INDOLO[3.2.1-JK]CARBAZOLE-6-CARBONITRILE DERIVATIVES AS BLUE FLUORESCENT EMISSANTS FOR USE IN OLEDS

Description

[0001] The present invention relates to aromatic compounds for use in electronic devices, in particular in organic electroluminescent devices, and to electronic devices, in particular organic electroluminescent devices, containing these aromatic compounds.

[0002] In organic electroluminescence devices, phosphorescent organometallic complexes or fluorescent compounds are frequently used as emitting materials. Generally, there is still room for improvement in electroluminescence devices.

[0003] Polycyclic compounds that can be used in organic electroluminescent devices are known from US 2010 / 0051928, WO 2010 / 104047 A1, US 2014 / 319507 A1, WO 2017 / 175690, US 2019 / 0393439, CN 110452226 A, WO 2019 / 132506 A1 and WO 2020 / 064666 A1. Indolo[3.2.1-jk]carbazole-6-carbonitrile derivatives are known as emitters for use in OLEDs from WO 2019 / 194617 A and WO 2019 / 111971 A1. John B. Henry et al. (Henry, John B. et al., The Journal of Physical Chemistry A, Vol. 115, No. 21, pages 5435-5442 (2011)) describes Indolo[3.2.1-jk]carbazole-5-carbonitrile as an emitter for use in OLEDs.

[0004] In general, there is still room for improvement with these heterocyclic compounds, for example for use as emitters, especially as fluorescent emitters, particularly with regard to lifetime, color purity, but also with regard to the efficiency and operating voltage of the device.

[0005] The object of the present invention is therefore to provide compounds which are suitable for use in an organic electronic device, in particular in an organic electroluminescence device, and which lead to good device properties when used in this device, as well as to provide the corresponding electronic device.

[0006] In particular, the object of the present invention is to provide connections that lead to a long service life, good efficiency and low operating voltage.

[0007] Furthermore, the compounds should exhibit excellent processability, and in particular, good solubility.

[0008] A further object of the present invention can be seen as providing compounds suitable for use in phosphorescent or fluorescent electroluminescent devices, in particular as emitters. In particular, it is an object of the present invention to provide emitters suitable for red, green, or blue electroluminescent devices, preferably for blue electroluminescent devices.

[0009] Furthermore, the compounds, especially when used as emitters in organic electroluminescent devices, should lead to devices that exhibit excellent color purity.

[0010] Another task can be seen as providing electronic devices with excellent performance as cost-effectively and with consistent quality as possible.

[0011] Furthermore, the electronic devices should be usable or adaptable for many purposes. In particular, the performance of the electronic devices should be maintained over a wide temperature range.

[0012] Surprisingly, it was found that certain compounds, described in more detail below, solve this problem, are very well suited for use in electroluminescent devices, and lead to organic electroluminescent devices that exhibit excellent properties, particularly with regard to lifetime, color purity, efficiency, and operating voltage. These compounds, as well as electronic devices, especially organic electroluminescent devices containing such compounds, are therefore the subject of the present invention.

[0013] The subject of the present invention is a compound according to formula (I), where the following applies to the symbols used: X, in each occurrence, represents N, C-CN, CYR y< or CR b< , preferably N, C-CN, or CYR y< , particularly preferably C-CN; Y, in each occurrence, represents CO, P(=O)R a< , SO, SO 2 , C(O)O, C(S)O, C(O)S, C(=O)NR a< , C(=O)NAr, preferably CO, P(=O)R a< , SO, SO 2 , particularly preferably CO; Is the same or different in each occurrence H, D, OH, F, Cl, Br, I, CN, NO 2 , N(Ar) 2 , N(R e< ) 2 , C(=O)N(Ar) 2 , C(=O)N(R e< ) 2 , C(Ar) 3 , C(R e< ) 3 , Si(Ar)3, Si(R e< ) 3 , B(Ar) 2 , B(R e< ) 2 , C(=O)Ar, C(=O)R e< , P(=O)(Ar) 2 , P(=O)( R e< ) 2 , P(Ar) 2 , P(R e< ) 2 , S(=O)Ar, S(=O)R e< , S(=O) 2 Ar, S(=O) 2 R e< , OSO 2 Ar, OSO 2 R e< , a straight-chain alkyl or alkoxy group with 1 to 40 C atoms or a branched or cyclic alkyl or alkoxy group with 3 to 20 C atoms, wherein the alkyl or alkoxy group may be substituted with one or more R e< residues,or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R e< residues, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted by one or more R e< residues, or an arylthio or heteroarylthio group with 5 to 60 aromatic ring atoms, which may be substituted by one or more R e< residues, or a diarylamino, arylheteroarylamino, diheteroarylamino group with 5 to 60 aromatic ring atoms, which may be substituted by one or more R e< residues, or an arylalkyl or heteroarylalkyl group with 5 to 60 aromatic ring atoms and 1 to 10 C atoms in the alkyl residue, which may be substituted by one or more R e< residues; In this process, a remainder R can be combined with another group,preferably R d< form a ring system; Arist, in each occurrence the same or different, is an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which may be substituted with one or more R e< residues, wherein two Ar residues bonding to the same C atom, Si atom, N atom, P atom or B atom may also be bridged by a single bond or a bridge selected from B(R e< ), C(R e< ) 2 , Si(R e< ) 2 , C=O, C=NR e< , C=C(R e< ) 2 , O, S, S=O, SO 2 , N(R e< ), P(R e< ) and P(=O)R e< , to each other; R a< , R b< , R c< , R d< , Re< is the same or different in each occurrence H, D, OH, F, Cl, Br, I, CN, NO 2 , N(Ar') 2 , N(R 1< ) 2 , C(=O)N(Ar') 2 , C(=O)N(R 1< ) 2 , C(Ar') 3 , C(R 1< ) 3 , Si(Ar') 3 , Si(R 1< ) 3 , B(Ar') 2 , B(R 1< ) 2 , C(=O)Ar', C(=O)R 1< , P(=O)(Ar') 2 , P(=O)(R 1< ) 2 , P(Ar') 2 , P(R 1< ) 2, S(=O)Ar', S(=O)R 1< , S(=O) 2 Ar', S(=O) 2 R 1< , OSO 2 Ar', OSO 2 R 1< ,a straight-chain alkyl or alkoxy group with 1 to 40 carbon atoms, or a branched or cyclic alkyl or alkoxy group with 3 to 20 carbon atoms, wherein the alkyl or alkoxy group may be substituted with one or more R1< groups, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R1< groups, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted by one or more R1< groups; wherein two R1< groups, ... R y< is the same or different in each occurrence: C(Ar') 3 , C(R 1< ) 3 , Si(Ar') 3 , Si(R 1< ) 3 , N(Ar') 2 , N(R 1< ) 2 , a straight-chain alkyl or alkoxy group with 1 to 40 C atoms or a branched or cyclic alkyl or alkoxy group with 3 to 20 C atoms,wherein the alkyl or alkoxy group can each be substituted with one or more R 1< residues, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which can be substituted by one or more R 1< residues; wherein two R y< residues can also form a ring system with each other or one R y< residue with a R a< , R b< , R c< , R d< , R e< residue, preferably a R a< ; Ar' is, in each occurrence, the same or different, an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which may be substituted with one or more R1< substituents. Two Ar' substituents bonding to the same C, Si, N, P, or B atom may also be connected by a single bond or a bridge selected from B(R1<), C(R1<)2, Si(R1<)2, C=O, C=NR1<, C=C(R1<)2, O, S, S=O, SO2, N(R1<), P(R1<), and P(=O)R1<.be bridged with each other; R1< is the same or different in each occurrence: H, D, F, Cl, Br, I, CN, NO2, N(Ar")2, N(R2<)2, C(=O)Ar, C(=O)R2<, P(=O)(Ar")2, P(Ar")2, B(Ar")2, B(R2<)2, C(Ar")3, C(R2<)3, Si(Ar")3, Si(R2<)3, a straight-chain alkyl or alkoxy group with 1 to 40 carbon atoms, or a branched or cyclic alkyl or alkoxy group with 3 to 40 carbon atoms, each of which may be substituted with one or more R2< groups, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 2< groups, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 2< groups, or an aralkyl or heteroaralkyl group with 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 2< groups,or a combination of these systems; wherein two or more, preferably adjacent residues R 1< can form a ring system together, wherein one or more residues R 1< can form a ring system with a further part of the compound; Ar" is, in each occurrence, the same or different aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which may be substituted with one or more R 2< substituents. Two Ar" substituents bonding to the same C atom, Si atom, N atom, P atom, or B atom may also be bridged by a single bond or a bridge selected from B(R 2< ), C(R 2< ) 2 , Si(R 2< ) 2 , C=O, C=NR 2< , C=C(R 2< ) 2 , O, S, S=O, SO 2 , N(R 2< ), P(R 2< ) and P(=O)R 2< . R 2< is, in each occurrence, the same or different selected from the group consisting of H, D, F, CN,an aliphatic hydrocarbon residue with 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, or CN, and which may be substituted by one or more alkyl groups, each with 1 to 4 carbon atoms, wherein two or more, preferably adjacent, substituents R<2> may form a ring system together, characterized in that two residues R form a condensed ring with the other groups to which the two residues R bind. Preferably, it can be provided that at least one, preferably at least two, of the residues R, R a , R b , R c , R d , R e are not equal to H preferably not equal to H, D, OH, NO 2 , F, Cl, Br, I. Equivalently, R is preferably chosen from CN, N(Ar) 2 , N(R in ) 2 , C(=O)N(Ar) 2 , C(=O)N(R in ) 2 , C(Ar) 3 , C(R in ) 3 , Si(Ar) 3 , Si(R in ) 3 , B(Ar) 2 , B(R in ) 2 , C(=O)Ar, C(=O)R in , P(=O)(Ar) 2 , P(=O)(R in ) 2 , Even) 2 , P(R in ) 2 , S(=O)Ar, S(=O)R in , S(=O) 2 Ar, S(=O) 2 R in , OSO 2 Ar, OSO 2 R e , a straight-chain alkyl or alkoxy group with 1 to 40 carbon atoms or a branched or cyclic alkyl or alkoxy group with 3 to 20 carbon atoms, wherein the alkyl or alkoxy group is each linked to one or more R groups e may be substituted, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each separated by one or more R groups e may be substituted, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, separated by one or more R groups e may be substituted, or an arylthio or heteroarylthio group with 5 to 60 aromatic ring atoms, separated by one or more R groups e may be substituted, or a diarylamino, arylheteroarylamino, diheteroarylamino group with 5 to 60 aromatic ring atoms, separated by one or more R groups e may be substituted, or an arylalkyl or heteroarylalkyl group with 5 to 60 aromatic ring atoms and 1 to 10 carbon atoms in the alkyl group, separated by one or more R groups e can be substituted; in this case, a residue R can be replaced by another group, preferably R d form a ring system; and / or at least one of the residues R a , R b , R c , R d , R e is preferably selected from CN, N(Ar') in the same or different way for each occurrence 2 , N(R 1 ) 2 , C(=O)N(Ar') 2 , C(=O)N(R 1 ) 2 , C(Ar') 3 , C(R 1 ) 3 , Si(Ar') 3 , Si(R 1 ) 3 , B(Ar') 2 , B(R 1 ) 2 , C(=O)Ar', C(=O)R 1 , P(=O)(Ar') 2 , P(=O)(R 1 ) 2 , P(Ar') 2 , P(R 1 ) 2 , S(=O)Ar', S(=O)R 1 , S(=O) 2 Ar', S(=O) 2 R 1 , OSO 2 Ar', OSO 2 R 1 , a straight-chain alkyl or alkoxy group with 1 to 40 carbon atoms or a branched or cyclic alkyl or alkoxy group with 3 to 20 carbon atoms, wherein the alkyl or alkoxy group is each linked to one or more R groups 1 may be substituted, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each separated by one or more R groups 1 may be substituted, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, separated by one or more R groups 1 can be substituted; in this case, two residues R can be involved. a , R b , R c , R d , R e also form a ring system with each other or with another group.

[0014] The previously stated explanations regarding preferred residues R a< must be taken into account.

[0015] Preferably, it can further be provided that at least one of the residues R c< , preferably both residues R c< , is / are not equal to H, wherein particularly preferably at least one of the residues R c< , preferably both residues R c< , is not equal to H, D, F, Cl, Br, I. The previously stated considerations regarding preferred residues R c< must be taken into account here.

[0016] Particularly preferably, it may be provided that at least one of the residues R a< and at least one of the residues R c< is not equal to H, preferably not equal to H, D, F, Cl, Br, I. Particularly preferred are both residues R a< and both residues R c< not equal to H, preferably not equal to H, D, F, Cl, Br, I. Here, the previously set out statements regarding preferred residues R a< and R c< must be taken into account.

[0017] It is further preferred that at least one, preferably at least two, of the residues R a< , R c< represent a straight-chain alkyl or alkoxy group with 1 to 40 C atoms or a branched or cyclic alkyl or alkoxy group with 3 to 20 C atoms, wherein the alkyl or alkoxy group may each be substituted with one or more residues R 1< .

[0018] In a preferred embodiment, the residue R can be an aromatic or heteroaromatic ring system with 5 to 13 aromatic ring atoms, which can be substituted with one or more residues R e<.

[0019] According to the invention, two residues R a< form a condensed ring with the further groups to which the two residues R a< bind, preferably an aliphatic or heteroaliphatic ring with 3 to 20, preferably 5 to 18, ring atoms or an aromatic or heteroaromatic ring with 5 to 13 ring atoms, particularly preferably an aliphatic or heteroaliphatic ring with 3 to 20, preferably 5 to 18, ring atoms, each of which may be substituted with one or more residues R 1<, wherein R 1< has the aforementioned meaning.

[0020] Furthermore, it may preferably be provided that two residues R c< form a condensed ring with the further groups to which the two residues R c< bind, preferably an aliphatic or heteroaliphatic ring with 3 to 20, preferably 5 to 18 ring atoms or an aromatic or heteroaromatic ring with 5 to 13 ring atoms, particularly preferably an aliphatic or heteroaliphatic ring with 3 to 20, preferably 5 to 18 ring atoms, each of which may be substituted with one or more residues R 1<, wherein R 1< has the aforementioned meaning.

[0021] In a particularly preferred embodiment, the residue R comprises an aromatic or heteroaromatic ring system with 5 to 13 aromatic ring atoms, which may be substituted with one or more residues R< e<, and at least two residues R< a< , R< c< form a condensed ring with the further groups to which the two residues R< a< , R< c< bind, each of which may be substituted with one or more residues R< 1<. Preferably, a compound / structure according to the invention thus comprises at least one, preferably two, condensed rings formed by the two residues R< a< and optionally R< c< with the further groups to which the two residues R< a< , R< c< bind, and the residue R represents an aromatic or heteroaromatic ring system with 5 to 13 aromatic ring atoms.Condensed rings can be aliphatic, heteroaliphatic, aromatic or heteroaromatic, with preferred embodiments set out above and below, wherein preferably an aliphatic or heteroaliphatic ring with 3 to 20, preferably 5 to 18 ring atoms or an aromatic or heteroaromatic ring with 5 to 13 ring atoms is formed, particularly preferably an aliphatic or heteroaliphatic ring with 3 to 20, preferably 5 to 18 ring atoms, each of which can be substituted with one or more residues R 1<.

[0022] If X represents a group CYR y<, it may be preferentially stipulated that: R y< is, in each occurrence, the same or different C(Ar') 3 , C(R 1< ) 3 , Si(Ar') 3 , Si(R 1< ) 3 , a straight-chain alkyl group with 1 to 40 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl group may be substituted with one or more R 1< residues, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 1< residues; in this respect, two R y< residues may also form a ring system with each other or one R y< residue with a R a< , R b< , R c< , R d< , R e< residue, preferably a R a< .

[0023] Furthermore, it may preferably be provided that the residue R y< bound to group Y and the residue R a< adjacent to the group form a condensed ring with the further groups to which the two residues R y< , R a< bind, preferably an aliphatic or heteroaliphatic ring with 3 to 20, preferably 5 to 18 ring atoms or an aromatic or heteroaromatic ring with 5 to 13 ring atoms, particularly preferably an aliphatic or heteroaliphatic ring with 3 to 20, preferably 5 to 18 ring atoms, which may be substituted with one or more residues R 1<, wherein R 1< has the aforementioned meaning. Furthermore, a residue R b< and a residue R y< can also form a condensed ring with the other groups to which the two residues R y< , R b< bind, as previously explained for the residue R a<, with ring formation via a residue R a< being preferred.

[0024] Furthermore, it is particularly preferred that the residue R y< bonded to group Y does not have an acidic proton in the vicinity of group Y, and preferably that keto-enol tautomerism is excluded in the case Y equals C=O. An acidic proton in this sense is a proton that has a high pKa value, wherein the pKa value of a proton is preferably at least 21, preferably at least 22, and particularly preferably at least 25. Preferably, a residue R y< bonded to group Y and the residue R a< or R b< adjacent to the group form a condensed, bridged ring with the other groups to which the two residues R y< and R a< bond, respectively, satisfying Bredt's rule, with the bridging atom bonding directly to group Y.

[0025] An aryl group according to this invention contains 6 to 40 carbon atoms; a heteroaryl group according to this invention contains 2 to 40 carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aryl group or heteroaryl group is understood to be either a simple aromatic cycle, i.e., benzene, or a simple heteroaromatic cycle, for example, pyridine, pyrimidine, thiophene, etc., or a fused (fused) aryl or heteroaryl group, for example, naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic compounds linked to each other by single bonds, such as biphenyl, are not referred to as aryl or heteroaryl groups, but rather as aromatic ring systems.

[0026] An electron-deficient heteroaryl group according to the present invention is a heteroaryl group comprising at least one heteroaromatic six-membered ring with at least one nitrogen atom. Further aromatic or heteroaromatic five-membered or six-membered rings may be fused to this six-membered ring. Examples of electron-deficient heteroaryl groups are pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline, or quinoxaline.

[0027] An aromatic ring system according to this invention contains 6 to 60 carbon atoms in the ring system, preferably 6 to 40 carbon atoms in the ring system. A heteroaromatic ring system according to this invention contains 2 to 60 carbon atoms, preferably 3 to 40 carbon atoms, and at least one heteroatom in the ring system, provided that the sum of carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N,O and / or S. For the purposes of this invention, an aromatic or heteroaromatic ring system is understood to be a system that does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups may also be linked by a non-aromatic unit, such as a carbon, nitrogen, or oxygen atom. For example, systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ethers, 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 short alkyl group. Preferably, the aromatic ring system is selected from fluorene, 9,9'-spirobifluorene, 9,9-diaryllamine, or groups in which two or more aryl and / or heteroaryl groups are linked to one another by single bonds.

[0028] Within the scope of the present invention, the following are preferably used as the groupings of an aliphatic hydrocarbon residue or an alkyl group or an alkenyl or alkynyl group, which may contain 1 to 20 carbon atoms and in which individual hydrogen atoms or CH₂ groups may also be substituted by the groups mentioned above: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, neo-pentyl, cyclopentyl, n-hexyl, neo-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, Cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentinyl, hexynyl, heptynyl or octynyl.Unter einer Alkoxygruppe 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-Trifluorethoxy verstanden. Unter einer Thioalkylgruppe mit 1 bis 40 C-Atomen werden insbesondere 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, Trifluormethylthio, Pentafluorethylthio, 2,2,2-Trifluorethylthio, Ethenylthio, Propenylthio, Butenylthio, Pentenylthio, Cyclopentenylthio, Hexenylthio, Cyclohexenylthio, Heptenylthio, Cycloheptenylthio, Octenylthio, Cyclooctenylthio, Ethinylthio, Propinylthio, Butinylthio, Pentinylthio, Hexinylthio, Heptinylthio oder Octinylthio verstanden.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 CH2 groups can be replaced by the groups mentioned above; furthermore, one or more H atoms can also be replaced by D, F, Cl, Br, I, CN or NO2, preferably F, Cl or CN, more preferably F or CN, particularly preferably CN.

[0029] An aromatic or heteroaromatic ring system with 5–60 or 5–40 aromatic ring atoms, respectively, which may be further substituted with the aforementioned substituents and which may be linked via any positions on the aromatic or heteroaromatic compound, is understood to include, 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, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene. Benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline,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-Tetrazin, 1,2,3,5-Tetrazin, Purin, Pteridin, Indolizin und Benzothiadiazol oder Gruppen,which are derived from combinations of these systems.

[0030] In the context of this description, the phrase "two or more residues can form a ring" means, among other things, that the two residues are linked to each other by a chemical bond involving the formal elimination of two hydrogen atoms. This is illustrated by the following scheme.

[0031] 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 diagram:

[0032] In a preferred embodiment, the compounds according to the invention can be selected from the compounds of formulas (I-1) to (I-83), where the symbols R a< , R b< , R c< , R d< , R e< and R y< have the meanings mentioned above, especially for formula (I), and the following applies to the symbols and indices used: X 1< represents N or CR e< in each occurrence, either the same or different, preferably CR e<, provided that no more than two of the groups X 1< represent N in a cycle; Y 1< represents C(R e< ) 2 , (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ), NR e< , NAr', O, S, SO, SO 2 , Se, P(O)R e< , BR e< or Si(R e< ) 2 , preferably C(Rf e< ) 2 , (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ), O or S, particularly preferably C(R e< ) 2 ;T 1< represents, in each instance, a condensed ring, preferably an aliphatic or heteroaliphatic ring with 3 to 20, preferably 5 to 18 ring atoms, or an aromatic or heteroaromatic ring with 5 to 13 ring atoms, particularly preferably an aliphatic or heteroaliphatic ring with 3 to 20, preferably 5 to 18 ring atoms, which may be substituted with one or more R 1< groups, wherein R 1< has the meaning given above, particularly for formula (I); nist 0, 1, 2 or 3, preferably 0, 1 or 2; mist 0, 1, 2, 3 or 4, preferably 0, 1 or 2.

[0033] Surprisingly, compounds / structures where the symbol X in formula (I) represents C-CN show unexpected advantages in terms of performance, particularly regarding color purity, such that compounds with two cyano substituents on the aromatic rings exhibit significantly narrower emission spectra. Surprisingly, the structures / compounds of formulas (I-1) to (I-13) are preferred, and those of formulas (I-1) to (I-7) are particularly preferred.

[0034] In a preferred embodiment of the present invention, it can be provided that at least two residues R, Ra< , Rb< , Rc< , Rd< , Re< , Ry< form a condensed ring with the further groups to which the two residues R, Ra< , Rb< , Rc< , Rd< , Re< , Ry< bind, wherein the two residues R, Ra< , Rb< , Rc< , Rd< , Re< , Ry< form at least one structure of the following formulas (Cy-1) to (Cy-10) where R 1< and R 2< have the meanings set out above, the dashed bonds represent the bonding points to the atoms of the groups to which the two residues R, Ra< , R b< , R c< , R d< , Re< , R y< bind, and furthermore: Z 1< , Z 3< is the same or different at each occurrence C(R 3< ) 2 , Si(R 3< ) 2 , O, S, NR 3< or C(=O); Z 2< is C(R 1< ) 2 , Si(R 1< ) 2 , O, S, NR 1< or C(=O), where two adjacent groups Z 2< can represent -CR 1< =CR 1< - or an ortho-linked arylene or heteroarylene group with 5 to 14 aromatic ring atoms, which may be substituted by one or more R 1< residues; Gist is an alkylene group with 1, 2 or 3 carbon atoms, which may be substituted with one or more R 1< substituents, -CR 1< =CR 1< - or an ortho-linked arylene or heteroarylene group with 5 to 14 aromatic ring atoms, which may be substituted by one or more R 1< substituents;R 3< is the same or different in each occurrence: H, D, F, Cl, Br, I, CN, NO 2 , N(Ar") 2 , N(R 2< ) 2 , C(=O)Ar", C(=O)R 2< , P(=O)(Ar") 2 , P(Ar") 2 , B(Ar") 2 , B(R 2< ) 2 , C(Ar") 3 , C(R 2< ) 3 , Si(Ar") 3 , Si(R 2< ) 3 , a straight-chain alkyl or alkoxy group with 1 to 40 carbon atoms, or a branched or cyclic alkyl or alkoxy group with 3 to 40 carbon atoms, each of which may be substituted with one or more R 2< residues, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 2< groups, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted by one or more R 2< groups, or an aralkyl or heteroaralkyl group with 5 to 60 aromatic ring atoms, which may be substituted by one or more R 2< groups, or a combination of these systems;Two R3< residues bonded to the same carbon atom can form an aliphatic or aromatic ring system together, thus spanning a spiro system; furthermore, R3< can form a ring system, preferably an aliphatic ring system, with a preferably adjacent residue R, Ra<, RC<, Rd<, Re<, or R1<. provided that in these groups no two heteroatoms are directly bonded to each other and no two groups C=O are directly bonded to each other.

[0035] In a preferred embodiment of the invention, R 3< is not equal to H and / or D.

[0036] If adjacent residues in the structures according to the invention form an aliphatic ring system, it is preferred that this system does not contain acidic benzylic protons. Benzylic protons are understood to be protons that bond to an alkyl carbon atom which is directly bonded to an aryl or heteroaryl group. This can be achieved by ensuring that the carbon atoms of the aliphatic ring system that bond directly to an aryl or heteroaryl group are fully substituted and do not contain any bonded hydrogen atoms. Thus, the absence of acidic benzylic protons in formulas (Cy-1) to (Cy-3) is achieved by defining Z<1 and Z<3, where they represent C(R<3)<2, such that R<3< is not equal to hydrogen.This can also be achieved by having the carbon atoms of the aliphatic ring system that bond directly to an aryl or heteroaryl group act as bridgeheads of a bi- or polycyclic structure. Due to the spatial structure of the bi- or polycycle, the protons bonded to these bridgehead carbon atoms are significantly less acidic than benzylic protons on carbon atoms not bound in a bi- or polycyclic structure and are considered non-acidic protons within the meaning of the present invention. Thus, the absence of acidic benzylic protons in formulas (Cy-4) to (Cy-10) is achieved by using a bicyclic structure, whereby R1, where it represents H, is significantly less acidic than benzylic protons because the corresponding anion of the bicyclic structure is not resonance-stabilized.Even though R 1< in formulas (Cy-4) to (Cy-10) stands for H, it is therefore a non-acidic proton within the meaning of the present application.

[0037] Preferably, it may be provided that, in particular in formulas (Cy-1) to (Cy-3), the following applies: R 3< is the same or different in each occurrence: F, Cl, Br, I, CN, NO 2 , N(Ar") 2 , N(R 2< ) 2 , C(=O)Ar", C(=O)R 2< , P(=O)(Ar") 2 , P(Ar") 2 , B(Ar") 2 , B(R 2< ) 2 , C(Ar") 3 , C(R 2< ) 3 , Si(Ar") 3 , Si(R 2< ) 3 , a straight-chain alkyl or alkoxy group with 1 to 40 carbon atoms, or a branched or cyclic alkyl or alkoxy group with 3 to 40 carbon atoms, each of which may be substituted with one or more R 2< substituents, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which each may be substituted by one or more R 2< groups, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted by one or more R 2< groups, or an aralkyl or heteroaralkyl group with 5 to 60 aromatic ring atoms, which may be substituted by one or more R 2< groups, or a combination of these systems;Two R3< groups bonded to the same carbon atom can form an aliphatic or aromatic ring system together, thus spanning a spiro system; furthermore, R3< can form a ring system, preferably an aliphatic ring system, with a preferably adjacent R, Ra<, RC<, Rd<, Re<, R1< or with another group.

[0038] Preferably, it may be provided that, in particular in formulas (Cy-1) to (Cy-3), the following applies: R 3< is the same or different in each occurrence F, a straight-chain alkyl or alkoxy group with 1 to 40 C atoms or a branched or cyclic alkyl or alkoxy group with 3 to 20 C atoms, wherein the alkyl or alkoxy group may each be substituted with one or more R 2< residues, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 2< residues, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted by one or more R 2< residues; Two residues R 3< can also form a ring system, preferably an aliphatic ring system, with each other, or with a residue R 3< with a residue R, R a< , R c< , R d< , R e< , R 1< or with a further group.

[0039] In a preferred embodiment of the structure according to formulas (Cy-1) to (Cy-10), at most one of the groups Z1<, Z2< and Z3< represents a heteroatom, in particular O or NR3<, respectively, and the other groups represent C(R3<)2 or C(R1<)2, respectively, or Z1< and Z3< represent O or NR3<, respectively, and Z2< represents C(R1<)2. In a particularly preferred embodiment of the invention, Z1< and Z3< represent C(R3<)2, respectively, or Z2< represents C(R1<)2, and Z2< represents C(R1<)2, and particularly preferably C(R3<)2 or CH2.

[0040] In a preferred embodiment of the invention, the residue R 1< , which is bonded to the bridgehead atom, preferably to the bridgehead atom according to formulas (Cy-4) to (Cy-10), is selected as the same or different at each occurrence from the group consisting of H, D, F, a straight-chain alkyl group with 1 to 10 C atoms, which may be substituted with one or more residues R 2<, but is preferably unsubstituted, a branched or cyclic alkyl group with 3 to 10 C atoms, which may be substituted with one or more residues R 2<, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system with 5 to 12 aromatic ring atoms, which may each be substituted by one or more residues R 2< .Particularly preferred is the residue R1, which is bonded to the bridgehead atom according to formula (CY-4), selected in each instance either identically or differently from the group consisting of H, F, a straight-chain alkyl group with 1 to 4 carbon atoms, a branched alkyl group with 3 or 4 carbon atoms, or a phenyl group which may be substituted by an alkyl group with 1 to 4 carbon atoms, but is preferably unsubstituted. Most particularly preferred is the residue R1, selected in each instance either identically or differently from the group consisting of H, methyl, or tert-butyl.

