Organic electronic device comprising an anode layer, a cathode layer, at least one light-emitting layer (EML) and at least one hole injection layer (HIL)

Abstract

The present invention relates to an organic electronic device comprising an anode layer, a cathode layer, at least one emitting layer (EML) and at least one hole injection layer (HIL). In particular, the present invention relates to an organic electronic device comprising an anode layer, a cathode layer, at least one emitting layer (EML) and at least one hole injection layer (HIL), wherein the hole injection layer is arranged between the anode layer and the at least one emitting layer.

Description

[0001] This application is a divisional application of Chinese Patent Application No. 202180011031.5, filed on January 27, 2021, entitled "Organic Electronic Device Including an Anode Layer, a Cathode Layer, at Least One Light Emitting Layer (EML) and at Least One Hole Injection Layer (HIL)". Technical Field

[0002] This invention relates to an organic electronic device comprising an anode layer, a cathode layer, at least one light-emitting layer (EML), and at least one hole injection layer (HIL). Specifically, this invention relates to an organic electronic device comprising an anode layer, a cathode layer, at least one light-emitting layer (EML), and at least one hole injection layer (HIL), wherein the hole injection layer comprises an organic matrix compound. Background Technology

[0003] Organic electronic devices, such as organic light-emitting diodes (OLEDs), are self-emissive and possess wide viewing angles, excellent contrast ratios, fast response times, high brightness, excellent operating voltage characteristics, and superior color reproduction. A typical OLED comprises an anode layer, a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and a cathode layer, sequentially stacked on a substrate. In this regard, HIL, HTL, EML, and ETL are thin films formed from organic compounds.

[0004] When a voltage is applied to the anode and cathode, holes injected from the anode move to the EML via the HIL and HTL, while electrons injected from the cathode move to the EML via the ETL. Holes and electrons recombine in the EML to generate excitons. Light emission occurs when the excitons transition from the excited state to the ground state. The injection and flow of holes and electrons should be balanced so that OLEDs with the above structure exhibit low operating voltage, excellent efficiency, and / or long lifetime.

[0005] The performance of organic light-emitting diodes can be affected by the characteristics of the hole injection layer, which in turn can be affected by the characteristics of the organic matrix compounds and metal complexes contained in the hole injection layer.

[0006] WO2017029370 relates to metal amines of general formula Ia and their use as hole injection layers (HILs) in organic light-emitting diodes (OLEDs), and a method for manufacturing an OLED comprising a hole injection layer containing a metal amine of general formula Ia. WO2017029370 discloses a hole transport layer, which may additionally comprise a triarylamine compound having formula VIIa. (VIIa).

[0007] The light-emitting layer (EML) can be formed by a combination of a host and dopants.

[0008] WO2017029366 relates to a hole injection layer for OLEDs, the hole injection layer comprising a triarylamine compound doped with an electrically neutral metal amine compound, characterized in that the thickness of the hole injection layer is at least about ≥20 nm to about ≤1000 nm, and the electrically neutral metal amine compound has formula Ia. WO2017029366 discloses a hole injection layer (HIL) comprising a triarylamine compound having formula VIIa: (VIIa).

[0009] The light-emitting layer (EML) can be formed by a combination of a host and dopants.

[0010] WO2017102861 relates to an organic electronic component (10) comprising at least one organic layer (3) having a fluorinated sulfonamide metal salt of formula 1: (1) wherein M is a divalent or higher valence metal with an atomic weight greater than 26 g / mol or a monovalent metal with an atomic weight greater than or equal to 39 g / mol, wherein 1 ≤ n ≤ 7, and wherein R1 and R2 are independently selected from fluorinated aryl groups, fluorinated alkyl groups, and fluorinated aryl-alkyl groups. The matrix material is a hole transport material. The organic electronic component includes a light-emitting layer.

[0011] US2016336519A1 discloses a novel light-emitting element, a light-emitting element with long lifetime, or a light-emitting element with high luminous efficiency. The light-emitting element includes an EL layer between a pair of electrodes. The EL layer includes at least one light-emitting layer containing a fluorescent material and a host material, a first electron transport layer containing a first electron transport material, and a second electron transport layer containing a second electron transport material, which are in contact with each other in this order. The LUMO energy levels of the host material and the second electron transport material are each higher than the LUMO energy level of the first electron transport material.

[0012] US patent 2019198789A1 discloses an organic light-emitting diode (OLED) and an organic light-emitting display including the OLED, wherein the OLED comprises: a first electrode; a light-emitting stack disposed on the first electrode; and a second electrode disposed on the light-emitting stack, wherein the light-emitting stack comprises a hole transport layer and a blue light-emitting layer, such that the hole transport layer and the blue light-emitting layer are sequentially stacked on the first electrode, wherein the blue light-emitting layer comprises a blue host material and a blue fluorescent dopant material, and the hole transport layer comprises a hole transport layer material. The LUMO energy level of the blue fluorescent dopant material is higher than that of the blue host material, and the HOMO energy level of the blue fluorescent dopant material is higher than that of the blue host material.

[0013] There is still a need to improve the performance of organic electronic devices by providing a hole injection layer with improved hole injection to at least one light-emitting layer, and in particular by improving the characteristics of the hole injection layer and the organic electronic devices to achieve improved operating voltage.

[0014] Another objective is to provide a hole injection layer comprising a compound that can be deposited by vacuum thermal evaporation under conditions suitable for large-scale production. Summary of the Invention

[0015] One aspect of the present invention provides an organic electronic device comprising an anode layer, a cathode layer, at least one light-emitting layer (EML), and at least one hole injection layer (HIL), wherein the hole injection layer is disposed between the anode layer and the at least one light-emitting layer; wherein

[0016] - The hole injection layer comprises an organic matrix compound (OMC) and a metal complex, wherein the metal complex has formula (II): (II), in M is a metal ion. n is the valence of M, where n is an integer from 1 to 4. L is a ligand; and - The at least one light-emitting layer comprises at least one light-emitting matrix compound (EMC). The HOMO energy levels of the luminescent matrix compound (EMC) and the organic matrix compound (OMC) satisfy the following equation: -0.24 eV < [HOMO level (EMC) – HOMO level (OMC)] ≤ 0.8 eV.

[0017] The term "HOMO level" is understood to refer to the highest occupied molecular orbital and is determined in eV (electron volts).

[0018] According to one embodiment, the organic electronic device includes an anode layer, a cathode layer, at least one light-emitting layer (EML), and at least one hole injection layer (HIL), wherein the hole injection layer is disposed between the anode layer and the at least one light-emitting layer; wherein

[0019] - The hole injection layer comprises an organic matrix compound (OMC) and a metal complex, wherein the metal complex has formula (II): (II), in M is a metal ion, where M is not Mo. n is the valence of M, where n is an integer from 1 to 4. L is a ligand; and - The at least one light-emitting layer comprises at least one light-emitting matrix compound (EMC). The HOMO energy levels of the luminescent matrix compound (EMC) and the organic matrix compound (OMC) satisfy the following equation: -0.24 eV < [HOMO level (EMC) – HOMO level (OMC)] ≤ 0.8 eV.

[0020] According to one embodiment, the organic electronic device includes an anode layer, a cathode layer, at least one light-emitting layer (EML), and at least one hole injection layer (HIL), wherein the hole injection layer is disposed between the anode layer and the at least one light-emitting layer; wherein

[0021] - The hole injection layer comprises an organic matrix compound (OMC) and a metal complex, wherein the metal complex has formula (II): (II), in M is a metal ion, where M is not Mo, Ir, or Pt. n is the valence of M, where n is an integer from 1 to 4. L is a ligand; and - The at least one light-emitting layer comprises at least one light-emitting matrix compound (EMC). The HOMO energy levels of the luminescent matrix compound (EMC) and the organic matrix compound (OMC) satisfy the following equation: -0.24 eV < [HOMO level (EMC) – HOMO level (OMC)] ≤ 0.8 eV.

[0022] According to one embodiment, the organic electronic device includes an anode layer, a cathode layer, at least one light-emitting layer (EML), and at least one hole injection layer (HIL), wherein the hole injection layer is disposed between the anode layer and the at least one light-emitting layer; wherein

[0023] - The hole injection layer comprises an organic matrix compound (OMC) and a metal complex, wherein the metal complex has formula (II): (II), in M is a metal ion, where M is not Mo. n is the valence of M, where n is an integer from 1 to 4. L is a ligand; and - The at least one light-emitting layer comprises at least one light-emitting matrix compound (EMC). The HOMO energy levels of the luminescent matrix compound (EMC) and the organic matrix compound (OMC) satisfy the following equation: -0.24 eV < [HOMO level (EMC) – HOMO level (OMC)] ≤ 0.8 eV; and This excludes metal phthalocyanine metal complexes, particularly copper phthalocyanine metal complexes (also known as CuPc), and / or optionally, the ligand L has a negative charge.

[0024] According to one embodiment, the organic electronic device includes an anode layer, a cathode layer, at least one light-emitting layer (EML), and at least one hole injection layer (HIL), wherein the hole injection layer is disposed between the anode layer and the at least one light-emitting layer; wherein

[0025] - The hole injection layer comprises an organic matrix compound (OMC) and a metal complex, wherein the metal complex has formula (II): (II), in M is a metal ion, where M is not Mo, Ir, or Pt. n is the valence of M, where n is an integer from 1 to 4. L is a ligand; and - The at least one light-emitting layer comprises at least one light-emitting matrix compound (EMC). The HOMO energy levels of the luminescent matrix compound (EMC) and the organic matrix compound (OMC) satisfy the following equation: -0.24 eV < [HOMO level (EMC) – HOMO level (OMC)] ≤ 0.8 eV; and This excludes metal phthalocyanine metal complexes, particularly copper phthalocyanine metal complexes (also known as CuPc), and / or optionally, the ligand L has a negative charge.

[0026] According to one embodiment, the organic electronic device includes an anode layer, a cathode layer, at least one light-emitting layer (EML), and at least one hole injection layer (HIL), wherein the hole injection layer is disposed between the anode layer and the at least one light-emitting layer; wherein

[0027] - The hole injection layer comprises an organic matrix compound (OMC) and a metal complex, wherein the metal complex has formula (II): (II), in M is a metal ion, where M is not Mo or Cu. n is the valence of M, where n is an integer from 1 to 4. L is a ligand; and - The at least one light-emitting layer comprises at least one light-emitting matrix compound (EMC). The HOMO energy levels of the luminescent matrix compound (EMC) and the organic matrix compound (OMC) satisfy the following equation: -0.24 eV < [HOMO level (EMC) – HOMO level (OMC)] ≤ 0.8 eV, and optionally, the ligand L has a negative charge.

[0028] According to one embodiment, the organic electronic device includes an anode layer, a cathode layer, at least one light-emitting layer (EML), and at least one hole injection layer (HIL), wherein the hole injection layer is disposed between the anode layer and the at least one light-emitting layer; wherein

[0029] - The hole injection layer comprises an organic matrix compound (OMC) and a metal complex, wherein the metal complex has formula (II): (II), in M is a metal ion, where M is not Mo, Cu, Ir, or Pt. n is the valence of M, where n is an integer from 1 to 4. L is a ligand; and - The at least one light-emitting layer comprises at least one light-emitting matrix compound (EMC). The HOMO energy levels of the luminescent matrix compound (EMC) and the organic matrix compound (OMC) satisfy the following equation: -0.24 eV < [HOMO level (EMC) – HOMO level (OMC)] ≤ 0.8 eV, and optionally, the ligand L has a negative charge.

[0030] According to one embodiment, the organic electronic device includes an anode layer, a cathode layer, at least one light-emitting layer (EML), and at least one hole injection layer (HIL), wherein the hole injection layer is disposed between the anode layer and the at least one light-emitting layer; wherein

[0031] - The hole injection layer comprises an organic matrix compound (OMC) and a metal complex, wherein the metal complex has formula (II): (II), in M is a metal ion. n is the valence of M, where n is an integer from 1 to 4. L is a ligand; and - The at least one light-emitting layer comprises at least one light-emitting matrix compound (EMC). The HOMO energy levels of the luminescent matrix compound (EMC) and the organic matrix compound (OMC) satisfy the following equation: -0.24 eV < [HOMO level (EMC) – HOMO level (OMC)] ≤ 0.8 eV.

[0032] The term "HOMO level" is understood to refer to the highest occupied molecular orbital and is determined in eV (electron volts). The ligand L of formula (II), also known as L, can be selected from the following: - At least three carbon atoms or at least four carbon atoms, and / or - At least two oxygen atoms, or one oxygen atom and one nitrogen atom, two to four oxygen atoms, two to four oxygen atoms and zero to two nitrogen atoms, and / or - At least one or more groups selected from the following: halogen, F, CN, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy; or two or more groups selected from the following: halogen, F, CN, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy; at least one or more groups selected from the following: halogen, F, CN, substituted C1 to C6 alkyl, substituted C1 to C6 alkoxy; or two or more groups selected from the following: halogen, F, CN, perfluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkoxy; or one or more groups selected from the following: substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C6 alkyl; 12 Aryl and / or substituted or unsubstituted C3 to C4 12 Mixed aromatics; The substituents are selected from: D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkyl, partially deuterated or fully deuterated C1 to C6 alkoxy, COR 6 COOR 6 Halogen, F or CN; Where R 6 It can be selected from: C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkyl, partially deuterated or fully deuterated C1 to C6 alkoxy; optionally, ligand L may be sulfur-free.

[0033] The term "HOMO level further from the vacuum level" should be understood as meaning that the absolute value of the HOMO level is higher than that of the reference compound. For example, the term "far from the vacuum level than the HOMO level of N4,N4'''-di(naphthyl-1-yl)-N4,N4'''-diphenyl-[1,1':4',1'':4'',1'''-tetraphenyl]-4,4'''-diamine" should be understood as meaning that the absolute value of the HOMO level of the organomatrix compound (OMC) is higher than that of the HOMO level of N4,N4'''-di(naphthyl-1-yl)-N4,N4'''-diphenyl-[1,1':4',1'':4'',1'''-tetraphenyl]-4,4'''-diamine.

[0034] The term "absolute value" should be understood as meaning a value that does not have a "-" sign.

[0035] Preferably, the HOMO energy levels of the luminescent matrix compound (EMC) and the organic matrix compound (OMC) satisfy the following equation: -0.2 eV < [HOMO level (EMC) – HOMO level (OMC)] ≤ 0.7 eV, Or -0.1 eV < [HOMO level (EMC) – HOMO level (OMC)] ≤ 0.7 eV, Or -0.05 eV < [HOMO level (EMC) – HOMO level (OMC)] ≤ 0.6 eV, Or -0.05 eV < [HOMO level (EMC) – HOMO level (OMC)] ≤ 0.55 eV.

[0036] According to one embodiment of the present invention, the HOMO energy level of the organic matrix compound (OMC) and the HOMO energy level of the luminescent matrix compound (EMC) can be calculated by quantum mechanical methods.

[0037] According to one embodiment of the present invention, the HOMO level of the organic matrix compound (OMC) and the HOMO level of the luminescent matrix compound (EMC) can be calculated using the package TURBOMOLE V6.5, which is available from TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany.

[0038] If HOMO levels are calculated using this method, prior art organic matrix compounds possess the following HOMO levels. For comparison, HOMO levels calculated from redox potentials are also provided.

[0039]

[0040] If the HOMO level is far from the vacuum level, accurate measurement of the redox potential becomes impractical. Therefore, unless otherwise stated, the HOMO level is determined in this specification by quantum mechanical methods.

[0041] It should be noted that the ligand L has a negative charge. According to one embodiment, the ligand L has a single negative charge; in other words, the ligand L is a monoanion. According to one embodiment, the negative charge of the ligand L may correspond to the valence of the metal ion M.

[0042] Another aspect is an organic electronic device comprising an anode layer, a cathode layer, at least one light-emitting layer (EML), and at least one hole injection layer (HIL), wherein the hole injection layer is disposed between the anode layer and the at least one light-emitting layer, wherein

[0043] - The hole injection layer comprises an organic matrix compound (OMC) and a metal complex, wherein

[0044] - The organic matrix compound (OMC) and the luminescent matrix compound (EMC) have formula (I): (Ar 1 ) k —(Ar 2 ) m —Ar 3 —(Ar 4 ) p —(Ar 5 ) q —(Ar 6 ) r (I), in k, m, q, and r are each independently 0, 1, or 2. p is 1, 2, or 3. Where 2 ≤ k+m+q+r+p ≤ 11, Ar 1 To Ar 6 Heterocycles independently selected from substituted or unsubstituted unsaturated 5- to 7-membered rings, substituted or unsubstituted C6 to C6 rings. 30 aryl or substituted or unsubstituted C3 to C 30The rings are selected from: (i) heterocyclic rings with unsaturated 5 to 7-membered rings, (ii) aromatic heterocyclic rings with 5 to 6 members, (iii) non-heterocyclic rings with unsaturated 5 to 7-membered rings, and (iv) aromatic non-heterocyclic rings with 6-membered rings. The substituents are selected from H, D, C1 to C. 12 Alkyl, unsubstituted C6 to C 18 Aryl, unsubstituted C3 to C 18 The heteroaryl group comprises a fused ring system containing 2 to 6 unsubstituted 5 to 7-membered rings, wherein the rings are selected from: unsaturated 5 to 7-membered heterocycles, 5 to 6-membered aromatic heterocycles, unsaturated 5 to 7-membered non-heterocycles, and 6-membered aromatic non-heterocycles. - The metal complex has formula (II): (II), in M is a metal ion. n is the valence of M, where n is an integer from 1 to 4. L is a ligand; Furthermore, the organic matrix compound (OMC) and the luminescent matrix compound (EMC) are selected to be the same or different.

[0045] According to one embodiment, the organic electronic device includes an anode layer, a cathode layer, at least one light-emitting layer (EML), and at least one hole injection layer (HIL), wherein the hole injection layer is disposed between the anode layer and the at least one light-emitting layer.

[0046] - The hole injection layer comprises an organic matrix compound (OMC) and a metal complex, wherein: - The organic matrix compound (OMC) and the luminescent matrix compound (EMC) have formula (I): (Ar 1 ) k —(Ar 2 ) m —Ar 3 —(Ar 4 ) p —(Ar 5 ) q —(Ar 6 ) r (I), in k, m, q, and r are each independently 0, 1, or 2. p is 1, 2, or 3. Where 2 ≤ k+m+q+r+p ≤ 11, Ar 1 To Ar 6 Independently selected from substituted or unsubstituted biphenylene groups, substituted or unsubstituted fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted terphenylene groups, substituted or unsubstituted tetraphenylene, substituted or unsubstituted benzo[b]anthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthone, substituted or unsubstituted carbazole, substituted or unsubstituted azacycloheptatriene, substituted or unsubstituted dibenzo[b]anthracene. [f]-Azaheptatriene, 9,9'-spirobis[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanton], substituted or unsubstituted 9,14-dihydrodibenzo[2,3:6,7]azaheptatrien[4,5-b]indole, or substituted or unsubstituted aromatic fused ring systems comprising at least three substituted or unsubstituted aromatic rings selected from substituted or unsubstituted non-heterocyclic rings, substituted or unsubstituted heterocyclic 5-membered rings, substituted or unsubstituted 6-membered rings, and / or substituted or unsubstituted 7-membered rings. The substituents are selected from H, D, C1 to C. 12 Alkyl, unsubstituted C6 to C 18 Aryl, unsubstituted C3 to C 18 A heteroaryl fused ring system comprising 2 to 6 unsubstituted 5- to 7-membered rings, wherein the rings are selected from unsaturated 5- to 7-membered heterocycles, 5- to 6-membered aromatic heterocycles, unsaturated 5- to 7-membered non-heterocycles, and 6-membered aromatic non-heterocycles; and The organic matrix compound (OMC) and the luminescent matrix compound (EMC) are selected to be the same or different.

