjacent. The maximum value of p+q for each cycle is determined by the substitutable positions. For example, if a ring system is attached to this cycle via Y 1 condensed, this system makes two positions no longer accessible for further substitution. The positions marked Y in the formulas 1 The condensable systems can be condensed in any way to adjacent carbon atoms of the respective rings to form a five-membered ring. Together with the ring, an aromatic or heteroaromatic system is then formed. In a preferred embodiment, Y 1on each occurrence, identically or differently, BR, BAr', C=O, C(R)2, NR, NAr', PR, SO2, SiR2, SiAr'2, P(O)R, P(O)Ar', O or S, particularly preferably BAr', C=O, C(R)2, NAr', PR, SO2, SiR2, SiAr'2, P(O)Ar', O or S, in particular BAr', C=O, C(R)2, NAr', PR, SO2, SiR2, SiAr'2, P(O)R, P(O)Ar', O or S. In a preferred embodiment, p is 0, 1 or 2, preferably 0 or 1. In a preferred embodiment, p is 0, 1 or 2, preferably 0 or 1, while R, if present, does not represent an aromatic or heteroaromatic ring system, preferably R is then identically or differently on each occurrence and represents H, D, F, CN or a Straight-chain alkyl group with 1 to 20 carbon atoms. In addition to the substituents, the suitability of the compound for different uses can be controlled by the presence or absence of Y or Z. In a preferred embodiment, m and n are 0 for use as an HTM (hole-transport material).If m+n is 1 and Y or Z is a single bond, the compounds are preferably suitable for hTMMs (hole-transporting triplet matrix materials). For FE (fluorescence emitters), it is preferred that n and / or m is or are 1 and Z and / or Y are BR, preferably BAr' (CABNA type). In a preferred embodiment, Y and / or Z, identical or different on each occurrence, are a single bond, BAr', C=O, C(R)2, NAr', PR, SO2, SiR2, SiAr'2, P(O)Ar', O or S, particularly preferably a single bond, BAr', C=O, C(R)2, SiR2, SiAr'2, P(O)Ar', O or S, in particular a single bond, BAr', or O. The following embodiments are particularly preferred:

[0013] In a preferred embodiment, the compounds based on formula (2) and its preferred embodiments are symmetrical, in particular C2-symmetrical. In a preferred embodiment, R is, identically or differently at each occurrence, D, F, Cl, Br, I, N(Ar')2, N(R 1 )2, OAr', SAr', B(R 1 )2, B(OR 1 )2, CHO, C(=O)R 1 , CR 1 =C(R 1 )2, C(=O)OR 1 , C(=O)NR 1 , Si(R 1 )3, NO2, P(R 1 )2, P(=O)(R 1 )2, OSO2R 1 , OR 1 , S(=O)R 1 , S(=O)2R 1 , SR 1, 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 1 may be substituted, with one or more non-adjacent CH2 groups being replaced by -R 1 C=CR 1 -, -C≡C-, Si(R 1 )2, NR 1 , CONR 1 , C=O, C=S, -C(=O)O-, P(=O)(R 1 ), -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, each substituted by one or more radicals R 1may be substituted, where two or more R radicals preferably bound to the same cycle may form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system which may be substituted with one or more R radicals 1 may be substituted. In a preferred embodiment, at least one group R represents an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, each substituted by one or more radicals R 1 may be substituted, where two or more R radicals preferably bound to the same cycle may form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system which may be substituted with one or more R radicals 1 may be substituted. Preferred substituents R, R', Ar', R 1 and R 2In a particularly preferred embodiment of the invention, the following preferences for R, R', Ar', R 1 and R 2 simultaneously and apply to the structures of formula (1) as well as to all preferred embodiments listed above. In a preferred embodiment of the invention, R is selected, identically or differently, at each occurrence from the group consisting of D, F, OR 1 , a straight-chain alkyl group having 1 to 10 C atoms or an alkenyl group having 2 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, wherein the alkyl or alkenyl group is each substituted with one or more radicals R 1may be substituted, but is preferably unsubstituted, and wherein one or more non-adjacent CH2 groups may be replaced by O, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, each substituted by one or more radicals R 1 may be substituted; two radicals R may also form an aliphatic, aromatic or heteroaromatic ring system with one another. Particularly preferably, R is selected, identically or differently at each occurrence, from the group consisting of D, CN, F, a straight-chain alkyl group having 1 to 6 C atoms, in particular having 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group having 3 to 6 C atoms, where the alkyl group is substituted in each case with one or more radicals R 1may be substituted, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each substituted by one or more radicals R 1 , preferably non-aromatic residues R 1 , may be substituted. Very particularly preferably, R is selected at each occurrence, identically or differently, from the group consisting of H or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each substituted by one or more radicals R 1 , preferably non-aromatic residues R 1 , may be substituted. In a preferred embodiment of the invention, R' is selected on each occurrence, identically or differently, from the group consisting of H, D, F, OR 1, a straight-chain alkyl group having 1 to 10 C atoms or an alkenyl group having 2 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, where the alkyl or alkenyl group may in each case be substituted by one or more radicals R, but is preferably unsubstituted, and where one or more non-adjacent CH2 groups may be replaced by O, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, each of which may be substituted by one or more radicals R; two radicals R can also form an aliphatic, aromatic or heteroaromatic ring system with one another. Particularly preferably, R' is selected, identically or differently at each occurrence, from the group consisting of H, D, F or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each of which is substituted by one or more radicals R, preferably non-aromatic radicals R,may be substituted. R' is very particularly preferably selected at each occurrence, identically or differently, from the group consisting of H, D or from an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each of which may be substituted by one or more radicals R. Suitable aromatic or heteroaromatic ring systems R and R' are selected from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, which can be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which can be linked via the 1-, 2-, 3- or 4-position, naphthalene, which can be linked via the 1- or 2-position, indole, benzofuran, benzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, carbazole, which can be linked via the 1-, 2-,3- or 4-position, dibenzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline, benzimidazole, phenanthrene, triphenylene or a combination of two or three of these groups, each of which can be linked to one or more radicals R, 1 may be substituted. If R and / or R' represents a heteroaryl group, in particular triazine, pyrimidine or quinazoline, aromatic or heteroaromatic radicals R 1 on this heteroaryl group. The groups R and R', when they represent an aromatic or heteroaromatic ring system, are preferably selected from the groups of the following formulae R-1 to R-163, where in the case of R', R 1 for R stands:

[0014] where R 1 has the meanings given above, the dashed bond represents the bond to formula (1) or formula (2) and furthermore: Ar 5 is at each occurrence, identically or differently, a bivalent aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, each of which is substituted by one or more radicals R 1 can be substituted; A 3 is the same or different each time it occurs BR 1 , C(R 1 )2, NR 1 , PR 1 , O or S, preferably C(R 1 )2, BR 1 , NR 1 , O or S; A 4 is the same or different at each occurrence C(R 1 )2, NR 1 , O or S; s is 0 or 1, where s = 0 means that the group Ar 5is not present and that the corresponding aromatic or heteroaromatic group is directly bonded to a carbon atom of the basic structure in formula (1); r is 0 or 1, where r = 0 means that no group A is present at this position. 3 and the corresponding carbon atoms are instead bound to residues R 1 In a preferred embodiment, Ar comprises 5 bivalent aromatic or heteroaromatic ring systems based on the groups R-1 to R-163, where s is 0 and the dashed bond and an R 1 represents the bond to the aromatic or heteroaromatic group after R-1 to R-163. If the above-mentioned groups R-1 to R-163 represent several groups A 3 all combinations from the definition of A 3 Preferred embodiments are then those in which a group A 3 for C(R 1 )2, BR 1 , NR 1, O or S and the other group A 3 for C(R 1 )2 or in which both groups A 3 stand for S or O or in which both groups A 3 stand for O or S. If A 3 for NR 1 the substituent R 1 which is bonded to the nitrogen atom, preferably represents an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which can also be substituted by one or more radicals R 2 In a particularly preferred embodiment, this substituent R 1identical or different on each occurrence for an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 12 aromatic ring atoms, which does not have any condensed aryl groups or heteroaryl groups in which two or more aromatic or heteroaromatic 6-ring groups are directly condensed to one another, and which in each case also by one or more radicals R 2 Particularly preferred are phenyl, biphenyl, terphenyl and quaterphenyl with linkage patterns as listed above for R-1 to R-35, where these structures are substituted by one or more radicals R 1 may be substituted, but are preferably unsubstituted. If A 3 for C(R 1 )2, the substituents R 1which 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 aromatic ring atoms, which can also be substituted by one or more radicals R 2 R is particularly preferably 1 represents a methyl group or a phenyl group. The radicals R 1 also form a ring system with each other, resulting in a spiro system. In a further preferred embodiment of the invention, R 1 identically or differently at each occurrence selected from the group consisting of H, D, F, OR 2, a straight-chain alkyl group having 1 to 10 C atoms or an alkenyl group having 2 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, wherein the alkyl or alkenyl group is each substituted with one or more radicals R 2 may be substituted and wherein one or more non-adjacent CH2 groups may be replaced by O, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, each substituted by one or more radicals R 2 may be substituted; two or more radicals R 1 together form an aliphatic ring system. In a particularly preferred embodiment of the invention, R 1identically or differently on each occurrence selected from the group consisting of H, a straight-chain alkyl group having 1 to 6 C atoms, in particular having 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group having 3 to 6 C atoms, where the alkyl group is substituted with one or more radicals R 2 may be substituted, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each substituted by one or more radicals R 2 may be substituted, but is preferably unsubstituted. In a further preferred embodiment of the invention, R 2 identically or differently on each occurrence, H, F, an alkyl group having 1 to 4 C atoms or an aryl group having 6 to 10 C atoms, which may be substituted by an alkyl group having 1 to 4 C atoms, but is preferably unsubstituted. In a further preferred embodiment of the invention, all radicals R1 , insofar as they represent an aromatic or heteroaromatic ring system, or R 2 as long as they represent aromatic or heteroaromatic groups selected from the groups R-1 to R-163, which, however, are then each substituted with R 2 , or the one at R 2mentioned groups are substituted. In a preferred embodiment, the radicals R do not form any further aromatic or heteroaromatic groups fused to the basic structure of formula (1), unless explicitly stated in the preferred embodiments. The alkyl groups in compounds according to the invention which are processed by vacuum evaporation preferably have no more than five C atoms, particularly preferably no more than 4 C atoms, very particularly preferably no more than 1 C atom. For compounds which are processed from solution, compounds which are substituted by alkyl groups, in particular branched alkyl groups, having up to 10 C atoms or which are substituted by oligoarylene groups, for example ortho-, meta-, para- or branched terphenyl or quaterphenyl groups, are also suitable.The above-mentioned preferred embodiments can be combined with one another as desired within the limitations defined in claim 1. In a particularly preferred embodiment of the invention, the above-mentioned preferences occur simultaneously. Examples of preferred compounds according to the above-mentioned embodiments are the compounds listed in the following table.

[0015] 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, Heck reaction, Hartwig-Buchwald coupling, cyanations, etc. The present invention therefore further provides a process for preparing the compounds according to the invention, characterized by the following steps: (A) Synthesis of the compound of formula (1) comprising A 1 A 2 -Ar 1 or formula (2) comprising Ar 1 A 2 Ar 1 ; (B) Introduce the group Ar 2 to A 1 A 2 -Ar 1 or Ar 1 A 2 Ar 1 ; (C) Ring closure between Ar 2 and Ar 1 introducing NR'; (D) Optionally further functionalization and / or replacement of R'. The introduction of the group Ar 2 occurs preferentially at the carbon with a covalent bond to A 1 , A 2and Ar 1 for formula (1), or with a covalent bond to both Ar 1 and A 2 for formula (2). An example of a synthesis is shown in Scheme 1. First, the basic structure of A 1 A 2 -Ar 1 provided, which is marked with X 2 has a coupling group, for example Br, Cl or I. To this is attached a coupling group X which is compatible with 3 and a nitrate group modified group Ar 2 Then the groups Ar 1 and Ar 2 via a Cadogan-type ring closure. In most cases, the compound of formula (1) with R' is H is obtained. Further coupling reactions can then replace R' with another group other than H, preferably Ar 3 . In further ring-closure reactions, the groups Y and / or Z can then be introduced. The compounds of formula (2) can be prepared analogously.

[0016] The compounds of the invention can be prepared starting from known compounds brominated or iodinated at the bridgehead carbon atom according to M. Oi et al., Chem. Sci., 2019, 10, 6107. In step 1, the bridgehead carbon atom is first lithiated by reacting the bromide with n-BuLi, followed by transmetalation with copper(I) chloride and subsequent palladium-catalyzed CC coupling with a 2-nitro-iodoaromatic compound. In step 2, the Cadogan-type reductive cyclization, e.g., according to AW Freeman et al., J. Org. Chem. 2005, 70, 5014-5019 or CN110845508, leads to the 9,10-dihydroacridan system. This can then be reacted in a CN coupling according to Buchwald-Hartwig or Ullmann with an aryl or heteroaryl halide (Ar 3 -X) to give further preferred products according to the invention. The 9,10-dihydro-acridan intermediate from step 2 as well as the product from step 3 (Scheme 2) can be regioselectively halogenated in the para position(s) to the N atom with N-haloimides such as N-chloro-, bromo-, or iodo-succinimide (see step 1, Scheme 3). The halogen functions thus introduced can be further functionalized in CC coupling reactions of the Suzuki, Negishi, Sonogashira, Heck type, etc., or in CN coupling reactions of the Buchwald-Hartwig or Ullmann type (see step 2, Scheme 3).