[0041] In a preferred embodiment of the present invention, it can be provided that at least two residues R, Ra< , Rb< , Rc< , Rd< , Re< , Ry< form a condensed ring with the further groups to which the two residues R, Ra< , Rb< , Rc< , Rd< , Re< , Ry< bind, wherein the two residues R, Ra< , Rb< , Rc< , Rd< , Re< , Ry< form at least one structure of formulas (RA-1) to (RA-13). where R 1< has the meaning set out above, the dashed bonds represent the attachment points through which the two residues R, R a< , R b< , R c< , R d< , R e< , R y< bind, and the other symbols have the following meaning: Y 2< is the same or different for each occurrence C(R 1< ) 2 , (R 1< ) 2 CC(R 1< ) 2 , (R 1< )C=C(R 1< ), NR 1< , NAr', O or S, preferably C(R 1< ) 2 , (R 1< ) 2 CC(R 1< ) 2 , (R 1< )C=C(R 1< ), O or S; R f< is the same or different for each occurrence F,a straight-chain alkyl or alkoxy group with 1 to 40 carbon atoms, or a branched or cyclic alkyl or alkoxy group with 3 to 20 carbon atoms, wherein the alkyl or alkoxy group may each be substituted with one or more R2< groups, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R2< groups, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted by one or more R2< groups; wherein two Rf< groups may also form a ring system with each other, or one Rf< group with one R1< group, or with another group; Rf< group 0, 1, 2, 3, or 4, preferably 0, 1, or 2, particularly preferably 0 or 1; sist 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1 or 2; tist 0, 1, 2, 3, 4, 5, 6, 7 or 8, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1 or 2;vist 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1 or 2. ;

[0042] Structures of formulas RA-1, RA-3, RA-4 and RA-5 are preferred, and structures of formulas RA-4 and RA-5 are particularly preferred.

[0043] In a preferred embodiment of the invention, at least two residues R, Ra< , Rb< , Rc< , Rd< , Re< , Ry< form a condensed ring with the further groups to which the two residues R, Ra< , Rb< , Rc< , Rd< , Re< , Ry< bind, wherein the two residues R, Ra< , Rb< , Rc< , Rd< , Re< , Ry< preferably form at least one of the structures of formulas (RA-1a) to (RA-4f). wherein the dashed bonds represent the attachment points through which the two residues R, R a< , R b< , R c< , R d< , R e< , R y< bind, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2 and the symbols R 1< , R 2< , R f< and the indices s and t have the meaning set forth above, in particular for formula (I) and / or formulas (RA-1) to (RA-13).

[0044] Structures of formulas RA-4f are preferred.

[0045] Furthermore, it may be provided that two residues R a< form the structures of the formulas (Cy-1) to (Cy-10), (RA-1) to (RA-13) and / or (RA-1a) to (RA-4f) and form a condensed ring.

[0046] Furthermore, it can be provided that a residue R a< and a residue R y< form structures of formulas (Cy-1) to (Cy-10), (RA-1) to (RA-13) and / or (RA-1a) to (RA-4f) and form a condensed ring, wherein the residue R a< and the residue R y< are preferably adjacent. Furthermore, a residue R b< and a residue R y< can also form structures of formulas (Cy-1) to (Cy-10), (RA-1) to (RA-13) and / or (RA-1a) to (RA-4f) and form a condensed ring, wherein ring formation via a residue R a< is preferred.

[0047] Furthermore, it can be provided that two residues R c< form the structures of the formulas (Cy-1) to (Cy-10), (RA-1) to (RA-13) and / or (RA-1a) to (RA-4f) and form a condensed ring.

[0048] In a further embodiment, two R groups can form the structures of formulas (Cy-1) to (Cy-10), (RA-1) to (RA-13) and / or (RA-1a) to (RA-4f) and create a condensed ring, with the R< groups preferably being adjacent. Furthermore, the two R< groups can also originate from different rings, with each ring bonding to the nitrogen atom of the core structure.

[0049] Furthermore, it may be provided that a residue R d< with a residue R or R e< form the structures of the formulas (Cy-1) to (Cy-10), (RA-1) to (RA-13) and / or (RA-1a) to (RA-4f) and form a condensed ring.

[0050] Furthermore, it can be provided that two residues R e< form the structures of formulas (Cy-1) to (Cy-10), (RA-1) to (RA-13) and / or (RA-1a) to (RA-4f) and form a condensed ring, wherein the residues R e< are preferably adjacent.

[0051] In this context, preferably two residues R a< , two residues R c< , one residue R d< with one residue R or R e< or two residues R e< form the structures of formulas (Cy-1) to (Cy-10), (RA-1) to (RA-13) and / or (RA-1a) to (RA-4f) and form at least one condensed ring, particularly preferably two residues R a< and / or two residues R c< . Particularly preferably, two residues R a< and two residues R c< each form one condensed ring.

[0052] In a further preferred embodiment, at least two residues R, Ra<, Rb<, Rc<, Rd<, Re<, Ry< form a condensed ring with the further groups to which the two residues R, Ra<, Rb<, Rc<, Rd<, Re<, Ry< bind, wherein the two residues R, Ra<, Rb<, Rc<, Rd<, Re<, Ry< form structures of the formula (RB). where R 1< has the meaning given above, especially for formula (I), the dashed bonds represent the attachment points through which the two residues R, R a< , R b< , R c< , R d< , R e< , R y< bind, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and Y 3< is C(R 1< ) 2 , NR 1< , NAr', BR 1< , BAr', O or S, preferably C(R 1< ) 2 , NAr' or O, where Ar' has the meaning given above, especially for formula (I).

[0053] It can be provided that a residue R d< forms a condensed ring with a residue R or R e<. Furthermore, it can be provided that two residues R e< form the condensed ring with the residues R e<, preferably being adjacent.

[0054] In particular, it may be provided that in preferred structures / compounds the sum of the indices r, s, t, v, m and n is preferably 0, 1, 2 or 3, and particularly preferably 1 or 2. It may also be preferably provided that the compounds have at least two condensed rings, wherein at least one condensed ring is formed by structures of formulas (RA-1) to (RA-13) and / or (RA-1a) to (RA-4f) and a further ring is formed by structures of formulas (RA-1) to (RA-13), (RA-1a) to (RA-4f) or (RB).

[0055] If the compounds have at least two condensed rings, preferably two residues R a< , two residues R c< , one residue R d< with one residue R or R e< or two residues R e< form the structures of formulas (Cy-1) to (Cy-10), (RA-1) to (RA-13) and / or (RA-1a) to (RA-4f) and each form at least one condensed ring, particularly preferably two residues R a< and two residues R c< .

[0056] Furthermore, it may preferably be provided that the condensed ring T 1< , which is set out in formulas (I-48) to (I-64) among others, is selected from a structure of formulas (TCY-1) to (TRA-13) or (TRA-4f) wherein the symbols R1< and R2< have the meanings mentioned above, in particular for formula (I), the symbols Z1<, Z2<, G and R3< have the meanings mentioned above, in particular for formulas (Cy-1) to (Cy-10), and Z4< is the same or different at each occurrence C(R3<)2, O, S or NR3<, preferably the same or different at each occurrence C(R3<)2, provided that in these groups no two heteroatoms are directly bonded to each other and no two groups C=O are directly bonded to each other, the symbols Y2< and Rf< and the indices r, s, t and v have the meanings mentioned above, in particular for formulas (RA-1) to (RA-13), the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, the dashed bonds are the bonding sites of the represent the condensed ring with the other groups.

[0057] Furthermore, it may be provided that the substituents R, Ra<, Rb<, Rc<, Rd<, Re<, Rf<, Ry<, R1<, and R2< according to the formulas above do not form a condensed aromatic or heteroaromatic ring system with the ring atoms of the ring system to which the substituents R, Ra<, Rb<, Rc<, Rd<, Re<, Rf<, Ry<, R1<, and R2< bind. This includes the formation of a condensed aromatic or heteroaromatic ring system with possible substituents R1< and R2<, which may be bonded to the residues R, Ra<, Rb<, Rc<, Rd<, Re<, Rf<, Ry<, and R1<.

[0058] If the compound according to the invention is substituted with aromatic or heteroaromatic groups R, R a< , R b< , R c< , R d< , R e< , R f< , R y< , R 1< or R 2< , it is preferred if these do not have aryl or heteroaryl groups with more than two directly fused aromatic six-membered rings. Particularly preferred are the substituents not having any aryl or heteroaryl groups with directly fused six-membered rings at all. This preference is due to the low triplet energy of such structures. Condensed aryl groups with more than two directly fused aromatic six-membered rings that are nevertheless also suitable according to the invention are phenanthrene and triphenylene, since these also exhibit a high triplet energy level.

[0059] Preferably, therefore, it can be provided that the residue R does not comprise a continuously conjugated anthracene group, preferably none of the residues R, R a< , R b< , R c< , R d< , R e< , R f< , R y< , R 1< , R 2< comprises a continuously conjugated anthracene group.

[0060] A complete conjugation of the anthracene group is formed as soon as direct bonds are formed between the anthracene group, the basic framework according to the invention, which is represented in formula (I), and an optional aromatic or heteroaromatic compound group. Further linkage between the aforementioned conjugated groups, for example via an S, N, or O atom or a carbonyl group, does not impair conjugation. In a fluorene system, the two aromatic rings are directly bonded, whereby the sp³-hybridized carbon atom at position 9, although it prevents condensation of these rings, can still conjugate, since this sp³-hybridized carbon atom at position 9 is not necessarily located between the groups that are linked via a compound group.In contrast, continuous conjugation can occur in a spirobifluorene structure if the connection between the groups linked via the spirobifluorene group occurs via the same phenyl group of the spirobifluorene structure or via phenyl groups of the spirobifluorene structure that are directly bonded to each other and lie in the same plane. If the connection between the groups linked via one spirobifluorene group occurs via different phenyl groups of the second spirobifluorene structure, which are linked via the sp³-hybridized carbon atom at position 9, the conjugation is interrupted.

[0061] Particularly preferably, it may be provided that the residue R does not comprise an anthracene group, preferably none of the residues R, R a< , R b< , R c< , R d< , R e< , R f< , R y< , R 1< , R 2< comprises an anthracene group.

[0062] It is particularly preferred that the residue R does not comprise an aromatic or heteroaromatic ring system having three linearly condensed aromatic rings, wherein preferably none of the residues R, R a< , R b< , R c< , R d< , R e< , R f< , R y< , R 1< , R 2< comprises an aromatic or heteroaromatic ring system having three linearly condensed aromatic rings.

[0063] Furthermore, it can be provided that the residue R< y< does not comprise or form a fluorenone group, preferably none of the residues R, R a< , R b< , R c< , R d< , Re< ) comprises or forms a fluorenone group. This includes substituents that bind to the residues R, R a< , R b< , R c< , R d< , Re< , R y< ). A fluorenone comprises a 5-membered ring with a CO group to which two aromatic 6-membered rings are fused.

[0064] When two substituents, which may be selected from R, Ra<, Rb<, Rc<, Rd<, Re<, Rf<, Ry<, R1<, and R2<, form a ring system, this system can be monocyclic or polycyclic, aliphatic, heteroaliphatic, aromatic, or heteroaromatic. The substituents forming the ring system can be adjacent, i.e., bonded to the same carbon atom or to carbon atoms directly bonded to one another, or they can be further apart. Furthermore, the ring systems containing the substituents R, Ra<, Rb<, Rc<, Rd<, Re<, Rf<, Ry<, R1<, and / or R2< can also be linked by a bond, thus resulting in ring closure. In this case, each of the corresponding bonding sites is preferably provided with a substituent R, R a< , R b< , R c< , R d< , R e< , R f< , R y< , R 1< and / or R 2<.

[0065] Preferably, the structure / compound can be symmetrical with respect to the residues R< a< and R< c<. Furthermore, the structure / compound can be symmetrical with respect to the residues R< a<, R< b< and R< c<. Furthermore, the structure / compound can be symmetrical with respect to the residues R< a<, R< b<, R< c< and R< d<.

[0066] Symmetric with respect to the residues R a< and R c< means, in particular, that the corresponding residues R a< and R c< are identical and do not differ. Here, the equality refers to both residues R a< and R c<. For example, if two residues R a< form a ring of structure RA-1, then both residues R c< form an identical ring of structure RA-1.

[0067] Structures / compounds in which the residues Ra< and Rc< are symmetrical are characterized by a surprisingly high color purity, which is reflected in particular in a narrow emission spectrum.

[0068] In a further embodiment, the structure / connection can be asymmetrical with respect to the residues R a< and R c<.

[0069] Furthermore, it may be provided that the residue R comprises at least one group selected from C(Ar) 3 , C(R e< ) 3 , N(Ar) 2 , N(R e< ) 2 , Si(Ar) 3 , Si(R e< ) 3 , B(R e< ) 2 , preferably selected from C(Ar) 3 , C(R e< ) 3 , N(Ar) 2 , Si(Ar) 3 , Si(R e< ) 3 , particularly preferably a fluorene group which may be substituted with one or more residues R e< , or forms with a residue R d< .

[0070] Furthermore, it may be provided that the residue R e< and / or R d< comprises at least one group selected from C(Ar') 3 , C(R 1< ) 3 , N(Ar') 2 , N(R 1< ) 2 , Si(Ar') 3 , Si(R 1< ) 3 , B(R 1< ) 2 , preferably selected from C(Ar') 3 , C(R 1< ) 3 , N(Ar') 2 , Si(Ar') 3 , Si(R 1< ) 3 , preferably a fluorene group which may be substituted with one or more residues R 1< , or forms with a residue R d< or R e< .

[0071] Structures / compounds with one of the aforementioned groups selected from C(Ar') 3 , C(R 1< ) 3 , Si(Ar') 3 , Si(R 1< ) 3 , N(Ar') 2 , N(R 1< ) 2 , B(R 1< ) 2 , particularly preferably a fluorene group, are characterized by a surprisingly high efficiency.

[0072] According to a preferred embodiment, a compound according to the invention can be represented by at least one of the structures according to formula (I) and / or (I-1) to (I-83). Preferably, compounds according to formula (I) and / or (I-1) to (I-83) have a molecular weight of less than or equal to 5000 g / mol, more preferably less than or equal to 4000 g / mol, particularly preferably less than or equal to 3000 g / mol, especially preferably less than or equal to 2000 g / mol, and most preferably less than or equal to 1200 g / mol.

[0073] Furthermore, preferred compounds according to the invention are characterized by being sublimable. These compounds generally have a molar mass of less than approximately 1200 g / mol.

[0074] Preferred aromatic or heteroaromatic ring systems Ar, R, Ra<, Rb<, Rc<, Rd<, Re<, Rf< and / or Ar' 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 may be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which may be linked via the 1-, 2-, 3- or 4-position, naphthalene, in particular 1- or 2-linked naphthalene, indole, benzofuran, benzothiophene, carbazole, which may be linked via the 1-, 2-, 3-, 4- or 9-position, dibenzofuran, which may be linked via the 1-, 2-, which may be linked at the 3rd or 4th position, dibenzothiophene, which may be linked at the 1st, 2nd, 3rd or 4th position, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene,which can each be substituted with one or more residues R e< , R 1< or R 2<.

[0075] Preferably, at least one substituent R, Ra<, Rb<, Rc<, Rd<, Re< may be selected, either the same or different, from the group consisting of H, D, a branched or cyclic alkyl or alkoxy group with 3 to 20 carbon atoms, or an aromatic or heteroaromatic ring system selected from the groups of the following formulas Ar-1 to Ar-75, wherein the substituents R, Ra<, Rb<, Rc<, Rd<, Re< preferably either form a ring according to the structures of formulas (RA-1) to (RA-13), (RA-1a) to (RA-4f), or (RB), or the substituent R, Ra<, Rb<, Rc<, Rd<, Re< may be selected, either the same or different, from the group consisting of H, D, or an aromatic or heteroaromatic ring system selected from the groups of the following Formulas Ar-1 to Ar-75, and / or the group Ar' is selected as the same or different at each occurrence from the groups of the following formulas Ar-1 to Ar-75, where R 1< has the meanings mentioned above, the dashed line represents the connection point to the corresponding group and the following also applies: Ar 1< is, in each occurrence, either the same or different, a bivalent aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, each of which may be substituted with one or more R 1< residues; A is, in each occurrence, either the same or different, C(R 1< ) 2 , NR 1< , O or S; p is 0 or 1, where p = 0 means that the group Ar 1< is not present and that the corresponding aromatic or heteroaromatic group is directly bonded to the corresponding residue; q is 0 or 1, where q = 0 means that no group A is bonded at this position and instead, residues R 1< are bonded to the corresponding carbon atoms.

[0076] The structures of formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16), (Ar-40), (Ar-41), (Ar-42), (Ar-43), (Ar-44), (Ar-45), (Ar-46), (Ar-69), (Ar-70), (Ar-75) are preferred, and structures of formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16) are particularly preferred.

[0077] If the aforementioned groups for Ar have multiple groups A, then all combinations from the definition of A are possible. Preferred embodiments are those in which one group A stands for NR 1< and the other group A for C(R 1< ) 2, or in which both groups A stand for NR 1<, or in which both groups A stand for O.

[0078] When A stands for NR 1<, the substituent R 1< bonded to the nitrogen atom preferably represents an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, which may also be substituted by one or more R 2< groups. In a particularly preferred embodiment, this substituent R 1< represents, in each instance, an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, in particular with 6 to 18 aromatic ring atoms, which has no fused aryl groups and no fused heteroaryl groups in which two or more aromatic or heteroaromatic 6-ring groups are directly fused to one another, and which may also be substituted by one or more R 2< groups.Phenyl, biphenyl, terphenyl, and quaterphenyl with linkage patterns as listed above for Ar-1 to Ar-11 are preferred, wherein these structures may be substituted by one or more R2< groups instead of R1<, but are preferably unsubstituted. Triazine, pyrimidine, and quinazoline as listed above for Ar-47 to Ar-50, Ar-57, and Ar-58 are also preferred, wherein these structures may be substituted by one or more R2< groups instead of R1<.

[0079] Preferred substituents R, R a< , R b< , R c< , R d< , R e< and R f< are described below.

[0080] In a preferred embodiment of the invention, R, R a< , R b< , R c< , R d< , R e< is selected, either the same or different at each occurrence, from the group consisting of H, D, F, CN, NO 2 , Si(R 1< ) 3 , B(OR 1< ) 2 , a straight-chain alkyl group with 1 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl group may be substituted with one or more R 1< groups, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, which may be substituted by one or more R 1< groups.

[0081] In a further preferred embodiment of the invention, substituent R, R a< , R b< , R c< , R d< , R e< is selected, either the same or different at each occurrence, from the group consisting of H, D, F, a straight-chain alkyl group with 1 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl group may be substituted with one or more R 1< groups, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, which may be substituted by one or more R 1< groups.

[0082] Furthermore, it may be provided that at least one substituent R, R a< , R b< , R c< , R d< , R e< is selected, either the same or different at each occurrence, from the group consisting of H, D, an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which may be substituted with one or more residues R 1<, or a group N(Ar') 2 . In a further preferred embodiment of the invention, the substituents R, R a< , R b< , R c< , R d< , Re< either form a ring according to the structures of formulas (RA-1) to (RA-13), (RA-1a) to (RA-4f) or (RB) or R, R a< , R b< , R c< , R d< , Re< is the same or different at each occurrence selected from the group consisting of H, D, an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which may be substituted with one or more R 1< substituents, or a group N(Ar') 2 .Particularly preferred is substituent R, R a< , R b< , R c< , R d< , R e< selected from the group consisting of H or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably with 6 to 13 aromatic ring atoms, each of which may be substituted with one or more R 1< groups.

[0083] InIn a preferred embodiment of the invention, R< f< is the same or different at each occurrence selected from the group consisting of a straight-chain alkyl group with 1 to 20 C atoms or a branched or cyclic alkyl group with 3 to 20 C atoms, wherein the alkyl group may be substituted with one or more R< 2< groups, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, which may be substituted by one or more R< 2< groups.

[0084] InIn a further preferred embodiment of the invention, R f< is the same or different at each occurrence selected from the group consisting of a straight-chain alkyl group with 1 to 10 C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, wherein the alkyl group may be substituted with one or more R 2< residues, or an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which may be substituted with one or more R 2< residues.Particularly preferred is R a< selected from the group consisting of a straight-chain alkyl group with 1 to 5 C atoms or a branched or cyclic alkyl group with 3 to 5 C atoms, wherein the alkyl group may be substituted with one or more R 2< groups, or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably with 6 to 13 aromatic ring atoms, which may each be substituted with one or more R 2< groups.

[0085] InIn a preferred embodiment of the invention, R f< is selected, in each occurrence, as the same or different from the group consisting of a straight-chain alkyl group with 1 to 6 C atoms or a cyclic alkyl group with 3 to 6 C atoms, wherein the alkyl group may be substituted with one or more R 2< residues, or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, which may each be substituted by one or more R 2< residues; two R f< residues may also form a ring system together.Particularly preferred is R< f< selected, in each occurrence, either identically or differently from the group consisting of a straight-chain alkyl group with 1, 2, 3, or 4 carbon atoms, or a branched or cyclic alkyl group with 3 to 6 carbon atoms, wherein the alkyl group may be substituted with one or more substituents R< 2<, but is preferably unsubstituted, or an aromatic ring system with 6 to 12 aromatic ring atoms, in particular with 6 aromatic ring atoms, which may be substituted by one or more, preferably non-aromatic, substituents R< 2<, but is preferably unsubstituted; two substituents R< f< may form a ring system together. Most particularly preferred is R< f< selected, in each occurrence, either identically or differently from the group consisting of a straight-chain alkyl group with 1, 2, 3, or 4 carbon atoms, or a branched alkyl group with 3 to 6 carbon atoms.R f< is particularly preferably a methyl group or a phenyl group, wherein two phenyl groups can form a ring system together, with a methyl group being preferred over a phenyl group.

[0086] Preferred aromatic or heteroaromatic ring systems for which the substituents R, Ra<, Rb<, Rc<, Rd<, Re<, Rf< or Ar, Ar' or Ar" stand, 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 may be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which may be linked via the 1-, 2-, 3- or 4-position, naphthalene, in particular 1- or 2-linked naphthalene, indole, benzofuran, benzothiophene, carbazole, which may be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, which may be linked via the dibenzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline,Quinazoline, quinoxaline, phenanthrene, or triphenylene, each of which may be substituted with one or more R< e< , R< 1< , or R< 2< respectively. The structures Ar-1 to Ar-75 listed above are particularly preferred, with structures of formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16), (Ar-40), (Ar-41), (Ar-42), (Ar-43), (Ar-44), (Ar-45), (Ar-46), (Ar-69), (Ar-70), (Ar-75) being particularly preferred. Regarding the structures Ar-1 to Ar-75, it should be noted that these are represented with a substituent R 1<. In the case of the Ar ring system, these substituents R 1< are to be replaced by R e<, and in the case Ar", R f<, these substituents R 1< are to be replaced by R 2<.

[0087] Further suitable groups R, Ra<, Rb<, Rc<, Rd<, Re< are groups of the formula -Ar4< -N(Ar2<)(Ar3<), where Ar2<, Ar3<, and Ar4<, whether identical or different, represent an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, each of which may be substituted with one or more R1< groups. The total number of aromatic ring atoms of Ar2<, Ar3<, and Ar4< is at most 60 and preferably at most 40.

[0088] Ar4< and Ar2< can be linked to each other and / or Ar2< and Ar3< can also be linked to each other by a group selected from C(R1<)2, NR1<, O, or S. Preferably, the linkage of Ar4< and Ar2< to each other or of Ar2< and Ar3< to each other is ortho to the position of the linkage with the nitrogen atom. In a further embodiment of the invention, none of the groups Ar2<, Ar3<, or Ar4< are linked to each other.

[0089] Preferably, Ar 4< is an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 12 aromatic ring atoms, each of which may be substituted with one or more R 1< groups. Particularly preferably, Ar 4< is selected from the group consisting of ortho-, meta-, or para-phenylenes or ortho-, meta-, or para-biphenyls, each of which may be substituted by one or more R 1< groups, but preferably are unsubstituted. Most preferably, Ar 4< is an unsubstituted phenylene group.

[0090] Preferably, Ar 2< and Ar 3< are the same or different at each occurrence an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, each of which may be substituted with one or more R 1< residues. Particularly preferred groups Ar 2< and Ar 3< are selected, either identically or differently at each occurrence, from the group consisting of benzene, ortho-, meta- or para-biphenyl, ortho-, meta-, para- or branched terphenyl, ortho-, meta-, para- or branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, 1- or 2-naphthyl, indole, benzofuran, benzothiophene, 1-, 2-, 3- or 4-carbazole, 1-, 2-, 3- or 4-dibenzofuran, 1-, 2-, 3- or 4-dibenzothiophene, indenocarbazole, indolocarbazole, 2-, 3- or 4-pyridine, 2-, 4- or 5-pyrimidine, pyrazine, Pyridazine, triazine, phenanthrene or triphenylene, each of which may be substituted with one or more R 1< residues.Particularly preferred are Ar 2< and Ar 3<, whether identical or different in each occurrence, selected from the group consisting of benzene, 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, in particular 1-, 2-, 3- or 4-fluorene, or spirobifluorene, in particular 1-, 2-, 3- or 4-spirobibfluorene.

[0091] In a further preferred embodiment of the invention, R 1< is selected, whether the same or different at each occurrence, from the group consisting of H, D, F, CN, a straight-chain alkyl group with 1 to 10 C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, wherein the alkyl group may be substituted with one or more R 2< groups, or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, which may be substituted by one or more R 2< groups.In a particularly preferred embodiment of the invention, R 1< is selected, whether the same or different, from the group consisting of H, a straight-chain alkyl group with 1 to 6 C atoms, in particular with 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group with 3 to 6 C atoms, wherein the alkyl group may be substituted with one or more R 2< groups, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system with 6 to 13 aromatic ring atoms, each of which may be substituted by one or more R 2< groups, but is preferably unsubstituted.

[0092] In a further preferred embodiment of the invention, R 2< is the same or different at each occurrence H, an alkyl group with 1 to 4 C atoms or an aryl group with 6 to 10 C atoms, which may be substituted with an alkyl group with 1 to 4 C atoms, but preferably is unsubstituted.

[0093] In compounds according to the invention, which are processed by vacuum evaporation, the alkyl groups preferably have no more than five carbon atoms, particularly preferably no more than four carbon atoms, and most preferably no more than one carbon atom. For compounds processed from solution, compounds substituted with alkyl groups, in particular branched alkyl groups, with up to ten carbon atoms, or substituted with oligoarylene groups, for example ortho-, meta-, para- or branched terphenyl or quaterphenyl groups, are also suitable.

[0094] Furthermore, it may be provided that the compound comprises exactly two or exactly three structures according to formula (I) and / or (I-1) to (1-83), wherein preferably one of the aromatic or heteroaromatic ring systems that can be represented by at least one of the groups R, R d< , Re< or to which the groups R, R d< , Re< bind, is shared by both structures.

[0095] In a preferred embodiment, the compounds are selected from compounds according to formula (D-1), (D2) or (D-3), wherein the group L 1< represents a compound group, preferably a bond or an aromatic or heteroaromatic ring system with 5 to 40, preferably 5 to 30 aromatic ring atoms, which may be substituted by one or more substituents R 1<, and R 1< and the other symbols used have the meanings mentioned above, in particular for formula (I).

[0096] In a further preferred embodiment of the invention, L1< represents a bond or an aromatic or heteroaromatic ring system with 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system with 6 to 12 carbon atoms, which may be substituted by one or more substituents R1<, but is preferably unsubstituted, wherein R1< may have the meaning mentioned above, particularly for formula (I). Particularly preferably, L1< represents an aromatic ring system with 6 to 10 aromatic ring atoms or a heteroaromatic ring system with 6 to 13 heteroaromatic ring atoms, each of which may be substituted by one or more substituents R2<, but is preferably unsubstituted, wherein R2< may have the meaning mentioned above, particularly for formula (I).

[0097] Furthermore preferably, the symbol L 1< shown, among other things, in formula (D3), whether the same or different, represents a bond or an aryl or heteroaryl residue with 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 ring atoms, such that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is directly bonded, i.e. via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group.

[0098] Furthermore, it may be provided that the group L 1< shown in formula (D3) comprises an aromatic ring system with at most two fused aromatic and / or heteroaromatic 6-membered rings, preferably no fused aromatic or heteroaromatic ring system. Accordingly, naphthyl structures are preferred over anthracene structures. Furthermore, fluorenyl, spirobifluorenyl, dibenzofuranyl and / or dibenzothienyl structures are preferred over naphthyl structures.

[0099] Structures that do not exhibit condensation, such as phenyl, biphenyl, terphenyl and / or quaterphenyl structures, are particularly preferred.

[0100] Examples of suitable aromatic or heteroaromatic ring systems L 1< are selected from the group consisting of ortho-, meta- or para-phenylenes, ortho-, meta- or para-biphenylenes, terphenylenes, in particular branched terphenylene, quaterphenylenes, in particular branched quaterphenylene, fluorenylenes, spirobifluorenylenes, dibenzofuranyles, dibenzothienylenes and carbazolylenes, each of which may be substituted by one or more residues R 1<, but are preferably unsubstituted.

[0101] The preferred embodiments mentioned above can be combined with one another as desired within the limitations defined in claim 1. In a particularly preferred embodiment of the invention, the preferences mentioned above occur simultaneously.

