Materials for organic light emitting devices

Abstract

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.

Description

[0001] Foreignfiling_text P24-239-SEC-WO01 20250919

[0002] 1

[0003] Materials for organic light emitting devices

[0004] 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 5 the second electrode comprising a hole transport region comprising at least two holetransporting layers and an emitting layer.

[0005] 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.

[0006] 15

[0007] 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.

[0008] 20 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 25 efficiently enable the transport of the holes from the anode to the emitting layer.

[0009] 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.

[0010] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0011] 2

[0012] 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 holetransport materials for the hole-transport layers of an electronic device.

[0013] 5

[0014] 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. The compounds lead to high lifetime, high efficiency and low operating voltage of the devices, while having improved capacitance and charging behaviour. Further preferably, the compounds found have a high glass transition temperature, high stability, stable lifetime properties at high temperatures, low sublimation temperature, good solubility, good synthetic accessibility and high conductivity for holes.

[0015] 15 Further, OLEDs comprising the compounds show only a small voltage increase over their lifetime, particularly when the compounds are used in an electron blocking layer, more particularly when used in an OLED stack which has two electron blocking layers which are adjacent to each other, where one of the two electron blocking layers, preferably the one which is not in contact with the emitting layer, comprises a compound according to the 20 invention, and the other comprises a compound with a chemical structure which is not according to the invention. Further, OLEDs comprising the compounds show only a small leakage current, particularly when the compounds are used in an electron blocking layer, more particularly when used in an OLED stack which has two electron blocking layers which are adjacent to each other, where one of the two electron blocking layers, preferably 25 the one which is not in contact with the emitting layer, comprises a compound according to the invention, and the other comprises a compound with a chemical structure which is not according to the invention.

[0016] The present application thus provides an electronic device comprising:

[0017] a first electrode;

[0018] a second electrode facing the first electrode;

[0019] an interlayer between the first electrode and the second electrode and comprising an emitting layer, wherein:

[0020] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0021] 3

[0022] the emitting layer comprises a host material and a dopant, where the dopant is selected from fluorescent emitters and phosphorescent emitters,

[0023] 5 the interlayer further comprises a hole transport region between the emitting layer and the first electrode,

[0024] 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,

[0025] the hole transport layer comprises a compound H selected from triarylamine-based compounds,

[0026] 15

[0027] the first auxiliary layer comprises a compound G1 selected from compounds of formula (II),

[0028] 20

[0029] 25

[0030]

[0031] where the following applies to the symbols and indices occurring: Foreignfiling_text P24-239-SEC-WO01 20250919

[0032] 4

[0033] 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;

[0034] 5 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 R23;

[0035] X1to X8stand on each occurrence, identically or differently, for CR20, CRA, CRBor N; where at least one of X1, X2, X3and X4is bonded to L20and stands for C;

[0036] Z1to Z11stand on each occurrence, identically or differently, for CR21, CRA, CRBor N; where the symbols Z1to Z11which are bonded to an adjacent group stand for C;

[0037] 15 R20, R20a, R20b, R21, R22, R23stand on each occurrence, identically or differently, for RB; or 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 20 more non-adjacent CH2groups 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 25 R21, two radicals R22or / and two radicals R23may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R;

[0038] RAstands on each occurrence, identically or differently, 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 in each case be substituted by one or more radicals Raor RB;

[0039] RBstands on each occurrence, identically or differently, for 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 Rb, where in said alkyl groups one or Foreignfiling_text P24-239-SEC-WO01 20250919

[0040] 5

[0041] 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;

[0042] 5 e1 is an integer from 0 to 5;

[0043] R, Ra, 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 15 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 Raand / or two radicals Rbmay form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R;

[0044] 20 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;

[0045] R stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a 25 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;

[0046] the second auxiliary layer comprises a compound G2;

[0047] characterized in that, in the compound of formula (II), where at least one symbol selected from X1to X8or Z1to Z11stands for CRA. Foreignfiling_text P24-239-SEC-WO01 20250919

[0048] 6

[0049] 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.

[0050] 5 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 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.

[0051] 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

[0052] 15 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 20 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.

[0053] An aryl or heteroaryl group, each of which may be substituted by the abovementioned 25 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, Foreignfiling_text P24-239-SEC-WO01 20250919

[0054] 7

[0055] 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, 5 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.

[0056] 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 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,

[0057] 15 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.

[0058] A heteroaromatic ring system conforms to the abovementioned definition of an aromatic 20 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 25 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. Foreignfiling_text P24-239-SEC-WO01 20250919

[0059] 8

[0060] 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 5 heterocyclic ring or as a ring atom of an aromatic heterocyclic ring.

[0061] 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".

[0062] 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, 15 spiroisotruxene, indenocarbazole, or from combinations of these groups.

[0063] 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 20 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, 25 hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl or octynyl radicals.

[0064] 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- 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0065] 9

[0066] 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, 5 ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio or octynylthio.

[0067] 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 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.

[0068] Preferably, the energy of the highest occupied molecular orbital of the compound H present in the hole-transport layer, HOMO (H), is:

[0069] 15 -5.25 ≤ HOMO (H) ≤ -5.00 eV

[0070] More preferably: -5.20 ≤ HOMO (H) ≤ -5.05 eV

[0071] Particularly preferably: -5.20 ≤ HOMO (H) ≤ -5.10 eV

[0072] 20 Preferably, the energy of the highest occupied molecular orbital of the compound G1 present in the first auxiliary layer, HOMO (G1), is:

[0073] -5.30 ≤ HOMO (G1) ≤ -5.05 eV

[0074] More preferably: -5.25 ≤ HOMO (G1) ≤ -5.10 eV

[0075] 25 Particularly preferably: -5.20 ≤ HOMO (G1) ≤ -5.10 eV

[0076] Preferably, the energy of the highest occupied molecular orbital of the compound G2 present in the first auxiliary layer, HOMO (G2), is:

[0077] -5.50 ≤ HOMO (G2) ≤ -5.20 eV

[0078] More preferably: -5.40 ≤ HOMO (G2) ≤ -5.20 eV

[0079] Particularly preferably: -5.40 ≤ HOMO (G2) ≤ -5.25 eV

[0080] 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 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0081] 10

[0082] 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 5 transitions) are computed using the optimized ground state geometry and the same method (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 "6-31 G(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:

[0083] HOMO(eV) = (HEh*0.90603) - 0.84836

[0084] LUMO(eV) = (LEh*0.99687) - 0.72445

[0085] 15 For the purposes of this application, these values are to be regarded as HOMO and LUMO energy levels respectively of the materials.

[0086] 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.

[0087] The lowest excited singlet state S1 is defined as the energy of the excited singlet state 20 having the lowest energy which arises from the quantum-chemical calculation described.

[0088] 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.).

[0089] 25 Preferably, the refractive index of the compound G1 present in the first auxiliary layer at 450 nm, RI (@450nm, G1), is:

[0090] RI (@450nm, G1) ≤ 1.83

[0091] More preferably: ≤ 1.80

[0092] Particularly preferably: ≤ 1.75

[0093] The refractive index at the wavelength of 450nm of layer is determined via Ellipsometer (J. A. Wollam Inc., USA). The measurement system covers the wavelength from 250 to 1000nm, the values are determined from the dispersion curve. The samples are fabricated 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0094] 11

[0095] and prepared on SiO2substrates, in there, examples are evaporated with three different layer thicknesses. And the refractive index as an average value are determined from the samples.

[0096] 5 Preferably, in the compound of formula (II), e1 is larger than 0.

[0097] Preferably, the compound of formula (II) comprises at least one, two, three or four symbols selected from X1to X8or Z1to Z11, which stand for CRA.

[0098] Preferably, in formula (II), one of the following conditions applies:

[0099] (0-1) one symbol selected from X5to X8and Z1to Z5stands for CRA;

[0100] (0-2) one symbol selected from X5and Z1to Z5stands for CRA;

[0101] (0-3) one symbol selected from X5, Z1and Z4stands for CRA;

[0102] (0-4) one symbol selected from X5and Z4stands for CRA.

[0103] 15

[0104] Preferably, the compound of formula (II) comprises at least one, two, three, four or five RB(s).

[0105] Preferably, in formula (II), at least one symbol selected from Z1to Z11and X1to X8stands 20 for CRB, at least one of R23stand for RB, and / or at least one of RAsubstituted by one or more radicals RB.

[0106] Preferably, in formula (II), at least one of the following conditions applies:

[0107] (1-1) at least one symbol selected from Z1to Z5stand(s) for CRB;

[0108] 25 (1-2) at least one symbol selected from Z6to Z11stand(s) for CRB;

[0109] (1-3) at least one symbol selected from X1to X4stand(s) for CRB;

[0110] (1-4) at least one symbol selected from X5to X8stand(s) for CRB;

[0111] (1-5) at least one of R23stand(s) for RB;

[0112] (1-6) at least one of RAsubstituted by one or more radicals RB.

[0113] Preferably, in formula (II), at least one of the following conditions applies:

[0114] (2-1) one or two symbols selected from Z1to Z5stand(s) for CRB;

[0115] (2-2) one or two symbols selected from Z6to Z11stand(s) for CRB;

[0116] (2-3) one symbol selected from Z1to Z5and one symbol selected from Z6to Z11stand for 35 CRB; Foreignfiling_text P24-239-SEC-WO01 20250919

[0117] 12

[0118] (2-4) one symbol selected from Z1to Z5and two symbols selected from Z6to Z11stand for CRB;

[0119] (2-5) two symbols selected from Z1to Z5and one symbol selected from Z6to Z11stand for CRB;

[0120] 5 (2-6) two symbols selected from Z1to Z5and two symbols selected from Z6to Z11stand for CRB;

[0121] (2-7) one or two symbols selected from X1to X4stand(s) for CRB;

[0122] (2-8) one or two symbols selected from X5to X8stand(s) for CRB;

[0123] (2-9) one symbol selected from X1to X4and one symbol selected from X5to X8stand for CRB;

[0124] (2-10) one symbol selected from X1to X4and two symbols selected from X5to X8stand for CRB;

[0125] (2-11) two symbols selected from X1to X4and two symbols selected from X5to X8stand for CRB;

[0126] 15 (2-12) one, two, three or four of R23stand(s) for RB;

[0127] (2-13) at least one of RAsubstituted by one, two, three or four of radicals RB;

[0128] (2-14) one symbol selected from Z1to Z5, one symbol selected from Z6to Z11stand for CRBand at least one of RAsubstituted by one or two radicals RB;

[0129] (2-15) one symbol selected from X5to X8stand for CRBand and at least one of RA

[0130] 20 substituted by one or two radicals RB;

[0131] (2-16) two symbols selected from Z6to Z11stand for CRBand at least one of RAsubstituted by one or two radicals RB.

[0132] Preferably, in formula (II), X2is connected with L20or when L20is a single bond, N atom of 25 amine.

[0133] Preferably, the compound G1 selected from compounds of formula (II-1-A) and formula (II- 1-B):

[0134] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0135] 13

[0136] 5

[0137]

[0138] 15

[0139] 20

[0140] 25

[0141]

[0142] Formula (II-1-B)

[0143] where the symbols X1to X8, L20, L21, L22, Ar22, Z2to Z11, R20a, R20b, RBand e1 have the same meaning as above;

[0144] where the compound of formula (II-1-A) comprises at least one symbol selected from X1to X8, Z2to Z5and Z6to Z10, which stands for CRA;

[0145] where the compound of formula (II-1-B) comprises at least one symbol selected from X1to 35 X8, Z3to Z5and Z6to Z9, which stands for CRA; Foreignfiling_text P24-239-SEC-WO01 20250919

[0146] 14

[0147] T20is O, S or C(R21a)(R21b); and

[0148] R21aand R21beach have the same meaning as R21above.

[0149] Preferably, in formula (II-1-A), at least one symbol selected from Z2to Z10and X1to X85 stands for CRB, at least one of R23stand for RB, and / or at least one of RAsubstituted by one or more radicals RB.

[0150] Preferably, in formula (II-1-A), at least one of the following conditions applies:

[0151] (3-1) one or two symbols selected from Z2to Z5stand(s) for CRB;

[0152] (3-2) one or two symbols selected from Z6to Z10stand(s) for CRB;

[0153] (3-3) one symbol selected from Z2to Z5and one symbol selected from Z6to Z10stand for CRB;

[0154] (3-4) one symbol selected from Z2to Z5and two symbols selected from Z6to Z10stand for 15 CRB;

[0155] (3-5) two symbols selected from Z2to Z5and one symbol selected from Z6to Z10stand for CRB;

[0156] (3-6) two symbols selected from Z2to Z5and two symbols selected from Z6to Z10stand for CRB;

[0157] 20 (3-7) one or two symbols selected from X1to X4stand(s) for CRB;

[0158] (3-8) one or two symbols selected from X5to X8stand(s) for CRB;

[0159] (3-9) one symbol selected from X1to X4and one symbol selected from X5to X8stand for CRB;

[0160] (3-10) one symbol selected from X1to X4and two symbols selected from X5to X8stand for 25 CRB;

[0161] (3-11) two symbols selected from X1to X4and two symbols selected from X5to X8stand for CRB;

[0162] (3-12) one, two, three or four of R23stand(s) for RB;

[0163] (3-13) at least one of RAsubstituted by one, two, three or four of radicals RB;

[0164] (3-14) one symbol selected from Z2to Z5, one symbol selected from Z6to Z10stand for CRBand at least one of RAsubstituted by one or two radicals RB;

[0165] (3-15) one symbol selected from X5to X8stand for CRBand and at least one of RAsubstituted by one or two radicals RB;

[0166] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0167] 15

[0168] (3-16) two symbols selected from Z6to Z10stand for CRBand at least one of RAsubstituted by one or two radicals RB.