[0047] According to one embodiment, the organic electronic device includes an anode layer, a cathode layer, at least one light-emitting layer (EML), and at least one hole injection layer (HIL), wherein the hole injection layer is disposed between the anode layer and the at least one light-emitting layer.

[0048] - The hole injection layer comprises an organic matrix compound (OMC) and a metal complex, wherein

[0049] - The organic matrix compound (OMC) and the luminescent matrix compound (EMC) have formula (I): (Ar 1 ) k —(Ar 2 ) m —Ar 3 —(Ar 4 )p —(Ar 5 ) q —(Ar 6 ) r (I), in k, m, q, and r can be independently selected from 0, 1, or 2. p is 1, 2, or 3. Where 2 ≤ k+m+q+r+p ≤ 11, Ar 1 To Ar 6 It can be independently selected from heterocycles of substituted or unsubstituted unsaturated 5 to 7-membered rings, and substituted or unsubstituted C6 to C6 rings. 30 Aryl, substituted or unsubstituted C3 to C 30 The rings are selected from: (i) heterocyclic rings with unsaturated 5 to 7-membered rings, (ii) aromatic heterocyclic rings with 5 to 6 members, (iii) non-heterocyclic rings with unsaturated 5 to 7-membered rings, and (iv) aromatic non-heterocyclic rings with 6-membered rings. The substituents are selected from H, D, C1 to C. 12 Alkyl, unsubstituted C6 to C 18 Aryl, unsubstituted C3 to C 18 A heteroaryl fused ring system comprising 2 to 6 unsubstituted 5- to 7-membered rings, wherein the rings are selected from unsaturated 5- to 7-membered heterocycles, 5- to 6-membered aromatic heterocycles, unsaturated 5- to 7-membered non-heterocycles, and 6-membered aromatic non-heterocycles; and - The metal complex has formula (II): (II), in M is a metal ion. n is the valence of M, where n is an integer from 1 to 4. L is a ligand containing at least two carbon atoms; wherein the organic matrix compound (OMC) and the luminescent matrix compound (EMC) are selected to be the same or different.

[0050] According to another aspect, the organic matrix compound (OMC) and the luminescent matrix compound (EMC) according to formula (I) can be hole transport compounds.

[0051] According to one embodiment, n can be an integer from 1 to 4, preferably an integer from 1 to 3, and even more preferably 2 or 3.

[0052] It should be noted that k, m, q, and r represent the substitution bases of adjacent Ar moieties. For example, for compound F13 according to formula (I): (F13), which is represented by Ar 3 = phenylene, k, m, q, and r = 0 and p = 3, where Ar 4 = (D8).

[0053] According to one embodiment, the hole injection layer is non-emissive.

[0054] According to one embodiment of the present invention, the hole injection layer and / or the organic matrix compound (OMC) of formula (I) and the emitter matrix compound (EMC) and / or the metal complex of formula (II) are non-emissive.

[0055] In the context of this specification, the term "substantially non-emissive" or "non-emissive" means that, relative to the visible emission spectrum, the contribution of the hole injection layer, the organic matrix compound (OMC) of formula (I), the emitter matrix compound (EMC), and / or the metal complex of formula (II) to the visible emission spectrum of an organic electronic device such as an OLED or a display device can be less than 10%, preferably less than 5%. The visible emission spectrum is an emission spectrum with wavelengths of approximately ≥380 nm to approximately ≤780 nm.

[0056] It should be noted that unless otherwise stated, throughout the application and claims, any Ar 1 to Ar 6 and so on always refer to the same moiety.

[0057] In this specification, when no other definition is provided, "substituted" means substituted by H, deuterium, C1 to C 12 alkyl, unsubstituted C6 to C 18 aryl, and unsubstituted C3 to C 18 heteroaryl.

[0058] In this specification, when no other definition is provided, an aryl group having at least 6 C ring atoms can be substituted by 1, 2, 3, 4, or 5 substituents. For example, a substituted C6 aryl group can have 1, 2, 3, 4, or 5 phenyl substituents. The following are examples of C6 aryl groups substituted by 4 phenyl groups: .

[0059] However, in this specification, "aryl-substituted" means substituted by one or more aryl groups, and the aryl groups themselves can be substituted by one or more aryl and / or heteroaryl groups.

[0060] Accordingly, in this specification, "heteroaryl substituted" means substituted by one or more heteroaryl groups, which may be substituted by one or more aryl and / or heteroaryl groups.

[0061] In this specification, unless otherwise defined, "alkyl group" refers to a saturated aliphatic hydrocarbon group. Alkyl groups can be C1 to C2. 12 Alkyl groups. More specifically, the alkyl groups can be C1 to C2. 10 Alkyl groups or C1 to C6 alkyl groups. For example, C1 to C4 alkyl groups include 1 to 4 carbons in the alkyl chain and can be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.

[0062] Specific examples of the alkyl group may be methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, branched pentyl group, and hexyl group.

[0063] The term "cycloalkyl" refers to a saturated hydrocarbon group derived from a cycloalkane by formally isolating a hydrogen atom from the ring atoms contained in the respective cycloalkane. Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, adamantyl, and so on.

[0064] The term "heteroatom" is understood to mean that in a structure that can be formed by covalently bonded carbon atoms, at least one carbon atom is replaced by another multivalent atom. Preferably, the heteroatom is selected from B, Si, N, P, O, and S; more preferably, it is selected from N, P, O, and S.

[0065] Preferred examples of compounds according to formula (I) that can be covalently bonded compounds are organic compounds consisting primarily of covalently bonded C, H, O, N, and S, and optionally also containing covalently bonded B, P, As, and Se. In one embodiment, a compound according to formula (I) that can be a covalently bonded compound does not contain metal atoms, and most of its skeleton atoms may be selected from C, O, S, and N. Alternatively, a covalently bonded compound according to formula (I) does not contain metal atoms, and most of its skeleton atoms may be selected from C and N.

[0066] According to one embodiment, the organic matrix compound (OMC) and the luminescent matrix compound (EMC), or the organic matrix compound (OMC) and the luminescent matrix compound (EMC) according to formula (I), may contain one or more heteroatoms selected from O, S, N, B, P or Si. Preferably, the heteroatoms are selected from O, S, N, B or Si, or the heteroatoms are selected from O, S, N or Si.

[0067] In this specification, "aryl group" and "aromatic ring" refer to hydrocarbon groups that can be produced by formally isolating a hydrogen atom from an aromatic ring in the corresponding aromatic hydrocarbon. An aromatic hydrocarbon is 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 includes a conjugated system of delocalized electrons satisfying Hückel's rule. Examples of aryl groups include monocyclic groups such as phenyl or tolyl, polycyclic groups containing multiple aromatic rings linked by single bonds such as biphenyl, and polycyclic groups containing fused rings such as naphthyl or fluorenyl.

[0068] Similarly, "heteroaryl" and "heteroaromatic" are particularly well understood as groups derived by formally isolating a cyclic hydrogen from a heterocyclic aromatic ring in a compound containing at least one such ring.

[0069] The term "non-heterocyclic" should be understood to mean a ring or ring system that does not contain heteroatoms as ring members.

[0070] The term "heterocycle" should be understood to mean that a heterocycle contains at least one ring containing one or more heteroatoms. A heterocycle containing more than one ring means that all rings contain heteroatoms, or that at least one ring contains heteroatoms and at least one ring contains only C atoms without heteroatoms.

[0071] Heterocyclic alkyl groups are particularly well understood as groups derived by formally isolating a cyclic hydrogen from a saturated cycloalkyl ring in a compound containing at least one such ring.

[0072] The terms "fused aryl ring" or "condensed aryl ring" should be understood as referring to a aryl ring sharing at least two common sp24-p- ... 2 When carbon atoms are hybridized, they are considered to be fused or condensed.

[0073] The term "fused ring system" should be understood to mean a ring system in which two or more rings share at least two atoms.

[0074] The terms "5-membered ring," "6-membered ring," or "7-membered ring" should be understood to mean a ring containing 5, 6, or 7 atoms. The atoms may be selected from carbon and one or more heteroatoms.

[0075] In this specification, a single key refers to a direct key.

[0076] In the context of this invention, "different" means that the compounds do not have the same chemical structure.

[0077] The terms "free from", "does not contain", and "does not include" do not exclude impurities that may be present in the compound according to formula (I) prior to deposition. Impurities have no technical effect on the objectives of this invention.

[0078] The term "adjacent" should be understood to mean that the distance between layers is less than 20 nm or that adjacent layers are in contact with each other. The term "contact sandwich" refers to a three-layer arrangement in which the middle layer is in direct contact with two adjacent layers.

[0079] The terms “light-emitting layer,” “light-emitting layer,” and “emitting layer” are used synonymously.

[0080] The terms “OLED,” “organic light-emitting diode,” and “organic light-emitting device” are used synonymously.

[0081] The terms anode, anode layer, and anode electrode are used synonymously.

[0082] The terms cathode, cathode layer, and cathode electrode are used synonymously.

[0083] The term "hole injection layer" should be understood as meaning a layer that improves charge injection from the anode layer to at least one light-emitting layer.

[0084] The term "hole transport layer" should be understood as meaning the layer that transports holes between the hole injection layer and at least one light-emitting layer and / or between the first light-emitting layer and the second light-emitting layer.

[0085] The operating voltage U is measured in volts.

[0086] In this specification, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductivity characteristics based on the highest occupied molecular orbital (HOMO) energy level, holes formed in the anode can be easily injected into and transported in the light-emitting layer.

[0087] Furthermore, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductivity of the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into and transported in the light-emitting layer.

[0088] Beneficial effects

[0089] Surprisingly, the organic electronic device according to the invention solves the fundamental problem of the invention by making organic electronic devices, such as organic light-emitting diodes, superior to known organic electronic devices in all respects, especially in terms of operating voltage.

[0090] Furthermore, it has been found that the fundamental problem of the present invention can be solved by providing compounds that are suitable for deposition by vacuum thermal evaporation under conditions suitable for large-scale production. In particular, the standard onset temperatures of the organic matrix compound (OMC), luminescent matrix compound (EMC), and metal complex of the present invention are within a range suitable for large-scale production.

[0091] According to one embodiment, when measured under the same conditions, the HOMO level of the said organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) is further away from the vacuum level than the HOMO level of N4,N4'''-di(naphthyl-1-yl)-N4,N4'''-diphenyl-[1,1':4',1'':4'',1'''-tetraphenyl]-4,4'''-diamine (-4.85 eV, calculated by the method described herein).

[0092] Preferably, the HOMO level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) is further from the vacuum level than the HOMO level of N,N'-((9H-fluorene-9,9-diyl)bis(4,1-phenyleneyl))bis(N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine) (-4.86 eV, calculated by the method described herein); or, the HOMO level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) is further from the vacuum level than the HOMO level of 9-phenyl-10-(3',4',5'-triphenyl-[1,1':2',1''-triphenyl]-3-yl)anthracene (-5.04 eV). The HOMO level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) is the same as or further from the vacuum level of the HOMO level of tris(4-(9H-carbazole-9-yl)phenyl)amine (-5.09 eV, calculated by the method described in this specification); or the HOMO level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) is the same as or further from the vacuum level of the HOMO level of tris(4-(9H-carbazole-9-yl)phenyl)amine (-5.09 eV, calculated by the method described in this specification).

[0093] According to one embodiment, when measured under the same conditions, the HOMO energy level of the said organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) is further away from the vacuum energy level than the HOMO energy level of N4,N4'''-di(naphthyl-1-yl)-N4,N4'''-diphenyl-[1,1':4',1'':4'',1'''-tetraphenyl]-4,4'''-diamine, and is further away from the vacuum energy level than the HOMO energy level of 4,4',4'' -(1,3,5-phenyltriyl)tri[dibenzothiophene] has the same or closer HOMO energy level to the vacuum level; preferably, the HOMO energy level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) is further from the vacuum level than the HOMO energy level of N,N'-((9H-fluorene-9,9-diyl)bis(4,1-phenyleneyl))bis(N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine). The HOMO energy level is the same as or closer to the vacuum energy level of 4,4',4''-(1,3,5-benzyl)tri[dibenzothiophene]; or, the HOMO energy level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) is the same as or further away from the vacuum energy level of 9-phenyl-10-(3',4',5'-triphenyl-[1,1':2',1''-terphenyl]-3-yl)anthracene. The HOMO level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) is further from the vacuum level than the HOMO level of tris(4-(9H-carbazole-9-yl)phenyl)amine, and is the same as or closer to the vacuum level than that of 4,4',4''-(1,3,5-phenyltriyl)tris[dibenzothiophene] (-5.67 eV, calculated by the methods described in this specification).

[0094] The term "HOMO level closer to the vacuum level" should be understood to mean that the absolute value of the HOMO level is lower than the absolute value of the HOMO level of the reference compound. For example, the term "closer to the vacuum level than the HOMO level of 4,4',4''-(1,3,5-phenyltriyl)tri[dibenzothiophene]" should be understood to mean that the absolute value of the HOMO level of the said organic matrix compound (OMC) is lower than the HOMO level of 4,4',4''-(1,3,5-phenyltriyl)tri[dibenzothiophene].

[0095] According to one embodiment, when measured under the same conditions, the HOMO energy level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) is further from the vacuum energy level than the HOMO energy level of N4,N4'''-di(naphthyl-1-yl)-N4,N4'''-diphenyl-[1,1':4',1'':4'',1'''-tetraphenyl]-4,4'''-diamine; wherein the HOMO energy level of N4,N4'''-di(naphthyl-1-yl)-N4,N4'''-diphenyl-[1,1':4',1'':4'',1'''-tetraphenyl]-4,4'''-diamine is -4.85 eV; Alternatively, the HOMO level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) is the same as or further away from the vacuum level than the HOMO level of N,N'-((9H-fluorene-9,9-diyl)bis(4,1-phenyleneyl))bis(N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine); wherein the HOMO level of N,N'-((9H-fluorene-9,9-diyl)bis(4,1-phenyleneyl))bis(N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine) is -4.86 eV; Alternatively, the HOMO level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) is the same as or further from the vacuum level of the HOMO level of 9-phenyl-10-(3',4',5'-triphenyl-[1,1':2',1''-terphenyl]-3-yl)anthracene; wherein the HOMO level of 9-phenyl-10-(3',4',5'-triphenyl-[1,1':2',1''-terphenyl]-3-yl)anthracene is -5.04 eV; or, the HOMO level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) is the same as or further from the vacuum level of the HOMO level of tris(4-(9H-carbazole-9-yl)phenyl)amine; wherein the HOMO level of tris(4-(9H-carbazole-9-yl)phenyl)amine is -5.09 eV.

[0096] Preferably, the HOMO level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) is further away from the vacuum level than the HOMO level of N,N'-((9H-fluorene-9,9-diyl)bis(4,1-phenyleneyl))bis(N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine) (-4.86 eV, calculated by the method described in this specification).

[0097] According to one embodiment, when measured under the same conditions, the HOMO energy levels of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) are further away from the vacuum energy level than the HOMO energy level of N4,N4'''-di(naphthyl-1-yl)-N4,N4'''-diphenyl-[1,1':4',1'':4'',1'''-tetraphenyl]-4,4'''-diamine, and are further away from the vacuum energy level than the HOMO energy level of 4,4',4''-(1,3,5-phenyltriyl)tris[dibenzo[] The HOMO level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) is the same as or closer to the vacuum level than the HOMO level of N,N'-((9H-fluorene-9,9-diyl)bis(4,1-phenyleneyl))bis(N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine), and is the same as or closer to the vacuum level than 4,4',4''-(1,3,5-phenyltriyl)tris[dibenzothiophene] (-5.67 eV, calculated by the method described in this specification).

[0098] According to one embodiment, when measured under the same conditions, the HOMO energy level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) is further from the vacuum energy level than the HOMO energy level of N4,N4'''-di(naphthyl-1-yl)-N4,N4'''-diphenyl-[1,1':4',1'':4'',1'''-tetraphenyl]-4,4'''-diamine; wherein the HOMO energy level of N4,N4'''-di(naphthyl-1-yl)-N4,N4'''-diphenyl-[1,1':4',1'':4'',1'''-tetraphenyl]-4,4'''-diamine is -4.85. eV, preferably, when measured under the same conditions, the HOMO energy level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) is further away from the vacuum energy level than the HOMO energy level of N,N'-((9H-fluorene-9,9-diyl)bis(4,1-phenyleneyl))bis(N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine); wherein the HOMO energy level of N,N'-((9H-fluorene-9,9-diyl)bis(4,1-phenyleneyl))bis(N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4-amine) is -4.86 eV.

[0099] According to one embodiment, the organic matrix compound (OMC) satisfies the following formula: -7 eV < HOMO level (OMC) < -4.85 eV, or -6 eV < HOMO level (OMC) < -4.86 eV, or -6 eV < HOMO level (OMC) < -4.9 eV, or -6 eV < HOMO level (OMC) < -5 eV, or -5.8 eV < HOMO level (OMC) < -5.05 eV, or -5.7 eV < HOMO level (OMC) < -5.1 eV.

[0100] According to one embodiment, the luminescent matrix compound (EMC) satisfies the following formula: -7 eV < HOMO level (EMC) < -4.85 eV, or -6 eV < HOMO level (EMC) < -4.86 eV, or -6 eV < HOMO level (EMC) < -4.9 eV, or -6 eV < HOMO level (EMC) < -5 eV, or -5.7 eV < HOMO level (EMC) ≤ -5.05 eV, or -5.3 eV ≤ HOMO level (EMC) ≤ -5.1 eV.

[0101] According to one embodiment, the organic matrix compound (OMC) and the luminescent matrix compound (EMC) satisfy the following formula: -7 eV < HOMO level (OMC) and HOMO level (EMC) < -4.85 eV, Preferably, the HOMO energy level (OMC) is -6 eV < and the HOMO energy level (EMC) is -4.86 eV. Alternatively, -6 eV < HOMO level (OMC) and HOMO level (EMC) < -4.9 eV, or -6 eV < HOMO level (OMC) and HOMO level (EMC) < -5 eV, or -5.7 eV < HOMO level (OMC) and HOMO level (EMC) ≤ -5.05 eV, or -5.3 eV ≤ HOMO level (OMC) and HOMO level (EMC) ≤ -5.1 eV.

[0102] Organic matrix compounds (OMCs) suitable for use as matrix materials in, for example, hole injection layers of organic electronic devices can have the following formula (I): (Ar 1 ) k —(Ar 2 ) m —Ar 3 —(Ar 4 ) p —(Ar 5 ) q —(Ar 6 ) r (I), in k, m, q, and r can be independently selected from 0, 1, or 2. p is 1, 2, or 3. Where 2 ≤ k+m+q+r+p ≤ 11, Ar 1 To Ar6 It can be independently selected from heterocycles of substituted or unsubstituted unsaturated 5 to 7-membered rings, and substituted or unsubstituted C6 to C6 rings. 30 Aryl, substituted or unsubstituted C3 to C 30 The rings are selected from: (i) heterocyclic rings with unsaturated 5 to 7-membered rings, (ii) aromatic heterocyclic rings with 5 to 6 members, (iii) non-heterocyclic rings with unsaturated 5 to 7-membered rings, and (iv) aromatic non-heterocyclic rings with 6-membered rings. The substituents are selected from H, D, C1 to C. 12 Alkyl, unsubstituted C6 to C 18 Aryl, unsubstituted C3 to C 18 The heteroaryl group comprises a fused ring system containing 2 to 6 unsubstituted 5 to 7-membered rings, wherein the rings are selected from: unsaturated 5 to 7-membered heterocycles, 5 to 6-membered aromatic heterocycles, unsaturated 5 to 7-membered non-heterocycles, and 6-membered aromatic non-heterocycles.

