Nitrogen-containing heterocycles for organic electroluminescent devices

Abstract

The present invention relates to nitrogen-containing heterocycles that are suitable for use in electronic devices, and to electronic devices, in particular organic electroluminescent devices, containing these heterocycles.

Description

[0001] Nitrogen-containing heterocycles for organic electroluminescent devices

[0002] The present invention relates to nitrogen-containing heterocycles for use in electronic devices, in particular in organic electroluminescent devices, as well as to electronic devices, in particular organic electroluminescent devices, containing these materials.

[0003] In organic electroluminescent devices, phosphorescent organometallic complexes are often used as emitting materials. For quantum mechanical reasons, up to four times the energy and power efficiency is possible when using organometallic compounds as phosphorescence emitters. In general, there is still room for improvement in electroluminescent devices, especially in electroluminescent devices that exhibit triplet emission (phosphorescence). The properties of phosphorescent electroluminescent devices are not only determined by the triplet emitters used. The other materials used, such as matrix materials, are also of particular importance. Improvements to these materials can therefore also lead to significant improvements in the properties of the electroluminescent devices.

[0004] In addition to an emission layer, many electroluminescent devices comprise additional layers, such as one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, and / or charge generation layers. These layers have a significant impact on the performance of electroluminescent devices.

[0005] Among other things, the electroluminescent devices described above are described in document WO 2014 / 015938 A1. In general, these materials, for example for use as matrix materials, still require improvement, particularly with regard to lifetime, but also with regard to the efficiency and operating voltage of the device.

[0006] 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.

[0007] In particular, the object of the present invention is to provide compounds that result in a long lifetime, good efficiency, and low operating voltage. Electron-injection materials, electron-transport materials, and hole-blocking materials contribute in particular to these properties. Furthermore, the properties of the matrix materials, also referred to herein as host materials, also have a significant influence on the lifetime and efficiency of the organic electroluminescent device.

[0008] Furthermore, it is the object of the present invention to provide compounds which are characterized by a low refractive index (RI).

[0009] A further object of the present invention can be seen in providing compounds suitable for use in phosphorescent or fluorescent electroluminescent devices, in particular as matrix materials. In particular, it is an object of the present invention to provide matrix materials suitable for green or blue phosphorescent electroluminescent devices and, optionally, also for red or yellow phosphorescent electroluminescent devices. Furthermore, the compounds, particularly when used as host material, electron injection material, electron transport material, or hole-blocking material in organic electroluminescent devices, should lead to devices exhibiting excellent color purity.

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

[0011] Furthermore, the electronic devices should be able to be used or adapted for a variety of purposes. In particular, the performance of the electronic devices should be maintained over a wide temperature range.

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

[0013] The present invention relates to a compound comprising at least one structure of formula (I), preferably a compound according to formula (I), where the symbols are:

[0014] Z a represents, the same or different at each occurrence, Ar, R c , L 1 -Q, or L 1-N(Ar)2, preferably for R c , L 1 -Q or L 1 -N(Ar)2;

[0015] Q represents, identically or differently at each occurrence, an electron transport group, preferably a nitrogen-containing heteroaryl group having 5 to 12 ring atoms, particularly preferably having 6 to 12 ring atoms, which may be substituted with one or more radicals R d can be substituted;

[0016] L 1 represents, identically or differently at each occurrence, a bond or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R;

[0017] R a is at each occurrence, identically or differently, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 10 C atoms, each of which is substituted by one or more radicals R 2may be substituted, or an aromatic or heteroaromatic ring system with 5 to 20 aromatic ring atoms, each substituted by one or more radicals R 2 may be substituted, preferably a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, each substituted by one or more radicals R 2 may be substituted, or a phenyl group, each substituted with one or more radicals R 2 can be substituted, two or more, preferably adjacent, substituents R a form a ring system with each other;

[0018] R b is, at each occurrence, identically or differently, H, D, straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 10 C atoms, each of which is substituted by one or more radicals R 2may be substituted, or an aromatic or heteroaromatic ring system with 5 to 20 aromatic ring atoms, each substituted by one or more radicals R 2 may be substituted, preferably H, D, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms or a phenyl group, each substituted with one or more radicals R 2 can be substituted, two, preferably adjacent substituents R b form a ring system with each other, particularly preferably H or D;

[0019] Ar is, on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R. Two radicals Ar which bind to the same N atom may also be bridged to one another by a single bond or a bridge selected from B(R), C(R)2, Si(R)2, C=O, C=NR, C=C(R)2, RC=CR, O, S, S=O, SO2, N(R), P(R), P(=O)R and an ortho-linked phenylene group which may be substituted by one or more radicals R, preferably selected from C(R)2, O, N(R) and an ortho-linked phenylene group which may be substituted by one or more radicals R. Preferably, Ar is, on each occurrence, identically or differently, an aryl or heteroaryl group having 6 to 40 aromatic ring atoms. which may be substituted by one or more radicals R, whereby two radicals Ar, which bind to the same N-atom,also be bridged together by a single bond or a bridge selected from B(R), C(R)2, Si(R)2, C=O, C=NR, C=C(R)2, RC=CR, O, S, S=O, SO2, N(R), P(R), P(=O)R and an ortho-linked phenylene group which may be substituted by one or more radicals R, preferably selected from C(R)2, O, N(R) and an ortho-linked phenylene group which may be substituted by one or more radicals R; R, R, c , R d is, at each occurrence, the same or different: H, D, OH, F, CI, Br, I, CN, NO2, N(Ar')2, N(R 1 )2, C(=O)N(Ar')2, C(=O)N(R 1 )2, C(Ar')3, C(R 1 )3, Si(Ar')3, Si(R 1 )3, B(Ar')2, B(R 1 )2, C(=O)Ar', C(=O)R 1 , P(=O)(Ar')2, P(=O)(R 1 )2, P(Ar')2, P(R 1 )2, S(=O)Ar', S(=O)R 1 , S(=O)2Ar', S(=O)2R 1 , OSO2Ar', OSO2R 1, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group is each substituted with one or more radicals R 1 may be substituted, wherein one or more non-adjacent CH2 groups are represented by R 1 C=CR 1 , C^C, Si(R 1 )2, C=O, C=S, C=Se, C=NR 1 , -C(=O)O-, -C(=O)NR 1 -, NR 1 , P(=O)(R 1 ), -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which is substituted by one or more radicals R 1 may be substituted, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1can be substituted, two radicals R, R d also with each other or a residue R, R d with another group, in particular a residue R c form a ring system;

[0020] Ar' is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is substituted with one or more radicals R 1 may be substituted, whereby two radicals Ar' which bind to the same C-atom, Si-atom, N-atom, P-atom or B-atom may also be connected by a single bond or a bridge selected from B(R 1 ), C(R 1 )2, Si(R 1 )2, C=O, C=NR 1 , C=C(R 1 )2, O, S, S=O, SO2, N(R 1 ), P(R 1 ) and P(=O)R 1 , be bridged together;

[0021] R 1 is, at each occurrence, the same or different: H, D, F, CI, Br, I, CN, NO2, N(Ar”)2, N(R 2 )2, C(=O)Ar”, C(=O)R 2, P(=O)(Ar”)2, P(Ar”)2, B(Ar”)2, B(R 2 )2, C(Ar”)3, C(R 2 )3, Si(Ar”)3, Si(R 2 )3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms or an alkenyl group having 2 to 40 C atoms, each of which is substituted by one or more radicals R 2 may be substituted, with one or more non-adjacent CH2 groups being replaced by -R 2 C=CR 2 -, -C=C-, Si(R 2 )2, C=O, C=S, C=Se, C=NR 2 , -C(=O)O-, -C(=O)NR 2 -, NR 2 , P(=O)(R 2 ), -O-, -S-, SO or SO2 and where one or more H atoms can be replaced by D, F, CI, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which is substituted by one or more radicals R 2may be substituted, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 2 may be substituted, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms which may be substituted with one or more radicals R 2 may be substituted, or a combination of these systems; two or more, preferably adjacent, radicals R 1 form a ring system, whereby one or more residues R 1 form a ring system with another part of the compound;

[0022] Ar” is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is substituted by one or more radicals R 2may be substituted, whereby two radicals Ar” which bind to the same C-atom, Si-atom, N-atom, P-atom or B-atom may also be linked by a single bond or a bridge selected from B(R 2 ), C(R 2 )2, Si(R 2 )2, C=O, C=NR 2 , C=C(R 2 )2, O, S, S=O, SO2, N(R 2 ), P(R 2 ) and P(=O)R 2 , be bridged together;

[0023] R 2 is selected, identically or differently at each occurrence, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D, F, CI, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms, where two or more, preferably adjacent, substituents R 2form a ring system with each other.

[0024] An aryl group within the meaning of this invention contains 6 to 40 C atoms; a heteroaryl group within the meaning of this invention contains 3 to 40 C atoms and at least one heteroatom, with the proviso that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aryl group or heteroaryl group is understood to be either a simple aromatic cycle, i.e. benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a condensed (fused) aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatics linked to one another by a single bond, such as biphenyl, are not referred to as aryl or heteroaryl groups, but as an aromatic ring system.

[0025] An electron-poor heteroaryl group within the meaning of the present invention is a heteroaryl group that has at least one heteroaromatic six-membered ring containing at least one nitrogen atom. Further aromatic or heteroaromatic five-membered rings or six-membered rings can be fused to this six-membered ring. Examples of electron-poor heteroaryl groups are pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline, or quinoxaline.

[0026] 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 3 to 60 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of C atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O, and / or S. An aromatic or heteroaromatic ring system within the meaning of this invention is understood to mean a system that does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups can also be connected by a non-aromatic unit, such as a C, N, or O atom. For example, systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc.are understood as aromatic ring systems within the meaning of this invention, as are systems in which two or more aryl groups are linked, for example, by a short alkyl group. The aromatic ring system is preferably selected from fluorene, 9,9'-spirobifluorene, 9,9-diarylamine, or groups in which two or more aryl and / or heteroaryl groups are linked by single bonds.

[0027] In the context of the present invention, an aliphatic hydrocarbon radical or an alkyl group or an alkenyl or alkynyl group which may contain 1 to 20 C atoms and in which individual H atoms or CH2 groups may be substituted by the above-mentioned groups, preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, neo-pentyl, cyclopentyl, n-hexyl, neo-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, Cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentinyl, hexynyl, heptynyl or octynyl.Unter einer Alkoxygruppe mit 1 bis 40 C-Atomen werden bevor- zugt 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, Cyclo- octyloxy, 2-Ethylhexyloxy, Pentafluorethoxy und 2,2,2-Trifluorethoxy ver- standen. Unter einer Thioalkylgruppe mit 1 bis 40 C-Atomen werden ins- besondere Methylthio, Ethylthio, n-Propylthio, i-Propylthio, n-Butylthio,.

[0028] 1-Butylthio, s-Butylthio, t-Butylthio, n-Pentylthio, s-Pentylthio, n-Hexylthio, Cyclohexylthio, n-Heptylthio, Cycloheptylthio, n-Octylthio, Cyclooctylthio,

[0029] 2-Ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio, or octynylthio. In general, alkyl, alkoxy, or thioalkyl groups according to the present invention can be straight-chain, branched, or cyclic, where one or more non-adjacent CH2 groups can be replaced by the above-mentioned groups; Furthermore, one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO2, preferably F, Cl or CN, more preferably F or CN, particularly preferably CN.

[0030] An aromatic or heteroaromatic ring system with 5 - 60 or 5 to 40 aromatic ring atoms, which may also be substituted with the above-mentioned radicals and which may be linked to the aromatic or heteroaromatic ring via any position, is understood to mean, in particular, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, iso- benzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, iso-quinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-chinolin, Phenothiazin, Phenoxazin, Pyrazol, Indazol, Imidazol, Benzimidazol, Naphthimidazol, Phenanthrimidazol, Pyridimidazol, Pyrazin- imidazol, Chinoxalinimidazol, Oxazol, Benzoxazol, Naphthoxazol, Anthroxazol, Phenanthroxazol, Isoxazol, 1 ,2-Thiazol, 1 ,3-Thiazol, Benzo- thiazol, Pyridazin, Hexaazatriphenylen, Benzopyridazin, Pyrimidin, Benz- pyrimidin, Chinoxalin, 1 ,5-Diazaanthracen, 2,7-Diazapyren, 2,3-Diaza- pyren, 1 ,6-Diazapyren, 1 ,8-Diazapyren, 4,5-Diazapyren, 4,5,9, 10-Tetra- azaperylen, 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-Oxa- diazol, 1 ,3,4-Oxadiazol, 1 ,2,3-Thiadiazol, 1 ,2,4-Thiadiazol, 1 ,2,5-Thiadi- azol, 1 ,3,4-Thiadiazol, 1 ,3,5-Triazin, 1 ,2,4-Triazin, 1 ,2,3-Triazin, Tetrazol, 1 ,2,4,5-Tetrazin, 1 ,2,3,4-Tetrazin, 1 ,2,3,5-Tetrazin, Purin, Pteridin, Indolizin und Benzothiadiazol oder Gruppen,which are derived from combinations of these systems. The phrase "two or more residues can form a ring" is understood, for the purposes of this description, to mean, among other things, that the two residues are linked by a chemical bond with the formal elimination of two hydrogen atoms. This is illustrated by the following scheme.

[0031] Furthermore, the above formulation should also be understood to mean that if one of the two residues represents hydrogen, the second residue binds to the position to which the hydrogen atom was bonded, forming a ring. This is illustrated by the following scheme:

[0032] In a preferred embodiment, the compounds according to the invention can preferably comprise at least one structure of the formulas (I-1) to (I-4), and are particularly preferably selected from the compounds of the formulas (I-1) to (I-4),

[0033] where the symbols Ar, Lr 1 , Q, R a , R b and R c have the meanings given above, in particular for formula (I).

[0034] The group Q represents, identically or differently at each occurrence, an electron transport group, where the electron transport group preferably represents a nitrogen-containing heteroaryl group having 5 to 12 ring atoms, particularly preferably having 6 to 12 ring atoms, which can be substituted with one or more radicals R dmay be substituted. The group Q preferably represents an electron-deficient heteroaryl group, which particularly preferably further exhibits the properties set out above and below.

[0035] Particular advantages can be achieved in particular by the group Q being a nitrogen-containing heteroaryl group having 6 to 12 ring atoms with at least two nitrogen atoms in a ring, which can be substituted with one or more radicals R d may be substituted, wherein the carbon atoms adjacent to at least two of the nitrogen atoms in a ring are not bonded to a hydrogen atom.

[0036] Electron-transport groups are widely known in the art and enhance the ability of compounds to transport and / or conduct electrons. These include, in particular, nitrogen-containing heteroaryl groups with 5 to 12 ring atoms, particularly preferably with 6 to 12 ring atoms, which are generally electron-poor heteroaryl groups.

[0037] Preferably, the group Q can be a pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, quinoline, isoquinoline, imidazole and / or benzimidazole group, preferably a pyrimidine, pyrazine, triazine, quinazoline, quinoxaline and / or benzimidazole group, particularly preferably a pyrimidine, triazine, quinazoline and / or quinoxaline group, particularly preferably a pyrimidine and / or triazine group, very particularly preferably a triazine group which is reacted with one or more radicals R d can be substituted.

[0038] It can be particularly preferably provided that the group Q represents a pyrimidine, pyrazine, triazine, quinazoline, quinoxaline and / or benzimidazole group, particularly preferably a pyrimidine, triazine, quinazoline and / or quinoxaline group, particularly preferably a pyrimidine and / or triazine group, very particularly preferably a triazine group, which is reacted with one or more radicals R d may be substituted, wherein the carbon atoms adjacent to at least two of the nitrogen atoms in a ring are not bonded to a hydrogen atom.

[0039] In a particularly preferred embodiment, the group Q can be a pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, imidazole and / or benzimidazole group, preferably a pyrimidine, pyrazine, triazine, quinazoline, quinoxaline and / or benzimidazole group, which can be substituted with one or more radicals R d may be substituted, wherein the carbon atoms adjacent to at least two of the nitrogen atoms are substituted by an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each substituted by one or more radicals R 1 can be substituted. Among the particular advantages that can be achieved by this embodiment is, in particular, a longer service life of the electronic devices.

