Organic electronic device and special materials for organic electronic devices
Patent Information
- Application Number
- EP2023818404
- Authority / Receiving Office
- EP · EP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2022-12-08
- Filing Date
- 2023-12-05
- Publication Date
- 2025-10-15
AI Technical Summary
Current organic electroluminescent devices (OLEDs) face limitations in efficiency, operating voltage, and service life, particularly when using phosphorescent emitters, and there is a need for improved matrix materials to enhance these properties, especially at low to medium emitter concentrations.
Incorporating specific 4H-naphtho[1,2,3,4-def]carbazole derivatives as a combination with other matrix materials in the light-emitting layer of organic electronic devices to improve device performance, including using them as matrix, hole transport, hole injection, or electron blocking materials.
The combination of 4H-naphtho[1,2,3,4-def]carbazole derivatives with other matrix materials in the light-emitting layer enhances the service life and maintains or improves operating efficiency and voltage stability of OLEDs, particularly at low to medium emitter concentrations.
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Abstract
Description
[0001] - 1 - Organic electronic device and special materials for organic electronic devices Technical field The present invention relates to an organic electronic device comprising an anode, a cathode and at least one light-emitting layer containing at least one 4H-naphtho[1,2,3,4-def]carbazole and a further matrix material, to special 4H-naphtho[1,2,3,4-def]carbazole derivatives, mixtures and formulations containing them and to electronic devices containing these special 4H-naphtho[1,2,3,4-def]carbazole derivatives, in particular organic electroluminescent devices or OLEDs containing these compounds, as matrix materials, hole transport materials, hole injection materials or electron blocking materials. State of the art Phosphorescent organometallic complexes are frequently used in organic electroluminescent devices (OLEDs).In general, there is still room for improvement in OLEDs, for example, with regard to efficiency, operating voltage, and lifetime. The properties of phosphorescent OLEDs are determined not only by the triplet emitters used. The other materials used, such as matrix materials, are also particularly important. Improvements to these materials can therefore also lead to significant improvements in OLED properties. Another possibility for improving the performance of organic electronic devices, especially organic electroluminescent devices, is to use combinations of two or more materials, particularly host materials or matrix materials.According to the prior art, carbazole derivatives, dibenzofuran derivatives, indenocarbazole derivatives, indolocarbazole derivatives, benzofurocarbazole derivatives, and benzothienocarbazole derivatives are used as matrix materials for phosphorescent emitters. WO2012 / 048781A1 and CN115626914 A describe, among other things, specific 4H-naphtho[1,2,3,4-def]carbazole derivatives as matrix materials. US2019315759A1, US2019036059A1, and WO2022 / 038065A1 describe, among other things, complex carbazole derivatives as matrix materials.
[0002] In general, there is still room for improvement in these materials, especially for use as matrix materials.
[0003] The object of the present invention is to provide compounds or combinations of compounds which are particularly suitable for use as matrix material, hole transport material, hole injection material or electron blocking material in a phosphorescent OLED. In particular, the object of the present invention is to provide matrix materials which are suitable for use in an organic electronic device, in particular in a fluorescent or phosphorescent OLED and which lead to good device properties, in particular with regard to an improved lifetime, as well as to provide the corresponding electronic device. This applies in particular to use in combination with a low to medium emitter concentration, ieEmitter concentrations in the order of 3 to 25%, in particular 3 to 15%, particularly preferably 4 to 10% and most preferably 4 to 8%, since the device lifetime is limited in particular here.
[0004] It has now been found that electronic devices comprising a light-emitting layer containing at least one compound of formula (1) and at least one further matrix material selected from the compounds of formulas (6), (7), (8), (9), or (10) exhibit improvements over the prior art. The use of such a material combination for producing the light-emitting layer in an organic electronic device leads to very good properties of these devices, particularly with regard to lifetime, especially with the same or improved operating voltage and comparable efficiency.
[0005] It has also been found that electroluminescent devices containing specific compounds of formula (1), as described below, exhibit improvements over the prior art, particularly when using the compounds as matrix material, as hole-transport material, as hole-injection material, or as electron-transport material for phosphorescent dopants. - 3 - Summary of the Invention A first aspect of the present invention is an organic electronic device comprising an anode, a cathode, and at least one light-emitting layer, containing at least one compound of formula (1) and at least one further matrix material. where the symbols and indices used are: L is a single bond, an aromatic ring system with 6 to 40 ring atoms or an electron-rich heteroaromatic ring system with 9 to 40 ring atoms, which are bonded to one or more radicals R 0 may be substituted; R0 is selected at each occurrence, identically or differently, from the group consisting of D, F, Cl, Br, I, CN, NO2, C(=O)R 2 , P(=O)(Ar)2, P(Ar)2, B(Ar)2, Si(Ar)3, Si(R 2 )3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 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 substituted by R 2 C=CR 2 , Si(R 2 )2, C=O, C=S, C=NR 2 , P(=O)(R 2 ), SO, SO2, NR 2 , O, S or CONR 2 and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which is substituted by one or more radicals R 2may be substituted, an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, which may be substituted with one or more radicals R 2 may be substituted, or an aralkyl or heteroaralkyl group having 5 to 40 ring atoms which may be substituted with one or more radicals R 2 may be substituted; Rx corresponds to one of the formulas (1-2) to (1-11) P22-240 SC - 5 - 5 10 15 20 25 , * denotes the bond to L; 30 L1 is, identically or differently at each occurrence, a bond, O, S, C(R)2 or N-Ar; V is O, S, Se, C(R)2, Si(R)3 or N-Ar3; R a , R b and R crepresent a monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution or no substitution and are on each occurrence, independently of one another, D, CN, F, a non-deuterated or partially or fully deuterated alkyl group having 1 to 10 C atoms or a non-deuterated or partially or fully deuterated aromatic ring system having 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl having 9 to 40 ring atoms; R is on each occurrence, identically or differently, 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 one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms are replaced by D, F,or CN or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which may be replaced by one or more substituents selected from D, F, CN, 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 one or more non-adjacent CH2 groups of the alkyl group may be replaced by O or S and where one or more H atoms of the alkyl group may be replaced by D, F, or CN, where two substituents R may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more substituents R, 1 may be substituted; Ar is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms which is substituted by one or more radicals R 2may be substituted; Ar1 is at each occurrence, identically or differently, an aromatic or electron-rich heteroaromatic ring system having 5 to 40 ring atoms, which is substituted by one or more radicals R 1 may be substituted; Ar2, Ar3 are at each occurrence, identically or differently, an aromatic or electron-rich heteroaromatic ring system having 5 to 40 ring atoms, which is substituted by one or more radicals R 2 may be substituted; R 1is selected, identically or differently at each occurrence, from the group consisting of D, F, CN, Si(Aryl)3, 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 one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms may be replaced by D, F, or CN or a non-deuterated or partially or fully deuterated aromatic ring system having 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl having 9 to 40 ring atoms; R 2is selected, identically or differently at each occurrence, from the group consisting of D, F, CN, Si(Aryl)3, 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 one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms may be replaced by D, F, or CN; Aryl is, at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms which may be replaced by one or more substituents selected from D, F, CN, 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 one or more non-adjacent CH2 groups of the alkyl group may be replaced by O or S and where one or more H atoms of the alkyl group may be replaced by D, F, or CN;u, v are independently 0 or 1 at each occurrence and u+v is 1 or 2; wherein the further matrix material corresponds to one or more of the compounds of formulas (6), (7), (8), (9) or (10), formula (6), formula (7), - 8 - formula (8), formula (9), 7; 5 (R ) b1 Ar NN Ar 5 Formula (10), where the following applies to the symbols and indices used: X is the same or different at each occurrence N or CR 6 , preferably N; L2 is at each occurrence, identically or differently, a single bond, an aromatic ring system having 5 to 20 ring atoms or a heteroaromatic ring system having 9 to 30 ring atoms, which are bonded to one or more radicals R 7 may be substituted; R## is at each occurrence, identically or differently, D, F, CN or an aromatic ring system having 6 to 20 ring atoms which is substituted with one or more radicals R 6may be substituted and two adjacent substituents R## may together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system which may be substituted with one or more radicals R 7 can be substituted; Y is at each occurrence independently the same or different N, CH, CR 7 or L2-Ar5, where it is excluded that two adjacent Y simultaneously represent N; V2 is O or S; R 6 is, at each occurrence, identically or differently, D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 - 9 - C atoms, where the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 7 may be substituted and wherein one or more non-adjacent CH2 groups are substituted by Si(R 7 )2, C=O, NR 7 , O, S or CONR 7may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, each of which is substituted by one or more radicals R 7 can be substituted; two radicals R 6 also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar5 * represents, identically or differently at each occurrence, independently an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which with one or more radicals R 7 may be substituted, wherein for the heteroaromatic ring system the heterocycles of the formulas (A) and (B) are excluded, , Ar5, identically or differently at each occurrence, independently represents an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which is substituted with one or more radicals R 7 may be substituted; R 7 is the same or different at each occurrence D, F, Cl, Br, I, N(R 8)2, CN, NO2, OR 8 , SR 8 , Si(R 8 )3, B(OR 8 )2, C(=O)R 8 , P(=O)(R 8 )2, S(=O)R 8 , S(=O)2R 8 , OSO2R 8 , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 8 may be substituted, with one or more non-adjacent CH2 groups being substituted by Si(R 8 )2, C=O, NR 8 , O, S or CONR 8 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which is substituted by one or more radicals R 8 may be substituted; two or more radicals R 7 form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; R 8is on each occurrence, identically or differently, H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, in particular a - 10 - hydrocarbon radical, having 1 to 20 C atoms, in which one or more H atoms may also be replaced by F; b1 is 0, 1, 2, 3 or 4; b2 is 0, 1, 2 or 3, excluding compounds of the formula (6) in which at least one substituent L2-Ar5* corresponds to one of the formulas (C) or (D) and a second substituent L2-Ar5* corresponds to the formula (E); where the following applies to the symbols and indices used: L4 is a single bond or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms; Z1 and Z2 are each independently O, S or Se; R1*, R2*, R3*, R4* are independently H, D or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms.The present invention further provides a compound according to formula (1), formula (1), - 11 - where the following applies to the symbols and indices used: L is a single bond, an aromatic ring system having 6 to 40 ring atoms or an electron-rich heteroaromatic ring system having 9 to 40 ring atoms which can be bonded to one or more radicals R. 0 may be substituted; R 0 is selected at each occurrence, identically or differently, from the group consisting of D, F, Cl, Br, I, CN, NO2, C(=O)R 2 , P(=O)(Ar)2, P(Ar)2, B(Ar)2, Si(Ar)3, Si(R 2 )3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 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 substituted by R 2 C=CR 2, Si(R 2 )2, C=O, C=S, C=NR 2 , P(=O)(R 2 ), SO, SO2, NR 2 , O, S or CONR 2 and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which is substituted by one or more radicals R 2 may be substituted, an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, which may be substituted with one or more radicals R 2 may be substituted, or an aralkyl or heteroaralkyl group having 5 to 40 ring atoms which may be substituted by one or more radicals R 2 may be substituted; Rx corresponds to one of the formulas (1-6) to (1-11)
[0006] - 12 - , * denotes the bond to L; L1 is, identically or differently at each occurrence, a bond, O, S, C(R)2 or N-Ar; V is O, S, Se, C(R)2, Si(R)3 or N-Ar3; R a , R b and R crepresent a monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution or no substitution and are, independently of one another, D, CN, F, a non-deuterated or partially or fully deuterated alkyl group having 1 to 10 C atoms or a non-deuterated or partially or fully deuterated aromatic ring system having 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl having 9 to 40 ring atoms; R is, on each occurrence, identically or differently 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 one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms are replaced by D, F,or CN - 13 - or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which may be replaced by one or more substituents selected from D, F, CN, 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 one or more non-adjacent CH2 groups of the alkyl group may be replaced by O or S and where one or more H atoms of the alkyl group may be replaced by D, F, or CN, where two substituents R may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which may be substituted by one or more substituents R, 1 may be substituted; Ar is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms which is substituted by one or more radicals R 2may be substituted; Ar1 is at each occurrence, identically or differently, an aromatic or electron-rich heteroaromatic ring system having 5 to 40 ring atoms, which is substituted by one or more radicals R 1 may be substituted; Ar2, Ar3 are at each occurrence, identically or differently, an aromatic or electron-rich heteroaromatic ring system having 5 to 40 ring atoms, which is substituted by one or more radicals R 2 may be substituted; R 1is selected, identically or differently at each occurrence, from the group consisting of D, F, CN, Si(Aryl)3, 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 one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms may be replaced by D, F, or CN or a non-deuterated or partially or fully deuterated aromatic ring system having 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl having 9 to 40 ring atoms; R 2is selected, identically or differently at each occurrence, from the group consisting of D, F, CN, Si(Aryl)3, 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 one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms may be replaced by D, F, or CN; - 14 - Aryl is, on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which may be replaced by one or more substituents selected