Organic electronic device comprising a compound of formula (I) and a compound of formula (III) and display device comprising the organic electronic device

Abstract

The present application relates to an organic electronic device comprising a compound of formula (I) and a compound of formula (III) and a display device comprising the organic electronic device.

Description

Technical Field

[0001] The present invention relates to organic electronic devices comprising compounds of formula (I) and formula (III), and display devices comprising organic electronic devices. Background Technology

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

[0003] When a voltage is applied to the anode and cathode, holes injected from the anode move to the EML via the HTL, while electrons injected from the cathode move to the EML via the ETL. Holes and electrons recombine in the EML to generate excitons. When the excitons transition from the excited state to the ground state, they emit light. The injection and flow of holes and electrons should be balanced to ensure that OLEDs with this structure exhibit excellent efficiency and / or long lifetime.

[0004] The performance of organic light-emitting diodes can be affected by the characteristics of the semiconductor layer, which in turn can be affected by the characteristics of the compounds contained in the semiconductor layer.

[0005] Further improvements are needed in the performance of organic electronic devices, particularly in achieving improved operating voltage, improved stability of operating voltage over time, and improved current efficiency. Furthermore, improvements are still needed in reducing electrical crosstalk between adjacent pixels in active-matrix OLED displays. Summary of the Invention

[0006] One aspect of the present invention provides an organic electronic device comprising a substrate, an anode layer, a cathode layer, a first photoactive layer, a second photoactive layer, a hole injection layer, and a charge generation layer. The charge generation layer includes a p-type charge generation layer and an n-type charge generation layer. The hole injection layer, charge generation layer, first photoactive layer, and second photoactive layer are arranged between the anode layer and the cathode layer. The hole injection layer is positioned closer to the anode layer than the p-type charge generation layer. The p-type charge generation layer is arranged closer to the cathode layer than the n-type charge generation layer, and the n-type charge generation layer is arranged closer to the anode layer than the p-type charge generation layer. The hole injection layer is in direct contact with the anode layer. The charge generation layer is arranged between the first photoactive layer and the second photoactive layer. The hole injection layer contains compounds of formula (I): (I), in: M is a metal ion; n is the valence of M and is selected from 1 to 4; L is a ligand independently selected from formula (II). (II), in A 1 Selected from C=O or SO2; X 1 Selected from CR 1 Or N; X 2 Selected from CR 2 Or N; X 3 Selected from CR 3 Or N; X 4 Selected from CR 4 Or N; Where X 1 X 2 X 3 X 4 The 0, 1, or 2 elements are selected from N; R 1 To R 4 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl groups, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated or perfluorinated C1 to C8 alkoxy, OCF3, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Heteroaryl, substituted or unsubstituted 6-membered heteroaryl, substituted or unsubstituted 6-membered C3 to C5 heteroaryl; substituted or unsubstituted 6-membered C4 to C5 heteroaryl; halogen, F, Cl or CN, and wherein any R k To R k+1 They can form a ring, where k is an integer selected from 1 to 3; R 5 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20Heteroaryl, substituted or unsubstituted 6-membered heteroaryl, substituted or unsubstituted 6-membered C3 to C5 heteroaryl; substituted or unsubstituted 6-membered C4 to C5 heteroaryl; Where R 1 To R 5 The replacement of C1 to C 12 Alkyl, substituted C1 to C8 alkoxy, substituted C6 to C 19 Aryl, substituted C2 to C 20 One or more substituents of a heteroaryl, a substituted 6-membered heteroaryl, a substituted 6-membered C3 to C5 heteroaryl, or a substituted 6-membered C4 to C5 heteroaryl are independently selected from D, an electron-withdrawing group, a halogen, Cl, F, CN, a partially fluorinated or perfluorinated C1 to C8 alkyl, or a partially or perfluorinated C1 to C8 alkoxy. AL is an auxiliary ligand that coordinates with metal M; m is an integer selected from 0 to 2; The p-type charge-generating layer includes organic compounds of formula (III). (III), in n is an integer selected from 0, 1, 2, 3, 4, 5 or 6, preferably 0, 2 or 4; m is an integer selected from 0 or 1; preferably 1; Y 1 Y 2 and Y 3 Independently selected from O, S, CR 1a R 2a CR 1b R 2b NR 3a NR 3b , or Y 1 Y 2 and Y 3 At least one of them forms a fused ring with A, wherein each Y 2 The choice is either the same or different, with a preference for the same, and each Y... 3 Choose between "same" or "different", with "same" being the preferred choice. R 1a R 2a R 1b and R 2b Independently selected from electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C8 alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C40 Aryl, substituted or unsubstituted C2 to C 40 Mixed aromatics, Where R 1a R 2a R 1b and R 2b One or more substituents are independently selected from D, electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 30 aryl groups, and substituted or unsubstituted C6 to C6 groups. 30 Mixed aromatics; C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, isocyanate, SCN, OCN, SF5, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, and perfluorinated C1 to C8 alkoxy. R 3a and R 3b Selected from electron-withdrawing groups, CN, partially fluorinated C1 to C6 alkyl groups, perfluorinated C1 to C6 alkyl groups, CF3, substituted or unsubstituted C6 to C6 alkyl groups. 30 aryl, or substituted or unsubstituted C3 to C4 30 Mixed aromatics, Where R 3a and R 3b One or more substituents are independently selected from D, electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C8 alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 30 aryl groups, and substituted or unsubstituted C6 to C6 groups. 30 Mixed aromatics; Among them, C6 to C 30 Aryl, C6 to C 30One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, isocyanate, SCN, OCN, SF5, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, and perfluorinated C1 to C8 alkoxy. A is selected from C3 to C4, whether substituted or unsubstituted. 40 Cyclic hydrocarbon group, substituted or unsubstituted C3 to C4 40 Cycloalkyl groups, containing one or more double bonds, substituted or unsubstituted C3 to C4 groups. 40 Cycloalkyl groups, substituted or unsubstituted C3 to C4 40 Cycloalkenyl groups, substituted or unsubstituted C2 to C3 40 Heterocyclic alkyl groups, containing one or more double bonds, substituted or unsubstituted C2 to C3 groups. 40 Heterocyclic alkyl groups, substituted or unsubstituted C2 to C3 40 Heterocyclic alkenyl groups, substituted or unsubstituted C6 to C6 groups 40 Aromatic groups, substituted or unsubstituted C2 to C3 40 heteroaryl groups, One or more substituents on A are independently selected from D, electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C8 alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Mixed aromatics, Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, isocyanate, SCN, OCN, SF5, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, and OCF3.

[0007] It should be noted that, unless otherwise noted, any A in the entire application and claims is a reference to the meaning of the word. n B n R n X n "Etc" always refers to the same part.

[0008] In this specification, unless otherwise defined, "replaced" refers to the substance replaced by deuterium, C1 to C2. 12 Alkyl and C1 to C 12 Alkyl-substituted.

[0009] However, in this specification, "aryl-substituted" means substituted by one or more aryl groups, which themselves may be substituted by one or more aryl and / or heteroaryl groups.

[0010] Accordingly, in this specification, "heteroaryl substituted" means substituted by one or more heteroaryl groups, which themselves may be substituted by one or more aryl and / or heteroaryl groups.

[0011] 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 contain 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.

[0012] Specific examples of alkyl groups can be methyl groups, ethyl groups, propyl groups, isopropyl groups, butyl groups, isobutyl groups, sec-butyl groups, tert-butyl groups, pentyl groups, and hexyl groups.

[0013] 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 corresponding cycloalkane. Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, adamantyl, and so on.

[0014] 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.

[0015] In this specification, "aryl group" refers to a hydrocarbon group formed by formally isolating a hydrogen atom from an aromatic ring in a 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 is a planar ring or ring system covalently bonded to a carbon atom, wherein the planar ring or ring system comprises 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 fluorene-2-yl.

[0016] Similarly, heteroaryl is particularly well understood as a group derived by formally isolating a cyclic hydrogen from a heterocyclic aromatic ring in a compound containing at least one heterocyclic aromatic ring.

[0017] Heterocyclic alkyl groups are particularly well understood as groups derived by formally isolating a cyclic hydrogen from a saturated cyclic alkyl ring in a compound containing at least one saturated cyclic alkyl ring.

[0018] In this specification, "C6 to C" 40 An "aromatic group" can be an aromatic group or a group containing at least one aromatic moiety; that is, an aromatic group can also contain a fused non-aromatic moiety. This moiety can contain different atoms.

[0019] In this specification, "C2 to C" 40 A "heteroaromatic group" can be a heteroaromatic group or a group containing at least one heteroaromatic moiety; that is, a heteroaromatic group can also contain a fused nonaromatic moiety. This moiety can contain different atoms.

[0020] The terms "fused aryl ring" or "condensed aryl ring" are understood to refer to a ring in which two aryl rings share at least two common sp... 2 When carbon atoms are hybridized, they are considered to be either fused or condensed.

[0021] The term "cyano moiety" refers to the CN substituent.

[0022] The term "electron-withdrawing group" refers to a chemical group in a molecule that can draw electrons away from adjacent parts of the molecule. The distance at which an electron-withdrawing group can exert its effect, i.e., the number of bonds crossed by the electron-withdrawing action, increases with conjugated π-electron systems such as aromatic systems. Examples of electron-withdrawing groups include NO2, CN, halogens, Cl, F, partially fluorinated or perfluorinated alkyl groups, and partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, partially fluorinated or perfluorinated alkoxy, partially fluorinated or perfluorinated C1 to C6 alkoxy.

[0023] In this specification, a single key refers to a direct key.

[0024] The term “n-type charge generation layer” is sometimes also referred to in the art as n-CGL or electron generation layer, and is intended to include both.

[0025] The term "p-type charge generation layer" is sometimes also referred to in the art as p-CGL or hole generation layer, and is intended to include both.

[0026] The terms "without," "containing," and "not including" do not exclude impurities that may be present in the compound before deposition. Impurities have no technical effect on the objectives achieved by this invention.

[0027] The term "contact sandwich" refers to a three-layer arrangement in which the middle layer is in direct contact with the two adjacent layers.

[0028] The terms "light-absorbing layer" and "light-absorbing layer" are used synonymously.

[0029] The terms "light-emitting layer", "light-emitting layer", and "light-emitting layer" are used synonymously.

[0030] The terms “OLED,” “organic light-emitting diode,” and “organic light-emitting device” are used synonymously.

[0031] The terms “anode,” “anode layer,” and “anode electrode” are used synonymously.

[0032] The terms “cathode,” “cathode layer,” and “cathode electrode” are used synonymously.

[0033] The term "top-emitting device" should be understood to refer to an organic electronic device that emits light through a cathode layer.

[0034] The term "bottom-emitting device" should be understood as referring to an organic electronic device that emits light through a substrate.

[0035] In this specification, hole characteristics refer to the ability of supplying electrons to form holes when an electric field is applied, and the holes formed in the anode due to the conductivity characteristics based on the highest occupied molecular orbital (HOMO) energy level can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0036] Furthermore, electronic properties refer to the ability of electrons that accept electrons when an electric field is applied and are formed in the cathode due to the conductivity of the lowest unoccupied molecular orbital (LUMO) energy level to be easily injected into and transported in the light-emitting layer.

[0037] Beneficial effects

[0038] Surprisingly, it has been found that the organic electronic device according to the present invention solves the fundamental problem of the present invention by enabling the device to outperform known organic electronic devices in several aspects, particularly in terms of improved operating voltage, improved stability, especially the stability of the operating voltage over time, and improved current efficiency. Furthermore, it reduces electrical crosstalk between adjacent pixels in active OLED displays.

[0039] Several advantageous embodiments of the layers of the device according to the invention will be described below, wherein the features can be combined arbitrarily: Hole injection layer According to one embodiment of the present invention, the thickness of the hole injection layer is in the range of 1 nm to 20 nm, preferably in the range of 1 nm to 15 nm, and more preferably in the range of 3 nm to 15 nm.

[0040] According to one embodiment, the atomic mass of M in the compound of formula (I) is selected in the range of ≥20 Da but ≤200 Da. Preferably, the atomic mass of M in the compound of formula (I) is in the range of ≥54 Da but ≤135 Da.

[0041] According to one embodiment, M of the compound of formula (I) may be selected from a metal ion, wherein the corresponding metal has an electronegativity value of ≥0.65 but ≤1.9 according to Allen.

[0042] The term “according to Allen’s electronegativity value” is especially relevant 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.

[0043] According to one embodiment, M can be selected from transition metals or group III or V metals.

[0044] According to one embodiment, the M of the compound in formula (I) is selected from Li(I), Na(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(II), Mn(III), Ru(III), In(III), Fe(II), Fe(III), Ce(IV).

[0045] According to one embodiment, the M of the compound in formula (I) is selected from Li(I), Na(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(II), Mn(III), Ru(III), In(III), Fe(II), Fe(III).

[0046] According to one embodiment, the M in the compound of formula (I) is selected from Cu(II), Zn(II), Ga(III), Mn(II), Mn(III), In(III), Fe(II), Fe(III).

[0047] According to one embodiment, the M in the compound of formula (I) is selected from Cu(II), Zn(II), Mn(II), In(III), and Fe(III).

[0048] Term "m"

[0049] The term "m" is an integer selected from 0 to 2, where m corresponds to the number of auxiliary ligands AL coordinated with metal M. According to one embodiment, "m" is an integer selected from 0 or 1. According to another embodiment, "m" is an integer selected from 1. According to yet another embodiment, "m" is an integer selected from 2. Preferably, "m" is an integer and can be selected from 0.

[0050] Another embodiment of the compound according to formula (I) wherein n = 2 or 3; and / or m is an integer selected from 0 or 1, preferably 0.

[0051] ligand L

[0052] "L is independently selected from formula (II)" means that if n>1, each L can be selected to be the same or different.

[0053] According to one implementation, each L in formula (II) is chosen to be the same.

[0054] According to one implementation, the L values ​​in equation (II) are the same when n > 1.

[0055] According to one embodiment, the molecular weight of L is selected in the range of ≤600 Da but ≥240 Da, preferably in the range of ≤500 Da but ≥280 Da.

[0056] According to one embodiment of the present invention, R 1 To R 4 One or zero of them are not H or D.

[0057] According to one embodiment of the present invention, the ligand of formula (II) does not contain an alkoxy group.

[0058] According to one embodiment, in the ligand of formula (II), R 1 To R 4 Independently selected from H, D, F, or CN, preferably H or D; and R 5 Selected from unsubstituted and substituted C1 to C6 alkyl groups, substituted or unsubstituted C6 to C6 alkyl groups.12 Aryl, substituted or unsubstituted C2 to C 12 Heteroaryl, substituted or unsubstituted 6-membered heteroaryl; Among them, substituted C1 to C6 alkyl groups, substituted C6 to C 12 Aryl, substituted C2 to C 12 The substituents in heteroaryl and substituted 6-membered heteroaryl are selected from halogens, F, Cl, CN, partially or perfluorinated C1 to C4 alkyl, partially or perfluorinated C1 to C4 alkoxy, C1 to C4 alkyl, and C1 to C4 alkoxy.

[0059] According to one embodiment of the present invention, the compound of formula (I) contains at least two fluorine atoms and / or at least one CN group and less than 50 fluorine atoms and / or less than 16 CN groups; preferably, the compound of formula (I) contains 2 to 36 fluorine atoms and / or 1 to 8 CN groups.

[0060] According to one embodiment, when the compound of formula (I) contains at least one CN group, it is particularly preferred that the CN group is present in group R. 1 To R 4 One or more of them, preferably present in R 2 Or R 3 One or more of them.

[0061] According to one embodiment, R is particularly preferred when the compound of formula (I) contains at least two fluorine atoms. 5 It contains at least two fluorine atoms.