[0169] 5 Preferably, in formula (II-1-B), at least one symbol selected from Z3to Z9and X1to X8stands for CRB, at least one of R23stand for RB, and / or at least one of RAsubstituted by one or more radicals RB.

[0170] Preferably, in formula (II-1-B), at least one of the following conditions applies:

[0171] (4-1) one or two symbols selected from Z3to Z5stand(s) for CRB;

[0172] (4-2) one or two symbols selected from Z6to Z9stand(s) for CRB;

[0173] (4-3) one symbol selected from Z3to Z5and one symbol selected from Z6to Z9stand for CRB;

[0174] 15 (4-4) one symbol selected from Z3to Z5and two symbols selected from Z6to Z9stand for CRB;

[0175] (4-5) two symbols selected from Z3to Z5and one symbol selected from Z6to Z9stand for CRB;

[0176] (4-6) two symbols selected from Z3to Z5and two symbols selected from Z6to Z9stand for 20 CRB;

[0177] (4-7) one or two symbols selected from X1to X4stand(s) for CRB;

[0178] (4-8) one or two symbols selected from X5to X8stand(s) for CRB;

[0179] (4-9) one symbol selected from X1to X4and one symbol selected from X5to X8stand for CRB;

[0180] 25 (4-10) one symbol selected from X1to X4and two symbols selected from X5to X8stand for CRB;

[0181] (4-11) two symbols selected from X1to X4and two symbols selected from X5to X8stand for CRB;

[0182] (4-12) one, two, three or four of R23stand(s) for RB;

[0183] (4-13) at least one of RAsubstituted by one, two, three or four of radicals RB;

[0184] (4-14) one symbol selected from Z3to Z5, one symbol selected from Z6to Z9stand for CRBand at least one of RAsubstituted by one or two radicals RB;

[0185] (4-15) one symbol selected from X5to X8stand for CRBand and at least one of RAsubstituted by one or two radicals RB;

[0186] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0187] 16

[0188] (4-16) two symbols selected from Z6to Z9stand for CRBand at least one of RAsubstituted by one or two radicals RB.

[0189] Preferably, the radical RAstands on each occurrence, identically or differently, for an 5 aromatic ring system having 6 to 40, preferably 6 to 25 aromatic ring atoms or heteroaromatic ring system having 5 to 40, preferably 6 to 25 aromatic ring atoms, which may in each case be substituted by one or more radicals Raor RB. More preferably, the radical RAstands on each occurrence, identically or differently, 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 or triazinyl, which may in each case be substituted by one or more radicals Raor RB. Very preferably, the radical RAstands on each occurrence, identically or differently, for an aromatic ring system having 6 to 25 aromatic ring atoms, which may in 15 each case be substituted by one or more radicals Raor RB. Particularly preferably, the radical RAstands on each occurrence, identically or differently, for phenyl, biphenyl, terphenyl, naphthyl or fluorenyl, especially 9,9'-dimethylfluorenyl and 9,9'-diphenylfluorenyl, which may in each case be substituted by one or more radicals Raor RB, most particularly preferably, the radical RAstands on each occurrence, identically or differently, for phenyl or 20 biphenyl, which may in each case be substituted by one or more radicals Raor RB.

[0190] Preferably, the radical RBstands for a straight-chain alkyl group having 1 to 10, preferably 1 to 6, more preferbaly 1 to 4 C atoms or branched or a cyclic alkyl group having 3 to 10, preferably 3 to 6 C atoms, each of which may be substituted by one or more radicals Rb, 25 where in said alkyl groups one or more H atoms may be replaced by D or F; and where two radicals RBmay form an aliphatic ring system together, which may be substituted by one or more radicals Rb.

[0191] Suitable examples of radicals RBare the groups (R-1) to (R-35) as depicted in the table below:

[0192] CH3CH2-CH3

[0193]

[0194] R-1 R-2 R-3

[0195] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0196] — CF3 — CF2CF3 —

[0197] R-4 R-5 R-6 5 OCF3SCF3 SF5

[0198] R-7 R-8 R-9 OCF2CF3 SCF2CF3

[0199] R-10 R-11 R-12

[0200] J— 1... A

[0201] R-13 R-14 R-15 15

[0202] F SCH2CH3 OCH2CH3

[0203] R-16 R-17 R-18 OCH3 SCH3 Si(CH3)3 20

[0204] R-19 R-20 R-21 Si(CH3)2(t-Bu) Si(iPr)3Si(CH3)2Ph

[0205] R-22 R-23 R-24 Si(Ph)3C(Ph)3CD3 25

[0206] R-25 R-26 R-27 CD-(CD3)2 CD2-CD3 C(CD3)3

[0207] R-28 R-29 R-30 CD2-C-(CD3)3 OCD3 SCD3

[0208] R-31 R-32 R-33 Si(CD3)3CH2-C-(CH3)3 CD2-CD-(CD3)2

[0209] 35

[0210]

[0211] R-34 R-35 R-36 Foreignfiling_text P24-239-SEC-WO01 20250919

[0212] 18

[0213] Where the dashed bond indicates the connection of the group RBto 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.

[0214] 5

[0215] When two radicals RBform an aliphatic ring system together, then they preferably form an aliphatic ring system of one of the formulae (RB-1) to (RB-7) below:

[0216] 15

[0217] 20

[0218]

[0219] (RB-5) (RB-6) (RB-7)

[0220] where

[0221] 25 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)2 or (Rb)2C-C(Rb)2;

[0222] Rband Ar have the same meaning as above; and

[0223] where the dashed bonds represent the connection of the ring formed by two radicals RBto the compound G1.

[0224] 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 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0225] 19

[0226] 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 5 radicals R.

[0227] Preferably, the compound G1 selected from compounds of formula (II-1-A) and formula (II- 1-B).

[0228] Preferably, a compound G1 selected from compounds of formula (II-2) and (II-3):

[0229] 15

[0230] 20

[0231]

[0232] Formula (II-2)

[0233] 25

[0234] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0235] 5

[0236]

[0237] Formula (II-3)

[0238] 15

[0239] where the symbols X1to X8, L20, L21, L22, Ar22, Z1to Z11, R20a, R20b, RA, RBand e1 have the same meaning as above;

[0240] Z12to Z17stand on each occurrence, identically or differently, for CR21, CRBor N; where the symbols Z12to Z17which are bonded to an adjacent group stand for C; and R21has the 20 same meaning as above.

[0241] Preferably, in formula (II-2), at least one symbol selected from Z1to Z3, Z5to Z11and X1to X8stands for CRB, at least one of R23stand for RB, and / or at least one of RAsubstituted by one or more radicals RB.

[0242] 25

[0243] Preferably, in formula (II-3), at least one symbol selected from Z1to Z11, X1to X4and X6to X8stands for CRB, at least one of R23stand for RB, and / or at least one of RAsubstituted by one or more radicals RB.

[0244] Preferably, the compound G1 selected from compounds of formula (II-2-1-A), (II-3-1-A) and formula (II-3-1-B):

[0245] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0246] 21

[0247] Formula (11-3-1-A)

[0248]

[0249] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0250] 22

[0251] 5

[0252]

[0253] where the symbols X1to X8, L20, L21, L22, Ar22, Z2to Z10, R20a, R20b, T20, RA, RBand e1 have 15 the same meaning as above.

[0254] Preferably, in formula (11-2-1 -A), at least one symbol selected from Z2, Z3, Z5to Z10and X1to X8stands for CRB, at least one of R23stand for RB, and / or at least one of RAsubstituted by one or more radicals RB.

[0255] 20

[0256] Preferably, in formula (11-2-1 -A), at least one of the following conditions applies:

[0257] (5-1) one or two symbols selected from Z2, Z3and Z5stand(s) for CRB;

[0258] (5-2) one or two symbols selected from Z6to Z10stand(s) for CRB;

[0259] 25 (5-3) one symbol selected from Z2to Z5and one symbol selected from Z6to Z10stand for CRB;

[0260] (5-4) one symbol selected from Z2to Z5and two symbols selected from Z6to Z10stand for CRB;

[0261] (5-5) two symbols selected from Z2to Z5and one symbol selected from Z6to Z10stand for CRB;

[0262] (5-6) two symbols selected from Z2to Z5and two symbols selected from Z6to Z10stand for CRB;

[0263] (5-7) one or two symbols selected from X1to X4stand(s) for CRB;

[0264] (5-8) one or two symbols selected from X5to X8stand(s) for CRB;

[0265] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0266] 23

[0267] (5-9) one symbol selected from X1to X4and one symbol selected from X5to X8stand for CRB;

[0268] (5-10) one symbol selected from X1to X4and two symbols selected from X5to X8stand for CRB;

[0269] 5 (5-11) two symbols selected from X1to X4and two symbols selected from X5to X8stand for CRB;

[0270] (5-12) one, two, three or four of R23stand(s) for RB;

[0271] (5-13) at least one of RAsubstituted by one, two, three or four of radicals RB;

[0272] (5-14) one symbol selected from Z2to Z5, one symbol selected from Z6to Z10stand for CRBand at least one of RAsubstituted by one or two radicals RB;

[0273] (5-15) one symbol selected from X5to X8stand for CRBand and at least one of RAsubstituted by one or two radicals RB;

[0274] (5-16) two symbols selected from Z6to Z10stand for CRBand at least one of RAsubstituted by one or two radicals RB.

[0275] 15

[0276] Preferably, in formula (11-3-1 -A), at least one symbol selected from Z2to Z10, X1to X4and X6to X8stands for CRB, at least one of R23stand for RB, and / or at least one of RAsubstituted by one or more radicals RB.

[0277] 20 Preferably, in formula (11-3-1 -A), at least one of the following conditions applies:

[0278] (6-1) one or two symbols selected from Z2to Z5stand(s) for CRB;

[0279] (6-2) one or two symbols selected from Z6to Z10stand(s) for CRB;

[0280] (6-3) one symbol selected from Z2to Z5and one symbol selected from Z6to Z10stand for 25 CRB;

[0281] (6-4) one symbol selected from Z2to Z5and two symbols selected from Z6to Z10stand for CRB;

[0282] (6-5) two symbols selected from Z2to Z5and one symbol selected from Z6to Z10stand for CRB;

[0283] (6-6) two symbols selected from Z2to Z5and two symbols selected from Z6to Z10stand for CRB;

[0284] (6-7) one or two symbols selected from X1to X4stand(s) for CRB;

[0285] (6-8) one or two symbols selected from X6to X8stand(s) for CRB;

[0286] (6-9) one symbol selected from X1to X4and one symbol selected from X6to X8stand for 35 CRB; Foreignfiling_text P24-239-SEC-WO01 20250919

[0287] 24

[0288] (6-10) one symbol selected from X1to X4and two symbols selected from X6to X8stand for CRB;

[0289] (6-11) two symbols selected from X1to X4and two symbols selected from X6to X8stand for CRB;

[0290] 5 (6-12) one, two, three or four of R23stand(s) for RB;

[0291] (6-13) at least one of RAsubstituted by one, two, three or four of radicals RB;

[0292] (6-14) one symbol selected from Z2to Z5, one symbol selected from Z6to Z10stand for CRBand at least one of RAsubstituted by one or two radicals RB;

[0293] (6-15) one symbol selected from X5to X8stand for CRBand and at least one of RAsubstituted by one or two radicals RB;

[0294] (6-16) two symbols selected from Z6to Z10stand for CRBand at least one of RAsubstituted by one or two radicals RB.

[0295] Preferably, in formula (11-3-1 -B), at least one symbol selected from Z3to Z9, X1to X4and X615 to X8stands for CRB, at least one of R23stand for RB, and / or at least one of RAsubstituted by one or more radicals RB.

