ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING COMPOUNDS OF Formula (I) AND COMPOUNDS OF Formula (II), AND DISPLAY DEVICE COMPRISING THE ORGANIC ELECTROLUMINESCENT DEVICE

Abstract

The present invention relates to an electroluminescent device comprising a compound of formula (I) and a compound of formula (II), and a display device comprising the organic electroluminescent device. # imgabs0 #

Description

Technical Field

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

[0002] Organic electronic devices, such as organic light-emitting diodes (OLEDs), which are self-luminous devices, have wide viewing angles, excellent contrast, rapid response, high brightness, excellent operating voltage characteristics, and color reproduction. A typical OLED comprises an anode, a hole transport layer HTL, an emission layer EML, an electron transport layer ETL, and a cathode, which are sequentially stacked 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 to the EML via the HTL, and electrons injected from the cathode move to the EML via the ETL. Holes and electrons recombine in the EML to generate excitons. When the excitons drop from the excited state to the 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 the organic light emitting diode may be affected by the characteristics of the semiconductor layer, and more particularly, by the characteristics 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, the organic electroluminescent device comprising an anode layer, a cathode layer, a hole injection layer, at least two light-emitting units and at least one charge generation layer, wherein the at least one charge generation layer comprises a p-type charge generation layer;

[0007] Each light-emitting unit comprises at least one light-emitting layer.

[0008] wherein each of the at least one charge generation layer is independently disposed between two adjacent light emitting units of a group of at least two light emitting units;

[0009] wherein the hole injection layer is arranged closer to the anode layer than the p-type charge generation layer;

[0010] The hole injection layer comprises a first radialene compound of formula (I) and a first hole transport host compound, wherein the first radialene compound of formula (I) is represented by the following formula:

[0011] , wherein in formula (I):

[0012] A 1 Independently selected from groups of formula (Ia):

[0013] ,in

[0014] Ar 1 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein

[0015] Ar 1 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 Heteroaryl; wherein

[0016] C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl and 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;

[0017] A 2 Independently selected from groups of formula (Ib):

[0018] ,in

[0019] Ar 2 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein

[0020] Ar 2 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30Aryl and substituted or unsubstituted C6 to C 30 Heteroaryl; wherein

[0021] 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;

[0022] A 3 Independently selected from groups of formula (Ic):

[0023] ,in

[0024] Ar 3 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein

[0025] Ar 3 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 Heteroaryl, wherein

[0026] 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;

[0027] in

[0028] In A 1 , A 2 and A 3 wherein each R' is independently selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 18heteroaryl, 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; wherein

[0029] C6 to C 18 Aryl, C6 to C 18 One or more substituents of heteroaryl and C1 to C8 alkyl are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, partially fluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy;

[0030] in

[0031] The LUMO energy level of the first olefin compound of formula (I) is ≤ -5.20 eV;

[0032] in

[0033] The p-type charge generation layer comprises a second radialene compound of formula (II) and a second hole transport host compound; and

[0034] The second olefin compound of formula (II) is represented by the following formula:

[0035] , wherein in formula (II):

[0036] B 1 Independently selected from groups of formula (IIa):

[0037] ,in

[0038] Er 1 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein

[0039] Er 1 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl, and

[0040] 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;

[0041] B 2 Independently selected from groups of formula (IIb):

[0042] ,in

[0043] Er 2 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein

[0044] Er 2 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl, and wherein

[0045] 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;

[0046] B 3 Independently selected from groups of formula (Ic):

[0047] ,in

[0048] Er 3 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein

[0049] Er 3The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl, and

[0050] 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;

[0051] in

[0052] In B 1 , B 2 and B 3 In the above formula, each R" is independently selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted 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;

[0053] Among them, C6 to C 18 Aryl, C6 to C 18 One or more substituents of heteroaryl and C1 to C8 alkyl are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, partially fluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy;

[0054] in

[0055] The first olefin compound of formula (I) and the second olefin compound of formula (II) are selected to be different from each other; and wherein the asterisk " ” indicates the binding position.

[0056] According to a preferred embodiment, the LUMO energy level can be calculated by applying the hybrid functional B3LYP and 6-31G in the gas phase. The basis sets were calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany).

[0057] According to a preferred embodiment, the organic electroluminescent device comprises an anode layer, a cathode layer, a hole injection layer, at least two light-emitting units and at least one charge generation layer, wherein the at least one charge generation layer comprises a p-type charge generation layer;

[0058] Each light-emitting unit comprises at least one light-emitting layer.

[0059] wherein each of the at least one charge generation layer is independently disposed between two adjacent light emitting units of a group of at least two light emitting units;

[0060] wherein the hole injection layer is arranged closer to the anode layer than the p-type charge generation layer;

[0061] The hole injection layer comprises a first radialene compound of formula (I) and a first hole transport host compound, wherein the first radialene compound of formula (I) is represented by the following formula:

[0062] , wherein in formula (I):

[0063] A 1 Independently selected from groups of formula (Ia):

[0064] ,in

[0065] Ar 1 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein

[0066] Ar 1 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 Heteroaryl; wherein

[0067] C6 to C 30 Aryl, C6 to C 30One or more substituents of heteroaryl, C1 to C8 alkyl and 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;

[0068] A 2 Independently selected from groups of formula (Ib):

[0069] ,in

[0070] Ar 2 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein

[0071] Ar 2 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 Heteroaryl; wherein

[0072] 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;

[0073] A 3 Independently selected from groups of formula (Ic):

[0074] ,in

[0075] Ar 3 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein

[0076] Ar 3The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 Heteroaryl, wherein

[0077] 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;

[0078] in

[0079] In A 1 , A 2 and A 3 wherein each R' is independently selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted 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; wherein

[0080] C6 to C 18 Aryl, C6 to C 18 One or more substituents of heteroaryl and C1 to C8 alkyl are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, partially fluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy;

[0081] in

[0082] When hybrid functionals B3LYP and 6-31G are applied in the gas phase When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the LUMO energy level of the first radialene compound of the formula (I) is ≤ -5.20 eV;

[0083] in

[0084] The p-type charge generation layer comprises a second radialene compound of formula (II) and a second hole transport host compound; and

[0085] The second olefin compound of formula (II) is represented by the following formula:

[0086] , wherein in formula (II):

[0087] B 1 Independently selected from groups of formula (IIa):

[0088] ,in

[0089] Er 1 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein

[0090] Er 1 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl, and

[0091] 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;

[0092] B 2 Independently selected from groups of formula (IIb):

[0093] ,in

[0094] Er 2 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein

[0095] Er 2The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl, and wherein

[0096] 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;

[0097] B 3 Independently selected from groups of formula (Ic):

[0098] ,in

[0099] Er 3 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein

[0100] Er 3 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl, and

[0101] 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;

[0102] in

[0103] In B 1 , B 2 and B 3 In the above formula, each R" is independently selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted 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;

[0104] Among them, C6 to C 18 Aryl, C6 to C 18 One or more substituents of heteroaryl and C1 to C8 alkyl are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, partially fluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy;

[0105] in

[0106] The first olefin compound of formula (I) and the second olefin compound of formula (II) are selected to be different from each other; and wherein the asterisk " ” indicates the binding position.

[0107] It should be noted that throughout this application and the claims, unless otherwise stated, any A 1 , A 2 and A 3 ,Ar 1 ,Ar 2 and Ar 3 , B 1 , B 2 and B 3 , Er 1 , Er 2 and Er 3 , R'; R", etc. always refer to the same part.

[0108] In the present specification, when no definition is provided otherwise, "substituted" means substituted by the following groups: 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 C8 30 Aryl and substituted or unsubstituted C6 to C 30 Heteroaryl; wherein C6 to C 30 Aryl, C6 to C 30One or more substituents of heteroaryl, C1 to C8 alkyl and 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.

[0109] 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.

[0110] 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.

[0111] In the present specification, when no definition is otherwise provided, an "alkyl group" refers to a saturated aliphatic hydrocarbon group.

[0112] The alkyl group may be a C1 to C8 alkyl group. More specifically, the alkyl group may be a C1 to C6 alkyl group or a C1 to C4 alkyl group. For example, the C1 to C4 alkyl group contains 1 to 4 carbons in the alkyl chain and may be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.

[0113] 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.

[0114] The term "cycloalkyl" refers to a saturated hydrocarbon group derived from a cycloalkane by formally separating 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, etc.

[0115] The term "hetero" is understood to mean that in a structure that can be formed by covalently bonded carbon atoms, at least one carbon atom is replaced by another polyvalent atom. Preferably, the heteroatom is selected from B, Si, N, P, O, S; more preferably, from N, P, O, S, and most preferably N.

[0116] In this specification, "aryl group" refers to a hydrocarbon group that can be produced by formally separating a hydrogen atom from the aromatic ring of the 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 the Hückel rule. Examples of aryl groups include: monocyclic groups such as phenyl or tolyl, polycyclic groups such as biphenyl containing multiple more aromatic rings connected by single bonds, and polycyclic groups such as naphthyl or fluorene-2-yl containing condensed rings.

[0117] In the present specification, the "aryl group" refers to a hydrocarbon group which may include a "fused aryl ring" or a "condensed aryl ring".

[0118] Similarly, heteroaryl is understood in particular to mean a radical which is derived by formal separation of a ring hydrogen from a heteroaromatic ring in compounds which contain at least one heteroaromatic ring.

[0119] In the present specification, the "heteroaryl group" may contain a "fused aromatic ring" or "fused aromatic ring" and / or a "fused heteroaromatic ring" or "fused heteroaromatic ring".

[0120] Heterocycloalkyl is understood in particular to be a radical which is derived by formal separation of a ring hydrogen from a saturated cycloalkyl ring in compounds which contain at least one saturated cycloalkyl ring.

[0121] The term "fused aromatic ring" or "fused aromatic ring" is understood to mean when two aromatic rings share at least two common sp 2 When carbon atoms are hybridized, they are said to be fused or fused.

[0122] The term "cyano moiety" refers to a CN substituent.

[0123] The term "electron withdrawing group" refers to a chemical group in a molecule that can withdraw electrons 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 expanded 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.

[0124] In this specification, a single bond means a direct bond.

[0125] The term "n-type charge generation layer" is also sometimes referred to in the art as n-CGL or electron generation layer, and is intended to include both.

[0126] The term "p-type charge generation layer" is also sometimes referred to in the art as p-CGL or hole generation layer, and is intended to include both.

[0127] The terms "without", "not containing", "not including" do not exclude impurities that may be present in the compound before deposition. Impurities have no technical effect on the purpose to be achieved by the present invention.

[0128] The term "sandwiched in contact" refers to a three-layer arrangement in which the middle layer is in direct contact with two adjacent layers.

[0129] The terms "light absorbing layer" and "light absorbing layer" are used synonymously.

[0130] The terms "light emitting layer", "light emitting layer" and "emissive layer" are used synonymously.

[0131] The terms "OLED," "organic light emitting diode," and "organic light emitting device" are used synonymously.

[0132] The terms "anode", "anode layer" and "anode electrode" are used synonymously.

[0133] The terms "cathode", "cathode layer" and "cathode electrode" are used synonymously.

[0134] The term "top emitting device" is to be understood as an organic electronic device wherein light is emitted through the cathode layer.

[0135] The term "bottom-emitting device" is to be understood as an organic electronic device in which light is emitted through the substrate.

[0136] In this specification, hole characteristics refer to the ability to supply electrons to form holes when an electric field is applied and the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) energy level.

[0137] In addition, the electronic property refers to the ability to accept electrons when an electric field is applied and the electrons formed in the cathode can be easily injected into the light emitting layer and transported in the light emitting layer due to the conductive property according to the lowest unoccupied molecular orbital (LUMO) energy level.

[0138] Beneficial Effects

[0139] 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 aspects, in particular in terms of improved operating voltage, improved stability of the operating voltage over time and improved current efficiency.

[0140] Furthermore, it was surprisingly found that radialene with a lower LUMO as a p-type dopant in the hole injection layer can significantly improve the voltage rise.

[0141] Furthermore, it was surprisingly found that an OLED comprising a hole injection layer and a p-type charge generation layer, wherein the radialene dopants in the hole injection layer (HIL) and the p-type charge generation layer (p-CGL) are different and the LUMO level of the radialene in the HIL is ≤-5.20 eV, results in a significantly reduced voltage rise over time.

