MATERIALS FOR ELECTRONIC DEVICES

Description

[0001] The present invention relates to compounds, compositions, formulations and electronic devices containing the compounds or compositions.

[0002] The construction of organic electroluminescent devices (e.g., OLEDs - organic light-emitting diodes or OLECs - organic light-emitting electrochemical cells), in which organic semiconductors are used as organic functional materials, is described, for example, in US 4,539,507, US 5,151,629, EP 0676461, and WO 98 / 27136. In addition to fluorescent emitters, organometallic complexes that exhibit phosphorescence are increasingly being used as emitting materials (MA Baldo et al., Appl. Phys. Lett. 1999, 75, 4-6). For quantum mechanical reasons, up to four times the energy and power efficiency is possible using organometallic compounds as phosphorescence emitters. In general, there is still room for improvement, both for OLEDs that exhibit singlet emission and for OLEDs that exhibit triplet emission, particularly with regard to efficiency, operating voltage, and lifetime.

[0003] The properties of organic electroluminescent devices are not only determined by the emitters used. The other materials used, such as host and matrix materials, hole-blocking materials, electron-transport materials, hole-transport materials, and electron- or exciton-blocking materials, are also of particular importance. Improvements to these materials can lead to significant improvements in electroluminescent devices.

[0004] Compounds containing both triazine and benzimidazole groups as electron transport materials are known in the art.

[0005] WO 2010 / 126270 A1 discloses such compounds. Both groups are bound to a fluorene core, with the two aromatic rings of the fluorene further present in an aromatic condensation.

[0006] KR 101257695 B also discloses fluorenes containing a triazine and a benzimidazole group. However, the triazine group is substituted in only two of the three carbon-containing positions.

[0007] WO 2013 / 100464 A1 discloses spirobifluorenes containing both a benzimidazole and a triazine group. However, the triazines are unsubstituted. Furthermore, a benzothiophene group has been fused to the spirobifluorene.

[0008] JP2007049055 A discloses an organic EL element material having a 9,9-diphenylfluorene structure and at least one nitrogen-containing heterocyclic substituent.

[0009] EP 2 749 560 A1 discloses benzimidazole derivatives and their use in organic electronic devices.

[0010] WO 2013 / 100464 A1 discloses a spiro(fluorene) derivative used for organic light-emitting devices.

[0011] KR 2010 0075079 A discloses an indene compound for organic photoelectric devices.

[0012] However, there is still room for improvement in the use of these materials, as with other materials, particularly with regard to the efficiency, operating voltage and lifetime of organic electronic devices.

[0013] 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.

[0014] Surprisingly, it has been found that certain compounds, described in more detail below, achieve these objectives and eliminate the disadvantage of the prior art. The use of these compounds leads to very good properties of organic electronic devices, in particular organic electroluminescent devices, particularly with regard to lifetime, efficiency, and operating voltage. Electronic devices, in particular organic electroluminescent devices, containing such compounds, as well as the corresponding preferred embodiments, are therefore the subject of the present invention.

[0015] The present invention relates to a chemical compound according to formula (33) of claim 1.

[0016] The present invention also relates to a compound of the general formula (4) wherein the indices and symbols are as defined in claim 2.

[0017] In a further preferred embodiment, the compound has the general formula (23) where the above definitions apply to the symbols and indices used and their preferred embodiments also represent preferred embodiments for the compound of formula (23).

[0018] Very preferred is a compound of the general formula (24), the above definitions applying to the symbols and indices used and the preferred embodiments of which also represent preferred embodiments for the compound of the formula (24).

[0019] Particularly preferred is a compound of the general formulas (25) and (26), the above definitions applying to the symbols and indices used and their preferred embodiments also representing preferred embodiments for the compound of the formulas (25) and (26).

[0020] Further preferred is a compound of the general formula (34) wherein the above definitions apply to the symbols and indices used and their preferred embodiments also represent preferred embodiments for the connection of the forms (34).

[0021] Further preferred is a compound of the general formula (35) wherein the above definitions apply to the symbols and indices used and their preferred embodiments also represent preferred embodiments for the connection of the forms (35).

[0022] Further preferred is a compound of the general formula (36) wherein the above definitions apply to the symbols and indices used and their preferred embodiments also represent preferred embodiments for the connection of the forms (36).

[0023] Further preferred is a compound of the general formula (37) wherein the above definitions apply to the symbols and indices used and their preferred embodiments also represent preferred embodiments for the connection of the forms (37).

[0024] Very preferred is a compound of the following general formulas (38) to (40), where the above definitions apply to the symbols and indices used and whose preferred embodiments also represent preferred embodiments for the compound of the formulas (38) to (40), wherein of the compounds of general formulas (38) to (40), those of formula (38) and (40) are particularly preferred.

[0025] Particularly preferred is a compound of the following general formula (41), wherein the above definitions apply to the symbols and indices used and whose preferred embodiments also represent preferred embodiments for the compound of formula (41).

[0026] Very particular preference is given to a compound of the following general formulas (42) and (43), wherein the above definitions apply to the symbols and indices used and whose preferred embodiments also represent preferred embodiments for the compound of the formulas (42) and (43).

[0027] In a further preferred embodiment, the compound has the general formula (44) where the above definitions apply to the symbols and indices used and their preferred embodiments also represent preferred embodiments for the compound of formula (44).

[0028] Very preferred is a compound of the general formula (45), the above definitions applying to the symbols and indices used and the preferred embodiments of which also represent preferred embodiments for the compound of the formula (45).

[0029] Particularly preferred is a compound of the general formulas (46) and (47), the above definitions applying to the symbols and indices used and their preferred embodiments also representing preferred embodiments for the compound of the formulas (46) and (47).

[0030] Very particular preference is given to a compound of the general formulas (48) to (51), the above definitions applying to the symbols and indices used and the preferred embodiments of which also represent preferred embodiments for the compound of the formulas (48) to (51).

[0031] Furthermore, very particular preference is given to a compound of the general formulas (52) to (55), the above definitions applying to the symbols and indices used and the preferred embodiments of which also represent preferred embodiments for the compound of the formulas (52) to (55).

[0032] It is particularly preferred if in the compounds of the above formulas either n or m is 0, and even more preferred if both n and m are 0.

[0033] Most preferred in the sense of the present invention is when a, b, q and p are 0 and u and v are independently either 0 or 1, where if v is 1, the group V is a phenylene group and if u is 1, the group U is a phenylene group.

[0034] It is further preferred if the radical R 1< is, on each occurrence, identically or differently, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 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<, or a combination of these systems.

[0035] It is very preferred if the radical R 1< is, on each occurrence, identically or differently, a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 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<.

[0036] It is particularly preferred if the radical R 1< is, on each occurrence, identically or differently, a straight-chain alkyl group having 1 to 40 C atoms, each of which may be substituted by one or more radicals R 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<.

[0037] It is very particularly preferred if the radical R 1< is, on each occurrence, identically or differently, a straight-chain alkyl group having 1 to 40 C atoms, and it is particularly preferred if the R 1< is, on each occurrence, identically or differently, a straight-chain alkyl group having 1 to 15 C atoms.

[0038] It is further preferred if R 5< is, identically or differently on each occurrence, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 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<, or a combination of these systems; where two or more adjacent substituents R 5< cannot form a mono- or polycyclic, aliphatic or aromatic ring system with each other.

[0039] It is very preferred if R 5< on each occurrence, identically or differently, is a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 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<, where two or more adjacent substituents R 5< cannot form a mono- or polycyclic, aliphatic or aromatic ring system with one another.

[0040] It is particularly preferred if R 5< on each occurrence, identically or differently, is a straight-chain alkyl group having 1 to 40 C atoms, each of which may be substituted by one or more radicals R 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<, where two or more adjacent substituents R 5< cannot form a mono- or polycyclic, aliphatic or aromatic ring system with one another.

[0041] It is very particularly preferred if R 5<, identically or differently, is on each occurrence a straight-chain alkyl group having 1 to 40 carbon atoms or an aromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R 2<, where two or more adjacent substituents R 5< cannot form a mono- or polycyclic, aliphatic, or aromatic ring system with one another. Very particularly preferred aromatic ring systems are selected from the group consisting of the phenyl, biphenyl, and terphenyl groups.

[0042] Furthermore, it is preferred if Ar 1< on each occurrence, identically or differently, is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 2<; two radicals Ar 1< may also be linked to one another by a single bond or a bridge selected from C(R 2<) 2, O and S; it is preferred if two radicals Ar 1< are not linked to one another.

[0043] Very preferred groups for Ar 1< are selected from the group consisting of the phenyl, biphenyl, terphenyl, quaternaryphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, benzimidazolyl, carbazolyl, indenocarbazolyl, indolocarbazolyl groups, where the groups may be substituted by one or more identical or different radicals R 2<, with the phenyl groups mentioned being most preferred.

[0044] For the purposes of this application, 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. This is illustrated by the following scheme:

[0045] 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:

[0046] An aryl group within the meaning of this invention contains at least 6 C atoms; a heteroaryl group within the meaning of this invention contains at least 2 C atoms and at least 1 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 aryl or heteroaryl group, for example naphthalene, anthracene, pyrene, quinoline, isoquinoline, etc.

[0047] 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 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. The heteroatoms are preferably selected from N, O and / or S. An aromatic or heteroaromatic ring system within the meaning of this invention is to be understood as a system that does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups can also be connected by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as, for example, an sp 3< -hybridized C, Si, N or O atom, an sp 2< -hybridized C or N atom or an sp-hybridized C atom. For example, systems such as 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 linear or cyclic alkyl, alkenyl, or alkynyl group, or by a silyl group. Furthermore, systems in which two or more aryl or heteroaryl groups are linked to one another via single bonds are also understood as aromatic or heteroaromatic ring systems within the meaning of this invention, for example systems such as biphenyl, terphenyl, or diphenyltriazine.