from D, F, CN, 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 one or more non-adjacent CH2 groups of the alkyl group may be replaced by O or S and where one or more H atoms of the alkyl group may be replaced by D, F, or CN; u,v is independently 0 or 1 at each occurrence, and u+v is 1 or 2. The invention further provides a mixture comprising at least one compound of the formula (1), wherein Rx corresponds to one of the formulas (1-6) to (1-11), as described above or preferably described later, and at least one further compound selected from the group of matrix materials, phosphorescent emitters, fluorescent emitters, and / or emitters exhibiting TADF (thermally activated delayed fluorescence). The invention further provides a formulation comprising at least one compound of the formula (1), wherein Rx corresponds to one of the formulas (1-6) to (1-11), as described above or preferably described later, or a mixture as described above, and at least one solvent. The invention further provides the use of a compound of the formula (1), wherein Rx corresponds to one of the formulas (1-6) to (1-11), as described above,in an organic electronic device, preferably an electroluminescent device, preferably in a hole-transporting layer, a hole-injecting layer, or an electron-blocking layer. Description of the invention In the present patent application, "D" or "D atom" denotes deuterium. An aryl group within the meaning of this invention contains 6 to 40 ring atoms, preferably C atoms. A heteroaryl group within the meaning of this invention contains 5 to 40 ring atoms, wherein the ring atoms comprise 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 defined as either a simple aromatic cycle, i.e., phenyl, derived from benzene, or a simple heteroaromatic cycle, for example, derived from pyridine, pyrimidine, or thiophene.or a condensed aryl or heteroaryl group, for example derived from naphthalene, anthracene, phenanthrene, quinoline or isoquinoline. An aryl group having 6 to 18 C atoms is therefore preferably phenyl, naphthyl, phenanthryl or triphenylenyl, whereby the attachment of the aryl group as a substituent is not restricted. The aryl or heteroaryl group within the meaning of this invention can carry one or more radicals, whereby the suitable radical is described below. If no such radical is described, the aryl group or heteroaryl group is unsubstituted. An aromatic ring system within the meaning of this invention contains 6 to 40 C atoms in the ring system. The aromatic ring system also includes aryl groups, as described above. An aromatic ring system having 6 to 18 C atoms is preferably composed of phenyl, fully deuterated phenyl, biphenyl, naphthyl,Phenanthryl and triphenylenyl are selected. A heteroaromatic ring system within the meaning of this invention contains 5 to 40 ring atoms and at least one heteroatom. A preferred heteroaromatic ring system has 9 to 40 ring atoms and at least one heteroatom. The heteroaromatic ring system also includes heteroaryl groups, as described above. The heteroatoms in the heteroaromatic ring system 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 interrupted by a non-aromatic unit (preferably less than 10% of the atoms other than H). For example, systems such as 9,9'-spirobifluorene, 9,9-dialkylfluorene, 9,9-Diarylfluorene are understood as aromatic ring systems within the meaning of this invention. Furthermore, systems in which two or more aryl or heteroaryl groups are directly bonded to one another, such as biphenyl, terphenyl, quaterphenyl, phenylpyridine, or bipyridine, are also encompassed by the definition of aromatic or heteroaromatic ring systems. An aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which can be linked to the aromatic or heteroaromatic ring via any position, is understood to mean, for example, groups derived - 16 - from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzfluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-monobenzoindenofluorene,cis- oder trans-Dibenzoindenofluoren, Truxen, Isotruxen, Spirotruxen, Spiroisotruxen, Furan, Benzofuran, Isobenzofuran, Dibenzofuran, Thiophen, Benzothiophen, Isobenzothiophen, Dibenzothiophen, Pyrrol, Indol, Isoindol, Carbazol, Indolocarbazol, Indenocarbazol, Pyridin, Chinolin, Isochinolin, Acridin, Phenanthridin, Benzo-5,6-chinolin, Benzo-6,7-chinolin, Benzo-7,8-chinolin, Phenothiazin, Phenoxazin, Pyrazol, Indazol, Imidazol, Benzimidazol, Naphthimidazol, Phenanthrimidazol, Pyridimidazol, Pyrazinimidazol, Chinoxalinimidazol, Oxazol, Benzoxazol, Naphthoxazol, Anthroxazol, Phenanthroxazol, Isoxazol, 1,2-Thiazol, 1,3- Thiazol, Benzothiazol, Pyridazin, Benzopyridazin, Pyrimidin, Benzpyrimidin, Chinoxalin, 1,5-Diazaanthracen, 2,7-Diazapyren, 2,3-Diazapyren, 1,6-Diazapyren, 1,8-Diazapyren, 4,5-Diazapyren, 4,5,9,10-Tetraazaperylen, Pyrazin, Phenazin, Phenoxazin, Pheno- thiazin, Fluorubin, Naphthyridin, Azacarbazol, Benzocarbolin, Phenanthrolin, 1,2,3- Triazol, 1,2,4-Triazol, Benzotriazol, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine, and benzothiadiazole. The abbreviations Ar and Ar5, identically or differently at each occurrence, mean an aromatic or heteroaromatic ring system with 5 to 40 ring atoms which is substituted by one or more radicals R, 2 or R 7 may be substituted, where the radical R 2 or R 7 or the substituents R 2 or R 7 has / have a meaning as described above or below. A preferred meaning of Ar and Ar5 is described below. The abbreviation Ar5 * represents, identically or differently at each occurrence, independently an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which with one or more radicals R7 may be substituted, whereby for the heteroaromatic ring system the heterocycles of formulas (A) and (B) are excluded, - 17 - The abbreviation Ar1 means an aromatic or electron-rich heteroaromatic ring system with 5 to 40 ring atoms, which is linked to one or more residues R 1 may be substituted. A preferred meaning of Ar1 is described below. The abbreviations Ar2 and Ar3, identically or differently at each occurrence, mean an aromatic or electron-rich heteroaromatic ring system having 5 to 40 ring atoms, which is substituted by one or more radicals R 2 may be substituted, where the radical R 2 or the substituents R 2has / have a meaning as described above or below. A preferred meaning of Ar2 and Ar3 is described below. An electron-rich heteroaromatic compound is a heterocyclic aromatic compound with a n-excess, i.e., a free electron pair of the heteroatom forms the cyclically delocalized electrons with the p-electrons of the carbon atoms. This definition also applies accordingly to an electron-rich heteroaromatic ring system. The abbreviation "aryl" means, identically or differently at each occurrence, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which may be replaced by one or more substituents selected from D, F, CN, 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 one or more non-adjacent CH2 groups of the alkyl group may be replaced by O or S, and wherein one or more H atoms of the alkyl group may be replaced by D, F, or CN. A cyclic alkyl, alkoxy, or thioalkyl group within the meaning of this invention is understood to mean a monocyclic, bicyclic, or polycyclic group. - 18 - In the context of the present invention, a straight-chain, branched or cyclic C1 to C20 alkyl group is understood to mean, for example, the radicals methyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-Methylcyclohexyl, n-Octyl, 2-Ethylhexyl, Cyclooctyl, 1-Bicyclo[2,2,2]octyl, 2-Bicyclo[2,2,2]octyl, 2-(2,6-Dimethyl)-octyl, 3-(3,7-Dimethyl)octyl, adamantyl, trifluoromethyl, pentafluoroethyl, 2,2,2-tri-fluoroethyl, 1,1-dimethyl-n-hex-1-yl-, 1,1-dimethyl-n-hept-1-yl-, 1,1-dimethyl-n-oct-1-yl-, 1,1-dimethyl-n-dec-1-yl-, 1,1-Dimethyl-n-dodec-1-yl-, 1,1-Dimethyl-n-tetradec-1-yl-, 1,1-Dimethyl-n-hexadec-1-yl-, 1,1-Dimethyl-n-octadec-1-yl-, 1,1-Diethyl-n-hex-1-yl-, 1,1-Diethyl-n-hept-1-yl-, 1,1-Diethyl-n-oct-1-yl-, 1,1-Diethyl-n-dec-1-yl-, 1,1-Diethyl-n-dodec-1-yl-, 1,1-Diethyl-n-tetradec-1-yl-, 1,1-Diethyl-n-hexadec-1-yl-, 1,1-Diethyl-n-octadec-1-yl-, 1-(n-Propyl)-cyclohex-1-yl-, 1-(n-Butyl)-cyclohex-1-yl-, 1-(n-Hexyl)-cyclohex-1-yl-, 1-(n-Octyl)-cyclohex-1-yl- and 1-(n-Decyl)-cyclohex-1-yl- are understood as meaning. The compounds of formula (1) and their preferred embodiments are described below. The preferred embodiments also apply to the mixture according to the invention,Formulation according to the invention and organic electronic or electroluminescent device according to the invention. In compounds of formula (1), the substituent L-Rx can be bonded at any position. Preferred compounds of formula (1) are compounds of formulas (1a) to (1j), - 19 - where Rx, L, R a , R b , R c and Ar1 have a meaning mentioned above or mentioned below with preference. - 20 - Particularly preferred compounds of formula (1) are the compounds of formulas (1a) and (1b), where Rx, L, R a , R b , R c and Ar1 have a meaning mentioned above or mentioned with preference below. In one embodiment of the invention, the linker L in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) is an aromatic or heteroaromatic ring system of the formulas L-1 to L-30, which can be substituted with one or more radicals R 0may be substituted, where R 0 has a meaning previously specified or subsequently specified: - 21 - where the dashed lines denote the bond to Rx or to the radical of formula (1) or the radical of formulas (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j); and V1 denotes O, S, Se or C(R)2 and R has a meaning mentioned above or mentioned with preference below. In linkers L-18 to L-30, V1 is preferably O or S. In linkers L-18 to L-30, V1 is very particularly preferably O. In a preferred embodiment of the invention, L in compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) is a single bond. This is a particularly preferred embodiment. In a preferred embodiment of the invention, the linker L in compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) is selected from the group of linkers L-1 to L-13, which are linked to one or more radicals R 0 may be substituted, where R 0has a meaning given above or below. In a particularly preferred embodiment of the invention, the linker L in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) is selected from the group of linkers L-1 to L-7, which are linked to one or more - 22 - radicals R 0 may be substituted, where R 0 has a meaning given above or below. The substituent R 0 is, when identical or different, preferably selected from the group D, F, CN, Si(Ar)3 or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, where Ar has a meaning mentioned above. The substituent R 0 is preferably D or non-deuterated or fully deuterated phenyl. Ar in Si(Ar)3 is preferably the same and is an aromatic ring system having 6 to 20 ring atoms, which is substituted by one or more radicals R 2 can be substituted. R2in Ar is preferably D, F or CN, particularly preferably D. In Si(Ar)3, Ar is particularly preferably selected from non-deuterated, partially deuterated or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl. In one embodiment of the invention, Rx in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) is of the formula (1-2) and the linker L has a meaning given above or with preference. This is a particularly preferred embodiment. In one embodiment of the invention, Rx in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) is of the formula (1-3) and the linker L has a meaning given above or with preference.In one embodiment of the invention, Rx in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) is of the formula (1-4) and the linker L has a meaning given above or with preference. This is a particularly preferred embodiment. In one embodiment of the invention, Rx in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) is of the formula (1-5) and the linker L has a meaning given above or with preference. In one embodiment of the invention, Rx in compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), and (1j) represents formula (1-6), and the linker L has a meaning previously indicated or preferably indicated. This is a particularly preferred embodiment.- 23 - In one embodiment of the invention, Rx in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) is of the formula (1-7) and the linker L has a meaning given above or preferred. In one embodiment of the invention, Rx in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) is of the formula (1-8) and the linker L has a meaning given above or preferred. In one embodiment of the invention, Rx in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) represents the formula (1-9) and the linker L has a meaning given above or preferred. In one embodiment of the invention, Rx in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) represents the formula (1-10) and the linker L has a meaning given above or preferred.In one embodiment of the invention, Rx in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) represents the formula (1-11) and the linker L has a meaning given above or preferred. In a particularly preferred embodiment of the organic electronic device according to the invention, Rx in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) represents one of the formulas (1-2), (1-4), (1-5), (1-6) or (1-7) and the linker L has a meaning given above or preferred. In a particularly preferred embodiment of the organic electronic device according to the invention, Rx in compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) represents one of formulas (1-3), (1-5), (1-7) or (1-11) and the linker L has a meaning given above or preferably given.In a particularly preferred embodiment of the compounds of formula (1) according to the invention, Rx in compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) represents one of the formulas (1-6) or (1-7) and the linker L has a meaning given above or preferred. In a particularly preferred embodiment of the compounds of formula (1) according to the invention, Rx in compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) represents one of the formulas (1-7) or (1-11) and the linker L has a meaning given above or preferred. In formulas (1-2), (1-4), (1-5) and (1-6), Ar2 is preferably selected, identically or differently, from the group Ar-1 to Ar-36 at each occurrence. - 25 - - 26 - - 27 - where Y 2 O, S or Se means Y 3 O, S, NAr3 or C(R # )2means R 3 H, R2 or an aromatic ring system with 6 to 40 ring atoms, which with one or more radicals R 2 may be substituted, the dashed bond represents the bond to the residue of formulas (1-2), (1-4), (1-5) and (1-6), Ar3 represents an aromatic or electron-rich heteroaromatic ring system with 5 to 40 ring atoms, which is substituted with one or more residues R 2 can be substituted, R # at each occurrence, identically or differently, H, D, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 C atoms, each of which is substituted by one or more radicals R 2may be substituted, where one or more H atoms may be replaced by D, F or CN or denotes an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, each of which may be substituted by one or more radicals R 2 may be substituted, or is an aryloxy or heteroaryloxy group having 5 to 40 ring atoms which may be substituted with one or more radicals R 2 may be substituted, or is an aralkyl or heteroaralkyl group having 5 to 40 ring atoms which may be substituted with one or more radicals R 2 may be substituted and where R 2 has a previously mentioned or a previously preferred meaning. R 2 in N-Ar3 is preferably D, F or CN, particularly preferably D. In the formulas Ar-12 to Ar-15, Ar3, when occurring in N-Ar3, is Y 3 particularly preferably selected from non-deuterated, partially deuterated or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl. The symbol Y 3in the formulas Ar-12 to Ar-15 preferably denotes N-Ar3, C(CH3)2, O or S, particularly preferably O or S, very particularly preferably O. - 28 - R 2 in Ar2 is preferably D, F or CN, particularly preferably D. Y 2 in the formulas Ar-25 to Ar-29 is preferably S or O, particularly preferably O. In the structures Ar-1 to Ar-36, the substituent R 3 preferably selected, identically or differently at each occurrence, from the group consisting of H, D, F, CN or an aromatic ring system having 6 to 30 ring atoms, each of which is substituted by one or more radicals R 2 can be substituted. In the structures Ar-1 to Ar-36, the substituent R 3 particularly preferably, at each occurrence, identically or differently selected from the group consisting of H, D, non-deuterated or partially or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl. In the structures Ar-1 to Ar-36, the substituent R 3very particularly preferably on each occurrence, identically or differently selected from the group consisting of H or D. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), in which Rx represents one of the formulas (1-2), (1-4), (1-5) or (1-6), Ar2 on each occurrence, identically or differently, is particularly preferably selected from the group Ar-1 to Ar-7 and Ar-22 to Ar-29, where R 3 has a meaning previously indicated or preferably indicated. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), in which Rx represents one of the formulas (1-2), (1-4), (1-5) or (1-6), Ar2, identically or differently, is very particularly preferably selected from the group Ar-1 to Ar-7 at each occurrence, where R 3has a meaning previously indicated or preferably indicated. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), in which Rx represents one of the formulas (1-2), (1-4), (1-5) or (1-6), Ar2, identically or differently, is very particularly preferably selected from the group Ar-25 to Ar-29 at each occurrence, where R 3 has a meaning previously indicated or preferably indicated. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), in which Rx represents one of the formulas (1-2), (1-4), (1-5) or (1-6), Ar2, identically or differently, is very particularly preferably selected from the group Ar-30 to Ar-36 at each occurrence, where R 3has a meaning previously given or preferably given. - 29 - In formulas (1-6) and (1-7), V is selected from the group O, S, Se, C(R)2, Si(R)3 or N-Ar3, where R has a meaning previously given or preferably given.In formulas (1-6) and (1-7), the substituent R in the definition of V is preferably selected, identically or differently, at each occurrence 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 one or more H atoms may be replaced by D, F, or CN, or an aromatic or heteroaromatic ring system having 5 to 20 ring atoms, which may be replaced by one or more substituents selected from 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 one or more H atoms of the alkyl group may be replaced by D, F, or CN, or the two substituents R form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which can be substituted with one or more substituents R. 1 can be substituted. R1 has a meaning given above or given below with preference. In formulas (1-6) and (1-7), the substituent R in C(R)2 in the symbol V particularly preferably represents a straight-chain alkyl group having 1 to 6 C atoms, where one or more H atoms may be replaced by D, or an aromatic ring system having 5 to 20 ring atoms, which may be partially or fully deuterated, or the two substituents R form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which, with one or more substituents R 1 can be substituted. R 1has a meaning given above or preferred below. In formulas (1-6) and (1-7), the substituent R in Si(R)3 in symbol V particularly preferably represents an aromatic ring system having 5 to 20 ring atoms, which may be partially or fully deuterated. In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), in which Rx represents one of formulas (1-6) or (1-7), V is preferably selected from O, S, C(R)2 or N-Ar3, where Ar3 has a meaning given above and C(R)2 has a meaning given above or preferred. If V is N-Ar3 in the formulas (1-6) or (1-7), Ar3 is, at each occurrence, identically or differently, preferably selected from the group Ar-1 to Ar-24 or Ar-30 to Ar-36 - 30 -, as previously described, where R 3has a meaning previously indicated or preferably indicated. If V is N-Ar3 in the formulas (1-6) or (1-7), Ar3 is, identically or differently, particularly preferably selected from the group Ar-1 to Ar-7 or Ar-22 to Ar-24 at each occurrence, where R 3 has a meaning previously indicated or preferably indicated. If V is N-Ar3 in the formulas (1-6) or (1-7), Ar3 is, identically or differently, particularly preferably selected from the group Ar-1 to Ar-7 at each occurrence, where R 3has a previously given or preferred meaning. In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), in which Rx represents one of formulas (1-6) or (1-7), V is preferably selected from O or N-Ar3, where Ar3 has a previously given or preferred meaning. In formulas (1-8) and (1-9), L1 independently represents at each occurrence a bond, O, S, C(R)2 or N-Ar, where R has a previously given or preferred meaning, u and v are each independently 0 or 1 and u+v is 1 or 2.In formulas (1-8) and (1-9), the substituent R in the definition of L1 is preferably selected, identically or differently, at each occurrence 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 one or more H atoms may be replaced by D, F, or CN, or an aromatic or heteroaromatic ring system having 5 to 20 ring atoms, which may be replaced by one or more substituents selected from 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 one or more H atoms of the alkyl group may be replaced by D, F, or CN.In formulas (1-8) and (1-9), the substituent R at C(R)2 in the linker L1 particularly preferably represents a straight-chain alkyl group having 1 to 6 C atoms, where one or more H atoms may be replaced by D, or an aromatic ring system having 5 to 20 ring atoms, which may be partially or fully deuterated. - 31 - In formulas (1-8) and (1-9), Ar at N-Ar in the linker L1 is preferably selected from the group Ar-1 to Ar-36, as described above, where R. 3 has a meaning previously indicated or preferably indicated. In formulas (1-8) and (1-9), Ar in N-Ar in linker L1 is particularly preferably selected from the group Ar-1 to Ar-7, as described above, where R 3 has a previously specified or preferred meaning. R 2in Ar is preferably D, F or CN, particularly preferably D. In the formulas (1-8) and (1-9), L1 at each occurrence independently preferably represents a bond or C(R)2, where R has a meaning given previously or preferably, u and v are each independently 0 or 1 and u+v is 1 or 2. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), in which Rx represents one of the formulas (1-8) or (1-9) and L1 has a meaning as described above or preferably described, u+v is preferably 1. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), in which Rx represents one of the formulas (1-8) or (1-9), u+v is preferably 1, and L1 particularly preferably represents a bond. In formula (1-10), Ar1 has a meaning as described above and preferably described below.In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) or preferred compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) without taking Rx into account, R. a , R b and R c a monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution or no substitution and R a , R b and R c are preferably, at each occurrence, independently of one another, D, CN, F, a non-deuterated or partially or fully deuterated alkyl group having 1 to 10 C atoms or a non-deuterated or partially or fully deuterated aromatic ring system having 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl having 9 to 40 ring atoms. With maximum permissible substitution, R a , R b and R cin compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) or preferred compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) without taking Rx into account, preferably represents D and a further substituent R a , R b or R c can preferably represent CN, F, a non-deuterated or partially or fully deuterated alkyl group having 1 to 10 C atoms or a non-deuterated or partially or fully deuterated aromatic ring system having 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl having 9 to 40 ring atoms. Preferably, with maximum substitution, all R a , R b and R c for D. In monosubstitution, R a , R b and R ceach independently of one another in compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) or preferred compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) without taking Rx into account preferably represents D, CN, F, a non-deuterated or partially or fully deuterated alkyl group having 1 to 10 C atoms or a non-deuterated or partially or fully deuterated aromatic ring system having 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl having 9 to 40 ring atoms. In one embodiment of the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), without considering Rx as a counting substituent, a substituent R a , R b or R c no substitution and two substituents R a , R b or R cpreferably represent D, CN, F, a non-deuterated or partially or fully deuterated alkyl group having 1 to 10 C atoms or a non-deuterated or partially or fully deuterated aromatic ring system having 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl having 9 to 40 ring atoms or preferably represent CN, F, a non-deuterated or partially or fully deuterated alkyl group having 1 to 10 C atoms or a non-deuterated or partially or fully deuterated aromatic ring system having 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl having 9 to 40 ring atoms. In a preferred embodiment of the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), without considering Rx as a counting substituent, two substituents Ra,Rb or Rc does not represent a substitution and a substituent Ra, Rb or Rc preferably represents D, CN, F, a non-deuterated or partially or fully deuterated alkyl group having 1 to 10 C atoms or a non-deuterated or partially or fully deuterated aromatic ring system having 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl having 9 to 40 ring atoms or preferably represents CN, F, a non-deuterated or partially or fully deuterated alkyl group having 1 to 10 C atoms or a non-deuterated or partially or fully deuterated aromatic ring system having 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl having 9 to 40 ring atoms. In a preferred embodiment of the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j),Without taking Rx into account as a counting substituent, Ra, Rb or Rc do not represent a substitution. With maximum permissible substitution, Ra, Rb and Rc when occurring in the formulas (1-2), (1-3), (1-4), (1-5), (1-6), (1-7), (1-8), (1-9), (1-10) and (1-11) preferably represent D and a further substituent Ra, Rb or Rc can preferably represent CN, F, a non-deuterated or partially or fully deuterated alkyl group having 1 to 10 C atoms or a non-deuterated or partially or fully deuterated aromatic ring system having 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl having 9 to 40 ring atoms. Preferably, with maximum substitution, all Ra, Rb and Rc when occurring in the formulas (1-2), (1-3), (1-4), (1-5), (1-6), (1-7), (1-8), (1-9), (1-10) and (1-11) are D. For the formulas (1-2), (1-3), (1-4), (1-5), (1-6), (1-7), (1-8), (1-9), (1-10) and (1-11) it is preferred if R,a , R b and R c represent maximum substitution or no substitution. However, the compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) or preferred compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) can also be partially deuterated, ie the substituents Ra, Rb and Rc represent D and each independently represent monosubstitution, disubstitution or trisubstitution. In compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) or preferred compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), Ar1 is an aromatic or electron-rich heteroaromatic ring system having 5 to 40 ring atoms, which is substituted by one or more radicals R 1 may be substituted; where R 1 has a meaning previously stated. R 1in Ar1 preferably means D, F, CN, Si(Aryl)3, where aryl on each occurrence, identically or differently, means an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which may be replaced by one or more substituents selected from D, F, CN, 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 one or more non-adjacent CH2 groups of the alkyl group may be replaced by O - 34 - or S and where one or more H atoms of the alkyl group may be replaced by D, F, or CN or R 1 is a non-deuterated or partially or fully deuterated aromatic ring system with 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl with 9 to 40 ring atoms. R 1in Ar1 particularly preferably denotes D, F, CN, non-deuterated or partially or fully deuterated phenyl, 1,4-biphenyl, 1,3-biphenyl or 1,2-biphenyl, very particularly preferably D denotes non-deuterated or partially or fully deuterated phenyl. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) or preferred compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), Ar1 is preferably selected from the group Ar-1 to Ar-36, as previously described or preferably described, where R 3 has a meaning previously given or preferably given. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) or preferred compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), Ar1 is preferably selected from the group Ar-1 to Ar-36, as previously described or preferably described, where R3 , Y 2 and Y 3 have a meaning previously given or preferably given. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) or preferred compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), Ar1 is particularly preferably selected from the group Ar-1 to Ar-7, Ar-12 to Ar-15, Ar-23 to Ar-29 or Ar-30 to Ar-36, as previously described or preferably described, where R 3 has a meaning previously given or preferably given. In compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) or preferred compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), Ar1 is most preferably selected from the group Ar-1 to Ar-7 or Ar-30 to Ar-36, as previously described or preferably described, where R 3has a meaning previously indicated or preferably indicated. The compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) or preferred compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) are preferably partially deuterated or fully deuterated.- 35 - If the compounds of formulae (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) are deuterated compounds, it is possible during their preparation, provided that the preparation is chosen by reacting a non-deuterated compound of one of formulae (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j) with a deuteration source or if deuterated starting compounds are chosen during the preparation which are a mixture of deuterated starting compounds, that a mixture of deuterated products of the same basic chemical structure is formed which differ only in the degree of deuteration and / or the deuteration patterns.Such mixtures of deuterated compounds with the same basic chemical structure of formula (1), which differ only in the degree of deuteration and / or the deuteration patterns, are understood by the term "at least one compound of formula (1)" within the meaning of the invention. In a preferred embodiment of the at least one compound of formula (1), as described above or preferably described, the average degree of deuteration is at least 50 mol% to 90 mol%, preferably 70 mol% to 100 mol%. Corresponding deuteration methods are known to the person skilled in the art and are described, for example, in KR2016041014, WO2017 / 122988, KR202005282, KR101978651 and WO2018 / 110887 or in Bulletin of the Chemical Society of Japan, 2021, 94(2), 600-605 or Asian Journal of Organic Chemistry, 2017, 6(8), 1063-1071.A suitable method for deuterating a compound by exchanging one or more H atoms for D atoms is to treat the compound to be deuterated in the presence of a platinum catalyst or palladium catalyst and a deuterium source. The term "deuterium source" refers to any compound containing one or more D atoms and capable of releasing them under suitable conditions. The platinum catalyst is preferably dry platinum on carbon, preferably 5% dry platinum on carbon. The palladium catalyst is preferably dry palladium on carbon, preferably 5% dry palladium on carbon. A suitable deuterium source is D2O, benzene-d6, chloroform-d3, acetonitrile-d3, acetone-d6, acetic acid-d4, methanol-d4, or toluene-d8. A preferred deuterium source is D2O or a combination of D2O and a fully deuterated organic solvent.A particularly preferred deuterium source is the combination of - 36 - D2O with a fully deuterated organic solvent, whereby the fully deuterated solvent is not restricted here. Particularly suitable fully deuterated solvents are benzene-d6 and toluene-d8. A particularly preferred deuterium source is a combination of D2O and toluene-d8. The reaction is preferably carried out with heating, more preferably with heating to temperatures between 100 °C and 200 °C. Furthermore, the reaction is preferably carried out under pressure. Examples of suitable compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), as previously described or preferably described, are the structures listed below in Table 1.
