BORON- AND NITROGEN-CONTAINING HETEROCYCLIC COMPOUNDS FOR ORGANIC ELECTROLUMINESCENT DEVICES

Description

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

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

[0003] Polycyclic compounds that can be used in organic electroluminescent devices are known from US Pat. No. 6,322,908, WO 03 / 001569 A2, and US Pat. No. 2019 / 0058124. Compounds according to the present invention are not disclosed.

[0004] In general, there is still room for improvement in the use of 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 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 electroluminescent device, and which, when used in this device, lead to good device properties, as well as to provide the corresponding electronic device.

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

[0007] Furthermore, the compounds should have excellent processability, with the compounds particularly showing good solubility.

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

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

[0010] A further object of the present invention can be seen in providing compounds suitable for use in phosphorescent or fluorescent electroluminescent devices, in particular as matrix materials. In particular, it is an object of the present invention to provide matrix materials suitable for red, yellow, and blue phosphorescent electroluminescent devices.

[0011] Furthermore, the compounds should lead to devices with excellent color purity, especially when used as matrix materials or as electron transport materials in organic electroluminescent devices.

[0012] Another task can be seen in providing electronic devices with excellent performance as cost-effectively as possible and in consistent quality

[0013] Furthermore, the electronic devices should be able to be used or adapted for a variety of purposes. In particular, the performance of the electronic devices should be maintained over a wide temperature range.

[0014] Surprisingly, it has been found that certain compounds, described in more detail below, achieve this objective, are highly suitable for use in electroluminescent devices, and lead to organic electroluminescent devices that exhibit very good properties, particularly with regard to lifetime, color purity, efficiency, and operating voltage. These compounds, as well as electronic devices, in particular organic electroluminescent devices, containing such compounds, are therefore the subject of the present invention.

[0015] The present invention relates to a compound comprising at least one structure of formula (I), preferably a compound according to formula (I), where the symbols used are: Z a< is, on each occurrence, the same or different from R a< or Ar a< , where Ar a< is, on each occurrence, the same or different from each other, and stands for an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals Ar or R a<, where two radicals Z a< can form a ring system; Z b< is, on each occurrence, the same or different from each other, R b< , Ar or the group Z b< forms a ring Ar b< with the adjacent group Z c<, where the ring Ar b< is, on each occurrence, the same or different from each other, and stands for an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals Ar or R b<, where the ring Ar b< together with the boron atom and the two nitrogen atoms forms a 5-membered ring, where the ring Ar b< together with a group Z a< or a ring Ar b< can form a ring system;Z°is the same or different on each occurrence and R c<, Ar or the group Z c< forms with the adjacent group Z b< a ring Ar b<, where the ring Ar b< is the same or different on each occurrence and represents an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals Ar or R b<, where the ring Ar b< together with the boron atom and the two nitrogen atoms forms a 5-membered ring; ; and for the other symbols and indices used: Ar is, identically or differently at each occurrence, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals R, where the group Ar may form a ring system with at least one group Ar, R, R a< , R b< , R c< or one further group; R, R a< , R b< , R c< 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, alkoxy or thioalkoxy group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, where the alkyl, alkoxy, thioalkoxy,Alkenyl or alkynyl group may each be substituted by one or more radicals R 1<, where one or more non-adjacent CH 2 groups may be replaced by R 1< C=CR 1< , C≡C, Si(R 1< ) 2 , C=O, C=S, C=Se, C=NR 1< , -C(=O)O-, -C(=O)NR 1< -, NR 1< , P(=O)(R 1< ), -O-, -S-, SO or SO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R 1<, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<; or heteroarylthio group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<, or a diarylamino, arylheteroarylamino, diheteroarylamino group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<,or an arylalkyl or heteroarylalkyl group having 5 to 60 aromatic ring atoms and 1 to 10 C atoms in the alkyl radical, which may be substituted by one or more radicals R 1<; two radicals R, R a<, R b<, R c< may also form a ring system with one another or with another group; Ar' is, at each occurrence, identical or different, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals R 1<, where two radicals Ar' which are bonded to the same C atom, Si atom, N atom, P atom or B atom may also be bridged to one another by a single bond or a bridge selected from B(R 1< ), C(R 1< ) 2 , Si(R 1< ) 2 , C=O, C=NR 1< , C=C(R 1< ) 2 , O, S, S=O, SO 2 , N(R 1< ), P(R 1< ) and P(=O)R 1< ; R 1< is, identically or differently at 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, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms or an alkenyl group having 2 to 40 C atoms, each of which may be substituted by one or more radicals R 2<, where one or more non-adjacent CH 2 groups are substituted by -R 2< C=CR 2< -, -C≡C-, Si(R 2< ) 2 , C=O, C=S, C=Se, C=NR 2< , -C(=O)O-, -C(=O)NR 2< -, NR 2< , P(=O)(R 2< ), -O-, -S-, SO or SO 2 and where one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO 2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which can be substituted by one or more radicals R 2<, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R 2<,or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 2<, or a combination of these systems; two or more, preferably adjacent radicals R 1< may form a ring system with one another, and one or more radicals R 1< may form a ring system with another part of the compound; Ar" is, at each occurrence, identical or different, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 2<, where two radicals Ar" which bind to the same C atom, Si atom, N atom, P atom or B atom may also be linked 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< ,be bridged together; R 2< is, at each occurrence, identical or different, 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, 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, two or more, preferably adjacent, substituents R 2< may form a ring system with one another.

[0016] An aryl group within the meaning of this invention contains 6 to 40 C atoms; a heteroaryl group within the meaning of this invention contains 2 to 40 C atoms and at least one heteroatom, with the proviso that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aryl group or heteroaryl group is understood to be either a simple aromatic cycle, i.e. benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a condensed (fused) aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatics linked to one another by a single bond, such as biphenyl, are not referred to as aryl or heteroaryl groups, but as an aromatic ring system.

[0017] An electron-poor heteroaryl group within the meaning of the present invention is a heteroaryl group that has at least one heteroaromatic six-membered ring containing at least one nitrogen atom. Further aromatic or heteroaromatic five-membered rings or six-membered rings can be fused to this six-membered ring. Examples of electron-poor heteroaryl groups are pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline, or quinoxaline.

[0018] An aromatic ring system within the meaning of this invention contains 6 to 60 C atoms in the ring system. A heteroaromatic ring system within the meaning of this invention contains 2 to 60 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O, and / or S. An aromatic or heteroaromatic ring system within the meaning of this invention is understood to mean a system that does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups can also be linked by a non-aromatic unit, such as a C, N, or O atom. For example, systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc.are 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. The aromatic ring system is preferably selected from fluorene, 9,9'-spirobifluorene, 9,9-diarylamine, or groups in which two or more aryl and / or heteroaryl groups are linked by single bonds.

[0019] In the context of the present invention, an aliphatic hydrocarbon radical or an alkyl group or an alkenyl or alkynyl group which may contain 1 to 20 C atoms and in which individual H atoms or CH 2 groups may be substituted by the above-mentioned groups, preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, 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 may be straight-chain, branched, or cyclic, wherein one or more non-adjacent CH 2 groups may be replaced by the above-mentioned groups; furthermore, one or more H atoms may also be replaced by D, F, Cl, Br, I, CN, or NO 2 , preferably F, Cl, or CN, more preferably F or CN, particularly preferably CN.

[0020] An aromatic or heteroaromatic ring system with 5 - 60 or 5 to 40 aromatic ring atoms, which may each be substituted by the above-mentioned radicals and which may be linked to the aromatic or heteroaromatic ring via any position, is understood to mean in particular groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, 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.,

[0021] For the purposes of this description, the phrase "two or more residues can form a ring" is understood to mean, among other things, that the two residues are linked by a chemical bond with the formal elimination of two hydrogen atoms. This is illustrated by the following scheme.

[0022] Furthermore, the above formulation should also be understood to mean that if one of the two residues represents hydrogen, the second residue binds to the position to which the hydrogen atom was bonded, forming a ring. This is illustrated by the following scheme:

[0023] In a preferred embodiment, the compounds according to the invention can comprise a structure of the formulas (II-1) to (II-6), particularly preferably the compounds according to the invention can be selected from the compounds of the formulas (II-1) to (II-6), where the symbols R a< , R b< , R c< , Ar a< and Ar b< have the meanings given above, in particular for formula (I).

[0024] Structures / compounds of the formulas (II-3) to (II-6) are preferred, structures / compounds of the formulas (II-5) and (II-6) are particularly preferred.

[0025] If a compound contains two or more nitrogen atoms, these nitrogen atoms are preferably not adjacent, so that no N—N bonds are present, apart from the N—N bond in formula (I) or the preferred embodiments of this structure / compound presented above and below.

[0026] In a further preferred embodiment, it can be provided that the compounds according to the invention comprise at least one structural element of the formulas (III-1) to (III-42), where dashed lines represent the bonds to the further structural elements of a compound according to formulas (I) and / or (II-1) to (II-6), the symbols Ar a< and R a< have the meanings set out above, in particular for formula (I), and the following applies to the further symbols: X, identical or different on each occurrence, is N or CR, preferably CR, with the proviso that no more than three, preferably no more than two of the groups X in a cycle are N, where R has the meaning set out above, in particular for formula (I); X a<, identical or different on each occurrence, is N or CR a<, preferably CR a<, with the proviso that no more than three, preferably no more than two of the groups X a< in a cycle are N, where R a< has the meaning set out above, in particular for formula (I);X b< is, on each occurrence, identical or different, N or CR b< , preferably CR b< , with the proviso that no more than three, preferably no more than two of the groups X b< in a cycle are N, where R b< has the meaning set out above, in particular for formula (I), Y 1< is, on each occurrence, identical or different, N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al(Ar), Al(R), Ga(Ar), Ga(R), C=O, C(R) 2 , Si(R) 2 , Ge(R) 2 , C=NR, C=NAr, C=C(R) 2 , C=C(R)(Ar), O, S, Se, S=O, or SO 2 , preferably N(Ar), N(R), B(Ar), B(R), P(=O)R, P(=O)Ar, C=O, C(R) 2 , C=C(R) 2 , C=C(R)(Ar), Si(R) 2 , O, S, Se, S=O or SO 2 , particularly preferably N(Ar), C(R) 2 , O or S, where R has the meaning set out above, in particular for formula (I);Y 2< is on each occurrence, identically or differently, a bond, N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al(Ar), Al(R), Ga(Ar), Ga(R), C=O, C(R) 2 , Si(R) 2 , Ge(R) 2 , C=NR, C=NAr, C=C(R) 2 , C=C(R)(Ar), O, S, Se, S=O, or SO 2 , preferably a bond, N(Ar), N(R), B(Ar), B(R), P(=O)R, P(=O)Ar, C=O, C(R) 2 , C=C(R) 2 , C=C(R)(Ar), Si(R) 2 , O, S, Se, S=O or SO 2 , especially preferably N(Ar), C(R) 2 , O or S, where R has the meaning set out above, in particular for formula (I);Y 3< is the same or different in every occurrence C=C(R) 2 , C=C(R)(Ar), O, S, Se, S=O, or SO 2 , preferably N(Ar), N(R), B(Ar), B(R), P(=O)R, P(=O)Ar, C=O, C(R) 2 , C=C(R) 2 , C=C(R)(Ar), Si(R) 2 , O, S, Se, S=O or SO 2 , particularly preferably N(Ar), C(R) 2 , O or S, where R has the meaning set out above, in particular for formula (I);Y 4< is on each occurrence, identically or differently, a bond, N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al(Ar), Al(R), Ga(Ar), Ga(R), C=O, C(R) 2 , Si(R) 2 , Ge(R) 2 , C=NR, C=NAr, C=C(R) 2 , C=C(R)(Ar), O, S, Se, S=O, or SO 2 , preferably a bond, N(Ar), N(R), B(Ar), B(R), P(=O)R, P(=O)Ar, C=O, C(R) 2 , C=C(R) 2 , C=C(R)(Ar), Si(R) 2 , O, S, Se, S=O or SO 2 , especially preferably N(Ar), C(R) 2 , O or S, where R has the meaning set out above, in particular for formula (I);

[0027] Structures / compounds of the formulas (III-19), (III-20), (III-25) to (III-28), (III-30) to (III-35) and (III-37) to (III-42) are preferred and structures of the formulas (III-20), (III-25), (III-26), (III-28), (III-30) to (III-33), (III-37), (III-38), (III-41) and (III-42) are particularly preferred.