[0048] An aromatic or heteroaromatic ring system with 5 - 60 aromatic ring atoms, which may each be substituted by radicals as defined above 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, benzphenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, Isoindole, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine,Phenoxazin, Pyrazol, Indazol, Imidazol, Benzimidazol, Naphthimidazol, Phenanthrimidazol, Pyridimidazol, Pyrazinimidazol, Chinoxalinimidazol, Oxazol, Benzoxazol, Naphthoxazol, Anthroxazol, Phenanthroxazol, Isoxazol, 1,2-Thiazol, 1,3-Thiazol, Benzothiazol, Pyridazin, Benzopyridazin, Pyrimidin, Benzpyrimidin, Chinoxalin, 1,5-Diazaanthracen, 2,7-Diazapyren, 2,3-Diazapyren, 1,6-Diazapyren, 1,8-Diazapyren, 4,5-Diazapyren, 4,5,9,10-Tetraazaperylen, Pyrazin, Phenazin, Phenoxazin, Phenothiazin, Fluorubin, Naphthyridin, Azacarbazol, Benzocarbolin, Phenanthrolin, 1,2,3-Triazol, 1,2,4-Triazol, Benzotriazol, 1,2,3-Oxadiazol, 1,2,4-Oxadiazol, 1,2,5-Oxadiazol, 1,3,4-Oxadiazol, 1,2,3-Thiadiazol, 1,2,4-Thiadiazol, 1,2,5-Thiadiazol, 1,3,4-Thiadiazol, 1,3,5-Triazin, 1,2,4-Triazin, 1,2,3-Triazin, Tetrazol, 1,2,4,5-Tetrazin, 1,2,3,4-Tetrazin, 1,2,3,5-Tetrazin, Purin, Pteridin, Indolizin und Benzothiadiazol oder Kombinationen dieser Gruppen.,

[0049] In the context of the present invention, a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, in which individual H atoms or CH 2 groups can also be substituted by the groups mentioned above in the definition of the radicals, preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, 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 or octynyl.Unter einer Alkoxy- oder Thioalkylgruppe 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, 2,2,2-Trifluorethoxy, 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.

[0050] The compounds of the invention can be prepared according to Schemes 1 and 2. The corresponding monoboronic acids are commercially available and can be converted into the corresponding target molecules by Suzuki coupling. where Ab represents a leaving group, preferably selected from Cl, Br, I, and triflate, most preferably Br. In addition to boron pinacol esters, other esters or boronic acid itself can also be used. These are well known to those skilled in the art.

[0051] The fluorenes of the invention can be prepared analogously by Suzuki coupling. Other boron compounds can also be used. These are well known to those skilled in the art.

[0052] The general process shown for synthesizing the compounds of the invention is exemplary. Those skilled in the art can develop alternative synthesis routes within the scope of their general technical knowledge.

[0053] The following overview contains an exemplary representation of compounds according to the invention which can be prepared by one of the processes described herein.

[0054] The compounds of the invention can be used in organic electronic devices. The compounds of the invention are used in electron-injecting, electron-transporting, and / or emitting layers.

[0055] A further subject of the present invention is therefore the use of a compound according to the invention in an electronic device, preferably in an electron-injecting, electron-transporting and / or in an emitting layer.

[0056] The compounds according to the invention can be the only component of a layer or can be used in combination with one or more other materials in a layer.

[0057] Further improvements in efficiency data of electronic devices containing the compounds can be achieved when the compounds according to the invention are used in compositions with other materials.

[0058] The compounds according to the invention are preferably used in composition with materials which are typically used in devices, in particular electronic devices such as electroluminescent devices.

[0059] The present invention therefore also relates to a composition comprising one or more compounds according to the invention and at least one additional functional molecule selected from the group consisting of fluorescent emitters, phosphorescent emitters, matrix materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocking materials, hole blocking materials and n-dopants.

[0060] In the literature, the term "host material" is often used instead of "matrix material." Some authors use the term "host material" for matrix materials for fluorescent emitters, whereas the term "matrix material" refers to materials used in conjunction with phosphorescent emitters in the emission layer. Here, the term "matrix material" is used independently of the emitter and refers to a material that can be used in the emission layer with fluorescent or phosphorescent emitters.

[0061] The specialist is well acquainted with the individual materials and has no difficulty selecting suitable compounds from a large repertoire.

[0062] In a preferred embodiment of the present invention, the organic electronic device contains one or more of the compounds of the invention in the electron-transport layer (ETL). The ETL can be a pure layer consisting of the compound of the invention or it can also contain at least one electron-transport material. The skilled person can select from a variety of known electron-transport materials. The combined use of the compound of the invention with an electron-transport material in the ETL leads to organic electronic devices with particularly good performance data.

[0063] The present invention therefore relates to a composition comprising at least one of the compounds according to the invention and at least one ETM. The ETM is preferably selected from the group of non-metallic electron-transport materials.

[0064] Preferred electron-transport materials for the composition according to the invention are selected from pyridines, pyrimidines, pyridazines, pyrazines, oxadiazoles, quinolines, quinoxalines, anthracenes, benzanthracenes, pyrenes, perylenes, benzimidazoles, triazines, ketones, lactams, oxazoles, phenanthrolines, phosphine oxides, and phenazines. Triazines and lactams are particularly preferred.

[0065] The layer thickness of the ETL is preferably 5 to 150 nm.

[0066] The concentration of the compound according to the invention in the ETL is preferably in the range from 10 vol% to 90 vol%, very preferably in the range from 20 vol% to 80 vol%, very particularly preferably in the range from 30 vol% to 70 vol% and especially preferably in the range from 40 vol% to 60 vol%, based on the entire electron transport layer.

[0067] In addition to the electron transport layer, the device according to the invention can also have an electron injection layer (EIL) located between the cathode and the electron transport layer. Preferred materials used as electron injection material (EIM) in the EIL are selected from the group of alkali metals, alkali metal complexes, in particular alkali oxinates (in particular substituted or unsubstituted Li hydroxyquinolines), as well as alkali metal or alkaline earth metal fluorides, and also their oxides or carbonates. Very preferred electron injection materials are Li, LiF, Li 2 O, BaF 2 , MgO, NaF, Cs, CsF, Cs 2 CO 3 , Liq, with LiF and Liq being particularly preferred and LiF being a very particularly preferred electron injection material.

[0068] The layer thickness of the EIL is preferably 0.5 to 5 nm.

[0069] Further preferred EIMs are substituted lithium 8-hydroxyquinolinates, in particular those disclosed in DE 102013013876.0 and especially those of the following formulas (C-1) to (C-34).

[0070] Further performance improvements in organic electronic devices can be achieved by using the compound of the invention in an electron-transport layer in combination with an n-dopant. The n-dopant can be either an inorganic or an organic material.

[0071] An n-dopant is understood here as an organic or inorganic compound that is capable of donating electrons (electron donor), i.e. a compound that acts as a reducing agent.

[0072] The compounds used for n-doping can be used as precursors, whereby these precursor compounds release n-dopants upon activation.

[0073] Preferred n-dopants are selected from electron-rich metal complexes; P=N compounds; N-heterocycles, particularly preferably naphthylenecarbodiimides, pyridines, acridines and phenazines; fluorenes and radical compounds.

[0074] Particularly preferred electron-rich metal complexes are described, inter alia, in WO 2005 / 86251 A2, which is incorporated into the present application by reference for disclosure purposes. Neutral electron-rich metal complexes are preferred.

[0075] Particularly preferred P=N compounds are disclosed, inter alia, in WO 2012 / 175535 A1, which document is incorporated into the present application by reference for disclosure purposes.

[0076] Another group of n-dopants are N-heterocycles. N-heterocycles are cyclic compounds whose ring structure contains at least one nitrogen atom in addition to hydrogen and carbon. These compounds can be saturated, partially unsaturated, or heteroaromatic.

[0077] N-Heterocycles can preferably be used as precursors, with precursor compounds being characterized by the fact that their effect as n-dopants only begins after activation. Preferred N-heterocycles that can be used in particular as precursors are described, inter alia, in WO 2009 / 00237 A1, which is incorporated by reference into the present application for disclosure purposes.

[0078] Another group of N-heterocycles that are suitable as n-dopants are naphthylenecarbodiimides. Naphthylenecarbodiimides comprise at least one carbodiimide group (N=C=N) and one naphthylene group.

[0079] Surprising advantages can be achieved by the naphthylenecarbodiimides described in WO 2012 / 168358 A1, which is incorporated by reference into the present application for disclosure purposes.

[0080] Preferred N-heterocylic compounds suitable for use as n-dopants also include pyridine, acridine, and phenazine derivatives. These compounds comprise pyridine, acridine, and phenazine structural elements and are known in the art. Preferred acridines and phenazines are described, among others, in US 2007 / 0145355 A1, which is incorporated by reference into the present application for disclosure purposes.

[0081] Surprising advantages can be achieved by the pyridines described in EP 2 452 946 A1 and EP 2 463 927 A1, which documents are incorporated by reference into the present application for disclosure purposes.

[0082] According to a particular embodiment of the present invention, fluorenes can be used as n-dopants. Preferred fluorenes are described, inter alia, in WO 2012 / 031735 A1, which is incorporated by reference into the present application for disclosure purposes.

[0083] Preferred n-dopants include radical compounds known in the art. Preferred radical compounds comprise heterocyclic groups. Particularly preferred radical compounds are disclosed, inter alia, in EP 1 837 926 A1 and WO 2007 / 107306 A1, which are incorporated by reference into the present application for disclosure purposes.

[0084] Of the n-dopants mentioned, the electron-rich metal complexes described in WO 2005 / 86251 A2 are particularly preferred, with the metal complexes of the formula W 2 (hpp) 4 being particularly preferred, where hpp represents the anion of 1, 3, 4, 6, 7, 8-hexahydro-2H-pyrimido[1,2-a]pyrimidine. Neutral electron-rich metal complexes are particularly preferred.

