ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING AN AXIENE OF Formula (I) AND AN ARYLAMININE COMPOUND, A DIARYLAMININE COMPOUND, A TRIARYLAMININE COMPOUND OR A COMPOUND OF Formula (IIA) OR Formula (IIb), AND DISPLAY DEVICE COMPRISING THE ORGANIC ELECTROLUMINESCENT DEVICE

Abstract

The present invention relates to an electroluminescent device comprising an axiene of formula (I) and an arylamine compound, a diarylamine compound, a triarylamine compound or a compound of formula (II), and to a display device comprising the organic electroluminescent device.

Description

Technical Field

[0001] The present invention relates to an electroluminescent device comprising a radialene of formula (I) and a compound of formula (II) and a display device comprising an organic electroluminescent device. Background Art

[0002] Organic electroluminescent devices, such as organic light-emitting diodes (OLEDs), which are self-luminous devices, have wide viewing angles, excellent contrast, fast response, high brightness, excellent operating voltage characteristics, and color reproducibility. A typical OLED comprises an anode, a hole transport layer HTL, an emission layer EML, an electron transport layer ETL, and a cathode stacked sequentially on a substrate. In this regard, HTL, EML, and ETL are thin films formed of organic compounds.

[0003] When voltage is applied to the anode and cathode, holes injected from the anode move toward the EML through the HTL, and electrons injected from the cathode move toward the EML through the ETL. Holes and electrons recombine in the EML to generate excitons. When the excitons drop from an excited state to a ground state, light is emitted. The injection and flow of holes and electrons should be balanced so that the OLED having the above structure has excellent efficiency and / or long life.

[0004] The performance of an organic light emitting diode may be affected by the properties of the semiconductor layer, and in particular, may be affected by the properties of the compound contained in the semiconductor layer.

[0005] There remains a need to improve the performance of organic electroluminescent devices, in particular to achieve improved operating voltage, improved stability of the operating voltage over time and improved current efficiency. Summary of the invention

[0006] One aspect of the present invention provides an organic electroluminescent device, comprising an anode layer, a cathode layer, a first light-emitting unit, a second light-emitting unit and at least one intermediate connection region, wherein the at least one intermediate connection region is arranged between the first light-emitting unit and the second light-emitting unit,

[0007] The first light-emitting unit comprises a first light-emitting layer,

[0008] wherein the second light-emitting unit comprises a second light-emitting layer,

[0009] wherein the at least one intermediate connection region comprises an n-type charge generation layer, an intermediate layer and a p-type charge generation layer,

[0010] wherein the n-type charge generation layer is arranged closer to the anode layer than the p-type charge generation layer;

[0011] wherein the p-type charge generation layer is arranged closer to the cathode layer than the n-type charge generation layer; and

[0012] wherein the intermediate layer is arranged between the n-type charge generation layer and the p-type charge generation layer,

[0013] in

[0014] wherein the n-type charge generation layer comprises a host compound and a metal dopant,

[0015] wherein the p-type charge generating layer comprises a hole transporting host compound and a radialene of formula (I),

[0016]

[0017] Wherein in formula (I),

[0018] -A 1 Independently selected from groups of formula (Ia):

[0019]

[0020] Among them, Ar 1 are independently selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

[0021] For Ar 1 In the case of being substituted, one or more substituents are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl; and

[0022] Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, C1 to C8 alkoxy are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy;

[0023] -A 2 Independently selected from groups of formula (Ib):

[0024]

[0025] Among them, Ar2 are independently selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

[0026] For Ar 2 In the case of being substituted, one or more substituents are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl; and

[0027] Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, C1 to C8 alkoxy are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy;

[0028] -A 3 Independently selected from groups of formula (Ic):

[0029]

[0030] Among them, Ar 3 are independently selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

[0031] For Ar 3 In the case of being substituted, one or more substituents are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl; and

[0032] Among them, C6 to C 30 Aryl, C6 to C 30One or more substituents of heteroaryl, C1 to C8 alkyl, C1 to C8 alkoxy are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy;

[0033] - and in which A 1 , A 2 and A 3 In which each R' is independently selected from substituted or unsubstituted C6 to C 18 Aryl, C3 to C 18 heteroaryl, electron withdrawing group, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, halogen, F and CN;

[0034] The intermediate layer comprises at least one hole transport compound selected from arylamine compounds, diarylamine compounds, triarylamine compounds, compounds of formula (IIa) or compounds of formula (IIb):

[0035]

[0036] in:

[0037] T 1 , T 2 , T 3 , T 4 and T 5 independently selected from a single bond, a phenylene group, a biphenylene group, a terphenylene group or a naphthalene group, preferably a single bond or a phenylene group;

[0038] T 6 is a phenyl subunit, a biphenyl subunit, a terphenyl subunit or a naphthalene subunit;

[0039] Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar' 4 and Ar' 5 independently selected from substituted or unsubstituted C6 to C 20 Aryl or substituted or unsubstituted C3 to C 20heteroarylidene, substituted or unsubstituted biphenylidene, substituted or unsubstituted fluorene, substituted 9-fluorene, substituted 9,9-fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted terphenylidene, substituted or unsubstituted tetracene, substituted or unsubstituted benzanthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthene, substituted or unsubstituted carbazole, substituted 9-phenylcarbazole, substituted or unsubstituted azepane, substituted or unsubstituted dibenzo[b,f]azepane, substituted or unsubstituted 9,9'- Spirobi[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanthene]; or a substituted or unsubstituted aromatic fused ring system comprising at least three substituted or unsubstituted aromatic rings selected from: substituted or unsubstituted non-heterocyclic, substituted or unsubstituted hetero 5-membered ring, substituted or unsubstituted 6-membered ring and / or substituted or unsubstituted 7-membered ring, substituted or unsubstituted fluorene; or a fused ring system comprising 2 to 6 substituted or unsubstituted 5 to 7-membered rings, and the rings are selected from: (i) heterocyclic unsaturated 5 to 7-membered rings, (ii) aromatic heterocyclic 5 to 6-membered rings, (iii) non-heterocyclic unsaturated 5 to 7-membered rings, (iv) aromatic non-heterocyclic 6-membered rings;

[0040] in

[0041] Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar' 4 and Ar' 5 The substituents are selected from the group consisting of H, D, F, C(=O)R' 2 、CN、Si(R' 2 )3. P(=O)(R' 2 )2. OR' 2 、S(=O)R' 2 、S(=O)2R' 2 , substituted or unsubstituted straight-chain alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted branched-chain alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl or alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aromatic ring systems having 6 to 40 aromatic ring atoms and substituted or unsubstituted heteroaromatic ring systems having 5 to 40 aromatic ring atoms, unsubstituted C6 to C 18 Aryl, unsubstituted C3 to C 18heteroaryl, a fused ring system comprising 2 to 6 unsubstituted 5 to 7 membered rings, and the rings are selected from: heterocyclic unsaturated 5 to 7 membered rings, aromatic heterocyclic 5 to 6 membered rings, non-heterocyclic unsaturated 5 to 7 membered rings and aromatic non-heterocyclic 6 membered rings,

[0042] Where R' 2 The alkyl radical may be selected from H, D, a linear alkyl radical having 1 to 6 carbon atoms, a branched alkyl radical having 1 to 6 carbon atoms, a cyclic alkyl radical having 3 to 6 carbon atoms, an alkenyl or alkynyl radical having 2 to 6 carbon atoms, a C6 to C 18 Aryl or C3 to C 18 Heteroaryl.

[0043] It should be noted that, unless otherwise indicated, throughout the application and claims, any A n , B n , R n , X n Etc. always refers to the same part.

[0044] In this specification, when no definition is provided otherwise, "substituted" refers to deuterium, C1 to C 12 Alkyl and C1 to C 12 Alkoxy substituted.

[0045] However, in the present specification, "aryl substituted" means substituted by one or more aryl groups, which may themselves be substituted by one or more aryl and / or heteroaryl groups.

[0046] Accordingly, in this specification, "heteroaryl substituted" means substituted by one or more heteroaryl groups, which may themselves be substituted by one or more aryl and / or heteroaryl groups.

[0047] In this specification, when no definition is provided otherwise, "alkyl group" refers to a saturated aliphatic hydrocarbon group. The alkyl group can be C1 to C 12 More specifically, the alkyl group may be C1 to C 10 An alkyl group or a C1 to C6 alkyl group. For example, a C1 to C4 alkyl group contains 1 to 4 carbons in the alkyl chain and can be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.

[0048] Specific examples of the alkyl group may be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group.

[0049] The term "cycloalkyl" refers to a saturated hydrocarbon group derived from a cycloalkane by formally extracting a hydrogen atom from a ring atom contained in the corresponding cycloalkane. Examples of the cycloalkyl group may be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, an adamantyl group, and the like.

[0050] The term "hetero" is understood to mean that at least one carbon atom in a structure that can be formed by covalently bonded carbon atoms is replaced by another polyvalent atom. Preferably, the heteroatom is selected from B, Si, N, P, O, S; more preferably, N, P, O, S.

[0051] In this specification, "aryl group" refers to a hydrocarbon group that can be generated by formally extracting a hydrogen atom from an aromatic ring in a corresponding aromatic hydrocarbon. Aromatic hydrocarbon refers to a hydrocarbon containing at least one aromatic ring or aromatic ring system. Aromatic ring or aromatic ring system refers to a planar ring or ring system of covalently bound carbon atoms, wherein the planar ring or ring system contains a conjugated system of delocalized electrons that satisfies Huckel's rule. Examples of aryl groups include monocyclic groups such as phenyl or tolyl, polycyclic groups such as biphenyl containing multiple aromatic rings connected by single bonds, and polycyclic groups such as naphthyl or fluorene-2-yl containing fused rings.

[0052] Similarly, heteroaryl is to be understood, where appropriate, in particular as a radical which is derived by abstraction of a ring hydrogen from this ring form in compounds which contain at least one heterocyclic aromatic ring.

[0053] Heterocycloalkyl is understood, where appropriate, in particular to mean a radical which is derived by formal abstraction of a ring hydrogen from at least one saturated cycloalkyl ring in compounds which contain such a ring.

[0054] The term "fused aryl ring" or "condensed aryl ring" is understood to mean when two aryl rings share at least two common sp 2 When carbon atoms are hybridized, they are considered fused or condensed.

[0055] The term "cyano moiety" refers to a CN substituent.

[0056] The term "electron withdrawing group" refers to a chemical group in a molecule that is capable of pulling electrons away from adjacent parts of the molecule. The distance over which the electron withdrawing group can exert its effect, i.e., the number of bonds spanned by the electron withdrawing effect, is enlarged by conjugated π-electron systems such as aromatic systems. Examples of electron withdrawing groups include NO2, CN, halogens, Cl, F, partially fluorinated or perfluorinated alkyl groups, and partially fluorinated or perfluorinated C1 to C 12 Alkyl, partially fluorinated or perfluorinated alkoxy, partially fluorinated or perfluorinated C1 to C6 alkoxy.

[0057] In this specification, a single bond means a direct bond.

[0058] The term "n-type charge generation layer" is sometimes also referred to in the art as n-CGL or electron generation layer, and is intended to include both.

[0059] The term "p-type charge generation layer" is sometimes also referred to in the art as a p-CGL or a hole generation layer, and is intended to include both.

[0060] The terms "does not contain", "does not contain", "does not include" do not exclude impurities that may be present in the compound before deposition. Impurities have no technical impact on the purpose to be achieved by the present invention.

[0061] The term "sandwiched in contact" refers to a three-layer arrangement in which a middle layer is in direct contact with two adjacent layers.

[0062] The terms "light absorbing layer" and "light absorbing layer" are used synonymously.

[0063] The terms "light emitting layer", "light emitting layer" and "emissive layer" are used synonymously.

[0064] The terms "OLED," "organic light emitting diode," and "organic light emitting device" are used synonymously.

[0065] The terms "anode", "anode layer" and "anode electrode" are used synonymously.

[0066] The terms "cathode", "cathode layer" and "cathode electrode" are used synonymously.

[0067] The term "top emitting device" is understood to mean an organic electroluminescent device wherein light is emitted via the cathode layer.

[0068] The term "bottom-emitting device" is understood to mean an organic electroluminescent device wherein the light is emitted through the substrate.

[0069] In this specification, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and holes formed in the anode due to conductive characteristics according to the highest occupied molecular orbital (HOMO) energy level can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0070] In addition, the electronic property refers to the ability to accept electrons when an electric field is applied, and electrons formed in the cathode due to the conductive property according to the lowest unoccupied molecular orbital (LUMO) energy level can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0071] Beneficial Effects

[0072] Surprisingly, it was found that the organic electroluminescent device according to the invention solves the problem underlying the invention by enabling the device to be superior to organic electroluminescent devices known in the art in several respects, in particular in terms of improved stability of the operating voltage over time.

[0073] According to one embodiment of the present invention, the interlayer consists essentially of one or more hole transport compounds.

[0074] According to one embodiment, the intermediate layer is an organic intermediate layer.

[0075] In the context of the present invention, the term "essentially consists of" especially means and / or comprises a ratio (wt. % / wt. %) of ≥95 wt. %, more preferably ≥97.0 wt. %, more preferably ≥97.25 wt. %, more preferably ≥97.5 wt. %, more preferably ≥97.75 wt. %, more preferably ≥98.0 wt. %, more preferably ≥99.0 wt. %, more preferably ≥99.5 wt. %, more preferably ≥99.75 wt. %, more preferably ≥99.80 wt. %, more preferably ≥99.85 wt. %, more preferably ≥99.9 wt. %, more preferably ≥99.95 wt. %, most preferably ≥99.99 wt. %.

[0076] According to one embodiment of the present invention, the hole transport compound of the intermediate layer is selected from arylamine, diarylamine, triarylamine, formula (IIa) and formula (IIb).

[0077] According to one embodiment of the present invention, the hole transport compound of the intermediate layer is selected from the compound of formula (IIa) or the compound of formula (IIb).

[0078] According to one embodiment of the present invention, the hole transport compound of the intermediate layer is selected from the compounds of formula (IIa).

[0079] According to one embodiment, the intermediate layer consists essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, formula (IIa) and formula (IIb).

[0080] According to one embodiment, the intermediate layer consists essentially of at least one compound selected from the group consisting of formula (IIa) and formula (IIb).

[0081] According to one embodiment, the at least one hole transport compound consists essentially of at least one compound selected from the group consisting of formula (IIa) and formula (IIb).

[0082] According to one embodiment, the intermediate layer consists essentially of at least one compound of formula (IIa).

[0083] According to one embodiment, the intermediate layer consists essentially of the compound of formula (IIa).

[0084] According to one embodiment, the at least one hole transport compound is a compound of formula (IIa).

[0085] According to one embodiment, the intermediate layer has a layer thickness of ≤20 nm, ≤15 nm, ≤10 nm, ≤5 nm, ≤4 nm, ≤3 nm, ≤2 nm, ≤1 nm, ≤0.5 nm.

[0086] According to one embodiment, the layer thickness of the intermediate layer is in a range of ≥0.05 nm to ≤20.0 nm, ≥0.1 nm to ≤15.0 nm, ≥0.2 nm to ≤10.0 nm, ≥0.3 nm to ≤5.0 nm, ≥0.4 nm to ≤4.0 nm, ≥0.5 nm to ≤3.0 nm, ≥0.5 nm to ≤2.0 nm, ≥0.5 nm to ≤1.5 nm, ≥0.5 nm to ≤1.25 nm, ≥0.5 nm to ≤1.0 nm.

[0087] According to one embodiment, the p-type charge generation layer is in direct contact with the intermediate layer.

[0088] According to one embodiment, the n-type charge generation layer is in direct contact with the intermediate layer.

[0089] According to one embodiment, the p-type charge generation layer is in direct contact with the intermediate layer, and the n-type charge generation layer is in direct contact with the intermediate layer.

[0090] According to one embodiment, the hole transport compound or compounds of the intermediate layer and the hole transport host compound of the p-type generating layer are selected to be identical.

[0091] According to one embodiment, the ratio of the layer thicknesses of the intermediate layer and the p-type charge generation layer is in a range of ≥0.01 to ≤10.0, ≥0.02 to ≤5.0, ≥0.03 to ≤2.5, ≥0.04 to ≤2.0, ≥0.05 to ≤1.0, ≥0.05 to ≤0.5, ≥0.05 to ≤0.4, ≥0.05 to ≤0.3, ≥0.05 to ≤0.2, ≥0.05 to ≤0.2.

[0092] According to one embodiment, the ratio of the layer thicknesses of the intermediate layer and the n-type charge generation layer is in a range of ≥0.01 to ≤10.0, ≥0.02 to ≤5.0, ≥0.03 to ≤2.5, ≥0.04 to ≤2.0, ≥0.05 to ≤1.0, ≥0.05 to ≤0.5, ≥0.05 to ≤0.4, ≥0.06 to ≤0.3.

[0093] According to one embodiment, the layer thickness ratio of the intermediate layer and the p-type charge generation layer is in the range of ≥0.01 to ≤10.0, ≥0.02 to ≤5.0, ≥0.03 to ≤2.5, ≥0.04 to ≤2.0, ≥0.05 to ≤1.0, ≥0.05 to ≤0.5, ≥0.05 to ≤0.4, ≥0.05 to ≤0.3, ≥0.05 to ≤0.2, ≥0.05 to ≤0.2, and the layer thickness ratio of the intermediate layer and the n-type charge generation layer is in the range of ≥0.01 to ≤10.0, ≥0.02 to ≤5.0, ≥0.03 to ≤2.5, ≥0.04 to ≤2.0, ≥0.05 to ≤1.0, ≥0.05 to ≤0.5, ≥0.05 to ≤0.4, ≥0.06 to ≤0.3.

[0094] According to one embodiment, the thickness ratio of the intermediate layer to the p-type charge generation layer is in the range of ≥0.05 to ≤0.2, and the thickness ratio of the intermediate layer to the n-type charge generation layer is in the range of ≥0.06 to ≤0.3.

[0095] According to one embodiment, the hole transport compound of the intermediate layer has a HOMO level calculated by using TURBOMOLEV6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, and the hole transport host compound of the p-type charge generation layer has a HOMO level calculated by using TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase,

[0096] The absolute value of the difference between the HOMO energy level of the hole transport compound of the intermediate layer and the HOMO energy level of the hole transport host compound of the p-type charge generation layer is ≤0.5eV, preferably ≤0.4eV, more preferably ≤0.3eV, even more preferably ≤0.2eV, even more preferably ≤0.1eV, and most preferably 0eV.

[0097] Radialene of formula (I):

[0098] According to one embodiment of the present invention, when using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO of the olefin of formula (I) is ≤-4.70 eV, preferably ≤-4.80 eV, more preferably ≤-4.90 eV, more preferably ≤-5.00 eV, more preferably ≤-5.10 eV, more preferably ≤-5.15 eV, and most preferably ≤-5.20 eV.

[0099] According to one embodiment of the present invention, when using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO of the radialene of formula (I) is in the range of ≥-7.00eV to ≤-4.70eV, preferably in the range of ≥-6.50eV to ≤-4.80eV, more preferably in the range of ≥-6.00eV to ≤-4.85eV, more preferably in the range of ≥-5.80eV to ≤-4.90eV, more preferably in the range of ≥-5.60eV to ≤-5.00eV, more preferably in the range of ≥-5.50eV to ≤-5.10eV, more preferably in the range of ≥-5.45eV to ≤-5.20eV.

[0100] According to one embodiment of the present invention, the radialene of formula (I) comprises at least one CF3 group.

[0101] According to one embodiment of the present invention, the radialene of formula (I) comprises one to three CF3 groups.

[0102] According to one embodiment of the present invention, the radialene of formula (I) comprises less than nine cyano moieties.

[0103] According to one embodiment of the present invention, the radialene of formula (I) comprises less than eight cyano moieties.

[0104] According to one embodiment of the present invention, the radialene of formula (I) comprises at least one cyano moiety.

[0105] According to one embodiment of the present invention, the radialene of formula (I) comprises at least two cyano moieties.

[0106] According to one embodiment of the present invention, the radialene of formula (I) comprises at least three cyano moieties.

[0107] According to one embodiment of the present invention, the radialene of formula (I) comprises at least four cyano moieties.

[0108] According to one embodiment of the present invention, the radialene of formula (I) comprises 3 to 8 cyano moieties.

[0109] According to one embodiment of the present invention, the radialene of formula (I) comprises 3 to 7 cyano moieties.

[0110] According to one embodiment of the present invention, the radialene of formula (I) comprises 4 to 7 cyano moieties.

[0111] According to one embodiment of the present invention, formula (I) contains at least 10 fluorine atoms, at least 12 fluorine atoms, at least 13 fluorine atoms, at least 14 fluorine atoms, at least 15 fluorine atoms, at least 16 fluorine atoms, at least 17 fluorine atoms or at least 18 fluorine atoms.

[0112] According to one embodiment of the present invention, formula (I) contains 10 to 20 fluorine atoms, or 10 to 18 fluorine atoms, or 12 to 18 fluorine atoms.

[0113] According to one embodiment of the present invention, formula (I) contains 4 to 7 cyano moieties and 12 to 18 fluorine atoms.

[0114] According to one embodiment of the present invention, in formula (I), A 1 , A 2 and A 3 At least two of are selected to be the same.

[0115] According to one embodiment of the present invention, in formula (I), A 2 and A 3 are the same.

[0116] According to one embodiment of the present invention, in formula (I), A 1 , A 2 and A 3 are the same.

[0117] According to one embodiment of the present invention, in formula (I), A 1 With A 2 and / or A 3 different.

[0118] According to one embodiment of the present invention, in formula (I), A 1 With A 2 and / or A 3 Different, and A 2 and A 3 are selected as identical.

[0119] According to one embodiment, in formula (I), Ar 1 is selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C3 to C 36 Heteroaryl.

[0120] According to one embodiment, Ar 1 ,Ar 2 and Ar 3 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C3 to C 36 Heteroaryl.

[0121] According to one embodiment, in formula (I), Ar 1 is selected from substituted or unsubstituted C6 to C 24 Aryl and substituted or unsubstituted C3 to C 24 Heteroaryl.

[0122] According to one embodiment, in formula (I), Ar 1 ,Ar 2 and Ar 3 independently selected from substituted or unsubstituted C6 to C 24 Aryl and substituted or unsubstituted C3 to C 24 Heteroaryl.