[0028] Preferably, in particular in formulas (III-1) to (III-42), it can be provided that not more than four, preferably not more than two groups X, X a< and X b< stand for N, particularly preferably all groups X, X a< and X b< stand for CR, CR a< or CR b<.

[0029] In a further preferred embodiment, it can be provided that the compounds according to the invention comprise at least one structural element of the formulas (IV-1) to (IV-53), where dashed lines represent the bonds to the further structural elements of a compound according to formulas (I) and / or (II-1) to (II-6), the symbols Ar a< , R, R a< and R b< have the meanings given above, in particular for formula (I), the symbols X, X a< , X b< , Y 1< , Y 2< , Y 3< and Y 4< have the meanings given above, in particular for formulas (III-1) to (III-42) and the following applies to the further symbols: l is 0, 1, 2, 3, 4 or 5, preferably 0, 1 or 2; m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2; n is 0, 1, 2 or 3, preferably 0, 1 or 2; j is 0, 1 or 2, preferably 0 or 1, k is 0 or 1.

[0030] Structures / compounds of the formulas (IV-19), (IV-20), (IV-25) to (IV-35) and (IV-37) to (IV-53) are preferred and structures of the formulas (IV-20), (IV-25), (IV-26), (IV-28), (IV-30) to (IV-33), (IV-37) to (IV-42), (IV-44), (IV-45), (IV-47), (IV-49), (IV-52) and (IV-53) are particularly preferred.

[0031] The sum of the indices k, j, m, n and l, in particular in structures / compounds of the formulas (IV-1) to (IV-53), is preferably at most 10, preferably at most 8, particularly preferably at most 6 and particularly preferably at most 4.

[0032] Preferably, the compound can comprise 2, 4, 6 or more structural elements of the formulas (III-1) to (III-42) and / or (IV-1) to (IV-53), wherein two adjacent nitrogen atoms are shared by two adjacent structural elements and the dashed lines represent the bonding sites to the further parts of the second, adjacent structural element.

[0033] In a preferred embodiment, the compounds according to the invention can comprise a structure of the formulas (V-1) to (V-52), particularly preferably the compounds according to the invention can be selected from the compounds of the formulas (V-1) to (V-52), where the symbols Ar a< and R a< have the meanings given above, in particular for formula (I), the symbols X, X a< , X b< , Y 1< , Y 2< , Y 3< and Y 4< have the meanings given above, in particular for formulas (III-1) to (III-42) and the following applies to the other symbols: Y 5 < is the same or different in every occurrence C=C(R) 2 , C=C(R)(Ar), O, S, Se, S=O, or SO 2 , preferably N(Ar), N(R), B(Ar), B(R), P(=O)R, P(=O)Ar, C=O, C(R) 2 , C=C(R) 2 , C=C(R)(Ar), Si(R) 2 , O, S, Se, S=O or SO 2 , particularly preferably N(Ar), C(R) 2 , O or S, where R has the meaning set out above, in particular for formula (I).

[0034] Structures / compounds of the formulas (V-17), (V-18) and (V-22) to (V-52) are preferred and structures / compounds of the formulas (V-23) to (V-25), (V-27), (V-28), (V-32), (V-36), (V-37), (V-41) to (V-44), (V-47), (V-48), (V-51) and (V-52) are particularly preferred.

[0035] Preferably, in particular in formulas (V-1) to (V-52), it can be provided that not more than four, preferably not more than two groups X, X a< and X b< stand for N, particularly preferably all groups X, X a< and X b< stand for CR, CR a< or CR b<.

[0036] In a particularly preferred embodiment, the compounds according to the invention can comprise a structure of the formulas (VI-1) to (VI-64), particularly preferably the compounds according to the invention can be selected from the compounds of the formulas (VI-1) to (VI-64), where the symbols Ar a< , R, R a< and R b< have the meanings given above, in particular for formula (I), the symbols Y 1< , Y 2< , Y 3< and Y 4< have the meanings given above, in particular for formulas (III-1) to (III-42), the symbol Y 5< has the meaning given above, in particular for formulas (V-1) to (V-52) and the following applies to the other symbols: l is 0, 1, 2, 3, 4 or 5, preferably 0, 1 or 2; m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2; n is 0, 1, 2 or 3, preferably 0, 1 or 2; j is 0, 1 or 2, preferably 0 or 1, k is 0 or 1.

[0037] Structures / compounds of the formulas (VI-17), (VI-18) and (VI-22) to (VI-64) are preferred.

[0038] The sum of the indices k, j, m, n and l, in particular in structures / compounds of the formulas (VI-1) to (VI-64), is preferably at most 10, preferably at most 8, particularly preferably at most 6 and particularly preferably at most 4.

[0039] Furthermore, in particular in structures / compounds of the formulas (III-1) to (III-42), (IV-1) to (IV-53), (V-1) to (V-52) and / or (VI-1) to (VI-64) it can be provided that the group Y 2< does not represent a bond.

[0040] Furthermore, it can be provided that the group Y 2< of the formulas (III-1) to (III-42), (IV-1) to (IV-53), (V-1) to (V-52) and / or (VI-1) to (VI-64) stands for a group C(R) 2 or Si(R) 2 , preferably C(R) 2 and the two radicals R each stand for an alkyl group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl, alkenyl or alkynyl group can each be substituted by one or more radicals R 1<, where one or more non-adjacent CH 2 groups are substituted by R 1< C=CR 1< , C≡C, Si(R 1< ) 2 , C=O, C=S, C=Se, C=NR 1< , -C(=O)O-, -C(=O)NR 1< -, NR 1< , P(=O)(R 1< ), -O-, -S-, SO or SO 2 , or represent an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R 1<,Two R radicals can also form a ring system with each other or with another group, preferably forming a spiro system.

[0041] Furthermore, it can be provided, inter alia, in formulas (I), (II-1) to (II-6), (III-1) to (III-42), (IV-1) to (IV-53), (V-1) to (V-52) and / or (VI-1) to (VI-64) and / or the preferred embodiments of these formulas set out below, that at least one radical R, R a< , R b< , R c< represents a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group is in each case substituted with one or more radicals R 1< may be substituted, where one or more non-adjacent CH 2 groups may be replaced by R 1< C=CR 1< , C≡C, Si(R 1< ) 2 , C=O, C=S, C=Se, C=NR 1< , -C(=O)O-, -C(=O)NR 1< -, NR 1< , P(=O)(R 1< ), -O-, -S-, SO or SO 2 , or represents an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms,which may be substituted by one or more radicals R 1<, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<; or a heteroarylthio group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<, or a diarylamino, arylheteroarylamino, diheteroarylamino group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<, or an arylalkyl or heteroarylalkyl group having 5 to 60 aromatic ring atoms and 1 to 10 C atoms in the alkyl radical, which may be substituted by one or more radicals R 1<.

[0042] Preferably, in formulas (I), (II-1) to (II-6), (III-1) to (III-42), (IV-1) to (IV-53), (V-1) to (V-52) and / or (VI-1) to (VI-64) and / or the preferred embodiments of these formulas set out below, it can be provided that at least one radical R, R a< , R b< , R c< represents an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1<, or represents an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<;or represents a heteroarylthio group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<, or represents a diarylamino, arylheteroarylamino, diheteroarylamino group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1<, or represents an arylalkyl or heteroarylalkyl group having 5 to 60 aromatic ring atoms and 1 to 10 C atoms in the alkyl radical, which may be substituted by one or more radicals R 1<, particularly preferably represents an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R 1<.;

[0043] Furthermore, it can preferably be provided that the structures / compounds of formulas (I), (II-1) to (II-6), (III-1) to (III-42), (IV-1) to (IV-53), (V-1) to (V-52) and / or (VI-1) to (VI-64) and / or the preferred embodiments of these formulas set out below have at most one, preferably no, free olefin-like double bond, with aromatic 6-membered rings preferably being fused to aromatic 5-membered rings. Free olefin-like double bonds are initially -C=C- groups that are not part of an aromatic or heteroaromatic system and preferably contain hydrogen atoms. In addition, free olefin-like double bonds are -C=C- groups that are part of a heteroaromatic 5-membered ring, as realized, for example, in furan or imidazole residues, whereby these groups must be free. This is particularly the case if the carbon atoms of the CC double bond are connected to a hydrogen atom.In the case of condensation of another aromatic or heteroaromatic ring, as occurs, for example, with dibenzofuran or benzimidazole residues, no olefin-like double bonds are present, since the -C=C- groups are not present freely. Furthermore, no olefin-like double bonds are present if the two carbon atoms of the CC double bond are connected by a ring, which is preferably formed by the groups of formulas (RA-1) to (RA-12), formulas (RA-1a) to (RA-4f), and / or formula (RB) described below.

[0044] In a preferred development of the present invention, it can be provided that at least two radicals R, R a< , R b< , R c< form a condensed ring with the further groups to which the two radicals R, R a< , R b< , R c< are bonded, wherein the two radicals R, R a< , R b< , R c< form at least one structure of the formulas (RA-1) to (RA-12) where R 1< has the meaning set out above, the dashed bonds represent the attachment points via which the two radicals R, R a< , R b< , R c< bind to the other groups, and the other symbols have the following meaning: Y 6< is, identically or differently at 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 d< is, identically or differently at each occurrence, F, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may each be substituted by one or more radicals R 2<, where one or more non-adjacent CH 2 groups are substituted by R 2< C=CR 2< , C≡C, Si(R 2< ) 2 , C=O, C=S, C=Se, C=NR 2< , -C(=O)O-, -C(=O)NR 2< -, NR 2< , P(=O)(R 1< ), -O-, -S-, SO or SO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R 2<, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 2<;two radicals R d< can also form a ring system with one another or one radical R d< can form a ring system with one radical R 1< or with another group; 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.

[0045] In a preferred embodiment of the invention, the at least two radicals R, R a< , R b< , R c< form a condensed ring with the further groups to which the two radicals R, R a< , R b< , R c< are bonded, wherein the two radicals R, R a< , R b< , R c< preferably form at least one of the structures of the formulas (RA-1a) to (RA-4f) where the dashed bonds represent the attachment points via which the two radicals R, R a< , R b< , R c< bind to the further groups, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2 and the symbols R 1< , R 2< , R d< and the indices s and t have the meaning set out above, in particular for formula (I) and / or formulas (RA-1) to (RA-12).

[0046] Furthermore, it can be provided that the at least two radicals R, R a< , R b< , R c< , which form structures of the formulas (RA-1) to (RA-12) and / or (RA-1a) to (RA-4f) and form a condensed ring, represent radicals R, R a< , R b< from adjacent groups X, X a< , X b< or represent radicals R, R a< , R b< , R c< which each bind to adjacent C atoms, wherein these C atoms are preferably connected via a bond.

[0047] In a further preferred embodiment, at least two radicals R, R a< , R b< , R c< form a condensed ring with the further groups to which the two radicals R, R a< , R b< , R c< are bonded, wherein the two radicals R, R a< , R b< , R c< form structures of the formula (RB), where R 1< has the meaning given above, in particular for formula (I), the dashed bonds represent the attachment points via which the two radicals R, R a< , R b< , R c< bind to the further groups, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and Y 7< is C(R 1< ) 2 , NR 1< , NAr', BR 1< , BAr', O or S, preferably C(R 1< ) 2 , NAr' or O.