[0085] With n-doping, an electron transfer occurs from the HOMO (highest occupied molecular orbital) level of the n-dopant to the LUMO (lowest unoccupied molecular orbital) level of the matrix material, whereby the electron is generally not strongly localized but is counted among the charge carriers.

[0086] A further development of the invention provides that the amount of a difference between the HOMO of the n-dopant and the LUMO of the compound according to the invention is preferably less than about 1 eV, more preferably the amount of the difference is less than about 0.5 eV.

[0087] Preferably, the compounds of the invention have a LUMO level of about 1 eV or greater, most preferably 1.5 eV or greater.

[0088] Molecular orbitals, in particular the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), their energy levels, as well as the energy of the lowest triplet state T1 and the lowest excited singlet state S1 of the materials, are determined using quantum chemical calculations. For the calculation of organic substances without metals, a geometry optimization is first performed using the "Ground State / Semi-Empirical / Default Spin / AM1 / Charge 0 / Spin Singlet" method. Subsequently, an energy calculation is performed based on the optimized geometry. The method "TD-SCF / DFT / Default Spin / B3PW91" with the "6-31G(d)" basis set is used (Charge 0, Spin Singlet). For metal-containing compounds, the geometry is optimized using the "Ground State / Hartree-Fock / Default Spin / LanL2MB / Charge 0 / Spin Singlet" method.The energy calculation is carried out analogously to the method described above for organic substances, with the difference that the basis set "LanL2DZ" is used for the metal atom and the basis set "6-31G(d)" for the ligands. The energy calculation yields the HOMO energy level HEh and the LUMO energy level LEh in Hartree units. From this, the HOMO and LUMO energy levels, calibrated using cyclic voltammetry measurements, are determined in electronvolts as follows: . HOMO eV = HEh ∗ 27.212 − 0.9899 / 1.1206 LUMO eV = LEh ∗ 27.212 − 2.0041 / 1.385

[0089] For the purposes of this application, these values ​​are to be regarded as HOMO or LUMO energy levels of the materials.

[0090] The lowest triplet state T 1 is defined as the energy of the triplet state with the lowest energy resulting from the quantum chemical calculation described.

[0091] The lowest excited singlet state S 1 is defined as the energy of the excited singlet state with the lowest energy resulting from the described quantum chemical calculation.

[0092] The method described here is independent of the software package used and always produces the same results. Examples of commonly used programs for this purpose are "Gaussian09W" (Gaussian Inc.) and Q-Chem 4.1 (Q-Chem, Inc.).

[0093] In yet another preferred embodiment of the present invention, the organic electronic device contains one or more of the compounds of the invention in the emission layer (EML). The compound of the invention is used as a matrix material in the EML together with one or more emitters. Both fluorescent and phosphorescent emitters are considered as emitters, with phosphorescent emitters being preferred.

[0094] The term phosphorescent emitter (also called phosphorescent dopant) typically includes compounds in which the light emission occurs predominantly through a spin-forbidden transition, for example a transition from a triplet state or a state with a higher spin quantum number, for example a quintet state.

[0095] Particularly suitable phosphorescent dopants are compounds which, upon suitable excitation, emit light, preferably in the visible range, and which also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80. Preferably, compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are used as phosphorescent dopants, in particular compounds containing iridium, platinum, or copper.

[0096] For the purposes of the present application, all luminescent iridium, platinum or copper complexes are considered to be phosphorescent compounds.

[0097] Preferably, the phosphorescent compounds are those that emit light from a triplet state.

[0098] The term fluorescent emitter (also fluorescent dopant) includes compounds that predominantly exhibit light emission by transition from an excited singlet state.

[0099] Both fluorescent and phosphorescent emitters are well known to the person skilled in the art and it is not difficult for him to select suitable emitters.

[0100] Examples of phosphorescent dopants can be found in applications WO 2000 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 2005 / 033244, WO 2005 / 019373, and US 2005 / 0258742. In general, all phosphorescent complexes as used in the prior art for phosphorescent OLEDs and as known to those skilled in the art in the field of organic electroluminescent devices are suitable for use in the devices according to the invention.

[0101] Explicit examples of phosphorescent dopants are listed in the following table.

[0102] In a further preferred embodiment of the invention, the compounds are used as a matrix component of mixed-matrix systems. The mixed-matrix systems preferably comprise two or three different matrix materials, particularly preferably two different matrix materials. Preferably, one of the two materials is a material with hole-transporting properties, and the other material is a material with electron-transporting properties. However, the desired electron-transporting and hole-transporting properties of the mixed-matrix components can also be combined primarily or entirely in a single mixed-matrix component, with the additional mixed-matrix component(s) fulfilling different functions.The two different matrix materials can be present in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, particularly preferably 1:10 to 1:1, and most preferably 1:4 to 1:1. Mixed-matrix systems are preferably used in phosphorescent organic electroluminescent devices. More detailed information on mixed-matrix systems can be found, among other things, in the application WO 2010 / 108579.

[0103] Particularly suitable matrix materials which can be used in combination with the compounds according to the invention as matrix components of a mixed matrix system are selected from the preferred matrix materials for phosphorescent dopants or the preferred matrix materials for fluorescent dopants listed below, depending on the type of dopant used in the mixed matrix system.

[0104] Materials from various classes of substances can be used as matrix materials, preferably for fluorescent dopants. Preferred matrix materials are selected from the classes of lactams (e.g. WO 2011 / 116865, WO 2011 / 137951, WO 2013 / 064206, WO 2014 / 056567, EP 13003343.4, EP 14000729.5), oligoarylenes (e.g. 2,2',7,7'-tetraphenylspirobifluorene according to EP 676461 or dinaphthylanthracene), in particular oligoarylenes containing condensed aromatic groups, oligoarylenevinylenes (e.g. DPVBi or spiro-DPVBi according to EP 676461), polypodal metal complexes (e.g. according to WO 2004 / 081017), hole-conducting compounds (e.g. according to WO 2004 / 058911), the electron-conducting compounds, in particular ketones, phosphine oxides, sulfoxides, etc. (e.g. according to WO 2005 / 084081 and WO 2005 / 084082), the atropisomers (e.g. according to WO 2006 / 048268), the boronic acid derivatives (e.g. according to WO 2006 / 117052) or the benzanthracenes (e.g. according to WO 2008 / 145239).Particularly preferred matrix materials are selected from the classes of oligoarylenes containing naphthalene, anthracene, benzanthracene, and / or pyrene, or atropisomers of these compounds, oligoarylenevinylenes, ketones, phosphine oxides, and sulfoxides. Very particularly preferred matrix materials are selected from the classes of oligoarylenes containing anthracene, benzanthracene, benzphenanthrene, and / or pyrene, or atropisomers of these compounds. An oligoarylene, within the meaning of this invention, is understood to mean a compound in which at least three aryl or arylene groups are bonded to one another.

[0105] Preferred matrix materials for phosphorescent dopants are aromatic amines, in particular, for example according to US 2005 / 0069729, carbazole derivatives (e.g. CBP, N,N-biscarbazolylbiphenyl) or compounds according to WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527 or WO 2008 / 086851, bridged carbazole derivatives, for example according to WO 2011 / 088877 and WO 2011 / 128017, indenocarbazole derivatives, for example according to WO 2010 / 136109 and WO 2011 / 000455, azacarbazole derivatives, for example. according to EP 1617710, EP 1617711, EP 1731584, JP 2005 / 347160, indolocarbazole derivatives, e.g. according to WO 2007 / 063754 or WO 2008 / 056746, ketones, e.g. according to WO 2004 / 093207 or WO 2010 / 006680, phosphine oxides, sulfoxides and sulfones, e.g. according to WO 2005 / 003253, oligophenylenes, bipolar matrix materials, e.g. according to WO 2007 / 137725, silanes, e.g. according to WO 2005 / 111172, azaboroles or boronic esters, e.g. B. according to WO 2006 / 117052, triazine derivatives, e.g. according to WO 2010 / 015306, WO 2007 / 063754 or WO 2008 / 056746, zinc complexes, e.g.according to EP 652273 or WO 2009 / 062578, aluminum complexes, e.g. BAlq, diazasilole and tetraazasilole derivatives, e.g. according to WO 2010 / 054729, diazaphosphole derivatives, e.g. according to WO 2010 / 054730 and aluminum complexes, e.g. BAIQ.

[0106] The present invention therefore also relates to a composition comprising at least one compound according to the invention and at least one further matrix material.

[0107] Furthermore, the present invention also relates to a composition comprising at least one compound according to the invention and at least one further matrix material and furthermore at least one fluorescent or phosphorescent emitter, preferably a phosphorescent emitter.

[0108] The present invention also relates to a composition comprising at least one compound according to the invention and at least one wide band gap material, wherein "wide band gap material" is understood to mean a material as disclosed in US Pat. No. 7,294,849. These systems exhibit particularly advantageous performance data in electroluminescent devices.

[0109] Systems comprising multiple matrix materials (mixed-matrix systems) are used in the light-emitting layers of organic electroluminescent devices. The light-emitting layer also contains one or more dopants.

[0110] The compounds and compositions according to the invention can be used in organic electronic devices. Therefore, the present invention also relates to an organic electronic device comprising one or more of the compounds or compositions according to the invention.

[0111] The organic electronic device according to the invention is preferably selected from the group consisting of organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic light-emitting transistors (OLETs), organic solar cells (OSCs), organic optical detectors, organic photoreceptors, organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs, LECs, or LEECs), organic laser diodes (O-lasers), and organic light-emitting diodes (OLEDs). Particular preference is given to organic electroluminescent devices, very particular preference to OLECs and OLEDs, and especially preference to OLEDs.

[0112] OLEDs in the sense of the present invention are understood to mean both organic light-emitting diodes containing small organic molecules (SMOLEDs) and polymer light-emitting diodes (PLEDs), with SMOLEDs being preferred OLEDs.

[0113] As already mentioned above, the organic layer containing the compound or composition according to the invention is preferably a layer of the device with an electron-transporting function. It is particularly preferably an electron injection layer (EIL), electron transport layer (ETL), hole blocking layer (HBL), or emitting layer (EML).