[0007] - 46 - Particularly suitable compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) and (1j), as described above or preferably described, are the compounds H1 to H30 of Table 2. - 47 - - 48 - - 49 - The compounds of formula (1), as described above, can be prepared by synthetic steps known to those skilled in the art, such as bromination, Suzuki coupling, Ullmann coupling, Hartwig-Buchwald coupling, etc. In the following synthesis schemes, the compounds are shown with a small number of substituents to simplify the structures. This does not exclude the presence of any other substituents in the processes. The processes shown for the synthesis of the compounds of the invention are to be understood as examples. The skilled person can develop alternative synthesis routes within the scope of their general technical knowledge. - 50 - - 51 - Detailed reaction conditions are known from the prior art or are described in the examples. By these processes, optionally followed by purification, such as recrystallization or sublimation, the compounds of formula (1) as described above or preferably described can be obtained in high purity, preferably more than 99% (determined by 1H-NMR and / or HPLC). For processing the compounds from the liquid phase, for example, by spin coating or printing processes, formulations of the compounds or mixtures of compounds with other functional materials, such as matrix materials, fluorescent emitters, phosphorescent emitters, and / or emitters exhibiting TADF, are required. These formulations can be, for example, solutions, dispersions, or emulsions. It may be preferable to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecyl benzene, ethyl benzoate, indane, NMP, p-cymene, phenetol, 1,4-diisopropylbenzene, dibenzyl ether, Diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1- Bis(3,4-dimethylphenyl)ethane, 2-methylbiphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, Ethyl octanoate, diethyl sebacate, octyl octanoate, heptylbenzene, menthyl isovalerate, cyclohexylhexanoate, or mixtures of these solvents. The compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), and (1j) according to the invention, where Rx corresponds to one of the formulas (1-6) to (1-11),as described above or preferably described, are suitable for use in an organic electroluminescent device, in particular as hole-transport material, as hole-injection material or as matrix material. - 52 - If the compound according to the invention of one of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j), where Rx corresponds to one of the formulas (1-6) to (1-11), is used as matrix material or synonymously host material in an emitting layer, it is preferably used in combination with another compound. A further subject of the invention is therefore a mixture comprising at least one compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j), where Rx corresponds to one of the formulas (1-6) to (1-11), or at least one preferred compound of one of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j),where Rx corresponds to one of the formulas (1-6) to (1-11), or at least one corresponding compound from Table 1 or at least one of the compounds H9, H10, H17, H18, H20, H23, H28, H29, and H30 and at least one further compound selected from the group of matrix materials, phosphorescent emitters, fluorescent emitters, and / or emitters exhibiting TADF (thermally activated delayed fluorescence). Suitable matrix materials and emitters that can be used in this mixture according to the invention are described below. The present invention furthermore also relates to a formulation comprising at least one compound according to the invention of one of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j), where Rx corresponds to one of the formulas (1-6) to (1-11), as described above, or a mixture according to the invention, as described above,and at least one solvent. The solvent can be one of the solvents mentioned above or a mixture of these solvents. The invention therefore further relates to a mixture comprising at least one compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j), where Rx corresponds to one of the formulas (1-6) to (1-11), or at least one preferred compound of one of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j), where Rx corresponds to one of the formulas (1-6) to (1-11), or at least one corresponding compound of Table 1 or at least one of the compounds H9, H10, H17, H18, H20, H23, H28, H29 and H30 and at least one further compound selected from the compounds of the formulas (6), (7), (8), (9) or (10), as described below or preferably described below. The organic electronic device can be made of, for example, organic integrated circuits (OICs),organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors, organic photoreceptors. The organic electronic device is preferably an organic electroluminescent device. The organic electroluminescent device according to the invention (synonymously organic electroluminescent device) is, for example, an organic light-emitting transistor (OLET), an organic field quench device (OFQD), an organic light-emitting electrochemical cell (OLEC, LEC, LEEC),an organic laser diode (O-laser) or an organic light-emitting diode (OLED). The organic electroluminescent device according to the invention is in particular an organic light-emitting diode or an organic light-emitting electrochemical cell. The device according to the invention is particularly preferably an OLED. The organic layer of the device according to the invention preferably contains, in addition to the light-emitting layer (EML), a hole injection layer (HIL), a hole transport layer (HTL), a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), an exciton blocking layer, an electron blocking layer and / or charge generation layers. The device according to the invention can also contain several layers from this group, preferably selected from EML, HIL, HTL, ETL, EIL and HBL.Interlayers can also be introduced between two emitting layers, which, for example, have an exciton-blocking function. If multiple emitting layers are present, they preferably have a total of several emission maxima between 380 nm and 750 nm, resulting in overall white emission, i.e., different emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. One emitting layer can also contain several fluorescent and / or phosphorescent compounds. Systems with three emitting layers are particularly preferred, with the three layers exhibiting blue, green, and orange or red emission. As an alternative to the combination as described above,An emitting layer can also exhibit yellow emission. Such combinations are known to the person skilled in the art. The organic electroluminescent device according to the invention can also be a tandem electroluminescent device, in particular for white-emitting OLEDs. The device can also contain inorganic materials or layers composed entirely of inorganic materials. A large number of materials known in the prior art can be used to select suitable materials for use in the previously described layers of the organic electroluminescent device. In doing so, the person skilled in the art will consider the chemical and physical properties of the materials, since it is known to himthat the materials in an organic electroluminescent device interact with one another. This applies, for example, to the energy positions of the orbitals (HOMO, LUMO) or the position of triplet and singlet energies, as well as other material properties. The compound according to the invention of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j), where Rx corresponds to one of the formulas (1-6) to (1-11), as described above or preferably described, can be used in different layers. Preferred is an organic electroluminescent device comprising at least one compound according to formula (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j), where Rx corresponds to one of the formulas (1-6) to (1-11) or the preferred embodiments described above in a light-emitting layer as matrix material for fluorescent emitters, phosphorescent emitters or for emitters,which exhibit TADF (thermally activated delayed fluorescence), in particular for phosphorescent emitters. Furthermore, the at least one compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j), where Rx corresponds to one of the formulas (1-6) to (1-11), can also be used in a hole-transporting layer or in a hole-injecting layer. The compound according to the invention of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j), where Rx corresponds to one of the formulas (1-6) to (1-11), is particularly preferably used as matrix material in a light-emitting layer. A further subject of the present invention is an organic electronic device as described above, wherein the organic layer contains at least one light-emitting layer comprising at least one compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h),(1i) or (1j) or which contains at least one preferred compound of one of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j) or at least one compound of Table 1 or at least one of the compounds H1 to H30, as described above, and at least one further matrix material, wherein the further matrix material corresponds to one or more of the compounds of the formulas (6), (7), (8), (9) or (10), as described above or preferably described below. The invention further provides the organic electronic device as described above, wherein the device, in addition to the light-emitting layer, contains at least one compound of the formula (1) or a preferred embodiment of the compound of the formula (1) and at least one further matrix material of one or more compounds of the formulas (6), (7), (8), (9) or (10),an electron-transporting layer or a hole-blocking layer which contains at least one compound of formula (1) or a preferred embodiment of the compound of formula (1). Suitable further matrix materials which can be used in combination with at least one compound of formula (1) and one or more of the compounds of formulas (6), (7), (8), (9) or (10) are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, triarylamines, carbazole derivatives, biscarbazoles, indolocarbazole derivatives, indenocarbazole derivatives, azacarbazole derivatives, bipolar matrix materials, azaboroles or boronic esters, triazine derivatives, zinc complexes, diazasilole or tetraazasilole derivatives, diazaphosphole derivatives, bridged carbazole derivatives, triphenylene derivatives or dibenzofuran derivatives. Likewise, another phosphorescent emitter, which emits at a shorter wavelength than the actual emitter,as a co-host in the mixture or a compound that does not participate, or does not participate to a significant extent, in charge transport, such as a wide band-gap compound. A wide-band-gap material is understood herein to mean a material within the meaning of the disclosure of US Pat. No. 7,294,849, which is characterized by a band gap of at least 3.5 eV, where band gap is understood to be the difference between the HOMO and LUMO energy of a material. The compounds of formulas (6), (7), (8), (9) or (10) are described below, which are combined in the device according to the invention with at least one compound of formulas (1), (1a), (1b), (1c), (1d), (1f), (1g), (1h), (1i) or (1j). Accordingly, the invention further provides an organic electronic device comprising an anode, a cathode, and at least one organic layer containing at least one light-emitting layer.wherein the at least - 56 - one light-emitting layer contains at least one compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j) as matrix material 1, as described above or described as preferred, and at least one compound of the formulas (6), (7), (8), (9) and / or (10) as matrix material 2, where the following applies to the symbols and indices used: X is the same or different at each occurrence N or CR 6 , preferably N; L2 is at each occurrence, identically or differently, a single bond, an aromatic ring system having 5 to 20 ring atoms or a - 57 - heteroaromatic ring system having 9 to 30 ring atoms which are bonded to one or more radicals R 7 may be substituted; R## is at each occurrence, identically or differently, D, F, CN or an aromatic ring system having 6 to 20 ring atoms which is substituted with one or more radicals R 6may be substituted and two adjacent substituents R## may together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system which may be substituted with one or more radicals R 7 can be substituted; Y is at each occurrence independently the same or different N, CH, CR 7 or L2-Ar5, where it is excluded that two adjacent Y simultaneously represent N; V2 is O or S; R 6 is, identically or differently at each occurrence, D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 7 may be substituted and wherein one or more non-adjacent CH2 groups are substituted by Si(R 7 )2, C=O, NR 7 , O, S or CONR 7may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, each of which is substituted by one or more radicals R 7 can be substituted; two radicals R 6 also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar5 * represents, identically or differently at each occurrence, independently an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which with one or more radicals R 7 may be substituted, whereby for the heteroaromatic ring system the heterocycles of formulas (A) and (B) are excluded, - 58 - Ar5, identically or differently at each occurrence, independently represents an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which is substituted by one or more radicals R 7 may be substituted; R 7is the same or different at each occurrence D, F, Cl, Br, I, N(R 8 )2, CN, NO2, OR 8 , SR 8 , Si(R 8 )3, B(OR 8 )2, C(=O)R 8 , P(=O)(R 8 )2, S(=O)R 8 , S(=O)2R 8 , OSO2R 8 , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 8 may be substituted, with one or more non-adjacent CH2 groups being substituted by Si(R 8 )2, C=O, NR 8 , O, S or CONR 8 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which is substituted by one or more radicals R 8 may be substituted; two or more radicals R 7form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; R 8 is, on each occurrence, identically or differently, H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, in particular a hydrocarbon radical, having 1 to 20 C atoms, in which one or more H atoms may also be replaced by F; b1 is 0, 1, 2, 3 or 4; b2 is 0, 1, 2 or 3, excluding compounds of the formula (6) in which at least one substituent L2-Ar5* corresponds to one of the formulas (C) or (D) and a second substituent L2-Ar5* corresponds to the formula (E), - 59 - where the following applies to the symbols and indices used: L4 is a single bond or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms; Z1 and Z2 are each independently O, S or Se; R1*, R2*, R3*, R4* are independently H, D or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms. In compounds of the formulas (7), (8), (9) and / or (10), Ar5 preferably at each occurrence, identically or differently, preferably represents a group Ar-1 to Ar-36, as described above, where R 3 , Y 2 , Y 3 , R 2 , R# has a previously indicated or preferred meaning. The designations of these substituents and symbols apply accordingly to compounds of formulas (6), (7), (8), (9) and (10). Preferred compounds of formula (6) are compounds of formula (6a), where the symbols and indices for this formula (6a) have the meaning: W means O, S, C(R W)2or N-Ar5*; R W is, on each occurrence, identically or differently, 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 one or more H atoms may be replaced by D, F, or CN, or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which may be replaced by one or more substituents selected from D, F, CN, 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 one or more H atoms of the alkyl group on the aromatic or heteroaromatic ring system may be replaced by D, F, or CN, where - 60 - the two radicals R W which bind to the same carbon atom also form a ring system with each other; A is the same or different at each occurrence CH, CR 7or N, where a maximum of two A groups per cycle stand for N and where A stands for C when L2 is bonded to this position; where L2, X, Ar5*, R 7 and R## have a meaning given above and wherein compounds of formula (6a) are excluded in which at least one substituent L2-Ar5* corresponds to one of the formulas (C) or (D), if the substituent corresponds to the formula (E*), where the following applies to the symbols and indices used: L4 is a single bond or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms; Z1* is O or S; Z2 is O, S or Se; R1*, R2*, R3*, R4* are independently H, D or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms. In a preferred embodiment of the compounds of the formula (6a), the substituents Ar5*, identical or different at each occurrence, independently represent an aromatic ring system having 6 to 40 ring atoms which is substituted by one or more radicals R 7may be substituted and L2 is a single bond or corresponds to a - 61 - linker of the formulas L-1 to L-30, as previously described, where the dashed lines represent the bond to Ar5* and the remainder of the formula (6a). In a particularly preferred embodiment of the compounds of the formula (6a), the substituents Ar5*, identical or different at each occurrence, independently represent an aromatic ring system Ar*-1 to Ar*-15, - 62 - where R 9 H or R 7 means and R 7 has a meaning given above or below. In compounds of the formula (6a), W is preferably O or N-Ar5*. The same preferred definition for Ar5* also applies to N-Ar5*. In compounds of the formula (6a), A is preferably, identically or differently, CH or CR on each occurrence. 