[0103] According to one embodiment, the organic matrix compound (OMC) and the luminescent matrix compound (EMC) have formula (I): (Ar 1 ) k —(Ar 2 ) m —Ar 3 —(Ar 4 ) p —(Ar 5 ) q —(Ar 6 ) r (I), in k, m, q, and r are each independently 0, 1, or 2. p is 1, 2, or 3. Where 2 ≤ k+m+q+r+p ≤ 11, Ar 1 To Ar 6 Independently selected from: heterocycles of unsaturated 5- to 7-membered rings, substituted or unsubstituted, C6 to C6 rings. 30 Aryl, substituted or unsubstituted C3 to C 30 The rings are selected from: (i) heterocyclic rings with unsaturated 5 to 7-membered rings, (ii) aromatic heterocyclic rings with 5 to 6 members, (iii) non-heterocyclic rings with unsaturated 5 to 7-membered rings, and (iv) aromatic non-heterocyclic rings with 6-membered rings. Ar 2 When k=1, Ar3 Ar 4 When q = 1, Ar 5 When r = 1: Heterocycles independently selected from substituted or unsubstituted unsaturated 5- to 7-membered rings, substituted or unsubstituted C6 to C6 rings. 30 Aranediol, substituted or unsubstituted C3 to C4 30 Heteroarylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted terphenylene, substituted or unsubstituted tetraphenylene, substituted or unsubstituted benzo[a]anthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthone, substituted or unsubstituted carbazole, substituted or unsubstituted azaheptatriene, substituted or unsubstituted diphenylene [b,f]-azacycloheptatriene, 9,9'-spirobis[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanton], substituted or unsubstituted 9,14-dihydrodibenzo[2,3:6,7]azacycloheptatriene[4,5-b]indole, or a substituted or unsubstituted aromatic fused ring system comprising at least three substituted or unsubstituted aromatic rings selected from: substituted or unsubstituted non-heterocyclic rings, substituted or unsubstituted heterocyclic 5-membered rings, substituted or unsubstituted 6-membered rings, and / or substituted or unsubstituted 7-membered rings; Ar 2 When k=0, Ar 3 When m=0 and k=0, Ar 4 When q and r = 0, Ar 5 When r = 0: Heterocycles independently selected from substituted or unsubstituted unsaturated 5- to 7-membered rings, substituted or unsubstituted C6 to C6 rings. 30 Aryl, substituted or unsubstituted C3 to C 30Heteroaryl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthrayl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted terphenylene, substituted or unsubstituted tetraphenyl, substituted or unsubstituted benzoanthrayl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthyl, substituted or unsubstituted carbazole, substituted or unsubstituted azaheptatriene, substituted or unsubstituted The substituted dibenzo[b,f]azacycloheptatriene, 9,9'-spirobis[fluorenyl], substituted or unsubstituted spiro[fluorenyl-9,9'-xanton], substituted or unsubstituted 9,14-dihydrodibenzo[2,3:6,7]azacycloheptatrien[4,5-b]indole, or a substituted or unsubstituted aromatic fused ring system comprising at least three substituted or unsubstituted aromatic rings selected from: substituted or unsubstituted non-heterocyclic rings, substituted or unsubstituted heterocyclic 5-membered rings, substituted or unsubstituted 6-membered rings and / or substituted or unsubstituted 7-membered rings; The substituents are selected from H, D, C1 to C. 12 Alkyl, unsubstituted C6 to C 18 Aryl, unsubstituted C3 to C 18 A heteroaryl fused ring system comprising 2 to 6 unsubstituted 5- to 7-membered rings, wherein the rings are selected from: unsaturated 5- to 7-membered heterocycles, 5- to 6-membered aromatic heterocycles, unsaturated 5- to 7-membered non-heterocycles, and 6-membered aromatic non-heterocycles; and The organic matrix compound (OMC) and the luminescent matrix compound (EMC) are selected to be the same or different, preferably different; wherein the metal complex has formula (II).

[0104] According to one implementation, Ar 1 To Ar 6It can be independently selected from: substituted or unsubstituted biphenylene groups, substituted or unsubstituted fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted terphenylene groups, substituted or unsubstituted tetraphenylene, substituted or unsubstituted benzo[b]anthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthone, substituted or unsubstituted carbazole, substituted or unsubstituted azacycloheptatriene, substituted or unsubstituted dibenzo[b]anthracene. [f]-Azaheptatriene, 9,9'-spirobis[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanton], substituted or unsubstituted 9,14-dihydrodibenzo[2,3:6,7]azaheptatriene[4,5-b]indole, or substituted or unsubstituted aromatic fused ring systems comprising at least three substituted or unsubstituted aromatic rings selected from: substituted or unsubstituted non-heterocyclic rings, substituted or unsubstituted heterocyclic 5-membered rings, substituted or unsubstituted 6-membered rings, and / or substituted or unsubstituted 7-membered rings. The substituents are selected from H, D, C1 to C. 12 Alkyl, unsubstituted C6 to C 18 Aryl, unsubstituted C3 to C 18 The heteroaryl group comprises a fused ring system containing 2 to 6 unsubstituted 5 to 7-membered rings, wherein the rings are selected from: unsaturated 5 to 7-membered heterocycles, 5 to 6-membered aromatic heterocycles, unsaturated 5 to 7-membered non-heterocycles, and 6-membered aromatic non-heterocycles.

[0105] According to one embodiment, the organic matrix compound (OMC) of formula (I) contained in the hole injection layer and / or the photoluminescent matrix compound (EMC) of formula (I) contained in the light-emitting layer (EML) may have a molecular weight Mw ≥ 400 g / mol and ≤ 2000 g / mol, preferably Mw ≥ 450 g / mol and ≤ 1500 g / mol, more preferably Mw ≥ 500 g / mol and ≤ 1000 g / mol, further preferably Mw ≥ 550 g / mol and ≤ 900 g / mol, and even more preferably Mw ≥ 600 g / mol and ≤ 800 g / mol.

[0106] According to one embodiment, the HOMO energy level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) may be less than -4.85 eV, preferably less than -4.9 eV, or less than -4.95 eV, or less than -5 eV, or less than -5.05 eV, or less than -5.09 eV.

[0107] According to one embodiment, the HOMO energy level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) may be less than -4.85 eV and greater than -7 eV, preferably less than -4.9 eV and greater than -7 eV, or less than -4.95 eV and greater than -7 eV, or less than -5 eV and greater than -7 eV, or less than -5.05 eV and greater than -7 eV, or less than -5.09 eV and greater than -7 eV.

[0108] According to one embodiment, the HOMO energy level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may be less than -4.85 eV, preferably less than -4.9 eV, or less than -4.95 eV, or less than -5 eV.

[0109] According to one embodiment, the HOMO energy level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may be less than -4.85 eV and greater than -7 eV, preferably less than -4.9 eV and greater than -7 eV, or less than -4.95 eV and greater than -7 eV, or less than -5 eV and greater than -7 eV.

[0110] According to one embodiment, the HOMO energy level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may be less than -4.85 eV and greater than -6.5 eV, preferably less than -4.9 eV and greater than -6.5 eV, or less than -4.95 eV and greater than -6.5 eV, or less than -5 eV and greater than -6.5 eV, or less than -5.05 eV and greater than -6.5 eV, or less than -5.09 eV and greater than -6.5 eV.

[0111] According to one embodiment, the HOMO energy level of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may be less than -4.85 eV and greater than -6 eV, preferably less than -4.9 eV and greater than -6 eV, or less than -4.95 eV and greater than -6 eV, or less than -5 eV and greater than -6 eV, or less than -5.05 eV and greater than -6 eV, or less than -5.09 eV and greater than -6 eV.

[0112] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may contain at least ≥1 to ≤6 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings.

[0113] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may contain at least ≥1 to ≤6 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings and at least ≥1 to ≤3 substituted or unsubstituted unsaturated 5- to 7-membered heterocycles, preferably ≥2 to ≤5 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings.

[0114] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may comprise at least ≥1 to ≤6 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings and at least ≥1 to ≤3 substituted or unsubstituted unsaturated 5- to 7-membered heterocycles, preferably ≥2 to ≤5 substituted heteroaromatic rings. The aromatic fused ring system comprises a substituted or unsubstituted aromatic ring system and a heterocycle comprising at least 1 to 3 substituted or unsubstituted unsaturated 5 to 7-membered rings, more preferably 3 or 4 substituted or unsubstituted aromatic ring systems comprising heterocyclic rings and optionally at least 1 to 3 substituted or unsubstituted unsaturated 5 to 7-membered rings, and further preferably the aromatic fused ring system comprising heterocyclic rings is an unsubstituted and optionally at least 1 to 3 unsubstituted unsaturated 5 to 7-membered rings.

[0115] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may contain at least ≥1 to ≤6 substituted or unsubstituted aromatic fused ring systems, preferably ≥2 to ≤5 substituted or unsubstituted aromatic fused ring systems, more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems.

[0116] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may comprise at least ≥1 to ≤6 substituted or unsubstituted aromatic fused ring systems, preferably ≥2 to ≤5 substituted or unsubstituted aromatic fused ring systems, more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems, wherein the aromatic fused ring system comprises substituted or unsubstituted heteroaromatic rings.

[0117] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may contain at least ≥1 to ≤3 or 2 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles.

[0118] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may contain at least 1 to 3 or 2 substituted or unsubstituted unsaturated 7-membered heterocycles.

[0119] According to one embodiment, the substituted or unsubstituted aromatic fused ring system of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the substituted or unsubstituted aromatic fused ring system of the luminescent matrix compound (EMC) of formula (I) may contain at least ≥1 to ≤3 or 2 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles.

[0120] According to one embodiment, the substituted or unsubstituted aromatic fused ring system of the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the substituted or unsubstituted aromatic fused ring system of the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may contain at least 1 to ≤3 or 2 substituted or unsubstituted unsaturated 7-membered heterocycles.

[0121] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may comprise at least ≥1 to ≤6 substituted or unsubstituted aromatic fused ring systems, preferably ≥2 to ≤5 substituted or unsubstituted aromatic fused ring systems, more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems, and wherein the aromatic fused ring system comprises a substituted or unsubstituted unsaturated 5- to 7-membered heterocycle.

[0122] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may comprise at least ≥1 to ≤6 substituted or unsubstituted aromatic fused ring systems, preferably ≥2 to ≤5 substituted or unsubstituted aromatic fused ring systems, more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems, wherein the aromatic fused ring system comprises substituted or unsubstituted heterocyclic rings, and wherein the aromatic fused ring system comprises substituted or unsubstituted unsaturated 5- to 7-membered heterocyclic rings.

[0123] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may comprise at least ≥1 to ≤6 substituted or unsubstituted aromatic fused ring systems, preferably ≥2 to ≤5 substituted or unsubstituted aromatic fused ring systems, more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems, wherein the aromatic fused ring system comprises at least ≥1 to ≤3 or 2 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles.

[0124] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may comprise at least ≥1 to ≤6 substituted or unsubstituted aromatic fused ring systems, preferably ≥2 to ≤5 substituted or unsubstituted aromatic fused ring systems, more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems, wherein the aromatic fused ring system comprises substituted or unsubstituted heteroaromatic rings, and wherein the aromatic fused ring system comprises at least ≥1 to ≤3 or 2 substituted or unsubstituted unsaturated 5 to 7-membered heterocyclic rings.

[0125] According to one implementation method - The organic matrix compound (OMC) and the luminescent matrix compound (EMC) comprise a substituted or unsubstituted aromatic fused ring system having at least 2 to ≤6, preferably 3 to ≤5, or 4 fused aromatic rings, wherein the fused aromatic rings are selected from: substituted or unsubstituted non-heteroaromatic rings, substituted or unsubstituted heterocyclic 5-membered rings, substituted or unsubstituted 6-membered rings, and / or substituted or unsubstituted unsaturated 5- to 7-membered heterocyclic rings; or - The organic matrix compound (OMC) and the luminescent matrix compound (EMC) or the organic matrix compound of formula (I) and the luminescent matrix compound of formula (I) comprise an unsubstituted aromatic fused ring system having at least 2 to ≤6, preferably 3 to ≤5 or 4 fused aromatic rings, wherein the fused aromatic rings are selected from: unsubstituted non-heteroaromatic rings, unsubstituted hetero 5-membered rings, unsubstituted 6-membered rings and / or unsubstituted unsaturated 5 to 7-membered heterocycles.

[0126] It should be noted here that the term "aromatic fused ring system" can include at least one aromatic ring and at least one substituted or unsubstituted unsaturated 5- to 7-membered ring. It should also be noted here that a substituted or unsubstituted unsaturated 5- to 7-membered ring is not necessarily an aromatic ring.

[0127] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may comprise at least 1 to ≤6, preferably 2 to ≤5, or more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems, wherein the aromatic fused ring system has: - At least one unsaturated 5-membered ring, and / or - At least one unsaturated 6-membered ring, and / or - At least one unsaturated 7-membered ring; wherein preferably at least one unsaturated 5-membered ring and / or at least one unsaturated 7-membered ring contains at least 1 to 3, preferably 1, heteroatom.

[0128] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may comprise at least 1 to 6, preferably 2 to 5, or more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems, wherein the aromatic fused ring system has: - At least one aromatic 5-membered ring, and / or - At least one aromatic 6-membered ring, and / or - At least one aromatic 7-membered ring; wherein preferably at least one aromatic 5-membered ring and / or at least one aromatic 7-membered ring contains at least 1 to 3, preferably 1, heteroatom; The substituted or unsubstituted aromatic fused ring system comprises at least 1 to 3 or 2 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles.

[0129] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may comprise: - At least 6 to 12, preferably 7 to 11, more preferably 8 to 10 or 9 aromatic rings; and / or - At least 4 to 11, preferably 5 to 10, more preferably 6 to 9, or even more preferably 7 or 8 non-heteroaromatic rings, preferably the non-heteroaromatic rings are aromatic C6 rings; and / or - At least 1 to 4, preferably 2 or 3, aromatic 5-membered rings, and more preferably heteroaromatic 5-membered rings; and / or - At least one or two heterocycles with unsaturated 5- or 7-membered rings, preferably at least one or two heterocycles with unsaturated 7-membered rings; and / or - At least 6 to 12, preferably 7 to 11, more preferably 8 to 10 or 9 aromatic rings; wherein thus At least 4 to 11, preferably 5 to 10, more preferably 6 to 9, or even more preferably 7 or 8, are non-heteroaromatic rings, and At least 1 to 4, preferably 2 or 3, aromatic rings are heterocyclic aromatic rings, wherein the total number of non-heterocyclic and heterocyclic aromatic rings does not exceed 12 aromatic rings; and / or - At least 6 to 12, preferably 7 to 11, more preferably 8 to 10 or 9 aromatic rings; wherein thus At least 4 to 11, preferably 5 to 10, more preferably 6 to 9, or even more preferably 7 or 8, are non-heteroaromatic rings, and At least 1 to 4, preferably 2 or 3, aromatic rings are heterocyclic aromatic rings, wherein the total number of non-heterocyclic and heterocyclic aromatic rings does not exceed 12 aromatic rings; and The organic matrix compound or the organic matrix compound according to Formula I and the luminescent matrix compound or the luminescent matrix compound of Formula I comprise at least 1 to ≤4, preferably 2 or 3, aromatic 5-membered rings, preferably heteroaromatic 5-membered rings, and / or The organic matrix compound or the organic matrix compound according to Formula I and the luminescent matrix compound or the luminescent matrix compound of Formula I contain at least one or two unsaturated 5- or 7-membered heterocycles, preferably at least one or two unsaturated 7-membered heterocycles.

[0130] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may contain heteroatoms, which may be selected from O, S, N, B or P, preferably, the heteroatoms may be selected from O, S or N.

[0131] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may comprise at least 1 to ≤6, preferably 2 to ≤5, or more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems, wherein the aromatic fused ring system has: - At least one aromatic 5-membered ring, and / or - At least one aromatic 6-membered ring, and / or - At least one aromatic 7-membered ring; wherein preferably at least one aromatic 5-membered ring and / or at least one aromatic 7-membered ring contains at least 1 to 3, preferably 1, heteroatom; The substituted or unsubstituted aromatic fused ring system optionally comprises at least 1 to 3 or 2 substituted or unsubstituted unsaturated 5- to 7-membered heterocycles; and the substituted or unsubstituted aromatic fused ring system comprises heteroatoms, which may be selected from O, S, N, B, P, As or Se, preferably selected from O, S or N.

[0132] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may not contain heteroatoms that are not part of an aromatic ring and / or part of an unsaturated 7-membered ring. Preferably, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) may not contain N atoms except for N atoms that are part of an aromatic ring or part of an unsaturated 7-membered ring.

[0133] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) comprises two carbazole groups, at least one dibenzofuran group, at least one dibenzothiophene group and / or at least one anthracene group.

[0134] According to one embodiment, the organic matrix compound (OMC) or the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) or the luminescent matrix compound (EMC) of formula (I) comprises two carbazole groups, one to three dibenzofuran groups, one to three dibenzothiophene groups and / or one to two anthracene groups.

[0135] According to one embodiment, for the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) of formula (I): - Ar 3 The selection can be from D1 to D17, with D1 to D6 and D16 being preferred: (D1) (D2) (D3) (D4) (D5) (D6); (D7) (D8) (D9) (D10); (D11) (D12) (D13) (D14) (D15) (D16) (D17)

[0136] According to one implementation, Ar is determined according to formula (I). 1 Selectable from D7 to D15 and D17. Ar 2 Options can be selected from D1 to D6, or D7 to D15 and D17. Ar 4 Options can be selected from D1 to D6, or D7 to D15 and D17. Ar 5 Options can be selected from D1 to D6, or D7 to D15 and D17. Ar 6 Selectable from D7 to D15 and D17.

[0137] According to one embodiment, the organic matrix compound (OMC) of formula (I) and / or the luminescent matrix compound (EMC) of formula (I): - Ar 3 Options are available from D1 to D17, with D1 to D6 and D16 being preferred: (D1) (D2) (D3) (D4) (D5) (D6); (D7) (D8) (D9) (D10); (D11) (D12) (D13) (D14) (D15) (D16) (D17); Ar 1 When m>0 and k>0, the selection is from D7 to D15 and D17; when k>0 and m=0, the selection is from D7 to D15 and D17; when k>1, the selection is from D1 to D6. Ar 2 When m>0 and k>0, the selection is from D1 to D6; or when m>0 and k=0, the selection is from D7 to D15 and D17. Ar 4 When q>0, select from D1 to D6; or when q=0 and r>0, select from D1 to D6; or when q and r=0, select from D7 to D15 and D17. Ar 5 When q>0 and r>0, the selection is from D1 to D6, or when q>0 and r=0, the selection is from D7 to D15 and D17; Ar 6 When r>0 and q>0, the selection is from D7 to D15 and D17; when r>0 and q=0, the selection is from D7 to D15 and D17; or when r>1, the selection is from D1 to D6.

[0138] According to one implementation, in formula (I), Ar 3 The group is selected from anthracene, carbazole, dibenzothiophene and / or dibenzofuran.

[0139] According to one implementation, in formula (I), Ar 3 The group was chosen to be anthracene.

[0140] According to one implementation, in formula (I), Ar 3 The group is selected from carbazole, dibenzothiophene and / or dibenzofuran.

[0141] According to one embodiment, the organic matrix compound (OMC) according to formula (I) and / or the luminescent matrix compound (EMC) according to formula (I) may be selected from F1 to F13: (F1) (F2) (F3) (F4) (F5) (F6) (F7) (F8) (F9) (F10) (F11) (F12) (F13).