[0062] According to one embodiment of the present invention, the ligand of formula (II) comprises at least two fluorine atoms and / or at least one CN group.

[0063] According to one embodiment of the invention, the ligand of formula (II) contains at least two fluorine atoms and / or at least one CN group and less than 25 fluorine atoms and / or less than 4 CN groups; preferably, the compound of formula (I) contains 2 to 13 fluorine atoms and / or 1 to 4 CN groups.

[0064] According to one embodiment of the invention, when the ligand of formula (II) contains at least one CN group, it is particularly preferred that the CN group is present in group R. 1 To R 4 One or more of them, preferably present in R 2 Or R 3 One or more of them.

[0065] According to one embodiment of the invention, R is particularly preferred when the ligand of formula (II) contains at least two fluorine atoms. 5It contains at least two fluorine atoms.

[0066] According to one embodiment of the present invention, group R 1 To R 4 None of them contain fluorine atoms.

[0067] According to one embodiment of the present invention, in the ligand of formula (II), R 1 To R 4 Independently selected from H, D, F, or CN, preferably H or D; and R 5 Selected from unsubstituted and substituted C1 to C6 alkyl groups, substituted or unsubstituted C6 to C6 alkyl groups. 12 Aryl, substituted or unsubstituted C2 to C 12 Heteroaryl, substituted or unsubstituted 6-membered heteroaryl; Among them, substituted C1 to C6 alkyl groups, substituted C6 to C 12 Aryl, substituted C2 to C 12 The substituents in heteroaryl and substituted 6-membered heteroaryl are selected from halogens, F, Cl, CN, partially or perfluorinated C1 to C4 alkyl, partially or perfluorinated C1 to C4 alkoxy, C1 to C4 alkyl, and C1 to C4 alkoxy. Where R 1 To R 4 and / or R 5 At least one of them contains at least two fluorine atoms and / or at least one CN group.

[0068] According to one embodiment of the present invention, in the ligand of formula (II), R 1 To R 4 Independently selected from H, D, or CN, preferably H or D; and R 5 Selected from the replaced C1 to C 12 Alkyl, substituted C6 to C 19 Aryl, substituted C2 to C 20 Heteroaryl, substituted 6-membered heteroaryl, substituted 6-membered C3 to C5 heteroaryl; substituted 6-membered C4 to C5 heteroaryl; Among which C1 to C are replaced 12 Alkyl, substituted C6 to C 19 Aryl, substituted C2 to C 20 Heteroaryl, substituted 6-membered heteroaryl, substituted 6-membered C3 to C5 heteroaryl; the substituents in the substituted 6-membered C4 to C5 heteroaryl are selected from halogens, F, Cl, CN, partially or perfluorinated C1 to C6 alkyl, C1 to C6 alkyl, C1 to C6 alkoxy. Where R 1 To R 4 and / or R 5At least one of them contains at least two fluorine atoms and / or at least one CN group.

[0069] According to one embodiment of the present invention, in the ligand of formula (II), R 1 To R 4 Independently selected from H or D; and R 5 Selected from the replaced C1 to C 12 Alkyl, substituted C6 to C 19 Aryl, substituted C2 to C 20 Heteroaryl, substituted 6-membered heteroaryl, substituted 6-membered C3 to C5 heteroaryl; substituted 6-membered C4 to C5 heteroaryl; Among which C1 to C are replaced 12 Alkyl, substituted C6 to C 19 Aryl, substituted C2 to C 20 Heteroaryl, substituted 6-membered heteroaryl, substituted 6-membered C3 to C5 heteroaryl; the substituents in the substituted 6-membered C4 to C5 heteroaryl are selected from halogens, F, Cl, CN, partially or perfluorinated C1 to C6 alkyl, C1 to C6 alkyl, C1 to C6 alkoxy. Where R 5 It contains at least two fluorine atoms and / or at least one CN group.

[0070] According to one embodiment of the present invention, in the ligand of formula (II), R 1 To R 4 Selected from H or D; and R 5 Selected from substituted C1 to C6 alkyl, substituted C6 aryl, substituted C2 to C5 heteroaryl, and substituted 6-membered heteroaryl; The substituents in the substituted C1 to C6 alkyl, substituted C6 aryl, substituted C2 to C5 heteroaryl, and substituted 6-membered heteroaryl are selected from halogens, F, Cl, CN, and partially or perfluorinated C1 to C6 alkyl, C1 to C6 alkyl, and C1 to C6 alkoxy groups. Where R 5 It contains at least two fluorine atoms and / or at least one CN group.

[0071] According to one implementation, R in equation (II) 1 To R 5 One or more substituents are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3, partially or perfluorinated C1 to C8 alkoxy groups, and OCF3.

[0072] According to one implementation, R in equation (II) 1 To R 5One or more substituents are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, and CF3.

[0073] According to one embodiment, formula (II) contains at least one fluorine atom, preferably at least two fluorine atoms, and more preferably at least three fluorine atoms.

[0074] According to one implementation, A 1 The formula is C=O and contains at least one fluorine atom, preferably at least two fluorine atoms, more preferably at least three fluorine atoms.

[0075] According to one embodiment, formula (II) comprises at least one partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl group.

[0076] According to one embodiment, formula (II) contains at least one CF3 group.

[0077] According to one embodiment, formula (II) comprises at least two partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl groups.

[0078] According to one embodiment, formula (II) contains at least two CF3 groups.

[0079] According to one implementation, R in equation (II) 1 To R 4 At least one of them contains at least one partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl moiety, and R of formula (II) 5 It contains at least one partially fluorinated or perfluorinated C1 to C4 alkyl moiety.

[0080] According to one implementation, R in equation (II) 1 To R 4 At least one of them contains at least one CF, and R of equation (II) 5 It contains at least one CF3.

[0081] According to one implementation, R in equation (II) 1 To R 5 One or more of the substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, partially or perfluorinated C1 to C8 alkoxy, OCF3, and formula (II) contains at least one partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl group.

[0082] According to one implementation, R in equation (II) 1 To R 5One or more substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3, and formula (II) contains at least one partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl group.

[0083] According to one implementation, R in equation (II) 1 To R 5 One or more of the substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3, partially or perfluorinated C1 to C8 alkoxy groups, OCF3; and formula (II) contains at least one CF3 group.

[0084] According to one implementation, R in equation (II) 1 To R 5 One or more substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3; and formula (II) contains at least one CF3 group.

[0085] According to one implementation, R in equation (II) 1 To R 5 One or more of the substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, partially or perfluorinated C1 to C8 alkoxy, OCF3; and formula (II) contains at least one fluorine atom.

[0086] According to one implementation, R in equation (II) 1 To R 5 One or more of the substituents are independently selected from halogens, Cl, F, CN, partially or perfluorinated C1 to C8 alkyl groups, CF3, partially or perfluorinated C1 to C8 alkoxy groups, OCF3; and formula (II) contains at least two fluorine atoms.

[0087] According to one implementation, R in equation (II) 1 To R 5 One or more of the substituents, if present, are independently selected from halogens, Cl, F, CN, partially or perfluorinated C1 to C8 alkyl, CF3, partially or perfluorinated C1 to C8 alkoxy, OCF3; and formula (II) contains at least three fluorine atoms.

[0088] According to one implementation, R in equation (II) 1 To R 5One or more substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3; and formula (II) contains at least one fluorine atom.

[0089] According to one implementation, R in equation (II) 1 To R 5 One or more substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3; and formula (II) contains at least two fluorine atoms.

[0090] According to one implementation, R in equation (II) 1 To R 5 One or more substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3; and formula (II) contains at least three fluorine atoms.

[0091] According to one embodiment, M in the compound of formula (I) is selected from Li(I), Na(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(II), Mn(III), Ru(III), In(III), Fe(II), Fe(III); and R in formula (II) 1 To R 5 One or more substituents, if present, are independently selected from halogens, Cl, F, CN, partially or perfluorinated C1 to C8 alkyl groups, CF3, partially or perfluorinated C1 to C8 alkoxy groups, and OCF3.

[0092] According to one embodiment, M in the compound of formula (I) is selected from Li(I), Na(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(II), Mn(III), Ru(III), In(III), Fe(II), Fe(III); and R in formula (II) 1 To R 5 One or more substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, and CF3.

[0093] According to one embodiment, M in the compound of formula (I) is selected from Cu(II), Mn(II), In(III), Fe(III); and R in formula (II)1 To R 5 One or more substituents, if present, are independently selected from halogens, Cl, F, CN, partially or perfluorinated C1 to C8 alkyl groups, CF3, partially or perfluorinated C1 to C8 alkoxy groups, and OCF3.

[0094] According to one embodiment, M in the compound of formula (I) is selected from Cu(II), Mn(II), In(III), Fe(III); and R in formula (II) 1 To R 5 One or more substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, and CF3.

[0095] According to one embodiment, M in the compound of formula (I) is selected from Li(I), Na(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(II), Mn(III), Ru(III), In(III), Fe(II), Fe(III); R in formula (II) 1 To R 5 One or more of the substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3, partially or perfluorinated C1 to C8 alkoxy groups, OCF3; and formula (II) contains at least one partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl group.

[0096] According to one embodiment, M in the compound of formula (I) is selected from Li(I), Na(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(II), Mn(III), Ru(III), In(III), Fe(II), Fe(III); R in formula (II) 1 To R 5 One or more substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3; and formula (II) contains at least one partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl group.

[0097] According to one embodiment, M in the compound of formula (I) is selected from Li(I), Na(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(II), Mn(III), Ru(III), In(III), Fe(II), Fe(III); R in formula (II) 1 To R 5 One or more of the substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3, partially or perfluorinated C1 to C8 alkoxy groups, OCF3; and formula (II) contains at least one CF3 group.

[0098] According to one embodiment, M in the compound of formula (I) is selected from Li(I), Na(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(II), Mn(III), Ru(III), In(III), Fe(II), Fe(III); R in formula (II) 1 To R 5 One or more substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3; and formula (II) contains at least one CF3 group.

[0099] According to one embodiment, M in the compound of formula (I) is selected from Cu(II), Mn(II), In(III), Fe(III); R in formula (II) 1 To R 5 One or more of the substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3, partially or perfluorinated C1 to C8 alkoxy groups, OCF3; and formula (II) contains at least one partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl group.

[0100] According to one embodiment, M in the compound of formula (I) is selected from Cu(II), Mn(II), In(III), Fe(III); R in formula (II) 1 To R 5 One or more substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3; and formula (II) contains at least one partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl group.

[0101] According to one embodiment, M in the compound of formula (I) is selected from Cu(II), Mn(II), In(III), Fe(III); R in formula (II) 1 To R 5 One or more of the substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3, partially or perfluorinated C1 to C8 alkoxy groups, OCF3; and formula (II) contains at least one CF3 group.

[0102] According to one embodiment, M in the compound of formula (I) is selected from Cu(II), Mn(II), In(III), Fe(III); R in formula (II) 1 To R 5 One or more substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3; and formula (II) contains at least one CF3 group.

[0103] According to one embodiment, M in the compound of formula (I) is selected from Li(I), Na(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(II), Mn(III), Ru(III), In(III), Fe(II), Fe(III); and M in the compound of formula (I) is selected from Li(I), Na(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(II), Mn(III), Ru(III), In(III), Fe(II), Fe(III); R in formula (II) 1 To R 5 One or more of the substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3, partially or perfluorinated C1 to C8 alkoxy groups, OCF3; and formula (II) contains at least one partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl group.

[0104] According to one embodiment, M in the compound of formula (I) is selected from Li(I), Na(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(II), Mn(III), Ru(III), In(III), Fe(II), Fe(III); and M in the compound of formula (I) is selected from Li(I), Na(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(II), Mn(III), Ru(III), In(III), Fe(II), Fe(III); R in formula (II) 1 To R 5 One or more substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3; Formula (II) contains at least one partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl group.

[0105] According to one embodiment, M in the compound of formula (I) is selected from Li(I), Na(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(II), Mn(III), Ru(III), In(III), Fe(II), Fe(III); R in formula (II) 1 To R 5 One or more of the substituents are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3, partially or perfluorinated C1 to C8 alkoxy groups, OCF3; and formula (II) contains at least one CF3 group.

[0106] According to one embodiment, M in the compound of formula (I) is selected from Li(I), Na(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(II), Mn(III), Ru(III), In(III), Fe(II), Fe(III); R in formula (II) 1 To R 5 One or more substituents are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3; and formula (II) contains at least one CF3 group.

[0107] According to one embodiment, M in the compound of formula (I) is selected from Cu(II), Mn(II), In(III), Fe(III); R in formula (II) 1 To R 5 One or more of the substituents are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3, partially or perfluorinated C1 to C8 alkoxy groups, OCF3; and formula (II) contains at least one partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl group.

[0108] According to one embodiment, M in the compound of formula (I) is selected from Cu(II), Mn(II), In(III), Fe(III); R in formula (II) 1 To R 5 One or more substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3; and formula (II) contains at least one partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl group.

[0109] According to one embodiment, M in the compound of formula (I) is selected from Cu(II), Mn(II), In(III), Fe(III); R in formula (II) 1 To R 5 One or more of the substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3, partially or perfluorinated C1 to C8 alkoxy groups, OCF3; and formula (II) contains at least one CF3 group.

[0110] According to one embodiment, M in the compound of formula (I) is selected from Cu(II), Mn(II), In(III), Fe(III); R in formula (II) 1 To R 5 One or more substituents, if present, are independently selected from halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3; and formula (II) contains at least one CF3 group.

[0111] According to one embodiment of the compound of formula (I), R 5 Selected from CF3, C2F5, C3F7, iso-C3F7, C4F9, tert-C4H9 or formulas (B1) to (B51). (B1) (B2) (B3) (B4) (B5) (B6) (B7) (B8) (B9) (B10) (B11) (B12) (B13) (B14) (B15) (B16) (B17) (B18) (B19) (B20) (B21) (B22) (B23) (B24) (B25) (B26) (B27) (B28) (B29) (B30) (B31) (B32) (B33) (B34) (B35) (B36) (B37) (B38) (B39) (B40) (B41) (B42) (B43) (B44) (B45) (B46) (B47) (B48) (B49) (B50) (B51); in" " indicates the binding position; preferably, R 5 Selected from CF3 or formulas (B1) to (B36), more preferably R 5 Selected from CF3 or formulas (B2) to (B25).

[0112] According to one embodiment of the present invention, the ligand of formula (II) is selected from one of the following formulas (C1) to (C141). (C1) (C2) (C3) (C4) (C5) (C6) (C7) (C8) (C9) (C10) (C11) (C12) (C13) (C14) (C15) (C16) (C17) (C18) (C19) (C20) (C21) (C23) (C24) (C25) (C26) (C27) (C28);

[0113] Preferably, the ligands of formula (II) are selected from (C1) to (C24), (C29) to (C136) and (C141), with (C1), (C13) and (C29) to (C136) being particularly preferred.

[0114] According to one embodiment of the present invention, the compound of formula (I) is selected from one of the following formulas (A1) to (A127): (A52)ぁ (A53)、 (A54)、 (A55)ぁ (A56)、 (A57)、 (A58)ぁ (A59)、 (A60)、 (A61)ぁ (A62)ぁ (A63) (A64) (A65)ぁ (A66)、 (A67)、 (A68) (A69) (A70)、 (A71)ぁ (A72)、 (A73) (A74)、 (A75)、 (A76) (A77)、 (A78)、 (A79) (A80)、 (A81)ぁ (A82)、 (A83) (A84) (A85)、 (A86) (A87) (A88) (A89) (A90)、 (A91)ぁ (A92)ぁ (A93) (A94)、 (A95)ぁ (A96)ぁ (A97)、 (A98) (A99)ぁ (A100)、 (A101)ぁ (A102)ぁ (A103) (A104) (A105)ぁ (A106) (A107) (A108) (A109) (A110)、 (A111)ぁ (A112)ぁ (A113) (A114) (A115) (A116) (A117) (A118) (A119) (A120) (A121) (A122) (A123) (A124) (A125) (A126) (A127).

