Organic electroluminescent device comprising compounds of formulations (i) and (II), and display device comprising organic electroluminescent

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.

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 the organic electroluminescent device. Background Art

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

[0003] When a voltage is applied to the anode and the cathode, holes injected from the anode move through the HTL to the EML, and electrons injected from the cathode move through the ETL to the EML. The holes and electrons recombine in the EML to generate excitons. When the excitons decay 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 an organic light-emitting diode can be affected by the characteristics of the semiconductor layer, and in particular, can be affected by the characteristics of the compounds contained in the semiconductor layer.

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

[0006] One aspect of the present invention provides an organic electroluminescent device comprising an anode layer, a cathode layer, a first light-emitting layer, a second light-emitting layer, a hole injection layer, and a first charge generation layer,

[0007] wherein the hole injection layer is in direct contact with the anode layer;

[0008] wherein the first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer;

[0009] wherein the first charge generation layer comprises a first n-type charge generation layer and a first p-type charge generation layer;

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

[0011] wherein the n-type charge generation layer comprises a metal dopant and a matrix compound,

[0012] wherein the first p-type charge generating layer comprises a second hole transport host compound and a compound of formula (I);

[0013]

[0014] Wherein in formula (I),

[0015] -A 1 independently selected from groups of formula (Ia):

[0016]

[0017] Among them, Ar 1 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 heteroaryl;

[0018] For Ar 1 In the case of substitution, one or more substituents are independently selected from D, electron withdrawing groups, halogen, Cl, F, CN, -NO2, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C6 to C 30 heteroaryl; and

[0019] 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;

[0020] -A 2 independently selected from groups of formula (Ib):

[0021]

[0022] Among them, Ar 2 independently selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 36 heteroaryl;

[0023] For Ar 2In the case of being substituted, one or more substituents are independently selected from D, an electron-withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1-C8 alkyl group, a partially fluorinated C1-C8 alkyl group, a perfluorinated C1-C8 alkyl group, a substituted or unsubstituted C1-C8 alkoxy group, a partially fluorinated C1-C8 alkoxy group, a perfluorinated C1-C8 alkoxy group, a substituted or unsubstituted C6-C 30 aryl group and a substituted or unsubstituted C6-C 30 heteroaryl group; and

[0024] wherein one or more substituents of the C6-C 30 aryl group, C6-C 30 heteroaryl group, C1-C8 alkyl group, and C1-C8 alkoxy group are independently selected from D, an electron-withdrawing group, a halogen, Cl, F, CN, -NO2, a partially fluorinated C1-C8 alkyl group, a perfluorinated C1-C8 alkyl group, a partially fluorinated C1-C8 alkoxy group, and a perfluorinated C1-C8 alkoxy group;

[0025] -A 3 is independently selected from the groups of formula (Ic):

[0026]

[0027] wherein Ar 3 is independently selected from a substituted or unsubstituted C6-C 36 aryl group and a substituted or unsubstituted C2-C 36 heteroaryl group;

[0028] wherein for Ar 3 in the case of being substituted, one or more substituents are independently selected from D, an electron-withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1-C8 alkyl group, a partially fluorinated C1-C8 alkyl group, a perfluorinated C1-C8 alkyl group, a substituted or unsubstituted C1-C8 alkoxy group, a partially fluorinated C1-C8 alkoxy group, a perfluorinated C1-C8 alkoxy group, a substituted or unsubstituted C6-C 30 aryl group and a substituted or unsubstituted C6-C 30 heteroaryl group; and

[0029] wherein one or more substituents of the C6-C 30 aryl group, C6-C 30 heteroaryl group, C1-C8 alkyl group, and C1-C8 alkoxy group are independently selected from D, an electron-withdrawing group, a halogen, Cl, F, CN, -NO2, a partially fluorinated C1-C8 alkyl group, a perfluorinated C1-C8 alkyl group, a partially fluorinated C1-C8 alkoxy group, and a perfluorinated C1-C8 alkoxy group;

[0030] and wherein in A1 and A 2 and A 3 each R' is independently selected from substituted or unsubstituted C6-C 18 aryl, C3-C 18 heteroaryl, an electron-withdrawing group, substituted or unsubstituted C1-C8 alkyl, partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, halogen, F, and CN;

[0031] wherein one or more substituents of the C6-C 18 aryl, C6-C 18 heteroaryl, and C1-C8 alkyl are independently selected from D, an electron-withdrawing group, halogen, Cl, F, CN, -NO2, partially fluorinated C1-C6 alkyl, perfluorinated C1-C6 alkyl, partially fluorinated C1-C6 alkoxy, and perfluorinated C1-C6 alkoxy;

[0032] wherein the hole injection layer comprises a first hole transport matrix compound and a compound of formula (II), and the compound of formula (II) is a metal compound selected from metal salts or metal complexes, and the metal salts or metal complexes comprise metal cations and at least one monoanion composed of at least 20 covalently bonded atoms and / or at least one monoanion ligand composed of at least 20 covalently bonded atoms.

[0033] It should be noted that unless otherwise indicated, throughout the application and claims, any A n 、B n 、R n 、X n etc. always refer to the same moiety.

[0034] In this specification, when no definition is provided otherwise, "substituted" means substituted with deuterium, C1-C 12 alkyl, and C1-C 12 alkoxy.

[0035] However, in this specification, "aryl-substituted" means substituted with one or more aryl groups, and the aryl groups themselves may be substituted with one or more aryl and / or heteroaryl groups.

[0036] Accordingly, in this specification, "heteroaryl-substituted" means substituted with one or more heteroaryl groups, and the heteroaryl groups themselves may be substituted with one or more aryl and / or heteroaryl groups.

[0037] In this specification, when no definition is provided otherwise, "alkyl group" means a saturated aliphatic hydrocarbon group. The alkyl group may be a C1-C 12 alkyl group. More specifically, the alkyl group may be a C1-C 10An alkyl group or a C1-C6 alkyl group. For example, a C1-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.

[0038] 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.

[0039] The term "cycloalkyl" refers to a saturated hydrocarbon group derived from a cycloalkane by formally removing one 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.

[0040] The term "hetero" should be understood that at least one carbon atom in a structure that can be formed by covalently bonded carbon atoms is replaced by another polyvalent atom. Preferably, the heteroatom is selected from B, Si, N, P, O, S; more preferably from N, P, O, S.

[0041] In this specification, an "aryl group" refers to a hydrocarbon group that can be produced by formally removing one hydrogen atom from an aromatic ring in the corresponding aromatic hydrocarbon. An aromatic hydrocarbon refers to a hydrocarbon containing at least one aromatic ring or aromatic ring system. An aromatic ring or aromatic ring system refers to a planar ring or ring system of covalently bonded carbon atoms, wherein the planar ring or ring system contains a conjugated system of delocalized electrons that satisfies Hückel's rule. Examples of aryl groups include monocyclic groups such as phenyl or tolyl, polycyclic groups containing multiple aromatic rings connected by single bonds such as biphenyl, and polycyclic groups containing fused rings such as naphthyl or fluoren-2-yl.

[0042] Similarly, a heteroaryl should be understood, in particular when appropriate, as a group derived by formally removing one ring hydrogen from such a ring in a compound containing at least one heteroaromatic ring.

[0043] A heterocycloalkyl should be understood, in particular when appropriate, as a group derived by formally removing one ring hydrogen from such a ring in a compound containing at least one saturated cycloalkyl ring.

[0044] The term "fused aryl ring" or "condensed aryl ring" should be understood that when two aryl rings share at least two common sp 2 hybridized carbon atoms, they are considered fused or condensed.

[0045] The term "cyano moiety" refers to a CN substituent.

[0046] The term "electron-withdrawing group" refers to a chemical group in a molecule that can pull electrons away from an adjacent part of the molecule. The distance over which an electron-withdrawing group can exert its effect, i.e., the number of bonds across which the electron-withdrawing effect extends, is enhanced by a conjugated π-electron system such as an aromatic system. 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 groups, partially fluorinated or perfluorinated alkoxy groups, and partially fluorinated or perfluorinated C1 to C6 alkoxy groups.

[0047] In this specification, a single bond means a direct bond.

[0048] The term "n-type charge generation layer" is sometimes also referred to in the art as n-CGL or electron generation layer and is intended to include both of these.

[0049] The term "p-type charge generation layer" is sometimes also referred to in the art as p-CGL or hole generation layer and is intended to include both of these.

[0050] The terms "free of", "not containing", "not comprising" do not exclude impurities that may be present in the compound prior to deposition. The impurities have no technical effect on the purposes to be achieved by the present invention.

[0051] The term "contact sandwich" refers to a three-layer arrangement in which an intermediate layer is in direct contact with two adjacent layers.

[0052] The terms "light-absorbing layer" and "photoabsorbing layer" are used synonymously.

[0053] The terms "light-emitting layer", "layer that emits light", and "light-emitting layer" are used synonymously.

[0054] The terms "OLED", "organic light-emitting diode", and "organic light-emitting device" are used synonymously.

[0055] The terms "anode", "anode layer", and "anode electrode" are used synonymously.

[0056] The terms "cathode", "cathode layer", and "cathode electrode" are used synonymously.

[0057] The term "top-emitting device" should be understood to mean an organic electronic device that emits light through the cathode layer.

[0058] The term "bottom-emitting device" should be understood to mean an organic electronic device that emits light through the substrate.

[0059] In this specification, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied. Due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0060] In addition, the electronic property refers to the ability to accept electrons when an electric field is applied. Due to the conductive property according to the lowest unoccupied molecular orbital (LUMO) energy level, the electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0061] Advantageous Effects

[0062] Surprisingly, it has been found that the organic electroluminescent device according to the present invention solves the fundamental problem of the present invention by enabling the device to be superior to the organic electroluminescent devices known in the prior art in multiple aspects, particularly in terms of improving the operating voltage, improving the stability of the operating voltage over time, and improving the current efficiency.

[0063] According to one embodiment of the present invention, when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the calculated LUMO energy level of the compound of formula (I) represented on an absolute scale with the reference vacuum energy level being zero is ≤ -4.90 eV, preferably ≤ -5.00 eV, more preferably ≤ -5.05 eV, and most preferably ≤ -5.10 eV.

[0064] According to one embodiment of the present invention, when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the calculated LUMO energy level of the compound of formula (I) represented on an absolute scale with the reference vacuum energy level being zero is in the range of ≤ -4.90 eV to ≥ -5.75 eV, preferably ≤ -5.00 eV to ≥ -5.75 eV, more preferably ≤ -5.05 eV to ≥ -5.75 eV, and most preferably ≤ -5.10 eV to ≥ -5.75 eV.

[0065] According to one embodiment of the present invention, relative to the total weight of the p-type charge generation layer, the amount of the compound of formula (I) present in the p-type charge generation layer is ≥ 1 wt% and ≤ 20 wt%, preferably ≥ 5 wt% and ≤ 10 wt%.

[0066] According to one embodiment, the compound of formula (I) is an organic p-type dopant.

[0067] According to one embodiment, in the compound of formula (I), the following compounds are excluded: 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-triyltris(cyanomethylidene))tris(2,3,5,6-tetrafluorobenzonitrile); (2E,2'E,2"E)-2,2',2"-(cyclopropane-1,2,3-triyl)tris(2-(2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)phenyl)acetonitrile); α,α',α"-1,2,3-cyclopropanetriyltris[2,3,4,5,6-pentafluorobenzeneacetonitrile]; and α,α',α"-1,2,3-cyclopropanetriyltris[2,3,5,6-tetrafluoro-4-(trifluoromethyl)benzeneacetonitrile].

[0068] According to one embodiment of the present invention, the compound of formula (I) contains at least one CF3 group.

[0069] According to one embodiment of the present invention, the compound of formula (I) contains one to three CF3 groups.

[0070] According to one embodiment of the present invention, the compound of formula (I) contains less than nine cyano moieties.

[0071] According to one embodiment of the present invention, the compound of formula (I) contains less than eight cyano moieties.

[0072] According to one embodiment of the present invention, the compound of formula (I) contains at least one cyano moiety.

[0073] According to one embodiment of the present invention, the compound of formula (I) contains at least two cyano moieties.

[0074] According to one embodiment of the present invention, the compound of formula (I) contains at least three cyano moieties.

[0075] According to one embodiment of the present invention, the compound of formula (I) contains at least four cyano moieties.

[0076] According to one embodiment of the present invention, the compound of formula (I) contains 3 to 8 cyano moieties.

[0077] According to one embodiment of the present invention, the compound of formula (I) contains 3 to 7 cyano moieties.

[0078] According to one embodiment of the present invention, the compound of formula (I) contains 4 to 7 cyano moieties.

[0079] According to one embodiment of the present invention, Formula (I) contains at least 10 fluorine atoms, at least 12 fluorine atoms, at least 13 fluorine atoms, at least 14 fluorine atoms, at least 15 fluorine atoms, at least 16 fluorine atoms, at least 17 fluorine atoms or at least 18 fluorine atoms.

[0080] According to one embodiment of the present invention, Formula (I) contains 10 to 20 fluorine atoms, or 10 to 18 fluorine atoms, or 12 to 18 fluorine atoms.

[0081] According to one embodiment of the present invention, Formula (I) contains 4 to 7 cyano moieties and 12 to 18 fluorine atoms.

[0082] According to one embodiment of the present invention, in Formula (I), A 1 , A 2 and A 3 at least two of which are selected to be the same.

[0083] According to one embodiment of the present invention, in Formula (I), A 2 and A 3 are the same.

[0084] According to one embodiment of the present invention, in Formula (I), A 1 , A 2 and A 3 are the same.

[0085] According to one embodiment of the present invention, in Formula (I), A 1 is different from A 2 and / or A 3 .

[0086] According to one embodiment of the present invention, in Formula (I), Ar 1 , Ar 2 and Ar 3 are independently selected from substituted or unsubstituted C6 to C 12 aryl and substituted or unsubstituted C3 to C 12 heteroaryl.

[0087] According to one embodiment of the present invention, in Formula (I), Ar 1 , Ar 2 and Ar 3 are independently selected from substituted or unsubstituted C6 aryl and substituted or unsubstituted C3 to C5 heteroaryl.

[0088] According to one embodiment of the present invention, in Formula (I), Ar 1 , Ar 2 and Ar 3The substituents on it are independently selected from electron-withdrawing groups, halogens, Cl, F, CN, partially fluorinated alkyl groups, and perfluorinated alkyl groups.

[0089] According to one embodiment of the present invention, in formula (I), Ar 1 , Ar 2 and Ar 3 The substituents on are independently selected from Cl, F, CN, and perfluorinated alkyl groups.

[0090] According to one embodiment of the present invention, in formula (I), Ar 1 , Ar 2 and Ar 3 The substituents on are independently selected from F, CN, and perfluorinated alkyl groups.

[0091] According to one embodiment of the present invention, in formula (I), Ar 1 , Ar 2 and Ar 3 The substituents on are independently selected from F, CN, and CF3.

[0092] According to one embodiment of the present invention, in formula (I), Ar 1 , Ar 2 and Ar 3 The substituents on are independently selected from CN and CF3.

[0093] According to one embodiment of the present invention, in formula (I), Ar 1 , Ar 2 and Ar 3 The substituents on are independently selected from CN.

[0094] According to one embodiment of the present invention, in formula (I), Ar 1 , Ar 2 and Ar 3 The substituents on are independently selected from CF3.

[0095] According to one embodiment of the present invention, in formula (I), Ar 1 , Ar 2 and Ar 3 Each independently contains more than one and less than five substituents, preferably more than two and less than four substituents, for example, 4 substituents.

[0096] According to one embodiment of the present invention, in formula (I), each R' is independently selected from electron-withdrawing groups, partially fluorinated C1-C8 alkyl groups, perfluorinated C1-C8 alkyl groups, halogens, F, and CN.

[0097] According to one embodiment of the present invention, in formula (I), each R' is independently selected from partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, halogen, F, and CN.

[0098] According to one embodiment of the present invention, in formula (I), each R' is independently selected from CF3, F, and CN.

[0099] According to one embodiment of the present invention, in formula (I), each R' is CN.

[0100] According to one embodiment of the present invention, in formula (I), Ar 1 、Ar 2 and Ar 3 are independently selected from the groups according to the following formula (III), and preferably each R' is selected from CN:

[0101]

[0102] where

[0103] E 1 is selected from CW 1 or N;

[0104] E 2 is selected from CW 2 or N;

[0105] E 3 is selected from CW 3 or N;

[0106] E 4 is selected from CW 4 or N;

[0107] E 5 is selected from CW 5 or N;

[0108] W 1 、W 2 、W 3 、W 4 and W 5 (if present) are independently selected from electron-withdrawing groups, CN, halogen, Cl, F, NO2, substituted or unsubstituted C1-C8 alkyl, partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, substituted or unsubstituted C1-C8 alkoxy, partially fluorinated C1-C8 alkoxy, perfluorinated C1-C6 alkoxy, OCF3, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl, D, or H,

[0109] wherein one or more substituents are independently selected from D, halogen, Cl, F, CN, NO2, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy,

[0110] The asterisk "*" indicates the binding position.

[0111] According to one embodiment of the present invention, in formula (III), W 1 、W 2 、W 3 、W 4 and W 5 (if present) are independently selected from electron withdrawing groups, CN, halogen, Cl, F, NO2, partially fluorinated or perfluorinated C1 to C8 alkyl, partially fluorinated or perfluorinated C1 to C6 alkoxy, D or H, wherein preferably each R' is selected from CN.

[0112] According to one embodiment of the present invention, in formula (I), Ar 1 、Ar 2 and / or Ar 3 are independently selected from B1 to B64, and preferably each R' is selected from CN:

[0113]

[0114]

[0115] The asterisk "*" indicates the binding position.

