Materials for organic light emitting devices
A hole transport region with triarylamine-based compounds and optimized HOMO levels in OLEDs addresses efficiency and lifetime challenges by improving hole transport and electron blocking, resulting in enhanced performance.
Patent Information
- Application Number
- PCT/EP2025/057543
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-03-22
- Filing Date
- 2025-03-19
- Publication Date
- 2025-09-25
AI Technical Summary
Existing organic light-emitting diodes (OLEDs) face challenges in achieving satisfactory performance in terms of efficiency, lifetime, and operating voltage, particularly due to the limitations of current hole-transporting layers, which also act as electron blockers.
The introduction of a hole transport region comprising a hole transport layer and two auxiliary layers, where the hole transport layer includes triarylamine-based compounds, and the auxiliary layers are defined by specific compounds of formula (II), optimizing the HOMO levels to enhance hole transport and electron blocking.
This configuration significantly improves OLED performance by enhancing efficiency and lifetime, with optimized HOMO levels and quantum-chemical calculations ensuring effective hole transport and electron blocking.
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Abstract
Description
[0001] Foreignfiling_text – P24-045 -1- Materials for organic light emitting devices The present application relates to an electronic device comprising a first electrode, a second electrode facing the first electrode, an interlayer between the first electrode and the second electrode comprising a hole transport region comprising at least two hole- transporting layers and an emitting layer. Electronic devices in the context of this application are understood to mean what are called organic electronic devices, which comprise organic semiconductor materials as functional materials. More particularly, these are understood to mean OLEDs (organic light-emitting diodes, organic electroluminescent devices). These are electronic devices which have one or more layers comprising organic compounds and emit light on application of electrical voltage. The construction and general principle of function of OLEDs are known to those skilled in the art. In electronic devices, especially OLEDs, there is great interest in an improvement in the performance data, especially lifetime, efficiency, operating voltage and colour purity. In these aspects, it has not yet been possible to find any entirely satisfactory solution. Hole-transporting layers in electronic devices, especially OLEDs, have a great influence on the abovementioned performance data of electronic devices. The hole-transporting layers may, as well as their hole-transporting function, also have an electron-blocking function, meaning that they block the passage of electrons from the emitting layer to the anode. In addition, the hole-transporting layers of the OLED preferably have suitable HOMO levels to efficiently enable the transport of the holes from the anode to the emitting layer. Materials for hole-transporting layers that are known in the prior art are primarily amine compounds, especially triarylamine compounds. Examples of such triarylamine compounds are spirobifluoreneamines, fluoreneamines, indenofluoreneamines, phenanthreneamines, carbazoleamines, xantheneamines, spirodihydroacridineamines, biphenylamines and combinations of these structural elements having one or more amino groups, and the person skilled in the art is aware of further structure classes. Foreignfiling_text – P24-045 -2- The present invention thus aims at providing electronic devices, more particularly Organic Light Emitting Devices (OLEDs) comprising at least two hole-transporting layers as defined below and a light emitting layer. The present invention also aims at providing suitable hole- transport materials for the hole-transport layers of an electronic device. It has now been found that, surprisingly, the devices and compounds described below are particularly suitable in the technical field of OLEDs. The devices and compounds described below lead to OLEDs having very good properties, especially in terms of efficiency, lifetime or charging response time of OLED pixels. A first object of the present application relates to an electronic device comprising: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and comprising an emitting layer, wherein: the emitting layer comprises a host material and a dopant, where the dopant is selected from fluorescent emitters and phosphorescent emitters, the interlayer further comprises a hole transport region between the emitting layer and the first electrode, the hole transport region comprises a hole transport layer, a first auxiliary layer and a second auxiliary layer, where the first auxiliary layer is located between the hole transport layer and the second auxiliary layer, and the second auxiliary layer is located between the first auxiliary layer and the emitting layer, the hole transport layer comprises a compound H selected from triarylamine-based compounds, the first auxiliary layer comprises a compound G1 selected from compounds of formula (II),
[0002] Foreignfiling_text – P24-045 -3- Formula (II) where the following applies to the symbols and indices occurring: L20, L21, L22, L23, L24are on each occurrence, identically or differently, a single bond, an aromatic ring system having 6 to 30 aromatic ring atoms or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R22; Ar22stands for an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R22; X1to X8and X1´to X8´stand on each occurrence, identically or differently, for CR20, CRAor N; where at least one of X1, X2, X3and X4is bonded to L20and stands for C; Z1to Z27stand on each occurrence, identically or differently, for CR21, CRAor N; where the symbols Z11to Z15, Z16to Z21and Z22to Z27which are bonded to an adjacent group stand for C; Foreignfiling_text – P24-045 -4- T20, T21are the same or different at each instance and are selected from single bond, O, S, NR21and C(R21)2; R20, R21, R22stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R)3, B(OR)2, N(R)2, N(Ar)2, OSO2R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non- adjacent CH2 groups may be replaced by RC=CR, C≡C, Si(R)2, Ge(R)2, Sn(R)2, C=O, C=S, C=Se, P(=O)(R), SO, SO2, O or S and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R; where two radicals R20, two radicals R21and / or two radicals R22may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R; RAstands on each occurrence, identically or differently, for F, Si(RB)3, a straight- chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals RB, where in said alkyl, alkoxy and thioalkyl groups one or more non- adjacent CH2 groups may be replaced by RBC=CRB, C≡C, Si(RB)2, Ge(RB)2, Sn(RB)2, C=O, C=S, C=Se, P(=O)(RB), SO, SO2, O or S and one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2; where two radicals RAmay form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals RB; R, RBstand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R´)3, B(OR´)2, N(R´)2, N(Ar)2, OSO2R´, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R´, where in each case one or more non- adjacent CH2groups may be replaced by R´C=CR´, C≡C, Si(R´)2, Ge(R´)2, Sn(R´)2, C=O, C=S, C=Se, P(=O)(R´), SO, SO2, O or S and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be Foreignfiling_text – P24-045 -5- substituted by one or more radicals R´; where two radicals R, two radicals RBmay form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R´; Ar is, on each occurrence, identically or differently, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case also be substituted by one or more radicals R´; R´stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, where in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic ring system having 6 to 24 aromatic ring atoms or heteroaromatic ring system having 5 to 24 aromatic ring atoms; m is 0 or 1; n is 0 or 1; p is 0 or 1; where, when m or n is 0, then the group in parentheses is absent and the two groups on either side of the group in parentheses are linked by a single bond; and the second auxiliary layer comprises a compound G2; characterized in that, in the compound of formula (II), at least one symbol selected from X1to X8, X1´to X8´or Z1to Z27stands for CRA. The definitions which follow are applicable to the chemical groups that are used in the present application. They are applicable unless any more specific definitions are given. An aryl group in the context of this invention is understood to mean either a single aromatic cycle, i.e. benzene, or a fused aromatic polycycle, for example naphthalene, phenanthrene or anthracene. A fused aromatic polycycle in the context of the present application consists of two or more single aromatic cycles fused to one another. Fusion between cycles is understood here to mean that the cycles share at least one edge with one another. An aryl Foreignfiling_text – P24-045 -6- group in the context of this invention contains 6 to 40 aromatic ring atoms. In addition, an aryl group does not contain any heteroatom as aromatic ring atom, but only carbon atoms. A heteroaryl group in the context of this invention is understood to mean either a single heteroaromatic cycle, for example pyridine, pyrimidine or thiophene, or a fused heteroaromatic polycycle, for example quinoline or carbazole. A fused heteroaromatic polycycle in the context of the present application consists of two or more single aromatic or heteroaromatic cycles that are fused to one another, where at least one of the aromatic and heteroaromatic cycles is a heteroaromatic cycle. Fusion between cycles is understood here to mean that the cycles share at least one edge with one another. A heteroaryl group in the context of this invention contains 5 to 40 aromatic ring atoms of which at least one is a heteroatom. The heteroatoms of the heteroaryl group are preferably selected from N, O and S. An aryl or heteroaryl group, each of which may be substituted by the abovementioned radicals, is especially understood to mean groups derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, triphenylene, fluoranthene, benzanthracene, benzophenanthrene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, benzimidazolo[1,2-a]benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazinimidazole, quinoxalinimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3- triazole, 1,2,4-triazole, benzotriazole, 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. An aromatic ring system in the context of this invention is a system which does not necessarily contain solely aryl groups, but which may additionally contain one or more Foreignfiling_text – P24-045 -7- nonaromatic rings fused to at least one aryl group. These nonaromatic rings contain exclusively carbon atoms as ring atoms. Examples of groups covered by this definition are tetrahydronaphthalene, fluorene and spirobifluorene. In addition, the term "aromatic ring system" includes systems that consist of two or more aromatic ring systems joined to one another via single bonds, for example biphenyl, terphenyl, 7-phenyl-2-fluorenyl, quaterphenyl and 3,5-diphenyl-1-phenyl. An aromatic ring system in the context of this invention contains 6 to 40 carbon atoms and no heteroatoms in the ring system. The definition of "aromatic ring system" does not include heteroaryl groups. A heteroaromatic ring system conforms to the abovementioned definition of an aromatic ring system, except that it must contain at least one heteroatom as ring atom. As is the case for the aromatic ring system, the heteroaromatic ring system need not contain exclusively aryl groups and heteroaryl groups, but may additionally contain one or more nonaromatic rings fused to at least one aryl or heteroaryl group. The nonaromatic rings may contain exclusively carbon atoms as ring atoms, or they may additionally contain one or more heteroatoms, where the heteroatoms are preferably selected from N, O and S. One example of such a heteroaromatic ring system is benzopyranyl. In addition, the term "heteroaromatic ring system" is understood to mean systems that consist of two or more aromatic or heteroaromatic ring systems that are bonded to one another via single bonds, for example 4,6-diphenyl-2-triazinyl. A heteroaromatic ring system in the context of this invention contains 5 to 40 ring atoms selected from carbon and heteroatoms, where at least one of the ring atoms is a heteroatom. The heteroatoms of the heteroaromatic ring system are preferably selected from N, O and S. The terms "heteroaromatic ring system" and "aromatic ring system" as defined in the present application thus differ from one another in that an aromatic ring system cannot have a heteroatom as ring atom, whereas a heteroaromatic ring system must have at least one heteroatom as ring atom. This heteroatom may be present as a ring atom of a nonaromatic heterocyclic ring or as a ring atom of an aromatic heterocyclic ring. In accordance with the above definitions, any aryl group is covered by the term "aromatic ring system", and any heteroaryl group is covered by the term "heteroaromatic ring system". Foreignfiling_text – P24-045 -8- An aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 5 to 40 aromatic ring atoms is especially understood to mean groups derived from the groups mentioned above under aryl groups and heteroaryl groups, and from biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, indenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, indenocarbazole, or from combinations of these groups. In the context of the present invention, a straight-chain alkyl group having 1 to 20 carbon atoms and a branched or cyclic alkyl group having 3 to 20 carbon atoms and an alkenyl or alkynyl group having 2 to 40 carbon atoms in which individual hydrogen atoms or CH2 groups may also be substituted by the groups mentioned above in the definition of the radicals are preferably understood to mean the methyl, ethyl, n-propyl, i-propyl, n-butyl, i- butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl or octynyl radicals. An alkoxy or thioalkyl group having 1 to 20 carbon atoms in which individual hydrogen atoms or CH2 groups may also be substituted by the groups mentioned above in the definition of the radicals is preferably understood to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, n- pentylthio, s-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2- trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio or octynylthio. The wording that two or more radicals together may form a ring, in the context of the present application, shall be understood to mean, inter alia, that the two radicals are joined to one another by a chemical bond. In addition, however, the abovementioned wording shall Foreignfiling_text – P24-045 -9- also be understood to mean that, if one of the two radicals is hydrogen, the second radical binds to the position to which the hydrogen atom was bonded, forming a ring. Preferably, the compound of formula (II) comprises at least two, three or four symbols selected from X1to X8, X1´to X8´and Z1to Z27, which stand for CRA. Preferably, the energy of the highest occupied molecular orbital of the compound H present in the hole-transport layer, HOMO (H), is: -5.25 ≤ HOMO (H) ≤ -5.00 eV More preferably: -5.20 ≤ HOMO (H) ≤ -5.05 eV Particularly preferably: -5.20 ≤ HOMO (H) ≤ -5.10 eV Preferably, the energy of the highest occupied molecular orbital of the compound G1 present in the first auxiliary layer, HOMO (G1), is: -5.30 ≤ HOMO (G1) ≤ -5.05 eV More preferably: -5.25 ≤ HOMO (G1) ≤ -5.10 eV Particularly preferably: -5.20 ≤ HOMO (G1) ≤ -5.10 eV Preferably, the energy of the highest occupied molecular orbital of the compound G2 present in the first auxiliary layer, HOMO (G2), is: -5.50 ≤ HOMO (G2) ≤ -5.15 eV More preferably: -5.40 ≤ HOMO (G2) ≤ -5.20 eV Particularly preferably: -5.40 ≤ HOMO (G2) ≤ -5.25 eV The energy levels of molecular orbitals, like the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), and of the lowest triplet state T1 or of the lowest excited singlet state S1 of materials are determined via quantum-chemical calculations. For all quantum-chemical calculations, the Gaussian program package is used (Gaussian16). The singlet ground state geometries are optimized at the B3LYP / 6-31G(d) level of theory. Subsequently, TD-DFT singlet and triplet excitation