[0114] A hole transport layer (HTL) according to the present application is a layer with hole transporting function, which is located between the anode and the emitting layer (EML).

[0115] An electron transport layer (ETL) according to the present application is a layer with electron transporting function, which is located between the cathode and the emitting layer (EML).

[0116] The structure of organic electronic devices, and in particular of organic electroluminescent devices, is well known to the person skilled in the art from the prior art.

[0117] An electronic, in particular electroluminescent, organic device according to the invention comprises at least one organic layer. An organic layer is characterized by containing at least one organic or organometallic compound. An organic device does not necessarily have to contain only layers composed of organic or organometallic materials. It is also possible for one or more layers to contain inorganic materials or to be composed entirely of inorganic materials.

[0118] The organic electronic device according to the invention contains an anode, a cathode and at least one organic layer which comprises at least one compound according to the invention.

[0119] As already mentioned, particularly preferred organic electronic devices within the meaning of the present invention are organic electroluminescent devices, and in particular OLEDs.

[0120] Metals with a low work function, metal alloys, or multilayer structures made of different metals are preferred as the cathode, such as alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Alloys made of an alkali or alkaline earth metal and silver, for example, an alloy of magnesium and silver, are also suitable. In multilayer structures, in addition to the metals mentioned, other metals with a relatively high work function can be used, such as Ag, in which case combinations of the metals, such as Mg / Ag, Ca / Ag, or Ba / Ag, are generally used. It may also be preferable to introduce a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor.Examples of suitable materials include alkali metal or alkaline earth metal fluorides, as well as the corresponding oxides or carbonates (e.g., LiF, Li 2 O, BaF 2 , MgO, NaF, CsF, Cs 2 CO 3 , etc.). Organic alkali metal complexes, such as Liq (lithium quinolinate) or substituted Li hydroxyquinolinates, are also suitable.

[0121] Materials with a high work function are preferred as the anode. The anode preferably has a work function greater than 4.5 eV vs. vacuum. Metals with a high redox potential, such as Ag, Pt, or Au, are suitable for this purpose. Metal / metal oxide electrodes (e.g., Al / Ni / NiO x , Al / PtO x ) may also be preferred. For some applications, at least one of the electrodes must be transparent or partially transparent to enable either the irradiation of the organic material (O-SC) or the coupling out of light (OLED / PLED, O-LASER). Preferred anode materials here are conductive mixed metal oxides. Particular preference is given to indium tin oxide (ITO) or indium zinc oxide (IZO). Also preferred are conductive, doped organic materials, in particular conductive doped polymers, e.g., PEDOT, PANI, or derivatives of these polymers.It is also preferred if a p-doped hole-transport material is applied to the anode as a hole-injection layer. Suitable p-dopants are metal oxides, such as MoO or WO 3 , or (per)fluorinated electron-deficient aromatics. Other suitable p-dopants are HAT-CN (hexacyanohexaazatriphenylene) or the compound NPD9 from Novaled. Such a layer simplifies hole injection in materials with a deep HOMO, i.e., a large HOMO.

[0122] According to a preferred embodiment, at least two organic layers can be arranged between the anode and the cathode.

[0123] In general, any materials used for the layers according to the prior art can be used in the further layers, and the person skilled in the art can combine any of these materials with the materials according to the invention in an electronic device without inventive effort. Typical ETMs, EIMs, emitters, and matrix materials have already been disclosed above.

[0124] An organic electroluminescent device contains a cathode, an anode, and at least one emitting layer (EML). In addition to these layers, it may contain further layers, for example, one or more hole injection layers (HIL), hole transport layers (HTL), hole blocking layers (HBL), electron transport layers (ETL), electron injection layers (EIL), exciton blocking layers (ExBL), electron blocking layers (EBL), charge generation layers, and / or organic or inorganic p / n junctions. A typical structure of an organic electroluminescent device is: anode / HIL / HTL / EML / ETL / EIL / cathode

[0125] It is possible for one or more hole-transport layers to be p-doped, for example, with metal oxides such as MoO or WO 3 or with (per)fluorinated electron-poor aromatics, and / or for one or more electron-transport layers to be n-doped. Interlayers can also be introduced between two emitting layers, which, for example, have an exciton-blocking function and / or control the charge balance in the electroluminescent device. It should be noted, however, that not all of these layers necessarily need to be present.

[0126] The organic electroluminescent device can contain one emitting layer or it can contain multiple emitting layers. If multiple emitting layers are present, these preferably have a total of multiple emission maxima between 380 nm and 750 nm, resulting in overall white emission, i.e. different emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. Particular preference is given to three-layer systems, wherein the three layers exhibit blue, green and orange or red emission (for the basic structure, see, for example, WO 2005 / 011013), or systems that have more than three emitting layers. It can also be a hybrid system, wherein one or more layers fluoresce and one or more other layers phosphoresce.

[0127] The device is structured accordingly (depending on the application), contacted and finally hermetically sealed, since the lifetime of such devices is drastically reduced in the presence of water and / or air.

[0128] Further preferred is an electronic device, in particular 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 typically less than 10 -5 mbar, preferably less than 10 -6 mbar. It is also possible for the initial pressure to be even lower or even higher, for example, less than 10 -7 mbar.

[0129] Also preferred is an electronic device, in particular 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 structured (e.g., BMS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

[0130] Further preferred is an electronic device, in particular 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, or nozzle printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing. Soluble compounds are required for this, which are obtained, for example, by suitable substitution.

[0131] The electronic device, in particular the organic electroluminescent device, can also be manufactured as a hybrid system by applying one or more layers from solution and vapor-depositing one or more other layers. For example, it is possible to apply an emitting layer containing at least one emitter and a matrix material from solution and then vacuum-deposit a hole-blocking layer and / or an electron-transport layer thereon.

[0132] These processes are generally known to the person skilled in the art and can be applied by him without difficulty to electronic devices, in particular organic electroluminescent devices containing a compound according to the invention.

[0133] For the production of organic electronic devices from solution, formulations containing the compound according to the invention or the composition according to the invention are required.

[0134] The present invention therefore also relates to a formulation comprising at least one compound according to the invention or at least one composition according to the invention and at least one solvent.

[0135] This formulation can be, for example, a solution, dispersion, or emulsion. It may be preferable to use mixtures of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, □-terpineol, benzothiazole, butylbenzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, Dodecyl benzene, ethyl benzoate, indane, methyl benzoate, NMP, p-cymene, phenetol, 1,4-diisopropylbenzene, dibenzyl ether, diethyhene 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-isopropyl naphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane or mixtures of these solvents.

[0136] Devices containing the compound or composition according to the invention can be used in a wide variety of ways. For example, electroluminescent devices can be used in displays for televisions, mobile phones, computers, and cameras. However, the devices can also be used in lighting applications. Furthermore, electroluminescent devices can be used in medicine or cosmetics for phototherapy. This allows a variety of diseases (psoriasis, atopic dermatitis, inflammation, acne, skin cancer, etc.) or the prevention or reduction of skin wrinkling, skin redness, and skin aging to be treated. Furthermore, the light-emitting devices can be used to keep drinks, food, or groceries fresh or to sterilize devices (e.g., medical devices).

[0137] The present invention therefore relates to an electronic device, preferably an organic electroluminescent device, very preferably an OLED or OLEC and very particularly preferably an OLED containing at least one compound according to the invention or at least one composition according to the invention for use in medicine for phototherapy.

[0138] A further preferred subject matter of the present invention relates to an electronic device, preferably an organic electroluminescent device, very preferably an OLED or OLEC and very particularly preferably an OLED containing at least one compound according to the invention or at least one composition according to the invention for use in the phototherapeutic treatment of skin diseases.

[0139] A further very preferred subject matter of the present invention relates to an electronic device, preferably an organic electroluminescent device, very preferably an OLED or OLEC and very particularly preferably an OLED containing at least one compound according to the invention or at least one composition according to the invention for use in the phototherapeutic treatment of psoriasis, atopic dermatitis, inflammatory diseases, vitiligo, wound healing, skin cancer and jaundice, in particular neonatal jaundice.

[0140] The present invention further relates to the use of the electronic device, preferably an organic electroluminescent device, very preferably an OLED or OLEC and very particularly preferably an OLED containing at least one compound according to the invention or at least one composition according to the invention in cosmetics, preferably for the treatment of acne, aging skin (skin aging), and cellulite.

[0141] The electronic devices according to the invention, in particular the organic electroluminescent devices, are characterized by the following surprising advantages over the prior art: 1. The organic electroluminescent devices according to the invention exhibit very high efficiency. 2. The organic electroluminescent devices according to the invention simultaneously exhibit an improved lifetime. 3. The organic electroluminescent devices according to the invention simultaneously exhibit a reduced operating voltage. 4. The compounds according to the invention can be prepared very easily and inexpensively, are readily processed, and evaporate very well, making the compounds according to the invention highly suitable for the commercial mass production of organic electronic devices, in particular organic electroluminescent devices.

[0142] The above-mentioned preferred embodiments can be combined with one another in any desired manner. In a particularly preferred embodiment of the invention, the above-mentioned preferred embodiments apply simultaneously.

[0143] 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.

[0144] 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).

[0145] 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.

[0146] The teaching of technical action disclosed in the present invention can be abstracted and combined with other examples.