[0102] In a further embodiment of the present invention, compounds according to formula (I) are preferred in which the residues R a< together form a ring, wherein these compounds have the following properties: Formula of the ring, the residues R a< form Z 1< Z 2< Z 3< Cy-1 C(R 3< ) 2 C(R 1< ) 2 C(R 3< ) 2 Cy-2 C(R 3< ) 2 C(R 1< ) 2 C(R 3< ) 2 Cy-3 C(R 3< ) 2 C(R 1< ) 2 C(R 3< ) 2 Cy-1 Si(R 3< ) 2 C(R 1< ) 2 Si(R 3< ) 2 Cy-2 Si(R 3< ) 2 C(R 1< ) 2 Si(R 3< ) 2 Cy-3 Si(R 3< ) 2 C(R 1< ) 2 Si(R 3< ) 2

[0103] In a further embodiment of the present invention, compounds according to formula (I) are preferred in which the residues R a< together form a ring, wherein these compounds have the following properties: Formula of the ring, the residues R a< form G R 1< Z 2< Cy-4 Alkylene group with 1, 2 or 3 carbon atoms H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-5 Alkylene group with 1, 2 or 3 carbon atoms H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-6 Alkylene group with 1, 2 or 3 carbon atoms H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-7 Alkylene group with 1, 2 or 3 carbon atoms H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-8 Alkylene group with 1, 2 or 3 carbon atoms H or Ar-1 to H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-9 Alkylene group with 1, 2 or 3 carbon atoms H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-10 Alkylene group with 1, 2 or 3 carbon atoms H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-4 -CR 1< =CR 1< - H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-5 -CR 1< =CR 1< - H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-6 -CR 1< =CR 1< - H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-7 -CR 1< =CR 1< - H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-8 -CR 1< =CR 1< - H or Ar-1 to H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-9 -CR 1< =CR 1< - H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-10 -CR 1< =CR 1< - H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-4 Arylene or heteroarylene group with 5 to 14 aromatic ring atoms H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-5 Arylene or heteroarylene group with 5 to 14 aromatic ring atoms H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-6 Arylene or heteroarylene group with 5 to 14 aromatic ring atoms H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-7 Arylene or heteroarylene group with 5 to 14 aromatic ring atoms H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-8 Arylene or heteroarylene group with 5 to 14 aromatic ring atoms H or Ar-1 to H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-9 Arylene or heteroarylene group with 5 to 14 aromatic ring atoms H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2 Cy-10 Arylene or heteroarylene group with 5 to 14 aromatic ring atoms H, Methyl or Ar-1 to Ar-75, preferably H C(R 1< ) 2

[0104] In a further embodiment, the previously stated preferences regarding ring formation of two residues R a< to structures of the formulas (Cy-1) to (Cy-10) apply to two residues R c< .

[0105] In a further embodiment, the previously stated preferences regarding ring formation of two residues R a< to structures of the formulas (Cy-1) to (Cy-10) apply to two residues R e< .

[0106] In a further embodiment of the present invention, compounds according to formula (I-1) are preferred, wherein the two residues R a< form a ring, the two residues R c< form a ring and wherein the residues R a< , R b< , R c< , R d< and R e< have the following meanings: Ra< R b< R c< R d< Re< RA-5 H, D, Alkyl RA-5 H, D, Alkyl H, D, Alkyl RA-4 H, D, Alkyl RA-4 H, D, Alkyl H, D, Alkyl RA-4f H, D, Alkyl RA-4f H, D, Alkyl H, D, Alkyl RA-3 H, D, Alkyl RA-3 H, D, Alkyl H, D, Alkyl RB H, D, Alkyl RB H, D, Alkyl H, D, Alkyl RA-5 H, D, Alkyl RA-5 H, D, alkyl and phenyl ring formation with Re< Phenyl ring formation with R d< RA-5 H, D, Alkyl RA-5 Aryl, heteroaryl and phenyl ring formation with Re< Phenyl ring formation with R d< RA-4 H, D, Alkyl RA-4 H, D, alkyl and phenyl ring formation with Re< Phenyl ring formation with R d< RA-4 H, D, Alkyl RA-4 Aryl, heteroaryl and phenyl ring formation with Re< Phenyl ring formation with R d< RA-4f H, D, Alkyl RA-4f H, D, alkyl and phenyl ring formation with Re< Phenyl ring formation with R d< RA-4f H, D, Alkyl RA-4f Aryl, heteroaryl and phenyl ring formation with Re< Phenyl ring formation with R d< RA-3 H, D, Alkyl RA-3 H, D, alkyl and phenyl ring formation with Re< Phenyl ring formation with R d< RA-3 H, D, Alkyl RA-3 Aryl, heteroaryl and phenyl ring formation with Re< Phenyl ring formation with R d< RB H, D, Alkyl RB H, D, alkyl and phenyl ring formation with Re< Phenyl ring formation with R d< RB H, D, Alkyl RB Aryl, heteroaryl and phenyl ring formation with Re< Phenyl ring formation with R d< RA-5 H, D, Alkyl RA-5 H, D, alkyl and heteroaryl ring formation with Re< Heteroaryl ring formation with R d< RA-5 H, D, Alkyl RA-5 Aryl, heteroaryl and heteroaryl ring formation with Re< Heteroaryl ring formation with R d< RA-4 H, D, Alkyl RA-4 H, D, alkyl and heteroaryl ring formation with Re< Heteroaryl ring formation with R d< RA-4 H, D, Alkyl RA-4 Aryl, heteroaryl and heteroaryl ring formation with Re< Heteroaryl Ring Formation with R d< RA-4f H, D, Alkyl RA-4f H, D, Alkyl and Heteroaryl Ring Formation with R e< Heteroaryl Ring Formation with R d< RA-4f H, D, Alkyl RA-4f Aryl, Heteroaryl, and Heteroaryl Ring Formation with R e< Heteroaryl Ring Formation with R d< RA-3 H, D, Alkyl RA-3 H, D, Alkyl and Heteroaryl Ring Formation with R e< Heteroaryl Ring Formation with R d< RA-3 H, D, Alkyl RA-3 Aryl, Heteroaryl, and Heteroaryl Ring Formation with R e< Heteroaryl Ring Formation with R d< RB H, D, Alkyl RB H, D, Alkyl and Heteroaryl Ring Formation with R e< Heteroaryl Ring Formation with R d< RB H, D, Alkyl RB Aryl, Heteroaryl, and Heteroaryl Ring Formation with R e< Heteroaryl Ring Formation with R d< RA-5 H, D, Alkyl RA-5 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RA-4 H, D, Alkyl RA-4 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RA-4f H, D, Alkyl RA-4f H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RA-3 H, D, Alkyl RA-3 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RB H, D, Alkyl RB H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RA-5 H, D, Alkyl RA-5 H, D, Alkyl and Ring Formation with R e< C(Ar') 3 , Si(Ar') 3 RA-4 H, D, Alkyl RA-4 H, D, Alkyl and Ring Formation with R e< C(Ar') 3 , Si(Ar') 3 RA-4f H, D, Alkyl RA-4f H, D, Alkyl and Ring Formation with R e< C(Ar') 3 , Si(Ar') 3 RA-3 H, D, Alkyl RA-3 H, D, Alkyl and Ring Formation with R e< C(Ar') 3 , Si(Ar') 3 RB H, D, Alkyl RB H, D, Alkyl and Ring Formation with R e< C(Ar') 3 , Si(Ar') 3 RA-5 H, D, Alkyl RA-5 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 RA-4 H, D, Alkyl RA-4 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 RA-4f H, D, Alkyl RA-4f H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 RA-3 H, D, Alkyl RA-3 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 RB H, D, Alkyl RB H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 RA-5 H, D, Alkyl RA-5 H, D, Alkyl and Ring Formation with R e< N(Ar') 3 , N(R 1< ) 3 RA-4 H, D, Alkyl RA-4 H, D, Alkyl and Ring Formation with R e< N(Ar') 3 , N(R 1< ) 3 RA-4f H, D, Alkyl RA-4f H, D, Alkyl and Ring Formation with R e< N(Ar') 3 , N(R 1< ) 3 RA-3 H, D, Alkyl RA-3 H, D, Alkyl and Ring Formation with R e< N(Ar') 3 , N(R 1< ) 3 RB H, D, Alkyl RB H, D, Alkyl and Ring Formation with R e< N(Ar') 3 , N(R 1< ) 3 RA-5 H, D, Alkyl RA-5 H, D, Alkyl and RA-5 ring formation with R e< RA-5 Ring Formation with R d< RA-4 H, D, Alkyl RA-4 H, D, alkyl and RA-4-rings with R e< RA-4-Ring with R d< RA-4f H, D, Alkyl RA-4f H, D, Alkyl and RA-4f-Ring with R e< RA-4f-ringbinding with R d< RA-3 H, D, Alkyl RA-3 H, D, alkyl and RA-3-rings with R e< RA-3-ringbinding with R d< RB H, D, Alkyl RB H, D, Alkyl and RB -Rings with R e< RB-Ring with R d< RA-5 H, D, Alkyl RA-5 H, D, Alkyl Ar-1 day Ar-75 RA-4 H, D, Alkyl RA-4 H, D, Alkyl Ar-1 day Ar-75 RA-4f H, D, Alkyl RA-4f H, D, Alkyl Ar-1 day Ar-75 RA-3 H, D, Alkyl RA-3 H, D, Alkyl Ar-1 day Ar-75 RB H, D, Alkyl RB H, D, Alkyl Ar-1 day Ar-75 RA-5 H, D, Alkyl RA-5 RA-2, RA-2c RA-2, RA-2c RA-4 H, D, Alkyl RA-4 RA-2, RA-2c RA-2, RA-2c RA-4f H, D, Alkyl RA-4f RA-2, RA-2c RA-2, RA-2c RA-3 H, D, Alkyl RA-3 RA-2, RA-2c RA-2, RA-2c RB H, D, Alkyl RB RA-2, RA-2c RA-2, RA-2c

[0107] In a further embodiment of the present invention, compounds according to formula (1-14) are preferred, wherein the two residues R a< form a ring, the two residues R c< form a ring and wherein the residues R a< , R b< , R c< , R d< and R e< have the following meanings: R a< R allele b< R c< R d< R e< RA-5 H, D, Alkyl RA-5 H, D, Alkyl H, D, Alkyl RA-4 H, D, Alkyl RA-4 H, D, Alkyl H, D, Alkyl RA-4f H, D, Alkyl RA-4f H, D, Alkyl H, D, Alkyl RA-3 H, D, Alkyl RA-3 H, D, Alkyl H, D, Alkyl RB H, D, Alkyl RB H, D, Alkyl H, D, Alkyl RA-5 H, D, Alkyl RA-5 H, D, alkyl and phenyl ring formation with Re< Phenyl ring formation with R d< RA-5 H, D, Alkyl RA-5 Aryl, heteroaryl and phenyl ring formation with Re< Phenyl ring formation with R d< RA-4 H, D, Alkyl RA-4 H, D, alkyl and phenyl ring formation with Re< Phenyl ring formation with R d< RA-4 H, D, Alkyl RA-4 Aryl, heteroaryl and phenyl ring formation with Re< Phenyl ring formation with R d< RA-4f H, D, Alkyl RA-4f H, D, alkyl and phenyl ring formation with Re< Phenyl ring formation with R d< RA-4f H, D, Alkyl RA-4f Aryl, heteroaryl and phenyl ring formation with Re< Phenyl ring formation with R d< RA-3 H, D, Alkyl RA-3 H, D, alkyl and phenyl ring formation with Re< Phenyl ring formation with R d< RA-3 H, D, Alkyl RA-3 Aryl, heteroaryl and phenyl ring formation with Re< Phenyl ring formation with R d< RB H, D, Alkyl RB H, D, alkyl and phenyl ring formation with Re< Phenyl ring formation with R d< RB H, D, Alkyl RB Aryl, heteroaryl and phenyl ring formation with Re< Phenyl ring formation with R d< RA-5 H, D, Alkyl RA-5 H, D, alkyl and heteroaryl ring formation with Re< Heteroaryl ring formation with R d< RA-5 H, D, Alkyl RA-5 Aryl, heteroaryl and heteroaryl ring formation with Re< Heteroaryl ring formation with R d< RA-4 H, D, Alkyl RA-4 H, D, alkyl and heteroaryl ring formation with Re< Heteroaryl ring formation with R d< RA-4 H, D, Alkyl RA-4 Aryl, heteroaryl and heteroaryl ring formation with Re< Heteroaryl ring formation with R d< RA-4f H, D, Alkyl RA-4f H, D, alkyl and heteroaryl ring formation with Re< Heteroaryl ring formation with R d< RA-4f H, D, Alkyl RA-4f Aryl, heteroaryl and heteroaryl ring formation with Re< Heteroaryl ring formation with R d< RA-3 H, D, Alkyl RA-3 H, D, alkyl and heteroaryl ring formation with Re< Heteroaryl ring formation with R d< RA-3 H, D, Alkyl RA-3 Aryl, heteroaryl and heteroaryl ring formation with Re< Heteroaryl ring formation with R d< RB H, D, Alkyl RB H, D, alkyl and heteroaryl ring formation with Re< Heteroaryl ring formation with R d< RB H, D, Alkyl RB Aryl, heteroaryl and heteroaryl ring formation with Re< Heteroaryl ring formation with R d< RA-5 H, D, Alkyl RA-5 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RA-4 H, D, Alkyl RA-4 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RA-4f H, D, Alkyl RA-4f H, D, Alkyl C(Ar) 3 , Si(Ar) 3 RA-3 H, D, Alkyl RA-3 H, D, Alkyl C(Ar) 3 , Si(Ar) 3 RB H, D, Alkyl RB H, D, Alkyl C(Ar) 3 , Si(Ar) 3 RA-5 H, D, Alkyl RA-5 H, D, alkyl and ring structures with R e< C(Ar) 3 , Si(Ar) 3 RA-4 H, D, Alkyl RA-4 H, D, alkyl and ring structures with R e< C(Ar) 3 , Si(Ar) 3 RA-4f H, D, Alkyl RA-4f H, D, alkyl and ring structures with R e< C(Ar) 3 , Si(Ar) 3 RA-3 H, D, Alkyl RA-3 H, D, alkyl and ring structures with R e< C(Ar) 3 , Si(Ar) 3 RB H, D, Alkyl RB H, D, alkyl and ring structures with R e< C(Ar) 3 , Si(Ar) 3 RA-5 H, D, Alkyl RA-5 H, D, Alkyl N(R) 3 , N(R 1< ) 3 RA-4 H, D, Alkyl RA-4 H, D, Alkyl N(R) 3 , N(R 1< ) 3 RA-4f H, D, Alkyl RA-4f H, D, Alkyl N(R) 3 , N(R 1< ) 3 RA-3 H, D, Alkyl RA-3 H, D, Alkyl N(R) 3 , N(R 1< ) 3 RB H, D, Alkyl RB H, D, Alkyl N(R) 3 , N(R 1< ) 3 RA-5 H, D, Alkyl RA-5 H, D, alkyl and ring structures with R e< N(R) 3 , N(R 1< ) 3 RA-4 H, D, Alkyl RA-4 H, D, alkyl and ring structures with R e< N(R) 3 , N(R 1< ) 3 RA-4f H, D, Alkyl RA-4f H, D, alkyl and ring structures with R e< N(R) 3 , N(R 1< ) 3 RA-3 H, D, Alkyl RA-3 H, D, alkyl and ring structures with R e< N(R) 3 , N(R 1< ) 3 RB H, D, Alkyl RB H, D, alkyl and ring structures with R e< N(R) 3 , N(R 1< ) 3 RA-5 H, D, Alkyl RA-5 H, D, Alkyl and RA-5-Ring with R e< RA-5-Ring with R d< RA-4 H, D, Alkyl RA-4 H, D, alkyl and RA-4-rings with R e< RA-4-Ring with R d< RA-4f H, D, Alkyl RA-4f H, D, Alkyl and RA-4f-Ring with R e< RA-4f-ringbinding with R d< RA-3 H, D, Alkyl RA-3 H, D, alkyl and RA-3-rings with R e< RA-3-ringbinding with R d< RB H, D, Alkyl RB H, D, Alkyl and RB -Rings with R e< RB-Ring with R d< RA-5 H, D, Alkyl RA-5 H, D, Alkyl Ar-1 day Ar-75 RA-4 H, D, Alkyl RA-4 H, D, Alkyl Ar-1 day Ar-75 RA-4f H, D, Alkyl RA-4f H, D, Alkyl Ar-1 day Ar-75 RA-3 H, D, Alkyl RA-3 H, D, Alkyl Ar-1 day Ar-75 RB H, D, Alkyl RB H, D, Alkyl Ar-1 day Ar-75 RA-5 H, D, Alkyl RA-5 RA-2, RA-2c RA-2, RA-2c RA-4 H, D, Alkyl RA-4 RA-2, RA-2c RA-2, RA-2c RA-4f H, D, Alkyl RA-4f RA-2, RA-2c RA-2, RA-2c RA-3 H, D, Alkyl RA-3 RA-2, RA-2c RA-2, RA-2c RB H, D, Alkyl RB RA-2, RA-2c RA-2, RA-2c

[0108] In a further embodiment of the present invention, compounds according to formula (1-2) are preferred, wherein the two residues R a< form a ring, the two residues R c< form a ring, wherein the index I is preferably less than or equal to 3, particularly preferably 0, 1 or 2 and especially preferably 0 or 1, and wherein the residues R a< , R b< , R c< , R d< and R e< have the following meanings: R a< R b< R c< R d< R e< (nur falls I ungleich 0 ist mindestens ein Rest R e< , andernfalls sind alle R e< H) RA-5 H, D, Alkyl RA-5 H, D, Alkyl D, Alkyl RA-4 H, D, Alkyl RA-4 H, D, Alkyl D, Alkyl RA-4f H, D, Alkyl RA-4f H, D, Alkyl D, Alkyl RA-3 H, D, Alkyl RA-3 H, D, Alkyl D, Alkyl RB H, D, Alkyl RB H, D, Alkyl D, Alkyl RA-5 H, D, Alkyl RA-5 H, D, Alkyl Ar-1 bis Ar-75 RA-4 H, D, Alkyl RA-4 H, D, Alkyl Ar-1 bis Ar-75 RA-4f H, D, Alkyl RA-4f H, D, Alkyl Ar-1 bis Ar-75 RA-3 H, D, Alkyl RA-3 H, D, Alkyl Ar-1 bis Ar-75 RB H, D, Alkyl RB H, D, Alkyl Ar-1 bis Ar-75 RA-5 H, D, Alkyl RA-5 Ar-1 bis Ar-75 D, Alkyl RA-4 H, D, Alkyl RA-4 Ar-1 bis Ar-75 D, Alkyl RA-4f H, D, Alkyl RA-4f Ar-1 bis Ar-75 D, Alkyl RA-3 H, D, Alkyl RA-3 Ar-1 bis Ar-75 D, Alkyl RB H, D, Alkyl RB Ar-1 bis Ar-75 D, Alkyl RA-5 H, D, Alkyl RA-5 Ar-1 bis Ar-75 Ar-1 bis Ar-75 RA-4 H, D, Alkyl RA-4 Ar-1 bis Ar-75 Ar-1 bis Ar-75 RA-4f H, D, Alkyl RA-4f Ar-1 bis Ar-75 Ar-1 bis Ar-75 RA-3 H, D, Alkyl RA-3 Ar-1 bis Ar-75 Ar-1 bis Ar-75 RB H, D, Alkyl RB Ar-1 bis Ar-75 Ar-1 bis Ar-75 RA-5 H, D, Alkyl RA-5 H, D, Alkyl und Ar-1 bis Ar-75 D, Alkyl RA-4 H, D, Alkyl RA-4 H, D, Alkyl und Ar-1 bis Ar-75 D, Alkyl RA-4f H, D, Alkyl RA-4f H, D, Alkyl und Ar-1 bis Ar-75 D, Alkyl RA-3 H, D, Alkyl RA-3 H, D, Alkyl und Ar-1 bis Ar-75 D, Alkyl RB H, D, Alkyl RB H, D, Alkyl und Ar-1 bis Ar-75 D, Alkyl RA-5 H, D, Alkyl RA-5 H, D, Alkyl und Ar-1 bis Ar-75 Ar-1 to Ar-75 RA-4 H, D, Alkyl RA-4 H, D, Alkyl und Ar-1 bis Ar-75 Ar-1 to Ar-75 RA-4f H, D, Alkyl RA-4f H, D, Alkyl und Ar-1 bis Ar-75 Ar-1 to Ar-75 RA-3 H, D, Alkyl RA-3 H, D, Alkyl und Ar-1 bis Ar-75 Ar-1 to Ar-75 RB H, D, Alkyl RB H, D, Alkyl und Ar-1 bis Ar-75 Ar-1 to Ar-75 RA-5 H, D, Alkyl RA-5 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RA-4 H, D, Alkyl RA-4 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RA-4f H, D, Alkyl RA-4f H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RA-3 H, D, Alkyl RA-3 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RB H, D, Alkyl RB H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RA-5 H, D, Alkyl RA-5 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 RA-4 H, D, Alkyl RA-4 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 RA-4f H, D, Alkyl RA-4f Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 RA-3 H, D, Alkyl RA-3 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 RB H, D, Alkyl RB Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 RA-5 H, D, Alkyl RA-5 H, D, Alkyl und Ar-1 bis Ar-75 C(Ar') 3 , Si(Ar') 3 RA-4 H, D, Alkyl RA-4 H, D, Alkyl und Ar-1 bis Ar-75 C(Ar') 3 , Si(Ar') 3 RA-4f H, D, Alkyl RA-4f H, D, Alkyl und Ar-1 bis Ar-75 C(Ar') 3 , Si(Ar') 3 RA-3 H, D, Alkyl RA-3 H, D, Alkyl und Ar-1 bis Ar-75 C(Ar') 3 , Si(Ar') 3 RB H, D, Alkyl RB H, D, Alkyl und Ar-1 bis Ar-75 C(Ar') 3 , Si(Ar') 3 RA-5 H, D, Alkyl RA-5 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 RA-4 H, D, Alkyl RA-4 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 RA-4f H, D, Alkyl RA-4f H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 RA-3 H, D, Alkyl RA-3 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 RB H, D, Alkyl RB H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 RA-5 H, D, Alkyl RA-5 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 RA-4 H, D, Alkyl RA-4 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 RA-4f H, D, Alkyl RA-4f Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 RA-3 H, D, Alkyl RA-3 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 RB H, D, Alkyl RB Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 RA-5 H, D, Alkyl RA-5 H, D, Alkyl und Ar-1 bis Ar-75 N(Ar') 3 , N(R 1< ) 3 RA-4 H, D, Alkyl RA-4 H, D, Alkyl und Ar-1 bis Ar-75 N(Ar') 3 , N(R 1< ) 3 RA-4f H, D, Alkyl RA-4f H, D, Alkyl und Ar-1 bis Ar-75 N(Ar') 3 , N(R 1< ) 3 RA-3 H, D, Alkyl RA-3 H, D, Alkyl und Ar-1 bis Ar-75 N(Ar') 3 , N(R 1< ) 3 RB H, D, Alkyl RB H, D, Alkyl und Ar-1 bis Ar-75 N(Ar') 3 , N(R 1< ) 3

[0109] In a further embodiment of the present invention, compounds according to formula (1-3) are preferred, wherein the two substituents R a< form a ring, the two substituents R c< form a ring, wherein the index m is preferably 0, 1 or 2 and particularly preferably 0 or 1, and wherein Rb is H, D, alkyl and the substituents R a< , R c< , R d< , Re< and Y 1< have the following meanings: R a< R c< R d< R e< am Phenyl ring (only if m ungleich 0 is at least one residue R e< , otherwise all R e< H) Y 1< RA-5 RA-5 H, D, Alkyl D, Alkyl C(R e< ) 2 RA-4 RA-4 H, D, Alkyl D, Alkyl C(R e< ) 2 RA-4f RA-4f H, D, Alkyl D, Alkyl C(R e< ) 2 RA-3 RA-3 H, D, Alkyl D, Alkyl C(R e< ) 2 RB RB H, D, Alkyl D, Alkyl C(R e< ) 2 RA-5 RA-5 H, D, Alkyl Ar-1 to Ar-75 C(R e< ) 2 RA-4 RA-4 H, D, Alkyl Ar-1 to Ar-75 C(R e< ) 2 RA-4f RA-4f H, D, Alkyl Ar-1 to Ar-75 C(R e< ) 2 RA-3 RA-3 H, D, Alkyl Ar-1 to Ar-75 C(R e< ) 2 RB RB H, D, Alkyl Ar-1 to Ar-75 C(R e< ) 2 RA-5 RA-5 Ar-1 to Ar-75 D, Alkyl C(R e< ) 2 RA-4 RA-4 Ar-1 to Ar-75 D, Alkyl C(R e< ) 2 RA-4f RA-4f Ar-1 to Ar-75 D, Alkyl C(R e< ) 2 RA-3 RA-3 Ar-1 to Ar-75 D, Alkyl C(R e< ) 2 RB RB Ar-1 to Ar-75 D, Alkyl C(R e< ) 2 RA-5 RA-5 Ar-1 to Ar-75 Ar-1 to Ar-75 C(R e< ) 2 RA-4 RA-4 Ar-1 to Ar-75 Ar-1 to Ar-75 C(R e< ) 2 RA-4f RA-4f Ar-1 to Ar-75 Ar-1 to Ar-75 C(R e< ) 2 RA-3 RA-3 Ar-1 to Ar-75 Ar-1 to Ar-75 C(R e< ) 2 RB RB Ar-1 to Ar-75 Ar-1 to Ar-75 C(R e< ) 2 RA-5 RA-5 H, D, Alkyl Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-4 RA-4 H, D, Alkyl Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-4f RA-4f H, D, Alkyl Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-3 RA-3 H, D, Alkyl Phenyl Ring Formation of 2 R e< C(R e< ) 2 RB RB H, D, Alkyl Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-5 RA-5 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-4 RA-4 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-4f RA-4f Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-3 RA-3 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< C(R e< ) 2 RB RB Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-5 RA-5 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-4 RA-4 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-4f RA-4f H, D, Alkyl C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-3 RA-3 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RB RB H, D, Alkyl C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-5 RA-5 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-4 RA-4 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-4f RA-4f Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-3 RA-3 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RB RB Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-5 RA-5 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-4 RA-4 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-4f RA-4f H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-3 RA-3 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RB RB H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-5 RA-5 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-4 RA-4 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-4f RA-4f Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-3 RA-3 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RB RB Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-5 RA-5 H, D, Alkyl D, Alkyl O, S RA-4 RA-4 H, D, Alkyl D, Alkyl O, S RA-4f RA-4f H, D, Alkyl D, Alkyl O, S RA-3 RA-3 H, D, Alkyl D, Alkyl O, S RB RB H, D, Alkyl D, Alkyl O, S RA-5 RA-5 H, D, Alkyl Ar-1 to Ar-75 O, S RA-4 RA-4 H, D, Alkyl Ar-1 to Ar-75 O, S RA-4f RA-4f H, D, Alkyl Ar-1 to Ar-75 O, S RA-3 RA-3 H, D, Alkyl Ar-1 to Ar-75 O, S RB RB H, D, Alkyl Ar-1 to Ar-75 O, S RA-5 RA-5 Ar-1 to Ar-75 D, Alkyl O, S RA-4 RA-4 Ar-1 to Ar-75 D, Alkyl O, S RA-4f RA-4f Ar-1 to Ar-75 D, Alkyl O, S RA-3 RA-3 Ar-1 to Ar-75 D, Alkyl O, S RB RB Ar-1 to Ar-75 D, Alkyl O, S RA-5 RA-5 Ar-1 to Ar-75 Ar-1 to Ar-75 O, S RA-4 RA-4 Ar-1 to Ar-75 Ar-1 to Ar-75 O, S RA-4f RA-4f Ar-1 to Ar-75 Ar-1 to Ar-75 O, S RA-3 RA-3 Ar-1 to Ar-75 Ar-1 to Ar-75 O, S RB RB Ar-1 to Ar-75 Ar-1 to Ar-75 O, S RA-5 RA-5 H, D, Alkyl Phenyl Ring Formation of 2 R e< O, S RA-4 RA-4 H, D, Alkyl Phenyl Ring Formation of 2 R e< O, S RA-4f RA-4f H, D, Alkyl Phenyl Ring Formation of 2 R e< O, S RA-3 RA-3 H, D, Alkyl Phenyl Ring Formation of 2 R e< O, S RB RB H, D, Alkyl Phenyl Ring Formation of 2 R e< O, S RA-5 RA-5 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< O, S RA-4 RA-4 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< O, S RA-4f RA-4f Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< O, S RA-3 RA-3 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< O, S RB RB Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< O, S RA-5 RA-5 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 O, S RA-4 RA-4 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 O, S RA-4f RA-4f H, D, Alkyl C(Ar') 3 , Si(Ar') 3 O, S RA-3 RA-3 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 O, S RB RB H, D, Alkyl C(Ar') 3 , Si(Ar') 3 O, S RA-5 RA-5 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 O, S RA-4 RA-4 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 O, S RA-4f RA-4f Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 O, S RA-3 RA-3 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 O, S RB RB Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 O, S RA-5 RA-5 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 O, S RA-4 RA-4 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 O, S RA-4f RA-4f H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 O, S RA-3 RA-3 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 O, S RB RB H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 O, S RA-5 RA-5 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 O, S RA-4 RA-4 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 O, S RA-4f RA-4f Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 O, S RA-3 RA-3 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 O, S RB RB Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 O, S RA-5 RA-5 H, D, Alkyl D, Alkyl N(Ar') RA-4 RA-4 H, D, Alkyl D, Alkyl N(Ar') RA-4f RA-4f H, D, Alkyl D, Alkyl N(Ar') RA-3 RA-3 H, D, Alkyl D, Alkyl N(Ar') RB RB H, D, Alkyl D, Alkyl N(Ar') RA-5 RA-5 H, D, Alkyl Ar-1 to Ar-75 N(Ar') RA-4 RA-4 H, D, Alkyl Ar-1 to Ar-75 N(Ar') RA-4f RA-4f H, D, Alkyl Ar-1 to Ar-75 N(Ar') RA-3 RA-3 H, D, Alkyl Ar-1 to Ar-75 N(Ar') RB RB H, D, Alkyl Ar-1 to Ar-75 N(Ar') RA-5 RA-5 Ar-1 to Ar-75 D, Alkyl N(Ar') RA-4 RA-4 Ar-1 to Ar-75 D, Alkyl N(Ar') RA-4f RA-4f Ar-1 to Ar-75 D, Alkyl N(Ar') RA-3 RA-3 Ar-1 to Ar-75 D, Alkyl N(Ar') RB RB Ar-1 to Ar-75 D, Alkyl N(Ar') RA-5 RA-5 Ar-1 to Ar-75 Ar-1 to Ar-75 N(Ar') RA-4 RA-4 Ar-1 to Ar-75 Ar-1 to Ar-75 N(Ar') RA-4f RA-4f Ar-1 to Ar-75 Ar-1 to Ar-75 N(Ar') RA-3 RA-3 Ar-1 to Ar-75 Ar-1 to Ar-75 N(Ar') RB RB Ar-1 to Ar-75 Ar-1 to Ar-75 N(Ar') RA-5 RA-5 H, D, Alkyl Phenyl Ring Formation of 2 R e< N(Ar') RA-4 RA-4 H, D, Alkyl Phenyl Ring Formation of 2 R e< N(Ar') RA-4f RA-4f H, D, Alkyl Phenyl Ring Formation of 2 R e< N(Ar') RA-3 RA-3 H, D, Alkyl Phenyl Ring Formation of 2 R e< N(Ar`) RB RB H, D, Alkyl Phenyl Ring Formation of 2 R e< N(Ar') RA-5 RA-5 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< N(Ar') RA-4 RA-4 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< N(Ar') RA-4f RA-4f Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< N(Ar') RA-3 RA-3 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< N(Ar') RB RB Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< N(Ar') RA-5 RA-5 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 N(Ar') RA-4 RA-4 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 N(Ar') RA-4f RA-4f H, D, Alkyl C(Ar') 3 , Si(Ar') 3 N(Ar') RA-3 RA-3 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 N(Ar') RB RB H, D, Alkyl C(Ar') 3 , Si(Ar') 3 N(Ar') RA-5 RA-5 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 N(Ar') RA-4 RA-4 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 N(Ar') RA-4f RA-4f Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 N(Ar') RA-3 RA-3 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 N(Ar') RB RB Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 N(Ar') RA-5 RA-5 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 N(Ar') RA-4 RA-4 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 N(Ar') RA-4f RA-4f H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 N(Ar') RA-3 RA-3 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 N(Ar') RB RB H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 N(Ar') RA-5 RA-5 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 N(Ar`) RA-4 RA-4 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 N(Ar`) RA-4f RA-4f Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 N(Ar`) RA-3 RA-3 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 N(Ar`) RB RB Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 N(Ar`) RA-5 RA-5 H, D, Alkyl D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 H, D, Alkyl D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f H, D, Alkyl D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 H, D, Alkyl D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB H, D, Alkyl D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 H, D, Alkyl Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 H, D, Alkyl Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f H, D, Alkyl Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 H, D, Alkyl Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB H, D, Alkyl Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 Ar-1 to Ar-75 D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 Ar-1 to Ar-75 D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f Ar-1 to Ar-75 D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 Ar-1 to Ar-75 D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB Ar-1 to Ar-75 D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 Ar-1 to Ar-75 Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 Ar-1 to Ar-75 Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f Ar-1 to Ar-75 Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 Ar-1 to Ar-75 Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB Ar-1 to Ar-75 Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 H, D, Alkyl Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 H, D, Alkyl Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f H, D, Alkyl Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 H, D, Alkyl Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB H, D, Alkyl Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f H, D, Alkyl C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB H, D, Alkyl C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< ) 2 CC(R e< )