[0115] Preferably, the compounds of formula (I) are selected from formulas (A1) to (A43) and (A52) to (A120) and (A127).

[0116] The compounds of formula (I) and the hole injection layers containing the compounds of formula (I) may be substantially non-luminescent or non-luminescent.

[0117] Based on the weight of the hole injection layer, the concentration of the compound of formula (I) can be selected from 1% by weight to 30% by weight, preferably 2% by weight to 25% by weight, and more preferably 3% by weight to 15% by weight.

[0118] Based on the volume of the hole injection layer, the concentration of the compound of formula (I) can be selected from 1 volume% to 30 volume, preferably 2 volume% to 25 volume, and more preferably 3 volume% to 15 volume.

[0119] p-type charge generation layer

[0120] P-type charge-generating layers can be formed on the anode or cathode layer via vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blodgett (LB) deposition, etc. When using vacuum deposition to form a p-type charge-generating layer, the deposition conditions can vary depending on the compound used to form the layer and the desired structure and thermal properties of the layer. However, typically, vacuum deposition conditions 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 nm / s to 10 nm / s.

[0121] When spin coating or printing is used to form a p-type charge-generating layer, the coating conditions can vary depending on the compound used to form the layer and the desired structure and thermal properties of the organic semiconductor layer. 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.

[0122] The thickness of the p-type charge generation layer can range from about 1 nm to about 20 nm, for example from about 2 nm to about 15 nm, or from about 2 nm to about 12 nm.

[0123] According to one embodiment, the organic compound of formula (III) has a LUMO energy level equal to or less than -4.30 eV, preferably -4.50 eV, more preferably -4.70 eV, even more preferably -4.90 eV, and most preferably -5.00 eV, wherein the hybrid functionals B3LYP and 6-31G are applied in the gas phase. The basis set was used to calculate the LUMO levels using the package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany).

[0124] According to one embodiment, based on the total volume of the first p-type charge generating layer, the amount of the organic compound of formula (III) present in the p-type charge generating layer is ≥0.01 vol% to ≤99.9 vol%, preferably ≥0.01 vol% to ≤99 vol%, more preferably ≥0.01 vol% to ≤95 vol%, more preferably ≥0.01 vol% to ≤90 vol%, more preferably ≥0.01 vol% to ≤80 vol%, more preferably ≥0.01 vol% to ≤70 vol%, more preferably 0.01 vol% to ≤60 vol%, more preferably ≥0.01 vol% to ≤50 vol%, more preferably ≥0.01 vol% to ≤40 vol%, more preferably ≥0.01 vol% to ≤30 vol%, more preferably ≥0.01 vol% to ≤20 vol%, more preferably ≥0.01 vol% to ≤10 vol%.

[0125] According to one embodiment, based on the total weight of the p-type charge generation layer, the amount of the compound of formula (III) present in the p-type charge generation layer is ≥0.01 wt% to ≤99.9 wt%, preferably ≥0.01 wt% to ≤99 wt%, more preferably ≥0.01 wt% to ≤95 wt%, more preferably ≥0.01 wt% to ≤90 wt%, more preferably ≥0.01 wt% to ≤80 wt%, more preferably ≥0.01 wt% to ≤70 wt%, more preferably ≥0.01 wt% to ≤60 wt%, more preferably ≥0.01 wt% to ≤50 wt%, more preferably ≥0.01 wt% to ≤40 wt%, more preferably ≥0.01 wt% to ≤30 wt%, more preferably ≥0.01 wt% to ≤20 wt%, more preferably ≥0.01 wt% to ≤10 wt%.

[0126] Thickness of the first p-type charge generation layer

[0127] The thickness of the first p-type charge generation layer may be in the range of 0.5 nm to 50 nm; or in the range of 1 nm to about 40 nm; or in the range of 2 nm to 30 nm; or in the range of 3 nm to 25 nm; or in the range of 4 nm to 20 nm; or in the range of 5 nm to 15 nm.

[0128] If a second p-type charge generating layer or a second and third p-type charge generating layer are present, the thickness of the second n-type charge generating layer or the third charge generating layer may be independently within the range of 0.5 nm to 50 nm; or within the range of 1 nm to about 40 nm; or within the range of 2 nm to 30 nm; or within the range of 3 nm to 25 nm; or within the range of 4 nm to 20 nm; or within the range of 5 nm to 15 nm.

[0129] Compounds of formula (III)

[0130] n

[0131] According to one implementation, n can be an integer selected from 0, 1, 2, 3 or 4.

[0132] According to a preferred embodiment, n can be an integer selected from 0, 1, or 2.

[0133] m

[0134] According to a preferred embodiment, m is 1.

[0135] Y 1 、Y 2 和Y 3

[0136] According to one implementation, Y 1 Y 2 and Y 3 Independently selected from CR 1a R 2a CR 1b R 2b NR 3a NR 3b ; where each Y 2 Choose to be the same or different, preferably the same, and each Y 3 You can choose to be the same or different.

[0137] According to one implementation, Y 1 Y 2 and Y 3 Independently selected from CR 1a R 2a CR 1b R 2b ; where each Y 2 The choice is either the same or different, with a preference for the same, and each Y... 2 The choice is either the same or different, with a preference for the same, and each Y... 3 You can choose to be the same or different.

[0138] According to one embodiment, in the organic compound of formula (III), A is selected from groups from H1 to H72: (H1) (H2), (H3) (H4) (H5) (H6) (H7) (H8) (H9) (H10) (H11)、 (H12)ぁ (H13)、 (H14)、 (H15)ぁ (H16)、 (H17)、 (H18)、 (H19)、 (H20)、 (H21)ぁ (H22)、 (H23)、 (H24)、 (H25)ぁ (H26)、 (H27)、 (H28)、 (H29)、 (H30)、 (H31)、 (H32)、 (H33)、 (H34)、 (H35)、 (H36)、 (H37)、 (H38)、 (H39)、 (H40)、 (H41)ぁ (H42)、 (H43)、 (H44)、 (H45)ぁ (H46)、 (E47)、 (E48)ぁ (H49)、 (H50) (H51)ぁ (H52)ぁ (H53)、 (H54)、 (H55)、 (H56)、 (H57)、 (H58)、 (H59)、 (H60)、 (H61)ぁ (H62)、 (H63) (H64) (H65) (H66) (H67) (H68) (H69) (H70) (H71) (H72), Among them, the asterisk " "Indicates the position of combination; R 1 R 2 R 3 R 4 R 5 R 6 R 7 and R 8 Independently selected from H, D, halogens, Cl, F, substituted or unsubstituted C1 to C6 alkyl groups, partially fluorinated C1 to C6 alkyl groups, perfluorinated C1 to C6 alkyl groups, CF3, substituted or unsubstituted C1 to C6 alkoxy groups, partially fluorinated C1 to C6 alkoxy groups, perfluorinated C1 to C6 alkoxy groups, OCF3, substituted or unsubstituted C6 to C 30 Aryloxy groups, partially fluorinated C6 to C6 30 Aryloxy groups, perfluorinated C6 to C6 groups 30 Aryloxy group, substituted or unsubstituted C6 to C6 30 Aryl, substituted or unsubstituted C3 to C4 30 Heteroaryl, CN, isocyanate, SCN, OCN, NO2, SF5 The substituents are selected from D, halogens, Cl, F, partially fluorinated C1 to C6 alkyl groups, perfluorinated C1 to C6 alkyl groups, CF3, partially fluorinated C1 to C6 alkoxy groups, perfluorinated C1 to C6 alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5. B 1 and B 2 They are selected independently from N and CR. 5A’ or CR 6A’ ,in CR 5A’ or CR 6A’ Each is independently selected from H, D, F, substituted or unsubstituted C6 to C6. 12 Aryl group, substituted or unsubstituted C1 to C2 groups having one to four heteroatoms selected from O, N, S and Si. 12 heteroaryl, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C1 to C2 12Alkoxy, substituted or unsubstituted C1 to C 12 Ether groups, CN, CF3, OCF3, halogens, Cl, F, Si(CH3)3, preferably R 1 To R 6 At least one of them contains CN, where CR 5A’ or CR 6A’ One or more substituents are independently selected from D, electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 30 aryl groups, and substituted or unsubstituted C6 to C6 groups. 30 Mixed aromatics, Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy, if present, are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, isocyanate, SCN, OCN, SF5, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, and perfluorinated C1 to C8 alkoxy.

[0139] According to one embodiment, in the organic compound of formula (III), A is selected from groups of H1 to H27, H44 to H46, H49, H50 and H66 to H72.

[0140] According to one embodiment, A of the organic compound of formula (III) is selected from one of the following:

[0141] According to one embodiment, A of the organic compound of formula (III) is selected from the following:

[0142] According to one embodiment, A of the organic compound of formula (III) is selected from the following:

[0143] According to one embodiment, A of the organic compound of formula (III) is selected from the following: (H2), (H66) (H67) or (H72).

[0144] According to one embodiment, the organic compound of formula (III) is selected from the organic compounds of formula (V): (V), In equation (V) - A 1 Groups independently selected from formula (Va): (Va), where Ar 1 Independently selected from substituted or unsubstituted aryl groups and substituted or unsubstituted heteroaryl groups, wherein for Ar 1 In the case of substitution, one or more of the substituents are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C8 alkoxy groups, substituted or unsubstituted C6 to C8 alkyl groups. 30 Aryl groups and substituted or unsubstituted C6 to C6 groups 30 Mixed aromatics, and Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy, if present, are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, and perfluorinated C1 to C8 alkoxy. - A 2 Groups independently selected from formula (Vb): (Vb), where Ar 2 Independently selected from substituted or unsubstituted aryl groups and substituted or unsubstituted heteroaryl groups, wherein for Ar 2 In the case of substitution, one or more of the substituents are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C8 alkoxy groups, substituted or unsubstituted C6 to C8 alkyl groups. 30 Aryl groups and substituted or unsubstituted C6 to C6 groups 30 Mixed aromatics, and Among them, C6 to C 30Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy, if present, are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, and perfluorinated C1 to C8 alkoxy. - A 3 Groups independently selected from formula (Vc): (Vc), where Ar 3 Independently selected from substituted or unsubstituted aryl groups and substituted or unsubstituted heteroaryl groups, wherein for Ar 3 In the case of substitution, one or more of the substituents are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C8 alkoxy groups, substituted or unsubstituted C6 to C8 alkyl groups. 30 Aryl groups and substituted or unsubstituted C6 to C6 groups 30 Mixed aromatics, and Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy, if present, are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, and perfluorinated C1 to C8 alkoxy. Among them, in A 1 A 2 A 3 In this context, each R' is independently selected from substituted or unsubstituted C6 to C6. 18 Aryl, C3 to C 18 Heteroaryl groups, electron-withdrawing groups, substituted or unsubstituted C1-C8 alkyl groups, partially fluorinated C1-C8 alkyl groups, perfluorinated C1-C8 alkyl groups, halogens, F, and CN; and The preferred formula (V) contains at least two compounds selected from C6 to C6. 19 aryl group or C3 to C 12 The heteroaryl group, wherein each of the C6 to C6 groups is a group of heteroaryl groups. 19 aryl group or C3 to C 12 The heteroaryl group is substituted, wherein one or more substituents are independently selected from halogens, F, CN, and partially perfluorinated C1 to C2 groups. 12Alkyl, perfluorinated C1 to C 12 Alkyl group, CF3.

[0145] According to one embodiment, in the organic compound of formula (III)

[0146] n is an even number, including 0, and preferably n is selected from 0, 2 or 4. m is an integer selected from 1. Y 1 Y 2 and Y 3 Independently selected from O, S, CR 1a R 2a CR 1b R 2b NR 3a NR 3b ; where each Y 3 You can choose to be the same or different. in Y 1 Y 2 and Y 3 They can form fused rings with A independently; Where R 1a R 2a R 1b and R 2b Independently selected from electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C8 alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups. Where R 1a R 2a R 1b and R 2b One or more substituents, when present, are independently selected from D, electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 30 aryl groups, and substituted or unsubstituted C6 to C6 groups. 30 Mixed aromatics; Among them, C6 to C 30 Aryl, C6 to C 30One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy, if present, are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, isocyanate, SCN, OCN, SF5, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, and perfluorinated C1 to C8 alkoxy. Where R 3a and R 3b Selected from electron-withdrawing groups, CN, partially fluorinated C1 to C6 alkyl groups, perfluorinated C1 to C6 alkyl groups, CF3, substituted or unsubstituted C6 to C6 alkyl groups. 30 aryl, or substituted or unsubstituted C3 to C4 30 Mixed aromatics, Where R 3a and R 3b One or more substituents, when present, are independently selected from D, electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C8 alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 30 aryl groups, and substituted or unsubstituted C6 to C6 groups. 30 Mixed aromatics; Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy, if present, are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, isocyanate, SCN, OCN, SF5, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, and perfluorinated C1 to C8 alkoxy. Where A is selected from substituted or unsubstituted C3 to C4 bonds containing at least one or more double bonds. 40 Cycloalkyl groups, substituted or unsubstituted C3 to C4 40 Cycloalkenyl groups, substituted or unsubstituted C2 to C3 40 Heterocyclic alkyl groups, containing one or more double bonds, substituted or unsubstituted C2 to C3 groups. 40 Heterocyclic alkyl groups, substituted or unsubstituted C2 to C3 40 Heterocyclic alkenyl groups, substituted or unsubstituted C6 to C6 groups 40 Aromatic groups, substituted or unsubstituted C2 to C3 40 heteroaromatic groups, wherein X 1 Each X 2 and each X3 They are conjugated to each other via the double bonds in A; One or more substituents on A, when present, are independently selected from D, electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C8 alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Mixed aromatics, Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy, if present, are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, isocyanate, SCN, OCN, SF5, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, and perfluorinated C1 to C8 alkoxy.

[0147] According to one embodiment, the organic compound of formula (III) comprises at least two compounds selected from C6 to C7. 19 aryl group or C3 to C 12 The heteroaryl group, wherein each of the C6 to C6 groups is a group of heteroaryl groups. 19 aryl group or C3 to C 12 The heteroaryl group is substituted, wherein one or more substituents are independently selected from halogens, F, CN, and partially perfluorinated C1 to C2 groups. 12 Alkyl, perfluorinated C1 to C 12 Alkyl group, CF3.