energies (vertical transitions) are computed using the optimized ground state geometry and the same method Foreignfiling_text – P24-045 -10- (B3LYP / 6-31G(d)). Default settings for SCF and geometry convergence are employed. For structures containing heavy metal atoms the calculation is carried out analogously to the above-described method for the organic substances, with the difference that the "LanL2DZ" base set is used for the metal atom and the "6-31G(d)" base set is used for the ligands. The energy calculation gives the HOMO energy level HEh or LUMO energy level LEh in hartree units. The HOMO and LUMO energy levels in electron volts calibrated with reference to cyclic voltammetry measurements are determined therefrom as follows: HOMO(eV) = (HEh*0.90603) - 0.84836 LUMO(eV) = (LEh*0.99687) - 0.72445 For the purposes of this application, these values are to be regarded as HOMO and LUMO energy levels respectively of the materials. The lowest triplet state T1 is defined as the energy of the triplet state having the lowest energy which arises from the quantum-chemical calculation described. The lowest excited singlet state S1 is defined as the energy of the excited singlet state having the lowest energy which arises from the quantum-chemical calculation described. The method described herein is independent of the software package used and always gives the same results. Examples of frequently used programs for this purpose are "Gaussian16" (Gaussian Inc.) and Q Chem 4.1 (Q Chem, Inc.). With regard to the indices m, n and p in formula (II), following combinations are preferred: 1) p = 0, m = 1 2) p = 0, m = 0 3) p = 1, n = 0, m = 0 4) p = 1, n = 0, m = 1 5) p = 1, n = 1, m = 0 6) p = 1, n = 1, m = 1 As mentioned above, when m or n is 0, then the group in parentheses is absent and the two groups on either side of the group in parentheses are linked by a single bond. Furthermore, when p is 0, then the group in parentheses is absent. For example, the combination 2), where p = 0 and m = 0 leads to the compound of formula (II-0): Foreignfiling_text – P24-045 -11- where the symbols X1to X8, X1´to X8´, T20, T21, L20, L21, L22, Ar22, Z1to Z5and Z11to Z15have the same meaning as above, and where the compound of formula (II-0) comprises at least one symbol selected from X1to X8, X1´to X8´, Z1to Z5and Z11to Z15, which stands for CRA. Preferably, the compound of formula (II-0) comprises at least two, three or four symbols selected from X1to X8, X1´to X8´, Z1to Z5and Z11to Z15, which stand for CRA. Preferably, in formula (II-0), one of the following conditions applies: (0-1) one or two symbols selected from Z1to Z5stand(s) for CRA; (0-2) one or two symbols selected from Z11to Z15stand(s) for CRA; (0-3) one symbol selected from Z1to Z5and one symbol selected from Z11to Z15stand for CRA; (0-4) two symbols selected from Z1to Z5and two symbols selected from Z11to Z15stand for CRA; (0-5) one or two symbols selected from X1to X4stand(s) for CRA; (0-6) one or two symbols selected from X5to X8stand(s) for CRA; (0-7) one symbol selected from X1to X4and one symbol selected from X5to X8stand for CRA; (0-8) two symbols selected from X1to X4and two symbols selected from X5to X8stand for CRA; (0-9) one or two symbols selected from X1´to X4´stand(s) for CRA; (0-10) one or two symbols selected from X5´to X8´stand(s) for CRA; Foreignfiling_text – P24-045 -12- (0-11) one symbol selected from X1´to X4´and one symbol selected from X5´to X8´stand for CRA; (0-12) two symbols selected from X1´to X4´and two symbols selected from X5´to X8´stand for CRA. The combination 4), where p = 1, n = 0 and m = 0 leads to the compound of formula (II-1): where the symbols X1to X8, X1´to X8´, T20, T21, L20, L21, L22, Ar22and Z1to Z15have the same meaning as above, and where the compound of formula (II-1) comprises at least one symbol selected from X1to X8, X1´to X8´, Z1to Z15, which stands for CRA. Preferably, the compound of formula (II-1) comprises at least two, three or four symbols selected from X1to X8, X1´to X8´, Z1to Z15, which stand for CRA. Preferably, in formula (II-1), one of the following conditions applies: (1-1) one or two symbols selected from Z1to Z5stand(s) for CRA; (1-2) one or two symbols selected from Z6to Z10stand(s) for CRA; (1-3) one symbol selected from Z1to Z5and one symbol selected from Z6to Z10stand for CRA; (1-4) two symbols selected from Z1to Z5and two symbols selected from Z6to Z10stand for CRA; (1-5) one or two symbols selected from X1to X4stand(s) for CRA; Foreignfiling_text – P24-045 -13- (1-6) one or two symbols selected from X5to X8stand(s) for CRA; (1-7) one symbol selected from X1to X4and one symbol selected from X5to X8stand for CRA; (1-8) two symbols selected from X1to X4and two symbols selected from X5to X8stand for CRA; (1-9) one or two symbols selected from X1´to X4´stand(s) for CRA; (1-10) one or two symbols selected from X5´to X8´stand(s) for CRA; (1-11) one symbol selected from X1´to X4´and one symbol selected from X5´to X8´stand for CRA; (1-12) two symbols selected from X1´to X4´and two symbols selected from X5´to X8´stand for CRA. Preferably, the radical RAstands on each occurrence, identically or differently, for a straight- chain alkyl, alkoxy or thioalkyl group having 1 to 10, preferably 1 to 6, more preferbaly 1 to 4 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 10, preferably 3 to 6 C atoms, each of which may be substituted by one or more radicals RB, where in said alkyl, alkoxy and thioalkyl groups one or more H atoms may be replaced by D or F; and where two radicals RAmay form an aliphatic ring system together, which may be substituted by one or more radicals RB. Suitable examples of radicals RAare the groups (R-1) to (R-35) as depicted in the table below: Foreignfiling_text – P24-045 -14- Where the dashed bond indicates the connection of the group RAto the structure of formula (II) and where the unsubstituted positions in the structures of formulae (R-1) to (R-35), can also be substituted by D or F. When two radicals RAform an aliphatic ring system together, then they preferably form an aliphatic ring system of one of the formulae (RA-1) to (RA-7) below: Foreignfiling_text – P24-045 -15- (RA-5) (RA-6) (RA-7) where G is the same or different at each instance and is C(RB)2, (RB)2C-C(RB)2, (RB)C=C(RB), NRB, NAr, O or S, preferably G stands for C(RB)2or (RB)2C-C(RB)2; RBand Ar have the same meaning as above; and where the dashed bonds represent the connection of the ring formed by two radicals RAto the compound G1. Preferably, RBstands on each occurrence, identically or differently, for H, D, F, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 10, preferably 1 to 6 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 10 preferably 3 to 6 C atoms, where one or more H atoms in the alkyl, alkoxy or thioalkyl groups above may be replaced by D, F or CN, an aromatic ring system having 6 to 18 aromatic ring atoms or heteroaromatic ring system having 6 to 18 aromatic ring atoms, which may in each case be substituted by one or more radicals R´; where two radicals RBmay form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R´. Preferably, the compound G1 is selected from compounds of formula (II-1). More preferably, the compound of formula (II-1) is selected from the compounds of formula (II-2), Foreignfiling_text – P24-045 -16- Formula (II-2) where the symbols X1to X8, X1´to X8´, T20, T21, L20, L21, L22, Ar22, Z1to Z15have the same meaning as above and where the compound of formula (II-2) comprises at least two, three or four symbols selected from X1to X8, X1´to X8´and Z1to Z15, which stand for CRA. Very preferably, the compound of formula (II-1) is selected from the compounds of formula (II-3), Formula (II-3) Foreignfiling_text – P24-045 -17- where the symbols X1to X8, X1´to X8´, T20, T21, L20, L21, L22, Ar22, Z1to Z15have the same meaning as above, and where the compound of formula (II-3) comprises at least two, three or four symbols selected from X1to X8, X1´to X8´and Z1to Z15, which stand for CRA. Particularly preferably, the compound of formula (II-1) is selected from compounds of one of the formulae (II-3-1) to (II-3-7), Formula (II-3-2) Foreignfiling_text – P24-045 -18- Foreignfiling_text – P24-045 -19- Formula (II-3-5) Formula (II-3-7) where the symbols X1to X8, X1´to X8´, T20, T21, L20, L21, L22, Ar22, Z1to Z5, Z6to Z10, Z11, Z12, Z13and RAhave the same meaning as above. Preferably, T20, T21are the same or different at each instance and are selected from single bond, O and C(R21)2, more preferably from single bond and O. In accordance with a preferred embodiment, T20and T21both stand for a single bond. In accordance with another preferred embodiment, T20and T21both stand for O. In accordance with another preferred embodiment, T20stands for O and T21stands for a single bond. Foreignfiling_text – P24-045 -20- In accordance with another preferred embodiment, T20stands for a single bond and T21stands for O. Preferably, L20, L21, L22are, identically or differently, a single bond or are selected from aromatic ring systems having 6 to 20, preferably 6 to 12 aromatic ring atoms or heteroaromatic ring system having 5 to 20, preferably 5 to 12 aromatic ring atoms, which may be substituted by one or more radicals R22. More preferably, L20, L21, L22are, identically or differently, a single bond or are selected from the group consisting of benzene, biphenyl, terphenyl, naphthyl, fluorenyl, indenofluorenyl, spirobifluorenyl, dibenzofuranyl and dibenzothiophenyl, and carbazolyl, which may each be substituted by one or more radicals R22. More preferably, L20, L21, L22are, identically or differently, a single bond or are selected from the group consisting of benzene, biphenyl, terphenyl, naphthyl, dibenzofuranyl and dibenzothiophenyl, and carbazolyl, which may be substituted by one or more radicals R22. Even more preferably, L20, L21, L22stand for a single bond or benzene, biphenyl or terphenyl, which may be substituted by one or more radicals R22. Preferably, Ar22stands for an aromatic ring system having 6 to 30, preferably 6 to 25, more preferably 6 to 18 aromatic ring atoms or heteroaromatic ring system having 5 to 30, preferably 6 to 25, more preferably 6 to 18 aromatic ring atoms, which may be substituted by one or more radicals R22. More preferably, Ar22is selected from the group consisting of phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, fluorenyl, especially 9,9'-dimethylfluorenyl and 9,9'- diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, dibenzofuranyl, dibenzothiophenyl, benzofuranyl, benzothiophenyl, indolyl, quinolinyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl and triazinyl, and combinations of two or three of these groups, which are each optionally substituted by one or more radicals R22. Particularly preferably, Ar22is selected from the group consisting of phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, fluorenyl, especially 9,9'-dimethylfluorenyl and 9,9'- diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, dibenzofuranyl, dibenzothiophenyl, benzofuranyl, benzothiophenyl, benzofused dibenzofuranyl, benzofused dibenzothiophenyl, naphthyl-substituted phenyl, fluorenyl-substituted phenyl, spirobifluorenyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzothiophenyl- Foreignfiling_text – P24-045 -21- substituted phenyl, pyridyl-substituted phenyl, pyrimidyl-substituted phenyl, and triazinyl- substituted phenyl, each of which may optionally be substituted by one or more radicals R22. Example of very suitable groups Ar22are the groups (Ar-1) to (Ar-276) depicted in the following table: Foreignfiling_text – P24-045 -22- Foreignfiling_text – P24-045 -23- Foreignfiling_text – P24-045 -24- Foreignfiling_text – P24-045 -25- Foreignfiling_text – P24-045 -26- Foreignfiling_text – P24-045 -27- Foreignfiling_text – P24-045 -28- Foreignfiling_text – P24-045 -29- Foreignfiling_text – P24-045 -30- Foreignfiling_text – P24-045 -31- Foreignfiling_text – P24-045 -32- Foreignfiling_text – P24-045 -33- Foreignfiling_text – P24-045 -34- Foreignfiling_text – P24-045 -35- Foreignfiling_text – P24-045 -36- Foreignfiling_text – P24-045 -37- where the dotted line represents the bond to the adjacent group, and where the groups (Ar- 1) to (Ar-276) may bear one or more substituents R other than H at the positions shown as being unsubstituted, and preferably bear H or D at the positions shown as being unsubstituted. Preferably, R20, R21, R22stand on each occurrence, identically or differently, for H, D, F, CN, Si(R)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40, preferably 1 to 20, more preferably 1 to 10 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group hav- ing 3 to 40, preferably 3 to 20, more preferably 3 to 10 C atoms, each of which may be substituted by one or more radicals R, where one or more H atoms in the alkyl, alkoxy or thioalkyl groups above may be replaced by D, F or CN, an aromatic ring system having 6 to 40, preferably 6 to 30, more preferably 6 to 24, even more preferably 6 to 18 aromatic ring atoms or heteroaromatic ring system having 5 to 40, preferably 5 to 30, more preferably 5 to 24, even more preferably 5 to 18 aromatic ring atoms, which may in each case be sub- stituted by one or more radicals R; where two radicals R20, two radicals R21and / or two radicals R22may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R. Preferably, R stands on each occurrence, identically or differently, for H, D, F, CN, Si(R´)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20, preferably 1 to 10 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 20, preferably 3 to 10 C atoms, each of which may be substituted by one or more radicals R´, where one or more H atoms may be replaced by D, F or CN, an aromatic ring system having 6 to 24, preferably 6 to 18 aromatic ring atoms or heteroaromatic ring system having 6 to 24, preferably 6 to 18 aromatic ring atoms, which may in each case be substituted by one or more radicals R´; where two radicals R may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R´. Preferably, Ar is, on each occurrence, identically or differently, an aromatic ring system having 6 to 30, preferably 6 to 24, more preferably 6 to 18 aromatic ring atoms or heteroaromatic ring system having 6 to 30, preferably 6 to 24, more preferably 6 to 18 Foreignfiling_text – P24-045 -38- aromatic ring atoms, which may in each case also be substituted by one or more radicals R´. Preferably, R´stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 6 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 6 C atoms, where one or more H atoms may be replaced by D or F, or an aromatic ring system having 6 to 18 aromatic ring atoms or heteroaromatic ring system having 6 to 18 aromatic ring atoms. In accordance with a preferred embodiment, the compound G1 is a deuterated compound. The term “deuterated compound” refers here to a compound in which deuterium is present in at least 100 times the natural abundance level. A higher deuteration degree than in nature can be achieved by using building blocks which have been previously enriched with deuterium via a deuteration method or by submitting a compound to a deuteration method. In accordance with the present invention, the deuteration degree corresponds to the number of deuterium atoms in a compound on the total number of deuterium atoms and protium atoms in the compound in %, as follows: Deuteration degree (%) = (ND * 100) / (NP + ND) where: ND is the number of deuterium atoms in the compound NP is the number of deuterium and protium atoms in the compounds Unless specified otherwise, the term hydrogen in the present invention design the protium isotope of hydrogen, which accounts for more that 99.98% of the natural occurring hydrogen in the oceans. Preferably, the compound G1 has a deuteration degree higher than 20%, 40%, 60% or 80%. Suitable examples of the compound G1 are depicted in the following table: Foreignfiling_text – P24-045 -39- In a general way, the compounds G1 disclosed in the table above might be deuterated, even if not explicitly disclosed in the table. Foreignfiling_text – P24-045 -40- Processes for synthesis of the compounds of the formula (II) are known in the prior art, especially in the publications WO2012 / 034627, WO2022 / 096172 and WO2022 / 129117. According to the present invention, the hole transport layer comprises a compound H selected from triarylamine-based compounds. Preferably, the compound H is selected