[0116] According to one embodiment, in the compound of formula (I), Ar 1 or 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, preferably in the compound of formula (I), Ar 1 or Ar 1 、Ar 2 and Ar 3 Independently selected from one of the following groups B2, B3, B4, B11, B13, B37, B43, B58, B59, B60, B61, B63 and B64.

[0117] According to one embodiment, in the compound of formula (I), Ar 1 or Ar 1 、Ar 2 and Ar 3Independently selected from one of the following groups B1 to B64, and preferably each R' and / or R" is selected from CN, preferably in the compound of formula (I), Ar 1 or Ar 1 、Ar 2 and Ar 3 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 preferably each R' and / or R" is selected from CN.

[0118] According to one embodiment, in the compound of formula (I), Ar 1 or Ar 1 、Ar 2 and Ar 3 Independently selected from one of the following groups:

[0119]

[0120] Wherein the asterisk "*" represents the binding position; and preferably each R' and / or R" is selected from CN.

[0121] According to one embodiment, in the compound of formula (I), Ar 1 or Ar 1 、Ar 2 and Ar 3 Independently selected from one of the following groups:

[0122]

[0123] Wherein the asterisk "*" represents the binding position; and preferably each R' and / or R" is selected from CN.

[0124] According to one embodiment, in the compound of formula (I), Ar 1 or Ar 1 、Ar 2 and Ar 3 Independently selected from one of the following groups:

[0125]

[0126] Wherein the asterisk "*" represents the binding position.

[0127] According to one embodiment, in the compound of formula (I), Ar 1 or Ar 1 、Ar 2 and Ar 3 Independently selected from one of the following groups:

[0128]

[0129] wherein the asterisk "*" represents the bonding position; and each R' is independently selected from CN.

[0130] According to one embodiment, the compound of formula (I) is selected from one of the following compounds BR1 to BR14, wherein R' is selected from CN, and A 1 of Ar 1 、A 2 of Ar 2 and A 3 of Ar 3 are selected as follows:

[0131]

[0132]

[0133] wherein the asterisk "*" represents the bonding position.

[0134] According to one embodiment, the compound of formula (I) is selected from one of the following compounds BR2 to BR6, wherein R' is selected from CN, and A 1 of Ar 1 、A 2 of Ar 2 and A 3 of Ar 3 are selected as follows:

[0135]

[0136]

[0137] wherein the asterisk "*" represents the bonding position.

[0138] According to one embodiment of the present invention, the compound of formula (I) is represented by one of the following formulas (IIIa) to (IIIh):

[0139]

[0140]

[0141] wherein Ar 1 、Ar 2 、Ar 3 and R' are independently selected as above.

[0142] According to one embodiment of the present invention, the hole injection layer comprises a mixture of at least two compounds selected from the compounds of formulas (IIIa) to (IIIh) as defined above as the compound of formula (I).

[0143] According to one embodiment, the LUMO energy level of the compound of formula (II) is ≥ -7.0 eV to ≤ -1.5 eV, which is implemented in the ORCA 5.0.3-f.1 version (Department of Theoretical and Spectroscopic Chemistry, Max Planck Institute for Coal Research, Kaiser Wilhelm Platz 1, 45470 Muelheim / Ruhr, Germany), and the calculation is carried out by applying the hybrid functional B3LYP in the gas phase, using the Def2-TZVP basis set and the SDD effective core potential (ECP) for metals.

[0144] According to a preferred embodiment, the LUMO energy level of the compound of formula (II) is ≥ -6.5 eV to ≤ -1.7 eV, or ≥ -6.0 eV to ≤ -2.0 eV, or ≥ -5.9 eV to ≤ -2.3 eV, or ≥ -5.8 eV to ≤ -2.7 eV, or ≥ -5.7 eV to ≤ -3.9 eV, or ≥ -5.6 eV to ≤ -4.2 eV, or preferably ≥ -5.5 eV to ≤ -4.3 eV.

[0145] According to one embodiment, the compound of formula (II) contains metal cations selected from Ce, Cu, Ag, alkali metals, alkaline earth metals, Bi, Al, Ga, In, Zr, Hf, Cr and / or Fe.

[0146] According to one embodiment, the compound of formula (II) contains metal cations selected from Ce, Cu, Ag, Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, Bi, In and / or Fe, preferably selected from Ce(IV), Cu(II), Ag(I), Li(I), Na(I), K(I), Rb(I), Cs(I), Be(II), Mg(II), Ca(II), Sr(II), Ba(II), Bi(III), In(III), Cr(III) and / or Fe(III).

[0147] According to one embodiment, the compound of formula (II) contains metal cations selected from Ce, Cu, Ag, Na, Cs, Bi and / or Fe, preferably selected from Ce(IV), Cu(II), Ag(I), Na(I), Cs(I), Bi(III), chromium(III) and / or iron(III).

[0148] According to one embodiment, the compound of formula (II) contains metal cations selected from Ce, Cu and / or Fe, preferably selected from Ce(IV), Cu(II) and / or Fe(III).

[0149] According to one embodiment, the compound of formula (II) is a metal complex.

[0150] According to one embodiment, the compound of formula (II) is a metal complex comprising a metal cation selected from Ce, Cu and / or Fe, preferably selected from Ce(IV), Cu(II) and / or Fe(III).

[0151] According to one embodiment, the compound of formula (II) is a metal complex having a LUMO energy level of ≥ -7.00 eV to ≤ -1.50 eV, which is implemented in the ORCA 5.0.3-f.1 version (Department of Theoretical and Spectroscopic Chemistry, Max Planck Institute for Coal Research, Kaiser Wilhelm Platz 1, 45470 Muelheim / Ruhr, Germany), and the calculation is carried out by applying the hybrid functional B3LYP in the gas phase, using the Def2-TZVP basis set and the SDD effective core potential (ECP) of the metal, wherein the metal complex comprises a metal cation selected from Ce, Fe and / or Cu, preferably Ce(IV), Cu(II) and / or Fe(III).

[0152] According to one embodiment, the compound of formula (II) comprises at least one CF3 group.

[0153] According to one embodiment, the compound of formula (II) comprises at least one CF3 group not bound to oxygen.

[0154] According to one embodiment, the compound of formula (II) comprises at least one monoanion composed of at least 20 covalently bonded atoms and / or at least one monoanionic ligand composed of at least 20 covalently bonded atoms, wherein the monoanion or the monoanionic ligand is L according to formula (IV) - is represented by, or the compound of formula (II) is represented by formula (IIa):

[0155]

[0156] (IIa), wherein

[0157] M is a metal ion;

[0158] p is the valence of M;

[0159] w is n;

[0160] wherein L - can be optionally the same or different;

[0161] wherein the compound of formula (IIa) may optionally comprise an auxiliary ligand (AL) coordinated to the metal cation or metal cation M p+ ;

[0162] wherein L - is represented by the following formula:

[0163]

[0164] m, n, p and q are independently selected from 0 or 1;

[0165] r, s, t and u are independently selected from 0 or 1;

[0166] At least one of r, s, t, and u is 1;

[0167] Z is selected from CR 1 , C, O, N, B;

[0168] If Z is selected from O, then n, p, q and are selected from 0, and s, t and u are selected from 0;

[0169] If Z is selected from N or CR 1 , then p and q are selected from 0, and t and u are selected from 0;

[0170] If Z is selected from C, then q is selected from 0, and u is selected from 0;

[0171] If Z is selected from B, then n, m, p and q are selected from 1, and r, s, t and u are selected from 1;

[0172] A 1 、A 2 、A 3 and A 4 Independently selected from C=O, CO, C=NR 2 、C-NR 3 , SO, SO2 or P(=O)R 4 ;

[0173] If A 1 、A 2 、A 3 and A 4 Selected from CO or C-NR 3 and Z is selected from N, O or CR 1 , or A 1 、A 2 、A 3 and A 4 Selected from CO or C-NR 3 And Z is selected from C, then Z can be 1 、A 2 、A 3 and A 4 Formation of double bonds;

[0174] and wherein optionally A 1 、A 2 、A 3 and A 4Two of them together can form a substituted or unsubstituted heterocycle or a substituted or unsubstituted carbocycle with Z, or optionally A 1 、A 2 、A 3 and A 4 One of them can form a substituted or unsubstituted heterocycle or a substituted or unsubstituted carbocycle with Z,

[0175] where one or more substituents on the heterocycle or carbocycle are independently selected from D, an electron-withdrawing group, a halogen, F, CN, NO2, SF5, an isonitrile, an ester group, a carboxyl group, a carbonyl group, an acyl group, a thio group, a sulfinyl group, a sulfonyl group, a phosphine group, a substituted or unsubstituted alkyl group, a partially perfluorinated C1 to C 12 alkyl group, a perfluorinated C1 to C 12 alkyl group, CF3, a partially perfluorinated C1 to C6 alkoxy group, a perfluorinated C1 to C6 alkoxy group, OCF3, a substituted or unsubstituted C6 to C 40 aryl group, a substituted or unsubstituted C2 to C 40 heteroaryl group, a substituted or unsubstituted C3 to C 30 carbocyclic group or a substituted or unsubstituted C2 to C 30 heterocyclic group;

[0176] R 1 is selected from H, D, an electron-withdrawing group, a halogen, Cl, F, CN, NO2, SF5, an isonitrile, an ester group, a carboxyl group, a carbonyl group, an acyl group, a thio group, a sulfinyl group, a sulfonyl group, a phosphine group, a substituted or unsubstituted C1 to C 12 alkyl group, a partially perfluorinated C1 to C 12 alkyl group, a perfluorinated C1 to C 12 alkyl group, CF3, a substituted or unsubstituted C1 to C 12 alkoxy group, a partially perfluorinated C1 to C6 alkoxy group, a perfluorinated C1 to C6 alkoxy group, CF3, a substituted or unsubstituted C6 to C 40 aryl group, a substituted or unsubstituted C2 to C 40 heteroaryl group, a substituted or unsubstituted C3 to C 30 carbocyclic group, a substituted or unsubstituted C3 to C 30 heterocyclic group;

[0177] where one or more substituents on R 1 are independently selected from D, an electron-withdrawing group, a halogen, F, CN, NO2, SF5, an isonitrile, an ester group, a carboxyl group, a carbonyl group, an acyl group, a thio group, a sulfinyl group, a sulfonyl group, a phosphine group, a partially perfluorinated C1 to C 12 alkyl group, a perfluorinated C1 to C 12Alkyl, CF3, partially perfluorinated C1-C6 alkoxy, perfluorinated C1-C6 alkoxy, OCF3, =N;

[0178] R 2 , R 3 and R 4 are independently selected from H, D, electron-withdrawing groups, halogen, Cl, F, CN, ester groups, carboxyl groups, carbonyl groups, acyl groups, thio groups, sulfinyl groups, sulfonyl groups, phosphine groups, substituted or unsubstituted alkyl, partially perfluorinated C1-C 12 alkyl, perfluorinated C1-C 12 alkyl, CF3, substituted or unsubstituted C1-C6 alkoxy, partially perfluorinated C1-C6 alkoxy, perfluorinated C1-C6 alkoxy, OCF3, substituted or unsubstituted C6-C 40 aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C3-C 30 carbocyclic group, substituted or unsubstituted C2-C 30 heterocyclic group,

[0179] wherein the substituents on R 2 , R 3 and R 4 are independently selected from D, electron-withdrawing groups, halogen, Cl, F, CN, NO2, SF5, isonitrile, ester groups, carboxyl groups, carbonyl groups, acyl groups, thio groups, sulfinyl groups, sulfonyl groups, phosphine groups, partially perfluorinated C1-C 12 alkyl, perfluorinated C1-C 12 alkyl, CF3, partially perfluorinated C1-C6 alkoxy, perfluorinated C1-C6 alkoxy, OCF3;

[0180] R a , R b , R c and R d are independently selected from H, D, electron-withdrawing groups, halogen, F, Cl, CN, substituted or unsubstituted C1-C 12 alkyl, partially perfluorinated C1-C 12 alkyl, perfluorinated C1-C 12 alkyl, CF3, substituted or unsubstituted C6-C 40 aryl, substituted or unsubstituted C2-C 30 heteroaryl, substituted or unsubstituted C3-C 40 carbocyclic group, substituted or unsubstituted C2-C 30 heterocyclic group, O, S, N, NR 5 , substituted or unsubstituted amine groups having 0 to 20 carbon atoms;

[0181] wherein R a 、R b 、R c and R d one or more substituents on are independently selected from an electron-withdrawing group, halogen, F, CN, NO2, SF5, isonitrile, ester group, carboxyl group, carbonyl group, acyl group, thio group, sulfinyl group, sulfonyl group, phosphine group, partially perfluorinated C1 to C 12 alkyl, perfluorinated C1 to C 12 alkyl, partially perfluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy, OCF3;

[0182] wherein R 5 is selected from substituted or unsubstituted C6 to C 40 aryl, substituted or unsubstituted C2 to C 40 heteroaryl, substituted or unsubstituted C1 to C 12 alkyl, partially perfluorinated C1 to C 12 alkyl, perfluorinated C1 to C 12 alkyl,

[0183] wherein one or more substituents on R 5 are selected from an electron-withdrawing group, halogen, F, CN, NO2, SF5, isonitrile, ester group, carboxyl group, carbonyl group, acyl group, thio group, sulfinyl group, sulfonyl group, phosphine group, partially fluorinated C1 to C 12 alkyl, perfluorinated C1 to C 12 alkyl, CF3, CF2CF3, partially fluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy, OCF3, OCF2CCF3;

[0184] Preferably, at least one of R a 、R b 、R c and R d is independently selected from substituted or unsubstituted C6 to C 40 aryl, substituted or unsubstituted C2 to C 40 heteroaryl, substituted or unsubstituted C1 to C 12 alkyl, substituted or unsubstituted C 30 3 to C 30 carbocyclic group, substituted or unsubstituted C2 to C

[0185] wherein R a 、R b 、R c and R dThe substituents on are independently selected from an electron-withdrawing group, halogen, F, CN, NO2, SF5, isonitrile, ester group, carboxyl group, carbonyl group, acyl group, thio group, sulfinyl group, sulfonyl group, phosphine group, partially perfluorinated C1 to C 12 alkyl, perfluorinated C1 to C 12 alkyl, CF3, partially perfluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy, OCF3;

[0186] wherein

[0187] optionally, one of R a , R b , R c , R d can independently form a substituted or unsubstituted heterocycle or a substituted or unsubstituted carbocycle with R 1 ,

[0188] wherein one or more substituents on the heterocycle or carbocycle are independently selected from D, electron-withdrawing group, halogen, F, CN, NO2, SF5, isonitrile, ester group, carboxyl group, carbonyl group, acyl group, thio group, sulfinyl group, sulfonyl group, phosphine group, substituted or unsubstituted alkyl, partially perfluorinated C1 to C 12 alkyl, perfluorinated C1 to C 12 alkyl, CF3, partially perfluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy, OCF3, substituted or unsubstituted C6 to C 40 aryl, substituted or unsubstituted C2 to C 40 heteroaryl, substituted or unsubstituted C3 to C 30 carbocyclic group or substituted or unsubstituted C2 to C 30 heterocyclic group;

[0189] wherein one or more substituents on the substituents on the heterocycle or carbocycle are independently selected from D, electron-withdrawing group, halogen, F, substituted or unsubstituted C1 to C 12 alkyl, partially perfluorinated C1 to C 12 alkyl, perfluorinated C1 to C 12 alkyl, CF3, partially perfluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy, OCF3.

[0190] According to one embodiment, R a , R b , R c and R d are not substituted or unsubstituted C3 to C 40 carbocyclic group.

[0191] Auxiliary ligand AL

[0192] The auxiliary ligands are defined as those ligands that provide an appropriate steric and electronic environment around the central element but remain non-reactive during any transformation that the compound undergoes. In contrast, the reactive ligands are those groups that undergo change.

[0193] According to one embodiment of the present application, AL is selected from H2O, C2 - C 40 monodentate or polydentate ethers and C2 - C 40 sulfides, C2 - C 40 amines, C2 - C 40 phosphines, C2 - C 20 alkyl nitriles or C2 - C 40 aryl nitriles, or a compound according to formula (AL-I);

[0194] wherein

[0195] R 6 and R 7 are independently selected from C1 - C 20 alkyl, C1 - C 20 heteroalkyl, C6 - C 20 aryl, heteroaryl having 5 to 20 ring atoms, halogenated or perhalogenated C1 - C 20 alkyl, halogenated or perhalogenated C1 - C 20 heteroalkyl, halogenated or perhalogenated C6 - C 20 aryl, halogenated or perhalogenated heteroaryl having 5 to 20 ring atoms, or at least one R 6 and R 7 bridge to form a 5 - to 20 - membered ring, or two R 6 and / or two R 7 bridge to form a 5 - to 40 - membered ring or form a 5 - to 40 - membered ring containing unsubstituted or C1 - C 12 substituted phenanthroline.

[0196] According to one embodiment, in formula (IV), A 1 , A 2 , A 3 and A 4 are independently selected from C═O, C - O or SO2.

