MATERIALS FOR ELECTRONIC DEVICES

Description

[0001] 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.

[0002] Electronic devices containing organic, organometallic, and / or polymeric semiconductors are becoming increasingly important. Due to their cost and performance, these semiconductors are used in many commercial products. 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 display devices, and 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 have the potential to become very important in the future.

[0003] 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, these electronic devices are electroluminescent devices such as OLEDs.

[0004] The structure of OLEDs, which use organic compounds as functional materials, is known to those skilled in the art. Generally, OLEDs are electronic devices that have one or more layers comprising organic compounds and emit light when a voltage is applied.

[0005] 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.

[0006] Hiroki Shioya et al. (2015 Appl. Phys. Express 8 121101) discloses a tripcene molecule with two nitrile groups. Document KR 2021 0100352 A discloses an OLED device comprising a tripcene derivative in the light-emitting auxiliary layer.

[0007] Electronic devices typically comprise a cathode, an anode, and at least one functional, preferably emissive, 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.

[0008] The hole transport layers and electron transport layers have a major influence on the performance of electronic devices.

[0009] 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 of hole transport layers or material of electron transport layers, and which lead to good properties there.

[0010] Surprisingly, it has been found that certain trypticenes, described in more detail below, solve this problem and are well suited for use in electronic devices, particularly OLEDs. These OLEDs exhibit, in particular, a long lifetime, high efficiency, and a low operating voltage. These compounds and electronic devices, particularly organic electroluminescent devices, containing these compounds are therefore the subject of the present invention.

[0011] The present invention relates to a compound according to formula (1), and enantiomers thereof, where the symbols used are: X is the same or different on each occurrence and is CR or N, with the proviso that a maximum of two X groups per cycle are N; Q is the same or different on each occurrence and is C-CN or CR', with the proviso that two Q groups are C-CN. R' is the same or different on each occurrence and is an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, which may each be substituted by one or more radicals R 1<; R is, identically or differently at each occurrence, H, D, F, Cl, Br, I, N(Ar') 2 , N(R 1< ) 2 , OAr', SAr', 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 , NO 2 , P(=O)(R 1< ) 2 , OSO 2 R 1< , OR 1< , S(=O)R 1< , S(=O) 2 R 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 may each be substituted by one or more radicals R 1<, where one or more non-adjacent CH 2 groups may be 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 SO 2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, which may each be substituted by one or more radicals R 1<, where two or more radicals R preferably bonded to the same ring may together form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system which may 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 may be substituted by one or more radicals R 1<; R 1< is, identically or differently on each occurrence, H, D, F, I, 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 , NO 2 , P(=O)(R 2< ) 2 , OSO 2 R 2< , SR 2< , OR 2< , S(=O)R 2< , S(=O) 2 R 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, where the alkyl, Alkenyl or alkynyl group may each be substituted by one or more radicals R 2< and wherein one or more CH 2 groups in the above-mentioned groups may be 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 SO 2 and wherein one or more H atoms in the above-mentioned groups may be replaced by D, F, Cl, Br, I, CN or NO 2,or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, each of which may be substituted by one or more radicals R 2<, where two or more radicals R 1< may form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R 2< is, on each occurrence, identical or different, 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 also be replaced by D or F; two or more substituents R 2< may be linked to one another to form a ring.

[0012] 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 ring, i.e. benzene, or a simple heteroaromatic ring, 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.

[0013] 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 or heteroaryl groups are directly linked to one another, such as: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.

[0014] An electron-rich heteroaromatic ring system is characterized by the fact that it is a heteroaromatic ring system that contains no electron-deficient heteroaryl groups. An electron-deficient 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 include pyrrole, furan, thiophene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, and indenocarbazole. An electron-rich heteroaryl group is also referred to as an electron-rich heteroaromatic radical.

[0015] 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.

[0016] 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.

[0017] A cyclic alkyl, alkoxy or thioalkoxy group in the sense of this invention is understood to mean a monocyclic, a bicyclic or a polycyclic group.

[0018] 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 CH 2 groups may be substituted by the abovementioned 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, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, 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 1< mit 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, Pentafluorethoxy und 2,2,2-Trifluoroethoxy is understood. A thioalkyl group SR 1< with 1 to 40 carbon atoms includes, 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, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, Cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, Butynylthio, pentynylthio, hexynylthio, heptynylthio or octynylthio. In general, alkyl, alkoxy or thioalkyl groups according to the present invention can be straight-chain, branched or cyclic, wherein one or more non-adjacent CH 2 groups can be replaced by the above-mentioned groups; furthermore, one or more H atoms can also be replaced by D, F, Cl, Br, I,CN or NO 2 , preferably F, Cl or CN, particularly preferably F or CN.,

[0019] 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, isobenzothiophene, dibenzothiophene, pyrrole, indole,Isoindol, Carbazol, Pyridin, Chinolin, 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, Hexaazatriphenylen, 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-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole or groups derived from combinations of these systems.

[0020] For the purposes of this description, the phrase "two or more residues can form a ring system" is understood 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:

[0021] 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:

[0022] Further preferred embodiments are shown by the following formula (2): and enantiomers thereof, where the symbols used have the meanings given above for formula (1) with the proviso that Q stands once for CR' and once for C-CN.

[0023] Further preferred embodiments are shown by the following formulas (2-1) and (2-2): and enantiomers thereof, where the symbols used have the meanings given above for formula (1).

[0024] In a preferred embodiment of the invention, a maximum of two symbols X per cycle represent N, particularly preferably a maximum of one symbol X.

[0025] In a preferred embodiment of the invention, X is CR.

[0026] In a preferred embodiment, all X's are CR, where R is H, D, F or CN.

[0027] In a preferred embodiment of the invention, the compound does not have a fused ring system formed by at least two radicals R.

[0028] Preferred embodiments of the compounds of formulas (2-1) and (2-2) are the following compounds of formulas (3-1) and (3-2): and enantiomers thereof, where the symbols, where present, have the meanings given for formula (1).

[0029] In a preferred embodiment of the invention, a maximum of 5 groups R in formulas (2-1) and (2-2), preferably in formulas (3-1) and (3-2), do not represent H, F or D, preferably a maximum of 2 groups R. Particularly preferably, all groups R represent H, F or D.

[0030] Preferred substituents R, R', Ar', R 1<, and R 2< are described below. In a particularly preferred embodiment of the invention, the following preferences for R, R', Ar', R 1<, and R 2< occur simultaneously and apply to the structures of formula (1) as well as to all preferred embodiments listed above.

[0031] 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 1<, but is preferably unsubstituted, and where one or more non-adjacent CH 2 groups may be replaced by O, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1<; 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, 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 may in each case be substituted by one or more radicals R 1<, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1<, preferably non-aromatic radicals R 1<. Very particularly preferably, R is selected, identically or differently at each occurrence, from the group consisting of H or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1< , preferably non-aromatic radicals R 1< .

[0032] In a preferred embodiment of the invention, R' is selected, identically or differently at each occurrence, from the group consisting of 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 1<; 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 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 1<, preferably non-aromatic radicals R 1<.Very particularly preferably, R' is selected, identically or differently at each occurrence, from the group consisting of an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1< , preferably non-aromatic radicals R 1< .

[0033] 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 may be linked to indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline, benzimidazole, phenanthrene, triphenylene or a combination of two or three of these groups,which may each be substituted by one or more radicals R 1<. If R represents a heteroaryl group, in particular triazine, pyrimidine, or quinazoline, aromatic or heteroaromatic radicals R 1< on this heteroaryl group may also be preferred.

[0034] 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 R 1< has the meanings given above, the dashed bond represents the bond to formula (1) and furthermore: Ar 3< is, identically or differently on each occurrence, a bivalent aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, each of which may be substituted by one or more radicals R 1<; A 1< is, identically or differently on each occurrence, BR 1<, C(R 1<) 2, NR 1<, O or S, preferably C(R 1<) 2, NR 1<, O or S; A 2< is, identically or differently on each occurrence, C(R 1<) 2, NR 1<, O or S; p is 0 or 1, where p = 0 means that the group Ar 3< is not present and that the corresponding aromatic or heteroaromatic group is bonded directly to a carbon atom of the basic structure in formula (1); r is 0 or 1, where r = 0 means that no group A 1< is bonded to this position and residues R 1< are bonded to the corresponding carbon atoms instead.