[0040] Accordingly, it can be provided with particular advantage that the group Q represents a pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, imidazole and / or benzimidazole group, preferably a pyrimidine, pyrazine, triazine, quinazoline, quinoxaline and / or benzimidazole group, which is reacted with one or more radicals R d may be substituted, wherein the carbon atoms adjacent to at least two of the nitrogen atoms are substituted by an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each substituted by one or more radicals R 1 may be substituted, or the group Q represents a pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, imidazole and / or benzimidazole group, preferably a pyrimidine, pyrazine, triazine, quinazoline, quinoxaline and / or benzimidazole group, which is substituted with one or more radicals R dmay be substituted, wherein the carbon atoms adjacent to at least two of the nitrogen atoms are linked to a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group adjacent to the C atom linked to the respective N atom does not have any acidic hydrogen atoms and is each linked to one or more radicals R 1 may be substituted, wherein the carbon atoms adjacent to at least two of the nitrogen atoms are preferably connected to an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which is substituted by one or more radicals R 1In a further preferred embodiment, it can be provided that the group Q is selected, identically or differently at each occurrence, from structures of the formulas (Q-1) to (Q-16), where R d which has been mentioned above, in particular for formula (I), the dashed bonds mark the attachment positions and the other symbols have the following meaning:

[0041] Y 1 stands for 0, S, NR d or C(R d )2, preferably 0, NR d or C(R d )2; n is independently 0, 1, 2 or 3 at each occurrence, preferably 0, 1 or 2; and m is independently 0, 1, 2, 3 or 4 at each occurrence, preferably 0, 1 or 2.

[0042] Here, the structures (Q-1) to (Q-14) are preferred, structures (Q-1) to (Q-8) are particularly preferred and the structures (Q-1), (Q-4), (Q-7) and (Q-12) are particularly preferred and the structure (Q-1) is very particularly preferred.

[0043] In a further preferred embodiment, it can be provided that the group Q is selected, identically or differently at each occurrence, from structures of the formulas (Q-1 ') to (Q-15'),

[0044] where R d which has been mentioned above, in particular for formula (I), the dashed bonds mark the attachment positions and the other symbols have the following meaning:

[0045] R e is at each occurrence, identically or differently, a group N(Ar')2 or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each substituted by one or more radicals R 1can be substituted, two radicals R e also with each other or a residue R e with another group, in particular a residue R e form a ring system;

[0046] Y 1 stands for 0, S, NR d or C(R d )2, preferably 0, NR d or C(R d )2;n is independently 0, 1, 2 or 3 at each occurrence, and n is independently 0, 1, 2 or 3 at each occurrence, preferably 0, 1 or 2, and m is independently 0, 1, 2, 3 or 4 at each occurrence, preferably 0, 1 or 2.

[0047] Here, the structures (Q'-1 ) to (Q'-14) are preferred, structures (Q'-

[0048] 1 ) to (Q'-12) are particularly preferred and the structures (Q'-1 ), (Q'-4), (Q'-7) and (Q'-12) are particularly preferred and the structure (Q'-1 ) is very particularly preferred.

[0049] In a further preferred embodiment, it can be provided that the group Q is selected, identically or differently on each occurrence, from structures of the formulas (Q-1a), (Q-1b), (Q-1c), (Q-1d), (Q-1e), (Q-1f), (Q-1g), (Q-1h), (Q-1i), (Q-1j), (Q-1k), (Q-11), (Q-1m) and / or (Q-1n),

[0050] where R 1 which has the formula (I) mentioned above, in particular the dashed bond marks the attachment position and the following applies to the indices used: j is, independently at each occurrence, 0, 1, 2 or 3, preferably 0, 1 or 2; h is, independently at each occurrence, 0, 1, 2, 3 or 4, preferably 0, 1 or 2;

[0051] I is on each occurrence independently 0, 1, 2, 3, 4 or 5, preferably 0, 1 or 2. Furthermore, it can be provided that the group Ar is selected, identically or differently on each occurrence, from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene, which may each be substituted by one or more radicals R, preferably phenyl, biphenyl, fluorene, dibenzofuran, triphenylene, indolocarbazole.

[0052] In a further preferred embodiment, it can be provided that the group L 1 identically or differently represents a bond or is selected from structures of the formulas (L 1 -1 ) to (L 1 -22),

[0053] Formula (L 1-10) Formula (L 1 -12)

[0054] Formula (L 1 -13) Formula (L 1 -15)

[0055] Formula (L 1 -16) Formula (L 1 -17) Formula (L 1 -18)

[0056] Rh

[0057] Formula (L 1 -19)

[0058] where the symbols used are:

[0059] Y is CR2, O, S or NR, preferably O or NR; j is at each occurrence independently 0, 1, 2 or 3, preferably 0, 1 or 2; h is at each occurrence independently 0, 1, 2, 3 or 4, preferably 0, 1 or 2

[0060] R has the meaning given above, in particular for formula (I), and the dashed bond marks the attachment position.

[0061] The sum of the indices i, j and h in structures of the formulas (L 1 -1 ) to (L 1- 22) is preferably at most 6, particularly preferably at most 4 and most preferably at most 2.

[0062] In one embodiment, it can be provided that the group Q does not contain a carbazole group, preferably a carbazole group and / or no substituents of the formula N(Ar')2, N(R 1 )2 and particularly preferably does not comprise a hole transport group.

[0063] In one embodiment, it can be provided that the group L 1 no carbazole group, preferably no carbazole group and / or no substituents of the formula N(Ar')2, N(R 1 )2 and particularly preferably does not comprise a hole transport group.

[0064] Compounds in which the groups L 1and / or Q do not comprise a hole transport group are particularly suitable as electron injection material, electron transport material or hole blocking material which are used in a corresponding layer, wherein this layer generally does not contain an emitting compound.

[0065] In a further embodiment, it can be provided that the group L 1 a hole transport group, preferably a carbazole group and / or a substituent of the formula N(Ar')2, and particularly preferably a carbazole group.

[0066] In a further embodiment, it can be provided that the group Q comprises a hole transport group, preferably a carbazole group and / or a substituent of the formula N(Ar')2, and particularly preferably a carbazole group.

[0067] Compounds in which the groups L 1and / or Q comprise a hole transport group are particularly suitable as host materials used in combination with an emitting compound.

[0068] Hole-transport groups are widely known in the scientific community. These include, in particular, di- and triarylamine groups, carbazole groups, and groups with similar properties.

[0069] In a further preferred embodiment, it can be provided that the compounds according to the invention comprise a structure of the formulas (II-1) to (II-44), wherein the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (II-1) to (II-44),

[0070] Formula (II-43) Formula (II-44) where the symbols R, R a , R b , R c and R dhave the meanings given above, in particular for formula (I) and the following applies to the other symbols:

[0071] X represents, at each occurrence, the same or different, N, CR or C, in the case of a group bonded to the structure;

[0072] X I represents N or CR, the same or different at each occurrence d , preferably for N;

[0073] X 2 represents N or CR, the same or different at each occurrence d , preferably for CR d ;

[0074] Y represents O, S, NR or C(R)2, preferably O, NR or C(R)2; and Y 1 stands for 0, S, NR d or C(R d )2, preferably 0, NR d or C(R d )2.

[0075] Structures / compounds of the formulas (II-1), (II-2), (II-3), (II-6), (II-7), (II-12), (II-17), (II-18), (II-23), (II-28), (II-29), (II-34), (II-39) and (II-40) are preferred and structures / compounds of the formulas (II-1), (II-6), (II-7), (II-12) and (II-34) are particularly preferred.

[0076] Preferably, in particular in structures / compounds of the formulas (II-1) to (II-44), it can be provided that at most three, preferably at most two groups X per ring stand for N, preferably all X stand for CR, preferably at least one, particularly preferably at least two of the groups X per ring are selected from CH and CD. Furthermore, in particular in structures / compounds of the formulas (II-1) to (II-44), it can be provided that no more than four, preferably no more than two groups X stand for N, particularly preferably all groups X stand for CR, where preferably at most 4, particularly preferably at most 3 and especially preferably at most 2 of the groups CR, which X stands for, are not equal to the group CH.

[0077] In a further embodiment, in particular in structures / compounds of the formulas (II-1) to (II-44), it can be provided that at most three, preferably at most two groups X 2 per ring for N, preferably all X2 for CR d preferably at least one, particularly preferably at least two of the groups X 2 per ring selected from CH and CD.

[0078] In a further preferred embodiment, in particular in structures / compounds of the formulas (II-1) to (II-44), it can be provided that not more than four, preferably not more than two groups X 2 represent N, especially preferably all groups X 2 for CR d where preferably at most 4, particularly preferably at most 3 and especially preferably at most 2 of the groups CR, for which X 2 is not equal to the group CH.

[0079] In a further preferred embodiment, it can be provided that the compounds according to the invention comprise a structure of the formulas (III-1) to (III-48), wherein the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (III-1) to (III-48),

[0080] Formula (111-1 ) Formula (HI-2)

[0081] Formula (HI-3) Formula (III-4)

[0082] Formula (HI-5) Formula (HI-6)

[0083] 35 Formula (111-11) Formula (111-12)

[0084] Formula (111-13) Formula (111-14)

[0085] Formula (111-15) Formula (111-16)

[0086] Formula (111-17) Formula (111-18)

[0087] Formula (111-19) Formula (HI-20)

[0088] Formula (HI-23) Formula (HI-24)

[0089] Formula (111-27) Formula (111-28)

[0090] Formula (111-29) Formula (111-30)

[0091] Formula (111-31) Formula (111-32)

[0092] (R)n

[0093] Formula (111-39) Formula (111-40)

[0094] Formula (111-41 ) Formula (III-42)

[0095] Formula (III-43) Formula (111-44)

[0096] Formula (HI-45) Formula (III-46)

[0097] Formula (HI-47) Formula (111-48) where the symbols R, R a , R b , R c and R d have the meanings given above, in particular for formula (I) and the following applies to the other symbols:

[0098] Y is O, S, NR or C(R)2, preferably O, NR or C(R)2;

[0099] Y 1 is 0, S, NR d or C(R d )2, preferably 0, NR d or C(R d )2; n is independently 0, 1, 2 or 3 at each occurrence, preferably 0, 1 or 2; m is independently 0, 1, 2, 3 or 4 at each occurrence, preferably 0, 1 or 2.

[0100] Structures / compounds of the formulas (III-1), (III-2), (III-3), (III-4), (III-7), (III-8), (III-13), (III-19), (HI-20), (HI-25), (III-31), (HI-32), (III-37), (III-43) and (III-44) are preferred and structures / compounds of the formulas (III-1), (HI-7), (III-8), (III-13) and (III-37) are particularly preferred.

[0101] Furthermore, in particular in structures / compounds of the formulas (III-1) to (III-48), the sum of the indices m and n may be at most 10, preferably at most 8, particularly preferably at most 6 and particularly preferably at most 4.

[0102] In a preferred embodiment, it can be provided that the radical R, R a , R c , R d does not comprise an aromatic or heteroaromatic ring system which has three linearly condensed aromatic 6 rings, wherein preferably none of the radicals R, R a , R c , R d an aromatic or heteroaromatic ring system having three linearly condensed aromatic 6-membered rings.

[0103] Particularly preferably, it can be provided that the radical R, R a , R c , R ddoes not comprise an aromatic or heteroaromatic ring system which has three fused aromatic 6 rings, wherein preferably none of the radicals R, R a , R c , R d comprises an aromatic or heteroaromatic ring system having three fused aromatic 6-membered rings. Furthermore, it is particularly preferred that the group L1 does not comprise an aromatic or heteroaromatic ring system having three fused aromatic 6-membered rings.

[0104] Furthermore, it can be particularly preferred that the group Q does not comprise an aromatic or heteroaromatic ring system which has three aromatic 6 rings fused to one another.

[0105] Furthermore, it can be particularly preferred that the group Ar does not comprise an aromatic or heteroaromatic ring system which has three aromatic 6 rings fused to one another.

[0106] Most preferably, the compound may not comprise an aromatic or heteroaromatic ring system having three aromatic 6 rings fused to one another.

[0107] In a preferred development of the present invention, it can be provided that at least two, preferably adjacent radicals R, R d with the other groups to which the two residues R, R d bind, forming a condensed ring, where the two residues R, R d form at least one structure of the formulas (RA-1) to (RA-12)

[0108] Formula RA-2 Formula RA-3

[0109] Formula RA-4 Formula RA-5 Formula RA-6

[0110] Formula RA-7 Formula RA-8 Formel RA ' 9

[0111] Formula RA-10 Formula RA-11 Formula RA-12 where R 1has the meaning explained above, the dashed bonds are the attachment points to the atoms of the groups to which the two radicals R, R d bind, represent, and the other symbols have the following meaning:

[0112] Y 3 is the same or different at each occurrence C(R 1 )2, (R 1 )2C-C(R 1 )2, (R 1 )C=C(R 1 ), NR 1 , NAr', 0 or S, preferably C(R 1 )2, (R 1 )2C-C(R 1 )2, (R 1 )C=C(R 1 ), 0 or S;

[0113] R f is, identically or differently at each occurrence, F, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group is each substituted with one or more radicals R2 may be substituted, wherein one or more non-adjacent CH2 groups are represented by R 2 C=CR 2 , C^C, Si(R 2 )2, C=O, C=S, C=Se, C=NR 2 , -C(=O)O-, -C(=O)NR 2 -, NR 2 , P(=O)(R 2 ), -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which is substituted by one or more radicals R 2 may be substituted, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 2 can be substituted; two radicals R f also with each other or a residue R f with a remainder R 1 or form a ring system with another group, where R 2has the meaning given in claim 1; r is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1; s is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2; t is 0, 1, 2, 3, 4, 5, 6, 7 or 8, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2; v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2.

[0114] Structures of the formulas RA-1, RA-3, RA-4 and RA-5 are preferred and structures of the formulas RA-4 and RA-5 are particularly preferred.

[0115] In a preferred embodiment of the invention, preferably at least two, preferably adjacent, radicals R, R d with the other groups to which the two residues R, R d bind, a condensed ring, where the two residues R, R d Form structures of formulas (RA-1 a) to (RA-4f)

[0116] ; f^7\ / VR ?"R

[0117] R f R f R f R 1 R\ 1 R 1 Rf

[0118] R 1 ' R 1

[0119] Formula RA-1 a Formula RA-1 b Formula RA- 1 c

[0120] Formula RA-2c

[0121] Formula RA-3a Formula RA-3b

[0122] Formula RA-4a Formula RA-4c where the dashed bonds represent the attachment points to the atoms of the groups to which the two radicals R, R d bind, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2 and the symbols R 1 , R 2 , R f and the indices s and t have the meaning set out above, in particular for formula (I) and / or formulas (RA-1) to (RA-12).

[0123] Structures of the formula RA-4f are preferred. Furthermore, it can be provided that the at least two radicals R, R d, which form structures of the formulas (RA-1 ) to (RA-12) and / or (RA-1 a) to (RA-4f) and form a condensed ring, radicals R, R d from neighboring groups X, X 2 represent or radicals R, R d which each bind to adjacent C atoms, whereby these C atoms are preferably connected via a bond.

[0124] In a further preferred embodiment, preferably at least two, preferably adjacent, radicals R, R d with the other groups to which the two residues R, R d bind, a condensed ring, where the two residues R, R d Form structures of the formula (RB)

[0125] Formula RB where R 1 has the meaning given above, in particular for formula (I), the dashed bonds represent the attachment points via which the two radicals R, R d bind, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and Y 4 C(R 1)2, NR 1 , NAr', BR 1 , BAr', O or S, preferably C(R 1 )2, NAr' or O, particularly preferably C(R 1 )2 or 0, where Ar' has the meaning given above, in particular for formula (I).

[0126] Furthermore, it can be provided that the at least two radicals R, R d , which form structures of the formula (RB) and form a condensed ring, residues R, R d from neighboring groups X, X 2 represent or radicals R, R d which each bind to adjacent C atoms, whereby these C atoms are preferably connected via a bond.

[0127] In particular, it can be provided that in preferred structures / compounds the sum of the indices r, s, t, v, m and n is preferably 0, 1, 2 or 3, particularly preferably 1 or 2. Particularly preferably, the compounds comprise at least one structure of the formulas (IV-1) to (IV-4), particularly preferably the

[0128] Compounds selected from compounds of formulas (IV-1) to (IV-4), wherein the compounds have at least one condensed ring,

[0129] Formula (IV-1)

[0130] Formula (IV-3) Formula (IV-4) where the symbols R, R a , R b , R c and R d have the meanings given above, in particular for formula (I), the symbol o stands for the condensation sites of the at least one condensed ring and the following applies to the further indices used: i is, independently at each occurrence, 0, 1 or 2, preferably 0 or 1.

[0131] Furthermore, in particular for structures / compounds of the formulas (IV-1) to (IV-4), it can be provided that the condensed ring is formed by structures of the formulas (RA-1) to (RA-12), (RA-1a) to (RA-4f) and / or (RB), as shown above, preferably by structures of the formulas (RA-1) to (RA-12) and / or (RA-1a) to (RA-4f). It can preferably be provided that the compounds have at least two condensed rings, wherein at least one condensed ring is formed by structures of the formulas (RA-1) to (RA-12) and / or (RA-1a) to (RA-4f) and a further ring is formed by structures of the formulas (RA-1) to (RA-12), (RA-1a) to (RA-4f) or (RB).

[0132] Furthermore, it can be provided that the substituents R, R c , R d , R e and R 1 according to the above formulas with the ring atoms of the ring system to which the substituents R, R c , R d , R e and R1 bind, do not form a fused aromatic or heteroaromatic ring system. This excludes the formation of a fused aromatic or heteroaromatic ring system with possible substituents R 1 and R 2 which are bound to the substituents R, R c , R d , R e and R 1 may be bound.