[0296] Preferably, in formula (11-3-1 -B), at least one of the following conditions applies:

[0297] 20 (7-1) one or two symbols selected from Z3to Z5stand(s) for CRB;

[0298] (7-2) one or two symbols selected from Z6to Z9stand(s) for CRB;

[0299] (7-3) one symbol selected from Z3to Z5and one symbol selected from Z6to Z9stand for CRB;

[0300] (7-4) one symbol selected from Z3to Z5and two symbols selected from Z6to Z9stand for 25 CRB;

[0301] (7-5) two symbols selected from Z3to Z5and one symbol selected from Z6to Z9stand for CRB;

[0302] (7-6) two symbols selected from Z3to Z5and two symbols selected from Z6to Z9stand for CRB;

[0303] (7-7) one or two symbols selected from X1to X4stand(s) for CRB;

[0304] (7-8) one or two symbols selected from X6to X8stand(s) for CRB;

[0305] (7-9) one symbol selected from X1to X4and one symbol selected from X6to X8stand for CRB;

[0306] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0307] 25

[0308] (7-10) one symbol selected from X1to X4and two symbols selected from X6to X8stand for CRB;

[0309] (7-11) two symbols selected from X1to X4and two symbols selected from X6to X8stand for CRB;

[0310] 5 (7-12) one, two, three or four of R23stand(s) for RB;

[0311] (7-13) at least one of RAsubstituted by one, two, three or four of radicals RB;

[0312] (7-14) one symbol selected from Z3to Z5, one symbol selected from Z6to Z9stand for CRBand at least one of RAsubstituted by one or two radicals RB;

[0313] (7-15) one symbol selected from X5to X8stand for CRBand and at least one of RAsubstituted by one or two radicals RB;

[0314] (7-16) two symbols selected from Z6to Z9stand for CRBand at least one of RAsubstituted by one or two radicals RB.

[0315] Preferably, the compound G1 selected from compounds of formula (II-4) and formula (II-5): 15

[0316] 20

[0317] 25

[0318]

[0319] Formula (I I-4)

[0320] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0321] 5

[0322] 15

[0323]

[0324] where the symbols X1to X8, L20, L21, L22, Ar22, Z1to Z11, R20a, R20b, RBand e1 have the same meaning as above;

[0325] 20 Z12to Z17stand on each occurrence, identically or differently, for CR21, CRBor N; where the symbols Z12to Z17which are bonded to an adjacent group stand for C; and R21has the same meaning as above.

[0326] Preferably, in formula (II-4), at least one symbol selected from Z1to Z17and X1to X8stands 25 for CRB, at least one of R23stand for RB, and / or at least one of RAsubstituted by one or more radicals RB.

[0327] Preferably, in formula (II-4), at least one of the following conditions applies:

[0328] (8-1) one or two symbols selected from Z1to Z5stand(s) for CRB;

[0329] (8-2) one or two symbols selected from Z6to Z11stand(s) for CRB;

[0330] (8-3) one or two symbols selected from Z12to Z17stand(s) for CRB;

[0331] (8-4) one symbol selected from Z6to Z11and one symbol selected from Z12to Z17stand for CRB;

[0332] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0333] 27

[0334] (8-5) one symbol selected from Z6to Z11and two symbols selected from Z12to Z17stand for CRB;

[0335] (8-6) two symbols selected from Z6to Z11and one symbol selected from Z12to Z17stand for CRB;

[0336] 5 (8-7) two symbols selected from Z6to Z11and two symbols selected from Z12to Z17stand for CRB;

[0337] (8-8) one or two symbols selected from X1to X4stand(s) for CRB;

[0338] (8-9) one or two symbols selected from X5to X8stand(s) for CRB;

[0339] (8-10) one symbol selected from X1to X4and one symbol selected from X5to X8stand for CRB;

[0340] (8-11) one symbol selected from X1to X4and two symbols selected from X5to X8stand for CRB;

[0341] (8-12) two symbols selected from X1to X4and two symbols selected from X5to X8stand for CRB;

[0342] 15 (8-13) one, two, three or four of R23stand(s) for RB.

[0343] Preferably, in formula (I I-5), at least one symbol selected from Z1to Z17and X1to X8stands for CRB, at least one of R23stand for RB, and / or at least one of RAsubstituted by one or more radicals RB.

[0344] 20

[0345] Preferably, in formula (II-5), at least one of the following conditions applies:

[0346] (9-1) one or two symbols selected from Z1to Z5stand(s) for CRB;

[0347] (9-2) one or two symbols selected from Z6to Z11stand(s) for CRB;

[0348] 25 (9-3) one or two symbols selected from Z12to Z17stand(s) for CRB;

[0349] (9-4) one symbol selected from Z1to Z5and one symbol selected from Z6to Z11stand for CRB;

[0350] (9-5) one symbol selected from Z1to Z5and two symbols selected from Z6to Z11stand for CRB;

[0351] (9-6) two symbols selected from Z1to Z5and one symbol selected from Z6to Z11stand for CRB;

[0352] (9-7) two symbols selected from Z1to Z5and two symbols selected from Z6to Z11stand for CRB;

[0353] (9-8) one or two symbols selected from X1to X4stand(s) for CRB;

[0354] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0355] 28

[0356] (9-9) one or two symbols selected from X5to X8stand(s) for CRB;

[0357] (9-10) one symbol selected from X1to X4and one symbol selected from X5to X8stand for CRB;

[0358] (9-11) one symbol selected from X1to X4and one or two symbols selected from Z12to Z175 stand for CRB;

[0359] (9-12) one symbol selected from X5to X8and one or two symbols selected from Z12to Z17stand for CRB;

[0360] (9-13) one, two, three or four of R23stand(s) for RB;

[0361] (9-14) one symbol selected from Z1to Z5, one symbol selected from Z6to Z11stand for CRBand one or two symbols selected from Z12to Z17stand for CRB;

[0362] (9-15) two symbols selected from Z6to Z11stand for CRBand one or two symbols selected from Z12to Z17stand for CRB.

[0363] Preferably, the compound G1 selected from compounds of formula (II-4-1-A), (II-5-1-A) and 15 (II-5-1-B):

[0364] 20

[0365] 25

[0366]

[0367] Formula (II-4-1-A)

[0368] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0369] 29

[0370] 5

[0371]

[0372] Formula (II-5-1-A)

[0373] 15

[0374] 20

[0375] 25

[0376]

[0377] Formula (II-5-1-B)

[0378] where the symbols X1to X8, L20, L21, L22, Ar22, Z2to Z10, Z12to Z16, R20a, R20b, T20, RBand e1 have the same meaning as above.

[0379] Preferably, in formula (11-4-1 -A), at least one symbol selected from Z2, Z3, Z5to Z10, Z12to Z16and X1to X8stands for CRB, at least one of R23stand for RB, and / or at least one of RAsubstituted by one or more radicals RB.

[0380] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0381] 30

[0382] Preferably, in formula (11-4-1 -A), at least one of the following conditions applies:

[0383] (10-1) one or two symbols selected from Z2, Z3and Z5stand(s) for CRB;

[0384] 5 (10-2) one or two symbols selected from Z6to Z10stand(s) for CRB;

[0385] (10-3) one or two symbols selected from Z12to Z16stand(s) for CRB;

[0386] (10-4) one symbol selected from Z6to Z10and one symbol selected from Z12to Z16stand for CRB;

[0387] (10-5) one symbol selected from Z6to Z10and two symbols selected from Z12to Z16stand for CRB;

[0388] (10-6) two symbols selected from Z6to Z10and one symbol selected from Z12to Z16stand for CRB;

[0389] (10-7) two symbols selected from Z6to Z10and two symbols selected from Z12to Z16stand for CRB;

[0390] 15 (10-8) one or two symbols selected from X1to X4stand(s) for CRB;

[0391] (10-9) one or two symbols selected from X5to X8stand(s) for CRB;

[0392] (10-10) one symbol selected from X1to X4and one symbol selected from X5to X8stand for CRB;

[0393] (10-11) one symbol selected from X1to X4and two symbols selected from X5to X8stand 20 for CRB;

[0394] (10-12) two symbols selected from X1to X4and two symbols selected from X5to X8stand for CRB;

[0395] (10-13) one, two, three or four of R23stand(s) for RB.

[0396] 25 Preferably, in formula (11-5-1 -A), at least one symbol selected from Z2to Z10, Z12to Z16, X1to X4and X6to X8stands for CRB, at least one of R23stand for RB, and / or at least one of RAsubstituted by one or more radicals RB.

[0397] Preferably, in formula (11-5-1 -A), at least one of the following conditions applies:

[0398] (11-1) one or two symbols selected from Z2to Z5stand(s) for CRB;

[0399] (11-2) one or two symbols selected from Z6to Z10stand(s) for CRB;

[0400] (11-3) one or two symbols selected from Z12to Z16stand(s) for CRB;

[0401] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0402] 31

[0403] (11-4) one symbol selected from Z2to Z5and one symbol selected from Z6to Z10stand for CRB;

[0404] (11-5) one symbol selected from Z2to Z5and two symbols selected from Z6to Z10stand for CRB;

[0405] 5 (11-6) two symbols selected from Z2to Z5and one symbol selected from Z6to Z10stand for CRB;

[0406] (11-7) two symbols selected from Z2to Z5and two symbols selected from Z6to Z10stand for CRB;

[0407] (11-8) one or two symbols selected from X1to X4stand(s) for CRB;

[0408] (11-9) one or two symbols selected from X6to X8stand(s) for CRB;

[0409] (11-10) one symbol selected from X1to X4and one symbol selected from X6to X8stand for CRB;

[0410] (11-11) one symbol selected from X1to X4and one or two symbols selected from Z12to Z16stand for CRB;

[0411] 15 (11-12) one symbol selected from X6to X8and one or two symbols selected from Z12to Z16stand for CRB;

[0412] (11-13) one, two, three or four of R23stand(s) for RB;

[0413] (11-14) one symbol selected from Z2to Z5, one symbol selected from Z6to Z10stand for CRBand one or two symbols selected from Z12to Z16stand for CRB;

[0414] 20 (11-15) two symbols selected from Z6to Z10stand for CRBand one or two symbols selected from Z12to Z16stand for CRB.

[0415] Preferably, in formula (11-5-1 -B), at least one symbol selected from Z3to Z9, Z12to Z16, X1to X4and X6to X8stands for CRB, at least one of R23stand for RB, and / or at least one of RA25 substituted by one or more radicals RB.

[0416] Preferably, in formula (11-5-1 -B), at least one of the following conditions applies:

[0417] (12-1) one or two symbols selected from Z3to Z5stand(s) for CRB;

[0418] (12-2) one or two symbols selected from Z6to Z9stand(s) for CRB;

[0419] (12-3) one or two symbols selected from Z12to Z16stand(s) for CRB;

[0420] (12-4) one symbol selected from Z3to Z5and one symbol selected from Z6to Z9stand for CRB;

[0421] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0422] 32

[0423] (12-5) one symbol selected from Z3to Z5and two symbols selected from Z6to Z9stand for CRB;

[0424] (12-6) two symbols selected from Z3to Z5and one symbol selected from Z6to Z9stand for CRB;

[0425] 5 (12-7) two symbols selected from Z3to Z5and two symbols selected from Z6to Z9stand for CRB;

[0426] (12-8) one or two symbols selected from X1to X4stand(s) for CRB;

[0427] (12-9) one or two symbols selected from X6to X8stand(s) for CRB;

[0428] (12-10) one symbol selected from X1to X4and one symbol selected from X6to X8stand for CRB;

[0429] (12-11) one symbol selected from X1to X4and one or two symbols selected from Z12to Z16stand for CRB;

[0430] (12-12) one symbol selected from X6to X8and one or two symbols selected from Z12to Z16stand for CRB;

[0431] 15 (12-13) one, two, three or four of R23stand(s) for RB;

[0432] (12-14) one symbol selected from Z3to Z5, one symbol selected from Z6to Z9stand for CRBand one or two symbols selected from Z12to Z16stand for CRB;

[0433] (12-15) two symbols selected from Z6to Z9stand for CRBand one or two symbols selected from Z12to Z16stand for CRB.

[0434] 20

[0435] Preferably, the compound G1 selected from compounds of formula (II-6-1-A), (II-7-1-A) and (II-7-1-B):

[0436] 25

[0437] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0438] 5

[0439]

[0440] 15

[0441] Formula (11-6-1 -A)

[0442] 20

[0443] 25

[0444]

[0445] Formula (II-7-1-A)

[0446] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0447] 5

[0448] 15

[0449]

[0450] where the symbols X1, X3to X8, L20, L21, L22, Ar22, Z2to Z10, Z12to Z16, R20a, R20b, T20, RBand 20 e1 have the same meaning as above.

[0451] Preferably, in formula (11-6-1 -A), at least one symbol selected from Z2, Z3, Z5to Z10, Z12to Z16, X1and X3to X8stands for CRB, at least one of R23stand for RB, and / or at least one of RAsubstituted by one or more radicals RB.