[0148] According to one embodiment, the compound of formula (III) is selected from compounds containing an indacenedione group, axial enes selected from compounds of formula (V), or compounds of formula (VIa) or (VIb): (VIa) (VIb), where B 1 and B 2 They are selected independently from N and CR. 5A’ or CR 6A’ , R 1A’ R 2A’ R 3A’ R 4A’ R5A’ and R 6A’ Selected independently from H, D, F, substituted or unsubstituted C6 to C6. 12 Aryl group, substituted or unsubstituted C1 to C2 groups having one to four heteroatoms selected from O, N, S and Si. 12 heteroaryl, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C1 to C2 12 Alkoxy, substituted or unsubstituted C1 to C 12 Ether groups, CN, CF3, OCF3, halogens, Cl, F, Si(CH3)3, preferably R 1 To R 6 At least one of them contains CN, where CR 5A’ or CR 6A’ One or more substituents are independently selected from D, electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 30 aryl groups, and substituted or unsubstituted C6 to C6 groups. 30 Mixed aromatics, among which C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy, if present, are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, isocyanate, SCN, OCN, SF5, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, and perfluorinated C1 to C8 alkoxy; X 1 and X 2 They are selected independently from equation (VII). (VII), where A and B are independently selected from H, D, substituted or unsubstituted C6 to C6. 12 Aryl group, substituted or unsubstituted C1 to C2 groups having one to four heteroatoms selected from O, N, S and Si. 12 heteroaryl, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C1 to C2 12 Alkoxy, substituted or unsubstituted C1 to C 12Ether groups, CN, CF3, OCF3, halogens, Cl, F, Si(CH3)3, and compounds of preferred formulas (VIa) or (VIb) contain at least two groups selected from C6 to C7. 19 aryl group or C3 to C 12 The heteroaryl group, wherein each of the C6 to C6 groups is a group of heteroaryl groups. 19 aryl group or C3 to C 12 The heteroaryl group is substituted, in which One or more substituents are independently selected from halogens, F, CN, and partially perfluorinated C1 to C2. 12 Alkyl, perfluorinated C1 to C 12 Alkyl group, CF3.

[0149] According to one embodiment, the organic compound of formula (III) is selected from compounds of formula (VIa) or (VIb), and the compound of formula (VIa) or (VIb) is represented by (VIIIa) or (VIIIb). (VIIIa) (VIIIb) in R 1A’ R 2A’ R 3A’ R 4A’ R 5A’ and R 6A’ Each is independently selected from H, D, substituted or unsubstituted C6 to C6. 12 Aryl group, substituted or unsubstituted C1 to C2 groups having one to four heteroatoms selected from O, N, S and Si. 12 heteroaryl, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C1 to C2 12 Alkoxy, substituted or unsubstituted C1 to C 12 Ether groups, CN, CF3, OCF3, halogens, Cl, F, Si(CH3)3, preferably R 1 To R 6 At least one of them contains CN; and X 1 and X 2 Each is selected independently from formula (IX). (IX) A and B are independently selected from H, D, and substituted or unsubstituted C6 to C6. 12 Aryl group, substituted or unsubstituted C1 to C2 groups having one to four heteroatoms selected from O, N, S and Si. 12 heteroaryl, substituted or unsubstituted C1 to C2 12Alkyl, substituted or unsubstituted C1 to C2 12 Alkoxy, substituted or unsubstituted C1 to C 12 Ether groups, CN, CF3, OCF3, halogens, Cl, F, Si(CH3)3, and compounds of preferred formula (VIIIa) or (VIIIb) contain at least two groups selected from C6 to C7. 19 aryl group or C3 to C 12 The heteroaryl group, wherein each of the C6 to C6 groups is a group of heteroaryl groups. 19 aryl group or C3 to C 12 The heteroaryl group is substituted, wherein one or more substituents are independently selected from halogens, F, CN, and partially perfluorinated C1 to C2 groups. 12 Alkyl, perfluorinated C1 to C 12 Alkyl group, CF3.

[0150] According to one embodiment, in formulas (III), (VIa), and (VIb), one or more substituents of the aryl, heteroaryl, alkyl, alkoxy, and ether groups, if present, are independently selected from C1 to C2 when present. 12 Alkyl, C1 to C 12 Alkoxy groups, having one to four heteroatoms selected from O, N, O, S, and Si, consisting of C1 to C2 atoms. 15 Heteroaryl, CN, halogen, Cl, F, CF3, OCF3, Si(CH3)3.

[0151] According to one embodiment, the organic compounds of formulas (III), (V), (VIa), (VIb), (VIIIIa) and / or (VIIIb) comprise at least one of the following portions:

[0152] B 1 Selected from CL 1 Or N; B 2 Selected from CL 2 Or N; B 3 Selected from CL 3 Or N; B 4 Selected from CL 4 Or N; B 5 Selected from CL 5 Or N; L 1 L 2 L 3 L 4 and L 5Independently selected from CN, isocyanate, SCN, OCN, NO2, SF5, partially fluorinated C1-C6 alkyl, perfluorinated C1-C6 alkyl, CF3, partially fluorinated C1-C6 alkoxy, perfluorinated C1-C6 alkoxy, OCF3, halogen, Cl, F, D or H; wherein the asterisk " "Indicates the position of combination.

[0153] According to one embodiment, the organic compounds of formulas (III), (V), (VIa), (VIb), (VIIIIa) and / or (VIIIb) comprise at least one of the following portions:

[0154] B 1 Selected from CL 1 Or N; B 2 Selected from CL 2 Or N; B 3 Selected from CL 3 Or N; B 4 Selected from CL 4 Or N; B 5 Selected from CL 5 Or N; L 1 L 2 L 3 L 4 and L 5 Independently selected from CN, partially fluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, CF3, OCF3, halogen, Cl, F, D or H; wherein the asterisk " "Indicates the position of combination.

[0155] According to one embodiment, the organic compounds of formulas (III), (V), (VIa), (VIb), (VIIIIa) and / or (VIIIb) comprise at least one of the following portions:

[0156] B 1 Selected from CL 1 Or N; B 2 Selected from CL 2 Or N; B 3 Selected from CL 3 Or N; B 4 Selected from CL 4 Or N; B5 Selected from CL 5 Or N; L 1 L 2 L 3 L 4 and L 5 Independently selected from CN, partially fluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, CF3, halogen, Cl, F, D or H; wherein the asterisk " "Indicates the position of combination.

[0157] According to one embodiment, the organic compounds of formulas (III), (V), (VIa), (VIb), (VIIIIa) and / or (VIIIb) comprise at least one of the following portions:

[0158] B 1 Selected from CL 1 Or N; B 2 Selected from CL 2 Or N; B 3 Selected from CL 3 Or N; B 4 Selected from CL 4 Or N; B 5 Selected from CL 5 Or N; L 1 L 2 L 3 L 4 and L 5 Independently selected from CN, partially fluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, CF3, halogen, Cl, F, D or H; wherein the asterisk " "Indicates the position of combination.

[0159] According to one embodiment, the organic compounds of formulas (III), (V), (VIa), (VIb), (VIIIIa) and / or (VIIIb) comprise at least one of the following portions:

[0160] B 1 Selected from CL 1 Or N; B 2 Selected from CL 2 Or N; B 3 Selected from CL 3 Or N; B 4 Selected from CL 4 Or N; B 5 Selected from CL 5 Or N; L 1 L 2 L 3 L 4 and L 5 Independently selected from CN, CF3, halogens, Cl, F, D, or H; wherein the asterisk " "Indicates the position of combination.

[0161] According to one embodiment, the organic compounds of formulas (III), (V), (VIa), (VIb), (VIIIIa) and / or (VIIIb) comprise at least one of the following portions: (XXa)

[0162] in

[0163] Z 1 Selected from CV 1 Or N; Z 2 Selected from CV 2 Or N; Z 3 Selected from CV 3 Or N; Z 4 Selected from CV 4 Or N; Z 5 Selected from CV 5 Or N; in V 1 V 2 V 3 V 4 and V 5 Independently selected from CN, isocyanate, SCN, OCN, NO2, SF5, partially fluorinated C1-C6 alkyl, perfluorinated C1-C6 alkyl, CF3, partially fluorinated C1-C6 alkoxy, perfluorinated C1-C6 alkoxy, OCF3, halogen, Cl, F, D or H; wherein the asterisk " "Indicates the position of combination.

[0164] According to one embodiment, the organic compounds of formulas (III), (V), (VIa), (VIb), (VIIIIa) and / or (VIIIb) comprise at least one of the following portions: (XXa)

[0165] in

[0166] Z 1 Selected from CV 1 Or N; Z 2 Selected from CV 2 Or N; Z 3 Selected from CV 3 Or N; Z 4 Selected from CV 4 Or N; Z 5 Selected from CV 5 Or N; in V 1 V 2 V 3 V 4 and V 5 Independently selected from CN, partially fluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, CF3, partially fluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy, OCF3, halogen, Cl, F, D or H; wherein the asterisk " "Indicates the position of combination.

[0167] According to one embodiment, the organic compounds of formulas (III), (V), (VIa), (VIb), (VIIIIa) and / or (VIIIb) comprise at least one of the following portions: (XXa)

[0168] in

[0169] Z 1 Selected from CV 1 Or N; Z 2 Selected from CV 2 Or N; Z 3 Selected from CV 3 Or N; Z 4 Selected from CV 4 Or N; Z 5 Selected from CV 5 Or N; in V 1 V 2 V 3 V 4 and V5 Independently selected from CN, partially fluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, CF3, halogen, Cl, F, D or H; wherein the asterisk " "Indicates the position of combination.

[0170] According to one embodiment, the organic compounds of formulas (III), (V), (VIa), (VIb), (VIIIIa) and / or (VIIIb) comprise at least one of the following portions: (XXa)

[0171] in

[0172] Z 1 Selected from CV 1 Or N; Z 2 Selected from CV 2 Or N; Z 3 Selected from CV 3 Or N; Z 4 Selected from CV 4 Or N; Z 5 Selected from CV 5 Or N; in V 1 V 2 V 3 V 4 and V 5 Independently selected from CN, CF3, halogens, Cl, F, D, or H; wherein the asterisk " "Indicates the position of combination.

[0173] According to one embodiment, the organic compounds of formulas (III), (V), (VIa), (VIb), (VIIIIa) and / or (VIIIb) comprise at least one of the following: (L1) (L2) (L3) (L4) (L5) (L6) (L7) (L8) (L9) (L10) (L11) (L12) (L13) (L14) (L15) (L16) (L17) (L18) (L19) (L20) (L21) (L22) (L23) (L24) (L25) (L26) (L27) (L28) (L29) (L30) (L31) (L32) (L33) (L34) (L35) (L36) (L37) (L38) (L39) (L40) (L41) (L42) (L43) (L44) (L45) (L46) (L47) (L48) (L49) (L50) (L51).

[0174] According to one embodiment, the compound of formula (III) is selected from compounds G1 to G27: (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).

[0175] Hole transport materials for pHIL and p-CGL

[0176] According to one embodiment, the hole injection layer and / or p-type charge generation layer comprises at least one arylamine compound, a diarylamine compound, a triarylamine compound, a compound of formula (IVa), or a compound of formula (IVb): (IVa) (IVb), in: T 1 T 2 T 3 T 4 and T 5 It is independently selected from single bond, phenylene group, biphenylene group, triphenylene group or naphthylene group, preferably single bond or phenylene group; T6 It can be phenylene oxide, biphenylene oxide, terphenylene oxide, or naphthylene oxide; Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 Selected independently from: substituted or unsubstituted C6 to C 20 aryl or substituted or unsubstituted C3 to C 20 Heteroarylene groups, substituted or unsubstituted biphenylidene, substituted or unsubstituted fluorene, substituted 9-fluorene, substituted 9,9-fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted triphenylidene, substituted or unsubstituted tetraphenylene, substituted or unsubstituted benzo[a]anthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthones, substituted or unsubstituted carbazole, substituted 9-phenylcarbazole, substituted or unsubstituted azaheptanyl, substituted or unsubstituted... The substituted dibenzo[b,f]azonium heterocyclic heptane, substituted or unsubstituted 9,9'-spirobis[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanton], 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 hetero 5-membered rings, substituted or unsubstituted 6-membered rings and / or substituted or unsubstituted 7-membered rings, substituted or unsubstituted fluorene, or fused-ring systems comprising 2 to 6 substituted or unsubstituted 5 to 7-membered rings, and 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; (IIIa) 6-membered aromatic non-heterocyclic rings; in Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 The substituents are selected from H, D, F, C(-O)R, either the same or different. 2 CN, Si(R) 2 3. P(-O)(R) 2 2. OR 2 S(-O)R 2 S(-O)2R 2Substituted or unsubstituted straight-chain alkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted branched alkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms; substituted or unsubstituted alkenyl or alkynyl groups having 2 to 20 carbon atoms; substituted or unsubstituted aromatic ring systems having 6 to 40 aromatic ring atoms; and substituted or unsubstituted heteroaromatic ring systems having 5 to 40 aromatic ring atoms; unsubstituted C6 to C6... 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 heterocyclic rings, 5 to 6-membered aromatic heterocyclic rings, unsaturated 5 to 7-membered non-heterocyclic rings, and 6-membered aromatic non-heterocyclic rings. Where R 2 The following can be selected from H, D, straight-chain alkyl groups having 1 to 6 carbon atoms, branched alkyl groups having 1 to 6 carbon atoms, cyclic alkyl groups having 3 to 6 carbon atoms, alkenyl or ynyl groups having 2 to 6 carbon atoms, C6 to C 18 Aryl or C3 to C 18 Mixed aromatic compounds.

[0177] Preferably, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 The substituents are selected from H, straight-chain alkyl groups having 1 to 6 carbon atoms, branched alkyl groups having 1 to 6 carbon atoms, cyclic alkyl groups having 3 to 6 carbon atoms, alkenyl or ynyl groups having 2 to 6 carbon atoms, and C6 to C6 substituents. 18 Aryl, C3 to C 18 The system comprises a heteroaryl group, a fused ring system comprising 2 to 4 unsubstituted 5 to 7-membered rings, wherein the rings are selected from: heterocyclic unsaturated 5 to 7-membered rings, aromatic heterocyclic 5 to 6-membered rings, non-heterocyclic unsaturated 5 to 7-membered rings, and aromatic non-heterocyclic 6-membered rings; more preferably, the substituents are selected from H, straight-chain alkyl groups having 1 to 4 carbon atoms, branched alkyl groups having 1 to 4 carbon atoms, cyclic alkyl groups having 3 to 4 carbon atoms, and / or phenyl groups.

[0178] Compounds of formula (IVa) and (IVb)

[0179] According to one embodiment, the hole injection layer and / or p-type charge generation layer comprises a compound of formula (IVa) or formula (IVb).

[0180] According to one embodiment of the invention, the compound of formula (IVa) or (IVb) is a matrix compound, preferably a substantially covalent matrix compound.

[0181] According to one embodiment, the substantially covalent matrix compound may have a molecular weight Mw of ≥400 g / mol but ≤2000 g / mol, preferably ≥450 g / mol but ≤1500 g / mol, more preferably ≥500 g / mol but ≤1000 g / mol, additionally preferably ≥550 g / mol but ≤900 g / mol, and even more preferably ≥600 g / mol but ≤800 g / mol.

[0182] According to one implementation, T 1 T 2 and T 3 It can be independently selected from single bonds, benzene groups, biphenylene groups, or triphenylene groups. According to one embodiment, T 1 T 2 and T 3 It can be independently selected from phenylene, biphenylene, or terphenylene, and T 1 T 2 and T 3 One of them is a single bond. According to one implementation, T 1 T 2 and T 3 It can be independently selected from phenylene group or biphenylene group, and T 1 T 2 and T 3 One of them is a single bond. According to one implementation, T 1 T 2 and T 3 It can be independently selected from phenylene group or biphenylene group, and T 1 T 2 and T 3 Two of them are single bonds.

[0183] According to one implementation, T 1 T 2 and T 3 It can be independently selected from the phenylene group, and T 1 T 2 and T 3 One of them is a single bond. According to one implementation, T 1 T 2 and T 3 It can be independently selected from the phenylene group, and T 1 T 2 and T 3 Two of them are single bonds.

[0184] According to one embodiment of the present invention, Ar 1 Ar 2 and Ar 3Selected independently from (E1) to (E16): (E1) (E2), (E3) (E4) (E5) (E6) (E7) (E8) (E9) (E10) (E11) (E12) (E13) (E14) (E15) (E16), Among them, the asterisk " "Indicates the position of combination.