[0133] The residues R a , R b , R c preferably do not form a ring system with other groups. If substituents R a form a ring system, this ring is preferably composed of exactly two residues R a which are bonded to a C atom.

[0134] If the compound according to the invention is reacted with aromatic or heteroaromatic groups R, R c , R d , R e , R 1 or R 2is substituted, it is preferred if these do not contain any aryl or heteroaryl groups with more than two directly fused aromatic six-membered rings. Particularly preferably, the substituents do not contain any aryl or heteroaryl groups with directly fused six-membered rings. This preference is due to the low triplet energy of such structures. Condensed aryl groups with more than two directly fused aromatic six-membered rings that are nevertheless also suitable according to the invention are phenanthrene and triphenylene, since these also have a high triplet level.

[0135] Furthermore, it can be provided that the remainder R, R c , R d , R e , R 1 or R 2does not comprise an aromatic or heteroaromatic ring system having three linearly condensed aromatic 6-rings, wherein preferably none of the radicals R comprises an aromatic or heteroaromatic ring system having three linearly condensed aromatic 6-rings.

[0136] Group Z can be preferred a , L 1 -Q, L 1 -N(Ar)2 with the group to which the group Z a , L 1 -Q, L 1-N(Ar)2 according to formula (I) or the preferred embodiments of this formula. Continuous conjugation of the aromatic or heteroaromatic systems is formed as soon as direct bonds are formed between adjacent aromatic or heteroaromatic rings. A further linkage between the aforementioned conjugated groups, for example, via an S, N, or O atom or a carbonyl group, does not harm the conjugation.

[0137] Furthermore, it can be provided that the substituents R, R c , R d , R e and R 1 according to the above formulas, do not form a condensed aromatic or heteroaromatic ring system with the ring atoms of the ring system, preferably not a condensed ring system. This excludes the formation of a condensed ring system with possible substituents R 1 and R 2which are bound to the residues R, R c , R d , R e , R 1 may be bound.

[0138] When two residues, which can be selected in particular from R, R c , R d , R e , R 1 and / or R 2 , form a ring system with each other, this can be mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic. The radicals forming a ring system can be adjacent, ie these radicals are bonded to the same carbon atom or to carbon atoms that are directly bonded to each other, or they can be further apart. Furthermore, the radicals bonded to the substituents R, R d , R e , R 1 and / or R 2 provided ring systems can also be connected to each other via a bond, so that a ring closure can be achieved.

[0139] Furthermore, it can be provided that at least one radical R, R d is selected identically or differently on each occurrence from the group consisting of a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms or an aromatic or heteroaromatic ring system selected from the groups of the following formulas Ar-1 to Ar-76, preferably the substituents R, R d either form a condensed ring, preferably according to the structures of formulas (RA-1) to (RA-12) or (RB) or the substituent R, R d , R e is selected, identically or differently on each occurrence, from the group consisting of an aromatic or heteroaromatic ring system selected from the groups of the following formulas Ar-1 to Ar-76, and / or the group Ar' is selected, identically or differently on each occurrence, from the groups of the following formulas Ar-1 to Ar-76,

[0140] Ar-7 Ar-8

[0141] Ar-11

[0142] Ar-15 Ar-16

[0143] Ar-26

[0144] Ar-29

[0145] Ar-36 Ar-37

[0146] Ar-43 Ar ' 44

[0147] Ar-45 Ar-46

[0148] Ar-47

[0149] Ar-67 Ar-68

[0150] Ar-75

[0151] Ar-76 where R 1 has the meanings given above, the dashed bond represents the bond to the corresponding group and furthermore:

[0152] Ar 1 is at each occurrence, identically or differently, a bivalent aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, each of which is substituted by one or more radicals R 1 can be substituted;

[0153] A is the same or different at each occurrence C(R 1 )2, NR 1 , 0 or S; p is 0 or 1 , where p = 0 means that the group Ar1 is not present and that the corresponding aromatic or heteroaromatic group is directly bonded to the corresponding residue; q is 0 or 1, where q = 0 means that no group A is bonded to this position and that the corresponding carbon atoms are bonded instead to residues R 1 are bound.

[0154] The previously presented structures of the formulas (Ar-1) to (Ar-76) represent preferred embodiments of the radicals Ar, as defined, for example, in structures of the formula (I), in which case the substituents R 1 in formulas (Ar-1 ) to (Ar-76) by R d are to be replaced, where R d has the meaning set out above, in particular for formula (I).

[0155] The previously presented structures of the formulas (Ar-1) to (Ar-76) represent preferred embodiments of the residues L 1as defined, for example, for structures of formula (I), where in this case the substituents R 1 in formulas (Ar-1) to (Ar-76) are to be replaced by R, where R has the meaning set out above, in particular for formula (I). Furthermore, the radicals L 1 another connection point.

[0156] Structures of the formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16), (Ar-40), (Ar-41), (Ar-42), (Ar-43), (Ar-44), (Ar-45), (Ar-46), (Ar-69), (Ar-70), (Ar-76) are preferred and structures of the formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16) are particularly preferred.

[0157] If the above-mentioned groups for structures of the formulas (Ar-1) to (Ar-76) have several groups A, all combinations from the definition of A are possible. Preferred embodiments are then those in which a group A represents NR 1and the other group A for C(R 1 )2 or in which both groups A for NR 1 or in which both groups A stand for 0.

[0158] If A for NR 1 the substituent R 1 which is bonded to the nitrogen atom, preferably represents an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which can also be substituted by one or more radicals R 2 In a particularly preferred embodiment, this substituent R 1identical or different on each occurrence for an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, in particular having 6 to 18 aromatic ring atoms, which has no condensed aryl groups and which has no condensed heteroaryl groups in which two or more aromatic or heteroaromatic 6-ring groups are directly fused to one another, and which in each case also by one or more radicals R 2 may be substituted. Phenyl, biphenyl, terphenyl and quaterphenyl are preferred. Triazine, pyrimidine and quinazoline are also preferred, as listed above for Ar-47 to Ar-50, Ar-57 and Ar-58, where these structures are substituted by R 1 by one or more residues R 2 can be substituted.

[0159] If A for C(R 1 )2, the substituents R 1which are bonded to this carbon atom, preferably identically or differently on each occurrence, represent a linear alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which can also be substituted by one or more radicals R 2 R is particularly preferably 1 represents a methyl group or a phenyl group. The radicals R 1 also form a ring system with each other, which leads to a spiro system.

[0160] Preferred substituents R, R a , R b , R c , R d , R e and R f described.

[0161] Preferably, it can be provided that the following applies to the symbols used in particular in formulas (I), (1-1) to (l-4), etc.:

[0162] R, R c , Rd is the same or different at each occurrence H, D, N(Ar')2, N(R 1 )2, C(Ar')3, C(R 1 )3, Si(Ar')3, Si(R 1 )3, B(Ar')2, B(R 1 )2, a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl group is in each case substituted with one or more radicals R 1 may be substituted, wherein one or more non-adjacent CH2 groups are represented by R 1 C=CR 1 , C^C, Si(R 1 )2, C=O, C=S, C=Se, C=NR 1 , -C(=O)O-, -C(=O)NR 1 -, NR 1 , P(=O)(R 1 ), -O-, -S-, SO or SÜ2, or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, each of which is substituted by one or more radicals R 1 can be substituted; two radicals R, R d also with each other or a residue R, R d with another group, in particular a residue Rc form a ring system.

[0163] In a preferred embodiment of the invention, R, R d identically or differently at each occurrence selected from the group consisting of H, D, F, CN, NO2, Si(R 1 )s, B(OR 1 )2, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl group is in each case substituted with one or more radicals R 1 may be substituted, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, each substituted by one or more radicals R 1 can be substituted.

[0164] In a further preferred embodiment of the invention, substituent RR didentically or differently on each occurrence selected from the group consisting of H, D, F, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl group is in each case substituted with one or more radicals R 1 may be substituted, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, each substituted by one or more radicals R 1 can be substituted.

[0165] Furthermore, it can be provided that at least one radical R, R d preferably a substituent R, R d is selected, identically or differently at each occurrence, from the group consisting of H, D, an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which is reacted with one or more radicals R 1may be substituted, or a group N(Ar')2, particularly preferably at least one substituent R, R d is selected, identically or differently on each occurrence, from the group consisting of an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which is substituted with one or more radicals R 1 may be substituted, or a group N(Ar')2. Especially preferred is at least one substituent R, R d is selected, identically or differently on each occurrence, from the group consisting of an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which is substituted with one or more radicals R 1 may be substituted. In a further preferred embodiment of the invention, the substituents R, R d either a ring according to the structures of the formulas (RA-1 ) to (RA-12), (RA-1 a) to (RA-4f) or (RB) or the substituent R, R dis selected, identically or differently at each occurrence, from the group consisting of H, D, an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which is reacted with one or more radicals R 1 may be substituted, or a group N(Ar')2. Particularly preferred is the radical R, R d preferably the substituent R, R d identically or differently on each occurrence selected from the group consisting of H or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, particularly preferably having 6 to 13 aromatic ring atoms, each of which is substituted with one or more radicals R 1 can be substituted.

[0166] Furthermore, it can be provided that at least one radical R, R d , R erepresents an aromatic or heteroaromatic ring system with 5 to 13 aromatic ring atoms, which is substituted by one or more radicals R 1 can be substituted.

[0167] With the limitations set out above, the limits for R d preferences set out for R e accordingly.

[0168] Preferably, it can be provided that at least one radical, preferably a substituent R, R d , R e is selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene, each of which is substituted with one or more radicals R 1may be substituted. Here, the term "substituent" means, in particular, that R is not H. Furthermore, the R substituents may be the same or different if two or more substituents are present which are selected from the aromatic or heteroaromatic groups mentioned.

[0169] Furthermore, it can be provided that the groups R bonded to a C atom a are equal.

[0170] Furthermore, it can be provided that the groups R bonded to different C atoms a are equal.

[0171] In addition, it can be provided that the groups R bonded to different C atoms a are different.

[0172] Preferably, it can be provided that the groups R bonded to a C atom aare selected from straight-chain alkyl groups having 1 to 10 C atoms or branched or cyclic alkyl groups having 3 to 10 C atoms, each of which is substituted by one or more radicals R 2 may be substituted, preferably deuterated, two or more, preferably adjacent, substituents R a form a ring system. If adjacent substituents R a form a ring system, this ring is preferably composed of exactly two residues R a formed.

[0173] Furthermore, it can preferably be provided that the groups R bonded to a C atom a are selected from aromatic or heteroaromatic ring systems having 5 to 20 aromatic ring atoms, each of which is substituted by one or more radicals R 2 may be substituted, preferably phenyl groups, each of which is substituted by one or more radicals R 2may be substituted, preferably deuterated, two or more, preferably adjacent, substituents R a form a ring system. If adjacent substituents R a form a ring system, this ring is preferably composed of exactly two residues R a Preferably, the group R a represents methyl, ethyl, propyl, phenyl or two groups R a which bond to the same C- atom form a cycloalkyl radical with 5 or 6, preferably 5 carbon atoms, where the group R a preferably represents methyl, whereby these groups may be deuterated

[0174] Preferably, it can be provided that the group R b represents methyl, ethyl, propyl or two groups R b which bond to the same C-atom form a cycloalkyl radical with 5 or 6, preferably 5 carbon atoms, where the group R bpreferably represents H, D, methyl, ethyl, propyl, where these groups may be deuterated, where the group R b particularly preferably represents H or D.

[0175] Preferably, it can be provided that the group R c represents H, D, methyl, ethyl, propyl, where these groups may be deuterated, where the group R c preferably represents H or D.

[0176] In a preferred embodiment of the invention, R f identically or differently on each occurrence selected from the group consisting of a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl group is in each case substituted with one or more radicals R 1 may be substituted, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, each substituted by one or more radicals R2 can be substituted.

[0177] In a further preferred embodiment of the invention, R f identically or differently on each occurrence selected from the group consisting of a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, where the alkyl group is in each case substituted with one or more radicals R 2 may be substituted, an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which is substituted with one or more radicals R 2 may be substituted. R is particularly preferably f identically or differently on each occurrence selected from the group consisting of a straight-chain alkyl group having 1 to 5 C atoms or a branched or cyclic alkyl group having 3 to 5 C atoms, where the alkyl group is in each case substituted with one or more radicals R 2may be substituted or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, particularly preferably having 6 to 13 aromatic ring atoms, each of which is substituted by one or more radicals R 2 can be substituted.

[0178] In a preferred embodiment of the invention, R f at each occurrence, identically or differently selected from the group consisting of a straight-chain alkyl group having 1 to 6 C atoms or a cyclic alkyl group having 3 to 6 C atoms, where the alkyl group is in each case substituted with one or more radicals R 2 may be substituted, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each substituted by one or more radicals R 2 can be substituted; two radicals R f also form a ring system with each other. R is particularly preferably fat each occurrence, identically or differently selected from the group consisting of a straight-chain alkyl group having 1, 2, 3 or 4 C atoms or a branched or cyclic alkyl group having 3 to 6 C atoms, where the alkyl group is in each case substituted with one or more radicals R 2 may be substituted, but is preferably unsubstituted, or an aromatic ring system having 6 to 12 aromatic ring atoms, in particular having 6 aromatic ring atoms, each substituted by one or more, preferably non-aromatic radicals R 2 may be substituted, but is preferably unsubstituted; two radicals R f form a ring system with each other. R is particularly preferably f at each occurrence, identically or differently selected from the group consisting of a straight-chain alkyl group having 1, 2, 3 or 4 C atoms, or a branched alkyl group having 3 to 6 C atoms. R is most preferably frepresents a methyl group or a phenyl group, where two phenyl groups together can form a ring system, with a methyl group being preferred over a phenyl group. Preferred aromatic or heteroaromatic ring systems for which the substituents R, R c , R d , R e , R for Ar or Ar' are selected from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, which may be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which may be linked via the 1-, 2-, 3- or 4-position, naphthalene, in particular 1- or -linked naphthalene, indole, benzofuran, benzothiophene, carbazole, which may be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, which may be linked via the 1-, 2-, 3- or 4-position, dibenzothiophene, which may be linked via the 1-, 2-, 3- or 4-position, Indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, anthracene, pyrene, perylene, chrysene, phenanthrene or triphenylene,which are each substituted with one or more radicals R, R, 1 or R 2 may be substituted. The structures Ar-1 to Ar-76 listed above are particularly preferred, with structures of the formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16), (Ar-69), (Ar-70), (Ar-76) being preferred and structures of the formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16) being particularly preferred. With regard to the structures Ar-1 to Ar-76, it should be noted that these can be substituted with a substituent R 1 In the case of the ring systems Ar, these substituents are R 1 by R and in case R f these substituents R 1 by R 2 to replace.

[0179] Other suitable groups R, R d , R e are groups of the formula -Ar 4 -N(Ar 2 )(Ar 3 ), where Ar 2 , Ar 3 and Ar 4identically or differently on each occurrence represent an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, each of which is substituted by one or more radicals R 1 The total number of aromatic ring atoms of Ar 2 , Ar 3 and Ar 4 maximum 60 and preferably maximum 40.

[0180] Ar 4 and Ar 2 with each other and / or Ar 2 and Ar 3 with each other also by a group selected from C(R 1 )2, NR 1 , O or S. Preferably, the linking of Ar 4 and Ar 2 with each other or from Ar 2 and Ar 3 are ortho to the position of the linkage to the nitrogen atom. In a further embodiment of the invention, none of the groups Ar 2 , Ar 3 or Ar 4 connected to each other.

[0181] Ar is preferred 4 an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 12 aromatic ring atoms, each of which is substituted by one or more radicals R 1 may be substituted. Particularly preferred is Ar 4 selected from the group consisting of ortho-, meta- or para-phenylene or ortho-, meta- or para-biphenyl, each of which is substituted by one or more radicals R 1 may be substituted, but are preferably unsubstituted. Ar is particularly preferred 4 an unsubstituted phenylene group.

[0182] Preference is given to Ar 2 and Ar 3 identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each substituted by one or more radicals R 1 Particularly preferred groups Ar 2 or Ar 3are, identically or differently at each occurrence, selected from the group consisting of benzene, ortho-, meta- or para-biphenyl, ortho-, meta-, para- or branched terphenyl, ortho-, meta-, para- or branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spiro-bifluorenyl, 1- or 2-naphthyl, indole, benzofuran, benzothiophene, 1-, 2-

[0183] 3- or 4-carbazole, 1-, 2-, 3- or 4-dibenzofuran, 1-, 2-, 3- or 4-di-benzothiophene, indenocarbazole, indolocarbazole, 2-, 3- or 4-pyridine, 2-,

[0184] 4- or 5-pyrimidine, pyrazine, pyridazine, triazine, phenanthrene or triphenylene, each of which is substituted with one or more radicals R 1 may be substituted. Particularly preferred are Ar 2 and Ar 3identically or differently on each occurrence selected from the group consisting of benzene, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, in particular 1-, 2-, 3- or 4-fluorene, or spirobifluorene, in particular 1-, 2-, 3- or 4-spirobifluorene.