7 and where A is C when L2 is bonded to this position. In compounds of formula (6a), at least one A is preferably CR 7 , where R7 means an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, which with one or more substituents R 8 Particularly preferred compounds of formulas (6) and (6a) are the compounds of formulas (6a-1) to (6a-5), - 63 - where the following applies to the symbols and indices used: Ar* is, identically or differently, an aromatic ring system with 6 to 40 ring atoms, which is substituted with one or more substituents R 8 may be substituted; L5 is a bond or an aromatic ring system with 6 to 40 ring atoms, which may be substituted by one or more substituents R 8 can be substituted, (R 7 )x, (R 7 )y, (R 8 )x1, (R 8 )y1 represent a monosubstitution, a disubstitution, a trisubstitution or the maximum permissible substitution with the substituent R 7 or R 8 dar, R 18is at each occurrence, identically or differently, a straight-chain alkyl group having 1 to 10 C atoms or an aryl group having 6 to 12 C atoms, where two substituents R 18 together can form a monocyclic or polycyclic, aliphatic, - 64 - aromatic or heteroaromatic ring system which, with one or more substituents R 8 may be substituted; where L2, R 7 and R 8 have a meaning mentioned above or a meaning mentioned above and below with preference, and Ar5*, identical or different at each occurrence, independently represents an aromatic ring system Ar*-1 to Ar*-15, as described above. In compounds of the formulas (6a-1), (6a-2), (6a-3), (6a-4) and (6a-5), the substituents R 7 and R 8 in (R 7 ) x , (R 7 ) y , (R 8 ) x1 , (R 8 ) y1when occurring preferably as indicated below, most preferably D. Preferred compounds of formula (6) are compounds of formula (6b) and (6c), where L2, X, Ar5*, R 7 and R## have a meaning given above, Ar* is the same or different and is an aromatic ring system having 6 to 40 ring atoms which, with one or more substituents R 8 may be substituted; and - 65 - excluding compounds of formulas (6b) and (6c) in which at least one substituent L2-Ar5* in compounds of formulas (6b) and (6c) corresponds to formula (E), where the following applies to the symbols and indices used: L4 is a single bond or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms; Z1 is O, S or Se; and R1*, R2*, R3*, R4* are independently H, D or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms. In a preferred embodiment of the compounds of the formula (6b) or (6c), the substituents Ar5*, identical or different at each occurrence, independently represent an aromatic ring system having 6 to 40 ring atoms, which is substituted by one or more radicals R 7may be substituted and L2 is a single bond or corresponds to a linker of the formulas L-1 to L-30, as previously described, wherein the dashed lines represent the bond to Ar5* and the remainder of the formulas (6b) or (6c). Compounds of the formula (6a-4), as previously described or preferably described, are also preferred embodiments of the compound of the formula (6c). Preferred compounds of the formula (6) are compounds of the formula (6d), - 66 - where the symbols and indices for this formula (6d) have the following meaning: a3 is, at each occurrence, identical or different, 0, 1, 2, 3 or 4; is derived from an aryl group having 6 to 20 ring atoms, which may be substituted by one or more substituents R##; W 1 means O, S, C(R W )2 or N-Ar5*; R Wis, on each occurrence, identically or differently, 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 one or more H atoms may be replaced by D, F, or CN, or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which may be replaced by one or more substituents selected from D, F, CN, 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 one or more H atoms of the alkyl group on the aromatic or heteroaromatic ring system may be replaced by D, F, or CN, where the two radicals R W which bind to the same carbon atom also form a ring system with each other; where L 2 , X, Ar5*, R 7and R## have the meanings given above. In a preferred embodiment of the compounds of the formula (6d), the substituents Ar5*, identical or different at each occurrence, independently represent an aromatic ring system having 6 to 40 ring atoms, which can be substituted with one or more radicals R 7 may be substituted and L2 is a single bond or corresponds to a linker of the formulas L-1 to L-30, as previously described, where the dashed lines represent the bond to Ar5* and the remainder of the formula (6d). In a particularly preferred embodiment of the compounds of the formulas (6b), (6c) and (6d), the substituents Ar5*, identical or different at each occurrence, independently represent an aromatic ring system Ar*-1 to Ar*-11, - 67 - where R 9 H or R 7 means and R 7 has a meaning given above or below. Preferred compounds of formula (6) are compounds of formula (6e), where the symbols and indices for this formula (6e) have the meaning: - 68 - L3 is an aromatic ring system with 6 to 40 ring atoms or a heteroaromatic ring system with 5 to 40 ring atoms, which are linked to one or more radicals R 7 may be substituted; where L2, X, Ar5, R 7 and R## have a meaning given above, and wherein compounds of formula (6e) are excluded in which at least one substituent L2-Ar5* corresponds to one of the formulas (C) or (D) and a second substituent L2-Ar5* corresponds to the formula (E), where the following applies to the symbols and indices used: L4 is a single bond or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms; Z1 and Z2 are each independently O, S or Se; R1*, R2*, R3*, R4* are independently H, D or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms. In a preferred embodiment of the compounds of the formula (6e), the substituents Ar5*, identical or different at each occurrence, independently represent an aromatic ring system having 6 to 40 ring atoms, which is substituted by one or more radicals R 7may be substituted and L2 is a single bond or corresponds to a linker of the formulas L-1 to L-30, as previously described, where the dashed lines represent the bond to Ar5* and the residue of formula (6d). and L3 corresponds to a linker of the formulas L-1 to L-30, as previously described, where the dashed lines represent the bond to the residue of formula (6e). - 69 - In compounds of formula (6e), L3 is preferably a heteroaromatic ring system having 9 to 30 ring atoms, which is linked to one or more residues R 7may be substituted. In compounds of formula (6e), L3 is preferably a linker of the formulas L-1 to L-30, as previously described, where the dashed lines represent the linkage to the residue of formula (6e), particularly preferably a linker of the formulas L-18 to L-30, where the dashed lines represent the linkage to the residue of formula (6e). Particularly preferred compounds of formulas (6) and (6e) are the compounds of formulas (6e-1) to (6e-3), - 70 - where the symbols and indices used are: (R 7 ) x , (R 7 ) y represent a monosubstitution, a disubstitution, a trisubstitution or the maximum permissible substitution with the substituent R 7 dar, R 18 is at each occurrence, identically or differently, a straight-chain alkyl group having 1 to 10 C atoms or an aryl group having 6 to 12 C atoms, where two substituents R 18together can form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which can be substituted with one or more substituents R 8 may be substituted; where L2 and R 7 have a meaning mentioned above or a meaning mentioned above and below with preference, and Ar5*, identical or different at each occurrence, independently represents an aromatic ring system Ar*-1 to Ar*-15, as described above. In compounds of the formulas (6e-1), (6e-2) and (6a-3), the substituents R 7 in (R 7 ) x , (R 7 ) y when occurring preferably as indicated below, most preferably D. Preferred compounds of formula (7) are the compounds of formula (7a), where Y, V 2 , L2 and R 7have a meaning given above, a3 is identical or different on each occurrence and is 0, 1, 2, 3 or 4, D corresponds to deuterium and a4 is 0, 1 or 2. - 71 - Preferred compounds of the formula (8) are the compounds of the formula (8a), where the symbols and indices for this formula (8a) have the following meaning: W1 means, identically or differently, O, S, C(R W )2or N-Ar5*; #X is CR or NAr5, preferably NAr5; R Wis, on each occurrence, the same or different, 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 one or more H atoms may be replaced by D, F or CN, or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms which may be replaced by one or more substituents selected from D, F, CN, 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 one or more H atoms of the alkyl group on the aromatic or heteroaromatic ring system may be replaced by D, F or CN; a3 is, on each occurrence, the same or different, 0, 1, 2, 3 or 4; Ring B is derived from an aryl group with 6 to 20 ring atoms, which may be substituted with one or more substituents R##, where L2, Ar5 and R## have a previously defined meaning. In compounds of formula (6d) or (8a), W1 is preferably O, C(R W )2 or N-Ar5*, particularly preferably N-Ar5*. In a preferred embodiment of the compounds of formulas (6), (6a), (6a-1), (6a-2), (6a-3), (6a-4), (6a-5), (6b), (6c), (6d), (6e), (6e-1), (6e-2), (6e-3), (7), (7a), (8), (8a), (9) or (10), which can be combined according to the invention with compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j) in the light-emitting layer, as described above, R 7 identically or differently on each - 72 - occurrence selected from the group consisting of D, F, CN, 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 8may be substituted, or an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, preferably having 5 to 40 ring atoms, each substituted by one or more radicals R 8 may be substituted. In a preferred embodiment of the compounds of formulas (6), (6a), (6a-1), (6a-2), (6a-3), (6a-4), (6a-5), (6b), (6c), (6d), (6e), (6e-1), (6e-2), (6e-3), (7), (7a), (8), (8a), (9) or (10), which can be combined according to the invention with compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j), as described above, R 7 identically or differently on each occurrence selected from the group consisting of D or an aromatic or heteroaromatic ring system having 6 to 30 ring atoms, which is reacted with one or more radicals R 8may be substituted. The preparation of the compounds of formulas (6), (6a), (6a-1), (6a-2), (6a-3), (6a-4), (6a-5), (6b), (6c), (6d), (6e), (6e-1), (6e-2), (6e-3), (7), (7a), (8), (8a), (9) and (10) are generally known and some of the compounds are commercially available. If compounds of the formulas (6), (6a), (6a-1), (6a-2), (6a-3), (6a-4), (6a-5), (6b), (6c), (6d), (6e), (6e-1), (6e-2), (6e-3), (7), (7a), (8), (8a), (9) and (10) are deuterated compounds, it is possible that the compound is a mixture of deuterated compounds of the same basic chemical structure, which only differ in the degree of deuteration. In a preferred embodiment of the organic electronic device according to the invention, partially or fully deuterated compounds of the formulas (6), (6a), (6a-1), (6a-2), (6a-3), (6a-4), (6a-5), (6b), (6c), (6d), (6e), (6e-1), (6e-2), (6e-3), (7), (7a), (8), (8a), (9) and (10) are used,wherein the average degree of deuteration of these compounds is at least 20mol% to 90mol%, preferably 30mol% to 100mol%. Suitable compounds of formula (6) are known, for example, from the following publications: WO2007 / 077810A1, WO2008 / 056746A1, WO2010 / 136109A1, WO2011 / 057706A2, WO2011 / 160757A1, WO2012 / 023947A1, WO2012 / 048781A1, WO2013 / 077352A1, WO2013147205A1, WO2013 / 083216A1, WO2014 / 094963A1, WO2014 / 007564A1, WO2014 / 015931A1, WO2015 / 090504A2, WO2015 / 105251A1, WO2015 / 169412A1, WO2016 / 015810A1, WO2016 / 013875A1, WO2016 / 010402A1, WO2016 / 033167A1, WO2017 / 178311A1, WO2017 / 076485A1, WO2017 / 186760A1, - 73 - WO2018 / 004096A1, WO2018 / 016742A1, WO2018 / 123783A1, WO2018 / 159964A1, WO2018 / 174678A1, WO2018 / 174679A1, WO2018 / 174681A1, WO2018 / 174682A1, WO2019 / 177407A1, WO2019 / 245164A1, WO2019 / 240473A1, WO2019 / 017730A1, WO2019 / 017731A1, WO2019 / 017734A1, WO2019 / 145316A1, WO2019 / 121458A1, WO2020 / 130381A1, WO2020 / 130509A1, WO2020 / 169241A1, WO2020 / 141949A1, WO2021 / 066623A1,WO2021 / 101220A1, WO2021 / 037401A1, WO2021 / 180614A1, WO2021 / 239772A1, WO2022 / 015084A1, WO2022 / 025714A1, WO2022 / 055169A1, EP3575296A1, EP3591728A1, US2014 / 0361254A1, US2014 / 0361268A1, KR20210036304A, KR20210036857A, KR2021147993A, JP2011 / 160367A2, JP2017 / 107992A2. Suitable compounds of formula (7) are known, for example, from the following publications: WO2015 / 182872A1, WO2015 / 105316A1, WO2017 / 109637A1, WO2018 / 060307A1, WO2018 / 151479A2, WO2018 / 088665A2, WO2018 / 060218A1, WO2018 / 234932A1, WO2019 / 058200A1, WO2019 / 017730A1, WO2019 / 017731A1, WO2019 / 066282A1, WO2019 / 059577A1, WO2020 / 141949A1, WO2020 / 067657A1, WO2022063744A1, WO2022 / 090108A1, WO2022 / 207678A1, KR2019035308A, KR2021147993A, CN110437241A, US2016 / 072078A1, US2019 / 148646A1. Suitable compounds of formula (8) are known, for example, from the following publications: WO2017 / 160089A1, WO2019 / 017730A1, WO2019 / 017731A1,WO2020 / 032424A1. Suitable compounds of formula (9) are known, for example, from the following publications: WO2015 / 093878A1, WO2016 / 033167A1, WO2017 / 183859A1, WO2017 / 188655A1, WO2018 / 159964A1. In a preferred embodiment of the electronic organic device according to the invention, a combination of the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j), as described above or preferably described, with in particular compounds of formulas (6), (6a), (6a-1), (6a-2), (6a-3), (6a-4), (6a-5), (6b), (6c), (6d), (6e), (6e-1), (6e-2), (6e-3), (7) and / or formula (7a) is used, as described above or preferably described, or corresponding compounds of Table 3 or 4 which fall under these formulas. In a particularly preferred embodiment of the electronic organic device according to the invention, a combination of the compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h),(1i) or (1j), as described above or preferably described, with in particular compounds of the formulas - 74 - (6), (6a), (6a-1), (6a-2), (6a-3), (6a-4), (6a-5) (6b), (6c), (6d), (6e), (6e-1), (6e-2) and / or (6e-3), as described above or preferably described or corresponding compounds of Table 3 or 4 which fall under these formulas. Further examples of suitable host materials of formulas (6), (6a), (6a-1), (6a-2), (6a-3), (6a-4), (6a-5), (6b), (6c), (6d), (6e), (6e-1), (6e-2), (6e-3), (7), (7a), (8), (8a), (9) and (10), for a combination with compounds of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j), as previously described or preferably described, are the structures of Table 3 and Table 4 mentioned below.