[0185] According to one implementation, Ar 1 Ar 2 and Ar 3 It can be selected independently from E1 to E15; or selected from E1 to E10 and E13 to E15.

[0186] According to one implementation, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It can be independently selected from E1, E2, E5, E7, E9, E10, E13 to E16.

[0187] When Ar 1 Ar 2 and Ar 3 When selected within this range, the standard starting temperature can be within a range particularly suitable for large-scale production.

[0188] Compounds according to formula (IVa) or (IVb) can also be called "hole transport compounds".

[0189] According to one embodiment, the compound according to formula (IVa) or (IVb) comprises at least one naphthyl group, carbazole group, dibenzofuran group, dibenzothiophene group and / or a substituted fluorenyl group, wherein the substituent is independently selected from methyl, phenyl or fluorenyl.

[0190] According to one embodiment of the invention, when determined by the same method, the compound of formula (IVa) or (IVb) has a smaller HOMO energy level than that of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirodi[fluorene]-2,2',7,7'-tetraamine, preferably smaller than that of N4,N4,N4',N4'-tetra(4-methoxyphenyl)biphenyl-4,4'-diamine, more preferably smaller than that of N4,N4'-bis(9,9-dimethyl-9H-fluorene-2-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine. When calculated in the gas phase using the hybrid functionals B3LYP and Def2-TZVP basis sets, and with the packages ORCA V5.0.3 (Max Planck Institute for Kohlenforschung, Kaiser Wilhelm Platz 1, 45470, Muelheim / Ruhr, Germany) and WEASEL 1.9.2 (FAccTs GmbH, Rolandstrasse 67, 50677 Köln, Germany), the HOMO level of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirodi[fluorene]-2,2',7,7'-tetraamine is -4.39 eV, and the HOMO level of N4,N4,N4',N4'-tetra(4-methoxyphenyl)biphenyl-4,4'-diamine is -4.53 eV. The HOMO level of N4,N4'-bis(9,9-dimethyl-9H-fluorene-2-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine is -4.84 eV.

[0191] According to one embodiment of the invention, when calculated using the hybrid functionals B3LYP and Def2-TZVP basis sets in the gas phase, and using the packages ORCA V5.0.3 (Max Planck Institute für Kohlenforschung, Kaiser Wilhelm Platz 1, 45470, Muelheim / Ruhr, Germany) and WEASEL 1.9.2 (FAccTs GmbH, Rolandstrasse 67, 50677 Köln, Germany), the compound of formula (IVa) or (IVb) has a HOMO level of less than -4.39 eV, preferably less than -4.53 eV, and even more preferably less than -4.84 eV.

[0192] In the context of this invention, the term "having a HOMO level less than..." means that the absolute value of the HOMO level is greater than the absolute value of the HOMO level to which it is compared. Specifically, in the context of this invention, the term "having a HOMO level less than..." means that the HOMO level is further away from the vacuum level than the value of the HOMO level to which it is compared.

[0193] According to one embodiment of the electronic device, the molecular weight of the compound of formula (IVa) or (IVb) is selected in the range of ≥600 Da but ≤900 Da, preferably ≥620 Da but ≤850 Da. When the molecular weight of the compound of formula (IVa) or (IVb) is selected in this range, the compound of formula (IVa) or (IVb) is particularly suitable for vacuum thermal deposition.

[0194] According to one embodiment of the present invention, the compound of formula (IVa) or formula (IVb) is selected from formulas (F1) to (F21): (F1) (F2) (F3) (F4) (F5) (F6) (F7) (F8) (F9) (F10) (F11) (F12) (F13) (F14) (F15) (F16) (F17) (F18) (F19) (F20) (F21); The compounds of preferred formula (IVa) or formula (IVb) are selected from formulas (F3) to (F21), and more preferably from formulas (F4) to (F21).

[0195] n-type charge generation layer

[0196] According to one embodiment, the organic electronic device further includes a layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0197] According to one embodiment, the organic electronic device further includes a hole injection layer, a first hole transport layer, a second hole transport layer, a first electron blocking layer, a second electron blocking layer, an optional first hole blocking layer, an optional second hole blocking layer, a first electron transport layer, a second electron transport layer, and an electron injection layer.

[0198] According to one embodiment, the first n-type charge generation layer is in direct contact with the first p-type charge generation layer.

[0199] According to one embodiment, the second n-type charge generation layer is in direct contact with the second p-type charge generation layer.

[0200] According to one embodiment, the third n-type charge generation layer is in direct contact with the third p-type charge generation layer.

[0201] According to one embodiment, at least two light-emitting units each include an electron transport layer.

[0202] According to one embodiment, the organic electronic device further includes an electron transport layer disposed between a first light-emitting layer and a second light-emitting layer, wherein the electron transport layer is disposed in direct contact with a first n-type charge-generating layer, and wherein the electron transport layer is disposed between the first light-emitting layer and the first n-type charge-generating layer.

[0203] According to one embodiment, the organic electronic device further includes an electron transport layer disposed between a first light-emitting layer and a second light-emitting layer, wherein the electron transport layer is disposed in direct contact with a first n-type charge-generating layer, and wherein the electron transport layer is disposed between the first light-emitting layer and the first n-type charge-generating layer, and wherein the first n-type charge-generating layer is in direct contact with a first p-type charge-generating layer.

[0204] According to one embodiment, the matrix compound of the first n-type charge generation layer is an electron transport material.

[0205] According to one embodiment, the matrix compound of the first n-type charge generation layer is an organic electron transport material.

[0206] According to one embodiment, the matrix compound of the first n-type charge generation layer comprises at least one C2 to C3 group. 24 N-heteroaryl or P=X group, wherein X is O, P, or Se, with P=O being particularly preferred.

[0207] According to one embodiment, at least C2 to C 24 The N-heteroaryl group can be selected from compounds containing at least one acridine group, preferably at least two acridine groups, and even more preferably three acridine groups.

[0208] According to one embodiment, the matrix compound of the first n-type charge-generating layer comprises at least one group selected from the following groups: pyridine, pyrimidine, triazine, imidazole, benzimidazole, benzo[2]azole, quinone, benzo[2]quinone, imidazole[1,5- a Pyridine, quinoxaline, benzoquinoxaline, acridine, phenanthrene, benzoacridine, dibenzoacridine, phosphine oxide, tripyridine.

[0209] According to one embodiment, the matrix compound of the first n-type charge-generating layer comprises at least one phenanthroline group, preferably two phenanthroline groups; one or more pyridine groups; one or more pyrimidine groups; one or more triazine groups; one or more imidazo[1,5-] a ]Pyridine group; or one or more phosphine oxide groups.

[0210] According to one embodiment, the matrix compound of the first n-type charge-generating layer contains at least one phenanthroline group, preferably two phenanthroline groups; one or more pyridine groups; one or more pyrimidine groups; or one or more phosphine oxide groups.

[0211] According to one embodiment, the matrix compound of the first n-type charge-generating layer contains at least one phenanthroline group, preferably two phenanthroline groups; a pyridine group; a pyrimidine group; or a phosphine oxide group.

[0212] According to one embodiment, the matrix compound of the first n-type charge-generating layer comprises at least one phenanthroline group, preferably two phenanthroline groups; one or more pyridine groups; one or more pyrimidine groups; and one or more triazine groups.

[0213] According to one embodiment, the matrix compound of the first n-type charge-generating layer is selected from: 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline], (3-(10-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)anthracene-9-yl)phenyl)dimethylphosphine oxide, 3-(3-(9,10-diphenylanthracene-2-yl)phenyl)-1-(pyridin-2-yl)imidazo[1,5-a]pyridine, 7-(3-(1,10-phenanthroline-2-yl)phenyl)dibenzo[c]pyridine [h] acridine, 7-(3-([2,2':6',2''-terpyridine]-4'-yl)phenyl)dibenzo[c,h] acridine, 4'-(4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-yl)-2,2':6',2''-terpyridine, 4'-(4-(fluoranthene-3-yl)phenyl)-2,2':6',2''-terpyridine or 3-(9,10-di-2-naphthyl-2-anthrayl)phenyl]dimethylphosphine oxide.

[0214] According to one embodiment, the matrix compound of the first n-type charge-generating layer contains at least one phenanthroline group, preferably two phenanthroline groups.

[0215] According to one embodiment, the metal dopant is selected from a metal having an electronegativity of ≤1.4 eV on the Pauling scale, or a metal alloy containing a metal having an electronegativity of ≤1.4 eV on the Pauling scale.

[0216] According to one embodiment, the metal dopant is selected from a metal having an electronegativity of ≤1.35 eV on the Boring scale, or a metal alloy containing a metal having an electronegativity of ≤1.35 eV on the Boring scale.

[0217] According to one embodiment, the metal dopant is a metal selected from Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eu, and Yb, or a metal alloy containing a metal selected from Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eu, and Yb.

[0218] According to one embodiment, the metal dopant is a metal selected from Li, Na, K, Cs, Mg, Ca, Ba, Sm, Eu, and Yb, or a metal alloy containing a metal selected from Li, Na, K, Cs, Mg, Ca, Ba, Sm, Eu, and Yb.

[0219] According to one embodiment, the metal dopant is a metal selected from Li, Mg, and Yb, or a metal alloy containing a metal selected from Li, Mg, and Yb.

[0220] According to one embodiment, the metal dopant of the first n-type charge generation layer is a metal selected from Li, Mg, and Yb, or a metal alloy containing a metal selected from Li, Mg, and Yb.

[0221] According to one embodiment, the metal dopant is a metal selected from Li and Yb, or a metal alloy containing a metal selected from Li and Yb.

[0222] According to one embodiment, the metal dopant is Yb, or a metal alloy containing a metal selected from Li and Yb.

[0223] According to one embodiment, the metal dopant is Yb.

[0224] According to one embodiment, the metal dopant is in an oxidation state of ±0.

[0225] According to one embodiment, based on the total volume of the layer, the amount of metal dopant present in the first n-type charge generation layer is ≤99.9% by volume, preferably ≤99% by volume, more preferably ≤95% by volume, more preferably ≤90% by volume, more preferably ≤80% by volume, more preferably ≤70% by volume, more preferably ≤60% by volume, more preferably ≤50% by volume, more preferably ≤40% by volume, more preferably ≤30% by volume, more preferably ≤20% by volume, more preferably ≤10% by volume, more preferably ≤5% by volume, more preferably ≤3.0% by volume, more preferably ≤2% by volume, more preferably ≤1.5% by volume, more preferably ≤1.25% by volume, and most preferably ≤1.0% by volume.

[0226] According to one embodiment, based on the total volume of the layers, the amount of the matrix compound present in the first n-type charge-generating layer is ≥0.1 vol%, preferably ≥1 vol%, more preferably ≥5 vol%, more preferably ≥10 vol%, more preferably ≥20 vol%, more preferably ≥30 vol%, more preferably ≥40 vol%, more preferably ≥50 vol%, more preferably ≥60 vol%, more preferably ≥70 vol%, more preferably ≥80 vol%, more preferably ≥90 vol%, more preferably ≥95 vol%, more preferably ≥97.0 vol%, more preferably ≥98 vol%, more preferably ≥98.25 vol%, more preferably ≥98.5 vol%, more preferably ≥98.75 vol%, and most preferably ≥99.0 vol%.

[0227] Hole injection layer

[0228] 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 vacuum deposition is used to form HILs, the deposition conditions can vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. However, typically, vacuum deposition conditions can include deposition temperatures ranging from 100°C to 500°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 nm / s to 10 nm / s.

[0229] When spin coating or printing is used to form HIL, the coating conditions can vary depending on the 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.

[0230] The thickness of the HIL can range from about 1 nm to about 100 nm, for example, from about 1 nm to about 25 nm. When the thickness of the HIL is within this range, the HIL can have excellent hole injection characteristics without substantially damaging the driving voltage.

[0231] According to one embodiment of the present invention, the hole injection layer is adjacent to the anode layer.

[0232] According to one embodiment of the present invention, the hole injection layer is in direct contact with the anode layer.

[0233] Other layers

[0234] According to the present invention, the organic electronic device may further comprise other layers besides 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, the substrate should be a transparent or translucent material, such as a glass substrate or a transparent plastic substrate. If light is to be emitted through the top surface, the substrate can be a transparent or opaque material, such as a glass substrate, a plastic substrate, a metal substrate, a silicon substrate, or a backplane.

[0235] Anode layer

[0236] The anode layer can be formed by deposition or sputtering of the material used to form the anode layer. The material used to form the anode layer can be a high work function material, thereby promoting hole injection. The anode material can also be selected from low work function materials (i.e., aluminum). The anode electrode can be a transparent or reflective electrode. Transparent conductive oxides such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), aluminum zinc oxide (AlZO), and zinc oxide (ZnO) can be used to form the anode electrode. The anode layer can also be formed using metals, typically silver (Ag), gold (Au), or metal alloys.

[0237] Hole transport layer

[0238] The organic electronic device according to the present invention may further include at least one hole transport layer (HTL). According to one embodiment of the present invention, at least one hole transport layer is included in one of at least two light-emitting units, wherein preferably at least one hole transport layer is included in each light-emitting unit.

[0239] Hole transport layers (HTLs) can be formed on hollow inlets (HILs) or cavitation galvanic layers (CGLs) via vacuum deposition, spin coating, slot die coating, printing, casting, and Langmuir-Blodgett (LB) deposition. When forming HTLs via vacuum deposition or spin coating, the deposition and coating conditions can be similar to those for forming HILs or CGLs. However, the conditions for vacuum or solution deposition can vary depending on the compound used to form the HTL.

[0240] HTLs can be formed from any compound commonly used to form HTLs. For example, compounds suitable for use are disclosed in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010, which are incorporated herein by reference. Examples of compounds that can be used to form HTLs include: carbazole derivatives such as N-phenylcarbazole or polyvinylcarbazole; benzidine derivatives such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthyl-1-yl)-N,N'-diphenylbenzidine (α-NPD); and triphenylamine compounds such as 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA). In these compounds, TCTA is capable of transporting holes and inhibiting exciton diffusion into the EML.

[0241] According to one embodiment of the invention, the hole transport layer may comprise a substantially covalent matrix compound as described above.

[0242] According to a preferred embodiment of the invention, the hole injection layer and the hole transport layer may comprise the same substantially covalent matrix compound as described above.

[0243] According to one embodiment of the present invention, the hole transport layer may contain compounds of formula (VII) or (VIII) as described above.

[0244] According to a preferred embodiment of the invention, the hole injection layer and the hole transport layer may contain the same compound of formula (VII) or (VIII) as described above.

[0245] According to a preferred embodiment of the present invention, the p-type charge generation layer, the hole injection layer, and the hole transport layer may comprise the same substantially covalent matrix compound.

[0246] According to a preferred embodiment of the present invention, the p-type charge generation layer, the hole injection layer and the hole transport layer may contain the same compound of formula (VII) or (VIII) as described above.

[0247] 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, further about 20 nm to about 190 nm, further about 40 nm to about 180 nm, further about 60 nm to about 170 nm, further about 80 nm to about 160 nm, further about 100 nm to about 160 nm, and further about 120 nm to about 140 nm. The preferred thickness of the HTL can be from 170 nm to 200 nm.

[0248] When the thickness of the HTL is within this range, the HTL can have excellent hole transport characteristics without substantially damaging the driving voltage.

[0249] Electron blocking layer

[0250] The function of the electron blocking layer (EBL) is to prevent electrons from transferring from the emissive layer to the hole transport layer, thereby confining electrons within the emissive layer. This improves efficiency, operating voltage, and / or lifetime. Typically, the electron blocking layer contains a triarylamine compound. The LUMO level of the triarylamine compound can be closer to the vacuum level than the LUMO level of the hole transport layer. Compared to the HOMO level of the hole transport layer, the electron blocking layer can have a HOMO level further away from the vacuum level. The thickness of the electron blocking layer can be selected between 2 nm and 20 nm.