[0123] According to one embodiment, in formula (I), Ar 1 is selected from substituted or unsubstituted C6 to C 18 Aryl and substituted or unsubstituted C3 to C 18 Heteroaryl.

[0124] According to one embodiment, in formula (I), Ar 1 ,Ar 2 and Ar 3 independently selected from substituted or unsubstituted C6 to C 18 Aryl and substituted or unsubstituted C3 to C 18 Heteroaryl.

[0125] According to one embodiment of the present invention, in formula (I), Ar 1 independently selected from substituted or unsubstituted C6 to C 12 Aryl and substituted or unsubstituted C3 to C 12 Heteroaryl.

[0126] According to one embodiment of the present invention, in formula (I), Ar 1 ,Ar 2 and Ar 3 independently selected from substituted or unsubstituted C6 to C 12Aryl and substituted or unsubstituted C3 to C 12 Heteroaryl.

[0127] According to one embodiment of the present invention, in formula (I), Ar 1 are independently selected from substituted or unsubstituted C6 aryl and substituted or unsubstituted C3 to C5 heteroaryl.

[0128] According to one embodiment of the present invention, in formula (I), Ar 1 ,Ar 2 and Ar 3 are independently selected from substituted or unsubstituted C6 aryl and substituted or unsubstituted C3 to C5 heteroaryl.

[0129] According to one embodiment of the present invention, in formula (I), Ar 1 The substituents on are independently selected from electron withdrawing groups, halogens, Cl, F, CN, NO2, partially fluorinated alkyls and perfluorinated alkyls.

[0130] According to one embodiment of the present invention, in formula (I), Ar 1 ,Ar 2 and Ar 3 The substituents on are independently selected from electron withdrawing groups, halogens, Cl, F, CN, NO2, partially fluorinated alkyls and perfluorinated alkyls.

[0131] According to one embodiment of the present invention, in formula (I), Ar 1 The substituents on are independently selected from electron withdrawing groups, halogens, Cl, F, CN, partially fluorinated alkyls and perfluorinated alkyls.

[0132] According to one embodiment of the present invention, in formula (I), Ar 1 ,Ar 2 and Ar 3 The substituents on are independently selected from electron withdrawing groups, halogens, Cl, F, CN, partially fluorinated alkyls and perfluorinated alkyls.

[0133] According to one embodiment of the present invention, in formula (I), Ar 1 The substituents on are independently selected from Cl, F, CN, NO2 and perfluorinated alkyl.

[0134] According to one embodiment of the present invention, in formula (I), Ar 1 ,Ar 2 and Ar 3 The substituents on are independently selected from Cl, F, CN, NO2 and perfluorinated alkyl.

[0135] According to one embodiment of the present invention, in formula (I), Ar1 The substituents on are independently selected from Cl, F, CN and perfluorinated alkyl.

[0136] According to one embodiment of the present invention, in formula (I), Ar 1 ,Ar 2 and Ar 3 The substituents on are independently selected from Cl, F, CN and perfluorinated alkyl.

[0137] According to one embodiment of the present invention, in formula (I), Ar 1 The substituents on R are independently selected from F, CN, NO2 and perfluorinated alkyl.

[0138] According to one embodiment of the present invention, in formula (I), Ar 1 ,Ar 2 and Ar 3 The substituents on R are independently selected from F, CN, NO2 and perfluorinated alkyl.

[0139] According to one embodiment of the present invention, in formula (I), Ar 1 The substituents on R are independently selected from F, CN and perfluorinated alkyl.

[0140] According to one embodiment of the present invention, in formula (I), Ar 1 ,Ar 2 and Ar 3 The substituents on R are independently selected from F, CN and perfluorinated alkyl.

[0141] According to one embodiment of the present invention, in formula (I), Ar 1 The substituents on are independently selected from F, CN, NO2 and CF3.

[0142] According to one embodiment of the present invention, in formula (I), Ar 1 ,Ar 2 and Ar 3 The substituents on are independently selected from F, CN, NO2 and CF3.

[0143] According to one embodiment of the present invention, in formula (I), Ar 1 The substituents on are independently selected from F, CN and CF3.

[0144] According to one embodiment of the present invention, in formula (I), Ar 1 ,Ar 2 and Ar 3 The substituents on are independently selected from F, CN and CF3.

[0145] According to one embodiment of the present invention, in formula (I), Ar1 Each independently contains more than one and less than five substituents, preferably more than two and less than four, for example 4 substituents.

[0146] According to one embodiment of the present invention, in formula (I), Ar 1 ,Ar 2 and Ar 3 Each independently contains more than one and less than five substituents, preferably more than two and less than four, for example 4 substituents.

[0147] According to one embodiment of the present invention, in formula (I), each R' is independently selected from an electron withdrawing group, a partially fluorinated C1 to C8 alkyl group, a perfluorinated C1 to C8 alkyl group, a halogen, F and CN.

[0148] According to one embodiment of the present invention, in formula (I), each R' is independently selected from partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, halogen, F and CN.

[0149] According to one embodiment of the present invention, in formula (I), each R' is independently selected from CF3, F and CN.

[0150] According to one embodiment of the present invention, in formula (I), each R' is CN.

[0151] According to one embodiment of the present invention, in formula (I), Ar 1 ,Ar 2 and Ar 3 are independently selected from groups according to the following formula (III), and preferably each R' is selected from CN:

[0152]

[0153] in

[0154] E 1 From The CW 1 or N;

[0155] E 2 From The CW 2 or N;

[0156] E 3 From The CW 3 or N;

[0157] E 4 From The CW 4 or N;

[0158] E 5 From The CW 5 or N;

[0159] W 1 , W 2 , W 3 , W 4 and W 5 (if present) are independently selected from electron withdrawing groups, CN, halogen, Cl, F, NO2, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C6 alkoxy, OCF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C3 to C 30 heteroaryl, D or H,

[0160] wherein one or more substituents are independently selected from D, halogen, Cl, F, CN, NO2, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy,

[0161] The asterisk "*" indicates the binding position.

[0162] According to one embodiment of the present invention, in formula (III),

[0163] W 1 , W 2 , W 3 , W 4 and W 5 (if present) is independently selected from an electron withdrawing group, CN, halogen, Cl, F, NO2, partially fluorinated or perfluorinated C1 to C8 alkyl, partially fluorinated or perfluorinated C1 to C6 alkoxy, D or H, and wherein preferably each R' is selected from CN.

[0164] According to one embodiment of the present invention, in formula (I), Ar 1 ,Ar 2 and / or Ar 3 Independently selected from one of the following groups, and preferably each R' is selected from CN:

[0165]

[0166]

[0167] The asterisk "*" indicates the binding position.

[0168] According to one embodiment of the present invention, in formula (I), Ar 1 is selected from one of the following groups, and preferably each R' is selected from CN:

[0169]

[0170]

[0171] The asterisk "*" indicates the binding position.

[0172] According to one embodiment of the present invention, in formula (I), Ar 1 ,Ar 2 and / or Ar 3 Independently selected from one of the following groups, and preferably each R' is selected from CN:

[0173]

[0174]

[0175] The asterisk "*" indicates the binding position.

[0176] According to one embodiment of the present invention, in formula (I), Ar 1 Independently selected from one of the following groups, and preferably each R' is selected from CN:

[0177]

[0178]

[0179] The asterisk "*" indicates the binding position.

[0180] According to one embodiment of the present invention, in formula (I), Ar 1 ,Ar 2 and / or Ar 3 Independently selected from one of the following groups, and preferably each R' is selected from CN:

[0181]

[0182] The asterisk "*" indicates the binding position.

[0183] According to one embodiment of the present invention, in formula (I), Ar 1 is selected from one of the following groups, and preferably each R' is selected from CN:

[0184]

[0185]

[0186] The asterisk "*" indicates the binding position.

[0187] According to one embodiment, Ar of formula (I) 1One selected from the following groups B1 to B64, preferably A 1 R' is CN, or Ar of formula (I) 1 ,Ar 2 and / or Ar 3 Independently selected from one of the following groups B1 to B64, and preferably A 1 , A 2 and A 3 Each R' is a CN:

[0188]

[0189]

[0190]

[0191] The asterisk "*" indicates the binding position.

[0192] According to one embodiment, Ar of formula (I) 1 One of the following groups, preferably A 1 R' is CN, or Ar of formula (I) 1 ,Ar 2 and Ar 3 Independently selected from one of the following groups, and preferably A 1 , A 2 and A 3 Each R' is a CN:

[0193]

[0194] The asterisk "*" indicates the binding position.

[0195] According to one embodiment, Ar 1 One of the following groups is selected, and preferably A 1 R' is CN, or Ar of formula (I) 1 ,Ar 2 and Ar 3 Independently selected from one of the following groups, and preferably A 1 , A 2 and A 3 Each R' is a CN:

[0196]

[0197] The asterisk "*" indicates the binding position.

[0198] According to one embodiment of the present invention, the radialene of formula (I) is selected from one of the following compounds A1 to A16, wherein R' is selected from CN, and A 1 Ar 1 , A 2 Ar 2 and A 3 Ar 3 The choices are as follows:

[0199]

[0200]

[0201]

[0202] The asterisk "*" indicates the binding position.

[0203] According to one embodiment of the present invention, the radialene of formula (I) is selected from one of compounds A2, A3, A5, A6, A11, A15 and A16.

[0204] According to one embodiment of the present invention, the radialene of formula (I) is represented by one of the following formulas (IIIa) to (IIIh):

[0205]

[0206] Among them, Ar 1 ,Ar 2 ,Ar 3 and R' are independently selected as above.

[0207] According to one embodiment of the present invention, the p-type generating layer comprises, as the radialene of formula (I), a mixture of at least two compounds selected from the group consisting of compounds of formula (IIIa) to formula (IIIh) as defined above.

[0208] Hole transport compounds

[0209] According to one embodiment of the present invention, when measured by the same method, the HOMO energy level of the hole transport compound is less than the HOMO energy level of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirobi[fluorene]-2,2',7,7'-tetramine, preferably less than the HOMO energy level of N4,N4,N4',N4'-tetra(4-methoxyphenyl)biphenyl-4,4'-diamine, more preferably less than the HOMO energy level of N4,N4'-bis(9,9-dimethyl-9H-fluorene-2-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine. When using TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the HOMO level of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirobi[fluorene]-2,2',7,7'-tetramine is -4.27 eV, the HOMO level of N4,N4,N4',N4'-tetrakis(4-methoxyphenyl)biphenyl-4,4'-diamine is -4.34 eV, and the HOMO level of N4,N4'-bis(9,9-dimethyl-9H-fluoren-2-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine is -4.64 eV when calculated by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase.

[0210] According to one embodiment of the present invention, when using TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase for calculation, the HOMO level of the hole transport compound is ≤-4.27 eV, preferably ≤-4.34 eV, more preferably ≤-4.40 eV, even more preferably ≤-4.45 eV, even more preferably ≤-4.50 eV, even more preferably ≤-4.55 eV, even more preferably ≤-4.60 eV, even more preferably ≤-4.65 eV.

[0211] According to one embodiment of the present invention, when using TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), when calculated by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the HOMO level of the hole transport compound is in the range of ≥-6.50 eV to ≤-4.27 eV, preferably in the range of ≥-6.00 eV to ≤-4.34 eV, more preferably in the range of ≥-5.50 eV to ≤-4.40 eV, even more preferably in the range of ≥-5.40 eV to ≤-4.45 eV, even more preferably in the range of ≥-5.30 eV to ≤-4.50 eV, even more preferably in the range of ≥-5.20 eV to ≤-4.55 eV, even more preferably in the range of ≥-5.10 eV to ≤-4.60 eV, even more preferably in the range of ≥-5.00 eV to ≤-4.65 eV.

[0212] In the context of the present invention, the term "HOMO level is less than" means that the absolute value of the HOMO level is greater than the absolute value of the HOMO level compared with it. In particular, in the context of the present invention, the term "HOMO level is less than" means that the HOMO level is further away from the vacuum level than the value of the HOMO level compared with it.

[0213] According to one embodiment, when using TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase for calculation, the LUMO energy level of the hole transport host compound is ≥-2.50 eV, preferably ≥-2.00 eV, more preferably ≥-1.50 eV, even more preferably ≥-1.40 eV, and most preferably ≥-1.30 eV.

[0214] According to one embodiment, when using TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase for calculation, the LUMO energy level of the hole transport host compound is in the range of ≥-2.50 eV to ≤0 eV, preferably in the range of ≥-2.00 eV to ≤-0.1 eV, more preferably in the range of ≥-1.50 eV to ≤-0.3 eV, even more preferably in the range of ≥-1.40 eV to ≤-0.5 eV, and most preferably in the range of ≥-1.30 eV to ≤-0.7 eV.

[0215] According to one embodiment, the molecular weight Mw of the hole transport compound is ≥400 g / mol and ≤2000 g / mol, preferably the molecular weight Mw is ≥450 g / mol and ≤1500 g / mol, more preferably the molecular weight Mw is ≥500 g / mol and ≤1000 g / mol, further preferably the molecular weight Mw is ≥550 g / mol and ≤900 g / mol, and further preferably the molecular weight Mw is ≥600 g / mol and ≤800 g / mol.

[0216] The hole transport compound may be free of HTM014, HTM081, HTM163, HTM222, EL-301, HTM226, HTM355, HTM133, HTM334, HTM604 and EL-22T. The abbreviation indicates the name of the manufacturer, for example Merck or Lumtec.

[0217] The intermediate layer may be free of HTM014, HTM081, HTM163, HTM222, EL-301, HTM226, HTM355, HTM133, HTM334, HTM604 and EL-22T. The abbreviations represent the names of manufacturers, such as Merck or Lumtec.

[0218] According to one embodiment, the hole transport compound is at least one compound selected from the group consisting of Formula (IIa) and Formula (IIb).

[0219] According to one embodiment, the hole transport compound is a compound of formula (IIa).

[0220] According to one embodiment, the compound according to formula (IIa) or formula (IIb) comprises at least one naphthyl group, carbazole group, dibenzofuran group, dibenzothiophene group and / or substituted fluorenyl group, wherein the substituents are independently selected from methyl, phenyl or fluorenyl.

[0221] According to one embodiment, wherein T 1 , T 2 , T 3 , T 4 and T 5 can be independently selected from a single bond, a phenyl group, a biphenyl group or a terphenyl group. According to one embodiment, wherein T 1 , T 2 , T 3 , T 4 and T 5 can be independently selected from a phenyl subunit, a biphenyl subunit or a terphenyl subunit, and T 1 , T 2 , T 3 , T4 and T 5 is a single bond. According to one embodiment, wherein T 1 , T 2 , T 3 , T 4 and T 5 may be independently selected from a phenylene group or a biphenylene group, and T 1 , T 2 , T 3 , T 4 and T 5 is a single bond. According to one embodiment, wherein T 1 , T 2 , T 3 , T 4 and T 5 may be independently selected from a phenylene group or a biphenylene group, and T 1 , T 2 , T 3 , T 4 and T 5 Two of them are single bonds.

[0222] According to one embodiment, wherein T 1 , T 2 and T 3 may be independently selected from phenylene groups, and T 1 , T 2 and T 3 is a single bond. According to one embodiment, wherein T 1 , T 2 and T 3 may be independently selected from phenylene groups, and T 1 , T 2 and T 3 Two of them are single bonds.

[0223] According to one embodiment, wherein T 6 It can be a phenyl subunit, a biphenyl subunit, or a terphenyl subunit. According to one embodiment, wherein T 6 According to one embodiment, wherein T 6 It can be a biphenyl subunit. According to one embodiment, wherein T 6 It may be a terphenyl subunit.

[0224] According to another aspect of the present invention, in formula (IIa) and / or formula (IIb), where applicable, T 1 , T 2 , T 3 , T 4 and T 5 may be independently selected from a single bond, a phenylene group, a biphenylene group or a terphenylene group.

[0225] According to one embodiment, in formula (IIa) and / or formula (IIb), where applicable, T 1 , T 2 , T 3 , T 4 and T 5 can be independently selected from a phenyl subunit, a biphenyl subunit or a terphenyl subunit, and T 1 , T 2 , T 3 , T 4 and T 5 One of them is a single bond.

[0226] According to one embodiment, in formula (IIa) and / or formula (IIb), where applicable, T 1 , T 2 , T 3 , T 4 and T 5 may be independently selected from a phenylene group or a biphenylene group, and T 1 , T 2 , T 3 , T 4 and T 5 One of them is a single bond.

[0227] According to one embodiment, in formula (IIa) and / or formula (IIb), where applicable, T 1 , T 2 , T 3 , T 4 and T 5 may be independently selected from a phenylene group or a biphenylene group, and T 1 , T 2 , T 3 , T 4 and T 5 Two of them are single bonds.

[0228] According to one embodiment, in formula (IIa) and / or formula (IIb), where applicable, T 1 , T 2 and T 3 may be independently selected from phenylene groups, and T 1 , T 2 and T 3 One of them is a single bond.

[0229] According to one embodiment, in formula (IIa) and / or formula (IIb), where applicable, T 1 , T 2 and T 3 may be independently selected from phenylene groups, and T1 、T 2 and T 3 Two of them are single bonds.

[0230] According to one embodiment, in formula (IIb), T 6 It can be a phenyl subunit, a biphenyl subunit, or a terphenyl subunit.

[0231] According to one embodiment, in formula (IIb), T 6 It is a phenylene group.

[0232] According to one embodiment, in formula (IIb), T 6 It is a biphenyl subunit.

[0233] According to one embodiment, in formula (IIb), T 6 It is a terphenyl subunit.

[0234] According to one embodiment, in formula (IIa) and / or formula (IIb), where applicable, Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar' 4 and / or Ar' 5 Independently selected from D1 to D16:

[0235]

[0236] The asterisk "*" indicates the binding position.

[0237] According to one embodiment, in formula (IIa) and / or formula (IIb), where applicable, Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar' 4 and / or Ar' 5 Independently selected from D1 to D15; or selected from D1 to D10 and D13 to D15.

[0238] According to one embodiment, in formula (IIa) and / or formula (IIb), where applicable, Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar' 4 and / or Ar' 5 Can be independently selected from D1, D2, D5, D7, D9, D10, D13 to D16.

[0239] When Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar'4 and Ar' 5 When selected within this range, the standard starting temperature can be in a range particularly suitable for mass production.

[0240] According to one embodiment, formula (IIa) and / or formula (IIb), where applicable, is selected from compound (IIc):

[0241]

[0242] in

[0243] T 1 , T 2 , T 3 independently selected from a single bond, a phenylene group, a biphenylene group, a terphenylene group or a naphthalene group, preferably a single bond or a phenylene group;

[0244] Ar 1 ,Ar 2 ,Ar 3 independently selected from substituted or unsubstituted C6 to C 20 Aryl or substituted or unsubstituted C3 to C 20 Heteroarylidene, substituted or unsubstituted biphenylidene, substituted or unsubstituted fluorene, substituted 9-fluorene, substituted 9,9-fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted terphenylidene, substituted or unsubstituted tetracene, substituted or unsubstituted benzanthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthene, substituted or unsubstituted carbazole, substituted 9-phenylcarbazole, substituted or unsubstituted azepane, substituted or unsubstituted dibenzo[b,f]azepane, substituted or unsubstituted 9,9' -spirobi[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanthene]; or a substituted or unsubstituted aromatic fused ring system comprising at least three substituted or unsubstituted aromatic rings selected from substituted or unsubstituted non-heterocyclic rings, substituted or unsubstituted hetero 5-membered rings, substituted or unsubstituted 6-membered rings and / or substituted or unsubstituted 7-membered rings, substituted or unsubstituted fluorene; or a fused ring system comprising 2 to 6 substituted or unsubstituted 5 to 7-membered rings, and the rings are selected from: (i) heterocyclic unsaturated 5 to 7-membered rings, (ii) aromatic heterocyclic 5 to 6-membered rings, (iii) non-heterocyclic unsaturated 5 to 7-membered rings, (iv) aromatic non-heterocyclic 6-membered rings;

[0245] in

[0246] Ar 1 ,Ar 2 ,Ar 3The substituents are selected from H, D, F, CN, Si(R 2 )3, substituted or unsubstituted straight-chain alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted branched-chain alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl or alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aromatic ring systems having 6 to 40 aromatic ring atoms and substituted or unsubstituted heteroaromatic ring systems having 5 to 40 aromatic ring atoms, unsubstituted C6 to C 18 Aryl, unsubstituted C3 to C 18 heteroaryl, a fused ring system comprising 2 to 6 unsubstituted 5 to 7 membered rings selected from heterocyclic unsaturated 5 to 7 membered rings, aromatic heterocyclic 5 to 6 membered rings, non-heterocyclic unsaturated 5 to 7 membered rings and aromatic non-heterocyclic 6 membered rings,

[0247] Where R 2 The alkyl radical may be selected from H, D, a linear alkyl radical having 1 to 6 carbon atoms, a branched alkyl radical having 1 to 6 carbon atoms, a cyclic alkyl radical having 3 to 6 carbon atoms, an alkenyl or alkynyl radical having 2 to 6 carbon atoms, a C6 to C 18 Aryl or C3 to C 18 Heteroaryl.

[0248] According to one embodiment of the electronic device, the one or more hole transport compounds and / or formula (IIa) and / or formula (IIb), where applicable, are selected from F1 to F18:

[0249]

[0250]

[0251]

[0252] According to one embodiment of the electronic device, formula (IIa) and / or formula (IIb), where applicable, is selected from F3 to F18.

[0253] p-type charge generation layer (pCGL)

[0254] According to one embodiment, the thickness of the p-type charge generation layer is ≤20 nm, ≤15 nm, or ≤10 nm.

[0255] According to one embodiment, the p-type charge generation layer has a thickness in a range of ≥1 nm to ≤20 nm, ≥2 nm to ≤15 nm, ≥3 nm to ≤15 nm, or ≥5 nm to ≤15 nm.

[0256] According to one embodiment, the amount of the hole transport host compound present in the p-type charge generation layer is ≥0.1 wt %, preferably ≥1 wt %, more preferably ≥5 wt %, more preferably ≥10 wt %, more preferably ≥20 wt %, more preferably ≥30 wt %, more preferably ≥40 wt %, more preferably ≥50 wt %, more preferably ≥60 wt %, more preferably ≥70 wt %, more preferably ≥80 wt %, more preferably ≥90 wt %, and most preferably ≥95 wt %.