[0017] If o-halogen-substituted aromatics are introduced in step 3, Scheme 2, by using 1,2-Cl,Br- or -Cl,I- or -Br,I-aromatics, these can be prepared, for example, according to PB Tiruveedhula et al., Org. & Biomol. Chem., 2015, 13(43), 10705 or F. Chen et al., RSC Adv., 2015, 5, 51512 or T. Kader et al., Chem. Europ. J., 2019, 25(17), 4412 or analogously to US 9,000,421 B1, palladium-catalyzed in the presence of a base and a tertiary phosphine or an NHC can be cyclized to carbazoles, see Scheme 4. The regioselectivity can be specifically controlled by steric and / or electronic influences of the substituents R. If o,o'-halogen-substituted aromatics are converted, 10H-benzo-[1,7]pyrrolizino[2,3,4,5,6-defg]acridines can be obtained in this way. The BN heterocycles of the invention can be prepared starting from the 9,10-dihydroacridan intermediates from step 2, Scheme 2 (see Scheme 5). First, an o,o'-bischloroarylene function is introduced via a Sn2-Ar reaction according to step 1a or alternatively via a Buchwald-Hartwig coupling according to step 1b (see Scheme 5). This is then converted into the o,o'-bislithioarylene function using t-BuLi and subsequently reacted in situ with BBr3. Double electrophilic cyclization in the presence of the base DIPEA and subsequent reaction of the remaining B-Br functionality with an aryllithium species yields the BN heterocycles of the invention. 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 are required. These formulations can be, for example, solutions, dispersions, or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, ^-terpineol, benzothiazole, butylbenzoate, cumene, cyclohexanol, cyclohexanone, Cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, NMP,p-Cymene, phenetole, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, 2-methylbiphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, diethyl sebacate, octyl octanoate, heptylbenzene, menthyl isovalerate, cyclohexylhexanoate or mixtures of these solvents. The present invention therefore further provides a formulation, in particular a solution, dispersion, or emulsion, comprising at least one compound according to the invention and at least one further compound. The further compound can, for example, be a solvent,in particular one of the above-mentioned solvents or a mixture of these solvents. The preparation of such solutions is known to the person skilled in the art and is described, for example, in WO 2002 / 072714, WO 2003 / 019694 and the literature cited therein. However, the further compound can also be at least one further organic or inorganic compound that is also used in the electronic device, for example an emitting compound and / or a matrix material. This further compound can also be polymeric. The compounds according to the invention are suitable for use in an electronic device,in particular in an organic electroluminescent device (OLED). Depending on the substitution, the compounds can be used in different functions and layers. A further subject of the present invention is therefore the use of a compound according to the invention in an electronic device. A still further subject of the present invention is an electronic device comprising at least one compound according to the invention. The compounds according to the invention can be present, in particular when used, as a racemate or as a pure enantiomer. An electronic device within the meaning of the present invention is a device which contains at least one layer containing at least one organic compound. The component can also contain inorganic materials or layers,which are constructed entirely of inorganic materials. The electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), dye-sensitized organic solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), and organic plasmon-emitting devices, but preferably organic electroluminescent devices (OLEDs). The device is particularly preferably an organic electroluminescent device comprising a cathode, an anode, and at least one emitting layer, wherein at least one organic layer,which may be an emitting layer, hole-transport layer, electron-transport layer, hole-blocking layer, electron-blocking layer, or another functional layer, comprises at least one compound according to the invention. The layer depends on the substitution of the compound. In addition to these layers, the organic electroluminescent device may contain further layers, for example, one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, exciton-blocking layers, electron-blocking layers, charge-generation layers, and / or organic or inorganic p / n junctions. Interlayers, which, for example, have an exciton-blocking function, may also be introduced between two emitting layers. However, it should be noted thatthat not every one of these layers necessarily has to be present. The organic electroluminescent device may contain one emitting layer, or it may contain multiple emitting layers. If multiple emitting layers are present, these preferably have a total of multiple emission maxima between 380 nm and 750 nm, resulting in overall white emission, i.e., different emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. Systems with three emitting layers are particularly preferred, with the three layers exhibiting blue, green, and orange or red emission (the basic structure is described, for example, in WO 2005 / 011013). The organic electroluminescent device according to the invention may also be a tandem OLED.in particular for white-emitting OLEDs. The compound according to formula (1) is preferably used in an organic electroluminescent device comprising one or more phosphorescent emitters. The compound according to the invention according to the embodiments listed above can be used in different layers, depending on the precise structure. The organic electroluminescent device can contain one emitting layer, or it can contain several emitting layers, with at least one layer containing at least one compound according to the invention. Furthermore, the compound according to the invention can also be used in an electron-transport layer and / or in a hole-blocking layer and / or in a hole-transporting layer and / or in an exciton-blocking layer. The term "phosphorescent compound" typically refers to compoundsin which the emission of light occurs through a spin-forbidden transition, e.g., a transition from an excited triplet state or a state with a higher spin quantum number, e.g., a quintet state. Suitable phosphorescent compounds (= triplet emitters) are, in particular, compounds which, upon suitable excitation, emit light, preferably in the visible range, and which 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. All luminescent complexes with transition metals or lanthanides are preferably considered as phosphorescent compounds, especially if they contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium, especially compounds containing iridium,Contain platinum or copper. For the purposes of the present invention, all luminescent iridium, platinum, or copper complexes are considered phosphorescent emitting compounds. Examples of the emitters described above can be found in the applications WO 00 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 05 / 033244, WO 05 / 019373, US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, WO 2010 / 102709, WO 2011 / 032626, WO 2011 / 066898, WO 2011 / 157339, WO 2012 / 007086, WO 2014 / 008982, WO 2014 / 023377, WO 2014 / 094961, WO 2014 / 094960, WO 2015 / 036074, WO 2015 / 104045, WO 2015 / 117718, WO 2016 / 015815, WO 2016 / 124304, WO 2017 / 032439, WO 2018 / 011186, WO 2018 / 041769, WO 2019 / 020538, WO 2018 / 178001, WO 2019 / 115423 and WO 2019 / 158453. In general, all phosphorescent complexes are suitable,as used according to the prior art for phosphorescent OLEDs and as known to the person skilled in the art in the field of organic electroluminescence, and the person skilled in the art can use further phosphorescent complexes without inventive step. It is also possible for the person skilled in the art, even without inventive step, to use further phosphorescent complexes in combination with the compounds of formula (1) in organic electroluminescent devices. Further examples are listed in a table below. According to the invention, it is also possible to use the compound of formula (1) in an electronic device containing one or more fluorescent emitting compounds. In a preferred embodiment of the invention, the compounds of formula (1) are used as hole-transporting material. In this case, the compounds are preferably present in a hole-transport layer,an electron-blocking layer or a hole-injection layer. Use in an electron-blocking layer is particularly preferred. A hole-transport layer in the sense of the present application is a layer with a hole-transporting function between the anode and the emitting layer. In the context of the present application, hole-injection layers and electron-blocking layers are understood to mean certain embodiments of hole-transport layers. In the case of a plurality of hole-transport layers between the anode and the emitting layer, a hole-injection layer is a hole-transport layer that is directly adjacent to the anode or is separated from it only by a single coating of the anode. In the case of several hole-transport layers between the anode and the emitting layer, an electron-blocking layer is the hole-transport layerwhich is directly adjacent to the emitting layer on the anode side. Preferably, the OLED according to the invention comprises two, three, or four hole-transporting layers between the anode and the emitting layer, of which preferably at least one, particularly preferably exactly one or two, contains a compound of formula (1). If the compound of formula (1) is used as a hole-transporting material in a hole-transporting layer, a hole-injecting layer, or an electron-blocking layer, the compound can be used as a pure material, i.e., in a proportion of 100%, in the hole-transporting layer, or it can be used in combination with one or more other compounds. In a preferred embodiment, the organic layer containing the compound of formula (1) then additionally contains one or more p-dopants. p-dopants used according to the present inventionare preferably those organic electron acceptor compounds that are capable of oxidizing one or more of the other compounds in the mixture. Particularly preferred embodiments of p-dopants are the compounds disclosed in WO 2011 / 073149, EP 1968131, EP 2276085, EP 2213662, EP 1722602, EP 2045848, DE 102007031220, US 8044390, US 8057712, WO 2009 / 003455, WO 2010 / 094378, WO 2011 / 120709, US 2010 / 0096600, WO 2012 / 095143, and DE 102012209523. Particularly preferred p-dopants are quinodimethane compounds, azaindenofluorenediones, azaphenylenes, azatriphenylenes, I2, metal halides, preferably transition metal halides, metal oxides, preferably metal oxides containing at least one transition metal or a metal of the 3rd main group, and transition metal complexes, preferably complexes of Cu, Co, Ni, Pd and Pt with ligands,which contain at least one oxygen atom as a bonding site. Transition metal oxides are also preferred as dopants, preferably oxides of rhenium, molybdenum, and tungsten, particularly preferably Re2O7, MoO3, WO3, and ReO3. The p-dopants are preferably present in a substantially homogeneous distribution in the p-doped layers. This can be achieved, for example, by co-evaporation of the p-dopant and the hole-transport material matrix. Preferred p-dopants are, in particular, the following compounds:

[0018] In a further preferred embodiment of the invention, the compound of formula (1) is used as a hole-transport material in combination with a hexaazatriphenylene derivative, as described in US 2007 / 0092755. Particular preference is given here to using the hexaazatriphenylene derivative in a separate layer. In a further embodiment of the present invention, the compound of formula (1) is used in an emitting layer as a matrix material in combination with one or more emitting compounds, preferably phosphorescent compounds. The proportion of matrix material in the emitting layer in this case is between 50.0 and 99.9 vol.%, preferably between 80.0 and 99.5 vol.%, particularly preferably between 92.0 and 99.5 vol.% for fluorescent emitting layers and between 85.0 and 97.0 vol.% for phosphorescent emitting layers.Accordingly, the proportion of the emitting compound is between 0.1 and 50.0 vol. %, preferably between 0.5 and 20.0 vol. %, particularly preferably between 0.5 and 8.0 vol. % for fluorescent emitting layers and between 3.0 and 15.0 vol. % for phosphorescent emitting layers. An emitting layer of an organic electroluminescent device can also comprise systems that contain a plurality of matrix materials (mixed matrix systems) and / or a plurality of emitting compounds. In this case, too, the emitting compounds are generally those that have the smaller proportion in the system and the matrix materials are those that have the larger proportion in the system. In individual cases, however, the proportion of an individual matrix material in the system can be lower than the proportion of an individual emitting compound. The compounds of formula (1) are preferably used as a component of mixed matrix systems.The mixed matrix systems preferably consist of two or three different matrix materials, particularly preferably of two different matrix materials. In this case, one of the two materials is preferably a material with hole-transporting properties and the other material is a material with electron-transporting properties. The compound of formula (1) is preferably the matrix material with hole-transporting properties. However, the desired electron-transporting and hole-transporting properties of the mixed matrix components can also be predominantly or completely combined in a single mixed matrix component, with the further mixed matrix component(s) fulfilling other functions. The two different matrix materials can be present in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, even more preferably 1:10 to 1:1, and most preferably 1:4 to 1:1.Mixed matrix systems are preferably used in phosphorescent organic electroluminescent devices. A source for more detailed information on mixed matrix systems is the application WO 2010 / 108579. The mixed matrix systems can contain one or more emitting compounds, preferably one or more phosphorescent compounds. In general, mixed matrix systems are preferably used in phosphorescent organic electroluminescent devices. Particularly suitable matrix materials that can be used in combination with the compounds according to the invention as matrix components of a mixed matrix system are selected from the preferred matrix materials for phosphorescent compounds or the preferred matrix materials for fluorescent compounds listed below, depending on the type of emitting compound used in the mixed matrix system.Preferred phosphorescent compounds for use in mixed matrix systems are the same as those described above as generally preferred phosphorescent emitter materials. Preferred embodiments of the various functional materials in the electronic device are listed below. Examples of phosphorescent compounds are listed below.