[0008]
[0009] - 79 -
[0010]
[0011]
[0012] - 94 - - 96 - Particularly suitable compounds of the formulas ((6), (6a), (6b), (6c), (6d), (6e) or (7), which are selected according to the invention and are preferably used in combination with at least one compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j) in the electroluminescent device according to the invention, are the compounds E1 to E45 of Table 4. - 97 - - 98 - - 99 - - 100 - The above-mentioned host materials of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j) and their preferred embodiments described or the compounds of Table 1 or the compounds H1 to H30 can be combined as desired in the - 101 - inventive device with the matrix materials / host materials of the formulas (6), (6a), (6a-1), (6a-2), (6a-3), (6a-4), (6a-5), (6b), (6c), (6d), (6e), (6e-1), (6e-2), (6e-3), (7), (7a), (8), (8a), (9) or (10), and their preferred embodiments described in Table 3 or the compounds E1 to E45 of Table 4.Very particularly preferred mixtures of the compounds of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j) with the host materials of the formulas (6), (6a), (6b), (6c), (6d), (6e) or (7) for the device according to the invention are obtained by combining the compounds H1 to H30 with the compounds E1 to E45 as shown below in Table 5. The first mixture M1, for example, is a combination of the compound H1 with E1. - 102 - - 103 - - 104 - - 105 - - 106 - - 107 - - 108 - - 109 - - 110 - - 111 - The concentration of the sum of all host materials of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j), as described above or preferably described, in the light-emitting layer of the device according to the invention is usually in the range from 5 wt.% to 90 wt.%, preferably in the range from 10 wt.% to 85 wt.%, more preferably in the range from 20 wt.% to 85 wt.%, - 112 - even more preferably in the range from 30 wt.% to 80 wt.%, very particularly preferably in the range from 20 wt.% to 60 wt.% and most preferably in the range from 30 wt.% to 50 wt.%, based on the total composition of the light-emitting layer. The concentration of the sum of all host materials of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j), as described above or described as preferred, in the light-emitting layer of the device according to the invention is usually in the range from 10 wt.% to 95 wt.-%, preferably in the range of 15 wt% to 90 wt%, more preferably in the range of 15 wt% to 80 wt%, even more preferably in the range of 20 wt% to 70 wt%, very particularly preferably in the range of 40 wt% to 80 wt% and most preferably in the range of 50 wt% to 70 wt%, based on the total composition of the light-emitting layer. The concentration of the sum of all host materials of the formulas ((6), (6a), (6a-1), (6a-2), (6a-3), (6a-4), (6a-5), (6b), (6c), (6d), (6e), (6e-1), (6e-2), (6e-3), (7), (7a), (8), (8a), (9) or (10), as described above or preferably described, in the light-emitting layer of the device according to the invention is usually in the range from 5 wt.% to 90 wt.%, preferably in the range from 10 wt.% to 85 wt.%, more preferably in the range from 20 wt.% to 85 wt.%, even more preferably in the range from 30 wt.% to 80 wt.%, very particularly preferably in the range from 20 wt.% to 60 wt.-% and most preferably in the range from 30 wt.% to 50 wt.%, based on the total composition of the light-emitting layer. The present invention also relates to an organic electronic device comprising a light-emitting layer comprising a mixture which, in addition to the above-mentioned host materials of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j), hereinafter referred to as host material 1, and the host material of at least one of the formulas (6), (6a), (6b), (6c), (6d), (6e), (7), (8), (8a), (9) or (10), hereinafter referred to as host material 2, as described above or preferably described, also contains at least one phosphorescent emitter. The present invention also relates to an organic electronic device comprising a light-emitting layer comprising a mixture selected from M1 to M1350, which also contains at least one phosphorescent emitter.- 113 - The term phosphorescent emitters typically encompasses compounds in which light emission occurs through a spin-forbidden transition from an excited state with higher spin multiplicity, i.e. a spin state > 1, for example through a transition from a triplet state or a state with an even higher spin quantum number, for example a quintet state. A transition from a triplet state is preferably understood here. Suitable phosphorescent emitters (= triplet emitters) are particularly compounds which, upon suitable excitation, emit light, preferably in the visible range, and which also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80, 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. For the purposes of the present invention, all luminescent compounds containing the above-mentioned metals are regarded as phosphorescent emitters. In general, all phosphorescent complexes as used according to the prior art for phosphorescent OLEDs and as known to the person skilled in the art in the field of organic electroluminescent devices are suitable. Preferred phosphorescent emitters according to the present invention correspond to formula (IIIa). where the symbols and indices for this formula (IIIa) have the meaning: n+m is 3, n is 1 or 2, m is 2 or 1, X is, identically or differently on each occurrence, N or CR, R is, identically or differently on each occurrence, H, D, F, CN or a branched or linear alkyl group having 1 to 10 C atoms or a partially or fully - 114 - deuterated branched or linear alkyl group having 1 to 10 C atoms or a cycloalkyl group having 4 to 7 C atoms which may be partially or fully substituted with deuterium or an aromatic or heteroaromatic ring system having 5 to 60 ring atoms which may be partially or fully substituted with deuterium.The invention accordingly further provides an organic electroluminescent device as described above or preferably described, characterized in that the light-emitting layer, in addition to the host materials 1 and 2, contains at least one phosphorescent emitter which corresponds to the formula (IIIa), as described above. In emitters of the formula (IIIa), n is preferably 1 and m is preferably 2. In emitters of the formula (IIIa), one X is preferably selected from N and the other Xs are CR or all Xs, identical or different on each occurrence, are CR. In emitters of the formula (IIIa), at least one R is preferably different from H. In emitters of the formula (IIIa), two Rs are preferably different from H and have one of the meanings otherwise given above for the emitters of the formula (IIIa). Preferred phosphorescent emitters according to the present invention correspond to the formulas (I), (II), (III), (IV) or (V). - 115 - - 116 - where the symbols and indices for these formulas (I), (II), (III), (IV) and (V) have the meaning: R1 is H or D, R2 is H, D, F, CN or a branched or linear alkyl group having 1 to 10 C atoms or a partially or fully deuterated branched or linear alkyl group having 1 to 10 C atoms or a cycloalkyl group having 4 to 10 C atoms, which may be partially or fully substituted with deuterium. Preferred phosphorescent emitters according to the present invention correspond to the formulas (VI), (VII) or (VIII), where the symbols and indices for these formulas (VI), (VII) and (VIII) have the meaning: - 117 - R1 is H or D, R2 is H, D, F, CN or a branched or linear alkyl group having 1 to 10 C atoms or a partially or fully deuterated branched or linear alkyl group having 1 to 10 C atoms or a cycloalkyl group having 4 to 10 C atoms, which may be partially or fully substituted with deuterium. Preferred examples of phosphorescent emitters are described in WO2019 / 007867 on pages 120 to 126 in Table 5 and on pages 127 to 129 in Table 6. The emitters are incorporated into the description by this reference. Particularly preferred examples of phosphorescent emitters are listed in Table 6 below. - 118 - - 120 - - 121 - In the mixtures according to the invention or in the light-emitting layer of the device according to the invention, each mixture selected from the sum of the mixtures M1 to M1350 is preferably combined with a compound of the formula (IIIa) or a compound of the formulas (I) to (VIII) or a compound from Table 6. The light-emitting layer in the organic electroluminescent device according to the invention comprising at least one phosphorescent emitter is preferably an infrared-emitting, yellow-, orange-, red-, green-, blue-, or ultraviolet-emitting layer, particularly preferably a yellow- or green-emitting layer, and very particularly preferably a green-emitting layer. A yellow-emitting layer is understood to mean a layer whose photoluminescence maximum is in the range from 540 to 570 nm.An orange-emitting layer is understood to be a layer whose photoluminescence maximum lies in the range from 570 to 600 nm. A red-emitting layer is understood to be a layer whose photoluminescence maximum lies in the range from 600 to 750 nm. A green-emitting layer is understood to be a layer whose photoluminescence maximum lies in the range from 490 to 540 nm. A blue-emitting layer is understood to be a layer whose photoluminescence maximum lies in the range from 440 to 490 nm.The photoluminescence maximum of the layer is determined by measuring the photoluminescence spectrum of the layer with a layer thickness of 50 nm at room temperature, wherein the layer contains the inventive combination of the host material 1 of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j) and the host material 2 of at least one of the formulas (6), (6a), (6b), (6c), (6d), (6e), (7), (8), (8a) and / or (9) and the corresponding emitter. The photoluminescence spectrum of the layer is recorded, for example, using a commercially available photoluminescence spectrometer. The photoluminescence spectrum of the selected emitter is generally measured in oxygen-free solution, 10. -5molar, measured at room temperature, and any solvent in which the selected emitter dissolves at the specified concentration is suitable. Particularly suitable solvents are usually toluene or 2-methyl-THF, but also dichloromethane. The measurement is carried out using a commercially available photoluminescence spectrometer. The triplet energy T1 in eV is determined from the photoluminescence spectra of the emitters. First, the peak maximum Plmax. (in nm) of the photoluminescence spectrum is determined. The peak maximum Plmax. (in nm) is then converted to eV according to: E(T1 in eV) = 1240 / E(T1 in nm) = 1240 / PLmax. (in nm). Preferred phosphorescent emitters are therefore yellow emitters, preferably of formula (IIIa), formulas (I) to (VIII) or from Table 6, whose triplet energy T1 is preferably between ~2.3 eV and ~2.1 eV.Preferred phosphorescent emitters are accordingly green emitters, preferably of formula (IIIa), of formulas (I) to (VIII) or from Table 6, whose triplet energy T1 is preferably between ~2.5 eV and ~2.3 eV. Particularly preferred phosphorescent emitters are accordingly green emitters, preferably of formula (IIIa), of formulas (I) to (VIII) or from Table 6, as described above, whose triplet energy T1 is preferably between ~2.5 eV and ~2.3 eV. Very particular preference is given to selecting green emitters, preferably of formula (IIIa), of formulas (I) to (VIII) or from Table 6, as described above, for the mixture according to the invention or the light-emitting layer according to the invention. - 123 - Fluorescent emitters can also be present in the light-emitting layer of the device according to the invention or in the mixture according to the invention.Preferred fluorescent-emitting compounds are selected from the class of arylamines, where preferably at least one of the aromatic or heteroaromatic ring systems of the arylamine is a fused ring system, particularly preferably having at least 14 ring atoms. Preferred examples of these are aromatic anthraceneamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic chryseneamines, or aromatic chrysenediamines. An aromatic anthraceneamine is understood to be a compound in which one diarylamino group is bonded directly to one anthracene group, preferably in the 9-position. An aromatic anthracenediamine is understood to be a compound in which two diarylamino groups are bonded directly to one anthracene group, preferably in the 9,10-position.Aromatic pyrenamines, pyrenediamines, chrysenamines, and chrysenediamines are defined analogously, with the diarylamino groups on the pyrene preferably being bonded in the 1-position or 1,6-position. Further preferred emitting compounds are indenofluorenamines or diamines, benzoindenofluorenamines or diamines, and dibenzoindenofluorenamines or diamines, as well as indenofluorene derivatives with fused aryl groups. Pyrenearylamines are also preferred. Also preferred are benzoindenofluoreneamines, benzofluoreneamines, extended benzoindenofluorenes, phenoxazines, and fluorene derivatives linked to furan units or thiophene units. Furthermore, the light-emitting device or the mixture according to the invention can also contain materials that exhibit TADF (thermally activated delayed fluorescence).In a further preferred embodiment of the invention, the at least one light-emitting layer of the organic electroluminescent device can comprise three or four different matrix materials, preferably three different matrix materials. These corresponding mixed-matrix systems can consist of the matrix materials described for host material 1 and host material 2, but they can also contain, as a third or fourth matrix material, for example, in addition to a host material 1 or host material 2, wide-band-gap materials, bipolar host materials, electron-transport materials (ETM), or hole-transport materials (HTM). The mixed-matrix system is preferably optimized for an emitter of formula (IIIa), formulas (I) to (VIII), or from Table 6.According to one embodiment of the present invention, the mixture for producing the light-emitting layer of the organic electronic device contains, in addition to the constituents of the host material of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), or (1j) as host material 1 and the host material 2 selected from one or more of the compounds of formulas (6), (6a), (6a-1), (6a-2), (6a-3), (6a-4), (6a-5), (6b), (6c), (6d), (6e), (6e-1), (6e-2), (6e-3), (7), (7a), (8), (8a), (9), or (10), as described above, no further constituents, i.e., functional materials. These are material mixtures that are used as such to produce the light-emitting layer. These mixtures are also referred to as premix systems, which are used as the sole material source during the evaporation of the host materials for the light-emitting layer and which have a constant mixing ratio during evaporation.This allows for the simple and rapid vapor deposition of a layer with a uniform distribution of components, without the need for precise control of multiple material sources. According to an alternative embodiment of the present invention, the mixture for producing the light-emitting layer of the organic electronic device contains, as a premix system, in addition to the components of host material 1 and 2, as described above, a phosphorescent emitter, as described above. With a suitable mixing ratio during vapor deposition, this mixture can also be used as the sole material source, as described above.Preferred are premix systems for producing the light-emitting layer of the organic electronic device consisting of two matrix materials, namely a compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j) and a compound of one of the formulas formulas (6), (6a), (6a-1), (6a-2), (6a-3), (6a-4), (6a-5), (6b), (6c), (6d), (6e), (6e-1), (6e-2), (6e-3), (7), (7a), (8), (8a), (9) or (10), wherein at the same time the remark regarding deuterated materials also applies in this case, as described above.Preferred are premix systems consisting of three matrix materials, namely a compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j) and two compounds of one of the formulas (6), (6a), (6a-1), (6a-2), (6a-3), (6a-4), (6a-5), (6b), (6c), (6d), (6e), (6e-1), (6e-2), (6e-3), (7), (7a), (8), (8a), (9) or (10), whereby the remark regarding deuterated materials also applies in this case, as described above. The components or constituents of the light-emitting layer of the device according to the invention can be processed by vapor deposition or from solution. The material combination of host materials 1 and 2, as described above or preferably described, optionally with the phosphorescent emitter, as described above or preferably described, - 125 - can be provided in a formulation containing at least one solvent. Suitable formulations have been described previously.The light-emitting layer in the device according to the invention according to the preferred embodiments and the emitting compound preferably contains between 99.9 and 1 vol.%, further preferably between 99 and 10 vol.%, particularly preferably between 98 and 60 vol.%, very particularly preferably between 97 and 80 vol.% of matrix material of at least one compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j) and at least one compound of the formulas (6), (6a), (6a-1), (6a-2), (6a-3), (6a-4), (6a-5), (6b), (6c), (6d), (6e), (6e-1), (6e-2), (6e-3), (7), (7a), (8), (8a), (9) or (10) according to the preferred embodiments, based on the total composition of Emitter and matrix material. Accordingly, the light-emitting layer in the device according to the invention preferably contains between 0.1 and 99 vol.%, more preferably between 1 and 90 vol.%, particularly preferably between 2 and 40 vol.%.