[0257] According to one embodiment of the present invention, relative to the total weight of the p-type charge generation layer, the amount of the olefin of formula (I) present in the p-type charge generation layer is ≤99.9% by weight, preferably ≤99% by weight, more preferably ≤95% by weight, more preferably ≤90% by weight, more preferably ≤80% by weight, more preferably ≤70% by weight, more preferably ≤60% by weight, more preferably ≤50% by weight, more preferably ≤40% by weight, more preferably ≤30% by weight, more preferably ≤20% by weight, more preferably ≤10% by weight, more preferably ≤5% by weight.

[0258] The hole transport host compound may be free of HTM014, HTM081, HTM163, HTM222, EL-301, HTM226, HTM355, HTM133, HTM334, HTM604 and EL-22T. The abbreviations represent the names of manufacturers, such as Merck or Lumtec.

[0259] The p-type charge generation layer may be free of HTM014, HTM081, HTM163, HTM222, EL-301, HTM226, HTM355, HTM133, HTM334, HTM604 and EL-22T. The abbreviation indicates the name of the manufacturer, such as Merck or Lumtec.

[0260] Hole transport host compounds

[0261] According to one embodiment, the hole transport host compound of the p-type charge generation layer comprises a material selected from an arylamine compound, a diarylamine compound, a triarylamine compound, a compound of formula (IIa) or a compound of formula (IIb), wherein all details and descriptions described in the case of the hole transport compound apply mutatis mutandis.

[0262] According to one embodiment of the present invention, the hole transport host compound of the p-type charge generation layer is selected from the compound of formula (IIa) or the compound of formula (IIb).

[0263] According to one embodiment of the present invention, the hole transport host compound of the p-type charge generation layer is selected from the compounds of formula (IIa).

[0264] According to one embodiment of the present invention, the hole transport compound of the intermediate layer is selected from the compound of formula (IIa) or the compound of formula (IIb), and the hole transport matrix compound of the p-type charge generation layer is selected from the compound of formula (IIa) or the compound of formula (IIb).

[0265] According to one embodiment of the present invention, the hole transport compound of the intermediate layer is selected from the compounds of formula (IIa), and the hole transport host compound of the p-type charge generation layer is selected from the compounds of formula (IIa).

[0266] According to one embodiment of the present invention, the one or more hole transport compounds and the one or more hole transport host compounds are identical.

[0267] According to one embodiment of the present invention, the one or more hole transport compounds and the one or more hole transport host compounds are different.

[0268] According to one embodiment of the present invention, when measured by the same method, the HOMO energy level of the hole transport host compound is less than the HOMO energy level of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirobi[fluorene]-2,2',7,7'-tetramine, preferably less than the HOMO energy level of N4,N4,N4',N4'-tetra(4-methoxyphenyl)biphenyl-4,4'-diamine, more preferably less than the HOMO energy level of N4,N4'-bis(9,9-dimethyl-9H-fluorene-2-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine. When using TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the HOMO level of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirobi[fluorene]-2,2',7,7'-tetramine is -4.27 eV, the HOMO level of N4,N4,N4',N4'-tetrakis(4-methoxyphenyl)biphenyl-4,4'-diamine is -4.34 eV, and the HOMO level of N4,N4'-bis(9,9-dimethyl-9H-fluoren-2-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine is -4.64 eV when calculated by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase.

[0269] According to one embodiment of the present invention, when using TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase for calculation, the HOMO energy level of the hole transport host compound is ≤-4.27 eV, preferably ≤-4.34 eV, more preferably ≤-4.40 eV, even more preferably ≤-4.45 eV, even more preferably ≤-4.50 eV, even more preferably ≤-4.55 eV, even more preferably ≤-4.60 eV, even more preferably ≤-4.65 eV.

[0270] According to one embodiment of the present invention, when using TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), when calculated by applying hybrid functional B3LYP with 6-31G* basis set in gas phase, the HOMO level of the hole transport host compound is in the range of ≥-6.50 eV to ≤-4.27 eV, preferably in the range of ≥-6.00 eV to ≤-4.34 eV, more preferably in the range of ≥-5.50 eV to ≤-4.40 eV, even more preferably in the range of ≥-5.40 eV to ≤-4.45 eV, even more preferably in the range of ≥-5.30 eV to ≤-4.50 eV, even more preferably in the range of ≥-5.20 eV to ≤-4.55 eV, even more preferably in the range of ≥-5.10 eV to ≤-4.60 eV, even more preferably in the range of ≥-5.00 eV to ≤-4.65 eV.

[0271] In the context of the present invention, the term "HOMO level is less than" means that the absolute value of the HOMO level is greater than the absolute value of the HOMO level compared with it. In particular, in the context of the present invention, the term "HOMO level is less than" means that the HOMO level is further away from the vacuum level than the value of the HOMO level compared with it.

[0272] n-type charge generation layer (nCGL)

[0273] According to one embodiment, the thickness of the n-type charge generation layer is ≤20 nm, ≤15 nm, or ≤10 nm.

[0274] According to one embodiment, the thickness of the n-type charge generation layer is in a range of ≥1 nm to ≤20 nm, ≥2 nm to ≤15 nm, ≥3 nm to ≤15 nm, or ≥5 nm to ≤15 nm.

[0275] According to one embodiment, the n-type charge generation layer is adjacent to the at least one electron transport layer.

[0276] According to one embodiment, the n-type charge generation layer is in direct contact with the at least one electron transport layer.

[0277] According to one embodiment, the host compound of the n-type charge generation layer is an electron transport host material.

[0278] According to one embodiment, the host compound of the n-type charge generation layer is an organic electron transport host material.

[0279] According to one embodiment, the molecular weight Mw of the matrix compound of the n-type charge generation layer can be ≥400 g / mol and ≤2000 g / mol, preferably the molecular weight Mw is ≥410 g / mol and ≤1500 g / mol, more preferably the molecular weight Mw is ≥420 g / mol and ≤1000 g / mol, further preferably the molecular weight Mw is ≥430 and g / mol≤900 g / mol, and further preferably the molecular weight Mw is ≥440 g / mol and ≤800 g / mol.

[0280] According to one embodiment of the present invention, when using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase for calculation, the LUMO energy level of the matrix compound of the n-type charge generation layer is ≤-1.70eV, preferably ≤-1.74eV, and more preferably ≤-1.75eV.

[0281] According to one embodiment of the present invention, when using the program package TURBOMOLE V6.5, by applying the hybrid functional B3LYP with the Gaussian 6-31G* basis set in the gas phase for calculation, the LUMO energy level of the matrix compound of the n-type charge generation layer is in the range of ≥-3.5eV to ≤-1eV, preferably in the range of ≥-2.5eV to ≤-1.5eV, more preferably in the range of ≥-2.25eV to ≤-1.7eV, more preferably in the range of ≥-2.1eV to ≤-1.74eV, and most preferably in the range of ≥-2.0eV to ≤-1.75eV.

[0282] According to one embodiment, the host compound of the n-type charge generation layer comprises at least one C2 to C 24 N-heteroaryl or P=X moiety, wherein X is O, P, Se, among which P=O is particularly preferred.

[0283] According to one embodiment, the at least one C2 to C24 The N-heteroaryl group may be selected from compounds comprising at least one azine moiety, preferably at least two azine moieties, and further preferably three azine moieties.

[0284] According to one embodiment, the host compound of the n-type charge generation layer comprises at least one moiety selected from the group consisting of pyridine, pyrimidine, triazine, imidazole, benzimidazole, benzo Azoles, quinones, benzoquinones, imidazo[1,5-a]pyridines, quinoxalines, benzoquinoxalines, acridines, phenanthrolines, benzoacridines, dibenzoacridines, phosphine oxides, and terpyridines.

[0285] According to one embodiment, the host compound of the n-type charge generation layer comprises at least one phenanthroline moiety (preferably two phenanthroline moieties), one or more pyridine moieties, one or more pyrimidine moieties, one or more triazine moieties, one or more imidazo[1,5-a]pyridine moieties or one or more phosphine oxide moieties.

[0286] According to one embodiment, the host compound of the n-type charge generation layer comprises at least one phenanthroline moiety (preferably two phenanthroline moieties), one or more pyridine moieties, one or more pyrimidine moieties, or one or more phosphine oxide moieties.

[0287] According to one embodiment, the host compound of the n-type charge generation layer comprises at least one phenanthroline moiety (preferably two phenanthroline moieties), a pyridine moiety, a pyrimidine moiety or a phosphine oxide moiety.

[0288] According to one embodiment, the host compound of the n-type charge generation layer compound comprises at least one phenanthroline moiety (preferably two phenanthroline moieties), one or more pyridine moieties, one or more pyrimidine moieties, one or more triazine moieties.

[0289] According to one embodiment, the host compound of the n-type charge generation layer is selected from 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline], (3-(10-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)anthracene-9-yl)phenyl)dimethylphosphine oxide, 3-(3-(9,10-diphenylanthracene-2-yl)phenyl)-1-(pyridin-2-yl)imidazo[1,5-a]pyridine, 7-(3-(1,10-phenanthroline-2-yl)phenyl)dibenzo[c ,h]acridine, 7-(3-([2,2':6',2"-terpyridine]-4'-yl)phenyl)dibenzo[c,h]acridine, 4'-(4'-(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-4-yl)-2,2':6',2"-terpyridine, 4'-(4-(fluoranthene-3-yl)phenyl)-2,2':6',2"-terpyridine or 3-(9,10-di-2-naphthyl-2-anthracenyl)phenyl]dimethylphosphine oxide.

[0290] According to one embodiment, the host compound of the n-type charge generation layer comprises at least one phenanthroline moiety, preferably two phenanthroline moieties.

[0291] According to one embodiment, the host compound of the n-type charge generation layer comprises at least one C2 to C 24 N-heteroaryl or P═X group, where X is O, P, Se, among which P═O is particularly preferred.

[0292] According to one embodiment, the at least one C2 to C 24 The N-heteroaryl radical may be selected from compounds comprising at least one azine group, preferably at least two azine groups, and more preferably three azine groups.

[0293] According to one embodiment, the host compound of the n-type charge generation layer comprises at least one group selected from the group consisting of pyridine, pyrimidine, triazine, imidazole, benzimidazole, benzo Azoles, quinones, benzoquinones, imidazo[1,5-a]pyridines, quinoxalines, benzoquinoxalines, acridines, phenanthrolines, benzoacridines, dibenzoacridines, phosphine oxides, and terpyridines.

[0294] According to one embodiment, the host compound of the n-type charge generation layer comprises at least one phenanthroline group (preferably two phenanthroline moieties), one or more pyridine groups, one or more pyrimidine groups, one or more triazine groups, one or more imidazo[1,5-a]pyridine groups or one or more phosphine oxide groups.

[0295] According to one embodiment, the host compound of the n-type charge generation layer comprises at least one phenanthroline group (preferably two phenanthroline moieties), one or more pyridine groups, one or more pyrimidine groups or one or more phosphine oxide groups.

[0296] According to one embodiment, the host compound of the n-type charge generation layer comprises at least one phenanthroline group (preferably two phenanthroline moieties), a pyridine group, a pyrimidine group or a phosphine oxide group.

[0297] According to one embodiment, the host compound of the n-type charge generation layer comprises at least one phenanthroline group (preferably two phenanthroline moieties), one or more pyridine groups, one or more pyrimidine groups or one or more triazine groups.

[0298] According to one embodiment, the host compound of the n-type charge generation layer is selected from: 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline], (3-(10-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)anthracene-9-yl)phenyl)dimethylphosphine oxide, 3-(3-(9,10-diphenylanthracene-2-yl)phenyl)-1-(pyridin-2-yl)imidazo[1,5-a]pyridine, 7-(3-(1,10-phenanthroline-2-yl)phenyl)dibenzo[ c,h]acridine, 7-(3-([2,2':6',2"-terpyridine]-4'-yl)phenyl)dibenzo[c,h]acridine, 4'-(4'-(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-4-yl)-2,2':6',2"-terpyridine, 4'-(4-(fluoranthene-3-yl)phenyl)-2,2':6',2"-terpyridine or 3-(9,10-di-2-naphthyl-2-anthracenyl)phenyl]dimethylphosphine oxide.

[0299] According to one embodiment, the host compound of the n-type charge generation layer comprises at least one phenanthroline group, preferably two phenanthroline groups.

[0300] According to one embodiment, the host compound of the n-type charge generation layer is represented by a compound of formula (IV):

[0301]

[0302] in

[0303] n is an integer selected from 0, 1, 2, 3, 4;

[0304] m is an integer selected from 0, 1, 2, 3, 4;

[0305] Where at least one of n or m is ≥ 1;

[0306] Each R a or each R b Can independently bind to Ring A, Ring B or Ring C;

[0307] Each R a (if present) is independently selected from H, D, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, an electron withdrawing group, CN;

[0308] Each R b (if present) is independently selected from H, D, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, an electron withdrawing group, CN;

[0309] wherein the one or more substituents are selected from D, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, partially fluorinated alkyl, perfluorinated alkyl, partially deuterated alkyl, perdeuterated alkyl, substituted or unsubstituted alkoxy, partially fluorinated alkoxy, perfluorinated alkoxy, partially deuterated alkoxy, perdeuterated alkoxy, electron withdrawing group, CN, -PX(R d 2. COR c 、COOR c , CONH2, NO2, F;

[0310] wherein the one or more substituents are selected from D, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, partially fluorinated alkyl, perfluorinated alkyl, partially deuterated alkyl, perdeuterated alkyl, substituted or unsubstituted alkoxy, partially fluorinated alkoxy, perfluorinated alkoxy, partially deuterated alkoxy, perdeuterated alkoxy, electron withdrawing group, CN, -PX(R d 2. COR c 、COOR c , CONH2, NO2, F;

[0311] wherein the one or more substituents are selected from D, aryl, heteroaryl, alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially deuterated C1 to C8 alkyl, perdeuterated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, partially deuterated C1 to C8 alkoxy, perdeuterated C1 to C8 alkoxy, CN, -PX(R) d 2. COR c 、COOR c , CONH2, NO2, F;

[0312] Where R c Independently selected from C6 to C 12 Aryl, C3 to C12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 alkoxy; and

[0313] R d Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 alkoxy; and

[0314] -Two R's d can be connected together to form a ring;

[0315] X is selected from S or O.

[0316] According to one embodiment, the host compound of the n-type charge generation layer is represented by a compound of formula (IV):

[0317]

[0318] in

[0319] n is an integer selected from 0, 1, 2, 3, 4;

[0320] m is an integer selected from 0, 1, 2, 3, 4;

[0321] Where at least one of n or m is ≥ 1;

[0322] Each R a or each R b Can independently bind to Ring A, Ring B or Ring C;

[0323] Each R a (if present) independently selected from H, D, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C3 to C 30 heteroaryl, substituted or unsubstituted C1 to C8 alkyl, electron withdrawing group, CN;

[0324] Each R b (if present) independently selected from H, D, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C3 to C 30 heteroaryl, substituted or unsubstituted C1 to C8 alkyl, electron withdrawing group, CN;

[0325] wherein the one or more substituents are selected from D, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C3 to C 30 heteroaryl, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially deuterated C1 to C8 alkyl, perdeuterated C1 to C8 alkyl, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, partially deuterated C1 to C8 alkoxy, perdeuterated C1 to C8 alkoxy, electron withdrawing group, CN, -PX(R d 2. COR c 、COOR c , CONH2, NO2, F;

[0326] wherein the one or more substituents are selected from D, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C3 to C 30 heteroaryl, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially deuterated C1 to C8 alkyl, perdeuterated C1 to C8 alkyl, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, partially deuterated C1 to C8 alkoxy, perdeuterated C1 to C8 alkoxy, electron withdrawing group, CN, -PX(R d 2. COR c 、COOR c , CONH2, NO2, F;

[0327] wherein the one or more substituents are selected from D, C6 to C 30 Aryl, C3 to C 30 heteroaryl, alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially deuterated C1 to C8 alkyl, perdeuterated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, partially deuterated C1 to C8 alkoxy, perdeuterated C1 to C8 alkoxy, CN, -PX(R d 2. COR c 、COOR c, CONH2, NO2, F;

[0328] Where R c Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 alkoxy; and

[0329] R d Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 alkoxy; and

[0330] -Two R's d can be connected together to form a ring;

[0331] X is selected from S or O.

[0332] According to one embodiment, the host compound of the n-type charge generation layer is represented by a compound of formula (IV):

[0333]

[0334] in

[0335] n is an integer selected from 0, 1, 2, 3, 4;

[0336] m is an integer selected from 0, 1, 2, 3, 4;

[0337] Where at least one of n or m is ≥ 1;

[0338] Each R a or each R b Can independently bind to Ring A, Ring B or Ring C;

[0339] Each R a (if present) independently selected from H, D, substituted or unsubstituted C6 to C24 Aryl, substituted or unsubstituted C3 to C 24 heteroaryl, substituted or unsubstituted C1 to C6 alkyl, electron withdrawing group, CN;

[0340] Each R b (if present) independently selected from H, D, substituted or unsubstituted C6 to C 24 Aryl, substituted or unsubstituted C3 to C 24 heteroaryl, substituted or unsubstituted C1 to C6 alkyl, electron withdrawing group, CN;

[0341] wherein the one or more substituents are selected from D, substituted or unsubstituted C6 to C 24 Aryl, substituted or unsubstituted C3 to C 24 heteroaryl, substituted or unsubstituted C1 to C6 alkyl, partially fluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, partially deuterated C1 to C6 alkyl, perdeuterated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially fluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy, partially deuterated C1 to C6 alkoxy, perdeuterated C1 to C6 alkoxy, electron withdrawing group, CN, -PX(R d 2. COR c 、COOR c , CONH2, NO2, F;

[0342] wherein the one or more substituents are selected from D, substituted or unsubstituted C6 to C 24 Aryl, substituted or unsubstituted C3 to C 24 heteroaryl, substituted or unsubstituted C1 to C6 alkyl, partially fluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, partially deuterated C1 to C6 alkyl, perdeuterated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially fluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy, partially deuterated C1 to C6 alkoxy, perdeuterated C1 to C6 alkoxy, electron withdrawing group, CN, -PX(R d 2. COR c 、COOR c , CONH2, NO2, F;

[0343] wherein the one or more substituents are selected from D, C6 to C 24 Aryl, C3 to C 24heteroaryl, C1 to C6 alkyl, partially fluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, partially deuterated C1 to C6 alkyl, perdeuterated C1 to C6 alkyl, partially fluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy, partially deuterated C1 to C6 alkoxy, perdeuterated C1 to C6 alkoxy, CN, -PX(R d 2. COR c 、COOR c , CONH2, NO2, F;

[0344] Where R c Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 alkoxy; and

[0345] R d Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 alkoxy; and

[0346] -Two R's d can be connected together to form a ring;

[0347] X is selected from S or O.

[0348] According to one embodiment, the host compound of the n-type charge generation layer is represented by a compound of formula (IV):

[0349]

[0350] in

[0351] n is an integer selected from 0, 1, 2, 3, 4;

[0352] m is an integer selected from 0, 1, 2, 3, 4;

[0353] Where at least one of n or m is ≥ 1;

[0354] Each R a or each R b Can independently bind to Ring A, Ring B or Ring C;

[0355] Each R a (if present) independently selected from H, D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 18 heteroaryl, substituted or unsubstituted C1 to C4 alkyl, electron withdrawing group, CN;

[0356] Each R b (if present) independently selected from H, D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 18 heteroaryl, substituted or unsubstituted C1 to C4 alkyl, electron withdrawing group, CN;

[0357] wherein the one or more substituents are selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 18 heteroaryl, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, partially deuterated C1 to C4 alkyl, perdeuterated C1 to C4 alkyl, substituted or unsubstituted C1 to C4 alkoxy, partially fluorinated C1 to C4 alkoxy, perfluorinated C1 to C4 alkoxy, partially deuterated C1 to C4 alkoxy, perdeuterated C1 to C4 alkoxy, electron withdrawing group, CN, -PX(R d 2. COR c 、COOR c , CONH2, NO2, F;

[0358] wherein the one or more substituents are selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 18 heteroaryl, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, partially deuterated C1 to C4 alkyl, perdeuterated C1 to C4 alkyl, substituted or unsubstituted C1 to C4 alkoxy, partially fluorinated C1 to C4 alkoxy, perfluorinated C1 to C4 alkoxy, partially deuterated C1 to C4 alkoxy, perdeuterated C1 to C4 alkoxy, electron withdrawing group, CN, -PX(R d 2. COR c 、COOR c , CONH2, NO2, F;

[0359] wherein the one or more substituents are selected from D, C6 to C 18 Aryl, C3 to C 18 heteroaryl, C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, partially deuterated C1 to C4 alkyl, perdeuterated C1 to C4 alkyl, partially fluorinated C1 to C4 alkoxy, perfluorinated C1 to C4 alkoxy, partially deuterated C1 to C4 alkoxy, perdeuterated C1 to C6 alkoxy, CN, -PX(R d 2. COR c 、COOR c , CONH2, NO2, F;

[0360] Where R c Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 alkoxy; and

[0361] R d Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 alkoxy; and

[0362] -Two R's d can be connected together to form a ring;

[0363] X is selected from S or O.

[0364] According to one embodiment, the compound of formula (IV) is selected from compounds of formula (IVa):

[0365]

[0366] The ring A, ring B and ring C may be independently partially or completely deuterated.

[0367] According to one embodiment, the compound of formula (IV) is selected from compounds of formula (IVb):

[0368]

[0369] The ring A, ring B and ring C may be independently partially or completely deuterated.