[0142] According to one embodiment, each of the at least one charge generation layer includes a p-type charge generation layer.

[0143] Organic electroluminescent devices

[0144] According to one embodiment, the organic electroluminescent device comprises at least three light emitting units and at least one charge generating layer, wherein each of the at least one charge generating layer is independently disposed between two adjacent light emitting units of a group of at least three light emitting units.

[0145] According to one embodiment, between a group of two adjacent light emitting units, no more than one charge generation layer is arranged, in particular, no more than one charge generation layer including a p-type charge generation layer and an n-type charge generation layer.

[0146] According to one embodiment, between each group of two adjacent light emitting units, no more than one charge generation layer is arranged, in particular, no more than one charge generation layer including a p-type charge generation layer and an n-type charge generation layer.

[0147] According to one embodiment, the organic electroluminescent device comprises at least three light-emitting units, and at least one or two charge generation layers, wherein each of the at least one charge generation layer is independently arranged between two adjacent light-emitting units of a group of at least three light-emitting units, wherein at least one or two charge generation layers comprise a p-type charge generation layer, wherein the p-type charge generation layer comprises a second olefin compound of formula (II) and a second hole transport matrix compound.

[0148] According to one embodiment, the organic electroluminescent device comprises at least three light-emitting units and at least two charge generation layers, wherein each of the at least two charge generation layers is independently arranged between two adjacent light-emitting units of a group of at least three light-emitting units; or the organic electroluminescent device comprises at least four light-emitting units and at least three charge generation layers, wherein each of the at least three charge generation layers is independently arranged between two adjacent light-emitting units of a group of at least four light-emitting units.

[0149] According to one embodiment, the organic electroluminescent device comprises at least four light-emitting units, and at least one, two or three charge generation layers, wherein each of the at least one, two or three charge generation layers is independently arranged between two adjacent light-emitting units of a group of at least four light-emitting units.

[0150] According to one embodiment, the organic electroluminescent device comprises at least four light-emitting units, and at least one, two or three charge generation layers, wherein each of the at least one, two or three charge generation layers is independently arranged between two adjacent light-emitting units of a group of at least four light-emitting units, wherein at least one charge generation layer comprises a p-type charge generation layer, wherein the p-type charge generation layer comprises a second olefin compound of formula (II) and a second hole transport matrix compound.

[0151] According to one embodiment, the organic electroluminescent device comprises at least three light-emitting units and at least two charge generation layers, wherein each of the at least two charge generation layers is independently arranged between two adjacent light-emitting units of a group of at least three light-emitting units, preferably between two adjacent light-emitting units of different groups.

[0152] According to one embodiment, the organic electroluminescent device comprises at least three light-emitting units and at least two charge generation layers, wherein each of the at least two charge generation layers is independently arranged between two adjacent light-emitting units of a group of at least three light-emitting units, preferably between two adjacent light-emitting units of different groups, wherein at least one, preferably at least two, charge generation layers comprise a p-type charge generation layer.

[0153] According to one embodiment, the organic electroluminescent device comprises at least three light-emitting units and at least two charge generation layers, wherein each of the at least two charge generation layers is independently arranged between two adjacent light-emitting units of a group of at least three light-emitting units, preferably between two adjacent light-emitting units of different groups, wherein each of the at least two charge generation layers comprises a p-type charge generation layer, wherein the p-type charge generation layer comprises a second olefin compound of formula (II) and a second hole transport matrix compound.

[0154] According to one embodiment, the organic electroluminescent device comprises at least four light-emitting units and at least three charge generation layers, wherein each of the at least three charge generation layers is independently arranged between two adjacent light-emitting units of a group of at least four light-emitting units, preferably between two adjacent light-emitting units of different groups.

[0155] According to one embodiment, the organic electroluminescent device comprises at least four light-emitting units and at least three charge generation layers, wherein each of the at least three charge generation layers is independently arranged between two adjacent light-emitting units of a group of at least four light-emitting units, preferably between two adjacent light-emitting units of different groups, wherein at least one, preferably at least two, and more preferably at least three charge generation layers comprise a p-type charge generation layer.

[0156] According to one embodiment, the organic electroluminescent device comprises at least four light-emitting units and at least three charge generation layers, wherein each of the at least three charge generation layers is independently arranged between two adjacent light-emitting units of a group of at least four light-emitting units, preferably between two adjacent light-emitting units of different groups, wherein each of the at least three charge generation layers comprises a p-type charge generation layer, wherein the p-type charge generation layer comprises a second olefin compound of formula (II) and a second hole transport matrix compound.

[0157] According to one embodiment, the organic electroluminescent device comprises at least four light-emitting units and at least three charge generation layers, wherein each of the at least three charge generation layers is independently arranged between two adjacent light-emitting units of a group of at least four light-emitting units, preferably between two adjacent light-emitting units of different groups, wherein at least one, preferably at least two, more preferably at least three charge generation layers comprise a p-type charge generation layer, wherein each of the at least three charge generation layers comprises a p-type charge generation layer, wherein the p-type charge generation layer comprises a second olefin compound of formula (II) and a second hole transport matrix compound.

[0158] According to one embodiment, the hole transport layer is arranged adjacent to the hole injection layer, preferably the hole transport layer is arranged between the light emitting unit and the hole injection layer.

[0159] According to one embodiment, the at least one charge generation layer further comprises an n-type charge generation layer.

[0160] According to one embodiment, the p-type charge generation layer of the at least one charge generation layer is arranged in direct contact with the n-type charge generation layer of the at least one charge generation layer.

[0161] According to one embodiment, at least one, at least two, at least three, or all of the light-emitting units further comprise a hole transport layer and an electron transport layer in addition to the light-emitting layer.

[0162] According to one embodiment, at least one, at least two, at least three or all of the light-emitting units further comprise a hole transport layer, an electron blocking layer, a hole blocking layer and an electron transport layer in addition to the light-emitting layer.

[0163] The first olefin compound of formula (I)

[0164] According to one embodiment, the first radialene compound of formula (I) comprises less than nine cyano moieties.

[0165] According to one embodiment, the first radialene compound of formula (I) comprises less than eight cyano moieties.

[0166] According to one embodiment, the first radialene compound of formula (I) comprises at least one cyano moiety.

[0167] According to one embodiment, the first radialene compound of formula (I) comprises at least two cyano moieties.

[0168] According to one embodiment, the first radialene compound of formula (I) comprises at least three cyano moieties.

[0169] According to one embodiment, the first radialene compound of formula (I) comprises at least four cyano moieties.

[0170] According to one embodiment, the first radialene compound of formula (I) comprises 3 to 8 cyano moieties.

[0171] According to one embodiment, the first radialene compound of formula (I) comprises 3 to 7 cyano moieties.

[0172] According to one embodiment, the first radialene compound of formula (I) comprises 4 to 7 cyano moieties.

[0173] According to one embodiment, the first radialene compound of formula (I) comprises 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.

[0174] According to one embodiment, the first radialene compound of formula (I) comprises 10 to 20 fluorine atoms, or 10 to 18 fluorine atoms, or 12 to 18 fluorine atoms.

[0175] According to one embodiment, the first radialene compound of formula (I) comprises 4 to 7 cyano moieties and 12 to 18 fluorine atoms.

[0176] According to one embodiment, the first radialene compound of formula (I) comprises at least one CF3 group.

[0177] According to one embodiment, the first radialene compound of formula (I) comprises at least one to three CF3 groups.

[0178] According to one embodiment, the amount of the first radial olefin compound of formula (I) present is ≤99.9% by weight based on the total weight of the hole injection layer, 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, more preferably ≤3.0% by weight, more preferably ≤2.75% by weight, more preferably ≤2.5% by weight, more preferably ≤2.25% by weight, and most preferably ≤2.0% by weight.

[0179] According to one embodiment, when the hybrid functional B3LYP and 6-31G When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the LUMO of the first olefin compound of formula (I) is ≤-4.70 eV, preferably ≤-4.80 eV, more preferably ≤-4.90 eV, even more preferably ≤-5.00 eV, even more preferably ≤-5.10 eV, even more preferably ≤-5.15 eV, and most preferably ≤-5.25 eV.

[0180] According to one embodiment, when the hybrid functional B3LYP and 6-31G When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the calculated LUMO level of the first radialene compound of formula (I) is ≤-5.21 eV, preferably ≤-5.22 eV; further preferably ≤-5.25 eV; further preferably ≤-5.29 eV.

[0181] According to one embodiment, when the hybrid functional B3LYP and 6-31G When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the calculated LUMO level of the first axial olefin compound of formula (I) is in the range of ≤-5.20 eV to ≥-5.75 eV, preferably in the range of ≤-5.20 eV to ≥-5.70 eV; further preferably in the range of ≤-5.20 eV to ≥-5.65 eV, also preferably in the range of ≤-5.20 eV to ≥-5.60 eV, further preferably in the range of ≤-5.22 eV to ≥-5.60 eV, further preferably in the range of ≤-5.25 eV to ≥-5.55 eV, more preferably in the range of ≤-5.25 eV to ≥-5.50 eV, even more preferably in the range of ≤-5.25 eV to ≥-5.45 eV.

[0182] The second olefin compound of formula (II)

[0183] According to one embodiment, the second radialene compound of formula (II) comprises less than nine cyano moieties.

[0184] According to one embodiment, the second radialene compound of formula (II) comprises less than eight cyano moieties.

[0185] According to one embodiment, the second radialene compound of formula (II) comprises at least one cyano moiety.

[0186] According to one embodiment, the second radialene compound of formula (II) comprises at least two cyano moieties.

[0187] According to one embodiment, the second radialene compound of formula (II) comprises at least three cyano moieties.

[0188] According to one embodiment, the second radialene compound of formula (II) comprises at least four cyano moieties.

[0189] According to one embodiment, the second radialene compound of formula (II) comprises 3 to 8 cyano moieties.

[0190] According to one embodiment, the second radialene compound of formula (II) comprises 3 to 7 cyano moieties.

[0191] According to one embodiment, the second radialene compound of formula (II) comprises 4 to 7 cyano moieties.

[0192] According to one embodiment, the second radialene compound of formula (II) comprises 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.

[0193] According to one embodiment, the second radialene compound of formula (II) comprises 10 to 20 fluorine atoms, or 10 to 18 fluorine atoms, or 12 to 18 fluorine atoms.

[0194] According to one embodiment, the second radialene compound of formula (II) comprises 4 to 7 cyano moieties and 12 to 18 fluorine atoms.

[0195] According to one embodiment, the second radialene compound of formula (II) comprises at least one CF3 group.

[0196] According to one embodiment, the second radialene compound of formula (II) comprises at least one to three CF3 groups.

[0197] According to one embodiment, the second radialene compound of formula (II) has a calculated LUMO energy level, wherein the LUMO energy level is calculated by applying the hybrid functional B3LYP and 6-31G in the gas phase. The basis sets were calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany).

[0198] Substituents R' and R"

[0199] According to one embodiment, in the first radiallyne compound of formula (I), R' is independently selected from halogen, F and CN.

[0200] According to one embodiment, in the first radialene compound of formula (I), R' is selected from CN.

[0201] According to one embodiment, each R′ in the first radiallyne compound of formula (I) 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.

[0202] According to one embodiment, each R′ in the first radiallyne compound of formula (I) is independently selected from partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, halogen, F and CN.

[0203] According to one embodiment, each R' in the first radiallyne compound of formula (I) is independently selected from CF3, F and CN.

[0204] According to one embodiment, in the second radiallyne compound of formula (I), R″ is independently selected from halogen, F and CN.

[0205] According to one embodiment, in the second radialene compound of formula (I), R″ is selected from CN.

[0206] According to one embodiment, each R″ in the second radial olefin compound of formula (II) 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.

[0207] According to one embodiment, each R″ in the second radial olefin compound of formula (II) is independently selected from partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, halogen, F and CN.

[0208] According to one embodiment, each R" in the second radial olefin compound of formula (II) is independently selected from CF3, F and CN.

[0209] According to one embodiment, wherein R' in the first radial ene compound of formula (I) and R", R' and R" in the second radial ene compound of formula (II), are independently selected from halogen, F and CN, preferably CN.