from compounds of formulae (IA), (IB) and (IC), Formula (IC) where the following applies to the symbols and indices occurring: Foreignfiling_text – P24-045 -41- L10, L11, L12are on each occurrence, identically or differently, a single bond, an aromatic ring system having 6 to 30 aromatic ring atoms or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R12; Ar11, Ar12are on each occurrence, identically or differently, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R12; X stands on each occurrence, identically or differently, for CR10or N; or X stands for C when it is bonded to an adjacent group; T10, T11, T12, T13, T14are the same or different at each instance and are selected from a single bond, O, S, NRN, and C(RC)2; with the proviso that T12, T13do not both stand for a single bond; RCstands on each occurrence, identically or differently, for H, D, F, Si(R)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40, preferably 1 to 20, more preferably 1 to 10 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40, preferably 3 to 20, more preferably 3 to 10 C atoms, each of which may be substituted by one or more radicals R, where one or more H atoms may be replaced by D or F, an aromatic ring system having 6 to 40, preferably 6 to 30, more preferably 6 to 18 aromatic ring atoms or heteroaromatic ring system having 5 to 40, preferably 6 to 30, more preferably 6 to 18 aromatic ring atoms, which may in each case be substituted by one or more radicals R; where two radicals RCmay form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R; RNstands for H, D, F, a straight-chain alkyl group having 1 to 40, preferably 1 to 30, more preferably 1 to 20 C atoms or branched or a cyclic alkyl group having 3 to 40, preferably 3 to 20, more preferably 3 to 10 C atoms, each of which may be substituted by one or more radicals R, where one or more H atoms may be replaced by D or F, an aromatic ring system having 6 to 40, preferably 6 to 30, more preferably 6 to 18 aromatic ring atoms or heteroaromatic ring system having 5 to 40, preferably 6 to 30, more preferably 6 to 18 aromatic ring atoms, which may in each case be substituted by one or more radicals R; Foreignfiling_text – P24-045 -42- R10, R11, R12stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R)3, B(OR)2, N(R)2, N(Ar)2, OSO2R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non- adjacent CH2 groups may be replaced by RC=CR, C≡C, Si(R)2, Ge(R)2, Sn(R)2, C=O, C=S, C=Se, P(=O)(R), SO, SO2, O or S and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R; where two radicals R10, two radicals R11and / or two radicals R12may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R; where R has the same definition as above. More preferably, the compound H is selected from compounds of formulae (IA-1), (IA-2), (IA-3), (IB-1), (IB-2), (IB-3) and (IC-1), Formula (IA-2) Foreignfiling_text – P24-045 -43- Formula (IB-3) Foreignfiling_text – P24-045 -44- Formula (IC-1) where the symbols X, RC, RN, L10, L11, L12, Ar11and Ar12have the same meaning as above. Among the compounds of formulae (IA-1), (IA-2), (IA-3), (IB-1), (IB-2), (IB-3) and (IC-1), the compounds of formulae (IA-1), (IA-2) and (IB-2) are preferred. Preferably, Ar11and Ar12stand on each occurrence, identically or differently, for an aromatic ring system having 6 to 30, preferably 6 to 25, more preferably 6 to 18 aromatic ring atoms or heteroaromatic ring system having 5 to 30, preferably 6 to 25, more preferably 6 to 18 aromatic ring atoms, which may be substituted by one or more radicals R12. More preferably, Ar11, Ar12are on each occurrence, identically or differently, selected from the group consisting of phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, fluorenyl, especially 9,9'-dimethylfluorenyl and 9,9'-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, dibenzofuranyl, dibenzothiophenyl, benzofuranyl, benzothiophenyl, indolyl, quinolinyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl and triazinyl, and combinations of two or three of these groups, which are each optionally substituted by one or more radicals R12. Particularly preferably, Ar11and Ar12are on each occurrence, identically or differently, selected from the group consisting of phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, fluorenyl, especially 9,9'-dimethylfluorenyl and 9,9'-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, dibenzofuranyl, dibenzothiophenyl, benzofuranyl, benzothiophenyl, benzofused dibenzofuranyl, benzofused dibenzothiophenyl, naphthyl- substituted phenyl, fluorenyl-substituted phenyl, spirobifluorenyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzothiophenyl-substituted phenyl, pyridyl-substituted Foreignfiling_text – P24-045 -45- phenyl, pyrimidyl-substituted phenyl, and triazinyl-substituted phenyl, each of which may optionally be substituted by one or more radicals R12. Suitable groups Ar11and Ar12are the groups (Ar-1) to (Ar-276) as depicted above. Particularly preferably, the compound H is selected from compounds of formulae (IA-1-1) to (IA-3-2), (IB-1-1) to (IB-3-2), (IC-1-1) and (IC-1-2), Formula (IA-1-2) Foreignfiling_text – P24-045 -46- Formula (IA-3-1) Foreignfiling_text – P24-045 -47- Formula (IB-1-2) Foreignfiling_text – P24-045 -48- Formula (IB-3-1) Foreignfiling_text – P24-045 -49- where the symbols X, RC, RN, L10, L11, L12and Ar11have the same meaning as above and: A1is equal to C(RC)2, O, S or equal to Foreignfiling_text – P24-045 -50- , where the dashed lines represent the bonds emanating from the group A1; Y stands on each occurrence, identically or differently, for CR10or N; or Y stands for C when it is bonded to the group L12, where R10has the same meaning as above. Among the compounds of formulae (IA-1-1) to (IA-3-2), (IB-1-1) to (IB-3-2), (IC-1-1) and (IC-1-2), the compounds of formulae (IA-1-1), (IA-1-2), (IA-2-1), (IA-2-2), (IB-2-1) and (IB-2- 2) are preferred. Preferably, L10, L11, L12are, identically or differently, a single bond or are selected from aromatic ring systems having 6 to 20, preferably 6 to 12 aromatic ring atoms or heteroaromatic ring system having 5 to 20, preferably 5 to 12 aromatic ring atoms, which may be substituted by one or more radicals R12. More preferably, L10, L11, L12are, identically or differently, a single bond or are selected from the group consisting of benzene, biphenyl, terphenyl, naphthyl, fluorenyl, indenofluorenyl, spirobifluorenyl, dibenzofuranyl and dibenzothiophenyl, and carbazolyl, which may each be substituted by one or more radicals R12. More preferably, L10, L11, L12are, identically or differently, a single bond or are selected from the group consisting of benzene, biphenyl, terphenyl, naphthyl, dibenzofuranyl and dibenzothiophenyl, and carbazolyl, which may be substituted by one or more radicals R12. Even more preferably, L10, L11, L12stand for a single bond or benzene, biphenyl or terphenyl, which may be substituted by one or more radicals R12. Preferably, R10, R11, R12stand on each occurrence, identically or differently, for H, D, F, CN, Si(R)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40, preferably 1 to 20, more preferably 1 to 10 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group hav- ing 3 to 40, preferably 3 to 20, more preferably 3 to 10 C atoms, each of which may be substituted by one or more radicals R, where one or more H atoms in the alkyl, alkoxy or thioalkyl groups above may be replaced by D, F or CN, an aromatic ring system having 6 to 40, preferably 6 to 30, more preferably 6 to 24, even more preferably 6 to 18 aromatic ring atoms or heteroaromatic ring system having 5 to 40, preferably 5 to 30, more preferably 5 Foreignfiling_text – P24-045 -51- to 24, even more preferably 5 to 18 aromatic ring atoms, which may in each case be sub- stituted by one or more radicals R; where two radicals R10, two radicals R11and / or two radicals R12may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R. In accordance with a preferred embodiment, the compound H is a deuterated compound. Preferably, the compound H has a deuteration degree higher than 20%, 40%, 60% or 80%. Examples of the compound H are depicted in the following table: Foreignfiling_text – P24-045 -52- Foreignfiling_text – P24-045 -53- Foreignfiling_text – P24-045 -54- Foreignfiling_text – P24-045 -55- In a general way, the compounds H disclosed in the table above might be deuterated, even if not explicitly disclosed in the table. Processes for synthesis of the compound H are known in the prior art, especially in the publications cited in the table below: Preferably, the hole transport layer comprising the compound H is an undoped layer, which means that the hole transport layer is not p-doped, i.e. the material of the hole transport layer is not doped with p-dopants. Foreignfiling_text – P24-045 -56- According to the present invention, the second auxiliary layer comprises a compound G2. Preferably, the compound G2 is selected from compounds of formulae (IIIA), (IIIB), (IIIC), (IIID), (IIIE) and (IIIF), Foreignfiling_text – P24-045 -57- where where the following applies to the symbols occurring: L30, L31, L32are on each occurrence, identically or differently, a single bond, an aromatic ring system having 6 to 30 aromatic ring atoms or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R32; Foreignfiling_text – P24-045 -58- Ar30, Ar31, Ar32are on each occurrence, identically or differently, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R32; V stands on each occurrence, identically or differently, for CR30or N; or V stands for C when it is bonded to the group L30; T30, T31, T32, T33, T34, T35are the same or different at each instance and are selected from a single bond, O, S, NRN, and C(RC)2; with the proviso that T32, T33do not both stand for a single bond; T36, T37are the same or different at each instance and are selected from O, S, NRN, and C(RC)2; R30, R31, R32stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R)3, B(OR)2, N(R)2, N(Ar)2, OSO2R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non- adjacent CH2 groups may be replaced by RC=CR, C≡C, Si(R)2, Ge(R)2, Sn(R)2, C=O, C=S, C=Se, P(=O)(R), SO, SO2, O or S and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R; where two radicals R30, two radicals R31and / or two radicals R32may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R; and R, RCand RNhave the same definition as above. More preferably, the compound G2 is selected from compounds of formulae (IIIA-1) to (IIIA- 4), (IIIB), (IIIC-1) to (IIIC-3), (IIID-1), (IIIE-1) and (IIIF-1), Foreignfiling_text – P24-045 -59- Formula (IIIA-4) Foreignfiling_text – P24-045 -60- Formula (IIIC-3) Foreignfiling_text – P24-045 -61- Formula (IIIF-1) where the symbols V, RC, RN, L30, L31, L32, Ar30, Ar31and Ar32have the same meaning as above. Among the compounds of formulae (IIIA-1) to (IIIA-4), (IIIB), (IIIC-1) to (IIIC-3), (IIID-1), (IIIE-1) and (IIIF-1), the compounds of formulae (IIIA-1) to (IIIA-4), (IIIC-1), (IIIC-3) and (IIID- 1) are preferred. Foreignfiling_text – P24-045 -62- Preferably, Ar31and Ar32stand on each occurrence, identically or differently, for an aromatic ring system having 6 to 30, preferably 6 to 25, more preferably 6 to 18 aromatic ring atoms or heteroaromatic ring system having 5 to 30, preferably 6 to 25, more preferably 6 to 18 aromatic ring atoms, which may be substituted by one or more radicals R32. More preferably, Ar30, Ar31, Ar32are on each occurrence, identically or differently, selected from the group consisting of phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, fluorenyl, especially 9,9'-dimethylfluorenyl and 9,9'-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, dibenzofuranyl, dibenzothiophenyl, benzofuranyl, benzothiophenyl, indolyl, quinolinyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl and triazinyl, and combinations of two or three of these groups, which are each optionally substituted by one or more radicals R32. Particularly preferably, Ar30, Ar31and Ar32are on each occurrence, identically or differently, selected from the group consisting of phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, fluorenyl, especially 9,9'-dimethylfluorenyl and 9,9'-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, dibenzofuranyl, dibenzothiophenyl, benzofuranyl, benzothiophenyl, benzofused dibenzofuranyl, benzofused dibenzothiophenyl, naphthyl- substituted phenyl, fluorenyl-substituted phenyl, spirobifluorenyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzothiophenyl-substituted phenyl, pyridyl-substituted phenyl, pyrimidyl-substituted phenyl, and triazinyl-substituted phenyl, each of which may optionally be substituted by one or more radicals R32. Suitable groups Ar30, Ar31and Ar32are the groups (Ar-1) to (Ar-276) as depicted above. Even more preferably, the compound G2 is selected from compounds of formulae (IIIA-1-1) to (IIIA-4-2), (IIIB-1), (IIIB-2), (IIIC-1-1) to (IIIC-3-2), (IIID-1-1), (IIID-1-2), (IIIE-1-1), (IIIE-1- 2), (IIIF-1-1) and (IIIF-1-2), Foreignfiling_text – P24-045 -63- Formula (IIIA-2-1) Foreignfiling_text – P24-045 -64- Formula (IIIA-3-2) Foreignfiling_text – P24-045 -65- Formuöa (IIIA-4-2)
[0003] Foreignfiling_text – P24-045 -66- Formula (IIIB-2) Foreignfiling_text – P24-045 -67- Formula (IIIC-2-1) Foreignfiling_text – P24-045 -68- Formula (IIIC-3-2) Foreignfiling_text – P24-045 -69- Formula (IIIE-1-1) Foreignfiling_text – P24-045 -70- Formula (IIIF-1-2) where the symbols V, RC, RN, L30, L31, L32, Ar30and Ar31have the same meaning as above, and where: Foreignfiling_text – P24-045 -71- A2is equal to C(RC)2, O, S or equal to , where the dashed lines represent the bonds emanating from the group A2; W stands on each occurrence, identically or differently, for CR30or N; or Y stands for C when it is bonded to the group L32. In accordance with a preferred embodiment, the compound G2 is selected from compounds of formulae (IIIA-1-1) to (IIIA-4-2), (IIIB-1), (IIIB-2), (IIIC-1-1) to (IIIC-3-2), (IIID-1-1), (IIID-1- 2), (IIIE-1-1), (IIIE-1-2), (IIIF-1-1) and (IIIF-1-2), where at least one, two three or four groups selected from V or W stand for CR30, where R30stands for a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40, preferably 1 to 20, more preferably 1 to 10 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40, preferably 3 to 20, more preferably 3 to 10 C atoms, each of which may be substituted by one or more radicals R, where one or more H atoms may be replaced by D or F, an aromatic ring system having 6 to 40, preferably 6 to 30, more preferably 6 to 18 aromatic ring atoms or heteroaromatic ring system having 5 to 40, preferably 6 to 30, more preferably 6 to 18 aromatic ring atoms, which may in each case be substituted by one or more radicals R. Preferably, L30, L31, L32are, identically or differently, a single bond or are selected from aromatic ring systems having 6 to 20, preferably 6 to 12 aromatic ring atoms or heteroaromatic ring system having 5 to 20, preferably 5 to 12 aromatic ring atoms, which may be substituted by one or more radicals R32. More preferably, L30, L31, L32are, identically or differently, a single bond or are selected from the group consisting of benzene, biphenyl, terphenyl, naphthyl, fluorenyl, indenofluorenyl, spirobifluorenyl, dibenzofuranyl and dibenzothiophenyl, and carbazolyl, which may each be substituted by one or more radicals R32. More preferably, L30, L31, L32are, identically or differently, a single bond or are selected from the group consisting of benzene, biphenyl, terphenyl, naphthyl, dibenzofuranyl and dibenzothiophenyl, and carbazolyl, which may be substituted by one or more radicals R32. Foreignfiling_text – P24-045 -72- Even more preferably, L30, L31, L32stand for a single bond or benzene, biphenyl or terphenyl, which may be substituted by one or more radicals R32. Preferably, R30, R31, R12stand on each occurrence, identically or differently, for H, D, F, CN, Si(R)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40, preferably 1 to 20, more preferably 1 to 10 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group hav- ing 3 to 40, preferably 3 to 20, more preferably 3 to 10 C atoms, each of which may be substituted by one or more radicals R, where one or more H atoms in the alkyl, alkoxy or thioalkyl groups above may be replaced by D, F or CN, an aromatic ring system having 6 to 40, preferably 6 to 30, more preferably 6 to 24, even more preferably 6 to 18 aromatic ring atoms or heteroaromatic ring system having 5 to 40, preferably 5 to 30, more preferably 5 to 24, even more preferably 5 to 18 aromatic ring atoms, which may in each case be sub- stituted by one or more radicals R; where two radicals R30, two radicals R31and / or two radicals R32may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R. In accordance with a preferred embodiment, the compound G2 is a deuterated compound. Preferably, the compound G2 has a deuteration degree higher than 20%, 40%, 60% or 80%. Preferably, the electronic device according to the invention comprises at least one deuterated compound selected compound G1, compound G2 and compound H. Examples of the compound G2 are depicted in the following table:
[0004] Foreignfiling_text – P24-045 -73- Foreignfiling_text – P24-045 -74- 10 15 20 25 In a general way, the compounds G2 disclosed in the table above might be deuterated, even if not explicitly disclosed in the table. 30 Processes for synthesis of the compounds G2 are known in the prior art, especially in the publications cited in the table below: 35 Foreignfiling_text – P24-045 -75- In accordance with a preferred embodiment, the hole transport region further comprises a hole injection layer between the first electrode and the hole transport layer comprising the compound H. In the present application, the hole transport layer comprising the compound H is called HTL and the hole injection layer between the first electrode and the hole transport layer HTL is called HIL. Both layers are hole-transporting layers. Preferably, the hole transport layer HTL consists of a compound H as defined above. Preferably, the hole injection layer is in direct contact with the first electrode, and more preferably in direct contact with the hole transport layer HTL. The hole injection layer HIL preferably conforms to one of the following embodiments: a) it contains a triarylamine and at least one p-dopant; or b) it contains a single electron- deficient material (electron acceptor). In a preferred embodiment of embodiment b), the electron-deficient material is a hexaazatriphenylene derivative as described in US 2007 / 0092755. It is further preferable that the hole injection layer HIL contains a compound Foreignfiling_text – P24-045 -76- of formula (IA), (IB) or (IC) as defined above and a p-dopant. In a preferred embodiment, the hole injection layer HIL comprises a compound of formula (IA), (IB) or (IC) as the main component, which is doped by a p-dopant. p-Dopants according to the present application are organic electron acceptor compounds. p-Dopants used are preferably those organic electron acceptor compounds capable of oxidizing one or more of the other compounds in the p-doped layer. Particularly preferred as p-dopants are quinodimethane compounds, azaindenofluorenediones, azaphenalenes, azatriphenylenes, I2, metal halides, preferably transition metal halides, metal oxides, preferably metal oxides comprising at least one transition metal or a metal from main group 3, and transition metal complexes, preferably complexes of Cu, Co, Ni, Pd and Pt with ligands containing at least one oxygen atom as binding site. Preference is further given to transition metal oxides as dopants, preferably oxides of rhenium, molybdenum and tungsten, more preferably Re2O7, MoO3, WO3 and ReO3. Still further preference is given to complexes of bismuth in the (III) oxidation state, more particularly bismuth(III) complexes with electron-deficient ligands, more particularly carboxylate ligands. The p-dopants are preferably in substantially homogeneous distribution in the p-doped layers. This can be achieved, for example, by co-evaporation of the p-dopant and the hole transport material matrix. The p-dopant is preferably present in a proportion of 1% to 10% in the p-doped layer. Preferred p-dopants are especially the compounds shown in WO2021 / 104749 on pages 99- 100 as (D-1) to (D-14). The p-dopants are preferably in substantially homogeneous distribution in the p-doped layers. This can be achieved, for example, by coevaporation of the p-dopant and the hole transport material matrix. Preferably, the hole transport layer HTL is in direct contact with the first auxiliary layer. Preferably, the first auxiliary layer consists of a compound G1 as described above. Foreignfiling_text – P24-045 -77- In accordance with a preferred embodiment, the first auxiliary layer is in direct contact with the second auxiliary layer, and the second auxiliary layer is in direct contact with the emitting layer. The hole transport region comprises in this sequence (from the first electrode to the emitting layer): - optionally a hole injection layer HIL, - a hole transport layer HTL comprising a compound H as defined above, - a first auxiliary layer AUX1 comprising a compound G1, - a second auxiliary layer AUX2 comprising a compound G2 as defined above. Layers HIL, HTL, AUX1 and AUX2 are all hole-transporting layers. Hole-transporting layers are understood here to mean all layers disposed between anode and emitting layer, preferably hole injection layers, hole transport layers, and electron blocker layers. A hole injection layer, like HIL, is understood here to mean a layer that preferably directly adjoins the anode. A hole transport layer, like HTL, is understood here to mean a layer which is between the anode and emitting layer but preferably does not directly adjoin the anode, and preferably does not directly adjoin the emitting layer either. An electron blocker layer is understood here to mean a layer which is between the anode and emitting layer and directly adjoins the emitting layer and preferably has a high-energy LUMO and hence prevents electrons from exiting from the emitting layer. The electron blocking layer may comprise one or more electron blocking layers. Layers AUX1 and AUX2 are preferably electron blocking layers. The hole transport layer HTL preferably has a thickness of 40 to 170 nm, more preferably of 50 to 145 nm. The first auxiliary layer AUX1 and the second auxiliary layer AUX2 are preferably electron blocker layers. Besides the layers HIL, HTL, AUX1 and AUX2, the hole tansport region may comprise further hole transport layers. The emitting layer comprises a host and a dopant selected from phosphorescent emitters. Foreignfiling_text – P24-045 -78- Preferably, the emitting layer comprises a host material, where the host material comprises a first compound selected from hole-transporting host materials and a second compound selected from electron-transporting host materials. Preferably, the first compound is a hole-transporting host material selected from the group of the carbazole and triarylamine derivatives, more particularly the biscarbazoles, the bridged carbazoles, the triarylamines, the dibenzofuran-carbazole derivatives or dibenzofuran-amine derivatives, and the carbazoleamines. Preferably, the second compound is an electron-transporting host material selected from compounds comprising a group selected from substituted or unsubstituted triazines, pyrimidines, lactams, benzimidazoles, quinazolines, quinoxalines, azadibenzofurans, diazadibenzofurans, azadibenzothiophenes, diazadibenzothiophenes, carbolines and triptycenes. Preferably, the emitting layer comprises a host and a dopant preferably selected from phosphorescent emitters. The term "phosphorescent emitters" typically encompasses compounds where the emitting of light is effected through a spin-forbidden transition, for example a transition from an excited triplet state or a state having a higher spin quantum number, for example a quintet state. Suitable phosphorescent emitters are especially compounds which, when suitably excited, emit light, preferably in the visible region, and also contain at least one atom of atomic number greater than 20, preferably greater than 38, and less than 84, more preferably greater than 56 and less than 80. Preference is given to using, as phosphorescent emitters, compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, especially compounds containing iridium, platinum or copper. In the context of the present invention, all luminescent iridium, platinum or copper complexes are considered to be phosphorescent compounds. Foreignfiling_text – P24-045 -79- Examples of the above-described emitting compounds can be found in applications WO 00 / 70655, WO 01 / 41512, WO 02 / 02714, WO 02 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 05 / 033244, WO 05 / 019373 and US 2005 / 0258742. In general, all phosphorescent complexes as used for phosphorescent OLEDs according to the prior art and as known to those skilled in the art in the field of organic electroluminescent devices are suitable. It is also possible for the person skilled in the art, without exercising inventive skill, to use further phosphorescent complexes. The emitting layer is preferably a green-emitting layer. What is meant by a green-emitting layer is a layer having a photoluminescence maximum within the range from 490 to 540 nm. The photoluminescence maximum of the layer is determined here by measuring the photoluminescence spectrum of the layer having a layer thickness of 50 nm at room temperature. The photoluminescence spectrum of the layer is recorded, for example, with a commercial photoluminescence spectrometer. The photoluminescence spectrum of the emitter chosen is generally measured in oxygen- free solution, 10-5molar, at room temperature, a suitable solvent being any in which the chosen emitter dissolves in the concentration mentioned. Particularly suitable solvents are typically toluene or 2-methyl-THF, but also dichloromethane. Measurement is effected with a commercial 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 by: E(T1 in eV) = 1240 / E(T1 in nm) = 1240 / PLmax. (in nm). Preferred phosphorescent emitters are accordingly green emitters, preferably selected from iridium or platinum complexes, which preferably have a triplet energy T1of ~2.5 eV to ~2.3 eV. In a preferred embodiment, the electronic device is part of an arrangement consisting of three or more, preferably three, electronic devices, of which one device contains a blue- Foreignfiling_text – P24-045 -80- emitting layer, one device a green-emitting layer, and one device a red-emitting layer (called an RGB side-by-side arrangement). The electronic device according to the application is preferably the green-emitting device in the arrangement. The electronic devices in the arrangement are preferably arranged alongside one another. In a particularly preferred embodiment, the arrangement contains a first device according to the application containing a hole transport layer HTL, a first auxiliary layer AUX1, a second auxiliary layer AUX2 and a green-phosphorescing layer, and a second device according to the application containing a blue-fluorescing or blue-phosphorescing emitting layer. There is preferably a third electronic device in the arrangement that contains a red-emitting layer, preferably a red-phosphorescing layer. Preferably, the hole transport layer HTL is identical, especially containing the same material, in the first and second devices according to the application in the arrangement, and preferably also in the third electronic device of the arrangement. In an alternative, likewise preferred embodiment, the electronic device contains multiple emitting layers arranged in succession, each having different emission maxima between 380 nm and 750 nm. In other words, different emitting compounds used in each of the multiple emitting layers fluoresce or phosphoresce and emit blue, green, yellow, orange or red light. In a preferred embodiment, the electronic device contains three emitting layers in succession in a stack, of which one in each case exhibits blue emission, one green emission, and one orange or red, preferably red, emission. Preferably, in this case, the blue-emitting layer is a fluorescent layer, and the green-emitting layer is a phosphorescent layer, and the red-emitting layer is a phosphorescent layer. Apart from cathode, anode, emitting layer, HTL, AUX1 and AUX2, the electronic device may comprise further layers. These are selected, for example, from in each case one or more hole injection layers, hole transport layers, hole blocker layers, electron transport layers, electron injection layers, electron blocker layers, exciton blocker layers, interlayers, charge generation layers and / or organic or inorganic p / n junctions. However, it should be pointed out that not every one of these layers need necessarily be present and the choice of layers always depends on the compounds used and especially also on whether the device is a fluorescent or phosphorescent electroluminescent device. Foreignfiling_text – P24-045 -81- Preferably, the first electrode is an anode and the second electrode is a cathode. The sequence of layers in the electronic device is preferably as follows: - first electrode, preferably anode - hole injection layer HIL, preferably p-doped - Hole transport layer HTL - optionally further hole transport layer(s) - first auxiliary layer AUX1 - second auxiliary layer AUX2 - emitting layer - optionally hole blocker layer - electron transport layer - electron injection layer - second electrode, preferably cathode. Preferred cathodes of the electronic device are metals having a low work function, metal alloys or multilayer structures composed of various metals, for example alkaline earth metals, alkali metals, main group metals or lanthanoids (e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Additionally suitable are alloys composed of an alkali metal or alkaline earth metal and silver, for example an alloy composed of magnesium and silver. In the case of multilayer structures, in addition to the metals mentioned, it is also possible to use further metals having a relatively high work function, for example Ag or Al, in which case combinations of the metals such as Ca / Ag, Mg / Ag or Ba / Ag, for example, are generally used. It may also be preferable to introduce a thin interlayer of a material having a high dielectric constant between a metallic cathode and the organic semiconductor. Examples of useful materials for this purpose are alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates (e.g. LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.). It is also possible to use lithium quinolinate (LiQ) for this purpose. The layer thickness of this layer is preferably between 0.5 and 5 nm. Preferred anodes are materials having a high work function. Preferably, the anode has a work function of greater than 4.5 eV versus vacuum. Firstly, metals having a high redox potential are suitable for this purpose, for example Ag, Pt or Au. Secondly, metal / metal oxide electrodes (e.g. Al / Ni / NiOx, Al / PtOx) may also be preferred. For some applications, at Foreignfiling_text – P24-045 -82- least one of the electrodes has to be transparent or partly transparent in order to enable either the irradiation of the organic material (organic solar cell) or the emitting of light (OLED, O-LASER). Preferred anode materials here are conductive mixed metal oxides. Particular preference is given to indium tin oxide (ITO) or indium zinc oxide (IZO). Preference is further given to conductive doped organic materials, especially conductive doped polymers. In addition, the anode may also consist of two or more layers, for example of an inner layer of ITO and an outer layer of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide. It is not obligatory for all the layers mentioned to be present, and / or further layers may additionally be present. Compounds that are preferably used in further hole-transporting layers of the device according to the application are indenofluoreneamine derivatives, amine derivatives, hexaazatriphenylene derivatives, amine derivatives with fused aromatic systems, monobenzoindenofluoreneamines, dibenzoindenofluoreneamines, spirobifluoreneamines, fluoreneamines, spirodibenzopyranamines, dihydroacridine derivatives, spirodibenzofurans and spirodibenzothiophenes, phenanthrenediarylamines, spirotribenzotropolones, spirobifluorenes having meta-phenyldiamine groups, spirobisacridines, xanthenediarylamines, and 9,10-dihydroanthracene spiro compounds having diarylamino groups. The electronic device preferably contains at least one electron transport layer. In addition, the electronic device preferably contains at least one electron injection layer. The electron injection layer preferably directly adjoins the cathode. In a preferred embodiment, the