[0370] According to one embodiment, the compound of formula (IV) is selected from compounds of formula (IVc):

[0371]

[0372] wherein the ring A, ring B, and ring C may be independently partially or completely deuterated,

[0373] Wherein l is an integer selected from 0, 1, 2, 3, 4;

[0374] Each R e independently selected from D;

[0375] Where R a (if present) independently selected from H, D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 18 heteroaryl, substituted or unsubstituted C1 to C4 alkyl, electron withdrawing group, CN;

[0376] Among them, Ar a is selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 18 Heteroaryl,

[0377] Where R a or Ar a The one or more substituents are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 18 heteroaryl, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, partially deuterated C1 to C4 alkyl, perdeuterated C1 to C4 alkyl, substituted or unsubstituted C1 to C4 alkoxy, partially fluorinated C1 to C4 alkoxy, perfluorinated C1 to C4 alkoxy, partially deuterated C1 to C4 alkoxy, perdeuterated C1 to C4 alkoxy, electron withdrawing group, CN, -PX(R d 2. COR c 、COOR c , CONH2, NO2, F;

[0378] wherein the one or more substituents are independently selected from D, C6 to C 18 Aryl, C3 to C 18 heteroaryl, C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, partially deuterated C1 to C4 alkyl, perdeuterated C1 to C4 alkyl, partially fluorinated C1 to C4 alkoxy, perfluorinated C1 to C4 alkoxy, partially deuterated C1 to C4 alkoxy, perdeuterated C1 to C6 alkoxy, CN, -PX(R d 2. COR c 、COOR c , CONH2, NO2, F;

[0379] Where R c Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 alkoxy; and

[0380] R d Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 alkoxy; and

[0381] -Two R's d can be connected together to form a ring;

[0382] X is selected from S or O.

[0383] According to one embodiment, m is selected from 1, and wherein ring A, ring B or ring C may be deuterated.

[0384] According to one embodiment, n is selected from 1, m is selected from 1, and wherein ring A, ring B or ring C may be deuterated.

[0385] According to one embodiment of the present invention, the n-type charge generation layer includes a metal dopant.

[0386] According to one embodiment of the present invention, the metal dopant is selected from a metal having an electronegativity of ≤1.4 eV according to the Pauling scale or a metal alloy containing a metal having an electronegativity of ≤1.4 eV according to the Pauling scale.

[0387] According to one embodiment of the present invention, the metal dopant is selected from a metal having an electronegativity of ≤1.35 eV according to the Pauling scale or a metal alloy containing a metal having an electronegativity of ≤1.35 eV according to the Pauling scale.

[0388] According to one embodiment of the present invention, the metal dopant is a metal selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eu and Yb, or a metal alloy comprising a metal selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eu and Yb.

[0389] According to one embodiment of the present invention, the metal dopant is a metal selected from the group consisting of Li, Na, K, Cs, Mg, Ca, Ba, Sm, Eu and Yb, or a metal alloy comprising a metal selected from the group consisting of Li, Na, K, Cs, Mg, Ca, Ba, Sm, Eu and Yb.

[0390] According to one embodiment of the present invention, the metal dopant is a metal selected from the group consisting of Li, Mg and Yb, or a metal alloy comprising a metal selected from the group consisting of Li, Mg and Yb.

[0391] According to one embodiment of the present invention, the metal dopant is a metal selected from the group consisting of Li and Yb, or a metal alloy comprising a metal selected from the group consisting of Li and Yb.

[0392] According to one embodiment of the present invention, the metal dopant is Yb, or a metal alloy comprising a metal selected from the group consisting of Li and Yb.

[0393] According to one embodiment of the present invention, the metal dopant is Yb.

[0394] According to one embodiment of the present invention, the amount of metal dopant present in the n-type charge generation layer is ≤99.9 wt. %, preferably ≤99 wt. %, more preferably ≤95 wt. %, more preferably ≤90 wt. %, more preferably ≤80 wt. %, more preferably ≤70 wt. %, more preferably ≤60 wt. %, more preferably ≤50 wt. %, more preferably ≤40 wt. %, more preferably ≤30 wt. %, more preferably ≤20 wt. %, more preferably ≤10 wt. %, more preferably ≤5 wt. %, more preferably ≤3.0 wt. %, more preferably ≤2.75 wt. %, more preferably ≤2.5 wt. %, more preferably ≤2.25 wt. %, and most preferably ≤2.0 wt. %.

[0395] According to one embodiment of the present invention, the amount of electron transport material present in the n-type charge generation layer is ≥0.1 wt.%, preferably ≥1 wt.%, more preferably ≥5 wt.%, more preferably ≥10 wt.%, more preferably ≥20 wt.%, more preferably ≥30 wt.%, more preferably ≥40 wt.%, more preferably ≥50 wt.%, more preferably ≥60 wt.%, more preferably ≥70 wt.%, more preferably ≥80 wt.%, more preferably ≥90 wt.%, more preferably ≥95 wt.%, more preferably ≥97.0 wt.%, more preferably ≥97.25 wt.%, more preferably ≥97.5 wt.%, more preferably ≥97.75 wt.%, and most preferably ≥98.0 wt.%.

[0396] According to one embodiment of the present invention, an organic electroluminescent device is provided, the organic electroluminescent device comprising an anode layer, a cathode layer, a first light-emitting layer, a second light-emitting layer and at least one intermediate connection region, wherein the at least one intermediate connection region is arranged between the first light-emitting layer and the second light-emitting layer,

[0397] wherein the intermediate connection region comprises an n-type charge generation layer, an intermediate layer and a p-type charge generation layer,

[0398] wherein the n-type charge generation layer is arranged closer to the anode layer than the p-type charge generation layer;

[0399] wherein the p-type charge generation layer is arranged closer to the cathode layer than the n-type charge generation layer; and

[0400] wherein the intermediate layer is arranged between the n-type charge generation layer and the p-type charge generation layer,

[0401] in

[0402] wherein the p-type charge generating layer comprises a hole transporting host compound and a radialene of formula (I),

[0403]

[0404]

[0405] Wherein in formula (I),

[0406] -A 1 Independently selected from groups of formula (Ia):

[0407]

[0408] The asterisk "*" indicates the binding position.

[0409] Among them, Ar 1 are independently selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

[0410] For Ar 1 In the case of being substituted, one or more substituents are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl; and

[0411] Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, C1 to C8 alkoxy are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy;

[0412] -A 2 Independently selected from groups of formula (Ib):

[0413]

[0414] The asterisk "*" indicates the binding position.

[0415] Among them, Ar 2 are independently selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

[0416] For Ar 2In the case of being substituted, one or more substituents are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl; and

[0417] Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, C1 to C8 alkoxy are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy;

[0418] -A 3 Independently selected from groups of formula (Ic):

[0419]

[0420] The asterisk "*" indicates the binding position.

[0421] Among them, Ar 3 are independently selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;

[0422] For Ar 3 In the case of being substituted, one or more substituents are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl; and

[0423] Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, C1 to C8 alkoxy are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy;

[0424] - and in which A1 , A 2 and A 3 In which each R' is independently selected from substituted or unsubstituted C6 to C 18 Aryl, C3 to C 18 heteroaryl, electron withdrawing group, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, halogen, F and CN;

[0425] The intermediate layer comprises at least one hole transport compound selected from an amine compound, a diarylamine compound, a triarylamine compound, a compound of formula (IIa) or a compound of formula (IIb):

[0426]

[0427] in:

[0428] T 1 , T 2 , T 3 , T 4 and T 5 independently selected from a single bond, a phenylene group, a biphenylene group, a terphenylene group or a naphthalene group, preferably a single bond or a phenylene group;

[0429] T 6 is a phenyl subunit, a biphenyl subunit, a terphenyl subunit or a naphthalene subunit;

[0430] Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar' 4 and Ar' 5 independently selected from substituted or unsubstituted C6 to C 20 Aryl or substituted or unsubstituted C3 to C 20heteroarylidene, substituted or unsubstituted biphenylidene, substituted or unsubstituted fluorene, substituted 9-fluorene, substituted 9,9-fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted terphenylidene, substituted or unsubstituted tetracene, substituted or unsubstituted benzanthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthene, substituted or unsubstituted carbazole, substituted 9-phenylcarbazole, substituted or unsubstituted azepane, substituted or unsubstituted dibenzo[b,f]azepane, substituted or unsubstituted 9,9'- Spirobi[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanthene]; or a substituted or unsubstituted aromatic fused ring system comprising at least three substituted or unsubstituted aromatic rings selected from: substituted or unsubstituted non-heterocyclic, substituted or unsubstituted hetero 5-membered ring, substituted or unsubstituted 6-membered ring and / or substituted or unsubstituted 7-membered ring, substituted or unsubstituted fluorene; or a fused ring system comprising 2 to 6 substituted or unsubstituted 5 to 7-membered rings, and the rings are selected from: (i) heterocyclic unsaturated 5 to 7-membered rings, (ii) aromatic heterocyclic 5 to 6-membered rings, (iii) non-heterocyclic unsaturated 5 to 7-membered rings, (iv) aromatic non-heterocyclic 6-membered rings;

[0431] in

[0432] Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar' 4 and Ar' 5 The substituents are selected from the group consisting of H, D, F, C(=O)R' 2 、CN、Si(R' 2 )3. P(=O)(R' 2 )2. OR' 2 、S(=O)R' 2 、S(=O)2R' 2 , substituted or unsubstituted straight-chain alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted branched-chain alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl or alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aromatic ring systems having 6 to 40 aromatic ring atoms and substituted or unsubstituted heteroaromatic ring systems having 5 to 40 aromatic ring atoms, unsubstituted C6 to C 18 Aryl, unsubstituted C3 to C 18heteroaryl, a fused ring system comprising 2 to 6 unsubstituted 5 to 7 membered rings, and the rings are selected from: heterocyclic unsaturated 5 to 7 membered rings, aromatic heterocyclic 5 to 6 membered rings, non-heterocyclic unsaturated 5 to 7 membered rings and aromatic non-heterocyclic 6 membered rings,

[0433] Where R' 2 The alkyl radical may be selected from H, D, a linear alkyl radical having 1 to 6 carbon atoms, a branched alkyl radical having 1 to 6 carbon atoms, a cyclic alkyl radical having 3 to 6 carbon atoms, an alkenyl or alkynyl radical having 2 to 6 carbon atoms, a C6 to C 18 Aryl or C3 to C 18 Heteroaryl.

[0434] method:

[0435] The present invention also relates to a method for preparing an organic light-emitting device, preferably an organic electroluminescent device as described above, the method comprising the following steps:

[0436] - forming an n-type charge generation layer by depositing a host compound and depositing a metal dopant;

[0437] - forming an intermediate layer by depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb);

[0438] - forming a p-type charge generation layer by depositing a hole transport host compound consisting essentially of at least one compound selected from arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb), and depositing a radialene of formula (I).

[0439] All details and instructions apply mutatis mutandis.

[0440] According to one embodiment of the present invention, the method for preparing the organic electroluminescent device as described above comprises the following steps:

[0441] - forming an n-type charge generation layer by depositing a host compound and depositing a metal dopant;

[0442] - forming an intermediate layer directly on the n-type charge generation layer by depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb);

[0443] - forming a p-type charge generation layer by depositing a hole transporting host compound consisting essentially of at least one compound according to formula (IIa) or formula (IIb) and depositing a radialene of formula (I);

[0444] The hole transport compound and the hole transport host compound are selected to be the same or different.

[0445] According to one embodiment of the present invention, the method for preparing the organic electroluminescent device as described above comprises the following steps:

[0446] - forming an n-type charge generation layer by depositing a host compound and depositing a metal dopant;

[0447] - forming an intermediate layer by depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb);

[0448] - forming a p-type charge generation layer directly on the intermediate layer by depositing a hole transport host compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb) and depositing a radialene of formula (I);

[0449] The hole transport compound and the hole transport host compound are selected to be the same or different.

[0450] According to one embodiment of the present invention, the method for preparing the organic electroluminescent device as described above comprises the following steps:

[0451] - forming an n-type charge generation layer by depositing a host compound and depositing a metal dopant;

[0452] - by depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb), direct forming an intermediate layer on the n-type charge generation layer;

[0453] - by depositing a hole transporting host compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb) and depositing a radialene of formula (I), direct forming a p-type charge generation layer on the intermediate layer;

[0454] The hole transport compound and the hole transport host compound are selected to be the same or different.

[0455] According to one embodiment of the present invention, the method for preparing the organic electroluminescent device as described above comprises the following steps:

[0456] a deposition source provided for depositing the radialene of formula (I) according to the invention, and

[0457] - a deposition source for depositing a hole transport compound selected from arylamines, diarylamines, triarylamines, formula (IIa) and formula (IIb) and a hole transport host compound consisting essentially of at least one compound selected from arylamines, diarylamines, triarylamines, formula (IIa) and formula (IIb);

[0458] or a deposition source for depositing a hole transport compound consisting essentially of at least one compound selected from arylamines, diarylamines, triarylamines, compounds of formula (IIa) or (IIb), and a deposition source for depositing a radialene of formula (I);

[0459] - providing a deposition source for depositing a matrix compound;

[0460] - providing a deposition source for depositing a metal dopant;

[0461] - forming an n-type charge generation layer by depositing a host compound released from a deposition source and a metal dopant released from the deposition source;

[0462] - forming an intermediate layer by depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb) released from a deposition source;

[0463] - forming a p-type charge generation layer by depositing a hole transport host compound consisting essentially of at least one compound selected from arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb) released from a deposition source, and a radialene of formula (I) released from the deposition source;

[0464] The hole transport compound and the hole transport host compound are selected to be the same or different.

[0465] According to one embodiment of the present invention, the method for preparing the organic electroluminescent device as described above comprises the following steps:

[0466] a deposition source provided for depositing the radialene of formula (I) according to the invention, and

[0467] - a deposition source provided for depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb), and a hole transport host compound according to formula (IIa) or formula (IIb);

[0468] or providing a deposition source for depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb), and providing a deposition source for depositing the radialene of formula (I);

[0469] - providing a deposition source for depositing a matrix compound;

[0470] - providing a deposition source for depositing a metal dopant;

[0471] - forming an n-type charge generation layer by depositing a host compound released from a deposition source and a metal dopant released from the deposition source;

[0472] - a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb), released from a deposition source by deposition, direct forming an intermediate layer on the n-type charge generation layer;

[0473] - forming a p-type charge generation layer by depositing a hole transport host compound consisting essentially of at least one compound selected from arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb) released from a deposition source, and a radialene of formula (I) released from the deposition source;

[0474] The hole transport compound and the hole transport host compound are selected to be the same or different.

[0475] According to one embodiment of the present invention, the method for preparing the organic electroluminescent device as described above comprises the following steps:

[0476] a deposition source provided for depositing the radialene of formula (I) according to the invention, and

[0477] - a deposition source for depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb) and a hole transport host compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb);

[0478] or providing a deposition source for depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb), and providing a deposition source for depositing the radialene of formula (I);

[0479] - providing a deposition source for depositing a matrix compound;

[0480] - providing a deposition source for depositing a metal dopant;

[0481] - forming an n-type charge generation layer by depositing a host compound released from a deposition source and a metal dopant released from the deposition source;

[0482] - forming an intermediate layer by depositing a hole transport compound consisting essentially of at least one compound according to formula (IIa) or formula (IIb) released from a deposition source;

[0483] a hole transporting host compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb) and a radialene of formula (I) released from a deposition source by deposition, direct forming a p-type charge generation layer on the intermediate layer;

[0484] The hole transport compound and the hole transport host compound are selected to be the same or different.

[0485] According to one embodiment of the present invention, the method for preparing the organic electroluminescent device as described above comprises the following steps:

[0486] a deposition source provided for depositing the radialene of formula (I) according to the invention, and

[0487] - a deposition source for depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) or (IIb) and a hole transport host compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and (IIb);

[0488] or a deposition source for depositing a hole transport compound consisting essentially of at least one compound selected from arylamines, diarylamines, triarylamines, compounds of formula (IIa) or (IIb), and a deposition source for depositing a radialene of formula (I);

[0489] - providing a deposition source for depositing a matrix compound;

[0490] - providing a deposition source for depositing a metal dopant;

[0491] - forming an n-type charge generation layer by depositing a host compound released from a deposition source and a metal dopant released from the deposition source;

[0492] - a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb), released from a deposition source by deposition, direct forming an intermediate layer on the n-type charge generation layer;

[0493] a hole transporting host compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb) and a radialene of formula (I) released from a deposition source by deposition, direct forming a p-type charge generation layer on the intermediate layer;

[0494] The hole transport compound and the hole transport host compound are selected to be the same or different.

[0495] According to one embodiment of the present invention, the method for preparing the organic electroluminescent device as described above comprises the following steps:

[0496] - providing a first deposition source for depositing the radialene of formula (I) according to the invention, and

[0497] a second deposition source arranged for depositing a hole transport compound consisting essentially of at least one compound according to formula (IIa) and formula (IIb) and a hole transport host compound according to formula (IIa) or formula (IIb);

[0498] or providing a second deposition source for depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb), and providing a second main deposition source for depositing the radialene of formula (I);

[0499] - providing a third deposition source for depositing a matrix compound;

[0500] - providing a fourth deposition source for depositing a metal dopant;

[0501] - forming an n-type charge generation layer by depositing a host compound released from a third deposition source and a metal dopant released from a fourth deposition source;

[0502] - forming an intermediate layer by depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb) released from a first deposition source;

[0503] - forming a p-type charge generation layer by depositing a hole transport host compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb) released from a second deposition source or a second main deposition source, and a radialene of formula (I) released from the first deposition source;

[0504] The hole transport compound and the hole transport host compound are selected to be the same or different.

[0505] According to one embodiment of the present invention, the method for preparing the organic electroluminescent device as described above comprises the following steps:

[0506] - providing a first deposition source for depositing the radialene of formula (I) according to the invention, and

[0507] - a second deposition source provided for depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and (IIb) and a hole transport host compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and (IIb);

[0508] or providing a second deposition source for depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb), and providing a second main deposition source for depositing the radialene of formula (I);

[0509] - providing a third deposition source for depositing a matrix compound;

[0510] - providing a fourth deposition source for depositing a metal dopant;

[0511] - forming an n-type charge generation layer by depositing a host compound released from a third deposition source and a metal dopant released from a fourth deposition source;

[0512] - a hole transport compound selected from arylamines, diarylamines, triarylamines, formula (IIa) and formula (IIb) released from the first deposition source by deposition, direct forming an intermediate layer on the n-type charge generation layer;

[0513] - forming a p-type charge generation layer by depositing a hole transport host compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb) released from a second deposition source or a second main deposition source, and a radialene of formula (I) released from the first deposition source;

[0514] The hole transport compound and the hole transport host compound are selected to be the same or different.

[0515] According to one embodiment of the present invention, the method for preparing the organic electroluminescent device as described above comprises the following steps:

[0516] - providing a first deposition source for depositing the radialene of formula (I) according to the invention, and

[0517] - a second deposition source provided for depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and (IIb) and a hole transport host compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and (IIb);

[0518] or providing a second deposition source for depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb), and providing a second main deposition source for depositing the radialene of formula (I);

[0519] - providing a third deposition source for depositing a matrix compound;

[0520] - providing a fourth deposition source for depositing a metal dopant;

[0521] - forming an n-type charge generation layer by depositing a host compound released from a third deposition source and a metal dopant released from a fourth deposition source;

[0522] - forming an intermediate layer by depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb) released from a first deposition source;

[0523] - forming a p-type charge generation layer directly on the intermediate layer by depositing a hole transport host compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb) released from the second deposition source or the second main deposition source and a radialene of formula (I) released from the first deposition source;

[0524] The hole transport compound and the hole transport host compound are selected to be the same or different.

[0525] According to one embodiment of the present invention, the method for preparing the organic electroluminescent device as described above comprises the following steps:

[0526] - providing a first deposition source for depositing the radialene of formula (I) according to the invention, and

[0527] - a second deposition source provided for depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and (IIb) and a hole transport host compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and (IIb);

[0528] or providing a second deposition source for depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb), and providing a second main deposition source for depositing the radialene of formula (I);

[0529] - providing a third deposition source for depositing a matrix compound;

[0530] - providing a fourth deposition source for depositing a metal dopant;

[0531] - forming an n-type charge generation layer by depositing a host compound released from a third deposition source and a metal dopant released from a fourth deposition source;

[0532] - a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb) released from a first deposition source by deposition, direct forming an intermediate layer on the n-type charge generation layer;

[0533] - forming a p-type charge generation layer directly on the intermediate layer by depositing a hole transport host compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb) released from the second deposition source or the second main deposition source and a radialene of formula (I) released from the first deposition source;

[0534] The hole transport compound and the hole transport host compound are selected to be the same or different.

[0535] According to one embodiment of the present invention, the hole transport host compound of the p-type charge generation layer is selected from the compound of formula (IIa) or the compound of formula (IIb).

[0536] According to one embodiment of the present invention, the hole transport host compound of the p-type charge generation layer is selected from the compounds of formula (IIa).

[0537] According to one embodiment of the present invention, the hole transport compound of the intermediate layer is selected from the compound of formula (IIa) or the compound of formula (IIb).

[0538] According to one embodiment of the present invention, the hole transport compound of the intermediate layer is selected from the compounds of formula (IIa).

[0539] According to one embodiment of the present invention, the hole transport compound of the intermediate layer is selected from the compound of formula (IIa) or the compound of formula (IIb), and the hole transport matrix compound of the p-type charge generation layer is selected from the compound of formula (IIa) or the compound of formula (IIb).

[0540] According to one embodiment of the present invention, the hole transport compound of the intermediate layer is selected from the compounds of formula (IIa), and the hole transport host compound of the p-type charge generation layer is selected from the compounds of formula (IIa).

[0541] According to one embodiment, the method may further include forming at least one layer on the anode electrode, wherein the at least one layer is selected from: forming a hole transport layer between the anode electrode and the cathode layer or forming a hole blocking layer, a light emitting layer and an n-type charge generating layer.

[0542] Suitable deposition methods may include:

[0543] -Deposition by vacuum thermal evaporation;

[0544] - deposition by solution processing, preferably selected from spin coating, printing, casting; and / or

[0545] -Slot die coating.

[0546] Preferably, the deposition method is vacuum thermal evaporation.

[0547] Setup of organic electroluminescent devices

[0548] According to one embodiment of the present invention, the organic electroluminescent device is an organic light emitting diode.

[0549] According to a preferred embodiment of the present invention, the organic electroluminescent device is an organic light emitting diode, wherein light is emitted through a cathode layer.

[0550] The present invention further relates to a display device, which comprises the organic electroluminescent device according to the present invention.

[0551] According to a preferred embodiment of the present invention, the display device comprises the organic electroluminescent device according to the present invention, wherein the cathode layer is transparent.

[0552] Other Implementations

[0553] According to one embodiment of the present invention, the organic electroluminescent device comprises a hole injection layer.

[0554] According to one embodiment of the present invention, the organic electroluminescent device comprises a hole injection layer, and wherein the hole injection layer is in direct contact with the anode layer.