[0210] Substituent A 1 , A 2 and A 3 and B 1 , B 2 and B 3

[0211] According to one embodiment, in the first radially olefin compound of formula (I), A 1 , A 2 and A 3 At least two of the choices are the same.

[0212] According to one embodiment, in the first radially olefin compound of formula (I), A 1 , A 2 and A 3 Select Same.

[0213] According to one embodiment, in the first radially olefin compound of formula (I), A 2 and A 3 Select Same.

[0214] According to one embodiment, in the first radially olefin compound of formula (I), A 1 and A 3 Select Same.

[0215] According to one embodiment, in the first radially olefin compound of formula (I), A 1 and A 2 Select Same.

[0216] According to one embodiment, in the first radially olefin compound of formula (I), A 1 Choose with A 2 and / or A 3 different.

[0217] According to one embodiment, in the second radial olefin compound of formula (II), B 1 , B 2 and B 3 At least two of the choices are the same.

[0218] According to one embodiment, in the second radial olefin compound of formula (II), B 1 , B 2 and B 3 Select Same.

[0219] According to one embodiment, in the second radial olefin compound of formula (II), B 2 and B 3 Select Same.

[0220] According to one embodiment, in the second radial olefin compound of formula (II), B 1 and B 3 Select Same.

[0221] According to one embodiment, in the second radial olefin compound of formula (II), B 1 and B 2 Select Same.

[0222] According to one embodiment, in the second radial olefin compound of formula (II), B 1 Choose B 2 and / or B 3 different.

[0223] According to one embodiment, in the first radially olefin compound of formula (I), A 1 , A 2 and A 3 At least two of the options are the same; and / or in the second olefin compound of formula (II), B 1 , B 2 and B 3 At least two of the choices are the same.

[0224] Substituent Ar 1 ,Ar 2 and Ar 3 and Er 1 , Er2 and Er 3

[0225] According to one embodiment, Ar 1 ,Ar 2 and Ar 3 independently selected from substituted or unsubstituted C6 to C 12 Aryl and substituted or unsubstituted C3 to C 12 Heteroaryl.

[0226] According to one embodiment, Ar 1 ,Ar 2 and Ar 3 are independently selected from substituted or unsubstituted C6 aryl and substituted or unsubstituted C3 to C5 heteroaryl.

[0227] According to one embodiment, 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.

[0228] According to one embodiment, Ar 1 ,Ar 2 and Ar 3 The substituents on are independently selected from Cl, F, CN and perfluorinated alkyl.

[0229] According to one embodiment, Ar 1 ,Ar 2 and Ar 3 The substituents on R are independently selected from F, CN and perfluorinated alkyl.

[0230] According to one embodiment, Ar 1 ,Ar 2 and Ar 3 The substituents on are independently selected from F, CN and CF3.

[0231] According to one embodiment, Ar 1 ,Ar 2 and Ar 3 The substituents on are independently selected from CN and CF3.

[0232] According to one embodiment, Ar 1 ,Ar 2 and Ar 3 The substituents on are independently selected from CN.

[0233] According to one embodiment, Ar 1 ,Ar 2 and Ar 3The substituents on are independently selected from CF3.

[0234] According to one embodiment, Ar 1 ,Ar 2 and Ar 3 Each independently contains more than one and less than five substituents, preferably contains more than two and less than four substituents, for example contains 4 substituents.

[0235] According to one embodiment, Er 1 , Er 2 and Er 3 independently selected from substituted or unsubstituted C6 to C 12 Aryl and substituted or unsubstituted C3 to C 12 Heteroaryl.

[0236] According to one embodiment, Er 1 , Er 2 and Er 3 are independently selected from substituted or unsubstituted C6 aryl and substituted or unsubstituted C3 to C5 heteroaryl.

[0237] According to one embodiment, Er 1 , Er 2 and Er 3 The substituents on are independently selected from electron withdrawing groups, halogens, Cl, F, CN, partially fluorinated alkyls and perfluorinated alkyls.

[0238] According to one embodiment, Er 1 , Er 2 and Er 3 The substituents on are independently selected from Cl, F, CN and perfluorinated alkyl.

[0239] According to one embodiment, Er 1 , Er 2 and Er 3 The substituents on R are independently selected from F, CN and perfluorinated alkyl.

[0240] According to one embodiment, Er 1 , Er 2 and Er 3 The substituents on are independently selected from F, CN and CF3.

[0241] According to one embodiment, Er 1 , Er 2 and Er 3 The substituents on are independently selected from CN and CF3.

[0242] According to one embodiment, Er 1 , Er 2and Er 3 The substituents on are independently selected from CN.

[0243] According to one embodiment, Er 1 , Er 2 and Er 3 The substituents on are independently selected from CF3.

[0244] According to one embodiment, Er 1 , Er 2 and Er 3 Each independently contains more than one and less than five substituents, preferably contains more than two and less than four substituents, for example contains 4 substituents.

[0245] According to one embodiment, in the first radialene compound of formula (I), Ar 1 ,Ar 2 and Ar 3 is independently selected from one of the following B1 to B64 groups, and / or in the second olefin compound of formula (II), Er 1 , Er 2 and Er 3 Independently selected from one of the following B1 to B64 groups:

[0246]

[0247] The asterisk " ” indicates the binding position.

[0248] According to one embodiment, in the first radialene compound of formula (I), Ar 1 ,Ar 2 and Ar 3 is independently selected from one of the following groups B1 to B8, B10 to B17, B19 to B21, B24 to B26, B33, B34, B37, B40, B43, B58 to B62 and B64, and / or in the second olefin compound of formula (II), Er 1 , Er 2 and Er 3 is independently selected from one of the following groups B1 to B8, B10 to B17, B19 to B21, B24 to B26, B33, B34, B37, B40, B43, B58 to B62 and B64, preferably in the first olefin compound of formula (I): 1 ,Ar 2 and Ar 3is independently selected from one of the following B2, B3, B4, B11, B13, B37, B43, B58, B59, B60, B61, B63 and B64 groups, and / or in the second olefin compound of formula (II), Er 1 , Er 2 and Er 3 Independently selected from one of the following B2, B3, B4, B11, B13, B37, B43, B58, B59, B60, B61, B63 and B64 groups.

[0249] According to one embodiment, in the first radialene compound of formula (I), Ar 1 ,Ar 2 and Ar 3 is independently selected from one of the following B1 to B64 groups, and / or in the second olefin compound of formula (II), Er 1 , Er 2 and Er 3 Independently selected from one of the following B1 to B64 groups, wherein preferably each R' and / or R" is selected from CN, preferably wherein in the first olefin compound of formula (I) Ar 1 ,Ar 2 and Ar 3 is independently selected from one of the following groups B1 to B5, B7, B8, B10 to B13, B15 to B17, B19 to B21, B37, B43, B58 to B61, B63 and B64, and / or in the second olefin compound of formula (II), Er 1 , Er 2 and Er 3 Independently selected from one of the following B1 to B5, B7, B8, B10 to B13, B15 to B17, B19 to B21, B37, B43, B58 to B61, B63 and B64 groups, wherein preferably each R' and / or R" is selected from CN.

[0250] According to one embodiment, in the first radialene compound of formula (I), Ar 1 ,Ar 2 and Ar 3 is independently selected from one of the following groups, and / or in the second olefin compound of formula (II), Er 1 , Er 2 and Er 3 Independently selected from one of the following groups:

[0251]

[0252] The asterisk " " represents a binding position; wherein preferably each R' and / or R" is selected from CN.

[0253] According to one embodiment, in the first olefin compound of formula (I), Ar 1 ,Ar 2 and Ar 3 is independently selected from one of the following groups, and / or in the second olefin compound of formula (II), Er 1 , Er 2 and Er 3 Independently selected from one of the following groups:

[0254]

[0255] The asterisk " " represents a binding position; wherein preferably each R' and / or R" is selected from CN.

[0256] According to one embodiment, in the first olefin compound of formula (I), Ar 1 ,Ar 2 and Ar 3 is independently selected from one of the following groups, and / or in the second olefin compound of formula (II), Er 1 , Er 2 and Er 3 Independently selected from one of the following groups:

[0257]

[0258] The asterisk " ” indicates the binding position.

[0259] According to one embodiment, in the first olefin compound of formula (I), Ar 1 ,Ar 2 and Ar 3 is independently selected from one of the following groups, and / or in the second olefin compound of formula (II), Er 1 , Er 2 and Er 3 Independently selected from one of the following groups:

[0260]

[0261] The asterisk " ” represents a binding position; wherein each R′ is selected from CN.

[0262] The first olefin compound of formula (I)

[0263] According to one embodiment, the first radial olefin compound of formula (I) is selected from one of the following compounds A1 to A8, wherein R' is selected from CN and A 1 Ar 1 , A 2 Ar 2 and A 3 Ar 3 Select according to Table 1.

[0264] Table 1

[0265]

[0266] The asterisk " ” indicates the binding position.

[0267] According to one embodiment, the first olefin compound of formula (I) is preferably selected from one of the following compounds A1 to A4 and A8, wherein R' is selected from CN and A 1 Ar 1 , A 2 Ar 2 and A 3 Ar 3 Select according to Table 2.

[0268] Table 2

[0269]

[0270] The asterisk " ” indicates the binding position.

[0271] According to one embodiment, the first olefin compound of formula (I) is preferably selected from one of the following compounds A1 to A4 and A8, wherein R' is selected from CN and A 1 Ar 1 , A 2 Ar 2 and A 3 Ar 3 Select according to Table 3.

[0272] Table 3

[0273]

[0274] The asterisk " ” indicates the binding position.

[0275] The second olefin compound of formula (II)

[0276] According to one embodiment, the second olefin compound of formula (II) is preferably selected from one of the following compounds B1 to B14, wherein R" is selected from CN and B 1Er 1 , B 2 Er 2 and B 3 Er 3 Select according to Table 4.

[0277] Table 4

[0278]

[0279] The asterisk " ” indicates the binding position.

[0280] According to one embodiment, the second olefin compound of formula (II) is preferably selected from one of the following compounds B2 to B5 and B7 to B12, wherein R" is selected from CN and B 1 Er 1 , B 2 Er 2 and B 3 Er 3 Select according to Table 5.

[0281] Table 5

[0282]

[0283] The asterisk " ” indicates the binding position.

[0284] According to one embodiment, the second olefin compound of formula (II) is preferably selected from one of the following compounds B2 to B5 and B7 to B12, wherein R" is selected from CN and B 1 Er 1 , B 2 Er 2 and B 3 Er 3 Select according to Table 6.

[0285] Table 6

[0286]

[0287] The asterisk " ” indicates the binding position.

[0288] Formula (III)

[0289] According to one embodiment, in the first radialene compound of formula (I), Ar 1 ,Ar 2 and Ar 3are independently selected from the group according to the following formula (III), and / or in the second olefin compound of formula (II), Er 1 , Er 2 and Er 3 is independently selected from a group according to the following formula (III), and wherein preferably each R' and / or R" is selected from CN:

[0290]

[0291] in

[0292] E 1 From The CW 1 or N;

[0293] E 2 From The CW 2 or N;

[0294] E 3 From The CW 3 or N;

[0295] E 4 From The CW 4 or N;

[0296] E 5 From The CW 5 or N;

[0297] W 1 , W 2 , W 3 , W 4 and W 5 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, CF3, 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,

[0298] Where W 1 , W 2 , W 3 , W 4 and W 5 The 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;

[0299] The asterisk " ” indicates the binding position.

[0300] According to one embodiment, in the first radialene compound of formula (I), Ar 1 ,Ar 2 and Ar 3 is independently selected from a group according to the following formula (III), and wherein preferably each R' and / or R" is selected from CN:

[0301]

[0302] in

[0303] E 1 From The CW 1 or N;

[0304] E 2 From The CW 2 or N;

[0305] E 3 From The CW 3 or N;

[0306] E 4 From The CW 4 or N;

[0307] E 5 From The CW 5 or N;

[0308] W 1 , W 2 , W 3 , W 4 and W 5 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, CF3, 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,

[0309] Where W 1 , W 2 , W 3 , W 4 and W 5 The 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;

[0310] The asterisk " ” indicates the binding position.