[0452] 25

[0453] Preferably, in formula (11-6-1 -A), at least one of the following conditions applies:

[0454] (13-1) one or two symbols selected from Z2, Z3and Z5stand(s) for CRB;

[0455] (13-2) one or two symbols selected from Z6to Z10stand(s) for CRB;

[0456] (13-3) one or two symbols selected from Z12to Z16stand(s) for CRB;

[0457] (13-4) one symbol selected from Z6to Z10and one symbol selected from Z12to Z16stand for CRB;

[0458] (13-5) one symbol selected from Z6to Z10and two symbols selected from Z12to Z16stand for CRB;

[0459] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0460] 35

[0461] (13-6) two symbols selected from Z6to Z10and one symbol selected from Z12to Z16stand for CRB;

[0462] (13-7) two symbols selected from Z6to Z10and two symbols selected from Z12to Z16stand for CRB;

[0463] 5 (13-8) one or two symbols selected from X1, X3and X4stand(s) for CRB;

[0464] (13-9) one or two symbols selected from X5to X8stand(s) for CRB;

[0465] (13-10) one symbol selected from X1, X3and X4and one symbol selected from X5to X8stand for CRB;

[0466] (13-11) one symbol selected from X1, X3and X4and two symbols selected from X5to X8stand for CRB;

[0467] (13-12) two symbols selected from X1, X3and X4and two symbols selected from X5to X8stand for CRB;

[0468] (13-13) one, two, three or four of R23stand(s) for RB.

[0469] 15 Preferably, in formula (11-7-1 -A), at least one symbol selected from Z2to Z10, Z12to Z16, X1, X3, X4and X6to X8stands for CRB, at least one of R23stand for RB, and / or at least one of RAsubstituted by one or more radicals RB.

[0470] Preferably, in formula (11-7-1 -A), at least one of the following conditions applies:

[0471] 20

[0472] (14-1) one or two symbols selected from Z2to Z5stand(s) for CRB;

[0473] (14-2) one or two symbols selected from Z6to Z10stand(s) for CRB;

[0474] (14-3) one or two symbols selected from Z12to Z16stand(s) for CRB;

[0475] (14-4) one symbol selected from Z2to Z5and one symbol selected from Z6to Z10stand for 25 CRB;

[0476] (14-5) one symbol selected from Z2to Z5and two symbols selected from Z6to Z10stand for CRB;

[0477] (14-6) two symbols selected from Z2to Z5and one symbol selected from Z6to Z10stand for CRB;

[0478] (14-7) two symbols selected from Z2to Z5and two symbols selected from Z6to Z10stand for CRB;

[0479] (14-8) one or two symbols selected from X1, X3and X4stand(s) for CRB;

[0480] (14-9) one or two symbols selected from X6to X8stand(s) for CRB; Foreignfiling_text P24-239-SEC-WO01 20250919

[0481] 36

[0482] (14-10) one symbol selected from X1, X3and X4and one symbol selected from X6to X8stand for CRB;

[0483] (14-11) one symbol selected from X1, X3and X4and one or two symbols selected from Z12to Z16stand for CRB;

[0484] 5 (14-12) one symbol selected from X6to X8and one or two symbols selected from Z12to Z16stand for CRB;

[0485] (14-13) one, two, three or four of R23stand(s) for RB;

[0486] (14-14) one symbol selected from Z2to Z5, one symbol selected from Z6to Z10stand for CRBand one or two symbols selected from Z12to Z16stand for CRB;

[0487] (14-15) two symbols selected from Z6to Z10stand for CRBand one or two symbols selected from Z12to Z16stand for CRB.

[0488] Preferably, in formula (11-7-1 -B), at least one symbol selected from Z3to Z9, Z12to Z16, X1, X3, X4and X6to X8stands for CRB, at least one of R23stand for RB, and / or at least one of RA15 substituted by one or more radicals RB.

[0489] Preferably, in formula (11-7-1 -B), at least one of the following conditions applies:

[0490] (15-1) one or two symbols selected from Z3to Z5stand(s) for CRB;

[0491] 20 (15-2) one or two symbols selected from Z6to Z9stand(s) for CRB;

[0492] (15-3) one or two symbols selected from Z12to Z16stand(s) for CRB;

[0493] (15-4) one symbol selected from Z3to Z5and one symbol selected from Z6to Z9stand for CRB;

[0494] (15-5) one symbol selected from Z3to Z5and two symbols selected from Z6to Z9stand for 25 CRB;

[0495] (15-6) two symbols selected from Z3to Z5and one symbol selected from Z6to Z9stand for CRB;

[0496] (15-7) two symbols selected from Z3to Z5and two symbols selected from Z6to Z9stand for CRB;

[0497] (15-8) one or two symbols selected from X1, X3and X4stand(s) for CRB;

[0498] (15-9) one or two symbols selected from X6to X8stand(s) for CRB;

[0499] (15-10) one symbol selected from X1, X3and X4and one symbol selected from X6to X8stand for CRB; Foreignfiling_text P24-239-SEC-WO01 20250919

[0500] 37

[0501] (15-11) one symbol selected from X1, X3and X4and one or two symbols selected from Z12to Z16stand for CRB;

[0502] (15-12) one symbol selected from X6to X8and one or two symbols selected from Z12to Z16stand for CRB;

[0503] 5 (15-13) one, two, three or four of R23stand(s) for RB;

[0504] (15-14) one symbol selected from Z3to Z5, one symbol selected from Z6to Z9stand for CRBand one or two symbols selected from Z12to Z16stand for CRB;

[0505] (15-15) two symbols selected from Z6to Z9stand for CRBand one or two symbols selected from Z12to Z16stand for CRB.

[0506] 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 15 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 20 dibenzothiophenyl, and carbazolyl, which may be substituted by one or more radicals R22.

[0507] 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.

[0508] Preferably, Ar22stands for an aromatic ring system having 6 to 30, preferably 6 to 25, more 25 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.

[0509] 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. Foreignfiling_text P24-239-SEC-WO01 20250919

[0510] 38

[0511] 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, 5 dibenzothiophenyl, benzofuranyl, benzothiophenyl, benzofused dibenzofuranyl, benzofused dibenzothiophenyl, naphthyl-substituted phenyl, fluorenyl-substituted phenyl, spirobifluorenyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzothiophenylsubstituted phenyl, pyridyl-substituted phenyl, pyrimidyl-substituted phenyl, and triazinyl- substituted phenyl, each of which may optionally be substituted by one or more radicals R22.

[0512] Example of very suitable groups Ar22are the groups (Ar-1) to (Ar-276) depicted in the following table:

[0513] 15

[0514] 20

[0515] 25

[0516]

[0517] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0518] Ar-10 Ar-11

[0519] 0

[0520] o o 5

[0521] Ar-13 Ar-14 Ar-15 Q^X) O^yO - OOOx-x "0

[0522] Ar-16 Ar-17 Ar-18

[0523] 15 OOuOuO " O / UO ^ O^ JOCJ

[0524] Ar-19 Ar-20 Ar-21

[0525] 20

[0526] Oi ^

[0527] Ar-22 Ar-23 Ar-24 25 0xx\

[0528] 0 ^00300 Ar-25 Ar-26 Ar-27

[0529] Okxx 'COOO OOOO

[0530]

[0531] Ar-28 Ar-29 Ar-30 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0532] ''OOOO Qo^

[0533] 0000

[0534] 5

[0535] Ar-31 Ar-32 Ar-33

[0536] OOx

[0537] 0 OOo ^00000 0000 ^OQOO^

[0538] ^00

[0539] 15 Ar-34 Ar-35 Ar-36

[0540] ''( ^OOOO^) " OooO OOx ^OOOC

[0541] ^OQ 0 / 0 20 0 I / O 0"^

[0542] Ar-37 Ar-38 Ar-39 O^JO 0

[0543] 25 ^O^OOx ooc "' oo

[0544] AMO Ar-41 Ar-42 ( ^YO^D c^o^o OOC

[0545] ^OQ

[0546]

[0547] Ar-43 Ar-44 Ar-45 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0548] ^ jQ]

[0549] 5 Q Y OCX

[0550] Ar-46 Ar-47 Ar-48

[0551] Q o cO

[0552] Ar-49 Ar-50 Ar-51

[0553] 15 O O O f O r Cy Ar-52 Ar-53 Ar-54 20 O O

[0554] YO-- Ar-55 Ar-56 Ar-57 25

[0555] Ar-58 Ar-59 Ar-60 O O O—O

[0556]

[0557] Ar-61 Ar-62 Ar-63 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0558] _,0

[0559] O— o " COO 0 l03 Ar-64 Ar-65 Ar-66 5

[0560] "003 COO Ar-67 Ar-68 Ar-69

[0561] _,oxo 0 0- l03 0 003

[0562] "w

[0563] Ar-70 Ar-71 Ar-72 5

[0564] OCO 0 \C03 o

[0565] Ar-73 Ar-74 Ar-75 20

[0566] ^ v3O3” O \ / 0x25 003

[0567] Ar-76 Ar-77 Ar-78 o O

[0568] _zy_ / °x O \ >-0x / 003 003 CO

[0569]

[0570] Ar-79 Ar-80 Ar-81

[0571] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0572] 9%

[0573] 5 0.0 fo

[0574] Ar-82 Ar-83 Ar-84

[0575] xs _zs 9% OCO 0—0 0 w

[0576] Ar-85 Ar-86 Ar-87zs

[0577] 15

[0578] OC o

[0579] O A / S \ / Sx_

[0580] O CO

[0581] 20 Ar-88 Ar-89 Ar-90

[0582] O O ^ vOO '' V / SX Axsx /

[0583] OOC

[0584] 25

[0585] Ar-91 Ar-92 Ar-93

[0586] xs O vOO ooc

[0587] o

[0588]

[0589] Ar-94 Ar-95 Ar-96

[0590] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0591] _ZSX_xs

[0592] —0 0—0 o (i 5 " O 0-0

[0593] Ar-97 Ar-98 Ar-99

[0594] / Q (5 Q Cr 033 0—0 033 Ar-100 Ar-101 Ar-102 Q Q Q Cr Q

[0595] 15 A / s\__ Q / '

[0596] OOJ 033 Ar-103 Ar-104 Ar-105

[0597] 20 A, SX /

[0598] OO^ 003 "033 Ar-106 Ar-107 Ar-108

[0599] 25

[0600] Q / N.

[0601] OOJ^ OO J^ 003

[0602]

[0603] Ar-109 Ar-110 Ar-111

[0604] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0605] Z-,

[0606] 5 oojs

[0607] 99—99

[0608] Ar-112 Ar-113 Ar-114

[0609] 9 N 0000 033

[0610] 0

[0611] Ar-115 Ar-116 Ar-117 c

[0612] 1 N 9N9 5 0-0 033 0_Q 0 O Ar o-118 Ar-119 Ar-120 20 o 0XN

[0613] OO J^ Qp 0 "0 99 25 Ar-121 Ar-122 Ar-123 -a 9 Q 9 9 Y / NX_N

[0614]

[0615] 0—0 003 OO0 <3

[0616] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0617] Ar-124 Ar-125 Ar-126

[0618] _ 0 QXN 5 "0^0 voO

[0619] Ar-127 Ar-128 Ar-129 q9 QQQ Q Q Q- O—

[0620] Ar-130 Ar-131 Ar-132 15

[0621] 0 Q9Q - / 9

[0622] 0 O o ^A O v5-O 0-0

[0623] 20 Ar-133 Ar-134 Ar-135

[0624] qQ 0

[0625] _

[0626] O 0-N9 \

[0627] yO QN

[0628] O 0-0

[0629] 25 oO,o o Ar-136 Ar-137 Ar-138

[0630] □0

[0631]

[0632] Ar-139 Ar-140 Ar-141

[0633] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0634] C45

[0635] 5 Ar-142 Ar-143 Ar-144

[0636] Ar-145 Ar-146 Ar-147 op

[0637] 15 o

[0638] Ar-148 Ar-149 Ar-150 Op ob' ob 20 o o Ar-151 Ar-152 Ar-153

[0639] 25 0^0 Ar-154 Ar-155 Ar-156

[0640] O^p

[0641]

[0642] Ar-157 Ar-158 Ar-159

[0643] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0644] (MX ) 5

[0645] Ar-160 Ar-161 Ar-162

[0646] Ar-163 Ar-164 Ar-165

[0647] 15 Qf'E’ xO

[0648] Ar-166 Ar-167 Ar-168

[0649] 20 ''CX QOX Ar-169 Ar-170 Ar-171 25

[0650] Qo Qo

[0651] QXE

[0652] Ar-172 Ar-173 Ar-174

[0653] n Qo ’-n Qo QQ

[0654]

[0655] ^0%

[0656] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0657] Ar-175 Ar-176 Ar-177 n Qo n Qo

[0658] 5 OuSo ^0%

[0659] Ar-178 Ar-179 Ar-180 Q QO QQo

[0660] ^0% Ar-181 Ar-182 Ar-183

[0661] 15 oQo Qo

[0662] O-o -O Qo (Y^O CX^J Ar-184 Ar-185 Ar-186 20

[0663] Qo Qo

[0664] 25 0

[0665] Ar-187 Ar-188 Ar-189 QQ QQ Qo"'

[0666] -0

[0667]

[0668] Ar-190 Ar-191 Ar-192

[0669] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0670] 50

[0671] Qo... QQ uO "0^0 5 Cx)

[0672] Ar-193 Ar-194 Ar-195 uO

[0673] OKn Qo" w v- Ar-196 Ar-197 Ar-198

[0674] 15 < 0^ CM - Ar-199 Ar-200 Ar-201

[0675] 20

[0676] Ar-202 Ar-203 Ar-204

[0677] 25 C o Ar-205 Ar-206 Ar-207 £? O CM

[0678] CQj C o 0-Q G'Xy

[0679]

[0680] Ar-208 Ar-209 Ar-210

[0681] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0682] 5 Q jn Opy Op)

[0683] Ar-211 Ar-212 Ar-213

[0684] o opr

[0685] yo

[0686] Ar-214 O Ar-215 Ar-216

[0687] 15 O- p CfQ bp Op) OOA opr 20 Ar-217 Ar-218 Ar-219

[0688] p O- ^0 Op)D- 25 Op) Cp)

[0689] Ar-220 Ar-221 Ar-222 CM PbQ

[0690] O^ p OypQ oxp...