electron transport layer contains a triazine derivative and lithium quinolinate. In a preferred embodiment, the electron injection layer contains a triazine derivative and lithium quinolinate. In a particularly preferred embodiment, the electron transport layer and / or the electron injection layer, most preferably the electron transport layer and the electron injection layer, contain a triazine derivative and lithium quinolinate (LiQ). In a preferred embodiment, the electronic device contains at least one hole blocker layer. This preferably has hole-blocking and electron-transporting properties, and directly adjoins this emitting layer on the cathode side in a device containing a single emitting layer. In a Foreignfiling_text – P24-045 -83- device comprising multiple emitting layers that are arranged in succession, the hole blocker layer directly adjoins those of the multiple emitting layers that are closest to the cathode on the cathode side. Suitable electron-transporting materials are, for example, the compounds disclosed in Y. Shirota et al., Chem. Rev.2007, 107(4), 953-1010, or other materials used in these layers according to the prior art. Materials used for the electron transport layer may be any materials that are used as electron transport materials in the electron transport layer according to the prior art. Especially suitable are aluminium complexes, for example Alq3, zirconium complexes, for example Zrq4, lithium complexes, for example Liq, 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. In a preferred embodiment, the electronic device is characterized in that one or more layers are applied by a sublimation process. In this case, the materials are applied by vapour deposition in vacuum sublimation systems at an initial pressure of less than 10-5mbar, preferably less than 10-6mbar. In this case, however, it is also possible that the initial pressure is even lower, for example less than 10-7mbar. Preference is likewise given to an electronic device, characterized in that one or more layers are coated by the OVPD (organic vapour phase deposition) method or with the aid of a carrier gas sublimation. In this case, the materials are applied at a pressure between 10-5mbar and 1 bar. A special case of this method is the OVJP (organic vapour jet printing) method, in which the materials are applied directly by a nozzle and thus structured (for example M. S. Arnold et al., Appl. Phys. Lett.2008, 92, 053301). Preference is additionally given to an electronic device, characterized in that one or more layers are produced from solution, for example by spin-coating, or by any printing method, for example screen printing, flexographic printing, nozzle printing or offset printing, but more preferably LITI (light-induced thermal imaging, thermal transfer printing) or inkjet printing. Foreignfiling_text – P24-045 -84- It is further preferable that an electronic device according to the application is produced by applying one or more layers from solution and one or more layers by a sublimation method. After application of the layers, according to the use, the device is structured, contact- connected and finally sealed, in order to rule out damaging effects of water and air. The electronic device may be used in displays, as light source in lighting applications, and as light source in medical and / or cosmetic applications. A second object of the present application relates to compounds of formula (II´), Formula (II´) where the following applies to the symbols and indices occurring: L20, L21, L22are on each occurrence, identically or differently, a single bond, an aromatic ring system having 6 to 30 aromatic ring atoms or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R22; Foreignfiling_text – P24-045 -85- Ar22stands for an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R22; X1to X8and X1´to X8´stand on each occurrence, identically or differently, for CR20or N; where one group selected from X1, X2, X3or X4is bonded to L20and stands for C; Z11, Z13, Z14stand on each occurrence, identically or differently, for CR21or N; Z1to Z5stand on each occurrence, identically or differently, for CR21or N; of for C when bonded to a radical RA; Z6to Z10stand on each occurrence, identically or differently, for CR21or N; or for C when bonded to a radical RA; T20, T21are the same or different at each instance and are selected from single bond, O, S, NR21and C(R21)2; R20, R21, R22stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R)3, B(OR)2, N(R)2, N(Ar)2, OSO2R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non- adjacent CH2 groups may be replaced by RC=CR, C≡C, Si(R)2, Ge(R)2, Sn(R)2, C=O, C=S, C=Se, P(=O)(R), SO, SO2, O or S and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R; where two radicals R20, two radicals R21and / or two radicals R22may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R; RAstands on each occurrence, identically or differently, for F, Si(RB)3, a straight- chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one Foreignfiling_text – P24-045 -86- or more radicals RB, where in said alkyl, alkoxy and thioalkyl groups one or more non- adjacent CH2 groups may be replaced by RBC=CRB, C≡C, Si(RB)2, Ge(RB)2, Sn(RB)2, C=O, C=S, C=Se, P(=O)(RB), SO, SO2, O or S and one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2; where two radicals RAmay form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals RB; R, RBstand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R´)3, B(OR´)2, N(R´)2, N(Ar)2, OSO2R´, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R´, where in each case one or more non- adjacent CH2 groups may be replaced by R´C=CR´, C≡C, Si(R´)2, Ge(R´)2, Sn(R´)2, C=O, C=S, C=Se, P(=O)(R´), SO, SO2, O or S and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R´; where two radicals R, two radicals RBmay form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R´; Ar is, on each occurrence, identically or differently, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case also be substituted by one or more radicals R´; R´stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, where in each case one or more non-adjacent CH2groups may be replaced by SO, SO2, O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic ring system having 6 to 24 aromatic ring atoms or heteroaromatic ring system having 5 to 24 aromatic ring atoms; q is an integer selected from 1, 2, 3, 4 or 5, preferably 1 or 2; r is an integer selected from 1,2,3, 4 or 5, preferbaly 1 or 2. Foreignfiling_text – P24-045 -87- Preferably, the compound of formula (II´) is selected from compounds of formulae (II´-1) to (II´-6), Formula (II´-2) Foreignfiling_text – P24-045 -88- Formula (II´-4)
[0005] Foreignfiling_text – P24-045 -89- Formula (II´-6) where the symbols X1to X8, X1´to X8´, RA, T20, T21, L20, L21, L22, Ar22, Z1to Z5, Z6to Z10, Z11, Z12and Z13have the same meaning as above. Furthermore, the preferred embodiments for the symbols RA, T20, T21, L20, L21, L22present in formulae (II´) and (II´-1) to (II´-6) are the same preferred embodiments as for the symbols RA, T20, T21, L20, L21, L22present in formulae (II), (II-1) to (II-3) and (II-3-1) to (II-3-5), which are described above. Particularly preferred are the compound of formula (II´) selected from compounds of formulae (II´-1a) to (II´-6a), Foreignfiling_text – P24-045 -90- Formula (II´-2a) Foreignfiling_text – P24-045 Foreignfiling_text – P24-045 -92- Formula (II´-6a) where the symbols X1to X8, X1´to X8´, RA, L20, L21, L22, Ar22, Z1to Z5, Z6to Z10, Z11, Z12and Z13have the same meaning as above. Examples of compound of formula (II´) are depicted in the table below: Foreignfiling_text – P24-045 -93- Foreignfiling_text – P24-045 -94- Foreignfiling_text – P24-045 -95- Foreignfiling_text – P24-045 -96- Foreignfiling_text – P24-045 -97- Foreignfiling_text – P24-045 -98- Foreignfiling_text – P24-045 -99- Foreignfiling_text – P24-045 -100- Foreignfiling_text – P24-045 -101- Foreignfiling_text – P24-045 -102- Foreignfiling_text – P24-045 -103- Foreignfiling_text – P24-045 -104- Foreignfiling_text – P24-045 -105- Foreignfiling_text – P24-045 -106- In a general way, the compounds of formula (II´) disclosed in the table above might be deuterated, even if not explicitly disclosed in the table. The compounds of the formula (II´) can be prepared using known reactions of organic chemistry, for example using bromination reactions, Buchwald coupling reactions and Suzuki coupling reactions. General processes for the preparation of the compounds of the formula (II´) are shown in the application WO2012 / 034627 and WO2022 / 129117. Additionally, specific examples of processes for the preparation of compounds of the formula (II´) are shown in the working examples. The compounds according to the present invention may be used or applied together with further organic functional materials, which are commonly used in electronic devices according to the prior art. A great variety of suitable organic functional materials is known to Foreignfiling_text – P24-045 -107- those skilled in the art in the field of electronic devices. The present invention therefore further provides for a composition comprising one or more compounds of formula (II´) and at least one further organic functional material selected from the group consisting of fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron transporting materials, electron injecting materials, hole transporting materials, hole injecting materials, electron blocking materials, hole blocking materials, wide band gap materials, delayed fluorescent emitters and delayed fluorescent hosts. Delayed fluorescent emitters and delayed fluorescent hosts are well known in the art and disclosed in, e.g., Ye Tao et al., Adv. Mater.2014, 26, 7931-7958, M. Y. Wong et al., Adv. Mater.2017, 29, 1605444, WO 2011 / 070963, WO 2012 / 133188, WO 2015 / 022974 and WO 2015 / 098975. Typically, the delayed fluorescent materials (emitters and / or hosts) are characterized in that they exhibit a rather small gap between their singlet energy (S1) and triplet energy (T1). Preferably ∆EST is equal to or smaller than 0.5 eV, very preferably equal to or smaller than 0.3 eV, particularly preferably equal to or smaller than 0.2 eV and most preferably equal to or small than 0.1 eV, wherein ∆EST represents the difference between the singlet energy (S1) and the triplet energy (T1). Within the present invention, wide band gap materials are understood to mean a material as disclosed in US 7,294,849, which is characterized in having a band gap of at least 3 eV, preferably at least 3.5 eV and very preferably at least 4.0 eV, wherein the term “band gap” means the energy gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO). Such systems exhibit particularly advantageous performance characteristics in electroluminescent devices. The compounds of the invention are suitable for use in electronic devices, especially in organic electroluminescent devices such as OLEDs. Depending on the substitution, the compounds are used in different functions and layers. The invention therefore further provides for the use of the compound of formula (II´), or a composition comprising one or more compounds of formula (II´) and at least one further organic functional material, as described above, in an electronic device. This electronic device is preferably selected from the group consisting of organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic solar Foreignfiling_text – P24-045 -108- cells (OSCs), organic optical detectors, organic photoreceptors and, more preferably, organic electroluminescent devices (EL devices). Preferred EL devices are organic light- emitting transistors (OLETs), organic field-quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O-lasers) and organic light emitting diodes (OLEDs), of which OLEDs are most preferred. Particularly preferably, the electronic device is an organic light emitting diode (OLED). In accordance with a preferred embodiment, the electronic device is an organic light emitting diode (OLED) comprising anode, at least one hole transport layer, at least one emitting layer, at least one electron transport layer and cathode, where the at least one hole transport layer comprises a compound of formula (II´). In accordance with a very preferred embodiment, the electronic device is an organic light emitting diode (OLED) comprising anode, at least one hole transport layer, at least one light emitting layer, at least one electron transport layer and cathode, where the at least one hole transport layer comprises a compound of formula (II´) and, where the at least one hole transport layer is formed between the anode and the light emitting layer and the at least one electron transport layer is formed between the light emitting layer and the cathode. In accordance with a particularly preferred embodiment, the electronic device is an organic light emitting diode (OLED) comprising anode, a hole transport layer, a light emitting layer, an electron transport layer and cathode, where the hole transport layer includes a first hole transport layer and a second hole transport layer, where the first hole transport layer is formed between the anode and the second hole transport layer and the second hole transport layer is formed between the first hole transport layer and the emitting layer, and where the second hole transport layer comprises a compound of formula (II´). Preferably, the second hole-transport layer is an electron-blocking layer. More preferably, the second hole-transport layer is an electron-blocking layer adjacent to the light emitting layer. The electron-blocking layer may include a first electron-blocking layer and a second electron- blocking layer, where the second electron-blocking layer is adjacent to the emitting layer. Preferably, the electron-blocking layer, more preferably the first electron-blocking layer, comprises the compound of formula (II´). Foreignfiling_text – P24-045 -109- More specifically, it is preferred that the electronic device is an organic light emitting diode (OLED) comprising, in the following order: - An anode - A first hole transport layer - An electron blocking layer - A light emitting layer - An electron transport layer - A cathode, where the at least one electron blocking layer comprises a compound of formula (II´). In accordance with a very preferred embodiment, the sequence of layers in the OLED is as follows: substrate, anode, optionally hole-injection layer HIL, preferably p-doped, p-HIL first hole-transport layer HTL electron blocking layer EBL1 optionally second electron blocking layer EBL2 emitting layer EML optionally a hole-blocking layer HBL, an electron-transport layer ETL, optionally an electron-injection layer EIL, and a cathode, where either EBL1 or, when present, EBL2 comprises a compounds of formula (II´), and where further layers may additionally be present in the OLED. Within the present invention, the term “organic layer” is understood to mean any layer of an electronic device which comprises one or more organic compounds as functional materials. Apart from the cathode, anode and layers described above, the organic light emitting diode may also comprise further layers. These are selected, for example, from hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, interlayers, charge generation layers (IDMC 2003, Taiwan; Session 21 OLED (5), T. Matsumoto, T. Nakada, J. Foreignfiling_text – P24-045 -110- Endo, K. Mori, N. Kawamura, A. Yokoi, J. Kido, Multiphoton Organic EL Device Having Charge Generation Layer) and / or organic or inorganic p / n junctions. The organic light emitting diode comprising the compound (II´) may contain two or more emitting layers. More preferably, these emission layers in this case have several emission maxima between 380 nm and 750 nm overall, such that the overall result is white emission; in other words, various emitting compounds which may fluoresce or phosphoresce and which emit blue, green, yellow, orange or red light are used in the emitting layers. Especially preferred are three-layer systems, i.e. systems having three emitting layers, where the three layers show blue, green and orange or red emission (for the basic construction see, for example, WO 2005 / 011013). The compounds of the invention are preferably present in the hole transport layer, hole injection layer or electron blocking layer, most preferably in the electron blocking layer. It is preferable in accordance with the