[0147] The person skilled in the art can produce further electronic devices according to the invention from the descriptions without inventive step and thus carry out the invention in the entire claimed scope. Examples Example 1 Synthesis of 2-[3-[7'-(4,6-diphenyl-1,3,5-triazin-2-yl)-9,9'-spirobi[fluoren]-2'-yl]phenyl]-1-phenyl-benzimidazole 6a

[0148] Synthesis of 2-[3-(7'-bromo-9,9'-spirobi[fluoren]-2'-yl)phenyl]-1-phenyl-benzimidazole (3a) Variant A

[0149] In a 2 L four-necked flask, 50.0 g (105 mmol, 1.00 eq) of 2,7-dibromo-9,9'-spirobifluorene 1a, 41.7 g (105 mmol, 1.00 eq) 1-phenyl-2-[e-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-y-yl)-phenyl]-1H-benzoimidazole 2a and 36.4 g (263 mmol, 2.50 eq) of potassium carbonate in 400 ml of toluene, 400 ml of 1,4-dioxane, and 200 ml of deionized water were initially charged and degassed. Then, 1.22 g (1.05 mmol, 0.01 eq) of tetrakis(triphenylphosphine)palladium(0) were added, and the mixture was heated to reflux overnight. After the reaction was complete, the mixture was cooled, filtered through Celite, and diluted with 1 L of toluene. The solution was washed three times with 300 ml portions of semisaturated sodium chloride solution and, after drying over sodium sulfate, concentrated to approximately 200 ml in a rotary evaporator. The precipitated solid was filtered off and dried under reduced pressure. The disubstituted by-product was removed by sublimation. 22.0 g (33.1 mmol, 32%) of the desired product 3areceive. Variant B

[0150] The procedure is analogous to that of variant A, but instead of tetrakis(triphenylphosphine)palladium(0) 0.01 eq palladium(II) acetate and 0.01 eq dicyclohexyl-(2',6'-dimethoxy-biphenyl-2-yl-phosphine (SPhos) are used.

[0151] The following are implemented analogously: Nr. Educt 1 Educt 2 Product 3 Var. Training 3b [171408-84-7] [1549686-33-0] A 54% 3c [67665-47-8] A 35% 3d [1257321-41-7] [1169709-19-6] B 41% 3e [67665-47-8] [1169709-19-6] A 59% 3f [67665-47-8] [1146340-38-6] B 32% 3g [1257321-41-7] [1505512-90-2] B 62% 3h [171408-84-7] [1172134-18-7] B 44% 3i [171408-84-7] [1553408-82-4] A 21% 3j [171408-84-7] [58534-74-0] B 15% 3k [1373114-50-1] [952514-86-2] A 64% 3l [1418299-83-8] [952514-86-2] A 38% 3m [28320-32-3] [1146340-38-6] B 32% 3n [865702-19-8] [952514-86-2] B 53% 3o [736138-41-3] [1549686-33-0] A 41% 3p [880800-04-4] [1384871-80-0] B 58% 3q [198142-65-3] [1219956-29-2] B 17% 3r [1303969-26-7] [1172134-16-5] A 39% 3s [28320-32-3] [1316275-47-4] B 28% Var. - variant; Yield - yield Synthesis of 1-phenyl-2-[3-[7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9'-spirobi[fluoren]-2'-yl]phenyl]benzimidazole 4a

[0152] In a 1 L four-necked flask, 22.0 g (33.1 mmol, 1.00 eq) of 2-[3-(7'-bromo-9,9'-spirobi[fluoren]-2'-yl)phenyl]-1-phenyl-benzimidazole 3a,8.84 g (30.1 mmol, 0.91 eq) of bis(pinacolato)diboron and 26.0 g (265 mmol, 8.00 eq) of potassium acetate were placed in 500 ml of dried 1,4-dioxane and degassed for 30 minutes. Then, 812 mg (0.995 mmol, 0.0300 eq) of 1,1-bis(diphenylphosphino)ferrocene dichloropalladium(II) complex with DCM were added and heated to an internal temperature of 80°C. After stirring overnight, the mixture was cooled, and the precipitated solid was filtered off with suction. The filtrate was concentrated to approximately 50 ml on a rotary evaporator, and the precipitated solid was also filtered off with suction. The solids were combined and dried. 21.0 g (29.5 mmol, 89%) of the boron ester are obtained 4a receive.

[0153] The following are implemented analogously: Nr. Educt 3 Product 4 Yield e 4b 95% 4c 87% 4d 97% 4e 94% 4f 88% 4g 47% 4h 81% 4i 79% 4j 74% 4k 55% 4l 47% 4m 85% 4n 82% 4o 87% 4p 66% 4q 58% 4r 84% 4s 77% Synthesis of 2-[3-[7'-(4,6-diphenyl-1,3,5-triazin-2-yl)-9,9'-spirobi[fluoren]-2'-yl]phenyl]-1-phenyl-benzimidazole 6a Variant A

[0154] In a 1 L three-necked flask, 21.0 g (29.5 mmol, 1.00 eq) of 1-phenyl-2-[3-[7'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9'-spirobi[fluoren]-2'-yl]phenyl]benzimidazole 4a and 7.90 g (29.5 mmol, 1.00 eq) 2-chloro-4,6-diphenyl-[1,3,5]triazine 5a together with 3.75 g (35.4 mmol, 1.20 eq) of sodium carbonate in 200 ml of toluene, 200 ml of 1,4-dioxane, and 100 ml of deionized water and degassed for 20 minutes. After adding 1.02 g (0.885 mmol, 0.0300 eq) of tetrakis(triphenylphosphine)palladium(0), the mixture is heated under reflux for 2 days and cooled after the reaction is complete. The precipitated solid is filtered off with suction, washed with water and a little toluene, and then recrystallized several times from toluene / heptane until an HPLC purity of >99.9% is achieved. After sublimation, 11.5 g (14.0 mmol, 43%) of a colorless solid are obtained. 6a receive. Variant B

[0155] The procedure is analogous to that of variant A, using 0.01 eq palladium(II) acetate and 0.04 eq tri(o-tolyl)phosphine instead of tetrakis(triphenylphosphine)palladium(0). Variant C

[0156] The procedure is analogous to that of variant A, but instead of tetrakis(triphenylphosphine)palladium(0) 0.01 eq palladium(II) acetate and 0.01 eq dicyclohexyl-(2',6'-dimethoxy-biphenyl-2-yl-phosphine (SPhos) are used.

[0157] Analogously, the following are produced: Nr. Educt 4 Educt 5 Product 6 Var. Training 6b [3842-55-5] B 57% 6c [12U0 / 46-61-3] A 38% 6d [1472729-25-1] A 42% 6e [1476785-42-8] C 61% 6f [2915-16-4] B 37% 6g [133785-60-1] C 39% 6h [3842-55-5] C 31% 6i [3842-55-5] A 48% 6j [21902-34-1] A 24% 6k [1472062-95-5] B 51% 6l [3842-55-5] B 38% 6m [29509-91-9] C 34% 6n [1205748-61-3] C 44% 6o [1396311-93-5] A 53% 6p [1015814-06-8] C 42% 6q [3842-55-5] B 31% 6r [3842-55-5] B 35% [3842-55-5] B 39% Var. - variant; Yield - yield Beispiel 2 2-(3-[1-phenyl-1 H -benzimidazol-2-yl)phenyl]-4-Phenyl-6-(9,9'-spirobi[9H-fluoren]-2-yl-1,3,5-triazin 11a

[0158] Synthesis of 2-chloro-4-phenyl-6-(9,9'-spirobi[9 H -fluoren]-2-yl)-1,3,5-triazine 9a Variant A

[0159] In a 2 L four-necked flask, 24.5 g (67.9 mmol, 1.00 eq) of 9,9'-spirobifluoren-2'-yl-brononic acid 7a, 15.4 g (68.3 mmol, 1.01 eq) 2,4-dichloro-6-phenyl-[1,3,5]triazine 8aand 9.04 g (85.3 mmol, 1.26 eq) of sodium carbonate in 300 ml of toluene, 300 ml of 1,4-dioxane and 300 ml of deionized water are initially charged and degassed. Then 0.850 g (0.736 mmol, 0.01 eq) of tetrakis(triphenylphosphine)palladium(0) is added and the mixture is heated under reflux for 24 hours. After the reaction is complete, the mixture is cooled and diluted with 100 ml of ethyl acetate. The phases are separated in a separatory funnel, the aqueous phase is extracted three times with ethyl acetate and the combined organic phases are washed once more with water. The mixture is then dried over sodium sulfate and the solution is concentrated until a brownish solid precipitates. The solid is filtered off, triturated with hot ethanol and, after further filtration, dried in vacuo. The product was purified by column chromatography using heptane / dichloromethane 5:1 as the eluent. 9.90 g (19.6 mmol, 29%) of a colorless solid were obtained. Variant B

[0160] The procedure is analogous to that of variant A, using 0.01 eq palladium(II) acetate and 0.04 eq tri(o-tolyl)phosphine instead of tetrakis(triphenylphosphine)palladium(0). Variant C

[0161] The procedure is analogous to that of variant A, but instead of tetrakis(triphenylphosphine)palladium(0) 0.01 eq palladium(II) acetate and 0.01 eq dicyclohexyl-(2',6'-dimethoxy-biphenyl-2-yl-phosphine (SPhos) are used. Variant D

[0162] The procedure is analogous to that of variant A, but instead of tetrakis(triphenylphosphine)palladium(0) 0.02 eq of 1,1-bis(diphenylphosphino)ferrocene dichloropalladium(II) complex with DCM and dried toluene are used as solvent.