[0035] In a preferred embodiment, Ar 3< comprises bivalent aromatic or heteroaromatic ring systems based on the groups R-1 to R-163, where p 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.

[0036] If the above-mentioned groups R-1 to R-163 have multiple A 1< groups for R and / or R', all combinations from the definition of A 1< are possible. Preferred embodiments are then those in which one A 1< group represents C(R 1< ) 2 , NR 1< , O or S and the other A 1< group represents C(R 1< ) 2 , or in which both A 1< groups represent S or O, or in which both A 1< groups represent O or S.

[0037] If A 1< stands for NR 1<, the substituent R 1< which is bonded to the nitrogen atom preferably stands for an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may also be substituted by one or more radicals R 2<. In a particularly preferred embodiment, this substituent R 1<, identical or different on each occurrence, stands 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 fused aryl groups or heteroaryl groups in which two or more aromatic or heteroaromatic 6-membered ring groups are directly fused to one another, and which may in each case also be substituted 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 may be substituted by one or more radicals R 1<, but are preferably unsubstituted.

[0038] If A 1< stands for C(R 1< ) 2, the substituents R 1< which are bonded to this carbon atom are preferably identical or different on each occurrence and are 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 may also be substituted by one or more radicals R 2<. R 1< very particularly preferably stands for a methyl group or a phenyl group. The radicals R 1< can also form a ring system with one another, resulting in a spiro system.

[0039] In one embodiment of the invention, at least one radical R and / or R', preferably R', represents an electron-rich heteroaromatic ring system. The electron-rich heteroaromatic ring system is preferably selected from the groups R-44 to R-74 shown above, where in the groups R-45 to R-48, R-50 to R-52, R-54 to R-56, R-59 to R-61, R-63 to R-65, and R-67 to R-69, at least one group A 1< represents NR 1<, where R 1< preferably represents an aromatic or heteroaromatic ring system, in particular an aromatic ring system.

[0040] In another particularly preferred embodiment of the invention, at least one radical R and / or R', preferably R', represents an electron-poor heteroaromatic ring system. The electron-poor heteroaromatic ring system is preferably selected from the groups R-79 to R-113, R-123, and R-141 to R-146 depicted above.

[0041] In a preferred embodiment, R is H, DF or an aromatic or heteroaromatic ring system selected from the groups R-1 to R-4, R-44 to R-48, where additionally R 1< is H, D or F and p, if present, is 0.

[0042] In a preferred embodiment, R is H, D or F, preferably H.

[0043] In a further preferred embodiment of the invention, R 1< is selected, identically or differently on each occurrence, from the group consisting of H, D, F, CN, 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, where the alkyl or alkenyl group may in each case be substituted by one or more radicals R 2< and where one or more non-adjacent CH 2 groups may be replaced by O, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2<; two or more radicals R 1< may form an aliphatic ring system with one another.In a particularly preferred embodiment of the invention, R 1< is selected, identically or differently on each occurrence, 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 may be substituted by one or more radicals R 2<, but is preferably unsubstituted, or 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 2<, but is preferably unsubstituted.

[0044] In a further preferred embodiment of the invention, R 2< is identical or different on each occurrence and is 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.

[0045] In a further preferred embodiment of the invention, all radicals R 1< , insofar as they represent an aromatic or heteroaromatic ring system, or R 2< , insofar as they represent aromatic or heteroaromatic groups, are selected from the groups R-1 to R-163, which, however, are then each substituted accordingly with R 2< , or the groups mentioned under R 2<.

[0046] In a preferred embodiment, the radicals R do not form any further aromatic or heteroaromatic groups fused to the basic structure of formula (1).

[0047] The alkyl groups in compounds according to the invention that are processed by vacuum evaporation preferably have no more than five carbon atoms, more preferably no more than four carbon atoms, and most preferably no more than one carbon atom. Also suitable for compounds that are processed from solution are compounds that are substituted by alkyl groups, in particular branched alkyl groups, with up to 10 carbon atoms, or that are substituted by oligoarylene groups, for example ortho-, meta-, para-, or branched terphenyl or quaterphenyl groups.

[0048] 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 advantages occur simultaneously.

[0049] Examples of preferred compounds according to the embodiments listed above are the compounds listed in the following table. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105

[0050] 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.

[0051] A further object of the present invention is therefore a process for the preparation of the compounds according to the invention, characterized by the following steps: (A) Synthesis of the basic framework according to formula (1); (B) Introduction of the radicals CN and R'.

[0052] The 1,2-dicyano-triptycenes according to the invention can be prepared starting from 9,10-dihydro-4-iodo-9,10[1',2']-benzenoanthracen-1-ol [1370032-70-4], by a) Suzuki coupling with an aryl / heteroaryl boronic acid or ester ((HO) 2 -Ar) or b) a Buchwald-Hartwig amination or alternatively a Ullmann coupling with a secondary amine or carbazole (HNAr 2 ), followed by iodination with N-iodosuccinimide in the o-position to the phenolic OH group, its esterification to the triflate and final double cyanation with copper cyanide, or alternatively by transition metal-catalyzed (Pd) cyanation with zinc cyanide or cyanoferrates, see Scheme 1.

[0053] The 1,4-dicyano-triptycenes according to the invention can be prepared starting from 9,10-dihydro-4-hydroxy-9,10[1',2']-benzenoanthracene-1-carbonitrile [1370032-71-5], by iodination with N-iodosuccinimide in the o-position to the phenolic OH group, followed by esterification of the phenolic OH group to the triflate, a) Suzuki coupling of the iodine function with an aryl / heteroaryl boronic acid or ester ((HO) 2 -Ar) or b) a Buchwald-Hartwig amination or alternatively a Ullmann coupling with a secondary amine or carbazole (HNAr 2 ), and final cyanation with copper cyanide, or alternatively by transition metal-catalyzed (Pd) cyanation with zinc cyanide or cyanoferrates, will be shown, see Scheme 2.

[0054] 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, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, Decalin, dodecylbenzene, ethyl benzoate, indane, NMP, p-cymene, phenetol,1,4-Diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-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.

[0055] 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 abovementioned 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 which is also used in the electronic device, for example an emitting compound and / or a matrix material. This further compound can also be polymeric.

[0056] The compounds of 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.

[0057] A further object of the present invention is therefore the use of a compound according to the invention in an electronic device.

[0058] A further subject of the present invention is an electronic device comprising at least one compound according to the invention.

[0059] The compounds according to the invention can be present, in particular when used, as a racemate or as a pure enantiomer.

[0060] An electronic device within the meaning of the present invention is a device that contains at least one layer containing at least one organic compound. The component may also contain inorganic materials or layers composed entirely of inorganic materials.

[0061] 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).

[0062] 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.

[0063] 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. It should be noted, however, that not all of these layers are necessarily present.

[0064] The organic electroluminescent device can contain one emitting layer or it can 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 can also be a tandem OLED, in particular for white-emitting OLEDs.

[0065] The compound of formula (1) is preferably used in an organic electroluminescent device comprising one or more phosphorescent emitters. The compound of the invention according to the embodiments listed above can be used in different layers, depending on the precise structure.

[0066] The organic electroluminescent device may contain one emitting layer or it may contain multiple 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-transport layer and / or in an exciton-blocking layer.

[0067] The term "phosphorescent compound" typically refers to compounds in which the emission of light occurs through a spin-forbidden transition, e.g., a transition from an excited triplet state or a state with a higher spin quantum number, e.g., a quintet state.

[0068] 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 regarded as phosphorescent compounds, in particular if they contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium, in particular compounds containing iridium, platinum, or copper. For the purposes of the present invention, all luminescent iridium, platinum, or copper complexes are regarded as phosphorescent emitting compounds.