invention when the compound of formula (II´) is used in an electronic device comprising one or more phosphorescent emitting compounds as described above. In this case, the compound may be present in different layers, preferably in a hole transport layer, an electron blocking layer, a hole injection layer or in an emitting layer. It is also possible in accordance with the invention to use the compound of formula (II´) in an electronic device comprising one or more fluorescent emitting compounds. Hole injection layers and electron blocking layers are understood in the context of the present application to be specific embodiments of hole transport layers as described above. If the compound of formula (II´) is used as hole transport material in a hole transport layer, a hole injection layer or an electron blocking layer, the compound can be used as pure material, i.e. in a proportion of 100%, in the hole transport layer, or it can be used in combination with one or more further compounds. In a preferred embodiment, the organic layer comprising the compound of the formula (II´) then additionally contains one or more p- dopants. Preferred p-Dopants have already been described above. Foreignfiling_text – P24-045 -111- In a further preferred embodiment of the invention, the compound of formula (II´) is used as hole transport material in combination with a hexaazatriphenylene derivative as described in US 2007 / 0092755. Particular preference is given here to using the hexaazatriphenylene derivative in a separate layer. Further hole transport materials that can be used in any of the layers that require materials with hole transporting capabilities, e.g. hole injection layer (HIL), hole transport layer (HTL), electron blocking layer (EBL) or the emissive layer (EML) are listed in the following table. The compounds can be prepared easily according to the disclosure cited for each of the compounds. The teachings on the use of the compounds and the methods of making the compounds contained in the above patent applications are hereby expressly incorporated by reference into the present disclosure. The compounds HT-1 to HT-40 exhibit excellent properties when used in OLEDs, in particular excellent liftime and efficiency. This is particularly the case when they are used in a hole transport layer of the OLED. Foreignfiling_text – P24-045 -112- Foreignfiling_text – P24-045 -113- Foreignfiling_text – P24-045 -114- Foreignfiling_text – P24-045 -115- In general, compounds can be deuterated according to the following generic deuteration protocol: The compound is dissolved in a deuterated water (99% deuterium atom) and toluene-d8 (99% deuterium atom) mixture and heated to 160 °C for 96 hours under pressure in presence of dry platinum on carbon (5%) as catalyst. After cooling down the reaction mixture, the phases are separated, and the aqueous phase extracted twice at the tetrahydrofuran and toluene mixture. The recombined organic phases are washed with a sodium chloride solution, dried over sodium sulfate and filtered. The solvent is removed in vacuo to afford the crude deuterated compound as the solid. The compound is further purified by extraction, crystallization and sublimation. In a further embodiment of the present invention, the compound of the formula (II´) is used in an emitting layer as matrix material in combination with one or more emitting compounds, preferably phosphorescent emitting compounds. The proportion of the matrix material in the emitting layer in this case is between 50.0% and 99.9% by volume, preferably between 80.0% and 99.5% by volume, and more preferably between 92.0% and 99.5% by volume for fluorescent emitting layers and between 85.0% and 97.0% by volume for phosphorescent emitting layers. Correspondingly, the proportion of the emitting compound is between 0.1% and 50.0% by volume, preferably between 0.5% and 20.0% by volume, and more preferably between 0.5% and 8.0% by volume for fluorescent emitting layers and between 3.0% and 15.0% by volume for phosphorescent emitting layers. An emitting layer of an organic light emitting diode may also comprise systems comprising a plurality of matrix materials (mixed matrix systems) and / or a plurality of emitting compounds. In this case too, the emitting compounds are generally those compounds having the smaller proportion in the system and the matrix materials are those compounds having the greater proportion in the system. In individual cases, however, the proportion of a single matrix material in the system may be less than the proportion of a single emitting compound. Foreignfiling_text – P24-045 -116- It is preferable that the compounds of formula (II´) are used as a component of mixed matrix systems. The mixed matrix systems preferably comprise two or three different matrix materials, more preferably two different matrix materials. Preferably, in this case, one of the two materials is a material having hole-transporting properties and the other material is a material having electron-transporting properties. The compound of the formula (II´) is preferably the matrix material having hole-transporting properties. The desired electron- transporting and hole-transporting properties of the mixed matrix components may, however, also be combined mainly or entirely in a single mixed matrix component, in which case the further mixed matrix component(s) fulfill(s) other functions. The two different matrix materials may be present in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, more preferably 1:10 to 1:1 and most preferably 1:4 to 1:1. Preference is given to using mixed matrix systems in phosphorescent organic light emitting diode. One source of more detailed information about mixed matrix systems is the application WO 2010 / 108579. The mixed matrix systems may comprise one or more emitting compounds, preferably one or more phosphorescent emitting compounds. In general, mixed matrix systems are preferably used in phosphorescent organic light emitting diode. Particularly suitable matrix materials which can be used in combination with the compounds of the invention as matrix components of a mixed matrix system are selected from the preferred matrix materials specified below for phosphorescent emitting compounds or the preferred matrix materials for fluorescent emitting compounds, according to what type of emitting compound is used in the mixed matrix system. Preferred phosphorescent emitting compounds for use in mixed matrix systems are the same as detailed further up as generally preferred phosphorescent emitter materials. Suitable examples of the different functional materials in the electronic device are listed hereinafter. Suitable phosphorescent emitting compounds are the following ones: Foreignfiling_text – P24-045 -117- Foreignfiling_text – P24-045 -118- Foreignfiling_text – P24-045 -119- Foreignfiling_text – P24-045 -120- Foreignfiling_text – P24-045 -121- Suitable fluorescent emitting compounds are selected from the class of the arylamines. An arylamine or an aromatic amine in the context of this invention is understood to mean a compound containing three substituted or unsubstituted aromatic or heteroaromatic ring systems bonded directly to the nitrogen. Preferably, at least one of these aromatic or heteroaromatic ring systems is a fused ring system, more preferably having at least 14 aromatic ring atoms. Preferred examples of these are aromatic anthracenamines, aromatic anthracenediamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic chrysenamines or aromatic chrysenediamines. An aromatic anthracenamine is understood to mean a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9 position. An aromatic anthracenediamine is understood to mean a compound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 9,10 positions. Aromatic pyrenamines, pyrenediamines, chrysenamines and chrysenediamines are defined analogously, where the diarylamino groups are bonded to the pyrene preferably in the 1 position or 1,6 positions. Further preferred emitting compounds are indenofluorenamines or -fluorenediamines, for example according to WO 2006 / 108497 or WO 2006 / 122630, benzoindenofluorenamines or -fluorenediamines, for example according to WO 2008 / 006449, and dibenzoindenofluoreneamines or -diamines, for example according to WO 2007 / 140847, and the indenofluorene derivatives having fused aryl groups disclosed in WO 2010 / 012328. Likewise, preferred are the pyrenearylamines disclosed in WO 2012 / 048780 and in WO 2013 / 185871. Likewise, preferred are the benzoindenofluorenamines disclosed in WO 2014 / 037077, the benzofluorenamines disclosed in WO 2014 / 106522, the extended benzoindenofluorenes disclosed in WO 2014 / 111269 and in WO 2017 / 036574, the phenoxazines disclosed in WO 2017 / 028940 and in WO 2017 / 028941, and the fluorene derivatives bonded to furan units or to thiophene units that are disclosed in WO 2016 / 150544. Foreignfiling_text – P24-045 -122- Useful matrix materials, preferably for fluorescent emitting compounds, include materials of various substance classes. Preferred matrix materials are selected from the classes of the oligoarylenes (e.g.2,2‘,7,7‘-tetraphenylspirobifluorene according to EP 676461 or dinaphthylanthracene), especially of the oligoarylenes containing fused aromatic groups, the oligoarylenevinylenes (e.g. DPVBi or spiro-DPVBi according to EP 676461), the polypodal metal complexes (for example according to WO 2004 / 081017), the hole- conducting compounds (for example according to WO 2004 / 058911), the electron- conducting compounds, especially ketones, phosphine oxides, sulphoxides, etc. (for example according to WO 2005 / 084081 and WO 2005 / 084082), the atropisomers (for example according to WO 2006 / 048268), the boronic acid derivatives (for example according to WO 2006 / 117052) or the benzanthracenes (for example according to WO 2008 / 145239). Particularly preferred matrix materials are selected from the classes of the oligoarylenes comprising naphthalene, anthracene, benzanthracene and / or pyrene or atropisomers of these compounds, the oligoarylenevinylenes, the ketones, the phosphine oxides and the sulphoxides. Very particularly preferred matrix materials are selected from the classes of the oligoarylenes comprising anthracene, benzanthracene, benzophenanthrene and / or pyrene or atropisomers of these compounds. An oligoarylene in the context of this invention shall be understood to mean a compound in which at least three aryl or arylene groups are bonded to one another. Preference is further given to the anthracene derivatives disclosed in WO 2006 / 097208, WO 2006 / 131192, WO 2007 / 065550, WO 2007 / 110129, WO 2007 / 065678, WO 2008 / 145239, WO 2009 / 100925, WO 2011 / 054442 and EP 1553154, the pyrene compounds disclosed in EP 1749809, EP 1905754 and US 2012 / 0187826, the benzanthracenylanthracene compounds disclosed in WO 2015 / 158409, the indenobenzofurans disclosed in WO 2017 / 025165, and the phenanthrylanthracenes disclosed in WO 2017 / 036573. Preferred matrix materials for phosphorescent emitting compounds are, as well as the compounds of the formula (II´), aromatic ketones, aromatic phosphine oxides or aromatic sulphoxides or sulphones, for example according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680, triarylamines, carbazole derivatives, e.g. CBP (N,N- biscarbazolylbiphenyl) or the carbazole derivatives disclosed in WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 288381, EP 1205527 or WO 2008 / 086851, indolocarbazole derivatives, for example according to WO 2007 / 063754 or WO 2008 / 056746, indenocarbazole derivatives, for example according to WO 2010 / 136109, WO 2011 / 000455 Foreignfiling_text – P24-045 -123- or WO 2013 / 041176, azacarbazole derivatives, for example according to EP 1617710, EP 1617711, EP 1731584, JP 2005 / 347160, bipolar matrix materials, for example according to WO 2007 / 137725, silanes, for example according to WO 2005 / 111172, azaboroles or boronic esters, for example according to WO 2006 / 117052, triazine derivatives, for example according to WO 2010 / 015306, WO 2007 / 063754 or WO 2008 / 056746, zinc complexes, for example according to EP 652273 or WO 2009 / 062578, diazasilole or tetraazasilole derivatives, for example according to WO 2010 / 054729, diazaphosphole derivatives, for example according to WO 2010 / 054730, bridged carbazole derivatives, for example according to US 2009 / 0136779, WO 2010 / 050778, WO 2011 / 042107, WO 2011 / 088877 or WO 2012 / 143080, triphenylene derivatives, for example according to WO 2012 / 048781, or lactams, for example according to WO 2011 / 116865 or WO 2011 / 137951. Suitable charge transport materials as usable in the hole injection or hole transport layer or electron blocking layer or in the electron transport layer of the electronic device of the invention are, as well as the compounds of the formula (II´), for example, the compounds disclosed in Y. Shirota et al., Chem. Rev.2007, 107(4), 953-1010, or other materials as used in these layers according to the prior art. Preferably, the inventive OLED comprises two or more different hole-transporting layers. The compound of the formula (II´) may be used here in one or more of or in all the hole- transporting layers. In a preferred embodiment, the compound of the formula (II´) is used in exactly one or exactly two hole-transporting layers, and other compounds, preferably aromatic amine compounds, are used in the further hole-transporting layers present. Further compounds which are used alongside the compounds of the formula (II´), preferably in hole-transporting layers of the OLEDs of the invention, are especially indenofluorenamine derivatives (for example according to WO 06 / 122630 or WO 06 / 100896), the amine derivatives disclosed in EP 1661888, hexaazatriphenylene derivatives (for example according to WO 01 / 049806), amine derivatives with fused aromatics (for example according to US 5,061,569), the amine derivatives disclosed in WO 95 / 09147, monobenzoindenofluorenamines (for example according to WO 08 / 006449), dibenzoindenofluorenamines (for example according to WO 07 / 140847), spirobifluorenamines (for example according to WO 2012 / 034627 or WO 2013 / 120577), fluorenamines (for example according to WO 2014 / 015937, WO 2014 / 015938, WO 2014 / 015935 and WO 2015 / 082056), spirodibenzopyranamines (for example according to Foreignfiling_text – P24-045 -124- WO 2013 / 083216), dihydroacridine derivatives (for example according to WO 2012 / 150001), spirodibenzofurans and spirodibenzothiophenes, for example according to WO 2015 / 022051, WO 2016 / 102048 and WO 2016 / 131521, phenanthrenediarylamines, for example according to WO 2015 / 131976, spirotribenzotropolones, for example according to WO 2016 / 087017, spirobifluorenes with meta-phenyldiamine groups, for example according to WO 2016 / 078738, spirobisacridines, for example according to WO 2015 / 158411, xanthenediarylamines, for example according to WO 2014 / 072017, and 9,10- dihydroanthracene spiro compounds with diarylamino groups according to WO 2015 / 086108. Very particular preference is given to the use of spirobifluorenes substituted by diarylamino groups in the 4 position as hole-transporting compounds, especially to the use of those compounds that are claimed and disclosed in WO 2013 / 120577, and to the use of spirobifluorenes substituted by diarylamino groups in the 2 position as hole-transporting compounds, especially to the use of those compounds that are claimed and disclosed in WO 2012 / 034627. Materials used for the electron transport layer may be any materials as used according to the prior art as electron transport materials in the electron transport layer. Especially suitable are aluminum complexes, for example Alq3, zirconium complexes, for example Zrq4, lithium complexes, for example Liq, 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. Further suitable materials are derivatives of the abovementioned compounds as disclosed in JP 2000 / 053957, WO 2003 / 060956, WO 2004 / 028217, WO 2004 / 080975 and WO 2010 / 072300. Preferred anodes and cathodes are described above. The device is structured appropriately (according to the application), contact-connected and finally sealed, in order to rule out damaging effects by water and air. In a preferred embodiment, the electronic device is characterized in that one or more layers are coated by a sublimation process. In this