[0251] If the electron blocking layer has a high triplet energy level, it can also be described as a triplet control layer.

[0252] If a phosphorescent green or 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 is selected from triarylamine compounds whose triplet energy level is higher than that of the phosphorescent emitter in the adjacent emitting layer. Suitable compounds, particularly triarylamine compounds, for triplet control layers are described in EP 2 722 908 A1.

[0253] Photoactive Alpha Layer (PAL)

[0254] According to the present invention, the organic electronic device comprises at least two photoactive layers.

[0255] In the context of this invention, a photoactive layer specifically refers to a layer that converts current into photons or photons into current.

[0256] The photoactive layer can be a light-emitting layer or a light-absorbing layer, especially a light-emitting layer.

[0257] According to one embodiment of the present invention, the first photoactive layer is a first light-emitting layer, and the second photoactive layer is a second light-emitting layer.

[0258] According to one embodiment of the present invention, the organic electronic device is an organic electroluminescent device and / or an organic light-emitting diode, wherein the first photoactive layer is a first light-emitting layer and the second photoactive layer is a second light-emitting layer.

[0259] According to one embodiment of the present invention, the organic electronic device is an organic electroluminescent device, particularly an organic light-emitting diode, wherein the first photoactive layer is a first light-emitting layer and the second photoactive layer is a second light-emitting layer.

[0260] According to one embodiment of the present invention, the organic electronic device is an organic electroluminescent device comprising a substrate, an anode layer, a cathode layer, a first light-emitting layer, a second light-emitting layer, a hole injection layer, and a charge generation layer, particularly an organic light-emitting diode (OLED). The charge generation layer includes a p-type charge generation layer and an n-type charge generation layer. The hole injection layer, charge generation layer, first light-emitting layer, and second light-emitting layer are arranged between the anode layer and the cathode layer. The hole injection layer is positioned closer to the anode layer than the p-type charge generation layer. The p-type charge generation layer is arranged closer to the cathode layer than the n-type charge generation layer, and the n-type charge generation layer is arranged closer to the anode layer than the p-type charge generation layer. The hole injection layer is in direct contact with the anode layer. The charge generation layer is arranged between the first light-emitting layer and the second light-emitting layer. The hole injection layer contains compounds of formula (I): (I), in: M is a metal ion; n is the valence of M and is selected from 1 to 4; L is a ligand selected from formula (II). (II), in A 1 Selected from C=O or SO2; X 1 Selected from CR 1 Or N; X 2 Selected from CR 2 Or N; X 3 Selected from CR 3 Or N; X 4 Selected from CR 4 Or N; Where X 1 X 2 X 3 X 4 The 0, 1, or 2 elements are selected from N; R 1 To R 4 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl groups, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated or perfluorinated C1 to C8 alkoxy, OCF3, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Heteroaryl, substituted or unsubstituted 6-membered heteroaryl, substituted or unsubstituted 6-membered C3 to C5 heteroaryl; substituted or unsubstituted 6-membered C4 to C5 heteroaryl; halogen, F, Cl or CN, and wherein any R k To R k+1 They can form a ring, where k is an integer selected from 1 to 3; R 5 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Heteroaryl, substituted or unsubstituted 6-membered heteroaryl, substituted or unsubstituted 6-membered C3 to C5 heteroaryl; substituted or unsubstituted 6-membered C4 to C5 heteroaryl; Where R 1 To R 5 The replacement of C1 to C 12 Alkyl, substituted C1 to C8 alkoxy, substituted C6 to C 19 Aryl, substituted C2 to C 20 Heteroaryl, substituted 6-membered heteroaryl, substituted 6-membered C3 to C5 heteroaryl; one or more substituents of the substituted 6-membered C4 to C5 heteroaryl are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, partially fluorinated or perfluorinated C1 to C8 alkyl, partially or perfluorinated C1 to C8 alkoxy. AL is an auxiliary ligand that coordinates with metal M; m is an integer selected from 0 to 2; The p-type charge-generating layer includes organic compounds of formula (III). (III), in n is an integer selected from 0, 1, 2, 3, 4, 5 or 6, preferably 0, 2 or 4; m is an integer selected from 0 or 1; preferably 1; Y 1 Y 2 and Y 3 Independently selected from O, S, CR 1a R 2a CR 1b R 2b NR 3a NR 3b , or Y 1 Y 2 and Y 3 At least one of them forms a fused ring with A, wherein each Y 2 The choice is either the same or different, with a preference for the same, and each Y... 3 Choose between "same" or "different", with "same" being the preferred choice. R 1a R 2a R 1b and R 2b Independently selected from electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C8 alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 40 Aryl, substituted or unsubstituted C2 to C 40 Mixed aromatics, Where R 1aR 2a R 1b and R 2b One or more substituents are independently selected from D, electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 30 aryl groups, and substituted or unsubstituted C6 to C6 groups. 30 Mixed aromatics; Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, isocyanate, SCN, OCN, SF5, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, and perfluorinated C1 to C8 alkoxy. R 3a and R 3b Selected from electron-withdrawing groups, CN, partially fluorinated C1 to C6 alkyl groups, perfluorinated C1 to C6 alkyl groups, CF3, substituted or unsubstituted C6 to C6 alkyl groups. 30 aryl, or substituted or unsubstituted C3 to C4 30 Mixed aromatics, Where R 3a and R 3b One or more substituents are independently selected from D, electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C8 alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 30 aryl groups, and substituted or unsubstituted C6 to C6 groups. 30 Mixed aromatics; Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, isocyanate, SCN, OCN, SF5, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, and perfluorinated C1 to C8 alkoxy. A is selected from C3 to C4, whether substituted or unsubstituted. 40 Cyclic hydrocarbon group, substituted or unsubstituted C3 to C4 40 Cycloalkyl groups, containing one or more double bonds, substituted or unsubstituted C3 to C4 groups. 40 Cycloalkyl groups, substituted or unsubstituted C3 to C4 40 Cycloalkenyl groups, substituted or unsubstituted C2 to C3 40 Heterocyclic alkyl groups, containing one or more double bonds, substituted or unsubstituted C2 to C3 groups. 40 Heterocyclic alkyl groups, substituted or unsubstituted C2 to C3 40 Heterocyclic alkenyl groups, substituted or unsubstituted C6 to C6 groups 40 Aromatic groups, substituted or unsubstituted C2 to C3 40 heteroaryl groups, One or more substituents on A are independently selected from D, electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C8 alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Mixed aromatics, Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, isocyanate, SCN, OCN, SF5, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, and OCF3.

[0261] Photoactive layers can be formed on HTLs via vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When forming photoactive layers via vacuum deposition or spin coating, the deposition and coating conditions can be similar to those for HIL formation. However, the deposition and coating conditions can vary depending on the compound used to form the photoactive layer.

[0262] Emissive Layer (EML)

[0263] According to one embodiment of the present invention, the organic electronic device may further include a light-emitting layer, wherein the light-emitting layer is disposed between the anode layer and the cathode layer.

[0264] EML can be formed on HTL via vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When using vacuum deposition or spin coating to form EML, the deposition and coating conditions can be similar to those for HIL formation. However, the deposition and coating conditions can vary depending on the compound used to form the EML.

[0265] The luminescent layer (EML) can be formed by a combination of a host and a luminescent dopant. Examples of hosts are: Alq3, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 4,4',4''-tris(carbazole-9-yl)triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-bis-2-naphthylanthracene (TBADN), stilbeneyl arylene (DSA), and bis(2-(2-hydroxyphenyl)benzothiazole)zinc (Zn(BTZ)2).

[0266] 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 higher efficiency. The luminescent material can be a small molecule or a polymer.

[0267] Examples of red-emitting dopants include PtOEP, Ir(piq)3, and Btp2Ir(acac), but are not limited to these. These compounds are phosphorescent; however, fluorescent red-emitting dopants can also be used.

[0268] Examples of phosphorescent green luminescent dopants are Ir(ppy)3 (ppy = phenylpyridine), Ir(ppy)2 (acac), and Ir(mpyp)3.

[0269] Examples of phosphorescent blue emitting electron dopants are: F₂Irpic, (F₂ppy)₂Ir(tmd), and Ir(dfppz)₃; as well as terfluorene. Examples of fluorescent blue emitting electron dopants are 4,4'-bis(4-diphenylaminostyryl)biphenyl (DPAVBi) and 2,5,8,11-tetratert-butylperylene (TBPe).

[0270] Based on 100 parts by weight of the host, the amount of luminescent dopant can range from about 0.01 parts by weight to about 50 parts by weight. Alternatively, the luminescent layer can be composed of a luminescent polymer. The EML can have a thickness of about 10 nm to about 100 nm, for example, about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML can exhibit excellent luminescence without substantially impairing the driving voltage.

[0271] According to a preferred embodiment of the present invention, the light-emitting layer comprises a light-emitting compound of formula (X): (X), in Z 1 Z 2 and Z 3 They may be the same as or different from each other, and each is independently selected from monocyclic to polycyclic aromatic hydrocarbon rings or monocyclic to polycyclic aromatic heterocycles; Ar 31 and Ar 32 They may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or combined with an adjacent substituent to form a substituted or unsubstituted aromatic ring or a substituted or unsubstituted aliphatic ring; R 31 R 32 and R 33 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amine groups, substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups, or adjacent substituents combined with each other to form substituted or unsubstituted aromatic rings or substituted or unsubstituted aliphatic rings. One or more of the substituents are selected from deuterium, alkyl groups having 1 to 6 carbon atoms, alkylsilyl groups having 1 to 30 carbon atoms, arylsilyl groups having 6 to 50 carbon atoms, alkylamine groups having 1 to 30 carbon atoms, alkylarylamine groups having 1 to 50 carbon atoms, arylamine groups having 6 to 50 carbon atoms, aryl groups having 6 to 30 carbon atoms, and heteroaryl groups having 2 to 30 carbon atoms, or substituents connected with two or more substituents selected from said groups, or adjacent substituents combined with each other to form an aliphatic hydrocarbon ring having 3 to 60 carbon atoms, said hydrocarbon ring being unsubstituted or substituted by said substituents; r 31 r 32 and r 33 Each is an integer of 0, 1, 2, 3, or 4, and when r 31 to r 33 When the value is 2 or greater, the substituents in the parentheses may be the same or different from each other.

[0272] According to one implementation, for equation (III): Z 1 Z 2 and Z 3They may be the same as or different from each other, and each is independently selected from monocyclic to bicyclic aromatic hydrocarbon rings, or monocyclic to bicyclic aromatic heterocycles containing O, N or S; Ar 31 and Ar 32 They may be the same as or different from each other, and each is independently selected from alkyl groups having 1 to 10 carbon atoms that are unsubstituted or substituted with aryl groups, aryl groups having 6 to 30 carbon atoms that are unsubstituted or substituted with aryl groups, or heteroaryl groups having 2 to 30 carbon atoms. R 31 R 32 and R 33 They may be identical or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted silyl groups, and substituted or unsubstituted aryl groups. Or substituted or unsubstituted heteroaryl groups.

[0273] According to one implementation, for equation (III): Z 1 Z 2 and Z 3 They may be the same as each other or different, and each is independently selected from the benzene ring or the thiophene ring; Ar 31 and Ar 32 They may be the same as or different from each other, and each is independently selected from phenyl group, biphenyl group, naphthyl group, dimethylfluorenyl group, diphenylfluorenyl group, dibenzofuran group or dibenzothiophene group; R 31 R 32 and R 33 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 5 to 50 carbon atoms, substituted or unsubstituted silyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms.

[0274] According to a preferred embodiment of the present invention, the light-emitting layer comprises a light-emitting compound of formula (X), selected from formulas (BD1) to (BD9): (BD1) (BD2) (BD3) (BD4) (BD5) (BD6) (BD7) (BD8) (BD9)

[0275] According to a preferred embodiment of the present invention, the light-emitting layer comprises an organic light-emitting host compound, wherein the organic light-emitting host compound comprises

[0276] - At least one fused aromatic ring system consisting of 3 to 5 rings; and

[0277] - 3 to 7 aromatic or heteroaromatic rings, wherein one or more daughter groups in the aromatic and / or heteroaromatic rings may fused to form a fused aromatic or heteroaromatic ring system; The molecular weight (Mw) of the organic light-emitting host compound is in the range of ≥400 g / mol but ≤2000 g / mol.

[0278] According to a preferred embodiment of the present invention, the organic light-emitting host compound has the formula (XI). (XI), where Ar 41 and Ar 42 Independently selected from substituted or unsubstituted C6 to C6. 24 Aryl, substituted or unsubstituted C3 to C4 24 Mixed aromatics; L 41 and L 42 Independently selected from direct bonds or substituted or unsubstituted C6 to C1 bonds. 24 Aranediols, substituted or unsubstituted C3 to C4 24 Mixed aromatic subunits; R 41 To R 48 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C6 to C6 19 Aryl, substituted or unsubstituted C3 to C4 12 Mixed aromatics; in Ar 41 Ar 42 L 41 L 42 R 41 To R 48 The substituents on the surface are independently selected from D, C6 to C6. 10Aryl, 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 or perfluorinated C1 to C 16 Alkyl, partially or perfluorinated C1 to C2 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, F or CN.

[0279] According to a preferred embodiment of the present invention, the organic light-emitting body and / or the compound of formula (XI) are selected from formulas (BH1) to (BH13): (BH1) (BH2) (BH3) (BH4) (BH5) (BH6) (BH7) (BH8) (BH9) (BH10) (BH11) (BH12) (BH13).

[0280] According to a preferred embodiment of the present invention, the light-emitting layer comprises a light-emitting dopant of formula (X) and an organic light-emitting body of formula (XI).

[0281] According to a preferred embodiment of the organic electronic device, the hole injection layer comprises a compound of formula (I) and a compound of formula (III), the hole transport layer comprises a compound of formula (III), preferably the hole injection layer and the hole transport layer comprise the same compound of formula (III), and the light-emitting layer comprises a light-emitting dopant of formula (X) and an organic light-emitting body of formula (XI). The hole transport layer is arranged between the hole injection layer and the light-emitting layer, and the light-emitting layer is arranged between the hole transport layer and the cathode layer.

[0282] According to a preferred embodiment of the organic electronic device, the hole injection layer comprises a compound of formula (I) and a compound of formula (III), the hole transport layer comprises a compound of formula (III), preferably the hole injection layer and the hole transport layer comprise the same compound of formula (III), and the light-emitting layer comprises a light-emitting dopant of formula (X) and an organic light-emitting body of formula (XI). The hole transport layer is arranged between the hole injection layer and the light-emitting layer, and the light-emitting layer is arranged between the hole transport layer and the cathode layer. The anode layer may include: a first anode sublayer containing Ag or Au with a thickness of 100 nm to 150 nm, a second anode sublayer containing or composed of transparent conductive oxide with a thickness of 3 nm to 20 nm, and a third anode sublayer containing or composed of transparent conductive oxide with a thickness of 3 nm to 20 nm, wherein the transparent conductive oxide is preferably selected from ITO or IZO.

[0283] Hole blocking layer (HBL)

[0284] Hole blocking layers (HBLs) can be formed on EMLs using methods such as vacuum deposition, spin coating, slot die coating, printing, casting, and LB deposition to prevent holes from diffusing into ETLs. When the EML contains phosphorescent dopants, the HBL can also have triplet exciton blocking functionality.

[0285] HBL can also be called auxiliary ETL or a-ETL.