[0185] In a further preferred embodiment of the invention, R 1 identically or differently on each occurrence selected from the group consisting of H, D, F, CN, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, where the alkyl group is in each case substituted with one or more radicals R 2 may be substituted, or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, each substituted by one or more radicals R2 may be substituted. In a particularly preferred embodiment of the invention, R 1 identically or differently on each occurrence selected from the group consisting of H, a straight-chain alkyl group having 1 to 6 C atoms, in particular having 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group having 3 to 6 C atoms, where the alkyl group is substituted with one or more radicals R 2 may be substituted, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 6 to 13 aromatic ring atoms, each substituted by one or more radicals R 5 can be substituted, but is preferably unsubstituted.

[0186] In a further preferred embodiment of the invention, R 2identical or different on each occurrence H, an alkyl group having 1 to 4 C atoms or an aryl group having 6 to 10 C atoms, which may be substituted by an alkyl group having 1 to 4 C atoms, but is preferably unsubstituted.

[0187] In compounds according to the invention that are processed by vacuum evaporation, the alkyl groups preferably have no more than five carbon atoms, particularly preferably no more than 4 carbon atoms, and most preferably no more than 1 carbon atom. Also suitable for compounds that are processed from solution are compounds that are substituted by alkyl groups, particularly branched alkyl groups, with up to 10 carbon atoms, or that are substituted by oligoarylene groups, for example ortho-, meta-, para-, or branched terphenyl or quaterphenyl groups.

[0188] When the compounds of formula (I) or the preferred embodiments are used as matrix material for a phosphorescent emitter or in a layer directly adjacent to a phosphorescent layer, it is further preferred if the compound does not contain any condensed aryl or heteroaryl groups in which more than two six-membered rings are directly condensed to one another. Exceptions to this are phenanthrene and triphenylene, which may be preferred due to their high triplet energy despite the presence of condensed aromatic six-membered rings.

[0189] Furthermore, it can be provided that the compound comprises exactly two or exactly three structures according to formula (I).

[0190] In a preferred embodiment, the compounds are selected from compounds of formula (D-1),

[0191] Formula (D-1 ) where the group L 2represents a connecting group, preferably a bond or an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R, and the further symbols and indices used have the meanings given in claim 1, wherein the group L 2 forms a bond to the basic structure instead of a hydrogen atom or a substituent, preferably the group L 2 to the remains L 1 , Q, Z a binds.

[0192] In a further preferred embodiment of the invention, L 2for a bond or for an aromatic or heteroaromatic ring system having 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system having 6 to 12 carbon atoms, which may be substituted by one or more radicals R, but is preferably unsubstituted, where R may have the meaning given above, in particular for formula (I).

[0193] Particularly preferred is L 2 represents an aromatic ring system having 6 to 10 aromatic ring atoms or a heteroaromatic ring system having 6 to 13 heteroaromatic ring atoms, each of which is substituted by one or more radicals R 1 may be substituted, but is preferably unsubstituted, where R 1 which may have the meaning given above, in particular for formula (I).

[0194] Furthermore, the symbol L shown inter alia in formula (D1 ) is preferably 2identical or different on each occurrence for a bond or an aryl or heteroaryl radical having 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 ring atoms, so that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is bonded directly, ie via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group.

[0195] Furthermore, it can be provided that the group L shown in formula (D1 ) 2an aromatic ring system with at most four, preferably at most three, particularly preferably at most two fused aromatic and / or heteroaromatic 6-membered rings, preferably no fused aromatic or heteroaromatic ring system. Accordingly, naphthyl structures are preferred over anthracene structures. Furthermore, fluorenyl, spirobifluorenyl, dibenzofuranyl, and / or dibenzothienyl structures are preferred over naphthyl structures.

[0196] Particularly preferred are structures which do not exhibit condensation, such as phenyl, biphenyl, terphenyl and / or quaterphenyl structures.

[0197] Examples of suitable aromatic or heteroaromatic ring systems L 2are selected from the group consisting of ortho-, meta- or para-phenylene, ortho-, meta- or para-biphenylene, terphenylene, in particular branched terphenylene, quaterphenylene, in particular branched quaterphenylene, fluorenylene, spirobifluorenylene, dibenzofuranylene, dibenzothienylene and carbazolylene, each of which is substituted by one or more radicals R 1 may be substituted, but are preferably unsubstituted.

[0198] According to a preferred embodiment, a compound according to the invention can be prepared by at least one of the structures according to formulas (I), (I-1) to (I-4), (II-1) to (III-44), (III-1) to (III-48) and / or (IV-1) to (IV-4). Compounds according to the invention, preferably comprising structures according to formulas (I), (I-1) to (I-4), (II-1) to (II-44), (III-1) to (III-48) and / or (IV-1) to (IV-4), preferably have a molecular weight of less than or equal to 5000 g / mol, preferably less than or equal to 4000 g / mol, particularly preferably less than or equal to 3000 g / mol, especially preferably less than or equal to 2000 g / mol, more especially preferably less than or equal to 1200 g / mol and very particularly preferably less than or equal to 900 g / mol.

[0199] Furthermore, preferred compounds according to the invention are characterized by their sublimability. These compounds generally have a molecular weight of less than approximately 1200 g / mol.

[0200] Preferably, the compound may not comprise any alkoxy, thioalkoxy or hydroxy groups.

[0201] In a further preferred embodiment, it can be provided that the compound does not comprise a cyclobutyl radical with two oxygen atoms bonded to this cyclobutyl radical.

[0202] Preferably, it can further be provided that the compound does not comprise a thiadiazyl group.

[0203] Furthermore, it can be provided that the ratio of electron transport groups, preferably pyrimidine, triazine, quinazoline and / or quinoxaline groups, to phenyl groups to which two cyclopentyl radicals are fused is at least 0.6, preferably at least 0.8, particularly preferably at least 0.9. Furthermore, it can be provided that the ratio of electron transport groups, preferably pyrimidine, triazine, quinazoline and / or quinoxaline groups, to phenyl groups to which two cyclopentyl radicals are fused is at most 10, preferably at most 4, particularly preferably at most 1.5.

[0204] Furthermore, it can be provided that the compound comprising structures according to formula (I), preferably the compound according to formula (I) or a preferred embodiment of this structure / compound is not in direct contact with a metal atom, preferably does not represent a ligand for a metal complex.

[0205] The above-mentioned preferred embodiments can be combined with each other as desired within the limitations defined in claim 1. In a particularly preferred embodiment of the invention, the above-mentioned advantages occur simultaneously.

[0206] Examples of preferred compounds according to the embodiments listed above are the compounds listed in the following table.

[0207]

[0208] The basic structure of the compounds of the invention can be prepared according to the methods outlined in the following schemes. The individual synthesis steps, such as coupling reactions leading to C–C and / or C–N bond formations, are known in principle to those skilled in the art. These include, among others, reactions according to BUCHWALD, SUZUKI, YAMAMOTO, STILLE, HECK, NEGISHI, SONOGASHIRA, and HIYAMA.

[0209] Further information on the synthesis of the compounds according to the invention can be found in the synthesis examples.

[0210] The following schemes describe the preparation of the compounds of the invention using explicit phenyl compounds to which one cyclopentyl group, preferably two cyclopentyl groups, is / are fused. This use is to be understood as exemplary, so that further compounds of the invention can be obtained via similar synthetic routes starting from other basic structures.

[0211] The synthesis of phenyl compounds to which one, preferably two, cyclopentyl groups are fused is widely known in the art. Many of these compounds are commercially available. These include, for example, the compounds mentioned in the synthesis examples.

[0212] The compounds according to the invention with electron transport groups, in particular compounds comprising structures according to formula (I), can be obtained starting from phenyl compounds (1) to which one cyclopentyl group, preferably two cyclopentyl groups, is / are condensed, by the following synthesis routes:

[0213] 1 ) by lithiation (2), transmetallation with copper(I) chloride to an organo-copper chloride (3) and subsequent palladium-phosphine-mediated CC coupling with a chlorine, bromine or iodo-

[0214] Heterocycle X-HetAr (HetAr: heterocycle containing pyridine, primidine,

[0215] triazine, quinazoline, quinoxaline, etc.) according to M. Oi et al., Chem. Sei.,

[0216] 2019, 10, 6107, are presented:

[0217] R: Alkyl, Aryl

[0218] X: H, D, alkyl, aryl, Br.

[0219] If the group X on the phenyl compound (1 ) to which a cyclopentyl group, preferably two cyclopentyl groups, is / are condensed, (1 ) is a bromine atom, the reaction sequence 1 ) or 2) can be repeated consecutively, so that symmetrically or asymmetrically di-substituted compounds according to the invention with -NAr2 or -Ar-NAr2 groups are obtained.

[0220] The scheme (1 ) is to be understood as an example, so that other groups X are also suitable, as shown in the examples.

[0221] The meaning of the symbols used in the scheme presented above essentially corresponds to that defined for formula (I), although for reasons of clarity, numbering and a complete representation of all symbols have been omitted. The present invention therefore further provides a process for preparing a compound according to the invention, wherein a phenyl compound to which a cyclopentyl group, preferably two cyclopentyl groups, is / are fused is synthesized and at least one aromatic or heteroaromatic radical is introduced, preferably by means of a nucleophilic aromatic substitution reaction or a coupling reaction.

[0222] By these processes, optionally followed by purification, such as recrystallization or sublimation, the compounds according to the invention can be obtained in high purity, preferably more than 99% (determined by 1H-NMR and / or HPLC).

[0223] The compounds of the invention can also be mixed with a polymer. It is also possible to covalently incorporate these compounds into a polymer. This is particularly possible with compounds substituted by reactive leaving groups, such as bromine, iodine, chlorine, boronic acid, or boronic acid esters, or by reactive, polymerizable groups, such as olefins or oxetanes. These can be used as monomers to produce corresponding oligomers, dendrimers, or polymers. The oligomerization or polymerization preferably takes place via the halogen functionality or the boronic acid functionality, or via the polymerizable group, respectively. It is also possible to crosslink the polymers via such groups. The compounds and polymers of the invention can be used as crosslinked or uncrosslinked layers.

[0224] The invention therefore further provides oligomers, polymers or dendrimers comprising one or more of the above-listed structures of the formula (I) and preferred embodiments of this formula or compounds according to the invention, wherein one or more bonds of the compounds according to the invention or of the structures of the formula (I) and preferred embodiments of this formula to the polymer, oligomer or dendrimer are present. Depending on the linkage of the structures of the formula (I) and preferred embodiments of this formula or of the compounds, these therefore form a side chain of the oligomer or polymer or are linked in the main chain. The polymers, oligomers or dendrimers can be conjugated, partially conjugated or non-conjugated. The oligomers or polymers can be linear, branched or dendritic.The same preferences as described above apply to the repeating units of the compounds according to the invention in oligomers, dendrimers and polymers.

[0225] To prepare the oligomers or polymers, the monomers according to the invention are homopolymerized or copolymerized with other monomers. Copolymers are preferred, wherein the units according to formula (I) or the preferred embodiments described above and below are present in amounts of 0.01 to 99.9 mol%, preferably 5 to 90 mol%, particularly preferably 20 to 80 mol%. Suitable and preferred comonomers which form the polymer backbone are selected from fluorenes (e.g. according to EP 842208 or WO 2000 / 022026), spirobifluorenes (e.g. according to EP 707020, EP 894107 or WO 2006 / 061181), para-phenylenes (e.g. according to WO 92 / 18552), carbazoles (e.g. according to WO 2004 / 070772 or WO 2004 / 113468), thiophenes (e.g. according to EP 1028136), dihydrophenanthrenes (e.g. according to WO 2005 / 014689), cis- and trans-indenofluorenes (e.g. according to WO 2004 / 041901 or WO 2004 / 113412), ketones (e.g. according to WO 2005 / 040302), phenanthrenes (e.g.according to WO 2005 / 104264 or WO 2007 / 017066) or several of these units. The polymers, oligomers, and dendrimers may contain further units, for example hole-transport units, in particular those based on triarylamines, and / or electron-transport units.

[0226] Of particular interest are also compounds according to the invention that are characterized by a high glass transition temperature. In this context, particular preference is given to compounds according to the invention comprising structures according to formula (I) or the preferred embodiments described above and below, which have a glass transition temperature of at least 70°C, more preferably of at least 110°C, most preferably of at least 125°C, and especially preferably of at least 150°C, determined according to DIN 51005 (version 2005-08).

[0227] For processing the compounds of the invention from the liquid phase, for example by spin coating or printing processes, formulations of the compounds of the invention are required. These formulations can be, for example, solutions, dispersions, or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, a-terpineol, benzothiazole, butylbenzoate, cumene, cyclohexanol, cyclohexanone, Cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, NMP,p-Cymene, phenetole, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butylmethyl ether, triethylene glycol butylmethyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, 2-methylbiphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, diethyl sebacate, octyloctanoate, heptylbenzene, menthyl isovalerate, cyclohexylhexanoate or mixtures of these solvents.

[0228] The present invention therefore further provides a formulation or a composition comprising at least one compound according to the invention and at least one further compound. The further compound can, for example, be a solvent, in particular one of the abovementioned solvents or a mixture of these solvents. If the further compound comprises a solvent, this mixture is referred to herein as a formulation. However, the further compound can also be at least one further organic or inorganic compound that is also used in the electronic device, for example an emitting compound and / or a further matrix material.Preferably, it can be provided that at least one further compound is selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF, host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocking materials and hole blocking materials, preferably host materials.

[0229] The present invention further relates to the use of a compound according to the invention in an electronic device, in particular in an organic electroluminescent device. Preferably, the compounds according to the invention can be used in an electronic device as a host material, electron transport material, electron injection material, or hole blocking material.

[0230] The present invention further relates to an electronic device comprising at least one compound according to the invention. An electronic device within the meaning of the present invention is a device that contains at least one layer containing at least one organic compound. The component may also contain inorganic materials or layers composed entirely of inorganic materials.

[0231] Particularly preferably, the electronic device is selected from the group consisting of organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes based on small molecules (sOLEDs), organic light-emitting diodes based on polymers (PLEDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), “organic plasmon emitting devices” (DM Koller et al., Nature Photonics 2008, 1- 4); organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs) and organic electrical sensors, preferably organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), particularly preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes based on small molecules (sOLEDs), organic light-emitting diodes based on polymers (PLEDs), in particular phosphorescent OLEDs.

[0232] The organic electroluminescent device contains a cathode, an anode, and at least one emitting layer. In addition to these layers, it may contain further layers, for example, one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, exciton-blocking layers, electron-blocking layers, and / or charge-generation layers. Interlayers, which, for example, have an exciton-blocking function, may also be inserted between two emitting layers. It should be noted, however, that not all of these layers are necessarily present. The organic electroluminescent device may contain one emitting layer or it may contain multiple emitting layers.If a plurality of emission layers are present, these preferably have a total of a plurality of emission maxima between 380 nm and 750 nm, resulting in an overall white emission, i.e. different emitting compounds which can fluoresce or phosphoresce are used in the emitting layers. Particular preference is given to systems with three emitting layers, wherein the three layers exhibit blue, green and orange or red emission. The organic electroluminescent device according to the invention can also be a tandem electroluminescent device, in particular for white-emitting OLEDs. The compound according to the invention can be used in different layers, depending on the precise structure. Preference is given to an organic electroluminescent device comprising a compound according to formula (I) orThe preferred embodiments described above in an emitting layer as a matrix material for phosphorescent emitters or for emitters exhibiting TADF (thermally activated delayed fluorescence), in particular for phosphorescent emitters. Furthermore, the compound according to the invention can also be used in an electron-transport layer and / or in a hole-blocking layer. The compound according to the invention is particularly preferably used as a matrix material for phosphorescent emitters, in particular for red, orange, blue, green, or yellow, preferably for blue or green phosphorescent emitters, in an emitting layer, as a host material, electron-transport material, electron-injection material, or hole-blocking material.

[0233] Preferably, it can be provided that the organic electroluminescent device comprises at least one emission layer and at least one electron transport layer and the electron transport layer contains the compound according to the present invention.

[0234] If the compound according to the invention is used as a matrix material for a phosphorescent compound in an emitting layer, it is preferably used in combination with one or more phosphorescent materials (triplet emitters). Phosphorescence, within the meaning of this invention, is understood to mean luminescence from an excited state with higher spin multiplicity, i.e., a spin state > 1, in particular from an excited triplet state. For the purposes of this application, all luminescent complexes with transition metals or lanthanides, in particular all iridium, platinum, and copper complexes, are to be considered phosphorescent compounds.