[0163] Analogously, the following are produced: Nr. Educt 7 Educt 8 Product 9 Var. Training 9b [1402225-89-1] [236389-21-2] A 34% 9c [20354-40-9] [236389-21-2] B 29% 9d [1700-02-3] [1361305-38-5] B 41% 9e [51800-19-2] [1241891-39-3] C 17% 9f [1491751-92-8] [1222537-26-9] A 26% 9g [1700-02-3] [1222007-94-4] A 11% 9h [10202-45-6] [1421789-05-0] B 25% 9i [1700-02-3] [1257321-47-3] D 18% 9j [59336-36-6] [1346007-05-3] B 54% 9k [1402225-89-1] [333432-28-3] C 41% 9l [1700-02-3] [1454287-24-1] B 31% 9m [1700-02-3] [866100-14-3] A 19% 9n [26032-72-4] [1092840-71-5] B 38% 9o [1402225-89-1] [881-11-75-7] C 42% 9p [1700-02-3] [881913-13-9] A 51% 9q [26032-72-4] [1292291-83-8] A 24% 9r [1700-02-3] [400607-32-1] D 18% 9s [1402225-89-1] [1246022-50-3] A 36% 9t [1700-02-3] [1241891-65-5] B 47% 9u [1700-02-3] [1160862-12-3] B 27% 9v [1700-02-3] [1260032-45-8] D 42% Var. - variant; Yield - yield Synthese von 2-(3-[1-phenyl-1 H -benzimidazol-2-yl)phenyl]-4-Phenyl-6-(9,9'-spirobi[9 H -fluoren]-2-yl-1,3,5-triazin 11a Variant A

[0164] In a 250 ml three-necked flask, 9.90 g (19.6 mmol, 1.00 eq) of 2-chloro-4-phenyl-6-(9,9'-spirobi[9 H -fluoren]-2-yl-1,3,5-triazine 9a, 8.53 g (21.5 mmol, 1.10 eq) 22-phenyl-2-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]1 H -benzimidazol 10aand 4.57 g (43.1 mmol, 2.20 eq) of sodium carbonate in 35 ml of toluene, 35 ml of 1,4-dioxane, and 35 ml of deionized water were initially charged and degassed. Then, 1.13 g (0.980 mmol, 0.05 eq) of tetrakis(triphenylphosphine)palladium(0) were added, and the mixture was heated to reflux for 48 hours. After the reaction was complete, the mixture was cooled, and the precipitated solid was filtered off with suction. The crude product obtained was purified by extraction, triple recrystallization from heptane / toluene, and sublimation. This yielded 4.83 g (6.54 mmol, 33%) of a solid with an HPLC purity of >99.9%. Variant B

[0165] The procedure is analogous to that of variant A, but instead of tetrakis(triphenylphosphine)palladium(0) 0.02 eq of 1,1-bis(diphenylphosphino)ferrocene dichloropalladium(II) complex with DCM and dried toluene are used as solvent. Variant C

[0166] To a solution of 10.2 g (22.2 mmol, 1.00 eq) of 2-biphenyl-3-yl-4-chloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-[1,3,5]triazine 9k and 4.31 g (22.2 mmol, 1.00 eq) 2-phenyl-1 H -benzimidazol 10k 4.15 ml (24.4 mmol, 1.10 eq) of diisopropylethylamine (Hünig's base) are added to 150 ml of THF at room temperature. The reaction mixture is stirred overnight, and after completion of the reaction, the solvent is removed in vacuo. After addition of 200 ml of dichloromethane, the solution is extracted three times with water, dried over sodium sulfate, and the solvent is removed using a rotary evaporator. Purification is carried out analogously to variant A. 5.57 g (9.02 mmol, 41%) of the desired product are obtained. 11k receive.

[0167] Analogously, the following are produced: Nr. Educt 9 Educt 10 Product 11 Var Training 11b [1256723-93-9] B 71% 11c [1507395-74-5] B 43% 11d [1256723-93-9] B 55% 11e [867044-33-5] A 29% 11f [1256723-93-9] B 47% 11g [897445-67-9] C 63% 11h [1214723-26-8] A 47% 11i [1256723-93-9] A 31% 11j [1214723-26-8] B 36% 11k [716-79-0] B 41% 11l [952514-79-3] A 58% 11m [1172134-16-5] A 26% 11n [952514-79-3] B 74% 11o [1553408-82-4] A 42% 11p [1256723-93-9] A 37% 11q [952514-79-3] B 32% 11r [1256723-93-9] A 21% 11s [1191061-90-1] A 62% 11t [1214723-26-8] B 33% 11u [1214723-26-8] A 29% 11v [1316275-47-4] A 58% Var - variant; Ausb - yield Example 3 Production and characterization of OLEDs

[0168] In the following examples V1 to E16 (see Tables 1 and 2) the data of different OLEDs are presented.

[0169] Pretreatment for examples V1-E16: Glass plates coated with 50 nm of patterned ITO (indium tin oxide) are coated with 20 nm of PEDOT:PSS (poly(3,4-ethylenedioxythiophene) poly(styrenesulfonate), supplied as CLEVIOS™< P VP AI 4083 from Heraeus Precious Metals GmbH, Germany, spin-coated from aqueous solution) for improved processing. These coated glass plates form the substrates onto which the OLEDs are applied.

[0170] OLEDs generally have the following layer structure: substrate / hole transport layer (HTL) / optional interlayer (IL) / electron blocking layer (EBL) / emission layer (EML) / optional hole blocking layer (HBL) / electron transport layer (ETL) / optional electron injection layer (EIL), and finally a cathode. The cathode is formed by a 100 nm thick aluminum layer. The exact structure of the OLEDs can be found in Table 1. The materials required for OLED production are shown in Table 3.

[0171] All materials are thermally evaporated in a vacuum chamber. The emission layer always consists of at least one matrix material (host material) and one emitting dopant (emitter), which is co-evaporated into the matrix material(s) in a specific volume fraction. A specification such as IC1:IC3:TEG1 (55%:35%:10%) means that the IC1 material is present in the layer at a volume fraction of 55%, IC3 at a volume fraction of 35%, and TEG1 at a volume fraction of 10%. Similarly, the electron-transport layer can also consist of a mixture of two materials.

[0172] OLEDs are characterized as standard. For this purpose, the electroluminescence spectra, current efficiency (measured in cd / A), power efficiency (measured in λm / W), and external quantum efficiency (EQE, measured in percent) are determined as a function of luminance, calculated from current-voltage-luminance curves (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 CIE 1931 x and y color coordinates are calculated from them. The value U1000 in Table 2 refers to the voltage required for a luminance of 1000 cd / m². SE1000 and LE1000 refer to the current and power efficiencies achieved at 1000 cd / m². Finally, EQE1000 refers to the external quantum efficiency at an operating luminance of 1000 cd / m 2< .The lifetime LD is defined as the time after which the luminance drops from the initial luminance to a certain percentage L1 when operating at a constant current. A value of L0;j0 = 4000 cd / m 2< and L1 = 70% in Table 2 means that the lifetime specified in column LD corresponds to the time after which the initial luminance drops from 4000 cd / m 2< to 2800 cd / m 2<. Similarly, L0;j0 = 20 mA / cm 2< , L1 = 80% means that the luminance drops to 80% of its initial value after the time LD when operating at 20 mA / cm 2<.

[0173] The data of the various OLEDs are summarized in Table 2. Examples V1-V3 are comparative examples according to the prior art, while examples E1-E16 show data from OLEDs according to the invention.

[0174] In the following, some of the examples are explained in more detail to illustrate the advantages of the OLEDs according to the invention. Use of mixtures according to the invention in the electron transport layer (ETL or EIL) of OLEDs

[0175] When used in the electron injection and electron transport layers in OLEDs, the materials of the invention provide significant improvements over the prior art in terms of component lifetime and / or efficiency. By using the compound EG1 of the invention, a lifetime increase of between 20% and 40% can be observed compared to the prior art (comparison of examples C1 and C2 with E1, and comparison of C3 with E2). A further technical advantage of the compounds of the invention is an increased efficiency of approximately 10% compared to the prior art (comparison of experiment C1 with E1). Table 1: Structure of the OLEDs HTL / IL (HATCN; 5 nm) / EBL / EML / HBL / ETL / EIL Example HTL EBL EML HBL ETL URGENT thickness thickness thickness thickness thickness thickness V1 SpA1 SpMA1 IC1:IC3:TEG1 --- SdT1 :LiQ --- 70nm 90nm (40%:40%:20%) 30nm (50%:50%) 40nm V2 SpA1 SpMA1 IC1:IC3:TEG1 --- SdT2:LiQ --- 70nm 90nm (40%:40%:20%) 30nm (50%:50%) 40nm V3 SpA1 SpMA1 IC1:TEG1 --- SdT3 LiF 70nm 90nm (90%:10%) 30nm 40nm 1nm E1 SpA1 SpMA1 IC1:IC3:TEG1 --- EG1:LiQ --- 70nm 90nm (40%:40%:20%) 30nm (50%:50%) 40nm E2 SpA1 SpMA1 IC1:TEG1 --- EG2 LiF 70nm 90nm (90%:10%) 30nm 40nm 1nm E3 SpA1 SpMA1 IC1:TEG1 IC1 EG3:LiQ --- 70nm 90nm (90%:10%) 30nm 10nm (50%:50%) 30nm E4 SpA1 SpMA1 IC1:TEG1 IC1 EG4 LiF 70nm 90nm (90%:10%) 30nm 10nm 30nm 1nm E5 SpA1 SpMA1 IC1:TEG1 EG5 EG5:LiQ --- 70nm 90nm (90%:10%) 30nm 10nm (50%:50%) 30nm E6 SpA1 SpMA1 IC1:TEG1 IC1 EG6 LiQ 70nm 90nm (90%:10%) 30nm 10nm 30nm 3nm E7 SpA1 SpMA1 IC1:IC3:TEG1 IC1 EG7:LiQ LiQ 70nm 90nm (60%:30%:10%) 30nm 10nm (50%:50%) 30nm 1nm E8 SpA1 SpMA1 H1:SEB --- EG8:LiQ --- 140nm 20nm (95%:5%) 20nm (50%:50%) 30nm E9 SpA1 SpMA1 H1:SEB --- EG9 LiQ 140nm 20nm (95%:5%) 20nm (50%:50%) 30nm 3nm E10 SpA1 SpMA1 H1:SEB --- EG10:LiQ --- 140nm 20nm (95%:5%) 20nm (50%:50%) 30nm E14 SpA1 SpMA1 H1:SEB --- EG11:LiQ --- 1 140nm 20nm (95%:5%) 20nm (50%:50%) 30nm E12 SpA1 SpMA1 H1:SEB --- EG12:LiQ --- 140nm 20nm (95%:5%) 20nm (50%:50%) 30nm E13 SpA1 SpMA1 EG13:IC3:TEG1 --- ST2:LiQ --- 70nm 90nm (45%:45%:10%) 30nm (50%:50%) 40nm E14 SpA1 SpMA1 IC5:TER3 --- EG14:LiQ --- 90nm 130nm (92%:8%) 40nm (50%:50%) 40nm E15 SpA1 SpMA1 IC5:TER3 --- EG15:LiQ --- 90nm 130nm (92%:8%) 40nm (50%:50%) 40nm E16 SpA1 SpMA1 IC5:TER3 --- EG16:LiQ --- 90nm 130nm (92%:8%) 40nm (50%:50%) 40nm Tabelle 2 : OLED data Bsp. U1000 (V) SE1000 (cd / A) LE1000 (Im / W) EQE 1000 CIE x / y bei 1000 cd / m 2< L 0 ; j 0 L1 % LD (h) V1 3.4 55 51 15.1% 0.33 / 0.63 20 mA / cm 2< 80 180 V2 3.3 60 57 16.5% 0.33 / 0.62 20 mA / cm 2< 80 160 V3 3.2 61 60 16.8% 0.34 / 0.62 20 mA / cm 2< 80 125 E1 3.3 59 56 16.4% 0.33 / 0.62 20 mA / cm 2< 80 220 E2 3.2 62 61 16.7% 0.33 / 0.63 20 mA / cm 2< 80 155 E3 3.4 57 53 16.2% 0.34 / 0.62 20 mA / cm 2< 80 135 E4 3.5 60 54 16.5% 032 / 0.64 20 mA / cm 2< 80 130 E5 3.6 59 51 16.0% 0.33 / 0.63 20 mA / cm 2< 80 120 E6 3.2 60 59 16.1% 0.31 / 0.64 20 mA / cm 2< 80 105 E7 3.6 61 53 16.6% 0.33 / 0.63 20 mA / cm 2< 80 235 E8 4.6 8.1 5.5 7.2% 0.13 / 014 6000 cd / m 2< 80 50 E9 4.5 7.8 5.2 6.7% 0.14 / 015 6000 cd / m 2< 80 25 E13 4.9 7.4 4.7 6.9% 0.14 / 0.13 6000 cd / m 2< 80 45 E11 4.7 8.3 5.5 7.5% 0.14 / 013 6000 cd / m 2< 80 40 E12 5.2 8.5 5.1 7.7% 0.14 / 013 6000 cd / m 2< 80 35 E13 3.4 58 54 15.4% 0.32 / 0.63 20 mA / cm 2< 80 105 E14 4.9 11.3 7.2 12.1% 0.67 / 0.33 4000 cd / m 2< 80 390 E15 4.3 11.3 8.3 12.3% 0.66 / 0.34 4000 cd / m 2< 80 360 E16 4.5 12.2 8.5 12.8% 0.67 / 0.33 4000 cd / m 2< 80 410 Tabelle 3: Structural formulas of the materials for OLEDs HATCN SpA1 SpMA1 LiQ SpMA2 TER1 IC1 ST2 IC3 TEG1 H1 SEB IC5 SdT1 SdT2 SdT3 EG1 EG2 EG3 EG4 EG5 EG6 EG7 EG8 EG9 EG10 EG11 EG12 EG13 EG14 EG15 EG16