[0048] It can be provided that the at least two radicals R, R a< , R b< , R c< , which form structures of the formula (RB) and form a condensed ring, represent radicals R, R a< , R b< from adjacent groups X, X a< , X b< , or represent radicals R, R a< , R b< , R c< which each bind to adjacent C atoms, wherein these C atoms are preferably connected to one another via a bond.

[0049] Particularly preferably, the compounds comprise at least one structure of the formulas (VII-1) to (VII-13), particularly preferably the compounds are selected from compounds of the formulas (VII-1) to (VII-13), wherein the compounds have at least one condensed ring, where the symbols R a< , R b< , Y 2< and Y 3< have the meanings given above, in particular for formula (I) and / or formulas (III-1) to (III-42), the symbol o stands for the attachment points and the other symbols have the following meaning: m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2; n is 0, 1, 2 or 3, preferably 0, 1 or 2; j is 0, 1 or 2, preferably 0 or 1, k is 0 or 1.

[0050] Preferably, the condensed ring, in particular in formulas (VII-1) to (VII-13), is formed by at least two radicals R, R a< , R b< , R c< and the further groups to which the radicals R, R a< , R b< , R c< are bonded, wherein the at least two radicals R, R a< , R b< , R c< form structures of the formulas (RA-1) to (RA-12) and / or of the formula (RB), preferably structures of the formulas (RA-1) to (RA-12).

[0051] Preferably, the compounds may have at least two condensed rings, wherein at least one condensed ring is formed by structures of the formulas (RA-1) to (RA-12) and / or (RA-1a) to (RA-4f) and a further ring is formed by structures of the formulas (RA-1) to (RA-12), (RA-1a) to (RA-4f) or (RB).

[0052] The compounds particularly preferably comprise at least one structure of the formulas (VIII-1) to (VIII-15), particularly preferably the compounds are selected from compounds of the formulas (VIII-1) to (VIII-15), wherein the compounds have at least two condensed rings where the symbols R a< , R b< , Y 2< and Y 3< have the meanings given above, in particular for formula (I) and / or formulas (III-1) to (III-42), the symbol o stands for the attachment points of the condensed ring and the other symbols have the following meaning: m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2; n is 0, 1, 2 or 3, preferably 0, 1 or 2; j is 0, 1 or 2, preferably 0 or 1, k is 0 or 1.

[0053] Preferably, at least one of the condensed rings, particularly preferably both of the condensed rings, in particular in formulas (VIII-1) to (VIII-13), are formed by at least two radicals R, R a< , R b< , R c< and the further groups to which the two radicals R, R a< , R b< , R c< are bonded, wherein the at least two radicals R, R a< , R b< , R c< form structures of the formulas (RA-1) to (RA-12) and / or of the formula (RB), preferably structures of the formulas (RA-1) to (RA-12).

[0054] In particular, in formulas (VII-1) to (VII-13) and / or (VIII-1) to (VIII-13), it can be provided that the sum of the indices k, j, n and m is preferably 0, 1, 2 or 3, particularly preferably 1 or 2.

[0055] Furthermore, it can be provided that the substituents R, R a< , R b< , R c< , R d< , R 1< and R 2< according to the above formulas do not form a condensed aromatic or heteroaromatic ring system with the ring atoms of the ring system to which the substituents R, R a< , R b< , R c< , R d< , R 1< and R 2< are bonded. This includes the formation of a condensed aromatic or heteroaromatic ring system with possible substituents R 1< and R 2<, which can be bonded to the radicals R, R a< , R b< , R c< , R d< and R 1<.

[0056] If two radicals, which can in particular be selected from R, Ra< , Rb< , Rc< , Rd< , R1< and / or R2< , form a ring system with one another, this can be mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic. The radicals which form a ring system with one another can be adjacent, i.e. these radicals are bonded to the same carbon atom or to carbon atoms which are directly bonded to one another, or they can be further apart from one another. Furthermore, the ring systems provided with the substituents R, Ra< , Rb< , Rc< , Rd< , R1< and / or R2< can also be linked to one another via a bond, so that a ring closure can be brought about in this way. In this case, each of the corresponding binding sites is preferably provided with a substituent R, R a< , R b< , R c< , R d< , R 1< and / or R 2<.

[0057] According to a preferred embodiment, a compound according to the invention can be represented by at least one of the structures according to formulas (I), (II-1) to (II-6), (III-1) to (III-42), (IV-1) to (IV-53), (V-1) to (V-52), (VI-1) to (VI-64), (VII-1) to (VII-13) and / or (VIII-1) to (VIII-13). Preferably, compounds according to the invention, preferably comprising structures according to formulas (I), (II-1) to (II-6), (III-1) to (III-42), (IV-1) to (IV-53), (V-1) to (V-52), (VI-1) to (VI-64), (VII-1) to (VII-13) and / or (VIII-1) to (VIII-13) have a molecular weight of less than or equal to 5000 g / mol, 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 very particularly preferably less than or equal to 1200 g / mol.

[0058] Furthermore, preferred compounds according to the invention are characterized by their sublimability. These compounds generally have a molecular weight of less than approximately 1200 g / mol.

[0059] Preferably, it can be provided that Ar a< is selected, identically or differently on each occurrence, 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, which may each be substituted by one or more radicals Ar or R a<.

[0060] Preferably, it can be provided that Ar b< is selected, identically or differently on each occurrence, 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, which may each be substituted by one or more radicals Ar or R b<.

[0061] Preferred aromatic or heteroaromatic ring systems R, R a< , R b< , R c< , R d< , Ar' 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-, 3- or 4-position, dibenzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene,which may each be substituted by one or more radicals R, R 1< or R 2<.,

[0062] Preferably, it can be provided that at least one substituent R, R a< , R b< , R c< is selected, identically or differently on each occurrence, from the group consisting of H, D, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms or an aromatic or heteroaromatic ring system selected from the groups of the following formulas Ar-1 to Ar-78, preferably the substituents R, R a< , R b< , R c< either form a condensed ring, preferably according to the structures of the formulas (RA-1) to (RA-12) or (RB) or the substituent R, R a< , R b< , R c< is selected, identically or differently on each occurrence, 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-78, and / or the group Ar' is selected, identically or differently on each occurrence, from the groups of the following formulas Ar-1 to Ar-78, where R 1< has the meanings given above, the dashed bond represents the attachment point and furthermore: Ar 1< is, on each occurrence, the same or different, a bivalent aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, each of which may be substituted by one or more radicals R 1<; A is, on each occurrence, 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 radical; q is 0 or 1, where q = 0 means that no group A is bonded to this position and radicals R 1< are bonded to the corresponding carbon atoms instead.

[0063] Structures of the formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16), (Ar-69), (Ar-70), (Ar-75) are preferred and structures of the formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16) are particularly preferred.

[0064] If the above-mentioned groups for structures of formulae (Ar-1) to (Ar-78) have multiple A groups, all combinations from the definition of A are possible. Preferred embodiments are then those in which one A group represents NR 1< and the other A group represents C(R 1< ) 2 , or in which both A groups represent NR 1<, or in which both A groups represent O.

[0065] When A stands for NR 1<, the substituent R 1< which is bonded to the nitrogen atom preferably stands for an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may also be substituted by one or more radicals R 2<. In a particularly preferred embodiment, this substituent R 1<, identical or different on each occurrence, stands for an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, in particular having 6 to 18 aromatic ring atoms, which does not have any fused aryl groups and which does not have any fused heteroaryl groups in which two or more aromatic or heteroaromatic 6-ring groups are directly fused to one another, and which may in each case also be substituted by one or more radicals R 2<.Phenyl, biphenyl, terphenyl, and quaterphenyl with linkage patterns as listed above for Ar-1 to Ar-11 are preferred, where these structures may be substituted by one or more R 2< radicals instead of R 1<, but are preferably unsubstituted. Also preferred are triazine, pyrimidine, and quinazoline, as listed above for Ar-47 to Ar-50, Ar-57, and Ar-58, where these structures may be substituted by one or more R 2< radicals instead of R 1<.

[0066] Preferred substituents R, R a< , R b< , R c< and R d< are described below.

[0067] In a preferred embodiment of the invention, R, R a< , R b< , R c< are the same or different on each occurrence and are selected from the group consisting of H, D, F, CN, NO 2 , Si(R 1< ) 3 , B(OR 1< ) 2 , a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 1<, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1<.

[0068] In a further preferred embodiment of the invention, substituent R, R a< , R b< , R c< is the same or different on each occurrence and is selected from the group consisting of H, D, F, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 1<, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1<.

[0069] Furthermore, it can be provided that at least one substituent R, R a< , R b< , R c< is selected, identically or differently on each occurrence, from the group consisting of H, D, an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may be substituted by one or more radicals 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< either form a ring according to the structures of the formulas (RA-1) to (RA-12), (RA-1a) to (RA-4f) or (RB) or the substituent R, R a< , R b< , R c< is the same or different on each occurrence and is selected from the group consisting of H, D, an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 1<, or a group N(Ar') 2 .Particularly preferably, substituent R, R a< , R b< , R c< are the same or different on each occurrence and are selected from the group consisting of H or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, particularly preferably having 6 to 13 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1<.

[0070] Preferably, it can be provided that at least one substituent R, R a< , R b< , R c< 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, which can each be substituted by one or more radicals R 1<. Here, the term substituent means in particular that R, R a< , R b< , R c< are not H. Furthermore, the substituents R, R a< , R b< , R c< can be the same or different if two or more substituents are present which are selected from the aromatic or heteroaromatic group mentioned.

[0071] In a further embodiment, it can be provided that at least one substituent R, R a< , R b< , R c< is selected from o-biphenyl, o,o'-terphenyl, o,o',p-quaterphenyl, 4,6-diphenyl-pyrimidin-2-yl, 4,6-diphenyl-trianin-2-yl, naphthalene, phenanthrene, chrysene, spiro-bifluorene, triphenylene, anthracene, benzanthracene, fluorene and / or pyrene, which can each be substituted by one or more radicals R 1<. Spiro-bifluorene, o-biphenyl, o,o'-terphenyl, o,o',p-quaterphenyl, 4,6-diphenyl-pyrimidin-2-yl, 4,6-diphenyl-trianin-2yl radicals are preferred here. The substituents R, R a< , R b< , R c< may be the same or different if two or more substituents are present which are selected from the aromatic group mentioned.

[0072] Structures / compounds with a group selected from o-biphenyl, o,o'-terphenyl, o,o',p-quaterphenyl, 4,6-diphenyl-pyrimidin-2-yl, 4,6-diphenyl-trianin-2-yl, naphthalene, phenanthrene, chrysene, spiro-bifluorene, triphenylene, anthracene, benzanthracene, fluorene and / or pyrene are particularly suitable for use as electron transport material and / or as matrix material.

[0073] In a preferred embodiment of the invention, R d< is the same or different on each occurrence and is selected from the group consisting of a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 1<, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2<.

[0074] In a further preferred embodiment of the invention, R d< is the same or different on each occurrence and is selected from the group consisting of a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 2<, an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 2<.Particularly preferably, R d< is selected, identically or differently on each occurrence, from the group consisting of a straight-chain alkyl group having 1 to 5 C atoms or a branched or cyclic alkyl group having 3 to 5 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 2< or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, particularly preferably having 6 to 13 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2<.