[0555] According to one embodiment of the present invention, the organic electroluminescent device comprises a hole injection layer, wherein the hole injection layer is in direct contact with the anode layer, and wherein the hole injection layer comprises an organic p-type dopant.

[0556] According to one embodiment of the present invention, the organic electroluminescent device comprises a hole injection layer, wherein the hole injection layer is in direct contact with the anode layer, and wherein the hole injection layer comprises an organic p-type dopant and a hole transport compound.

[0557] According to one embodiment of the present invention, the organic electroluminescent device comprises an electron injection layer.

[0558] According to one embodiment of the present invention, the organic electroluminescent device comprises an electron injection layer, and wherein the electron injection layer is in direct contact with the cathode layer.

[0559] According to one embodiment of the present invention, the organic electroluminescent device comprises an electron transport layer.

[0560] According to one embodiment of the present invention, the organic electroluminescent device comprises a hole transport layer.

[0561] According to one embodiment of the present invention, the organic electroluminescent device comprises an electron transport layer and a hole transport layer.

[0562] According to one embodiment of the present invention, the organic electroluminescent device comprises an electron transport layer and a hole transport layer, wherein the hole transport layer is arranged closer to the anode than the at least one electron transport layer.

[0563] According to one embodiment of the present invention, the organic electroluminescent device comprises at least one electron transport layer and at least one hole transport layer, wherein the first light-emitting layer is arranged between the at least one hole transport layer and the at least one electron transport layer, wherein preferably, the at least one hole transport layer is arranged closer to the anode than the at least one electron transport layer.

[0564] According to one embodiment of the present invention, the organic electroluminescent device comprises an electron blocking layer and a hole blocking layer, wherein the electron blocking layer is preferably arranged between the hole transport layer and the first light-emitting layer, and the hole blocking layer is arranged between the electron transport layer and the first light-emitting layer.

[0565] According to one embodiment of the present invention, the electroluminescent device further comprises at least one electron transport layer.

[0566] According to one embodiment of the present invention, the at least one electron transport layer is included in one of the first light emitting unit or the second light emitting unit.

[0567] According to one embodiment of the present invention, the organic electroluminescent device comprises a first electron transport layer and a second electron transport layer.

[0568] According to one embodiment of the present invention, the electron transport layer does not contain a metal dopant, in particular does not contain a metal dopant in oxidation state (0).

[0569] According to one embodiment of the present invention, the n-type charge generation layer is adjacent to the first electron transport layer.

[0570] According to one embodiment of the present invention, the n-type charge generation layer is adjacent to the first electron transport layer and adjacent to the intermediate layer.

[0571] According to one embodiment of the present invention, the n-type charge generation layer is in direct contact with the first electron transport layer.

[0572] According to one embodiment of the present invention, the n-type charge generation layer is in direct contact with the first electron transport layer and is adjacent to the intermediate layer.

[0573] According to one embodiment of the present invention, the n-type charge generation layer is in direct contact with the first electron transport layer and in direct contact with the intermediate layer.

[0574] According to one embodiment of the present invention, the n-type charge generation layer of each of the at least one charge generation layer is in direct contact with the at least one electron transport layer and is adjacent to the p-type charge generation layer of the at least one charge generation layer.

[0575] According to one embodiment of the present invention, the organic electroluminescent device comprises a first hole transport layer and a second hole transport layer.

[0576] According to one embodiment of the present invention, the p-type charge generation layer is adjacent to the at least one hole transport layer.

[0577] According to one embodiment of the present invention, the p-type charge generation layer is in direct contact with the hole transport layer.

[0578] According to one embodiment of the present invention, the p-type charge generation layer is adjacent to the intermediate layer and adjacent to the at least one hole transport layer.

[0579] According to one embodiment of the present invention, the p-type charge generation layer is in direct contact with the intermediate layer and in direct contact with the at least one hole transport layer.

[0580] According to one embodiment of the present invention, the p-type charge generation layer of each of the at least one intermediate connection region is adjacent to the at least one hole transport layer.

[0581] According to one embodiment of the present invention, the p-type charge generation layer of each of the at least one intermediate connection region is in direct contact with the at least one hole transport layer.

[0582] According to one embodiment of the present invention, the p-type charge generation layer of each of the at least one intermediate connection region is adjacent to the n-type charge generation layer of the at least one intermediate connection region and to the at least one hole transport layer.

[0583] According to one embodiment of the present invention, the p-type charge generation layer of each of the at least one intermediate connection region is in direct contact with the n-type charge generation layer of the at least one intermediate interconnect region and with the at least one hole transport layer.

[0584] According to one embodiment of the present invention, the organic electroluminescent device further comprises a third light-emitting unit, and wherein the third light-emitting unit comprises a third light-emitting layer.

[0585] According to one embodiment of the present invention, the organic electroluminescent device further comprises a third light-emitting unit and a fourth light-emitting unit, wherein the third light-emitting unit comprises a third light-emitting layer, and wherein the fourth light-emitting unit comprises a fourth light-emitting layer.

[0586] According to one embodiment of the present invention, the organic electroluminescent device comprises at least two intermediate connection regions and further comprises a third light-emitting unit, wherein the third light-emitting unit comprises a third light-emitting layer.

[0587] According to one embodiment of the present invention, the organic electroluminescent device comprises at least three intermediate connection regions, and further comprises a third light-emitting unit and a fourth light-emitting unit, wherein the third light-emitting unit comprises a third light-emitting layer, and wherein the fourth light-emitting unit comprises a fourth light-emitting layer.

[0588] According to one embodiment of the present invention, an organic electroluminescent device is provided, which includes: a substrate, an anode layer, a first hole injection layer, a first hole transport layer, a first optional electron blocking layer, a first light-emitting layer, a first optional hole blocking layer, a first electron transport layer, an intermediate connecting region including an n-type charge generation layer, an intermediate layer and a p-type charge generation layer, a second hole transport layer, a second optional electron blocking layer, a second light-emitting layer, a second optional hole blocking layer, a second electron transport layer, an electron injection layer and a cathode layer.

[0589] According to one embodiment of the present invention, an organic electroluminescent device is provided, which includes: a substrate, an anode layer, a first hole injection layer, a first hole transport layer, a first electron blocking layer, a first light-emitting layer, a first optional hole blocking layer, a first electron transport layer, an intermediate connecting region including an n-type charge generation layer, an intermediate layer and a p-type charge generation layer, a second hole transport layer, a second electron blocking layer, a second light-emitting layer, a second optional hole blocking layer, a second electron transport layer, an electron injection layer and a cathode layer.

[0590] According to one embodiment of the present invention, an organic electroluminescent device is provided, which includes: a substrate, an anode layer, a first hole injection layer, a first hole transport layer, a first electron blocking layer, a first light-emitting layer, a first electron transport layer, an intermediate connection region including an n-type charge generation layer, an intermediate layer and a p-type charge generation layer, a second hole transport layer, a second electron blocking layer, a second light-emitting layer, a hole blocking layer, a second electron transport layer, an electron injection layer and a cathode layer.

[0591] According to one embodiment of the present invention, an organic electroluminescent device is provided, which includes: a substrate, an anode layer, a hole injection layer, a first hole transport layer, a first optional electron blocking layer, a first light-emitting layer, a first optional hole blocking layer, a first electron transport layer, a first intermediate connecting region including a first n-type charge generation layer, a first intermediate layer and a first p-type charge generation layer, a second hole transport layer, a second optional electron blocking layer, a second light-emitting layer, a second optional hole blocking layer, a second electron transport layer, a second intermediate connecting region including a second n-type charge generation layer, a second intermediate layer and a second p-type charge generation layer, a third hole transport layer, a third optional electron blocking layer, a third light-emitting layer, a third optional hole blocking layer, a third electron transport layer, an electron injection layer and a cathode layer.

[0592] According to one embodiment of the present invention, an organic electroluminescent device is provided, which includes: a substrate, an anode layer, a hole injection layer, a first hole transport layer, a first electron blocking layer, a first light-emitting layer, a first optional hole blocking layer, a first electron transport layer, a first intermediate connecting region including a first n-type charge generation layer, a first intermediate layer and a first p-type charge generation layer, a second hole transport layer, a second electron blocking layer, a second light-emitting layer, a second optional hole blocking layer, a second electron transport layer, a second intermediate connecting region including a second n-type charge generation layer, a second intermediate layer and a second p-type charge generation layer, a third hole transport layer, a third electron blocking layer, a third light-emitting layer, a third optional hole blocking layer, a third electron transport layer, an electron injection layer and a cathode layer.

[0593] According to one embodiment of the present invention, an organic electroluminescent device is provided, which includes: a substrate, an anode layer, a hole injection layer, a first hole transport layer, a first electron blocking layer, a first light-emitting layer, an electron transport layer, a first intermediate connecting region including a first n-type charge generating layer, a first intermediate layer and a first p-type charge generating layer, a second hole transport layer, a second electron blocking layer, a second light-emitting layer, a first optional hole blocking layer, a second electron transport layer, a second intermediate connecting region including a second n-type charge generating layer, a second intermediate layer and a second p-type charge generating layer, a third hole transport layer, a third electron blocking layer, a third light-emitting layer, a second optional hole blocking layer, a third electron transport layer, an electron injection layer and a cathode layer.

[0594] According to one embodiment of the present invention, an organic electroluminescent device is provided, which comprises: a substrate, an anode layer, a hole injection layer, a first hole transport layer, a first electron blocking layer, a first light-emitting layer, an electron transport layer, a first intermediate connecting region comprising a first n-type charge generating layer, a first intermediate layer and a first p-type charge generating layer, a second hole transport layer, a second electron blocking layer, a second light-emitting layer, a second electron transport layer, a second intermediate connecting region comprising a second n-type charge generating layer, a second intermediate layer and a second p-type charge generating layer, a third hole transport layer, a third electron blocking layer, a third light-emitting layer, an optional hole blocking layer, a third electron transport layer, an electron injection layer and a cathode layer.

[0595] According to one embodiment of the present invention, an organic electroluminescent device is provided, which includes: a substrate, an anode layer, a hole injection layer, a first hole transport layer, a first optional electron blocking layer, a first light-emitting layer, a first optional hole blocking layer, a first electron transport layer, a first intermediate connecting region including a first n-type charge generation layer, a first intermediate layer and a first p-type charge generation layer, a second hole transport layer, a second optional electron blocking layer, a second light-emitting layer, a second optional hole blocking layer, a second electron transport layer, a second intermediate connecting region including a second n-type charge generation layer, a second intermediate layer and a second p-type charge generation layer, a third hole transport layer, a third optional electron blocking layer, a third light-emitting layer, a third optional hole blocking layer, a third electron transport layer, a third intermediate connecting region including a third n-type charge generation layer, a third intermediate layer and a third p-type charge generation layer, a fourth hole transport layer, a fourth optional electron blocking layer, a fourth light-emitting layer, a fourth optional hole blocking layer, a fourth electron transport layer, an electron injection layer and a cathode layer.

[0596] According to one embodiment of the present invention, an organic electroluminescent device is provided, which includes: a substrate, an anode layer, a hole injection layer, a first hole transport layer, a first electron blocking layer, a first light-emitting layer, a first optional hole blocking layer, a first electron transport layer, a first intermediate connecting region including a first n-type charge generation layer, a first intermediate layer and a first p-type charge generation layer, a second hole transport layer, a second electron blocking layer, a second light-emitting layer, a second optional hole blocking layer, a second electron transport layer, a second intermediate connecting region including a second n-type charge generation layer, a second intermediate layer and a second p-type charge generation layer, a third hole transport layer, a third electron blocking layer, a third light-emitting layer, a third optional hole blocking layer, a third electron transport layer, a third intermediate connecting region including a third n-type charge generation layer, a third intermediate layer and a third p-type charge generation layer, a fourth hole transport layer, a fourth electron blocking layer, a fourth light-emitting layer, a fourth optional hole blocking layer, a fourth electron transport layer, an electron injection layer and a cathode layer.

[0597] According to one embodiment of the present invention, an organic electroluminescent device is provided, which includes: a substrate, an anode layer, a hole injection layer, a first hole transport layer, a first electron blocking layer, a first light-emitting layer, a first electron transport layer, a first intermediate connecting region including a first n-type charge generation layer, a first intermediate layer and a first p-type charge generation layer, a second hole transport layer, a second electron blocking layer, a second light-emitting layer, a first optional hole blocking layer, a second electron transport layer, a second intermediate connecting region including a second n-type charge generation layer, a second intermediate layer and a second p-type charge generation layer, a third hole transport layer, a third electron blocking layer, a third light-emitting layer, a second optional hole blocking layer, a third electron transport layer, a third intermediate connecting region including a third n-type charge generation layer, a third intermediate layer and a third p-type charge generation layer, a fourth hole transport layer, a fourth electron blocking layer, a fourth light-emitting layer, a third optional hole blocking layer, a fourth electron transport layer, an electron injection layer and a cathode layer.

[0598] According to one embodiment of the present invention, an organic electroluminescent device is provided, which includes: a substrate, an anode layer, a hole injection layer, a first hole transport layer, a first electron blocking layer, a first light-emitting layer, a first electron transport layer, a first intermediate connecting region including a first n-type charge generation layer, a first intermediate layer and a first p-type charge generation layer, a second hole transport layer, a second electron blocking layer, a second light-emitting layer, a second electron transport layer, a second intermediate connecting region including a second n-type charge generation layer, a second intermediate layer and a second p-type charge generation layer, a third hole transport layer, a third electron blocking layer, a third light-emitting layer, a first optional hole blocking layer, a third electron transport layer, a third intermediate connecting region including a third n-type charge generation layer, a third intermediate layer and a third p-type charge generation layer, a fourth hole transport layer, a fourth electron blocking layer, a fourth light-emitting layer, a second optional hole blocking layer, a fourth electron transport layer, an electron injection layer and a cathode layer.

[0599] According to one embodiment of the present invention, an organic electroluminescent device is provided, which includes: a substrate, an anode layer, a hole injection layer, a first hole transport layer, a first electron blocking layer, a first light-emitting layer, a first electron transport layer, a first intermediate connecting region including a first n-type charge generation layer, a first intermediate layer and a first p-type charge generation layer, a second hole transport layer, a second electron blocking layer, a second light-emitting layer, a second electron transport layer, a second intermediate connecting region including a second n-type charge generation layer, a second intermediate layer and a second p-type charge generation layer, a third hole transport layer, a third electron blocking layer, a third light-emitting layer, a third electron transport layer, a third intermediate connecting region including a third n-type charge generation layer, a third intermediate layer and a third p-type charge generation layer, a fourth hole transport layer, a fourth electron blocking layer, a fourth light-emitting layer, an optional hole blocking layer, a fourth electron transport layer, an electron injection layer and a cathode layer.

[0600] Essentially covalent matrix compound

[0601] According to one embodiment of the present invention, the substantially covalent matrix compound may be selected from at least one organic compound. The substantially covalent matrix may consist essentially of covalently bound C, H, O, N, S, optionally further comprising covalently bound B, P, As and / or Se.

[0602] According to one embodiment of the invention, the substantially covalent matrix compound may be selected from organic compounds consisting essentially of covalently bound C, H, O, N, S and optionally further comprising covalently bound B, P, As and / or Se.

[0603] Organometallic compounds containing covalently bonded carbon-metals, metal complexes containing organic ligands, and metal salts of organic acids are other examples of organic compounds that can be used as substantially covalent host compounds of the hole injection layer.

[0604] In one embodiment, the substantially covalent matrix compound lacks metal atoms, and its backbone atoms are mostly selected from C, O, S, and N. Alternatively, the substantially covalent matrix compound lacks metal atoms, and its backbone atoms are mostly selected from C and N.

[0605] According to one embodiment, the molecular weight Mw of the substantially covalent matrix compound may be ≥400 g / mol and ≤2000 g / mol, preferably the molecular weight Mw is ≥450 g / mol and ≤1500 g / mol, more preferably the molecular weight Mw is ≥500 g / mol and ≤1000 g / mol, further preferably the molecular weight Mw is ≥550 g / mol and ≤900 g / mol, further preferably the molecular weight Mw is ≥600 g / mol and ≤800 g / mol.

[0606] Preferably, the substantially covalent matrix compound comprises at least one arylamine moiety, or a diarylamine moiety, or a triarylamine moiety.

[0607] Preferably, the substantially covalent matrix compound is free of metal and / or ionic bonds.

[0608] The compound of formula (VII) or the compound of formula (VIII)

[0609] According to another aspect of the present invention, the substantially covalent matrix compound may comprise at least one arylamine compound, diarylamine compound, triarylamine compound, a compound of formula (VII) or a compound of formula (VIII):

[0610]

[0611] in:

[0612] T 1 , T 2 , T 3 , T 4 and T 5 independently selected from a single bond, a phenylene group, a biphenylene group, a terphenylene group or a naphthalene group, preferably a single bond or a phenylene group;

[0613] T 6 is a phenyl subunit, a biphenyl subunit, a terphenyl subunit or a naphthalene subunit;

[0614] Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar' 4 and Ar' 5 independently selected from substituted or unsubstituted C6 to C 20 Aryl or substituted or unsubstituted C3 to C20 heteroarylidene, substituted or unsubstituted biphenylidene, substituted or unsubstituted fluorene, substituted 9-fluorene, substituted 9,9-fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted terphenylidene, substituted or unsubstituted tetracene, substituted or unsubstituted benzanthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthene, substituted or unsubstituted carbazole, substituted 9-phenylcarbazole, substituted or unsubstituted azepane, substituted or unsubstituted dibenzo[b,f]azepane, substituted or unsubstituted 9,9'- Spirobi[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanthene]; or a substituted or unsubstituted aromatic fused ring system comprising at least three substituted or unsubstituted aromatic rings selected from: substituted or unsubstituted non-heterocyclic, substituted or unsubstituted hetero 5-membered ring, substituted or unsubstituted 6-membered ring and / or substituted or unsubstituted 7-membered ring, substituted or unsubstituted fluorene; or a fused ring system comprising 2 to 6 substituted or unsubstituted 5 to 7-membered rings, and the rings are selected from: (i) heterocyclic unsaturated 5 to 7-membered rings, (ii) aromatic heterocyclic 5 to 6-membered rings, (iii) non-heterocyclic unsaturated 5 to 7-membered rings, (iv) aromatic non-heterocyclic 6-membered rings;

[0615] in

[0616] Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar' 4 and Ar' 5 The substituents are selected from the group consisting of H, D, F, C(=O)R' 2 、CN、Si(R' 2 )3. P(=O)(R' 2 )2. OR' 2 、S(=O)R' 2 、S(=O)2R' 2 , substituted or unsubstituted straight-chain alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted branched-chain alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl or alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aromatic ring systems having 6 to 40 aromatic ring atoms and substituted or unsubstituted heteroaromatic ring systems having 5 to 40 aromatic ring atoms, unsubstituted C6 to C 18 Aryl, unsubstituted C3 to C 18heteroaryl, a fused ring system comprising 2 to 6 unsubstituted 5 to 7 membered rings, and the rings are selected from: heterocyclic unsaturated 5 to 7 membered rings, aromatic heterocyclic 5 to 6 membered rings, non-heterocyclic unsaturated 5 to 7 membered rings and aromatic non-heterocyclic 6 membered rings,

[0617] Where R' 2 The alkyl radical may be selected from H, D, a linear alkyl radical having 1 to 6 carbon atoms, a branched alkyl radical having 1 to 6 carbon atoms, a cyclic alkyl radical having 3 to 6 carbon atoms, an alkenyl or alkynyl radical having 2 to 6 carbon atoms, a C6 to C 18 Aryl or C3 to C 18 Heteroaryl.

[0618] According to one embodiment, wherein T 1 , T 2 , T 3 , T 4 and T 5 can be independently selected from a single bond, a phenyl group, a biphenyl group or a terphenyl group. According to one embodiment, wherein T 1 , T 2 , T 3 , T 4 and T 5 can be independently selected from a phenyl subunit, a biphenyl subunit or a terphenyl subunit, and T 1 , T 2 , T 3 , T 4 and T 5 is a single bond. According to one embodiment, wherein T 1 , T 2 , T 3 , T 4 and T 5 may be independently selected from a phenylene group or a biphenylene group, and T 1 , T 2 , T 3 , T 4 and T 5 is a single bond. According to one embodiment, wherein T 1 , T 2 , T 3 , T 4 and T 5 may be independently selected from a phenylene group or a biphenylene group, and T 1 , T 2 , T 3 , T 4 and T 5 Two of them are single bonds.

[0619] According to one embodiment, wherein T 1 , T 2 and T3 may be independently selected from phenylene groups, and T 1 , T 2 and T 3 is a single bond. According to one embodiment, wherein T 1 , T 2 and T 3 may be independently selected from phenylene groups, and T 1 , T 2 and T 3 Two of them are single bonds.

[0620] According to one embodiment, wherein T 6 It can be a phenyl subunit, a biphenyl subunit, or a terphenyl subunit. According to one embodiment, wherein T 6 According to one embodiment, wherein T 6 It can be a biphenyl subunit. According to one embodiment, wherein T 6 It may be a terphenyl subunit.

[0621] According to one embodiment, wherein Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar' 4 and Ar' 5 Can be independently selected from D1 to D16:

[0622]

[0623]

[0624] The asterisk "*" indicates the binding position.

[0625] According to one embodiment, wherein Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar' 4 and Ar' 5 Can be independently selected from D1 to D15; or selected from D1 to D10 and D13 to D15.

[0626] According to one embodiment, wherein Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar' 4 and Ar' 5 Can be independently selected from D1, D2, D5, D7, D9, D10, D13 to D16.

[0627] When Ar' 1 ,Ar' 2 ,Ar' 3,Ar' 4 and Ar' 5 When selected within this range, the standard starting temperature can be in a range particularly suitable for mass production.

[0628] The “host compound of formula (VII) or formula (VIII)” may also be referred to as a “hole transport compound”.

[0629] According to one embodiment, the substantially covalent matrix compound comprises at least one naphthyl group, carbazole group, dibenzofuran group, dibenzothiophene group and / or substituted fluorenyl group, wherein the substituents are independently selected from methyl, phenyl or fluorenyl.

[0630] According to one embodiment of the electronic device, the matrix compound of formula (VII) or formula (VIII) is selected from F1 to F18:

[0631]

[0632]

[0633] According to one embodiment of the present invention, the organic electroluminescent device is an organic light emitting diode.