[0142] Preferably, the organic matrix compound (OMC) and / or the luminescent matrix compound are free of metal and / or ionic bonds.

[0143] The hole injection layer and / or the organic matrix compound (OMC) and / or luminescent matrix compound (EMC) according to formula (I) may be free of HTM014, HTM081, HTM163, HTM222, EL-301, HTM226, HTM355, HTM133, HTM334, HTM604, and EL-22T. Abbreviations represent the manufacturer's name, such as Merck Ltd. or Lumtec Technology Co., Ltd.

[0144] The hole injection layer and / or the organic matrix compound (OMC) and / or luminescent matrix compound (EMC) according to formula (I) may be free of N,N'-bis(naphthyl-1-yl)-N,N'-bis(phenyl)-9,9-dimethylfluorene, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-9,9-dimethylfluorene, N,N'-bis(naphthyl-1-yl)-N,N'-bis(phenyl)-9,9-dimethylfluorene, N,N'-bis(naphthyl-1-yl)-N,N'-bis(phenyl)-2,2-dimethylbenzidine, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-9,9-spirodifluorene, 2,2',7,7'-tetra(N,N- Diphenylamino)-9,9'-spirodifluorene, N,N'-bis(naphthyl-1-yl)-N,N'-bis(phenyl)-benzidine, N,N'-bis(naphthyl-2-yl)-N,N'-bis(phenyl)-benzidine, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-benzidine, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-9,9-dimethylfluorene, N,N'-bis(naphthyl-1-yl)-N,N'-bis(phenyl)-9,9-spirodifluorene, di-[4-(N,N-dimethylamino)-phenyl]cyclohexane, 2,2',7,7'-tetra(N,N-dimethylamino)spirodifluorene, 9,9-bis[4-(N,N] [-bis-biphenyl-4-yl-amino)phenyl]-9H-fluorene, 2,2',7,7'-tetra(N,N-naphthyl(phenyl)-amino]-9,9'-spirodifluorene, 2,7-bis(N,N-bis(9,9-spiro-difluorene-2-yl)-amino]-9,9'-spirodifluorene, 2,2'-bis(N,N-bis(biphenyl-4-yl)amino]-9,9'-spirodifluorene, N,N'-bis(phenanthrene-9-yl)-N,N'-bis(phenyl)-benzidine, N,N,N',N'-tetra(naphthyl-2-yl)-benzidine, 2,2'-bis(N,N-di-phenyl-amino)-9,9-spirodifluorene, 9,9-bis[4-(N,N-bis-naphthyl-2-yl-amino)phenyl]-9H-fluorene -fluorene, 9,9-bis[4-(N,N'-bis-naphthyl-2-yl-N,N'-bis-phenyl-amino)-phenyl]-9H-fluorene, titanium phthalocyanine, copper phthalocyanine, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl ether, 4,4'4''-tris(N-3-methylphenyl-N-phenyl-amino)triphenylamine, 4,4',4''-tris(N-(2-naphthyl)-N-phenyl-amino)triphenylamine, 4,4',4''-tris(N-(1-naphthyl)-N-phenyl-amino)triphenylamine, 4,4',4''-tris(N,N-diphenyl-amino)triphenylamine, pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarboxynitrile, N,N,N',N'-Tetra(4-methoxyphenyl)benzidine, HTM014, HTM081, HTM163, HTM222, EL-301, HTM226, HTM355, HTM133, HTM334, HTM604, and EL-22T. The abbreviations represent the manufacturer's name, such as those used by Merck or Lumtec.

[0145] Metal complex of formula (II)

[0146] The metal complex according to formula (II) may be non-luminescent. In the context of this specification, the terms "substantially non-luminescent" or "non-luminescent" mean that, relative to the visible emission spectrum, the metal complex according to formula (II) contributes less than 10%, preferably less than 5%, to the visible emission spectrum of organic electronic devices such as OLEDs or display devices. The visible emission spectrum is an emission spectrum with wavelengths from about ≥380 nm to about ≤780 nm.

[0147] According to one embodiment, the metal ion M in formula (II) can be selected from metal ions, wherein the corresponding metal has an electronegativity value of less than 2.4 according to Allen. Preferably, M can be selected from alkali metals, alkaline earth metals, rare earth metals or transition metals. More preferably, M can be selected from metals with an atomic weight ≥ 24 Da. Furthermore, it is preferred that M can be selected from metals with an atomic weight ≥ 24 Da and M has an oxidation number ≥ 2.

[0148] The term “according to Allen’s electronegativity values” specifically refers to Allen, Leland C. (1989). “Electronegativity is the average one-electron energy of the valence-shell electrons in ground-state free atoms.” Journal of the American Chemical Society 111 (25): 9003-9014.

[0149] According to one embodiment of the present invention, the valence n of M is 1 or 2.

[0150] According to one embodiment of the invention, M is selected from metal ions, wherein the corresponding metal has an electronegativity value of less than 2.4 according to Allen's electronegativity value, preferably less than 2, more preferably less than 1.9, and the valence n of M is 1 or 2.

[0151] According to one embodiment of the present invention, M is selected from alkali metals, alkaline earth metals, rare earth metals or transition metals, or M is selected from alkali metals, alkaline earth metals, transition metals or main group metals of period 4 or 5.

[0152] According to one embodiment of the present invention, M is selected from Li, Na, K, Cs, Mg, Mn, Cu, Zn, Ag, Bi and Mo; preferably, M is selected from Na, K, Cs, Mg, Mn, Cu, Zn and Ag; even more preferably, M is selected from Na, K, Mg, Mn, Cu, Zn and Ag, wherein if M is Cu, then n is 2.

[0153] According to one embodiment of the present invention, M is not Li.

[0154] According to one embodiment of the present invention, M is neither Li nor K.

[0155] According to one embodiment of the present invention, M is not Ag.

[0156] According to one embodiment of the present invention, M is not Cu.

[0157] According to one embodiment of the present invention, M is not Mo.

[0158] According to one embodiment of the present invention, M is not Ir and / or Pt.

[0159] According to another embodiment, the metal complex according to formula (II) may have a molecular weight Mw ≥ 287 g / mol and ≤ 2000 g / mol, preferably a molecular weight Mw ≥ 400 g / mol and ≤ 1500 g / mol, more preferably a molecular weight Mw ≥ 580 g / mol and ≤ 1500 g / mol, and further preferably a molecular weight Mw ≥ 580 g / mol and ≤ 1400 g / mol.

[0160] According to another embodiment, the ligand L of formula (II), also known as L, can be selected from: - At least three carbon atoms or at least four carbon atoms, and / or - At least two oxygen atoms, or one oxygen atom and one nitrogen atom, two to four oxygen atoms, two to four oxygen atoms and zero to two nitrogen atoms, and / or - At least one or more groups selected from the following: halogen, F, CN, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy; or two or more groups selected from the following: halogen, F, CN, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy; at least one or more groups selected from the following: halogen, F, CN, substituted C1 to C6 alkyl, substituted C1 to C6 alkoxy; or two or more groups selected from the following: halogen, F, CN, perfluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkoxy; or one or more groups selected from the following: substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C6 alkyl; 12 aryl, and / or substituted or unsubstituted C3 to C4 12 Mixed aromatics; The substituents are selected from: D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkyl, partially deuterated or fully deuterated C1 to C6 alkoxy, COR 6 COOR 6 Halogen, F or CN; Where R 6 It can be selected from: C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkyl, partially deuterated or fully deuterated C1 to C6 alkoxy.

[0161] According to another embodiment, the ligand L of formula (II) may be selected from: at least two carbon atoms, or at least three carbon atoms, at least one oxygen atom, at least two oxygen atoms, at least one oxygen atom and / or a nitrogen atom, one nitrogen atom and at least two oxygen atoms, at least two carbon atoms and at least one oxygen atom, at least two carbon atoms and two oxygen atoms, or one oxygen atom and one nitrogen atom, at least one or more groups selected from: halogen, F, CN, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy; or two One or more groups selected from the following: halogen, F, CN, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy; at least one or more groups selected from the following: halogen, F, CN, substituted C1 to C6 alkyl, substituted C1 to C6 alkoxy; or two or more groups selected from the following: halogen, F, CN, perfluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkoxy; one or more groups selected from the following: substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C6 alkyl; or two or more groups selected from the following: halogen, F, CN, perfluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkoxy; or ... two or more groups selected from the following: substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C6 alkyl; or two or more groups selected from the following: substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkyl; or two or more groups selected from the following: substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkyl; or two or more groups selected from the following: substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkyl; or two or more groups selected from the following: substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkyl; or two or more groups selected from the following: substituted or unsubstituted C1 to C6 alkyl; or two or more groups selected from the following: substituted or unsubstituted C1 to C6 alkyl; or two or more groups selected from 12 Aryl and / or substituted or unsubstituted C3 to C4 12 Mixed aromatics; The substituents are selected from: D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkyl, partially deuterated or fully deuterated C1 to C6 alkoxy, COR 6 COOR 6 Halogen, F or CN; Where R 6 Selectable from: C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkyl, partially deuterated or fully deuterated C1 to C6 alkoxy.

[0162] According to another embodiment, the ligand L of formula (II) may be selected from: F, CN, perfluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy.

[0163] The substituents may be selected from: D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkyl, partially deuterated or fully deuterated C1 to C6 alkoxy, COR 6 COOR 6 Halogen, F or CN; Where R 6 It can be selected from C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkyl, partially deuterated or fully deuterated C1 to C6 alkoxy.

[0164] According to another embodiment, ligand L does not contain sulfur atoms. According to another embodiment, ligand L does not contain sulfur atoms or phthalocyanine groups.

[0165] According to another embodiment, the ligand L of formula (II) can be independently selected from G1 to G64, preferably G1 to G62: (G1) (G2) (G3) (G4) (G5) (G6) (G7) (G8) (G9) (G10) (G11) (G12) (G13) (G14) (G15) (G16) (G17) (G18) (G19)、 (G20)、 (G21)、 (G22)、 (G23)、 (G24)、 (G25)、 (G26)、 (G27)、 (G28)、 (G29)、 (G30)、 (G31)、 (G32)、 (G33)、 (G34)、 (G35)、 (G36)、 (G37)、 (G38)、 (G39)、 (G40)、 (G41)、 (G42)、 (G43)、 (G44)、 (G45)、 (G46)、 (G47)、 (G48)、 (G49)、 (G50)、 (G51)、 (G52)、 (G53)、 (G54)、 (G55)、 (G56)、 (G57)、 (G58) (G59) (G60) (G61) (G62) (G63) (G64).

[0166] The negative charge in the metal complex of formula (II) can be partially or completely delocalized on ligand L.

[0167] According to another embodiment, L is selected from (G1) to (G52) and (G60) to (G64).

[0168] Preferably, L is selected from (G2) to (G59), or L is selected from (G2) to (G52).

[0169] Metal complexes of formulas (IIa) to (IIe)

[0170] According to one embodiment, the metal complex may be selected from formulas (IIa) to (IIe), and preferably from formulas (IIa) to (IId): (IIa) (IIb) (IIc) (IId) (IIe), in M is a metal ion; n is the valence of M, where preferably n is an integer from 1 to 4; A 1 and A 2 It can be independently selected from substituted or unsubstituted C1 to C1. 12 Alkyl, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 12 Mixed aromatics; A 3 Selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 12 Mixed aromatics; Where A 1 A 2 and / or A 3The substituents may be independently selected from: D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkyl, partially deuterated or fully deuterated C1 to C6 alkoxy, COR 1 COOR 1 halogen, F or CN, among which R 1 Selectable from: C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkyl, partially deuterated or fully deuterated C1 to C6 alkoxy.

[0171] The negative charge in the metal complexes of formulas (IIa), (IIb), (IIc), and / or (IId) can be present in carbon atoms, heteroatoms, and A atoms. 1 A 2 and / or A 3 The upper part or the entire domain is off-domain.

[0172] According to one implementation, A 1 A 2 and / or A 3 At least one of them may contain a substituent, wherein A 1 A 2 and / or A 3 At least one of the substituents may be independently selected from: C3 to C9 heteroaryl, C1 to C6 alkoxy, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkoxy, COR 1 COOR 1 Halogen, F or CN; preferably A 1 and A 2 and / or A 3 At least one of them contains at least two substituents, wherein

[0173] A 1 A 2 and / or A3 The substituents on the molecule can be independently selected from: C3 to C9 heteroaryl, C1 to C6 alkoxy, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C9 alkoxy, etc. 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkoxy, COR 1 COOR 1 Halogen, F or CN; more preferably A 1 A 2 and / or A 3 It may contain at least one substituent independently selected from: halogen, F, CF3, C2F5, C3F7, C4F9, OCF3, OC2F5 or CN; and preferably A. 1 A 2 and / or A 3 It may contain at least two independent substituents selected from the following: halogen, F, CF3, C2F5, C3F7, C4F9, OCF3, OC2F5 or CN.

[0174] According to one embodiment of the present invention, A 1 A 2 and / or A 3 It can be independently selected from: CF3, C2F5, C3F7, C4F9, C5F 11 C6F 13 And / or phenyl groups substituted with two to five independently selected groups chosen from F or CF3, or C2F5, C3F7, C4F9, C5F 11 C6F 13 And / or phenyl groups substituted with two to five independently selected groups chosen from F or CF3, or CF3, C2F5, C3F7, C4F9, C5F 11 C6F 13 Or a phenyl group substituted with zero to two CF3 groups and / or zero to five F atoms.

[0175] According to one embodiment of the present invention, the metal complex may be selected from...

[0176] - Formula (IIa), where M is selected from alkali metals, alkaline earth metals, transition metals, or rare earth metals; and / or

[0177] - Formula (IIb), where M is selected from alkali metals, alkaline earth metals, transition metals, or rare earth metals; and / or

[0178] - Formula (IIc), where M is selected from alkali metals, alkaline earth metals or main group metals.

[0179] According to one embodiment of the present invention, the metal complex may be selected from formula (IIa) or formula (IIb). Wherein M is selected from metal ions, wherein the corresponding metal has an electronegativity value of less than 2.4 according to Allen, preferably M is selected from alkali metals, alkaline earth metals, rare earth metals or transition metals, more preferably M is selected from metals with an atomic weight ≥ 24 Da, further preferably M is selected from metals with an atomic weight ≥ 24 Da and M has an oxidation number ≥ 2; and / or formula (IIc), wherein M is selected from Bi.

[0180] The following metal complexes are particularly preferred:

[0181] According to one embodiment, the metal complex may be TFSI-free. Therefore, the metal complex is particularly suitable for the large-scale production of organic electronic devices.

[0182] Hole injection layer

[0183] According to another embodiment, the hole injection layer may comprise an organic matrix compound (OMC) and a metal complex, wherein the metal complex has formula (II): (II), in M is a metal ion. n is the valence of M, where n is an integer from 1 to 4. L is a ligand.

[0184] According to another embodiment, the hole injection layer may comprise an organic matrix compound (OMC) and a metal complex: - The matrix compound (OMC) described therein has formula (I): (Ar 1 ) k —(Ar 2 ) m —Ar 3 —(Ar 4 ) p —(Ar 5 ) q —(Ar 6 ) r (I), in k, m, q, and r can be independently selected from 0, 1, or 2. p is 1, 2, or 3. Where 2 ≤ k+m+q+r+p ≤ 11, Ar 1 To Ar 6 It can be independently selected from heterocycles of substituted or unsubstituted unsaturated 5 to 7-membered rings, and substituted or unsubstituted C6 to C6 rings. 30 Aryl, substituted or unsubstituted C3 to C 30 The rings are selected from: (i) heterocyclic rings with unsaturated 5 to 7-membered rings, (ii) aromatic heterocyclic rings with 5 to 6 members, (iii) non-heterocyclic rings with unsaturated 5 to 7-membered rings, and (iv) aromatic non-heterocyclic rings with 6-membered rings. Ar 2 When k=1, Ar 3 Ar 4 When q = 1, Ar 5 When r = 1: It can be independently selected from: substituted or unsubstituted unsaturated 5- to 7-membered heterocycles, substituted or unsubstituted C6 to C6 rings. 30 Aranediol, substituted or unsubstituted C3 to C4 30 Heteroarylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted terphenylene, substituted or unsubstituted tetraphenylene, substituted or unsubstituted benzo[b]anthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthone, substituted or unsubstituted carbazole, substituted or unsubstituted azaheptatriene, substituted or unsubstituted dibenzo[b] f] azaheptatriene, 9,9'-spirobis[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanton], substituted or unsubstituted 9,14-dihydrodibenzo[2,3:6,7]azaheptatriene[4,5-b]indole, or a substituted or unsubstituted aromatic fused ring system comprising at least three, preferably three to six, substituted or unsubstituted aromatic rings selected from: substituted or unsubstituted non-heterocyclic rings, substituted or unsubstituted heterocyclic 5-membered rings, substituted or unsubstituted 6-membered rings, and / or substituted or unsubstituted 7-membered rings; Ar 2 When k=0, Ar 3 When m=0 and k=0, Ar 4 When q and r = 0, Ar 5 When r = 0: It can be independently selected from: substituted or unsubstituted unsaturated 5- to 7-membered heterocycles, substituted or unsubstituted C6 to C6 rings. 30 Aryl, substituted or unsubstituted C3 to C 30Heteroaryl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted terphenylene, substituted or unsubstituted tetraphenyl, substituted or unsubstituted benzoanthrayl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthyl, substituted or unsubstituted carbazole, substituted or unsubstituted azacycloheptatriene, substituted or unsubstituted di Benzo[b,f]-heptacyclic heptarylene, 9,9'-spirobis[fluorenyl], substituted or unsubstituted spiro[fluorenyl-9,9'-xanton], substituted or unsubstituted 9,14-dihydrodibenzo[2,3:6,7]-heptacyclic heptarylene[4,5-b]indole, or substituted or unsubstituted aromatic fused ring systems comprising at least three, preferably three to six, substituted or unsubstituted aromatic rings selected from: substituted or unsubstituted non-heterocyclic rings, substituted or unsubstituted heterocyclic 5-membered rings, substituted or unsubstituted 6-membered rings and / or substituted or unsubstituted 7-membered rings; The substituents are selected from H, D, C1 to C. 12 Alkyl, unsubstituted C6 to C 18 aryl or unsubstituted C3 to C 18 Mixed aromatics; - The metal complex described therein has formula (II): (II), in M is a metal ion. n is the valence of M, where n is an integer from 1 to 4. L is a ligand containing at least two carbon atoms.

[0185] According to one implementation, n is an integer from 1 to 4, preferably an integer from 1 to 3, and even more preferably 2 or 3.

[0186] Preferably, the hole injection layer is free of ionic liquids, metal phthalocyanines, CuPc, HAT-CN, pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarboxynitrile, F4TCNQ, metal fluorides, and / or metal oxides, wherein the metal in the metal oxide is selected from Re and / or Mo. Thus, the hole injection layer can be deposited under conditions suitable for large-scale production.

[0187] According to one embodiment, the hole injection layer is arranged to be in direct contact with the anode layer.

[0188] Hole-injected layers (HILs) can be formed on the anolyte layer via vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blodgett (LB) deposition, etc. When using vacuum deposition to form HILs, the deposition conditions can vary depending on the organic matrix compound used to form the HIL and the desired structure and thermal properties of the HIL. However, generally, conditions used for vacuum deposition can include deposition temperatures ranging from 100°C to 350°C, and 10... -8 Up to 10 -3 The pressure of Torr (1 Torr equals 133.322 Pa) and the deposition rate from 0.1 to 10 nm / s.