case, the materials are applied by vapour Foreignfiling_text – P24-045 -125- deposition in vacuum sublimation systems at an initial pressure of less than 10-5mbar, preferably less than 10-6mbar. In this case, however, it is also possible that the initial pressure is even lower, for example less than 10-7mbar. Preference is likewise given to an electronic device, characterized in that one or more layers are coated by the OVPD (organic vapour phase deposition) method or with the aid of a carrier gas sublimation. In this case, the materials are applied at a pressure between 10-5mbar and 1 bar. A special case of this method is the OVJP (organic vapour jet printing) method, in which the materials are applied directly by a nozzle and thus structured (for example M. S. Arnold et al., Appl. Phys. Lett.2008, 92, 053301). Preference is additionally given to an electronic device, characterized in that one or more layers are produced from solution, for example by spin-coating, or by any printing method, for example screen printing, flexographic printing, nozzle printing or offset printing, but more preferably LITI (light-induced thermal imaging, thermal transfer printing) or inkjet printing. For this purpose, soluble compounds of formula (II´) are needed. High solubility can be achieved by suitable substitution of the compounds. It is further preferable that an electronic device of the invention is produced by applying one or more layers from solution and one or more layers by a sublimation method. According to the invention, the electronic devices comprising one or more compounds of formula (II´) can be used in displays, as light sources in lighting applications and as light sources in medical and / or cosmetic applications (e.g. light therapy). The compounds according to the present invention and the electronic devices according to the present invention, respectively, exhibit the following surprising and advantageous effects compared to the prior art: 1 The compounds according to the present invention are particularly suitable as hole- transporting materials in an electron blocking layer in electronic devices, such as electroluminescent devices, which is particularly due to their very good electron-blocking properties and hole-conducting properties Foreignfiling_text – P24-045 -126- 2. The compounds according to the present invention are characterized by low sublimation temperature, high thermal stability, high oxidation stability, high glass transition temperature and high solubility, which is advantageous in terms of their processability, for example from the liquid phase or from the gaseous phase and makes them particularly suitable for being used in electronic devices. 3. When used in electronic devices, in particular as hole-transporting materials, the compounds according to the present invention lead to excellent results in terms of lifetime, operating voltage and quantum efficiency of the devices. 4. The compounds containing deuterium are more thermally stable, the devices containing the compounds show a longer lifetime and an improved efficiency The invention is described in more detail below with the help of examples which are not to be considered as limiting the scope of the invention. Examples A) Synthesis examples Synthesis of Int-1 40.0 g (98 mmol) 2-Bromo-1,4-diiodobenzene, 46.7 g (200 mmol) 3,5-di-t- butylphenylboronic acid and54.1 g (390 mmol) potassium carbonate are dissolved in 1.5 L toluene / ethanol / water (10:1:4).2.06 g (3 mmol) PdCl2(PPh3)2 are added, and the reaction mixture is stirred for 16 hours at 77 °C. The reaction mixture is allowed to come to room temperature, 300 ml water are added and the phases are separated. The organic phase is washed with water (2x300ml) and brine, dried over sodium sulfate and the solvents are removed under reduced pressure. The product is obtained by crystallization out of ethanol. Yield: 31.3 g (59 mmol, 61%) Foreignfiling_text – P24-045 -127- Following intermediate materials can be synthesized in analogous manner: Foreignfiling_text – P24-045 -128- Synthesis of compound 1 28.0 g (52 mmol) of Int-1, 27.5 g (52 mmol) N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'- spirobi[fluoren]-7-amine and 9.1 g (79mmol) sodium tert-butoxide are dissolved in 600 ml toluene.0.48 g (0.52 mmol) Pd2(dba)3 and 0.30 g (1.0 mmol) Tri-tert-butylphosphonium tetrafluoroborate are added and the mixture is refluxed for 18 hours. The reaction is allowed to come to room temperature and 300 ml water are added. The phases are separated, and the organic phase is washed with water (2x300 ml) and 300 ml brine and dried over sodium sulfate. The organic solvet is removed under reduced pressure and the crude is purified by column chromatography (SiO2, heptane / DCM) an crystallization out of toluene / heptane. The product is obtained after sublimation (310°C at 10-5bar) with a HPLC purity > 99.9%. Yield: 15.5 g(16 mmol, 31%) Following compounds can be synthesized in analogous manner: Foreignfiling_text – P24-045 -129- Foreignfiling_text – P24-045 -130- B) Device examples 1. Preparation of OLED stacks OLEDs are produced according to the following process, and their properties are characterized, as described below in detail. Glass plaques which are coated with structured ITO (indium tin oxide) in a thickness of 50 nm are used as the substrates to which the OLEDs are applied. The OLEDs have the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layers (EBL, or EBL1 and EBL2) / emission layer (EML) / hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) and finally a cathode. The cathode is formed by an aluminum layer of thickness 100 nm. All materials mentioned in the following are applied by thermal vapor deposition in a vacuum chamber. Examples 1 to 4 (E1 to E3 and E20) and comparative example 1 (CE1): The devices of examples 1 to 4 (E1 to E3 and E20) and of the comparative example 1 (CE1) comprise a hole injection layer (HIL) of 10nm, which consists of the compounds EH1 and D as follows: EH1:D (95%:5%), meaning here that the material EH1 is present in the layer in a proportion by volume of 95% and the dopant D in a proportion of 5%. A hole transport layer (HTL) of 50 nm is deposited on the HIL. The hole transport layer consists of the compound EH1. An electron blocking layer (EBL) of 35 nm is deposited on the HTL. The electron blocking layer consists of a material as described in Table 1 below. An emission layer (EML) of 35 nm is deposited on the EBL and consists of matrix materials T11 and T12 (host materials) and an emitting dopant T13, which is added to the matrix materials in a particular proportion by volume by co-evaporation. The ratio T11:T12:T13 Foreignfiling_text – P24-045 -131- corresponds to 32%:60%:8%, meaning that the material T11 is present in the layer in a proportion by volume of 32%, T12 in a proportion of 60% and T13 in a proportion of 8%. A hole blocking layer (HBL) of 5 nm consisting of the compound E is deposited on the EML. Then, an electron transport layer (ETL) of 30 nm consisting of the compound F and LiQ as follows F:LiQ (50%:50%) is deposited on the HBL. Finally, an electron injection layer (EIL) of 1 nm consisting of LiQ is deposited on the HBL. The materials used for production of the OLEDs are shown in Table 5. Examples 5 to 23 (E4 to E19 and E21 to E23) and comparative examples 2 and 3 (CE2 and CE3): The devices of examples 5 to 23 (E4 to E19 and E21 to E23) and of the comparative examples 2 and 3 (CE2 and CE3) comprise a hole injection layer HIL (10nm), a hole transport layer HTL (50 nm) deposited on HIL, a first electron blocking layer EBL1 (25 nm) deposited on HTL and a second electron blocking layer EBL2 (5nm) deposited on EBL1. HIL, HTL, EBL1 and EBL2 comprise the materials as described in Table 2 below. An emission layer EML of 38 nm is deposited on EBL2 and consists of matrix materials T21 and T22 (host materials) and an emitting dopant T23, which is added to the matrix materials in a particular proportion by volume by co-evaporation. The ratio T21:T22:T23 corresponds to 35%:53%:12%. A hole blocking layer HBL (5 nm) consisting of compound E is deposited on the EML. Then, an electron transport layer ETL of 30 nm consisting of compound F and LiQ as follows F:LiQ (50%:50%) is deposited on the HBL. Finally, an electron injection layer EIL of 1 nm consisting of LiQ is deposited on the HBL. The materials used for production of the OLEDs are shown in Table 5. Foreignfiling_text – P24-045 -132- 2. Characterization of the performance of the OLED stacks External Quantum Efficiency and voltage The external quantum efficiency (EQE, measured in %) as a function of the luminance, calculated from current-voltage-luminance characteristics assuming Lambertian radiation characteristics, is determined. The parameter EQE @ 10 mA / cm² refers to the external quantum efficiency which is attained at current density of 10 mA / cm². Relative EQE’s are then given by the ratio of a given example Ei to the respective comparison examples Cj, generally written: Foreignfiling_text – P24-045 -133- The voltage is extracted from voltage current density characteristics for current densities of 10 mA / cm². Relative voltages are then given by the ratio of a given example Ei to the respective comparison examples Cj, generally written: Light output adjusted lifetime Generally, lifetime is compared at a certain current density, or compared at a certain light intensity of the OLED. For commercial success of an OLED, it is important what the lifetime at a certain light intensity is. If an OLED is more efficient, it reaches the same light intensity at a lower current density. So, less stress needs to be put on the OLED to obtain the same result. Therefore, further aspect of lifetime, i.e., "light output adjusted lifetime" is determined to assess the performance of the OLED. Lifetime values LT90are measured as time passed (in hrs) until luminance is dropped to 90% of initial luminance L0at 80 mA / cm² constant current stress. To better compare lifetimes, the latter are converted to lifetimes at same ^.^initial luminance L* being 15000 cd / m², calculated by ^^∗ = ^^ ^^^^ ∗ ^^^^^^ cd / m²^, 1.5 being the acceleration factor used for conversion. Relative lifetimes are then given by the ratio of the given example Ei to the comparison example Cj: rel ^^C∗omparison example3. Results Table 3: relative performance of the OLEDs given in Table 1 Rel. EQE @10mA / cm² Rel. U @10 mA / cm² Rel LT CE1 100% 100% 100% E1 108% 100% 101% E2 105% 99% 102% E3 108% 100% 99% E20 107% 99% 103% Foreignfiling_text – P24-045 -134- In table 3, the devices E1, E2 and E20 comprising the inventive compounds EB2, EB4 and EB9 show an improved EQE of 5% or more compared to the comparative example CE1 for similar operating voltages and lifetimes. From a commercial perspective, for a new model, a display manufacturer typically demands that the efficiency of OLED increases by around 10-15%. These efficiency gains can come from multiple layers, not only from one layer. Thus, if a new material for one layer contributes a 2-5% increase in efficiency, this is already a significant and very good result. In consideration of EQE, the compounds EB2, EB4 and EB9 of the examples E1, E2 and E20 show performance improvement over the comparative example CE1. Example E3 comprising the compound EB5 is also showing a very good EQE with unchanged relative voltage and lifetime. The OLED examples E4 and E5 give at least 5% EQE improvement compared to respective comparative examples CE2 and CE3 with a lifetime increase of more than 10%. The OLED examples E6 to E19 and E21 to E23 give at least 3% of improvement in EQE while lifetime is increased at least by 7%-17% Foreignfiling_text – P24-045 -135- Hence, in consideration of EQEs and lifetimes shown in table 4, in particular the comparison of E4, E5 to CE2, CE3, the compounds EB1 to EB5 and EB9 of the examples E4 to E19 and E21 toE23 show outstanding performance. Structures of the compounds used in OLED stacks: Foreignfiling_text – P24-045 -136- Foreignfiling_text – P24-045 -137- Foreignfiling_text – P24-045 -138-
Claims
Foreignfiling_text – P24-045 -139- Claims 1. An electronic device comprising: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and comprising an emitting layer, wherein: the emitting layer comprises a host material and a dopant, where the dopant is selected from fluorescent emitters and phosphorescent emitters, the interlayer further comprises a hole transport region between the emitting layer and the first electrode, the hole transport region comprises a hole transport layer, a first auxiliary layer and a second auxiliary layer, where the first auxiliary layer is located between the hole transport layer and the second auxiliary layer, and the second auxiliary layer is located between the first auxiliary layer and the emitting layer, the hole transport layer comprises a compound H selected from triarylamine-based compounds, the first auxiliary layer comprises a compound G1 selected from compounds of formula (II),Foreignfiling_text – P24-045 -140-Formula (II) where the following applies to the symbols and indices occurring: L20, L21, L22, L23, L24are on each occurrence, identically or differently, a single bond, an aromatic ring system having 6 to 30 aromatic ring atoms or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R22; Ar22stands for an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R22; X1to X8and X1´to X8´stand on each occurrence, identically or differently, for CR20, CRAor N; where at least one of X1, X2, X3and X4is bonded to L20and stands for C; Z1to Z27stand on each occurrence, identically or differently, for CR21, CRAor N; where the symbols Z11to Z15, Z16to Z21and Z22to Z27which are bonded to an adjacent group stand for C;Foreignfiling_text – P24-045 -141- T20, T21are the same or different at each instance and are selected from single bond, O, S, NR21and C(R21)2; R20, R21, R22stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R)3, B(OR)2, N(R)2, N(Ar)2, OSO2R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non- adjacent CH2 groups may be replaced by RC=CR, C≡C, Si(R)2, Ge(R)2, Sn(R)2, C=O, C=S, C=Se, P(=O)(R), SO, SO2, O or S and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R; where two radicals R20, two radicals R21and / or two radicals R22may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R; RAstands on each occurrence, identically or differently, for F, Si(RB)3, a straight- chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals RB, where in said alkyl, alkoxy and thioalkyl groups one or more non- adjacent CH2 groups may be replaced by RBC=CRB, C≡C, Si(RB)2, Ge(RB)2, Sn(RB)2, C=O, C=S, C=Se, P(=O)(RB), SO, SO2, O or S and one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2; where two radicals RAmay form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals RB; R, RBstand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R´)3, B(OR´)2, N(R´)2, N(Ar)2, OSO2R´, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R´, where in each case one or more non- adjacent CH2groups may be replaced by R´C=CR´, C≡C, Si(R´)2, Ge(R´)2, Sn(R´)2, C=O, C=S, C=Se, P(=O)(R´), SO, SO2, O or S and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic ring system having 6 to 40 aromaticForeignfiling_text – P24-045 -142- ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R´; where two radicals R, two radicals RBmay form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R´; Ar is, on each occurrence, identically or differently, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case also be substituted by one or more radicals R´; R´stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, where in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic ring system having 6 to 24 aromatic ring atoms or heteroaromatic ring system having 5 to 24 aromatic ring atoms; m is 0 or 1; n is 0 or 1; p is 0 or 1; where, when m or n is 0, then the group in parentheses is absent and the two groups on either side of the group in parentheses are linked by a single bond; and the second auxiliary layer comprises a compound G2; characterized in that, in the compound of formula (II), at least one symbol selected from X1to X8, X1´to X8´or Z1to Z27stands for CRA.
2. An electronic device according to claim 1, characterized in that the compound G1 is selected from the compounds of formula (II), where at least two, three or four symbols selected from X1to X8or X1´to X8´and Z1to Z27stand for CRA.