[0634] According to a preferred embodiment of the present invention, the organic electroluminescent device is an organic light emitting diode, wherein light is emitted through a cathode layer.

[0635] The present invention further relates to a display device, which comprises the organic electroluminescent device according to the present invention.

[0636] According to a preferred embodiment of the present invention, the display device comprises the organic electroluminescent device according to the present invention, wherein the cathode layer is transparent.

[0637] p-type charge generation layer (different from the p-type charge generation layer in the middle region)

[0638] The p-type charge generation layer may be formed on the anode layer or cathode layer by vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blodgett (LB) deposition, etc. When the p-type charge generation layer is formed using vacuum deposition, the deposition conditions may vary depending on the compound or compounds used to form the layer and the desired structure and thermal properties of the layer. However, in general, the conditions for vacuum deposition may include a deposition temperature of 100° C. to 350° C., a ... -8 Support up to 10 -3 Torr pressure (1 Torr equals 133.322 Pa) and a deposition rate of 0.1 nm / s to 10 nm / s.

[0639] When the p-type charge generation layer is formed using spin coating or printing, the coating conditions may vary with the one or more compounds used to form the layer and the desired structure and thermal properties of the organic semiconductor layer. For example, the coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80° C. to about 200° C. After coating, the solvent is removed by heat treatment.

[0640] The thickness of the p-type charge generation layer may be in the range of about 1 nm to about 20 nm, for example, in the range of about 2 nm to about 15 nm or about 2 nm to about 12 nm.

[0641] Hole injection layer

[0642] The hole injection layer (HIL) may be formed on the anode layer by vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blodgett (LB) deposition, etc. When the HIL is formed using vacuum deposition, the deposition conditions may vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. However, in general, the vacuum deposition conditions may include a deposition temperature of 100° C. to 500° C., a ... -8 Support up to 10 -3 Torr pressure (1 Torr equals 133.322 Pa) and a deposition rate of 0.1 nm / s to 10 nm / s.

[0643] When the HIL is formed using spin coating or printing, the coating conditions may vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. For example, the coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80° C. to about 200° C. After coating, the heat treatment removes the solvent.

[0644] According to a preferred embodiment of the present invention, the hole injection layer may comprise a substantially covalent matrix compound.

[0645] The thickness of the HIL may be in the range of about 1 nm to about 100 nm, for example, about 1 nm to about 25 nm. When the thickness of the HIL is within this range, the HIL may have excellent hole injection characteristics without substantially deteriorating driving voltage.

[0646] Preferably, the HIL is in direct contact with the anode layer.

[0647] The hole injection layer may contain an organic p-type dopant.

[0648] The organic p-type dopant may be a radialene of formula (I).

[0649] The hole injection layer may contain a hole transport compound.

[0650] The hole injection layer may include an organic p-type dopant and a hole transport compound.

[0651] Other layers

[0652] According to the present invention, in addition to the layers mentioned above, the organic electroluminescent device may further comprise other layers. Exemplary embodiments of the various layers are described below:

[0653] Base

[0654] The substrate can be any substrate commonly used in the manufacture of electronic devices such as organic light emitting diodes. If light is to be emitted through the substrate, the substrate should be a transparent or translucent material, such as a glass substrate or a transparent plastic substrate. If light is to be emitted through the top surface, the substrate can be both a transparent material and an opaque material, such as a glass substrate, a plastic substrate, a metal substrate, a silicon substrate, or a backplane.

[0655] Anode layer

[0656] The anode layer can be formed by depositing or sputtering the material for forming the anode layer. The material for forming the anode layer can be a high work function material, thereby promoting hole injection. The anode material can also be selected from low work function materials (i.e., aluminum). The anode electrode can be a transparent or reflective electrode. Transparent conductive oxides such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), aluminum zinc oxide (AlZO) and zinc oxide (ZnO) can be used to form the anode electrode. Metals can also be used, typically silver (Ag), gold (Au) or metal alloys are used to form the anode layer.

[0657] Hole transport layer

[0658] The organic electroluminescent device according to the present invention may further comprise at least one hole transport layer (HTL). According to one embodiment of the present invention, the at least one hole transport layer is included in one of the first light-emitting unit or the second light-emitting unit, wherein preferably at least one hole transport layer is included in each light-emitting unit.

[0659] A hole transport layer (HTL) may be formed on the HIL or CGL by vacuum deposition, spin coating, slot die coating, printing, casting, Langmuir-Blodgett (LB) deposition, etc. When the HTL is formed by vacuum deposition or spin coating, the deposition and coating conditions may be similar to those used to form the HIL or CGL. However, the conditions for vacuum or solution deposition may vary depending on the compound used to form the HTL.

[0660] The HTL can be formed of any compound commonly used to form the HTL. For example, Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010 disclose applicable compounds and are incorporated herein by reference. Examples of compounds that can be used to form the HTL are: carbazole derivatives, such as N-phenylcarbazole or polyvinylcarbazole; benzidine derivatives, such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine (α-NPD); and triphenylamine compounds, such as 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA). Among these compounds, TCTA can transport holes and inhibit the diffusion of excitons into the EML.

[0661] According to one embodiment of the present invention, the hole transport layer may comprise a substantially covalent host compound as described above.

[0662] According to a preferred embodiment of the present invention, the hole injection layer and the hole transport layer may comprise the same substantially covalent matrix compound as described above.

[0663] According to one embodiment of the present invention, the hole transport layer may include the compound of formula (VII) or formula (VIII) as described above.

[0664] According to a preferred embodiment of the present invention, the hole injection layer and the hole transport layer may contain the same compound of formula (VII) or formula (VIII) as described above.

[0665] According to a preferred embodiment of the present invention, the p-type charge generation layer, the hole injection layer and the hole transport layer may comprise the same substantially covalent host compound.

[0666] According to a preferred embodiment of the present invention, the p-type charge generation layer, the hole injection layer and the hole transport layer may comprise the same compound of formula (VII) or formula (VIII) as described above.

[0667] The thickness of the HTL may be in the range of about 5 nm to about 250 nm, preferably about 10 nm to about 200 nm, more preferably about 20 nm to about 190 nm, more preferably about 40 nm to about 180 nm, more preferably about 60 nm to about 170 nm, more preferably about 80 nm to about 160 nm, more preferably about 100 nm to about 160 nm, more preferably about 120 nm to about 140 nm. The preferred thickness of the HTL may be 170 nm to 200 nm.

[0668] When the thickness of the HTL is within this range, the HTL may have excellent hole transport characteristics without substantially deteriorating driving voltage.

[0669] Electron blocking layer

[0670] The function of the electron blocking layer (EBL) is to prevent electrons from being transferred from the light-emitting layer to the hole transport layer, and thereby confine the electrons to the light-emitting layer. Thus, efficiency, operating voltage and / or life are improved. Typically, the electron blocking layer comprises a triarylamine compound. The LUMO energy level of the triarylamine compound can be closer to the vacuum energy level than the LUMO energy level of the hole transport layer. The HOMO energy level of the electron blocking layer can be further away from the vacuum energy level than the HOMO energy level of the hole transport layer. The thickness of the electron blocking layer can be selected between 2nm and 20nm.

[0671] If the electron blocking layer has a high triplet energy level it can also be described as a triplet controlling layer.

[0672] If a phosphorescent green or blue emitting layer is used, the function of the triplet control layer is to reduce triplet quenching. Thus, a higher luminous efficiency of the phosphorescent emitting layer can be achieved. The triplet control layer is selected from triarylamine compounds whose triplet energy level is higher than the triplet energy level of the phosphorescent emitter in the adjacent emitting layer. Compounds suitable for triplet control layers, in particular triarylamine compounds, are described in EP 2 722 908 A1.

[0673] Photoactive Layer (PAL)

[0674] According to one embodiment of the present invention, the organic electroluminescent device may further include a photoactive layer, wherein the photoactive layer is arranged between the anode layer and the cathode layer.

[0675] The photoactive layer converts electric current into photons or converts photons into electric current.

[0676] The PAL can be formed on the HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When the PAL is formed using vacuum deposition or spin coating, the deposition and coating conditions may be similar to those used to form the HIL. However, the deposition and coating conditions may vary depending on the compound used to form the PAL.

[0677] The photoactive layer can be a light-emitting layer or a light-absorbing layer, in particular a light-emitting layer.

[0678] Emission layer (EML)

[0679] According to one embodiment of the present invention, the organic electroluminescent device may further include a light-emitting layer, wherein the light-emitting layer is arranged between the anode layer and the cathode layer.

[0680] The EML can be formed on the HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When the EML is formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for forming the HIL. However, the conditions for deposition and coating may vary depending on the compound used to form the EML.

[0681] The light-emitting layer (EML) may be formed of a combination of a host and a light-emitting dopant. Examples of the host are Alq3, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 4,4',4"-tri(carbazole-9-yl)-triphenylamine (TCTA), 1,3,5-tri(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), distyrylarene (DSA), and bis(2-(2-hydroxyphenyl)benzothiazole)zinc (Zn(BTZ)2).

[0682] The emitter dopant may be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters that emit light via a thermally activated delayed fluorescence (TADF) mechanism may be preferred due to their higher efficiency. The emitter may be a small molecule or a polymer.

[0683] Examples of red emitter dopants are PtOEP, Ir(piq)3 and Btp2Ir(acac), but are not limited thereto. These compounds are phosphorescent emitters, however, fluorescent red emitter dopants may also be used.

[0684] Examples of phosphorescent green emitter dopants are Ir(ppy)3 (ppy=phenylpyridine), Ir(ppy)2(acac), Ir(mpyp)3.

[0685] Examples of phosphorescent blue emitter dopants are F2Irpic, (F2ppy)2Ir(tmd) and Ir(dfppz)3 and trifluorene. 4,4'-bis(4-diphenylaminophenylvinyl)biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe) are examples of fluorescent blue emitter dopants.

[0686] The amount of the luminophore dopant may be in the range of about 0.01 parts by weight to about 50 parts by weight relative to 100 parts by weight of the host. Alternatively, the luminescent layer may be composed of a luminescent polymer. The thickness of the EML may be about 10 nm to about 100 nm, for example, about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML may have excellent luminescence without causing substantial damage to the driving voltage.

[0687] Hole Blocking Layer (HBL)

[0688] A hole blocking layer (HBL) may be formed on the EML to prevent holes from diffusing into the ETL by using vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When the EML includes a phosphorescent dopant, the HBL may also have a triplet exciton blocking function.

[0689] HBL may also be referred to as auxiliary ETL or a-ETL.

[0690] When the HBL is formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for forming the HIL. However, the conditions for deposition and coating may vary depending on the compound used to form the HBL. Any compound commonly used to form the HBL may be used. Examples of compounds used to form the HBL include Oxadiazole derivatives, triazole derivatives, phenanthroline derivatives and azine derivatives, preferably triazine or pyrimidine derivatives.

[0691] The thickness of the HBL may be in a range of about 5 nm to about 100 nm, for example, about 10 nm to about 30 nm. When the thickness of the HBL is within this range, the HBL may have excellent hole blocking properties without substantially compromising driving voltage.

[0692] Electron Transport Layer (ETL)

[0693] The organic electroluminescent device according to the present invention may further comprise at least one electron transport layer (ETL). According to one embodiment of the present invention, the at least one electron transport layer is included in one of the first light-emitting unit or the second light-emitting unit, wherein preferably at least one electron transport layer is included in each light-emitting unit.

[0694] According to another embodiment of the present invention, the electron transport layer may further comprise an azine compound, preferably a pyridine, pyrimidine or triazine compound, most preferably a triazine compound or a pyrimidine compound.

[0695] According to another embodiment of the present invention, the electron transport layer may further include 2-([1,1'-biphenyl]-4-yl)-4-(9,9-diphenyl-9H-fluorene-4-yl)-6-phenyl-1,3,5-triazine, 2-(3-(2,6-dimethylpyridin-3-yl)-5-(phenanthrene-9-yl)phenyl)-4,6-diphenyl-1,3,5-triazine, 3'-(4-phenyl-6-(spiro[fluorene-9,9'-xanthene]-2'-yl)-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-4-carbonitrile and 4'-(4-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalen-1-yl)-[1,1'-biphenyl]-4-carbonitrile.

[0696] In one embodiment, the electron transport layer may further comprise a dopant selected from alkali metal organic complexes, preferably LiQ.

[0697] The thickness of the ETL may be in the range of about 15 nm to about 50 nm, for example, in the range of about 20 nm to about 40 nm. When the thickness of the ETL is within this range, the ETL may have satisfactory electron injection performance without substantially deteriorating the driving voltage.

[0698] According to another embodiment of the present invention, the organic electroluminescent device may further comprise a hole blocking layer and an electron transport layer, wherein the hole blocking layer and the electron transport layer comprise an azine compound. Preferably, the azine compound is a pyridine, pyrimidine or triazine compound, most preferably a triazine compound.

[0699] Electron injection layer (EIL)

[0700] An optional EIL capable of facilitating electron injection from the cathode may be formed on the ETL, preferably closest to the cathode, and more preferably directly on the electron transport layer. Examples of materials for forming the EIL include 8-hydroxyquinoline lithium (LiQ), LiF, NaCl, CsF, Li2O, BaO, Ca, Ba, Yb, and Mg known in the art. The deposition and coating conditions for forming the EIL are similar to those for forming the HIL, but the deposition and coating conditions may vary depending on the material for forming the EIL.

[0701] The thickness of the EIL may be within a range of about 0.1 nm to about 10 nm, for example, within a range of about 0.5 nm to about 9 nm. When the thickness of the EIL is within this range, the EIL may have satisfactory electron injection performance without substantially deteriorating driving voltage.

[0702] Cathode layer

[0703] A cathode layer is formed on the ETL or the optional EIL. The cathode layer may be formed of a metal, an alloy, a conductive compound, or a mixture thereof. The cathode electrode may have a low work function. For example, the cathode layer may be formed of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), etc. Alternatively, the cathode electrode may be formed of a transparent conductive oxide such as ITO or IZO.

[0704] The thickness of the cathode layer may be in the range of about 5 nm to about 1000 nm, for example, in the range of about 10 nm to about 100 nm. When the thickness of the cathode layer is in the range of about 5 nm to about 50 nm, the cathode layer may be transparent or translucent even if it is formed of a metal or a metal alloy.

[0705] In a preferred embodiment, the cathode layer comprises a metal or a metal alloy and is transparent.

[0706] It is to be understood that the cathode layer is not part of the electron injection layer or the electron transport layer. BRIEF DESCRIPTION OF THE DRAWINGS

[0707] The above-mentioned components in the described embodiments as well as the components claimed and used according to the invention do not have any special exceptions in terms of their size, shape, material selection and technical principles, so that the selection criteria known in the relevant field can be applied without restriction.

[0708] Other details, features and advantages of the purpose of the present invention are disclosed in the dependent claims and the description of the corresponding drawings below, which show preferred embodiments according to the present invention in an exemplary manner. However, any embodiment may not necessarily represent the full scope of the present invention, so reference is made to the claims and this document to interpret the scope of the present invention. It should be understood that the above general description and the following detailed description are only exemplary and illustrative, and are intended to further illustrate the invention claimed.

[0709] Figure 1 is a schematic cross-sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.

[0710] Figure 2 is a schematic cross-sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.

[0711] Figure 3 is a schematic cross-sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.

[0712] Figure 4 is a schematic cross-sectional view of a stacked organic electroluminescent device according to another exemplary embodiment of the present invention.

[0713] Figure 5 is a schematic cross-sectional view of a stacked organic electroluminescent device according to another exemplary embodiment of the present invention.

[0714] Figure 6 is a schematic cross-sectional view of a stacked organic electroluminescent device according to another exemplary embodiment of the present invention.

[0715] Figure 7 is a schematic cross-sectional view of a stacked organic electroluminescent device according to another exemplary embodiment of the present invention.

[0716] Figure 8 is a schematic cross-sectional view of a stacked organic electroluminescent device according to another exemplary embodiment of the present invention.

[0717] Fig. 9 is a schematic cross-sectional view of a stacked organic electroluminescent device according to another exemplary embodiment of the present invention.

[0718] Fig.10 is a schematic cross-sectional view of a stacked organic electroluminescent device according to another exemplary embodiment of the present invention.

[0719] Fig.11 is a schematic cross-sectional view of a stacked organic electroluminescent device according to another exemplary embodiment of the present invention.

[0720] Fig.12 is a schematic cross-sectional view of a stacked organic electroluminescent device according to another exemplary embodiment of the present invention.

[0721] Fig.13 is a schematic cross-sectional view of a stacked organic electroluminescent device according to another exemplary embodiment of the present invention.

[0722] Fig.14 is a schematic cross-sectional view of an anode layer 120 on a substrate 110 .

[0723] The accompanying drawings are described in more detail below with reference to embodiments. However, the present disclosure is not limited to the following drawings.

[0724] In this document, when a first element is referred to as being formed or disposed "on" or "over" a second element, the first element may be disposed directly on the second element, or one or more other elements may be disposed between them. When a first element is referred to as being "formed or disposed directly on" or "formed or disposed directly onto" a second element, no other elements are disposed between them.

[0725] Figure 1 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0726] refer to Figure 1The organic electroluminescent device 100 comprises an anode layer 120, a first light-emitting unit 140, a first intermediate connection region (ICR1) 150 comprising a first n-type charge generation layer (n-CGL1) 151, a first intermediate layer (IL1) 153 and a first p-type charge generation layer (p-CGL1) 152, wherein the n-type charge generation layer (n-CGL1) comprises a host compound and a metal dopant, wherein the first intermediate layer (IL1) 153 comprises a hole transport compound, and wherein the first p-type charge generation layer (p-CGL1) 152 comprises a radialene of formula (I) and a hole transport host compound. The organic electroluminescent device 100 further comprises a second light-emitting unit 240 and a cathode layer (CAT) 190.

[0727] Figure 2 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0728] refer to Figure 2 The organic electroluminescent device 100 comprises an anode layer 120, a hole injection layer (HIL) 130, a first light emitting unit 140, a first intermediate connection region (ICR1) 150 comprising a first n-type charge generation layer (n-CGL1) 151, a first intermediate layer (IL1) 153 and a first p-type charge generation layer (p-CGL1) 152, wherein the n-type charge generation layer (n-CGL1) comprises a host compound and a metal dopant, wherein the first intermediate layer (IL1) 153 comprises a hole transport compound, and wherein the first p-type charge generation layer (p-CGL1) 152 comprises a radialene of formula (I) and a hole transport host compound. The organic electroluminescent device 100 further comprises a second light emitting unit 240, an electron injection layer (EIL) 180 and a cathode layer (CAT) 190.

[0729] Figure 3 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0730] refer to Figure 3The organic electroluminescent device 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 including a radialene of formula (I), and a first light-emitting unit 140, wherein the first light-emitting unit 140 includes a first hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, a first light-emitting layer (EML1) 143, a first hole blocking layer (HBL1) 144 and a first electron transport layer (ETL1) 145. The organic electroluminescent device 100 further comprises a first intermediate connecting region (ICR1) 150, the first intermediate connecting region (ICR1) 150 comprises a first n-type charge generation layer (n-CGL1) 151, a first intermediate layer (IL1) 153 and a first p-type charge generation layer (p-GCL1) 152, wherein the n-type charge generation layer (n-CGL1) comprises a host compound and a metal dopant, wherein the first intermediate layer (IL1) 153 comprises a hole transport compound, and wherein the first p-type charge generation layer (p-CGL1) 152 comprises a radialene of formula (I) and a hole transport host compound. The organic electronic device 100 further comprises a second light emitting unit 240, the second light emitting unit 240 comprises a second hole transport layer (HTL2) 241, a second electron blocking layer (EBL2) 242, a second light emitting layer (EML2) 243, a second hole blocking layer (HBL2) 244 and a second electron transport layer (ETL2) 245. The organic electroluminescent device 100 further includes an electron injection layer (EIL) 180 and a cathode layer (CAT) 190 .

[0731] Figure 4 is a schematic cross-sectional view of a stacked organic electroluminescent device 100 according to another exemplary embodiment of the present invention. Figure 4 and Figure 3 The difference is that Figure 3 The organic electroluminescent device 100 further comprises a second intermediate connection region (ICR2) 250 disposed on the second light-emitting unit 240, wherein the second intermediate connection region comprises a second n-type charge generation layer (n-CGL2) 251, a second intermediate layer (IL2) 253, and a second p-type charge generation layer (p-GCL2) 252, wherein the second n-type charge generation layer (n-CGL2) 251 may further optionally comprise a matrix compound and a metal dopant, wherein the second intermediate layer (IL2) 253 may further optionally comprise a hole transport compound, and wherein the second p-type charge generation layer (p-CGL2) 252 may further optionally comprise a radialene of formula (I) and a hole transport matrix compound. Figure 4 The organic electroluminescent device 100 and Figure 3The difference is that it also includes a third light-emitting unit 340 arranged on the second intermediate connecting region (ICR2) 250, and the third light-emitting unit 340 includes a third hole transport layer (HTL3) 341, a third electron blocking layer (EBL3) 342, a third light-emitting layer (EML3) 343, a third hole blocking layer (HBL3) 344 and a third electron transport layer (ETL3) 345.

[0732] Figure 5 is a schematic cross-sectional view of a stacked organic electroluminescent device 100 according to another exemplary embodiment of the present invention. Figure 5 and Figure 4 The difference is that Figure 4 The organic electroluminescent device 100 further comprises a third intermediate connecting region (ICR3) 350 disposed on the third light-emitting unit 340, wherein the third intermediate connecting region (ICR3) 350 comprises a third n-type charge generation layer (n-CGL3) 351, a third intermediate layer (IL3) 353 and a third p-type charge generation layer (p-GCL3) 352, wherein the third n-type charge generation layer (n-CGL3) 351 may also optionally comprise a matrix compound and a metal dopant, wherein the third intermediate layer (IL3) 353 may also optionally comprise a hole transport compound, and wherein the third p-type charge generation layer (p-CGL3) 352 may also optionally comprise a radialene of formula (I) and a hole transport matrix compound. Figure 5 The organic electroluminescent device 100 and Figure 3 The difference is that it also includes a fourth light-emitting unit 440 arranged on the third intermediate connecting region (ICR3) 350, and the fourth light-emitting unit includes a fourth hole transport layer (HTL4) 441, a fourth electron blocking layer (EBL4) 442, a fourth light-emitting layer (EML4) 443, a fourth hole blocking layer (HBL4) 444 and a fourth electron transport layer (ETL4) 445.