[0189] When spin coating or printing is used to form HILs, the coating conditions can vary depending on the organic matrix compound used to form the HIL and the desired structure and thermal properties of the HIL. For example, coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80°C to about 200°C. After coating, heat treatment removes the solvent.

[0190] HIL can be formed from any organic matrix compound of formula (I) and metal complexes of formula (II), (IIa) to (IIe), and preferably formula (II), (IIa) to (IId).

[0191] The thickness of HIL can range from about 1 nm to about 15 nm, for example from about 2 nm to about 12 nm, or from about 3 nm to about 10 nm.

[0192] When the thickness of HIL is within this range, HIL can have excellent hole injection characteristics without causing substantial damage to the operating voltage.

[0193] According to one embodiment of the present invention, the hole injection layer may comprise: - At least about ≥5% by weight to about ≤90% by weight, preferably about ≥30% by weight to about ≤80% by weight, more preferably about ≥40% by weight to about ≤80% by weight, and even more preferably about ≥50% by weight to about ≤80% by weight of an organic matrix compound or an organic matrix compound of formula (I), and - At least about ≥10% by weight to about ≤95% by weight, preferably about ≥20% by weight to about ≤70% by weight, more preferably about ≥20% by weight to about ≤60% by weight, and even more preferably about ≥20% by weight to about ≤50% by weight of metal complexes of formula (II), (IIa) to (IIe), and more preferably formula (II), (IIa) to (IId); preferably, the weight percentage of the metal complexes of formula (II), (IIa) to (IIe), and more preferably formula (II), (IIa) to (IId) is less than the weight percentage of the organic matrix compound or the organic matrix according to formula (I); wherein the weight percentage of the components is based on the total weight of the hole injection layer.

[0194] According to one embodiment of the present invention, the hole injection layer may include: - At least about ≥5% by volume to about ≤90% by volume, preferably about ≥30% by volume to about ≤80% by volume, more preferably about ≥40% by volume to about ≤80% by volume, and even more preferably about ≥50% by volume to about ≤80% by volume of an organic matrix compound or an organic matrix compound of formula (I), and - At least about ≥10 volume% to about ≤95 volume%, preferably about ≥20 volume% to about ≤70 volume%, more preferably about ≥20 volume% to about ≤60 volume%, and even more preferably about ≥20 volume% to about ≤50 volume% of metal complexes of formula (II), (IIa) to (IIe), and more preferably formula (II), (IIa) to (IId); preferably, the volume% of the metal complexes of formula (II), (IIa) to (IIe), and more preferably formula (II), (IIa) to (IId) is less than the volume% of the organic matrix compound or the organic matrix according to formula (I); wherein the weight% of the components is based on the total weight of the hole injection layer.

[0195] Preferably, the hole injection layer is free of ionic liquids, metal phthalocyanines, ZnPc, CuPc, HAT-CN, pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarboxynitrile, F4TCNQ, metal fluorides, and / or metal oxides, wherein the metal in the metal oxide is selected from Re and / or Mo. Thus, the hole injection layer can be deposited under conditions suitable for large-scale production.

[0196] Organic electronic devices

[0197] According to one embodiment, the organic electronic device may include a hole injection layer comprising a first sublayer containing a metal complex of formula (II) and a second sublayer containing an organic matrix compound or an organic matrix compound (OMC) of formula (I), wherein the first sublayer is disposed closer to the anode layer and the second sublayer is disposed closer to the at least one light-emitting layer. Preferably, the metal complex in both sublayers, such as the first and second sublayers, is the same.

[0198] According to one embodiment, the organic electronic device may include a hole injection layer comprising a first sublayer containing a metal complex of formula (II) and a second sublayer containing an organic matrix compound (OMC) and a metal complex, wherein the first sublayer is disposed closer to the anode layer and the second sublayer is disposed closer to the at least one light-emitting layer.

[0199] According to one embodiment, the organic electronic device may include a hole injection layer comprising a first sublayer containing a metal complex of formula (II) and a second sublayer containing an organic matrix compound (OMC) according to the invention and a metal complex of formula (II), wherein the first sublayer is disposed closer to the anode layer and the second sublayer is disposed closer to the at least one light-emitting layer.

[0200] According to one embodiment of the present invention, the organic electronic device may include a hole injection layer comprising a first sublayer composed of a metal complex of formula (II) and a second sublayer containing an organic matrix compound (OMC) according to the present invention, wherein the first sublayer is disposed closer to the anode layer and the second sublayer is disposed closer to at least one light-emitting layer.

[0201] In the context of this specification, the term "consistently of..." particularly means and / or includes a concentration of ≥90% (volume / volume), more preferably ≥95% (volume / volume), and most preferably ≥99% (volume / volume). According to one embodiment of the invention, the organic electronic device may include a hole injection layer comprising a first sublayer composed of a metal complex of formula (II) and a second sublayer containing an organic matrix compound (OMC) according to the invention, wherein the first sublayer is disposed closer to the anode layer and the second sublayer is disposed closer to at least one light-emitting layer, wherein in formula (II), M is selected from Li, Na, K, Cs, Mg, Mn, Cu, Zn, Ag, Bi, and Mo, or Mg, Mn, Cu, Zn, Ag, Bi, and Mo, or Cu, Zn, Ag, or Bi.

[0202] According to one embodiment, the organic electronic device may include a hole injection layer comprising a first sublayer containing a metal complex of formula (II) and a second sublayer containing an organic matrix compound (OMC) according to the invention and a metal complex, wherein the first sublayer is disposed closer to the anode layer and the second sublayer is disposed closer to the at least one light-emitting layer.

[0203] Other layers

[0204] The organic electronic device according to the present invention may include layers other than those already mentioned above. Exemplary embodiments of each layer are described below: base The substrate can be any substrate commonly used in the manufacture of electronic devices, such as organic light-emitting diodes (OLEDs). If light is to be emitted through the substrate, it should be a transparent or translucent material, such as a glass substrate or a transparent plastic substrate. If light is to be emitted through the top surface, the substrate can be either a transparent or opaque material, such as a glass substrate, a plastic substrate, a metal substrate, or a silicon substrate.

[0205] Anode layer

[0206] The anode layer can be formed by deposition or sputtering of a material used to form the anode layer. The material used to form the anode layer can be a high work function material to facilitate hole injection. The anode material can also be selected from low work function materials (i.e., aluminum). The anode layer 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 layer. The anode layer can also be formed using a metal, typically silver (Ag), gold (Au), or a metal alloy.

[0207] Hole transport layer

[0208] According to one embodiment, the organic electronic device further includes a hole transport layer, wherein the hole transport layer is disposed between a hole injection layer and at least one light-emitting layer.

[0209] According to one embodiment, the organic electronic device may further include a hole transport layer, wherein the hole transport layer may be disposed between a hole injection layer and at least one light-emitting layer.

[0210] According to one embodiment, the hole transport layer comprises an organic matrix compound (OMC) according to the invention, preferably, the organic matrix compound (OMC) in the hole injection layer and the hole transport layer are selected to be the same.

[0211] According to one embodiment, the organic electronic device may include a hole transport layer, wherein the hole transport layer comprises the organic matrix compound or an organic matrix compound of formula (I), preferably, the organic matrix compound or the organic matrix compound of formula (I) in the hole injection layer and the hole transport layer may be the same.

[0212] According to one embodiment, the hole injection layer and the hole transport layer comprise an organic matrix compound (OMC) of formula (I), and the at least one light-emitting layer comprises a photoluminescent matrix compound (EMC) of formula (I), wherein in formula (I), Ar 3 The same functional groups were selected.

[0213] According to one embodiment, the hole injection layer and the hole transport layer comprise an organic matrix compound (OMC) of formula (I), and the at least one light-emitting layer comprises a photoluminescent matrix compound (EMC) of formula (I), wherein in formula (I), Ar 3 The group was chosen to be anthracene.

[0214] According to another embodiment, the organic electronic device may include a hole transport layer, wherein the hole transport layer may contain an organic matrix compound or an organic matrix compound of formula (I); wherein the organic matrix compound or the organic matrix compound of formula (I) in the hole injection layer and the hole transport layer is selected to be the same.

[0215] According to one embodiment, the hole transport layer may comprise an organic matrix compound or an organic matrix compound of formula (I); wherein the organic matrix compound or the organic matrix compound of formula (I) may be free of heteroatoms that are not part of an aromatic ring and / or a part of an unsaturated 7-membered ring, preferably the organic matrix compound or the organic matrix compound of formula (I) may be free of N atoms except for N atoms that are part of an aromatic ring or a part of an unsaturated 7-membered ring.

[0216] According to one embodiment, the hole transport layer may comprise an organic matrix compound or an organic matrix compound of formula (I); wherein the organic matrix compound or the organic matrix compound of formula (I) in the hole injection layer and the hole transport layer is selected to be the same, and the organic matrix compound or the organic matrix compound of formula (I) comprises two carbazole groups, at least one dibenzofuran group, at least one dibenzothiophene group and / or at least one anthracene group.

[0217] According to one embodiment, the hole transport layer may comprise an organic matrix compound or an organic matrix compound of formula (I); wherein the organic matrix compound or the organic matrix compound of formula (I) in the hole injection layer and the hole transport layer is selected to be the same, and the organic matrix compound or the organic matrix compound of formula (I) comprises two carbazole groups, one to three dibenzofuran groups, one to three dibenzothiophene groups and / or one to two anthracene groups.

[0218] According to one embodiment, the hole transport layer may comprise an organic matrix compound or an organic matrix compound of formula (I); wherein the organic matrix compound or the organic matrix compound of formula (I) in the hole injection layer and the hole transport layer is selected to be the same, and wherein for the organic matrix compound according to formula (I): - Ar 3 Options are available from D1 to D15, with D1 to D6 being preferred: (D1) (D2) (D3) (D4) (D5) (D6); (D7) (D8) (D9) (D10); (D11) (D12) (D13) (D14) (D15).

[0219] According to one implementation, Ar 1 Selectable from D7 to D13. Ar 2 Options are available from D1 to D6 or D7 to D13. Ar 4 Options are available from D1 to D6 or D7 to D13. Ar 5 Options are available from D1 to D6 or D7 to D13. Ar 6 Selectable from D7 to D13.

[0220] According to one implementation, in formula (I), Ar 3 The group is selected from anthracene, carbazole, dibenzothiophene and / or dibenzofuran.

[0221] According to one implementation, in formula (I), Ar 3 The group was chosen to be anthracene.

[0222] According to one implementation, in formula (I), Ar 3 The group is selected from carbazole, dibenzothiophene and / or dibenzofuran.

[0223] According to one embodiment, the hole transport layer may comprise an organic matrix compound or an organic matrix compound of formula (I); the organic matrix compound or the organic matrix compound of formula (I) in the hole injection layer and the hole transport layer is selected to be the same, and the organic matrix compound or the organic matrix compound of formula (I) may be selected from F1 to F13: (F1) (F2) (F3) (F4) (F5) (F6) (F7) (F8) (F9) (F10) (F11) (F12) (F13).

[0224] The hole transport layer may not include HTM014, HTM081, HTM163, HTM222, EL-301, HTM226, HTM355, HTM133, HTM334, HTM604, and EL-22T. Abbreviations represent the manufacturer's name, such as Merck or Lumtec.

[0225] The hole transport layer may not contain: N,N'-bis(naphthyl-1-yl)-N,N'-bis(phenyl)-9,9-dimethylfluorene, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-9,9-dimethylfluorene, N,N'-bis(naphthyl-1-yl)-N,N'-bis(phenyl)-9,9-dimethylfluorene, N,N'-bis(naphthyl-1-yl)-N,N'-bis(phenyl)-2,2-dimethylbenzidine, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-9,9-spirodifluorene, 2,2',7,7'-tetra(N,N-diphenylamino)-9,9'-spirodifluorene, N,N'-bis(naphthyl-1-yl) N,N'-bis(phenyl)-benzidine, N,N'-bis(naphthyl-2-yl)-N,N'-bis(phenyl)-benzidine, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-benzidine, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-9,9-dimethylfluorene, N,N'-bis(naphthyl-1-yl)-N,N'-bis(phenyl)-9,9-spirodifluorene, di-[4-(N,N-xylyl-amino)-phenyl]cyclohexane, 2,2',7,7'-tetra(N,N-xylyl)amino-spirodifluorene, 9,9-bis[4-(N,N-bis-biphenyl-4-yl-amino)phenyl]-9H -fluorene, 2,2',7,7'-tetratetra(N,N-naphthyl(phenyl)-amino]-9,9'-spirodifluorene, 2,7-bis(N,N-bis(9,9-spiro-difluorene-2-yl)-amino]-9,9'-spirodifluorene, 2,2'-bis(N,N-bis(biphenyl-4-yl)amino]-9,9'-spirodifluorene, N,N'-bis(phenanthrene-9-yl)-N,N'-bis(phenyl)-benzidine, N,N,N',N'-tetratetra(naphthyl-2-yl)-benzidine, 2,2'-bis(N,N-di-phenyl-amino)-9,9-spirodifluorene, 9,9-bis[4-(N,N-bis-naphthyl-2-yl-amino)phenyl]-9H-fluorene, 9,9-bis[4 -(N,N'-bis-naphthyl-2-yl-N,N'-bis-phenyl-amino)-phenyl]-9H-fluorene, titanium phthalocyanine, copper phthalocyanine, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl 4,4'4''-tris(N-3-methylphenyl-N-phenyl-amino)triphenylamine, 4,4',4''-tris(N-(2-naphthyl)-N-phenyl-amino)triphenylamine, 4,4',4''-tris(N-(1-naphthyl)-N-phenyl-amino)triphenylamine, 4,4',4''-tris(N,N-diphenyl-amino)triphenylamine, pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarboxynitrile, N,N,N',N'-Tetra(4-methoxyphenyl)benzidine, HTM014, HTM081, HTM163, HTM222, EL-301, HTM226, HTM355, HTM133, HTM334, HTM604, and EL-22T. The abbreviations represent the manufacturer's name, such as those used by Merck or Lumtec.

[0226] The hole transport layer (HTL) can be formed on the HIL by vacuum deposition, spin coating, slot die coating, printing, casting, Langmuir-Blodgett (LB) deposition, etc. When forming the HTL by vacuum deposition or spin coating, the conditions used for deposition and coating can be similar to those used for forming the HIL. However, the conditions used for vacuum or solution deposition can vary depending on the compound used to form the HTL.

[0227] 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, even more preferably about 20 nm to about 190 nm, even more preferably about 40 nm to about 180 nm, even more preferably about 60 nm to about 170 nm, even more preferably about 80 nm to about 200 nm, even more preferably about 100 nm to about 180 nm, even more preferably about 120 nm to about 170 nm.

[0228] When the thickness of the HTL is within this range, the HTL can have excellent hole transport characteristics without causing substantial damage to the operating voltage.

[0229] Electron blocking layer

[0230] The function of the electron blocking layer (EBL) is to prevent electrons from moving from the light-emitting layer to the hole transport layer, thereby confining electrons within the light-emitting layer. This can improve efficiency, operating voltage, and / or lifetime.

[0231] If the electron blocking layer has a high triplet energy level, it can also be described as a triplet control layer.

[0232] If a phosphorescent green or phosphorescent blue emitting layer is used, the function of the triplet control layer is to reduce triplet quenching. This allows for higher luminous efficiency of the phosphorescent emitting layer. The triplet control layer can be selected from triarylamine compounds whose triplet energy levels are higher than those of the phosphorescent emitters in adjacent emitting layers.

[0233] The thickness of the electron blocking layer can be selected between 2 nm and 20 nm.

[0234] Emissive Layer (EML)

[0235] According to one embodiment, the organic electronic device of the present invention includes a first light-emitting layer and a second light-emitting layer, wherein the first light-emitting layer and the second light-emitting layer are disposed between the hole injection layer and the cathode layer. Other light-emitting layers may be disposed between the second light-emitting layer and the cathode layer.

[0236] At least one luminescent layer (EML) can be formed on HTL or EBL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When forming at least one EML using vacuum deposition or spin coating, the conditions for deposition and coating can be similar to those for forming HIL. However, the conditions for deposition and coating can vary depending on the compound used to form at least one EML.

[0237] It may be specified that at least one luminescent layer does not contain an organic matrix compound of formula (I).

[0238] At least one light-emitting layer (EML) may be formed by a combination of a light-emitting matrix compound (EMC) and a light-emitting dopant.

[0239] The luminescent dopant can be a phosphorescent or fluorescent luminescent material. Phosphorescent luminescent materials and those emitting light via thermally activated delayed fluorescence (TADF) are preferred due to their high efficiency. The luminescent material can be a small molecule or a polymer.

[0240] Examples of red luminescent dopants include PtOEP, Ir(piq)3, and Btp2Ir(acac), but are not limited to these. These compounds are phosphorescent; however, red fluorescent dopants can also be used.

[0241] Examples of phosphorescent green luminescent dopants are Ir(ppy)3 (ppy = phenylpyridine), Ir(ppy)2(acac), and Ir(mpyp)3.

[0242] Examples of phosphorescent blue emitting electron dopants are F₂Irpic, (F₂ppy)₂Ir(tmd), Ir(dfppz)₃, and terfluorene. Examples of fluorescent blue emitting electron dopants are 4,4'-bis(4-diphenylaminostyryl)biphenyl (DPAVBi) and 2,5,8,11-tetra-tert-butylperylene (TBPe).

[0243] The amount of luminescent dopant can range from about 0.01 to about 50 parts by weight per 100 parts by weight of the main body. Alternatively, the luminescent layer can be composed of a luminescent polymer.

[0244] According to one embodiment, the organic electronic device may include at least one light-emitting layer, wherein the at least one light-emitting layer may be disposed between a hole injection layer and a cathode layer. Preferably, the organic electronic device of the present invention includes a light-emitting layer, wherein the light-emitting layer is disposed between a hole injection layer and a cathode layer.

[0245] According to one embodiment, the organic electronic device includes at least one light-emitting layer and a hole transport layer, wherein the at least one light-emitting layer may be disposed between the hole transport layer and the cathode layer.

[0246] According to one embodiment, the organic electronic device includes a hole injection layer containing an organic matrix compound of formula (I), a hole transport layer containing an organic matrix compound of formula (I), and a light-emitting layer containing at least one light-emitting matrix compound of formula (I). Preferably, the organic matrix compound of formula (I) and the light-emitting matrix compound of formula (I) are selected to be different.

[0247] According to one embodiment, the luminescent matrix compound or the luminescent matrix compound of formula (I) comprises two carbazole groups, at least one dibenzofuran group, at least one dibenzothiophene group and / or at least one anthracene group.

[0248] According to one embodiment, the luminescent matrix compound or the luminescent matrix compound of formula (I) comprises two carbazole groups, one to three dibenzofuran groups, one to three dibenzothiophene groups and / or one to two anthracene groups.

[0249] According to one embodiment, the at least one light-emitting layer may comprise a light-emitting matrix compound or a light-emitting matrix compound of formula (I); wherein for the light-emitting matrix compound of formula (I): - Ar 3 Options are available from D1 to D15, with D1 to D6 being preferred: (D1) (D2) (D3) (D4) (D5) (D6); (D7) (D8) (D9) (D10); (D11) (D12) (D13) (D14) (D15).

[0250] According to one implementation, Ar 1 Selectable from D7 to D13. Ar 2 Options are available from D1 to D6 or D7 to D13. Ar 4 Options are available from D1 to D6 or D7 to D13. Ar 5 Options are available from D1 to D6 or D7 to D13. Ar 6 Selectable from D7 to D13.