[0075] In a preferred embodiment of the invention, R d< is selected, identically or differently at each occurrence, from the group consisting of a straight-chain alkyl group having 1 to 6 C atoms or a cyclic alkyl group having 3 to 6 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 2<, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2<; two radicals R d< may also form a ring system with one another.Particularly preferably, R d< is selected, identically or differently at each occurrence, from the group consisting of a straight-chain alkyl group having 1, 2, 3 or 4 C atoms or a branched or cyclic alkyl group having 3 to 6 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 2<, but is preferably unsubstituted, or an aromatic ring system having 6 to 12 aromatic ring atoms, in particular having 6 aromatic ring atoms, which may in each case be substituted by one or more, preferably non-aromatic radicals R 2<, but is preferably unsubstituted; two radicals R d< can form a ring system with one another. Very particularly preferably, R d< is selected, identically or differently at each occurrence, from the group consisting of a straight-chain alkyl group having 1, 2, 3 or 4 C atoms, or a branched alkyl group having 3 to 6 C atoms.Most preferably, R d< represents a methyl group or a phenyl group, where two phenyl groups together can form a ring system, with a methyl group being preferred over a phenyl group.

[0076] Preferred aromatic or heteroaromatic ring systems for which substituents R, R a< , R b< , R c< or 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 1-, 2-, 3- or 4-position, Dibenzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline,Phenanthrene or triphenylene, which may each be substituted by one or more radicals R, R 1< or R 2<. The structures Ar-1 to Ar-78 listed above are particularly preferred, with structures of the formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16), (Ar-69), (Ar-70), (Ar-75) being preferred and structures of the formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16) being particularly preferred. With regard to the structures Ar-1 to Ar-78, it should be noted that these are represented with a substituent R 1<. In the case of the ring systems Ar, these substituents R 1< are to be replaced by R and in the case of R c< these substituents R 1< are to be replaced by R 2<.

[0077] Further suitable groups R, R a< , R b< , R c< are groups of the formula -Ar 4< -N(Ar 2< )(Ar 3< ), where Ar 2< , Ar 3< and Ar 4<, identical or different on each occurrence, represent an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, each of which may be substituted by one or more radicals R 1<. The total number of aromatic ring atoms of Ar 2< , Ar 3< and Ar 4< is a maximum of 60 and preferably a maximum of 40.

[0078] Ar 4< and Ar 2< can be linked to one another and / or Ar 2< and Ar 3< can also be linked to one another by a group selected from C(R 1< ) 2 , NR 1< , O, or S. Preferably, Ar 4< and Ar 2< are linked to one another, or Ar 2< and Ar 3< are linked to one another, in each case ortho to the position of the linkage to the nitrogen atom. In a further embodiment of the invention, none of the groups Ar 2< , Ar 3<, or Ar 4< are linked to one another.

[0079] Preferably, Ar 4< is an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 12 aromatic ring atoms, each of which may be substituted by one or more R 1< radicals. Ar 4< is particularly preferably selected from the group consisting of ortho-, meta-, or para-phenylene or ortho-, meta-, or para-biphenyl, each of which may be substituted by one or more R 1< radicals, but is preferably unsubstituted. Most preferably, Ar 4< is an unsubstituted phenylene group.

[0080] Preferably, Ar 2< and Ar 3<, identical or different on each occurrence, are an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each of which may be substituted by one or more radicals R 1<. Particularly preferred groups Ar 2< and Ar 3< are, identically or differently at each occurrence, selected 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 by one or more radicals R 1<.Very particularly preferably, Ar 2< and Ar 3< are selected, identically or differently on each occurrence, 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-spirobifluorene.

[0081] In a further preferred embodiment of the invention, R 1< is selected, identically or differently on each occurrence, from the group consisting of H, D, F, CN, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 2<, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2<.In a particularly preferred embodiment of the invention, R 1< is selected, identically or differently on each occurrence, from the group consisting of H, a straight-chain alkyl group having 1 to 6 C atoms, in particular having 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group having 3 to 6 C atoms, where the alkyl group may be substituted by one or more radicals R 5<, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 6 to 13 aromatic ring atoms, each of which may be substituted by one or more radicals R 5<, but is preferably unsubstituted.

[0082] In a further preferred embodiment of the invention, R 2< is identical or different on each occurrence and is H, an alkyl group having 1 to 4 C atoms or an aryl group having 6 to 10 C atoms, which may be substituted by an alkyl group having 1 to 4 C atoms, but is preferably unsubstituted.

[0083] In compounds according to the invention that are processed by vacuum evaporation, the alkyl groups preferably have no more than five carbon atoms, more preferably no more than four carbon atoms, and most preferably no more than one carbon atom. For compounds that are processed from solution, compounds substituted by alkyl groups, especially branched alkyl groups, with up to 10 carbon atoms, or substituted by oligoarylene groups, for example ortho-, meta-, para-, or branched terphenyl or quaterphenyl groups, are also suitable.

[0084] Furthermore, it can be provided that the compound comprises exactly two or exactly three structures according to formulas (I), (II-1) to (II-6), (III-1) to (III-42), (IV-1) to (IV-53), (V-1) to (V-52) and / or (VI-1) to (VI-64), (VII-1) to (VII-13) and / or (VIII-1) to (VIII-13).

[0085] In a preferred embodiment, the compounds are selected from compounds of formula (D-1), where the group L' represents a linking group, preferably a bond or an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 1<, and the other symbols used have the meanings given above, in particular for formula (I).

[0086] In a further preferred embodiment of the invention, L 1< represents a bond or an aromatic or heteroaromatic ring system having 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system having 6 to 12 carbon atoms, which may be substituted by one or more radicals R 1<, but is preferably unsubstituted, where R 1< may have the meaning given above, in particular for formula (I). More preferably, L' represents an aromatic ring system having 6 to 10 aromatic ring atoms or a heteroaromatic ring system having 6 to 13 heteroaromatic ring atoms, each of which may be substituted by one or more radicals R 2<, but is preferably unsubstituted, where R 2< may have the meaning given above, in particular for formula (I).

[0087] Furthermore, the symbol L' shown inter alia in formula (D1) is preferably identical or different on each occurrence and represents a bond or an aryl or heteroaryl radical having 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 ring atoms, so that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is bonded directly, ie via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group.

[0088] Furthermore, it can be provided that the group L 1< shown in formula (D1) comprises an aromatic ring system with at most four, preferably at most three, particularly preferably 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.

[0089] Particularly preferred are structures that do not exhibit condensation, such as phenyl, biphenyl, terphenyl and / or quaterphenyl structures.

[0090] Examples of suitable aromatic or heteroaromatic ring systems L 1< are selected from the group consisting of ortho-, meta- or para-phenylene, ortho-, meta- or para-biphenylene, terphenylene, in particular branched terphenylene, quaterphenylene, in particular branched quaterphenylene, fluorenylene, spirobifluorenylene, dibenzofuranylene, dibenzothienylene and carbazolylene, which may each be substituted by one or more radicals R 1<, but are preferably unsubstituted.

[0091] The above-mentioned preferred embodiments can be combined with each other as desired within the limitations defined in claim 1. In a particularly preferred embodiment of the invention, the above-mentioned advantages occur simultaneously.

[0092] Examples of preferred compounds according to the embodiments listed above are the compounds listed in the following table: 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 36 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90

[0093] Preferred embodiments of compounds according to the invention are explained in more detail in the examples, whereby these compounds can be used alone or in combination with others for all purposes according to the invention.

[0094] Provided that the conditions stated in claim 1 are met, the above-mentioned preferred embodiments can be combined with one another in any way. In a particularly preferred embodiment of the invention, the above-mentioned preferred embodiments apply simultaneously.

[0095] The compounds of the invention can, in principle, be prepared by various methods. However, the methods described below have proven particularly suitable.

[0096] Therefore, a further subject of the present invention is a process for preparing the compounds according to the invention, in which a basic skeleton with at least one of the groups Z b< or a precursor of one of the groups Z b< is synthesized and an aromatic or heteroaromatic radical is introduced by means of a nucleophilic aromatic substitution reaction or a coupling reaction.

[0097] Suitable compounds comprising a basic skeleton with a group Z b< can often be obtained commercially, the starting compounds presented in the examples being obtainable by known processes, so that reference is made thereto.

[0098] These compounds can be reacted with other compounds by known coupling reactions, the necessary conditions for this being known to the person skilled in the art and detailed information in the examples assisting the person skilled in the art in carrying out these reactions.

[0099] Particularly suitable and preferred coupling reactions, all of which lead to CC and / or CN bond formations, are those according to BUCHWALD, SUZUKI, YAMAMOTO, STILLE, HECK, NEGISHI, SONOGASHIRA, and HIYAMA. These reactions are widely known, and the examples provide further guidance to the skilled person.

[0100] The compounds of the invention can be prepared, inter alia, according to Schemes 1 and 2. Scheme 1 illustrates, in particular, the preparation of compounds of the invention starting from meta-aryl / heteroaryl-Y-substituted anilines (1). These are first converted into the analogous phenylhydrazines by diazotization and in situ reduction of the diazonium salt with tin in hydrochloric acid, e.g., according to A. Minkkilä et al., ChemMedChem 2009, 4, 1253.

[0101] The phenylhydrazines can be converted into symmetric 1,1-diarylhydrazines after protection of the primary amino function with Boc in a Cu-catalyzed homocoupling and subsequent deprotection, e.g., according to J.-Q. Zhang et al., Org. Biomol. Chem., 2015, 13.

[0102] Unsymmetrical 1,1-diphenylhydrazines can be obtained by Cu-catalyzed coupling of phenylhydrazines with corresponding boronic acids followed by deprotection, also according to J.-Q. Zhang et al., Org. Biomol. Chem., 2015, 13. In Scheme 1, the symbols R' and Y' are shown for unsymmetrical compounds instead of the sketchy symbols Y and R.

[0103] The symmetrical and unsymmetrical 1,1-diphenylhydrazines can be converted into the corresponding bistrimethylaminostannanes using diethylaminotrimethylstannane, e.g., according to K. Jones et al., J. Chem. Soc., 1965, 1944. Subsequent transmetalation with boron trichloride yields the bisdichloroaminoboranes, e.g., according to S. Diemer et al., Eur. J. Inorg. Chem. 1999, 1765. These can be cyclized in the presence of the Lewis acid aluminum(III) chloride and the base 2,2,6,6-tetramethylpiperidine in o-dichlorobenzene at 150 °C to give the compounds of the invention.

[0104] Scheme 2 depicts a synthesis route without the Y 2< group, which is provided as a general synthesis route. Starting from 1,1-diphenylhydrazines in 1,2-dichlorobenzene, the corresponding bis-boronic acid esters can be prepared according to US 2017 / 018721 by adding BBr 3 and subsequent alcoholysis with i-PrOH.

[0105] The compounds according to the invention can be prepared analogously to WO 2020 / 208051 A1 by reacting them with a diorganolithium compound. In Scheme 2, an aryl group with two aromatic nuclei is explicitly used in step 2. Of course, compounds that do not have two aromatic nuclei connected via a bond, as shown in Scheme 2, can also be used in this step. For example, di-lithio compounds of a simple aromatic system, such as 1,2-di-lithiobenzene, or di-lithio compounds of a larger aromatic system, such as 1,8-di-lithionaphthalene, 4,5-di-lithiofluorene, 4,5-di-lithiocarbazole, 1,9-di-lithiodibenzofuran, 1,7-dilithiobenzimidazole, etc., can also be used. Furthermore, mono-lithium compounds can also be used in appropriate amounts.

[0106] The meaning of the symbols used in Schemes 1 and 2 essentially corresponds to that defined for formula (I) or preferred embodiments of these structures, although numbering and a complete representation of all symbols have been omitted for reasons of clarity. Furthermore, for reasons of clarity, the use of symbols to represent possible nitrogen atoms in the heteroaromatic rings has often been omitted, as they are represented in particular in formulas (III-1) to (III-42) and / or (V-1) to (V-52) by the symbols X, X a< and X b<. These details are therefore to be understood as examples, and the person skilled in the art is able to transfer the syntheses presented above and below, in particular in the examples, to compounds in which one or more of the symbols X, X a< and X b< stand for nitrogen.

[0107] The principles of the preparation processes described above are, in principle, known from the literature for similar compounds and can be easily adapted by those skilled in the art to prepare the compounds of the invention. Further information can be found in the examples.

[0108] By these processes, 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).