[0069] Examples of the emitters described above can be found in applications WO 00 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 05 / 033244, WO 05 / 019373, US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, WO 2010 / 102709, WO 2011 / 032626, WO 2011 / 066898, WO 2011 / 157339, WO 2012 / 007086, WO 2014 / 008982, WO 2014 / 023377, WO 2014 / 094961, WO 2014 / 094960, WO 2015 / 036074, WO 2015 / 104045, WO 2015 / 117718, WO 2016 / 015815, WO 2016 / 124304, WO 2017 / 032439, WO 2018 / 011186, WO 2018 / 041769, WO 2019 / 020538, WO 2018 / 178001, WO 2019 / 115423, and WO 2019 / 158453. 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 electroluminescence are suitable, and the person skilled in the art can use further phosphorescent complexes without inventive step.It is possible for the skilled person, even without inventive step, to use other phosphorescent complexes in combination with the compounds of formula (1) in organic electroluminescent devices. Further examples are listed in the table below.

[0070] 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.

[0071] In a preferred embodiment of the invention, the compounds of formula (1) are used as hole-transporting materials. In this case, the compounds are preferably contained in a hole-transport layer, an electron-blocking layer, or a hole-injection layer. Use in an electron-blocking layer is particularly preferred.

[0072] A hole transport layer within the meaning of the present application is a layer with a hole transporting function between the anode and the emitting layer.

[0073] In the context of the present application, hole injection layers and electron blocking layers are understood to mean specific 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 directly borders the anode or is separated from it only by a single coating of the anode. In the case of multiple hole transport layers between the anode and the emitting layer, an electron blocking layer is the hole transport layer that directly borders the emitting layer on the anode side. The OLED according to the invention preferably 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).

[0074] If the compound of formula (1) is used as a hole-transport material in a hole-transport layer, a hole-injection layer, or an electron-blocking layer, the compound can be used as a pure material, i.e., in a proportion of 100%, in the hole-transport layer, or it can be used in combination with one or more 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 invention are preferably those organic electron-accepting compounds that are capable of oxidizing one or more of the other compounds in the mixture.

[0075] 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.

[0076] Particularly preferred p-dopants are quinodimethane compounds, azaindenofluorenediones, azaphenylenes, azatriphenylenes, I 2 , metal halides, preferably transition metal halides, metal oxides, preferably metal oxides containing at least one transition metal or a metal of main group 3, and transition metal complexes, preferably complexes of Cu, Co, Ni, Pd, and Pt with ligands containing at least one oxygen atom as a bonding site. Also preferred are transition metal oxides as dopants, preferably oxides of rhenium, molybdenum, and tungsten, particularly preferably Re 2 O 7 , MoO 5 , WO 3 , and ReO 5 .

[0077] The p-dopants are preferably present in a substantially homogeneous distribution throughout the p-doped layers. This can be achieved, for example, by coevaporation of the p-dopant and the hole-transport material matrix.

[0078] Preferred p-dopants are in particular the following compounds: (D-1) (D-2) (D-3) (D-4) (D-5) (D-6) (D-7) (D-8) (D-9) (D-10) (D-11) (D-12) (D-13)

[0079] 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. Particularly preferably, the hexaazatriphenylene derivative is used in a separate layer.

[0080] 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.

[0081] In this case, the proportion of matrix material in the emitting layer 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.

[0082] 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.

[0083] An emitting layer of an organic electroluminescent device can also comprise systems containing 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 with the smaller proportion in the system, and the matrix materials those with the larger proportion. In individual cases, however, the proportion of a single matrix material in the system may be lower than the proportion of a single emitting compound.

[0084] 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 additional 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, 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.

[0085] The mixed matrix systems can contain one or more emitting compounds, preferably one or more phosphorescent compounds. Mixed matrix systems are generally preferred for use in phosphorescent organic electroluminescent devices.

[0086] Particularly suitable matrix materials which 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 mentioned below, depending on the type of emitting compound used in the mixed matrix system.

[0087] Preferred phosphorescent compounds for use in mixed matrix systems are the same as those described above as generally preferred phosphorescent emitter materials.

[0088] Preferred embodiments of the various functional materials in the electronic device are listed below.

[0089] Examples of phosphorescent compounds are listed below.

[0090] Preferred fluorescent-emitting compounds are selected from the class of arylamines. For the purposes 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 bonded directly to the nitrogen. Preferably, at least one of these aromatic or heteroaromatic ring systems is a fused ring system, particularly preferably having 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 compound in which two diarylamino groups are directly bonded 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 benzofluorenediamines, 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. Also preferred are the pyrenearylamines disclosed in WO 2012 / 048780 and WO 2013 / 185871.Also preferred are the benzoindenofluorenamines disclosed in WO 2014 / 037077, the benzoindenofluorenamines disclosed in WO 2014 / 106522, the extended benzoindenofluorenes disclosed in WO 2014 / 111269 and in WO 2017 / 036574, the phenoxazines disclosed in WO 2017 / 028940 and in WO 2017 / 028941 and the fluorine derivatives bound to furan units or to thiophene units disclosed in WO 2016 / 150544. Furthermore, boron compounds according to WO2020208051, WO2015102118, WO2016152418, WO2018095397, WO2019004248, WO2019132040, US20200161552, WO2021089450 can be used.

[0091] Useful matrix materials, preferably for fluorescent compounds, include materials from different 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), atropisomers (for example according to WO 2006 / 048268), 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, oligoarylenevinylenes, ketones, phosphine oxides, and sulfoxides. Very particularly preferred matrix materials are selected from the classes of oligoarylenes comprising 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 pyrene compounds disclosed in WO 2017 / 036573 disclosed phenanthrylanthracenes.

[0092] 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. CBP (N,N-bis-carbazolylbiphenyl) or WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or WO 2013 / 041176, indolocarbazole derivatives, e.g. B. according to WO 2007 / 063754 or WO 2008 / 056746, indenocarbazole derivatives, e.g. B. 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. B. according to WO 2007 / 137725, silanes, e.g. B. according to WO 2005 / 111172, azaboroles or boronate esters, e.g. B. 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. according to WO 2010 / 054729, diazaphosphole derivatives, e.g. according to WO 2010 / 054730, bridged carbazole derivatives, e.g. B. according to WO 2011 / 042107, WO 2011 / 060867, WO 2011 / 088877 and WO 2012 / 143080, triphenylene derivatives, e.g. B. according to WO 2012 / 048781, lactams, e.g. B. 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 in the mixture as a co-host or a compound that does not participate or does not participate to a significant extent in the charge transport, as described, for example, in WO 2010 / 108579.

[0093] Suitable charge transport materials which 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 which are used in these layers according to the prior art.

[0094] The OLED according to the invention preferably comprises two or more different hole-transporting layers. The compound of formula (1) can be used in one or more or in all of the hole-transporting layers. In a preferred embodiment, the compound of formula (1) is used in exactly one or exactly two hole-transporting layers, and other compounds, preferably aromatic amine compounds, are used in the other hole-transporting layers present. 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.

[0095] 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.

[0096] All materials that are used in the prior art as electron-transport materials in the electron-transport layer can be used as materials for the electron-transport layer. Particularly suitable are aluminum complexes, 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. Other 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.

[0097] Preferred cathodes of the electronic component are metals with a low work function, metal alloys, or multilayer structures made of different metals, e.g., alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Alloys of an alkali or alkaline earth metal and silver, e.g., 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 can also be used, e.g., Ag or Al, with combinations of the metals, such as Ca / Ag, Mg / Ag, or Ba / Ag, generally being used. It can also be advantageous to introduce a thin intermediate layer made of a material with a high dielectric constant between a metallic cathode and the organic semiconductor.Examples of suitable materials include alkali 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 for this purpose. The thickness of this layer is preferably between 0.5 and 5 nm.

[0098] Preferred anodes are materials with a high work function. The anode preferably has a work function of more than 4.5 eV against a vacuum. Firstly, metals with a high redox potential, e.g., Ag, Pt, or Au, are suitable for this purpose. Secondly, metal / metal oxide electrodes (e.g., Al / Ni / NiOx, Al / PtOx) may also be preferred. For some applications, at least one of the electrodes must be transparent or semi-transparent to enable irradiation of the organic material (organic solar cell) or the emission of light (OLED, O-laser). Preferred anode materials here are conductive mixed metal oxides. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred. Further preferred are conductively doped organic materials, in particular conductively doped polymers.In addition, the anode can also consist of two or more layers, for example an inner layer of ITO and an outer layer of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.