[0110] In the tables above, the residues listed in the column under the group R e< represent the substituents on the phenyl ring of the framework, which is also substituted by the aforementioned residue R d< (see for example formula (I-1)), or the substituents on the phenyl ring that binds to the phenyl ring of the framework, which is also substituted by the aforementioned residue R d< (see for example formula (1-2) and (1-3)). In the group C(R e< ) 2, the residue R e< particularly represents the groups set out above, wherein R e< in the group C(R e< ) 2 preferably represents, in each instance, a linear alkyl group with 1 to 10 C atoms, or a branched or cyclic alkyl group with 3 to 10 C atoms, or an aromatic or heteroaromatic ring system with 5 to 24, preferably 5 to 13, aromatic ring atoms, which may also be substituted by one or more residues R 1<.Particularly preferably, R< represents a methyl group or a phenyl group. The R< substituents can also form a ring system with each other, leading to a spiro system. In the groups (R< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) the substituent R< represents, in particular, the groups described above, where R< in groups (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) preferably represents H, C 1 to C 4 alkyl, or an aryl or heteroaryl group with 5 to 13 carbon atoms, the aryl or heteroaryl group being potentially linked. Here, two groups R e< can form a condensed ring system in the group (R e< ) 2 CC(R e< ) 2 or (R e< )C=C(R e< ).

[0111] In a further embodiment of the present invention, compounds according to formula (1-4) are preferred, wherein the two residues R a< form a ring, the two residues R c< form a ring, wherein the index n is preferably 0, 1 or 2 and particularly preferably 0 or 1, and in the case of the Remaining R a< , R b< , R c< , R e< and Y 1< specify the following meanings: R a< R b< R c< R e< am Phenyl ring (only if m ungleich 0 is at least one residue R e< , otherwise all R e< H) Y 1< RA-5 H, D, Alkyl RA-5 D, Alkyl C(R e< ) 2 RA-4 H, D, Alkyl RA-4 D, Alkyl C(R e< ) 2 RA-4f H, D, Alkyl RA-4f D, Alkyl C(R e< ) 2 RA-3 H, D, Alkyl RA-3 D, Alkyl C(R e< ) 2 RB H, D, Alkyl RB D, Alkyl C(R e< ) 2 RA-5 H, D, Alkyl RA-5 Ar-1 to Ar-75 C(R e< ) 2 RA-4 H, D, Alkyl RA-4 Ar-1 to Ar-75 C(R e< ) 2 RA-4f H, D, Alkyl RA-4f Ar-1 to Ar-75 C(R e< ) 2 RA-3 H, D, Alkyl RA-3 Ar-1 to Ar-75 C(R e< ) 2 RB H, D, Alkyl RB Ar-1 to Ar-75 C(R e< ) 2 RA-5 H, D, Alkyl RA-5 Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-4 H, D, Alkyl RA-4 Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-4f H, D, Alkyl RA-4f Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-3 H, D, Alkyl RA-3 Phenyl Ring Formation of 2 R e< C(R e< ) 2 RB H, D, Alkyl RB Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-5 H, D, Alkyl RA-5 C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-4 H, D, Alkyl RA-4 C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-4f H, D, Alkyl RA-4f C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-3 H, D, Alkyl RA-3 C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RB H, D, Alkyl RB C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-5 H, D, Alkyl RA-5 N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-4 H, D, Alkyl RA-4 N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-4f H, D, Alkyl RA-4f N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-3 H, D, Alkyl RA-3 N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RB H, D, Alkyl RB N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-5 H, D, Alkyl RA-5 D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 H, D, Alkyl RA-4 D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f H, D, Alkyl RA-4f D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 H, D, Alkyl RA-3 D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB H, D, Alkyl RB D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 H, D, Alkyl RA-5 Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 H, D, Alkyl RA-4 Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f H, D, Alkyl RA-4f Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 H, D, Alkyl RA-3 Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB H, D, Alkyl RB Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 H, D, Alkyl RA-5 Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 H, D, Alkyl RA-4 Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f H, D, Alkyl RA-4f Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 H, D, Alkyl RA-3 Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB H, D, Alkyl RB Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 H, D, Alkyl RA-5 C(Ar') 3 , Si(Ar') 3 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) RA-4 H, D, Alkyl RA-4 C(Ar') 3 , Si(Ar') 3 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) RA-4f H, D, Alkyl RA-4f C(Ar') 3 , Si(Ar') 3 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) RA-3 H, D, Alkyl RA-3 C(Ar') 3 , Si(Ar') 3 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) RB H, D, Alkyl RB C(Ar') 3 , Si(Ar') 3 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) RA-5 H, D, Alkyl RA-5 N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) RA-4 H, D, Alkyl RA-4 N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) RA-4f H, D, Alkyl RA-4f N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) RA-3 H, D, Alkyl RA-3 N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) RB H, D, Alkyl RB N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) RA-5 H, D, Alkyl RA-5 D, Alkyl O, S RA-4 H, D, Alkyl RA-4 D, Alkyl O, S RA-4f H, D, Alkyl RA-4f D, Alkyl O, S RA-3 H, D, Alkyl RA-3 D, Alkyl O, S RB H, D, Alkyl RB D, Alkyl O, S RA-5 H, D, Alkyl RA-5 Ar-1 bis Ar-75 O, S RA-4 H, D, Alkyl RA-4 Ar-1 bis Ar-75 O, S RA-4f H, D, Alkyl RA-4f Ar-1 bis Ar-75 O, S RA-3 H, D, Alkyl RA-3 Ar-1 bis Ar-75 O, S RB H, D, Alkyl RB Ar-1 bis Ar-75 O, S RA-5 H, D, Alkyl RA-5 Phenyl-Ringbildung von 2 R e< O, S RA-4 H, D, Alkyl RA-4 Phenyl-Ringbildung von 2 R e< O, S RA-4f H, D, Alkyl RA-4f Phenyl-Ringbildung von 2 R e< O, S RA-3 H, D, Alkyl RA-3 Phenyl-Ringbildung von 2 R e< O, S RB H, D, Alkyl RB Phenyl-Ringbildung von 2 R e< O, S RA-5 H, D, Alkyl RA-5 C(Ar') 3 , Si(Ar') 3 O, S RA-4 H, D, Alkyl RA-4 C(Ar') 3 , Si(Ar') 3 O, S RA-4f H, D, Alkyl RA-4f C(Ar') 3 , Si(Ar') 3 O, S RA-3 H, D, Alkyl RA-3 C(Ar') 3 , Si(Ar') 3 O, S RB H, D, Alkyl RB C(Ar') 3 , Si(Ar') 3 O, S RA-5 H, D, Alkyl RA-5 N(Ar') 3 , N(R 1< ) 3 O, S RA-4 H, D, Alkyl RA-4 N(Ar') 3 , N(R 1< ) 3 O, S RA-4f H, D, Alkyl RA-4f N(Ar') 3 , N(R 1< ) 3 O, S RA-3 H, D, Alkyl RA-3 N(Ar') 3 , N(R 1< ) 3 O, S RB H, D, Alkyl RB N(Ar') 3 , N(R 1< ) 3 O, S RA-5 H, D, Alkyl RA-5 D, Alkyl O, S und C(R e< ) 2 RA-4 H, D, Alkyl RA-4 D, Alkyl O, S und C(R e< ) 2 RA-4f H, D, Alkyl RA-4f D, Alkyl O, S und C(R e< ) 2 RA-3 H, D, Alkyl RA-3 D, Alkyl O, S und C(R e< ) 2 RB H, D, Alkyl RB D, Alkyl O, S and C(R e< ) 2 RA-5 H, D, Alkyl RA-5 Ar-1 to Ar-75 O, S and C(R e< ) 2 RA-4 H, D, Alkyl RA-4 Ar-1 to Ar-75 O, S and C(R e< ) 2 RA-4f H, D, Alkyl RA-4f Ar-1 to Ar-75 O, S and C(R e< ) 2 RA-3 H, D, Alkyl RA-3 Ar-1 to Ar-75 O, S and C(R e< ) 2 RB H, D, Alkyl RB Ar-1 to Ar-75 O, S and C(R e< ) 2 RA-5 H, D, Alkyl RA-5 Phenyl Ring Formation of 2 R e< O, S and C(R e< ) 2 RA-4 H, D, Alkyl RA-4 Phenyl Ring Formation of 2 R e< O, S and C(R e< ) 2 RA-4f H, D, Alkyl RA-4f Phenyl Ring Formation of 2 R e< O, S and C(R e< ) 2 RA-3 H, D, Alkyl RA-3 Phenyl Ring Formation of 2 R e< O, S and C(R e< ) 2 RB H, D, Alkyl RB Phenyl Ring Formation of 2 R e< O, S and C(R e< ) 2 RA-5 H, D, Alkyl RA-5 C(Ar') 3 , Si(Ar') 3 O, S and C(R e< ) 2 RA-4 H, D, Alkyl RA-4 C(Ar') 3 , Si(Ar') 3 O, S and C(R e< ) 2 RA-4f H, D, Alkyl RA-4f C(Ar') 3 , Si(Ar') 3 O, S and C(R e< ) 2 RA-3 H, D, Alkyl RA-3 C(Ar') 3 , Si(Ar') 3 O, S and C(R e< ) 2 RB H, D, Alkyl RB C(Ar') 3 , Si(Ar') 3 O, S and C(R e< ) 2 RA-5 H, D, Alkyl RA-5 N(Ar') 3 , N(R 1< ) 3 O, S and C(R e< ) 2 RA-4 H, D, Alkyl RA-4 N(Ar') 3 , N(R 1< ) 3 O, S und C(R e< ) 2 RA-4f H, D, Alkyl RA-4f N(Ar') 3 , N(R 1< ) 3 O, S und C(R e< ) 2 RA-3 H, D, Alkyl RA-3 N(Ar') 3 , N(R 1< ) 3 O, S und C(R e< ) 2 RB H, D, Alkyl RB N(Ar') 3 , N(R 1< ) 3 O, S und C(R e< ) 2 RA-5 H, D, Alkyl RA-5 D, Alkyl (R e< ) 2 C-C(R e< ) 2 , und C(R e< ) 2 RA-4 H, D, Alkyl RA-4 D, Alkyl (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-4f H, D, Alkyl RA-4f D, Alkyl (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-3 H, D, Alkyl RA-3 D, Alkyl (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RB H, D, Alkyl RB D, Alkyl (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-5 H, D, Alkyl RA-5 Ar-1 bis Ar-75 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-4 H, D, Alkyl RA-4 Ar-1 bis Ar-75 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-4f H, D, Alkyl RA-4f Ar-1 bis Ar-75 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-3 H, D, Alkyl RA-3 Ar-1 bis Ar-75 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RB H, D, Alkyl RB Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-5 H, D, Alkyl RA-5 Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-4 H, D, Alkyl RA-4 Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-4f H, D, Alkyl RA-4f Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-3 H, D, Alkyl RA-3 Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RB H, D, Alkyl RB Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-5 H, D, Alkyl RA-5 C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-4 H, D, Alkyl RA-4 C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-4f H, D, Alkyl RA-4f C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-3 H, D, Alkyl RA-3 C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RB H, D, Alkyl RB C(Ar') 3 , Si(Ar') 3 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-5 H, D, Alkyl RA-5 N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-4 H, D, Alkyl RA-4 N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-4f H, D, Alkyl RA-4f N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-3 H, D, Alkyl RA-3 N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RB H, D, Alkyl RB N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) und C(R e< ) 2 RA-5 H, D, Alkyl RA-5 D, Alkyl O, S und (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) RA-4 H, D, Alkyl RA-4 D, Alkyl O, S und (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) RA-4f H, D, Alkyl RA-4f D, Alkyl O, S und (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) RA-3 H, D, Alkyl RA-3 D, Alkyl O, S und (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) RB H, D, Alkyl RB D, Alkyl O, S und (R e< ) 2 C-C(R e< ) 2 , (R e< )C=C(R e< ) RA-5 H, D, Alkyl RA-5 Ar-1 bis Ar-75 O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 H, D, Alkyl RA-4 Ar-1 to Ar-75 O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f H, D, Alkyl RA-4f Ar-1 to Ar-75 O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 H, D, Alkyl RA-3 Ar-1 to Ar-75 O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB H, D, Alkyl RB Ar-1 to Ar-75 O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 H, D, Alkyl RA-5 Phenyl Ring Formation of 2 R e< O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 H, D, Alkyl RA-4 Phenyl Ring Formation of 2 R e< O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f H, D, Alkyl RA-4f Phenyl Ring Formation of 2 R e< O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 H, D, Alkyl RA-3 Phenyl Ring Formation of 2 R e< O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB H, D, Alkyl RB Phenyl Ring Formation of 2 R e< O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 H, D, Alkyl RA-5 C(Ar') 3 , Si(Ar') 3 O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 H, D, Alkyl RA-4 C(Ar') 3 , Si(Ar') 3 O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f H, D, Alkyl RA-4f C(Ar') 3 , Si(Ar') 3 O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 H, D, Alkyl RA-3 C(Ar') 3 , Si(Ar') 3 O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB H, D, Alkyl RB C(Ar') 3 , Si(Ar') 3 O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 H, D, Alkyl RA-5 N(Ar') 3 , N(R 1< ) 3 O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 H, D, Alkyl RA-4 N(Ar') 3 , N(R 1< ) 3 O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f H, D, Alkyl RA-4f N(Ar') 3 , N(R 1< ) 3 O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 H, D, Alkyl RA-3 N(Ar') 3 , N(R 1< ) 3 O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB H, D, Alkyl RB N(Ar') 3 , N(R 1< ) 3 O, S und (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< )

[0112] In the table above, the substituents listed in the column under group R e< represent the substituents on the phenyl ring linked to group Y 1<. In group C(R e< ) 2, the substituent R e< represents, in particular, the groups described above, wherein R e< in group C(R e< ) 2 preferably represents, either the same or different in each instance, a linear alkyl group with 1 to 10 carbon atoms, or a branched or cyclic alkyl group with 3 to 10 carbon atoms, or an aromatic or heteroaromatic ring system with 5 to 24, preferably 5 to 13, aromatic ring atoms, which may also be substituted by one or more R 1< substituents. R e< most preferably represents a methyl group or a phenyl group. The R e< substituents may also form a ring system with each other, leading to a spiro system.In the groups (Re<)2CC(Re<)2, (Re<)C=C(Re<), the substituent Re< particularly represents the groups described above, where Re< in groups (Re<)2CC(Re<)2, (Re<)C=C(Re<) preferably represents H, C1 to C4 alkyl, or an aryl or heteroaryl group with 5 to 13 carbon atoms, the aryl or heteroaryl group being potentially linked. Two Re< groups in the group (Re<)2CC(Re<)2 or (Re<)C=C(Re<) can form a fused ring system.

[0113] In a further embodiment of the present invention, compounds according to formula (1-5) are preferred, wherein the two substituents R a< form a ring, the two substituents R c< form a ring, wherein the index m is preferably 0, 1 or 2 and particularly preferably 0 or 1, and wherein R b< is H, D, alkyl and the substituents R a< , R c< , R d< , Re< and Y 1< are the following Definitions: R a< R c< R d< R e< am Phenyl ring (only if I unequal 0 is at least one residue Re, otherwise all R e< H) Y 1< RA-5 RA-5 H, D, Alkyl D, Alkyl C(R e< ) 2 RA-4 RA-4 H, D, Alkyl D, Alkyl C(R e< ) 2 RA-4f RA-4f H, D, Alkyl D, Alkyl C(R e< ) 2 RA-3 RA-3 H, D, Alkyl D, Alkyl C(R e< ) 2 RB RB H, D, Alkyl D, Alkyl C(R e< ) 2 RA-5 RA-5 H, D, Alkyl Ar-1 to Ar-75 C(R e< ) 2 RA-4 RA-4 H, D, Alkyl Ar-1 to Ar-75 C(R e< ) 2 RA-4f RA-4f H, D, Alkyl Ar-1 to Ar-75 C(R e< ) 2 RA-3 RA-3 H, D, Alkyl Ar-1 to Ar-75 C(R e< ) 2 RB RB H, D, Alkyl Ar-1 to Ar-75 C(R e< ) 2 RA-5 RA-5 Ar-1 to Ar-75 D, Alkyl C(R e< ) 2 RA-4 RA-4 Ar-1 to Ar-75 D, Alkyl C(R e< ) 2 RA-4f RA-4f Ar-1 to Ar-75 D, Alkyl C(R e< ) 2 RA-3 RA-3 Ar-1 to Ar-75 D, Alkyl C(R e< ) 2 RB RB Ar-1 to Ar-75 D, Alkyl C(R e< ) 2 RA-5 RA-5 Ar-1 to Ar-75 Ar-1 to Ar-75 C(R e< ) 2 RA-4 RA-4 Ar-1 to Ar-75 Ar-1 to Ar-75 C(R e< ) 2 RA-4f RA-4f Ar-1 to Ar-75 Ar-1 to Ar-75 C(R e< ) 2 RA-3 RA-3 Ar-1 to Ar-75 Ar-1 to Ar-75 C(R e< ) 2 RB RB Ar-1 to Ar-75 Ar-1 to Ar-75 C(R e< ) 2 RA-5 RA-5 H, D, Alkyl Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-4 RA-4 H, D, Alkyl Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-4f RA-4f H, D, Alkyl Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-3 RA-3 H, D, Alkyl Phenyl Ring Formation of 2 R e< C(R e< ) 2 RB RB H, D, Alkyl Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-5 RA-5 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-4 RA-4 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-4f RA-4f Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-3 RA-3 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< C(R e< ) 2 RB RB Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< C(R e< ) 2 RA-5 RA-5 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-4 RA-4 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-4f RA-4f H, D, Alkyl C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-3 RA-3 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RB RB H, D, Alkyl C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-5 RA-5 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-4 RA-4 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-4f RA-4f Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-3 RA-3 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RB RB Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 C(R e< ) 2 RA-5 RA-5 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-4 RA-4 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-4f RA-4f H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-3 RA-3 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RB RB H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-5 RA-5 Ar-1 bis Ar-75 N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-4 RA-4 Ar-1 bis Ar-75 N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-4f RA-4f Ar-1 bis Ar-75 N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-3 RA-3 Ar-1 bis Ar-75 N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RB RB Ar-1 bis Ar-75 N(Ar') 3 , N(R 1< ) 3 C(R e< ) 2 RA-5 RA-5 H, D, Alkyl D, Alkyl O, S RA-4 RA-4 H, D, Alkyl D, Alkyl O, S RA-4f RA-4f H, D, Alkyl D, Alkyl O, S RA-3 RA-3 H, D, Alkyl D, Alkyl O, S RB RB H, D, Alkyl D, Alkyl O, S RA-5 RA-5 H, D, Alkyl Ar-1 bis Ar-75 O, S RA-4 RA-4 H, D, Alkyl Ar-1 bis Ar-75 O, S RA-4f RA-4f H, D, Alkyl Ar-1 bis Ar-75 O, S RA-3 RA-3 H, D, Alkyl Ar-1 bis Ar-75 O, S RB RB H, D, Alkyl Ar-1 bis Ar-75 O, S RA-5 RA-5 Ar-1 bis Ar-75 D, Alkyl O, S RA-4 RA-4 Ar-1 bis Ar-75 D, Alkyl O, S RA-4f RA-4f Ar-1 bis Ar-75 D, Alkyl O, S RA-3 RA-3 Ar-1 bis Ar-75 D, Alkyl O, S RB RB Ar-1 bis Ar-75 D, Alkyl O, S RA-5 RA-5 Ar-1 bis Ar-75 Ar-1 bis Ar-75 O, S RA-4 RA-4 Ar-1 bis Ar-75 Ar-1 bis Ar-75 O, S RA-4f RA-4f Ar-1 bis Ar-75 Ar-1 bis Ar-75 O, S RA-3 RA-3 Ar-1 to Ar-75 Ar-1 to Ar-75 O, S RB RB Ar-1 to Ar-75 Ar-1 to Ar-75 O, S RA-5 RA-5 H, D, Alkyl Phenyl Ring Formation of 2 R e< O, S RA-4 RA-4 H, D, Alkyl Phenyl Ring Formation of 2 R e< O, S RA-4f RA-4f H, D, Alkyl Phenyl Ring Formation of 2 R e< O, S RA-3 RA-3 H, D, Alkyl Phenyl Ring Formation of 2 R e< O, S RB RB H, D, Alkyl Phenyl Ring Formation of 2 R e< O, S RA-5 RA-5 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< O, S RA-4 RA-4 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< O, S RA-4f RA-4f Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< O, S RA-3 RA-3 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< O, S RB RB Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< O, S RA-5 RA-5 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 O, S RA-4 RA-4 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 O, S RA-4f RA-4f H, D, Alkyl C(Ar') 3 , Si(Ar') 3 O, S RA-3 RA-3 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 O, S RB RB H, D, Alkyl C(Ar') 3 , Si(Ar') 3 O, S RA-5 RA-5 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 O, S RA-4 RA-4 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 O, S RA-4f RA-4f Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 O, S RA-3 RA-3 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 O, S RB RB Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 Oh, S RA-5 RA-5 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 Oh, S RA-4 RA-4 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 Oh, S RA-4f RA-4f H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 Oh, S UK-3 UK-3 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 Oh, S RB RB H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 Oh, S RA-5 RA-5 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 Oh, S RA-4 RA-4 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 Oh, S RA-4f RA-4f Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 Oh, S UK-3 UK-3 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 Oh, S RB RB Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 Oh, S RA-5 RA-5 H, D, Alkyl D, Alkyl N(On') RA-4 RA-4 H, D, Alkyl D, Alkyl N(On') RA-4f RA-4f H, D, Alkyl D, Alkyl N(On') UK-3 UK-3 H, D, Alkyl D, Alkyl N(On') RB RB H, D, Alkyl D, Alkyl N(On') RA-5 RA-5 H, D, Alkyl Ar-1 to Ar-75 N(On') RA-4 RA-4 H, D, Alkyl Ar-1 to Ar-75 N(On') RA-4f RA-4f H, D, Alkyl Ar-1 to Ar-75 N(On') UK-3 UK-3 H, D, Alkyl Ar-1 to Ar-75 N(On') RB RB H, D, Alkyl Ar-1 to Ar-75 N(On') RA-5 RA-5 Ar-1 to Ar-75 D, Alkyl N(On') RA-4 RA-4 Ar-1 to Ar-75 D, Alkyl N(On') RA-4f RA-4f Ar-1 to Ar-75 D, Alkyl N(On') UK-3 UK-3 Ar-1 to Ar-75 D, Alkyl N(On') RB RB Ar-1 to Ar-75 D, Alkyl N(Ar') RA-5 RA-5 Ar-1 to Ar-75 Ar-1 to Ar-75 N(Ar') RA-4 RA-4 Ar-1 to Ar-75 Ar-1 to Ar-75 N(Ar') RA-4f RA-4f Ar-1 to Ar-75 Ar-1 to Ar-75 N(Ar') RA-3 RA-3 Ar-1 to Ar-75 Ar-1 to Ar-75 N(Ar') RB RB Ar-1 to Ar-75 Ar-1 to Ar-75 N(Ar') RA-5 RA-5 H, D, Alkyl Phenyl Ring Formation of 2 R e< N(Ar') RA-4 RA-4 H, D, Alkyl Phenyl Ring Formation of 2 R e< N(Ar') RA-4f RA-4f H, D, Alkyl Phenyl Ring Formation of 2 R e< N(Ar') RA-3 RA-3 H, D, Alkyl Phenyl Ring Formation of 2 R e< N(Ar') RB RB H, D, Alkyl Phenyl Ring Formation of 2 R e< N(Ar') RA-5 RA-5 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< N(Ar') RA-4 RA-4 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< N(Ar') RA-4f RA-4f Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< N(Ar') RA-3 RA-3 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< N(Ar') RB RB Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< N(Ar') RA-5 RA-5 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 N(Ar`) RA-4 RA-4 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 N(Ar`) RA-4f RA-4f H, D, Alkyl C(Ar') 3 , Si(Ar') 3 N(Ar`) RA-3 RA-3 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 N(Ar`) RB RB H, D, Alkyl C(Ar') 3 , Si(Ar') 3 N(Ar') RA-5 RA-5 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 N(Ar') RA-4 RA-4 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 N(Ar') RA-4f RA-4f Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 N(Ar') RA-3 RA-3 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 N(Ar') RB RB Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 N(Ar') RA-5 RA-5 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 N(Ar') RA-4 RA-4 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 N(Ar') RA-4f RA-4f H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 N(Ar') RA-3 RA-3 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 N(Ar') RB RB H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 N(Ar') RA-5 RA-5 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 N(Ar') RA-4 RA-4 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 N(Ar') RA-4f RA-4f Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 N(Ar') RA-3 RA-3 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 N(Ar') RB RB Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 N(Ar`) RA-5 RA-5 H, D, Alkyl D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 H, D, Alkyl D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f H, D, Alkyl D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 H, D, Alkyl D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB H, D, Alkyl D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 H, D, Alkyl Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 H, D, Alkyl Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f H, D, Alkyl Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 H, D, Alkyl Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB H, D, Alkyl Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 Ar-1 to Ar-75 D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 Ar-1 to Ar-75 D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f Ar-1 to Ar-75 D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 Ar-1 to Ar-75 D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB Ar-1 to Ar-75 D, Alkyl (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 Ar-1 to Ar-75 Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 Ar-1 to Ar-75 Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f Ar-1 to Ar-75 Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 Ar-1 to Ar-75 Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB Ar-1 to Ar-75 Ar-1 to Ar-75 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 H, D, Alkyl Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 H, D, Alkyl Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f H, D, Alkyl Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 H, D, Alkyl Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB H, D, Alkyl Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB Ar-1 to Ar-75 Phenyl Ring Formation of 2 R e< (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f H, D, Alkyl C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB H, D, Alkyl C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-5 RA-5 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4 RA-4 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-4f RA-4f Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RA-3 RA-3 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< ) RB RB Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 (R e< ) 2 CC(R e< ) 2 , (R e< )C=C(R e< )

[0114] In the table above, the substituents listed in the column under group R e< represent the substituents on the phenyl ring linked to group Y 1<. In group C(R e< ) 2, the substituent R e< represents, in particular, the groups described above, wherein R e< in group C(R e< ) 2 preferably represents, either the same or different in each instance, a linear alkyl group with 1 to 10 carbon atoms, or a branched or cyclic alkyl group with 3 to 10 carbon atoms, or an aromatic or heteroaromatic ring system with 5 to 24, preferably 5 to 13, aromatic ring atoms, which may also be substituted by one or more R 1< substituents. R e< most preferably represents a methyl group or a phenyl group. The R e< substituents may also form a ring system with each other, leading to a spiro system.