[0019] Preferred fluorescent-emitting compounds are selected from the class of arylamines. In the context of the present invention, an arylamine or an aromatic amine is understood to mean a compound containing three substituted or unsubstituted aromatic or heteroaromatic ring systems that are bonded directly to the nitrogen. Preferably, at least one of these aromatic or heteroaromatic ring systems is a condensed ring system, particularly preferably with at least 14 aromatic ring atoms. Preferred examples thereof are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic chrysenamines, or aromatic chrysenediamines. An aromatic anthraceneamine is understood to mean a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in position 9. An aromatic anthracenediamine is understood to mean a compoundin which two diarylamino groups are bonded directly to an anthracene group, preferably in positions 9 and 10. Aromatic pyrenamines, pyrenediamines, chrysenamines, and chrysenediamines are defined analogously, in which the diarylamino groups are preferably bonded to the pyrene in the 1-position or 1,6-position. Further preferred emitting compounds are indenofluorenamines or fluorenediamines, for example according to WO 2006 / 108497 or WO 2006 / 122630, benzoindenofluorenamines or -fluorenediamines, for example according to WO 2008 / 006449, and dibenzoindenofluorenamines or -diamines, for example according to WO 2007 / 140847, as well as the indenofluorene derivatives with fused aryl groups disclosed in WO 2010 / 012328. Likewise preferred are the pyrenarylamines disclosed in WO 2012 / 048780 and WO 2013 / 185871. Also preferred are the benzoindenofluorenamines disclosed in WO 2014 / 037077, the benzofluorenamines disclosed in WO 2014 / 106522,the extended benzoindenofluorenes disclosed in WO 2014 / 111269 and WO 2017 / 036574, the phenoxazines disclosed in WO 2017 / 028940 and WO 2017 / 028941, and the fluoro derivatives bound to furan units or thiophene units disclosed in WO 2016 / 150544. Useful matrix materials, preferably for fluorescent compounds, include materials from various substance classes. Preferred matrix materials are selected from the classes of oligoaryls (e.g. 2,2',7,7'-tetraphenylspirobifluorene according to EP 676461 or dinaphthylanthracene), in particular oligoaryls with fused aromatic groups, oligoarylenevinylenes (e.g. DPVBi or spiro-DPVBi according to EP 676461), polypodal metal complexes (e.g. according to WO 2004 / 081017), hole-conducting compounds (e.g. according to WO 2004 / 058911), electron-conducting compounds, in particular ketones, phosphine oxides, sulfoxides, etc. (for example according to WO 2005 / 084081 and WO 2005 / 084082),the atropisomers (for example, according to WO 2006 / 048268), the boronic acid derivatives (for example, according to WO 2006 / 117052), or the benzanthracenes (for example, according to WO 2008 / 145239). Particularly preferred matrix materials are selected from the classes of oligoarylenes containing naphthalene, anthracene, benzanthracene, and / or pyrene, or atropisomers of these compounds, the oligoarylenevinylenes, the ketones, the phosphine oxides, and the sulfoxides. Very particularly preferred matrix materials are selected from the classes of oligoarylenes containing anthracene, benzanthracene, benzophenanthrene, and / or pyrene, or atropisomers of these compounds. For the purposes of the present invention, an oligoarylene is understood to mean a compound in which at least three aryl or arylene groups are bonded to one another. Further preferred are the anthracene derivatives disclosed in WO 2006 / 097208, WO 2006 / 131192, WO 2007 / 065550, WO 2007 / 110129, WO 2007 / 065678, WO 2008 / 145239, WO 2009 / 100925, WO 2011 / 054442 and EP 1553154,the pyrene compounds disclosed in EP 1749809, EP 1905754 and US 2012 / 0187826, the benzanthracenylanthracene compounds disclosed in WO 2015 / 158409, the indenobenzofurans disclosed in WO 2017 / 025165 and the phenanthrylanthracenes disclosed in WO 2017 / 036573. Preferred matrix materials for phosphorescent compounds are, as well as compounds according to formula (1), aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680, triarylamines, carbazole derivatives, e.g. B. CBP (N,N-biscarbazolylbiphenyl) or WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or WO 2013 / 041176, indolocarbazole derivatives, e.g. according to WO 2007 / 063754 or WO 2008 / 056746, indenocarbazole derivatives, e.g. according to WO 2010 / 136109, WO 2011 / 000455, WO 2013 / 041176 or WO 2013 / 056776, azacarbazole derivatives, e.g. B. according to EP 1617710, EP 1617711, EP 1731584, JP 2005 / 347160,bipolar matrix materials, e.g. according to WO 2007 / 137725, silanes, e.g. according to WO 2005 / 111172, azaboroles or boronate esters, e.g. according to WO 2006 / 117052, triazine derivatives, e.g. according to WO 2007 / 063754, WO 2008 / 056746, WO 2010 / 015306, WO 2011 / 057706, WO 2011 / 060859 or WO 2011 / 060877, zinc complexes, e.g. according to EP 652273 or WO 2009 / 062578, diazasilole or tetraazasilole derivatives, e.g. B. according to WO 2010 / 054729, diazaphosphole derivatives, e.g. according to WO 2010 / 054730, bridged carbazole derivatives, e.g. according to WO 2011 / 042107, WO 2011 / 060867, WO 2011 / 088877 and WO 2012 / 143080, triphenylene derivatives, e.g. according to WO 2012 / 048781, lactams, e.g. according to WO 2011 / 116865 or WO 2011 / 137951, or dibenzofuran derivatives, e.g. B. according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO 2017 / 148565. Likewise, another phosphorescent emitter, which emits at a shorter wavelength than the actual emitter, can be present as a co-host in the mixture or a compound,which does not participate, or does not participate to a significant extent, in charge transport, as described, for example, in WO 2010 / 108579. Suitable charge transport materials, such as can be used in the hole injection or hole transport layer or in the electron barrier layer or in the electron transport layer of the electronic component according to the invention, are, in addition to the compounds of formula (1), for example, those described in Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010, or other materials as used in these layers according to the prior art. Preferably, the OLED according to the invention comprises two or more different hole-transporting layers. The compound of formula (1) can be used in one or more or in all hole-transporting layers. In a preferred embodiment, the compound of formula (1) is used in exactly one or exactly two hole-transporting layers,and in the other existing hole-transporting layers, other compounds, preferably aromatic amine compounds, are used. Further compounds which, in addition to the compounds of formula (1), are preferably used in hole-transporting layers of the OLEDs according to the invention are, in particular, indenofluorenamine derivatives (e.g. according to WO 06 / 122630 or WO 06 / 100896), the amine derivatives disclosed in EP 1661888, hexaazatriphenylene derivatives (e.g. according to WO 01 / 049806), amine derivatives with fused aromatics (for example according to US 5,061,569), the amine derivatives disclosed in WO 95 / 09147, monobenzoindenofluorenamines (for example according to WO 08 / 006449), dibenzoindenofluorenamines (for example according to WO 07 / 140847), spirobifluorenamines (for example according to WO 2012 / 034627 or WO 2013 / 120577), fluorenamines (for example according to WO 2014 / 015937, WO 2014 / 015938, WO 2014 / 015935 and WO 2015 / 082056), spirodibenzopyranamines (for example according to WO 2013 / 083216),Dihydroacridine derivatives (for example according to WO 2012 / 150001), spirodibenzofurans and spirodibenzothiophenes (for example according to WO 2015 / 022051, WO 2016 / 102048 and WO 2016 / 131521), phenanthrenediarylamines (for example according to WO 2015 / 131976), spirotribenzotropolones (for example according to WO 2016 / 087017), spirobifluorenes with meta-phenyldiamine groups (for example according to WO 2016 / 078738), spirobisacridines (for example according to WO 2015 / 158411), xanthenediarylamines (for example according to WO 2014 / 072017), and 9,10-dihydroanthracene spiro compounds with diarylamino groups according to WO 2015 / 086108. Very particular preference is given to the use of spirobifluorenes substituted by diarylamino groups in the 4-position as hole-transporting compounds, in particular the use of those compounds claimed and disclosed in WO 2013 / 120577, and the use of spirobifluorenes substituted by diarylamino groups in the 2-position as hole-transporting compounds,in particular, the use of those compounds claimed and disclosed in WO 2012 / 034627. All materials that are used according to the prior art as electron-transport materials in the electron-transport layer can be used as materials for the electron-transport layer. Particularly suitable are aluminum complexes, e.g., Alq3; zirconium complexes, e.g., Zrq4; lithium complexes, e.g., Liq; benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives, and phosphine oxide derivatives. Further suitable materials are derivatives of the aforementioned compounds, as disclosed in JP 2000 / 053957, WO 2003 / 060956, WO 2004 / 028217, WO 2004 / 080975 and WO 2010 / 072300. In the further layers of the organic electroluminescent device according to the invention, all materials can be used.as they are commonly used in the prior art. Therefore, the person skilled in the art can, without inventive step, use all materials known for organic electroluminescent devices in combination with the compounds according to the invention according to formula (1) or the preferred embodiments described above. Also preferred is an organic electroluminescent device characterized in that one or more layers are coated using a sublimation process. The materials are coated 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 -7mbar. Also preferred is an organic electroluminescent device, characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or by means of carrier gas sublimation. The materials are sublimated at a pressure between 10 -5mbar and 1 bar. A special case of this process is the OVJP (Organic Vapour Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured. Also preferred is an organic electroluminescent device, characterized in that one or more layers are produced from solution, for example by spin coating, or using any printing process, such as screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), inkjet printing or nozzle printing. This requires soluble compounds, which are obtained, for example, by suitable substitution. 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.These processes are generally known to the person skilled in the art and can be applied by him without inventive step to organic electroluminescent devices comprising the compounds according to the invention. According to the invention, the electronic devices comprising one or more compounds of the formula (1) can be used in displays, as light sources in lighting applications and as light sources in medical and / or cosmetic applications (e.g. light therapy). The compounds according to the invention and the organic electroluminescent devices according to the invention are characterized by one or more of the following properties: 1. The compounds according to the invention lead to long lifetimes. 2. The compounds according to the invention lead to high efficiencies, in particular to a high EQE. 3. The compounds according to the invention lead to low operating voltages.The invention is explained in more detail by the following examples, without intending to restrict it thereby. The person skilled in the art can carry out the invention within the entire disclosed scope from the descriptions and, without inventive step, prepare further compounds according to the invention and use them in electronic devices or apply the process according to the invention. Examples: Unless otherwise stated, the following syntheses are carried out under a protective gas atmosphere in dried solvents. The solvents and reagents can be obtained, for example, from Sigma-ALDRICH or ABCR. The respective information in square brackets or the numbers given for individual compounds refer to the CAS numbers of the compounds known from the literature. For compounds that can have multiple enantiomeric, diastereomeric or tautomeric forms, one form is shown representatively. 1) Synthons known from the literature LS:.