[0235] The mixture of the compound according to the invention and the emitting compound contains between 99 and 1 vol.%, preferably between 98 and 10 vol.%, particularly preferably between 97 and 60 vol.%, in particular between 95 and 80 vol.% of the compound according to the invention, based on the total mixture of emitter and matrix material. Accordingly, the mixture contains between 1 and 99 vol.%, preferably between 2 and 90 vol.%, particularly preferably between 3 and 40 vol.%, in particular between 5 and 20 vol.% of the emitter, based on the total mixture of emitter and matrix material.

[0236] In one embodiment of the invention, the compound according to the invention is used as the sole matrix material (“single host”) for the phosphorescent emitter.

[0237] A further embodiment of the present invention is the use of the compound according to the invention as a matrix material for a phosphorescent emitter in combination with another matrix material. Suitable matrix materials that can be used in combination with the compounds according to the invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g., according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627, or WO 2010 / 006680, triarylamines, carbazole derivatives, e.g., B. CBP (N,N-biscarbazolylbiphenyl) or those in WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527, WO 2008 / 086851 or WO 2013 / 041176, indolocarbazole derivatives, e.g. according to WO 2007 / 063754 or WO 2008 / 056746, indenocarbazole derivatives, e.g. according to WO 2010 / 136109, WO 2011 / 000455, WO 2013 / 041176 or WO 2013 / 056776, azacarbazole derivatives, e.g. B. according to EP 1617710, EP 1617711 , EP 1731584, JP 2005 / 347160, bipolar matrix materials, e.g.according to WO 2007 / 137725, silanes, e.g. according to WO 2005 / 111172, azaboroles or boronate esters, e.g. according to WO 2006 / 117052, triazine derivatives, e.g. according to WO 2007 / 063754, WO 2008 / 056746, WO 2010 / 015306, WO 2011 / 057706, WO 2011 / 060859 or WO 2011 / 060877, zinc complexes, e.g. according to EP 652273 or WO 2009 / 062578, diazasilole or tetraazasilole derivatives, e.g. according to WO 2010 / 054729, diazaphosphole derivatives, e.g. B. according to WO 2010 / 054730, bridged carbazole derivatives, e.g. according to WO 2011 / 042107, WO 2011 / 060867, WO 2011 / 088877 and WO 2012 / 143080, triphenylene derivatives, e.g. according to WO 2012 / 048781, dibenzofuran derivatives, e.g. according to WO 2015 / 169412, WO 2016 / 015810, WO 2016 / 023608, WO 2017 / 148564 or WO 2017 / 148565 or biscarbazoles, e.g. according to JP 3139321 B2.

[0238] Likewise, another phosphorescent emitter, which emits at a shorter wavelength than the actual emitter, can be present in the mixture as a co-host. Particularly good results are achieved when a red-phosphorescent emitter is used as the emitter and a yellow-phosphorescent emitter is used as the co-host in combination with the compound according to the invention.

[0239] Furthermore, a compound can be used as co-host which does not participate, or does not participate to a significant extent, in charge transport, as described, for example, in WO 2010 / 108579. In particular, compounds which have a large band gap and themselves do not participate, or at least do not participate to a significant extent, in the charge transport of the emitting layer are suitable as co-matrix material in combination with the compound according to the invention. Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009 / 124627 or WO 2010 / 006680. In this context, it should be noted that compounds according to the invention without special functional groups, for example hole transport groups and / or electron transport groups, have advantageous properties.

[0240] Particularly suitable phosphorescent compounds (= triplet emitters) are compounds that emit light upon suitable excitation, preferably in the visible range, and also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80, in particular a metal with this atomic number. Compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold, or europium are preferably used as phosphorescent emitters, in particular compounds containing iridium or platinum.Examples of the emitters described above can be found in the applications WO 00 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 05 / 033244, WO 05 / 019373, US 2005 / 0258742, WO 2009 / 146770, WO 2010 / 015307, WO 2010 / 031485, WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 086089, WO 2010 / 099852, WO 2010 / 102709, WO 2011 / 032626, WO 2011 / 066898, WO 2011 / 157339, WO 2012 / 007086, WO 2014 / 008982, WO 2014 / 023377, WO 2014 / 094961, WO 2014 / 094960, WO 2015 / 036074, WO 2015 / 104045, WO 2015 / 117718, WO 2016 / 015815, WO 2016 / 124304, WO 2017 / 032439 and WO 2018 / 011186. In general, all phosphorescent complexes as used according to the prior art for phosphorescent electroluminescent devices and as known to the person skilled in the art in the field of organic electroluminescence are suitable, and the person skilled in the art can use further phosphorescent complexes without inventive step.

[0241] Examples of phosphorescent dopants are listed in the following table.

[0242]

[0243] The compounds according to the invention are also particularly suitable as matrix materials for phosphorescent emitters in organic electroluminescent devices, as described, for example, in WO 98 / 24271, US 2011 / 0248247 and US 2012 / 0223633. In these multi-color display components, an additional blue emission layer is vapor-deposited over the entire area of ​​all pixels, even those with a color other than blue. In a further embodiment of the invention, the organic electroluminescent device according to the invention does not contain a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, ie the emitting layer directly adjoins the hole injection layer or the anode, and / or the emitting layer directly adjoins the electron transport layer or the electron injection layer or the cathode, as described, for example, in WO 2005 / 053051.Furthermore, it is possible to use a metal complex that is the same or similar to the metal complex in the emitting layer directly adjacent to the emitting layer as a hole transport or hole injection material, as described, for example, in WO 2009 / 030981.

[0244] In the further layers of the organic electroluminescent device according to the invention, all materials commonly used in the prior art can be used. Therefore, the skilled person can, without inventive step, use all materials known for organic electroluminescent devices in combination with the compounds according to formula (I) according to the invention or the preferred embodiments described above.

[0245] Also preferred is an organic electroluminescent device, characterized in that one or more layers are coated using a sublimation process. The materials are sublimated in vacuum sublimation systems at an initial pressure of less than 10' 5 mbar, preferably less than 10' 6 mbar. However, it is also possible that the initial pressure is even lower, for example less than 10' 7 mbar.

[0246] Also preferred is an organic electroluminescent device, characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or by means of carrier gas sublimation. The materials are sublimated at a pressure between 10' 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.

[0247] Also preferred is an organic electroluminescent device characterized in that one or more layers are produced from solution, such as by spin coating, or by any printing process, such as screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), inkjet printing, or nozzle printing. Soluble compounds are required for this, which are obtained, for example, by suitable substitution.

[0248] Formulations for applying a compound according to formula (I) or the preferred embodiments thereof set out above are novel. A further subject of the present invention is therefore a formulation comprising at least one solvent and a compound according to formula (I) or the preferred embodiments thereof set out above.

[0249] Furthermore, hybrid processes are possible, in which, for example, one or more layers are applied from solution and one or more further layers are deposited by vapor deposition.

[0250] These processes are generally known to the person skilled in the art and can be applied by him without inventive step to organic electroluminescent devices containing the compounds according to the invention.

[0251] The compounds of the invention and the organic electroluminescent devices of the invention are distinguished from the prior art in particular by a low refractive index (RI). Furthermore, these compounds and the organic electroluminescent devices obtainable therefrom exhibit an improved lifetime. The other electronic properties of the electroluminescent devices, such as efficiency or operating voltage, remain at least equally good. In a further variant, the compounds of the invention and the organic electroluminescent devices of the invention are distinguished from the prior art in particular by improved efficiency and / or operating voltage and a longer lifetime.

[0252] The electronic devices according to the invention, in particular organic electroluminescent devices, are characterized by one or more of the following surprising advantages over the prior art:

[0253] 1. Electronic devices, in particular organic electroluminescent devices containing compounds of formula (I) or the preferred embodiments described above and below, in particular as matrix material or as electron-conducting materials, exhibit excellent efficiency. Compounds of the invention according to formula (I) or the preferred embodiments described above and below achieve a low operating voltage when used in electronic devices.

[0254] 2. Electronic devices, in particular organic electroluminescent devices containing compounds according to formula (I) or the preferred embodiments described above and below, in particular as matrix material or as electron-conducting materials, exhibit a very long lifetime. These compounds, in particular, result in low roll-off, i.e., a low drop in the power efficiency of the device at high luminance levels.

[0255] 3. The compounds according to the invention according to formula (I) or the preferred embodiments described above and below show a very high stability and lifetime.

[0256] 4. Electronic devices, in particular organic electroluminescent devices containing compounds according to formula (I) or the preferred embodiments described above and below, in particular as matrix material or as electron-conducting materials, have a very low refractive indices.

[0257] 5. Using compounds according to formula (I) or the preferred embodiments described above and below, the formation of optical loss channels can be avoided in electronic devices, particularly organic electroluminescent devices. As a result, these devices are characterized by high PL and thus high EL efficiency of emitters and excellent energy transfer from the matrices to dopants.

[0258] 6. Compounds according to formula (I) or the preferred embodiments described above and below have excellent glass film formation.

[0259] 7. Compounds according to formula (I) or the preferred embodiments described above and below form very good films from solutions.

[0260] These advantages mentioned above are not accompanied by an excessive deterioration of the other electronic properties.

[0261] 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 as an example of a generic series or as an equivalent or similar feature. 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).

[0262] It should further be noted that many of the features, and in particular 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.

[0263] The teaching of technical action disclosed in the present invention can be abstracted and combined with other examples.

[0264] The invention is further illustrated by the following examples, without intending to limit it. From these descriptions, one skilled in the art can practice the invention within the entire disclosed scope and, without inventive step, prepare further compounds according to the invention and use them in electronic devices or apply the method according to the invention.

[0265] Examples:

[0266] Unless otherwise stated, the following syntheses are carried out under a protective gas atmosphere in dried solvents. The metal complexes are also handled in the absence of light or under yellow light. The solvents and reagents can be obtained, for example, from Sigma-ALDRICH or ABCR. The respective information in square brackets or the numbers given for individual compounds refer to the CAS numbers of the known compounds. For compounds that can exhibit multiple enantiomeric, diastereomeric, or tautomeric forms, one form is shown as a representative example.

[0267] Literature-known Synthone LS:

[0268] LS1 LS2

[0269] Br

[0270] 67476-86-2 1142818-90-3

[0271] LS3 LS4 vQ Q

[0272] Br\ / Br\1142818-95-8 960079-28-1 jCXX l

[0273] LS5 LS6 _ / Br \ _ 2 1359120-33-4 1142819-14-4 y-

[0274] \ — A / Br /

[0275] LS7 LS8

[0276] XJU VCJ

[0277] 1202051-00-0 2762987-85-7

[0278] A) Synthesis of synthons S compounds B according to the invention:

[0279] Example B1:

[0280] Procedure according to M. Oi et al., Chem. Sci., 2019, 10, 6107, Ex. 36. Preparation: 34.9 g (100 mmol) LS1, 39.5 g (110 mmol) 2-iodo-4,6-diphenyl-1,3,5-triazine [83819-97-0] instead of the 4-iodobenzoic acid methyl ester, in a stirred autoclave, 120 °C, 24 h. Further purification is carried out by chromatography and / or repeated hot extraction crystallization (conventional organic solvents or combinations thereof, preferably acetonitrile-dichloromethane (DCM), 1:3 to 3:1 vv) and fractional sublimation or annealing under high vacuum. Yield: 31.7 g (63 mmol) 63%; Purity: approx. 99.9% according to HPLC.

[0281] The following compounds can be prepared analogously. The yields depend on the steric demand of LS1 to LS8, typically following a decreasing sequence: LS1 ~ LS2 ~ LS3 > LS4 > LS5 ~ LS6 ~ LS7 ~ LS8. For the heteroaryl-halogen coupling partners listed above, they are typically in the range of 25-50% for chlorides, 40-60% for bromides, and 50-70% for iodides.

[0282]  LS1

[0283] B100 / N= ^—

[0284] ■

[0285] 2415143-30-3

[0286] LS2 / N=<^

[0287] ,CI

[0288] Cl 1 \ V=\ VN

[0289] B101 N iQ

[0290] O

[0291] 2245879-89-2 o

[0292] LS4 \ / 11 _

[0293] B102 fyr ya A / \^N

[0294] 2724236-69-3

[0295] LS5

[0296] / V°yN

[0297] ( yjT

[0298] B103 A / \^N

[0299] III

[0300] N

[0301] 2363033-70-7

[0302] LS6

[0303] ( yjT y Br v9x)

[0304] A / \^N

[0305] B104 / \ v / — / N= / C / C jl \ N \ o

[0306] 2414945-43-8 AOU LS7 x2o

[0307] ( yjT or NW / N= CC J

[0308] B105 \ / — Xr J l \ N \ D d D D

[0309] 1821152-29-7 VDD

[0310] LS2

[0311] ( yjT y ci

[0312] ^=Z \^N \H^ N= VO

[0313] / )=<

[0314] B107

[0315] Q

[0316] People

[0317] N

[0318] N

[0319] 2454627-86-0

[0320] LS1

[0321] C '== / YX \=N v / \ V / A / N= CT J l\ N \

[0322] B108 oo

[0323] 1821152-34-4

[0324] LS1

[0325] / Y°y N ,

[0326] (yX V

[0327] \==NM / N= cr j

[0328] B109 \ / A

[0329] ! \ N \

[0330] QXJ

[0331] 1801368-86-4 LS1

[0332] Z^f z '°V' N (yjr vzv / N= cr j

[0333] \ / A

[0334] / \ N \

[0335] B110 ncV

[0336] 1821152-54-8

[0337] LS1 c '== / Cz \==vN ci Zy7 J= vO

[0338] B111

[0339] CR) 1821152-56-0

[0340] LS1

[0341] (\XV

[0342] V ==z \=NZ \V / / N= / Cf J / ( N IT\ /

[0343] B112

[0344] 0 CCQ ^

[0345] 2201128-31-4 o

[0346] LS1

[0347] / V°y N A T V ^= / \==N

[0348] B113

[0349] 0

[0350] 2206809-98-3

[0351] LS1

[0352] \ I yN}-ci / \ V / A / N= / CT j

[0353] / N / \ N \

[0354] B114 jr0 \_ / ~~s O 2375148-96-0 LS1

[0355] O-T / ST-N

[0356] M / N= cr i

[0357] B115 r N \ / A / V\ w A 0=C N w

[0358] 1821152-68-4

[0359] LS4

[0360] B116 / Opy

[0361] Cl \ S4 / O 2084128-66-3 >Cf

[0362] LS1

[0363] / Q

[0364] B117

[0365] / A N= \

[0366] O — A N CI

[0367] 2268732-45-0

[0368] LS5

[0369] ( yX v

[0370] ^=Z \^N or

[0371] B118 and O

[0372] / \ / ^ N \ D x V − d D D

[0373] 1821152-73-1 D / \

[0374] DD

[0375] LS1 f

[0376] \^N < w

[0377] B119 N= y

[0378] \=Z ,=,

[0379] MO

[0380] 1821152-80-0 LS1

[0381] C\jr or TZ \^N

[0382] B120 or AO

[0383] C XTo

[0384] 1R821153J-05-2 XT

[0385] LS1 f ZW '== / yJ VTN =N y- c| AA N= yO

[0386] B121

[0387] ^A)

[0388] Q

[0389] 1821152-94-6

[0390] LS1

[0391] A — < ( S V' N ^=zyX yN V

[0392] B122

[0393] (TV / 11 QQ j\ 0 2206810-00-4 A /

[0394] LS1

[0395] (\jr v

[0396] B123 Z A r N ty A w

[0397] 2084128-80-1

[0398] LS1 i y y / A r N AA / N A / T v^ 1

[0399] B124 \ T y) A

[0400] A AA 1821153-11-0 LS1 s-y N y cl W F / \ 0=

[0401] B125 / XJÖ

[0402] / j(j

[0403] Y i oLjx

[0404] 1835205-90-7

[0405] LS1 A / ~- / s y ^=Z T N x v \=N ÖÖ C M r\_ / N N= V \CJ

[0406] B126 o cPo

[0407] 1835206-09-1

[0408] LS1

[0409] / X / \

[0410] A y--V s VT' N yci Z \Ä / A / N= CT J r\ N \

[0411] B127

[0412] CJ^ O Z~

[0413] 1821152-99-1

[0414] LS1

[0415] B128 Q-QA)