- %, very particularly preferably between 3 and 20 vol. % of the emitter based on the total composition of the light-emitting layer consisting of emitter and matrix material. If the compounds are processed from solution, the corresponding amounts in wt. % are preferably used instead of the above-specified amounts in vol. %. The present invention also relates to an organic electroluminescent device as described above or preferably described, wherein the organic layer contains a hole injection layer (HIL) and / or a hole transport layer (HTL), the hole-injecting material and hole-transporting material of which belongs to the class of arylamines. The sequence of layers in the organic electroluminescent device according to the invention is preferably the following: anode / hole injection layer / hole transport layer / emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode.This sequence of layers is a preferred sequence. It should be noted again that not all of the layers mentioned need to be present and / or that additional layers may be present. - 126 - All materials used in the prior art as electron-transport materials in the electron-transport layer can be used as materials for the electron-transport layer. Particularly suitable are aluminum complexes, for example Alq3, zirconium complexes, for example Zrq4, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives, and phosphine oxide derivatives.Suitable cathodes for the device according to the invention include metals with low work functions, metal alloys, or multilayer structures made of different metals, such as alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Alloys made of an alkali or alkaline earth metal and silver, for example, an alloy of magnesium and silver, are also suitable. In multilayer structures, in addition to the metals mentioned, other metals with a relatively high work function, such as Ag or Al, can also be used. Combinations of the metals, such as Ca / Ag, Mg / Ag, or Ba / Ag, are then generally used. It may also be preferable to introduce a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor.Suitable materials for this purpose include alkali metal or alkaline earth metal fluorides, as well as the corresponding oxides or carbonates (e.g., LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.). Lithium quinolinate (LiQ) can also be used. The layer thickness of this layer is preferably between 0.5 and 5 nm. Materials with a high work function are preferred as the anode. The anode preferably has a work function greater than 4.5 eV vs. vacuum. Metals with a high redox potential, such as Ag, Pt, or Au, are suitable for this purpose. Metal / metal oxide electrodes (e.g., Al / Ni / NiOx, Al / PtOx) may also be preferred. For some applications, at least one of the electrodes must be transparent or partially transparent to enable either the irradiation of the organic material (organic solar cell) or the extraction of light (OLED, O-LASER). Preferred anode materials here are conductive mixed metal oxides.Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred. Also preferred are conductive, doped organic materials, in particular conductive doped polymers. Furthermore, the anode can also consist of multiple layers, for example an inner layer of ITO and an outer layer of a metal oxide, preferably tungsten oxide, molybdenum oxide, or vanadium oxide. - 127 - The organic electroluminescent device according to the invention is structured, contacted, and finally sealed during production (depending on the application), since the service life of the devices according to the invention is shortened in the presence of water and / or air. The production of the device according to the invention is not restricted in this case. It is possible for one or more organic layers, including the light-emitting layer, to be coated using a sublimation process.The materials are sublimated in vacuum 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 -7mbar. The organic electroluminescent device according to the invention is preferably characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or with the aid of carrier gas sublimation. The materials are applied at a pressure between 10-5 mbar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus structured (e.g. BMS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301). Furthermore, the organic electroluminescent device according to the invention is preferably characterized in that one or more organic layers containing the composition according to the invention are coated from solution, for example by spin coating, or using any printing process, such asScreen printing, flexographic printing, nozzle printing, or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing, are used. Soluble host materials 1 and 2 and phosphorescent emitters are required for this. Solution processing has the advantage that, for example, the light-emitting layer can be applied very easily and cost-effectively. This technique is particularly suitable for the mass production of organic electroluminescent devices. Hybrid processes are also possible, in which, for example, one or more layers are applied from solution and one or more further layers are vapor-deposited. These processes are generally known to those skilled in the art and can be applied to organic electroluminescent devices.- 128 - When produced by vapor deposition, there are basically two ways in which the organic layer according to the invention, preferably the light-emitting layer, can be applied or vapor-deposited onto any desired substrate or the previous layer. Firstly, the materials used can each be placed in a material source and then evaporated from the various material sources ("co-evaporation"). Secondly, the various materials can be premixed ("premixed", premix systems) and the mixture placed in a single material source, from which it is then evaporated ("premix evaporation"). This allows the vapor deposition of the light-emitting layer with a uniform distribution of the components to be achieved in a simple and rapid manner, without the need for precise control of a large number of material sources.The following methods are possible: A method for producing the organic electroluminescent device according to the invention, as described above or preferably described, characterized in that the organic layer, preferably the light-emitting layer, the electron transport layer and / or hole blocking layer, is applied by vapor phase deposition, in particular with a sublimation method and / or with an OVPD (Organic Vapor Phase Deposition) method and / or with the aid of carrier gas sublimation, or from solution, in particular by spin coating or with a printing method.A method for producing the device according to the invention, characterized in that the light-emitting layer of the organic layer is applied by vapor deposition, wherein the at least one compound of the formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j) together with the further materials which form the light-emitting layer are deposited successively or simultaneously from at least two material sources from the vapor phase.A method for producing the device according to the invention, characterized in that the light-emitting layer of the organic layer is applied by vapor deposition, wherein the at least one compound of formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), or (1j) is deposited from the vapor phase together with at least one further matrix material as a premix, sequentially or simultaneously with the light-emitting materials selected from the group of phosphorescent emitters, fluorescent emitters, and / or emitters exhibiting TADF (thermally activated delayed fluorescence). The electronic devices according to the invention, in particular organic electroluminescent devices, are characterized by one or more of the following surprising advantages over the prior art: 1.Electronic devices, in particular organic electroluminescent devices comprising compounds according to formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j) or the preferred embodiments set out above and below in combination with at least one compound of the formulas (6), (6a), (6a-1), (6a-2), (6a-3), (6a-4), (6a-5), (6b), (6c), (6d), (6e), (6e-1), (6e-2), (6e-3), (7), (7a), (8), (8a), (9) or (10) as matrix material, have a very good lifetime. These compounds according to formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j) particularly result in low roll-off, i.e., a low drop in the power efficiency of the device at high luminance levels. 2. The compounds according to formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j) or the preferred embodiments described above and below exhibit very high stability and service life. 3.When using compounds according to formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j) 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. 4. The compounds according to formulas (1), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i) or (1j) or the preferred embodiments described above and below have a deep triplet level T1, which can be in the range of 2.40 eV - 2.90 eV. These advantages mentioned above are not accompanied by an excessive deterioration of the other electronic properties.- 130 - 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, an equivalent, or a 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 one another in any way, unless certain features and / or steps are mutually exclusive. This applies in particular to the combination of preferred features of the present invention.The technical teaching disclosed by the present invention can be abstracted and combined with other examples. The invention is explained in more detail by the following examples, without intending to limit it. Examples General Methods: The Gaussian16 program package (Rev. B.01) is used in all quantum chemical calculations. The neutral singlet ground state is optimized at the B3LYP / 6-31G(d) level of theory. HOMO and LUMO values are determined at the B3LYP / 6-31G(d) level for the ground state energy optimized with B3LYP / 6-31G(d). TD-DFT singlet and triplet excitations (vertical excitations) are then calculated using the same method (B3LYP / 6-31G(d)) and the optimized ground state geometry. The standard settings for SCF and gradient convergence are used. From the energy calculation, the HOMO is obtained as the last orbital occupied by two electrons (Alpha occ.eigenvalues) and LUMO as the first unoccupied orbital (alpha virt. eigenvalues) in Hartree units, where HEh and LEh represent the HOMO energy in Hartree units and the LUMO energy in Hartree units, respectively. From this, the HOMO and LUMO values in electronvolts, calibrated using cyclic voltammetry measurements, are determined as follows: HOMOcorr = 0.90603 * HOMO - 0.84836 LUMOcorr = 0.99687 * LUMO - 0.72445 - 131 - The triplet level T1 of a material is defined as the relative excitation energy (in eV) of the lowest-energy triplet state, which results from quantum chemical energy calculations. The singlet level S1 of a material is defined as the relative excitation energy (in eV) of the second-lowest energy singlet state, resulting from quantum chemical energy calculations. The lowest energy singlet state is referred to as S0.The method described here is independent of the software package used and always delivers the same results. Examples of frequently used programs for this purpose are "Gaussian09" (Gaussian Inc.) and Q-Chem 4.1 (Q-Chem, Inc.). In this case, the program package "Gaussian16 (Rev. B.01)" is used to calculate the energies. Synthesis examples: Unless otherwise stated, the following syntheses are carried out under a protective gas atmosphere in dried solvents. The solvents and reagents can be obtained, for example, from Sigma-ALDRICH or ABCR. The corresponding CAS numbers are given for the compounds known from the literature. 1) 1-Bromo-4H-Naphtho[1,2,3,4-def]carbazole)-d. 10 3.7 g (15.5 mmol; 1.00 eq) of 4H-naphtho[1,2,3,4-def]carbazole and 20.0 g of 5% Pt on activated carbon were suspended in 400 g (502 mmol; 1.00 eq) of deuterium oxide [CAS 7789-20-0] and 200 g (778 mmol; 1.55 eq) of toluene-d8 [CAS 2037-26-5]. The reaction mixture was stirred for 5 days at 165°C under elevated autogenous pressure. After cooling, the mixture was extracted twice with tetrahydrofuran, and the combined organic phases were washed with brine and dried over sodium sulfate. After filtration, the solvent was removed under reduced pressure. The product shown above, in a mixture with portions of H / D isotopomers and H / D isotopologues, is obtained after further purification by extraction, recrystallization, and sublimation. - 132 - The yield is 1.7 g (6.9 mmol), corresponding to 47% of theory. 2) 1-Bromo-4H-Naphtho[1,2,3,4-def]carbazole 43 g (180.0 mmol) of 4H-naphtho[1,2,3,4-def]carbazole are suspended in 1500 mL of DMF. 32 g (180 mmol) of NBS (N-bromosuccinimide) are added portionwise to this suspension at 0°C and stirred for 5 hours in the dark, during which the temperature slowly increases to 30°C. Water / ice is then added, the solid is separated, and the residue is washed with ethanol. The residue is recrystallized from toluene / ethanol (1:1). The yield is 39 g (123 mmol), corresponding to 69% of theory. The following compounds are prepared analogously: - 133 - 3) 1-Bromo-4-phenyl-naphtho[1,2,3,4-def]carbazole 7.9 g (24.8 mmol, 1.00 eq) of 1-bromo-4H-naphtho[1,2,3,4-def]carbazole, 26.1 g (128 mmol, 5.2 eq) of iodobenzene, and 7.1 g (74.4 mmol, 3 eq) of NaOtBu were placed in 220 ml of dried DMF and made inert with argon. Subsequently, 0.62 g (2.7 mmol, 0.11 eq) of 1,3-di(2-pyridyl)-1,3-propanedione and 0.52 g (2.7 mmol, 0.11 eq) of copper(I) iodide were added, and the mixture was heated at 140°C for three days. After the reaction, the reaction mixture was carefully concentrated using a rotary evaporator, the precipitated solid was filtered off with suction, and the residue was washed with water and ethanol. The crude product is purified twice using a hot extractor (toluene / heptane 1:1), and the resulting solid is recrystallized from toluene. The yield after sublimation is 8.3 g (20.9 mmol), 85% of theory. The following compounds are prepared analogously: - 136 - 4) 4-Phenyl-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-1-yl)naphtho[1,2,3,4-def]carbazole 8.7 g (22 mmol) of 1-bromo-4-phenyl-naphtho[1,2,3,4-def]carbazole, 6.2 g (24 mmol) of bis(pinacolato)diborane, and 6.3 g (64 mmol) of potassium acetate are suspended in 75 ml of dioxane. 0.53 g (0.66 mmol) of 1,1-bis(diphenylphosphino)ferrocene dichloropalladium(II) complex with DCM (dichloromethane) is added to this suspension. The reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated, washed three times with 50 mL of water, and then evaporated to dryness. The residue is recrystallized from toluene. The yield after sublimation is 7.2 g (16.2 mmol), 74% of theory. - 138 - 5) 1-[9-phenyl-9H-carbazol-3-yl)]-9-phenyl-4H-naptho[1,2,3,4-def]carbazole 51.5 g (160 mmol) of 4-phenyl-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-1-yl)-naphtho[1,2,3,4-def]carbazole, 77 g (175 mmol) of 3-bromo-N-phenylcarbazole, and 36 g (340 mmol) of sodium carbonate are suspended in 1000 mL of ethylene glycol diamine ether and 280 mL of water. 1.8 g (1.5 mmol) of tetrakis(triphenylphosphine)palladium(0) are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated, filtered through silica gel, washed three times with 200 mL of water, and then evaporated to dryness. The product is purified by column chromatography on silica gel with toluene / heptane (1:2) and finally evaporated in high vacuum (p = 5 x 10 -7 mbar) (purity 99.9%). The yield is 81 g (145 mmol), corresponding to 61% of theory. The following compounds are prepared analogously: - 140 - - 141 - - 142 - - 144 - - 145 - 6) 1-[3-phenyl-9H-carbazol-3-yl)]-9-phenyl-4H-naptho[1,2,3,4-def]carbazole A degassed solution of 59 g (150 mmol) of 1-bromo-4-phenyl-naphtho[1,2,3,4-def]carbazole and 36 g (150 mmol) of 3-phenyl-9H-carbazole in 600 mL of toluene was saturated with N2 for 1 h. The solution was then treated first with 2.09 mL (8.6 mmol) of P(tBu)3, followed by 1.39 g (6.1 mmol) of palladium(II) acetate, and then with 17.8 g (185 mmol) of NaOtBu in the solid state. The reaction mixture was heated under reflux for 1 h. After cooling to room temperature, 500 mL of water was carefully added. The aqueous phase was washed with 3 x 50 mL of toluene, dried over MgSO4, and the solvent removed in vacuo. The crude product is then purified by chromatography on silica gel using heptane / acetic acid ester (20 / 1). The residue is recrystallized from toluene and finally concentrated under high vacuum (p = 5 x 10 -6mbar). The yield is 62 g (112 mmol), corresponding to 75% of theory. - 146 - The following compounds are prepared analogously: - 147 - - 149 - - 150 - 7) 1-[9-{[1,1'-Biphenyl]-4yl}-9H-carbazol-3-yl)]-9-phenyl-4H-naptho[1,2,3,4-def]carbazol-d 26 - 151 - 30 g (48.0 mmol; 1.00 eq) of 1-[9-{[1,1'-biphenyl]-4-yl}-9H-carbazol-3-yl)]-9-phenyl-4H-naptho[1,2,3,4-def]carbazole is suspended in 640 mL (120 eq) of toluene-d8 [CAS 2037-26-5]. 16.6 mL (6.00 eq) of trifluoromethanesulfonic acid is added to this mixture while cooling. The reaction mixture is stirred at ambient temperature for 6 hours. Subsequently, 120 mL (130 eq) of deuterium oxide [CAS 7789-20-0] is added dropwise at 0°C. After neutralization with a potassium sulfate solution, the mixture is extracted with toluene, and the combined organic phases are washed with brine and dried over sodium sulfate. After filtration, the solvent is removed under reduced pressure. 25.1 g (40 mmol, 85% of theory) of the product shown above, in a mixture with portions of H / D isotopomers and H / D isotopologues, are obtained after chromatographic purification and finally concentrated under high vacuum (p = 5 x 10 -7mbar) (purity 99.9%). The following compounds are prepared analogously: - 152 - - 153 - Production of the OLEDs The following examples V1 to V6 and B1 to B21 (see Tables 7 and 8) present the data for various OLEDs. Examples B1 to B24 show data for OLEDs according to the invention. The substrate for the OLEDs in Table 7 is glass flakes coated with structured ITO (indium tin oxide) with a thickness of 50 nm. The exact structure of the OLEDs can be found in Table 7. The materials required to produce the OLEDs are shown in Table 9, unless previously described. All materials are thermally vapor-deposited in a vacuum chamber. The emission layer always consists of at least one matrix material (also called host material) and an emitting dopant (dopant, emitter), which is admixed with the matrix material(s) in a specific volume fraction by co-evaporation.A specification such as H1: E8:TEG1 (46%:42%:12%) 40nm means that material H1 is present in a volume fraction of 46% as host material 1, compound E8 as host material 2 in a fraction of 42%, and TEG1 in a fraction of 12% in a 40nm-thick layer. Analogously, the electron-transport layer can also consist of a mixture of two materials. OLEDs are characterized as standard. For this purpose, the electroluminescence spectra and current-voltage-luminance characteristics (IUL characteristics) are measured, from which the EQE is calculated. The calculation assumes a Lambertian radiation pattern. The electroluminescence spectra are determined at a luminance of 1000 cd / m², and the CIE 1931 x and y color coordinates are calculated from these. EQE1000 refers to the external quantum efficiency at an operating luminance of 1000 cd / m².- 154 - The lifetime LD is defined as the time after which the luminance drops from an initial luminance L0 (in cd / m²) to a certain proportion L1 (in cd / m²) when operated at a constant current density j0 in mA / cm². A value of L1 = 80% in Table 8 means that the lifetime specified in column LD corresponds to the time (in hours) after which the luminance drops to 80% of its initial value (L0). Use of compounds and mixtures according to the invention in OLEDs The compounds or material combinations according to the invention can be used in the emission layer in phosphorescent green OLEDs. The data for the various OLEDs are summarized in Table 8. Examples C1 to C6 are comparative examples according to the prior art, while Examples B1 to B24 show data for OLEDs according to the invention. The examples according to the invention show a clear advantage in the lifetime of the device. - 155 - - 156 - - 157 - Table 9: Materials used, unless previously described - 158 -