[0115] In the groups (Re<)2CC(Re<)2, (Re<)C=C(Re<), the substituent Re< particularly represents the groups described above, where Re< in groups (Re<)2CC(Re<)2, (Re<)C=C(Re<) preferably represents H, C1 to C4 alkyl, or an aryl or heteroaryl group with 5 to 13 carbon atoms, the aryl or heteroaryl group being potentially linked. Two Re< groups in the group (Re<)2CC(Re<)2 or (Re<)C=C(Re<) can form a fused ring system.

[0116] In a further embodiment of the present invention, compounds according to formula (I-6) are preferred, wherein the two residues R a< form a ring, the two residues R c< form a ring, wherein the sum of the indices m and n is preferably less than or equal to 4, particularly preferably 0, 1 or 2 and especially preferably 0 or 1, and wherein the residues R a< , R b< , R c< , R d< and R e< have the following meanings: R a< R b< R c< R d< R e< (only if n or possibly 0 is at least one remainder R e< , otherwise all R e< H) RA-5 H, D, Alkyl RA-5 H, D, Alkyl D, Alkyl RA-4 H, D, Alkyl RA-4 H, D, Alkyl D, Alkyl RA-4f H, D, Alkyl RA-4f H, D, Alkyl D, Alkyl RA-3 H, D, Alkyl RA-3 H, D, Alkyl D, Alkyl RB H, D, Alkyl RB H, D, Alkyl D, Alkyl RA-5 H, D, Alkyl RA-5 H, D, Alkyl Ar-1 bis Ar-75 RA-4 H, D, Alkyl RA-4 H, D, Alkyl Ar-1 bis Ar-75 RA-4f H, D, Alkyl RA-4f H, D, Alkyl Ar-1 bis Ar-75 RA-3 H, D, Alkyl RA-3 H, D, Alkyl Ar-1 bis Ar-75 RB H, D, Alkyl RB H, D, Alkyl Ar-1 bis Ar-75 RA-5 H, D, Alkyl RA-5 Ar-1 bis Ar-75 D, Alkyl RA-4 H, D, Alkyl RA-4 Ar-1 bis Ar-75 D, Alkyl RA-4f H, D, Alkyl RA-4f Ar-1 bis Ar-75 D, Alkyl RA-3 H, D, Alkyl RA-3 Ar-1 bis Ar-75 D, Alkyl RB H, D, Alkyl RB Ar-1 bis Ar-75 D, Alkyl RA-5 H, D, Alkyl RA-5 Ar-1 bis Ar-75 Ar-1 bis Ar-75 RA-4 H, D, Alkyl RA-4 Ar-1 bis Ar-75 Ar-1 bis Ar-75 RA-4f H, D, Alkyl RA-4f Ar-1 bis Ar-75 Ar-1 bis Ar-75 RA-3 H, D, Alkyl RA-3 Ar-1 bis Ar-75 Ar-1 bis Ar-75 RB H, D, Alkyl RB Ar-1 bis Ar-75 Ar-1 bis Ar-75 RA-5 H, D, Alkyl RA-5 H, D, Alkyl und Ar-1 bis Ar-75 D, Alkyl RA-4 H, D, Alkyl RA-4 H, D, Alkyl und Ar-1 bis Ar-75 D, Alkyl RA-4f H, D, Alkyl RA-4f H, D, Alkyl und Ar-1 bis Ar-75 D, Alkyl RA-3 H, D, Alkyl RA-3 H, D, Alkyl und Ar-1 bis Ar-75 D, Alkyl RB H, D, Alkyl RB H, D, Alkyl und Ar-1 bis Ar-75 D, Alkyl RA-5 H, D, Alkyl RA-5 H, D, Alkyl und Ar-1 bis Ar-75 Ar-1 to Ar-75 RA-4 H, D, Alkyl RA-4 H, D, Alkyl und Ar-1 bis Ar-75 Ar-1 to Ar-75 RA-4f H, D, Alkyl RA-4f H, D, Alkyl und Ar-1 bis Ar-75 Ar-1 to Ar-75 RA-3 H, D, Alkyl RA-3 H, D, Alkyl und Ar-1 bis Ar-75 Ar-1 to Ar-75 RB H, D, Alkyl RB H, D, Alkyl und Ar-1 bis Ar-75 Ar-1 to Ar-75 RA-5 H, D, Alkyl RA-5 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RA-4 H, D, Alkyl RA-4 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RA-4f H, D, Alkyl RA-4f H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RA-3 H, D, Alkyl RA-3 H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RB H, D, Alkyl RB H, D, Alkyl C(Ar') 3 , Si(Ar') 3 RA-5 H, D, Alkyl RA-5 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 RA-4 H, D, Alkyl RA-4 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 RA-4f H, D, Alkyl RA-4f Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 RA-3 H, D, Alkyl RA-3 Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 RB H, D, Alkyl RB Ar-1 to Ar-75 C(Ar') 3 , Si(Ar') 3 RA-5 H, D, Alkyl RA-5 H, D, Alkyl und Ar-1 bis Ar-75 C(Ar') 3 , Si(Ar') 3 RA-4 H, D, Alkyl RA-4 H, D, Alkyl und Ar-1 bis Ar-75 C(Ar') 3 , Si(Ar') 3 RA-4f H, D, Alkyl RA-4f H, D, Alkyl und Ar-1 bis Ar-75 C(Ar') 3 , Si(Ar') 3 RA-3 H, D, Alkyl RA-3 H, D, Alkyl und Ar-1 bis Ar-75 C(Ar') 3 , Si(Ar') 3 RB H, D, Alkyl RB H, D, Alkyl und Ar-1 bis Ar-75 C(Ar') 3 , Si(Ar') 3 RA-5 H, D, Alkyl RA-5 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 RA-4 H, D, Alkyl RA-4 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 RA-4f H, D, Alkyl RA-4f H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 RA-3 H, D, Alkyl RA-3 H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 RB H, D, Alkyl RB H, D, Alkyl N(Ar') 3 , N(R 1< ) 3 RA-5 H, D, Alkyl RA-5 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 RA-4 H, D, Alkyl RA-4 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 RA-4f H, D, Alkyl RA-4f Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 RA-3 H, D, Alkyl RA-3 Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 RB H, D, Alkyl RB Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 RA-5 H, D, Alkyl RA-5 H, D, Alkyl und Ar-1 bis Ar-75 N(Ar') 3 , N(R 1< ) 3 RA-4 H, D, Alkyl RA-4 H, D, Alkyl und Ar-1 bis Ar-75 N(Ar') 3 , N(R 1< ) 3 RA-4f H, D, Alkyl RA-4f H, D, Alkyl und Ar-1 bis Ar-75 N(Ar') 3 , N(R 1< ) 3 RA-3 H, D, Alkyl RA-3 H, D, Alkyl and Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3 RB H, D, Alkyl RB H, D, Alkyl and Ar-1 to Ar-75 N(Ar') 3 , N(R 1< ) 3

[0117] The term "alkyl" in the tables above includes in particular straight-chain alkyl groups or branched or cyclic alkyl groups according to the definition previously set out for the respective group.

[0118] The term "aryl-, heteroaryl" in the tables above particularly includes aryl or heteroaryl groups with 5 to 40 aromatic ring atoms according to the previously set out definition for the respective group, wherein the aryl groups preferably have 6 to 12, particularly preferably 6 ring atoms and the heteroaryl groups preferably have 5 to 13, particularly preferably 5 ring atoms. Heteroaryl groups particularly preferably comprise one or two heteroatoms, preferably N, O or S.

[0119] The designations "RA-3", RA-4"," RA-4f", "RA-5", "Ar-1", "Ar-75" refer to the structural formulas presented above and below.

[0120] Phenyl ring formation with one group means that the two groups together form a phenyl group, which can each be substituted with R< substituents according to the previously stated definition for the respective group. Typically, this results in the formation of a naphthyl group with the phenyl group bonded to the nitrogen atom, which is substituted by R< d< and R< or R< e< substituents. The same applies to the other ring formation definitions.

[0121] The term "and," particularly when describing preferred groups Rd, means that the two residues are different, with one residue Rd corresponding to a first definition and the other to a second definition. The expression "aryl, heteroaryl, and phenyl ring formation with Re" means that one of the residues Rd represents an aryl or heteroaryl group, and the second residue Rd forms a phenyl ring with Re"". If a field does not contain the expression "and," then all residues represent a corresponding group. The expression "Ar-1 to Ar-75" for the group Rd means that both residues Rd represent an aryl or heteroaryl residue according to the formulas Ar-1 to Ar-75 above or below.

[0122] The same applies to the further use of the term "and" in the tables above.

[0123] The preferences set out for formulas (I-1), (I-2), (I-3), (I-4), (I-5), (I-6) with regard to the various substituents R a< , R b< , R c< , R d< and R e< as well as, where applicable, Y 1< apply of course also to the further formulas (I-7), (I-8), (I-9), (I-10), (1-11), (I-12) and (I-13) set out above.

[0124] Furthermore, it should be noted that these preferences set out for formulas (I-1), (I-2), (I-3), (I-4), (I-5), (I-6) with regard to the various substituents R a< , R b< , R c< ,R d< and R e< as well as, where applicable, Y 1< also apply to compounds with X equal to N, CYR y< , CR b< according to formulas (I-15) to (I-47) and (I-65) to (I-83).

[0125] In the case where X is equal to CYR y< and the group R y< with an adjacent residue R a< a ring according to formula (T 1< ) is formed, the preferences set out for formulas (I-1), (I-2), (I-3), (I-4), (I-5), (I-6) apply with regard to the various substituents R a< , R b< , R c< , R d< and R e< and optionally Y 1< accordingly, wherein preferably a ring between the groups R c< according to the above definitions and a ring T 1< according to the corresponding formulas (TCY-1) to (TRA-13) or (TRA-4f) is formed, wherein, for example, a ring between two R c< according to formula (CY-1) corresponds to a ring T 1< according to formula (TCY-1).

[0126] Furthermore, the preferences previously set out for formulas (I-1), (I-2), (I-3), (I-4), (I-5), (I-6) apply, in particular with regard to the various substituents R<b, R<d, and R<e, and, where applicable, Y<1, if the two substituents R<a, R<c) do not form a ring or form a ring of formulas (Cy-1) to (Cy-10), (RA-1) to (RA-13), (RA-1a) to (RA-4f) not listed in the tables. These preferences also apply if the two substituents R<a, R<c) form different rings of formulas (Cy-1) to (Cy-10), (RA-1) to (RA-13), (RA-1a) to (RA-4f).

[0127] If the two substituents R c< do not form a ring, these substituents R c< are preferably selected from H, D, alkyl, aryl, heteroaryl according to the previously set out definition for the groups R c< .

[0128] The preferences previously set out, in particular for formulas (I-1), (I-2), (I-3), (I-4), (I-5), (I-6) with regard to the various substituents R a< , R b< , R c< ,R d< and R e< as well as, where applicable, Y 1< and the explanations set out below regarding formulas (I-7) to (I-83) as well as the case where the substituents R a< , R c< do not form a ring or form a ring of formulas (Cy-1) to (Cy-10), (RA-1) to (RA-13), (RA-1a) to (RA-4f) which is not mentioned in the tables, continue to apply to compounds with exactly two or three structures according to formula (I) and / or (I-1) to (I-83).

[0129] Examples of preferred connections according to the embodiments listed above are the connections listed in the following table (connections 1-194, 237-259, 479, 533, 539, 551-553, 569-571, 574, 575, 580-619, 629 not according to the invention): 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 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 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 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157 158 159 160 161 162 163 CN CN 164 165 166 167 168 169 170 171 172 173 174 175 176 177 178 179 180 181 182 183 184 185 186 187 188 189 190 191 192 192 193 194 195 196 197 198 199 200 201 202 203 204 205 206 207 208 209 210 211 212 213 214 215 216 217 218 219 220 221 222 223 224 225 226 227 228 229 230 231 232 233 234 235 236 237 238 239 240 241 242 243 244 245 246 247 248 249 250 251 252 253 254 255 256 257 258 258 259 260 261 262 263 264 265 266 267 268 269 270 271 272 272 273 274 275 276 277 278 279 280 282 283 284 285 286 287 288 289 290 291 292 293 294 295 296 297 298 299 300 301 302 303 304 305 306 307 308 309 310 311 312 313 314 315 316 317 318 319 320 321 322 323 324 325 326 327 328 329 330 331 332 333 334 335 336 337 338 339 340 341 342 343 344 345 346 347 348 349 350 351 352 353 354 355 356 357 358 359 360 361 362 363 364 365 366 367 368 369 370 371 372 373 374 375 376 377 378 379 380 381 382 383 384 385 386 387 388 389 390 391 392 393 394 395 396 397 398 399 400 401 402 403 404 405 406 407 408 409 410 411 412 413 414 415 416 417 418 419 420 421 422 423 424 425 426 427 428 429 430 431 432 433 434 435 436 437 438 439 440 441 442 443 444 445 446 447 448 449 450 451 452 453 454 455 456 457 458 459 460 461 462 463 464 465 466 467 468 469 470 471 472 473 474 475 476 477 478 479 480 481 482 483 484 485 486 487 488 489 490 491 492 493 494 495 496 497 498 499 500 501 502 503 504 505 506 507 508 509 510 511 512 513 514 515 516 517 518 519 520 521 522 523 524 525 526 527 528 529 530 531 532 533 534 535 536 537 538 539 540 541 542 543 544 545 546 547 548 549 550 551 552 553 554 555 556 557 558 559 560 561 562 563 564 565 566 567 568 569 570 571 572 573 574 575 576 577 578 579 580 581 582 583 584 585 586 587 588 589 590 591 592 593 594 595 596 597 598 599 600 601 602 603 604 605 606 607 608 609 610 611 612 613 614 615 616 617 618 619 620 621 622 623 624 625 626 627 628 629 630 631 632 633 634 635 636 637 638 639 640 640 642 643 644 645 646 647 648 649 650 651 652 653 654 655 656 657 658 659 660 661 662 663 664 665 666 667 668 669 670 671 672 673 674 675

[0130] Preferred embodiments of the compounds according to the invention are described in more detail in the examples, wherein these compounds can be used alone or in combination with others for all uses according to the invention.

[0131] Provided that the conditions specified in claim 1 are met, the preferred embodiments mentioned above can be combined with one another as desired. In a particularly preferred embodiment of the invention, the preferred embodiments mentioned above apply simultaneously.

[0132] The compounds according to the invention can in principle be produced by various methods. However, the methods described below have proven to be particularly suitable.

[0133] Therefore, a further object of the present invention is a method for producing the compounds according to the invention, in which a basic framework with an aromatic amino group is synthesized and at least one aromatic or heteroaromatic residue is introduced, preferably by means of a nucleophilic aromatic substitution reaction or a coupling reaction.

[0134] Suitable compounds comprising a basic framework with an aromatic amino group can often be obtained commercially, with the starting compounds presented in the examples being obtainable by known methods, which are therefore referenced here.

[0135] These connections can be implemented with other connections through known coupling reactions, the necessary conditions for which are known to the person skilled in the art, and detailed information in the examples assists the person skilled in the art in carrying out these conversions.

[0136] Particularly suitable and preferred coupling reactions, all leading to CC couplings and / or CN couplings, are those according to BUCHWALD, SUZUKI, YAMAMOTO, STILLE, HECK, NEGISHI, SONOGASHIRA and HIYAMA. These reactions are widely known, and the examples provided offer further guidance to those skilled in the art.

[0137] The principles of the manufacturing processes described above are known from the literature for similar compounds and can be easily adapted by a person skilled in the art to produce the compounds according to the invention. Further information can be found in the examples.

[0138] By these methods, optionally followed by purification, such as recrystallization or sublimation, the compounds according to the invention can be obtained in high purity, preferably more than 99% (determined by 1< H-NMR and / or HPLC).

[0139] The compounds according to the invention can also be mixed with a polymer. It is also possible to covalently incorporate these compounds into a polymer. This is particularly possible with compounds substituted with reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic acid esters, or with reactive, polymerizable groups, such as olefins or oxetanes. These can be used as monomers for the production of corresponding oligomers, dendrimers, or polymers. The oligomerization or polymerization preferably proceeds via the halogen functionality or the boronic acid functionality, or via the polymerizable group. It is also possible to crosslink the polymers via such groups. The compounds and polymers according to the invention can be used as crosslinked or uncrosslinked layers.

[0140] A further aspect of the invention is therefore oligomers, polymers, or dendrimers containing one or more of the structures of formula (I) and preferred embodiments of this formula listed above, or compounds according to the invention, wherein one or more bonds of the compounds according to the invention or of the structures of formula (I) and preferred embodiments of this formula are present with the polymer, oligomer, or dendrimer. Depending on the linkage of the structures of formula (I) and preferred embodiments of this formula or of the compounds, these therefore form a side chain of the oligomer or polymer or are linked in the main chain. The polymers, oligomers, or dendrimers can be conjugated, partially conjugated, or non-conjugated. The oligomers or polymers can be linear, branched, or dendritic.The same preferences apply to the repeating units of the compounds according to the invention in oligomers, dendrimers and polymers as described above.

[0141] To produce the oligomers or polymers, the monomers according to the invention are homopolymerized or copolymerized with further monomers. Copolymers are preferred, wherein the units according to formula (I) or the preferred embodiments described above and below are present in amounts of 0.01 to 99.9 mol%, preferably 5 to 90 mol%, and particularly preferably 20 to 80 mol%. Suitable and preferred comonomers forming the polymer backbone are selected from fluorenes (e.g., according to EP 842208 or WO 2000 / 022026), spirobifluorenes (e.g., according to EP 707020, EP 894107 or WO 2006 / 061181), para-phenylenes (e.g., according to WO 92 / 18552), carbazoles (e.g., according to WO 2004 / 070772 or WO 2004 / 113468), thiophenes (e.g., according to EP 1028136), dihydrophenanthrenes (e.g., according to WO 2005 / 014689), cis- and trans-indenofluorenes (e.g., according to WO 2004 / 041901 or WO 2004 / 113412). Ketones (e.g. according to WO 2005 / 040302), phenanthrenes (e.g.(according to WO 2005 / 104264 or WO 2007 / 017066) or several of these units. The polymers, oligomers and dendrimers may contain further units, for example hole transport units, in particular those based on triarylamines, and / or electron transport units.

[0142] Of particular interest are compounds according to the invention which are characterized by a high glass transition temperature. In this context, compounds according to the invention are particularly preferred, comprising structures according to formula (I) or the preferred embodiments described above and below, which have a glass transition temperature of at least 70 °C, particularly preferably at least 110 °C, most preferably at least 125 °C and most preferably at least 150 °C, as determined according to DIN 51005 (version 2005-08).

[0143] For processing the compounds according to the invention from the liquid phase, for example by spin coating or by printing processes, formulations of the compounds according to 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 include, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrol, 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 sebacic acid ester, octyl octanoate, heptylbenzene, menthyrosevalerate, cyclohexylhexanoate or mixtures of these solvents.

[0144] A further object of the present invention is therefore a formulation or composition comprising at least one compound according to the invention and at least one further compound. The further compound may, for example, be a solvent, in particular one of the solvents mentioned above or a mixture of these solvents. If the further compound comprises a solvent, this mixture is referred to herein as the formulation. The further compound may also be at least one further organic or inorganic compound that is also used in the electronic device, for example, an emitter and / or a matrix material, wherein these compounds differ from the compounds according to the invention. Suitable emitters and matrix materials are listed later in connection with the organic electroluminescence device. The further compound may also be a polymer.

[0145] Another object of the present invention is therefore a composition comprising a compound according to the invention and at least one further organically functional material. Functional materials are generally the organic or inorganic materials introduced between the anode and cathode. Preferably, the organically functional material is selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF (thermally activated delayed fluorescence), host materials, electron transport materials, electron injection materials, hole guide materials, hole injection materials, electron blocking materials, hole blocking materials, wide-band-gap materials, and n-dopeds, preferably host materials.

[0146] A further object of the present invention is the use of a compound according to the invention in an electronic device, in particular in an organic electroluminescent device, preferably as an emitter, particularly preferably as a green, red or blue emitter, and especially preferably as a blue emitter. Here, compounds according to the invention preferably exhibit fluorescent properties and thus preferably provide fluorescent emitters.

[0147] A further object of the present invention is an electronic device comprising at least one compound according to the invention. An electronic device within the meaning of the present invention is a device comprising at least one layer containing at least one organic compound. The component may also contain inorganic materials or layers composed entirely of inorganic materials.

[0148] The electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), preferably organic light-emitting diodes (OLEDs), small molecule-based organic light-emitting diodes (sOLEDs), polymer-based organic light-emitting diodes (PLEDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), "organic plasmon emitting devices" (DM Koller et al.)., Nature Photonics 2008, 1-4); organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs) and organic electrical sensors, preferably organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), particularly preferably organic light-emitting diodes (OLEDs), small molecule-based organic light-emitting diodes (sOLEDs), polymer-based organic light-emitting diodes (PLEDs), especially phosphorescent OLEDs.

[0149] The organic electroluminescent device contains a cathode, an anode, and at least one emitting layer. In addition to these layers, it may contain further layers, such as 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. Interlayers, which may, for example, have an exciton blocking function, may also be introduced between two emitting layers. It should be noted, however, that not every one of these layers is necessarily present. The organic electroluminescent device may contain a single emitting layer, or it may contain multiple emitting layers.If multiple emission layers are present, these preferably exhibit several emission maxima between 380 nm and 750 nm, resulting in overall white emission. This means that different emitting compounds capable of fluorescence or phosphorescence are used in the emitting layers. Systems with three emitting layers exhibiting blue, green, and orange or red emission are particularly preferred. The organic electroluminescence device according to the invention can also be a tandem electroluminescence device, especially for white-emitting OLEDs.

[0150] The compound according to the invention can be used in different layers, depending on the precise structure. A preferred method is an organic electroluminescent device containing a compound according to formula (I) or the preferred embodiments described above in an emitting layer as an emitter, preferably a red, green, or blue emitter, particularly preferably a blue emitter.

[0151] When the compound according to the invention is used as an emitter in an emitting layer, a suitable matrix material, which is known as such, is preferably used.

[0152] A preferred mixture of the compound according to the invention and a matrix material contains between 99 and 1 vol%, preferably between 98 and 10 vol%, particularly preferably between 97 and 60 vol%, and especially between 95 and 80 vol% of matrix material, based on the total mixture of emitter and matrix material. Similarly, the mixture contains between 1 and 99 vol%, preferably between 2 and 90 vol%, and especially preferably between 3 and 40 vol%, and particularly between 5 and 20 vol% of the emitter, based on the total mixture of emitter and matrix material.

[0153] Suitable matrix materials that can be used in combination with the compounds according to the invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, 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-biscarbazolylbiphenyl) or those in 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. according to WO 2010 / 136109, WO 2011 / 000455, WO 2013 / 041176 or WO 2013 / 056776, azacarbazole derivatives, e.g. according to EP 1617710, EP 1617711, EP 1731584, JP 2005 / 347160, bipolar matrix materials, e.g. according to WO 2007 / 137725, silanes, e.g. according to WO 2005 / 111172, azaborols or boron esters, e.g. according to WO 2006 / 117052, triazine derivatives, e.g.according to WO 2007 / 063754, WO 2008 / 056746, WO 2010 / 015306, WO 2011 / 057706, WO 2011 / 060859 or WO 2011 / 060877, zinc complexes, e.g. according to EP 652273 or WO 2009 / 062578, diazasilol or tetraazasilol derivatives, e.g. according to WO 2010 / 054729, diazaphosphol 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. according to WO 2012 / 048781, dibenzofuran derivatives, e.g. according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO 2017 / 148565 or biscarbazoles, e.g. according to JP 3139321 B2.

[0154] Furthermore, a compound that does not participate, or does not participate to a significant extent, in charge transport, as described, for example, in WO 2010 / 108579, can be used as a co-host. In particular, compounds with a large band gap that do not participate, or at least not to a significant extent, in charge transport of the emitting layer are suitable as co-matrix materials in combination with the compound according to the invention. Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009 / 124627 or WO 2010 / 006680.

[0155] In a preferred embodiment, a compound according to the invention, which is used as an emitter, is preferably used in combination with one or more phosphorescent materials (triplet emitters) and / or a compound that represents a TADF (thermally activated delayed fluorescence) host material. A hyperfluorescence and / or hyperphosphorescence system is preferably formed in this way.

[0156] WO 2015 / 091716 A1 and WO 2016 / 193243 A1 disclose OLEDs that contain both a phosphorescent compound and a fluorescent emitter in the emission layer, with energy being transferred from the phosphorescent compound to the fluorescent emitter (hyperphosphorescence). In this context, the phosphorescent compound behaves like a host material. As is known to those skilled in the art, host materials have higher singlet and triplet energies compared to the emitters, so that the energy of the host material is transferred to the emitter as efficiently as possible. The systems disclosed in the prior art exhibit precisely such an energy ratio.

[0157] Phosphorescence within the meaning of this invention is understood to mean luminescence from an excited state with a higher spin multiplicity, i.e., a spin state > 1, in particular from an excited triplet state. For the purposes of this application, all luminescent complexes with transition metals or lanthanides, in particular all iridium, platinum, and copper complexes, are to be considered phosphorescent compounds.

[0158] Suitable phosphorescent compounds (= triplet emitters) are, in particular, compounds that emit light, preferably in the visible range, upon suitable excitation and also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, and especially preferably greater than 56 and less than 80, particularly a metal with this atomic number. Compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are preferred as phosphor emitters, especially compounds containing iridium or platinum.

[0159] Examples of the issuers 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 / 001990, WO 2018 / 019687, WO 2018 / 019688, WO 2018 / 041769, WO 2018 / 054798, WO 2018 / 069196, WO 2018 / 069197, WO 2018 / 069273, WO 2018 / 178001, WO 2018 / 177981, WO 2019 / 020538, WO 2019 / 115423, WO 2019 / 158453 and WO 2019 / 179909.In general, all phosphorescent complexes as used in phosphorescent electroluminescence devices according to the prior art and as known to the skilled person in the field of organic electroluminescence are suitable, and the skilled person can use further phosphorescent complexes without inventive effort.

[0160] A compound according to the invention can preferably be used in combination with a TADF host material and / or a TADF emitter, as previously explained.

[0161] The process known as thermally activated delayed fluorescence (TADF) is described, for example, by BH Uoyama et al., Nature 2012, Vol. 492, 234. To enable this process, a relatively small singlet-triplet distance ΔE(S1 - T1) of, for example, less than approximately 2000 cm⁻¹ is required in the emitter. To open the otherwise spin-forbidden transition T1 → S1, another compound with strong spin-orbit coupling can be included in the matrix next to the emitter. This allows inter-system crossing via the spatial proximity and the resulting interaction between the molecules. Alternatively, the spin-orbit coupling can be generated via a metal atom contained in the emitter.

[0162] Further valuable information on hyperfluorescence systems is set out in WO2012 / 133188 (Idemitsu), WO2015 / 022974 (Kyushu Univ.), WO2015 / 098975 (Idemitsu), WO2020 / 053150 (Merck) and DE202019005189 (Merck), among others.

[0163] Further valuable information on hyperphosphorescence systems is set out in WO2015 / 091716 A1, WO2016 / 193243 A1 (BASF), WO01 / 08230 A1 (Princeton Univ. (Mark Thompson)), US2005 / 0214575A1 (Fuji), WO2012 / 079673 (Merck), WO2020 / 053314 (Merck) and WO2020 / 053315 (Merck).

[0164] In a further embodiment of the invention, the organic electroluminescent device according to the invention does not contain a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer; i.e., the emitting layer is directly adjacent to the hole injection layer or the anode, and / or the emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode, as described, for example, in WO 2005 / 053051. Furthermore, it is possible to use a metal complex that is identical or similar to the metal complex in the emitting layer directly adjacent to the emitting layer as a hole transport or hole injection material, as described, for example, in WO 2009 / 030981.

[0165] In the further layers of the organic electroluminescent device according to the invention, all materials commonly used in the prior art can be employed. Therefore, without any inventive effort, a person skilled in the art can use all materials known for organic electroluminescent devices in combination with the compounds according to formula (I) or the preferred embodiments described above.

[0166] A further preferred organic electroluminescent device is characterized in that one or more layers are coated using a sublimation process. The materials are 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.

[0167] A preferred method is also an organic electroluminescence device, characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or with the aid 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 structured.

[0168] A further preferred organic electroluminescent device is characterized in that one or more layers are produced from solution, e.g., by spin coating, or by any printing process, e.g., 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 purpose, which can be obtained, for example, by suitable substitution.