Claims

1. Compound of the general formula (33): where the following definitions apply to the symbols and indices used: R1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(Ar1)2, C(=O)Ar1, P(=O)(Ar1)2, S(=O)Ar1, S(=O)2Ar1, CR2=CR2Ar1, CN, NO2, Si(R2)3, B(OR2)2, B(R2)2, B(N(R2)2)2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may in each case be substituted by one or more radicals R2, where one or more, preferably non-adjacent CH2 groups may be replaced by R2C=CR2, C=C, Si(R2)2, Ge(R2)2, Sn(R2)2, C=O, C=S, C=Se, C=NR2, P(=O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or 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 R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R2, or a combination of these systems; two or more adjacent substituents R1 may form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R3)2, CN, NO2, Si(R3)3, B(OR3)2, C(=O)R3, P(=O)(R3)2, S(=O)R3, S(=O)2R3, OSO2R3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, which may in each case be substituted by one or more radicals R3, where one or more non-adjacent CH2 groups may be replaced by R3C=CR3, C=C, Si(R3)2, Ge(R3)2, Sn(R3)2, C=O, C=S, C=Se, C=NR3, P(=O)(R3), SO, SO2, NR3, O, S or CONR3 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or 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 R3, or an aryloxy, arylalkoxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R3, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R3, or a combination of two or more of these groups; two or more adjacent radicals R2 may form a mono- or polycyclic, aliphatic or aromatic ring system with one another; where it is preferred if two or more adjacent substituents R2 do not form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R3 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by F; two or more substituents R3 may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; where it is preferred if two or more adjacent substituents R3 do not form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R5 is on each occurrence, identically or differently, F, Cl, Br, I, CHO, N(Ar1)2, C(=O)Ar1, P(=O)(Ar1)2, S(=O)Ar1, S(=O)2Ar1, CR2=CR2Ar1, CN, NO2, Si(R2)3, B(OR2)2, B(R2)2, B(N(R2)2)2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may in each case be substituted by one or more radicals R2, where one or more, preferably non-adjacent CH2 groups may be replaced by R2C=CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C=O, C=S, C=Se, C=NR2, P(=O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or 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 R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R2, or a combination of these systems; where two or more adjacent substituents R5 cannot form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R4 and R6 are on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(Ar1)2, C(=O)Ar1, P(=O)(Ar1)2, S(=O)Ar1, S(=O)2Ar1, CR2=CR2Ar1, CN, NO2, Si(R2)3, B(OR2)2, B(R2)2, B(N(R2)2)2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may in each case be substituted by one or more radicals R2, where one or more, preferably non-adjacent CH2 groups may be replaced by R2C=CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C=O, C=S, C=Se, C=NR2, P(=O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or 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 R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R2, or a combination of these systems; where two or more adjacent substituents R4 cannot form a mono- or polycyclic, aliphatic or aromatic ring system with one another; where two or more adjacent substituents R6 may form a mono- or polycyclic, aliphatic or aromatic ring system with one another, where it is preferred if two or more adjacent substituents R6 cannot form a mono- or polycyclic, aliphatic or aromatic ring system with one another; Q is C=O, C=S, S, C(R2)2, NR2 or O, preferably C(R2)2, NR2 or O, very preferably C(R2)2 or NR2 and particularly preferably C(R2)2; n is 0 or 1, where n = 0 is preferred and n = 0 means that the two aromatic rings A and B are not linked to one another via the group Q, but instead by a single bond; p is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, very preferably 0 or 1 and particularly preferably equal to 0; q is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, very preferably 0 or 1 and particularly preferably equal to 0; r is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, very preferably 0 or 1 and r is particularly preferably equal to 0; X is, identically or differently on each occurrence, N or CR1, where at least one X is equal to N, preferably at least two of the X are equal to N and very preferably all three X are equal to N; Ar1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R2; two of the radicals Ar1 may also be linked to one another 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; it is preferred if two radicals Ar1 are not linked to one another; V is a divalent group; U is a divalent group; v is 0 or 1, where v = 0 means that the ring D is connected directly to the remainder of the compound via a single covalent bond; u is 0 or 1; where u = 0 means that the ring C is connected directly to the remainder of the compound via a single covalent bond.

2. Compound of the general formula (4): where the following definitions apply to the symbols and indices used: R1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(Ar1)2, C(=O)Ar1, P(=O)(Ar1)2, S(=O)Ar1, S(=O)2Ar1, CR2=CR2Ar1, CN, NO2, Si(R2)3, B(OR2)2, B(R2)2, B(N(R2)2)2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may in each case be substituted by one or more radicals R2, where one or more, preferably non-adjacent CH2 groups may be replaced by R2C=CR2, C=C, Si(R2)2, Ge(R2)2, Sn(R2)2, C=O, C=S, C=Se, C=NR2, P(=O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or 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 R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R2, or a combination of these systems; two or more adjacent substituents R1 may form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R3)2, CN, NO2, Si(R3)3, B(OR3)2, C(=O)R3, P(=O)(R3)2, S(=O)R3, S(=O)2R3, OSO2R3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, which may in each case be substituted by one or more radicals R3, where one or more non-adjacent CH2 groups may be replaced by R3C=CR3, C=C, Si(R3)2, Ge(R3)2, Sn(R3)2, C=O, C=S, C=Se, C=NR3, P(=O)(R3), SO, SO2, NR3, O, S or CONR3 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or 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 R3, or an aryloxy, arylalkoxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R3, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R3, or a combination of two or more of these groups; two or more adjacent radicals R2 may form a mono- or polycyclic, aliphatic or aromatic ring system with one another; where it is preferred if two or more adjacent substituents R2 do not form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R3 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by F; two or more substituents R3 may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; where it is preferred if two or more adjacent substituents R3 do not form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R5 is on each occurrence, identically or differently, F, Cl, Br, I, CHO, N(Ar1)2, C(=O)Ar1, P(=O)(Ar1)2, S(=O)Ar1, S(=O)2Ar1, CR2=CR2Ar1, CN, NO2, Si(R2)3, B(OR2)2, B(R2)2, B(N(R2)2)2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may in each case be substituted by one or more radicals R2, where one or more, preferably non-adjacent CH2 groups may be replaced by R2C=CR2, C=C, Si(R2)2, Ge(R2)2, Sn(R2)2, C=O, C=S, C=Se, C=NR2, P(=O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or 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 R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R2, or a combination of these systems; where two or more adjacent substituents R6 cannot form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R4 and R6 are on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(Ar1)2, C(=O)Ar1, P(=O)(Ar1)2, S(=O)Ar1, S(=O)2Ar1, CR2=CR2Ar1, CN, NO2, Si(R2)3, B(OR2)2, B(R2)2, B(N(R2)2)2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may in each case be substituted by one or more radicals R2, where one or more, preferably non-adjacent CH2 groups may be replaced by R2C=CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C=O, C=S, C=Se, C=NR2, P(=O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or 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 R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R2, or a combination of these systems; where two or more adjacent substituents R4 cannot form a mono- or polycyclic, aliphatic or aromatic ring system with one another; where two or more adjacent substituents R6 may form a mono- or polycyclic, aliphatic or aromatic ring system with one another, where it is preferred if two or more adjacent substituents R6 cannot form a mono- or polycyclic, aliphatic or aromatic ring system with one another; Q is C=O, C=S, S, C(R2)2, NR2 or O, preferably C(R2)2, NR2 or O, very preferably C(R2)2 or NR2 and particularly preferably C(R2)2; n is 0 or 1, where n = 0 is preferred and n = 0 means that the two aromatic rings A and B are not linked to one another via the group Q, but instead by a single bond; p is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, very preferably 0 or 1 and particularly preferably equal to 0; q is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, very preferably 0 or 1 and particularly preferably equal to 0; r is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, very preferably 0 or 1 and r is particularly preferably equal to 0; X is, identically or differently on each occurrence, N or CR1, where at least one X is equal to N, preferably at least two of the X are equal to N and very preferably all three X are equal to N; Ar1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R2; two of the radicals Ar1 may also be linked to one another 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; it is preferred if two radicals Ar1 are not linked to one another; Q' are, identically to or differently from one another, C=O, C=S, S, C(R2)2, NR2 or O, preferably C(R2)2, NR2 or O, very preferably C(R2)2 or NR2 and particularly preferably C(R2)2; a is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, very preferably 0 or 1 and particularly preferably equal to 0; b is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, very preferably 0 or 1 and particularly preferably equal to 0; a+b is always less than or equal to 7, a+b is preferably equal to 0, 1, 2 or 3, a+b is very preferably equal to 0, 1 or 2, a+b is particularly preferably equal to 0 or 1 and a+b is very particularly preferably equal to 0; m is 0 or 1, where m = 0 is preferred and m = 0 means that the two aromatic rings are not linked to one another via the group Q', but instead by a single bond; V is a divalent group; U is a divalent group; v is 0 or 1, where v = 0 means that the ring D is connected directly to the remainder of the compound via a single covalent bond; u is 0 or 1; where u = 0 means that the ring C is connected directly to the remainder of the compound via a single covalent bond.