[0691]

[0692] Ar-223 Ar-224 Ar-225

[0693] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0694] 52

[0695] On F\ / ^x V

[0696] 5 / / z / —

[0697] Ar-226 Ar-227 Ar-228

[0698] Ar-229 Ar-230 Ar-231 ( z - y.. / /

[0699] ^ 0 [A oc O115

[0700] Ar-232 Ar-233 Ar-234 z / —

[0701] / / ' OXx OOx O

[0702] 20 O'

[0703] Ar-235 Ar-236 Ar-237 XO ^F

[0704] ^ ILX1?' 25 Ar-238 Ar-239 Ar-240 ''O\ "0^ XX

[0705] Ar-241 Ar-242 Ar-243zl / r 1 2 r 3 XX JO^Q

[0706]

[0707] Ar-244 Ar-245 Ar-246

[0708] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0709] 53

[0710] 00^

[0711] 5

[0712] Ar-247 Ar-248 Ar-249

[0713] 0

[0714] 0

[0715] Ar-250 Ar-251 Ar-252 >h

[0716] Ph.. Ph

[0717] i

[0718] 15

[0719] 0

[0720] (

[0721] 0

[0722] 20 Ar-253 Ar-254 Ar-255

[0723] 3h

[0724] Ph.. Ph

[0725] D^\'C >3 X T XJH

[0726] ) V —D

[0727] 25

[0728] Ar3-256 Ar-257 Ar-258 □ i

[0729] D\ / \^D

[0730] X XDXX>=(

[0731] D□ I ^ JL / ~CI

[0732] o — \ >

[0733]

[0734] Ar-259 Ar-260 Ar-261

[0735] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0736] 5

[0737] 15

[0738] 20

[0739]

[0740] 25

[0741] 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.

[0742] Preferably, R20, R20a, R20b, R21, R22, R23stand on each occurrence, identically or differently, for RB; or 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 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 in the 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0743] 55

[0744] 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 5 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.

[0745] 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 15 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.

[0746] Preferably, Ar is, on each occurrence, identically or differently, an aromatic ring system 20 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 aromatic ring atoms, which may in each case also be substituted by one or more radicals R.

[0747] 25 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.

[0748] In accordance with a preferred embodiment, the compound G1 is a deuterated compound.

[0749] 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 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0750] 56

[0751] 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.

[0752] In accordance with the present invention, the deuteration degree corresponds to the 5 number of deuterium atoms in a compound on the total number of deuterium atoms and protium atoms in the compound in %, as follows:

[0753] Deuteration degree (%) = (ND* 100) / (NP+ ND)

[0754] where:

[0755] NDis the number of deuterium atoms in the compound

[0756] NPis the number of deuterium and protium atoms in the compounds

[0757] 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

[0758] 15 hydrogen in the oceans.

[0759] Preferably, the compound G1 has a deuteration degree higher than 20%, 40%, 60% or 80%.

[0760] 20 Suitable examples of the compound G1 are depicted in the following table:

[0761] 25

[0762]

[0763] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0764] 5

[0765] 15

[0766] 20 25

[0767]

[0768] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0769] 58

[0770] 5

[0771] 15

[0772] 20

[0773] 25

[0774]

[0775] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0776] 5

[0777] 15

[0778] 20 25

[0779]

[0780] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0781] 5

[0782] 15

[0783] 20 25

[0784]

[0785] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0786] 5

[0787] 15

[0788] 20

[0789]

[0790] In a general way, the compounds G1 disclosed in the table above might be deuterated, even if not explicitly disclosed in the table.

[0791] 25

[0792] Processes for synthesis of the compounds of the formula (II) are known in the prior art, especially in the publications WO2019 / 115577 and WO2024 / 170605.

[0793] 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),

[0794] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0795] 62

[0796] 5

[0797] Formula (IA)

[0798] Ar11

[0799] L_Zi

[0800]

[0801] 15

[0802] Formula (IB)

[0803] 20

[0804]

[0805] Formula (IC)

[0806] 25

[0807] where the following applies to the symbols and indices occurring:

[0808] 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;

[0809] 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;

[0810] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0811] 63

[0812] X stands on each occurrence, identically or differently, for CR10or N; or X stands for C when it is bonded to an adjacent group;

[0813] T10, T11, T12, T13, T14are the same or different at each instance and are selected from a 5 single bond, O, S, NRN, and C(RC)2; with the proviso that T12, T13do not both stand for a single bond;

[0814] 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 15 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;

[0815] RNstands for H, D, F, a straight-chain alkyl group having 1 to 40, preferably 1 to 30, more 20 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 25 aromatic ring atoms, which may in each case be substituted by one or more radicals R;

[0816] 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 CH2groups 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 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0817] 64

[0818] 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.

[0819] 5

[0820] 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),

[0821] 15

[0822] 20

[0823]

[0824] 25

[0825]

[0826] Formula (IA-3)

[0827] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0828] 65

[0829] 5

[0830]

[0831] 15

[0832]

[0833] 20

[0834] 25

[0835] Formula (IC-1)

[0836]

[0837] where the symbols X, Rc, RN, L10, L11, L12, Ar11and Ar12have the same meaning as above.

[0838] 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.

[0839] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0840] 66

[0841] 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.

[0842] 5

[0843] 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.

[0844] Particularly preferably, Ar11and Ar12are on each occurrence, identically or differently, selected from the group consisting of phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, 15 fluorenyl, especially 9,9'-dimethylfluorenyl and 9,9'-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, dibenzofuranyl, dibenzothiophenyl, benzofuranyl, benzothiophenyl, benzofused dibenzofuranyl, benzofused dibenzothiophenyl, naphthylsubstituted phenyl, fluorenyl-substituted phenyl, spirobifluorenyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzothiophenyl-substituted phenyl, pyridyl-substituted 20 phenyl, pyrimidyl-substituted phenyl, and triazinyl-substituted phenyl, each of which may optionally be substituted by one or more radicals R12.

[0845] Suitable groups Ar11and Ar12are the groups (Ar-1) to (Ar-276) as depicted above.

[0846] 25 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),

[0847] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0848] 67

[0849] 5

[0850]

[0851] 15

[0852] 20

[0853]

[0854] Formula (IA-1-2)

[0855] 25

[0856]

[0857] Formula (IA-2-1)

[0858] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0859] 68

[0860] 5

[0861]

[0862] Formula (IA-2-2)

[0863] 15

[0864] 20

[0865]

[0866] Formula (IA-3-1)

[0867] 25

[0868]

[0869] Formula (IA-3-2)

[0870] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0871] 69

[0872] Formula (IB-2-1)

[0873]

[0874] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0875] 70

[0876] 5

[0877] Formula (IB-2-2)

[0878] 15

[0879]

[0880] Formula (IB-3-1)

[0881] 20

[0882] 25

[0883]

[0884] Formula (IB-3-2)

[0885] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0886] 71

[0887] 5

[0888] 15

[0889]

[0890] Formula (IC-1-2)

[0891] 20

[0892] where the symbols X, Rc, RN, L10, L11, L12and Ar11have the same meaning as above and:

[0893] A1is equal to C(RC)2, O, S or equal to

[0894] 25

[0895] where the dashed lines represent the bonds emanating from the group A1;

[0896]

[0897] 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.

[0898] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0899] 72

[0900] 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.

[0901] 5 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, 10 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.

[0902] 15 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.

[0903] 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, 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 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 25 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 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.

[0904] 30

[0905] In accordance with a preferred embodiment, the compound H is a deuterated compound.

[0906] Preferably, the compound H has a deuteration degree higher than 20%, 40%, 60% or 80%.

[0907] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0908] 73

[0909] Examples of the compound H are depicted in the following table:

[0910] 5

[0911] 15

[0912] 20

[0913] 25

[0914]

[0915] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0916] 74

[0917] 15

[0918] 20

[0919] 25

[0920]

[0921] Foreignfiling_text P24-239-SEC-WO01 20250919

[0922] 75

[0923] 10 20 25

[0924]

[0925] Foreignfiling_text P24-239-SEC-WO01 20250919

[0926] 76

[0927] 15

[0928]

[0929] In a general way, the compounds H disclosed in the table above might be deuterated, even if not explicitly disclosed in the table.

[0930] Processes for synthesis of the compound H are known in the prior art, especially in the publications cited in the table below:

[0931] Structure type Publication

[0932] 4-Fluorenylamines W02007 / 072952; WO2019 / 168320 2-Fluorenylamines WO2014 / 015938, WO2014 / 034795 3-Fluorenylamines W02016 / 006710

[0933] 2-Spirobifluorenylamines WO2012 / 034627; WO2019 / 115577

[0934]

[0935] Foreignfiling_text P24-239-SEC-WO01 20250919

[0936] 77

[0937] 4-Spirobifluorenylamines KR20140045154A, WO2019 / 168320 Spirobifluorenes with amino WO2013 / 120577, WO2017 / 016632, group in 1, 3 or 4 position WO2017 / 102063, WO2017 / 102064 4-Spirobifluorenylamines with WO2017 / 133829

[0938] 5 spacer group between

[0939] spirobifluorenyl and amine

[0940] Aminocarbazoles US2005 / 0221124 Diarylaminicarbazoles WO2008 / 062636

[0941]

[0942] 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.

[0943] According to the present invention, the second auxiliary layer comprises a compound G2.

[0944] 15 Preferably, the compound G2 is selected from compounds of formulae (IIIA), (HUB), (IIIC), (HID), (HID’), (HIE) and (IIIF),

[0945] 20

[0946]

[0947] Formula (IIIA)

[0948] 25

[0949] Ar30

[0950]

[0951] Formula (IIIB)

[0952] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0953] 78

[0954] 5

[0955] Ar31 / L31

[0956] 15

[0957]

[0958] Formula (IIID)

[0959] Ar3120

[0960] 25

[0961]

[0962] Formula (HID’)

[0963] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0964] 79

[0965] 5

[0966] Formula (IIIE)

[0967] 15

[0968]

[0969] Formula (IIIF)

[0970] where

[0971] where the following applies to the symbols occurring:

[0972] 20

[0973] 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;

[0974] 25

[0975] Ar30, Ar31, Ar32, Ar33are 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;

[0976] V stands on each occurrence, identically or differently, for CR30or N; or V stands for C when it is bonded to the group L30;

[0977] 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;

[0978] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0979] 80

[0980] T36, T37are the same or different at each instance and are selected from O, S, NRN, and C(RC)2;

[0981] 5 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 15 radicals R32may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R; and

[0982] R, Rcand RNhave the same definition as above.

[0983] More preferably, the compound G2 is selected from compounds of formulae (IIIA-1) to (IIIA- 20 4), (IIIB), (IIIC-1) to (IIIC-3), (IIID-1), (IIID’-1), (IIIE-1) and (IIIF-1),

[0984] 25

[0985] Formula (IIIA-1)

[0986]

[0987] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0988] 81

[0989] 5

[0990] Formula (IIIA-2)

[0991] 15

[0992]

[0993] Formula (IIIA-3)

[0994] 20

[0995]

[0996] 25 Formula (IIIA-4)

[0997] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[0998] 5

[0999] Formula (IIIB)

[1000] 15

[1001]

[1002] 20

[1003]

[1004] 25

[1005]

[1006] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1007] 83

[1008] Ar31 / L31

[1009] 5

[1010]

[1011] Formula (IIID-1) Ar31

[1012] 15

[1013] 2

[1014]

[1015] 0

[1016] Formula (IIID’-1)

[1017] 25

[1018] Formula (IIIE-1)

[1019]

[1020] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1021] 84

[1022] 5

[1023] Formula (IIIF-1)

[1024]

[1025] where the symbols V, Rc, RN, L30, L31, L32, Ar30, Ar31, Ar32and Ar33have the same meaning as above.

[1026] Among the compounds of formulae (111 A- 1 ) to (IIIA-4), (111 B), (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- 15

[1027] 1), (I II D’-1) are preferred.

[1028] Preferably, Ar31, Ar32and Ar33stand 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

[1029] 20

[1030] preferably 6 to 18 aromatic ring atoms, which may be substituted by one or more radicals R32.