[0109] 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 by reactive leaving groups, such as bromine, iodine, chlorine, boronic acid, or boronic acid esters, or by reactive, polymerizable groups, such as olefins or oxetanes. These can be used as monomers to produce corresponding oligomers, dendrimers, or polymers. The oligomerization or polymerization preferably takes place via the halogen functionality or the boronic acid functionality, or via the polymerizable group, respectively. 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.

[0110] The invention therefore further provides oligomers, polymers or dendrimers comprising one or more of the above-listed structures of the formula (I) and preferred embodiments of this formula or compounds according to the invention, wherein one or more bonds of the compounds according to the invention or of the structures of the formula (I) and preferred embodiments of this formula to the polymer, oligomer or dendrimer are present. Depending on the linkage of the structures of the 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 as described above apply to the repeating units of the compounds according to the invention in oligomers, dendrimers and polymers.

[0111] To prepare the oligomers or polymers, the monomers according to the invention are homopolymerized or copolymerized with other 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%, particularly preferably 20 to 80 mol%. Suitable and preferred comonomers which form 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.

[0112] Of particular interest are also compounds according to the invention that are characterized by a high glass transition temperature. In this context, particular preference is given to compounds according to the invention 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, more preferably of at least 110°C, most preferably of at least 125°C, and especially preferably of at least 150°C, determined according to DIN 51005 (version 2005-08).

[0113] For processing the compounds of the invention from the liquid phase, for example by spin coating or printing processes, formulations of the compounds of the invention are required. These formulations can be, for example, solutions, dispersions, or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butylbenzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, Decalin, dodecylbenzene, ethyl benzoate, indane, NMP, p-cymene, phenetol,1,4-Diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, 2-methylbiphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, diethyl sebacate, octyl octanoate, heptylbenzene, menthyl isovalerate, cyclohexylhexanoate or mixtures of these solvents.

[0114] A further subject of the present invention is therefore a formulation or a composition comprising at least one compound according to the invention and at least one further compound.

[0115] The further compound can, for example, be a solvent, in particular one of the above-mentioned solvents or a mixture of these solvents. If the further compound comprises a solvent, this mixture is referred to herein as a formulation. However, the further compound can also be at least one further organic or inorganic compound that is also used in the electronic device, for example an emitter and / or a matrix material, wherein these compounds differ from the compounds according to the invention. Suitable emitters and matrix materials are listed below in connection with the organic electroluminescent device. The further compound can also be polymeric.

[0116] The present invention therefore further provides a composition comprising a compound according to the invention and at least one further organic functional material. Functional materials are generally the organic or inorganic materials introduced between the anode and cathode. The organic functional material is preferably 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-conductor materials, hole-injection materials, electron-blocking materials, hole-blocking materials, wide-band-gap materials, and n-dopants.

[0117] The present invention further provides for 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. Compounds according to the invention preferably exhibit fluorescent properties and thus preferably provide fluorescent emitters.

[0118] Preferably, it can be provided that structures / compounds according to formulas (V-22) to (V-52) and / or (VI-22) to (VI-64) are used as emitters.

[0119] Furthermore, compounds of formula (I) or an oligomer, polymer, or dendrimer comprising structures of formula (I) can be used as host materials and / or electron-transport materials. Preferably, it can be provided that structures / compounds with an anthracene group (Ar-76) to (Ar-78), preferably (Ar-78), and / or structures / compounds of formulas (V-17) to (V-21) and / or (VI-17) to (VI-21), preferably (V-17) to (V-20) and / or (VI-17) to (VI-20) are used as electron-transport material and / or matrix material.

[0120] The present invention further relates to 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 that contains at least one layer containing at least one organic compound. The component may also contain inorganic materials or layers composed entirely of inorganic materials.

[0121] The electronic device is preferably selected from the group consisting of Particularly preferred electronic device is selected from the group consisting of organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes based on small molecules (sOLEDs), organic light-emitting diodes based on polymers (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), organic light-emitting diodes based on small molecules (sOLEDs), organic light-emitting diodes based on polymers (PLEDs), in particular phosphorescent OLEDs.

[0122] 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, for example, one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, exciton-blocking layers, electron-blocking layers, and / or charge-generation layers. Interlayers, which, for example, have an exciton-blocking function, may also be inserted between two emitting layers. It should be noted, however, that not all of these layers are necessarily present. The organic electroluminescent device may contain one emitting layer or it may contain multiple emitting layers.If multiple emission layers are present, they preferably have a total of multiple emission maxima between 380 nm and 750 nm, resulting in overall white emission. This means that different emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. Systems with three emitting layers are particularly preferred, with the three layers exhibiting blue, green, and orange or red emission. The organic electroluminescent device according to the invention can also be a tandem electroluminescent device, particularly for white-emitting OLEDs.

[0123] The compound according to the invention can be used in different layers, depending on the precise structure. Preference is given to an organic electroluminescent device comprising a structure / compound according to formula (I) or the preferred embodiments outlined above in an emitting layer as an emitter, preferably a red, green, or blue emitter. Very preferred is an organic electroluminescent device comprising a structure / compound according to formula (I) or the preferred embodiments outlined above in an emitting layer as a fluorescent blue emitter. In this case, compounds structures / compounds according to formulas (V-22) to (V-52) and / or (VI-22) to (VI-64) are particularly preferred and structures / compounds of the formulas (V-23) to (V-25), (V-27), (V-28), (V-32), (V-36), (V-37), (V-41) to (V-44), (V-47), (V-48), (V-51), (V-52) and / or (VI-23) to (VI-64) are particularly preferred.

[0124] When the compound according to the invention is used as an emitter in an emitting layer, a suitable matrix material (also called host material) is preferably used, which is known as such.

[0125] 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.%, in particular between 95 and 80 vol.% of matrix material, based on the total mixture of emitter and matrix material. Accordingly, the mixture contains between 1 and 99 vol.%, preferably between 2 and 90 vol.%, particularly preferably between 3 and 40 vol.%, in particular between 5 and 20 vol.% of the emitter, based on the total mixture of emitter and matrix material.

[0126] Suitable matrix materials which 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. B. according to WO 2010 / 136109, WO 2011 / 000455, WO 2013 / 041176 or WO 2013 / 056776, azacarbazole derivatives, e.g. B. according to EP 1617710, EP 1617711, EP 1731584, JP 2005 / 347160, bipolar matrix materials, e.g. B. according to WO 2007 / 137725, silanes, e.g. B. according to WO 2005 / 111172, azaboroles or boronic esters, e.g. B. according to WO 2006 / 117052, triazine derivatives, e.g.according to WO 2007 / 063754, WO 2008 / 056746, WO 2010 / 015306, WO 2011 / 057706, WO 2011 / 060859 or WO 2011 / 060877, zinc complexes, e.g. according to EP 652273 or WO 2009 / 062578, diazasilole or tetraazasilole derivatives, e.g. according to WO 2010 / 054729, diazaphosphole derivatives, e.g. according to WO 2010 / 054730, bridged carbazole derivatives, e.g. B. according to WO 2011 / 042107, WO 2011 / 060867, WO 2011 / 088877 and WO 2012 / 143080, triphenylene derivatives, e.g. B. according to WO 2012 / 048781, dibenzofuran derivatives, e.g. B. according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO 2017 / 148565 or biscarbazoles, e.g. B. according to JP 3139321 B2.

[0127] Furthermore, a compound that does not participate, or does not participate to a significant extent, in charge transport can be used as a co-host, as described, for example, in WO 2010 / 108579. Particularly suitable co-matrix materials in combination with the compound according to the invention are compounds that have a large band gap and do not participate, or at least do not participate to a significant extent, in the charge transport of the emitting layer. Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009 / 124627 or WO 2010 / 006680.

[0128] In a preferred embodiment, a compound containing a structure / compound according to formula (I) or the preferred embodiments described above, 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. This preferably forms a hyperfluorescence system as described in WO 2012 / 133188 and / or a hyperphosphorescence system as described in US 2017271611. This combination represents a preferred composition according to the present invention.

[0129] WO 2015 / 091716 A1 and WO 2016 / 193243 A1 disclose OLEDs containing both a phosphorescent compound and a fluorescent emitter in the emission layer, with the energy being transferred from the phosphorescent compound to the fluorescent emitter (hyperphosphorescence). In this context, the phosphorescent compound therefore behaves like a host material. As those skilled in the art know, host materials have higher singlet and triplet energies than the emitters, so that the energy of the host material is transferred to the emitter as optimally as possible. The systems disclosed in the prior art exhibit precisely such an energy relationship.

[0130] For the purposes of this invention, phosphorescence refers to luminescence from an excited state with 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 considered phosphorescent compounds.

[0131] Particularly suitable phosphorescent compounds (= triplet emitters) are compounds that emit light upon suitable excitation, preferably in the visible range, and also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80, in particular a metal with this atomic number. Compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are preferably used as phosphorescent emitters, in particular compounds containing iridium or platinum.

[0132] Examples of the emitters described above can be found in the applications WO 00 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 05 / 033244, WO 05 / 019373, US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, WO 2010 / 102709, WO 2011 / 032626, WO 2011 / 066898, WO 2011 / 157339, WO 2012 / 007086, WO 2014 / 008982, WO 2014 / 023377, WO 2014 / 094961, WO 2014 / 094960, WO 2015 / 036074, WO 2015 / 104045, WO 2015 / 117718, WO 2016 / 015815, WO 2016 / 124304, WO 2017 / 032439, WO 2018 / 011186, WO 2018 / 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 according to the prior art for phosphorescent electroluminescent devices and as known to the person skilled in the art in the field of organic electroluminescence are suitable, and the person skilled in the art can use further phosphorescent complexes without inventive step.

[0133] 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.

[0134] 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 comparatively small singlet-triplet separation ΔE(S 1 - T 1 ) of, for example, less than about 2000 cm -1 is required in the emitter. To open the inherently spin-forbidden transition T 1 → S 1 , another compound can be provided in the matrix next to the emitter. This compound exhibits strong spin-orbit coupling, enabling inter-system crossing through 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.

[0135] Further valuable information on hyperfluorescence systems is provided in WO2012 / 133188 (Idemitsu), WO2015 / 022974 (Kyushu Univ.), WO2015 / 098975 (Idemitsu), WO2020 / 053150 (Merck) and DE202019005189 (Merck), among others.

[0136] Further valuable information on hyperphosphorescence systems is provided, among others, 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).

[0137] 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 directly adjoins the hole-injection layer or the anode, and / or the emitting layer directly adjoins 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 the same as or similar to the metal complex in the emitting layer as a hole-transport or hole-injection material directly adjacent to the emitting layer, as described, for example, in WO 2009 / 030981.

[0138] Furthermore, an organic electroluminescent device is preferred, comprising a structure / compound according to formula (I) or the preferred embodiments described above in an electron-conducting layer as electron-transport material. In particular, compounds containing an anthracene group, preferably a group according to formulas (Ar-76) to (Ar-78), preferably (Ar-78), and / or structures / compounds according to formulas (V-17) to (V-21) and / or (VI-17) to (VI-21), preferably (V-17) to (V-20) and / or (VI-17) to (VI-20) are used.

[0139] In the further layers of the organic electroluminescent device according to the invention, all materials commonly used in the prior art can be used. Therefore, the skilled person can, without inventive step, use all materials known for organic electroluminescent devices in combination with the structure / compound according to formula (I) or the preferred embodiments described above.

[0140] Also preferred is an organic electroluminescent device characterized in that one or more layers are coated using a sublimation process. The materials are vapor-deposited in vacuum sublimation systems at an initial pressure of less than 10 -5 mbar, preferably less than 10 -6 mbar. However, it is also possible for the initial pressure to be even lower, for example, less than 10 -7 mbar.

[0141] Also preferred is an organic electroluminescent device, characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or by means of carrier gas sublimation. The materials are applied at a pressure between 10 -5 mbar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus patterned.