[0311] According to one embodiment, in the second olefin compound of formula (II), Er 1 , Er 2 and Er 3 is independently selected from a group according to the following formula (III), and wherein preferably each R' and / or R" is selected from CN:

[0312]

[0313] in

[0314] E 1 From The CW 1 or N;

[0315] E 2 From The CW 2 or N;

[0316] E 3 From The CW 3 or N;

[0317] E 4 From The CW 4 or N;

[0318] E 5 From The CW 5 or N;

[0319] W 1 , W 2 , W 3 , W 4 and W 5 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, CF3, 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,

[0320] Where W 1 , W 2 , W 3 , W 4 and W 5 The 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;

[0321] The asterisk " ” indicates the binding position.

[0322] According to one embodiment, wherein in formula (III), W 1 , W 2 , W 3 , W 4 and W 5 Independently selected from electron withdrawing groups, CN, halogen, Cl, F, NO2, partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, partially fluorinated or perfluorinated C1 to C6 alkoxy, OCF3, D or H, and preferably each R' and / or R" is CN.

[0323] Formula (IVa) to (IVh)

[0324] According to one embodiment, the compound of the first radial olefin compound of formula (I) and the compound of the second radial olefin compound of formula (II) are independently represented by one of the following formulae (IVa) to (IVh),

[0325]

[0326] Among them, Ar 1 ,Ar 2 ,Ar 3 and R' are independently selected from halogen, F and CN, preferably CN.

[0327] According to one embodiment, the compound of the first radial olefin compound of formula (I) and the compound of the second radial olefin compound of formula (II) are independently represented by one of formulas (IVa) to (IVh), wherein Ar 1 ,Ar 2 ,Ar 3 and R' are independently selected from halogen, F and CN, preferably CN; and wherein the first radial ene compound of formula (I) and the second radial ene compound of formula (II) are selected to be different from each other.

[0328] According to one embodiment, the organic electroluminescent device comprises, as compound of formula (I), a mixture of at least two compounds selected from the group consisting of the formulae (IVa) to (IVh) as defined above.

[0329] According to one embodiment, the organic electroluminescent device comprises, as compound of formula (I), a mixture of at least two compounds selected from the group consisting of the formulae (IVa) to (IVh) as defined above.

[0330] First hole transport host compound

[0331] According to one embodiment, wherein the first hole transporting host compound is a covalent host compound, preferably the first hole transporting host compound is a substantially covalent host compound.

[0332] According to one embodiment, the hole injection layer comprises a first hole transporting host compound.

[0333] The first hole transporting matrix compound is a covalent matrix compound, which may be selected from at least one organic compound. The covalent matrix compound and preferably the substantially covalent matrix may consist essentially of covalently bound C, H, O, N, S, which may optionally further contain covalently bound B, P, As and / or Se.

[0334] According to one embodiment, the covalent matrix compound and preferably the substantially covalent matrix may be selected from organic compounds consisting essentially of covalently bound C, H, O, N, S, optionally further comprising covalently bound B, P, As and / or Se.

[0335] 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 serve as covalent, preferably substantially covalent, host compounds of the hole injection layer.

[0336] In one embodiment, the covalent host compound and preferably the substantially covalent host compound has no metal atoms and the majority of its backbone atoms may be selected from C, O, S, N. Alternatively, the covalent host compound and preferably the substantially covalent host compound has no metal atoms and the majority of its backbone atoms may be selected from C and N.

[0337] According to one embodiment, the molecular weight Mw of the covalent matrix compound and preferably the substantially covalent matrix compound can be ≥400 g / mol and ≤2000 g / mol, preferably the molecular weight Mw is ≥450 g / mol and ≤1500 g / mol, further 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 also preferably the molecular weight Mw is ≥600 g / mol and ≤800 g / mol.

[0338] Preferably, the covalent matrix compound, and preferably the substantially covalent matrix compound, comprises at least one arylamine moiety, or a diarylamine moiety, or a triarylamine moiety.

[0339] Preferably, the covalent matrix compound and preferably the substantially covalent matrix compound is free of metallic and / or ionic bonds.

[0340] According to one embodiment, based on the total weight of the hole injection layer, the amount of the first hole transport host compound present in the hole injection layer is ≥0.1% by weight, preferably ≥1% by weight, more preferably ≥5% by weight, more preferably ≥10% by weight, more preferably ≥20% by weight, more preferably ≥30% by weight, more preferably ≥40% by weight, more preferably ≥50% by weight, more preferably ≥60% by weight, more preferably ≥70% by weight, more preferably ≥80% by weight, more preferably ≥90% by weight, more preferably ≥95% by weight, more preferably ≥97.0% by weight, more preferably ≥97.25% by weight, more preferably ≥97.5% by weight, more preferably ≥97.75% by weight, and most preferably ≥98.0% by weight.

[0341] According to one embodiment, when the hybrid functional B3LYP and 6-31G When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the calculated HOMO level of the first hole-transport matrix compound, preferably the first hole-transport matrix compound of the hole injection layer, is in the range of ≤-4.27 eV to ≥-5.1 eV, preferably in the range of <-4.3 eV and >-5.0 eV, further preferably in the range of <-4.5 eV and >-5.0 eV, also preferably in the range of <-4.5 eV and >-4.9 eV, further preferably in the range of <-4.6 eV and >-4.9 eV.

[0342] According to one embodiment, the first hole transport host compound of the hole injection layer and the second hole transport host compound of the p-type charge generation layer may be selected to be the same.

[0343] Second hole transport host compound

[0344] According to one embodiment, wherein the second hole transporting host compound is a covalent host compound, preferably the second hole transporting host compound is a substantially covalent host compound.

[0345] According to one embodiment, the p-type charge generation layer includes a second hole transport host compound.

[0346] The second hole transporting matrix compound is a covalent matrix compound, which may be selected from at least one organic compound. The covalent matrix compound and the preferred substantially covalent matrix may consist essentially of covalently bound C, H, O, N, S, which may optionally further contain covalently bound B, P, As and / or Se.

[0347] According to one embodiment, the covalent matrix compound and preferably the substantially covalent matrix may be selected from organic compounds consisting essentially of covalently bound C, H, O, N, S, optionally further comprising covalently bound B, P, As and / or Se.

[0348] 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 serve as covalent, preferably substantially covalent, host compounds of the hole injection layer.

[0349] In one embodiment, the covalent host compound and preferably the substantially covalent host compound has no metal atoms and the majority of its backbone atoms may be selected from C, O, S, N. Alternatively, the covalent host compound and preferably the substantially covalent host compound has no metal atoms and the majority of its backbone atoms may be selected from C and N.

[0350] According to one embodiment, the molecular weight Mw of the covalent matrix compound and preferably the substantially covalent matrix compound can be ≥400 g / mol and ≤2000 g / mol, preferably the molecular weight Mw is ≥450 g / mol and ≤1500 g / mol, further 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 also preferably the molecular weight Mw is ≥600 g / mol and ≤800 g / mol.

[0351] Preferably, the covalent matrix compound, and preferably the substantially covalent matrix compound, comprises at least one arylamine moiety, or a diarylamine moiety, or a triarylamine moiety.

[0352] Preferably, the covalent matrix compound and preferably the substantially covalent matrix compound is free of metallic and / or ionic bonds.

[0353] According to one embodiment, the amount of the second hole transport host compound present in the p-type charge generation layer is ≥0.1 wt % based on the total weight of the p-type charge generation layer, and is 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 %.

[0354] According to one embodiment, when the hybrid functional B3LYP and 6-31G When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the calculated LUMO level of the second hole transport host compound of formula (II) is ≤−5.21 eV.

[0355] According to one embodiment, when the hybrid functional B3LYP and 6-31G When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the calculated LUMO energy level of the second hole transport host compound of formula (II) is in the range of ≤-4.60 eV, more preferably in the range of ≤-4.75 eV; also preferably in the range of ≤-5.00 eV; also preferably in the range of ≤-5.10 eV; further preferably in the range of ≤-5.15 eV; more preferably in the range of ≤-5.19 eV.

[0356] According to one embodiment, when the hybrid functional B3LYP and 6-31G When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the calculated HOMO level of the second hole transport host compound is in the range of ≤-4.27 eV to ≥-5.1 eV, preferably in the range of <-4.3 eV and >-5.0 eV, further preferably in the range of <-4.5 eV and >-5.0 eV, also preferably in the range of <-4.5 eV and >-4.9 eV, and further preferably in the range of <-4.6 eV and >-4.9 eV.

[0357] According to one embodiment, the calculated LUMO energy level of the second radialene compound of formula (II) may be selected to be higher than the LUMO energy level of the first radialene compound of formula (I).

[0358] According to one embodiment, the first hole transport host compound of the hole injection layer and the second hole transport host compound of the p-type charge generation layer may be selected to be the same.

[0359] The compound of formula (VII) or the compound of formula (VIII)

[0360] According to another aspect of the present invention, the covalent matrix compound or substantially covalent matrix compound may comprise at least one arylamine compound, diarylamine compound, triarylamine compound, compound of formula (VII) or compound of formula (VIII):

[0361] ,

[0362] in:

[0363] 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;

[0364] T 6 is a phenyl subunit, a biphenyl subunit, a terphenyl subunit or a naphthalene subunit;

[0365] 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 condensed 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 condensed ring system comprising 2 to 6 substituted or unsubstituted 5 to 7-membered rings, and the rings are selected from: (i) unsaturated 5 to 7-membered heterocyclic rings, (ii) 5 to 6-membered aromatic heterocyclic rings, (iii) unsaturated 5 to 7-membered non-heterocyclic rings, (iv) aromatic non-heterocyclic 6-membered rings;

[0366] Among them, Ar' 1,Ar' 2 ,Ar' 3 ,Ar' 4 and Ar' 5 The substituents are selected from 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 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,

[0367] 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.

[0368] 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 5is 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.

[0369] 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.

[0370] 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.

[0371] According to one embodiment, wherein Ar' 1 ,Ar' 2 ,Ar' 3 ,Ar' 4 and Ar' 5 Can be independently selected from D1 to D16:

[0372]

[0373] The asterisk " ” indicates the binding position.

[0374] 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.

[0375] 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.

[0376] 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 that is particularly suitable for mass production.

[0377] The “host compound of formula (VII) or formula (VIII)” may also be referred to as a “hole transport compound”.

[0378] 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.

[0379] According to one embodiment of the electronic device, the covalent or substantially covalent matrix compound of formula (VII) or formula (VIII) is selected from F1 to F19:

[0380]

[0381] Hole injection layer

[0382] According to one embodiment, the hole injection layer is also referred to as an “organic semiconductor layer”.

[0383] According to one embodiment, the hole injection layer is adjacent to the anode layer.

[0384] According to one embodiment, the hole injection layer is in direct contact with the anode layer.

[0385] The hole injection layer (HIL) can be formed on the anode layer by vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blodgett (LB) deposition, etc. When vacuum deposition is used to form the HIL, the deposition conditions may vary according to the compound used to form the HIL and the desired structure and thermal properties of the HIL. However, in general, the conditions for vacuum deposition 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 / sec to 10 nm / sec.

[0386] When the HIL is formed using spin coating or printing, the coating conditions may vary according to 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.

[0387] 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.

[0388] According to one embodiment, the hole injection layer further comprises a hole transport host compound, wherein the hole transport host compound may be an organic hole transport material.

[0389] According to one embodiment, the hole transporting host compound may be a substantially covalent host compound.

[0390] According to one embodiment, based on the total weight of the hole injection layer, the amount of the first radial olefin compound of formula (I) present in the hole injection 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, more preferably ≤3.0% by weight, more preferably ≤2.75% by weight, more preferably ≤2.5% by weight, more preferably ≤2.25% by weight, and most preferably ≤2.0% by weight.

[0391] According to one embodiment, the first radial olefin compound of formula (I) is present in the hole injection layer in an amount of ≤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 %, most preferably ≤2.0 wt %. %; and based on the total weight of the hole injection layer, the first hole transport host compound is present in the hole injection layer in an amount of ≥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%.

[0392] According to one embodiment, based on the total weight of the hole injection layer, the amount of the first hole transport host compound present in the hole injection layer is ≥0.1% by weight, preferably ≥1% by weight, more preferably ≥5% by weight, more preferably ≥10% by weight, more preferably ≥20% by weight, more preferably ≥30% by weight, more preferably ≥40% by weight, more preferably ≥50% by weight, more preferably ≥60% by weight, more preferably ≥70% by weight, more preferably ≥80% by weight, more preferably ≥90% by weight, more preferably ≥95% by weight, more preferably ≥97.0% by weight, more preferably ≥97.25% by weight, more preferably ≥97.5% by weight, more preferably ≥97.75% by weight, and most preferably ≥98.0% by weight.