[0197] According to one embodiment, wherein in formula (IV), if A 1 , A 2 , A 3 and A 4 are selected from C - O or C - NR 3 and Z is selected from N, O or CR 1 , or A 1 , A 2, A 3 and A 4 is selected from C—O or C—NR 3 and if Z is selected from C, then Z may be combined with A 1 , A 2 , A 3 and A 4 to form a double bond;

[0198] and optionally two of A 1 , A 2 , A 3 and A 4 together may form a substituted or unsubstituted heterocyclic ring or a substituted or unsubstituted carbocyclic ring with Z, or optionally one of A 1 , A 2 , A 3 and A 4 may form a substituted or unsubstituted heterocyclic ring or a substituted or unsubstituted carbocyclic ring with Z,

[0199] where one or more substituents on the heterocyclic ring or carbocyclic ring are independently selected from D, an electron-withdrawing group, a halogen, F, CN, NO2, SF5, a partially perfluorinated C1-C6 alkyl group, a perfluorinated C1-C6 alkyl group, CF3, a partially perfluorinated C1-C6 alkoxy group, a perfluorinated C1-C6 alkoxy group, OCF3, a substituted or unsubstituted C6-C 12 aryl, a substituted or unsubstituted C3-C 12 heteroaryl, a substituted or unsubstituted C3-C 12 carbocyclic group or a substituted or unsubstituted C3-C 12 heterocyclic group.

[0200] According to one embodiment, in formula (IV), R 1 is selected from CN, a substituted or unsubstituted C1-C 12 alkyl group, a perfluorinated C1-C 12 alkyl group or CF3.

[0201] According to one embodiment, in formula (IV), R 1 is selected from CN or a substituted or unsubstituted C1-C 12 alkyl group.

[0202] According to one embodiment, in formula (IV), R a , R b , R c and R d are independently selected from H, D, an electron-withdrawing group, a halogen, F, Cl, CN, a substituted or unsubstituted C1-C6 alkyl group, a partially perfluorinated C1-C6 alkyl group, a perfluorinated C1-C6 alkyl group, CF3, a substituted or unsubstituted C6-C 12Aryl, substituted or unsubstituted C3 to C 12 Heteroaryl, substituted or unsubstituted C3 to C 12 Heterocyclic group, O, S, N, NR 5 , a substituted or unsubstituted amine group having 0 to 20 carbon atoms;

[0203] wherein R a , R b , R c and R d one or more substituents on are independently selected from electron-withdrawing groups, halogen, F, CN, NO2, SF5, partially perfluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkoxy, OCF3;

[0204] wherein R 5 is selected from substituted or unsubstituted C6 to C 12 aryl, substituted or unsubstituted C3 to C 12 heteroaryl, substituted or unsubstituted C1 to C6 alkyl, partially perfluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl,

[0205] wherein R 5 one or more substituents on are selected from electron-withdrawing groups, halogen, F, CN, NO2, SF5, CF3, CF2CF3, partially fluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy, OCF3, OCF2CCF3;

[0206] Preferably, at least one of R a , R b , R c and R d is independently selected from substituted or unsubstituted C6 to C 12 aryl, substituted or unsubstituted C3 to C 12 heteroaryl, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C3 to C 12 heterocyclic group,

[0207] wherein R a , R b , R c and R d substituents on are independently selected from electron-withdrawing groups, halogen, F, CN, NO2, SF5, perfluorinated C1 to C6 alkyl, CF3, perfluorinated C1 to C6 alkoxy, OCF3;

[0208] wherein

[0209] Optionally, R a , R b , R c , Rd One of them can be independently combined with R 1 to form a substituted or unsubstituted heterocycle or a substituted or unsubstituted carbocycle,

[0210] wherein one or more substituents on the heterocycle or carbocycle are independently selected from D, an electron-withdrawing group, a halogen, F, CN, NO2, SF5, a partially perfluorinated C1 to C 12 alkyl group, a perfluorinated C1 to C 12 alkyl group, CF3, a partially perfluorinated C1 to C6 alkoxy group, a perfluorinated C1 to C6 alkoxy group, OCF3, a substituted or unsubstituted C6 to C 12 aryl group, a substituted or unsubstituted C3 to C 12 heteroaryl group, a substituted or unsubstituted C3 to C 12 carbocyclic group or a substituted or unsubstituted C3 to C 12 heterocyclic group;

[0211] wherein one or more substituents on the substituents on the heterocycle or carbocycle are independently selected from D, an electron-withdrawing group, a halogen, F, a perfluorinated C1 to C6 alkyl group, CF3, a perfluorinated C1 to C6 alkoxy group, OCF3.

[0212] According to one embodiment, in formula (IV), R 2 , R 3 and R 4 are independently selected from a substituted or unsubstituted alkyl group, a partially perfluorinated C1 to C 12 alkyl group, a perfluorinated C1 to C 12 alkyl group, CF3, a substituted or unsubstituted C1 to C6 alkoxy group, a partially perfluorinated C1 to C6 alkoxy group, a perfluorinated C1 to C6 alkoxy group, OCF3, a substituted or unsubstituted C6 to C 40 aryl group, a substituted or unsubstituted C2 to C 30 heteroaryl group, a substituted or unsubstituted C3 to C 30 carbocyclic group, a substituted or unsubstituted C2 to C 30 heterocyclic group,

[0213] wherein the substituents on R 2 , R 3 and R 4 are independently selected from D, F, CN, NO2, SF5.

[0214] According to one embodiment, in formula (IV), A 1 , A 2 , A 3 and A 4 are independently selected from C=O, C-O or SO2;

[0215] wherein if A1 , A 2 , A 3 and A 4 is selected from C-O or C-NR 3 and Z is selected from N, O or CR 1 , or A 1 , A 2 , A 3 and A 4 is selected from C-O or C-NR 3 and if Z is selected from C, then Z can form a double bond with A 1 , A 2 , A 3 and A 4 ;

[0216] and optionally two of A 1 , A 2 , A 3 and A 4 together can form a substituted or unsubstituted heterocycle or a substituted or unsubstituted carbocycle with Z, or optionally one of A 1 , A 2 , A 3 and A 4 can form a substituted or unsubstituted heterocycle or a substituted or unsubstituted carbocycle with Z,

[0217] where one or more substituents on the heterocycle or carbocycle are independently selected from D, an electron-withdrawing group, a halogen, F, CN, NO2, SF5, a partially perfluorinated C1-C6 alkyl group, a perfluorinated C1-C6 alkyl group, CF3, a partially perfluorinated C1-C6 alkoxy group, a perfluorinated C1-C6 alkoxy group, OCF3, a substituted or unsubstituted C6-C 12 aryl, a substituted or unsubstituted C3-C 12 heteroaryl, a substituted or unsubstituted C3-C 12 carbocyclic group or a substituted or unsubstituted C3-C 12 heterocyclic group;

[0218] R 1 is selected from CN, a substituted or unsubstituted C1-C 12 alkyl group, a perfluorinated C1-C 12 alkyl group or CF3;

[0219] R 2 , R 3 and R 4 are independently selected from a substituted or unsubstituted alkyl group, a partially perfluorinated C1-C 12 alkyl group, a perfluorinated C1-C 12Alkyl, CF3, substituted or unsubstituted C1-C6 alkoxy, partially perfluorinated C1-C6 alkoxy, perfluorinated C1-C6 alkoxy, OCF3, substituted or unsubstituted C6-C 40 Aryl, substituted or unsubstituted C2-C 30 Heteroaryl, substituted or unsubstituted C3-C 30 Carbocyclic group, substituted or unsubstituted C2-C 30 Heterocyclic group,

[0220] wherein the substituents on R 2 , R 3 and R 4 are independently selected from D, F, CN, NO2, SF5;

[0221] R a , R b , R c and R d are independently selected from H, D, electron-withdrawing groups, halogens, F, Cl, CN, substituted or unsubstituted C1-C6 alkyl, partially perfluorinated C1-C6 alkyl, perfluorinated C1-C6 alkyl, CF3, substituted or unsubstituted C6-C 12 Aryl, substituted or unsubstituted C3-C 12 Heteroaryl, substituted or unsubstituted C3-C 12 Heterocyclic group, O, S, N, NR 5 , substituted or unsubstituted amine groups having 0 to 20 carbon atoms;

[0222] wherein one or more of the substituents on R a , R b , R c and R d are independently selected from electron-withdrawing groups, halogens, F, CN, NO2, SF5, partially perfluorinated C1-C6 alkyl, perfluorinated C1-C6 alkyl, perfluorinated C1-C6 alkoxy, OCF3;

[0223] wherein R 5 is selected from substituted or unsubstituted C6-C 12 Aryl, substituted or unsubstituted C3-C 12 Heteroaryl, substituted or unsubstituted C1-C6 alkyl, partially perfluorinated C1-C6 alkyl, perfluorinated C1-C6 alkyl,

[0224] wherein one or more of the substituents on R 5 are selected from electron-withdrawing groups, halogens, F, CN, NO2, SF5, CF3, CF2CF3, partially fluorinated C1-C6 alkoxy, perfluorinated C1-C6 alkoxy, OCF3, OCF2CCF3;

[0225] Preferably, R a , R b , R c and R d at least one of them is independently selected from substituted or unsubstituted C6 - C 12 aryl, substituted or unsubstituted C3 - C 12 heteroaryl, substituted or unsubstituted C1 - C6 alkyl, substituted or unsubstituted C3 - C 12 heterocyclic group,

[0226] wherein the substituents on R a , R b , R c and R d are independently selected from electron - withdrawing groups, halogens, F, CN, NO2, SF5, perfluorinated C1 - C6 alkyl, CF3, perfluorinated C1 - C6 alkoxy, OCF3;

[0227] wherein

[0228] Optionally, one of R a , R b , R c , R d can independently form a substituted or unsubstituted heterocycle or a substituted or unsubstituted carbocycle with R 1 ,

[0229] wherein one or more substituents on the heterocycle or carbocycle are independently selected from D, electron - withdrawing groups, halogens, F, CN, NO2, SF5, partially perfluorinated C1 - C 12 alkyl, perfluorinated C1 - C 12 alkyl, CF3, partially perfluorinated C1 - C6 alkoxy, perfluorinated C1 - C6 alkoxy, OCF3, substituted or unsubstituted C6 - C 12 aryl, substituted or unsubstituted C3 - C 12 heteroaryl, substituted or unsubstituted C3 - C 12 carbocyclic group or substituted or unsubstituted C3 - C 12 heterocyclic group;

[0230] wherein one or more substituents on the substituents of the heterocycle or carbocycle are independently selected from D, electron - withdrawing groups, halogens, F, perfluorinated C1 - C6 alkyl, CF3, perfluorinated C1 - C6 alkoxy, OCF3.

[0231] According to one embodiment, in formula (IV), if Z is selected from N and p and q are selected from 0, t and u are selected from 0, m and n are selected from 1, r and s are selected from 1, then if A 1 and A 2 one of them is selected from SO2, then A1 and A 2 the other in 2 cannot be C=O or C-O.

[0232] According to one embodiment, in formula (IV), if Z is selected from N and p and q are selected from 0, and t and u are selected from 0, then if A 1 and A 2 one of them is selected from SO2, then A 1 and A 2 the other in 2 cannot be C=O or C-O.

[0233] According to one embodiment, the monoanion or the monoanion ligand L - is selected from (V), (VI), (VII), (VIII) or (IX):

[0234]

[0235] R a' is independently selected from substituted or unsubstituted C1 to C 12 alkyl, substituted or unsubstituted C6 to C 19 aryl, substituted or unsubstituted C2 to C 20 heteroaryl or substituted or unsubstituted 6-membered heteroaryl;

[0236] R b' is selected from substituted or unsubstituted C1 to C 12 alkyl, substituted or unsubstituted C6 to C 19 aryl, substituted or unsubstituted C2 to C 20 heteroaryl, substituted or unsubstituted 6-membered heteroaryl or CN;

[0237] wherein

[0238] at least one substituent of the substituted C1 to C 12 alkyl, substituted C6 to C 19 aryl, substituted C2 to C 20 heteroaryl or substituted 6-membered heteroaryl is independently selected from halogen, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl, partially fluorinated or perfluorinated C1 to C8 alkoxy;

[0239] wherein in formula (VI),

[0240] R a' , R b' and R a or at least one of R a' , R b' and R a in the group contains at least three atoms selected from halogen, Cl, F or N;

[0241] - The remaining Rs are the same as those defined above.

[0242] According to one embodiment, L - is represented by formula (X):

[0243]

[0244] and wherein Z is selected from O, N or CR 1 ,

[0245] wherein if Z is selected from O, then n is selected from 0 and s is selected from 0.

[0246] According to one embodiment, L - is represented by formula (XI):

[0247]

[0248] wherein Z is selected from N or CR 1 .

[0249] According to one embodiment, in formula (IV), if Z is selected from N or CR 1 , then p and q are selected from 0, and t and u are selected from 0, and

[0250] if Z is selected from N, then A 1 and A 2 are selected from SO2,

[0251] if Z is selected from CR 1 , then A 1 and A 2 are selected from C═O or C—O.

[0252] According to one embodiment, in formula (X), if Z is selected from N, and

[0253] if Z is selected from N, then A 1 and A 2 are selected from SO2,

[0254] if Z is selected from CR 1 , then A 1 and A 2 are selected from C═O or C—O.

[0255] According to one embodiment, in formula (X), if Z is selected from N, m and n are selected from 1, and r and s are selected from 1, then if one of A 1 and A 2 is selected from SO2, then the other of A 1 and A 2 cannot be C═O or CO.

[0256] According to one embodiment, in formula (X), if Z is selected from N, then if A 1 and A 2 one of which is selected from SO2, then A 1 and A 2 the other of which cannot be C═O or CO.

[0257] According to one embodiment, in formula (X), if Z is selected from N, then if A 1 and A 2 one of which is selected from SO2, then A 1 and A 2 the other of which cannot be C═O or CO.

[0258] According to one embodiment, the monoanion or the monoanionic ligand L - is selected from (V), (VI) or (VII):

[0259]

[0260] -R is the same as defined above.

[0261] According to one embodiment, the monoanion or the monoanionic ligand L - is selected from (V) or (VI):

[0262]

[0263] According to one embodiment, the monoanion or the monoanionic ligand L - is selected from (V):

[0264]

[0265] wherein two adjacent substituents R a 、R b and R 1 may optionally be linked to form a heterocyclic or carbocyclic ring.

[0266] According to one embodiment, the monoanionic ligand L - is selected from (V):

[0267]

[0268] R a and R b are independently selected from perfluorinated C1 to C6 alkyl, CF3, substituted or unsubstituted C6 to C 40 aryl, 3,5-CF3-phenyl, N, NR 5 、substituted or unsubstituted C2 to C 40Heteroaryl, 2,6-CF3-pyridyl, a substituted or unsubstituted amine group having from 0 to 20 carbon atoms;

[0269] wherein R 1 one or more substituents on are independently selected from D, an electron-withdrawing group, halogen, F, CN, NO2, SF5, isonitrile, an ester group, a carboxyl group, a carbonyl group, an acyl group, a thio group, a sulfinyl group, a sulfonyl group, a phosphine group, a partially perfluorinated C1 to C 12 alkyl, a perfluorinated C1 to C 12 alkyl, CF3, a partially perfluorinated C1 to C6 alkoxy group, a perfluorinated C1 to C6 alkoxy group, OCF3, =N;

[0270] R 1 is selected from H, D, CN, a substituted or unsubstituted C1 to C8 alkyl;

[0271] wherein R 1 one or more substituents on are independently selected from D, an electron-withdrawing group, halogen, F, CN, NO2, SF5, isonitrile, an ester group, a carboxyl group, a carbonyl group, an acyl group, a thio group, a sulfinyl group, a sulfonyl group, a phosphine group, a partially perfluorinated C1 to C 12 alkyl, a perfluorinated C1 to C 12 alkyl, CF3, a partially perfluorinated C1 to C6 alkoxy group, a perfluorinated C1 to C6 alkoxy group, OCF3, =N;

[0272] wherein two adjacent substituents R a , R b and R 1 may optionally be joined to form a heterocyclic or carbocyclic ring.

[0273] According to one embodiment, the monoanionic ligand L - is selected from (V):

[0274]

[0275] R a and R b are independently selected from a perfluorinated C1 to C6 alkyl, CF3, 3,5-CF3-phenyl, N, NR 5 , 2,6-CF3-pyridyl, a substituted or unsubstituted amine group having from 0 to 20 carbon atoms;

[0276] wherein one or more substituents are independently selected from wherein R 1One or more substituents on are independently selected from D, an electron-withdrawing group, a halogen, F, CN, NO2, SF5, isonitrile, an ester group, a carboxyl group, a carbonyl group, an acyl group, a thio group, a sulfinyl group, a sulfonyl group, a phosphine group, a partially perfluorinated C1 to C 12 alkyl, a perfluorinated C1 to C 12 alkyl, CF3, a partially perfluorinated C1 to C6 alkoxy group, a perfluorinated C1 to C6 alkoxy group, OCF3, ═N;

[0277] R 1 is selected from H, D, CN, a substituted or unsubstituted C1 to C8 alkyl;

[0278] wherein one or more substituents on R 1 are independently selected from D, an electron-withdrawing group, a halogen, F, CN, NO2, SF5, isonitrile, an ester group, a carboxyl group, a carbonyl group, an acyl group, a thio group, a sulfinyl group, a sulfonyl group, a phosphine group, a partially perfluorinated C1 to C 12 alkyl, a perfluorinated C1 to C 12 alkyl, CF3, a partially perfluorinated C1 to C6 alkoxy group, a perfluorinated C1 to C6 alkoxy group, OCF3, ═N;

[0279] wherein two adjacent substituents R a 、R b and R 1 may optionally be joined to form a heterocyclic or carbocyclic ring.