[0099] The device is structured, contacted and finally sealed accordingly (depending on the application) to exclude harmful influences from water and air.

[0100] In the further layers of the organic electroluminescent device according to the invention, all materials commonly used in the prior art can be used. Therefore, the skilled person can, without inventive step, use all materials known for organic electroluminescent devices in combination with the compounds according to formula (1) according to the invention or the preferred embodiments described above.

[0101] Also preferred is an organic electroluminescent device characterized in that one or more layers are coated using a sublimation process. The materials are vapor-deposited 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 for the initial pressure to be even lower, for example, less than 10 -7 mbar.

[0102] 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 applied 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 patterned.

[0103] Also preferred is an organic electroluminescent device characterized in that one or more layers are produced from solution, such as by spin coating, or by any printing process, such as screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), inkjet printing, or nozzle printing. Soluble compounds are required for this, which are obtained, for example, by suitable substitution.

[0104] 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.

[0105] 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 containing the compounds according to the invention.

[0106] According to the invention, the electronic devices containing one or more compounds of 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).

[0107] 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 of the invention lead to long lifetimes. 2. The compounds of the invention lead to high efficiencies, in particular a high EQE. 3. The compounds of the invention lead to low operating voltages.

[0108] The invention is further illustrated by the following examples, without intending to limit it. From the descriptions, those skilled in the art can practice the invention within the entire disclosed scope and, without inventive step, prepare further compounds according to the invention and use them in electronic devices or apply the method according to the invention. Examples:

[0109] Unless otherwise stated, the following syntheses were carried out under a protective gas atmosphere in dried solvents. The metal complexes were also handled in the absence of light or under yellow light. The solvents and reagents can be obtained from Sigma-ALDRICH or ABCR, for example. The respective information in square brackets or the numbers given for individual compounds refer to the CAS numbers of the known compounds. For compounds that can exhibit multiple enantiomeric, diastereomeric, or tautomeric forms, one form is shown as a representative example. 1) Synthesis of 1,2-dicyano-triptycenes: Example B1:

[0110] A) Suzuki clutch

[0111]

[0112] A well-stirred mixture of 39.6 g (100 mmol) 9,10-dihydro-4-iodo-9,10[1',2']-benzenoanthracen-1-ol [1370032-70-4], 12.8 g (105 mmol) phenylboronic acid [98-80-6], 21.2 g (200 mmol) sodium carbonate, 0.72 g (1 mmol) bis(triphenylphosphino)palladium dichloride (alternatively, tetrakistriphenylphosphinopalladium(0), or S-Phos, X-Phos, RuPhos, AmPhos in combination with palladium acetate can be used), 100 g glass beads (3 mm diameter), 400 ml acetonitrile and 400 ml methanol is stirred for 16 h at 50 °C. After complete conversion, the residue is concentrated under vacuum, taken up in 500 ml of dichloromethane (DCM) and 300 ml of water, acidified by slowly adding 200 ml of 2N aqueous HCl while stirring well and cooling with ice, and the organic phase is separated, washed twice with 300 ml of water and once with 200 ml of saturated sodium chloride solution, and dried over sodium sulfate.The drying agent is filtered through a silica gel bed pre-slurried with DCM. The filtrate is slowly concentrated in a rotary evaporator. The distilled DCM is successively replaced with approximately 200 ml of methanol. The crystallized product is filtered off with suction, washed with a little methanol, and dried in vacuo. Yield: 31.2 g (90 mmol) 90%; Purity: approximately 97% by 1< H NMR. B) iodination

[0113]

[0114] A well-stirred solution of 34.6 g (100 mmol) of S1 (step A) in 300 ml of trifluoroethanol (TFE) is added portionwise to 22.5 g (100 mmol) of N-iodosuccinimide [516-12-1]. After complete conversion (approx. 6 h), the mixture is concentrated under vacuum, taken up in 500 ml of DCM and 300 ml of water, the organic phase is separated, washed twice with 300 ml of water and once with 200 ml of saturated brine, and dried over sodium sulfate. The drying agent is removed by filtration, the filtrate is slowly concentrated in a rotary evaporator, the distilled DCM is successively replaced with approximately 200 ml of methanol, the crystallized product is filtered off with suction, washed with a little methanol, and dried under vacuum. Yield: 44.1 g (93 mmol) 93%; Purity: approximately 97% according to 1< H-NMR. C) Triflatization

[0115]

[0116] A solution of 47.2 g (100 mmol) of S1 (step B) in 500 ml of DCM, cooled to 5 °C, is treated with 20.9 ml (150 mmol) of triethylamine and then dropwise with 20.2 ml (120 mmol) of trifluoromethanesulfonic anhydride (105 mmol is used for amines and carbazoles). The mixture is stirred for 30 min at 5 °C, allowed to warm to RT, stirred for 1 h, carefully hydrolyzed with 300 ml of ice-water, the organic phase is separated, washed once with 200 ml of water, once with 200 ml of saturated sodium bicarbonate solution, once with 200 ml of saturated sodium chloride solution, and dried over sodium sulfate. The drying agent is filtered off, the filtrate is slowly concentrated in a rotary evaporator, the distilled DCM is successively replaced with approximately 200 ml of methanol, the crystallized product is filtered off with suction, washed with a little methanol, and dried in vacuo. Yield: 52.2 g (95 mmol) 95%; Purity: approximately 97% by 1< H NMR. D) Cyanation

[0117] A well-stirred mixture of 55.0 g (100 mmol) S1 (step C), 21.5 g (240 mmol) copper(I) cyanide, 100 g glass beads (3 mm diameter) and 500 ml dimethylacetamide (DMAc) is heated to 150 °C for 24 h. The mixture is filtered off with suction while still hot through a bed of Celite pre-slurried with DMAc, the filtrate is largely concentrated, the residue is taken up in 500 ml DCM, washed twice with 300 ml of 5 N ammonia solution each time, twice with 300 ml of water each time, once with 200 ml saturated sodium chloride solution and dried over sodium sulfate. The desiccant is filtered through a silica gel bed pre-slurried with DCM, the filtrate is slowly concentrated in a rotary evaporator, the distilled DCM is successively replaced with approximately 200 ml of methanol, the crystallized product is filtered off with suction, washed with a little methanol, and dried in vacuo. Further purification is carried out by repeated hot extraction crystallization (conventional organic solvents or acetic acid).their combinations, preferably acetonitrile-DCM, 1:3 to 3:1 vv) or chromatography and fractional sublimation or annealing in high vacuum.

[0118] Yield: 24.1 g (63 mmol) 63%; Purity: approximately 99.9% by HPLC.

[0119] If a Hartwig-Buchwald or Ullmann coupling is carried out instead of a Suzuki coupling in step A), followed by the above-mentioned steps B), C) and D), the following compounds can be obtained: Example C1:

[0120]

[0121] Yield over all steps: 20.4 g (33 mmol) 33%; Purity: approximately 99.9% by HPLC. A) Ullmann coupling

[0122]

[0123] Procedure analogous to N. Liu et al., RCS Advances, 2004, 4(93), 51133. A well-stirred mixture of 39.6 g (100 mmol) 9,10-dihydro-4-iodo-9,10[1',2']-benzenoanthracen-1-ol [1370032-70-4], 33.5 g (105 mmol) 3,6-diphenyl-9H-carbazole [56525-79-2], 97.7 g (300 mmol) cesium carbonate, 953 mg (5 mmol) copper iodide, 100 g glass beads (3 mm diameter), 500 ml propionitrile is stirred under reflux for 24 h. After complete conversion, the residue is largely concentrated in vacuo, taken up in 800 ml of dichloromethane (DCM) and 300 ml of water, acidified with vigorous stirring and ice-cooling by slowly adding 300 ml of 2N aqueous HCl, separated, washed twice with 300 ml of water and once with 200 ml of saturated sodium chloride solution, and dried over sodium sulfate. The drying agent is filtered off through a silica gel bed pre-slurried with DCM, the filtrate is slowly concentrated in a rotary evaporator, and the distilled DCM is successively substituted with approx.200 ml of methanol, the crystallized product is filtered off with suction, washed with a little methanol, and dried in vacuo. Yield: 40.0 g (68 mmol) 68%; Purity: approximately 97% by 1< H-NMR.