[0169] Formulations for applying a compound according to formula (I) or its previously described preferred embodiments are novel. A further object of the present invention is therefore a formulation comprising at least one solvent and a compound according to formula (I) or its previously described preferred embodiments.

[0170] Hybrid processes are also possible, in which, for example, one or more layers of solution are applied and one or more further layers are vapor-deposited.

[0171] These methods are generally known to those skilled in the art and can be applied by them without inventive effort to organic electroluminescent devices containing the compounds according to the invention.

[0172] The compounds and organic electroluminescent devices according to the invention are distinguished from the prior art in particular by an improved lifetime and higher color purity. The other electronic properties of the electroluminescent devices, such as efficiency or operating voltage, remain at least as good. In a further embodiment, the compounds and organic electroluminescent devices according to the invention are distinguished from the prior art in particular by improved efficiency and / or operating voltage and a longer lifetime.

[0173] The compounds according to the invention can also be used for color conversion. They can preferably be used for color conversion of light-emitting devices. Preferred areas of application are pixels in displays, surface elements in signs, and lighting elements.

[0174] The light-emitting device can be selected from the multitude of known devices. Two selected examples of light-emitting devices are LEDs and organic electroluminescent devices.

[0175] For the purpose of color conversion, the compounds are incorporated into a composition, which is then processed into pixels or planar layers using known methods (spin coating, slit coating, raking, screen printing, nozzle printing, ink-jet printing, etc.).

[0176] The compositions typically contain, in addition to one or more compounds according to the invention, crosslinkable components (monomers, oligomers, polymers), e.g., based on acrylates, acrylamides, polyesters, silicones, etc., and one or more thermally or photochemically activatable starter components. Furthermore, additional components such as organic excipients (antioxidants, stabilizers, leveling agents, viscosity moderators, etc.) or inorganic fillers (SiO₂, TiO₂, Al₂O₃, etc.) may be incorporated. It may also be preferred if the composition contains one or more additional fluorescent materials that differ from the compounds according to the invention. All fluorescent materials known to those skilled in the art are suitable. Both inorganic and organic fluorescent materials can be used.

[0177] The principle of color conversion, color conversion films, their manufacture and components are well known to those skilled in the art (e.g. WO 2017 / 054898 A1, WO2019 / 002239 A1, X. Bai et al, 30, SID DIGEST 2019, JE Kwon, JA Chem. Soc., 135, .30, 11239, 2013, WH Kim et al, Appl. Sci, 10, 2112, 2020).

[0178] The present invention therefore also relates to a composition comprising one or more compounds according to the invention and a crosslinkable component. The crosslinkable component can be any component that a person skilled in the art would consider for this purpose. Preferably, the crosslinkable component is an acrylate, acrylamide, polyester, or silicone; acrylates are most preferably used. Most preferably, the composition comprises, in addition to one or more compounds according to the invention and the crosslinkable component, a starter component, and it is even more preferred if the composition additionally comprises one or more excipients, wherein the excipients mentioned above are suitable.

[0179] Furthermore, the present invention also relates to a color conversion film containing one or more of the compounds according to the invention. By using the color conversion films, efficient and pure emission colors with narrow emission bands can be achieved. The color conversion films can, for example, be applied to a blue-emitting organic electroluminescent device. The compounds according to the invention absorb at least a portion of the light emitted by the organic electroluminescent device and re-emit light of a longer wavelength (color down-conversion). Depending on the compounds according to the invention used, efficient, color-pure, and narrowband blue, green, yellow, red, or infrared emissions can be obtained in this way. In this case, the compound according to the invention is used not as an electroluminescent, but as a phololuminescent component.

[0180] The present invention further relates to a light-emitting device comprising an organic electroluminescent device and a color conversion film. Preferably, the color conversion film is arranged in the light-emitting region of the organic electroluminescent device.

[0181] Furthermore, the present invention relates to color conversion using the compounds according to the invention in the agricultural industry, in order to modify the radiation emitted by a source, for example, the radiation of the sun or an artificial light source, so that biological material, preferably plants, algae, or fungi, experience tailored conditions. This allows the condition and growth of the biological material to be optimally adjusted and influenced. For this purpose, the compounds according to the invention are preferably incorporated into a film. However, the compounds according to the invention can also be installed in the roofs of greenhouses. Another possibility is the processing of the compounds according to the invention in a solution or dispersion that can be sprayed directly onto the biological material.

[0182] The electronic devices according to the invention, in particular organic electroluminescence devices, are characterized by one or more of the following surprising advantages over the prior art: 1. Electronic devices, in particular organic electroluminescent devices containing compounds according to formula (I) or the previously and subsequently described preferred embodiments as emitters, exhibit very narrow emission bands with low FWHM values ​​( F ull W idth H alf Maximum) and lead to particularly color-pure emission, recognizable by the small CIE y-values. Particularly surprising is the fact that both blue emitters with low FWHM values ​​and emitters with low FWHM values ​​that emit in the green, yellow, or red regions of the color spectrum are provided. 2. The emission bands exhibit a shoulder or secondary maximum in the long-wavelength emission edge, each with less than 40%, often less than 30%, of the intensity of the main maximum. This results in a favorablely low viewing angle dependence of the color impression in top-emission OLED devices compared to prior art narrowband boron-containing emitters, which often lack such shoulders or secondary maxima and exhibit a greater viewing angle dependence of the color impression. 3. Electronic devices, in particular organic electroluminescent devices containing compounds according to formula (I) orThe preferred embodiments described above and below, particularly as emitters, exhibit a very good lifetime. In particular, these compounds result in a low roll-off, i.e., a low drop in the power efficiency of the device at high luminance levels. 4. Electronic devices, in particular organic electroluminescent devices containing compounds according to formula (I) or the preferred embodiments described above and below as emitters, exhibit excellent efficiency. Here, the compounds according to formula (I) or the preferred embodiments described above and below result in a low operating voltage when used in electronic devices. 5. The compounds according to formula (I) or the preferred embodiments described above and below exhibit very high stability and lifetime. 6. With compounds according to formula (I) orIn the preferred embodiments described above and below, the formation of optical loss channels can be avoided in electronic devices, particularly organic electroluminescent devices. This results in these devices exhibiting high PL and thus high EL efficiency of emitters, or excellent energy transfer from the matrices to the dopants. Exciton energy is typically transferred from a matrix or host in the emission layer to the emitter via either Dexter or Förster energy transfer. Förster energy transfer (FRET) from a host or matrix to the emitter according to the invention is particularly preferred because it is especially efficient, leading to electronic devices with particularly good performance characteristics (e.g., efficiency, voltage, and lifetime).It is shown that the energy transfer from a host or matrix to the compounds according to the invention preferably occurs via Förster transfer. 7. Compounds according to formula (I) or the preferred embodiments described above and below exhibit excellent glass film formation. 8. Compounds according to formula (I) or the preferred embodiments described above and below form very good films from solutions and exhibit excellent solubility. illustration

[0183] Figure 1 Figure 1 shows the photoluminescence spectra (PL spectra) of compounds ES1, ES94 and 675, measured with a Hitachi F-4500 PL PL spectrometer in approximately 10⁻⁵ molar degassed toluene solution at room temperature (approximately 25 °C).

[0184] These aforementioned advantages do not come at the cost of an excessively high deterioration of other electronic properties.

[0185] It should be noted that variations of the embodiments described in the present invention fall within the scope of this invention. Unless explicitly excluded, each feature disclosed in the present invention may be replaced by alternative features serving the same, an equivalent, or a similar purpose. Thus, unless otherwise stated, each feature disclosed in the present invention is to be considered as an example of a generic series or as an equivalent or similar feature.

[0186] All features of the present invention can be combined with one another in any way, unless certain features and / or stages are mutually exclusive. This applies in particular to preferred features of the present invention. Likewise, features of non-essential combinations can be used separately (and not in combination).

[0187] It should further be noted that many of the features, and in particular those of the preferred embodiments of the present invention, are themselves inventive and not merely to be considered part of the embodiments of the present invention. Independent protection for these features may be sought in addition to or as an alternative to any currently claimed invention.

[0188] The teaching on technical action disclosed in the present invention can be abstracted and combined with other examples.

[0189] The invention is further explained by the following examples, without being intended to limit it. A person skilled in the art can implement the invention in its entire disclosed scope from the descriptions and, without inventive effort, create further connections according to the invention and use them in electronic devices or apply the method according to the invention. Examples:

[0190] Unless otherwise stated, the following syntheses are carried out under a protective gas atmosphere in dried solvents. The solvents and reagents can be obtained, for example, from Sigma-Aldrich or ABCR. The information in square brackets and the numbers given for individual compounds refer to the CAS numbers of the compounds known from the literature. For compounds that can exhibit several configurational isomers, enantiomers, diastereomers, or tautomeric forms, one form is shown as a representative example. 1) Representation of the synthons 1.1) Nitriles: Example S1

[0191]

[0192] S1 can be produced on the above route, according to the following literature, with a yield of 69%: Stages 1 and 2: WS Tan et al., J. Chin. Chem. Soc., 2012, 59, 399. Stage 3: JM Herbert et al., J. Label. Compd. Radiopharm., 2007, 50, 440.

[0193] The cleaning process is carried out via flash chromatography on a column-based automated system (Combi-Flash Torrent, Axel Semrau).

[0194] The following synthons can be represented analogously. Example. Educt product yield S2 1403327-05-8, Level 3 85 % S3 664364-61-8, Level 3 83 % S4 1560647-41-7, Level 1 - 3 64 % Alternative presentation method:

[0195] Alternatively, S1 to S4 can be represented with improved yield via the following route: Steps 1 and 3: Analogous to WS Tan et al., J. Chin. Chem. Soc., 2012, 59, 399. Yield of step 1 - 95%, yield of step 3 quantitative. Step 2: Iodination with N-iodosuccinimide in trifluoroethanol (TFE) or hexafluoroisopropanol analogous to R.-J. Tang et al. J. Org. Chem., 2018, 83, 930. Yield 93%. Example S1b:

[0196]

[0197] Similarly, the corresponding bromine triflates can be obtained using N-bromosuccinimide. Yield over 3 steps: 87%. Example S1c:

[0198]

[0199] Similarly, the corresponding chlorine triflates can be obtained using N-chlorosuccinimide. Yield over 3 steps: 69%. Example S1d:

[0200]

[0201] Similarly, the corresponding fluorine triflates can be obtained by fluorination in step 2, analogous to RD Chambers et al., J. Fluor. Chem., 2000, 102, 169. Yield over 3 steps: 30%. Example S1e:

[0202]

[0203] IF exchange analogous to CS Hartley et al., Chem. Mater. 2004, 16, 5297. Yield 28%.

[0204] Alternatively, S1e can be represented as follows: Step 1: Analogous to MA Zolfigol et al., Molecules 2001, 6, 614. Yield: 93%. Step 2: G. Ralf et al. Journal fuer Praktische Chemie 1987, 329(6), 945. Yield: 89%. Step 3: Analogous to JH Clark et al., Chem. & Ind. 1991, 436. Yield: 38%. Optimized synthesis of S1e: Stage 1:

[0205] A solution of 29.5 g (100 mmol) of 1-cyano-4-hydroxytriptycene, cooled to 0 °C, is added dropwise for 1 h to a mixture of 19.0 g of 65 wt% nitric acid and 20.0 g of 96 wt% nitric acid. The mixture is stirred for another 30 min and then carefully poured (foaming may occur!) onto a mixture of 37.8 g (450 mmol) of sodium bicarbonate and 3 l of ice water while stirring very well. The organic phase is separated, the aqueous phase is extracted three times with 200 mL of DCM each time, the combined organic phases are dried with saturated saline solution, and the solution is set on magnesium sulfate. The evaporation is filtered off from the drying agent, the DCM is removed under vacuum, and the residue (silica gel, n-heptane / EE 5:1) is chromatographed. Yield: 31.5 g (93 mmol) 93%; Purity approx. 98% ig n. 1< H-NMR. Stage 2:

[0206] A well-stirred mixture of 34.0 g (100 mmol) of 1-cyano-3-nitro-4-hydroxytriptycene and 93.5 mL (1 mol) of phosphoryl chloride is mixed with 21.0 mL (120 mmol) of diisopropylethylamine (DIPEA) and heated under reflux for 4 h. The reaction mixture is then slowly poured (exothermic, induction period!) onto 2 L of ice water with very good stirring and stirred for 30 min. The aqueous phase is extracted five times with 200 mL of DCM each time. The combined organic phases are dried with saturated saline and set on magnesium sulfate. The mixture is filtered off the drying agent, the DCM is deionized under vacuum, and the residue (silica gel, n-heptane / EE 5:1) is chromatographed. Yield: 40.1 g (89 mmol) 89%. Purity approx. 97% n. 1< H-NMR. Stage 3:

[0207] Analogous to JH Clark et al., Chem. & Ind. 1991, 436. Yield: 38%.

[0208] Alternatively, S1e can be represented in improved yield as follows: Stage 1: Analogous to S. Chandrappa et al., Synlett 2010, 3019. Yield: 87%. Stage 2: DJ Milner et al., Synth. Commun., 1992, 22(1), 73. Yield: 77%. Optimized synthesis of S1e: Stage 1:

[0209] A well-stirred suspension of 35.9 g (100 mmol) of 1-cyano-3-nitro-4-chlorotriptycene and 25.1 g (450 mmol) of iron powder in 700 ml of ethanol is treated dropwise under reflux for 30 min with 75.0 ml of 37 wt% aqueous hydrochloric acid (Caution: hydrogen evolution!). The mixture is stirred under reflux for 3 h, allowed to cool, diluted with 2 l of water and 2 l of DCM, and adjusted to alkaline (pH ~ 9) by carefully adding (foaming may occur!) solid sodium carbonate. The mixture is filtered through Celite, the organic phase of the filtrate is separated, the aqueous phase is extracted five times with 100 ml of DCM each time, the combined organic phases are dried by washing twice with 300 ml of saturated saline solution each time, and adjusted to magnesium sulfate. The desiccant is filtered off, the DCM is removed under vacuum, the crude product is drawn onto isotopes and chromatographed (silica gel, n-heptane / DCM 1:1 > 1:2). If necessary, chromatography is repeated until the product is white to light beige. Yield: 28%.5 g (87 mmol) 87%; purity approx. 98% ig n. 1< H-NMR. Stage 2:

[0210] A well-stirred solution of 12.9 g (110 mmol) of nitrosyltetrafluoroborate [NO][BF₄] in 500 ml DCM, cooled to 0 °C, is treated portionwise with 32.9 g (100 mmol) of 1-cyano-3-amino-4-chlorotriptycene over 10 min. Stirring continues for another 30 min, the mixture is filtered from the diazonium salt, which is washed once with 100 ml DCM / n-heptane (1:2, vv) and once with 100 ml n-heptane alone, and dried briefly at room temperature under vacuum. Yield: 40.6 g (97%).

[0211] The diazonium salt thus obtained is decomposed in a rotating flask in a gentle stream of argon at 220–230 °C until nitrogen evolution ceases (approx. 1 h). The cooled residue is extracted with 500 ml of DCM. Insoluble components are filtered off, the filtrate is concentrated to dryness, and the residue is chromatographed (silica gel, n-heptane / DCM 2:1). Yield: 25.4 g (77 mmol); Purity: approx. 98% n.1 < ¹H NMR.

[0212] The following synthons can be represented analogously. Yield over 4 or 5 steps. Example. Educt product yield S2e 1403327-04-7 42 % S3e 89682-91-7 44 % S4e 1560647-41-7 35 % Example S10:

[0213]

[0214] Procedure analogous to WS Tan et al., J. Chin. Chem. Soc., 2012, 59, 399. Dimethylacetamide (DMAC) is used instead of DMF, resulting in improved yields. Yield 66%.

[0215] Analogous to S1 (alternative representation) and S10, the following Svnthone can be represented. Example. Educt product yield S10b S1b 68 % S11 S2 57 % S12 S3 64 % S13 S4 57 % S14 1588404-75-4 48 % S15 1419387-01-1 49 % S16 17938-69-1 50 % S17 93257-53-5 43 % 1.2) Bicyclic ketones: Example S50:

[0216] A) Via Grignard route:

[0217]

[0218] S50 can be prepared via the Grignard route from the starting materials mentioned above, according to the following literature, in 34% yield: Level 1-4: BM Fox et al., J. Med. Chem., 2014, 52, 3464. Level 5: I. Dragutan et al., Org. Prep. Proced., Int., 1975, 7, 2, 75.

[0219] The purification, in particular the separation of regioisomers from the cyclization in step 5, is carried out via flash chromatography on a column chromatograph (Combi-Flash Torrent, Axel Semrau). B) Via Suzuki route:

[0220]

[0221] S50 can also be prepared via the aforementioned Suzuki route, starting from the aforementioned starting materials, according to the following literature, in 41% yield: Stage 1 to 3: C. Dolente et al., WO 2011 / 120877 Stage 4: I. Dragutan et al., Org. Prep. Proced., Int., 1975, 7, 2, 75.

[0222] The purification, in particular the separation of regioisomers from the cyclization in step 4, is carried out via flash chromatography on a column chromatograph (Combi Flash Torrent, Axel Semrau). Example S51:

[0223] C) Via Friedel-Crafts Alkylation and Acylation

[0224]

[0225] S51 can be prepared in 28% yield via the Friedel-Crafts route, according to the following literature, using 2-chloroanisole instead of anisole: Level 1: Ismailov, AG et al., Nauch. Tr. Azerb. Un-t. Ser. Khim. N, 1979, (4),47. Level 2: Ismailov, AG et al., Zhurnal Organicheskoi Khimii, 1978, 14(4), 811. Levels 3 and 4: ML Maddess et al., Org. Process Res. Dev. 2014, 18, 528-538.

[0226] The purification, in particular the separation of regioisomers from the cyclization in stage 2, is carried out via flash chromatography on a column chromatograph (Combi-Flash Torrent, Axel Semrau).

[0227] The following synths can be represented analogously: Example. Educt product yield S52 1222103-23-2 30 % S53 1222103-24-3 23 % S54 108793-30-2 27 % S55 21280-29-5 25 % S56 64390-25-6 22 % S57 1076197-47-1 30 % Example S58:

[0228]

[0229] S58 can be prepared in 55% yield via the Grignard route A) according to the literature or according to the Grignard route described by GM Castanedo et al., J. Med. Chem., 2017, 60, 627, by using 1-bromo-2-chloro-4-iodobenzene instead of 1-bromo-2-fluoro-4-iodobenzene. 1.3) Synthesis of the substitute iodo-chloropyridines Synthesis scheme using the example of a homoadamtan enamine:

[0230]

[0231] Stages 1 to 5 are carried out analogously to syntheses known from the literature: Levels 1 to 4: M. Adachi et al., Tetrahedron Letters, 37 (49), 8871, 1996; EP 0 556 008 B1. Level 5: JD Eckelbarger et al., US 8835409; EA Krasnokutskaya et al., Synthesis, 2007,1, 81. A) Synthesis of enamines:

[0232] The enamines can be prepared from the ketones and morpholine shown in yields of approximately 60-80% according to the method described in WO 2020 / 064662, page 108, or are known from the literature. Example. Reactant Ketone / Morpholine Enamin product S100 24669-56-5 S101 2716-23-6 S102 591 17-09-8 S103 6372-63-0 S104 73164-06-4 S105 15189-14-7 S106 6308-02-7 S107 1781-82-4 S108 51209-49-5 S109 4694-115 S110 96676-35-6 S111 180690-80-6 S112 --- 124032-58-2 S113 54193-73-6 S114 126495-32-7 S115 --- 1195901-19-9 S116 --- 73129-56-3 S117 26465-81-6 S118 26465-81-6 S119 36449-72-6 S120 55010-17-8 S121 866762-72-3 S122 --- 56639-83-9 B) Synthesis of substituted pyridines: Level 1: Example S200

[0233]

[0234] A mixture of 23.3 g (100 mmol) S100 (analogous for the other 6- and 7-ring enamines), 22.6 g (120 mmol) 4-(Aminomethylene)-2-phenyl-5(4H)-oxazolone [3674-51-9], 47.3 mL (500 mmol) acetic anhydride [108-24-7], and 150 mL toluene is stirred for 4 h at 100 °C (5-ring enamines are reacted in o-xylene at 130 °C / 4 h in an autoclave). The mixture is concentrated completely under vacuum, the oil is treated with 70 mL of methanol, stirred for 3 h, the crystallized product is filtered off by suction, washed once with 25 mL of ice-cold methanol, and dried under vacuum. The crude product thus obtained is reacted further without purification. Yield: 26.2 g (78 mmol), 78% E,Z isomer mixture; Purity: approx. 95% n. 1< H-NMR. Level 2: Example S300

[0235]

[0236] A mixture of 33.4 g (100 mmol) of S200 and 200 ml of 1-methyl-2-pyrrolidinone (NMP) is stirred for 1.5 h at 200–205 °C. The mixture is allowed to cool to approximately 100 °C, the NMP is largely removed under vacuum, the glassy, ​​viscous residue is dissolved in 100 ml of warm acetonitrile, stirred for 12 h at room temperature, filtered from the crystallized product, and dried under vacuum. Yield: 25.1 g (75 mmol), 75%; purity: approximately 95%, < 1H NMR. Level 3: Example S400

[0237]

[0238] A suspension of 33.4 g (100 mmol) of S300 in a mixture of 150 ml of N,N-dimethylformamide (DMF) is treated dropwise with 14.0 ml (150 mmol) of phosphoryl chloride in 50 ml of DMF under ice-salt cooling (approx. -10 °C) and then stirred for 16 h at room temperature. The reaction mixture is carefully poured onto 1000 ml of ice water, stirred for 10 min, 200 ml of dichloromethane (DCM) is added, stirred for 10 min, and the organic phase is separated. The aqueous phase is made basic (pH 8-9) by carefully adding concentrated aqueous ammonia solution, extracted three times with 200 ml of ethyl acetate each time, and the combined ethyl acetate extracts are washed twice with 200 ml of ice water each time and once with 200 ml of saturated ammonia solution. Sodium bicarbonate solution and twice with 100 ml of saturated saline solution each time. Dry over a mixture of magnesium sulfate and sodium carbonate, filter off the drying agent, and concentrate the organic solution.The phase is introduced under vacuum and the residue is recrystallized once from acetonitrile upon addition of ethyl acetate (EE). Yield: 24.7 g (81 mmol), 81%; Purity: approx. 95% n.l. < ¹H NMR. Level 4: Example S500

[0239]

[0240] A mixture of 30.4 g (100 mmol) of S400, 100 mL of 3 N sulfuric acid, and 200 mL of dioxane is stirred for 1.5 h at 100 °C. After cooling, the reaction mixture is diluted with 1000 mL of ice water and then adjusted to pH ~7.5 with 3 N NaOH while cooling under ice. The aqueous phase is extracted three times with 200 mL of DCM each time. The combined organic phases are washed twice with 200 mL of water each time, once with 200 mL of saturated sodium chloride, and dried over magnesium sulfate. The filtrate is filtered off the drying agent, concentrated to dryness, and recrystallized from methanol. Yield: 23.1 g (93 mmol), 93%; Purity: approx. 95%. < 1H NMR. Level 5: Example S600

[0241] Option 1:

[0242] 24.9 g (100 mmol) of S500 are stirred thoroughly into 500 ml of concentrated hydrochloric acid cooled to 3–5 °C. The suspension is stirred dropwise for 15 min with a cold solution of 10.4 g (150 mmol) of sodium nitrite in 50 ml of water, and then stirred for approximately 20 min at 5 °C. The resulting diazonium solution is poured into a well-stirred solution of 90.0 g (600 mmol) of potassium iodide in 5000 ml of water, cooled to 5 °C, to which 1000 ml of DCM has been added (Caution: foaming may occur!). After nitrogen evolution has ceased (approximately 25 min), sodium bisulfite solution is added until the solution decolorizes, and the pH is carefully adjusted to approximately 7.5 with 5 N NaOH under very good cooling. The solution is diluted with a further 1500 ml of DCM, the organic phase is separated, the aqueous phase is re-extracted twice with 500 ml of DCM each time, the combined organic phases are washed twice with 500 ml of water and twice with 500 ml of saturated saline solution, and then dried over magnesium sulfate.After removal of the DCM under vacuum, the residue is flash-chromatographed (Combi-Flash Torrent from A. Semrau). Yield: 22.9 g (63 mmol), 63%; Purity: approx. 97% n.l. < H-NMR. Option 2:

[0243] A solution of 24.9 g (100 mmol) of S500 in 500 ml of acetonitrile is fractionally treated with 57.1 g (300 mmol) of p-toluenesulfonic acid monohydrate [6192-52-5] and then cooled to 10 °C in an ice bath. The suspension is then fractionally treated with a solution of 13.9 g (200 mmol) of sodium nitrite and 37.5 g (250 mmol) of potassium iodide in 60 ml of water, stirring for 15 min at 10 °C, while stirring well and cooling in an ice bath. The mixture is then allowed to warm to room temperature and stirred for 70 min. It is then diluted with 1500 ml of water, adjusted to pH 9.5 by adding saturated sodium bicarbonate solution, and treated with 200 ml of 2M sodium bisulfite solution. The precipitated crude product is filtered off, washed twice with 50 ml of water each time, and briefly dried. The crude product is then dissolved in 500 ml of DCM, the solution is dried over sodium sulfate, the drying agent is removed by filtering, and the crude product is drawn onto isolates. Purification is carried out by flash chromatography (Combi-Flash Torrent from A. Semrau).Yield: 25.0 g (72 mmol), 72%; Purity: approx. 97% y n. 1< H-NMR.

[0244] Analogous to stages 1 to 5, the following pyridines can be obtained. Yield over five stages (stages 1-5): Example. Enamin product yield S601 S101 28 % S602 S102 25 % S603 S103 30 % S604 S104 23 % S605 S105 24 % S606 S106 26 % S607 S107 19 % S608 S108 32 % S609 S109 19 % S610 S110 15 % S611 S111 23 % S612 S112 21 % S613 S113 20 % S614 S114 20 % S615 S115 22 % S616 S116 18 % S617 S117 23 % S618 S118 21 % S619 S119 18 % S620 S120 19 % S621 S121 17 % S622 S122 24 % 1.4) Synthesis of anilines Example 700:

[0245]

[0246] Procedure analogous to S. Bhagwanth et al., Tetrahedron Letters 50 (2009) 1582. Starting material: 38 g (100 mmol) bromide; glass beads are added to the mechanically stirred reaction mixture. Yield: 21.6 g (67 mmol) 67%; Purity: approx. 97% µg n. 1 < H-NMR. Example. Starting materials product yield S701 1898280-80-2 55 % S702 1579280-82-2 61 % S703 1678504-51-2 64 % S704 1914081-14-3 60 % S705 1147894-96-9 70 % 1.5) Synthesis of symmetrically substituted amines Example A1

[0247] variant 1: Buchwald coupling

[0248] Procedure analogous to the following literature: PB Tiruveedhula et al., Organic & Biomolecular Chemistry, 13 (43), 10705, 2015. K. Revunova et al., Polyhedron, 2013, 52, 1118.

[0249] A mixture of 60.9 g (110 mmol) S1, 4.57 ml (50 mmol) aniline, 65.2 g (200 mmol) cesium carbonate, 2.18 g (3.5 mmol) rac-BINAP [98327-87-8] , 561 mg (2.5 mmol) palladium(II) acetate, 500 ml toluene, and 50 g glass beads (3 mm diameter) is stirred first for 4 h at 60 °C and then for 12–16 h at 100 °C. The reaction mixture is allowed to cool to 60 °C, and the salts are filtered off through a Celite bed pre-flourished with toluene. The filtrate is concentrated to dryness, the residue is boiled with 200 ml of methanol, the solid is filtered off by suction, washed twice with 50 ml of methanol each time, dried under vacuum, and flash-chromatographed (Combi-Flash Torrent from A. Semrau). Yield: 31.2 g (33 mmol), 66%; Purity: approx. 95%, < ¹H NMR.

[0250] Alternatively, other phosphines (e.g., tri-tert-butylphosphine, di-tert-butylmethylphosphine, SPhos, XPhos, AmPhos, etc.) and bases (e.g., alcoholates such as sodium tert-butoxide) can be used. Variant 2: Jourdan-Ullmann coupling

[0251] Procedure analogous to the following literature: Y.-L- Tasi et al., J. Luminesc., 2007, 127, 41.

[0252] A mixture of 60.9 g (110 mmol) S1, 4.57 ml (50 mmol) aniline, 27.6 g (200 mmol) potassium carbonate, 42.7 g (300 mmol) sodium sulfate, 954 mg (15 mmol) copper powder, 500 ml nitrobenzene, and 1000 g glass beads (3 mm diameter) is stirred at 160 °C for 12–16 h. The reaction mixture is allowed to cool to 60 °C, and the salts are filtered off using a Celite bed pre-flourished with toluene. The filtrate is concentrated to dryness, the residue is boiled with 200 ml methanol, the solid is filtered off using suction filtration, washed twice with 50 ml methanol each time, dried under vacuum, and flash-chromatographed (Combi-Flash Torrent from A. Semrau). Yield: 27.9 g (29.5 mmol), 59%; Purity: approx. 95% y n. 1< H-NMR. 1.6) Synthesis of unsymmetrically substituted amines Example A500:

[0253]

[0254] A mixture of 27.7 g (50 mmol) S1, 4.57 ml (50 mmol) aniline, 65.2 g (200 mmol) cesium carbonate, 2.18 g (3.5 mmol) rac-BINAP [98327-97-8] , 561 mg (2.5 mmol) palladium(II) acetate, 500 ml toluene, and 50 g glass beads (3 mm diameter) is stirred at 60 °C until complete conversion (TLC control, typically 2–4 h). Then, 18.0 g (50 mmol) S600 is added, and the temperature is increased to 100 °C. After complete conversion (TLC control, typically 12–16 h), the reaction mixture is allowed to cool to 60 °C and filtered off the salts through a Celite bed pre-flourished with toluene. The filtrate is concentrated to dryness, the residue is boiled with 200 ml of methanol, the solid is filtered off by suction, washed twice with 50 ml of methanol each time, dried under vacuum, and flash-chromatographed (Combi-Flash Torrent from A. Semrau). Yield: 21.0 g (28 mmol), 56%; Purity: approx. 95%, < ¹H NMR.