[0251] According to one embodiment, the at least one light-emitting layer may comprise a light-emitting matrix compound or a light-emitting matrix compound of formula (I); wherein for the light-emitting matrix compound of formula (I): Ar 3 Options are available from D1 to D15, with D1 to D6 being preferred: (D1) (D2) (D3) (D4) (D5) (D6); (D7) (D8) (D9) (D10); (D11) (D12) (D13) (D14) (D15); Ar 1 When m>0 and k>0, the options are from D7 to D15, or when k>0 and m=0, the options are from D7 to D15, or when k>1, the options are from D1 to D6. Ar 2 When m>0 and k>0, the options are D1 to D6; or when m>0 and k=0, the options are D7 to D15. Ar 4 When q>0, the options are D1 to D6, or when q=0 and r>0, the options are D1 to D6; or when q and r=0, the options are D7 to D15. Ar 5 When q>0 and r>0, the options are D1 to D6, or when q>0 and r=0, the options are D7 to D15. Ar 6When r>0 and q>0, the options are from D7 to D15, or when r>0 and q=0, the options are from D7 to D15, or when r>1, the options are from D1 to D6.

[0252] According to one embodiment, the luminescent matrix compound or the luminescent matrix compound of formula (I) may contain anthracene groups, or Ar... 3 Anthracene can be selected.

[0253] According to one embodiment, the luminescent matrix compound or the luminescent matrix compound of formula (I) may be selected from F1 to F13: (F1) (F2) (F3) (F4) (F5) (F6) (F7) (F8) (F9) (F10) (F11) (F12) (F13).

[0254] According to one embodiment, the luminescent matrix compound or the luminescent matrix compound of formula (I) may be selected from F1 to F11, and preferably from F2 to F6.

[0255] The thickness of the at least one EML can be from about 10 nm to about 100 nm, for example, from about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML can have excellent luminescence without causing substantial damage to the operating voltage.

[0256] Hole blocking layer (HBL)

[0257] A hole blocking layer (HBL) can be formed on at least one EML using methods such as vacuum deposition, spin coating, slot die coating, printing, casting, or LB deposition to prevent holes from diffusing into the ETL. When the at least one EML contains a phosphorescent dopant, the HBL may also have a triplet exciton blocking function.

[0258] The HBL can also be referred to as auxiliary ETL or a-ETL.

[0259] When forming HBLs using vacuum deposition or spin coating, the conditions for deposition and coating can be similar to those for forming HILs. However, the conditions for deposition and coating can vary depending on the compound used to form the HBL. Generally, any compound used to form HBLs can be used. Examples of compounds used to form HBLs include diazole derivatives, triazole derivatives, phenanthrene-rholine derivatives, and triazine derivatives.

[0260] The thickness of the HBL can range from about 5 nm to about 100 nm, for example, from about 10 nm to about 30 nm. When the thickness of the HBL is within this range, the HBL can have excellent hole blocking properties without causing substantial damage to the operating voltage.

[0261] Electron Transport Layer (ETL)

[0262] The organic electronic device according to the present invention may further include an electron transport layer (ETL).

[0263] According to another embodiment of the invention, the electron transport layer may further comprise an azazine compound, preferably a triazine compound.

[0264] In one embodiment, the electron transport layer may further comprise a dopant selected from alkali metal organocomplexes, preferably LiQ.

[0265] The thickness of the EIL can 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 EIL is within this range, the EIL can have satisfactory electron injection characteristics without causing substantial damage to the operating voltage.

[0266] According to another embodiment of the present invention, the organic electronic device may further include a hole-blocking layer and an electron transport layer, wherein the hole-blocking layer and the electron transport layer comprise an azazine compound. Preferably, the azazine compound is a triazine compound.

[0267] Electron Injection Layer (EIL)

[0268] An optional electron transport layer (EIL) that facilitates electron injection from the cathode can be formed on the ETL, preferably directly on the electron transport layer. Examples of materials used to form the EIL include lithium 8-hydroxyquinoline (LiQ), LiF, NaCl, CsF, Li₂O, BaO, Ca, Ba, Yb, and Mg, which are 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.

[0269] The thickness of the EIL can range from about 0.1 nm to about 10 nm, for example, from about 0.5 nm to about 9 nm. When the thickness of the EIL is within this range, the EIL can have satisfactory electron injection characteristics without causing substantial damage to the operating voltage.

[0270] cathode layer

[0271] A cathode layer is formed on the ETL or optionally the EIL. The cathode layer may be formed of a metal, alloy, conductive compound, or a mixture thereof. The cathode layer 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 layer may be formed of a transparent conductive oxide such as ITO or IZO.

[0272] The thickness of the cathode layer can 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 can be transparent or translucent even if it is formed of metal or metal alloy.

[0273] It should be understood that the cathode layer is not part of the electron injection layer or the electron transport layer.

[0274] Organic light-emitting diode (OLED)

[0275] The organic electronic device according to the present invention can be a light-emitting device or a display device.

[0276] According to one aspect of the present invention, an organic light-emitting diode (OLED) is provided, the OLED comprising: a substrate; an anode layer formed on the substrate; a hole injection layer comprising an organic matrix compound or an organic matrix compound of formula (I) and a metal complex of formula (II); a hole transport layer; at least one light-emitting layer comprising at least one light-emitting matrix compound or a light-emitting matrix compound of formula (I); an electron transport layer; and a cathode layer.

[0277] According to another aspect of the present invention, an organic electronic device is provided, the organic electronic device comprising an anode layer, a cathode layer, at least one light-emitting layer (EML) and at least one hole injection layer (HIL), wherein the hole injection layer is disposed between the anode layer and the at least one light-emitting layer, or the hole injection layer is in direct contact with the anode layer.

[0278] According to another aspect of the present invention, an OLED is provided, the OLED comprising: a substrate; an anode layer formed on the substrate; a hole injection layer of the present invention, the hole injection layer comprising a first sublayer and a second sublayer; a hole transport layer; at least one light-emitting layer; a hole blocking layer; an electron transport layer; an electron injection layer; and a cathode layer. The first sub-layer is arranged adjacent to the anode layer, and the second sub-layer is arranged adjacent to the hole transport layer. The first sublayer comprises or is composed of a metal complex of formula (II), and the second sublayer comprises or is composed of an organic matrix compound of formula (I).

[0279] According to another aspect of the present invention, an OLED is provided, the OLED comprising: a substrate; an anode layer formed on the substrate; a hole injection layer comprising an organic matrix compound or an organic matrix compound of formula (I) and a metal complex of formula (II); a hole transport layer; an electron blocking layer; at least one light-emitting layer; a hole blocking layer; an electron transport layer; and a cathode layer.

[0280] According to another aspect of the present invention, an OLED is provided, the OLED comprising: a substrate; an anode layer formed on the substrate; a hole injection layer of the present invention, the hole injection layer comprising a first sublayer and a second sublayer; a hole transport layer; an electron blocking layer; a light-emitting layer; a hole blocking layer; an electron transport layer; an electron injection layer; and a cathode layer. The first sub-layer is arranged adjacent to the anode layer, and the second sub-layer is arranged adjacent to the hole transport layer. The first sublayer comprises or is composed of a metal complex of formula (II), and the second sublayer comprises or is composed of an organic matrix compound of formula (I).

[0281] According to another aspect of the present invention, an OLED is provided, the OLED comprising: a substrate; an anode layer formed on the substrate; a hole injection layer comprising an organic matrix compound or an organic matrix compound of formula (I) and a metal complex of formula (II); a hole transport layer; an electron blocking layer; at least one light-emitting layer; a hole blocking layer; an electron transport layer; an electron injection layer; and a cathode layer.

[0282] According to another aspect of the present invention, an OLED is provided, the OLED comprising: a substrate; an anode layer formed on the substrate; a hole injection layer of the present invention, the hole injection layer comprising a first sublayer and a second sublayer; a hole transport layer; an electron blocking layer; a light-emitting layer; a hole blocking layer; an electron transport layer; an electron injection layer; and a cathode layer. The first sub-layer is arranged adjacent to the anode layer, and the second sub-layer is arranged adjacent to the hole transport layer. The first sublayer comprises or is composed of a metal complex of formula (II), and the second sublayer comprises or is composed of an organic matrix compound of formula (I).

[0283] According to various embodiments of the present invention, OLED layers can be provided arranged between the aforementioned layers, on a substrate, or on a top electrode.

[0284] For example, according to Figure 2 The OLED can be formed by the following method, wherein on a substrate (110), an anode layer (120), a hole injection layer (130) comprising an organic matrix compound or an organic matrix compound of formula (I) and a metal complex of formula (II), a hole transport layer (140), an electron blocking layer (145), a light emitting layer (150), a hole blocking layer (155), an electron transport layer (160), an electron injection layer (180), and a cathode layer (190) are formed sequentially.

[0285] Manufacturing method

[0286] According to another aspect of the present invention, a method for manufacturing an organic electronic device is provided, the method using: - At least one sedimentary source, preferably two sedimentary sources, more preferably at least three sedimentary sources.

[0287] Suitable deposition methods include: - Deposition is performed via vacuum thermal evaporation; - Deposition via solution processing, preferably spin coating, printing, casting; and / or - Slit-type die coating.

[0288] According to various embodiments of the present invention, a method is provided, the method using: - A first deposition source to release an organic matrix compound (OMC) according to formula (I) of the invention, and - Second deposition source, releasing metal complex of type (II).

[0289] The method includes the step of forming a hole injection layer; wherein, for organic light-emitting diodes (OLEDs): - The cavity injection layer is formed by releasing an organic matrix compound (OMC) of formula (I) according to the invention from the first deposition source and a metal complex of formula (II) from the second deposition source.

[0290] According to various embodiments of the present invention, the method may further include forming at least one layer selected from the following on the hole injection layer: forming a hole transport layer; forming a hole blocking layer; forming a light-emitting layer, the light-emitting layer may contain a light-emitting matrix compound (EMC) having formula (I); forming a hole blocking layer; forming an electron transport layer; and / or forming an electron injection layer; and / or forming a cathode layer.

[0291] According to various embodiments of the present invention, the method may further include the step of forming an organic light-emitting diode (OLED), wherein

[0292] - Form an anode layer on the substrate. - A hole injection layer is formed on the anode layer, the hole injection layer comprising an organic matrix compound (OMC) of formula (I) and a metal complex of formula (II). - A hole transport layer is formed on the hole injection layer, the hole injection layer comprising an organic matrix compound (OMC) of formula (I) and a metal complex of formula (II). - A light-emitting layer is formed on the hole transport layer, the light-emitting layer may contain a light-emitting matrix compound (EMC) having formula (I). - An electron transport layer is formed on the light-emitting layer, and optionally a hole blocking layer is formed on the light-emitting layer. - Finally, the cathode layer is formed. - An optional hole-blocking layer is formed sequentially between the hole injection layer and the light-emitting layer. - An optional electron injection layer is formed between the electron transport layer and the cathode layer.

[0293] According to various embodiments, the OLED may have the following layer structure, wherein the layers have the following order: An anode layer; a hole injection layer comprising an organic matrix compound (OMC) of formula (I) and a metal complex of formula (II); a hole transport layer; an optional electron blocking layer; a light-emitting layer comprising a light-emitting matrix compound (EMC) of formula (I); an optional hole blocking layer; an electron transport layer; an optional electron injection layer; and a cathode layer.

[0294] According to one embodiment, the organic electronic device of the present invention is formed by vacuum deposition of a hole injection layer and a cathode layer.

[0295] According to another aspect, an electronic device is provided, the electronic device comprising at least one organic light-emitting device according to any embodiment of the present application, preferably, the electronic device comprising an organic light-emitting diode as described in one of the embodiments of the present application. More preferably, the organic electronic device is a display device.

[0296] The embodiments are described in more detail below. However, this disclosure is not limited to the embodiments described below. Exemplary aspects will now be referred to in detail. Attached Figure Description

[0297] The aforementioned components in the described embodiments, as well as the claimed components and the components used according to the invention, have no particular exceptions in terms of their size, shape, material selection, and technical principles, and therefore selection criteria known in the relevant field can be applied without restriction.

[0298] Additional details, features, and advantages of the invention are disclosed in the dependent claims and the following description of the various drawings, which illustrate preferred embodiments of the invention by way of example. However, any embodiment is not necessarily representative of the full scope, and the scope of the invention should be interpreted with reference to the claims and this document. It should be understood that the foregoing general description and the following detailed description are merely exemplary and explanatory, and are intended to further explain the claimed invention.

[0299] Figure 1 This is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment of the present invention; Figure 2 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention; Figure 3 This is a schematic cross-sectional view of an OLED according to an exemplary embodiment of the present invention.

[0300] The embodiments are illustrated in more detail in the following drawings. However, this disclosure is not limited to the following drawings.

[0301] In this document, when a first element is referred to as being formed or disposed "on" or "to" a second element, the first element may be directly disposed on the second element, or one or more other elements may be disposed therebetween. When a first element is referred to as being formed or disposed "directly" on or "to" a second element, there are no other elements in between.

[0302] Figure 1This is a schematic cross-sectional view of an organic electronic device 100 according to an exemplary embodiment of the present invention. The organic electronic device 100 includes a substrate 110, an anode layer 120, and a hole injection layer (HIL) (130). The HIL 130 is disposed on the anode layer 120. A light-emitting layer (EML) 150 and a cathode layer 190 are disposed on the HIL 130.

[0303] Hole injection layer (HIL) 130 may include a first sublayer and a second sublayer, wherein the first sublayer is disposed on the anode and the second sublayer is disposed on the first sublayer. Photoactive layer (PAL) 170 is disposed on the second sublayer.

[0304] Figure 2 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) 100 according to an exemplary embodiment of the present invention. The OLED 100 includes a substrate 110, an anode layer 120, and a hole injection layer (HIL) (130). The HIL 130 is disposed on the anode layer 120. A hole transport layer (HTL) 140, an emissive layer (EML) 150, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180, and a cathode layer 190 are disposed on the HIL 130. Optionally, an electron transport layer stack (ETL) can be used instead of a single electron transport layer 160.

[0305] The hole injection layer (HIL) 130 may include a first sublayer and a second sublayer, wherein the first sublayer is disposed on the anode and the second sublayer is disposed on the first sublayer. The hole transport layer (HTL) 140 is disposed on the second sublayer.

[0306] Figure 3 This is a schematic cross-sectional view of an OLED 100 according to another exemplary embodiment of the present invention. Figure 2 and Figure 1 The difference is that, Figure 2 The OLED 100 includes an electron blocking layer (EBL) 145 and a hole blocking layer (HBL) 155.

[0307] refer to Figure 3 The OLED 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130, a hole transport layer (HTL) 140, an electron blocking layer (EBL) 145, an emissive layer (EML) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180, and a cathode layer 190.

[0308] although Figure 1 , Figure 2 and Figure 3Not shown, but a sealing layer may also be formed on the cathode layer 190 to seal the organic electronic device 100. Furthermore, various other modifications may be applied thereto.

[0309] The embodiments are illustrated in more detail below. However, this disclosure is not limited to the following embodiments. Detailed Implementation

[0310] Furthermore, the present invention is illustrated by the following embodiments, which are merely exemplary and not restrictive.

[0311] Organic matrix compounds of formula (I), metal complexes of formula (II), and luminescent matrix compounds of formula (I) can be prepared as described in the literature.

[0312] Standard starting temperature

[0313] The standard onset temperature (T) was determined by loading 100 mg of an organic matrix compound into a VTE source. RO As a VTE source, use point sources of organic materials supplied by companies such as Kurt J. Lesker Company (www.lesker.com) or CreaPhys GmbH (http: / / www.creaphys.com). In less than 10 -5 The VTE source was heated at a constant rate of 15 K / min under a pressure of millibars, and the internal temperature of the VTE source was measured using thermocouples. Evaporation of the organic matrix compound was detected using a QCM detector, which detected the deposition of the organic matrix compound on a quartz crystal of the detector. The deposition rate on the quartz crystal was measured in Å / s. To determine the standard onset temperature, the deposition rate was plotted against the VTE source temperature. The standard onset is the temperature at which significant deposition occurs on the QCM detector. To obtain accurate results, the VTE source was heated and cooled three times, and only the results of the second and third runs were used to determine the standard onset temperature.

[0314] To achieve good control over the evaporation rate of the metal complex of formula (II), the standard starting temperature can be in the range of ≥110°C to ≤300°C, preferably ≥115°C to ≤290°C. If the standard starting temperature is too low, evaporation may be too rapid and therefore difficult to control. If the standard starting temperature is too high, the evaporation rate may be too low, which may result in low cycle time and / or decomposition of the metal complex of formula (II) in the VTE source due to prolonged exposure to high temperatures.

[0315] To achieve good control over the evaporation rate of the organic matrix compound and / or luminescent matrix compound of the present invention, the standard starting temperature can be in the range of 120°C to 300°C. If the standard starting temperature is too low, evaporation may be too rapid and therefore difficult to control. If the standard starting temperature is too high, the evaporation rate may be too low, resulting in a low cycle time.

[0316] The standard onset temperature is an indirect measure of a compound's volatility. The higher the standard onset temperature, the lower the compound's volatility.

[0317] HOMO and LUMO

[0318] The HOMO and LUMO levels were calculated using the package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). The calculations were performed by applying the hybrid functional B3LYP with 6-31G in the gas phase. A basis set is used to determine the optimized geometry of the molecular structure, as well as the HOMO and LUMO energy levels. If more than one conformation is feasible, the conformation with the lowest total energy can be selected. The HOMO and LUMO energy levels are recorded in electron volts (eV).

[0319] General process for manufacturing OLEDs, including a hole injection layer and a light-emitting layer containing a blue phosphor.

[0320] For OLEDs, referring to Examples 1 to 11 and Comparative Examples 1 to 3 in Tables 4 and 5, a 15 Ω / cm OLED with 90nm ITO was used. 2 A glass substrate (available from Corning Co.) was cut into 50 mm × 50 mm × 0.7 mm pieces, ultrasonically cleaned with isopropanol for 5 minutes, ultrasonically cleaned with pure water for 5 minutes, and then cleaned with UV ozone for 30 minutes to prepare the anode layer.

[0321] Then, 70 vol% of the organic matrix compound and 30 vol% of the metal complex were vacuum co-deposited on the anode layer to form a hole injection layer (HIL) with a thickness of 10 nm. The composition of the hole injection layer is shown in Tables 4 and 5. In Comparative Examples 1 to 3, 70 vol% of the organic matrix compound and 30 vol% of HAT-CN were vacuum co-deposited on the anode layer to form an HIL with a thickness of 10 nm.

[0322] Then, an organic matrix compound was vacuum deposited onto the HIL to form an HTL with a thickness of 128 nm. The organic matrix compound in the HTL was selected to be the same as the organic matrix compound in the HIL. The organic matrix compounds are shown in Tables 4 and 5.

[0323] Then, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1''-terphenyl]-4-amine (CAS 1198399-61-9) was vacuum deposited on the HTL to form an electron blocking layer (EBL) with a thickness of 5 nm.

[0324] Then, 97 vol% EMC-6 as the luminescent matrix compound and 3 vol% BD200 (Sun Fine Chemicals, Korea) as the fluorescent blue luminescent dopant were deposited on the EBL to form a blue luminescent EML with a thickness of 20 nm.

[0325] Then, a hole-blocking layer with a thickness of 5 nm is formed by depositing 2-(3'-(9,9-dimethyl-9H-fluorene-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine on the light-emitting layer EML.

[0326] Then, an electron transport layer with a thickness of 31 nm 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)naphth-1-yl)-[1,1'-biphenyl]-4-carboxynitrile and 50 wt% LiQ.

[0327] Then in 10 -7 Al is evaporated at a rate of 0.01 to 1 Å / s under millibars to form a cathode layer with a thickness of 100 nm on the electron transport layer.

[0328] The OLED stack is protected from environmental conditions by encapsulating the device with a glass slide. This creates a cavity that may include getter material for further protection.