[0280] According to one embodiment, at least one of R a 、R b X、R c or R d or at least one of R a 、R b 、R c and R d is independently selected from D1 to D105:

[0281]

[0282]

[0283]

[0284] -CF3 (D72), -C2F5 (D73), -C3F7 (D74), -CF2CF2CF3 (D75), -C4F9 (D77), -CF2CF2CF2CF3 (D78), -C5F 11(D81), -C6F 13 (D82), -CH3 (D83), -C2H5 (D84), -CH(CH3)2 (D85), -C(CH3)3 (D86),

[0285] wherein "*" or "-" represents the bonding position.

[0286] According to one embodiment, wherein R a , R b , R c or R d or at least one of R a , R b , R c and R d are independently selected from D1 to D105 or NR 5 , wherein R 5 is independently selected from D1 to D105.

[0287] According to one embodiment, wherein the monoanion or the monoanion ligand is selected from L1 to L405:

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311] According to one embodiment, the monoanion or the monoanion ligand is selected from L1 to L315, L319 to L327, L331 to L405.

[0312] According to one embodiment, the monoanion or the monoanion ligand is selected from L1 to L315 and L331 to L405.

[0313] According to one embodiment, the monoanion or the monoanion ligand is selected from L1 to L265 and L331 to L405.

[0314] According to one embodiment, the monoanion or the monoanion ligand is selected from L1 to L265.

[0315] According to one embodiment, the monoanion or the monoanion ligand is selected from L1 to L54.

[0316] According to one embodiment, the monoanion or the monoanion ligand is selected from L55 to L265.

[0317] According to one embodiment, the compound of formula (II) is selected from the following compounds M1 to M17:

[0318]

[0319]

[0320] According to an embodiment of the present invention, relative to the total number of molecules in the hole injection layer, the amount of the compound of formula (II) present in the hole injection layer is ≤99.9 mol%, preferably ≤99 mol%, more preferably ≤95 mol%, more preferably ≤90 mol%, more preferably ≤80 mol%, more preferably ≤70 mol%, more preferably ≤60 mol%, more preferably ≤50 mol%, more preferably ≤40 mol%, more preferably ≤30 mol%, more preferably ≤20 mol%, more preferably ≤10 mol%, more preferably ≤7 mol%, more preferably ≤6 mol%, more preferably ≤5 mol%, more preferably ≤4 mol%, and most preferably ≤3.0 mol%.

[0321] According to an embodiment of the present invention, relative to the total number of molecules in the hole injection layer, the amount of the first hole transport matrix compound present in the hole injection layer is ≥0.1 mol%, preferably ≥1 mol%, more preferably ≥5 mol%, more preferably ≥10 mol%, more preferably ≥20 mol%, more preferably ≥30 mol%, more preferably ≥40 mol%, more preferably ≥50 mol%, more preferably ≥60 mol%, more preferably ≥70 mol%, more preferably ≥80 mol%, more preferably ≥90 mol%, more preferably ≥93 mol%, more preferably ≥94 mol%, more preferably ≥95 mol%, more preferably ≥96 wt%, and most preferably ≥97.0 mol%.

[0322] According to an embodiment of the present invention, the organic electroluminescent device further includes a third light-emitting layer.

[0323] According to an embodiment of the present invention, no more than one charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer, particularly no more than one charge generation layer including a p-type charge generation layer and an n-type charge generation layer.

[0324] According to an embodiment of the present invention, no more than one charge generation layer is disposed between the second light-emitting layer and the third light-emitting layer, particularly no more than one charge generation layer including a p-type charge generation layer and an n-type charge generation layer.

[0325] According to an embodiment of the present invention, a third light-emitting layer and a second charge generation layer, wherein the second charge generation layer is disposed between the second light-emitting layer and the third light-emitting layer, wherein the second charge generation layer includes a second p-type charge generation layer and a second n-type charge generation layer, and wherein the second n-type charge generation layer is closer to the anode layer than the second p-type charge generation layer

[0326] wherein the second n-type charge generation layer includes a metal dopant and a matrix compound

[0327] Wherein the second p-type charge generation layer comprises a second hole transport matrix compound and a compound of formula (I).

[0328] According to an embodiment of the present invention, the organic electroluminescent device further comprises a third light-emitting layer and a fourth light-emitting layer.

[0329] According to an embodiment of the present invention, the organic electroluminescent device comprises

[0330] Comprising a third light-emitting layer, a fourth light-emitting layer, a second charge generation layer and a third charge generation layer, wherein the second charge generation layer is disposed between the second light-emitting layer and the third light-emitting layer, and wherein the third charge generation layer is disposed between the third light-emitting layer and the fourth light-emitting layer,

[0331] Wherein the second charge generation layer comprises a second p-type charge generation layer and a second n-type charge generation layer,

[0332] Wherein the third charge generation layer comprises a third p-type charge generation layer and a third n-type charge generation layer,

[0333] Wherein the second n-type charge generation layer is closer to the anode layer than the second p-type charge generation layer,

[0334] Wherein the third n-type charge generation layer is closer to the anode layer than the third p-type charge generation layer,

[0335] Wherein the second n-type charge generation layer comprises a metal dopant and a matrix compound,

[0336] Wherein the third n-type charge generation layer comprises a metal dopant and a matrix compound,

[0337] Wherein the second p-type charge generation layer comprises a second hole transport matrix compound and a compound of formula (I),

[0338] Wherein the third p-type charge generation layer comprises a third hole transport matrix compound and a compound of formula (I).

[0339] According to one embodiment, the organic electroluminescent device further comprises a layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer.

[0340] According to one embodiment, the organic electroluminescent device further comprises a hole injection layer, a first hole transport layer, a second hole transport layer, a first electron blocking layer, a second electron blocking layer, optionally a first hole blocking layer, optionally a second hole blocking layer, a first electron transport layer, a second electron transport layer and an electron injection layer.

[0341] According to one embodiment of the present invention, the first n-type charge generation layer is in direct contact with the first p-type charge generation layer.

[0342] According to one embodiment of the present invention, the second n-type charge generation layer is in direct contact with the second p-type charge generation layer.

[0343] According to one embodiment of the present invention, the third n-type charge generation layer is in direct contact with the third p-type charge generation layer.

[0344] According to one embodiment of the present invention, each of the at least two light-emitting units includes an electron transport layer.

[0345] According to one embodiment of the present invention, the organic electroluminescent device further includes an electron transport layer, wherein the electron transport layer is disposed between the first light-emitting layer and the second light-emitting layer, wherein the electron transport layer is disposed to be in direct contact with the first n-type charge generation layer, and wherein the electron transport layer is disposed between the first light-emitting layer and the first n-type charge generation layer.

[0346] According to one embodiment of the present invention, the organic electroluminescent device further includes an electron transport layer, wherein the electron transport layer is disposed between the first light-emitting layer and the second light-emitting layer, wherein the electron transport layer is disposed to be in direct contact with the first n-type charge generation layer, wherein the electron transport layer is disposed between the first light-emitting layer and the first n-type charge generation layer, and wherein the first n-type charge generation layer is in direct contact with the first p-type charge generation layer.

[0347] According to one embodiment of the present invention, the host compound of the first n-type charge generation layer is an electron transport material.

[0348] According to one embodiment of the present invention, the host compound of the first n-type charge generation layer is an organic electron transport material.

[0349] According to one embodiment of the present invention, the host compound of the first n-type charge generation layer contains at least one C2 to C 24 N-heteroaryl or P═X group, wherein X is O, P, Se, and particularly preferably P═O.

[0350] According to one embodiment of the present invention, the at least one C2 to C 24 N-heteroaryl may be selected from compounds containing at least one azine group, preferably at least two azine groups, and more preferably three azine groups.

[0351] According to one embodiment of the present invention, the matrix compound of the first n-type charge generation layer comprises at least one group selected from the following groups: pyridine, pyrimidine, triazine, imidazole, benzimidazole, benzo oxazole, quinone, benzoquinone, imidazo[1,5-a]pyridine, quinoxaline, benzoquinoxaline, acridine, phenanthroline, benzoacridine, dibenzoacridine, phosphine oxide, terpyridine.

[0352] According to one embodiment of the present invention, the matrix compound of the first n-type charge generation layer 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.

[0353] According to one embodiment of the present invention, the matrix compound of the first n-type charge generation layer 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.

[0354] According to one embodiment of the present invention, the matrix compound of the first n-type charge generation layer comprises at least one phenanthroline group (preferably two phenanthroline groups), pyridine group, pyrimidine group or phosphine oxide group.

[0355] According to one embodiment of the present invention, the matrix compound of the first n-type charge generation layer 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.

[0356] According to one embodiment of the present invention, the matrix compound of the first n-type charge generation layer is selected from 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline], (3-(10-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)anthracen-9-yl)phenyl)dimethylphosphine oxide, 3-(3-(9,10-diphenylanthracen-2-yl)phenyl)-1-(pyridin-2-yl)imidazo[1,5-a]pyridine, 7-(3-(1,10-phenanthrolin-2-yl)phenyl)dibenzo[c,h]acridine, 7-(3-([2,2':6',2"-terpyridin]-4'-yl)phenyl)dibenzo[c,h]acridine, 4'-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-2,2':6',2"-terpyridine, 4'-(4-(fluoranthen-3-yl)phenyl)-2,2':6',2"-terpyridine or 3-(9,10-di-2-naphthalen-2-yl-2-anthracenyl)phenyl]dimethylphosphine oxide.

[0357] According to an embodiment of the present invention, the matrix compound of the first n-type charge generation layer contains at least one phenanthroline group, preferably two phenanthroline groups.

[0358] According to an embodiment of the present invention, the metal dopant is selected from metals with an electronegativity ≤ 1.4 eV according to the Pauling scale or metal alloys containing metals with an electronegativity ≤ 1.4 eV according to the Pauling scale.

[0359] According to an embodiment of the present invention, the metal dopant is selected from metals with an electronegativity ≤ 1.35 eV according to the Pauling scale or metal alloys containing metals with an electronegativity ≤ 1.35 eV according to the Pauling scale.

[0360] According to an embodiment of the present invention, the metal dopant is a metal selected from Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eu, and Yb, or a metal alloy containing a metal selected from Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eu, and Yb.

[0361] According to an embodiment of the present invention, the metal dopant is a metal selected from Li, Na, K, Cs, Mg, Ca, Ba, Sm, Eu, and Yb, or a metal alloy containing a metal selected from Li, Na, K, Cs, Mg, Ca, Ba, Sm, Eu, and Yb.

[0362] According to an embodiment of the present invention, the metal dopant is a metal selected from Li, Mg, and Yb, or a metal alloy containing a metal selected from Li, Mg, and Yb.

[0363] According to an embodiment of the present invention, the metal dopant is a metal selected from Li and Yb, or a metal alloy containing a metal selected from Li and Yb.

[0364] According to an embodiment of the present invention, the metal dopant is Yb, or a metal alloy containing a metal selected from Li and Yb.

[0365] According to an embodiment of the present invention, the metal dopant is Yb.

[0366] According to an embodiment of the present invention, the metal dopant is in an oxidation state of ±0.

[0367] According to an embodiment of the present invention, with respect to the total volume of the first n-type charge generation layer, the amount of the metal dopant present in the layer is ≤99.9% by volume, preferably ≤99% by volume, more preferably ≤95% by volume, more preferably ≤90% by volume, more preferably ≤80% by volume, more preferably ≤70% by volume, more preferably ≤60% by volume, more preferably ≤50% by volume, more preferably ≤40% by volume, more preferably ≤30% by volume, more preferably ≤20% by volume, more preferably ≤10% by volume, more preferably ≤5% by volume, more preferably ≤3.0% by volume, more preferably ≤2% by volume, more preferably ≤1.5% by volume, more preferably ≤1.25% by volume, and most preferably ≤1.0% by volume.

[0368] According to an embodiment of the present invention, with respect to the total volume of the first n-type charge generation layer, the amount of the matrix compound present in the layer is ≥0.1% by volume, preferably ≥1% by volume, more preferably ≥5% by volume, more preferably ≥10% by volume, more preferably ≥20% by volume, more preferably ≥30% by volume, more preferably ≥40% by volume, more preferably ≥50% by volume, more preferably ≥60% by volume, more preferably ≥70% by volume, more preferably ≥80% by volume, more preferably ≥90% by volume, more preferably ≥95% by volume, more preferably ≥97.0% by volume, more preferably ≥98% by volume, more preferably ≥98.25% by volume, more preferably ≥98.5% by volume, more preferably ≥98.75% by volume, and most preferably ≥99.0% by volume.

[0369] According to an embodiment of the present invention, with respect to the total number of molecules in the p-type charge generation layer, the amount of the compound of formula (I) present in the first p-type charge generation layer is ≤99.9 mol%, preferably ≤99 mol%, more preferably ≤95 mol%, more preferably ≤90 mol%, more preferably ≤80 mol%, more preferably ≤70 mol%, more preferably ≤60 mol%, more preferably ≤50 mol%, more preferably ≤40 mol%, more preferably ≤30 mol%, more preferably ≤20 mol%, more preferably ≤10 mol%, and more preferably ≤7 mol%.

[0370] According to an embodiment of the present invention, with respect to the total number of molecules in the p-type charge generation layer, the amount of the second hole-transporting matrix compound present in the first p-type charge generation layer is ≥0.1 mol%, preferably ≥1 mol%, more preferably ≥5 mol%, more preferably ≥10 mol%, more preferably ≥20 mol%, more preferably ≥30 mol%, more preferably ≥40 mol%, more preferably ≥50 mol%, more preferably ≥60 mol%, more preferably ≥70 mol%, more preferably ≥80 mol%, more preferably ≥90 mol%, and more preferably ≥93 mol%.

[0371] According to an embodiment of the present invention, the electroluminescent device further includes at least one hole transport layer.

[0372] According to an embodiment of the present invention, the organic electroluminescent device further includes a hole transport layer, wherein the hole transport layer is disposed between the first light-emitting layer and the second light-emitting layer, wherein the hole transport layer is disposed in direct contact with the first p-type charge generation layer, and wherein the hole transport layer is disposed between the first p-type charge generation layer and the second light-emitting layer.

[0373] According to an embodiment of the present invention, the organic electroluminescent device further includes a hole transport layer, wherein the hole transport layer is disposed between the first light-emitting layer and the second light-emitting layer, wherein the hole transport layer is disposed in direct contact with the first p-type charge generation layer, wherein the hole transport layer is disposed between the first p-type charge generation layer and the second light-emitting layer, and wherein the first n-type charge generation layer is disposed in direct contact with the hole transport layer.

[0374] According to an embodiment of the present invention, when calculated by applying the hybrid functional B3LYP and the 6-31G* basis set in the gas phase using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the calculated HOMO energy level of the first hole transport matrix compound represented on an absolute scale with the reference vacuum level being zero is ≤ -4.27 eV to ≥ -5.1 eV, preferably ≤ -4.3 eV to ≥ -5.0 eV, more preferably ≤ -4.4 eV and ≥ -5.0 eV, more preferably ≤ -4.5 eV and ≥ -5.0 eV, more preferably ≤ -4.5 eV and ≥ -4.9 eV, and most preferably ≤ -4.6 eV and ≥ -4.9 eV.

[0375] According to an embodiment of the present invention, the first hole transport matrix compound is a substantially covalent matrix compound.

[0376] According to an embodiment of the present invention, the first hole transport matrix compound is an organic hole transport matrix compound.

[0377] According to an embodiment of the present invention, the first hole transport matrix compound is a substantially covalent organic matrix compound.

[0378] According to an embodiment of the present invention, the first hole transport matrix compound of the p-type charge generation layer is a substantially covalent matrix compound.

[0379] According to an embodiment of the present invention, the organic hole transport matrix compound of the charge generation layer is the same as the organic hole transport matrix compound of the p-type charge generation layer.

[0380] According to an embodiment of the present invention, the second hole transport matrix compound of the p-type charge generation layer is the same as the first hole transport matrix compound of the hole injection layer.

[0381] According to an embodiment of the present invention, when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the calculated HOMO energy level of the first hole transport matrix compound of the hole injection layer represented on an absolute scale with the reference vacuum level being zero is in the range of ≤ -4.27 eV to ≥ -5.1 eV, preferably ≤ -4.3 eV to ≥ -5.0 eV, more preferably ≤ -4.4 eV and ≥ -5.0 eV, more preferably ≤ -4.5 eV and ≥ -5.0 eV, more preferably ≤ -4.5 eV and ≥ -4.9 eV, and most preferably ≤ -4.6 eV and ≥ -4.9 eV.

[0382] According to an embodiment of the present invention, the first hole transport matrix compound is a substantially covalent matrix compound.

[0383] According to an embodiment of the present invention, the first hole transport matrix compound is an organic hole transport matrix compound.

[0384] According to an embodiment of the present invention, the first hole transport matrix compound is a substantially covalent organic matrix compound.

[0385] According to an embodiment of the present invention, relative to the total number of molecules in the hole injection layer, the amount of the first hole transport matrix compound present in the hole injection layer is ≥ 0.1 mol%, preferably ≥ 1 mol%, more preferably ≥ 5 mol%, more preferably ≥ 10 mol%, more preferably ≥ 20 mol%, more preferably ≥ 30 mol%, more preferably ≥ 40 mol%, more preferably ≥ 50 mol%, more preferably ≥ 60 mol%, more preferably ≥ 70 mol%, more preferably ≥ 80 mol%, more preferably ≥ 90 mol%, more preferably ≥ 93 mol%, more preferably ≥ 94 mol%, more preferably ≥ 95 mol%, more preferably ≥ 96 wt%, and most preferably ≥ 97.0 mol%.

[0386] According to an embodiment of the present invention, the organic hole transport matrix compound of the p-type charge generation layer is the same as the organic hole transport layer of the hole injection layer.