[0020] 2) Synthesis of synthons S: Example S1: Step 1: Preparation analogous to M. Oi et al., Chem. Sci., 2019, 10, 6107, Example 9. Preparation: 33.3 g (100 mmol) of 9-bromotriptycene, using 27.4 g (110 mmol) of 2-iodo-nitrobenzene instead of methyl 2-iodobenzoate. Purification by flash chromatography (automated column from A. Semrau, silica gel, eluent n-heptane:ethyl acetate, gradient). Yield: 23.0 g (61 mmol), 61%; Purity: 97% pure. 1 H-NMR. Step 2:

[0021] Preparation according to AW Freeman et al., J. Org. Chem. 2005, 70, 5014. Batch: 37.5 g (100 mmol) S1, step 1, 65.6 g (250 mmol) PPh3, 250 mL o-dichlorobenzene (o-DCB), RF, 16 h. Workup: Remove o-DCB in vacuo, precipitate OPH3 using cyclohexane, filter with suction, and concentrate the filtrate. Purification by flash chromatography (automated column from A. Semrau, silica gel, eluent n-heptane:DCM, gradient). Yield: 29.6 g (87 mmol) 87%; Purity: 97% nn 1H-NMR. The following compounds can be obtained analogously:

[0022] Example S100: Preparation analogous to Y. Hu et al., ACS Appl. Polymer Mat. 2019, 1(2), 221. 1.05 eq of NBS was used per CH function para to NH. Batch: 34.4 g (100 mmol) of S1. Yield: 44.8 g (89 mmol), 89%. Purity: 97% nn 1 H-NMR. The following compounds can be obtained analogously:

[0023] Example S200: Preparation analogous to B. van Veller et al., J. Am. Chem. Soc., 2012, 134(17), 7282. Batch: 50.1 g (100 mmol) S100. Yield: 43.4 g (88 mmol), 88%. Purity: 97% nn 1 H-NMR. The following compounds can be obtained analogously:

[0024] Example S300:

[0025] Preparation analogous to CM Tonge et al., J. Am. Chem. Soc., 2019, 141, 35, 13970. Batch: 34.3 g (100 mmol) S1. Yield: 29.1 g (64 mmol) 64%. Purity: 97% nn 1 H-NMR. The following compounds can be obtained analogously:

[0026] 3) Synthesis of the compounds according to the invention: Example B1: Preparation analogous to a) S. S. Reddy et al., Dyes and Pigments, (2016), 134, 315, or b) X. Liu et al., Angew. Chem. IE, 2021, 60(5), 2455, or c) W.- L. Tsai et al., Chem. Commun, 2015, 51(71), 13662. According to a), batch: 34.4 g (100 mmol) of S1. Purification is carried out by repeated hot extraction crystallization (conventional organic solvents or combinations thereof, preferably acetonitrile-DCM, 1:3 to 3:1 vv) or chromatography and fractional sublimation or annealing under high vacuum. Yield: 38.2 g (91 mmol) 91%; Purity: > 99.9% by HPLC. The following compounds can be obtained analogously:

[0027] Example B100A & B100B: Procedure analogous to a) T. Kader et al., Chem. Europ. J., 2019, 25(17), 4412 or analogous to b) US 9,000,421 B1 using tricyclohexylphosphonium tetrafluoroborate or with c) NHC-Pd complexes such as allyl-[1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene]-chloropalladium(II). According to a), batch: 45.4 g (100 mmol) S300. The regioisomers are separated by flash chromatography (Torrent automated column system, A. Semrau). Purification is carried out by repeated hot extraction crystallization (common organic solvents or combinations thereof, preferably acetonitrile-DCM, 1:3 to 3:1 vv) or chromatography and fractional sublimation or annealing under high vacuum. Yield: B100A 11.3 g (27 mmol) 27%; B100B 12.8 g (31 mmol) 31%. Purity: > 99.9% by HPLC. The following compounds can be obtained analogously: Example dopant D1A and D1B: Steps 1 to 3 of the following sequence are carried out as a three-step, one-pot reaction. The workup in step 3 is carried out under protective gas. Step 1: Lithiation of S300 45.4 g (100 mmol) of S300 in 1400 ml of tert-butylbenzene are placed in a baked, argon-inertized four-neck flask equipped with a magnetic stirrer bar, dropping funnel, water separator, reflux condenser, and argon blanket. The reaction mixture is cooled to −40 °C, and then 110.5 ml (210 mmol) of tert-butyllithium, 1.9 M in n-pentane is added dropwise over a period of 30 min. The mixture is stirred for a further 30 min at −40 °C, allowed to warm to room temperature, then heated to 70 °C, while the n-pentane is distilled off over the water separator over a period of approximately 1 h. Step 2: Transmetalation and Cyclization The reaction mixture is cooled again to −40 °C. Over a period of approximately 10 minutes, 10.4 ml (110 mmol) of boron tribromide are added dropwise. After the addition, the reaction mixture is stirred at RT for 1 h. The reaction mixture is then cooled to 0 °C and 19 is added dropwise over a period of approximately 30 minutes.2 ml (110 mmol) of diisopropylethylamine are added. The reaction mixture is then stirred at 160 °C for 16 h. After cooling, the diisopropylethylammonium hydrobromide is filtered off with suction through a reverse frit, and the filtrate is cooled to −78 °C. Step 3: Arylation: In a second, evaporated, argon-inert Schlenk flask equipped with a magnetic stirrer bar, 29.9 g (150 mmol) of 2-bromo-1,3,5-trimethylbenzene [576-83-0] in 1000 ml of diethyl ether are placed and cooled to −78 °C. 60.0 ml (150 mmol) of n-butyllithium, 2.5 M in n-hexane, is added dropwise over approximately 20 min, and the mixture is then stirred for 30 min. The reaction mixture is allowed to warm to RT, stirred for 1 h, and the solvent is completely removed under vacuum. The organolithium compound is suspended in 300 ml of toluene and transferred to the cryogenic reaction mixture from step 2. Stirred for 1 h, and the reaction mixture is allowed to warm to RT overnight.The reaction mixture is carefully added to 15 ml of acetone and evaporated to dryness. The oily residue is extracted with DCM to isolate. ® absorbed and filtered hot through a silica gel bed with an n-pentane-DCM mixture (10:1). The filtrate is evaporated to dryness. The regioisomers are separated by flash chromatography (silica gel, n-heptane / ethyl acetate, Torrent column chromatography, A. Semrau). Purification is carried out by repeated hot extraction crystallization (common organic solvents or combinations thereof, preferably acetonitrile-DCM, 1:3 to 3:1 vv) or chromatography and fractional sublimation or annealing under high vacuum. Yield: D1A 9.4 g (17 mmol) 17%; D1B 8.0 g (15 mmol) 15%. Purity: > 99.9% by HPLC. The following compounds can be obtained analogously:

[0028] Example: Production of OLEDs 1) Vacuum-processed devices: The production of OLEDs according to the invention and OLEDs according to the prior art is carried out according to a general process according to WO 2004 / 058911, which is adapted to the conditions described here (layer thickness variation, materials used). The following examples present the results for various OLEDs. Cleaned glass plates (cleaned in a Miele laboratory dishwasher, Merck Extran cleaner) coated with 50 nm thick structured ITO (indium tin oxide) are pretreated with UV ozone for 25 minutes (UV ozone generator PR-100, UVP). These coated glass plates form the substrates onto which the OLEDs are applied. 1a) Blue Fluorescence OLED Devices – BF: The compounds of the invention can be used in the hole injection layer (HIL), hole transport layer (HTL) and electron blocking layer (EBL).All materials are thermally evaporated in a vacuum chamber. The emission layer (EML) always consists of at least one matrix material (host material) SMB (see Table 1) and an emissive dopant (emitter) D, which is mixed into the matrix material(s) by co-evaporation in a specific volume fraction. A specification such as SMB:D (97:3%) means that the SMB material is present in the layer in a volume fraction of 97% and the dopant D in a volume fraction of 3%. Analogously, the electron transport layer can also consist of a mixture of two materials, see Table 1. The materials used to manufacture the OLEDs are shown in Table 5. The OLEDs are characterized as standard.For this purpose, the electroluminescence spectra, the current efficiency (measured in cd / A), the power efficiency (measured in lm / W), and the external quantum efficiency (EQE, measured in percent) are determined as a function of luminance, calculated from current-voltage-luminance characteristics (IUL characteristics) assuming a Lambertian radiation pattern, as well as the lifetime. The EQE is specified in (%) and the voltage in (V) at a luminance of 1000 cd / m². 2 . The lifetime is determined at a starting luminance of 10000 cd / m 2The measured time in which the brightness of the reference decays to 80% of the initial brightness is set to 100%. The lifetime of the OLED components containing the compounds according to the invention is given as a percentage of the reference. The OLEDs have the following layer structure: Substrate Hole injection layer (HIL) made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm Hole transport layer (HTL), see Table 1 Electron blocking layer (EBL), see Table 1 Emission layer (EML), see Table 1 Electron transport layer (ETL), made of ETM1:ETM2 (50%:50%), 30 nm Electron injection layer (EIL) made of ETM2, 1 nm Cathode made of aluminum, 100 nm Table 1: Structure of blue fluorescence OLED components

[0029] Table 2: Results of blue fluorescent OLED devices

[0030] 1b) Phosphorescent OLED components: The compounds B according to the invention can be used in the hole injection layer (HIL), the hole transport layer (HTL), the electron blocking layer (EBL), and in the emission layer (EML) as matrix material (host material). For this purpose, all materials are thermally vapor-deposited in a vacuum chamber. The emission layer always consists of at least one or more matrix materials M and a phosphorescent dopant Ir, which is added to the matrix material(s) by co-evaporation in a specific volume fraction. A specification such as M1:M2:Ir (55%:35%:10%) means that the material M1 is present in the layer in a volume fraction of 55%, M2 in a volume fraction of 35%, and Ir in a volume fraction of 10%. Analogously, the electron transport layer can also consist of a mixture of two materials. The exact structure of the OLEDs can be found in Table 3.The materials used to manufacture the OLEDs are shown in Table 5. The OLEDs are characterized as standard. For this purpose, the electroluminescence spectra, the current efficiency (measured in cd / A), the power efficiency (measured in lm / W), and the external quantum efficiency (EQE, measured in percent) are determined as a function of luminance, calculated from current-voltage-luminance characteristics (IUL characteristics) assuming a Lambertian radiation pattern, as well as the lifetime. The EQE (%) and the voltage (V) are given at a luminance of 1000 cd / m². 2 . The lifetime is determined at a starting luminance of 1000 cd / m 2 (Blue, Red) or 10000 cd / m 2(Green, yellow) is determined. The measured time in which the brightness of the reference decays to 80% of the initial brightness is set to 100%. The lifetime of the OLED components containing the compounds according to the invention is given as a percentage of the reference. The OLEDs have the following layer structure: Substrate, hole injection layer (HIL) made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm hole transport layer (HTL), see Table 3, electron blocking layer (EBL), see Table 3, emission layer (EML), see Table 3, hole blocking layer (HBL), see Table 3, electron transport layer (ETL), made of ETM1:ETM2 (50%:50%), 30 nm, electron injection layer (EIL) made of ETM2, 1 nm cathode made of aluminum, 100 nm Table 3: Structure of phosphorescent OLED components