[0393] Light emitting unit

[0394] According to one embodiment, at least one light-emitting unit, at least two light-emitting units comprise at least one electron transport layer, and preferably each light-emitting unit comprises at least one electron transport layer.

[0395] According to one embodiment, at least one emitting unit comprises at least one hole transport layer, preferably each emitting unit comprises at least one hole transport layer.

[0396] According to one embodiment, at least one light-emitting unit comprises at least one electron transport layer and at least one hole transport layer, preferably each light-emitting unit comprises at least one electron transport layer and at least one hole transport layer.

[0397] According to one embodiment, at least one light-emitting unit comprises at least one electron transport layer and at least one hole transport layer, preferably each light-emitting unit comprises at least one electron transport layer and at least one hole transport layer, wherein at least one hole transport layer is arranged closer to the anode than at least one electron transport layer.

[0398] According to one embodiment, at least one light-emitting unit comprises at least one electron transport layer and at least one hole transport layer, preferably each light-emitting unit comprises at least one electron transport layer and at least one hole transport layer, wherein at least one light-emitting layer is arranged between at least one hole transport layer and at least one electron transport layer, wherein preferably, at least one hole transport layer is arranged closer to the anode than at least one electron transport layer.

[0399] According to one embodiment, at least one light-emitting unit comprises an electron blocking layer and a hole blocking layer, wherein the electron blocking layer is preferably arranged between the first hole transport layer and the at least one light-emitting layer, and the hole blocking layer is arranged between the first electron transport layer and the at least one light-emitting layer.

[0400] Charge generation layer

[0401] According to one embodiment, the at least one charge generation layer further comprises an n-type charge generation layer.

[0402] According to one embodiment, each of the at least one charge generation layer comprises an n-type charge generation layer.

[0403] According to one embodiment, an n-type charge generation layer of the at least one charge generation layer is closer to the anode layer than a p-type charge generation layer of the at least one charge generation layer.

[0404] According to one embodiment, the n-type charge generation layer of the at least one charge generation layer is arranged adjacent to the p-type charge generation layer of the at least one charge generation layer.

[0405] According to one embodiment, the n-type charge generation layer of the at least one charge generation layer is in direct contact with the p-type charge generation layer of the at least one charge generation layer.

[0406] According to one embodiment, the n-type charge generation layer of each of the at least one charge generation layer is closer to the anode layer than the p-type charge generation layer of the at least one charge generation layer.

[0407] According to one embodiment, the n-type charge generation layer of each of the at least one charge generation layer is arranged adjacent to the p-type charge generation layer of the at least one charge generation layer.

[0408] According to one embodiment, the n-type charge generation layer of each of the at least one charge generation layer is in direct contact with the p-type charge generation layer of the at least one charge generation layer.

[0409] n-type charge generation layer

[0410] According to one embodiment, the charge generation layer includes an n-type charge generation layer.

[0411] According to one embodiment, the n-type charge generation layer of the at least one charge generation layer is adjacent to the at least one electron transport layer.

[0412] According to one embodiment, the n-type charge generation layer of the at least one charge generation layer is adjacent to the at least one electron transport layer and adjacent to the p-type charge generation layer of the at least one charge generation layer.

[0413] According to one embodiment, the n-type charge generation layer of the at least one charge generation layer is in direct contact with the at least one electron transport layer.

[0414] According to one embodiment, the n-type charge generation layer 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.

[0415] According to one embodiment, the n-type charge generation layer of the at least one charge generation layer is in direct contact with the at least one electron transport layer and in direct contact with the p-type charge generation layer of the at least one charge generation layer.

[0416] According to one embodiment, the n-type charge generation layer of each of the at least one charge generation layer is adjacent to the at least one electron transport layer.

[0417] According to one embodiment, the n-type charge generation layer of each of the at least one charge generation layer is adjacent to the at least one electron transport layer and adjacent to the p-type charge generation layer of the at least one charge generation layer.

[0418] According to one embodiment, 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.

[0419] According to one embodiment, 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.

[0420] According to one embodiment, the n-type charge generation layer is in direct contact with the p-type charge generation layer, wherein the n-type charge generation layer is closer to the anode layer than the p-type charge generation layer.

[0421] According to one embodiment, the n-type charge generation layer includes a metal dopant.

[0422] According to one embodiment, the n-type charge generation layer includes an electron transport host compound.

[0423] According to one embodiment, the electron transporting host compound is an organic electron transporting host compound.

[0424] According to one embodiment, the electron transporting matrix compound is a substantially covalent matrix compound.

[0425] According to one embodiment, the electron transporting matrix compound is a substantially covalent organic matrix compound.

[0426] According to one embodiment, the n-type charge generation layer includes a metal dopant and an electron transport host compound.

[0427] According to one embodiment, 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 with the p-type charge generation layer of the at least one charge generation layer.

[0428] According to one embodiment, the n-type charge generation layer further includes an electron transport material.

[0429] According to one embodiment, the n-type charge generation layer further includes an organic electron transport material.

[0430] According to one embodiment, the electron transport material comprises at least one C2 to C 24 The N-heteroaryl group or the P=X group, wherein X is O, P, Se, and P=O is particularly preferred.

[0431] According to one embodiment of the present invention, at least one C2 to C 24 The N-heteroaryl radical of can be selected from compounds comprising at least one azine group, preferably at least two azine groups, also preferably three azine groups.

[0432] According to one embodiment of the present invention, the electron transport material comprises at least one group selected from the group consisting of pyridine, pyrimidine, triazine, imidazole, benzimidazole, benzoxazole, quinone, benzoquinone, imidazo[1,5-a]pyridine, quinoxaline, benzoquinoxaline, acridine, phenanthroline, benzoacridine, dibenzoacridine, phosphine oxide, and terpyridine.

[0433] According to one embodiment of the present invention, the electron transport material comprises at least one phenanthroline group, preferably two phenanthroline groups, 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.

[0434] According to one embodiment of the present invention, the organic electron transport material comprises at least one phenanthroline group, preferably two phenanthroline groups, one or more pyridine groups, one or more pyrimidine groups, or one or more phosphine oxide groups.

[0435] According to one embodiment of the present invention, the electron transport material comprises at least one phenanthroline group, preferably two phenanthroline groups, a pyridine group, a pyrimidine group or a phosphine oxide group.

[0436] According to one embodiment of the present invention, the electron transport material compound comprises at least one phenanthroline group, preferably two phenanthroline groups, one or more pyridine groups, one or more pyrimidine groups, and one or more triazine groups.

[0437] According to one embodiment of the present invention, the electron transport material 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.

[0438] According to one embodiment of the present invention, the electron transport material comprises at least one phenanthroline group, preferably two phenanthroline groups.

[0439] According to one embodiment of the present invention, the n-type charge generation layer includes a metal dopant.

[0440] According to one embodiment, the metal dopant is selected from a metal having an electronegativity of ≤1.4 eV according to the Pauling standard, or a metal alloy containing a metal having an electronegativity of ≤1.4 eV according to the Pauling standard.

[0441] According to one embodiment, the metal dopant is selected from a metal having an electronegativity of ≤1.35 eV according to the Pauling standard, or a metal alloy containing a metal having an electronegativity of ≤1.35 eV according to the Pauling standard.

[0442] According to one embodiment, 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 containing a metal selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eu and Yb.

[0443] According to one embodiment, 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 containing a metal selected from the group consisting of Li, Na, K, Cs, Mg, Ca, Ba, Sm, Eu and Yb.

[0444] According to one embodiment, the metal dopant is a metal selected from the group consisting of Li, Mg and Yb, or a metal alloy containing a metal selected from the group consisting of Li, Mg and Yb.

[0445] According to one embodiment, the metal dopant is a metal selected from Li and Yb, or a metal alloy containing a metal selected from Li and Yb.

[0446] According to one embodiment, the metal dopant is Yb or a metal alloy containing a metal selected from Li and Yb.

[0447] According to one embodiment, the metal dopant is Yb.

[0448] According to one embodiment, based on the total weight of the hole injection layer, the amount of the metal dopant present in the n-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, more preferably ≤3.0% by weight, more preferably ≤2.75% by weight, more preferably ≤2.5% by weight, more preferably ≤2.25% by weight, and most preferably ≤2.0% by weight.

[0449] According to one embodiment, based on the total weight of the hole injection layer, the amount of the electron transport material present in the n-type charge generation layer is ≥0.1% by weight, preferably ≥1% by weight, more preferably ≥5% by weight, more preferably ≥10% by weight, more preferably ≥20% by weight, more preferably ≥30% by weight, more preferably ≥40% by weight, more preferably ≥50% by weight, more preferably ≥60% by weight, more preferably ≥70% by weight, more preferably ≥80% by weight, more preferably ≥90% by weight, more preferably ≥95% by weight, more preferably ≥97.0% by weight, more preferably ≥97.25% by weight, more preferably ≥97.5% by weight, more preferably ≥97.75% by weight, and most preferably ≥98.0% by weight.

[0450] p-type charge generation layer

[0451] The p-type charge generation layer can be formed on the n-type charge generation layer by vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blodgett (LB) deposition, etc. When vacuum deposition is used to form the p-type charge generation layer, the deposition conditions may vary depending on the compound 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 / sec to 10 nm / sec.

[0452] When spin coating or printing is used to form the p-type charge generation layer, the coating conditions may vary depending on the compound used to form the layer and the desired structure and thermal properties of the p-type charge generation 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 heat treatment removes the solvent.

[0453] The thickness of the p-type charge generation layer may be in a range of about 1 nm to about 20 nm, for example, about 2 nm to about 15 nm, or about 2 nm to about 12 nm.

[0454] According to one embodiment, the p-type charge generation layer of each of the at least one charge generation layer is adjacent to the n-type charge generation layer of the at least one charge generation layer.

[0455] According to one embodiment, the p-type charge generation layer of each of the at least one charge generation layer is in direct contact with the n-type charge generation layer of the at least one charge generation layer.

[0456] According to one embodiment, the p-type charge generation layer of each of the at least one charge generation layer is adjacent to the at least one hole transport layer.

[0457] According to one embodiment, the p-type charge generation layer of each of the at least one charge generation layer is in direct contact with the at least one hole transport layer.

[0458] According to one embodiment, the p-type charge generation layer of each of the at least one charge generation layer is adjacent to the n-type charge generation layer of the at least one charge generation layer and is adjacent to at least one hole transport layer.

[0459] According to one embodiment, the p-type charge generation layer of each of the at least one charge generation layer is in direct contact with the n-type charge generation layer of the at least one charge generation layer and with the at least one hole transport layer.

[0460] According to one embodiment, based on the total weight of the p-type charge generation layer, the amount of the second olefin of formula (II) 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.

[0461] According to one embodiment, based on the total weight of the p-type charge generation layer, the amount of the second olefin of formula (II) 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, and based on the total weight of the p-type charge generation layer, the amount of the second hole transport host compound in the p-type charge generation layer is ≥0.1% by weight, preferably ≥1% by weight, more preferably ≥5% by weight, more preferably ≥10% by weight, more preferably ≥20% by weight, more preferably ≥30% by weight, more preferably ≥40% by weight, more preferably ≥50% by weight, more preferably ≥60% by weight, more preferably ≥70% by weight, more preferably ≥80% by weight, more preferably ≥90% by weight, more preferably ≥95% by weight.

[0462] According to one embodiment, based on the total weight of the p-type charge generation layer, the second hole transport host compound is present in the p-type charge generation layer in an amount of ≥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%.

[0463] According to one embodiment, the p-type charge generation layer of the at least one charge generation layer is adjacent to the n-type charge generation layer of the at least one charge generation layer.

[0464] According to one embodiment, the p-type charge generation layer of the at least one charge generation layer is in direct contact with the n-type charge generation layer of the at least one charge generation layer.