[0387] According to one embodiment of the present invention, when calculating by applying the hybrid functional B3LYP and the 6-31G* basis set in the gas phase using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the calculated HOMO energy level of the second hole transport matrix compound of the p-type charge generation layer represented on an absolute scale with the reference vacuum level being zero is in the range of ≤ -4.27 eV to ≥ -5.1 eV, preferably ≤ -4.3 eV to ≥ -5.0 eV, more preferably ≤ -4.4 eV to ≥ -5.0 eV, more preferably ≤ -4.5 eV and ≥ -5.0 eV, more preferably ≤ -4.5 eV and ≥ -4.9 eV, and most preferably ≤ -4.6 eV and ≥ -4.9 eV.

[0388] According to one embodiment of the present invention, the second hole transport matrix compound is a substantially covalent matrix compound.

[0389] According to one embodiment of the present invention, the second hole transport matrix compound is an organic hole transport matrix compound.

[0390] According to one embodiment of the present invention, the second hole transport matrix compound is a substantially covalent organic matrix compound.

[0391] According to one embodiment of the present invention, the amount of the second hole transport matrix compound present in the p-type charge generation layer is ≥ 0.1 mol%, preferably ≥ 1 mol%, more preferably ≥ 5 mol%, more preferably ≥ 10 mol%, more preferably ≥ 20 mol%, more preferably ≥ 30 mol%, more preferably ≥ 40 mol%, more preferably ≥ 50 mol%, more preferably ≥ 60 mol%, more preferably ≥ 70 mol%, more preferably ≥ 80 mol%, more preferably ≥ 90 mol%, more preferably ≥ 93 mol%, relative to the total number of molecules in the p-type charge generation layer.

[0392] According to one embodiment of the present invention, the organic electroluminescent device includes at least one electron injection layer (EIL).

[0393] According to one embodiment of the present invention, the electron injection layer is in direct contact with the cathode layer.

[0394] According to one embodiment of the present invention, the organic hole transport matrix compound of the p-type charge generation layer is a substantially covalent matrix compound and is the same as the organic hole transport matrix compound of the hole injection layer.

[0395] Fundamental covalent matrix compound

[0396] According to one embodiment of the present invention, the substantially covalent matrix compound may be selected from at least one organic compound. The substantially covalent matrix may consist essentially of covalently bonded C, H, O, N, S, and optionally additionally contain covalently bonded B, P, As, and / or Se.

[0397] According to one embodiment of the present invention, the substantially covalent matrix compound may be selected from organic compounds consisting essentially of covalently bonded C, H, O, N, S and optionally additionally containing covalently bonded B, P, As, and / or Se.

[0398] Organometallic compounds containing covalent bond carbon-metal, metal complexes containing organic ligands, and metal salts of organic acids are other examples of organic compounds that can be used as the substantially covalent matrix compound for the hole injection layer.

[0399] In one embodiment, the substantially covalent matrix compound lacks metal atoms, and most of its skeletal atoms may be selected from C, O, S, N. Alternatively, the substantially covalent matrix compound lacks metal atoms, and most of its skeletal atoms may be selected from C and N.

[0400] According to one embodiment, the molecular weight Mw of the substantially covalent matrix compound may be ≥400 and ≤2000 g / mol, preferably the molecular weight Mw is ≥450 and ≤1500 g / mol, more preferably the molecular weight Mw is ≥500 and ≤1000 g / mol, additionally preferably the molecular weight Mw is ≥550 and ≤900 g / mol, and still preferably the molecular weight Mw is ≥600 and ≤800 g / mol.

[0401] Preferably, the substantially covalent matrix compound contains at least one arylamine moiety, or diarylamine moiety, or triarylamine moiety.

[0402] Preferably, the substantially covalent matrix compound does not contain metals and / or ionic bonds.

[0403] Compound of formula (XII) or compound of formula (XIII)

[0404] According to another aspect of the present invention, the substantially covalent matrix compound may contain at least one arylamine compound, diarylamine compound, triarylamine compound, compound of formula (XII) or compound of formula (XIII):

[0405]

[0406] Wherein:

[0407] T 1 、T 2 、T 3 、T 4and T 5 is independently selected from a single bond, a phenylene group, a biphenylene group, a terphenylene group or a naphthylene group, preferably a single bond or a phenylene group;

[0408] T 6 is a phenylene group, a biphenylene group, a terphenylene group or a naphthylene group;

[0409] Ar' 1 , Ar' 2 , Ar' 3 , Ar' 4 and Ar' 5 are independently selected from substituted or unsubstituted C6-C20 aryl groups, or substituted or unsubstituted C3-C20 heteroarylene groups, substituted or unsubstituted bibenzylidene, 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 azepine, substituted or unsubstituted dibenzo[b,f]azepine, substituted or unsubstituted 9,9'-spirobi[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanthene], or substituted or unsubstituted aromatic fused ring systems, said ring systems comprising at least three substituted or unsubstituted aromatic rings, said aromatic rings being selected from substituted or unsubstituted non-hetero 5-membered rings, substituted or unsubstituted hetero 5-membered rings, substituted or unsubstituted 6-membered rings and / or substituted or unsubstituted 7-membered rings, substituted or unsubstituted fluorene, or fused ring systems comprising 2 to 6 substituted or unsubstituted 5 to 7-membered rings, and said rings being selected from (i) heterocyclic unsaturated rings having 5 to 7 members, (ii) aromatic heterocyclic rings having 5 to 6 members, (iii) non-heterocyclic unsaturated rings having 5 to 7 members, (iv) aromatic non-heterocyclic 6-membered rings;

[0410] wherein

[0411] Ar' 1 , Ar' 2 , Ar' 3 , Ar' 4 and Ar' 5 have substituents that are the same or different and 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, a substituted or unsubstituted straight-chain alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched-chain alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl or alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic ring system having 6 to 40 aromatic ring atoms, and a substituted or unsubstituted heteroaromatic ring system having 5 to 40 aromatic ring atoms, unsubstituted C6 to C 18 aryl, unsubstituted C3 to C 18 heteroaryl, a fused ring system containing 2 to 6 unsubstituted 5- to 7-membered rings, and said 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,

[0412] wherein R' 2 is optionally selected from H, D, a straight-chain alkyl group having 1 to 6 carbon atoms, a branched-chain alkyl group having 1 to 6 carbon atoms, a cyclic alkyl group having 3 to 6 carbon atoms, an alkenyl or alkynyl group having 2 to 6 carbon atoms, C6 to C 18 aryl or C3 to C 18 heteroaryl.

[0413] According to one embodiment, wherein T 1 , T 2 , T 3 , T 4 , and T 5 can independently be selected from a single bond, phenylene, biphenylene, or terphenylenylidene. According to one embodiment, wherein T 1 z, T 2 , T 3 , T 4 , and T 5 can independently be selected from phenylene, biphenylene, or terphenylenyl, and one of 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 can independently be selected from phenylene or biphenylene, and one of T 1 , T 2 , T 3 , T[[ID=?3]] 4 , and T 5 is a single bond. According to one embodiment, wherein T 1 , T 2 , T3 , T 4 and T 5 can be independently selected from phenylene or biphenylene, and T 1 , T 2 , T 3 , T 4 and T 5 Two of them are single bonds.

[0414] According to one embodiment, wherein T 1 , T 2 and T 3 can be independently selected from phenylene, and one of T 1 , T 2 and T 3 is a single bond. According to one embodiment, wherein T 1 , T 2 and T 3 can be independently selected from phenylene, and two of T 1 , T 2 and T 3 are single bonds.

[0415] According to one embodiment, wherein T 6 can be phenylene, biphenylene or terphenylenyl. According to one embodiment, wherein T 6 can be phenylene. According to one embodiment, wherein T 6 can be biphenylene. According to one embodiment, wherein T 6 can be terphenylenyl.

[0416] According to one embodiment, wherein Ar' 1 , Ar' 2 , Ar' 3 , Ar' 4 and Ar' 5 can be independently selected from E1 to E16:

[0417]

[0418] wherein the asterisk "*" represents the bonding position.

[0419] According to one embodiment, wherein Ar' 1 , Ar' 2 , Ar' 3 , Ar' 4 and Ar' 5 can be independently selected from E1 to E15; or selected from E1 to E10 and E13 to E15.

[0420] According to one embodiment, wherein Ar' 1 , Ar'2 , Ar' 3 , Ar' 4 and Ar' 5 can be independently selected from E1, E2, E5, E7, E9, E10, E13 to E16.

[0421] When Ar' is selected within this range 1 , Ar' 2 , Ar' 3 , Ar' 4 and Ar' 5 the standard starting temperature can be within a range that is particularly suitable for mass production.

[0422] The "matrix compound of formula (XII) or formula (XIII)" can also be referred to as a "hole transport compound".

[0423] According to one embodiment, the substantially covalent matrix compound comprises at least one naphthyl group, carbazole group, dibenzofuran group, dibenzothiophene group, and / or substituted fluorene group, wherein the substituents are independently selected from methyl, phenyl, or fluorene.

[0424] According to one embodiment of the electronic device, wherein the matrix compound of formula (XII) or formula (XIII) is selected from F1 to F20:

[0425]

[0426]

[0427]

[0428] According to one embodiment of the present invention, the electronic organic device is an organic light emitting diode.

[0429] According to a preferred embodiment of the present invention, the electroluminescent device is an organic light emitting diode, wherein light is emitted through the cathode layer.

[0430] The present invention also relates to a display device comprising the organic electroluminescent device according to the present invention.

[0431] According to a preferred embodiment of the present invention, the display device comprises the organic electroluminescent device according to the present invention, wherein the cathode layer is transparent.

[0432] p-type charge generation layer

[0433] The p-type charge generation layer can be formed on the anode layer or the cathode layer by vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blodgett (LB) deposition, etc. When the p-type charge generation layer is formed by vacuum deposition, the deposition conditions can vary according to one or more compounds used to form the layer and the desired structure and thermal properties of the layer. However, generally speaking, the conditions for vacuum deposition can include a deposition temperature of 100 °C to 350 °C, 10 -8 torr to 10 -3 torr of pressure (1 torr is equal to 133.322 Pa) and a deposition rate of 0.1 nm / s to 10 nm / s.

[0434] When the p-type charge generation layer is formed by spin coating or printing, the coating conditions can vary according to one or more compounds used to form the layer and the desired structure and thermal properties of the organic semiconductor layer. For example, the coating conditions can include a coating speed of about 2000 rpm to about 5000 rpm, and a heat treatment temperature of about 80 °C to about 200 °C. After coating, the solvent is removed by heat treatment.

[0435] The thickness of the p-type charge generation layer can be in the range of about 1 nm to about 20 nm, for example, in the range of about 2 nm to about 15 nm or about 2 nm to about 12 nm.

[0436] Hole injection layer

[0437] 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 the HIL is formed by vacuum deposition, the deposition conditions can vary according to the compound used to form the HIL and the desired structure and thermal properties of the HIL. However, generally speaking, the conditions for vacuum deposition can include a deposition temperature of 100 °C to 500 °C, 10 -8 torr to 10 -3 torr of pressure (1 torr is equal to 133.322 Pa) and a deposition rate of 0.1 nm / s to 10 nm / s.

[0438] When the HIL is formed by spin coating or printing, the coating conditions can 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 can include a coating speed of about 2000 rpm to about 5000 rpm, and a heat treatment temperature of about 80 °C to about 200 °C. After coating, the solvent is removed by heat treatment.

[0439] The thickness of the HIL can be in the range of about 1 nm to about 100 nm, for example, in the range of about 1 nm to about 25 nm. When the thickness of the HIL is within this range, the HIL can have excellent hole injection characteristics and will not cause substantial damage to the driving voltage.

[0440] Other layers

[0441] According to the present invention, in addition to the layers mentioned above, the organic electroluminescent device may further include other layers. Exemplary embodiments of the corresponding layers are described below:

[0442] Substrate

[0443] The substrate may 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 may be either a transparent material or an opaque material, such as a glass substrate, a plastic substrate, a metal substrate, a silicon substrate, or a backplane.

[0444] Anode layer

[0445] The anode layer can be formed by depositing or sputtering a material for forming the anode layer. The material for forming the anode layer can be a high work function material to facilitate hole injection. The anode material may also be selected from low work function materials (i.e., aluminum). The anode electrode can be a transparent or reflective electrode. Transparent conductive oxides such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), aluminum zinc oxide (AlZO), and zinc oxide (ZnO) can be used to form the anode electrode. Metals can also be used, and typically silver (Ag), gold (Au), or metal alloys are used to form the anode layer.

[0446] Hole transport layer

[0447] The organic electronic device according to the present invention may further include at least one hole transport layer (HTL). According to one embodiment of the present invention, at least one hole transport layer is included in one of at least two light-emitting units, and preferably at least one hole transport layer is included in each light-emitting unit.

[0448] 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 for deposition and coating can be similar to those for forming the HIL or CGL. However, the conditions for vacuum or solution deposition can vary depending on the compound used to form the HTL.

[0449] The HTL can be formed from any compound commonly used to form the HTL. For example, Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953 - 1010 disclose applicable compounds and are incorporated herein by reference. Examples of compounds that can be used to form the HTL are carbazole derivatives such as N - phenylcarbazole or polyvinylcarbazole; benzidine derivatives such as N,N'-bis(3 - methylphenyl)-N,N'-diphenyl-[1,1 - biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen - 1 - yl)-N,N'-diphenylbenzidine (α - NPD); and triphenylamine - based compounds such as 4,4',4"-tris(N - carbazolyl)triphenylamine (TCTA). Among these compounds, TCTA can transport holes and inhibit exciton diffusion into the EML.

[0450] According to one embodiment of the present invention, the hole - transporting layer may comprise the substantially covalent matrix compound as described above.

[0451] According to a preferred embodiment of the present invention, the hole - injecting layer and the hole - transporting layer may comprise the same substantially covalent matrix compound as described above.

[0452] According to one embodiment of the present invention, the hole - transporting layer may comprise the compound of formula (XII) or formula (XIII) as described above.

[0453] According to a preferred embodiment of the present invention, the hole - injecting layer and the hole - transporting layer may comprise the same compound of formula (XII) or formula (XIII) as described above.

[0454] According to a preferred embodiment of the present invention, the p - type charge - generating layer, the hole - injecting layer, and the hole - transporting layer may comprise the same substantially covalent matrix compound.

[0455] According to a preferred embodiment of the present invention, the p - type charge - generating layer, the hole - injecting layer, and the hole - transporting layer may comprise the same compound of formula (XII) or formula (XIII) as described above.

[0456] The thickness of the HTL can be in the range of about 5 nm to about 250 nm, preferably about 10 nm to about 200 nm, more preferably about 20 nm to about 190 nm, more preferably about 40 nm to about 180 nm, more preferably about 60 nm to about 170 nm, more preferably about 80 nm to about 160 nm, more preferably about 100 nm to about 160 nm, more preferably about 120 nm to about 140 nm. The preferred thickness of the HTL can be 170 nm to 200 nm.

[0457] When the thickness of the HTL is within this range, the HTL can have excellent hole transport characteristics and will not cause substantial damage to the driving voltage.

[0458] Electron blocking layer

[0459] The function of the electron blocking layer (EBL) is to prevent electrons from transferring from the light-emitting layer to the hole transport layer and thus confine the electrons in the light-emitting layer. Thereby, the efficiency, operating voltage, and / or lifetime are improved. Generally, the electron blocking layer contains a triarylamine compound. The LUMO energy level of the triarylamine compound can be closer to the vacuum energy level than the LUMO energy level of the hole transport layer. The HOMO energy level of the electron blocking layer can be farther from the vacuum energy level than the HOMO energy level of the hole transport layer. The thickness of the electron blocking layer can be selected between 2 nm and 20 nm.

[0460] If the electron blocking layer has a high triplet energy level, it can also be described as a triplet control layer.

[0461] If a phosphorescent green or blue light-emitting layer is used, the function of the triplet control layer is to reduce triplet quenching. Thereby, a higher luminous efficiency of the phosphorescent light-emitting layer can be achieved. The triplet control layer is selected from triarylamine compounds having a triplet energy level higher than the triplet energy level of the phosphorescent emitter in the adjacent light-emitting layer. EP 2 722 908 A1 describes compounds suitable for the triplet control layer, especially triarylamine compounds.

[0462] Photoactive layer (PAL)

[0463] According to an embodiment of the present invention, the organic electronic device may further include a photoactive layer, wherein the photoactive layer is disposed between the anode layer and the cathode layer.

[0464] The photoactive layer converts current into photons or photons into current.

[0465] 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 by vacuum deposition or spin coating, the conditions for deposition and coating can be similar to the conditions for forming the HIL. However, the conditions for deposition and coating can vary depending on the compound used to form the PAL.

[0466] The photoactive layer can be a light-emitting layer or a light-absorbing layer, especially a light-emitting layer.

[0467] Emitting layer (EML)

[0468] According to an embodiment of the present invention, the organic electronic device may further include an emitting layer, wherein the emitting layer is disposed between the anode layer and the cathode layer.

[0469] The EML can be formed on the HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When the EML is formed by vacuum deposition or spin coating, the conditions for deposition and coating can be similar to those for forming the HIL. However, the conditions for deposition and coating can vary depending on the compound used to form the EML.

[0470] The emitting layer (EML) can be formed by a combination of a host and an emitter dopant. Examples of the host are Alq3, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalen-2-yl)anthracene (ADN), 4,4',4"-tris(carbazol-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), distyrylarylene (DSA), and bis(2-(2-hydroxyphenyl)benzothiazole)zinc (Zn(BTZ)2).

[0471] The emitter dopant can be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters that emit light through the thermally activated delayed fluorescence (TADF) mechanism can be preferred because of their higher efficiency. The emitter can be a small molecule or a polymer.