[0286] When using vacuum deposition or spin coating to form HBLs, the deposition and coating conditions can be similar to those used to form HILs. However, the deposition and coating conditions can vary depending on the compound used to form the HBL. Any compound commonly used to form HBLs can be used. Examples of compounds used to form HBLs include diazole derivatives, triazole derivatives, phenanthrene-rhein derivatives, and azazine derivatives, preferably triazine or pyrimidine derivatives.

[0287] HBLs can have a thickness in the range of about 5 nm to about 100 nm, for example, about 10 nm to about 30 nm. When the thickness of the HBL is within this range, the HBL can have excellent hole blocking properties without substantially impairing the driving voltage.

[0288] Electron Transport Layer (ETL)

[0289] The organic electronic device according to the present invention may further include at least one electron transport layer (ETL). According to one embodiment of the present invention, at least one electron transport layer is included in at least one of at least two light-emitting units, wherein preferably at least one electron transport layer is included in each light-emitting unit.

[0290] According to another embodiment of the invention, the electron transport layer may further comprise an azazine compound, preferably a pyridine, pyrimidine, or triazine compound, most preferably a triazine or pyrimidine compound.

[0291] According to another embodiment of the present invention, the electron transport layer may further comprise 2-([1,1'-biphenyl]-4-yl)-4-(9,9-diphenyl-9H-fluorene-4-yl)-6-phenyl-1,3,5-triazine, 2-(3-(2,6-dimethylpyridin-3-yl)-5-(phenanthrene-9-yl)phenyl)-4,6-diphenyl-1,3,5-triazine, 3'-(4-phenyl-6-(spiro[fluorene-9,9'-xanthan]-2'-yl)-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-4-carboxylonite and 4'-(4-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthyl-1-yl)-[1,1'-biphenyl]-4-carboxylonite.

[0292] In one embodiment, the electron transport layer may further comprise a dopant selected from alkali metal organic complexes, preferably LiQ.

[0293] The thickness of the ETL can range from about 15 nm to about 50 nm, for example, from about 20 nm to about 40 nm. When the thickness of the ETL is within this range, the ETL can have satisfactory electron injection characteristics without substantially impairing the driving voltage.

[0294] 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 azine compound. Preferably, the azine compound is a pyridine, pyrimidine, or triazine compound, with a triazine compound being most preferred.

[0295] Electron Injection Layer (EIL)

[0296] Optional electron transport layers (EILs) that facilitate electron injection from the cathode can be formed on the electron transport layer (ETL), preferably on the ETL closest to the cathode, and more preferably directly on the electron transport layer. Examples of materials used to form EILs 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 EILs are similar to those for forming HILs, but the deposition and coating conditions may vary depending on the material used to form the EIL.

[0297] 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 properties without substantially impairing the driving voltage.

[0298] cathode layer

[0299] The cathode layer is formed on an ETL or optionally an EIL. The cathode layer can be formed of a metal, alloy, conductive compound, or a mixture thereof. The cathode electrode can have a low work function. For example, the cathode layer can be formed of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), etc. Alternatively, the cathode electrode can be formed of a transparent conductive oxide such as ITO or IZO.

[0300] 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, it can be transparent or translucent even if the cathode layer is formed of metal or metal alloy.

[0301] In a preferred embodiment, the cathode layer comprises a metal or metal alloy and is transparent.

[0302] It should be understood that the cathode layer is not part of the electron injection layer or the electron transport layer.

[0303] Devices

[0304] According to one embodiment of the present invention, the electronic organic device is an organic electroluminescent device and / or an organic light-emitting diode.

[0305] According to a preferred embodiment of the present invention, the electronic device is an organic light-emitting diode, wherein light is emitted through a cathode layer.

[0306] The present invention also relates to a display device comprising organic electronic devices according to the present invention.

[0307] According to a preferred embodiment of the invention, the display device includes an organic electronic device according to the invention, wherein the cathode layer is transparent. Attached Figure Description

[0308] In the described embodiments, the components described above, as well as the claimed components and the components used according to the invention, are without any particular exceptions in terms of their size, shape, material selection, and technical concept, so that selection criteria known in the relevant field can be applied without restriction.

[0309] Further details, features, and advantages of the invention are disclosed in the dependent claims and the following description of the various accompanying drawings, which illustrate preferred embodiments of the invention by way of example. However, any embodiment is not necessarily representative of the full scope of the invention, and therefore the scope of the invention is to 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 provide further explanation of the claimed invention.

[0310] Figure 1 This is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment of the present invention.

[0311] Figure 2 This is a schematic cross-sectional view of a multilayer organic electronic device according to another exemplary embodiment of the present invention.

[0312] Figure 3 This is a schematic cross-sectional view of a multilayer organic electronic device according to another exemplary embodiment of the present invention.

[0313] Figure 4 This is a schematic cross-sectional view of the anode layer 120 on the substrate 110.

[0314] The accompanying drawings will now be described in more detail with reference to embodiments. However, the present invention is not limited to the following drawings.

[0315] In this document, when a first element is referred to as being formed or arranged "on" or "above" a second element, the first element may be arranged directly on the second element, or one or more other elements may be arranged between them. When a first element is referred to as being "directly" formed or arranged "on" or "above" a second element, no other elements are arranged between them.

[0316] Figure 1 This is a schematic cross-sectional view of an organic electronic device 100 according to an exemplary embodiment of the present invention.

[0317] refer to Figure 1The organic electronic device 100 includes: a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 comprising a compound of formula (I) and optionally at least one arylamine compound, a diarylamine compound, a triarylamine compound, a compound of formula (IVa) or a compound of formula (IVb), and a first photoactive layer, particularly a first light-emitting layer 140, which includes a first hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, a first light-emitting layer (EML1) 143, a first hole blocking layer (HBL1) 144, and a first electron transport layer (ETL1) 145. The organic electronic device 100 further includes: a first charge generating layer (CGL1) 150, which includes a first n-type charge generating layer (n-CGL1) 151 and a first p-type charge generating layer (p-CGL1) 152, wherein the first p-type charge generating layer (p-CGL1) 152 includes an organic compound of formula (III) and optionally at least one arylamine compound, a diarylamine compound, a triarylamine compound, a compound of formula (IVa) or a compound of formula (IVb).

[0318] The organic electronic device 100 further includes: a second photoactive layer, particularly a second light-emitting layer 240, which includes a second hole transport layer (HTL2) 241, a second electron blocking layer (EBL2) 242, a second light-emitting layer (EML2) 243, a second hole blocking layer (HBL2) 244, and a second electron transport layer (ETL2) 245. The organic electronic device 100 also includes an electron injection layer (EIL) 180 and a cathode layer (CAT) 190.

[0319] Figure 2 This is a schematic cross-sectional view of a multilayer organic electronic device 100 according to another exemplary embodiment of the present invention. Figure 2 and Figure 1 The difference is that, Figure 1 The organic electronic device 100 further includes a second charge generating layer (CGL2) 250 disposed on the second photoactive layer, particularly the second light-emitting layer 240, which includes a second n-type charge generating layer (n-CGL2) 251 and a second p-type charge generating layer (p-CGL2) 252, wherein the second p-type charge generating layer (p-CGL2) 252 may optionally contain an organic compound of formula (III) and optionally at least one arylamine compound, diarylamine compound, triarylamine compound, compound of formula (IVa), or compound of formula (IVb). Figure 2 Organic electronic devices 100 and Figure 1The difference lies in that it also includes a third light-emitting layer 340 disposed on the second charge generation layer (CGL2) 250, which includes a third hole transport layer (HTL3) 341, a third electron blocking layer (EBL3) 342, a third light-emitting layer (EML3) 343, a third hole blocking layer (HBL3) 344, and a third electron transport layer (ETL3) 345.

[0320] Figure 3 This is a schematic cross-sectional view of a multilayer organic electronic device 100 according to another exemplary embodiment of the present invention. Figure 3 and Figure 2 The difference is that, Figure 2 The organic electronic device 100 further includes a third charge generating layer (CGL3) 350 disposed on the third light-emitting layer 340, which includes a third n-type charge generating layer (n-CGL3) 351 and a third p-type charge generating layer (p-CGL3) 352, wherein the third p-type charge generating layer (p-CGL3) 352 may optionally contain an organic compound of formula (III) and optionally at least one arylamine compound, diarylamine compound, triarylamine compound, compound of formula (IVa), or compound of formula (IVb). Figure 3 Organic electronic devices 100 and Figure 2 The difference lies in that it also includes a fourth light-emitting layer 440 disposed on the third charge-generating layer (CGL3) 350, which includes a fourth hole transport layer (HTL4) 441, a fourth electron blocking layer (EBL4) 442, a fourth light-emitting layer (EML4) 443, a fourth hole blocking layer (HBL4) 444 and a fourth electron transport layer (ETL4) 445.

[0321] Despite Figure 1 , Figure 2 and Figure 3 Not shown, but a capping layer and / or sealing layer may be further formed on the cathode layer 190 to seal the organic electronic device 100. Furthermore, various other modifications may be made thereto.

[0322] Figure 4 This is a schematic cross-sectional view of the anode layer 120 on the substrate 110. The anode layer 120 includes a first anode sublayer 121, a second anode sublayer 122, and a third anode sublayer 123.

[0323] In the following description, one or more exemplary embodiments of the present invention will be described in detail with reference to the following examples. However, these examples are not intended to limit the purpose and scope of the one or more exemplary embodiments of the present invention. Detailed Implementation

[0324] The present invention is also illustrated by the following exemplary and non-binding embodiments.

[0325] The protonated form LH of the ligand of formula (II) can be obtained by methods known in the art, such as J. G. Lombardino. J. Org. Chem. Prepared using the method described in 1968, 33, 10, 3938–3941.

[0326] The compounds of formula (I) can be prepared by methods known in the art and as described below.

[0327] Compounds of formula (I), where M is Cu, Zn, Cd, Pb and n is 2, can be obtained through Enchev, Venelin et al. J. Mol. Struct. Prepared by the method described in , 2001, 595(1-3), 67-76.

[0328] Compounds of formula (I), where M is Fe and n is 3, can be obtained by Ahmedova, Anife et al. Inorg. Chim . Acta Prepared by the method described in , 2006, 359(10), 3123-3128.

[0329] Compounds of formula (I), where M is Fe and n is 2, can be obtained from Rusanov, Ventzislav, et al. Eur. J. Chem. , 2014, 5 Prepared by the method described in (1), 176-180.

[0330] The compounds of formula (I) can be prepared by methods known in the art and as described below.

[0331] Synthesis of bis(1-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)-2,2,2-trifluoroethoxy)copper (Al)

[0332] 2.42 g (10 mmol) of 3-hydroxy-2-(2,2,2-trifluoroacetyl)-1H-inden-1-one and 1 g (5 mmol) of copper acetate monohydrate were added to 50 mL of methanol and stirred vigorously for 3 days. The suspension was filtered and the solid was washed with methanol. After drying under high vacuum at 60 °C, 2.39 g (95%) of the product as a light green powder was obtained, which was further purified by vacuum sublimation.

[0333] Tris((2-(3,5-bis(trifluoromethyl)benzoyl)-1,1-dioxobenzo[b]thiophen-3-yl)oxy)iron Synthesis of (A91)

[0334] 3 g (7.1 mmol) of (3,5-bis(trifluoromethyl)phenyl)(3-hydroxy-1,1-dioxobenzo[b]thiophene-2-yl) methyl ketone was dissolved in 30 mL of 2-methyltetrahydrofuran, and 0.38 g (7.1 mmol) of sodium methoxide and 0.41 g (2.49 mmol) of ferric chloride were added. The mixture was stirred at room temperature for 2 hours. The precipitate was filtered off, and the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane, and the product was precipitated by adding hexane. After filtration, the product was dried under high vacuum to obtain 2.82 g (90%) of deep red solid, which was further purified by vacuum sublimation.

[0335] bis((2-(3,5-bis(trifluoromethyl)benzoyl)-1,1-dioxobenzo[b]thiophene-3-yl)oxy)manganese Synthesis of (A116)

[0336] 4.0 g (9.47 mmol) of (3,5-bis(trifluoromethyl)phenyl)(3-hydroxy-1,1-dioxobenzo[b]thiophene-2-yl) methyl ketone was dissolved in 40 mL of ethanol, and a solution of 1.16 g (4.74 mmol) of manganese acetate tetrahydrate in 35 mL of ethanol was added. The mixture was stirred under reflux for 2 hours. After cooling, the precipitate was filtered off, washed with ethanol, and the solvent was removed under reduced pressure. The residue was dissolved in tetrahydrofuran and precipitated with hexane. The solid was filtered off, washed with hexane, and dried under high vacuum to obtain 2.41 g (57%) of a pale orange solid, which was further purified by sublimation under vacuum.

[0337] Compounds of formula (III) can be prepared by methods known in the art, such as US 2005121667 A1, or as described later.

[0338] Option 1: A method for preparing compounds of formula (III)

[0339] Starting material E is transformed into intermediate A

[0340] The conversion of diketones to dihalides was achieved using the scheme published by Bucsis and Friedrichs in Chem. Ber. 1976, 109, 2462–2468.

[0341] Intermediate B (conditions a / b)

[0342] In a three-necked round flask equipped with a reflux condenser, dropping funnel, and septum, 2.4 equivalents of sodium hydride were suspended in dry DMF under an inert atmosphere and cooled to below 10°C using an ice bath. After adding a solution of 2.3 equivalents of XH2 dropwise to anhydrous DMF (condition b: anhydrous DME), the mixture was stirred at 0°C to 10°C for 15 minutes. Then, 1 equivalent of compound A (starting material or intermediate) was added in a single addition (condition b: followed by 0.05 equivalents of catalyst), and the mixture was stirred at 0°C for 15 minutes, then at room temperature for 15 minutes, and finally at 80°C (under reflux for condition b) overnight. If the reaction was not complete by the next morning, the reaction mixture was added dropwise to a suspension of compound B deprotonated with a slight excess of sodium hydride (0.6 equivalents to 2.1 equivalents, respectively), and stirred at 80°C for an additional 24 hours. After the reaction was complete, the mixture was poured onto an ice / water mixture and acidified with hydrochloric acid. The aqueous phase was extracted twice with ethyl acetate, and the organic phase was washed three times with semi-concentrated brine, then washed again with concentrated brine, and dried over sodium sulfate. After removing the solvent, the product was stirred overnight in DCM at room temperature, filtered, and redissolved in a small amount of ethyl acetate. The concentrated solution was then added dropwise to an 8-fold excess of dichloromethane. The precipitate was filtered, washed twice with dichloromethane, and dried.

[0343] Intermediate C

[0344] In a three-necked round flask equipped with a reflux condenser, dropping funnel, and septum, 1.2 to 1.6 equivalents of sodium hydride were suspended in dry DME under an inert atmosphere and cooled to below 10°C using an ice bath. After adding 1.1 to 1.5 equivalents of a solution of XH2 dropwise to the dry DME, the mixture was stirred at 0 to 10°C for 15 minutes. Then, 1 equivalent of compound A (starting material or intermediate) as a solid was added in a single batch, and the mixture was stirred at 0°C for 15 minutes and then stirred overnight at room temperature. If the reaction was found to be incomplete the next morning, the reaction mixture was added dropwise to an additional 0.5 to 1 equivalent of a suspension of XH2 deprotonated with a slight excess of sodium hydride (0.6 to 1.1 equivalents, respectively), and stirred at room temperature for another 24 hours. After the reaction was complete, the mixture was poured onto an ice / water mixture and acidified with hydrochloric acid. The aqueous phase was extracted twice with ethyl acetate, and the organic phase was washed three times with semi-concentrated brine, then washed again with concentrated brine, and dried over sodium sulfate. After removing the solvent, the product was stirred overnight in toluene at room temperature, filtered, washed several times with toluene, and dried.