[0329] General process for manufacturing OLEDs, including a hole injection layer and a light-emitting layer containing a green phosphorescent emitter.

[0330] For OLEDs, referring to Examples 12 and 13 and Comparative Examples 4 and 5 in Table 5, a 15 Ω / cm OLED with 90 nm ITO was used. 2 A glass substrate (available from Corning Co.) was cut into 50 mm × 50 mm × 0.7 mm pieces, ultrasonically cleaned with isopropanol for 5 minutes, ultrasonically cleaned with pure water for 5 minutes, and then cleaned with UV ozone for 30 minutes to prepare the anode layer.

[0331] Then, 70 vol% of the organic matrix compound and 30 vol% of the metal complex were vacuum co-deposited on the anode layer to form a hole injection layer (HIL) with a thickness of 10 nm. The composition of the hole injection layer is shown in Table 6. In Comparative Examples 4 and 5, 70 vol% of the organic matrix compound and 30 vol% of HAT-CN were vacuum co-deposited on the anode layer to form an HIL with a thickness of 10 nm.

[0332] Then, an organic matrix compound was vacuum deposited onto the HIL to form an HTL with a thickness of 165 nm. The organic matrix compound in the HTL was selected to be the same as the organic matrix compound in the HIL. The organic matrix compounds are shown in Table 6.

[0333] Then, 90 volume % GH-1 and 10 volume % GD-1 were vacuum co-deposited on the HTL to form a green emitting layer with a thickness of 40 nm. GH-1 contains EMC-4 and GET-1 in a molar ratio of 1:1. The formulas for GET-1 and GD-1 are as follows: (GET-1) (GD-1).

[0334] Then, a hole-blocking layer with a thickness of 25 nm is formed by depositing 2,4-diphenyl-6-(3'-(triphenyl-2-yl)-[1,1'-biphenyl]-3-yl)-1,3,5-triazine on the light-emitting layer EML.

[0335] Then, an electron transport layer with a thickness of 10 nm is formed on the hole blocking layer by depositing 99 vol% 3-phenyl-3H-benzo[b]dinaphtho[2,1-d:1',2'-f]3-phosphine oxide and 1 vol% Yb.

[0336] Then, in 10 -7 Al is evaporated at a rate of 0.01 to 1 Å / s under millibars to form a cathode layer with a thickness of 100 nm on the electron transport layer.

[0337] By encapsulating the device with a glass slide, the OLED stack is protected from environmental conditions. This creates a cavity that may include getter material for further protection.

[0338] General process for manufacturing OLEDs including hole injection layers containing a first sublayer and a second sublayer

[0339] For OLEDs, referring to Examples 14 to 28 and Comparative Examples 6 to 11 in Table 7, a 15 Ω / cm OLED with 90 nm ITO was used. 2A glass substrate (available from Corning Co.) was cut into 50 mm × 50 mm × 0.7 mm pieces, ultrasonically cleaned with isopropanol for 5 minutes, ultrasonically cleaned with pure water for 5 minutes, and then cleaned with UV ozone for 30 minutes to prepare the anode layer.

[0340] Then, a hole injection layer comprising a first sublayer and a second sublayer is vacuum deposited on the anode layer. First, a metal complex is vacuum deposited on the anode layer to form a first sublayer with a thickness of 3 or 5 nm, see Table 7. In Comparative Examples 6 to 11, HAT-CN is vacuum deposited on the anode layer to form a first sublayer with a thickness of 3 or 5 nm, see Table 7.

[0341] Then, an organic matrix compound is vacuum deposited on the first sublayer to form a second sublayer with a thickness of 7 or 5 nm, see Table 7.

[0342] Then, an organic matrix compound is vacuum-deposited on the hole injection layer to form an HTL. The organic matrix compound in the HTL is selected to be the same as that in the HIL, see Table 7. The thickness is selected such that the total thickness of the second sublayer and the HTL reaches 128 nm.

[0343] Then, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1''-terphenyl]-4-amine (CAS 1198399-61-9) was vacuum deposited on the HTL to form an electron blocking layer (EBL) with a thickness of 5 nm.

[0344] Then, 97 vol% EMC-6 as the luminescent matrix compound and 3 vol% BD200 (Sun Fine Chemicals, Korea) as the fluorescent blue luminescent dopant were deposited on the EBL to form a blue luminescent EML with a thickness of 20 nm.

[0345] Then, a hole-blocking layer with a thickness of 5 nm is formed by depositing 2-(3'-(9,9-dimethyl-9H-fluorene-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine on the light-emitting layer EML.

[0346] Then, an electron transport layer with a thickness of 31 nm was formed by depositing 50 wt% 4'-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphth-1-yl)-[1,1'-biphenyl]-4-carboxynitrile and 50 wt% LiQ on the hole blocking layer.

[0347] Then, in 10 -7Al is evaporated at a rate of 0.01 to 1 Å / s under millibars to form a cathode layer with a thickness of 100 nm on the electron transport layer.

[0348] By encapsulating the device with a glass slide, the OLED stack is protected from environmental conditions. This creates a cavity that may include getter material for further protection.

[0349] To evaluate the performance of the embodiments of the present invention compared to the prior art, current efficiency was measured at 20°C. Using a Keithley 2635 source measurement unit, the current-voltage characteristics were determined by providing an operating voltage U (in V) and measuring the current flowing through the device under test (in mA). The voltage applied to the device varied in 0.1 V steps within the range of 0 V to 10 V. To protect the instrument from damage, the measurement was stopped at 10 V.

[0350] Technical effect

[0351] In order to investigate the usefulness of the stacks of the present invention, preferred materials were tested in view of their physical properties, see Tables 1 to 3.

[0352] Table 1 shows the HOMO levels and the standard onset temperature T0 of the organomatrix compounds of this invention, calculated using the program TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). RO .

[0353] Table 1: Chemical formulas and physical properties of organic matrix compounds

[0354] As shown in Table 1, the standard onset temperature of organic matrix compounds is applicable to the large-scale production of organic electronic devices.

[0355] Table 2 shows the standard onset temperature T of the metal complex of formula (II). RO .

[0356] Table 2: Metal complexes of formula (II)

[0357] As can be seen from Table 2, the standard onset temperature of the metal complex of formula (II) is suitable for the large-scale production of organic electronic devices.

[0358] Table 3 shows the HOMO level and the standard onset temperature T0 of the luminescent matrix compound of the present invention, calculated using the program TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). RO .

[0359] Table 3: Chemical formulas and physical properties of luminescent matrix compounds

[0360] As shown in Table 3, the standard onset temperature of the luminescent matrix compound is suitable for the large-scale production of organic electronic devices.

[0361] Table 4 shows the OLED performance at 10 mA / cm², including a hole injection layer containing 70 vol% organic matrix compound OMC-10 and 30 vol% metal complex of formula (II) and an emitting layer containing 97 vol% emitting matrix compound EMC-6 and 3 vol% blue phosphor dopant. 2 The operating voltage is specified. The HOMO level of OMC-10 is -5.30 eV. The HOMO level of the luminescent matrix compound EMC-6 is -5.13 eV.

[0362] The shift between the HOMO energy level of the luminescent matrix compound and the HOMO energy level of the organic matrix compound is 0.17 eV.

[0363] Table 4: Performance of OLEDs containing fluorescent blue emitting diodes and emitting diode matrix compound EMC-6

[0364] In Comparative Example 1, the existing material HAT-CN was used at a concentration of 30% by volume. HAT-CN has the following formula: (HAT-CN).

[0365] The HAT-CN has a HOMO of -8.83 eV. It operates at voltages exceeding 10 V.

[0366] In Example 1, the hole injection layer contains Cu(TFSI)₂ as a metal complex. The operating voltage is significantly improved to 6.9 V.

[0367] In Example 2, the hole injection layer comprises a different Cu(II) complex, namely MC-24. Compared to Example 1, the TFSI ligand is replaced by an amide ligand comprising a trifluoromethyl group and a substituted aryl group. The operating voltage is further improved to 6.3 V.

[0368] In Example 3, the hole injection layer comprises MC-6. Compared to Example 1, Cu(II) cations are replaced by Mn(II) cations. Compared to Example 1, the operating voltage is improved from 6.9 V to 5.3 V.

[0369] In Example 4, the hole injection layer comprises a Mg complex. Compared to Example 2, Cu(II) cations are replaced by Mg(II) cations. The operating voltage is improved from 6.3 V to 5.4 V.

[0370] In Example 5, the hole injection layer comprises a Zn(II) complex. Compared to Example 4, the Mg(II) cation is replaced by a Zn(II) cation, and the amide ligand is replaced by a ligand containing an N-aryl group. The operating voltage remains within the range acceptable for large-scale production.

[0371] Table 5 shows the performance of OLED at 10 mA / cm². 2 The OLED, operating at a voltage specified below, comprises a fluorescent blue emitting element, a hole injection layer containing 70 vol% organic matrix compound and 30 vol% metal complex of formula (II), and an emitting layer containing 97 vol% emitting element matrix compound EMC-6 and 3 vol% fluorescent blue emitting element.

[0372] The HOMO level of the luminescent matrix compound EMC-6 is -5.13 eV.

[0373] Table 5: Performance of OLEDs containing fluorescent blue emitting diodes and emitting diode matrix compound EMC-6

[0374] In Comparative Example 2, the hole injection layer comprises an organic matrix compound OMC-5 and 30 vol% HAT-CN. HAT-CN is free of metal complexes. OMC-5 contains anthracene groups. The HOMO level of OMC-5 is -5.10 eV. The HOMO level shift between the luminescent matrix compound and the organic matrix compound is -0.03 eV. The operating voltage exceeds 10 V.

[0375] In Comparative Example 3, the hole injection layer comprises an organic matrix compound OMC-13 and 30 vol% HAT-CN. OMC-13 contains three dibenzofuranyl groups. The HOMO level is -5.67 eV. The HOMO level shift between the luminescent matrix compound and the organic matrix compound is 0.54 eV. The operating voltage exceeds 10 V.

[0376] In Example 6, the hole injection layer comprises OMC-5 and the metal complex MC-29. The operating voltage is significantly reduced to 4.1 V.

[0377] In Example 7, the hole injection layer comprises OMC-6 and MC-29. OMC-6 comprises anthracene and dibenzofuranyl groups. The hole injection layer and the luminescent layer use the same compound. The HOMO level shift between the luminescent matrix compound and the organic matrix compound is 0 eV. The operating voltage remains constant at 4.1 V.

[0378] In Example 8, the hole injection layer comprised OMC-7 and MC-29. OMC-7 comprised anthracene and dibenzofuranyl groups. The HOMO level was -5.13 eV. The HOMO level shift between the luminescent matrix compound and the organic matrix compound was 0 eV. The operating voltage was slightly higher than in Example 7. However, compared to Comparative Examples 2 and 3, the operating voltage was significantly lower.

[0379] In Example 9, the hole injection layer comprised OMC-9 and MC-29. OMC-9 comprised dibenzo-acrylidine and carbazole groups. The HOMO level was -5.28 eV. The HOMO level shift between the luminescent matrix compound and the organic matrix compound increased to 0.15 eV. The operating voltage was slightly higher than in Example 8. However, compared to Comparative Examples 2 and 3, the operating voltage was significantly lower.

[0380] In Example 10, the hole injection layer comprised OMC-10 and MC-29. OMC-10 contained two carbazole groups. The HOMO level was -5.30 eV. The HOMO level shift between the luminescent matrix compound and the organic matrix compound increased to 0.17 eV. Compared to Comparative Examples 2 and 3, the operating voltage was still significantly reduced.

[0381] In Example 11, the hole injection layer comprised OMC-13 and MC-29. OMC-13 comprised three dibenzofuranyl groups. The HOMO level was -5.67 eV. The HOMO level shift between the luminescent matrix compound and the organic matrix compound was further increased to 0.54 eV. The operating voltage was slightly higher than in Example 10. However, compared to Comparative Examples 2 and 3, the operating voltage was significantly lower.

[0382] Table 6 shows the performance of OLED at 10 mA / cm². 2 The OLED, operating at a specified voltage, comprises a phosphorescent green emitter, a hole injection layer containing an organic matrix compound and a metal complex of formula (II) at 30 vol% volume, and an emissive layer comprising 70 vol% volume of a composition containing EMC-4 and GET-1 in a molar ratio of 1:1 and 30 vol% volume of phosphorescent green emitter GD-1. If the emissive layer comprises a composition of two or more emitter matrix compounds, an emitter matrix compound with a HOMO energy level closer to the vacuum energy level is considered.

[0383] The HOMO level of the luminescent matrix compound EMC-4 is -5.09 eV. In contrast, the HOMO level of GET-1 is -5.69 eV.

[0384] Table 6: Performance of OLEDs Containing Phosphorescent Green Emitters

[0385] In Comparative Example 4, the hole injection layer comprises an organic matrix compound OMC-5 and 30 vol% HAT-CN. HAT-CN is free of metal complexes. OMC-5 contains anthracene groups. The HOMO level of OMC-5 is -5.10 eV. The HOMO level shift between the luminescent matrix compound and the organic matrix compound is 0.01 eV. The operating voltage exceeds 10 V.

[0386] In Example 12, the hole injection layer comprises OMC-5 and the metal complex MC-29. The operating voltage is significantly reduced to 4.1 V.

[0387] In Comparative Example 5, the hole injection layer comprises an organic matrix compound OMC-10 and 30 vol% HAT-CN. OMC-10 contains two carbazole groups. The HOMO level of OMC-10 is -5.30 eV. The HOMO level shift between the luminescent matrix compound and the organic matrix compound is 0.21 eV. The operating voltage exceeds 10 V.

[0388] In Example 13, the hole injection layer comprises OMC-10 and the metal complex MC-29. The operating voltage is significantly reduced to 6.3 V.

[0389] Table 7 shows the performance of OLEDs including blue phosphors and hole injection layers at 10 mA / cm². 2 The operating voltage is specified below, wherein the hole injection layer comprises a first sublayer consisting of a metal complex of formula (II) and a second sublayer consisting of an organic matrix compound. The luminescent layer comprises 97 vol% luminescent matrix compound EMC-6 and 3 vol% fluorescent blue luminescent material.

[0390] In Comparative Example 6, the first sublayer contains HAT-CN as a prior art hole injection material, with a thickness of 3 nm. HAT-CN does not contain metal complexes. The second sublayer contains the organic matrix compound OMC-6. The HOMO level shift between the luminescent matrix compound and the organic matrix compound is -0.03 eV. The operating voltage exceeds 10 V.

[0391] In Comparative Example 7, the first sublayer contains HAT-CN, and the second sublayer contains the organic matrix compound OMC-7. The HOMO level shift between the luminescent matrix compound and the organic matrix compound is 0.15 eV. The operating voltage exceeds 10 V.

[0392] In Comparative Example 8, the first sublayer contains HAT-CN, and the second sublayer contains the organic matrix compound OMC-10. The HOMO level shift between the luminescent matrix compound and the organic matrix compound is 0.17 eV. The operating voltage exceeds 10 V.

[0393] In Example 14, the first sublayer comprised a metal complex MC-29 with a thickness of 3 nm. The second sublayer comprised an organic matrix compound OMC-6. The HOMO level shift between the luminescent matrix compound and the organic matrix compound was -0.03 eV. The operating voltage was 4.0 V, resulting in a significant improvement compared to Comparative Example 6.

[0394] In Examples 15 to 17, the first sublayer was the same as in Example 14. The second sublayer contained various organic matrix compounds whose HOMO energy levels were further away from the vacuum energy level than OMC-6. The HOMO energy level shift between the luminescent matrix compound and the organic matrix compound was in the range of 0 to 0.17 eV. Compared with Comparative Examples 6, 7, and 8, the operating voltage was significantly improved in all examples.

[0395] In Examples 18 to 20, the first sublayer comprised the metal complex MC-27. MC-27 differs from MC-29 in the metal cation and ligand, as shown in Table 2. The second sublayer comprised various organic matrix compounds. The HOMO energy level shift between the luminescent matrix compound and the organic matrix compound ranged from -0.03 to 0.15 eV. Compared to Comparative Examples 6, 7, and 8, the operating voltage was significantly improved in all examples.

[0396] In Example 21, the first sublayer comprises the metal complex MC-30. MC-30 differs from MC-29 in the metal cation and ligand, see Table 2. The second sublayer comprises OMC-7. The HOMO level shift between the luminescent matrix compound and the organic matrix compound is 0.15 eV. The operating voltage is 6.6 V, thus representing an improvement over Comparative Example 7.

[0397] In Comparative Examples 9 to 11, the first sublayer contained HAT-CN as a prior art hole injection material, with a thickness of 5 nm. The second sublayer contained various organic matrix compounds. The HOMO level shift between the luminescent matrix compound and the organic matrix compound ranged from -0.03 to 0.17 eV. The operating voltage exceeded 10 V.

[0398] In Example 22, the first sublayer comprised a metal complex MC-29 with a thickness of 5 nm. The second sublayer comprised an organic matrix compound OMC-6. The HOMO level shift between the luminescent matrix compound and the organic matrix compound was -0.03 eV. The operating voltage was 4.0 V, resulting in a significant improvement compared to Comparative Example 9. The performance was comparable to that of Example 14.

[0399] In Examples 23 to 25, the first sublayer was the same as in Example 22. The second sublayer contained various organic matrix compounds whose HOMO energy levels were further away from the vacuum energy level than OMC-6. The HOMO energy level shift between the luminescent matrix compound and the organic matrix compound was in the range of 0 to 0.17 eV. Compared with Comparative Examples 9, 10, and 11, the operating voltage was significantly improved in all examples.

[0400] In Examples 26 and 27, the first sublayer comprised the metal complex MC-27. MC-27 differs from MC-29 in the metal cation and ligand, see Table 2. The second sublayer comprised various organic matrix compounds. The HOMO level shift between the luminescent matrix compound and the organic matrix compound ranged from 0 to 0.15 eV. Compared to Comparative Examples 9, 10, and 11, the operating voltage was significantly improved in all examples.

[0401] In Example 28, the first sublayer comprises the metal complex MC-30. MC-30 differs from MC-29 in the metal cation and ligand, see Table 2. The second sublayer comprises OMC-7. The HOMO level shift between the luminescent matrix compound and the organic matrix compound is 0.15 eV. The operating voltage is 5.4 V, thus representing an improvement over Comparative Example 10.

[0402] In summary, significant improvements have been achieved in terms of operating voltage for OLEDs incorporating the hole injection layer according to the present invention.

[0403] Lowering the operating voltage can help reduce power consumption and improve battery life, especially in mobile devices.

[0404] Table 7: Performance of OLEDs including a hole injection layer (HIL), wherein the hole injection layer comprises a first sublayer and a second sublayer.

[0405] It is obvious that the device according to the invention exhibits much better performance than the comparative device.

[0406] The specific combinations of elements and features in the embodiments detailed above are merely exemplary; these teachings are also explicitly considered to be interchangeable and superseded by other teachings herein and in patents / applications incorporated by reference. As will be appreciated by those skilled in the art, variations, modifications, and other embodiments of the content described herein can be conceived by those of ordinary skill in the art without departing from the spirit and scope of the claimed invention. Therefore, the foregoing description is by way of example only and is not intended to be limiting. In the claims, the word “comprising” does not exclude other elements or steps, and the indefinite articles “a” or “an” do not exclude plural. The fact that specific measures are enumerated in dissimilar dependent claims does not imply that combinations of these measures cannot be used advantageously. The scope of the invention is defined by the claims and their equivalents. Furthermore, the reference numerals used in the description of the invention and the claims do not limit the scope of the claimed invention.