[0142] Also preferred is an organic electroluminescent device characterized in that one or more layers are produced from solution, such as by spin coating, or by any printing process, such as screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), inkjet printing, or nozzle printing. Soluble compounds are required for this, which are obtained, for example, by suitable substitution.

[0143] Formulations for applying a compound according to formula (I) or the preferred embodiments thereof set out above are novel. A further subject of the present invention is therefore a formulation comprising at least one solvent and a compound according to formula (I) or the preferred embodiments thereof set out above.

[0144] Furthermore, hybrid processes are possible, in which, for example, one or more layers are applied from solution and one or more further layers are vapor-deposited.

[0145] These processes are generally known to the person skilled in the art and can be applied by him without inventive step to organic electroluminescent devices containing the compounds according to the invention.

[0146] The compounds according to the invention and the organic electroluminescent devices according to the invention are distinguished from the prior art, in particular by an improved lifetime. The other electronic properties of the electroluminescent devices, such as efficiency or operating voltage, remain at least as good. In a further variant, the compounds according to the invention and the organic electroluminescent devices according to the invention are distinguished from the prior art, in particular by an improved efficiency and / or operating voltage and a longer lifetime.

[0147] The electronic devices according to the invention, in particular organic electroluminescent devices, are characterized by one or more of the following surprising advantages over the prior art: 1. Electronic devices, in particular organic electroluminescent devices comprising structures / compounds according to formula (I) or the preferred embodiments set out above and below as emitters, have very narrow emission bands with low FWHM (Full Width Half Maximum) values ​​and lead to particularly color-pure emission, as can be recognized by the small CIE y values. What is particularly surprising here is that both blue emitters with low FWHM values ​​and emitters with low FWHM values ​​are provided which emit in the green, yellow or red region of the color spectrum. 2. The structures / compounds according to formula (I) according to the invention or the preferred embodiments set out above and below display very high stability and lifetime. 3. With structures / 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. As a result, these devices are characterized by high PL and thus high EL efficiency of emitters and excellent energy transfer from the matrices to dopants. Exciton energy is typically transferred from a matrix or host in the emission layer to the emitter either via Dexter or Förster transfer. Förster energy transfer (FRET) from a host or matrix to the emitter according to the invention is particularly preferred because it is particularly efficient, leading to electronic devices with particularly good performance data (e.g., efficiency, voltage, and lifetime). It has been shown that energy transfer from a host or matrix to the compounds according to the invention preferably occurs via Förster transfer. In particular, triplet Dexter transfer from the host or the sensitizer to the emitter in hyperphosphorescent components can be effectively suppressed by the strong steric shielding of the emitters according to the invention through suitable substitution with aryl and / or alkyl groups, which leads to very good efficiencies in these components.

[0148] These advantages mentioned above are not accompanied by an excessive deterioration of the other electronic properties.

[0149] It should be noted that variations of the embodiments described in the present invention fall within the scope of this invention. Any feature disclosed in the present invention may, unless explicitly excluded, be replaced by alternative features serving the same, equivalent, or similar purpose. Thus, unless otherwise stated, any feature disclosed in the present invention is to be considered an example of a generic series or an equivalent or similar feature.

[0150] All features of the present invention may be combined with each other in any way, unless certain features and / or steps are mutually exclusive. This applies in particular to preferred features of the present invention. Likewise, features of non-essential combinations may be used separately (and not in combination).

[0151] It should further be noted that many of the features, and particularly those of the preferred embodiments of the present invention, are inventive in their own right and should not be considered merely part of the embodiments of the present invention. Independent protection may be sought for these features in addition to or alternatively to any presently claimed invention.

[0152] The teaching of technical action disclosed in the present invention can be abstracted and combined with other examples.

[0153] The invention is further illustrated by the following examples, without intending to limit it. From these descriptions, one skilled in the art can practice the invention within the entire disclosed scope and, without inventive step, prepare further compounds according to the invention and use them in electronic devices or apply the method according to the invention. Examples:

[0154] Unless otherwise stated, the following syntheses were carried out under a protective gas atmosphere in dried solvents. Solvents and reagents can be purchased from Sigma-ALDRICH or ABCR, for example. The respective information in square brackets or the numbers given for individual compounds refer to the CAS numbers of the known compounds. For compounds that can exhibit multiple enantiomeric, diastereomeric, or tautomeric forms, one form is shown as a representative example. 1. Synthesis of synthons: Example S1:

[0155]

[0156] Implementation analogous to AA Mikhailine et al., Org. Lett. 2018, 20, 2301-2305.

[0157] Use of 32.1 g (100 mmol) of N-phenyl[1,1':3',1"-terphenyl]-2'-amine [1401351-39-0]. Yield: 27.5 g (67 mmol) 67%; purity approx. 95% according to 1< H-NMR.

[0158] The following connections can be represented analogously: e.g. reactants product yield S2 2648402-57-5 56 % S3 1401351-40-3 59 % S4 2432990-39-9 61 % S5 2570464-73-0 49 % S6 2591484-29-4 55 % S7 2410066-90-7 57 % S8 2648406-13-5 47 % S9 2031157-81-8 63 % S10 2387168-57-0 66 % S11 1180505-74-1 71 % S12 2648545-91-7 61 % S13 2583631-83-6 55 % S14 2648147-43-5 57 % S15 2648401-61-8 59 % S16 2647492-78-0 64 % S17 1989638-57-4 60 % S18 2468082-60-0 62 % S19 2648402-91-7 67 % S20 2648545-71-3 62 % S21 Synthesis according to WO2017056052 from 1049127-52-7 and 1369161-12-5 only level 2 & 3 60 % S22 Synthesis according to WO2017056052 from 4857-06-1 and 1369161-12-5 only level 2 & 3 59 % S23 Synthesis according to WO2017056052 from 112485-93-5 and 1369161-12-5 only level 2 & 3 63 % S24 Synthesis according to WO2017056052 from 1342904-06-6 and 1369161-12-5 only level 2 & 3 48 % S25 Synthesis according to WO2017056052 from 933747-50-3 and 1369161-12-5 only level 2 & 3 50 % S26 Synthesis according to WO2017056052 from 86604-94-6 and 1369161-12-5 only level 2 & 3 52 %

[0159] Procedure analogous to A. Minkkilä et al., ChemMedChem 2009, 4, 1253. 21.3 g (100 mmol) of 3-(2,4-dimethylphenoxy)aniline [1512169-66-2] was used. Yield: 17.9 g (78 mmol) 78%; Purity: approximately 97% by 1< H NMR.

[0160] The following connections can be represented analogously: e.g. reactants product yield S101 887579-72-8 80 % S102 887579-79-5 77 % S103 1713781-27-1 73 % S104 1708328-08-8 75 % S105 1708859-34-0 70 % S106 1489252-59-6 68 % S107 1519341-65-1 72 % S108 1489253-19-1 71 % S109 1786434-59-0 77 % S110 114999-33-6 68 % S111 116724-06-2 65 % S112 186494-31-5 63 % S113 186494-32-6 60 % S114 S1 67 % S115 S2 64 % S116 S3 58 % S117 S4 62 % S118 S5 55 % S119 S6 58 % S120 S7 57 % S121 S8 47 % S122 S9 63 % S123 S10 77 % S124 S11 75 % S125 S12 65 % S126 S13 48 % S127 S14 51 % S128 S15 50 % S129 S16 47 % S130 S17 49 % S131 S18 50 % S132 S19 55 % S133 S20 49 % S134 S21 43 % S135 S22 47 % S136 S23 45 % S137 S24 49 % S138 S25 44 % S140 S26 41 % Example S200:

[0161]

[0162] Procedure analogous to J.-Q. Zhang et al., Org. Biomol. Chem., 2015, 13, 2055. 20.0 g (100 mmol) of (3-phenoxyphenyl)hydrazine [104997-24-2] was used. Yield: 12.1 g (33 mmol) 66%; Purity: approximately 97% by 1< H NMR.

[0163] The following connections can be represented analogously: e.g. reactants product yield S201 60 % 1895939-75-9 S202 S100 58 % S203 S101 60 % S204 S102 55 % S205 S103 53 % S206 S104 55 % S207 S105 57 % S208 S106 60 % S209 S107 61 % S210 S108 57 % S211 S109 65 % S212 S110 60 % S213 S111 55 % S214 S112 57 % S215 S113 54 % S216 S114 50 % S217 S115 53 % S218 S116 49 % S219 S117 52 % S220 S118 48 % S221 S119 51 % S222 S120 55 % S223 S121 54 % S224 S122 58 % S225 S123 52 % S226 S124 55 % S227 S125 54 % S228 S126 57 % S229 S127 60 % S230 S128 45 % S231 S129 57 % S232 S130 39 % S233 S131 40 % S234 S132 43 % S235 S133 35 % S236 S134 38 % S237 S135 41 % S238 S136 44 % S239 S137 35% S240 S138 33 % S241 S140 41 % Example S300:

[0164]

[0165] Procedure analogous to J.-Q. Zhang et al., Org. Biomol. Chem., 2015, 13, 2055. 20.0 g (100 mmol) of (3-phenoxyphenyl)hydrazine [104997-24-2] and 25.5 g (110 mmol) of (2-fluoro-5-phenoxyphenyl)boronic acid [1256355-01-7] were used. Yield: 26.3 g (68 mmol) 68%; Purity: approximately 97% by 1< H NMR.

[0166] The following connections can be represented analogously: e.g. reactants product yield S301 S120 63 % 221006-66-2 S302 S120 65 % 2568850-35-9 S303 S119 60 % 943899-12-5 S304 S110 63 % 180994-95-0 S305 S110 67 % 1292285-28-9 S306 S110 60 % 2415582-15-7 S307 S118 58 % 1648571-13-4 S308 S120 58 % 1914082-44-2 S309 2415582-15-7 61 % 1776936-42-5 S310 1292285-28-9 57 % 2334467-23-9 S311 S119 54 % 943899-12-5 S312 S119 50 % 2414505-75-0 S313 S120 51 % 2415917-91-6 S314 2415582-15-7 47 % 2681352-08-7 S315 S123 61 % 2415582-15-7 S316 S124 65 % 2415917-91-6 S317 S125 60 % 1292285-28-9 S318 S126 57 % 2334467-23-9 S319 S127 59 % 2415582-15-7 S320 S128 54 % 1776936-42-5 S321 S129 56 % 2415582-15-7 S322 S130 53 % 1292285-28-9 S323 S131 50 % 1292285-28-9 S324 S132 49 % 1292285-28-9 S325 S133 46 % 2415582-15-7 S326 S134 33 % 1776936-42-5 S327 S135 36 % 2415582-15-7 S328 S136 30 % 2415582-15-7 S329 S137 33 % 1292285-28-9 S330 S138 27 % 1292285-28-9 S331 S140 34 % 1776936-42-5 2. Synthesis of the compounds B according to the invention Example B1:

[0167] Level 1:

[0168] Procedure analogous to K. Jones et al., J. Chem. Soc., 1965, 1944. A solution of 3.68 g (10 mmol) of S200 in 50 ml of toluene, cooled to + 5 °C, is treated dropwise with 4.72 g (20 mmol) of N,N-diethylamino-1,1,1-trimethylstannane [1068-74-2]. The mixture is allowed to warm to room temperature, stirred for 12 h, and all volatiles are removed at 60 °C under vacuum (p ∼ 0.1 mbar). Level 2:

[0169] Procedure analogous to S. Diemer et al., Eur. J. Inorg. Chem. 1999, 1765. The residue from step 1 is taken up in 200 ml of dichloromethane (DCM), the solution is cooled to -78 °C, 20 ml (20 mmol) of boron trichloride, 1 N in n-heptane are slowly added dropwise with very good stirring, stirred for 1 h, then allowed to warm to room temperature, stirred for 16 h and all volatile components are removed at 60 °C in vacuum (p ∼ 0.01 mbar). Level 3:

[0170] The residue from step 2 is taken up in 300 ml of o-dichlorobenzene, 7.7 ml (45 mmol) of 2,2,6,6-tetramethylpiperidine and 16.0 g (120 mmol) of anhydrous aluminum trichloride are added, and the mixture is stirred at 150 °C for 20 h. After cooling, a mixture of 11.9 ml (120 mmol) of 1,4-diazabicyclo[2.2.2.]octane and 100 ml of o-dichlorobenzene is added dropwise, the mixture is stirred for 1 h, and the mixture is filtered through a bed of Celite pre-slurried with o-dichlorobenzene, washed with o-dichlorobenzene, and the filtrate is evaporated to dryness. Further purification is carried out by continuous hot extraction (common organic solvents or their combination, preferably DCM or acetonitrile / DCM 3:1 to 1:3) or by flash chromatography (CombiFlash Torrent column system from A. Semrau, silica gel, RP silica gels, aluminum oxide, eluent: toluene / n-heptane / triethylamine, acetonitrile / THF, or DCM) and subsequent fractional sublimation or annealing under high vacuum (typically T approx. 200-400 °C, p approx. 10 -5 < to 10 -6 < mbar). Yield: 886 mg (2nd3 mmol), 23%; purity: approx. 99.9% according to 1< H-NMR.