[0465] According to one embodiment, when the hybrid functional B3LYP and 6-31G When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the calculated LUMO level of the second axial olefin compound of formula (II) in the p-type charge generation layer is in the range of ≤-5.00 eV to ≥-5.75 eV, preferably in the range of ≤-5.10 eV to ≥-5.70 eV; further preferably in the range of ≤-5.15 eV to ≥-5.65 eV, further preferably in the range of ≤-5.19 eV to ≥-5.65 eV, further preferably in the range of ≤-5.20 eV to ≥-5.60 eV, more preferably in the range of ≤-5.22 eV to ≥-5.55 eV, still more preferably in the range of ≤-5.22 eV to ≥-5.55 eV, even more preferably in the range of ≤-5.22 eV to ≥-5.50 eV, and even more preferably in the range of ≤-5.22 eV to ≥-5.45 eV. in the eV range.

[0466] Other layers

[0467] 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:

[0468] Base

[0469] 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 a transparent as well as an opaque material, such as a glass substrate, a plastic substrate, a metal substrate, a silicon substrate or a backplane.

[0470] Anode layer

[0471] 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. The anode layer can also be formed using metals, typically silver (Ag), gold (Au) or metal alloys.

[0472] Hole transport layer

[0473] The organic electroluminescent device may further comprise at least one hole transport layer (HTL). According to one embodiment, at least one hole transport layer is contained in one of the at least two emission units, wherein preferably at least one hole transport layer is contained in each emission unit.

[0474] According to one embodiment, a hole transport layer is included in each of the at least two light emitting units.

[0475] According to one embodiment, a p-type charge generation layer of the at least one charge generation layer is adjacent to the at least one hole transport layer.

[0476] According to one embodiment, the p-type charge generation layer of the at least one charge generation layer is in direct contact with the at least one hole transport layer.

[0477] According to one embodiment, the p-type charge generation layer of the at least one charge generation layer is adjacent to the n-type charge generation layer of the at least one charge generation layer and is adjacent to the at least one hole transport layer.

[0478] According to one embodiment, the p-type charge generation layer of the at least one charge generation layer is in direct contact with the n-type charge generation layer of the at least one charge generation layer and is in direct contact with the at least one hole transport layer.

[0479] The hole transport layer (HTL) can 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 conditions of deposition and coating can be similar to those of forming the HIL or CGL. However, the conditions of vacuum or solution deposition may vary according to the compound used to form the HTL.

[0480] The HTL can be formed of any compound commonly used to form the HTL. For example, compounds that can be suitably used are disclosed in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010, which is 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.

[0481] According to one embodiment, the hole transport layer may comprise a substantially covalent host compound as described above.

[0482] 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.

[0483] According to one embodiment, the hole transport layer may include the compound of formula (VII) or (VIII) as described above.

[0484] 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 (VIII) as described above.

[0485] 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 matrix compound.

[0486] 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 (VIII) as described above.

[0487] 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, further preferably about 20 nm to about 190 nm, further preferably about 40 nm to about 180 nm, further preferably about 60 nm to about 170 nm, further preferably about 80 nm to about 160 nm, further preferably about 100 nm to about 160 nm, further preferably about 120 nm to about 140 nm. The preferred thickness of the HTL may be 170 nm to 200 nm.

[0488] When the thickness of the HTL is within this range, the HTL may have excellent hole transport characteristics without substantial deterioration in driving voltage.

[0489] Electron blocking layer

[0490] 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 thus 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. Compared with the HOMO 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. The thickness of the electron blocking layer can be selected between 2 nm and 20 nm.

[0491] If the electron blocking layer has a high triplet energy level, it may also be described as a triplet control layer.

[0492] If a phosphorescent green or blue emitting layer is used, the function of the triplet control layer is to reduce the quenching of the triplet state. 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. Suitable compounds for triplet control layers, in particular triarylamine compounds, are described in EP 2 722 908 A1.

[0493] Photoactive Layer (PAL)

[0494] According to one embodiment of the present invention, the organic electronic device may further include a photoactive layer, wherein the photoactive layer is arranged between the anode layer and the cathode layer.

[0495] However, according to a preferred embodiment, the organic electronic device is free of a photoactive layer.

[0496] The photoactive layer converts electric current into photons or converts photons into electric current.

[0497] 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 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 PAL.

[0498] The photoactive layer may be a light-emitting layer or a light-absorbing layer, and a light-emitting layer is particularly preferred.

[0499] Emitting Layer (EML)

[0500] According to one embodiment of the present invention, the organic electronic device may further include a light emitting layer, wherein the light emitting layer is arranged between the anode layer and the cathode layer.

[0501] The EML can be formed on the HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When vacuum deposition or spin coating is used to form the EML, the conditions for deposition and coating can 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.

[0502] 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).

[0503] The emitter dopant may be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters emitting 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.

[0504] 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.

[0505] Examples of phosphorescent green emitter dopants are Ir(ppy)3 (ppy=phenylpyridine), Ir(ppy)2(acac), Ir(mpyp)3.

[0506] 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.

[0507] The amount of the luminescent dopant may be in the range of about 0.01 parts by weight to about 50 parts by weight based on 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 substantial impairment of the driving voltage.

[0508] Hole blocking layer (HBL)

[0509] 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.

[0510] HBL can also be called auxiliary ETL or a-ETL.

[0511] When vacuum deposition or spin coating is used to form the HBL, 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.

[0512] The thickness of the HBL may be in the 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 deteriorating driving voltage.

[0513] Electron Transport Layer (ETL)

[0514] The organic electroluminescent device may further comprise at least one electron transport layer (ETL). According to one embodiment, at least one electron transport layer is comprised in one of the at least two emission units, wherein preferably at least one electron transport layer is comprised in each emission unit.

[0515] According to one embodiment, each of the at least two light-emitting units comprises an electron transport layer.

[0516] According to one embodiment, the electron transport layer is free of metal dopants, in particular free of metal dopants in oxidation state (0).

[0517] 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.

[0518] 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.

[0519] In one embodiment, the electron transport layer may further comprise a dopant selected from alkali metal organic complexes, preferably LiQ.

[0520] The thickness of the ETL may be in a range of about 15 nm to about 50 nm, for example, in a 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 properties without substantially impairing driving voltage.

[0521] According to another embodiment of the present invention, the organic electronic 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.

[0522] Electron injection layer (EIL)

[0523] An optional EIL that can facilitate electron injection from the cathode can 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, 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 according to the material for forming the EIL.

[0524] According to one embodiment, the organic electroluminescent device comprises at least one electron injection layer (EIL).

[0525] According to one embodiment, the electron injection layer is provided on the light emitting unit.

[0526] According to one embodiment, the electron injection layer is disposed on the light emitting unit closest to the cathode of the organic electroluminescent device.

[0527] According to one embodiment, the electron injection layer is disposed between the light emitting unit closest to the cathode and the cathode.

[0528] According to one embodiment, the electron injection layer is arranged adjacent to the light emitting unit closest to the cathode.

[0529] According to one embodiment, the electron injection layer is disposed between the light emitting unit closest to the cathode and the cathode, and is adjacent to the light emitting unit closest to the cathode.

[0530] According to one embodiment, the electron injection layer is disposed between the light emitting unit closest to the cathode and the cathode, and is adjacent to the cathode.

[0531] According to one embodiment, the electron injection layer is disposed between the light emitting unit closest to the cathode and the cathode, and is adjacent to the light emitting unit closest to the cathode and the cathode.

[0532] According to one embodiment, the electron injection layer is disposed between the light emitting unit closest to the cathode and the cathode, and is in contact with the light emitting unit closest to the cathode and the cathode.

[0533] The thickness of the EIL may be in the range of about 0.1 nm to about 10 nm, for example, in the 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 properties without substantially impairing driving voltage.

[0534] Cathode layer

[0535] The cathode layer is formed on the ETL or the optional EIL. The cathode layer can be formed of a metal, an alloy, a conductive compound or a mixture thereof. The cathode electrode can have a low work function. For example, the cathode layer can 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 can be formed of a transparent conductive oxide such as ITO or IZO. According to a preferred embodiment, the cathode layer is transparent.

[0536] 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, even if the cathode layer is formed of a metal or a metal alloy, it may be transparent or translucent.

[0537] In a preferred embodiment, the cathode layer comprises a metal or a metal alloy and is transparent.

[0538] It should be understood that the cathode layer is not part of the electron injection layer or the electron transport layer.

[0539] Electronic Devices

[0540] According to one embodiment, the electronic device comprises an organic electroluminescent device.

[0541] According to one embodiment, the electronic device comprises an organic electroluminescent device, wherein the electronic device is preferably a display device, a light-emitting device, a thin film transistor, a battery, a display device or a photovoltaic device, preferably a light-emitting device, and preferably the electronic device is part of a display device or a lighting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0542] The components described above and claimed and used according to the invention in the described embodiments do not have any special exceptions in terms of their size, shape, material selection and technical concept, so that selection criteria known in the relevant field can be applied without restriction.

[0543] More details, features and advantages of the purpose of the present invention are disclosed in the dependent claims and the following description of the various drawings, which show preferred embodiments according to the present invention in an exemplary manner. However, any embodiment does not necessarily represent the full scope of the present invention, so the scope of the present invention is interpreted with reference to the claims and this document. It should be understood that the above general description and the following detailed description are only exemplary and explanatory, and are intended to provide further explanation of the invention claimed.

[0544] Figure 1 is a schematic cross-sectional view of an organic electroluminescent device according to an exemplary embodiment.

[0545] Figure 2 is a schematic cross-sectional view of a stacked organic electroluminescent device according to another exemplary embodiment.

[0546] Figure 3 is a schematic cross-sectional view of a stacked organic electroluminescent device according to another exemplary embodiment.

[0547] Figure 4 is a schematic cross-sectional view of an anode layer 120 on a substrate 110 .

[0548] Hereinafter, the accompanying drawings will be described in more detail in conjunction with the embodiments. However, the present invention is not limited to the following drawings.

[0549] 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 therebetween. When a first element is referred to as being formed or disposed "directly" "on" or "over" a second element, no other elements are disposed therebetween.

[0550] Figure 1 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0551] Reference Figure 1The organic electroluminescent device 100 comprises: a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 comprising a first radialene compound of formula (I) and a first hole transport host compound, and a first light emitting unit 140 comprising 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 charge generation layer (CGL1) 150 comprising a first n-type charge generation layer (n-CGL1) 151 and a first p-type charge generation layer (p-CGL1) 152, wherein the first p-type charge generation layer (p-CGL1) 152 comprises a second radialene compound of formula (II) and a second hole transport host compound. The organic electronic device 100 further includes: a second light-emitting unit 240 including 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.

[0552] Figure 2 is a schematic cross-sectional view of a stacked organic electroluminescent device 100 according to another exemplary embodiment of the present invention. Figure 2 and Figure 1 The difference is that Figure 1 The organic electroluminescent device 100 further comprises: a second charge generation layer (CGL2) 250 disposed on the second light-emitting unit 240, wherein the second charge generation layer (CGL2) 250 comprises a second n-type charge generation layer (n-CGL2) 251 and a second p-type charge generation layer (p-GCL2) 252, wherein the second p-type charge generation layer (p-CGL2) 252 may also optionally comprise a second axial olefin compound of formula (II) and a second hole transport matrix compound. Figure 2 The organic electroluminescent device 100 and Figure 1 The difference is that it also includes: a third light-emitting unit 340 arranged on the second charge generation layer (CGL2) 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.

[0553] Figure 3 is a schematic cross-sectional view of a stacked organic electroluminescent device 100 according to another exemplary embodiment of the present invention. Figure 3 and Figure 2 The difference is that Figure 2 The organic electroluminescent device 100 further comprises: a third charge generation layer (CGL3) 350 disposed on the third light-emitting unit 340, wherein the third charge generation layer (CGL3) 350 comprises a third n-type charge generation layer (n-CGL3) 351 and a third p-type charge generation layer (p-CGL3) 352, wherein the third p-type charge generation layer (p-CGL3) 352 may also optionally comprise a second axial olefin compound of formula (II) and a second hole transport matrix compound. Figure 3 The organic electroluminescent device 100 and Figure 2 The difference is that it also includes: a fourth light-emitting unit 440 arranged on the third charge generation layer (CGL3) 350, 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.

[0554] Despite Figure 1 , Figure 2 and Figure 3 Although not shown in the figure, a capping layer and / or a sealing layer may be further formed on the cathode layer 190, thereby sealing the organic electronic device 100. In addition, various other modifications may be implemented thereto.