[0472] 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 can also be used.

[0473] Examples of phosphorescent green emitter dopants are Ir(ppy)3 (ppy = phenylpyridine), Ir(ppy)2(acac), and Ir(mpyp)3.

[0474] Examples of phosphorescent blue emitter dopants are F2Irpic, (F2ppy)2Ir(tmd), and Ir(dfppz)3; and truxene. Examples of fluorescent blue emitter dopants are 4,4'-bis(4-diphenylaminostyryl)biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe).

[0475] The amount of the emitter dopant can be in the range of about 0.01 parts by weight to about 50 parts by weight relative to 100 parts by weight of the host. Alternatively, the emitting layer can be composed of an emitting polymer. The thickness of the EML can 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 can have excellent luminescence and will not cause substantial damage to the driving voltage.

[0476] Hole blocking layer (HBL)

[0477] A hole blocking layer (HBL) can be formed on the EML by using vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. to prevent holes from diffusing into the ETL. When the EML contains a phosphorescent dopant, the HBL may also have a triplet exciton blocking function.

[0478] The HBL can also be referred to as an auxiliary ETL or a-ETL.

[0479] When the HBL is formed by vacuum deposition or spin coating, the conditions for deposition and coating can be similar to those for forming the HIL. However, the conditions for deposition and coating can vary depending on the compound used to form the HBL. Any compound commonly used to form the HBL can be used. Examples of compounds used to form the HBL include diazole derivatives, triazole derivatives, phenanthroline derivatives, and azine derivatives, preferably triazine or pyrimidine derivatives.

[0480] The thickness of the HBL can 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 can have excellent hole blocking performance and will not cause substantial damage to the driving voltage.

[0481] Electron transport layer (ETL)

[0482] The organic electronic device according to the present invention may further include at least one electron transport layer (ETL). According to one embodiment of the present invention, at least one electron transport layer is included in one of at least two light-emitting units, and preferably at least one electron transport layer is included in each light-emitting unit.

[0483] According to another embodiment of the present invention, the electron transport layer may further include an azine compound, preferably a pyridine, pyrimidine, or triazine compound, and most preferably a triazine compound or a pyrimidine compound.

[0484] 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-fluoren-4-yl)-6-phenyl-1,3,5-triazine, 2-(3-(2,6-dimethylpyridin-3-yl)-5-(phenanthren-9-yl)phenyl)-4,6-diphenyl-1,3,5-triazine, 3'-(4-phenyl-6-(spiro[fluorene-9,9'-xanthene]-2'-yl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, and 4'-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalen-1-yl)-[1,1'-biphenyl]-4-carbonitrile.

[0485] In one embodiment, the electron transport layer may further comprise a dopant selected from alkali metal organic complexes, preferably LiQ.

[0486] The thickness of the ETL may be in the range of about 15 nm to about 50 nm, for example, in the range of about 20 nm to about 40 nm. When the thickness of the ETL is within this range, the ETL may have satisfactory electron injection performance and will not cause substantial damage to the driving voltage.

[0487] 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, and most preferably a triazine compound.

[0488] Electron injection layer (EIL)

[0489] An optional EIL capable of facilitating electron injection from the cathode may be formed on the ETL, preferably closest to the cathode, and more preferably directly on the electron transport layer. Examples of materials for forming the EIL include lithium 8-hydroxyquinolate (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 depending on the material used to form the EIL.

[0490] 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 performance and will not cause substantial damage to the driving voltage.

[0491] Cathode layer

[0492] The cathode layer is formed on the ETL or the optional EIL. The cathode layer may be formed of a metal, an alloy, a conductive compound, or a mixture thereof. The cathode electrode may have a low work function. For example, the cathode layer may be formed of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), etc. Alternatively, the cathode electrode may be formed of a transparent conductive oxide such as ITO or IZO.

[0493] The thickness of the cathode layer may be in the range of about 5 nm to about 1000 nm, for example, in the range of about 10 nm to about 100 nm. When the thickness of the cathode layer is in the range of about 5 nm to about 50 nm, the cathode layer may be transparent or translucent even if formed of a metal or a metal alloy.

[0494] In a preferred embodiment, the cathode layer comprises a metal or a metal alloy and is transparent.

[0495] It should be understood that the cathode layer is not part of the electron injection layer or the electron transport layer.

[0496] Other layouts of the organic electroluminescent device

[0497] According to one embodiment of the present invention, the organic electroluminescent device preferably comprises an anode layer; a hole injection layer; a first hole transport layer; a first electron blocking layer; a first light emitting layer; a first optional hole blocking layer; and a first electron transport layer in this order; wherein the hole injection layer is in direct contact with the anode layer, and wherein the hole injection layer comprises a first hole transport matrix compound and a compound of formula (II), and the compound of formula (II) is a metal compound selected from metal salts or metal complexes, and the metal salts or metal complexes comprise metal cations and at least one monoanion composed of at least 20 covalently bonded atoms and / or at least one monoanion ligand composed of at least 20 covalently bonded atoms; a first charge generation layer disposed on the first electron transport layer, wherein the first charge generation layer comprises a first n-type charge generation layer and a first p-type charge generation layer, wherein the first p-type charge generation layer comprises a second hole transport matrix compound and a compound of formula (I), wherein the first n-type charge generation layer comprises a matrix compound and a metal dopant, and preferably the metal dopant is selected from ytterbium, lithium or magnesium; a second hole transport layer; a second electron blocking layer; a second light emitting layer; a second optional hole blocking layer, an electron transport layer, an electron injection layer and a cathode layer.

[0498] According to one embodiment of the present invention, the organic electroluminescent device preferably includes an anode layer, a hole injection layer, a hole transport layer, a first electron blocking layer, and a first light-emitting layer in this order, wherein the hole injection layer contains a first hole transport matrix compound and a compound of formula (II), the compound of formula (II) is a metal compound selected from metal salts or metal complexes, the metal salts or metal complexes contain metal cations and at least one monoanion composed of at least 20 covalently bonded atoms and / or at least one monoanion ligand composed of at least 20 covalently bonded atoms, and wherein the hole injection layer is in direct contact with the anode layer; a first optional hole blocking layer, a first electron transport layer, a first charge generation layer disposed on the first electron transport layer, wherein the first charge generation layer contains a first n-type charge generation layer and a first p-type charge generation layer, wherein the first p-type charge generation layer contains a second hole transport matrix compound and a compound of formula (I), wherein the first n-type charge generation layer contains a matrix compound and a metal dopant, and preferably the metal dopant is selected from ytterbium, lithium, or magnesium; a second hole transport layer and a second electron blocking layer; a second light-emitting layer; a second optional hole blocking layer; a second electron transport layer; a second charge generation layer disposed on the second electron transport layer, wherein the second charge generation layer contains a second n-type charge generation layer and a second p-type charge generation layer, wherein the second p-type charge generation layer contains a second hole transport matrix compound and a compound of formula (I), wherein the second n-type charge generation layer contains a matrix compound and a metal dopant, and preferably the metal dopant is selected from ytterbium, lithium, magnesium; a third hole transport layer (HTL3) and a third electron blocking layer; a third light-emitting layer; a third optional hole blocking layer, an electron transport layer, an electron injection layer, and a cathode layer (CAT).

[0499] According to one embodiment of the present invention, the organic electroluminescent device preferably includes an anode layer, a hole injection layer, a hole transport layer, a first electron blocking layer, and a first light emitting layer in this order; wherein the hole injection layer includes a first hole transport matrix compound and a compound of formula (II), and the compound of formula (II) is a metal compound selected from metal salts or metal complexes, and the metal salts or metal complexes include metal cations and at least one monoanion composed of at least 20 covalently bonded atoms and / or at least one monoanion ligand composed of at least 20 covalently bonded atoms, and wherein the hole injection layer is in direct contact with the anode layer; a first optional hole blocking layer; a first electron transport layer; a first charge generation layer disposed on the first electron transport layer, wherein the first charge generation layer includes a first n-type charge generation layer and a first p-type charge generation layer, wherein the first p-type charge generation layer includes a second hole transport matrix compound and a compound of formula (I), wherein the first n-type charge generation layer includes a matrix compound and a metal dopant, and preferably the metal dopant is selected from ytterbium, lithium, or magnesium; a second hole transport layer and a second electron blocking layer; a second light emitting layer; a second optional hole blocking layer; a second electron transport layer; a second charge generation layer disposed on the second electron transport layer, wherein the second charge generation layer includes a second n-type charge generation layer and a second p-type charge generation layer, wherein the second p-type charge generation layer includes a second hole transport matrix compound and a compound of formula (I), and wherein the second n-type charge generation layer (n-CGL2) includes a matrix compound and a metal dopant, and preferably the metal dopant is selected from ytterbium, lithium, magnesium; a third hole transport layer and a third electron blocking layer; a third light emitting layer; a third optional hole blocking layer; a third electron transport layer; a charge generation layer disposed on the third electron transport layer, wherein the third charge generation layer includes a third n-type charge generation layer and a third p-type charge generation layer; wherein the third p-type charge generation layer includes a second hole transport matrix compound and a compound of formula (I), and wherein the third n-type charge generation layer includes a matrix compound and a metal dopant, and preferably the metal dopant is selected from ytterbium, lithium, or magnesium; a fourth hole transport layer; a fourth electron blocking layer; a fourth light emitting layer; a fourth optional hole blocking layer, electron transport layer, electron injection layer, and cathode layer. Description of the Drawings

[0500] There are no special exceptions in terms of the dimensions, shapes, material selections, and technical principles of the above components in the described embodiments, as well as the claimed components and the components used according to the present invention. Therefore, the known selection criteria in the relevant fields can be applied without limitation.

[0501] Other details, features, and advantages of the objects of the present invention are disclosed in the dependent claims and the following description of the corresponding drawings, which illustrate, by way of example, preferred embodiments according to the present invention. However, any embodiment may not necessarily represent the full scope of the present invention, and thus the scope of the present invention is interpreted with reference to the claims and this specification. It should be understood that the above general description and the following detailed description are merely exemplary and explanatory and are intended to further illustrate the claimed invention.

[0502] Figure 1 is a schematic cross-sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.

[0503] Figure 2 is a schematic cross-sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.

[0504] Figure 3 is a schematic cross-sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.

[0505] Figure 4 is a schematic cross-sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.

[0506] The drawings are described in more detail below with reference to the embodiments. However, the present disclosure is not limited by the following drawings.

[0507] In this document, when a first element is said to be formed or disposed "on" or "above" a second element, the first element may be directly disposed on the second element, or one or more other elements may be disposed between them. When a first element is said to be formed or disposed "directly on" or "directly above" a second element, no other elements are disposed between them.

[0508] Reference Figure 1 [[ID=D27]] shows that the organic electroluminescent device 100 includes an anode layer (ANO) 120, a hole injection layer (HIL) 130, and a first emission layer (EML1) 145, wherein the hole injection layer (HIL) 130 contains a hole transport matrix compound and a metal compound, and the metal compound is selected from a metal salt or a metal complex, and the metal salt or the metal complex contains a metal cation and at least one monoanion composed of at least 20 covalently bonded atoms and / or at least one monoanion ligand composed of at least 20 covalently bonded atoms.

[0509] The organic electroluminescent device further includes a first charge generation layer (CGL1) 160, wherein the first charge generation layer (CGL1) 160 includes a first n-type charge generation layer (n-CGL1) 161 and a first p-type charge generation layer (p-CGL1) 162, wherein the first n-type charge generation layer (n-CGL1) 161 includes a matrix compound and a metal dopant, and preferably the metal dopant is selected from ytterbium, lithium or magnesium.

[0510] The organic electroluminescent device 100 further includes a second emission layer (EML2) 245 and a cathode layer (CAT) 190.

[0511] Figure 2 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0512] Reference Figure 2 , the organic electroluminescent device 100 includes an anode layer (ANO) 120, a hole injection layer (HIL) 130, a first hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, a first emission layer (EML1) 145, a first optional hole blocking layer (HBL1) 147 and a first electron transport layer (ETL1) 149, wherein the hole injection layer (HIL) 130 includes a first hole transport matrix compound and a compound of formula (II), and the compound of formula (II) is a metal compound selected from metal salts or metal complexes, and the metal salts or metal complexes include metal cations and at least one monoanion composed of at least 20 covalently bonded atoms and / or at least one monoanion ligand composed of at least 20 covalently bonded atoms.

[0513] The organic electroluminescent device further includes a first charge generation layer (CGL1) 160 disposed on the first electron transport layer (ETL1) 149, wherein the first charge generation layer (CGL1) 160 includes a first n-type charge generation layer (n-CGL1) 161 and a first p-type charge generation layer (p-CGL1) 162, and the first p-type charge generation layer (p-CGL1) 162 includes a second hole transport matrix compound and a compound of formula (I);

[0514] wherein the first n-type charge generation layer (n-CGL1) 161 includes a matrix compound and a metal dopant, and preferably the metal dopant is selected from ytterbium, lithium or magnesium.

[0515] The organic electroluminescent device 100 further includes a second hole transport layer (HTL2) 241 and a second electron blocking layer (EBL2) 242.

[0516] The organic electroluminescent device 100 further includes a second emission layer (EML2) 245.

[0517] The organic electroluminescent device 100 further includes a second optional hole blocking layer (HBL2) 247, an electron transport layer (ETL) 148, an electron injection layer (EIL) 180, and a cathode layer (CAT) 190.

[0518] Figure 3 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0519] Reference Figure 3 , the organic electroluminescent device 100 includes an anode layer (ANO) 120, a hole injection layer (HIL) 130, a hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, and a first emission layer (EML1) 145; wherein the hole injection layer (HIL) 130 includes a first hole transport matrix compound and a compound of formula (II), and the compound of formula (II) is a metal compound selected from metal salts or metal complexes, and the metal salts or metal complexes include metal cations and at least one monoanion composed of at least 20 covalently bonded atoms and / or at least one monoanion ligand composed of at least 20 covalently bonded atoms.

[0520] The organic electroluminescent device 100 further includes a first optional hole blocking layer (HBL1) 147.

[0521] The organic electroluminescent device 100 further includes a first electron transport layer (ETL1) 149.

[0522] The organic electroluminescent device further includes a first charge generation layer (CGL1) 160 disposed on the first electron transport layer (ETL1) 149, wherein the first charge generation layer (CGL1) 160 includes a first n-type charge generation layer (n-CGL1) 161 and a first p-type charge generation layer (p-CGL1) 162, and the first p-type charge generation layer (p-CGL1) 162 includes a second hole transport matrix compound and a compound of formula (I);

[0523] wherein the first n-type charge generation layer (n-CGL1) 161 includes a matrix compound and a metal dopant, and preferably the metal dopant is selected from ytterbium, lithium, or magnesium.

[0524] The organic electroluminescent device 100 further includes a second hole transport layer (HTL2) 241 and a second electron blocking layer (EBL2) 242.

[0525] The organic electroluminescent device 100 further includes a second emission layer (EML2) 245.

[0526] The organic electroluminescent device 100 further includes a second optional hole blocking layer (HBL2) 247.

[0527] The organic electroluminescent device 100 further includes a second electron transport layer (ETL2) 249.

[0528] The organic electroluminescent device further includes a second charge generation layer (CGL2) 260 disposed on the second electron transport layer (ETL2) 249, wherein the second charge generation layer (CGL2) 260 includes a second n-type charge generation layer (n-CGL2) 261 and a second p-type charge generation layer (p-CGL2) 262, and the second p-type charge generation layer (p-CGL2) 262 includes a second hole transport matrix compound and a compound of formula (I);

[0529] wherein the second n-type charge generation layer (n-CGL2) 261 includes a matrix compound and a metal dopant, and preferably the metal dopant is selected from ytterbium, lithium, and magnesium.

[0530] The organic electroluminescent device 100 further includes a third hole transport layer (HTL3) 341 and a third electron blocking layer (EBL3) 342.

[0531] The organic electroluminescent device 100 further includes a third light emitting layer (EML3) 345.

[0532] The organic electroluminescent device 100 further includes a third optional hole blocking layer (HBL3) 347, an electron transport layer (ETL) 148, an electron injection layer (EIL) 180, and a cathode layer (CAT) 190.

[0533] Figure 4 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0534] Reference Figure 4 , the organic electroluminescent device 100 includes an anode layer (ANO) 120, a hole injection layer (HIL) 130, a hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, and a first light emitting layer (EML1) 145; wherein the hole injection layer (HIL) 130 includes a first hole transport matrix compound and a compound of formula (II), and the compound of formula (II) is a metal compound selected from metal salts or metal complexes, and the metal salts or metal complexes include metal cations and at least one monoanion composed of at least 20 covalently bonded atoms and / or at least one monoanion ligand composed of at least 20 covalently bonded atoms.

[0535] The organic electroluminescent device 100 further includes a first optional hole blocking layer (HBL1) 147.

[0536] The organic electroluminescent device 100 further includes a first electron transport layer (ETL1) 149.

[0537] The organic electroluminescent device further includes a first charge generation layer (CGL1) 160 disposed on the first electron transport layer (ETL1) 149, wherein the first charge generation layer (CGL1) 160 includes a first n-type charge generation layer (n-CGL1) 161 and a first p-type charge generation layer (p-CGL1) 162, and the first p-type charge generation layer (p-CGL1) 162 includes a second hole transport matrix compound and a compound of formula (I);

[0538] wherein the first n-type charge generation layer (n-CGL1) 161 includes a matrix compound and a metal dopant, and preferably the metal dopant is selected from ytterbium, lithium or magnesium.