[0416] Ö

[0417] 1835206-15-9

[0418] LS4

[0419] B129 oXr° \ OJ^Y Cl x S4 yC / S 2084128-65-2 >Qf LS1 0

[0420] B130 in ^ ULo

[0421] 2376527-32-9

[0422] LS1

[0423] Q > <YY

[0424] _ y Nx ,

[0425] B131 CKO

[0426] N = / / A N= \

[0427] {^f in Ky-S

[0428] 2084128-68-5

[0429] LS1

[0430] NKU j

[0431] B132 OIj CO / Hey C Ü z J Zx o /

[0432] 2268732-70-1

[0433] LS1

[0434] Br

[0435] B200

[0436] N^N a v No. 2349-08-3

[0437] LS1 DD Br

[0438] \ / \ / D — ( Y-D

[0439] D D r \

[0440] D / y A '~ D \—L >=( N=( D

[0441] B201 D N^Sxl D \ )=( / — y—\ N— \ D DX5C N CCC D 7 X d d / X D— f V- D

[0442] D D

[0443] 2569012-82-2 D Z D LS1

[0444] Br o

[0445] ^ty = VvX / N c = b^

[0446] \= / N— c

[0447] B202 N^N ^x zz o A ^a o ö 1911641-83-2 Qu C

[0448] LS2

[0449] Br

[0450] / =\ / N= ^

[0451] B203 , \ \ )=( / — / / / N

[0452] 2102445-23-6 QQ v

[0453] LS1 Q CQ

[0454] Br ö ö

[0455] B204 N^N

[0456] 2304744-54-3

[0457] LS4

[0458] Br

[0459] B205

[0460] 2222454-76-2

[0461] LS1

[0462] B206

[0463] Q QIJ 2306076-62-8 LS1

[0464] Br

[0465] == N =^~

[0466] B207 Q

[0467] |AN W O \= / — vJ^ N _ / ^ C i cAYr 2412962-51-5

[0468] LS1

[0469] Br

[0470] B208 N^N

[0471] 2222422-14-0

[0472] LS2 Br Q CQ

[0473] N^N

[0474] B209 / ö=\

[0475] \ \ O )=< — /

[0476] 2145074-66-2

[0477] LS1

[0478] Br

[0479] $ O \= / — V / M /

[0480] B210

[0481] 2305965-75-5

[0482] LS1

[0483] Br

[0484] N A N O — vJA. , N

[0485] B211 A |Q

[0486] 2305366-94-1 LS5

[0487] Br

[0488] \ / vJY\

[0489] $

[0490] B212 HOUSE N \ o'Ar

[0491] 1ST

[0492] N= /

[0493] 1931932-25-0

[0494] LS1

[0495] Br

[0496] / =V / N= ^ o

[0497] B213 |THE

[0498] YYIRP oYj / *

[0499] 2360972-19-4 Q

[0500] LS2 VX> <

[0501] Br

[0502] $ o

[0503] B214

[0504] Qp S 9 2241862-28-0

[0505] LS1

[0506] Br

[0507] \ \= / / — \ / p N- / ^ / N

[0508] B215 0 X a v ~o

[0509] 2366135-33-1

[0510] LS1

[0511] Br

[0512] 7=\ N=^~

[0513] B216 N %N \ / - VJHO oP z

[0514] >U< 1616413-67-2 LS1

[0515] Br o u

[0516] B217

[0517] 2379260-80-5

[0518] LS1

[0519] B218 N^N AÄ 0 T=\ N Z / V< > iy - A o 1476799-05-9 <r

[0520] LS1 ^^ / Br u y-n / =\

[0521] N^Sl

[0522] B219 N 2\=N HJ J o^ o

[0523] 1955546-91 -4

[0524] LS1 u

[0525] B220

[0526] ^=N

[0527] 2102445-21 -4

[0528] LS1

[0529] ^^Br u

[0530] B221 N^Sl

[0531] 2304744-52-1 LS1 u

[0532] N^Sl

[0533] B222

[0534] ■ ;

[0535] 1354469-59-2

[0536] LS5 r vvk 0.

[0537] \ _ / \ / / o

[0538] B223 A Q

[0539] 7 < / N / — k /

[0540] ^=N OA

[0541] 2102445-28-1

[0542] LS2

[0543] B224

[0544] - V :

[0545] 1613700-80-3

[0546] LS1 c*

[0547] N^Sl

[0548] B225 0- / =\ rA'i ^=N

[0549] ° v °9

[0550] 2640603-70-7

[0551] LS1

[0552] M 3 ' x. A YES / =\

[0553] B226 or

[0554] Q-0 Dear Reader

[0555] 2360972-14-9 LS1

[0556] ACAA >O< / ^V / =\

[0557] B227 vs. O

[0558]

[0559] 2360972-15-0 Ci

[0560] LS1

[0561] ‘^cy^ >“ N K / — \

[0562] B228 vO OR

[0563] 2583051 -98-1 oi 5O v

[0564] ​LS1 O v Ov

[0565] QT JA A

[0566] B229 N \=N >~V7 UL ADI

[0567] 2448198-86-3

[0568] 5

[0569] LS2 c*

[0570] A

[0571] B230 a 1 -^

[0572] B2583051 -63-0

[0573] LS2 u

[0574] AN

[0575] B231

[0576] 2311845-38-0 LS1 fi

[0577] B232 N^N [ / ■Xi 77989-15-2 a

[0578] LS1 -A o n

[0579] J E

[0580] B233 QAAQX) cf r° 2377798-35-9

[0581] LS1 fl

[0582] Y E

[0583] B234 aX of 17 2173555-84-3

[0584] LS2 fl

[0585] Y Er

[0586] I\XN

[0587] B235 A X

[0588] Qi N

[0589] XO

[0590] 2454451 -45-5

[0591] LS1

[0592] X

[0593] N^N

[0594] B236

[0595] 2640603-76-3 LS1 fjl

[0596] B237

[0597] N^Sl A : < cA

[0598] 1606981-69-4

[0599] LS1

[0600] B238

[0601] N^N yN / =\ cA 2=N

[0602] 1606981-68-3

[0603] LS1

[0604] 0%

[0605] B239 NX' RR YES / N^ THEY cA o

[0606] 1822310-63-6 ' (AA

[0607] LS1 o

[0608] B240 QT

[0609] N^Sl OR —

[0610] OA Q

[0611] 1266389-19-8

[0612] LS1

[0613] Br 0^ 0

[0614] B241 N^Sl O' 0^9 O N RESPONSIBILITY <T NA Q 1821221-55-9 LS1 _ ,0. _

[0615] The CM3

[0616] B242

[0617] N^Sj CO^O \ O 2102445-25-8

[0618] LS1 rj and rk / ^ O

[0619] Ö

[0620] B243 NA M QJO^Ü V ö 2375516-15-5

[0621] LS2

[0622] Br rQ SQCT-

[0623] B244

[0624] N^Sj

[0625] N 1 X—^ y=N

[0626] 2241438-12-8 o

[0627] LS1

[0628] ■?

[0629] M^N

[0630] -?

[0631] (M o

[0632] B245 N

[0633] BAAQ I and 03Mr

[0634] Q

[0635] 1613576-58-1

[0636] LS1

[0637] Oh~ Br M WMyyV

[0638] B246 M

[0639] N^Sj

[0640] N^N RESPONSIBILITY

[0641] 2497781 -71-0 LS1

[0642] Br 0 5

[0643] O

[0644] B247 O o N^Sj AZA \= / w NV z cM o 1421827-56-6

[0645] LS1

[0646] KW

[0647] CQX

[0648] B248 N^Sl VX-Rr P^v) >c6

[0649] XV avW

[0650] 2178073-69-1

[0651] LS1

[0652] The Br

[0653] B249 NN^N CH NJN^N Cr^-Q 0-V^

[0654] 1612144-78-1

[0655] LS1

[0656] CHZXT VYZ^Br

[0657] B250 N^N N ^ N N z

[0658] (# 0

[0659] 1872269-02-7 cV ü

[0660] LS1

[0661] B251 N Yv ( YVK

[0662] Z KW N Y ÖZ-Ö

[0663] (XX

[0664] 2100830-80-4 °YZ Ä z

[0665] LS1 II

[0666] Br

[0667] / =\ N^ QÖ=I<

[0668] B252 N^SJ \ \ / — 4 ) — C / i ? = /

[0669] 457613-56-8 0

[0670] LS1

[0671] Br < \XX

[0672] $

[0673] B253 N^N f\L / ~

[0674] ^ •0

[0675] 2036122-73-1

[0676] LS2

[0677] Br

[0678] Ö

[0679] B254 N^N / UVVvZ

[0680] U LJ

[0681] 2305965-80-2

[0682] LS1

[0683] Br

[0684] N^SJ

[0685] / =\ N=<

[0686] B255 \ y= / / — C ) — C N ^ / z \ \= / /

[0687] ~ £) ooc

[0688] 2305965-77-7

[0689] LS1

[0690] Br z=\ N=< z=\

[0691] $

[0692] B256 N^N \ / — C ) — C / X / y=< N— e

[0693] COCO

[0694] ^0

[0695] 1869142-13-1 LS1

[0696] Br yy / =\ N=<

[0697] B257 N^SJ \ / — C ) — C r~® r\N \ J<

[0698] 2023764-12-5

[0699] LS2 Br

[0700] [ \—L / =\ N= /

[0701] B258 N^N , \ / — C ) — CZ^o

[0702] \ >=< n — \ i

[0703] 2023764-12-5

[0704] LS5 Br yX / =\ N=<

[0705] B259 N A N \ / — C / —— ,r C ff "--

[0706] IX

[0707] \ / \ / / _

[0708] CxpO

[0709] 1782925-24-9

[0710] LS1 g'

[0711] B260 HOUSE

[0712] Qi ^O

[0713] 864377-22-0

[0714] LS1

[0715] B261 ?" O !J V°

[0716] 2036122-81-1 LS1 z> Z z

[0717] V z /

[0718] O'" -TCLJOU^l J HJO \ —L

[0719] B262 ^^ ^^^ zz== — '

[0720] ' Oh

[0721] 1797458-19-5

[0722] LS1 on

[0723] B263 HOUSE

[0724] 1 J.

[0725] 1906924-47-7

[0726] LS1

[0727] Q

[0728] I, n

[0729] B264 (X N XrT

[0730] NAI

[0731] O

[0732] 0%

[0733] 2286404-97-3

[0734] LS1 or N

[0735] B265

[0736] N^Sl O^ u

[0737] OR 2491650-65-6

[0738] LS1 on

[0739] B266 N^N oY c N 2415637-66-8 LS1 gx -kCOk / / Z - _ \ / N XAjO

[0740] B267 xx

[0741] TIX jTXg / - UXQX

[0742] 2756568-80-4 ' 0

[0743] LS1 oi

[0744] Xg" xO°

[0745] B268 HOUSE

[0746] C^ u

[0747] 2110445-25-3

[0748] LS1 ' Ö

[0749] C y^iBr

[0750] B269 N^N

[0751] XXZZ < V -x \ / \ / / _ C^ u 2435673-56-4

[0752] LS1

[0753] Q ~~rx

[0754] X^Br JO

[0755] B270 N^N

[0756] XXX XvO i

[0757] (J OR X

[0758] N

[0759] 2407453-15-8 OR

[0760] LS1

[0761] X

[0762] B271 NXI

[0763] COCO

[0764] 2222194-05-8 LS1

[0765] The Br

[0766] B276 ) — \ / — N \

[0767] C= / °

[0768] 2583051-86-7 rvo

[0769] LS1

[0770] B QÖ

[0771] Ö and V_P

[0772] B277 O^CXO

[0773] 2390035-66-0

[0774] LS1 Br

[0775] B278 N^SI xx N \ cA xg

[0776] 2361287-12-7

[0777] LS1

[0778] Bf

[0779] N

[0780] B279 I\XN

[0781] C^ u

[0782] 1266389-15-4

[0783] LS1

[0784] Vfl N

[0785] B280 N'-'XM

[0786] N^N

[0787] C* u

[0788] 1345807-78-4 LS1

[0789] CW N -X / TAJQ C)

[0790] B281 |XN y1y z L N «yi — ] - ' _ ^ N J ( / O

[0791] 1960410-80-3 0-0

[0792] LS1 Q rx^ ßr Cdx N y=N

[0793] N

[0794] B282 NXI _ _ L_

[0795] -T zXXXX o , \_ / oXo 1476799-11-7

[0796] LS1 Br or CdO N

[0797] B283 x / C YxX DOOR / N ^\

[0798] |XN |l JXI \ _ / NA J pl Ap, p O o 1702359-63-4

[0799] LS1

[0800] ,Br

[0801] N

[0802] The B284 NXI

[0803] 2222194-20-7

[0804] LS1 Q

[0805] Xr Br X'N ,==\

[0806] B285 N^N / — f— QZQ AIT O 2583051-74-3 LS1

[0807] The N

[0808] B286

[0809] Br

[0810] 1613576-60-5

[0811] __ LS1 OXo _

[0812] CH jQ to yW

[0813] The −N

[0814] B287 , .N.

[0815] 0-0

[0816] Br z VJ VLOQ w O

[0817] 2412439-58-6

[0818] LS1

[0819] N=<'

[0820] B288 -A / r QYO ' TY A-

[0821] 0 N — jV

[0822] 1256170-11-2

[0823] 1 / 2 of eq 6 o

[0824] LS1

[0825] Br

[0826] N=<

[0827] Br~<\ /

[0828] N \

[0829] B289

[0830] Ö

[0831] 1584221-36-2

[0832] 1 / 2 eq Ö

[0833] LS1

[0834] Br

[0835] N=( Br— < ,NN \

[0836] B290

[0837] 2414974-88-0

[0838] 1 / 2 eq

[0839] Example: Production of OLEDs

[0840] 1) Vacuum-processed devices:

[0841] The production of OLEDs according to the invention as well as OLEDs that serve as reference is carried out according to a general process according to WO 2004 / 058911 , which is adapted to the conditions described here (layer thickness variation, materials used).

[0842] The following examples present the results of various OLEDs. Cleaned glass plates (cleaned in a Miele laboratory dishwasher using Merck Extran cleaner) coated with 50 nm thick structured ITO (indium tin oxide) are pretreated with UV ozone for 25 minutes (UV ozone generator PR-100, UVP). These coated glass plates form the substrates onto which the OLEDs are applied.

[0843] 1a) Blue Fluorescence OLED Components - BF:

[0844] The compounds according to the invention can be used in the hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL). All materials are thermally vapor-deposited in a vacuum chamber. The emission layer (EML) always consists of at least one matrix material (host material) SMB (see Table 1) and an emitting dopant (dopant, emitter) D, which is admixed to the matrix material(s) by co-evaporation in a specific volume fraction. A specification such as SMB:D (97:3%) means that the SMB material is present in a volume fraction of 97% and the dopant D is present in a volume fraction of 3% in the layer. Analogously, the electron transport layer can also consist of a mixture of two materials, see Table 1. The materials used to produce the OLEDs are shown in Table 5 or refer to the previously presented synthesis examples.

[0845] OLEDs are characterized as standard. For this purpose, the electroluminescence spectra, current efficiency (measured in cd / A), power efficiency (measured in λ / W), and external quantum efficiency (EQE, measured in percent) are determined as a function of luminance, calculated from current-voltage-luminance characteristics (IUL characteristics) assuming a Lambertian radiation pattern, as well as the lifetime. The EQE is specified in (%) and the voltage in (V) at a luminance of 1000 cd / m². 2 The lifetime is determined at a starting luminance of 10000 cd / m 2 The measured time during which the brightness of the reference decays to 80% of the initial brightness is set to 100%. The lifetime of the OLED components containing the compounds of the invention is expressed as a percentage of the reference.