[0124] The following connections can be represented analogously: e.g. Educt - boronic acid / ester product yield B2 5720-05-8 51 % B2 126747-14-6 56 % B3 123324-71-0 50 % B4 169126-63-0 57 % B5 1562418-16-9 55 % B6 5122-94-1 61 % B7 406482-73-3 60 5 B8 5122-95-2 54 % B9 914675-52-8 52 % B10 128388-545 55 % B11 1257248-43-3 63 % B12 881911-81-5 62 % B13 13922-41-3 58 % B14 1280709-91-2 57 % B15 372521-91-0 69 % B16 68572-87-2 60 % B17 1188094-10-1 57 % B18 146746-63-6 60 % B19 654664-63-8 66 % B20 1115639-92-3 63 % B21 1430392-46-3 60 % B22 1152130-45-4 62 % B23 359012-63-8 52 % B24 1253912-58-1 21 % B25 100124-06-9 53 % B26 402936-15-6 57 % B27 395087-89-5 55 % B28 162607-19-4 52 % B29 796071-96-0 60 % B30 1271726-52-3 52 % B31 1010068-85-5 50 % B32 2360830-98-2 55 % B33 2186731-24-6 56 % B34 1199349-99-9 58 % B35 1846603-10-8 63 % B36 2226031-08-7 57 % B37 108847-20-7 54 % B38 108847-24-1 51% B39 1245943-60-5 50 % B40 1307859-67-1 49 % B41 1115640-18-0 51 % B42 1821151-81-8 56 % B43 333432-28-3 59 % B44 236389-21-2 57 % B45 1251773-34-8 56 % B46 1246022-50-3 52 % B47 1316311-18-8 48 % B48 1637323-21-7 44 % B49 1257248-19-3 47 % B50 1375111-22-0 50 % B51 2448326-07-4 46 % B52 1351870-19-3 50 % B53 1454807-18-1 46 % B54 1637323-11-5 48 % B55 2448326-02-9 50 % B56 2448325-93-5 46 % B57 100124-07-0 45 % B58 41 % B59 943836-24-6 22 % B60 952514-79-3 59 % B61 867044-33-5 62 % B62 1269508-31-7 60 % B63 1219956-23-6 65 % B64 2168567-62-0 63 % B65 1361094-91-8 60 % B66 2138490-96-5 56 % C2 2569012-63-9 37 % C3 37500-95-1 34 % C4 2036293-60-2 40 % C5 910897-97-1 29% C6 1259484-54-2 31 % C7 1257248-57-9 38 % C8 1257220-49-7 35 % C9 1346669-43-9 37 % C10 1419577-64-2 33 % C11 1567814-86-1 35 % C12 955959-91-8 30 % C13 31 % C14 51-17-2 36 % C15 28890-99-5 30 % C16 19 % 2) Synthesis of 1,4-dicyano-triptycenes: Example B100:

[0125] A) Iodination

[0126]

[0127] A well-stirred solution of 29.5 g (100 mmol) of 9,10-dihydro-4-hydroxy-9,10[1',2']-benzenoanthracene-1-carbonitrile [1370032-71-5] in 300 ml of trifluoroethanol (TFE) was added portionwise to 22.5 g (100 mmol) of N-iodosuccinimide [516-12-1] and stirred at RT for 6 h. After complete conversion, the residue was concentrated in vacuo, taken up in 500 ml of dichloromethane (DCM) and 300 ml of water, the organic phase was separated, washed twice with 300 ml of water, once with 200 ml of saturated sodium chloride solution, and dried over sodium sulfate. The drying agent is filtered off, the filtrate is slowly concentrated in a rotary evaporator, the distilled DCM is successively replaced with approximately 150 ml of methanol, the crystallized product is filtered off with suction, washed with a little methanol, and dried in vacuo. Yield: 37.9 g (90 mmol) 90%; Purity: approximately 97% by 1< H NMR. B) Triflatization

[0128]

[0129] A solution of 42.1 g (100 mmol) of S100 (step A) in 500 ml of DCM, cooled to 5 °C, is treated with 20.9 ml (150 mmol) of triethylamine and then dropwise with 20.2 ml (120 mmol) of trifluoromethanesulfonic anhydride. The mixture is stirred for 30 min at 5 °C, allowed to warm to RT, stirred for 1 h, carefully hydrolyzed with 300 ml of ice-water, and the organic phase is separated, washed once with 200 ml of water, once with 200 ml of saturated sodium bicarbonate solution, once with 200 ml of saturated sodium chloride solution, and dried over sodium sulfate. The drying agent is filtered off, the filtrate is slowly concentrated in a rotary evaporator, the distilled DCM is successively replaced with approximately 200 ml of methanol, the crystallized product is filtered off with suction, washed with a little methanol, and dried in vacuo. Yield: 52.6 g (95 mmol) 95%; Purity: approximately 97% by 1< H NMR. C) Suzuki clutch

[0130]

[0131] A well-stirred mixture of 55.3 g (100 mmol) S100 (stage B), 12.8 g (105 mmol) phenylboronic acid [98-80-6], 21.2 g (200 mmol) sodium carbonate, 0.72 g (1 mmol) bis(triphenylphosphino)palladium dichloride (alternatively, tetrakistriphenylphosphinopalladium(0) or S-Phos, X-Phos, RuPhos, AmPhos in combination with palladium acetate can be used), 100 g glass beads (3 mm diameter), 400 ml acetonitrile and 400 ml methanol is stirred for 16 h at 50 °C. After complete conversion, the residue is largely concentrated in vacuo, taken up in 500 ml dichloromethane (DCM) and 300 ml water, and the org. The phase is separated, washed twice with 300 ml of water, once with 200 ml of saturated sodium chloride solution, and dried over sodium sulfate. The drying agent is filtered off through a silica gel bed pre-slurried with DCM, the filtrate is slowly concentrated in a rotary evaporator, and the distilled DCM is successively substituted with approx.200 ml of methanol, the crystallized product is filtered off with suction, washed with a little methanol, and dried in vacuo. Yield: 45.4 g (90 mmol) 90%; Purity: approximately 97% by 1< H-NMR. D) Cyanation

[0132] A well-stirred mixture of 50.4 g (100 mmol) S100 (stage C), 10.8 g (120 mmol) copper(I) cyanide, 100 g glass beads (3 mm diameter) and 500 ml dimethylacetamide (DMAc) is heated to 150 °C for 24 h. While still hot, the mixture is filtered off with suction through a bed of Celite pre-slurried with DMAc, the filtrate is largely concentrated, the residue is taken up in 500 ml DCM, washed twice with 300 ml of 5 N ammonia solution each time, twice with 300 ml of water each time, once with 200 ml saturated sodium chloride solution and dried over sodium sulfate. The desiccant is filtered through a silica gel bed pre-slurried with DCM, the filtrate is slowly concentrated in a rotary evaporator, the distilled DCM is successively replaced with approximately 200 ml of methanol, the crystallized product is filtered off with suction, washed with a little methanol, and dried in vacuo. Further purification is carried out by repeated hot extraction crystallization (conventional organic solvents or acetic acid).combinations thereof, preferably acetonitrile-DCM, 1:3 to 3:1 vv) or chromatography and fractional sublimation or annealing under high vacuum. Yield: 26.9 g (71 mmol) 71%; Purity: approximately 99.9% by HPLC.