Claims
- 159 - Claims 1. Organic electronic device comprising an anode, a cathode and at least one light-emitting layer, containing at least one compound of formula (1) and at least one further matrix material, where the symbols and indices used are: L is a single bond, an aromatic ring system with 6 to 40 ring atoms or an electron-rich heteroaromatic ring system with 9 to 40 ring atoms, which are bonded to one or more radicals R 0 may be substituted; R 0 is selected at each occurrence, identically or differently, from the group consisting of D, F, Cl, Br, I, CN, NO2, C(=O)R 2 , P(=O)(Ar)2, P(Ar)2, B(Ar)2, Si(Ar)3, Si(R 2)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 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 substituted by R 2 C=CR 2 , Si(R 2 )2, C=O, C=S, C=NR 2 , P(=O)(R 2 ), SO, SO2, NR 2 , O, S or CONR 2 and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which is substituted by one or more radicals R 2 may be substituted, an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, which may be substituted with one or more radicals R 2may be substituted, or an aralkyl or heteroaralkyl group having 5 to 40 ring atoms which may be substituted with one or more radicals R 2 may be substituted; Rx corresponds to one of the formulas (1-2) to (1-11) - 161 - * denotes the bond to L; L1 is, at each occurrence, the same or different, a bond, O, S, C(R)2 or N-Ar; R a , R b and R c represent a monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution or no substitution and R a , R b and R c are at each occurrence independently D, CN, F, a non-deuterated or partially or fully deuterated - 162 - Alkyl group having 1 to 10 C atoms or a non-deuterated or partially or fully deuterated aromatic ring system having 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl having 9 to 40 ring atoms; V is O, S, Se, C(R)2, Si(R)3 or N-Ar3; R is, at each occurrence, identically or differently 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 one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms may be replaced by D, F, or CN or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms which is substituted with one or more substituents selected from D, F, CN,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 one or more non-adjacent CH2 groups of the alkyl group may be replaced by O or S and where one or more H atoms of the alkyl group may be replaced by D, F, or CN, where two substituents R may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted with one or more substituents R, 1 may be substituted; Ar is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms which is substituted by one or more radicals R 2 may be substituted; Ar1 is at each occurrence, identically or differently, an aromatic or electron-rich heteroaromatic ring system having 5 to 40 ring atoms, which is substituted by one or more radicals R 1may be substituted; Ar2, Ar3 are at each occurrence, identically or differently, an aromatic or electron-rich heteroaromatic ring system having 5 to 40 ring atoms, which is substituted by one or more radicals R 2 may be substituted; R 1 is selected at each occurrence, identically or differently, from the group consisting of D, F, CN, Si(Aryl)3, a straight-chain alkyl group with 1 - 163 - to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms may be replaced by D, F, or CN or a non-deuterated or partially or fully deuterated aromatic ring system having 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl having 9 to 40 ring atoms; R 2is selected, identically or differently at each occurrence, from the group consisting of D, F, CN, Si(Aryl)3, 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 one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms may be replaced by D, F, or CN; Aryl is, at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms which may be replaced by one or more substituents selected from D, F, CN, 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 one or more non-adjacent CH2 groups of the alkyl group may be replaced by O or S and where one or more H atoms of the alkyl group may be replaced by D, F, or CN;u, v are independently 0 or 1 at each occurrence and u+v is 1 or 2; wherein the further matrix material corresponds to one or more of the compounds of formulas (6), (7), (8), (9) or (10); - 164 - where the following applies to the symbols and indices used: X is the same or different at each occurrence N or CR 6 , preferably N; L2 is at each occurrence, identically or differently, a single bond, an aromatic ring system having 5 to 20 ring atoms or a heteroaromatic ring system having 9 to 30 ring atoms, which are bonded to one or more radicals R 7 may be substituted; R## is at each occurrence, identically or differently, D, F, CN or an aromatic ring system having 6 to 20 ring atoms which is substituted with one or more radicals R 6may be substituted and two adjacent substituents R## may together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system which may be substituted with one or more radicals R 7 can be substituted; - 165 - Y is the same or different at each occurrence, independently of each other N, CH, CR 7 or L2-Ar5, where it is excluded that two adjacent Y simultaneously represent N; V2 is O or S; R 6 is, identically or differently at each occurrence, D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 7 may be substituted and wherein one or more non-adjacent CH2 groups are substituted by Si(R 7 )2, C=O, NR 7 , O, S or CONR 7may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, each of which is substituted by one or more radicals R 7 can be substituted; two radicals R 6 also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar5 * represents, identically or differently at each occurrence, independently an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which with one or more radicals R 7 may be substituted, whereby for the heteroaromatic ring system the heterocycles of formulas (A) and (B) are excluded, Ar5, identically or differently at each occurrence, independently represents an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which is substituted by one or more radicals R 7 may be substituted; R 7is the same or different at each occurrence D, F, Cl, Br, I, N(R 8 )2, CN, NO2, OR 8 , SR 8 , Si(R 8 )3, B(OR 8 )2, C(=O)R 8 , P(=O)(R 8 )2, S(=O)R 8 , S(=O)2R 8 , OSO2R 8 , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, - 166 - wherein the alkyl, alkenyl or alkynyl group is each substituted with one or more radicals R 8 may be substituted, with one or more non-adjacent CH2 groups being substituted by Si(R 8 )2, C=O, NR 8 , O, S or CONR 8 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which is substituted by one or more radicals R 8 may be substituted; two or more radicals R 7form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; R 8 is, on each occurrence, identically or differently, H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, in particular a hydrocarbon radical, having 1 to 20 C atoms, in which one or more H atoms may also be replaced by F; b1 is 0, 1, 2, 3 or 4; b2 is 0, 1, 2 or 3, excluding compounds of the formula (6) in which at least one substituent L2-Ar5* corresponds to one of the formulas (C) or (D) and a second substituent L2-Ar5* corresponds to the formula (E), where the symbols and indices used are: L4 is a single bond or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms; Z1 and Z2 are each independently O, S or Se; R1*, R2*, R3*, R4* are independently H, D or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms. - 167 - 2. The organic electronic device according to claim 1, wherein the electronic device is selected from organic light-emitting transistors (OLETs), organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers), and organic light-emitting diodes (OLEDs).
3. The organic electronic device according to claim 1 or 2, wherein the light-emitting layer contains a phosphorescent emitter.
4. The organic electronic device according to one or more of claims 1 to 3, wherein the device contains, in addition to the light-emitting layer, an electron-transporting layer or a hole-blocking layer containing at least one compound of formula (1). 5.Organic electronic device according to one or more of claims 1 to 4, wherein in compounds of formula (1), L corresponds to a single bond or to one of the formulae L-1 to L-30 which is substituted by one or more radicals R. 0 can be substituted: - 168 - where the dashed lines indicate the bond to Rx or to the radical of formula (1); and V1 is O, S, Se, or C(R)2.
6. The organic electronic device according to one or more of claims 1 to 5, where Rx corresponds to one of formulas (1-2), (1-4), (1-5), (1-6), or (1-7). - 169 - 7. Organic electronic device according to one or more of claims 1 to 6, wherein the compound of formula (1) is selected from the compounds H1 to H30: - 170 - - 171 - - 172 - 8. Compound according to formula (1), where the symbols and indices used are: L is a single bond, an aromatic ring system with 6 to 40 ring atoms or an electron-rich heteroaromatic ring system with 9 to 40 ring atoms, which are bonded to one or more radicals R 0 may be substituted; R 0 is selected at each occurrence, identically or differently, from the group consisting of D, F, Cl, Br, I, CN, NO2, C(=O)R 2 , P(=O)(Ar)2, P(Ar)2, B(Ar)2, Si(Ar)3, Si(R 2 )3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 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 substituted by R 2 C=CR 2 , Si(R 2 )2, C=O, C=S, C=NR 2 , P(=O)(R 2 ), SO, SO2, NR 2, O, S or CONR 2 and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system with 5 to 40 - 173 - ring atoms, each of which is linked to one or more residues R 2 may be substituted, an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, which may be substituted with one or more radicals R 2 may be substituted, or an aralkyl or heteroaralkyl group having 5 to 40 ring atoms which may be substituted with one or more radicals R 2 may be substituted; Rx corresponds to one of the formulas (1-6) to (1-11), , * denotes the connection to L; - 174 - L1 is, at each occurrence, the same or different, a bond, O, S, C(R)2 or N-Ar; R a , R b and R crepresent a monosubstitution, a disubstitution, a trisubstitution, the maximum permissible substitution or no substitution and R a , R b and R care, independently of one another at each occurrence, D, CN, F, a non-deuterated or partially or fully deuterated alkyl group having 1 to 10 C atoms or a non-deuterated or partially or fully deuterated aromatic ring system having 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl having 9 to 40 ring atoms; V is O, S, Se, C(R)2, Si(R)3 or N-Ar3; R is, at each occurrence, identically or differently 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 one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms may be replaced by D, F, or CN or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms which is substituted with one or more substituents selected from D, F, CN,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 one or more non-adjacent CH2 groups of the alkyl group may be replaced by O or S and where one or more H atoms of the alkyl group may be replaced by D, F, or CN, where two substituents R may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted with one or more substituents R, 1 may be substituted; Ar is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms which is substituted by one or more radicals R 2 may be substituted; Ar1 is at each occurrence, identically or differently, an aromatic or electron-rich heteroaromatic ring system with 5 to 40 - 175 - ring atoms, which with one or more residues R 1may be substituted; Ar2, Ar3, identically or differently at each occurrence, is an aromatic or electron-rich heteroaromatic ring system having 5 to 40 ring atoms, which is substituted by one or more radicals R 2 may be substituted; R 1 is selected, identically or differently at each occurrence, from the group consisting of D, F, CN, Si(Aryl)3, 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 one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms may be replaced by D, F, or CN or a non-deuterated or partially or fully deuterated aromatic ring system having 6 to 40 ring atoms or a non-deuterated or partially or fully deuterated electron-rich heteroaryl having 9 to 40 ring atoms; R 2is selected, identically or differently at each occurrence, from the group consisting of D, F, CN, Si(Aryl)3, 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 one or more non-adjacent CH2 groups may be replaced by O or S and where one or more H atoms may be replaced by D, F, or CN; Aryl is, at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms which may be replaced by one or more substituents selected from D, F, CN, 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 one or more non-adjacent CH2 groups of the alkyl group may be replaced by O or S and where one or more H atoms of the alkyl group may be replaced by D, F, or CN;u, v are independently 0 or 1 at each occurrence and u+v is 1 or 2.; - 176 - 9. A compound according to claim 8, wherein L corresponds to a single bond or to one of the formulas L-1 to L-30 which is substituted with one or more radicals R 0 can be substituted: - 177 - where the dashed lines indicate the bond to Rx or to the rest of formula (1); and V1 is O, S, Se or C(R)2 and R and R 0have a meaning according to claim 8.
10. A compound according to claim 8 or 9, wherein L is a single bond.
11. A compound according to one or more of claims 8 to 10, wherein Rx corresponds to formula (1-6) or formula (1-7).
12. A mixture comprising at least one compound according to one or more of claims 8 to 11 and at least one further compound selected from the group of matrix materials, phosphorescent emitters, fluorescent emitters, and / or emitters exhibiting TADF (thermally activated delayed fluorescence).
13. A mixture comprising at least one compound according to one or more of claims 8 to 11 and at least one further matrix material, wherein the further matrix material corresponds to one or more of the compounds of formulas (6), (7), (8), (9), or (10), - 178 - where the following applies to the symbols and indices used: X is the same or different at each occurrence N or CR 6 , preferably N; L2 is at each occurrence, identically or differently, a single bond, an aromatic ring system having 5 to 20 ring atoms or a heteroaromatic ring system having 9 to 30 ring atoms, which are bonded to one or more radicals R 7 can be substituted; - 179 - R## is, identically or differently at each occurrence, D, F, CN or an aromatic ring system with 6 to 20 ring atoms, which is reacted with one or more radicals R 6 may be substituted and two adjacent substituents R## may together form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system which may be substituted with one or more radicals R 7 can be substituted; Y is at each occurrence independently the same or different N, CH, CR 7or L2-Ar5, where it is excluded that two adjacent Y simultaneously represent N; V2 is O or S; R 6 is, identically or differently at each occurrence, D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 7 may be substituted and wherein one or more non-adjacent CH2 groups are substituted by Si(R 7 )2, C=O, NR 7 , O, S or CONR 7 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 ring atoms, each of which is substituted by one or more radicals R 7 can be substituted; two radicals R 6 also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar5 *represents, identically or differently at each occurrence, independently an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which with one or more radicals R 7 may be substituted, whereby for the heteroaromatic ring system the heterocycles of formulas (A) and (B) are excluded, Ar5, identically or differently at each occurrence, independently represents an aromatic or heteroaromatic ring system with 5 to 40 - 180 - ring atoms, which with one or more residues R 7 may be substituted; R 7 is the same or different at each occurrence D, F, Cl, Br, I, N(R 8 )2, CN, NO2, OR 8 , SR 8 , Si(R 8 )3, B(OR 8 )2, C(=O)R 8 , P(=O)(R 8 )2, S(=O)R 8 , S(=O)2R 8 , OSO2R 8, a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group is each substituted by one or more radicals R 8 may be substituted, with one or more non-adjacent CH2 groups being substituted by Si(R 8 )2, C=O, NR 8 , O, S or CONR 8 may be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 ring atoms, each of which is substituted by one or more radicals R 8 may be substituted; two or more radicals R 7 form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; R 8is on each occurrence, identically or differently, H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, in particular a hydrocarbon radical, having 1 to 20 C atoms, in which one or more H atoms may also be replaced by F; b1 is 0, 1, 2, 3 or 4; b2 is 0, 1, 2 or 3.
14. Use of a compound of formula (1) according to one or more of claims 8 to 11 in an organic electronic device.
15. Use according to claim 14, wherein the compound of formula (1) is present in a hole-transporting layer, a hole-injecting layer or an electron-blocking layer.