3. Compound according to Claim 1 or 2, characterised in that the compound is a small molecule having a molecular weight of at most 3000 g / mol.

4. Compound according to Claim 2 or 3, if dependent on Claim 2, characterised in that the compound has the general formula (23), preferably the general formula (24).

5. Compound according to one or more of Claims 2 to 4, if dependent on Claim 2, characterised in that the compound has the general formula (25) or (26).

6. Compound according to Claim 1, characterised in that two or more adjacent substituents R1 do not form a mono- or polycyclic, aliphatic or aromatic ring system with one another.

7. Compound of the general formula (34): where the following definitions apply to the symbols and indices used: R1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(Ar1)2, C(=O)Ar1, P(=O)(Ar1)2, S(=O)Ar1, S(=O)2Ar1, CR2=CR2Ar1, CN, NO2, Si(R2)3, B(OR2)2, B(R2)2, B(N(R2)2)2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may in each case be substituted by one or more radicals R2, where one or more, preferably non-adjacent CH2 groups may be replaced by R2C=CR2, C=C, Si(R2)2, Ge(R2)2, Sn(R2)2, C=O, C=S, C=Se, C=NR2, P(=O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or 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 R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R2, or a combination of these systems; two or more adjacent substituents R1 may form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R3)2, CN, NO2, Si(R3)3, B(OR3)2, C(=O)R3, P(=O)(R3)2, S(=O)R3, S(=O)2R3, OSO2R3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, which may in each case be substituted by one or more radicals R3, where one or more non-adjacent CH2 groups may be replaced by R3C=CR3, C=C, Si(R3)2, Ge(R3)2, Sn(R3)2, C=O, C=S, C=Se, C=NR3, P(=O)(R3), SO, SO2, NR3, O, S or CONR3 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or 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 R3, or an aryloxy, arylalkoxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R3, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R3, or a combination of two or more of these groups; two or more adjacent radicals R2 may form a mono- or polycyclic, aliphatic or aromatic ring system with one another; where it is preferred if two or more adjacent substituents R2 do not form a mono-or polycyclic, aliphatic or aromatic ring system with one another; R3 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by F; two or more substituents R3 may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; where it is preferred if two or more adjacent substituents R3 do not form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R5 is on each occurrence, identically or differently, F, Cl, Br, I, CHO, N(Ar1)2, C(=O)Ar1, P(=O)(Ar1)2, S(=O)Ar1, S(=O)2Ar1, CR2=CR2Ar1, CN, NO2, Si(R2)3, B(OR2)2, B(R2)2, B(N(R2)2)2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may in each case be substituted by one or more radicals R2, where one or more, preferably non-adjacent CH2 groups may be replaced by R2C=CR2, C=C, Si(R2)2, Ge(R2)2, Sn(R2)2, C=O, C=S, C=Se, C=NR2, P(=O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or 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 R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R2, or a combination of these systems; where two or more adjacent substituents R6 cannot form a mono- or polycyclic, aliphatic or aromatic ring system with one another; R4 and R6 are on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(Ar1)2, C(=O)Ar1, P(=O)(Ar1)2, S(=O)Ar1, S(=O)2Ar1, CR2=CR2Ar1, CN, NO2, Si(R2)3, B(OR2)2, B(R2)2, B(N(R2)2)2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may in each case be substituted by one or more radicals R2, where one or more, preferably non-adjacent CH2 groups may be replaced by R2C=CR2, C=C, Si(R2)2, Ge(R2)2, Sn(R2)2, C=O, C=S, C=Se, C=NR2, P(=O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or 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 R2, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R2, or a combination of these systems; where two or more adjacent substituents R4 cannot form a mono- or polycyclic, aliphatic or aromatic ring system with one another; where two or more adjacent substituents R6 may form a mono- or polycyclic, aliphatic or aromatic ring system with one another, where it is preferred if two or more adjacent substituents R6 cannot form a mono- or polycyclic, aliphatic or aromatic ring system with one another; Q is C=O, C=S, S, C(R2)2, NR2 or O, preferably C(R2)2, NR2 or O, very preferably C(R2)2 or NR2 and particularly preferably C(R2)2; n is 0 or 1, where n = 0 is preferred and n = 0 means that the two aromatic rings A and B are not linked to one another via the group Q, but instead by a single bond; p is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, very preferably 0 or 1 and particularly preferably equal to 0; q is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, very preferably 0 or 1 and particularly preferably equal to 0; r is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, very preferably 0 or 1 and r is particularly preferably equal to 0; X is, identically or differently on each occurrence, N or CR1, where at least one X is equal to N, preferably at least two of the X are equal to N and very preferably all three X are equal to N; Ar1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R2; two of the radicals Ar1 may also be linked to one another 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; it is preferred if two radicals Ar1 are not linked to one another; Q' are, identically to or differently from one another, C=O, C=S, S, C(R2)2, NR2 or O, preferably C(R2)2, NR2 or O, very preferably C(R2)2 or NR2 and particularly preferably C(R2)2; a is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, very preferably 0 or 1 and particularly preferably equal to 0; b is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, very preferably 0 or 1 and particularly preferably equal to 0; a+b is always less than or equal to 7, a+b is preferably equal to 0, 1, 2 or 3, a+b is very preferably equal to 0, 1 or 2, a+b is particularly preferably equal to 0 or 1 and a+b is very particularly preferably equal to 0; m is 0 or 1, where m = 0 is preferred and m = 0 means that the two aromatic rings are not linked to one another via the group Q', but instead by a single bond; V is a divalent group; U is a divalent group; v is 0 or 1, where v = 0 means that the ring D is connected directly to the remainder of the compound via a single covalent bond; u is 0 or 1, where u = 0 means that the ring C is connected directly to the remainder of the compound via a single covalent bond.

8. Compound according to one or more of Claims 1, 3, if dependent on Claim 1, 6 or 7, characterised in that the compound has the general formula (35), preferably the general formula (36) or (37).

9. Compound according to Claim 7, characterised in that the compound has the general formula (44), preferably the general formula (45).

10. Compound according to Claim 7 or 9, characterised in that the compound has the general formula (46) or (47).

11. Composition comprising at least one compound according to one or more of Claims 1 to 10 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, matrix materials, electron-transport materials, electron-injection materials, hole-conductor materials, hole-injection materials, electron-blocking materials and hole-blocking materials, wide band gap materials and n-dopants, where the further compound is preferably an electron-transport material or matrix material.

12. Formulation comprising at least one compound according to one or more of Claims 1 to 10 or at least one composition according to Claim 11 and at least one solvent.

13. Use of at least one compound according to one or more of Claims 1 to 10 or at least one composition according to Claim 11 in an electronic device, preferably in an organic electroluminescent device, very preferably in an organic light-emitting diode (OLED) or organic light-emitting electrochemical cell (OLEC, LEEC, LEC), very particularly preferably in an OLED, preferably in an emission layer (EML), electron-transport layer (ETL) and in a hole-blocking layer (HBL), and very preferably in an EML and ETL.

14. Electronic device containing at least one compound according to one or more of Claims 1 to 10 or at least one composition according to Claim 11, preferably in an emission layer (EML), electron-transport layer (ETL) and in a hole-blocking layer (HBL), and very preferably in an EML or ETL and very particularly preferably in the ETL, where the electronic device is preferably selected from organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors, organic photoreceptors, more preferably is an organic electroluminescent device.

15. Electronic device according to Claim 14, characterised in that it is an organic electroluminescent device selected from the group consisting of organic light-emitting transistors (OLETs), organic field-quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O-lasers) and organic light-emitting diodes (OLEDs), preferably OLECs and OLEDs, very preferably OLEDs.

16. Process for the production of an electronic device according to Claim 14 or 15, characterised in that at least one organic layer is applied by gas-phase deposition or from solution.