[0133] If the above steps are carried out in the order A) iodination, C) instead of a Suzuki coupling a Hartwig-Buchwald or Ullmann coupling (see below), followed by the steps B) triflatization and finally D) cyanation, the following compounds can be obtained: Example C100:

[0134]

[0135] Yield over all steps: 23.2 g (37 mmol) 37%; Purity: approximately 99.9% by HPLC. B) Ullmann coupling

[0136]

[0137] Procedure analogous to N. Liu et al., RCS Advances, 2004, 4(93), 51133. A well-stirred mixture of 42.1 g (100 mmol) (step A), 33.5 g (105 mmol) of 3,6-diphenyl-9H-carbazole [56525-79-2], 97.7 g (300 mmol) of cesium carbonate, 953 mg (5 mmol) of copper iodide, 100 g of glass beads (3 mm diameter), and 500 ml of propionitrile is stirred under reflux for 24 h. After complete conversion, the mixture is largely concentrated in vacuo, taken up in 800 ml of DCM and 300 ml of water, acidified by slow addition of 300 ml of 2N aqueous HCl with thorough stirring and ice-cooling, and the org. The phase is separated, washed twice with 300 ml of water, once with 200 ml of saturated brine, and dried over sodium sulfate. The drying agent is filtered off through a silica gel bed pre-slurried with DCM. The filtrate is slowly concentrated in a rotary evaporator. The distilled DCM is successively replaced with approximately 200 ml of methanol. The crystallized product is filtered off with suction, washed with a little methanol, and dried in vacuo. Yield: 45.9 g (75 mmol) 75%; purity: approx. 97% according to 1< H-NMR.

[0138] The following connections can be represented analogously: e.g. Educt - boronic acid / ester product yield B101 5720-05-8 51 % B102 126747-14-6 50 % B103 123324-71-0 55 % B104 169126-63-0 55 % B105 1562418-16-9 53 % B106 5122-94-1 58 % B107 406482-73-3 56 % B108 5122-95-2 53 % B109 914675-52-8 50 % B110 128388-545 60 % B111 1257248-43-3 58 % B112 881911-81-5 62 % B113 13922-41-3 60 % B114 1280709-91-2 62 % B115 372521-91-0 63 % B116 68572-87-2 65 % B117 1188094-10-1 65 % B118 146746-63-6 63 % B119 654664-63-8 67 % B120 1115639-92-3 63 % B122 1430392-46-3 60 % B123 1152130-45-4 62 % B124 359012-63-8 57 % B125 100124-06-9 55 % B126 402936-15-6 54 % B127 395087-89-5 57 % B128 162607-19-4 52 % B129 796071-96-0 55 % B130 1271726-52-3 57 % B131 1010068-85-5 54 % B132 2360830-98-2 56 % B133 2186731-24-6 59 % B134 1199349-99-9 58 % B135 1846603-10-8 64 % B136 2226031-08-7 60 % B137 108847-20-7 56 % B138 108847-24-1 57 % B139 1245943-60-5 53 % B140 1307859-67-1 56 % B141 1115640-18-0 51 % B142 1821151-81-8 63 % B143 333432-28-3 55 % B144 236389-21-2 57 % B145 1251773-34-8 53 % B146 1246022-50-3 50 % B147 854952-58-2 57 % B148 81359833-28-5 60 % B149 1416814-68-0 59 % B150 1391729-66-0 64 % B151 1316311-17-7 63 % B152 1133057-98-3 59 % B153 1133057-97-2 55 % B154 1547397-15-8 53 % B155 1637323-05-7 60 % B156 1373359-67-1 57 % B157 1373359-70-6 64 % B158 918137-86-7 60 % B159 1813537-15-3 60 % B160 1001911-63-2 56 % B161 1370555-65-9 54 % B162 1333002-41-7 51 % B163 1240963-55-6 60 % B164 419536-33-7 63 % B165 1398394-82-5 60 % B166 854952-60-6 60 % B167 864377-33-3 57 % B168 1369587-64-3 62 % B169 1189047-28-6 53 % B170 1369369-44-7 60 % B171 1454807-26-1 59 % B172 2068731-68-8 55 % B173 1289472-63-4 54 % B174 854952-51-5 64 % B175 100124-07-0 56 % B176 108847-21-8 49 % B177 201802-67-7 53 % B178 1084334-86-0 56 % B179 943836-24-6 59 % B180 1608462-54-9 56 % B181 950986-07-9 59 % B182 1265177-27-2 63 % B183 1959599-90-6 60 % B184 2410401-87-3 55 % B185 1648570-88-0 60 % B186 2126887-02-1 63 % B187 1428329-78-5 57 % B188 1960443-69-9 60 % B189 1246021-61-3 53 % B190 1421701-43-0 65 % B191 1825336-99-9 64 % B192 1620895-07-9 65 % B193 1246021-67-9 60 % B194 943899-12-5 57 % B195 1776936-65-2 59 % B196 1610950-84-9 60 % B197 2334467-29-5 57 % B198 962514-79-3 60 % B199 867044-33-5 62 % B200 1269508-31-7 58 % B201 1219956-23-6 64 % B202 2168567-62-0 61 % B203 1361094-91-8 59 % B204 2138490-96-5 50 % C101 1326650-26-3 43 % C102 2265205-18-1 29 % C103 1269266-70-7 36 % C104 1365891-56-0 33 % C105 1439927-87-3 39 % C106 1807860-06-5 38 % C107 2055969-54-3 40 % C108 102113-98-4 37 % C109 955959-89-4 35 % C110 a 2088681-91-6 21 % C110 b 18 % C111 2470374-39-9 38 % C112 2641780-78-9 20 % C113 2172957-83-2 27 % Example: Production of OLEDs 1) Vacuum-processed devices:

[0139] 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).

[0140] The following examples present the results of various OLEDs. Cleaned glass plates (cleaned in a Miele laboratory dishwasher using 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 Components - BF:

[0141] The compounds according to the invention can be used in the electron transport layer (ETL) and the hole blocking layer (HBL). All materials are thermally vapor-deposited in a vacuum chamber. The emission layer (EML) always consists of at least one matrix material (host material) SMB (see Table 1) and an emitting dopant (emitter) D, which is admixed to 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 produce the OLEDs are shown in Table 5.

[0142] OLEDs are characterized as standard. For this purpose, the electroluminescence spectra, current efficiency (measured in cd / A), power efficiency (measured in lm / W), and external quantum efficiency (EQE, measured in percent) are determined as a function of luminance, calculated from current-voltage-luminance (IUL) curves 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. The lifetime is determined at an initial luminance of 10000 cd / m². The LT80 value in (h) is the measured time for the brightness to decay to 80% of the initial brightness. The OLEDs have the following layer structure: Substrat

[0143] Hole injection layer (HIL) made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm hole transport layer (HTL) made of HTM1, 180 nm electron blocking layer (EBL) made of EBM1, 10 nm emission layer (EML), see Table 1. Hole blocking layer (HBL), see Table 1. Electron transport layer (ETL), see Table 1. Electron injection layer (EIL) made of ETM2, 1 nm cathode made of aluminum, 100 nm Table 1: Structure of blue fluorescent OLED components e.g. EML thickness HBL thickness ETL thickness BF1 SMB1:D1 (95%:5%) HBM1 B4:ETM2 (50%:50%) 20 nm 5 nm 30 nm BF2 SMB1:D1 (95%:5%) HBM1 B21:ETM2 (50%:50%) 20 nm 5 nm 30 nm BF3 SMB1:D1 (95%:5%) HBM1 B30:ETM2 (50%:50%) 20 nm 10 nm 30 nm BF4 SMB1:D1 (95%:5%) B36 ETM1:ETM2 (50%:50%) 20 nm 5 nm 30 nm BF5 SMB1:D1 (95%:5%) B36 B30:ETM2 (50%:50%) 20 nm 5 nm 30 nm BF6 SMB1:D1 (95%:5%) B136 B30:ETM2 (50%:50%) 20 nm 5 nm 30 nm BF7 SMB1:D1 (95%:5%) B136 B136:ETM2 (50%:50%) 20 nm 5 nm 30 nm Table 2: Results of blue fluorescent OLED devices e.g. EQE (%) 1000 cd / m 2 Voltage (V) 1000 cd / m 2< LT80 (h) 10000 cd / m 2 BF1 6.7 3.9 55 BF2 6.5 4.0 50 BF3 6.6 4.0 45 BF4 6.5 3.9 60 BF5 7.1 3.8 50 BF6 6.9 3.9 50 BF7 7.0 3.8 65 1b) Phosphorescent OLED components:

[0144] The compounds according to the invention can be used in the electron transport layer (ETL), the hole blocking layer (HBL), and in the emission layer (EML) as matrix material (host material) M (see Table 5) or (Table 3). 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 admixed 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 fabricate the OLEDs are shown in Table 5.