[0539] The organic electroluminescent device 100 further includes a second hole transport layer (HTL2) 241 and a second electron blocking layer (EBL2) 242.

[0540] The organic electroluminescent device 100 further includes a second light emitting layer (EML2) 245.

[0541] The organic electroluminescent device 100 further includes a second optional hole blocking layer (HBL2) 247.

[0542] The organic electroluminescent device 100 further includes a second electron transport layer (ETL2) 249.

[0543] The organic electroluminescent device further includes a second charge generation layer (CGL2) 260 disposed on the second electron transport layer (ETL2) 249, wherein the second charge generation layer (CGL2) 260 includes a second n-type charge generation layer (n-CGL2) 261 and a second p-type charge generation layer (p-CGL2) 262, and the second p-type charge generation layer (p-CGL2) 262 includes a second hole transport matrix compound and a compound of formula (I),

[0544] wherein the second n-type charge generation layer (n-CGL2) 261 includes a matrix compound and a metal dopant, and preferably the metal dopant is selected from ytterbium, lithium, magnesium.

[0545] The organic electroluminescent device 100 further includes a third hole transport layer (HTL3) 341 and a third electron blocking layer (EBL3) 342.

[0546] The organic electroluminescent device 100 further includes a third emitting layer (EML3) 345.

[0547] The organic electroluminescent device 100 further includes a third optional hole blocking layer (HBL3) 347.

[0548] The organic electroluminescent device 100 further includes a third electron transport layer (ETL3) 349.

[0549] The organic electroluminescent device further includes a charge generation layer (CGL3) 360 disposed on the third electron transport layer (ETL3) 349, wherein the third charge generation layer (CGL3) 360 includes a third n-type charge generation layer (n-CGL3) 361 and a third p-type charge generation layer (p-CGL3) 362.

[0550] Wherein the third p-type charge generation layer (p-CGL3) 362 includes a second hole transport matrix compound and a compound of formula (I);

[0551] Wherein the third n-type charge generation layer (n-CGL3) 361 includes a matrix compound and a metal dopant, and preferably the metal dopant is selected from ytterbium, lithium or magnesium.

[0552] The organic electroluminescent device 100 further includes a fourth hole transport layer (HTL4) 441 and a fourth electron blocking layer (EBL4) 442.

[0553] The organic electroluminescent device 100 further includes a fourth emitting layer (EML4) 345.

[0554] The organic electroluminescent device 100 further includes a fourth optional hole blocking layer (HBL4) 447, an electron transport layer (ETL) 148, an electron injection layer (EIL) 180 and a cathode layer (CAT) 190.

[0555] 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

[0556] The present invention is also illustrated by the following examples, which are merely exemplary and not restrictive.

[0557] The compound of formula (I) can be prepared as described in EP2180029A1 and WO2016097017A1.

[0558] Calculating HOMO and LUMO

[0559] The HOMO of the hole transport matrix compound and the LUMO of the compound of formula (I) were calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). The optimized geometry of the molecular structure and the HOMO and LUMO energy levels were determined by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase.

[0560] As implemented in the program package ORCA 5.0.3-f.1 version (Department of Theoretical and Spectroscopic Chemistry, Max Planck Institute for Coal Research, Kaiser Wilhelm Platz 1, 45470 Muelheim / Ruhr, Germany), the LUMO value of the compound of formula (II) was calculated by applying the hybrid functional B3LYP in the gas phase, using the Def2-TZVP basis set and the SDD effective core potential (ECP) for the metal.

[0561] If more than one conformation is feasible, the conformation with the lowest total energy is selected.

[0562] General procedure for manufacturing OLED

[0563] OLED and comparative device comprising a charge generation layer (CGL) according to the present invention

[0564] For the examples, a glass substrate with an anode layer having a first anode sublayer of 8 nm ITO, a second anode sublayer of 120 nm Ag, and a third anode sublayer of 10 nm ITO was cut into pieces of 25 mm × 25 mm × 0.7 mm, ultrasonically washed with water for 60 minutes, and then ultrasonically washed with isopropanol for 20 minutes. The liquid film was removed in a nitrogen stream, and then plasma treatment was carried out to prepare the anode layer. The plasma treatment was carried out in a nitrogen atmosphere or in an atmosphere containing 98 vol% nitrogen and 2 vol% oxygen.

[0565] Then, a hole injection layer (HIL) with a thickness of 10 nm was formed on the anode layer by co-depositing F3 (N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine) or CuPC (see the description in the following table) and the metal salt or metal complex according to Table 3 or the comparative example.

[0566] Then, a first hole transport layer (HTL1) with a thickness of 27 nm was formed on the HIL by depositing F3 (N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine).

[0567] Then, a first electron blocking layer (EBL1) with a thickness of 5 nm is formed on HTL1 by depositing N-([1,1'-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(triphenylsilyl)phenyl)-9H-fluorene-2-amine.

[0568] Then, a first emitting layer (EML1) with a thickness of 20 nm is formed on EBL1 by co-depositing 97 vol% of H09 (Sun Fine Chemicals, Korea) as the EML host and 3 vol% of BD200 (Sun Fine Chemicals, Korea) as the fluorescent blue dopant.

[0569] Then, a first hole blocking layer (HBL1) with a thickness of 5 nm is formed on the first emitting layer by depositing 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[0570] Then, a first electron transport layer (ETL1) with a thickness of 20 nm is formed on the first emitting layer by co-depositing 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%.

[0571] Then, an n-CGL with a thickness of 10 nm is formed on ETL by co-depositing 99 vol% of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 vol% of Yb.

[0572] Then, a p-CGL with a thickness of 10 nm is formed on n-CGL by co-depositing F3 (N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine) as the matrix compound and a dopant compound. The composition of p-CGL can be seen in Table 3.

[0573] Then, a second hole transport layer (HTL2) with a thickness of 24 nm is formed on p-CGL by depositing F3 (N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine).

[0574] Then, a second electron blocking layer (EBL2) with a thickness of 5 nm is formed on HTL2 by depositing N-([1,1'-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(triphenylsilyl)phenyl)-9H-fluorene-2-amine.

[0575] Then, a second emitting layer (EML2) with a thickness of 20 nm is formed on EBL2 by co-depositing 97 vol% of H09 (Sun Fine Chemicals, Korea) as the EML host and 3 vol% of BD200 (Sun Fine Chemicals, Korea) as the fluorescent blue dopant.

[0576] Then, a second hole blocking layer (HBL2) with a thickness of 5 nm is formed on EML2 by depositing 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[0577] Then, a second electron transport layer (ETL2) with a thickness of 30 nm is formed on HBL by co-depositing 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%.

[0578] Then, an electron injection layer (EIL) with a thickness of 2 nm is formed on ETL by depositing Yb.

[0579] Then, by at 10 -7 mbar at a rate of to co-deposit Ag:Mg (90:10 vol%), a cathode layer with a thickness of 13 nm is formed on EIL.

[0580] Then, a cover layer with a thickness of 75 nm is 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).

[0581] The OLED stack is protected from environmental conditions by encapsulating the device with a glass slide. Thus, a cavity is formed, which includes a getter material for further protection.

[0582] OLED containing a hole injection layer but no charge generation layer as a comparative example

[0583] For a top-emitting OLED device, a substrate with dimensions of 150 mm × 150 mm × 0.7 mm is ultrasonically cleaned in a 2% aqueous solution of Deconex FPD 211 for 7 minutes, then ultrasonically cleaned in pure water for 5 minutes, and dried in a spin dryer for 15 minutes. Subsequently, Ag is deposited on the substrate as the anode at a pressure of 10 -5 to 10 -7 mbar.

[0584] Then, N-({[1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine} (Compound F3, see above) or CuPC (see the following description) and the compound of formula (II) or the comparative compound according to Table 1 are vacuum deposited on the anode to form a 10 nm thick HIL. The amount of the compound of formula (II) in the HIL is shown in Table 4.

[0585] Then, N-({[1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine} is vacuum deposited on the HIL to form a 128 nm thick first HTL.

[0586] Then, N-([1,1'-biphenyl]-4-yl)-9,9-diphenyl-N-(4-triphenylsilyl)phenyl)-9H-fluorene-2-amine (CAS 1613079-70-1) is vacuum deposited on the HTL to form a 5 nm thick electron blocking layer (EBL).

[0587] Then, 97 vol% of H09 (Sun Fine Chemicals, Korea) as the EML host and 3 vol% of BD200 (Sun Fine Chemicals, Korea) as the fluorescent blue dopant are deposited on the EBL to form a 20 nm thick first blue light-emitting EML.

[0588] Then, 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine is deposited on the light-emitting layer to form a 5 nm thick hole blocking layer.

[0589] Then, a 31 nm thick electron transport layer (ETL) is formed on the hole blocking layer by depositing 50 wt% of 4'-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalen-1-yl)-[1,1'-biphenyl]-4-carbonitrile and 50 wt% of LiQ.

[0590] Then, at 10 -7 mbar at a to rate, Yb is evaporated on the electron transport layer to form a 2 nm thick electron injection layer.

[0591] At 10 -7 mbar at a to Evaporate Ag / Mg (90:10 vol%) at a rate to form a cathode with a thickness of 13 nm.

[0592] Then, vacuum deposit N-({[1,1'-biphenyl]-4-yl}-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine) on the cathode layer to form a cover layer with a thickness of 75 nm.

[0593] Protect the OLED stack from environmental conditions by encapsulating the device with a glass slide. Thus, a cavity is formed, which includes a getter material for further protection.

[0594] To evaluate the performance of the inventive example compared with the prior art, measure the current efficiency at 20 °C. Use a Keithley 2635 source measurement unit to determine the current-voltage characteristics by providing a voltage (in V) and measuring the current flowing through the device under test (in mA). The voltage applied to the device varies in the range between 0 V and 10 V in steps of 0.1 V. Similarly, measure the luminous density (in cd / m 2 to determine the luminous density-voltage characteristics and CIE coordinates. Determine the cd / A efficiency at 15 mA / cm 2 by interpolating the luminous density-voltage and current-voltage characteristics respectively.

[0595] In a bottom-emitting device, the light emission is mainly Lambertian and is quantified as a percentage of the external quantum efficiency (EQE). To determine the efficiency EQE (in %), measure the light output of the device at 15 mA / cm 2 using a calibrated photodiode.

[0596] In a top-emitting device, the light emission is forward, non-Lambertian, and also highly dependent on the microcavity. Therefore, the efficiency EQE will be higher compared with the bottom-emitting device. To determine the efficiency EQE (in %), measure the light output of the device at 15 mA / cm 2 using a calibrated photodiode.

[0597] Use a Keithley 2400 source meter to measure the lifetime LT of the device at environmental conditions (20 °C) and 30 mA / cm 2 and record it in hours.

[0598] The brightness of the device is measured using a calibrated photodiode. The lifetime LT is defined as the time until the brightness of the device drops to 97% of its initial value.

[0599] The increment ΔU of the operating voltage is used as a measure of the operating voltage stability of the device.

[0600] Furthermore, during the LT measurement, this increment is determined by subtracting the operating voltage after 100 hours from the operating voltage after 1 hour after the device starts to operate.

[0601] ΔU = [U(100 h) - U(1h)]

[0602] The smaller the value of ΔU, the better the operating voltage stability.

[0603] Technical effects of the present invention

[0604] Table 1: Calculated LUMO of Compounds

[0605] The calculated LUMO levels of several compounds of formula (II) and comparative compounds are shown below:

[0606] Table 1: LUMO of Several Selected Compounds of Formula (II)

[0607]

[0608]

[0609]

[0610]

[0611] In Table 2 below, the LUMO of several compounds of formula (I) is shown.

[0612] Table 2: LUMO of Several Selected Compounds of Formula (I)

[0613]

[0614]

[0615]

[0616] Table 3 shows the settings and performances of several comparative examples (C-1 to C-5) and inventive examples (I-1 to I-20). N-({[1,1'-Biphenyl]-4-yl}-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine} is used as the p-HIL hole transport matrix compound in all the examples, but CuPC in C-4 and C-5:

[0617]

[0618] The chemical formula of CNHAT is as follows:

[0619]

[0620] The chemical formula of compound CR1 is as follows:

[0621]

[0622] All the inventive devices exhibit a lower operating voltage, and considering the cavity CIEY, the current efficiency is higher than that of the comparative devices.

[0623]

[0624] The comparative devices C-1 to C-3 contain WO3 as a dopant in the hole injection layer (HIL), and an organic p-type dopant BR1 in the p-type charge generation layer (p-CGL).

[0625] The comparative devices C-4 and C-5 contain CuPC and CNHAT in the HIL, and an organic p-type dopant BR1 in the p-CGL.

[0626] The comparative device C-6 contains the metal compound M19 in the HIL and the metal compound M19 in the p-CGL. The comparative device does not work, i.e., it does not emit light.

[0627] The comparative device C-7 contains the metal compound M18 in the HIL and the metal compound M18 in the p-CGL. The comparative device does not work, i.e., it does not emit light.

[0628] The comparative device C-8 contains the organic p-type dopant CR1 in the HIL and the metal compound M18 in the p-CGL. The comparative device does not work, i.e., it does not emit light.

[0629] The comparative device C-9 contains the organic p-type dopant CR1 in the HIL and the organic p-type dopant BR1 in the p-CGL.

[0630] The inventive devices I-1 to I-5 contain a metal compound in the HIL and an organic p-type dopant BR1 in the p-CGL.

[0631] The inventive devices I-6 to I-20 contain a metal compound in the HIL and the organic p-type dopants BR1 to BR5 respectively in the p-CGL.

[0632] The inventive device I-21 comprises a metal compound M18 in the HIL and an organic p-type dopant BR1 in the p-CGL.

[0633] Overall, all of the inventive devices I-1 to I-21 exhibit a higher current efficiency than the comparative devices C1 to C-9.

[0634] Compared with the present invention, the comparative devices C-8 and C-9 both comprise an organic p-type dopant in the HIL. In addition, the comparative device C-9 differs from C-8 in that it comprises the organic p-type dopant BR1 instead of the metal compound M18. From this comparison, it is clear that the use of only an organic p-type dopant in the p-CGL is not sufficient to achieve the high efficiency shown by the inventive devices that use a metal compound in the HIL and an axylene in the p-CGL.

[0635] The comparative devices C-6 to C-7, which use a metal compound in both the HIL and the p-CGL, do not even emit light (C-6 and C-7).

[0636] The comparative devices C6 and C-7 represent the devices of the prior art.

[0637] In addition, the comparative device C-8, which uses an organic p-type dopant in the HIL and a metal compound in the p-CGL, also does not even emit light.

[0638] Therefore, surprisingly, it can be demonstrated that a working OLED can only be fabricated by a specific combination of HIL and p-CGL dopants, and furthermore, the current efficiency can be significantly increased.

[0639] To further exemplify the effects of the present invention, several single-stack devices (constructed as described above) were investigated.

[0640] Table 4 shows the settings and performances of these devices (all of the comparative devices, C6 to C26).

[0641] In all of the examples, N-({[1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine} was used as the p-HIL hole transport matrix compound, except for CuPC in C-8.

[0642] Table 4: Settings and Performances of Several Comparative Single-Stack Devices

[0643]

[0644]

[0645] Obviously, when the compound of formula (II) is used instead of the comparative compound, no substantial change occurs.

[0646] The specific combinations of elements and features in the embodiments described above in detail are merely exemplary; the interchange and substitution of these teachings with other teachings in this application and the patents / applications incorporated by reference are also clearly contemplated. As those skilled in the art will recognize, without departing from the spirit and scope of the claimed invention, variations, modifications, and other embodiments of what is described herein can be conceived by those of ordinary skill in the art. Therefore, the above description is provided by way of example and not intended to be limiting. In the claims, the word "comprising" does not exclude other elements or steps, and the indefinite article "a" or "an" does not exclude a plurality. The fact that certain measures are recited in mutually different dependent claims does not indicate that a combination of these measures cannot be used to advantage. The scope of the invention is defined in the claims and their equivalents. In addition, the reference numerals used in the description and the claims do not limit the scope of the claimed invention.