[0171] The following connections can be represented analogously: e.g. reactant product yield B2 S201 21% B3 S202 24 % B4 S203 20 % B5 S204 18 % B6 S205 12 % B7 S206 20 % B8 S207 25% B9 S208 24 % B10 S209 25 % B11 S210 13 % B12 S211 18 % B13 S212 20 % B14 S213 33 % B15 S214 30 % B16 S215 30 % B17 S216 34 % B18 S217 33 % B19 S218 29% B20 S219 31 % B21 S220 21 % B22 S221 33 % B23 S222 30 % B24 S223 16 % B25 S224 25 % B100 S300 20 % B101 S301 26 % B102 S302 17 % B103 S303 25% B104 S304 23 % B105 S305 20 % B106 S306 22 % B107 S307 21 % B108 S308 34 % B109 S309 17 % B110A S310 11 % B110B 8% B111 S311 34 % B112 S312 22 % B113 S313 18 % B114 S314 27 % B115 S315 23% B116 S316 26 % B117 S317 25% B118 S318 16 % B119 S319 27 % B120 S320 17 % B121 S321 23% B122 S322 14 % B123 S323 22 % B124 S324 19 % B125 S325 18 % B126 S326 17 % Use of 5 mmol B127 S327 21 % Use of 5 mmol B128 S328 19 % Use of 5 mmol B129 S329 7% Use of 5 mmol B130 S330 19 % Use of 5 mmol B131 S331 14 % Use of 5 mmol 3. Synthesis of the linked compound C1 according to the invention

[0172] Level 1:

[0173] Preparation of the boric acid ester. Procedure analogous to US201701872. A well-stirred solution of 5.0 g (27 mmol) of 1,1'-diphenylhydrazine [530-50-7] in 150 ml of 1,2-dichlorobenzene is added dropwise to 60 ml (60 mmol) of BBr 3 1M in DCM. The reaction mixture is heated using a water separator, the DCM is distilled off, and then stirred under reflux for 18 h. The mixture is then cooled to room temperature, and the volatile components are removed under reduced pressure. The residue is taken up in 200 ml of DCM, 100 ml of a mixture of i-PrOH and triethylamine (5:1 vv) is added dropwise while cooling with ice, and the mixture is stirred at room temperature for 5 h. The mixture is concentrated in vacuo to approximately 100 ml, the precipitated solid is filtered off, the residue is washed once with 20 ml of methanol and the mixture is dried in vacuo. Level 2:

[0174] Preparation of the compound according to the invention analogously to WO 2020 / 208051. The solid from step 1 is dissolved in 100 ml of THF, cooled to -78°C, and treated dropwise with 30 ml (30 mmol) of a 1 M 2,2'-lithiobiphenyl solution in THF (freshly prepared from 2,2'-dibromobiphenyl and n-BuLi in THF) over a period of 3 h. The mixture is then allowed to warm slowly to room temperature, and all volatile components are removed in vacuo. The residue is purified by column chromatography (CombiFlash Torrent automated column system from A. Semrau, silica gel, RP silica gel, alumina, eluent: methanol / THF, acetonitrile / THF, or DCM) and subsequent fractional sublimation or annealing under high vacuum (typically T approx. 200-400 °C, p approx. 10 -5 < to 10 -6 < mbar). Yield: 1.44 g (4.1 mmol), 19%.

[0175] The following connections can be represented analogously: e.g. reactant product yield C2 1802664-10-3 13 % C3 617707-29-6 15 % Example: Production of OLEDs 1) Vacuum-processed devices:

[0176] The production of OLEDs according to the invention as well as OLEDs according to the prior art is carried out according to a general process according to WO 2004 / 058911, which is adapted to the conditions described here (layer thickness variation, materials used).

[0177] The following examples present the results of various OLEDs. Cleaned glass plates (cleaned in a Miele laboratory dishwasher using Merck Extran cleaner) coated with 50 nm thick structured ITO (indium tin oxide) are pretreated with UV ozone for 25 minutes (UV ozone generator PR-100, UVP). Within 30 minutes, they are coated with 20 nm of PEDOT:PSS (poly(3,4-ethylenedioxythiophene)poly(styrenesulfonate), purchased as CLEVIOS™< P VP AI 4083 from Heraeus Precious Metals GmbH, Germany, spin-coated from aqueous solution) for improved processing. They are then baked at 180 °C for 10 minutes. These coated glass plates form the substrates onto which the OLEDs are applied. 1a) Blue and Green Fluorescence OLED Devices - BF and GF:

[0178] All materials are thermally evaporated in a vacuum chamber. The emission layer (EML) always consists of at least one matrix material (host material) SMB (see Table 1) and an emissive dopant (emitter) B, which is added to the matrix material(s) by co-evaporation in a specific volume fraction. A specification such as SMB:B (97:3%) means that the SMB material is present in the layer at a volume fraction of 97% and the dopant B at a volume fraction of 3%. Similarly, the electron transport layer can also consist of a mixture of two materials, see Table 1. The materials used to manufacture the OLEDs are shown in Table 5.

[0179] The OLEDs are characterized as standard. For this purpose, the electroluminescence spectra, current efficiency (measured in cd / A), power efficiency (measured in lm / W), and external quantum efficiency (EQE, measured in percent) are determined as a function of luminance, calculated from current-voltage-luminance (IUL) curves assuming a Lambertian radiation pattern, as well as the lifetime. The electroluminescence spectra are determined at a luminance of <1000 cd / m², and the color and full width half maximum (FWHM) are determined from these values. The OLEDs have the following layer structure: Substrat

[0180] 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, 140 nm. Hole transport layer 2 (HTL2) made of HTM2, 10 nm. Emission layer (EML), see Table 1. Electron transport layer (ETL2), see Table 1. Electron transport layer (ETL1), see Table 1. Electron injection layer (EIL) made of ETM2, 1 nm. Cathode made of aluminum, 100 nm. Table 1: Structure of blue and green fluorescent OLED components e.g. EML ETL2 ETL1 Ref-BF1 SMB1: Ref.-D1 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm BF1 SMB1: B1 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm BF2 SMB1: B2 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm BF3 SMB1: B3 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm BF4 SMB1: B7 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm BF5 SMB1: B12 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm BF6 SMB1:B14 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm BF7 SMB2:B17 (95:5%) ETM1 ETM1:ETM2 (50:50%) 20 nm 5 nm 30 nm BF8 SMB2:B21 (95:5%) ETM1 ETM1:ETM2 (50:50%) 20 nm 5 nm 30 nm BF9 SMB1:B100 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm BF10 SMB1:B101 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm BF11 SMB1:B102 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm BF12 SMB2:B103 (95:5%) ETM1 ETM1:ETM2 (50:50%) 20 nm 5 nm 30 nm BF13 SMB1:B104 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm BF14 SMB1:B109 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm BF15 SMB1:B114 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm BF16 SMB1:B130 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm BF17 SMB1:C1 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm BF18 SMB1:C2 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm BF19 SMB1:C3 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm GF1 SMB1:B9 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm GF2 SMB1:B13 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm GF3 SMB1:B105 (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm GF4 SMB2:B108 (95:5%) ETM1 ETM1:ETM2 (50:50%) 20 nm 5 nm 30 nm GF5 SMB1:B110B (97:3%) --- ETM1:ETM2 (50:50%) 20 nm 30 nm Table 2: Results of blue (420-499 nm) and green (500-540 nm) fluorescent OLED devices e.g. EQE [%] 1000 cd / m 2 Voltage [V] 1000 cd / m 2< Color FWHM [eV] Ref-BF1 6.6 4.4 blue 0.17 BF1 9.2 3.8 blue 0.15 BF2 8.3 3.7 blue 0.15 BF3 8.8 3.8 blue 0.15 BF4 8.0 3.9 deep blue 0.15 BF5 8.4 3.7 blue 0.16 BF6 8.7 3.5 blue 0.14 BF7 7.9 3.6 blue 0.15 BF8 8.5 3.5 blue 0.15 BF9 9.4 3.7 blue 0.15 BF10 9.0 3.6 blue 0.15 BF11 9.2 3.6 blue 0.16 BF12 8.4 3.8 blue 0.15 BF13 7.9 3.7 blue 0.17 BF14 9.6 3.6 blue 0.19 BF15 8.6 3.7 blue 0.19 BF16 8.2 3.8 deep blue 0.15 BF17 8.9 3.7 blue 0.17 BF18 8.5 3.6 blue 0.15 BF19 8.7 3.6 blue 0.16 GF1 10.2 3.4 green 0.17 GF2 9.9 3.4 green 0.17 GF3 9.7 3.4 green 0.16 GF4 9.4 3.3 green 0.15 GF5 10.5 3.4 green 0.14 1 b) Blue and green hyperphosphorescent OLED devices:

[0181] All materials are thermally evaporated 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 B. The sensitizer PS and fluorescent emitter B are mixed into the host material TMM by co-evaporation in a specific volume fraction. A specification such as TMM:PS(8%):B(1%) means that the TMM material is present in the layer at a volume fraction of 91%, PS at a fraction of 8%, and fluorescent emitter B at a fraction of 1%. Blue and Green Hyperphosphorescent OLED Devices BH:

[0182] The OLEDs basically have the following layer structure: Substrat

[0183] 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 and green hyperphosphorescent OLED components e.g. HTL2 EML ETL2 Ref-BH1 HTM3 TMM1:PS1 (8%):Ref.-D1 (1%) ETM3 10 nm 25 nm 10 nm BH1 HTM3 TMM1:PS1 (8%):B18 (1%) ETM3 10 nm 25 nm 10 nm BH2 HTM3 TMM1:PS1 (8%):B20 (1%) ETM3 10 nm 25 nm 10 nm BH3 HTM3 TMM1:PS1 (8%):B112 (1%) ETM3 10 nm 25 nm 10 nm GH1 HTM3 TMM1:PS2 (8%):B111 (2%) ETM3 10 nm 30 nm 10 nm Table 4: Results of blue and green hyperphosphorescent OLED devices e.g. EQE (%) 100 cd / m 2 Voltage (V) 100 cd / m 2< Color EL-FWHM [eV] Ref-BH1 17.0 4.0 blue 0.18 BH1 18.9 3.7 blue 0.20 BH2 17.7 3.7 blue 0.19 BH3 17.3 3.8 blue 0.17 GH1 15.3 3.7 green 0.16 Table 5: Structural formulas of the materials used HTM1 HTM2 136463-07-5 1450933-44-4 HTM3 TMM1 = ETM3 1206465-62-4 1201800-83-0 SMB1 SMB2 [1087346-88-0] [667940-34-3] [1805802-42-9] PS1 Ref.-D1 [1615218-73-9] PS2 ETM1 1541114-98-0 1233200-52-6 ETM2 25387-93-3

[0184] The abbreviations shown in Tables 1 and 3 with respect to the materials according to the invention, such as B1, B2, B3, B7, B9, B12, B13, B14, B17, B18, B20, B21, B100, B101, B102, B103, B104, B105, B108, B109, B110B, B111, B112, B114, B130, C1, C2 and C3 etc. refer to the compounds detailed in the synthesis examples above.