[0733] Figure 6 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0734] refer to Figure 6, the organic electroluminescent device 100 comprises a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 comprising a radialene of formula (I), and a first light-emitting unit 140, wherein the first light-emitting unit 140 comprises a first hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, a first light-emitting layer (EML1) 143, a first hole blocking layer (HBL1) 144, and a first electron transport layer (ETL1) 145. The organic electroluminescent device 100 further comprises an n-type charge generation layer 161 and a p-type charge generation layer 162. The organic electroluminescent device 100 further comprises a second light-emitting unit 240, wherein the second light-emitting unit 240 comprises a second hole transport layer (HTL2) 241, a second electron blocking layer (EBL2) 242, a second light-emitting layer (EML2) 243, a second hole blocking layer (HBL2) 244, and a second electron transport layer (ETL2) 245.

[0735] The organic electroluminescent device 100 also includes a first intermediate connecting region (ICR1) arranged on the second light-emitting unit 240, the first intermediate connecting region (ICR1) including an n-type first charge generation layer (n-CGL1) 151, a first intermediate layer (IL1) 153 and a first p-type charge generation layer (p-CGL1) 152 of the first intermediate connecting region, wherein the first n-type charge generation layer (n-CGL1) 151 of the first intermediate connecting region includes a host compound and a metal dopant, wherein the first intermediate layer (IL1) 153 includes a hole transport compound, and wherein the first p-type charge generation layer (p-CGL1) 152 of the first intermediate connecting region includes a radialene of formula (I) and a hole transport host compound.

[0736] The organic electroluminescent device 100 further includes a third light-emitting unit 340 disposed on the first intermediate connecting region (ICR1) 150, and the third light-emitting unit 340 includes a third hole transport layer (HTL3) 341, a third electron blocking layer (EBL3) 342, a third light-emitting layer (EML3) 343, a third hole blocking layer (HBL3) 344 and a third electron transport layer (ETL3) 345.

[0737] The organic electroluminescent device 100 further includes an electron injection layer (EIL) 180 and a cathode layer (CAT) 190 .

[0738] Figure 7 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0739] refer to Figure 7The organic electroluminescent device 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 including a radialene of formula (I), and a first light-emitting unit 140, wherein the first light-emitting unit 140 includes a first hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, a first light-emitting layer (EML1) 143, a first hole blocking layer (HBL1) 144 and a first electron transport layer (ETL1) 145. The organic electroluminescent device 100 also includes a first intermediate connecting region (ICR1) arranged on the first light-emitting unit 140, the first intermediate connecting region (ICR1) including a first n-type charge generation layer (n-CGL1) 151 of the first intermediate connecting region, a first intermediate layer (IL1) 153 and a first p-type charge generation layer (p-GCL1) 152 of the first intermediate connecting region, wherein the first n-type charge generation layer (n-CGL1) 151 of the first intermediate connecting region includes a host compound and a metal dopant, wherein the first intermediate layer (IL1) 153 includes a hole transport compound, and wherein the first p-type charge generation layer (p-CGL1) 152 of the first intermediate connecting region includes a radialene of formula (I) and a hole transport host compound.

[0740] The organic electroluminescent device 100 further includes a second light-emitting unit 240 disposed on the first intermediate connecting region (ICR1) 150, and the second light-emitting unit 240 includes a second hole transport layer (HTL2) 241, a second electron blocking layer (EBL2) 242, a second light-emitting layer (EML2) 243, a second hole blocking layer (HBL2) 244 and a second electron transport layer (ETL2) 245.

[0741] The organic electroluminescent device 100 further includes an n-type charge generation layer 161 disposed on the second light emitting unit 240. The p-type charge generation layer 162 is disposed on the n-type charge generation layer 161.

[0742] The organic electroluminescent device 100 further includes a third light-emitting unit 340 disposed on the p-type charge generation layer 162, and the third light-emitting unit 340 includes a third hole transport layer (HTL3) 341, a third electron blocking layer (EBL3) 342, a third light-emitting layer (EML3) 343, a third hole blocking layer (HBL3) 344 and a third electron transport layer (ETL3) 345.

[0743] The organic electroluminescent device 100 further includes an electron injection layer (EIL) 180 and a cathode layer (CAT) 190 .

[0744] Figure 8is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0745] refer to Figure 8 , the organic electroluminescent device 100 comprises a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 comprising a radialene of formula (I), and a first light-emitting unit 140, wherein the first light-emitting unit 140 comprises a first hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, a first light-emitting layer (EML1) 143, a first hole blocking layer (HBL1) 144, and a first electron transport layer (ETL1) 145. The organic electroluminescent device 100 further comprises an n-type charge generation layer 161 and a p-type charge generation layer 162. The organic electroluminescent device 100 further comprises a second light-emitting unit 240, wherein the second light-emitting unit 240 comprises a second hole transport layer (HTL2) 241, a second electron blocking layer (EBL2) 242, a second light-emitting layer (EML2) 243, a second hole blocking layer (HBL2) 244, and a second electron transport layer (ETL2) 245.

[0746] The organic electroluminescent device 100 also includes a first intermediate connecting region (ICR1) 150 arranged on the second light-emitting unit 240, the first intermediate connecting region (ICR1) 150 including an n-type first charge generating layer (n-CGL1) 151 of the first intermediate connecting region, a first intermediate layer (IL1) 153 and a first p-type charge generating layer (p-CGL1) 152 of the first intermediate connecting region, wherein the first n-type charge generating layer (n-CGL1) 151 of the first intermediate connecting region includes a host compound and a metal dopant, wherein the first intermediate layer (IL1) 153 includes a hole transport compound, and wherein the first p-type charge generating layer (p-CGL1) 152 of the first intermediate connecting region includes a radialene of formula (I) and a hole transport host compound.

[0747] The organic electroluminescent device 100 further includes a third light-emitting unit 340 disposed on the first intermediate connecting region (ICR1) 150, and the third light-emitting unit 340 includes a third hole transport layer (HTL3) 341, a third electron blocking layer (EBL3) 342, a third light-emitting layer (EML3) 343, a third hole blocking layer (HBL3) 344 and a third electron transport layer (ETL3) 345.

[0748] The organic electroluminescent device 100 also includes a second intermediate connecting region (ICR2) 250 arranged on the third light-emitting unit 340, and the second intermediate connecting region (ICR2) 250 includes an n-type second charge generation layer (n-CGL2) 251, a second intermediate layer (IL2) 253 and a second p-type charge generation layer (p-GCL2) 252 of the second intermediate connecting region, wherein the second n-type charge generation layer (n-CGL2) 251 of the second intermediate connecting region may also optionally include a matrix compound and a metal dopant, wherein the second intermediate layer (IL2) 253 may also optionally include a hole transport compound, and wherein the second p-type charge generation layer (p-CGL2) 252 of the second intermediate connecting region may also optionally include a radialene of formula (I) and a hole transport matrix compound.

[0749] The organic electroluminescent device 100 further includes a fourth light-emitting unit 440 disposed on the second intermediate connecting region (ICR2) 250, and the fourth light-emitting unit 440 includes a fourth hole transport layer (HTL4) 441, a fourth electron blocking layer (EBL4) 442, a fourth light-emitting layer (EML4) 443, a fourth hole blocking layer (HBL4) 444 and a fourth electron transport layer (ETL4) 445.

[0750] The organic electroluminescent device 100 further includes an electron injection layer (EIL) 180 and a cathode layer (CAT) 190 .

[0751] Fig. 9 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0752] refer to Fig. 9 The organic electroluminescent device 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 including a radialene of formula (I), and a first light-emitting unit 140, wherein the first light-emitting unit 140 includes a first hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, a first light-emitting layer (EML1) 143, a first hole blocking layer (HBL1) 144 and a first electron transport layer (ETL1) 145.

[0753] The organic electroluminescent device 100 also includes a first intermediate connecting region (ICR1) 150 arranged on the first light-emitting unit 140, the first intermediate connecting region (ICR1) 150 including an n-type first charge generating layer (n-CGL1) 151 of the first intermediate connecting region, a first intermediate layer (IL1) 153 and a first p-type charge generating layer (p-CGL1) 152 of the first intermediate connecting region, wherein the first n-type charge generating layer (n-CGL1) 151 of the first intermediate connecting region includes a host compound and a metal dopant, wherein the first intermediate layer (IL1) 153 includes a hole transport compound, and wherein the first p-type charge generating layer (p-CGL1) 152 of the first intermediate connecting region includes a radialene of formula (I) and a hole transport host compound.

[0754] The organic electroluminescent device 100 further includes a second light-emitting unit 240 disposed on the first intermediate connecting region (ICR1) 150, and the second light-emitting unit 240 includes a second hole transport layer (HTL2) 241, a second electron blocking layer (EBL2) 242, a second light-emitting layer (EML2) 243, a second hole blocking layer (HBL2) 244 and a second electron transport layer (ETL2) 245.

[0755] The organic electroluminescent device 100 further includes an n-type charge generation layer 161 and a p-type charge generation layer 162 .

[0756] The organic electroluminescent device 100 further includes a third light-emitting unit 340 disposed on the p-type charge generation layer 162, and the third light-emitting unit 340 includes a third hole transport layer (HTL3) 341, a third electron blocking layer (EBL3) 342, a third light-emitting layer (EML3) 343, a third hole blocking layer (HBL3) 344 and a third electron transport layer (ETL3) 345.

[0757] The organic electroluminescent device 100 also includes a second intermediate connecting region (ICR2) 250 arranged on the third light-emitting unit 340, and the second intermediate connecting region (ICR2) 250 includes an n-type second charge generation layer (n-CGL2) 251, a second intermediate layer (IL2) 253 and a second p-type charge generation layer (p-CGL2) 252 of the second intermediate connecting region, wherein the second n-type charge generation layer (n-CGL2) 251 of the second intermediate connecting region may also optionally include a matrix compound and a metal dopant, wherein the second intermediate layer (IL2) 253 may also optionally include a hole transport compound, and wherein the second p-type charge generation layer (p-CGL3) 252 of the second intermediate connecting region may also optionally include a radialene of formula (I) and a hole transport matrix compound.

[0758] The organic electroluminescent device 100 further includes a fourth light-emitting unit 440 disposed on the second intermediate connecting region (ICR2) 250, and the fourth light-emitting unit 440 includes a fourth hole transport layer (HTL4) 441, a fourth electron blocking layer (EBL4) 442, a fourth light-emitting layer (EML4) 443, a fourth hole blocking layer (HBL4) 444 and a fourth electron transport layer (ETL4) 445.

[0759] The organic electroluminescent device 100 further includes an electron injection layer (EIL) 180 and a cathode layer (CAT) 190 .

[0760] Fig.10 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0761] refer to Fig.10 The organic electroluminescent device 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 including a radialene of formula (I), and a first light-emitting unit 140, wherein the first light-emitting unit 140 includes a first hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, a first light-emitting layer (EML1) 143, a first hole blocking layer (HBL1) 144 and a first electron transport layer (ETL1) 145.

[0762] The organic electroluminescent device 100 also includes a first intermediate connecting region (ICR1) 150 arranged on the first light-emitting unit 140, the first intermediate connecting region (ICR1) 150 including an n-type first charge generating layer (n-CGL1) 151 of the first intermediate connecting region, a first intermediate layer (IL1) 153 and a first p-type charge generating layer (p-CGL1) 152 of the first intermediate connecting region, wherein the first n-type charge generating layer (n-CGL1) 151 of the first intermediate connecting region includes a host compound and a metal dopant, wherein the first intermediate layer (IL1) 153 includes a hole transport compound, and wherein the first p-type charge generating layer (p-CGL1) 152 of the first intermediate connecting region includes a radialene of formula (I) and a hole transport host compound.

[0763] The organic electroluminescent device 100 further includes a second light-emitting unit 240 disposed on the first intermediate connecting region (ICR1) 150, and the second light-emitting unit 240 includes a second hole transport layer (HTL2) 241, a second electron blocking layer (EBL2) 242, a second light-emitting layer (EML2) 243, a second hole blocking layer (HBL2) 244 and a second electron transport layer (ETL2) 245.

[0764] The organic electroluminescent device 100 also includes a second intermediate connecting region (ICR2) 250 arranged on the second light-emitting unit 240, and the second intermediate connecting region (ICR2) 250 includes an n-type second charge generation layer (n-CGL2) 251, a second intermediate layer (IL2) 253 and a second p-type charge generation layer (p-CGL2) 252 of the second intermediate connecting region, wherein the second n-type charge generation layer (n-CGL2) 251 of the second intermediate connecting region may also optionally include a matrix compound and a metal dopant, wherein the second intermediate layer (IL2) 253 may also optionally include a hole transport compound, and wherein the second p-type charge generation layer (p-CGL3) 252 of the second intermediate connecting region may also optionally include a radialene of formula (I) and a hole transport matrix compound.

[0765] The organic electroluminescent device 100 further includes a third light-emitting unit 340 disposed on the second intermediate connecting region (ICR2) 250, and the third light-emitting unit 340 includes a third hole transport layer (HTL3) 341, a third electron blocking layer (EBL3) 342, a third light-emitting layer (EML3) 343, a third hole blocking layer (HBL3) 344 and a third electron transport layer (ETL3) 345.

[0766] The organic electroluminescent device 100 further includes an n-type charge generation layer 161 and a p-type charge generation layer 162 .

[0767] The organic electroluminescent device 100 further includes a fourth light-emitting unit 440 disposed on the p-type charge generation layer 162, and the fourth light-emitting unit 440 includes a fourth hole transport layer (HTL4) 441, a fourth electron blocking layer (EBL4) 442, a fourth light-emitting layer (EML4) 443, a fourth hole blocking layer (HBL4) 444 and a fourth electron transport layer (ETL4) 445.

[0768] The organic electroluminescent device 100 further includes an electron injection layer (EIL) 180 and a cathode layer (CAT) 190 .

[0769] Fig.11 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0770] refer to Fig.11The organic electroluminescent device 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 including a radialene of formula (I), and a first light-emitting unit 140, wherein the first light-emitting unit 140 includes a first hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, a first light-emitting layer (EML1) 143, a first hole blocking layer (HBL1) 144 and a first electron transport layer (ETL1) 145.

[0771] The organic electroluminescent device 100 further includes an n-type charge generation layer 161 and a p-type charge generation layer 162 .

[0772] The organic electroluminescent device 100 further includes a second light-emitting unit 240 disposed on the p-type charge generation layer 162, and the second light-emitting unit 240 includes a second hole transport layer (HTL2) 241, a second electron blocking layer (EBL2) 242, a second light-emitting layer (EML2) 243, a second hole blocking layer (HBL2) 244 and a second electron transport layer (ETL2) 245.

[0773] The organic electroluminescent device 100 further includes an n-type charge generation layer 261 and a p-type charge generation layer 262 .

[0774] The organic electroluminescent device 100 further includes a third light-emitting unit 340 disposed on the p-type charge generation layer 262, and the third light-emitting unit 340 includes a third hole transport layer (HTL3) 341, a third electron blocking layer (EBL3) 342, a third light-emitting layer (EML3) 343, a third hole blocking layer (HBL3) 344 and a third electron transport layer (ETL3) 345.

[0775] The organic electroluminescent device 100 also includes a first intermediate connecting region (ICR1) 150 arranged on the third light-emitting unit 340, the first intermediate connecting region (ICR1) 150 including an n-type first charge generating layer (n-CGL1) 151 of the first intermediate connecting region, a first intermediate layer (IL1) 153 and a first p-type charge generating layer (p-CGL1) 152 of the first intermediate connecting region, wherein the first n-type charge generating layer (n-CGL1) 151 of the first intermediate connecting region includes a host compound and a metal dopant, wherein the first intermediate layer (IL1) 153 includes a hole transport compound, and wherein the first p-type charge generating layer (p-CGL1) 152 of the first intermediate connecting region includes a radialene of formula (I) and a hole transport host compound.

[0776] The organic electroluminescent device 100 further includes a fourth light-emitting unit 440 disposed on the first intermediate connecting region (ICR1) 150, and the fourth light-emitting unit 440 includes a fourth hole transport layer (HTL4) 441, a fourth electron blocking layer (EBL4) 442, a fourth light-emitting layer (EML4) 443, a fourth hole blocking layer (HBL4) 444 and a fourth electron transport layer (ETL4) 445.

[0777] The organic electroluminescent device 100 further includes an electron injection layer (EIL) 180 and a cathode layer (CAT) 190 .

[0778] Fig.12 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0779] refer to Fig.12 The organic electroluminescent device 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 including a radialene of formula (I), and a first light-emitting unit 140, wherein the first light-emitting unit 140 includes a first hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, a first light-emitting layer (EML1) 143, a first hole blocking layer (HBL1) 144 and a first electron transport layer (ETL1) 145.

[0780] The organic electroluminescent device 100 also includes a first intermediate connecting region (ICR1) 150 arranged on the first light-emitting unit 140, the first intermediate connecting region (ICR1) 150 including an n-type first charge generating layer (n-CGL1) 151 of the first intermediate connecting region, a first intermediate layer (IL1) 153 and a first p-type charge generating layer (p-CGL1) 152 of the first intermediate connecting region, wherein the first n-type charge generating layer (n-CGL1) 151 of the first intermediate connecting region includes a host compound and a metal dopant, wherein the first intermediate layer (IL1) 153 includes a hole transport compound, and wherein the first p-type charge generating layer (p-CGL1) 152 of the first intermediate connecting region includes a radialene of formula (I) and a hole transport host compound.

[0781] The organic electroluminescent device 100 further includes a second light-emitting unit 240 disposed on the first intermediate connecting region (ICR1) 150, and the second light-emitting unit 240 includes a second hole transport layer (HTL2) 241, a second electron blocking layer (EBL2) 242, a second light-emitting layer (EML2) 243, a second hole blocking layer (HBL2) 244 and a second electron transport layer (ETL2) 245.

[0782] The organic electroluminescent device 100 further includes an n-type charge generation layer 161 and a p-type charge generation layer 162 .

[0783] The organic electroluminescent device 100 further includes a third light-emitting unit 340 disposed on the p-type charge generation layer 162, and the third light-emitting unit 340 includes a third hole transport layer (HTL3) 341, a third electron blocking layer (EBL3) 342, a third light-emitting layer (EML3) 343, a third hole blocking layer (HBL3) 344 and a third electron transport layer (ETL3) 345.

[0784] The organic electroluminescent device 100 further includes an n-type charge generation layer 261 and a p-type charge generation layer 262 .

[0785] The organic electroluminescent device 100 further includes a fourth light-emitting unit 440 disposed on the p-type charge generation layer 262, and the fourth light-emitting unit 440 includes a fourth hole transport layer (HTL4) 441, a fourth electron blocking layer (EBL4) 442, a fourth light-emitting layer (EML4) 443, a fourth hole blocking layer (HBL4) 444 and a fourth electron transport layer (ETL4) 445.

[0786] The organic electroluminescent device 100 further includes an electron injection layer (EIL) 180 and a cathode layer (CAT) 190 .

[0787] Fig.13 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0788] refer to Fig.13 The organic electroluminescent device 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 including a radialene of formula (I), and a first light-emitting unit 140, wherein the first light-emitting unit 140 includes a first hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, a first light-emitting layer (EML1) 143, a first hole blocking layer (HBL1) 144 and a first electron transport layer (ETL1) 145.

[0789] The organic electroluminescent device 100 further includes an n-type charge generation layer 161 and a p-type charge generation layer 162 .

[0790] The organic electroluminescent device 100 further includes a second light-emitting unit 240 disposed on the p-type charge generation layer 162, and the second light-emitting unit 240 includes a second hole transport layer (HTL2) 241, a second electron blocking layer (EBL2) 242, a second light-emitting layer (EML2) 243, a second hole blocking layer (HBL2) 244 and a second electron transport layer (ETL2) 245.

[0791] The organic electroluminescent device 100 also includes a first intermediate connecting region (ICR1) 150 arranged on the second light-emitting unit 240, the first intermediate connecting region (ICR1) 150 including an n-type first charge generating layer (n-CGL1) 151 of the first intermediate connecting region, a first intermediate layer (IL1) 153 and a first p-type charge generating layer (p-CGL1) 152 of the first intermediate connecting region, wherein the first n-type charge generating layer (n-CGL1) 151 of the first intermediate connecting region includes a host compound and a metal dopant, wherein the first intermediate layer (IL1) 153 includes a hole transport compound, and wherein the first p-type charge generating layer (p-CGL1) 152 of the first intermediate connecting region includes a radialene of formula (I) and a hole transport host compound.

[0792] The organic electroluminescent device 100 further includes a third light-emitting unit 340 disposed on the intermediate connecting region (ICR1) 150, and the third light-emitting unit 340 includes a third hole transport layer (HTL3) 341, a third electron blocking layer (EBL3) 342, a third light-emitting layer (EML3) 343, a third hole blocking layer (HBL3) 344 and a third electron transport layer (ETL3) 345.

[0793] The organic electroluminescent device 100 further includes an n-type charge generation layer 261 and a p-type charge generation layer 262 .

[0794] The organic electroluminescent device 100 further includes a fourth light-emitting unit 440 disposed on the p-type charge generation layer 262, and the fourth light-emitting unit 440 includes a fourth hole transport layer (HTL4) 441, a fourth electron blocking layer (EBL4) 442, a fourth light-emitting layer (EML4) 443, a fourth hole blocking layer (HBL4) 444 and a fourth electron transport layer (ETL4) 445.

[0795] The organic electroluminescent device 100 further includes an electron injection layer (EIL) 180 and a cathode layer (CAT) 190 .

[0796] Fig.141 is a schematic cross-sectional view of an anode layer 120 on a substrate 110 , wherein the anode layer 120 includes a first anode sublayer 121 , a second anode sublayer 122 and a third anode sublayer 123 .

[0797] Hereinafter, one or more exemplary embodiments of the present invention will be described in detail with reference to the following examples. However, these examples are not intended to limit the purpose and scope of one or more exemplary embodiments of the present invention. DETAILED DESCRIPTION

[0798] The invention is further illustrated by the following examples, which are intended to be illustrative only and not limiting.

[0799] Compounds of formula (I) can be prepared as described in EP2180029A1 and WO2016097017A1.