[0846] The OLEDs have the following layer structure:

[0847] Substrat

[0848] Hole injection layer (HIL) made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm

[0849] Hole transport layer (HTL), made of HTM1, 180 nm

[0850] Electron blocking layer (EBL), see Table 1

[0851] Emission layer (EML), see Table 1

[0852] Hole blocking layer (HBL), see Table 1 Electron transport layer (ETL), see Table 1

[0853] Electron injection layer (EIL) made of ETM2, 1 nm

[0854] Cathode made of aluminum, 100 nm

[0855] Table 1 : Structure of blue fluorescent OLED device

[0856] EBL EML HBL ETL Thickness Thickness Thickness

[0857] SMB1 :D1 Ref-ETM1 :ETM2

[0858] EBM1

[0859] BF-Ref1 (95%:5%) — (50%:50%)

[0860] 10 nm 20 nm 30 nm

[0861] SMB1 :D1 Ref-ETM2:ETM2

[0862] EBM1

[0863] <h2 style=";text-align:left;direction:ltr">BF-Ref2 (95%: 5%) — (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0864] <h2 style=";text-align:left;direction:ltr"> 10 nm 20 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0865] <h2 style=";text-align:left;direction:ltr"> SMB1:D1 B9:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0866] <h2 style=";text-align:left;direction:ltr"> EBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0867] <h2 style=";text-align:left;direction:ltr"> BF1 (95%:5%) — (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0868] <h2 style=";text-align:left;direction:ltr"> 10 nm 20 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0869] <h2 style=";text-align:left;direction:ltr"> SMB1:D1 B202:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0870] <h2 style=";text-align:left;direction:ltr"> EBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0871] <h2 style=";text-align:left;direction:ltr"> BF2 (95%:5%) — (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0872] <h2 style=";text-align:left;direction:ltr"> 10 nm 20 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0873] <h2 style=";text-align:left;direction:ltr"> SMB1:D1 B2:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0874] <h2 style=";text-align:left;direction:ltr"> EBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0875] <h2 style=";text-align:left;direction:ltr"> BF3 (95%:5%) — (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0876] <h2 style=";text-align:left;direction:ltr"> 10 nm 20 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0877] <h2 style=";text-align:left;direction:ltr"> SMB1:D1 B10:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0878] <h2 style=";text-align:left;direction:ltr"> EBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0879] <h2 style=";text-align:left;direction:ltr"> BF4 (95%:5%) — (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0880] <h2 style=";text-align:left;direction:ltr"> 10 nm 20 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0881] <h2 style=";text-align:left;direction:ltr"> SMB1:D1 B11:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0882] <h2 style=";text-align:left;direction:ltr"> EBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0883] <h2 style=";text-align:left;direction:ltr"> BF5 (95%:5%) — (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0884] <h2 style=";text-align:left;direction:ltr"> 10 nm 20 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0885] <h2 style=";text-align:left;direction:ltr"> SMB1:D1 B15:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0886] <h2 style=";text-align:left;direction:ltr"> EBM1<h2 style=";text-align:left;direction:ltr">

[0887] BF6 (95%: 5%) — (50%:50%)

[0888] 10 nm 20 nm 30 nm

[0889] SMB1 :D1 B31 :ETM2

[0890] EBM1

[0891] BF7 (95%: 5%) — (50%:50%)

[0892] 10 nm 20 nm 30 nm

[0893] SMB1 :D1 B204:ETM2

[0894] EBM1

[0895] BF8 (95%: 5%) — (50%:50%)

[0896] 10nm 20nm 30nm SMB1 :D1 B219:ETM2

[0897] EBM1

[0898] BF9 (95%: 5%) — (50%:50%)

[0899] 10 nm 20 nm 30 nm

[0900] SMB1 :D1 B219:ETM2

[0901] EBM1

[0902] BF10 (95%: 5%) B219 (50%:50%)

[0903] 10 nm 20 nm 5 nm 30 nm

[0904] Table 2: Results of blue fluorescent OLED devices

[0905] EQE (%) Voltage (V) LT80 [%]

[0906] Example: 1000 cd / m 2 1000 cd / m 2 10000 cd / m 2

[0907] BF-Ref1 7.7 4.1 100

[0908] BF-Ref2 7.8 4.0 100

[0909] BF1 8.1 3.9 170

[0910] BF2 8.3 4.0 150

[0911] BF3 8.2 4.0 160

[0912] BF4 7.9 3.9 155

[0913] BF5 7.7 3.8 135

[0914] BF6 8.1 3.9 125

[0915] BF7 8.0 3.9 155

[0916] BF8 8.0 4.1 165

[0917] BF9 7.7 3.9 150

[0918] BF10 7.8 4.0 145

[0919] 1 b) Phosphorescent OLED components:

[0920] The compounds A according to the invention can be used in the hole injection layer (HIL), the hole transport layer (HTL), the electron blocking layer (EBL), and in the emission layer (EML) as matrix material (host material) M (see Table 5) or A (see materials according to the invention). For this purpose, all materials are thermally vapor-deposited in a vacuum chamber. The emission layer always consists of at least one or more matrix materials M and a phosphorescent dopant Ir, which is admixed to the matrix material(s) by co-evaporation in a specific volume fraction. A specification such as M1:M2:Ir (55%:35%:10%) means that the material M1 is present in the layer in a volume fraction of 55%, M2 in a volume fraction of 35%, and Ir in a volume fraction of 10%. Analogously, the electron transport layer can also consist of a mixture of two materials.The exact structure of the OLEDs can be found in Table 3. The materials used to fabricate the OLEDs are shown in Table 5 or refer to the synthesis examples presented previously.

[0921] OLEDs are characterized as standard. For this purpose, the electroluminescence spectra, current efficiency (measured in cd / A), power efficiency (measured in λ / W), and external quantum efficiency (EQE, measured in percent) are determined as a function of luminance, calculated from current-voltage-luminance characteristics (IUL characteristics) assuming a Lambertian radiation pattern, as well as the lifetime. The EQE is specified in (%) and the voltage in (V) at a luminance of 1000 cd / m². 2 The lifetime is determined at a starting luminance of 1000 cd / m 2 for blue and red and 10000 cd / m 2for green and yellow. The measured time in which the brightness of the reference decays to 80% of the initial brightness is set to 100%. The lifetime of the OLED components containing the compounds of the invention is given as a percentage of the respective analogously constructed reference or, when using the compounds of the invention as matrix material, of the component containing Ref-ETM2 in the ETL and HBM2 in the HBL.

[0922] The OLEDs have the following layer structure:

[0923] Substrat

[0924] Hole injection layer (HIL) made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm

[0925] Hole transport layer (HTL) made of HTM1, 180 nm for blue, 50 nm for green, yellow and red

[0926] Electron blocking layer (EBL), see Table 3 Emission layer (EML), see Table 3

[0927] Hole blocking layer (HBL), see Table 3

[0928] Electron transport layer (ETL), see Table 3

[0929] Electron injection layer (EIL) made of ETM2, 1 nm

[0930] Cathode made of aluminum, 100 nm

[0931] Table 3: Structure of phosphorescent OLED components

[0932] EML

[0933] EBL HBL ETL

[0934] Example: Thickness Thickness Thickness Thickness

[0935] Blue

[0936] M3:M4:lrB1 Ref-ETM1 :ETM2

[0937] EBM2 HBM2

[0938] BP-Ref1 (30% (50%:50%)

[0939] 20nm: 65%: 5%) 5nm 25nm 30nm

[0940] M3:M4:lrB1 Ref-ETM2:ETM2

[0941] EBM2 HBM2

[0942] BP-Ref2 (30%: (50%:50%)

[0943] 20nm 65%: 5%) 5nm 25nm 30nm

[0944] M3:M4:lrB1 B9:ETM2

[0945] EBM2 HBM2

[0946] BP1 (30 (50%:50%)

[0947] 20nm %: 65%: 5%) 5nm 25nm 30nm

[0948] M3:M4:lrB1 B202:ETM2

[0949] EBM2 HBM2

[0950] BP2 (30%: 65%: 5%) (50%:50%) 20 nm 5 nm 25 nm 30 nm

[0951] M3:M4:lrB1 B9:ETM2

[0952] EBM2 B55

[0953] BP3 (50%:50%) 20 nm (30%: 65%: 5%) 5 nm 25 nm 30 nm

[0954] M3:M4:lrB1 B202:ETM2

[0955] EBM2 B55

[0956] BP4 (30%: 65%: 5%) (50%:50%) 20 nm 5 nm 25 nm 30 nm

[0957] B5:M4:lrB1 ETMTETM2

[0958] EBM2 HBM2

[0959] BP5 (30%: 65%: 5%) (50%:50%) 20 nm 5 nm 25 nm 30 nm

[0960] B20:M4:lrB1 ETMTETM2

[0961] EBM2 HBM2

[0962] BP6 (30%: 65%: 5%) (50%:50%) 20 nm 5 nm 25 nm 30 nm B21 :M4:lrB1 ETM1 :ETM2

[0963] EBM2 HBM2

[0964] BP7 (30%: 65%: 5%) (50%:50%) 20 nm 5 nm 25 nm 30 nm

[0965] B24:M4:lrB1 ETM1 :ETM2

[0966] EBM2 HBM2

[0967] BP8 (30%: 65%: 5%) (50%:50%) 20 nm 5 nm 25 nm 30 nm

[0968] B32:M4:lrB1 ETM1 :ETM2

[0969] EBM2 HBM2

[0970] BP9 (30%: 65%: 5%) (50%:50%) 20 nm 5 nm 25 nm 30 nm

[0971] B201 :M4:lrB1 ETM1 :ETM2

[0972] EBM2 HBM2

[0973] BP10 (30%: 65%: 5%) (50%:50%) 20 nm 5 nm 25 nm 30 nm

[0974] B216:M4:lrB1 ETM1 :ETM2

[0975] EBM2 HBM2

[0976] BP11 (50%:50% 0 nm (30%: 6 ) 2 5%: 5%) 5 nm 25 nm 30 nm

[0977] B220:M4:lrB1 ETM1 :ETM2

[0978] EBM2 HBM2

[0979] BP12 ( (50%:50%) 20 nm 30%: 65%: 5%) 5 nm 25 nm 30 nm

[0980] B300:M4:lrB1 ETM1 :ETM2

[0981] EBM2 HBM2

[0982] BP13 (30% (50%:50%) 20 nm : 65%: 5%) 5 nm 25 nm 30 nm

[0983] Grün

[0984] M1 :M2:lrG1 Ref-ETM1 :ETM2

[0985] EBM1 HBM1

[0986] GP-Ref1 (30%:60%:10%) (50%:50%)

[0987] 20 nm 5 nm 40 nm 30 nm

[0988] M1 :M2:lrG1 Ref-ETM2:ETM2

[0989] EBM1 HBM1

[0990] GP-Ref2 (30%:60%:10%) (50%:50%)

[0991] 20 nm 5 nm 40 nm 30 nm

[0992] M1 :M2:lrG1 Ref- Ref-ETM2:ETM2

[0993] EBM1

[0994] GP-Ref2 (30%:60%:10%) HBM1 (50%:50%)

[0995] 20 nm 40 nm 5 nm 30 nm

[0996] M1 :M2:lrG1 B9:ETM2

[0997] EBM1 HBM1

[0998] GP1 (30%:60%:10%) (50%:50%)

[0999] 20 nm 5 nm 40 nm 30 nm

[1000] M1 :M2:lrG1 B202:ETM2

[1001] EBM1 HBM1

[1002] GP2 (30%:60%:10%) (50%:50%)

[1003] 20 nm 5 nm 40 nm 30 nm

[1004] M1 :M2:lrG1 B202:ETM2

[1005] EBM1 B202

[1006] GP3 (30%:60%:10%) (50%:50%) <h2 style=";text-align:left;direction:ltr">

[1007] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm M1 :M2:lrG1 B16:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1008] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1009] <h2 style=";text-align:left;direction:ltr"> GP4 (30%:60%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1010] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1011] <h2 style=";text-align:left;direction:ltr"> M1:M2:lrG1 B19:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1012] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1013] <h2 style=";text-align:left;direction:ltr"> GP5 (30%:60%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1014] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1015] <h2 style=";text-align:left;direction:ltr"> M1:M2:lrG1 B34:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1016] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1017] <h2 style=";text-align:left;direction:ltr"> GP6 (30%:60%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1018] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1019] <h2 style=";text-align:left;direction:ltr"> M1:M2:lrG1 B49:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1020] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1021] <h2 style=";text-align:left;direction:ltr"> GP7 (30%:60%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1022] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1023] <h2 style=";text-align:left;direction:ltr"> M1:M2:lrG1 B205:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1024] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1025] <h2 style=";text-align:left;direction:ltr"> GP8 (30%:60%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1026] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1027] <h2 style=";text-align:left;direction:ltr"> M1:M2:lrG1 B293:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1028] <h2 style=";text-align:left;direction:ltr">EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1029] <h2 style=";text-align:left;direction:ltr"> GP9 (30%:60%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1030] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1031] <h2 style=";text-align:left;direction:ltr"> M1:M2:lrG1 B9:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1032] <h2 style=";text-align:left;direction:ltr"> EBM1 B26<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1033] <h2 style=";text-align:left;direction:ltr"> GP10 (30%:60%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1034] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1035] <h2 style=";text-align:left;direction:ltr"> M1:M2:lrG1 B9:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1036] <h2 style=";text-align:left;direction:ltr"> EBM1 B47<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1037] <h2 style=";text-align:left;direction:ltr"> GP11 (30%:60%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1038] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1039] <h2 style=";text-align:left;direction:ltr"> B50:M2:lrG1 ETM1 :ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1040] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1041] <h2 style=";text-align:left;direction:ltr"> GP12 (30%:60%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1042] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1043] <h2 style=";text-align:left;direction:ltr"> B60:M2:lrG1 ETM1 :ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1044] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1045] <h2 style=";text-align:left;direction:ltr"> GP13 (30%:60%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1046] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1047] <h2 style=";text-align:left;direction:ltr"> B108:M2:lrG1 ETM1 :ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1048] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1049] <h2 style=";text-align:left;direction:ltr"> GP14 (30%:60%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr">

[1050] 20 nm 5 nm 40 nm 30 nm

[1051] Gelb

[1052] M1 :M2:lrG2 Ref-ETM1 :ETM2

[1053] GP- EBM1 HBM1 (30%:70%:10%) (50%:50%) Ref50 20 nm 5 nm 40 nm 30 nm

[1054] M1 :M2:lrG2 Ref-ETM2:ETM2

[1055] GP- EBM1 HBM1 (30%:70%:10%) (50%:50%)

[1056] Ref51 20 nm 5 nm 40 nm 30 nm

[1057] M1 :M2:lrG2 Ref- Ref-ETM2:ETM2

[1058] GP- EBM1 (30%:60%:10%) HBM1 (50%:50%) Ref52 20 nm 40 nm 5 nm 30 nm M1 :M2:lrG2 B9:ETM2

[1059] EBM1 HBM1

[1060] GP50 (30%:70%:10%) (50%:50%)

[1061] 20 nm 5 nm 40 nm 30 nm

[1062] M1 :M2:lrG2 B202:ETM2

[1063] EBM1 HBM1

[1064] GP51 (30%:70%:10%) (50%:50%)

[1065] 20 nm 5 nm 40 nm 30 nm

[1066] M1 :M2:lrG2 B202:ETM2

[1067] EBM1 B202

[1068] GP52 (30%:60%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1069] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1070] <h2 style=";text-align:left;direction:ltr"> M1:M2:lrG2 B38:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1071] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1072] <h2 style=";text-align:left;direction:ltr"> GP53 (30%:70%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1073] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1074] <h2 style=";text-align:left;direction:ltr"> M1:M2:lrG2 B54:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1075] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1076] <h2 style=";text-align:left;direction:ltr"> GP54 (30%:70%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1077] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1078] <h2 style=";text-align:left;direction:ltr"> M1:M2:lrG2 B9:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1079] <h2 style=";text-align:left;direction:ltr"> EBM1 B17<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1080] <h2 style=";text-align:left;direction:ltr"> GP55 (30%:60%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1081] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1082] <h2 style=";text-align:left;direction:ltr"> M1:M2:lrG2 B9:ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1083] <h2 style=";text-align:left;direction:ltr"> EBM1 B246<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1084] <h2 style=";text-align:left;direction:ltr"> GP56 (30%:60%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1085] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1086] <h2 style=";text-align:left;direction:ltr"> B23:M2:lrG2 ETM1 :ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1087] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1088] <h2 style=";text-align:left;direction:ltr"> GP57 (30%:70%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1089] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1090] <h2 style=";text-align:left;direction:ltr">B28:M2:lrG2 ETM1 :ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1091] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1092] <h2 style=";text-align:left;direction:ltr"> GP58 (30%:70%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1093] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1094] <h2 style=";text-align:left;direction:ltr"> B64:M2:lrG2 ETM1 :ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1095] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1096] <h2 style=";text-align:left;direction:ltr"> GP59 (30%:70%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1097] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1098] <h2 style=";text-align:left;direction:ltr"> B110:M2:lrG2 ETM1 :ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1099] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1100] <h2 style=";text-align:left;direction:ltr"> GP60 (30%:70%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1101] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1102] <h2 style=";text-align:left;direction:ltr"> B115:M2:lrG2 ETM1 :ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1103] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1104] <h2 style=";text-align:left;direction:ltr"> GP61 (30%:70%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1105] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1106] <h2 style=";text-align:left;direction:ltr"> B217:M2:lrG2 ETM1 :ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1107] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1108] <h2 style=";text-align:left;direction:ltr"> GP62 (30%:70%:10%) (50%:50%)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1109] <h2 style=";text-align:left;direction:ltr"> 20 nm 5 nm 40 nm 30 nm<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1110] <h2 style=";text-align:left;direction:ltr"> B226:M2:lrG2 ETM1 :ETM2<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[1111] <h2 style=";text-align:left;direction:ltr"> EBM1 HBM1<h2 style=";text-align:left;direction:ltr">

[1112] GP63 (30%:70%:10%) (50%:50%)

[1113] 20 nm 5 nm 40 nm 30 nm

[1114] Rot M5:lrR1 Ref-ETM1 :ETM2

[1115] EBM1 HBM1

[1116] RP-Ref1 (95%: 5%) (50%:50%)

[1117] 20 nm 5 nm 35 nm 30 nm

[1118] M5:lrR1 Ref-ETM2:ETM2

[1119] EBM1 HBM1

[1120] RP-Ref2 (95%: 5%) (50%:50%)

[1121] 20 nm 5 nm 35 nm 30 nm

[1122] M5:lrR1 Ref- Ref-ETM2:ETM2

[1123] EBM1

[1124] RP-Ref3 (95%: 5%) HBM1 (50%:50%)

[1125] 20 nm 35 nm 5 nm 30 nm

[1126] M5:lrR1 B9:ETM2

[1127] EBM1 HBM1

[1128] RP1 (95%: 5%) (50%:50%)

[1129] 20 nm 5 nm 35 nm 30 nm

[1130] M5:lrR1 B202:ETM2

[1131] EBM1 HBM1

[1132] RP2 (95%: 5%) (50%:50%)