[0555] Figure 4 1 is a schematic cross-sectional view of the anode layer 120 on the substrate 110. The anode layer 120 includes a first anode sublayer 121, a second anode sublayer 122 and a third anode sublayer 123.

[0556] 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

[0557] The present invention is further illustrated by the following examples, which are intended to be illustrative only and not restrictive.

[0558] Compounds of formula (I) can be prepared as described in EP 2180029 A1 and WO 2016097017 A1.

[0559] Compounds of formula (II) can be prepared as described in EP 2180029 A1 and WO 2016097017 A1.

[0560] Calculated HOMO and LUMO

[0561] The HOMO and LUMO levels 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 calculated by applying the hybrid functional B3LYP and 6-31G in the gas phase. If more than one conformation is feasible, the one with the lowest overall energy is chosen.

[0562] General procedure for making OLEDs

[0563] Table 7 shows compounds generally used in the fabrication of OLEDs.

[0564] Table 7

[0565]

[0566] For the embodiment, a glass substrate having an anode layer including a first anode sublayer of Ag of 120 nm, a second anode sublayer of ITO of 8 nm, and a third anode sublayer of ITO of 10 nm 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, followed by plasma treatment to prepare the anode layer. The plasma treatment was carried out in a nitrogen atmosphere or an atmosphere containing 98% by volume of nitrogen and 2% by volume of oxygen.

[0567] 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 F3 (N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine) and 1 wt % of the compound of formula (I) or according to the comparative example of Table 9.

[0568] Then, a first hole transport layer (HTL1) was formed with a thickness of 27 nm on the HIL by depositing Compound F3 (N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine).

[0569] Then, a first electron blocking layer (EBL1) having a thickness of 5 nm was formed on HTL1 by depositing Compound F19 N-([1,1′-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(triphenylsilyl)phenyl)-9H-fluoren-2-amine.

[0570] Then, a first light emitting layer (EML1) with a thickness of 20 nm was formed on EBL1 by co-depositing 97 vol % of H09 (Sun Fine Chemicals, Korea) as an EML host and 3 vol % of BD200 (Sun Fine Chemicals, Korea) as a fluorescent blue dopant.

[0571] Then, a first hole blocking layer (HBL1) having a thickness of 5 nm was formed on the first light emitting layer by depositing Compound F20 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[0572] Then, a first electron transport layer (ETL1) with a thickness of 20 nm was formed on the first light emitting layer by co-depositing Compound F21 4'-(4-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalen-1-yl)-[1,1'-biphenyl]-4-carbonitrile and LiQ at a ratio of 50:50 wt %.

[0573] Then, an n-CGL having a thickness of 10 nm was formed on the ETL by co-depositing 99 vol % of Compound F22 2,2′-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol % of Yb.

[0574] Then, a p-CGL having a thickness of 10 nm was formed on the n-CGL by co-depositing 93 wt % of compound F3 (N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine) as a matrix compound and 7 wt % of the compound of formula (II) or according to the comparative example of Table 9. The composition of the p-CGL can be seen in Tables 8 and 9.

[0575] Then, a second hole transport layer (HTL2) with a thickness of 24 nm was formed on the p-CGL by depositing F3 (N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine).

[0576] Then, a second electron blocking layer (EBL2) having a thickness of 5 nm was formed on HTL2 by depositing Compound F19 N-([1,1′-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(triphenylsilyl)phenyl)-9H-fluoren-2-amine.

[0577] Then, a second light emitting layer (EML2) with a thickness of 20 nm was formed on the EBL2 by co-depositing 97 vol% of H09 (Sun Fine Chemicals, Korea) as an EML host and 3 vol% of BD200 (Sun Fine Chemicals, Korea) as a fluorescent blue dopant.

[0578] Then, a second hole blocking layer (HBL2) with a thickness of 5 nm was formed on the EML2 by depositing Compound 20 2-(3′-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1′-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[0579] Then, a second electron transport layer (ETL2) with a thickness of 30 nm was formed on the HBL by co-depositing Compound 21 4′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalen-1-yl)-[1,1′-biphenyl]-4-carbonitrile and LiQ in a ratio of 50:50 wt %.

[0580] Then, an electron injection layer (EIL) was formed on the ETL2 with a thickness of 2 nm by depositing Yb.

[0581] Then, by -7 Ag:Mg (90 vol %:10 vol %) was co-deposited at a rate of 0.01 Å / s to 1 Å / s at 400 mbar to form a cathode layer with a thickness of 13 nm on the EIL.

[0582] Then, a capping layer having a thickness of 75 nm was formed on the cathode layer by depositing Compound F3 (N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine).

[0583] The OLED stack is protected from environmental conditions by encapsulating the device with a glass slide. A cavity is thereby formed which contains a getter material for further protection.

[0584] In order to evaluate the performance of the examples of the present invention relative to the prior art, the current efficiency was measured at 20°C. The current-voltage characteristics were determined using a Keithley 2635 source measurement unit by providing a voltage in V and measuring the current in mA flowing through the device under test. The voltage applied to the device varied in steps of 0.1 V in the range between 0 V and 10 V. Similarly, the brightness-voltage characteristics and CIE coordinates were measured in cd / m at various voltage values ​​using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungs stelle (DAkkS)). 2 The brightness at 15 mA / cm is determined by interpolating the brightness-voltage and current-voltage characteristics, respectively. 2 cd / A efficiency under .

[0585] In bottom-emitting devices, the emission is primarily Lambertian and is quantified as a percentage of the external quantum efficiency (EQE). To determine the efficiency EQE in %, a calibrated photodiode was used at 15 mA / cm 2 The light output of the device was measured.

[0586] In a top-emitting device, the emission is forward-oriented, 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.

[0587] The device lifetime LT was measured using a Keithley 2400 source meter at ambient conditions (20°C) and 30 mA / cm 2 Measure and record in hours.

[0588] 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 decreases to 97% of its initial value.

[0589] The increase in the operating voltage ∆U is used as a measure of the operating voltage stability of the device.

[0590] This increase is also determined during the LT measurement by subtracting the operating voltage after 1 hour of device operation from the operating voltage after 100 hours.

[0591] ∆U=[U(100 h)-U(1 h)]

[0592] The smaller the ΔU value is, the better the operating voltage stability is.

[0593] Technical Effects of the Invention

[0594] Table 1: Calculated LUMO of compounds

[0595] The LUMO energy was calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). The optimized geometry of the molecular structure as well as the HOMO and LUMO energy levels were calculated by applying the hybrid functional B3LYP and 6-31G in the gas phase. If more than one conformation is feasible, the one with the lowest overall energy is chosen.

[0596] A compound of formula (I) or formula (II), selected from one of the following compounds P1 to P15,

[0597] Wherein R' is selected from CN, and A 1 Ar 1 , A 2 Ar 2 and A 3 Ar 3 Select according to Table 8 below:

[0598] Table 8 Compounds used in the examples and their respective LUMO energy levels.

[0599]

[0600] The asterisk " ” indicates the binding position.

[0601] Table 9: Experimental data.

[0602]

[0603] Inventive Examples 1 to 7 of Table 9 exhibit lower operating voltages than Comparative Examples 1 to 2 of Table 9.

[0604] Using the same dopant in the hole injection layer and the p-type charge generation layer (Comparative Example 1) exhibited a higher operating voltage than Inventive Examples 1 to 7 in which the hole transport layer and the p-type charge generation layer did not contain the same p-type dopant.

[0605] When the LUMO level of the p-type dopant in the hole injection layer is increased compared with Comparative Example 1 (Comparative Example 2), the operating voltage is even increased compared with Comparative Example 1.

[0606] Lower operating voltage can be important for reducing power consumption and improving battery life, especially in mobile devices.

[0607] Inventive Examples 1 to 7 showed a lower voltage rise over time than Comparative Examples 1 to 3.

[0608] Using the same dopant in the hole injection layer and the p-type charge generation layer (Comparative Example 1) showed a higher voltage rise over time than Inventive Examples 1 to 7 in which the hole transport layer and the p-type charge generation layer did not contain the same p-type dopant.

[0609] When the LUMO level of the p-type dopant in the hole injection layer increases compared with Comparative Example 2 (Comparative Example 2), the voltage rise over time also increases.

[0610] Furthermore, when the LUMO level of the p-type dopant in the p-type charge generation layer is lowered, the voltage rise over time is even increased compared to Comparative Example 1.

[0611] However, when the LUMO energy level of the radialene in the hole injection layer is lower than that of the radialene of Comparative Examples 1 to 3, the voltage rise over time can be reduced, thereby being significantly improved.

[0612] It is known to those skilled in the art that the stability of more layers at the interface decreases and the voltage rise is determined by more layers at the interface. Since CGL contains n-CGL and p-CGL, those skilled in the art believe that CGL is an important factor affecting the voltage rise over time.

[0613] Thus, it could surprisingly be demonstrated that the effect of lower LUMO radialene as p-type dopant in the hole injection layer on the voltage rise over time is even higher than the effect of using lower LUMO radialene in the p-type charge generation layer.

[0614] A lower voltage rise over time may result in improved long-term stability of the electronic device.

[0615] The specific combination of elements and features in the above detailed embodiments is exemplary only; the exchange and substitution of these teachings by other teachings in the special columns / applications incorporated herein and by reference is also expressly contemplated. As will be appreciated by those skilled in the art, changes, variants and other embodiments described herein can be conceived by those skilled in the art without departing from the spirit and scope of the invention as claimed. Therefore, the above description is only by way of example and is not intended to be limiting. In the claims, the word "comprising" does not exclude other elements or steps, and the singular form "one" or "a kind" does not exclude plural indicators. The fact that specific measures are listed in mutually different dependent claims does not mean that a combination of these measures cannot be used to advantage. The scope of the invention is defined by the claims and their equivalents. In addition, the figure marks used in the specification and claims are not used to limit the scope of the invention as claimed.

Claims

1. An organic electroluminescent device, comprising an anode layer, a cathode layer, a hole injection layer, at least two light-emitting units and at least one charge generation layer, wherein at least one charge generation layer comprises a p-type charge generation layer; Each light-emitting unit comprises at least one light-emitting layer. wherein each of the at least one charge generation layer is independently disposed between two adjacent light emitting units of a group of the at least two light emitting units; wherein the hole injection layer is arranged closer to the anode layer than the p-type charge generation layer; The hole injection layer comprises a first radialene compound of formula (I) and a first hole transport host compound, wherein the first radialene compound of formula (I) is represented by the following formula: , wherein in the first radially olefin compound of formula (I): A 1 Independently selected from groups of formula (Ia): ,in Ar 1 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein Ar 1 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 Heteroaryl; wherein C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl and 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): ,in Ar 2 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein Ar 2 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 Heteroaryl; wherein 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): ,in Ar 3 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein Ar 3 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 Heteroaryl, wherein 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; in In A 1 , A 2 and A 3 wherein each R' is independently selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted 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; wherein C6 to C 18 Aryl, C6 to C 18 One or more substituents of heteroaryl and C1 to C8 alkyl are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, partially fluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy; in The LUMO energy level of the first olefin compound of formula (I) is ≤-5.20 eV; in The p-type charge generation layer comprises a second radialene compound of formula (II) and a second hole transport host compound; and The second olefin compound of formula (II) is represented by the following formula: , wherein in the second radial olefin compound of formula (II): B 1 Independently selected from groups of formula (IIa): ,in Er 1 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein Er 1 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a 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; B 2 Independently selected from groups of formula (IIb): ,in Er 2 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein Er 2 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl, and wherein 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; B 3 Independently selected from groups of formula (Ic): ,in Er 3 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein Er 3 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a 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; in In B 1 , B 2 and B 3 In the above formula, each R" is independently selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted 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; Among them, C6 to C 18 Aryl, C6 to C 18 One or more substituents of heteroaryl and C1 to C8 alkyl are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, partially fluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy; in The first radialene compound of formula (I) and the second radialene compound of formula (II) are selected to be different from each other; and The asterisk " ” indicates the binding position.