[1031] More preferably, Ar30, Ar31, Ar32and Ar33are on each occurrence, identically or differently, selected from the group consisting of phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, 25

[1032] 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.

[1033] Particularly preferably, Ar30, Ar31, Ar32and Ar33are 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, 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1034] 85

[1035] benzofuranyl, benzothiophenyl, benzofused dibenzofuranyl, benzofused dibenzothiophenyl, naphthyl-substituted phenyl, fluorenyl-substituted phenyl, spirobifluorenyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzothiophenyl-substituted phenyl, pyridylsubstituted phenyl, pyrimidyl-substituted phenyl, and triazinyl-substituted phenyl, each of 5 which may optionally be substituted by one or more radicals R32.

[1036] Suitable groups Ar30, Ar31, Ar32and Ar33are the groups (Ar-1) to (Ar-276) as depicted above.

[1037] 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), (IIID’-1-1), (III D’-1- 2), (IIID’-1-3), (IIID’-2-1), (IIID’-2-2), (IIIE-1-1), (IIIE-1-2), (IIIF-1-1) and (IIIF-1-2),

[1038] 15

[1039] 20

[1040]

[1041] Formula (IIIA-1-1)

[1042] 25

[1043]

[1044] Formula (IIIA-1-2)

[1045] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1046] 5

[1047]

[1048] Formula (IIIA-2-1)

[1049] 15

[1050] 20

[1051]

[1052] 25

[1053]

[1054] Formula (IIIA-3-1)

[1055] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1056] 5

[1057]

[1058] Formula (IIIA-3-2)

[1059] 15

[1060] 20

[1061]

[1062] 25

[1063]

[1064] Formuõa (IIIA-4-2)

[1065] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1066] Ar305

[1067]

[1068] 15

[1069] Formula (IIIB-1)

[1070] Ar3020

[1071] 25

[1072]

[1073] Formula (IIIB-2)

[1074] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1075] 5

[1076] Ar31 /

[1077] 15

[1078]

[1079] Formula (IIIC-1-2)

[1080] 20

[1081] Ar31 /

[1082] 25

[1083]

[1084] Formula (IIIC-2-1)

[1085] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1086] 90

[1087] Ar31

[1088] 5

[1089] Formula (IIIC-2-2)

[1090] Ar31 / L31

[1091] 15

[1092]

[1093] Formula (IIIC-3-1)

[1094] 20

[1095] Ar31 / L31

[1096] 25

[1097]

[1098] Formula (IIIC-3-2)

[1099] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1100] Ar31 / L31

[1101] 5

[1102]

[1103] Formula (IIID-1-1)

[1104] Ar31 / L31

[1105] 15

[1106] 2

[1107]

[1108] 0

[1109] Formula (IIID-1-2)

[1110] Ar31

[1111] 25

[1112]

[1113] Formula (IIID’-1-1)

[1114] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1115] 92

[1116] 5

[1117] 15

[1118]

[1119] 20 Formula (IIID’-1-3)

[1120] Ar3125

[1121]

[1122] Formula (IIID’-2-1)

[1123] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1124] 93

[1125] Ar31

[1126] 5

[1127] Formula (IIID’-2-2)

[1128] 15

[1129]

[1130] Formula (IIIE-1-1)

[1131] 20

[1132] 25

[1133] Formula (IIIE-1-2)

[1134]

[1135] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1136] 5

[1137]

[1138] 15

[1139] 2

[1140]

[1141] 0

[1142] Formula (IIIF-1-2)

[1143] where the symbols V, Rc, RN, L30, L31, L32, Ar30, Ar31and Ar33have the same meaning as above, and where:

[1144] 25

[1145] A2is equal to C(RC)2, O, S or equal to

[1146]

[1147] where the dashed lines represent the bonds emanating from the group A2;

[1148] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1149] 95

[1150] W stands on each occurrence, identically or differently, for CR30or N; or Y stands for C when it is bonded to the group L32.

[1151] In accordance with a preferred embodiment, the compound G2 is selected from compounds 5 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), (IIID’-1-1), (IIID’-1-2), (IIID’-1-3), (IIID’-2-1), (IIID’-2-2), (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 15 substituted by one or more radicals R.

[1152] 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 20 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 25 from the group consisting of benzene, biphenyl, terphenyl, naphthyl, dibenzofuranyl and dibenzothiophenyl, and carbazolyl, which may be substituted by one or more radicals R32. 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.

[1153] 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 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 in the alkyl, alkoxy or 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1154] 96

[1155] 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 sub5 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.

[1156] In accordance with a preferred embodiment, the compound G2 is a deuterated compound.

[1157] Preferably, the compound G2 has a deuteration degree higher than 20%, 40%, 60% or 80%.

[1158] Preferably, the electronic device according to the invention comprises at least one

[1159] 15 deuterated compound selected compound G1, compound G2 and compound H.

[1160] Examples of the compound G2 are depicted in the following table:

[1161] 20

[1162] 25

[1163] 35

[1164]

[1165] Foreignfiling_text P24-239-SEC-WO01 20250919

[1166]

[1167] Foreignfiling_text P24-239-SEC-WO01 20250919

[1168] 98

[1169] 5

[1170] 15

[1171] 20

[1172] 25

[1173]

[1174] In a general way, the compounds G2 disclosed in the table above might be deuterated, even if not explicitly disclosed in the table.

[1175] Processes for synthesis of the compounds G2 are known in the prior art, especially in the publications cited in the table below:

[1176] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1177] 99

[1178] Structure type Publication

[1179] 4-Fluorenylamines W02007 / 072952; WO2019 / 168320, WO2014 / 015935

[1180] 2-Fluorenylamines WO2014 / 015938, WO2014 / 034795 5 3-Fluorenylamines WO2016 / 006710

[1181] 2-Spirobifluorenylamines WO2012 / 034627; WO2019 / 115577 4-Spirobifluorenylamines KR20140045154A, WO2019 / 168320 Substituted spirobifluorenylamines WO2022 / 096172

[1182] Spirobifluorenes with amino group in WO2013 / 120577, WO2017 / 016632, 1, 3 or 4 position WO2017 / 102063, WO2017 / 102064 4-Spirobifluorenylamines with spacer WO2017 / 133829

[1183] group between spirobifluorenyl and

[1184] amine

[1185] Spiroxanthenes WO2014 / 072017

[1186] 15

[1187] Spiroacridines WO2015 / 158411 Indenofluorenylamines WO2019 / 048443 Diphenylfluorenylamines WO2021 / 206478, W02024 / 005492 Bisfluorenylamines WO2019 / 192954

[1188]

[1189] 20

[1190] 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.

[1191] In the present application, the hole transport layer comprising the compound H is called 25

[1192] 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.

[1193] Preferably, the hole transport layer HTL consists of a compound H as defined above.

[1194] 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.

[1195] 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- 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1196] 100

[1197] 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 of formula (I A), (IB) or (IC) as defined above and a p-dopant. In a preferred embodiment, 5 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.

[1198] 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.

[1199] 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 15 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, WO3and ReO3. Still further preference is given to complexes of bismuth in the (III) oxidation state, 20 more particularly bismuth(lll) complexes with electron-deficient ligands, more particularly carboxylate ligands.

[1200] 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 25 transport material matrix. The p-dopant is preferably present in a proportion of 1% to 10% in the p-doped layer.

[1201] Preferred p-dopants are especially the compounds shown in WO2021 / 104749 on pages 99- 100 as (D-1) to (D-14).

[1202] 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.

[1203] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1204] 101

[1205] Preferably, the hole transport layer HTL is in direct contact with the first auxiliary layer.

[1206] Preferably, the first auxiliary layer consists of a compound G1 as described above.

[1207] 5 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.

[1208] The hole transport region comprises in this sequence (from the first electrode to the emitting layer):

[1209] optionally a hole injection layer HIL,

[1210] a hole transport layer HTL comprising a compound H as defined above,

[1211] a first auxiliary layer ALIX1 comprising a compound G1,

[1212] a second auxiliary layer ALIX2 comprising a compound G2 as defined above.

[1213] 15

[1214] 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 20 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 25 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.

[1215] The hole transport layer HTL preferably has a thickness of 40 to 170 nm, more preferably of 50 to 145 nm.

[1216] The first auxiliary layer AUX1 and the second auxiliary layer AUX2 are preferably electron blocker layers.

[1217] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1218] 102

[1219] Besides the layers HI L, HTL, ALIX1 and ALIX2, the hole tansport region may comprise further hole transport layers.

[1220] The emitting layer comprises a host and a dopant selected from phosphorescent emitters.

[1221] 5

[1222] 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.

[1223] 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.

[1224] 15 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.

[1225] 20

[1226] Preferably, the emitting layer comprises a host and a dopant preferably selected from phosphorescent emitters.

[1227] The term "phosphorescent emitters" typically encompasses compounds where the emitting 25 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.

[1228] 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,

[1229] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1230] 103

[1231] rhodium, iridium, palladium, platinum, silver, gold or europium, especially compounds containing iridium, platinum or copper.

[1232] In the context of the present invention, all luminescent iridium, platinum or copper

[1233] 5 complexes are considered to be phosphorescent compounds.

[1234] 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.

[1235] 15 The emitting layer is preferably a green-emitting layer.

[1236] 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 20 thickness of 50 nm at room temperature.

[1237] The photoluminescence spectrum of the layer is recorded, for example, with a commercial photoluminescence spectrometer.

[1238] 25 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(T 1 in eV) = 1240 / E(T 1 in nm) = 1240 / PLmax. (in nm).

[1239] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1240] 104

[1241] Preferred phosphorescent emitters are accordingly green emitters, preferably selected from iridium or platinum complexes, which preferably have a triplet energy Ti of ~2.5 eV to ~2.3 eV.

[1242] 5 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 blueemitting 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.

[1243] 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 ALIX1, a second auxiliary layer ALIX2 and a green-phosphorescing layer, and a second device according to 15 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 20 arrangement.

[1244] 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 25 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.

[1245] 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 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1246] 105

[1247] 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 5 device is a fluorescent or phosphorescent electroluminescent device.

[1248] Preferably, the first electrode is an anode and the second electrode is a cathode.

[1249] The sequence of layers in the electronic device is preferably as follows:

[1250] - first electrode, preferably anode

[1251] - hole injection layer HIL, preferably p-doped

[1252] - Hole transport layer HTL

[1253] - optionally further hole transport layer(s)

[1254] - first auxiliary layer ALIX1

[1255] 15 - second auxiliary layer ALIX2

[1256] - emitting layer

[1257] - optionally hole blocker layer

[1258] - electron transport layer

[1259] - electron injection layer

[1260] 20 - second electrode, preferably cathode.

[1261] 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, 25 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. Li F, U2O, BaF2, MgO, NaF, CsF, CS2CO3,

[1262] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1263] 106

[1264] 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.

[1265] Preferred anodes are materials having a high work function. Preferably, the anode has a 5 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 / N i / N iOx, AI / PtOx) may also be preferred. For some applications, at 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-I-ASER). Preferred anode materials here are conductive mixed metal oxides. Particular preference is given to indium tin oxide (ITO) or indium zinc oxide (IZO).

[1266] 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, 15 molybdenum oxide or vanadium oxide.

[1267] It is not obligatory for all the layers mentioned to be present, and / or further layers may additionally be present.

[1268] 20 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 25 and spirodibenzothiophenes, phenanthrenediarylamines, spirotribenzotropolones, spirobifluorenes having meta-phenyldiamine groups, spirobisacridines, xanthenediarylamines, and 9,10-dihydroanthracene spiro compounds having diarylamino groups.

[1269] 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

[1270] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1271] 107

[1272] 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).

[1273] 5 In a preferred embodiment, the electronic device contains at least one hole blocker layer.

[1274] 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 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.

[1275] 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.

[1276] 15

[1277] 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.

[1278] Especially suitable are aluminium complexes, for example Alqa, zirconium complexes, for example Zrq4, lithium complexes, for example Liq, benzimidazole derivatives, triazine 20 derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives and phosphine oxide derivatives.

[1279] In a preferred embodiment, the electronic device is characterized in that one or more layers 25 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.

[1280] 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)

[1281] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1282] 108

[1283] 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).

[1284] Preference is additionally given to an electronic device, characterized in that one or more 5 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.

[1285] 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.

[1286] 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.

[1287] 15 The electronic device may be used in displays, as light source in lighting applications, and as light source in medical and / or cosmetic applications.

[1288] 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.

[1289] 20

[1290] Examples

[1291] A) Synthesis examples

[1292] 25 Synthesis of Amine-1

[1293] NH2

[1294]

[1295] 70728-90-4

[1296] A solution of SM-A (57.3 g, 167 mol) and 9,9-dimethyl-9H-fluorene-2-amine (35.0 g, 167 mmol) in degassed toluene (1000 mL) is mixed with S-Phos (1.22 g, 3 mmol), Pd2(dba)s (0.93 g, 1 mmol) and sodium tert-butoxide (59.3 g, 215 mmol), and the mixture is heated 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1297] 109

[1298] under reflux for 20 h. The reaction mixture is cooled to room temperature, diluted with toluene and filtered through Celite. The filtrate is diluted with water and again extracted with toluene, and the combined organic phases are dried and concentrated in vacuum. The residue is filtered through silica gel (heptane / dichloromethane) and crystallized from

[1299] 5 isopropanol, pale-yellow solid. Yield (72.8 g, 93% of theory).