Claims

1. An organic electroluminescent device, the organic electroluminescent device comprising an anode layer, a cathode layer, a first light-emitting layer, a second light-emitting layer, a hole injection layer, and a first charge generation layer; wherein the hole injection layer is in direct contact with the anode layer; wherein the first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer; wherein the first charge generation layer comprises a first n-type charge generation layer and a first p-type charge generation layer; wherein the first n-type charge generation layer is closer to the anode layer than the first p-type charge generation layer; wherein the first n-type charge generation layer comprises a metal dopant and a matrix compound, wherein the first p-type charge generation layer comprises a second hole transport matrix compound and a compound of formula (I); wherein in formula (I), -A 1 independently selected from the group of formula (Ia): wherein Ar 1 is independently selected from substituted or unsubstituted C6-C 36 aryl and substituted or unsubstituted C2-C 36 heteroaryl; For Ar 1 in the case of substitution, one or more substituents are independently selected from D, an electron-withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1-C8 alkyl group, a partially fluorinated C1-C8 alkyl group, a perfluorinated C1-C8 alkyl group, a substituted or unsubstituted C1-C8 alkoxy group, a partially fluorinated C1-C8 alkoxy group, a perfluorinated C1-C8 alkoxy group, a substituted or unsubstituted C6-C 30 aryl and a substituted or unsubstituted C6-C 30 heteroaryl; and Among them, C6 to C 30 aryl, C6 to C 30 One or more substituents of heteroaryl, C1-C8 alkyl, C1-C8 alkoxy are independently selected from D, an electron-withdrawing group, halogen, Cl, F, CN, -NO2, partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy, perfluorinated C1-C8 alkoxy; -A 2 independently selected from the groups of formula (Ib): wherein Ar 2 is independently selected from substituted or unsubstituted C6-C 36 aryl and substituted or unsubstituted C2-C 36 heteroaryl; Among them, for Ar 2 in the case of being substituted, one or more substituents are independently selected from D, an electron-withdrawing group, a halogen, Cl, F, CN, -NO2, a substituted or unsubstituted C1-C8 alkyl group, a partially fluorinated C1-C8 alkyl group, a perfluorinated C1-C8 alkyl group, a substituted or unsubstituted C1-C8 alkoxy group, a partially fluorinated C1-C8 alkoxy group, a perfluorinated C1-C8 alkoxy group, a substituted or unsubstituted C6-C 30 aryl group and a substituted or unsubstituted C6-C 30 heteroaryl group; and Among them, C6 to C 30 aryl, C6 to C 30 One or more substituents of heteroaryl, C1-C8 alkyl, C1-C8 alkoxy are independently selected from D, an electron-withdrawing group, halogen, Cl, F, CN, -NO2, partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy, perfluorinated C1-C8 alkoxy; -A 3 independently selected from the group of formula (Ic): wherein Ar 3 is independently selected from substituted or unsubstituted C6-C 36 aryl and substituted or unsubstituted C2-C 36 heteroaryl; Among them, for Ar 3 in the case of being substituted, one or more substituents are independently selected from D, an electron-withdrawing group, halogen, Cl, F, CN, -NO2, substituted or unsubstituted C1-C8 alkyl, partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, substituted or unsubstituted C1-C8 alkoxy, partially fluorinated C1-C8 alkoxy, perfluorinated C1-C8 alkoxy, substituted or unsubstituted C6-C 30 aryl and substituted or unsubstituted C6-C 30 heteroaryl; and Among them, C6 to C 30 aryl, C6 to C 30 One or more substituents of heteroaryl, C1-C8 alkyl, C1-C8 alkoxy are independently selected from D, an electron-withdrawing group, halogen, Cl, F, CN, -NO2, partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy, perfluorinated C1-C8 alkoxy; and wherein at A 1 , A 2 and A 3 , each R' is independently selected from substituted or unsubstituted C6 to C 18 aryl, C3 to C 18 heteroaryl, an 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, C1-C8 alkyl are independently selected from D, an electron-withdrawing group, halogen, Cl, F, CN, -NO2, partially fluorinated C1-C6 alkyl, perfluorinated C1-C6 alkyl, partially fluorinated C1-C6 alkoxy, perfluorinated C1-C6 alkoxy; wherein the hole injection layer comprises a first hole transport matrix compound and a compound of formula (II), the compound of formula (II) being a metal compound selected from metal salts or metal complexes, the metal salts or metal complexes comprising a metal cation and at least one monoanion composed of at least 20 covalently bonded atoms and / or at least one monoanion ligand composed of at least 20 covalently bonded atoms.

2. The organic electroluminescent device according to claim 1, wherein the LUMO energy level of the compound of formula (II) is ≥ -7.0 eV to ≤ -1.5 eV, which is implemented in the ORCA 5.0.3-f.1 version (Department of Theoretical and Spectroscopic Chemistry, Max Planck Institute for Coal Research, Kaiser Wilhelm Platz 1, 45470 Muelheim / Ruhr, Germany), and the calculation is carried out by applying the hybrid functional B3LYP in the gas phase, using the Def2-TZVP basis set and the SDD effective core potential (ECP) for the metal.

3. The organic electroluminescent device according to claim 1 or 2, wherein the compound of formula (II) comprises at least one monoanion consisting of at least 20 covalently bonded atoms and / or at least one monoanion ligand consisting of at least 20 covalently bonded atoms, wherein the monoanion or the monoanion ligand is represented by L according to formula (IV) - is represented, or the compound of formula (II) is represented by formula (IIa): wherein M is a metal ion; p is the valence of M; w is n; where L - can be selected to be the same or different; wherein the compound of formula (IIa) may optionally comprise an auxiliary ligand (AL) coordinated to a metal cation or metal cation M p+ ; where L - is represented by the following formula: m, n, p, and q are independently selected from 0 or 1; r, s, t, and u are independently selected from 0 or 1; at least one of r, s, t, and u is 1; Z is selected from CR 1 , C, O, N, B; if Z is selected from O, then n, p, q, and are selected from 0, and s, t, and u are selected from 0; If Z is selected from N or CR 1 , then p and q are selected from 0, and t and u are selected from 0; if Z is selected from C, then q is selected from 0, and u is selected from 0; if Z is selected from B, then n, m, p, and q are selected from 1, and r, s, t, and u are selected from 1; A 1 and A 2 and A 3 and A 4 are independently selected from C=O, C-O, C=NR 2 , C-NR 3 , SO, SO2 or P(=O)R 4 ; Wherein if A 1 、A 2 、A 3 and A 4 are selected from C—O or C—NR 3 and Z is selected from N, O or CR 1 , or A 1 、A 2 、A 3 and A 4 are selected from C—O or C—NR 3 and Z is selected from C, then Z may form a double bond with A 1 、A 2 、A 3 and A 4 ; and optionally A 1 、A 2 、A 3 and A 4 two of 1 , 2 , 3 and 4 together may form a substituted or unsubstituted heterocycle or a substituted or unsubstituted carbocycle with Z, or optionally one of 1 , 2 , 3 and 4 1 、A 2 、A 3 and A 4 may form a substituted or unsubstituted heterocycle or a substituted or unsubstituted carbocycle with Z; One or more substituents on the heterocycle or carbocycle are independently selected from D, an electron-withdrawing group, a halogen, F, CN, NO2, SF5, isonitrile, an ester group, a carboxyl group, a carbonyl group, an acyl group, a thio group, a sulfinyl group, a sulfonyl group, a phosphine group, a substituted or unsubstituted alkyl group, a partially perfluorinated C1 to C 12 alkyl group, a perfluorinated C1 to C 12 alkyl group, CF3, a partially perfluorinated C1 to C6 alkoxy group, a perfluorinated C1 to C6 alkoxy group, OCF3, a substituted or unsubstituted C6 to C 40 aryl group, a substituted or unsubstituted C2 to C 40 heteroaryl group, a substituted or unsubstituted C3 to C 30 carbocyclic group or a substituted or unsubstituted C2 to C 30 heterocyclic group; R 1 selected from H, D, an electron-withdrawing group, a halogen, Cl, F, CN, NO2, SF5, isonitrile, an ester group, a carboxyl group, a carbonyl group, an acyl group, a thio group, a sulfinyl group, a sulfonyl group, a phosphine group, a substituted or unsubstituted C1 to C 12 alkyl, a partially perfluorinated C1 to C 12 alkyl, a perfluorinated C1 to C 12 alkyl, CF3, a substituted or unsubstituted C1 to C 12 alkoxy, a partially perfluorinated C1 to C6 alkoxy, a perfluorinated C1 to C6 alkoxy, CF3, a substituted or unsubstituted C6 to C 40 aryl, a substituted or unsubstituted C2 to C 40 heteroaryl, a substituted or unsubstituted C3 to C 30 carbocyclic group, a substituted or unsubstituted C3 to C 30 heterocyclic group; wherein R 1 one or more substituents on are independently selected from D, an electron-withdrawing group, a halogen, F, CN, NO2, SF5, isonitrile, an ester group, a carboxyl group, a carbonyl group, an acyl group, a thio group, a sulfinyl group, a sulfonyl group, a phosphine group, a partially perfluorinated C1 to C 12 alkyl, a perfluorinated C1 to C 12 alkyl, CF3, a partially perfluorinated C1 to C6 alkoxy, a perfluorinated C1 to C6 alkoxy, OCF3, =N; R 2 、R 3 and R 4 are independently selected from H, D, an electron-withdrawing group, a halogen, Cl, F, CN, an ester group, a carboxyl group, a carbonyl group, an acyl group, a thio group, a sulfinyl group, a sulfonyl group, a phosphine group, a substituted or unsubstituted alkyl group, a partially perfluorinated C1 to C 12 alkyl group, a perfluorinated C1 to C 12 alkyl group, CF3, a substituted or unsubstituted C1 to C6 alkoxy group, a partially perfluorinated C1 to C6 alkoxy group, a perfluorinated C1 to C6 alkoxy group, OCF3, a substituted or unsubstituted C6 to C 40 aryl group, a substituted or unsubstituted C2 to C 30 heteroaryl group, a substituted or unsubstituted C3 to C 30 carbocyclic group, a substituted or unsubstituted C2 to C 30 heterocyclic group, wherein R 2 , R 3 and R 4 The substituents on are independently selected from D, an electron-withdrawing group, a halogen, Cl, F, CN, NO2, SF5, isonitrile, an ester group, a carboxyl group, a carbonyl group, an acyl group, a thio group, a sulfinyl group, a sulfonyl group, a phosphine group, a partially perfluorinated C1 to C 12 alkyl, a perfluorinated C1 to C 12 alkyl, CF3, a partially perfluorinated C1 to C6 alkoxy group, a perfluorinated C1 to C6 alkoxy group, OCF3; R a 、 R b 、 R c and R d are independently selected from H, D, an electron-withdrawing group, a halogen, F, Cl, CN, a substituted or unsubstituted C1 to C 12 alkyl group, a partially perfluorinated C1 to C 12 alkyl group, a perfluorinated C1 to C 12 alkyl group, CF3, a substituted or unsubstituted C6 to C 40 aryl group, a substituted or unsubstituted C2 to C 30 heteroaryl group, a substituted or unsubstituted carbocyclic group, a substituted or unsubstituted C2 to C 30 heterocyclic group, O, S, N, NR 5 , a substituted or unsubstituted amine group having 0 to 20 carbon atoms; wherein R a , R b , R c and R d one or more substituents on are independently selected from an electron-withdrawing group, halogen, F, CN, NO2, SF5, isonitrile, ester group, carboxyl group, carbonyl group, acyl group, thio group, sulfinyl group, sulfonyl group, phosphine group, partially perfluorinated C1 to C 12 alkyl, perfluorinated C1 to C 12 alkyl, partially perfluorinated C1 to C6 alkoxy, perfluorinated C being 1 to C6 alkoxy, OCF3; wherein R 5 is selected from substituted or unsubstituted C6 - C 40 aryl, substituted or unsubstituted C2 - C 40 heteroaryl, substituted or unsubstituted C1 - C 12 alkyl, partially perfluorinated C1 - C 12 alkyl, perfluorinated C1 - C 12 alkyl, wherein R 5 one or more substituents on are selected from an electron-withdrawing group, halogen, F, CN, NO2, SF5, isonitrile, ester group, carboxyl group, carbonyl group, acyl group, thio group, sulfinyl group, sulfonyl group, phosphine group, partially fluorinated C1 to C 12 alkyl, perfluorinated C1 to C 12 alkyl, CF3, CF2CF3, partially fluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy, OCF3, OCF2CCF3; Preferably, R a , R b , R c and R d at least one of which is independently selected from substituted or unsubstituted C6-C 40 aryl, substituted or unsubstituted C2-C 40 heteroaryl, substituted or unsubstituted C1-C 12 alkyl, substituted or unsubstituted C3-C 30 carbocyclic group, substituted or unsubstituted C2-C 30 heterocyclic group, wherein R a , R b , R c and R d substituents on are independently selected from an electron-withdrawing group, halogen, F, CN, NO2, SF5, isonitrile, ester group, carboxyl group, carbonyl group, acyl group, thio group, sulfinyl group, sulfonyl group, phosphine group, partially perfluorinated C1 to C 12 alkyl, perfluorinated C1 to C 12 alkyl, CF3, partially perfluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy, OCF3; wherein Optionally, R a 、R b 、R c 、R d One of them can be independently connected with R 1 Forming a substituted or unsubstituted heterocyclic ring or a substituted or unsubstituted C3 to C 40 Carbon ring, One or more substituents on the heterocycle or carbocycle are independently selected from D, an electron-withdrawing group, a halogen, F, CN, NO2, SF5, isonitrile, an ester group, a carboxyl group, a carbonyl group, an acyl group, a thio group, a sulfinyl group, a sulfonyl group, a phosphine group, a substituted or unsubstituted alkyl group, a partially perfluorinated C1 to C 12 alkyl group, a perfluorinated C1 to C 12 alkyl group, CF3, a partially perfluorinated C1 to C6 alkoxy group, a perfluorinated C1 to C6 alkoxy group, OCF3, a substituted or unsubstituted C6 to C 40 aryl group, a substituted or unsubstituted C2 to C 40 heteroaryl group, a substituted or unsubstituted C3 to C 30 carbocyclic group or a substituted or unsubstituted C2 to C 30 heterocyclic group; One or more substituents on the substituents on the heterocyclic or carbocyclic ring are independently selected from D, an electron-withdrawing group, a halogen, F, a substituted or unsubstituted C1 to C 12 alkyl, a partially perfluorinated C1 to C 12 alkyl, a perfluorinated C1 to C 12 alkyl, CF3, a partially perfluorinated C1 to C6 alkoxy group, a perfluorinated C1 to C6 alkoxy group, OCF3.

4. The organic electroluminescent device according to any one of claims 1 or 3, wherein the monoanion or the monoanion ligand L - is selected from (V), (VI), (VII), (VIII) or (IX): wherein R a' independently selected from substituted or unsubstituted C1-C 12 alkyl, substituted or unsubstituted C6-C 19 aryl, substituted or unsubstituted C2-C 20 heteroaryl or substituted or unsubstituted 6-membered heteroaryl; R b' selected from substituted or unsubstituted C1 to C 12 alkyl, substituted or unsubstituted C6 to C 19 aryl, substituted or unsubstituted C2 to C 20 heteroaryl, substituted or unsubstituted 6-membered heteroaryl or CN; wherein Substituted C1 to C 12 alkyl, substituted C6 to C 19 aryl, substituted C2 to C 20 heteroaryl or at least one substituent of a substituted 6-membered heteroaryl is independently selected from halogen, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl, partially fluorinated or perfluorinated C1 to C8 alkoxy; wherein in formula (VI), R a' 、R b' and R a At least one or R a' 、R b' and R a The group comprises at least three atoms selected from halogen, Cl, F or N; - The remaining R is the same as defined above.

5. The organic electroluminescent device according to any one of claims 1 to 4, wherein R a , R b , R c or R d or at least one of R a , R b , R c and R d are independently selected from D1 to D105: -CF3 (D72), -C2F5 (D73), -C3F7 (D74), -CF2CF2CF3 (D75), -C4F9 (D77), -CF2CF2CF2CF3 (D78), -C5F 11 (D81), -C6F 13 (D82), -CH3 (D83), -C2H5 (D84), -CH(CH3)2 (D85), -C(CH3)3 (D86), wherein "*" or "-" represents the bonding position.

6. The organic electroluminescent device according to claim 5, wherein the monoanion or the monoanion ligand is selected from L1 to L405:

7. The organic electroluminescent device according to any one of claims 1 to 6, wherein the amount of the compound of formula (I) present in the p-type charge generation layer is ≥ 1 wt% and ≤ 20 wt% relative to the total weight of the p-type charge generation layer.

8. The organic electroluminescent device according to any one of claims 1 to 7, wherein the compound of formula (I) comprises at least one CF3 group.

9. The organic electroluminescent device according to any one of claims 1 to 8, wherein in formula (I), Ar 1 , Ar 2 and Ar 3 are independently selected from the group according to the following formula (III), and preferably each R' is selected from CN: wherein E 1 selected from CW 1 or N; E 2 selected from CW 2 or N; E 3 selected from CW 3 or N; E 4 selected from CW 4 or N; E 5 selected from CW 5 or N; W 1 、W 2 、W 3 、W 4 and W 5 (if present) are independently selected from an electron-withdrawing group, CN, halogen, Cl, F, NO2, substituted or unsubstituted C1-C8 alkyl, partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, substituted or unsubstituted C1-C8 alkoxy, partially fluorinated C1-C8 alkoxy, perfluorinated C1-C6 alkoxy, OCF3, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl, D or H, One or more of the substituents are independently selected from D, halogen, Cl, F, CN, NO2, partially fluorinated C1-C8 alkyl, perfluorinated C1-C8 alkyl, partially fluorinated C1-C8 alkoxy, perfluorinated C1-C8 alkoxy, wherein the asterisk "*" represents the bonding position.

10. The organic electroluminescent device according to any one of claims 1 to 9, wherein in formula (III), W 1 , W 2 , W 3 , W 4 and W 5 (if present) are independently selected from an electron-withdrawing group, CN, a halogen, Cl, F, NO2, a partially fluorinated or perfluorinated C1 to C8 alkyl group, a partially fluorinated or perfluorinated C1 to C6 alkoxy group, D or H, and preferably each R' is selected from CN.

11. The organic electroluminescent device according to any one of claims 1 to 10, wherein in formula (I), Ar 1 , Ar 2 and Ar 3 are independently selected from B1 to B64, and preferably each R' is selected from CN: wherein the asterisk "*" represents the bonding position.

12. The organic electroluminescent device according to any one of claims 1 to 11, wherein the metal dopant of the first n-type charge generation layer is a metal selected from Li, Mg, and Yb or a metal alloy containing a metal selected from Li, Mg, and Yb.

13. The organic electroluminescent device according to any one of claims 1 to 12, wherein the metal dopant of the first n-type charge generation layer is Yb or a metal alloy containing a metal selected from Li and Yb.

14. The organic electroluminescent device according to any one of claims 1 to 13, wherein the organic light-emitting device is an organic light-emitting diode.

15. A display device comprising the organic electroluminescent device according to any one of claims 1 to 14.

Images