[0255] The unsymmetrical amines obtained in this way can be converted to the emitters EAS according to the invention as described in section 2. 2.) Synthesis of the emitters according to the invention: 2.1) Synthesis of symmetrically substituted emitters: Example ES1

[0256] variant 1:

[0257] Procedure analogous to the following literature: T. Kader et al., Chem. Eur. J., 2019, 25, 4412 - 4425.

[0258] A mixture of 47.2 g (50 mmol) A1, 27.6 g (200 mmol) potassium carbonate, 1.72 g (3 mmol) (NHC)Pd(allyl)CI [478980-03-9], 50 g glass beads (3 mm diameter) and 500 ml N,N,-dimethylacetamide (DMAc) is heated to 150 °C for 16 h with good stirring. After cooling to 80 °C, 1000 ml of water is added dropwise, the precipitated solid is filtered off, washed twice with 100 ml of water, twice with 50 ml of methanol, and dried under vacuum. The crude product is flash chromatographed (Combi-Flash Torrent from A. Semrau, DCM: 2% MeOH) and subsequently purified by repeated hot extraction crystallization (DCM:acetonitrile 1:3 to 2:1) and subsequent fractional sublimation or by annealing under high vacuum. Yield: 14.9 g (23 mmol), 46%; Purity: > 99.9% n. HPLC.

[0259] Instead of (NHC)Pd(allyl)Cl, 4 mmol [(tBu) 3 PH][BF 4 ] and 2 mmol Pd(OAc) 2 can also be used. Option 2:

[0260] Procedure analogous to the following literature: AW Jones et al., Adv. Synth. Catal. 2015, 357, 945.

[0261] A mixture of 47.2 g (50 mmol) A1, 3.1 g (10 mmol) palladium(II) pivalate [106224-36-6], 27.8 g (120 mmol) silver(I) oxide [20667-12-3], 9.6 g (120 mmol) copper(II) oxide [1317-38-0], 50 g glass beads (3 mm diameter), and 200 ml pivalic acid (PivOH) is heated to 130 °C for 24 h with good stirring. After cooling to 80 °C, 1000 ml of water is added dropwise, the precipitated solid is filtered off, washed twice with 100 ml of water, twice with 50 ml of methanol, and dried under vacuum. The crude product is flash chromatographed (Combi-Flash Torrent from A. Semrau, DCM: 2% MeOH), then purified by repeated hot extraction crystallization (DCM:acetonitrile 1:3 to 2:1) and subsequent fractional sublimation or by annealing under high vacuum. Yield: 12.3 g (19 mmol), 38%; Purity: > 99.9% n. HPLC.

[0262] Analogous to stages 1.4 and 2.1, the following emitter ES can be represented, yield over two stages: Example. Nitrile amine product yield ES2 S1 36 % 769-92-6 ES3 S1 38 % 1459-48-9 ES4 S2 35 % 91-59-8 ES5 S1 33 % 92-67-1 ES6 S1 36 % 7293-45-0 ES7 S3 40 % 25660-12-2 ES8 S4 33 % 76302-58-4 ES9 S1 3% 118951-68-1 ES10 S1 37 % 2018346-63-7 ES11 S1 35 % 2295808-71-6 ES12 S4 37 % 101283-00-5 ES13 S1 39 % 1416158-30-9 ES14 S1 30 % 129667-70-5 ES15 S1 32 % 861046-41-5 ES16 S1 35 % 37521-66-7 ES17 S1 38 % 1609130-36-0 ES18 S4 33 % 13177-26-9 ES19 S1 35 % 1639349-82-8 ES20 S1 34 % 1882060-04-9 ES21 S1 34 % 2379812-68-5 ES22 S3 35 % 2086712-51-6 ES23 S4 32 $ 22948-06-7 ES24 S1 33 % 343239-58-7 ES25 S4 39 % 1801716-11-9 ES26 S1 34 % 1884138-08-2 ES27 S1 36 % 31997-11-2 ES28 S1 37 % 4106-66-5 ES29 S1 31 % 93951-94-1 ES30 S4 33 % 37521-64-5 ES31 S1 35 % 1846604-58-7 ES32 S1 34 % 789-47-9 ES33 S1 29 % 1409971-49-8 ES34 S1 40 % 2281888-57-9 ES35 S1 38 % 1642327-33-0 ES36 S1 39 % 2460139-08-4 ES37 S1 34 % 2411114-95-7 ES38 S1 36 % 2226959-71-1 ES39 S1 35 % 1225219-95-3 ES40 S1 37 % 1448337-95-8 ES41 S4 38 % ES42 S1 37 % 1268519-74-9 ES43 S1 28 % 174152-47-7 ES44 S1 33 % 1520097-73-7 ES45 S1 35 % 25288-76-0 ES46 S1 38 % 17169-81-2 ES47 S1 26 % 1820037-24-8 ES48 S1 39 % 2364548-23-0 ES49 S1 29 % 93618-98-5 ES50 S4 37 % 1093882-02-0 ES51 S1 35 % 667919-05-3 ES52 S1 33 % 1421789-14-1 ES53 S1 35 % 2411114-70-8 ES54 S1 31 % 53897-95-3 ES55 S1 38 % 1853250-47-1 ES56 S1 36 % 1644466-73-8 ES57 S1 37 % 3693-22-9 ES58 S4 35 % 1940112-89-9 ES59 S1 30 % 1191512-09-0 ES60 S4 28 % 130595-01-6 ES61 S1 36 % 2129673-55-6 ES62 S1 38 % 2179038-73-2 ES63 S3 27 % 1346517-64-3 ES64 S1 32 % 43215-86-7 ES65 S2 21 % 106-50-3 25 mmol ES66 S1 22 % 2243-67-6 25 mmol ES67 S1 19 % 64535-41-7 25 mmol ES68 S1 12 % 866464-33-7 25 mmol ES69 S1 21 % 5896-30-0 25 mmol ES70 S1 20 % 92-87-5 25 mmol ES71 S4 18 % 167559-51-5 25 mmol 2.2) Synthesis of unsymmetrically substituted emitters EAS: Example EAS1

[0263] variant 1:

[0264] Procedure analogous to the following literature: T. Kader et al., Chem. Eur. J., 2019, 25, 4412 - 4425.

[0265] A mixture of 37.5 g (50 mmol) A500, 27.6 g (200 mmol) potassium carbonate, 1.72 g (3 mmol) (NHC)Pd(allyl)Cl [478980-03-9], 50 g glass beads (3 mm diameter), and 500 ml N,N,-dimethylacetamide (DMAc) is heated to 140 °C for 16 h with good stirring. After cooling to 80 °C, 1000 ml of water is added dropwise, the precipitated solid is filtered off, washed twice with 100 ml of water and twice with 50 ml of methanol, and dried under vacuum. The crude product is flash-chromatographed (Combi-Flash Torrent from A. Semrau, DCM: 2% MeOH), which also separates any isomers that may be present. Finally, the emitters thus obtained are purified by repeated hot extraction crystallization (DCM:acetonitrile 1:3 to 2:1) and subsequent fractional sublimation or by annealing under high vacuum. Yield: 14.0 g (25 mmol), 50%; Purity: > 99.9% n. HPLC.

[0266] Instead of (NHC)Pd(allyl)Cl, 4 mmol [(tBu) 3 PH][BF 4 ] and 2 mmol Pd(OAc) 2 can also be used.

[0267] Analogous to stages 1.5 and 2.2, the following emitter EAS can be represented, yield over two stages: Example. Synthone S Amin product yield EAS2A S1 17 % S601 EAS2B 1191512-09-0 17 % EAS3A S1 19 % S602 2179038-73-2 EAS3B 17 % EAS4A S1 19 % S603 31997-11-2 EAS4B 15 % EAS5 S1 33 % S604 92-67-1 EAS6 S1 30 % S605 1093882-02-0 EAS7 S1 35 % S606 43215-86-7 EAS8 S1 30 % S607 1801716-11-9 EAS9 S1 32 % S608 1459-48-9 EAS10 S1 22 % S609 1346517-64-3 EAS 11 S1 33 % S610 22948-06-7 EAS12 S1 25 % S611 1093882-02-0 EAS13 S1 39 % S612 101283-00-5 EAS14 S1 38 % S613 101283-00-5 EAS15A S1 17 % S614 3693-22-9 EAS15B 19 % EAS16 S1 37 % S615 1093882-02-0 EAS17 S1 37 % S616 1093882-02-0 EAS18 S1 22 % S622 106-50-3 25 mmol EAS19 S1 20 % S620 1644466-73-8 EAS20 S1 31 % S622 92-87-5 25 mmol EAS21A S1 20 % 2445776-20-3 EAS21B 2179038-73-2 15 % EAS22* S1 36 % 2500975-91-5 1801716-11-9 EAS23A* S1 18% 2492439-24-2 EAS23B* 2018346-63-7 19 % EAS24A* S4 19 % 1801624-64-5 EAS24B* 861046-41-5 20% EAS25* S4 34 % 52776-04-2 101283-00-5 EAS26* S3 23 % S503 2304436-80-2 106-50-3 25 mmol EAS27 S1 35 % S4 1801716-11-9 EAS28 S1 34 % S3 1093882-02-0 EAS29 S1 33 % S4 101283-00-5 EAS30A S2 34% S3 3693-22-9 EAS30B Isomerenmic ESA31* S1 30 % S50 1093882-02-0 EAS32A* S1 19 % S51 2179038-73-2 EAS32B* 17 % EAS33A* S1 19 % S57 EAS33B* 31997-11-2 16 % EAS34* S4 35 % S53 92-67-1 EAS35* S3 35% S52 1093882-02-0 EAS36* S1 30 % S54 43215-86-7 EAS37* S4 36 % S51 1801716-11-9 EAS38* S1 35 % S52 22948-06-7 EAS39* S1 37 % S57 101283-00-5 EAS40A* S1 19 % S57 EAS40B* 3693-22-9 21% EAS41* S4 35 % S58 1093882-02-0 EAS42* S1 20 % S57 1644466-73-8 EAS43* S1 25 % S57 106-50-3 25 mmol EAS44* S4 28 % S57 92-87-5 25 mmol *not according to the invention Alternative synthesis routes:

[0268] The compounds according to the invention can be prepared, in some cases with improved yields, via the following alternative synthesis routes: 2.3) Alternative procedure A:

[0269] Stepwise construction via two consecutive Buchwald couplings followed by a Pd-catalyzed, intramolecular cyclization using ES1 as an example: Stage 1): Buchwald coupling 1

[0270]

[0271] A mixture of 43.7 g (100 mmol) S10, 9.13 ml (100 mmol) aniline [62-53-3], 20.2 g (210 mmol) sodium tert-butanoate [865-48-5], 1.11 g (2 mmol) bis-diphenylphosphinoferrocene (dppf) [12150-46-8], 499 mg (2 mmol) palladium(II) acetate, 500 ml toluene, and 50 g glass beads (3 mm diameter) is stirred under gentle reflux until complete conversion (approx. 1 h). The reaction mixture is allowed to cool to 60 °C, 300 ml water is added, the organic phase is separated, washed once with 300 ml water and once with 300 ml saturated saline, and dried over magnesium sulfate. The mixture is filtered through a silica gel bed pre-flourished with toluene, washed with 500 ml of ethyl acetate, and the filtrate is concentrated to dryness. The residue is purified chromatographically (silica gel, cyclohexane / EE, Combi-Flash Torrent from A. Semrau). Yield: 32.7 g (81 mmol), 81%; Purity: approx. 97% n.l. < H-NMR. Stage 2: Buchwald coupling 2

[0272]

[0273] A mixture of 40.4 g (100 mmol) of stage 1, 43.7 g (110 mmol) of S10, 20.2 g (210 mmol) of sodium tert-butanolate [865-48-5], 725 mg (2.5 mmol) of tri-tert-butylphosphonium tetrafluoroborate [131274-22-1], 449 mg (2 mmol) of palladium(II) acetate, 500 ml of toluene, and 50 g of glass beads (3 mm diameter) is stirred under gentle reflux until complete conversion (approx. 12 h). The reaction mixture is allowed to cool to 60 °C, 300 ml of water is added, the organic phase is separated, washed once with 300 ml of water and once with 300 ml of saturated saline solution, and dried over magnesium sulfate. The mixture is filtered through a silica gel bed pre-flourished with toluene, washed with 500 ml of ethyl acetate, and the filtrate is concentrated to dryness. The residue is purified chromatographically (silica gel, cyclohexane / EE, Combi-Flash Torrent from A. Semrau). Yield: 55.6 g (77 mmol), 77%; Purity: approx. 97% n.l. < ¹H NMR. Stage 3): Cyclization

[0274] A mixture of 71.7 g (100 mmol) of stage 2, 41.5 g (300 mmol) of potassium carbonate, 725 mg (2.5 mmol) of tri-tert-butylphosphonium tetrafluoroborate [131274-22-1], 449 mg (2 mmol) of palladium(II) acetate, 1000 ml of dimethylacetamide, and 50 g of glass beads (3 mm diameter) is stirred at 150 °C until complete conversion (approx. 12 h). After cooling to 80 °C, 2000 ml of water is added dropwise, the precipitated solid is filtered off by suction, washed twice with 200 ml of water each time, twice with 50 ml of methanol each time, and dried under vacuum. The crude product is flash chromatographed (RP silica gel, acetonitrile / THF, Combi-Flash Torrent from A. Semrau), then purified by repeated hot extraction crystallization (DCM:acetonitrile 1:3 to 3:1) and subsequent fractional sublimation or by annealing under high vacuum. Yield: 36.5 g (56 mmol), 56%; Purity: > 99.9% n. HPLC.

[0275] The alternative method A is not only suitable for the construction of symmetrically substituted emitters, but also specifically for the construction of asymmetrically substituted emitters, by using two different iodine-chlorobenzonitriles in step 1) and step 2).

[0276] The following connections can be represented analogously: Example. Starting materials product yield ES72 S13 13 % 1609130-36-0 ES73 S10 37 % 228107-17-3 ES74 S10 38 % 199392-14-8 ES75 S10 34 % 37521-66-7 ES76 S14 29 % 2268818-23-9 ES77 S15 35 % 2097255-51-9 ES78* S16 41 % 2609787-30-4 ES79* S17 30 % 2379812-68-5 EAS45A S10 Level 1 19 % S14 Level 2 EAS45B 37521-66-7 10 % *not according to the invention 2.4) Alternative procedure B: Stepwise amination - Cyclization via a carbazole intermediate:

[0277]

[0278] Step 1: Standard Buchwald coupling process for the synthesis of sec. amines from an aniline and the iodochlorobenzonitrile, e.g. analogous to U. Masanobu, et al., J. Am. Chem. Soc., 2004, 126(28), 8755 or PB Tiruveedhula, et al., Org. & Biomol. Chem., 2015, 13(43), 10705. Typical yields 70–95%.

[0279] Step 2: Intramolecular cyclization to carbazole analogous to PB Tiruveedhula, et al., Org. & Biomol. Chem., 2015, 13(43), 10705 or F. Chen et al., RSC Adv., 2015, 5, 51512. When using asymmetrically substituted anilines, the regioisomeric carbazoles are isolated as a mixture and reacted further. Typical yields 60–90%.

[0280] Step 3: Standard Buchwald coupling procedure for the synthesis of N-arylated carbazoles; alternatively, an Ullmann coupling can be performed, e.g., analogous to JH Cho et al., Bull. Korean Chem. Soc., (2011), 32(7), 2461. Typical yields 40–80%.

[0281] Step 4: Intramolecular cyclization, analogous to step 2, e.g., analogous to T. Kader et al., Chem. Europ. J., 2019, 25(17), 4412 or analogous to US 9,000,421 B1 using tricyclohexylphosphonium tetrafluoroborate or with NHC-Pd complexes such as allyl-[1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene]-chloropalladium(II). Typical yields 50–80%.

[0282] Alternatively, the carbazole intermediates can be constructed as follows:

[0283] Step 1: Standard Buchwald coupling process for the synthesis of sec. amines from an aniline and the iodochlorobenzonitrile, e.g. analogous to U. Masanobu, et al., J. Am. Chem. Soc., 2004, 126(28), 8755 or PB Tiruveedhula, et al., Org. & Biomol. Chem., 2015, 13(43), 10705. Typical yields 70–95%.

[0284] Level 2: see above.

[0285] Preferably, stage 3 can also be carried out with 3-fluoro-4-triflate or 3-fluoro-4-chlorobenzonitriles as follows: Stage 3 Stage 3: analogous to WO2019063288. Typical yields 60-80%. Stage 4: see above. Optimized synthesis of ES94: Stage 1:

[0286]

[0287] A well-stirred mixture of 32.9 g (100 mmol) 1-cyano-3-amino-4-chlorotriptycene (see p. 228), 20.7 g (100 mmol) 2-bromonaphthalene, 28.8 g (300 mmol) sodium tert-butoxide, 1.11 g (2 mmol) dppf, and 225 mg (1 mmol) palladium(II) acetate in 500 ml toluene is heated under reflux for 1 hour. It is allowed to cool to 70 °C, 500 ml water is added, the mixture is stirred for 10 minutes, the organic phase is separated, washed twice with 300 ml of water each time, once with 300 ml saturated saline solution, and dried over magnesium sulfate. The mixture is filtered over a Celite bed pre-flourished with toluene, the filtrate is concentrated under vacuum, the residue is dissolved in 300 ml of DCM and removed under vacuum, with the distilled DCM being substituted by simultaneous addition of EtOH. The crystallized product is filtered by suction, washed three times with 50 ml of EtOH each time, and dried under vacuum. Yield: 42.3 g (93 mmol) 93%; Purity: approx. 98% by <1H NMR. Stage 2:

[0288]

[0289] A well-stirred mixture of 45.4 g (100 mmol) of the amine, 500 mmol potassium carbonate, 1.16 g (4 mmol) tri-tert-butylphosphonium tetrafluoroborate, 449 mg (2 mmol) palladium(II) acetate, 100 g glass beads (3 mm diameter), and 1000 ml dimethylacetamide (DMAC) is stirred for 1 h at 150 °C. While still hot, the mixture is filtered through a Clite bed pre-flourished with DMAC, the filtrate is concentrated to dryness, the residue is dissolved in 500 ml DCM, and this is removed under vacuum, with the distilled DCM being substituted by the simultaneous addition of 300 ml EtOH. The crystallized product is filtered by suction filtration, washed three times with 50 ml of EtOH each time, and dried under vacuum. Yield: 32.9 g (78 mmol) 78%; Purity: approx. 98% by < 1H NMR. Stages 3 and 4: One-pot reaction

[0290]

[0291] A well-stirred mixture of 20.9 g (50 mmol) of carbazole, 19.6 g (50 mmol) of S1e, 34.6 g (250 mmol) of potassium carbonate, 100 g of glass beads (3 mm diameter), and 500 ml of DMAC is stirred for 20 h at 150 °C. The reaction mixture is allowed to cool to room temperature, 1.16 g (4 mmol) of tri-tert-butylphosphonium tetrafluoroborate and 449 mg (2 mmol) of palladium(II) acetate are added, and the mixture is stirred again for 7 h at 150 °C. While still hot, the mixture is filtered through a Clite bed pre-flourished with DMAC, the littrate is concentrated to dryness, the residue is dissolved in 500 ml of DCM, and this is removed under vacuum, with the distilled DCM being substituted by the simultaneous addition of 300 ml of EtOH. The crystallized crude product is filtered off, washed three times with 50 ml of EtOH each time, and dried under vacuum. The crude product is purified by five hot extraction crystallizations (DCM:acetonitrile 2:1) followed by fractional sublimation under high vacuum (T ~ 300 °C, p ~ 10⁻⁵ < mbar). Yield: 20.0 g (29 mmol), 58%; Purity: > 99.9% n. HPLC.

[0292] The alternative method B is not only suitable for the construction of symmetrically substituted emitters, but also specifically for the regiodirectional construction of asymmetrically substituted emitters, by using two different iodine-chlorobenzonitriles in step 1) and step 3) or 3-fluoro-4-triflate or 3-fluorochlorobenzonitrile in step 3).

[0293] The following connections can be represented analogously: Example. Starting materials product yield ES80 S10 Level 1 & 3 30 % S700 ES80 S10 Level 1 ES80 37 % S1d Stage 3 S700 ES80 S10 Level 1 ES80 54 % S1e Level 3 S700 ES81 S14 Level 1 & 3 28 % S701 ES82 S10 Level 1 & 3 20 % S702 ES83 S10 Level 1 & 3 27 % S703 ES83 S10 Level 1 ES83 35 % S1d Stage 3 S703 ES83 S10 Level 1 ES83 52 % S1e Level 3 S703 ES84 S13 Level 1 & 3 29 % S704 ES84 S13 Level 1 ES84 49 % S4e Level 3 S704 EAS46A S10 Level 1 19 % EAS46B S14 Level 3 6 S705 2.5) Alternative procedure C: Construction by Suzuki coupling of 2,6-bis-boranyl anilines with the halogenated benzonitriles and subsequent double, cyclizing Buchwald amination:

[0294]

[0295] Step 1: Borylation analogous to A. Osichow et al., Organomet. 2013, 32(18), 5239. Typical yields 60–90%.

[0296] Step 2: Regioselective Suzuki coupling at the chlorine triflates or chlorine bromides / iodides, preferably using Hal 1< / Hal 2< combinations are OTf / Cl or I / Cl or Br / Cl analogous to MI Dawson et al., Journal of Medicinal Chemistry, 2007, 50(11), 2622 or WO2021121371. Typical yields 50–80%.

[0297] Stage 3: Cyclization analogous to US 2017 / 0324045. Typical yields 30–60%.

[0298] The following connections can be represented analogously: Example. Starting materials product yield ES85 S1c 31 % 1642-18-8 ES86* 57418-97-0 34 % 667937-52-2 ES87* 2384544-52-7 36 % 133953-35-2 *not according to the invention 2.6) Alternative procedure D: Construction from 3-fluoro-4-halogenated benzonitriles via Suzuki coupling and intramolecular cyclization via SN2Ar reaction:

[0299]

[0300] Step 1: Balz-Schiemann reaction analogous to G. Balz et al., Chem. Ber., 1927, 5, 1186 or via NOBF 4 analogous to DJ Milner et al., Synth. Commun., 1992, 22, 73. See also optimized synthesis of 1e. Typical yields 30–85%.

[0301] Stage 2: Suzuki coupling to the 3-fluoro-4-halogenated benzonitriles. Typical yields 40–80%.

[0302] Step 3: Intramolecular cyclization via SN2Ar reaction, e.g., analogous to CN108727396. Typical yields 40–80%.

[0303] The following connections can be represented analogously: Example. Starting materials product yield ES88 * 2385618-00-6 34 % 840507-06-4 ES89 S1e 14 % 2385618-00-6 ES90 * 916792-15-9 32 % 1500101-93-8 *not according to the invention 2.7) Alternative procedure E: Construction from 2,6-dichloroanilines via Buchwald coupling and Pd-catalyzed intramolecular cyclization:

[0304]

[0305] Stage 1 and Stage 2: e.g. analogous to US 2021 / 0005826. Typical yields across both stages 20-50%.

[0306] The following connections can be represented analogously: Example. Starting materials product yield ES91 843744-23-0 48 % 2113577-09-4 ES92 133618-04-9 46 % 2113577-09-4 ES93 71585-31-4 22 % 1895095-05-2 Measurement of photoluminescence spectra (PL spectra):

[0307] Figure 1 Figure 1 shows PL spectra of the compounds ES1, ES94 and Verb. 675 (sS 204) according to the invention, measured with a Hitachi F-4500 PL PL spectrometer in approximately 10⁻⁵ molar degassed toluene solution at room temperature (approximately 25 °C).

[0308] Top-emission OLED spectra exhibit very narrow emission bands with low FWHM values ​​(< 0.18 eV) and result in particularly color-pure emission. Furthermore, they show a shoulder or secondary peak in the long-wavelength emission slope, each with less than 40% of the intensity of the main peak. This leads to a favorablely low viewing angle dependence of the color perception in top-emission OLED devices compared to state-of-the-art narrowband boron-containing emitters, which often lack such shoulders or secondary peaks and exhibit a greater viewing angle dependence of the color perception. Manufacturing of OLED components 1) Vacuum-processed components

[0309] The compounds according to the invention can be used, among other things, as dopants in the emission layer in fluorescent and hyperphosphorescent OLED components.

[0310] The production of OLEDs according to the invention (organic light emittingThe production of diodes and OLEDs according to the state of the art is carried out according to a general procedure in accordance with WO 2004 / 058911, which is adapted to the conditions described here (layer thickness variation, materials used).

[0311] The following examples present the results of various OLED production processes. Purified glass plates (cleaned in a Miele laboratory dishwasher using Merck Extran detergent) coated with 50 nm thick structured ITO (indium tin oxide) are pretreated with UV ozone for 25 minutes (UV ozone generator PR-100, UVP) and, within 30 minutes, coated with 20 nm PEDOT:PSS (poly(3,4-ethylenedioxythiophene)poly(styrenesulfonate), sourced as CLEVIOS™< P VP AI 4083 from Heraeus Precious Metals GmbH Germany, centrifugally applied from aqueous solution) for improved processing. The plates are then baked out at 180°C for 10 minutes. These coated glass plates form the substrates onto which the OLEDs are applied. After fabrication, the OLEDs are encapsulated to protect them from oxygen and water vapor. The exact layer structure of the electroluminescent OLEDs can be seen in the examples.The materials required to manufacture the OLEDs are shown in Table 10.