[0145] OLEDs are characterized as standard. For this purpose, the electroluminescence spectra, current efficiency (measured in cd / A), power efficiency (measured in λm / W), and external quantum efficiency (EQE, measured in percent) are determined as a function of luminance, calculated from current-voltage-luminance (IUL) curves 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. The lifetime is determined at an initial luminance of 1000 cd / m² for blue- and red-emitting components, and 10000 cd / m² for green- and yellow-emitting components. The LT80 value in (h) is the measured time for the brightness to decay to 80% of the initial brightness. The OLEDs have the following layer structure: Substrat

[0146] Hole injection layer (HIL) made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm Hole transport layer (HTL) made of HTM1, 180 nm for blue, 50 nm for green, 40 nm for yellow, 90 nm for red Electron blocking layer (EBL) 20 nm made of EBM2 for blue, 20 nm made of EBM1 for green and yellow, 10 nm for red Emission layer (EML), see Table 3 Hole blocking layer (HBL), see Table 3 Electron transport layer (ETL), see Table 3 Electron injection layer (EIL) made of ETM2, 1 nm Cathode made of aluminum, 100 nm Table 3: Structure of phosphorescent OLED components e.g. EML thickness HBL thickness ETL thickness Blue BP1 M3:M4:IrB1 (30%:65%:5%) B46 ETM1:ETM2 (50%:50%) 25 nm 5 nm 30 nm BP2 M3:M4:IrB1 (30%:65%:5%) B46 B46:ETM2 (50%:50%) 25 nm 5 nm 30 nm BP3 B9:M4:IrB1 ETM1:ETM2 (40%:60%:5%) 25 nm 5 nm HBM2 (50%:50%) 30 nm BP4 B52:M4:IrB1 (30%:65%:5%) HBM2 ETM1:ETM2 (50%:50%) 25 nm 5 nm 30 nm Green GP1 M1:M2:IrG1 (30%:60%:10%) B18 ETM1:ETM2 (50%:50%) 40 nm 5 nm 30 nm GP2 M1:M2:IrG1 (30%:60%:10%) B44 ETM1:ETM2 (50%:50%) 40 nm 5 nm 30 nm GP3 B47:M2:IrG1 (30%:60%:10%) HBM1 ETM1:ETM2 (50%:50%) 40 nm 5 nm 30 nm GP4 B51:M2:IrG1 (35%:65%:10%) HBM1 ETM1:ETM2 (50%:50%) 40 nm 5 nm 30 nm Yellow GP50 M1:M2:IrG2 (22%:66%:12%) B43 ETM1:ETM2 (50%:50%) 40 nm 5 nm 30 nm GP51 M1:M2:IrG2 (22%:66%:12%) B54 ETM1:ETM2 (50%:50%) 40 nm 5 nm 30 nm GP52 B48:M2:IrG2 (22%:66%:12%) HBM1 ETM1:ETM2 (50%:50%) 40 nm 5 nm 30 nm GP53 <h2 style=";text-align:left;direction:ltr">B49:M2:IrG2 (22%:66%:12%) <h2 style=";text-align:left;direction:ltr"> HBM1 <h2 style=";text-align:left;direction:ltr"> ETM1:ETM2 (50%:50%) <h2 style=";text-align:left;direction:ltr"> 40 nm <h2 style=";text-align:left;direction:ltr"> 5 nm <h2 style=";text-align:left;direction:ltr"> 30 nm <h2 style=";text-align:left;direction:ltr"> GP54 <h2 style=";text-align:left;direction:ltr"> B50:M2:IrG2 (22%:66%:12%) <h2 style=";text-align:left;direction:ltr"> HBM1 <h2 style=";text-align:left;direction:ltr"> ETM1:ETM2 (50%:50%) <h2 style=";text-align:left;direction:ltr"> 40 nm <h2 style=";text-align:left;direction:ltr"> 5 nm <h2 style=";text-align:left;direction:ltr"> 30 nm <h2 style=";text-align:left;direction:ltr"> GP55 <h2 style=";text-align:left;direction:ltr"> B55:M2:IrG2 (30%:60%:10%) <h2 style=";text-align:left;direction:ltr"> HBM1 <h2 style=";text-align:left;direction:ltr"> ETM1:ETM2 (50%:50%) <h2 style=";text-align:left;direction:ltr"> 40 nm <h2 style=";text-align:left;direction:ltr"> 5 nm <h2 style=";text-align:left;direction:ltr"> 30 nm <h2 style=";text-align:left;direction:ltr"> GP56 <h2 style=";text-align:left;direction:ltr"> B56:M2:IrG2 (22%:66%:12%) <h2 style=";text-align:left;direction:ltr"> HBM1 <h2 style=";text-align:left;direction:ltr"> ETM1:ETM2 (50%:50%) <h2 style=";text-align:left;direction:ltr"> 40 nm <h2 style=";text-align:left;direction:ltr"> 5 nm <h2 style=";text-align:left;direction:ltr"> 30 nm <h2 style=";text-align:left;direction:ltr"> GP57 <h2 style=";text-align:left;direction:ltr"> B151:M2:IrG2 (22%:66%:12%) <h2 style=";text-align:left;direction:ltr"> HBM1 <h2 style=";text-align:left;direction:ltr"> ETM1:ETM2 (50%:50%) <h2 style=";text-align:left;direction:ltr"> 40 nm <h2 style=";text-align:left;direction:ltr"> 5 nm <h2 style=";text-align:left;direction:ltr"> 30 nm <h2 style=";text-align:left;direction:ltr"> GP58 <h2 style=";text-align:left;direction:ltr"> B157:M2:IrG2 (22%:66%:12%) <h2 style=";text-align:left;direction:ltr"> HBM1 <h2 style=";text-align:left;direction:ltr"> ETM1:ETM2 (50%:50%) <h2 style=";text-align:left;direction:ltr"> 40 nm <h2 style=";text-align:left;direction:ltr"> 5 nm <h2 style=";text-align:left;direction:ltr"> 30 nm <h2 style=";text-align:left;direction:ltr"> GP59 <h2 style=";text-align:left;direction:ltr"> B158:M2:IrG2 (40%:50%:10%) <h2 style=";text-align:left;direction:ltr"> HBM1 <h2 style=";text-align:left;direction:ltr"> ETM1:ETM2 (50%:50%) <h2 style=";text-align:left;direction:ltr"> 40 nm <h2 style=";text-align:left;direction:ltr"> 5 nm <h2 style=";text-align:left;direction:ltr"> 30 nm <h2 style=";text-align:left;direction:ltr"> Rot <h2 style=";text-align:left;direction:ltr"> RP1 <h2 style=";text-align:left;direction:ltr"> M5:IrR1 (92%:8%) <h2 style=";text-align:left;direction:ltr"> HBM1 <h2 style=";text-align:left;direction:ltr"> B60:ETM2 (50%:50%) <h2 style=";text-align:left;direction:ltr"> 35 nm <h2 style=";text-align:left;direction:ltr"> 10 nm <h2 style=";text-align:left;direction:ltr"> 30 nm <h2 style=";text-align:left;direction:ltr"> RP2 <h2 style=";text-align:left;direction:ltr"> M5:IrR1 (92%:8%) B65 <h2 style=";text-align:left;direction:ltr"> ETM1:ETM2 (50%:50%) <h2 style=";text-align:left;direction:ltr"> 5 nm <h2 style=";text-align:left;direction:ltr"> 35 nm <h2 style=";text-align:left;direction:ltr"> 30 nm <h2 style=";text-align:left;direction:ltr"> RP3 <h2 style=";text-align:left;direction:ltr"> M5:IrR1 (92%:8%) B66 <h2 style=";text-align:left;direction:ltr"> B60:ETM2 (50%:50%) <h2 style=";text-align:left;direction:ltr"> 35 nm <h2 style=";text-align:left;direction:ltr"> 5 nm <h2 style=";text-align:left;direction:ltr"> 30 nm <h2 style=";text-align:left;direction:ltr"> RP4 <h2 style=";text-align:left;direction:ltr"> M5:IrR1 (92%:8%) B203 <h2 style=";text-align:left;direction:ltr"> B60:ETM2 (50%:50%) <h2 style=";text-align:left;direction:ltr"> 35 nm <h2 style=";text-align:left;direction:ltr"> 5 nm <h2 style=";text-align:left;direction:ltr"> 30 nm <h2 style=";text-align:left;direction:ltr"> RP5 <h2 style=";text-align:left;direction:ltr"> B59:IrR1 (92%:8%) <h2 style=";text-align:left;direction:ltr"> HBM1 <h2 style=";text-align:left;direction:ltr"> ETM1:ETM2 (50%:50%) <h2 style=";text-align:left;direction:ltr"> 35 nm <h2 style=";text-align:left;direction:ltr"> 10 nm <h2 style=";text-align:left;direction:ltr"> 30 nm <h2 style=";text-align:left;direction:ltr"> RP6 <h2 style=";text-align:left;direction:ltr"> B156:IrR1 (92%:8%) <h2 style=";text-align:left;direction:ltr"> HBM1 <h2 style=";text-align:left;direction:ltr"> ETM1:ETM2 (50%:50%) <h2 style=";text-align:left;direction:ltr"> 35 nm <h2 style=";text-align:left;direction:ltr"> 10 nm <h2 style=";text-align:left;direction:ltr"> 30 nm <h2 style=";text-align:left;direction:ltr"> RP7 <h2 style=";text-align:left;direction:ltr"> C9:IrR1 (90%:10%) <h2 style=";text-align:left;direction:ltr"> HBM1 <h2 style=";text-align:left;direction:ltr"> ETM1:ETM2 (50%:50%) <h2 style=";text-align:left;direction:ltr"> 35 nm <h2 style=";text-align:left;direction:ltr"> 10 nm <h2 style=";text-align:left;direction:ltr"> 30 nm <h2 style=";text-align:left;direction:ltr"> RP8 <h2 style=";text-align:left;direction:ltr"> C11:IrR1 (90%:10%) <h2 style=";text-align:left;direction:ltr"> HBM1 <h2 style=";text-align:left;direction:ltr"> ETM1:ETM2 (50%:50%) <h2 style=";text-align:left;direction:ltr"> 35 nm <h2 style=";text-align:left;direction:ltr"> 10 nm <h2 style=";text-align:left;direction:ltr"> 30 nm <h2 style=";text-align:left;direction:ltr"> RP9 <h2 style=";text-align:left;direction:ltr"> C101:IrR1 (90%:10%) <h2 style=";text-align:left;direction:ltr"> HBM1 <h2 style=";text-align:left;direction:ltr"> ETM1:ETM2 (50%:50%) <h2 style=";text-align:left;direction:ltr"> 35 nm <h2 style=";text-align:left;direction:ltr"> 10 nm <h2 style=";text-align:left;direction:ltr"> 30 nm Table 4: Results of phosphorescent OLED devices Blue e.g. EQE (%) 1000 cd / m 2 Voltage (V) 1000 cd / m 2< LT80 (h) 1000 cd / m 2 BP1 23.4 4.2 190 BP2 23.6 4.1 210 BP3 23.5 4.0 180 BP4 20.1 4.0 145 Green e.g. EQE (%) 1000 cd / m 2 Voltage (V) 1000 cd / m 2< LT80 (h) 10000 cd / m 2 GP1 23.0 3.1 3000 GP2 23.3 3.2 3300 GP3 23.2 3.3 3100 GP4 22.4 3.3 3000 Yellow GP50 31.5 3.0 16000 GP51 31.2 3.1 17500 GP52 30.5 2.9 15000 GP53 30.3 3.0 16500 GP54 30.6 3.1 16000 GP55 31.7 3.2 14000 GP56 30.9 2.9 16000 GP57 30.3 2.8 15000 GP58 30.5 2.7 15000 GP59 31.5 2.8 14000 Red e.g. EQE (%) 1000 cd / m 2 Voltage (V) 1000 cd / m 2< LT80 (h) 1000 cd / m 2 RP1 17.6 3.4 12000 RP2 17.2 3.4 17000 RP3 17.3 3.2 18000 RP4 16.9 3.0 17500 RP5 16.9 3.1 20000 RP6 17.0 3.1 21000 FP7 16.2 3.4 12000 RP8 16.0 3.5 13000 RP9 16.5 3.3 11000 Table 5: Structural formulas of the materials used HTM1 EBM1 1365840-52-3 1450933-44-4 EBM2 M1 1206465-62-4 1822310-86-0 M2 M3 = HBM2 1643479-47-3 1201800-83-0 M4 M5 342638-54-4 1398395-92-0 HBM1 1955543-57-3 <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> ETM2 <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr"> SMB3 25387-93-3 1627916-48-6 Fluorescent Blue Phosphorescent Blue D1 1827604-67-0 IrB1 1541114-98-0 Phosphorescent Green Phosphorescent Yellow IrG1 IrG2 2245866-06-0 2245945-28-0 Phosphorescent Deep Red IrR1 1562420-79-4