Claims

1. An organic electronic device, the organic electronic device comprising an anode layer, a cathode layer, at least one light-emitting layer (EML), and at least one hole injection layer (HIL), wherein the hole injection layer is disposed between the anode layer and the at least one light-emitting layer; wherein - The hole injection layer comprises an organic matrix compound (OMC) and a metal complex, wherein the metal complex has formula (II): (II), in M is a metal ion. n is the valence of M, where n is an integer from 1 to 4. L is a ligand; and - The at least one light-emitting layer comprises at least one photoluminescent matrix compound (EMC), wherein the HOMO energy level of the photoluminescent matrix compound (EMC) and the HOMO energy level of the organic matrix compound (OMC) satisfy the following equation: -0.24 eV < [HOMO level (EMC) – HOMO level (OMC)] ≤ 0.8 eV; The molecular weight Mw of the organic matrix compound (OMC) or the luminescent matrix compound (EMC) in the hole injection layer is ≥400 g / mol and ≤2000 g / mol.

2. An organic electronic device, the organic electronic device comprising an anode layer, a cathode layer, at least one light-emitting layer (EML), and at least one hole injection layer (HIL), wherein the hole injection layer is disposed between the anode layer and the at least one light-emitting layer, wherein - The hole injection layer comprises an organic matrix compound (OMC) and a metal complex, wherein - The organic matrix compound (OMC) and the luminescent matrix compound (EMC) have formula (I): (Ar 1 ) k ─(Ar 2 ) m ─On 3 ─(Ar 4 ) p ─(Ar 5 ) q ─(Ar 6 ) r (I), in k, m, q, and r are each independently 0, 1, or 2. p is 1, 2, or 3. Where 2 ≤ k+m+q+r+p ≤ 11, Ar 1 To Ar 6 Heterocycles independently selected from substituted or unsubstituted unsaturated 5- to 7-membered rings, substituted or unsubstituted C6 to C6 rings. 30 aryl or substituted or unsubstituted C3 to C 30 The rings are selected from: (i) heterocyclic rings with unsaturated 5 to 7-membered rings, (ii) aromatic heterocyclic rings with 5 to 6 members, (iii) non-heterocyclic rings with unsaturated 5 to 7-membered rings, and (iv) aromatic non-heterocyclic rings with 6-membered rings. The substituents are selected from: H, D, C1 to C. 12 Alkyl, unsubstituted C6 to C 18 Aryl, unsubstituted C3 to C 18 The heteroaryl group comprises a fused ring system containing 2 to 6 unsubstituted 5 to 7-membered rings, wherein the rings are selected from: unsaturated 5 to 7-membered heterocycles, 5 to 6-membered aromatic heterocycles, unsaturated 5 to 7-membered non-heterocycles, and 6-membered aromatic non-heterocycles. -The metal complex has formula (II): (II), in M is a metal ion. n is the valence of M, where n is an integer from 1 to 4. L is a ligand; Furthermore, the organic matrix compound (OMC) and the luminescent matrix compound (EMC) are selected to be the same or different; The molecular weight Mw of the organic matrix compound (OMC) or the luminescent matrix compound (EMC) in the hole injection layer is ≥400 g / mol and ≤2000 g / mol.

3. The organic electronic device according to claim 1 or 2, wherein the hole injection layer is non-luminescent.

4. The organic electronic device according to claim 1 or 2, wherein the hole injection layer is arranged adjacent to the anode layer or in direct contact with the anode layer.

5. The organic electronic device according to claim 1 or 2, wherein, when measured under the same conditions, the HOMO level of the organic matrix compound (OMC) is further from the vacuum level than the HOMO level of N4,N4'''-di(naphthyl-1-yl)-N4,N4'''-diphenyl-[1,1':4',1'':4'',1'''-tetraphenyl]-4,4'''-diamine.

6. The organic electronic device according to claim 1 or 2, wherein the organic matrix compound (OMC) satisfies the following formula: -7 eV < HOMO level (OMC) < -4.85 eV; where The HOMO level was calculated using the TURBOMOLE V6.5 package.

7. The organic electronic device according to claim 1 or 2, wherein the organic matrix compound (OMC) and the luminescent matrix compound (EMC) have formula (I): (Ar 1 ) k ─(Ar 2 ) m ─On 3 ─(Ar 4 ) p ─(Ar 5 ) q ─(Ar 6 ) r (I), in k, m, q, and r are each independently 0, 1, or 2. p is 1, 2, or 3. Where 2 ≤ k+m+q+r+p ≤ 11, Ar 1 To Ar 6 Independently selected from substituted or unsubstituted biphenylene groups, substituted or unsubstituted fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted terphenylene groups, substituted or unsubstituted tetraphenylene, substituted or unsubstituted benzo[b,f]-anthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthones, substituted or unsubstituted carbazole, substituted or unsubstituted azacycloheptatriene, substituted or unsubstituted dibenzo[b,f]azacycloheptatriene, 9,9'-spirodi[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanthones], substituted or unsubstituted 9,14 -dihydrodibenzo[2,3:6,7]azapyronetrien[4,5-b]indole, or a substituted or unsubstituted aromatic fused ring system comprising at least three substituted or unsubstituted aromatic rings selected from substituted or unsubstituted non-heterocyclic rings, substituted or unsubstituted heterocyclic 5-membered rings, substituted or unsubstituted 6-membered rings, or substituted or unsubstituted 7-membered rings, substituted or unsubstituted fluorene, or a fused ring system comprising 2 to 6 substituted or unsubstituted 5 to 7-membered rings, and the rings are selected from: (i) unsaturated 5 to 7-membered heterocyclic rings, (ii) 5 to 6-membered aromatic heterocyclic rings, (iii) unsaturated 5 to 7-membered non-heterocyclic rings, and (iv) 6-membered aromatic non-heterocyclic rings. The substituents are selected from: H, D, C1 to C. 12 Alkyl, unsubstituted C6 to C 18 Aryl, unsubstituted C3 to C 18 The heteroaryl group comprises a fused ring system containing 2 to 6 unsubstituted 5 to 7-membered rings, wherein the rings are selected from: unsaturated 5 to 7-membered heterocycles, 5 to 6-membered aromatic heterocycles, unsaturated 5 to 7-membered non-heterocycles, and 6-membered aromatic non-heterocycles. Furthermore, the organic matrix compound (OMC) and the luminescent matrix compound (EMC) are selected to be the same or different.

8. The organic electronic device according to claim 1 or 2, wherein M is selected from metal ions in which the corresponding metal has an electronegativity value of less than 2.4 according to Allen, alkali metals, alkaline earth metals, rare earth metals or transition metals, metals with an atomic weight ≥ 24 Da, or metals with an atomic weight ≥ 24 Da and an oxidation number ≥ 2.

9. The organic electronic device according to claim 1 or 2, wherein the molecular weight Mw of the metal complex is ≥287 g / mol and ≤2000 g / mol.

10. The organic electronic device according to claim 1 or 2, wherein L is selected from: - At least three carbon atoms or at least four carbon atoms, or - At least two oxygen atoms, or one oxygen atom and one nitrogen atom, two to four oxygen atoms, two to four oxygen atoms and zero to two nitrogen atoms, or - At least one or more groups selected from the following: halogen, F, CN, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy; or two or more groups selected from the following: halogen, F, CN, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy; at least one or more groups selected from the following: halogen, F, CN, substituted C1 to C6 alkyl, substituted C1 to C6 alkoxy; or two or more groups selected from the following: halogen, F, CN, perfluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkoxy; or one or more groups selected from the following: substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C6 alkyl; 12 aryl or substituted or unsubstituted C3 to C 12 Mixed aromatics, The substituents are selected from: D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkyl, partially deuterated or fully deuterated C1 to C6 alkoxy, COR 6 COOR 6 Halogen, F or CN; Where R 6 Selected from: C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkyl, partially deuterated or fully deuterated C1 to C6 alkoxy.

11. The organic electronic device according to claim 1 or 2, wherein the metal complex according to formula (II) is non-luminescent.

12. The organic electronic device according to claim 1 or 2, wherein the organic matrix compound (OMC) and the luminescent matrix compound (EMC) have formula (I): (Ar 1 ) k ─(Ar 2 ) m ─On 3 ─(Ar 4 ) p ─(Ar 5 ) q ─(Ar 6 ) r (I), in k, m, q, and r are each independently 0, 1, or 2. p is 1, 2, or 3. Where 2 ≤ k+m+q+r+p ≤ 11, Ar 1 To Ar 6 Heterocycles independently selected from substituted or unsubstituted unsaturated 5- to 7-membered rings, substituted or unsubstituted C6 to C6 rings. 30 Aryl, substituted or unsubstituted C3 to C 30 The rings are selected from: (i) heterocyclic rings with unsaturated 5 to 7-membered rings, (ii) aromatic heterocyclic rings with 5 to 6 members, (iii) non-heterocyclic rings with unsaturated 5 to 7-membered rings, and (iv) aromatic non-heterocyclic rings with 6-membered rings. Ar 2 When k=1, Ar 3 Ar 4 When q = 1, Ar 5 When r = 1: Independently selected from: heterocycles of unsaturated 5- to 7-membered rings, substituted or unsubstituted, C6 to C6 rings. 30 Aranediol, substituted or unsubstituted C3 to C4 30 Heteroarylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted terphenylene, substituted or unsubstituted tetraphenylene, substituted or unsubstituted benzo[a]anthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthone, substituted or unsubstituted carbazole, substituted or unsubstituted azaheptatriene, substituted or unsubstituted diphenylene Benzo[b,f]-heptacyclic hepttriene, 9,9'-spirobis[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanton], substituted or unsubstituted 9,14-dihydrodibenzo[2,3:6,7]-heptacyclic hepttrien[4,5-b]indole, or a substituted or unsubstituted aromatic fused ring system comprising at least three substituted or unsubstituted aromatic rings selected from: substituted or unsubstituted non-heterocyclic rings, substituted or unsubstituted heterocyclic 5-membered rings, substituted or unsubstituted 6-membered rings, or substituted or unsubstituted 7-membered rings; Ar 2 When k=0, Ar 3 When m=0 and k=0, Ar 4 When q and r = 0, Ar 5 When r = 0: Independently selected from: heterocycles of unsaturated 5- to 7-membered rings, substituted or unsubstituted, C6 to C6 rings. 30 Aryl, substituted or unsubstituted C3 to C 30 Heteroaryl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthrayl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted terphenylene, substituted or unsubstituted tetraphenyl, substituted or unsubstituted benzoanthrayl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthyl, substituted or unsubstituted carbazole, substituted or unsubstituted azaheptatriene, substituted or unsubstituted The substituted dibenzo[b,f]azacycloheptatriene, 9,9'-spirobis[fluorenyl], substituted or unsubstituted spiro[fluorenyl-9,9'-xanton], substituted or unsubstituted 9,14-dihydrodibenzo[2,3:6,7]azacycloheptatrien[4,5-b]indole, or a substituted or unsubstituted aromatic fused ring system comprising at least three substituted or unsubstituted aromatic rings selected from: substituted or unsubstituted non-heterocyclic rings, substituted or unsubstituted heterocyclic 5-membered rings, substituted or unsubstituted 6-membered rings, or substituted or unsubstituted 7-membered rings; The substituents are selected from: H, D, C1 to C. 12 Alkyl, unsubstituted C6 to C 18 Aryl, unsubstituted C3 to C 18 The heteroaryl group comprises a fused ring system containing 2 to 6 unsubstituted 5 to 7-membered rings, wherein the rings are selected from: unsaturated 5 to 7-membered heterocycles, 5 to 6-membered aromatic heterocycles, unsaturated 5 to 7-membered non-heterocycles, and 6-membered aromatic non-heterocycles. Furthermore, the organic matrix compound (OMC) and the luminescent matrix compound (EMC) are selected to be the same or different; wherein the metal complex has formula (II).

13. The organic electronic device according to claim 1 or 2, wherein the organic matrix compound (OMC) and the luminescent matrix compound (EMC) are selected from compounds comprising at least 1 to 6 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings, at least 1 to 3 substituted or unsubstituted unsaturated 5- to 7-membered heterocycles, at least 2 to 5 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings, at least 1 to 3 substituted or unsubstituted unsaturated 5- to 7-membered heterocycles, at least 3 or 4 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings, at least 1 to 3 substituted or unsubstituted unsaturated 5- to 7-membered heterocycles, at least one aromatic fused ring system containing heteroaromatic rings that is unsubstituted, or at least 1 to 3 unsubstituted unsaturated 5- to 7-membered heterocycles.

14. The organic electronic device according to claim 1 or 2, wherein the organic matrix compound (OMC) and the luminescent matrix compound (EMC) are selected from compounds comprising substituted or unsubstituted aromatic fused ring systems having at least ≥2 to ≤6 fused aromatic rings, the fused aromatic rings being selected from: substituted or unsubstituted non-heteroaromatic rings, substituted or unsubstituted hetero 5-membered rings, substituted or unsubstituted 6-membered rings, substituted or unsubstituted heterocyclic rings of unsaturated 5 to 7-membered rings, and unsubstituted aromatic fused ring systems having at least ≥2 to ≤6 fused aromatic rings, the fused aromatic rings being selected from: unsubstituted non-heteroaromatic rings, unsubstituted hetero 5-membered rings, unsubstituted 6-membered rings, or unsubstituted heterocyclic rings of unsaturated 5 to 7-membered rings.

15. The organic electronic device according to claim 1 or 2, wherein the organic matrix compound (OMC) and the luminescent matrix compound (EMC) are selected from compounds comprising at least 1 to 6 substituted or unsubstituted aromatic fused ring systems having at least one unsaturated 5-membered ring, at least 1 to 6 substituted or unsubstituted aromatic fused ring systems having at least one unsaturated 6-membered ring, at least 1 to 6 substituted or unsubstituted aromatic fused ring systems having at least one unsaturated 7-membered ring, at least 1 to 6 substituted or unsubstituted aromatic fused ring systems having at least one unsaturated 5-membered ring containing at least 1 to 3 heteroatoms, or at least 1 to 6 substituted or unsubstituted aromatic fused ring systems having at least one unsaturated 7-membered ring containing at least 1 to 3 heteroatoms.

16. The organic electronic device according to claim 1 or 2, wherein the organic matrix compound (OMC) and the luminescent matrix compound (EMC) contain heteroatoms selected from O, S, N, B, P or Si.

17. The organic electronic device according to claim 1 or 2, wherein the organic matrix compound (OMC) and the luminescent matrix compound (EMC) do not contain heteroatoms that are not part of an aromatic ring or an unsaturated 7-membered ring.

18. The organic electronic device according to claim 1 or 2, wherein the organic matrix compound (OMC) and the luminescent matrix compound (EMC) are selected from compounds comprising at least 6 to 12 aromatic rings, at least 4 to 11 non-heteroaromatic rings, at least 1 to 4 heteroaromatic 5-membered rings, at least 1 or 2 heterocyclic rings with unsaturated 5- to 7-membered rings, at least 6 to 12 aromatic rings, wherein at least 4 to 11 are non-heteroaromatic rings, and at least 1 to 4 are heteroaromatic rings. The aromatic rings, wherein the total number of non-heteroaromatic rings and heteroaromatic rings does not exceed 12 aromatic rings, and the aromatic rings consist of at least 6 to 12 aromatic rings, wherein at least 4 to 11 are non-heteroaromatic rings, and at least 1 to 4 are heteroaromatic rings, wherein the total number of non-heteroaromatic rings and heteroaromatic rings does not exceed 12 aromatic rings; and the hole-transporting compound or the hole-transporting compound according to Formula I is selected from compounds containing at least 1 to 4 heteroaromatic 5-membered rings, or at least 1 or 2 heterocycles with unsaturated 5 to 7-membered rings.

19. The organic electronic device according to claim 1 or 2, wherein for formula (I): -Ar 3 Selected from D1 to D17: (D7)、 (D8)、 (D9)、 (D10); (D11) (D12) (D13) (D14) (D15)、 (D16)、 (D17); Ar 1 When m>0 and k>0, the selection is from D7 to D15 and D17; when k>0 and m=0, the selection is from D7 to D15 and D17; when k>1, the selection is from D1 to D6. Ar 2 When m>0 and k>0, the selection is from D1 to D6; or when m>0 and k=0, the selection is from D7 to D15 and D17. Ar 4 When q>0, select from D1 to D6; or when q=0 and r>0, select from D1 to D6; or when q and r=0, select from D7 to D15 and D17. Ar 5 When q>0 and r>0, the selection is from D1 to D6, or when q>0 and r=0, the selection is from D7 to D15 and D17; Ar 6 When r>0 and q>0, the selection is from D7 to D15 and D17; when r>0 and q=0, the selection is from D7 to D15 and D17; or when r>1, the selection is from D1 to D6.

20. The organic electronic device according to claim 1 or 2, wherein the organic matrix compound (OMC) or the luminescent matrix compound (EMC) according to formula (I) is selected from F1 to F13: (F1)、 (F2)、 (F3)、 (F4)、 (F5)、 (F6)、 (F7)、 (F8)、 (F9)、 (F10)、 (F11)、 (F12)、 (F13)。 21. The organic electronic device according to claim 1 or 2, wherein n is an integer from 1 to 4.

22. The organic electronic device according to claim 1 or 2, wherein the metal complex is selected from the following formulas (IIa) to (IIe): (IIa)、 (IIb)、 (IIc)、 (IId)、 (IIe), in M is a metal ion; n is the valence of M, where n is an integer from 1 to 4; A 1 and A 2 Independently selected from substituted or unsubstituted C1 to C1 12 Alkyl, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 12 Mixed aromatics; A 3 Selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 12 Mixed aromatics; Where A 1 A 2 Or A 3 The substituents are independently selected from: D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkyl, partially deuterated or fully deuterated C1 to C6 alkoxy, COR 1 COOR 1 Halogen, F or CN, Where R 1 Selected from: C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkyl, partially deuterated or fully deuterated C1 to C6 alkoxy.

23. The organic electronic device according to claim 22, wherein A 1 A 2 and A 3 At least one of them contains a substituent, wherein A 1 A 2 and A 3 At least one of the substituents is independently selected from: C3 to C9 heteroaryl, C1 to C6 alkoxy, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C6 alkoxy, COR 1 COOR 1 Halogen, F or CN.

24. The organic electronic device according to claim 1 or 2, wherein L is independently selected from G1 to G64: (G63)、 (G64).

25. The organic electronic device according to claim 1 or 2, wherein the hole injection layer comprises a first sublayer containing a metal complex of formula (II) and a second sublayer containing the organic matrix compound (OMC), wherein the first sublayer is disposed closer to the anode layer and the second sublayer is disposed closer to the at least one light-emitting layer.

26. The organic electronic device according to claim 1 or 2, wherein the hole injection layer comprises a first sublayer containing a metal complex of formula (II) and a second sublayer containing the organic matrix compound (OMC) and the metal complex, wherein the first sublayer is disposed closer to the anode layer and the second sublayer is disposed closer to the at least one light-emitting layer.

27. The organic electronic device according to claim 25 or 26, wherein the organic electronic device further comprises a hole transport layer, wherein the hole transport layer is disposed between the hole injection layer and the at least one light-emitting layer.

28. The organic electronic device of claim 1 or 2, wherein the hole transport layer comprises an organic matrix compound (OMC), wherein the organic matrix compound (OMC) in the hole injection layer and the hole transport layer is selected to be different or the same.

29. The organic electronic device according to claim 1 or 2, wherein the hole injection layer and the hole transport layer comprise an organic matrix compound (OMC), and the at least one light-emitting layer comprises a light-emitting matrix compound (EMC) of formula (I), wherein in formula (I), Ar 3 The same functional groups were selected.

30. The organic electronic device according to claim 1 or 2, wherein the organic electronic device is a light-emitting device or a display device.

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