[0031] Table 4: Results of phosphorescent OLED devices Table 5: Structural formulas of the materials used

Claims

Claim 1. Compound according to one of formulas (1) or (2), where the following applies to the symbols used: Ar 1 , Ar 2 are, in each occurrence, the same or different, an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which may be substituted by one or more R groups, wherein Ar 1 and / or Ar 2 each can be linked to R' via a residue R or a single bond; A 1 , A 2 In each occurrence, the numbers represent, in the same or different ways, a bivalent alkylene group with 1 to 4 carbon atoms, a bivalent alkenylene group with 2 to 4 carbon atoms, or a bivalent arylene or heteroarylene group with 5 to 60 ring atoms, whereby the alkylene, alkenylene, arylene, or heteroarylene groups may each be substituted with one or more groups R; R' is the same or different in each occurrence H, D, F, Cl, Br, I, OAr', SAr', B(R 1 )2, B(OR 1)2, CHO, C(=O)R, CR=C(R)2, CN, C(=O)OR, C(=O)NR, Si(R)3, NO2, P(=O)(R)2, OSO2R, OR, S(=O)R, S(=O)2R, SR, 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 may each be substituted with one or more R substituents, wherein one or more non-adjacent CH2 groups are replaced by -RC=CR-, -C≡C-, Si(R)2, NR, CONR, C=O, C=S, -C(=O)O-, P(=O)(R), -O-, -S-, SO or SO2 can be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, each of which can be substituted by one or more R groups, wherein two or more R groups can form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system with one or more R groups 1may be substituted; R is the same or different in each occurrence H, D, F, Cl, Br, I, N(Ar')2, N(R 1 )2, OAr', SAr', B(R 1 )2, B(OR 1 )2, CHO, C(=O)R 1 , CR 1 =C(R 1 )2, CN, C(=O)OR 1 , C(=O)NR 1 , Si(R 1 )3, NO2, P(R 1 )2, P(=O)(R 1 )2, OSO2R 1 , OR 1 , S(=O)R 1 , S(=O)2R 1 , SR 1 , 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 1 can be substituted, where one or more non-adjacent CH2 groups are replaced by -R 1 C=CR 1 -, -C≡C-, Si(R 1 )2, NR 1 , CONR 1 , C=O, C=S, -C(=O)O-, P(=O)(R 1), -O-, -S-, SO or SO2 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, each of which is replaced by one or more R groups 1 can be substituted, wherein two or more substituents R, preferably bonded to the same cycle or the same carbon atom, are linked to each other and / or to R' forming an aliphatic, hetero-aliphatic, aromatic or heteroaromatic ring system can form that with one or more residues R 1 may be substituted; Ar' is, in each occurrence, the same or different aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, which is separated by one or more R groups. 1 may be substituted; R 1 is the same or different in each occurrence H, D, F, I, B(R) 2 )2, B(OR 2 )2, N(R 2 )2, CHO, C(=O)R 2 , CR 2 =C(R 2)2, CN, C(=O)OR 2 , Si(R 2 )3, NO2, P(R 2 )2, P(=O)(R 2 )2, OSO2R 2 , SR 2 , OR 2 , S(=O)R 2 , S(=O)2R 2 , 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 2 can be substituted and where one or more CH2 groups in the above-mentioned groups are replaced by -R 2 C=CR 2 -, -C≡C-, Si(R 2 )2, C=O, C=S, -C(=O)O-, NR 2 , CONR 2 , P(=O)(R 2), -O-, -S-, SO or SO2 may be replaced and wherein one or more H atoms in the above-mentioned groups may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, each of which is replaced by one or more R groups 2 can be substituted, with two or more residues R 1 together they can form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R 2 The substance is either the same or different in each occurrence: H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic residue with 1 to 20 C atoms, in which one or more H atoms may also be replaced by D or F; two or more substituents R may be present. 2 1. be linked together and form a ring.

2. Compound according to claim 1, selected from one of the compounds of formulas (3) or (4): wherein the symbols used have the meanings mentioned in claim 1 and additionally the following applies: Ar 3 In each occurrence, it is the same or different aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which may be substituted by one or more R groups; m,n are the same or different 0 or 1 in each occurrence; Y, Z are the same or different in each occurrence, a single bond, BR, BAr', C=O, C(R)2, -RC=CR-, o-arylene, NR, NAr', PR, SO2, SiR2, SiAr'2, P(O)R, P(O)Ar', O or S.

3. Compound according to one or more of claims 1 or 2, selected from the compounds of formulas (5) and (6), wherein the symbols used have the meanings specified in claims 1 and 2 and additionally: X is the same as or different from C at each occurrence where Z or Y is bonded there, CR, CH, CD or N, with the proviso that a maximum of three groups X per cycle represent N.

4. Compound according to one or more of claims 1 to 3, selected from the compounds of formulas (5-1) to (5-4) and (6-1) to (6-4), wherein the symbols used have the meanings specified in claims 1, 2 and 3.

5. Method for producing a compound according to one or more of claims 1 to 4, characterized by the following steps: (A) Synthesis of the compound according to formula (1) comprising A 1 A 2 -Ar 1 or formula (2) comprising Ar 1 A 2 Ar 1 ; (B) Introducing the Ar group 2 an A 1 A 2 -Ar 1 or Ar 1 A 2 Ar1 ; (C) Ring closure between Ar 2 and Ar 1(D) Optionally, further functionalization and / or replacement of R'.

6. Oligomer, polymer, or dendrimer comprising one or more compounds according to formula (1) according to one or more of claims 1 to 4, wherein the bond(s) to the oligomer, polymer, or dendrimer may be formed at any position in formula (1).

7. Formulation comprising at least one compound according to one or more of claims 1 to 4 and at least one further compound and / or at least one solvent.

8. Use of a compound according to one or more of claims 1 to 4 and / or a formulation according to claim 7 in an electronic device.

9. Electronic device comprising at least one compound according to one or more of claims 1 to 4 and / or at least one oligomer, polymer, or dendrimer according to claim 6. 10.Electronic device according to claim 9, wherein it is an organic electroluminescent device, characterized in that the device comprises an anode, a cathode and at least one emitting layer, wherein at least one organic layer, which may be an emitting layer, hole transport layer, electron transport layer, hole blocking layer, electron blocking layer or another functional layer, comprises at least one compound according to one or more of claims 1 to 4.

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