Claims

1. Compound of the formula (1), and enantiomers thereof, where the following applies to the symbols used: X is, identically or differently on each occurrence, CR or N, with the proviso that a maximum of two groups X per ring stand for N; Q is, identically or differently on each occurrence, C-CN or CR', with the proviso that two groups Q stand for C-CN. R' is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R1; R is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(Ar')2, N(R1)2, OAr', SAr', B(OR1)2, CHO, C(=O)R1, CR1=C(R1)2, CN, C(=O)OR1, C(=O)NR1, Si(R1)3, NO2, P(=O)(R1)2, OSO2R1, OR1, S(=O)R1, S(=O)2R1, SR1, 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 in each case be substituted by one or more radicals R1, where one or more non-adjacent CH2 groups may be replaced by -R1C=CR1-, -C=C-, Si(R1)2, NR1, CONR1, C=O, C=S, -C(=O)O-, P(=O)(R1), -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, which may in each case be substituted by one or more radicals R1, where two or more radicals R, which are preferably bonded to the same ring, may form with one another an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more radicals R1; Ar' is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R1; R1 is on each occurrence, identically or differently, H, D, F, I, B(OR2)2, N(R2)2, CHO, C(=O)R2, CR2=C(R2)2, CN, C(=O)OR2, Si(R2)3, NO2, P(=O)(R2)2, OSO2R2, SR2, OR2, S(=O)R2, S(=O)2R2, 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 in each case be substituted by one or more radicals R2 and where one or more CH2 groups in the above-mentioned groups may be replaced by -R2C=CR2-, -C≡C-, Si(R2)2, C=O, C=S, -C(=O)O-, NR2, CONR2, P(=O)(R2), -O-, -S-, SO or SO2 and where 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, which may in each case be substituted by one or more radicals R2, where two or more radicals R1 may form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system with one another; R2 is on each occurrence, identically or differently, H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by D or F; two or more substituents R2 may be linked to one another and form a ring.

2. Compound according to Claim 1, selected from the compound of the formula (2) and enantiomers thereof, where the symbols used have the meanings given in Claim 1, with the proviso that Q stands once for CR' and once for C-CN.

3. Compound according to one or more of Claims 1 or 2, selected from the compounds of the formulae (2-1) and (2-2), and enantiomers thereof, where the symbols used have the meanings given in Claim 2.

4. Process for the preparation of a compound according to one or more of Claims 1 to 3, characterised by the following steps: (A) synthesis of the skeleton of the formula (1); (B) introduction of the radicals CN and R'.

5. Oligomer, polymer or dendrimer comprising one or more compounds of the formula (1) according to one or more of Claims 1 to 3, where the bond(s) to the oligomer, polymer or dendrimer can take place at any desired positions in formula (1).

6. Formulation comprising at least one compound according to one or more of Claims 1 to 3 and at least one further compound and / or at least one solvent.

7. Use of a compound according to one or more of Claims 1 to 3 and / or a formulation according to Claim 6 in an electronic device.

8. Electronic device containing at least one compound according to one or more of Claims 1 to 3 and / or at least one oligomer, polymer or dendrimer according to Claim 5.

9. Electronic device according to Claim 8, which is an organic electroluminescent device, characterised in that the device comprises an anode, a cathode and at least one emitting layer, where at least one organic layer, which can 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 of the formula (1).