[0800] The compounds of formula (II) can be prepared by methods known in the art.

[0801] Calculate HOMO and LUMO

[0802] HOMO and LUMO were calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). The optimized geometry of the molecular structure and the HOMO and LUMO energy levels were determined by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase. If more than one conformation is feasible, the conformation with the lowest total energy is selected.

[0803] Selected radialenes with corresponding LUMO levels

[0804]

[0805]

[0806]

[0807] The asterisk "*" indicates the binding position.

[0808] The selected compound of formula (II) having the corresponding LUMO energy level

[0809]

[0810]

[0811]

[0812]

[0813]

[0814] General procedure for manufacturing OLED

[0815] For the embodiment, a glass substrate having an anode layer comprising a first anode sublayer of 120 nm Ag, a second anode sublayer of 8 nm ITO, and a third anode sublayer of 10 nm ITO was cut into a size of 50 mm × 50 mm × 0.7 mm, ultrasonically washed with water for 60 minutes, and then ultrasonically washed with isopropanol for 20 minutes. The liquid film was removed in a nitrogen stream, and then plasma treatment was performed to prepare the anode layer. The plasma treatment was performed in a nitrogen atmosphere or in an atmosphere comprising 98% by volume nitrogen and 2% by volume oxygen.

[0816] Then, a hole injection layer (HIL) having a thickness of 10 nm was formed on the anode layer by co-depositing 99 wt % of compound F16 (N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine) and 1 wt % of 4,4',4"-((1E,1'E,1"E)-cyclopropyl-1,2,3-triylidenetris(cyanomethylylidene))tris(2,3,5,6-tetrafluorobenzonitrile).

[0817] Then, a first hole transport layer (HTL1) was formed with a thickness of 29 nm on the HIL by depositing Compound F16 (N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine).

[0818] Then, a first electron blocking layer (EBL1) with a thickness of 5 nm was formed on HTL1 by depositing a compound N,N-di([1,1′-biphenyl]-4-yl)-3′-(9H-carbazole-9-yl)-[1,1′-biphenyl]-4-amine.

[0819] Then, a first light-emitting layer (EML1) with a thickness of 19 nm was formed on EBL1 by co-depositing 99 vol% of 7-(phenyl-2,3,4,5,6-d)-1-[10-(phenyl-2,3,4,5,6-d)-9-anthracenyl]dibenzofuran [2457172-82-4] as an EML host and 1 vol% of 2,7,11-tris(1,1-dimethylethyl)-5,9-bis[4-(1,1-dimethylethyl)phenyl]-5H,9H-[1]benzothieno[2',3':5,6][1,4]azaborolino[2,3,4-kl]benzoazaborolane [2482607-57-6] as a blue dopant.

[0820] Then, a first electron transport layer (ETL1) with a thickness of 20 nm was formed on the first light emitting layer by co-depositing a compound of 2,2′-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and LiQ in a ratio of 50:50 wt %.

[0821] Then, an n-CGL with a thickness of 15 nm was formed on the ETL by co-depositing 90 wt % of a compound of 2,2′-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 10 wt % of Yb.

[0822] In the inventive example, as a next step, an intermediate layer having a thickness as described in the description of the corresponding embodiment is formed on the n-CGL by depositing a compound as described below.

[0823] Then, in the inventive example, a p-CGL with a thickness of 10 nm is formed on the intermediate layer by co-depositing the matrix compound and the radialene of formula (I). The composition of the p-CGL can be found in the description of the corresponding embodiment.

[0824] Then, a second hole transport layer (HTL2) was formed on the p-CGL with a thickness of 43 nm by depositing the same compound as the host compound of the p-CGL.

[0825] Then, a second electron blocking layer (EBL2) with a thickness of 5 nm was formed on the HTL2 by depositing a compound N,N-di([1,1′-biphenyl]-4-yl)-3′-(9H-carbazole-9-yl)-[1,1′-biphenyl]-4-amine.

[0826] Then, a second light-emitting layer (EML2) with a thickness of 19 nm was formed on EBL2 by co-depositing 99 vol% of 7-(phenyl-2,3,4,5,6-d)-1-[10-(phenyl-2,3,4,5,6-d)-9-anthryl]dibenzofuran[2457172-82-4] as the EML host and 1 vol% of 2,7,11-tris(1,1-dimethylethyl)-5,9-bis[4-(1,1-dimethylethyl)phenyl]-5H,9H-[1]benzothieno[2',3':5,6][1,4]azaborolidine[2,3,4-kl]benzoazaborolane as a blue dopant.

[0827] Then, a first hole blocking layer (HBL1) with a thickness of 5 nm was formed on the EML2 by depositing a compound 4-([1,1′-biphenyl]-4-yl)-6-(3′-(9,9-dimethyl-9H-fluoren-4-yl)-[1,1′-biphenyl]-4-yl)-2-phenylpyrimidine.

[0828] Then, a second electron transport layer (ETL2) with a thickness of 31 nm was formed on the HBL by co-depositing a compound of 6,6′-(naphthalene-1,2-diylbis(4,1-phenylene))bis(2,4-diphenyl-1,3,5-triazine) and LiQ in a ratio of 50:50 wt %.

[0829] Then, an electron injection layer (EIL) was formed on the ETL2 with a thickness of 2 nm by depositing Yb.

[0830] Then, by -7 mbar to Ag:Mg (90:10 vol %) was co-deposited at a rate of 1.1 % to form a cathode layer with a thickness of 13 nm on the EIL.

[0831] Then, a capping layer having a thickness of 75 nm was formed on the cathode layer by depositing Compound F16 (N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine).

[0832] The OLED stack is protected from environmental conditions by encapsulating the device with a glass slide. Thus, a cavity is formed, which includes getter material for further protection.

[0833] In order to evaluate the performance of the inventive examples compared to the prior art, the current efficiency was measured at 20°C. The current-voltage characteristic line was determined by providing a voltage (in V) and measuring the current (in mA) flowing through the device under test using a Keithley 2635 source measurement unit. The voltage applied to the device varied in steps of 0.1 V in the range between 0 V and 10 V. Similarly, the luminous density (in cd / m2) at each voltage value was measured using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)). 2 The luminous density-voltage characteristic line and CIE coordinates are determined by interpolating the luminous density-voltage and current-voltage characteristic lines respectively. 2 cd / A efficiency under .

[0834] In bottom-emitting devices, the emission is primarily Lambertian and is quantified as the external quantum efficiency (EQE) percentage. To determine the efficiency EQE (in %), a calibrated photodiode was used at 15 mA / cm 2 The light output of the device was measured.

[0835] In a top-emitting device, the emission is forward, non-Lambertian, and also highly dependent on the microcavity. Therefore, the efficiency EQE will be higher compared to a bottom-emitting device. To determine the efficiency EQE (in %), a calibrated photodiode was used at 15 mA / cm 2 The light output of the device was measured.

[0836] At ambient conditions (20°C) or 85°C and 30mA / cm 2 The device lifetime LT was measured using a Keithley 2400 source meter and recorded in hours.

[0837] The brightness of the device is measured using a calibrated photodiode. The lifetime LT is defined as the time until the brightness of the device drops to 97% of its initial value.

[0838] The operating voltage increase ΔU is used as a measure of the operating voltage stability of the device.

[0839] This increment is also determined during the LT measurement by subtracting the operating voltage after 1 hour from the operating voltage after 100 hours from the start of device operation.

[0840] ΔU=[U(100h)-U(1h)]

[0841] The smaller the ΔU value is, the better the operating voltage stability is.

[0842] Technical Effects of the Invention

[0843] Table 1: Performance and lifetime data of comparative OLED devices and inventive OLED devices

[0844]

[0845] (C refers to comparative example, I refers to inventive example)

[0846] If an intermediate layer is present, the thickness of the intermediate layer is always 1 nm. In the case of Example C-1b, the thickness of the intermediate layer and the p-type charge generation layer is a total of 10 nm. All Examples use Compound N-1 as n-CGL host material and Yb as n-CGL metal dopant. All Examples except C-1b (without p-CGL dopant) use a mixture of 91 wt. % of the corresponding p-CGL host material (as shown in the table) and 9 wt. % of Compound A2 as p-CGL dopant.

[0847] Compound N-1 has the following structure:

[0848]

[0849] CNHAT has the following structure:

[0850]

[0851] CuPC has the following structure:

[0852]

[0853] In the arrangement according to Table 1, a variety of different compounds were used for the intermediate layer, and in addition, some comparative examples had no intermediate layer or p-CGL doping layer.

[0854] The use of CNHAT as a p-type charge generation layer and CNHAT as an intermediate layer (Comparative Example 1b), instead of using Compound F18 as a hole transport host compound and using Compound A2 as a p-type charge generation layer without an intermediate layer (Comparative Example 1a), resulted in an increase in voltage rise over time and reduced the life of the organic electroluminescent device.

[0855] Using F18 as a hole transport host compound and using compound A2 as a p-type charge generating layer and using compound CuPc as an intermediate layer (Comparative Example 1c), rather than using compound F18 as a hole transport host compound and using compound A2 as a p-type charge generating layer and no intermediate layer (Comparative Example 1a), results in an increase in voltage rise over time and a decrease in the life of the organic electroluminescent device.

[0856] Using F18 as an intermediate layer and using compound A2 as a p-type charge generation layer and using CNHAT as an intermediate layer (Comparative Example 1d), instead of using compound F18 as a hole transport host compound and using compound A2 as a p-type charge generation layer without the presence of an intermediate layer (Comparative Example 1a), results in an increase in voltage rise over time and a decrease in the life of the organic electroluminescent device.

[0857] Compared with Comparative Example 1, in Inventive Example 1a, Compound F18 as a hole transport host compound and Compound A2 as an organic p-type dopant in a p-type charge generating layer and a hole transport compound F18 as an intermediate layer exhibited significantly reduced voltage increase over time and increased lifetime, while the current efficiency of the organic electroluminescent device increased or remained unchanged.

[0858] Compared with Comparative Example 1, in Inventive Example 1b, Compound F18 as a hole transport host compound, Compound A2 as an organic p-type dopant in a p-type charge generating layer, and a hole transport compound F3 as an intermediate layer exhibited significantly reduced voltage increase over time and increased lifetime, while the current efficiency of the organic electroluminescent device increased or remained unchanged.

[0859] Compared with Comparative Example 1, in Inventive Example 1c, Compound F18 as a hole transport host compound, Compound A2 as an organic p-type dopant in the p-type charge generation layer, and Hole Transport Compound F4 as an intermediate layer exhibited significantly reduced voltage increase over time and increased lifetime, while the current efficiency of the organic electroluminescent device increased or remained unchanged.

[0860] In Comparative Example 1b and Comparative Example 1c, Compound F18 is used as a hole transport host compound, Compound A2 is used as an organic p-type dopant in a p-type charge generation layer, and CuPc or CNHAT is used as an intermediate layer, respectively. Compared with Comparative Example 1, Comparative Example 1b and Comparative Example 1c show a higher voltage increase over time and a lower lifespan of the organic electroluminescent device.

[0861] Other properties of the comparative OLED device and the inventive OLED device are shown in Table 4:

[0862] Table 2: Performance and lifetime data of comparative OLED devices and inventive OLED devices

[0863]

[0864] (C refers to comparative example, I refers to inventive example)

[0865] Table 2 shows the performance of the comparative examples and the inventive examples. The inventive examples differ from each of the comparative examples in that an intermediate layer consisting of a 1 nm layer of the F18 compound is used each time. In addition, all examples use the compound N-1 as the n-CGL host compound and Yb as the n-CGL metal dopant, and in addition all examples use the compound F18 as the p-CGL host material.

[0866] It can be seen that, compared with the respective comparative examples, in all devices according to Inventive Examples 2 to 7, when an intermediate layer containing amine as a hole transport compound is used, a reduced voltage increase over time and an increased lifespan can be seen, while the current efficiency increases or remains unchanged.

[0867] Therefore, by adding an interlayer containing an amine as a hole transport compound, the voltage rise can be reduced.

[0868] By adding an interlayer containing an amine as a hole transport compound, the current efficiency can be increased.

[0869] The voltage rise can be reduced and the current efficiency can be increased at the same time.

[0870] High or good current efficiency can be beneficial in reducing power consumption and improving battery life, especially in mobile devices.

[0871] Long lifetime can improve the long-term stability of electronic devices.

[0872] The low voltage increase over time can improve the long-term stability of electronic devices.

[0873] Table 3: Performance and lifetime data of comparative OLED devices and inventive OLED devices as a function of the thickness of the intermediate layer

[0874]

[0875] (C refers to comparative example, I refers to inventive example)

[0876] In Table 3, for all inventive examples, compound F-18 was used as the interlayer. In addition, compound N-1 was used as the n-CGL host compound and Yb was used as the n-CGL metal dopant in all examples. The thickness of the interlayer varied. All examples in Table 3 used a mixture of 86 wt % of the corresponding p-CGL host material (as shown in the table) and 14 wt % of compound A3 as the p-CGL dopant.

[0877] Obviously, the addition of an interlayer containing an amine as a hole transport compound reduces the voltage rise of the organic electroluminescent device over time, which is independent of the thickness of the organic electroluminescent device.

[0878] However, if the thickness of the intermediate layer is equal to or lower than 1 nm, it is even possible to reduce the operating voltage or keep it stable, and also improve other performance data and lifetime.

[0879] Low or relatively low operating voltage can be important for battery life of organic electroluminescent devices, especially mobile devices.

[0880] The low voltage increase over time can improve the long-term stability of electronic devices.

[0881] The specific combination of elements and features in the embodiments described in detail above is merely exemplary; it is also explicitly contemplated to interchange and replace these teachings with other teachings in the present application and the patents / applications incorporated by reference. As will be appreciated by those skilled in the art, those of ordinary skill in the art can think of changes, modifications and other implementations of the contents described herein without departing from the spirit and scope of the claimed invention. Therefore, the above description is only intended to be restrictive as an example. In the claims, the word "comprising" does not exclude other elements or steps, and the indefinite article "one" or "an" does not exclude pluralities. The fact that certain measures are described in mutually different dependent claims does not mean that a combination of these measures cannot be used to advantage. The scope of the present invention is defined in the claims and their equivalents. In addition, the figure marks used in the specification and claims do not limit the scope of the claimed invention.

Claims

1. An organic electroluminescent device, comprising an anode layer, a cathode layer, a first light-emitting unit, a second light-emitting unit and at least one intermediate connection region, wherein the at least one intermediate connection region is arranged between the first light-emitting unit and the second light-emitting unit, The first light-emitting unit comprises a first light-emitting layer, wherein the second light-emitting unit comprises a second light-emitting layer, wherein the at least one intermediate connection region comprises an n-type charge generation layer, an intermediate layer and a p-type charge generation layer, wherein the n-type charge generation layer is arranged closer to the anode layer than the p-type charge generation layer; wherein the p-type charge generation layer is arranged closer to the cathode layer than the n-type charge generation layer; and wherein the intermediate layer is arranged between the n-type charge generation layer and the p-type charge generation layer, in wherein the n-type charge generation layer comprises a host compound and a metal dopant, wherein the p-type charge generating layer comprises a hole transporting host compound and a radialene of formula (I), Wherein in formula (I), -A 1 Independently selected from groups of formula (Ia): Among them, Ar 1 are independently selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl; For Ar 1 In the case of being substituted, one or more substituents are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl; and Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, C1 to C8 alkoxy are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy; -A 2 Independently selected from groups of formula (Ib): Among them, Ar 2 are independently selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl; For Ar 2 In the case of being substituted, one or more substituents are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl; and Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, C1 to C8 alkoxy are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy; -A 3 Independently selected from groups of formula (Ic): Among them, Ar 3 are independently selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl; For Ar 3 In the case of being substituted, one or more substituents are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl; and Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, C1 to C8 alkoxy are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy; And in A 1 , A 2 and A 3 In which each R' is independently selected from substituted or unsubstituted C6 to C 18 Aryl, C3 to C 18 heteroaryl, electron withdrawing group, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, halogen, F and CN; The intermediate layer comprises at least one hole transport compound selected from arylamine compounds, diarylamine compounds, triarylamine compounds, compounds of formula (IIa) or compounds of formula (IIb): in: T 1 , T 2 , T 3 , T 4 and T 5 independently selected from a single bond, a phenylene group, a biphenylene group, a terphenylene group or a naphthalene group, preferably a single bond or a phenylene group; T 6 is a phenyl subunit, a biphenyl subunit, a terphenyl subunit or a naphthalene subunit; Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar' 4 and Ar' 5 independently selected from substituted or unsubstituted C6 to C 20 Aryl or substituted or unsubstituted C3 to C 20 heteroarylidene, substituted or unsubstituted biphenylidene, substituted or unsubstituted fluorene, substituted 9-fluorene, substituted 9,9-fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted terphenylidene, substituted or unsubstituted tetracene, substituted or unsubstituted benzanthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthene, substituted or unsubstituted carbazole, substituted 9-phenylcarbazole, substituted or unsubstituted azepane, substituted or unsubstituted dibenzo[b,f]azepane, substituted or unsubstituted 9,9'- Spirobi[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanthene]; or a substituted or unsubstituted aromatic fused ring system comprising at least three substituted or unsubstituted aromatic rings selected from: substituted or unsubstituted non-heterocyclic, substituted or unsubstituted hetero 5-membered ring, substituted or unsubstituted 6-membered ring and / or substituted or unsubstituted 7-membered ring, substituted or unsubstituted fluorene; or a fused ring system comprising 2 to 6 substituted or unsubstituted 5 to 7-membered rings, and the rings are selected from: (i) heterocyclic unsaturated 5 to 7-membered rings, (ii) aromatic heterocyclic 5 to 6-membered rings, (iii) non-heterocyclic unsaturated 5 to 7-membered rings, (iv) aromatic non-heterocyclic 6-membered rings; in Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar' 4 and Ar' 5 The substituents are selected from the group consisting of H, D, F, C(=O)R' 2 、CN、Si(R' 2 )3. P(=O)(R' 2 )2. OR' 2 、S(=O)R' 2 、S(=O)2R' 2 , substituted or unsubstituted straight-chain alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted branched-chain alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl or alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aromatic ring systems having 6 to 40 aromatic ring atoms and substituted or unsubstituted heteroaromatic ring systems having 5 to 40 aromatic ring atoms, unsubstituted C6 to C 18 Aryl, unsubstituted C3 to C 18 heteroaryl, a fused ring system comprising 2 to 6 unsubstituted 5 to 7 membered rings, and the rings are selected from: heterocyclic unsaturated 5 to 7 membered rings, aromatic heterocyclic 5 to 6 membered rings, non-heterocyclic unsaturated 5 to 7 membered rings and aromatic non-heterocyclic 6 membered rings, Where R' 2 The alkyl radical may be selected from H, D, a linear alkyl radical having 1 to 6 carbon atoms, a branched alkyl radical having 1 to 6 carbon atoms, a cyclic alkyl radical having 3 to 6 carbon atoms, an alkenyl or alkynyl radical having 2 to 6 carbon atoms, a C6 to C 18 Aryl or C3 to C 18 Heteroaryl. 2 . The organic electroluminescent device according to claim 1 , wherein the intermediate layer consists essentially of one or more of the hole transport compounds. 3 . The organic electroluminescent device according to claim 1 , wherein the intermediate layer has a layer thickness of ≤20 nm. 4 . The organic electroluminescent device according to claim 1 , wherein the p-type charge generation layer is in direct contact with the intermediate layer. 5 . The organic electroluminescent device according to claim 1 , wherein the n-type charge generation layer is in direct contact with the intermediate layer.

6. The organic electroluminescent device according to any one of claims 1 to 5, wherein the hole transport compound of the intermediate layer has a HOMO level calculated by using TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, and the hole transport host compound of the p-type charge generation layer has a HOMO level calculated by using TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase. 19, 76135 Karlsruhe, Germany), the HOMO energy level calculated by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, and wherein the absolute value of the difference between the HOMO energy level of the hole transport compound of the intermediate layer and the HOMO energy level of the hole transport matrix compound of the p-type charge generating layer is ≤0.5 eV, preferably ≤0.4 eV, more preferably ≤0.3 eV, even more preferably ≤0.2 eV, even more preferably ≤0.1 eV, and most preferably 0 eV. 7 . The organic electroluminescent device according to claim 1 , wherein the at least one hole transport compound of the intermediate layer and the at least one hole transport host compound of the p-type charge generating layer are selected to be identical. 8 . The organic electroluminescent device according to claim 1 , wherein a ratio of the layer thickness of the intermediate layer to the p-type charge generation layer is in the range of ≧0.01 to ≦10.

0. 9 . The organic electroluminescent device according to claim 1 , wherein a ratio of the layer thickness of the intermediate layer to the n-type charge generation layer is in the range of ≧0.01 to ≦10.

0.

10. The organic electroluminescent device according to any one of claims 1 to 9, wherein in formula (I), Ar 1 ,Ar 2 and / or Ar 3 Independently selected from one of the following groups, and preferably each R' is selected from CN: The asterisk "*" indicates the binding position.

11. An organic electroluminescent device according to any one of claims 1 to 10, wherein the at least one hole transport compound consists essentially of at least one compound selected from formula (IIa) and formula (IIb), preferably the at least one hole transport compound consists essentially of at least one compound selected from formula (IIa).

12. The organic electroluminescent device according to any one of claims 1 to 11, wherein in formula (IIa) and / or formula (IIb), where applicable, Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar' 4 and / or Ar' 5 Independently selected from D1 to D16: The asterisk "*" indicates the binding position.

13. The organic electroluminescent device according to any one of claims 1 to 12, wherein the at least one hole transport compound and / or formula (IIa) and / or (IIb), where applicable, is selected from F1 to F18: 14 . A display device comprising the organic electroluminescent device according to claim 1 .

15. A method for preparing an organic electroluminescent device, preferably an organic electroluminescent device according to any one of claims 1 to 13, the method comprising the following steps: - forming an n-type charge generation layer by depositing a host compound and depositing a metal dopant; - forming an intermediate layer by depositing a hole transport compound consisting essentially of at least one compound selected from the group consisting of arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb); - forming a p-type charge generation layer by depositing a hole transport host compound consisting essentially of at least one compound selected from arylamines, diarylamines, triarylamines, compounds of formula (IIa) and formula (IIb), and depositing a radialene of formula (I).

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