3. An electronic device according to one or more of the preceding claims, characterized in that:Foreignfiling_text – P24-045 -143- RAstands on each occurrence, identically or differently, for a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 10 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 10 C atoms, each of which may be substituted by one or more radicals RB, where in said alkyl, alkoxy and thioalkyl groups one or more H atoms may be replaced by D or F; and where two radicals RAmay form an aliphatic ring system together, which may be substituted by one or more radicals RB.
4. An electronic device according to one or more of the preceeding claims, characterized in that the compound G1 is selected from compounds of formula (II-0) or (II-1),Formula (II-0)Foreignfiling_text – P24-045 -144-Formula (II-1) where the symbols X1to X8, X1´to X8´, T20, T21, L20, L21, L22, Ar22, Z1to Z15have the same meaning as above, and: where the compound of formula (II-0) comprises at least one symbol selected from X1to X8, X1´to X8´, Z1to Z5and Z11to Z15, which stands for CRA; where the compound of formula (II-1) comprises at least one symbol selected from X1to X8, X1´to X8´, Z1to Z15, which stands for CRA.
5. An electronic device according to one or more of the preceding claims, characterized in that the compound G1 is selected from compounds of formula (II-2),Foreignfiling_text – P24-045 -145-Formula (II-2) where the symbols X1to X8, X1´to X8´, T20, T21, L20, L21, L22, Ar22, Z1to Z15have the same meaning as in claim 1, where the compound of formula (II-2) comprises at least two, three or four symbols selected from X1to X8, X1´to X8´and Z1to Z15, which stand for CRA.
6. An electronic device according to one or more of the preceding claims, characterized in that the compound G1 is selected from compound of formula (II-3),Formula (II-3)Foreignfiling_text – P24-045 -146- where the symbols X1to X8, X1´to X8´, T20, T21, L20, L21, L22, Ar22, Z1to Z15have the same meaning as in claim 1, where the compound of formula (II-3) comprises at least two, three or four symbols selected from X1to X8, X1´to X8´and Z1to Z15, which stand for CRA.
7. An electronic device according to one or more of the preceding claims, characterized in that the compound H is selected from compounds of formulae (IA), (IB) and (IC),Formula (IC) where the following applies to the symbols and indices occurring:Foreignfiling_text – P24-045 -147- L10, L11, L12are on each occurrence, identically or differently, a single bond, an aromatic ring system having 6 to 30 aromatic ring atoms or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R12; Ar11, Ar12are on each occurrence, identically or differently, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R12; X stands on each occurrence, identically or differently, for CR10or N; or X stands for C when it is bonded to an adjacent group; T10, T11, T12, T13, T14are the same or different at each instance and are selected from a single bond, O, S, NRN, and C(RC)2; with the proviso that T12, T13do not both stand for a single bond; RCstands on each occurrence, identically or differently, for H, D, F, Si(R)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where one or more H atoms may be replaced by D or F, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R; where two radicals RCmay form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R; RNstands for H, D, F, a straight-chain alkyl group having 1 to 40 C atoms or branched or a cyclic alkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where one or more H atoms may be replaced by D or F, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R; where R has the same meaning as in claim 1. R10, R11, R12stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R)3, B(OR)2, N(R)2, N(Ar)2, OSO2R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms orForeignfiling_text – P24-045 -148- branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non- adjacent CH2 groups may be replaced by RC=CR, C≡C, Si(R)2, Ge(R)2, Sn(R)2, C=O, C=S, C=Se, P(=O)(R), SO, SO2, O or S and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R; where two radicals R10, two radicals R11and / or two radicals R12may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R; R has the same definition as in claim 1.
8. An electronic device according to one or more of the preceding claims, characterized in that the compound H is selected from compounds of formulae (IA-1), (IA-2), (IA-3), (IB-1), (IB-2), (IB-3) and (IC-1),Formula (IA-2)Foreignfiling_text – P24-045 -149-Foreignfiling_text – P24-045 -150-Formula (IC-1) where the symbols X, RC, RN, L10, L11, L12, Ar11and Ar12have the same meaning as in claim 7.
9. An electronic device according to one or more of the preceding claims, characterized in that the compound H is selected from compounds of formulae (IA-1-1) to (IA-3-2), (IB-1-1) to (IB-3-2), (IC-1-1) and (IC-1-2),Formula (IA-1-1)Foreignfiling_text – P24-045 -151-Formula (IA-2-2)Foreignfiling_text – P24-045 -152-Formula (IB-1-1)Foreignfiling_text – P24-045 -153-Formula (IB-2-2)Foreignfiling_text – P24-045 -154-Formula (IC-1-1)Foreignfiling_text – P24-045 -155-Formula (IC-1-2) where A1is equal to C(RC)2, O, S or equal to, where the dashed lines represent the bonds emanating from the group A1; Y stands on each occurrence, identically or differently, for CR10or N; or Y stands for C when it is bonded to the group L12; and where the symbols X, RC, RN, L10, L11, L12, Ar11and Ar12have the same meaning as above.
10. An electronic device according to one or more of the preceeding claims, characterized in that the compound G2 is selected from compounds of formulae (IIIA), (IIIB), (IIIC), (IIID), (IIIE) and (IIIF),Foreignfiling_text – P24-045 -156-Foreignfiling_text – P24-045 -157-where where the following applies to the symbols occurring: L30, L31, L32are on each occurrence, identically or differently, a single bond, an aromatic ring system having 6 to 30 aromatic ring atoms or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R32; Ar30, Ar31, Ar32are on each occurrence, identically or differently, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R32; V stands on each occurrence, identically or differently, for CR30or N; or V stands for C when it is bonded to the group L30;Foreignfiling_text – P24-045 -158- T30, T31, T32, T33, T34, T35are the same or different at each instance and are selected from a single bond, O, S, NRN, and C(RC)2; with the proviso that T32, T33do not both stand for a single bond; T36, T37are the same or different at each instance and are selected from O, S, NRN, and C(RC)2; R30, R31, R32stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R)3, B(OR)2, N(R)2, N(Ar)2, OSO2R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non- adjacent CH2 groups may be replaced by RC=CR, C≡C, Si(R)2, Ge(R)2, Sn(R)2, C=O, C=S, C=Se, P(=O)(R), SO, SO2, O or S and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R; where two radicals R30, two radicals R31and / or two radicals R32may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R; where R has the same definition as in claim 1, RCand RNhave the same mening as in claim 7.
11. An electronic device according to one or more of the preceding claims, characterized in that the compound G2 is selected from compounds of formulae (IIIA-1) to (IIIA-4), (IIIB), (IIIC-1) to (IIIC-3), (IIID-1), (IIIE-1) and (IIIF-1),Foreignfiling_text – P24-045 -159-Formula (IIIA-4)Foreignfiling_text – P24-045 -160-Formula (IIIC-3)Foreignfiling_text – P24-045 -161-Formula (IIIF-1) where the symbols V, L30, L31, L32, Ar30, Ar31and Ar32have the same meaning as in claim 10, RCand RNhave the same meaning as in claim 7.
12. An electronic device according to one or more of the preceding claims, characterized in that the compound G2 is selected from compounds of formulae (IIIA-1-1) to (IIIA-4-2),Foreignfiling_text – P24-045 -162- (IIIB-1), (IIIB-2), (IIIC-1-1) to (IIIC-3-2), (IIID-1-1), (IIID-1-2), (IIIE-1-1), (IIIE-1-2), (IIIF-1-1) and (IIIF-1-2),Formula (IIIA-2-1)Foreignfiling_text – P24-045 -163-Formula (IIIA-3-2)Foreignfiling_text – P24-045 -164-Formuöa (IIIA-4-2)Foreignfiling_text – P24-045 -165-Formula (IIIB-2)Foreignfiling_text – P24-045 -166-Formula (IIIC-2-1)Foreignfiling_text – P24-045 -167-Formula (IIIC-3-2)Foreignfiling_text – P24-045 -168-Formula (IIIE-1-1)Foreignfiling_text – P24-045 -169-Formula (IIIF-1-2) Where A2is equal to C(RC)2, O, S or equal toForeignfiling_text – P24-045 -170-, where the dashed lines represent the bonds emanating from the group A2; W stands on each occurrence, identically or differently, for CR30or N; or Y stands for C when it is bonded to the group L32; and where the symbols V, L30, L31, L32, Ar30, Ar31and Ar32have the same meaning as in claim 10, and RCand RNhave the same meaning as in claim 7..
13. An electronic device according to one or more of the preceding claims, characterized in that the emitting layer comprises a host material and a dopant, where the dopant is selected from phosphorescent emitters.
14. An electronic device according to one or more of the preceding claims, characterized in that the emitting layer comprises a host material, where the host material comprises a first compound selected from hole-transporting host materials and a second compound selected from electron-transporting host materials.
15. An electronic device according to claim 14, characterized in that the first compounds is a hole-transporting host material selected from the group of the carbazole and triarylamine derivatives, more particularly the biscarbazoles, the bridged carbazoles, the triarylamines, the dibenzofuran-carbazole derivatives or dibenzofuran-amine derivatives, and the carbazoleamines.
16. An electronic device according to claim 14 or 15, characterized in that that the second compound is an electron-transporting host material selected from compounds comprising a group selected from substituted or unsubstituted triazines, pyrimidines, lactams, benzimidazoles, quinazolines, quinoxalines, azadibenzofurans, diazadibenzofurans, azadibenzothiophenes, diazadibenzothiophenes, carbolines and triptycenes.Foreignfiling_text – P24-045 -171- 17. An electronic device according to one or more of the preceding claims, characterized in that: -5.30 ≤ HOMO (G1) ≤ -5.05 eV where HOMO (G1) corresponds to the energy of the highest occupied molecular orbital of the compound G1 as determined by quantum-chemical calculation.
18. An electronic device according to one or more of the preceding claims, characterized in that: -5.50 ≤ HOMO (G2) ≤ -5.15 eV where HOMO (G2) corresponds to the energy of the highest occupied molecular orbital of the compound G2 as determined by quantum-chemical calculation.
19. An electronic device according to one or more of the preceding claims, according to one or more of the preceding claims, characterized in that: -5.25 ≤ HOMO (H) ≤ -5.00 eV where HOMO (H) corresponds to the energy of the highest occupied molecular orbital of the compound H as determined by quantum-chemical calculation.
20. An electronic device according to one of more of the preceding claims, characterized in that at least one compound selected from compound G1, compound G2 and compound H is a deuterated compound.
21. An electronic device according to one or more of the preceding claims, characterized in that the first auxiliary layer comprising the compound G1 is in direct contact with the second auxiliary layer comprising the compound G2.
22. An electronic device according to one or more of the preceding claims, characterized in that the second auxiliary layer comprising the compound G2 is in direct contact with the emitting layer.
23. An electronic device according to one or more of the preceding claims, characterized in that the hole transport layer comprising the compound H is in direct contact with the first auxiliary layer comprising the compound G1.Foreignfiling_text – P24-045 -172- 24. An electronic device according to one or more of the preceding claims, characterized in that the hole transport layer comprising the compound H is not doped with p-dopants 25. An electronic device according to one or more of the preceding claims, characterized in that the hole transport region further comprises a hole injection layer between the first electrode and the hole transport layer comprising the compound H.
26. A compound of the formula (II´),Formula (II´) where the following applies to the symbols and indices occurring: L20, L21, L22are on each occurrence, identically or differently, a single bond, an aromatic ring system having 6 to 30 aromatic ring atoms or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R22; Ar22stands for an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R22;Foreignfiling_text – P24-045 -173- X1to X8and X1´to X8´stand on each occurrence, identically or differently, for CR20or N; where one group selected from X1, X2, X3or X4is bonded to L20and stands for C; Z11, Z13, Z14stand on each occurrence, identically or differently, for CR21or N; Z1to Z5stand on each occurrence, identically or differently, for CR21or N; of for C when bonded to a radical RA; Z6to Z10stand on each occurrence, identically or differently, for CR21or N; or for C when bonded to a radical RA; T20, T21are the same or different at each instance and are selected from single bond, O, S, NR21and C(R21)2; R20, R21, R22stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R)3, B(OR)2, N(R)2, N(Ar)2, OSO2R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non- adjacent CH2 groups may be replaced by RC=CR, C≡C, Si(R)2, Ge(R)2, Sn(R)2, C=O, C=S, C=Se, P(=O)(R), SO, SO2, O or S and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R; where two radicals R20, two radicals R21and / or two radicals R22may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R; RAstands on each occurrence, identically or differently, for F, Si(RB)3, a straight- chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals RB, where in said alkyl, alkoxy and thioalkyl groups one or more non- adjacent CH2groups may be replaced by RBC=CRB, C≡C, Si(RB)2, Ge(RB)2, Sn(RB)2, C=O, C=S, C=Se, P(=O)(RB), SO, SO2, O or S and one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2; where two radicals RAmay form an aliphatic, aromatic orForeignfiling_text – P24-045 -174- heteroaromatic ring system together, which may be substituted by one or more radicals RB; R, RBstand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R´)3, B(OR´)2, N(R´)2, N(Ar)2, OSO2R´, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R´, where in each case one or more non- adjacent CH2 groups may be replaced by R´C=CR´, C≡C, Si(R´)2, Ge(R´)2, Sn(R´)2, C=O, C=S, C=Se, P(=O)(R´), SO, SO2, O or S and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R´; where two radicals R, two radicals RBmay form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R´; Ar is, on each occurrence, identically or differently, an aromatic ring system having 6 to 40 aromatic ring atoms or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case also be substituted by one or more radicals R´; R´stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, where in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic ring system having 6 to 24 aromatic ring atoms or heteroaromatic ring system having 5 to 24 aromatic ring atoms; q is an integer selected from 1, 2, 3, 4 or 5; r is an interger selected from 1,2,3, 4 or 5.
27. A compound according to claim 26, which is selected from compounds of formulae (II´- 1) to (II´-6),Foreignfiling_text – P24-045 -175-Formula (II´-3)Foreignfiling_text – P24-045 -176-Foreignfiling_text – P24-045 -177- Formula (II´-6) where the symbols X1to X8, X1´to X8´, RA, T20, T21, L20, L21, L22, Ar22, Z1to Z5, Z6to Z10, Z11, Z12and Z13have the same meaning as in claim 26.
28. Organic electroluminescent device comprising at least one compound according to claim 26 or 27.
29. Organic electroluminescent device according to claim 28, characterized in that the compound according to claim 26 or 27 is employed as a hole transport material in a hole transporting layer of the device.
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