[1300] The following compounds are synthesized analogously:

[1301] 15 Synthesis of compound 1

[1302] 20

[1303]

[1304] SM-1 compound 1

[1305] S-Phos (1,06 g, 2,6 mmol), Pd2(dba)3 (1,18 g, 1,29 mmol) and sodium tert-butoxide (48,3 g, 25 85,9 mmol) are added to a solution of N-{[1,1'-biphenyl]-2-yl}-9,9-dimethyl-9H-fluoren-2- amine (15,5g, 42,9 mmol) and SM-1 (15 g, 42,9 mmol) in degassed toluene (200 ml), and the mixture is heated under reflux for 10 h. The reaction mixture is cooled to room temperature, extended with toluene and filtered through Celite. The filtrate is evaporated in vacuo, and the residue is crystallised from toluene / heptane. The crude product is extracted in a Soxhlet extractor (toluene) and purified by zone sublimation in vacuo twice. The product is isolated in the form of an off-white solid (14 g, 48% of theory).

[1306] Following compounds are synthesized in analogous manner:

[1307] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1308] 110

[1309] Comp. SM Amine Product 2

[1310] . o O0

[1311] o— HN

[1312] 5 o CMTYVXP synthesized in

[1313] CAS 1198395-24-2

[1314] analogous manner

[1315] like Ex.4b in

[1316] WO2024 / 170605

[1317] 3

[1318] o-p o Q-CrCIHN

[1319] Ay o

[1320] 15

[1321] synthesized in

[1322] CAS 1198395-24-2

[1323] analogous manner

[1324] like Ex.3a in J | H WO19115577

[1325] zo^

[1326] 4

[1327] 20 v C^ A /

[1328] Q-CrCIHN

[1329] o

[1330] O-Y

[1331] v Vz 'X)

[1332] synthesized in

[1333] 25 CAS2225845-23-6

[1334] analogous manner

[1335] like Ex.3a in

[1336] WO19115577

[1337] 5

[1338] 7~~^ HN / V

[1339] CAS 382602-31-5 O

[1340]

[1341] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1342] 111

[1343] 6

[1344] CH>clHN

[1345] Q

[1346] 5 o

[1347] CAS 2356109-79-8

[1348] 7

[1349] HN

[1350] o

[1351] cVv y=\ L A, synthesized in

[1352] analogous manner

[1353] like Ex.3a in

[1354]

[1355] WO19115577

[1356] 15

[1357] B) Device examples

[1358] J

[1359] 1. Preparation of OLED stacks

[1360] 20 The OLEDs are produced according to the following process, and their properties are characterized, as described below in detail.

[1361] Glass plaques which have been coated with structured ITO / Ag / ITO (indium tin oxide) in a thickness of 100 nm are used as the substrates to which the OLEDs are applied. The 25 materials used for production of the OLEDs are shown in Table 4.

[1362] The OLEDs have the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electron blocker 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 with capping layer. The cathode is formed by a mixture of Ag (91%) and Mg (9%) layer of thickness 12 nm, followed by a capping layer HT-01 with a thickness of 80 nm. All materials mentioned in the following are applied by thermal vapor deposition in a vacuum chamber.

[1363] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1364] 112

[1365] The exact structure of the OLEDs are given in table 1, where the comparative examples CE1 and CE2 and examples E1-E7 with EBL materials used in OLEDs are summarized. The EML (38 nm thickness) is identical for all given examples and consists of matrix materials T21 and T22 (host materials) and an emitting dopant T23 which is added to the 5 matrix materials in a particular proportion by volume by co-evaporation. Details are given by T21: T22: T23 (35%:53%:12%) meaning here that the material T21 is present in the layer in a proportion by volume of 35% and T22 in a proportion of 53% and T23 in a proportion of 12%. In analogous manner, the ETL (31 nm thickness) is identical for all given examples and consists of E: LiQ (50%:50%). The HBL (5 nm thickness) is identical for all given examples and consists of compound G and the EIL (1.5 nm thickness) is identical for all examples and consists of Yb.

[1366] Table 1:

[1367] Ex. HIL HTL EBL1 EBL2

[1368] 15

[1369] CE1 EH2: D (99%:1%) EH2 C1 C2

[1370] 10nm 150nm 23.5nm 5nm

[1371] CE2 EH2: D (99%:1%) EH2 C3 C2

[1372] 10nm 150nm 23.5nm 5nm

[1373] E1 EH2: D (99%:1%) EH2 EB3 EB2

[1374] 10nm 150nm 23.5nm 5nm

[1375] E2 EH2: D (99%:1%) EH2 EB4 EB2

[1376] 10nm 150nm 23.5nm 5nm

[1377] 20 E3 EH2: D (99%:1%) EH2 EB5 EB2

[1378] 10nm 150nm 23.5nm 5nm

[1379] E4 EH2: D (99%:1%) EH2 EB6 EB2

[1380] 10nm 150nm 23.5nm 5nm

[1381] E5 EH2: D (99%:1%) EH2 EB7 EB1

[1382] 10nm 150nm 23.5nm 5nm

[1383] E6 EH2: D (99%:1%) EH2 EB8 EB2

[1384]

[1385] 10nm 150nm 23.5nm 5nm

[1386] 25

[1387] 2. Characterization of the performance of the OLED stacks

[1388] The properties of OLEDs are characterized in a standard manner, as explained below.

[1389] External Quantum Efficiency and voltage

[1390] The external quantum efficiency (EQE, measured in %) as a function of the luminance, calculated from current-voltage-luminance characteristics assuming Lambertian radiation

[1391] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1392] 113

[1393] characteristics, is determined. The parameter EQE @ 10 mA / cm2refers to the external quantum efficiency which is attained at current density of 10 mA / cm2.

[1394] The voltage is extracted from voltage current density characteristics for current densities of 10 mA / cm2.

[1395] 5

[1396] Lifetime

[1397] Generally, lifetime is compared at a certain current density, or compared at a certain light intensity of the OLED at room temperature. 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. Furthermore, lifetime at elevated temperatures is an additional measure which becomes more and more important for state-of-the-art OLED devices.

[1398] 15

[1399] Therefore, lifetime is determined to assess the performance of the OLED. Lifetime values LT90 are measured as time passed (in hrs) until luminance is dropped to 90% of initial luminance Lo of 45000 cd / m2.

[1400] 20 3. Results

[1401] Table 2: LT90 and EQE of the OLEDs given in Table 1

[1402] EQE @ 10 mA / cm2LT90(h)

[1403] CE2 40.7 27

[1404] 25

[1405] E1 42.3 570

[1406] E2 42.5 560

[1407] E3 42.9 580

[1408] E4 42.2 570

[1409] E5 42.1 670

[1410]

[1411] E6 42.3 560

[1412] In table 2, all devices E1 to E6 comprising the inventive compounds EB3 to EB8 show very good EQE and lifetime at room temperature and operational voltage.

[1413] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1414] 114

[1415] Devices E1, E3 and E6 comprising inventive compounds EB3, EB5 and EB8 respectivley, also show good lifetimes at high temperature (at 70°C).

[1416] In general, using the inventive compounds as the first auxiliary layer leads to better device performance than using them as the second auxiliary layer. In particular, an increased 5 efficiency and lifetime at room temperature is achieved over CE2. By this a better OLED stability against high temperature and current density stress can be achieved by using the inventive compounds as the first auxiliary layer.

[1417] Structures of the compounds used in OLED stacks:

[1418] 15

[1419] 20

[1420] 25

[1421]

[1422] 35 Foreignfiling_text P24-239-SEC-WO01 20250919

[1423] 115

[1424] Mi Ml

[1425] Li^NO

[1426] 5 XJuOQ

[1427] Cj 0-^0 °'O

[1428] G LiQ

[1429] o CJ? JM

[1430] MXX /

[1431] v xJrV'"\ ^ f \=~ / \ '•■■,. ‘r’'p^\ _

[1432] r ‘;' < \CCMK

[1433] HT-01 EH2

[1434] 15 «

[1435] . L > r-s "1! J

[1436] ft <-•■■<.,n"'X v "\ i!,--• x V o ■ J II

[1437] L / ’x: i ' i

[1438] 20 i <u" ~

[1439] '1

[1440] EB1 EB2

[1441] '.> Nl'OK's{Y> f I X »<*■""*

[1442] ".* A » -v ~

[1443] 25 x*-* 'r- •* /

[1444] ■-;-, - -t

[1445] "1- -J- '

[1446] EB3 EB4

[1447] JO

[1448] rrLx- >\_t. CMZ\ 'A / JZM vzXz

[1449] EB5 EB6

[1450] 35

[1451]

[1452] Foreignfiling_text P24-239-SEC-WO01 20250919

[1453] 116

[1454] 5

[1455] 15

[1456]

[1457] 20

[1458] 25

[1459] 35

Claims

1. Foreignfiling_text P24-239-SEC-WO01 202509192.1173.Claims1. An electronic device comprising:5.5 a first electrode;6.a second electrode facing the first electrode;7.an interlayer between the first electrode and the second electrode and comprising an emitting layer, wherein:8.the emitting layer comprises a host material and a dopant, where the dopant is selected from fluorescent emitters and phosphorescent emitters,9.the interlayer further comprises a hole transport region between the emitting layer and the first electrode,10.1511.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,12.2013.the hole transport layer comprises a compound H selected from triarylamine-based compounds,14.the first auxiliary layer comprises a compound G1 selected from compounds of formula 25 (II),15.35 Foreignfiling_text P24-239-SEC-WO01 2025091916.

518. 20.1521.where the following applies to the symbols and indices occurring:22.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 20 having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R22;23.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 R23;24.2525.X1to X8stand on each occurrence, identically or differently, for CR20, CRA, CRBor N; where at least one of X1, X2, X3and X4is bonded to L20and stands for C;26.Z1to Z11stand on each occurrence, identically or differently, for CR21, CRA, CRBor N; where the symbols Z1to Z11which are bonded to an adjacent group stand for C;27.R20, R20a, R20b, R21, R22, R23stand on each occurrence, identically or differently, for RB; or 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 35 Foreignfiling_text P24-239-SEC-WO01 2025091928.11929.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 5 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 R21; two radicals R22and / or two radicals R23may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R;30.RAstands on each occurrence, identically or differently, 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 in each case be substituted by one or more radicals Raor RB; 1531.RBstands on each occurrence, identically or differently, for 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 Rb, where in said alkyl groups one or more non-adjacent CH2 groups may be replaced by RbC=CRb, C=C, Si(Rb)2, Ge(Rb)2, 20 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;32.e1 is an integer from 0 to 5;33.25 R, Ra, 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 Foreignfiling_text P24-239-SEC-WO01 2025091934.12035.Raor / and two radicals Rbmay form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R;36.Ar is, on each occurrence, identically or differently, an aromatic ring system having 6 to 40 5 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;37.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;38.15 the second auxiliary layer comprises a compound G2;39.characterized in that, in the compound of formula (II), where at least one symbol selected from X1to X8or Z1to Z11stands for CRA.40.20 2. An electronic device according to claim 1, characterized in that the compound G1 is selected from the compounds of formula (II), e1 is larger than 0.

3. An electronic device according to one or more of the preceeding claims, characterized in that the compound G1 is selected from the compounds of formula (II) and at least one of 25 X5to X8and Z1to Z5stands for CRA, preferably at least one of X5and Z1to Z5stands for CRA, more preferably at least one of X5, Z1and Z4stands for CRA, and most preferable at least one of X5and Z4stands for CRA.

4. An electronic device according to one or more of the preceding claims, characterized in that a compound G1 selected from compounds of formula (11-1 -A) and formula (11-1 -B)Foreignfiling_text P24-239-SEC-WO01 2025091943.12144.545.1047. 49.1550.2052. 54.Formula (II-1-B)55.where the symbols X1to X8, L20, L21, L22, Ar22, Z2to Z5, Z7to Z11, R20a, R20b, RBand e1 have the same meaning as in claim 1;56.2557.where the compound of formula (II-1-A) comprises at least one symbol selected from X1to X8, Z2to Z5and Z7to Z11, which stands for CRA;58.where the compound of formula (II-1-B) comprises at least one symbol selected from X1to X8, Z3to Z5and Z7to Z10, which stands for CRA;59.T20is O, S or C(R21a)(R21b); and60.3061.R21aand R21beach have the same meaning as R21in claim 1.

5. An electronic device according to one or more of the preceding claims, characterized in that a compound G1 selected from compounds of formula (II-2) and (II-3),Foreignfiling_text P24-239-SEC-WO01 2025091963.12264.

566. 68.1569.070.