[0185] The compounds according to the invention have narrow electroluminescence spectra, which can be recognized by the lower EL-FWHM values ​​( EL electroluminescence - F ull W idth H alf M aximum - width of the EL emission spectra in eV at half peak height). Narrow electroluminescence spectra lead to significantly improved color purity (smaller CIE y values). In addition, very good EQE values ​​( E external Q uantes E efficiencies) at low operating voltages, which leads to significantly improved performance efficiencies of the device and thus to lower power consumption.

Claims

1. Compound comprising at least one structure of the formula (I) where the further symbols used are as follows: Za is the same or different at each instance and is Ra or Ara, where Ara is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more Ar or Ra radicals; at the same time, two Za radicals may form a ring system; Zb is the same or different at each instance and is Rb, Ar, or the Zb group together with the adjacent Zc group forms a ring Arb, where the ring Arb is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more Ar or Rb radicals, where the ring Arb together with the boron atom and the two nitrogen atoms forms a 5-membered ring; at the same time, the ring Arb may form a ring system together with a Za group or an Arb ring; Zc is the same or different at each instance and is Rc, Ar, or the Zc group together with the adjacent Zb group forms a ring Arb, where the ring Arb is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more Ar or Rb radicals, where the ring Arb together with the boron atom and the two nitrogen atoms forms a 5-membered ring; and the further symbols and indices used are as follows: Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R radicals; the Ar group here may form a ring system with at least one Ar, R, Ra, Rb, Rc group or a further group; R, Ra, Rb, Rc is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO2, N(Ar')2, N(R1)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, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may in each case be substituted by one or more R1 radicals, where one or more nonadjacent CH2 groups may be replaced by R1C=CR1, C≡C, Si(R1)2, C=O, C=S, C=Se, C=NR1, -C(=O)O-, -C(=O)NR1-, NR1, P(=O)(R1), -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R1 radicals; or heteroarylthio group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R1 radicals, or a diarylamino, arylheteroarylamino, diheteroarylamino group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R1 radicals, or an aralkyl or heteroarylalkyl group which has 5 to 60 aromatic ring atoms and 1 to 10 carbon atoms in the alkyl radical and may be substituted by one or more R1 radicals; at the same time, two R, Ra, Rb, Rc radicals together or with a further group may also form a ring system; Ar' is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R1 radicals; at the same time, it is possible for two Ar' radicals bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge 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, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by -R2C=CR2-, -C≡C-, Si(R2)2, C=O, C=S, C=Se, C=NR2, -C(=O)O-, -C(=O)NR2-, NR2, P(=O)(R2), -O-, -S-, SO or SO2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals, or a combination of these systems; at the same time, two or more R1 radicals together may form a ring system; at the same time, 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 which has 5 to 30 aromatic ring atoms and may be substituted by one or more R2 radicals; at the same time, it is possible for two Ar'' radicals bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge 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 hydrocarbyl radical having 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; at the same time, two or more substituents R2 together may form a ring system.

2. Compound according to Claim 1, comprising at least one structure of the formula (II-1) to (II-6): where the symbols Ra, Rb, Rc, Ara and Arb have the definitions given in Claim 1.

3. Compound according to Claim 1 or 2, comprising at least one structural element of the formulae (III-1) to (III-42): where dotted lines represent the bonds to the further structural elements of a compound of formulae (I) and / or (II-1) to (II-6), the symbols Ara and Ra have the definitions given in Claim 1 and the further symbols are as follows: X is the same or different at each instance and is N or CR, with the proviso that not more than three of the X groups in one cycle are N, where R has the definition detailed in Claim 1; Xa is the same or different at each instance and is N or CRa, with the proviso that not more than three of the Xa groups in one cycle are N, where Ra has the definition detailed in Claim 1; Xb is the same or different at each instance and is N or CRb, with the proviso that not more than three of the Xb groups in one cycle are N, where Rb has the definition detailed in Claim 1, Y1 is the same or different at each instance and is N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al(Ar), Al(R), Ga(Ar), Ga(R), C=O, C(R)2, Si(R)2, Ge(R)2, C=NR, C=NAr, C=C(R)2, C=C(R)(Ar), O, S, Se, S=O, or SO2, where R has the definition detailed in Claim 1; Y2 is the same or different at each instance and is a bond, N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al(Ar), Al(R), Ga(Ar), Ga(R), C=O, C(R)2, Si(R)2, Ge(R)2, C=NR, C=NAr, C=C(R)2, C=C(R)(Ar), O, S, Se, S=O, or SO2, where R has the definition detailed in Claim 1; Y3 is the same or different at each instance and is N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al(Ar), Al(R), Ga(Ar), Ga(R), C=O, C(R)2, Si(R)2, Ge(R)2, C=NR, C=NAr, C=C(R)2, C=C(R)(Ar), O, S, Se, S=O, or SO2, where R has the definition detailed in Claim 1; Y4 is the same or different at each instance and is a bond, N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al(Ar), Al(R), Ga(Ar), Ga(R), C=O, C(R)2, Si(R)2, Ge(R)2, C=NR, C=NAr, C=C(R)2, C=C(R)(Ar), O, S, Se, S=O, or SO2, where R has the definition detailed in Claim 1.

4. Compound according to one or more of Claims 1 to 3, comprising at least one structural element of the formulae (IV-1) to (IV-53): where dotted lines represent the bonds to the further structural elements of a compound of formulae (I) and / or (II-1) to (II-6), the symbols Ara, R, Ra und Rb have the definitions given in Claim 1, the symbols Y1, Y2, Y3 and Y4 have the definitions given in Claim 3, and the further symbols are as follows: l is 0, 1, 2, 3, 4 or 5; m is 0, 1, 2, 3 or 4; n is 0, 1, 2 or 3; j is 0, 1 or 2; k is 0 or 1.

5. Compound according to one or more of Claims 1 to 4, comprising at least one structure of the formula (V-1) to (V-52): where the symbols Ara and Ra have the definitions given in Claim 1 and the symbols X, Xa, Xb, Y1, Y2, Y3 and Y4 have the definitions given in Claim 3, and the further symbols are as follows: Y5 is the same or different at each instance and is N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al(Ar), Al(R), Ga(Ar), Ga(R), C=O, C(R)2, Si(R)2, Ge(R)2, C=NR, C=NAr, C=C(R)2, C=C(R)(Ar), O, S, Se, S=O, or SO2, where R has the definition detailed above, especially for formula (I).

6. Compound according to one or more of Claims 1 to 5, comprising at least one structure of the formula (VI-1) to (VI-64): where the symbols Ara, R, Ra and Rb have the definitions given in Claim 1, the symbols Y1, Y2, Y3 and Y4 have the definitions given in Claim 3, the symbol Y5 has the definition given in Claim 5, and the further symbols are as follows: l is 0, 1, 2, 3, 4 or 5; m is 0, 1, 2, 3 or 4; n is 0, 1, 2 or 3; j is 0, 1 or 2; k is 0 or 1.

7. Compound according to one or more of Claims 1 to 6, characterized in that at least two R, Ra, Rb, Rc radicals together with the further groups to which the two R, Ra, Rb, Rc radicals bind form a fused ring, where the two R, Ra, Rb, Rc radicals form at least one structure of the formulae (RA-1) to (RA-12): where R1 has the definition detailed above, the dotted bonds represent the sites of attachment to the atoms of the groups to which the two R, Ra, Rb, Rc radicals bind, and the further symbols are defined as follows: Y6 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; Rd is the same or different at each instance and is F, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may be substituted in each case by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by R2C=CR2, C≡C, Si(R2)2, C=O, C=S, C=Se, C=NR2, -C(=O)O-, -C(=O)NR2-, NR2, P(=O)(R1), -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals; at the same time, it is also possible for two Rd radicals together or one Rd radical together with an R1 radical or together with a further group to form a ring system; s is 0, 1, 2, 3, 4, 5 or 6; t is 0, 1, 2, 3, 4, 5, 6, 7 or 8; v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

8. Compound according to one or more of Claims 1 to 7, characterized in that at least two R, Ra, Rb, Rc radicals together with the further groups to which the two R, Ra, Rb, Rc radicals bind form a fused ring, where the two R, Ra, Rb, Rc radicals form structures of the formula (RB), where R1 has the definition detailed in Claim 1, the dotted bonds represent the sites of attachment to the atoms of the groups to which the two R, Ra, Rb, Rc radicals bind, the index m is 0, 1, 2, 3 or 4 and Y7 is C(R1)2, NR1, NAr', BR1, BAr', O or S.

9. Compound according to one or more of Claims 1 to 8, comprising at least one structure of the formulae (VII-1) to (VII-13), where the compounds have at least one fused ring: where the symbols Ra, Rb, Y2 and Y3 have the definitions given in Claim 1 or Claim 3, the symbol o represents the sites of attachment, and the further symbols have the following definition: m is 0, 1, 2, 3 or 4; n is 0, 1, 2 or 3; j is 0, 1 or 2; k is 0 or 1.

10. Compound according to one or more of Claims 1 to 9, characterized in that at least one substituent R, Ra, Rb, Rc is the same or different at each instance and is selected from the group consisting of H, D, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms or an aromatic or heteroaromatic ring system selected from the groups of the following formulae Ar-1 to Ar-78: where R1 has the definitions given above, the dotted bond represents the bond to the corresponding group and in addition: Ar1 is the same or different at each instance and is a bivalent aromatic or heteroaromatic ring system which has 6 to 18 aromatic ring atoms and may be substituted in each case by one or more R1 radicals; A is the same or different at each instance and is C(R1)2, NR1, O or S; p is 0 or 1, where p = 0 means that the Ar1 group is absent and that the corresponding aromatic or heteroaromatic group is bonded directly to the corresponding radical; q is 0 or 1, where q = 0 means that no A group is bonded at this position and R1 radicals are bonded to the corresponding carbon atoms instead.

11. Compound according to at least one of the preceding Claims 1 to 10, characterized in that the compound comprises exactly two or exactly three structures of formula (I), (II-1) to (II-6), (III-1) to (III-42), (IV-1) to (IV-53), (V-1) to (V-52) and / or (VI-1) to (VI-64) and / or (VII-1) to (VII-13).

12. Oligomer, polymer or dendrimer containing one or more compounds according to any of Claims 1 to 10, wherein, in place of a hydrogen atom or a substituent, there are one or more bonds of the compounds to the polymer, oligomer or dendrimer.

13. Formulation comprising at least one compound according to one or more of Claims 1 to 11 or an oligomer, polymer or dendrimer according to Claim 12 and at least one further compound, where the further compound is preferably selected from one or more solvents.

14. Composition comprising at least one compound according to one or more of Claims 1 to 11 or an oligomer, polymer or dendrimer according to Claim 12 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters that exhibit TADF, host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocker materials and hole blocker materials.

15. Process for preparing a compound according to one or more of Claims 1 to 11, characterized in that a base skeleton having at least one of the Zb groups or a precursor of one of the Zb groups is synthesized, and an aromatic or heteroaromatic radical is introduced by means of a nucleophilic aromatic substitution reaction or a coupling reaction.

16. Use of a compound according to one or more of Claims 1 to 11 or an oligomer, polymer or dendrimer according to Claim 12 in an electronic device.

17. Electronic device comprising at least one compound according to one or more of Claims 1 to 11 or an oligomer, polymer or dendrimer according to Claim 12.