[0312] The OLEDs are characterized according to standard procedures. For this purpose, the electroluminescence spectra, current efficiency (measured in cd / A), power efficiency (measured in imp / W), and external quantum efficiency (EQE, measured in percent) are calculated as a function of luminance from current-voltage-luminance curves (IUL curves) assuming a Lambertian emission characteristic. The electroluminescence spectra are determined at a luminance of 100 or 1000 cd / m², and the emission color and the EL-FWHM values ​​are derived from them. EL ectroluminescence - F ull W idth H alf M aximum - width of the EL emission spectra at half peak height in eV, taken for better comparability across the entire spectral range). Fluorescent OLED components:

[0313] 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 and one emitting dopant (emitter) ES or EAS, which is added to the matrix material(s) by co-evaporation in a specific volume fraction. A specification such as SMB:ES or EAS (97:3%) means that the material SMB is present in a volume fraction of 97% and the dopant ES or EAS in a volume fraction of 3% in the layer. Similarly, the electron transport layer can also consist of a mixture of two materials, e.g., as shown here, ETM1 (50%) and ETM2 (50%), see Table 1. The materials used to fabricate the OLEDs are shown in Table 10. For comparison, the compounds D-Ref.1, see Table 10, are used according to the state of the art. Blue Fluorescent OLED Components BF:

[0314] OLEDs generally have the following layer structure: Substrate Hole injection layer 1 (HIL1) made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm; Hole transport layer 1 (HTL1) made of HTM1, 160 nm; Hole transport layer 2 (HTL2), see Table 1; Emission layer (EML), see Table 1; Electron transport layer (ETL2), see Table 1; Electron transport layer (ETL1) made of ETM1 (50%) and ETM2 (50%), 30 nm; Electron injection layer (EIL) made of ETM2, 1 nm; Aluminum cathode, 100 nm Table 1: Structure of Blue Fluorescent OLED Components Example. HTL2 EML ETL2 Ref-BF1 HTM2 10 nm SMB1:Ref.-D1 (97:3%) 20 nm ETM1 10 nm Ref-BF2 HTM2 10 nm SMB1:Ref.-D2 (97:3%) 20 nm ETM1 10 nm BF1 HTM2 10 nm SMB1:ES44 (97:3%) 20 nm ETM1 10 nm BF2 HTM2 10 nm SMB2:ES44 (95:5%) 20 nm ETM1 10 nm BF3 HTM2 10 nm SMB3:ES56 (97:3%) 20 nm ETM1 10 nm BF4 HTM2 10 nm SMB1:ES9 (97:3%) 20 nm ETM1 10 nm BF5 HTM2 10 nm SMB1:ES10 (95:5%) 20 nm ETM1 10 nm BF6 HTM2 10 nm SMB1:ES11 (97:3%) 20 nm ETM1 10 nm BF7 HTM2 10 nm SMB1:ES21 (97:3%) 20 nm ETM1 10 nm BF8 HTM2 10 nm SMB1:ES37 (97:3%) 20 nm ETM1 10 nm BF9 HTM2 10 nm SMB1:ES40 (97:3%) 20 nm ETM1 10 nm BF10 HTM2 10 nm SMB1:ES59 (97:3%) 20 nm ETM1 10 nm BF11 HTM2 10 nm SMB1:61 (97:3%) 20 nm ETM1 10 nm BF12 HTM2 10 nm SMB1:EAS2A (96:4%) 20 nm ETM1 10 nm BF13 HTM2 10 nm SMB1:EAS2B (96:4%) 20 nm ETM1 10 nm BF14 HTM2 10 nm SMB1:EAS3A (97:3%) 20 nm ETM1 10 nm BF15 HTM2 10 nm SMB1:EAS15B (97:3%) 20 nm ETM1 10 nm BF16* HTM2 10 nm SMB1:EAS42 (97:3%) 20 nm ETM1 10 nm BF17 HTM2 10 nm SMB1:ES 73 (97:3%) 20 nm ETM1 10 nm BF18* HTM2 10 nm SMB1:ES78 (95:5%) 20 nm ETM1 10 nm BF19 HTM2 10 nm SMB1:EAS46A (97:3%) 20 nm ETM1 10 nm BF20 HTM2 10 nm SMB1:ES94 (97:3%) 20 nm ETM1 10 nm *Referenzbeispiel Tabelle 2: Ergebnisse Bsp. EQE (%) 1000 cd / m 2< Voltage (V) 1000 cd / m²< Color EL-FWHM [eV] Ref-BF1 6.3 4.5 Blue 0.17 Ref-BF2 7.9 4.3 Blue 0.43 BF1 8.4 4.3 Blue 0.15 BF2 7.9 4.2 Blue 0.15 BF3 8.2 4.2 Blue 0.15 BF4 6.6 4.4 Deep blue 0.13 BF5 7.9 4.6 Blue 0.15 BF6 7.3 4.4 Deep blue 0.13 BF7 8.3 4.3 Blue 0.15 BF8 8.0 4.4 Blue 0.16 BF9 8.6 4.5 Blue 0.15 BF10 7.9 4.3 Blue 0.13 BF11 8.8 4.3 Blue 0.15 BF12 7.6 4.4 Blue 0.14 BF13 7.9 4.4 Blue 0.15 BF14 8.3 4.3 Blue 0.16 BF15 7.8 4.3 Blue 0.15 BF16* 7.7 4.4 Blue 0.14 BF17 7.6 4.4 Blue 0.14 BF18* 8.1 4.3 Blue 0.16 BF19 8.5 4.3 Blue 0.15 BF20 8.9 4.2 Blue 0.13 *Reference example Hyperphosphorescent OLED components:

[0315] All materials are thermally vapor-deposited in a vacuum chamber. The emission layer (EML) or layers always consist of at least one matrix material (host material) TMM, a (phosphorescent) sensitizer PS, and a fluorescent emitter ES or EAS. The matrix material TMM can consist of two components that are vaporized as a mixture (premixed host, e.g., TMM2). The components and their composition are also shown in Table 10. The sensitizer PS and the fluorescent emitter ES or EAS are added to the host material TMM by cover vapor deposition in a specific volume fraction. A specification such as TMM:PS(5%):ES or EAS(3%) means that the material TMM is present in the layer at a volume fraction of 92%, PS at a fraction of 5%, and ES or EAS at a fraction of 3%. Blue hyperphosphorescent OLED components BH:

[0316] OLEDs generally have the following layer structure: Substrate: Hole injection layer 1 (HIL1) made of HTM2 doped with 5% NDP-9 (commercially available from Novaled), 20 nm; Hole transport layer 1 (HTL1) made of HTM2, 30 nm; Hole transport layer 2 (HTL2), see Table 3; Emission layer (EML), see Table 3; Electron transport layer (ETL2), see Table 3; Electron transport layer (ETL1) made of ETM1 (50%) and ETM2 (50%), 20 nm; Electron injection layer (EIL) made of ETM2, 1 nm; Cathode made of aluminum, 100 nm Table 3: Structure of Blue Hyperphosphorescent OLED Components Example. HTL2 EML ETL2 BH1 HTM3 10 nm TMM1:PS1(7%):ES37(1.5%) 25 nm ETM3 10 nm BH2 HTM3 10 nm TMM1:PS1(7%):ES37(2%) 25 nm ETM3 10 nm BH3 HTM3 10 nm TMM1:PS1(7%):EAS19(2%) 25 nm ETM3 10 nm BH4 HTM3 10 nm TMM1:PS3(7%):ES80(2%) 25 nm ETM3 10 nm BH5 HTM3 10 nm TMM1:PS3(7%):EAS46(2%) 25 nm ETM3 10 nm BH6* HTM3 10 nm TMM1:PS3(7%):EAS42(2%) 25 nm ETM3 10 nm *Reference example Table 4: Results Example. EQE (%) 100 cd / m²< Voltage (V) 100 cd / m²< Color EL-FWHM [eV] BH1 13.4 3.4 Blue 0.16 BH2 11.1 3.4 Blue 0.16 BH3 12.8 3.3 Blue 0.17 BH4 20.1 3.2 Blue 0.17 BH5 23.4 3.2 Blue 0.16 BH6* 21.2 3.3 Blue 0.17 *Reference example Green hyperphosphorescent OLED components GH:

[0317] OLEDs generally have the following layer structure: Substrate: Hole injection layer 1 (HIL1) made of HTM2 doped with 5% NDP-9 (commercially available from Novaled), 20 nm; Hole transport layer 1 (HTL1) made of HTM2, 30 nm; Hole transport layer 2 (HTL2), see Table 5; Emission layer (EML), see Table 5; Electron transport layer (ETL2), see Table 5; Electron transport layer (ETL1) made of ETM1 (50%) and ETM2 (50%), 30 nm; Electron injection layer (EIL) made of ETM2, 1 nm; Cathode made of aluminum, 100 nm Table 5: Structure of Green Hyperphosphorescent OLED Components Example. HTL2 EML ETL2 GH1 HTM3 10 nm TMM1:PS1(8%):ES39(2%) 25 nm ETM3 10 nm GH2 HTM3 10 nm TMM1:PS3(8%):ES39(2%) 25 nm ETM3 10 nm Table 6: Results Example. EQE (%) 100 cd / m²< Voltage (V) 100 cd / m²< Color EL-FWHM [eV] GH1 19.3 3.4 Green 0.16 GH2 22.4 3.3 Green 0.16 Orange-red hyperphosphorescent OLED components RH:

[0318] OLEDs generally have the following layer structure: Substrate: Hole injection layer 1 (HIL1) made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm; Hole transport layer 1 (HTL1) made of HTM1, 30 nm; Hole transport layer 2 (HTL2), see Table 7; Emission layer (EML), see Table 7; Electron transport layer (ETL2), see Table 7; Electron transport layer (ETL1) made of ETM1 (50%) and ETM2 (50%), 45 nm; Electron injection layer (EIL) made of ETM2, 1 nm; Cathode made of aluminum, 100 nm Table 7: Structure of Organ-Red Hyperphosphorescent OLED Components Example. HTL2 EML ETL2 RH1 HTM2 10 nm TMM2:PS2(8%):ES67(2%) 20 nm ETM1 10 nm Table 8: Results Example. EQE (%) 100 cd / m²< Voltage (V) 100 cd / m²< Color EL-FWHM [eV] RH1 20.2 3.2 Red 0.15 2) Solution-processed components:

[0319] The fabrication of solution-based OLEDs is generally described in the literature, e.g., in WO 2004 / 037887 and WO 2010 / 097155. In the following examples, both fabrication methods (gas-phase deposition and solution processing) were combined, such that up to and including the emission layer was processed from solution, and the subsequent layers (hole-blocking layer / electron transport layer) were evaporated under vacuum. The previously described general methods are adapted and combined as follows to suit the conditions described here (layer thickness variation, materials).

[0320] The setup used is therefore as follows: Substrate ITO, 50 nm PEDOT, 20 nm Hole transport layer HIL-Sol, made of HTM-Sol, 20 nm Emission layer made of SMB4(97%) and ES(3%) or EAS(3%), 50 nm Electron transport layer (ETL1) made of ETM1 (50%) and ETM2 (50%), 25 nm Cathode made of aluminum, 100 nm

[0321] Glass platelets coated with a 50 nm thick, structured ITO (indium tin oxide) serve as the substrate. For improved processing, these are coated with the buffer (PEDOT) Clevios P ​​VP AI 4083 (Heraeus Clevios GmbH, Leverkusen). Spin coating is performed in air using water. The layer is then baked at 180°C for 10 minutes. The hole transport layer and the emissive layer are then applied to the coated glass platelets. The hole transport layer is the polymer HTM-Sol, with the structure shown in Table 10, which was synthesized according to WO2010 / 097155. The polymer is dissolved in toluene, resulting in a typical solids content of approximately 5 g / l when, as in this case, the typical device thickness of 20 nm is to be achieved via spin coating. The layers are spun in an inert gas atmosphere, in this case argon, and baked for 60 minutes at 180°C.

[0322] The emission layer always consists of at least one matrix material (host material) and one emitting dopant (emitter). A specification such as SMB4 (97%) and ES or EAS (3%) means that the SMB4 material is present in the emission layer at a weight fraction of 97% and the ES or EAS dopant at a weight fraction of 3%. The mixture for the emission layer is dissolved in toluene or chlorobenzene. The typical solids content of such solutions is approximately 18 g / l when, as in this case, the typical layer thickness of 50 nm for a device is to be achieved by spin coating. The layers are spin-coated in an inert gas atmosphere, in this case argon, and baked out for 10 minutes at 140° to 160°C. The materials used are shown in Table 10.

[0323] The materials for the electron transport layer and the cathode are thermally vapor-deposited in a vacuum chamber. The electron transport layer, for example, can consist of more than one material, which are mixed together in specific volume fractions by co-evaporation. A specification such as ETM1 (50%) and ETM2 (50%) means that materials ETM1 and ETM2 are each present in the layer at a volume fraction of 50%. The materials used in this case are shown in Table 10. Table 9: Results of solution-processed OLEDs at 1000 cd / m² Example. Dotand EQE (%) Voltage (V) Color EL-FWHM [eV] Sol-BF1 ES15 7.8 4.4 Blue 0.15 Table 10: Structural formulas of the materials used HTM1 [1365840-52-3] HTM2 [1450933-44-4] HTM3 [1401068-29-8] SMB1 [1087346-88-0] SMB2 [667940-34-3] SMB3 [1627916-48-6] SMB4 [1818872-85-3] TMM1 / ETM3 [1201800-83-0] [1643476-29-2] (40%) TMM2 [1822310-86-0] (60%) [1805802-42-9] Ref.-D1 [2222555-03-3] Ref.-D2 PS1 [1541114-98-0] PS2 [2245865-85-2] PS3 [1615218-73-9] ETM1 [1233200-52-6] ETM2 [25387-93-3] HTM-Sol

[0324] The abbreviations of the compounds according to the invention, which are used in the tables previously set out with regard to the OLED components, refer to the abbreviations provided in the synthesis examples above.

[0325] The compounds according to the invention show narrower electroluminescence spectra compared to the references, recognizable by the lower or equal EL-FWHM values ​​( EL ectroluminescence - F ull W idth H alf M aximum - width of the EL emission spectra in eV at half peak height). Narrower electroluminescence spectra lead to significantly improved color purity (smaller CIE y values). Furthermore, the EQE values ​​( E external Q uanten E efficiency) significantly larger and operating voltages lower compared to the reference, resulting in significantly improved power efficiencies of the device and thus lower power consumption. Manufacturing of components for color conversion

[0326] The compounds according to the invention can be used for color conversion. For this purpose, the compounds are incorporated into a composition, which is then processed into pixels or planar layers using known methods (spin coating, slit coating, raking, screen printing, nozzle printing, inkjet printing, etc.). The compositions typically consist of crosslinkable components (monomers, oligomers, polymers), e.g., based on acrylates, acrylamides, polyesters, silicones, etc., and one or more thermally or photochemically activatable starter components. In addition, further components such as organic additives (antioxidants, stabilizers, flow agents, viscosity moderators, etc.) or inorganic fillers (SiO₂, TiO₂, Al₂O₃, etc.) can be incorporated. General manufacturing procedure of the composition and derived layers:

[0327] 0.5 g of the inventive compound ES or EAS, 0.2 g titanium dioxide (TiO₂ ToyoColor, Toyo Ink Group) and 10 g OE-6550 Optical Encapsulant (Dow Corning) are homogenized under very thorough stirring (magnetic stirrer) and ultrasound (ultrasonic bath) at 40 °C. Layers with a thickness of approximately 15 µm are produced by doctor blade application and then cured by baking under a nitrogen atmosphere (150 °C, 1 hour). Spectral measurement of the layers:

[0328] Fluorescence spectra and EQE values ​​(External Quantum Efficiency, EQE = Emitted Photons / Absorbed Photons) of the layers are determined in a fluorescence spectrometer (C9920, Hamamatsu photonics) with integrating sphere and fiber optics (excitation wavelength CWL: 420 - 440 nm for blue, 450 nm for green, yellow and red emitters, reference measurement in air at room temperature). Results

[0329] Table 11 summarizes the results: Example. material Color FWHM [eV] EQE [%] CCG1 ES39 Deep green 0.16 26.4 CCG2 ES65 Yellow 0.15 26.8 CCG3 ES66 Yellow 0.14 27.6 CCG4 ES84 Green 0.15 29.6 CCR2 ES67 Red 0.15 25.0 CCB3 ES5 Deep blue 0.14 25.2 CCB4 ES13 Blue 0.15 27.4 CCB5 ES16 Blue 0.15 25.6 CCB6 ES17 Blue 0.15 27.3 CCB7 ES19 Blue 0.14 28.6 CCB8 ES20 Deep blue 0.14 24.3 CCB9 ES22 Deep blue 0.15 24.0 CCB10 ES26 Deep blue 0.15 26.7 CCB11 ES29 Blue 0.15 32.1 CCB12 ES32 Blue 0.16 34.0 CCB13 ES33 Blue 0.15 29.4 CCB14 ES35 Blue 0.15 30.1 CCB15 ES36 Deep blue 0.15 29.6 CCB16 ES45 Deep blue 0.14 21.6 CCB17 ES46 Blue 0.14 33.5 CCB18 ES53 Blue 0.14 30.3 CCB19 ES57 Blue 0.15 31.4 CCB20 EAS5 Deep blue 0.15 29.9 CCB21 EAS16 Deep blue 0.17 25.8 CCB22 EAS25 Deep blue 0.16 24.9 CCB23* EAS33A Deep blue 0.15 26.8 CCB24* EAS39 Deep blue 0.15 27.8 CCB25* EAS40B Blue 0.15 31.0 CCB26* EAS42 Blue 0.15 30.3 CCB27 ES72 Blue 0.19 31.4 CCB28 ES74 Blue 0.14 29.9 CCB29 ES75 Blue 0.14 30.4 CCB30 ESA45A Blue 0.15 29.1 CCB31 ES80 Blue 0.14 28.9 CCB32 ES81 Blue 0.18 28.7 CCB33 ES85 Blue 0.15 30.3 CCB34 ES89 Deep blue 0.16 31.2 *Reference example

Claims

1. A compound according to formula (I), wherein the symbols and indices used are as follows: X is the same or different at each instance and is N, C-CN, C-Y-Ry, or CRb, preferably N, C-CN, or C-Y-Ry, particularly preferably C-CN; Y is the same or different at each instance and is CO, P(=O)Ra, SO, SO2, C(O)O, C(S)O, C(O)S, C(=O)NRa, C(=O)NAr, preferably CO, P(=O)Ra, SO, SO2, particularly preferably CO; R is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar)2, N(Re)2, C(=O)N(Ar)2, C(=O)N(Re)2, C(Ar)3, C(Re)3, Si(Ar)3, Si(Re)3, B(Ar)2, B(Re)2, C(=O)Ar, C(=O)Re, P(=O)(Ar)2, P(=O)(Re)2, P(Ar)2, P(Re)2, S(=O)Ar, S(=O)Re, S(=O)2Ar, S(=O)2Re, OSO2Ar, OSO2Re, a straight-chain alkyl or alkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, wherein the alkyl or alkoxy group may each be substituted with one or more Re radicals, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may be substituted by one or more Re radicals, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms and which may be substituted by one or more Re radicals, or an arylthio or heteroarylthio group having 5 to 60 aromatic ring atoms and which may be substituted by one or more Re radicals, or a diarylamino, arylheteroarylamino, diheteroarylamino group having 5 to 60 aromatic ring atoms and which may be substituted by one or more Re radicals, or an arylalkyl or heteroarylalkyl group having 5 to 60 aromatic ring atoms and 1 to 10 carbon atoms in the alkyl radical, and which may be substituted by one or more radicals Re; wherein any R radical may form a ring system with a further group, preferably Rd; Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which may be substituted with one or more Re radicals, wherein two Ar radicals bonded to the same C atom, Si atom, N atom, P atom, or B atom may also be joined by a single bond or a bridge selected from B(Re), C(Re)2, Si(Re)2, C=O, C=NRe , C=C(Re)2, O, S, S=O, SO2, N(Re), P(Re) and P(=O)Re; Ra, Rb, Rc, Rd, Re is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar')2, N(Re)2, C(=O)N(Ar')2, C(=O)N(R1)2, C(Ar')3, C(R1)3, Si(Ar')3, Si(R1)3, B(Ar')2, B(R1)2, C(=O)Ar', C(=O)R1, P(=O)(Ar')2, P(=O)(R1)2, P(Ar')2, P(R1)2, S(=O)Ar', S(=O)R1, S(=O)2Ar', S(=O)2R1, OSO2Ar', OSO2R1, a straight-chain alkyl or alkoxy group with 1 to 40 C atoms or a branched or cyclic alkyl or alkoxy group with 3 to 20 carbon atoms, wherein the alkyl or alkoxy group may each be substituted with one or more R1 radicals, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may each be substituted by one or more R1 radicals, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms and which may be substituted by one or more R1 radicals; wherein two radicals Ra, Rb, Rc, Rd, Re may also form a ring system together or with a further group, preferably R or Ry; Ry is the same or different at each instance and is C(Ar')3, C(R1)3, Si(Ar')3, Si(R1)3, N(Ar')2, N(Re)2, a straight-chain alkyl or alkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, wherein the alkyl or alkoxy group may be substituted in each case by one or more R1 radicals, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms and which may be substituted by one or more R1 radicals; wherein two Ry radicals may also form a ring system with one another, or one Ry radical may form a ring system with one radical Ra, Rb, Rc, Rd, Re, preferably a Ra radical; Ar' is the same or different at each instance and is an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms and which may be substituted by one or more R1 radicals, wherein two radicals Ar', which are bonded to the same C atom, Si atom, N atom, P atom, or B atom, may also be joined together by a single bond or a bridge selected from B(R1), C(R1)2, Si(R1)2, C=O, C=NR1, C=C(R1)2, O, S, S=O, SO2, N(R1), P(R1) and P(=O)R1; R1 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO2, N(Ar")2, N(R2)2, C(=O)Ar", C(=O)R2, P(=O)(Ar")2, P(Ar")2, B(Ar")2, B(R2)2, C(Ar")3, C(R2)3, Si(Ar")3, Si(R2)3, a straight-chain alkyl or alkoxy group with 1 to 40 C atoms or a branched or cyclic alkyl or alkoxy group with 3 to 40 C atoms, which each may be substituted by one or more R2 radicals, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which each may be substituted by one or more R2 radicals, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms and which may be substituted by one or more radicals R2, or an aralkyl or heteroaralkyl group with 5 to 60 aromatic ring atoms and which may be substituted by one or more R2 radicals, or a combination of these systems; wherein two or more, preferably adjacent, R1 radicals may form a ring system with one another, wherein one or more R1 radicals may form a ring system with a further part of the compound; Ar" is the same or different at each instance and is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and may be substituted with one or more R2 radicals, wherein two Ar" radicals bonded to the same C atom, Si atom, N atom, P atom, or B atom may also be joined together by a single bond or a bridge selected from B(R2), C(R2)2, Si(R2)2, C=O, C=NR2, C=C(R2)2,O, S, S=O, SO2, N(R2), P(R2) and P(=O)R2; R2 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and in which one or more H atoms may be replaced by D, F, Cl, Br, I, or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms, wherein two or more, preferably adjacent substituents R2 together may form a ring system; characterized in that two radicals Ra together with the further groups to which the two radicals Ra bind form a fused ring.

2. The compound according to claim 1, characterized in that at least one, preferably at least two, of the R, Ra, Rb, Rc, Rd, Re radicals are not H, preferably are not H, D, OH, NO2, F, Cl, Br, I.

3. The compound according to claim 1 or 2, characterized in that at least one, preferably at least two, of the Ra, Rc radicals are a straight-chain alkyl or alkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, wherein the alkyl or alkoxy group may be substituted in each case by one or more radicals R1.

4. The compound according to one or more of claims 1 to 3, characterized in that the R radical is an aromatic or heteroaromatic ring system having 5 to 13 aromatic ring atoms and which may be substituted with one or more radicals Re.

5. The compound according to one or more of claims 1 to 4, characterized in that two Ra radicals together with the further groups to which the two Ra radicals bind form an aliphatic or heteroaliphatic ring having 3 to 20 or an aromatic or heteroaromatic ring having 5 to 13 ring atoms.

6. The compound according to one or more of claims 1 to 5, characterized in that two Rc radicals together with the further groups to which the two Rc radicals bind form a fused ring, preferably an aliphatic or heteroaliphatic ring having 3 to 20, preferably 5 to 18 ring atoms, or an aromatic or heteroaromatic ring having 5 to 13 ring atoms, particularly preferably an aliphatic or heteroaliphatic ring having 3 to 20, preferably 5 to 18 ring atoms.

7. The compound according to one or more of claims 1 to 6, which is a compound according to one of formulae (1-1) to (1-83), wherein the symbols Ra, Rb, Rc, Rd, Re and Ry have the meanings given in claim 1 and the further symbols and indices used are as follows: X1 is the same or different at each instance and is N or CRe, preferably CRe, with the proviso that not more than two of the X1 groups in one cycle are N; Y1 is the same or different at each instance and is C(Re)2, (Re)2-C(Re)2, (Re)C=C(Re), NRe, NAr', O, S, SO, SO2, Se, P(O)Re, BRe or Si(Re)2, preferably C(Re)2, (Re)2-C(Re)2, (Re)C=C(Re), O or S, particularly preferably C(Re)2; T1 is the same or different at each instance and is a condensed ring, preferably an aliphatic or heteroaliphatic ring having 3 to 20, preferably 5 to 18 ring atoms, or an aromatic or heteroaromatic ring having 5 to 13 ring atoms, particularly preferably for an aliphatic or heteroaliphatic ring having 3 to 20, preferably 5 to 18 ring atoms, which may be substituted by one or more R1, wherein R1 has the meaning given in claim 1; n is 0, 1, 2, or 3, preferably 0, 1, or 2; m is 0, 1, 2, 3, or 4, preferably 0, 1, or 2.

8. The compound according to one or more of claims 1 to 7, characterized in that at least two R, Ra, Rb, Rc, Rd, Re, Ry radicals together with the further groups to which the two R, Ra, Rb, Rc, Rd, Re, Ry radicals bind, form a condensed ring, wherein the two R, Ra, Rb, Rc, Rd, Re, Ry radicals form at least one structure of the following formulae (Cy-1) to (Cy-10), wherein R1 and R2 have the meanings given in claim 1, the dashed bonds represent the sites of attachment to the atoms of the groups to which the two R, Ra, Rb, Rc, Rd, Re, Ry radicals bind, and furthermore: Z1, Z3 is the same or different at each instance and is C(R3)2, O, S, NR3 or C(=O); Z2 is C(R1)2, O, S, NR1, or C(=O), wherein two adjacent groups Z2 represent -CR1=CR1- or an ortho-bonded arylene or heteroarylene group having 5 to 14 aromatic ring atoms which may be substituted by one or more R1 radicals; G is an alkylene group having 1, 2, or 3 C atoms and which may be substituted by one or more R1 radicals, -CR1=CR1- or an ortho-bonded arylene or heteroarylene group having 5 to 14 aromatic ring atoms which may be substituted by one or more R1 radicals; R3 is the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO2, N(Ar")2, N(R2)2, C(=O)Ar", C(=O)R2, P(=O)(Ar")2, P(Ar")2, B(Ar")2, B(R2)2, C(Ar")3, C(R2)3, Si(Ar")3, Si(R2)3, a straight-chain alkyl or alkoxy group with 1 to 40 C atoms or a branched or cyclic alkyl or alkoxy group with 3 to 40 C atoms, each of which may be substituted by one or more R2 radicals, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and each of which may be substituted by one or more R2 radicals, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms and which may be substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms and which may be substituted by one or more R2 radicals, or a combination of these systems; wherein two R3 radicals bonded to the same carbon atom may be joined together to form an aliphatic or aromatic ring system, thus forming a spiro system; furthermore, R3 may form a ring system with a R, Ra, Rc, Rd, Re, or R1 radical; with the proviso that no two heteroatoms in these groups are bonded directly to one another and no two C=O groups are bonded directly to one another.

9. The compound according to one or more of claims 1 to 8, characterized in that at least two R, Ra, Rb, Rc, Rd, Re, Ry radicals form a fused ring together with the further groups to which the two R, Ra, Rb, Rc, Rd, Re, Ry radicals bind, wherein the two R, Ra, Rb, Rc, Rd, Re, Ry radicals form at least one structure of the formulae (RA-1) to (RA-13): wherein R1 has the meaning given above, the dashed lines represent the sites of attachment to the atoms of the groups to which the two R, Ra, Rb, Rc, Rd, Re, Ry radicals bind, and the further symbols used are as follows: Y2 is the same or different at each instance and is C(R1)2, (R1)2C-C(R1)2, (R1)C=C(R1), NR1, NAr', O, or S, preferably C(R1)2, (R1)2C-C(R1)2, (R1)C=C(R1), O, or S; Rf is the same or different at each instance and is F, a straight-chain alkyl or alkoxy group with 1 to 40 C atoms or a branched or cyclic alkyl or alkoxy group with 3 to 20 carbon atoms, wherein the alkyl or alkoxy group may be substituted in each case with one or more R2 radicals, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms and which may be substituted in each case by one or more R2 radicals, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which may be substituted by one or more R2 radicals; wherein two Rf radicals may also form a ring system with one another, or one Rf radical may form a ring system with one Rf radical or with a further group; r is 0, 1, 2, 3, or 4, preferably 0, 1, or 2, particularly preferably 0 or 1; s is 0, 1, 2, 3, 4, 5, or 6, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1, or 2; t is 0, 1, 2, 3, 4, 5, 6, 7, or 8, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1, or 2; v is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1, or 2, wherein structures of the formulae RA-1, RA-3, RA-4, and RA-5 are preferred and structures of the formulae RA-4 and RA-5 are particularly preferred.

10. The compound according to one or more of claims 1 to 9, wherein at least two R, Ra, Rb, Rc, Rd, Re, Ry radicals form a fused ring together with the further groups to which the two R, Ra, Rb, Rc, Rd, Re, Ry radicals bind, wherein the two R, Ra, Rb, Rc, Rd, Re, Ry radicals form structures of formula (RB): wherein R1 has the meaning set forth in claim 1, the dashed bonds represent the sites of attachment via which the two R, Ra, Rb, Rc, Rd, Re, Ry radicals bind, the index m is 0, 1, 2, 3, or 4, preferably 0, 1, or 2, and Y3 is C(R1)2,NR1, NAr', BR1, BAr', O or S, preferably C(R1)2, NAr' or O.

11. The compound according to one or more of claims 1 to 10, characterized in that R or Ar is the same or different at each instance and is selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, or triphenylene, and each of which may be substituted with one or more Re radicals.

12. The compound according to at least one of the preceding claims, characterized in that the compound is symmetrical with respect to the Ra and Rc radicals.

13. The compound according to at least one of the preceding claims, characterized in that the Re and / or Rd radical comprises at least one group selected from C(Ar')3, C(R1)3, Si(Ar')3, Si(R1)3, B(R1)2, preferably selected from C(Ar')3, C(R1)3, Si(Ar')3, Si(R1)3, preferably a fluorene group that is substituted with one or more R1 radicals or that forms a fluorene group with a Rd or Re radical, respectively.

14. The compound according to at least one of the preceding claims, characterized in that the compound comprises exactly two or exactly three structures according to formula (I) and / or (I-1) to (I-81).

15. An oligomer, polymer, or dendrimer containing one or more compounds according to any one of claims 1 to 14, wherein one or more bonds of the compounds to the polymer, oligomer, or dendrimer are present instead of a hydrogen atom or a substituent.

16. A formulation comprising at least one compound according to one or more of claims 1 to 14 or an oligomer, polymer, or dendrimer according to claim 15, and at least one further compound, wherein the further compound is preferably selected from one or more solvents.

17. A composition comprising at least one compound according to one or more of claims 1 to 14 or an oligomer, polymer or dendrimer according to claim 15, and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF, host materials, electron transport materials, electron injection materials, hole conducting materials, hole injection materials, electron blocking materials, and hole blocking materials, preferably host materials.

18. The composition according to claim 17, characterized in that the composition comprises at least one further compound which is a TADF host material and / or at least one further compound which is a phosphorescent emitter (triplet emitter), wherein the further compounds together with a compound according to one or more of claims 1 to 14 or an oligomer, polymer or dendrimer according to claim 15, preferably form a hyperfluorescence and / or hyperphosphorescence system.

19. A method for producing a compound according to one or more of claims 1 to 14, characterized in that a basic structure having an aromatic amino group is synthesized and at least one aromatic or heteroaromatic residue is introduced, preferably by means of a nucleophilic aromatic substitution reaction or a coupling reaction.

20. A use of a compound according to one or more of claims 1 to 14 or an oligomer, polymer, or dendrimer according to claim 15 in an electronic device, preferably as a blue emitter.

21. An electronic device comprising at least one compound according to one or more of claims 1 to 14 or an oligomer, polymer, or dendrimer according to claim 15, wherein the compound according to one or more of claims 1 to 14 or the oligomer, polymer, or dendrimer according to claim 15 is preferably comprised in an emitting layer as a blue emitter.