572. 74.Formula (II-3)75.where the symbols X1to X8, L20, L21, L22, Ar22, Z1to Z11, R20a, R20b, RA, RBand e1 have the same meaning as in claim 1. Foreignfiling_text P24-239-SEC-WO01 2025091976.1236. An electronic device according to one or more of the preceding claims, characterized in that a compound G1 selected from compounds of formula (II-2-1-A), (II-3-1-A) and (II-3-1-B),78.579.1581. 83.2084.2586.

89. 91.35 Foreignfiling_text P24-239-SEC-WO01 2025091992.12493.

595. 97.Formula (II-3-1-B)98.where the symbols X1to X8, L20, L21, L22, Ar22, Z2to Z10, R20a, R20b, RA, RBand e1 have the same meaning as in claim 1.99.

157. An electronic device according to one or more of the preceding claims, characterized in that a compound G1 selected from compounds of formula (II-4) and formula (II-5),101.20102.25104.

107. 109.35 Foreignfiling_text P24-239-SEC-WO01 20250919110.125111.5113.

114. 15115.Formula (II-5)116.where the symbols X1to X8, L20, L21, L22, Ar22, Z1to Z11, R20a, R20b, RBand e1 have the same meaning as in claim 1;117.Z12to Z17stand on each occurrence, identically or differently, for OR21, CRBor N; where 20 the symbols Z12to Z17which are bonded to an adjacent group stand for C; and R21has the same meaning as in claim 1.

8. An electronic device according to one or more of the preceding claims, characterized in that a compound G1 selected from compounds of formula (II-4-1-A), (II-5-1-A) and (II-5-1-25119.B),120.35 Foreignfiling_text P24-239-SEC-WO01 20250919121.126122.5124.

125. 15 Formula (II-4-1-A)126.20127.25128. 130.Formula (II-5-1-A)131.35 Foreignfiling_text P24-239-SEC-WO01 20250919132.5134. 136.Formula (II-5-1-B)137.15 where the symbols X1to X8, L20, L21, L22, Ar22, Z2to Z10, R20a, R20b, T20, RBand e1 have the same meaning as in claim 1; and138.Z12to Z16stand on each occurrence, identically or differently, for CR21, CRBor N; where the symbols Z12to Z17which are bonded to an adjacent group stand for C; and R21has the same meaning as in claim 1.139.

209. 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),141.25143.

144. Formula (IA)145.35 Foreignfiling_text P24-239-SEC-WO01 20250919146.128147.Ar11148.5149.Formula (IB)151. 153.15154.Formula (IC)155.where the following applies to the symbols and indices occurring:156.L10, L11, L12are on each occurrence, identically or differently, a single bond, an157.20158.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;159.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 25160.aromatic ring atoms, which may be substituted by one or more radicals R12;161.X stands on each occurrence, identically or differently, for CR10or N; or X stands for C when it is bonded to an adjacent group;162.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;163.35 Foreignfiling_text P24-239-SEC-WO01 20250919164.129165.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 5 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;166.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; 15 where R has the same meaning as in claim 1.167.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 20 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 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 25 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;168.R has the same definition as in claim 1.

10. An electronic device according to one or more of the preceeding claims, characterized in that the compound H is selected from compounds of formulae (IA), (IB) and (IC),170.35 Foreignfiling_text P24-239-SEC-WO01 20250919171.130172.5173.Formula (IA)174.Ar11175.L_Zi177. 179.15180.Formula (IB)181.20183. 185.Formula (IC)186.25187.where the following applies to the symbols and indices occurring:188.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;189.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;190.35 Foreignfiling_text P24-239-SEC-WO01 20250919191.131192.X stands on each occurrence, identically or differently, for CR10or N; or X stands for C when it is bonded to an adjacent group;193.T10, T11, T12, T13, T14are the same or different at each instance and are selected from a 5 single bond, O, S, NRN, and C(RC)2; with the proviso that T12, T13do not both stand for a single bond;194.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 15 together, which may be substituted by one or more radicals R;195.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 20 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 1.196.R10, R11, R12stand on each occurrence, identically or differently, for H, D, F, Cl, 25 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 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 R11197.35 Foreignfiling_text P24-239-SEC-WO01 20250919198.132199.and / or two radicals R12may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R;200.R has the same definition as in claim 1.201.

511. 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),203.15204.20206. 208.25210. 212.Formula (IA-3)213.35 Foreignfiling_text P24-239-SEC-WO01 20250919214.133215.Ar11216.5218. 220.Formula (IB-1)221.15222.20224. 226.25227.Formula (IC-1)229. 231.where the symbols X, Rc, RN, L10, L11, L12, Ar11and Ar12have the same meaning as in claim 10.232.35 Foreignfiling_text P24-239-SEC-WO01 20250919233.13412. 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),235.5237. 239.15240.20242. 244.25245.Formula (IA-1-2)246.35 Foreignfiling_text P24-239-SEC-WO01 20250919247.135248.5250. 252.15253.20254. 256.Formula (IA-2-2)257.25259. 261.Formula (IA-3-1)262.35 Foreignfiling_text P24-239-SEC-WO01 20250919263.136264.5265.Formula (IA-3-2)266.15268.

269. 20271. 273.25275.

276. Formula (IB-1-2)277.35 Foreignfiling_text P24-239-SEC-WO01 20250919278.137279.5280.15282. 284.Formula (IB-2-2)285.20286.25288. 290.Formula (IB-3-1)291.35 Foreignfiling_text P24-239-SEC-WO01 20250919292.138293.5294.15296. 298.Formula (IC-1-1)299.20300.25302. 304.Formula (IC-1-2)305.where306.A1is equal to C(RC)2, O, S or equal to307.35 Foreignfiling_text P24-239-SEC-WO01 20250919308.139309.5310. 312.where the dashed lines represent the bonds emanating from the group A1;313.Y stands on each occurrence, identically or differently, for CR10or N; or Y stands for C when it is bonded to the group L12; and314.where the symbols X, Rc, RN, L10, L11, L12, Ar11and Ar12have the same meaning as in claim 10.

13. An electronic device according to one or more of the preceeding claims, characterized 15 in that the compound G2 is selected from compounds of formulae (IIIA), (HUB), (IIIC), (HID), (HID’), (HIE) and (HIF),316.20318. 320.25 Formula (IIIA)322. 324.Formula (IIIB)325.35 Foreignfiling_text P24-239-SEC-WO01 20250919326.140327.5328.Ar31 / L31329.15330. 332.Formula (IIID)333.Ar3120334.25335. 337.Formula (HID’)338.35 Foreignfiling_text P24-239-SEC-WO01 20250919339.141340.5341.Formula (IIIE)342.15344. 346.Formula (IIIF)347.where348.where the following applies to the symbols occurring:349.20350.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;351.25352.Ar30, Ar31, Ar32, Ar33are 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;353.V stands on each occurrence, identically or differently, for CR30or N; or V stands for C when it is bonded to the group L30;354.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;355.35 Foreignfiling_text P24-239-SEC-WO01 20250919356.142357.T36, T37are the same or different at each instance and are selected from O, S, NRN, and C(RC)2;358.5 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 CH2groups 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 R3115 and / or two radicals R32may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R;359.where Rhas the same definition as in claim 1, Rcand RNhave the same mening as in claim 10.360.2014. 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), (IIID’-1), (IIIE-1) and (IIIF-1),362.25364. 366.Formula (IIIA-1)367.35 Foreignfiling_text P24-239-SEC-WO01 20250919368.143369.5370.Formula (IIIA-2)371.15372. 374.Formula (IIIA-3)375.20377.

378. 25 Formula (IIIA-4)379.35 Foreignfiling_text P24-239-SEC-WO01 20250919380.144381.5382.Formula (IIIB)383.15384.

385. 20387.

388. 25390.

391. 35 Foreignfiling_text P24-239-SEC-WO01 20250919392.145393.Ar31 / L31394.5396.

397. Formula (IIID-1) Ar31398.15399.2400.

401. 0402.Formula (IIID’-1)403.25404.Formula (IIIE-1)406. 408.35 Foreignfiling_text P24-239-SEC-WO01 20250919409.146410.5411.Formula (IIIF-1)413. 415.where the symbols V, L30, L31, L32, Ar30, Ar31, Ar32and Ar33have the same meaning as in claim 13, Rcand RNhave the same meaning as in claim 10.

15. 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 (111 A-4-2), 15 (IIIB-1), (IIIB-2), (IIIC-1-1) to (IIIC-3-2), (IIID-1-1), (IIID-1-2), (IIID’-1-1), (IIID’-1-2), (IIID-1- 3), (IIID’-2-1), (IIID’-2-2), (IIIE-1-1), (IIIE-1-2), (IIIF-1-1) and (IIIF-1-2),417.20418.25420. 422.Formula (IIIA-1-1)423.35 Foreignfiling_text P24-239-SEC-WO01 20250919424.5426. 428.Formula (IIIA-1-2)429.15430.20431. 433.25435. 437.Formula (IIIA-2-2)438.35 Foreignfiling_text P24-239-SEC-WO01 20250919439.148440.\ / W=w Formula (IIIA-4-1)441.

442. Foreignfiling_text P24-239-SEC-WO01 20250919443.5444. 446.Formuöa (IIIA-4-2)447.Ar30448.15449.20451.

452. 25453.Formula (IIIB-1)454.35 Foreignfiling_text P24-239-SEC-WO01 20250919455.150456.Ar30457.5459. 461.15 Formula (IIIB-2)462.Ar31463.20465. 467.Formula (IIIC-1-1)468.25469.Ar31 / 471. 473.Formula (IIIC-1-2)474.35 Foreignfiling_text P24-239-SEC-WO01 20250919475.5476.Ar31 / 477.15479. 481.Formula (IIIC-2-2)482.20483.Ar31 / L31484.25486. 488.Formula (IIIC-3-1) Foreignfiling_text P24-239-SEC-WO01 20250919489.5490.Formula (IIIC-3-2)491.Ar31 / L3115492.

493. 20494.Formula (IIID-1-1)495.Ar31 / L3125496.Formula (IIID-1-2)497.

498. Foreignfiling_text P24-239-SEC-WO01 20250919499.153500.Ar31501.5502.Formula (IIID’-1-1)503.Ar31504.15506.

507. 20 Formula (IIID’-1-2)508.Ar31509.25510.Formula (IIID’-1-3)511. 513.35 Foreignfiling_text P24-239-SEC-WO01 20250919514.154515.Ar31 / 516.5518. 520.Formula (IIID’-2-1)521.Ar31522.15523.2524.

525. 0526.Formula (IIID’-2-2)527.25529.

530. Formula (IIIE-1-1)531.35 Foreignfiling_text P24-239-SEC-WO01 20250919532.155533.5534.15536.

537. 20538. 540.25542. 544.Formula (IIIF-1-2)545.Where A2is equal to C(RC)2, O, S or equal to546.35 Foreignfiling_text P24-239-SEC-WO01 20250919547.156548.5549. 551.where the dashed lines represent the bonds emanating from the group A2;552.W stands on each occurrence, identically or differently, for CR30or N; or Y stands for C when it is bonded to the group L32; and553.where the symbols V, L30, L31, L32, Ar30, Ar31, Ar32and Ar33have the same meaning as in claim 13, and Rcand RNhave the same meaning as in claim 10.

16. 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 15 selected from phosphorescent emitters.

17. 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 20 selected from electron-transporting host materials.

18. An electronic device according to claim 17, 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, 25 the dibenzofuran-carbazole derivatives or dibenzofuran-amine derivatives, indolocarbazole and the carbazoleamines.

19. An electronic device according to claim 17 or 18, 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.558.35 Foreignfiling_text P24-239-SEC-WO01 20250919559.15720. An electronic device according to one or more of the preceding claims, characterized in that:561.-5.30 ≤ HOMO (G1) ≤ -5.05 eV562.where HOMO (G1) corresponds to the energy of the highest occupied molecular orbital 5 of the compound G1 as determined by quantum-chemical calculation.

21. An electronic device according to one or more of the preceding claims, characterized in that:564.-5.50 ≤ HOMO (G2) ≤ -5.20 eV565.where HOMO (G2) corresponds to the energy of the highest occupied molecular orbital of the compound G2 as determined by quantum-chemical calculation.

22. An electronic device according to one or more of the preceding claims, according to one or more of the preceding claims, characterized in that:567.15 -5.25 ≤ HOMO (H) ≤ -5.00 eV568.where HOMO (H) corresponds to the energy of the highest occupied molecular orbital of the compound H as determined by quantum-chemical calculation.

23. An electronic device according to one of more of the preceding claims, characterized in 20 that at least one compound selected from compound G1, compound G2 and compound H is a deuterated compound.

24. 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 25 second auxiliary layer comprising the compound G2.

25. 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.

26. 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 G1.573.35 Foreignfiling_text P24-239-SEC-WO01 20250919574.15827. 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-dopants28. An electronic device according to one or more of the preceding claims, characterized in 5 that the hole transport region further comprises a hole injection layer between the first electrode and the hole transport layer comprising the compound H.577.15578.20579.25580.35

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