[1133] 20 nm 5 nm 35 nm 30 nm

[1134] M5:lrR1 B202:ETM2

[1135] EBM1 B202

[1136] RP3 (95%: 5%) (50%:50%)

[1137] 20 nm 5 nm 35 nm 30 nm

[1138] B65:lrR1 ETM1 :ETM2

[1139] EBM1 HBM1

[1140] RP4 (95%: 5%) (50%:50%)

[1141] 20 nm 5 nm 35 nm 30 nm

[1142] B86:lrR1 ETM1 :ETM2

[1143] EBM1 HBM1

[1144] RP5 (92%:8%) (50%:50%)

[1145] 20 nm 5 nm 35 nm 30 nm

[1146] B89:lrR1 ETM1 :ETM2

[1147] EBM1 HBM1

[1148] RP6 (95%: 5%) (50%:50%)

[1149] 20 nm 5 nm 35 nm 30 nm

[1150] B101 :lrR1 ETM1 :ETM2

[1151] EBM1 HBM1

[1152] RP7 (95%: 5%) (50%:50%)

[1153] 20 nm 5 nm 35 nm 30 nm

[1154] B127:lrR1 ETM1 :ETM2

[1155] EBM1 HBM1

[1156] RP8 (95%: 5%) (50%:50%)

[1157] 20 nm 5 nm 35 nm 30 nm

[1158] B256:lrR1 ETM1 :ETM2

[1159] EBM1 HBM1

[1160] RP9 (95%: 5%) (50%:50%)

[1161] 20 nm 5 nm 35 nm 30 nm

[1162] B257:lrR1 ETM1 :ETM2

[1163] EBM1 HBM1

[1164] RP10 (95%: 5%) (50%:50%)

[1165] 20 nm 5 nm 35 nm 30 nm

[1166] B282:lrR1 ETM1 :ETM2

[1167] EBM1 HBM1

[1168] RP11 (95%: 5%) (50%:50%)

[1169] 20 nm 5 nm 35 nm 30 nm

[1170] B287:lrR1 ETM1 :ETM2

[1171] EBM1 HBM1

[1172] RP12 (95%: 5%) (50%:50%)

[1173] 20 nm 5 nm 35 nm 30 nm Tabelle 4: Ergebnisse Phosphoreszenz-OLED-Bauteile

[1174] Blau

[1175] EQE (%) Spannung (V) LT80 (%)

[1176] Bsp. 1000 cd / m 2 1000 cd / m 21000 cd / m 2

[1177] BP-Ref1 21.0 4.4 100

[1178] BP-Ref2 21.3 4.2 100

[1179] BP1 21.5 4.3 170

[1180] BP2 21.7 4.2 145

[1181] BP3 22.1 4.1 155

[1182] BP4 22.0 4.1 165

[1183] BP5 22.0 4.1 150

[1184] BP6 21.6 4.0 140

[1185] BP7 22.3 4.2 160

[1186] BP8 21.9 4.1 160

[1187] BP9 22.0 4.1 135

[1188] BP10 21.7 4.1 190

[1189] BP11 22.2 4.0 160

[1190] BP12 21.9 4.0 140

[1191] BP13 22.0 4.1 170

[1192] Grün

[1193] EQE (%) Spannung (V) LT80 (%)

[1194] Bsp. 1000 cd / m 2 1000 cd / m 2 10000 cd / m 2

[1195] GP-Ref1 22.2 3.2 100

[1196] GP-Ref2 22.1 3.2 100

[1197] GP-Ref3 22.7 3.3 100

[1198] GP1 22.1 3.3 180

[1199] GP2 22.7 3.3 140 GP3 22.5 3.4 175

[1200] GP4 22.1 3.3 140

[1201] GP5 22.4 3.1 145

[1202] GP6 22.0 3.2 130

[1203] GP7 21.9 3.2 190

[1204] GP8 22.1 3.3 155

[1205] GP9 22.0 3.2 140

[1206] GP10 22.3 3.2 155

[1207] GP11 22.6 3.1 170

[1208] GP12 22.2 3.2 130

[1209] GP13 22.1 3.2 165

[1210] GP14 22.5 3.1 135

[1211] Gelb

[1212] GP-Ref50 29.4 3.0 100

[1213] GP-Ref51 29.0 3.0 100

[1214] GP-Ref52 29.2 3.1 100

[1215] GP50 29.5 3.2 170

[1216] GP51 30.0 3.1 150

[1217] GP52 29.6 3.2 165

[1218] GP53 30.2 3.0 120

[1219] GP54 30.0 2.9 140

[1220] GP55 30.3 3.2 160

[1221] GP56 30.7 3.1 175

[1222] GP57 29.5 3.1 140

[1223] GP58 30.0 3.1 190

[1224] GP59 30.4 3.2 150

[1225] GP60 29.8 3.1 135 GP61 29.8 3.1 140

[1226] GP62 30.1 3.2 145

[1227] GP63 30.3 3.2 140

[1228] Rot

[1229] EQE (%) Spannung (V) LT80 (%)

[1230] Bsp. 1000 cd / m 2 1000 cd / m 2 1000 cd / m 2

[1231] RP-Ref1 16.5 3.3 100

[1232] RP-Ref2 16.8 3.4 100

[1233] RP-Ref3 16.6 3.3 100

[1234] RP1 16.6 3.4 180

[1235] RP2 16.7 3.4 145

[1236] RP3 16.9 3.5 160

[1237] RP4 16.8 3.4 110

[1238] RP5 16.6 3.4 140

[1239] RP6 16.8 3.3 165

[1240] RP7 16.5 3.4 145

[1241] RP8 16.4 3.5 150

[1242] RP9 16.5 3.3 160

[1243] RP10 16.8 3.4 160

[1244] RP11 16.8 3.3 190

[1245] RP12 16.3 3.4 180 Table 5: Structural formulas of the materials used

[1246]

[1247] Fluorescent Blue Phosphorescent Blue

[1248] D1 1182175-27-4 lrB1

[1249] 1541114-98-0

[1250] Phosphorescent Green Phosphorescent Yellow lrG1 2245866-06-0 lrG2 2245945-28-0

Claims

Claims Compound comprising at least one structure of formula (I), Formula (I) where the symbols are: Z a represents, the same or different at each occurrence, Ar, R c , L 1 - Q, or L 1 -N(Ar)2; Q, the same or different at each occurrence, represents an electron transport group; L 1 represents, identically or differently at each occurrence, a bond or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R; R a is at each occurrence, identically or differently, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 10 C atoms, each of which is substituted by one or more radicals R 2may be substituted, or an aromatic or heteroaromatic ring system with 5 to 20 aromatic ring atoms, each substituted by one or several residues R 2 can be substituted, two or more substituents R a form a ring system with each other; R b is, at each occurrence, identically or differently, H, D, straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 10 C atoms, each of which is substituted by one or more radicals R 2 may be substituted, or an aromatic or heteroaromatic ring system with 5 to 20 aromatic ring atoms, each substituted by one or more radicals R 2 can be substituted, two substituents R b form a ring system with each other; Ar is, at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals R, where two radicals Ar which bind to the same N atom may also be bridged to one another by a single bond or a bridge selected from B(R), C(R)2, Si(R)2, C=O, C=NR, C=C(R)2, RC=CR, O, S, S=O, SO2, N(R), P(R), P(=O)R and an ortho-linked phenylene group which may be substituted by one or more radicals R; R, R c , R d is, at each occurrence, the same or different: H, D, OH, F, CI, Br, I, CN, NO2, N(Ar')2, N(R 1 )2, C(=O)N(Ar')2, C(=O)N(R 1 )2, C(Ar')3, C(R 1 )3, Si(Ar')3, Si(R 1 )3, B(Ar')2, B(R 1 )2, C(=O)Ar', C(=O)R 1 , P(=O)(Ar')2, P(=O)(R 1 )2, P(Ar')2, P(R 1 )2, S(=O)Ar', S(=O)R 1 , S(=O)2Ar', S(=O)2R 1, OSO2Ar', OSO2R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group is each substituted with one or more radicals R 1 be substituted where one or more non-adjacent CH2 groups are represented by R 1 C=CR 1 , CEC, Si(R 1 )2, C=O, C=S, C=Se, C=NR 1 , -C(=O)O-, -C(=O)NR 1 -, NR 1 , P(=O)(R 1 ), -O-, -S-, SO or SO2, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which is substituted by one or more radicals R 1 may be substituted, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R1 can be substituted, two radicals R, R d also with each other or a residue R, R d with another group, in particular a residue R c form a ring system; Ar' is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is substituted with one or more radicals R 1 may be substituted, whereby two radicals Ar' which bind to the same C-atom, Si-atom, N-atom, P-atom or B-atom may also be substituted by a single bond or a bridge selected from B(R 1 ), C(R 1 )2, Si(R 1 )2, C=O, C=NR 1 , C=C(R 1 )2, 0, S, S=O, SO2, N(R 1 ), P(R 1 ) and P(=O)R 1 , be bridged together; R 1 is, at each occurrence, the same or different: H, D, F, CI, Br, I, CN, NO2, N(Ar”)2, N(R 2 )2, C(=O)Ar”, C(=O)R 2, P(=O)(Ar”)2, P(Ar”)2, B(Ar”)2, B(R 2 )2, C(Ar”)3, C(R 2 )3, Si(Ar”)3, Si(R 2 )3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms or an alkenyl group having 2 to 40 C atoms, each of which is substituted by one or more radicals R 2 may be substituted, wherein one or more non-adjacent CH2 groups are substituted by - R 2 C=CR 2 -, -CEC-, Si(R 2 )2, C=O, C=S, C=Se, C=NR 2 , -C(=O)O- -C(=O)NR 2 -, NR 2 , P(=O)(R 2 ), -O-, -S-, SO or SO2 and where one or more H atoms are replaced by D, F, CI, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which is substituted by one or more radicals R 2may be substituted, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 2 may be substituted, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms which may be substituted with one or more radicals R 2 may be substituted, or a combination of these systems; two or more radicals R 1 form a ring system, whereby one or more residues R 1 form a ring system with another part of the compound; Ar” is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is substituted by one or more radicals R 2 may be substituted, whereby two radicals Ar” which bind to the same C-atom, Si-atom, N-atom, P-atom or B-atom can also be linked by a single bond or a bridge selected from B(R 2 ), C(R 2)2, Si(R 2 )2, C=O, C=NR 2 , C=C(R 2 )2, O, S, S=O, SO2, N(R 2 ), P(R 2 ) and P(=O)R 2 , be bridged together; R 2 is selected, identically or differently at each occurrence, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D, F, CI, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms, where two or more substituents R 2 form a ring system with each other. A compound according to claim 1, comprising at least one structure of formulas (I-1) to (I-4), Formula (1-1 ) Formula (I-2) where the symbols Ar, Lr 1 , Q, R a , R b and R chave the meanings given in claim 1. Compound according to claim 1 or 2, characterized in that the group Q represents a pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, quinoline, isoquinoline, imidazole and / or benzimidazole group which is substituted with one or more radicals R d A compound according to one or more of claims 1 to 3, characterized in that the group Q represents a nitrogen-containing Heteroaryl group with 6 to 12 ring atoms with at least two nitrogen atoms in a ring, which with one or more radicals R dmay be substituted, wherein the carbon atoms adjacent to at least two of the nitrogen atoms in a ring are not bonded to a hydrogen atom. Compound according to at least one of the preceding claims 1 to 4, characterized in that the group Ar is selected, identically or differently at each occurrence, from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene, which may each be substituted by one or more radicals R. Compound according to one or more of claims 1 to 5, characterized in that the group L 1 identically or differently represents a bond or is selected from structures of the formulas (L 1 -1 ) to (L1 -22), Formula (L 1 -4) Formula (L 1 -5) Formula (L 1 -6) Formula (L 1 -7) Formula (L 1 -9) Formula (L 1 -10) Formula (L 1 -11 ) Formula (L 1 -12) Formula (L 1 -13) Formula (L 1 -14) Formula (L 1 -15) Formula (L 1 -17) Formula (L 1 -18) Formula (L 1 -19) Formula (L 1 -20) Formula (L 1 -21 ) Formula (L 1 -22) where the symbols used are: Y is CR2, O, S or NR; j is 0, 1, 2 or 3 at each occurrence; h is 0, 1, 2, 3 or 4 at each occurrence; R has the meaning given above, in particular for claim 1, and the dashed bonds mark the attachment positions. A compound according to one or more of claims 1 to 6, characterized in that the group Q is selected, identically or differently at each occurrence, from structures of the formulas (Q-1) to (Q-16), R d (Q-1 ) (Q-2) (Q-3) where R d has the meaning mentioned above, in particular for claim 1, the dashed bonds mark the attachment positions and the other symbols have the following meaning: Y 1 stands for 0, S, NR d or C(R d )2; n is independently 0, 1, 2 or 3 at each occurrence; and m is independently 0, 1, 2, 3 or 4 at each occurrence. A compound according to one or more of claims 1 to 7, comprising at least one structure of the formulas (II-1) to (II-44), Formula (11-1 ) Formula (II-2) Formula (II-3) Formula (II-4) Formula (II-5) Formula (II-6) Formula (II-7) Formula (II-8) Formula (11-13) Formula (11-14) Formula (11-15) Formula (11-16) Formula (11-17) Formula (11-18) Formula (11-21 ) Formula (II-22) Formula (II-23) Formula (II-24) Formula (II-32) Formula (11-31) Formula (II-37) Formula (II-38) Formula (II-39) Formula (II-40) Formula (11-41 ) Formula (II-42) Formula (II-43) Formula (II-44) where the symbols R, R a , R b , R c and R d have the meanings given in claim 1 and the following applies to the other symbols: X represents, at each occurrence, the same or different, N, CR or C, in the case of a group bonded to the structure; X I represents N or CR, the same or different at each occurrence d ; X 2represents N or CR, the same or different at each occurrence d ; Y represents O, S, NR or C(R)2, preferably O, NR or C(R)2; and Y 1 stands for 0, S, NR d or C(R d )2. A compound according to one or more of claims 1 to 8, comprising at least one structure of the formulas (III-1) to (III-48), Formula (111-1 ) Formula (III-2) Formula (III-3) Formula (III-4) Formula (III-5) Formula (III-6) Formula (HI-7) Formula (HI-8) Formula (III-9) Formula (111-10) Formula (111-11 ) Formula (111-12) Formula (111-13) Formula (111-14) Formula (111-17) Formula (111-18) Formula (111-19) Formula (HI-20) Formula (HI-23) Formula (HI-24) Formula (HI-25) Formula (HI-26) Formula (HI-27) Formula (HI-28) Formula (III-29) Formula (III-30) Formula (111-31 ) Formula (III-32) Formula (III-33) Formula (HI-34) Formula (III-35) Formula (III-36) (R)n Formula (III-39) Formula (III-40) Formula (111-41 ) Formula (HI-42) Formula (HI-43) Formula (HI-44) Formula (HI-45) Formula (HI-46) Formula (III-47) Formula (III-48) where the symbols R, R a , R b , R c and R d have the meanings given in claim 1 and the symbols used are: Y is O, S, NR or C(R)2; Y 1 is 0, S, NR d or C(R d )2; n is 0, 1, 2, or 3 on each occurrence independently; m is 0, 1, 2, 3, or 4 on each occurrence independently. Compound according to at least one of the preceding claims 1 to 9, characterized in that the group R crepresents H, D, methyl, ethyl, propyl, where these groups may be deuterated. A compound according to at least one of the preceding claims 1 to 10, characterized in that none of the radicals R, R a , R c , R dan aromatic or heteroaromatic ring system having three fused aromatic 6-membered rings. An oligomer, polymer, or dendrimer comprising one or more compounds according to any one of claims 1 to 11, wherein, instead of a hydrogen atom or a substituent, one or more bonds of the compounds to the polymer, oligomer, or dendrimer are present. A formulation comprising at least one compound according to one or more of claims 1 to 11 or an oligomer, polymer, or dendrimer according to claim 12 and at least one further compound, wherein the further compound is preferably selected from one or more solvents.A composition comprising at least one compound according to one or more of claims 1 to 11 or an oligomer, polymer, or dendrimer according to claim 12 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF, host materials, electron-transport materials, electron-injection materials, hole-conductor materials, hole-injection materials, electron-blocking materials, and hole-blocking materials. A process for preparing a compound according to one or more of claims 1 to 11, characterized in that a phenyl compound to which a cyclopentyl group is fused is synthesized, and at least one aromatic or heteroaromatic radical is introduced, preferably by means of a... nucleophilic aromatic substitution reaction or a coupling reaction. Use of a compound according to one or more of claims 1 to 11 or an oligomer, polymer, or dendrimer according to claim 12 in an electronic device, preferably as a host material, electron injection material, electron transport material, or hole blocking material. Electronic device comprising at least one compound according to one or more of claims 1 to 11 or an oligomer, polymer, or dendrimer according to claim 12.

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