2. The organic electroluminescent device according to claim 1, wherein at least one charge generation layer comprises a p-type charge generation layer; Each light-emitting unit comprises at least one light-emitting layer. wherein each of the at least one charge generation layer is independently disposed between two adjacent light emitting units of a group of the at least two light emitting units; wherein the hole injection layer is arranged closer to the anode layer than the p-type charge generation layer; The hole injection layer comprises a first radialene compound of formula (I) and a first hole transport host compound, wherein the first radialene compound of formula (I) is represented by the following formula: , wherein in the first radially olefin compound of formula (I): A 1 Independently selected from groups of formula (Ia): ,in Ar 1 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein Ar 1 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 Heteroaryl; wherein C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl and 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): ,in Ar 2 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein Ar 2 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 Heteroaryl; wherein 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): ,in Ar 3 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein Ar 3 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 Heteroaryl, wherein 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; in In A 1 , A 2 and A 3 wherein each R' is independently selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted 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; wherein C6 to C 18 Aryl, C6 to C 18 One or more substituents of heteroaryl and C1 to C8 alkyl are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, partially fluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy; in When the hybrid functional B3LYP and 6-31G When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the LUMO energy level of the first radialene compound of the formula (I) is ≤ -5.20 eV; in The p-type charge generation layer comprises a second radialene compound of formula (II) and a second hole transport host compound; and The second olefin compound of formula (II) is represented by the following formula: , wherein in the second radial olefin compound of formula (II): B 1 Independently selected from groups of formula (IIa): ,in Er 1 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein Er 1 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a 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; B 2 Independently selected from groups of formula (IIb): ,in Er 2 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein Er 2 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl, and wherein 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; B 3 Independently selected from groups of formula (Ic): ,in Er 3 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 Heteroaryl; wherein Er 3 The one or more substituents are independently selected from D, an electron withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1 to C8 alkyl, a partially fluorinated C1 to C8 alkyl, a perfluorinated C1 to C8 alkyl, a substituted or unsubstituted C1 to C8 alkoxy, a partially fluorinated C1 to C8 alkoxy, a perfluorinated C1 to C8 alkoxy, a 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; in In B 1 , B 2 and B 3 In the above formula, each R" is independently selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted 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; Among them, C6 to C 18 Aryl, C6 to C 18 One or more substituents of heteroaryl and C1 to C8 alkyl are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, partially fluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, partially fluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy; in The first radialene compound of formula (I) and the second radialene compound of formula (II) are selected to be different from each other; and The asterisk " ” indicates the binding position.

3. An organic electroluminescent device according to claim 1 or 2, wherein the organic electroluminescent device comprises at least three light-emitting units and at least two charge generating layers, wherein each of the at least two charge generating layers is independently arranged between two adjacent light-emitting units of a group of the at least three light-emitting units; or the organic electroluminescent device comprises at least four light-emitting units and at least three charge generating layers, wherein each of the at least three charge generating layers is independently arranged between two adjacent light-emitting units of a group of the at least four light-emitting units. 4 . The organic electroluminescent device according to claim 1 , wherein the hole injection layer is in direct contact with the anode layer.

5. The organic electroluminescent device according to any one of claims 1 to 4, wherein the organic electroluminescent device further comprises a hole transport layer, wherein the hole transport layer is arranged adjacent to the hole injection layer, and preferably the hole transport layer is arranged between the light emitting unit and the hole injection layer. 6 . The organic electroluminescent device according to claim 1 , wherein the at least one charge generation layer further comprises an n-type charge generation layer. 7 . The organic electroluminescent device according to claim 1 , wherein the p-type charge generation layer of the at least one charge generation layer is arranged in direct contact with the n-type charge generation layer of the at least one charge generation layer.

8. The organic electroluminescent device according to any one of claims 1 to 7, wherein at least one light-emitting unit or all light-emitting units further comprise a hole transport layer, an electron blocking layer, a hole blocking layer and an electron transport layer in addition to the light-emitting layer.

9. The organic electroluminescent device according to any one of claims 1 to 8, wherein in the first radialene compound of formula (I) and formula (II), R' and R" are independently selected from halogen, F and CN, preferably CN.

10. The organic electroluminescent device according to any one of claims 1 to 9, wherein in the first radialene compound of formula (I), A 1 , A 2 and A 3 At least two of the above are the same; and / or in the second olefin compound of formula (II), B 1 , B 2 and B 3 At least two of the choices are the same.

11. The organic electroluminescent device according to any one of claims 1 to 10, wherein in the first radialene compound of formula (I), Ar 1 ,Ar 2 and Ar 3 is independently selected from one of the following B1 to B64 groups, and / or in the second olefin compound of formula (II), Er 1 , Er 2 and Er 3 Independently selected from one of the following B1 to B64 groups: The asterisk " ” indicates the binding position.

12. The organic electroluminescent device according to claim 11, wherein in the first radialene compound of formula (I), Ar 1 ,Ar 2 and Ar 3 is independently selected from one of the following groups B1 to B8, B10 to B17, B19 to B21, B24 to B26, B33, B34, B37, B40, B43, B58 to B62 and B64, and / or in the second olefin compound of formula (II), Er 1 , Er 2 and Er 3 is independently selected from one of the following groups B1 to B8, B10 to B17, B19 to B21, B24 to B26, B33, B34, B37, B40, B43, B58 to B62 and B64. Preferably, in the first olefin compound of formula (I), Ar 1 ,Ar 2 and Ar 3 is independently selected from one of the following B2, B3, B4, B11, B13, B37, B43, B58, B59, B60, B61, B63 and B64 groups, and / or in the second olefin compound of formula (II), Er 1 , Er 2 and Er 3 Independently selected from one of the following B2, B3, B4, B11, B13, B37, B43, B58, B59, B60, B61, B63 and B64 groups.

13. The organic electroluminescent device according to claim 12, wherein in the first radialene compound of formula (I), Ar 1 ,Ar 2 and Ar 3 is independently selected from one of the following B1 to B64 groups, and preferably each R' and / or R" is selected from CN, preferably wherein in the first olefin compound of formula (I) Ar 1 ,Ar 2 and Ar 3 is independently selected from one of the following groups B1 to B5, B7, B8, B10 to B13, B15 to B17, B19 to B21, B37, B43, B58 to B61, B63 and B64, and / or in the second olefin compound of formula (II), Er 1 , Er 2 and Er 3 Independently selected from one of the following B1 to B5, B7, B8, B10 to B13, B15 to B17, B19 to B21, B37, B43, B58 to B61, B63 and B64 groups, and wherein preferably each R' and / or R" is selected from CN.

14. The organic electroluminescent device according to any one of claims 1 to 13, wherein in the first radialene compound of formula (I), Ar 1 ,Ar 2 and Ar 3 is independently selected from the group according to the following formula (III), and / or in the second olefin compound of formula (II), Er 1 , Er 2 and Er 3 is independently selected from a group according to the following formula (III), and wherein preferably each R' and / or R" is selected from CN: in E 1 From The CW 1 or N; E 2 From The CW 2 or N; E 3 From The CW 3 or N; E 4 From The CW 4 or N; E 5 From The CW 5 or N; W 1 , W 2 , W 3 , W 4 and W 5 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, CF3, 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, Where W 1 , W 2 , W 3 , W 4 and W 5 The 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; The asterisk " ” indicates the binding position.

15. The organic electroluminescent device according to claim 14, wherein in formula (III) W 1 , W 2 , W 3 , W 4 and W 5 Independently selected from electron withdrawing groups, CN, halogen, Cl, F, NO2, partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, partially fluorinated or perfluorinated C1 to C6 alkoxy, OCF3, D or H, and preferably each R' and / or R" is CN.

16. The organic electroluminescent device according to any one of claims 1 to 15, wherein the second radialene of formula (II) has a calculated LUMO energy level, and the first radialene of formula (I) has a calculated LUMO energy level, wherein the LUMO energy level is calculated by applying the hybrid functional B3LYP and 6-31G in the gas phase. The basis sets were calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany).

17. The organic electroluminescent device according to any one of claims 1 to 16, wherein - When the hybrid functional B3LYP and 6-31G are applied in the gas phase When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the calculated LUMO level of the first radialene compound of formula (I) is ≤-5.21 eV, preferably ≤-5.22 eV; further preferably ≤-5.25 eV; further preferably ≤-5.29 eV; or - When the hybrid functional B3LYP and 6-31G are applied in the gas phase When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the calculated LUMO level of the first axial olefin compound of the formula (I) is in the range of ≤-5.20 eV to ≥-5.75 eV, preferably in the range of ≤-5.20 eV to ≥-5.70 eV; further preferably in the range of ≤-5.20 eV to ≥-5.65 eV, also preferably in the range of ≤-5.20 eV to ≥-5.60 eV, further preferably in the range of ≤-5.22 eV to ≥-5.60 eV, further preferably in the range of ≤-5.25 eV to ≥-5.55 eV, more preferably in the range of ≤-5.25 eV to ≥-5.50 eV, and even more preferably in the range of ≤-5.25 eV to ≥-5.45 eV.

18. The organic electroluminescent device according to any one of claims 1 to 17, wherein when the hybrid functional B3LYP and 6-31G When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the calculated HOMO energy level of the first hole transport host compound is in the range of ≤-4.27 eV to ≥-5.1 eV, preferably in the range of <-4.3 eV and >-5.0 eV, further preferably in the range of <-4.5 eV and >-5.0 eV, also preferably in the range of <-4.5 eV and >-4.9 eV, and further preferably in the range of <-4.6 eV and >-4.9 eV.

19. The organic electroluminescent device according to any one of claims 1 to 18, wherein - When the hybrid functional B3LYP and 6-31G are applied in the gas phase When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the calculated LUMO energy level of the second olefin compound of formula (II) is ≤ -5.21 eV; or - When the hybrid functional B3LYP and 6-31G are applied in the gas phase When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the calculated LUMO energy level of the second olefin compound of formula (II) is in the range of ≤-4.60 eV, more preferably in the range of ≤-4.75 eV; further preferably in the range of ≤-5.00 eV; also preferably in the range of ≤-5.10 eV; further preferably in the range of ≤-5.15 eV; more preferably in the range of ≤-5.19 eV.

20. The organic electroluminescent device according to any one of claims 1 to 19, wherein the calculated LUMO energy level of the second radialene compound of formula (II) is selected to be higher than the LUMO energy level of the first radialene compound of formula (I).

21. The organic electroluminescent device according to any one of claims 1 to 20, wherein when the hybrid functional B3LYP and 6-31G When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the calculated LUMO level of the second olefin compound of formula (II) in the p-type charge generation layer is in the range of ≤-5.00 eV to ≥-5.75 eV, preferably in the range of ≤-5.10 eV to ≥-5.70 eV; further preferably in the range of ≤-5.15 eV to ≥-5.65 eV, further preferably in the range of ≤-5.19 eV to ≥-5.65 eV, further preferably in the range of ≤-5.20 eV to ≥-5.60 eV, more preferably in the range of ≤-5.22 eV to ≥-5.55 eV, still more preferably in the range of ≤-5.22 eV to ≥-5.55 eV, even more preferably in the range of ≤-5.22 eV to ≥-5.60 eV, and even more preferably in the range of ≤-5.22 eV to ≥-5.70 eV. eV to ≥-5.45 eV.

22. The organic electroluminescent device according to any one of claims 1 to 21, wherein when the hybrid functional B3LYP and 6-31G When the basis set is calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the calculated HOMO energy level of the second hole transport host compound is in the range of ≤-4.27 eV to ≥-5.1 eV, preferably in the range of <-4.3 eV and >-5.0 eV, further preferably in the range of <-4.5 eV and >-5.0 eV, also preferably in the range of <-4.5 eV and >-4.9 eV, and further preferably in the range of <-4.6 eV and >-4.9 eV.

23. The organic electroluminescent device according to any one of claims 1 to 22, wherein the compound of the first radialene compound of formula (I) and the compound of the second radialene compound of formula (II) are independently represented by one of the following formulae (IVa) to (IVh): Among them, Ar 1 ,Ar 2 ,Ar 3 and R' are independently selected from halogen, F and CN, preferably CN; wherein the first radial ene compound of formula (I) and the second radial ene compound of formula (II) are selected to be different from each other.

24. An electronic device, comprising the organic electroluminescent device according to any one of claims 1 to 23, wherein the electronic device is preferably a display device, a light-emitting device, a thin film transistor, a battery, a display device or a photovoltaic device, preferably a light-emitting device, and preferably the electronic device is a part of a display device or a lighting device.

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