[0345] Intermediate D

[0346] In a three-necked round flask equipped with a reflux condenser, dropping funnel, and septum, 1.5 equivalents of sodium hydride were suspended in dry DMF under an inert atmosphere and cooled to below 10°C using an ice bath. After adding 1.4 equivalents of a solution of XH2 dropwise to anhydrous DMF, the mixture was stirred at 0°C to 10°C for 15 minutes. Then, 1 equivalent of intermediate C as a solid was added in a single addition, and the mixture was stirred at 0°C for 15 minutes, then at room temperature for 15 minutes, and finally at 80°C overnight. If the reaction was not complete by the next morning, the reaction mixture was added dropwise to an additional 0.5 to 1.5 equivalents of a suspension of compound XH2 deprotonated with a slight excess of sodium hydride (0.6 to 1.6 equivalents, respectively), and stirred at 80°C for an additional 24 hours. After the reaction was complete, the mixture was poured onto an ice / water mixture and acidified with hydrochloric acid. The aqueous phase was extracted twice with ethyl acetate, and the organic phase was washed three times with semi-concentrated brine, then washed again with concentrated brine, and dried over sodium sulfate. After removing the solvent, the product was stirred overnight in DCM at room temperature, filtered, and redissolved in a small amount of ethyl acetate. The concentrated solution was then added dropwise to an 8-fold excess of dichloromethane. The precipitate was filtered, washed twice with dichloromethane, and dried.

[0347] Compound (II) derived from intermediate B / D

[0348] Prior to oxidation, intermediates B / D were converted to potassium salts by suspension in a potassium carbonate solution. The salts were then extracted with ethyl acetate, and the solution was concentrated under vacuum. The potassium salt was precipitated by dropwise addition of the concentrate to excess n-hexane and filtered off. After drying under vacuum for two hours, the potassium salts were suspended in dry DCM under an inert atmosphere, and 1.1 equivalents of PIFA were added in a single addition. The mixture was stirred overnight at room temperature in the dark. The product was filtered off, washed three times with DCM, and purified by stirring in 50% acetic acid followed by stirring in hot chloroform. The mother liquor was removed by filtration and washed with chloroform. The product can be further purified by methods known in the art, such as those in US 2005121667 A1.

[0349] Compound (III) derived from starting material E

[0350] The conversion of diketones to quinone dimethylamine was achieved using Lehnerts' reagent as described in J. Org. Chem. 1995, 60, 13, 4077–4084. The synthesis of N,N-dicyanoquinone diimine was carried out using bis(trimethylsilyl)carbodiimine following the scheme of Hünigs and Aumüllers (Liebigs Annalen der Chemie 1986 (1), 142–164).

[0351] Calculation of HOMO and LUMO using Equation (III)

[0352] HOMO and LUMO were calculated using the package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). The calculations were performed by applying hybrid functionals B3LYP and 6-31G in the gas phase. The basis set determines the optimal 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 is selected.

[0353] LUMO calculations for compounds of formula (I) and comparative compounds

[0354] The energies of the lowest unoccupied molecular orbitals (LUMOs) of compounds and comparative compounds of Equation (I) were calculated using the packages ORCA V5.0.3 (Max Planck Institute for Kohlenforschung, Kaiser Wilhelm Platz 1, 45470, Muelheim / Ruhr, Germany) and WEASEL 1.9.2 (FAccTs GmbH, Rolandstrasse 67, 50677 Köln, Germany). The LUMO levels of the molecular structures were determined by applying the hybrid functionals B3LYP and Def2-TZVP basis sets and the Stuttgart / Dresden (SDD) effective nuclear potential (ECP) for metals to the optimized geometries obtained by applying the effective nuclear potential (ECP) for metals to the Stuttgart / Dresden (SDD) basis sets. For materials containing Ce(IV) cations, the LUMO levels of the molecular structure were determined by applying the hybrid functional B3LYP and the SARC-ZORA-TZVP basis set for the metal and the ZORA-Def2-TZVP basis set for all other atoms, based on optimized geometries obtained by applying the functional BP86 and the SARC-ZORA-TZVP basis set for the metal and the ZORA-Def2-TZVP basis set for all other atoms. All calculations were performed in the gas phase. All relativistic calculations were performed by applying the zero-order rule approximation (ZORA). If more than one conformation was feasible, the conformation with the lowest total energy was selected. Different multistates may be applied depending on the metal cation. For the following metal cations, the multistates are shown in parentheses: Cu 2+ (Dual state), Cr 3+ (Quadtet), Mn 2+ (sixtet state), Mn 3+ (pentet state), Fe 3+ (six-fold state), Co3+ (quintet state), Al 3+ (singlet state), In 3+ (singlet state), Ru 3+ (six-fold state), Ce 4+ (Singlet state). Unless otherwise noted, the LUMO values ​​in Tables 1 and 2 are calculated using this method.

[0355] According to one embodiment of the compound of formula (I), the LUMO of the compound of formula (I) is selected in the range of ≤-3.4 eV but ≥-6.5 eV, preferably ≤-3.45 eV but ≥-6 eV, more preferably ≤-3.5 eV but ≥-5.8 eV; wherein the LUMO is calculated by the method described above.

[0356] General procedures for manufacturing OLEDs

[0357] For the embodiments and comparative examples according to the present invention in Table 4, glass substrates having an anode layer comprising a first anode sublayer of 10 nm ITO, a second anode sublayer of 120 nm Ag, and a third anode sublayer of 8 nm ITO were cut to dimensions of 100 mm × 100 mm × 0.7 mm, ultrasonically washed with water for 60 minutes, and then ultrasonically washed with isopropanol for 20 minutes. The liquid film was removed in a nitrogen stream, followed by plasma treatment, as shown in Table 4, to prepare the anode layer. This plasma treatment was performed in an atmosphere containing 97.6 vol% nitrogen and 2.4 vol% oxygen.

[0358] Then, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine (N-1, see Table 1), which serves as the first hole transport matrix compound, is vacuum deposited with 5% by weight of a compound or comparative compound according to formula (I) in Table 2 to form a hole injection layer (pHIL) with a thickness of 5 nm.

[0359] Then, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine (N-1) was vacuum deposited to form a first hole transport layer with a thickness of 33 nm.

[0360] Then, N,N-bis([1,1'-biphenyl]-4-yl)-3'-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine (N-2, see Table 1) was vacuum deposited on HTL to form an electron blocking layer (EBL) with a thickness of 5 nm.

[0361] Then, a first luminescent layer (EML1) with a thickness of 19 nm was formed on EBL1 by co-depositing 99 vol% of dibenzofuran, 7-(phenyl-2,3,4,5,6-d)-1-[10-(phenyl-2,3,4,5,6-d)-9-anthrayl] [2457172-82-4] as the EML host and 1 vol% of 5H,9H-[1]benzothiopheno[2′,3′:5,6][1,4]azaboroxane[2,3,4-kl]azaboroxane, 2,7,11-tris(1,1-dimethylethyl)-5,9-bis[4-(1,1-dimethylethyl)phenyl] [2482607-57-6].

[0362] Then, a first electron transport layer (ETL1) with a thickness of 15 nm is formed on the first luminescent layer by depositing (3-(10-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)anthracene-9-yl)phenyl)dimethylphosphine oxide (N-3, see Table 1).

[0363] Then, a first n-type charge generation layer (n-CGL1) with a thickness of 7.5 nm was formed on the first electron transport layer (ETL1) by co-deposition of 98 vol% of 2,2'-(1,3-phenyleneyl)bis[9-phenyl-1,10-phenanthroline (N-4, see Table 1) and 2 vol% of Yb.

[0364] Then, a first p-type charge-generating layer (p-CGL) with a thickness of 10 nm is formed on the first n-type CGL by co-depositing 91.09 wt% of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine (N-5, see Table 1) and 12 wt% of a compound or comparative compound according to formula (III) in Table 3 as a dopant.

[0365] Then, a second hole transport layer with a thickness of 43 nm was formed on the first p-type CGL by depositing N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine (N-5, see Table 1).

[0366] Then, a second electron blocking layer with a thickness of 5 nm is formed on the second hole transport layer by depositing N,N-bis([1,1'-biphenyl]-4-yl)-3'-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine (N-2).

[0367] Then, a second luminescent layer (EML2) with a thickness of 19 nm was formed on EBL1 by co-depositing 99 vol% of dibenzofuran, 7-(phenyl-2,3,4,5,6-d)-1-[10-(phenyl-2,3,4,5,6-d)-9-anthrayl] [2457172-82-4] as the EML host and 1 vol% of 5H,9H-[1]benzothiopheno[2′,3′:5,6][1,4]azaboroxane[2,3,4-kl]azaboroxane, 2,7,11-tris(1,1-dimethylethyl)-5,9-bis[4-(1,1-dimethylethyl)phenyl] [2482607-57-6].

[0368] Then, a first hole-blocking layer (HBL1) with a thickness of 5 nm was formed on EML2 by depositing the compound 4-([1,1'-biphenyl]-4-yl)-6-(3'-(9,9-dimethyl-9H-fluorene-4-yl)-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine (N-6).

[0369] Then, a second electron transport layer (ETL2) with a thickness of 31 nm was formed on HBL1 by co-deposition of compound 6,6'-(naphthalene-1,2-dimethylbis(4,1-phenylene))bis(2,4-diphenyl-1,3,5-triazine) (N-7, see Table 1) and LiQ (N-8) in a 50:50 wt% ratio.

[0370] Then, in 10 -7 Yb was evaporated at a rate of 0.01 Å / s to 1 Å / s under millibars to form an electron injection layer (EIL) with a thickness of 1.3 nm on the electron transport layer.

[0371] In 10 -7 Ag / Mg (10 vol% Mg) was evaporated at a rate of 0.01 Å / s to 1 Å / s under millibars to form a cathode with a thickness of 13 nm.

[0372] Then, N-({[1,1-'biphenyl]-4-yl)-9,9,dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine} (N-1) was vacuum deposited on the cathode layer to form a capping layer with a thickness of 75 nm.

[0373] To evaluate the performance of the invention compared to existing technologies, current efficiency was measured at 20°C. Using a Keithley 2635 source measurement unit, the current-voltage characteristics were determined by applying a voltage 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 increments within the range of 0 V to 10 V. Similarly, the luminance-voltage characteristics and CIE coordinates were measured in cd / m² at various voltage values ​​using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)). 2 The brightness was determined by interpolating the brightness-voltage and current-voltage characteristics, respectively, to determine 15 mA / cm². 2 The CD / A efficiency under these conditions.

[0374] In bottom-emitting devices, emission is primarily Lambertian and quantized as a percentage of external quantum efficiency (EQE). To determine the efficiency EQE as a percentage, a calibrated photodiode at 15 mA / cm² was used. 2 The light output of the measuring device.

[0375] In top-emitting devices, emission is forward-oriented, non-Lambertian, and highly dependent on the microcavity. Therefore, the efficiency EQE will be higher compared to bottom-emitting devices. To determine the efficiency EQE as a percentage, a calibrated photodiode at 15 mA / cm² was used. 2 The light output of the measuring device.

[0376] Under ambient conditions (20℃) and 10 mA / cm 2 or 30 mA / cm 2 Below, a Keithley 2400 source meter was used to measure the device lifetime LT and recorded in hours.

[0377] The brightness of the device is measured using a calibrated photodiode. Lifetime LT is defined as the time until the brightness of the device drops to 97% of its initial value.

[0378] The increment ΔU of the operating voltage is used as a measure of the device's operating voltage stability. This increment is determined during LT measurements by subtracting the operating voltage one hour after the device starts operating from the operating voltage after 100 hours.

[0379] ΔU=[U(100 h)- U(1 h)].

[0380] The smaller the ΔU value, the better the stability of the operating voltage.

[0381] Table 1: Compounds used

[0382] Table 2: Comparative devices and metal compounds according to formula (I)

[0383] Table 3: Comparison of organic compounds in the device and organic compounds according to formula (III)

[0384] Table 4 shows the setup and performance of several comparative and inventive examples.

[0385] Table 4: Setup and Performance of Multiple Comparative Examples and Invention Examples

[0386] The comparator Comp. Ex. 1 contains metal compound MC-1 as a p-type dopant in both the hole injection layer (HIL) and the p-type charge generation layer (p-CGL). MC-1 is not a metal compound according to formula (I).

[0387] The comparator Comp. Ex. 2 contains the same metal compound MC-1 as the p-type dopant in the HIL as in Comp. Ex. 1, but in the p-CGL, it contains the organic compound OC-1 as the p-type dopant in the p-CGL. OC-1 is not an organic compound according to formula (III).

[0388] The comparator Comp. Ex. 3 contains the metal compound Al27 according to formula (I) as a p-type dopant in HIL, and contains the same organic compound OC-1 as in Comp. Ex. 2 as a p-type dopant in p-CGL.

[0389] The comparator Comp. Ex. 4 contains the metal compound A5 according to formula (I) as a p-type dopant, and the p-CGL contains the same organic compound OC-1 as in Comp. Ex. 2 and Comp. Ex. 3 as a p-type dopant.

[0390] The comparator Comp. Ex. 5 contains metal compound A127 according to formula (I) as a p-type dopant in HIL and metal compound MC-1 as a p-type dopant in p-CGL.

[0391] The comparator Comp. Ex. 6 contains a metal compound MC-1 as a p-type dopant in HIL and an organic compound according to formula (III) as a p-type dopant in p-CGL.

[0392] The comparator Comp. Ex. 7 contains the metal compound MC-1 as a p-type dopant in HIL and the organic compound C1 as a p-type dopant in p-CGL.

[0393] Inventive Example 1 contains a metal compound Al27 of formula (I) as a p-type dopant in HIL, and an organic compound G8 of formula (III) as a p-type dopant in p-CGL.

[0394] Inventive Example 3 contains a metal compound Al27 of formula (I) as a p-type dopant in HIL, and an organic compound G5 of formula (III) as a p-type dopant in p-CGL.

[0395] Inventive Example 4 contains a metal compound A1 of formula (I) as a p-type dopant in HIL, and an organic compound G1 of formula (III) as a p-type dopant in p-CGL.

[0396] Inventive Example Inv. Ex. 5 contains a metal compound A52 of formula (I) as a p-type dopant in HIL, and an organic compound G11 of formula (III) as a p-type dopant in p-CGL.

[0397] Inventive Example Inv. Ex. 6 contains a metal compound A91 of formula (I) as a p-type dopant in HIL, and an organic compound G8 of formula (III) as a p-type dopant in p-CGL.

[0398] Inventive Example Inv. Ex. 7 contains a metal compound A91 of formula (I) as a p-type dopant in HIL, and an organic compound G6 of formula (III) as a p-type dopant in p-CGL.

[0399] Inventive Example Inv. Ex. 8 contains a metal compound Al116 of formula (I) as a p-type dopant in HIL, and an organic compound G2 of formula (III) as a p-type dopant in p-CGL.

[0400] Inventive Example Inv. Ex. 9 contains a metal compound A52 of formula (I) as a p-type dopant in HIL, and an organic compound G25 of formula (III) as a p-type dopant in p-CGL.

[0401] Typically, when the following combinations are compared with the inventive devices Inv. Ex. 1 and Inv. Ex. 9, it can be seen that all the inventive devices exhibit lower operating voltage (Vop), higher external quantum efficiency (EQE), higher current efficiency (Ceff), and lower operating voltage over time: The combination of HIL and p-CGL each contains two metal compounds, which are not the compounds in HIL and p-CGL as defined in this invention (Comp. Ex. 1); Alternatively, a combination of HIL and p-CGL, wherein HIL contains a metal compound which is not a compound of the present invention, and wherein p-CGL contains an organic compound which is not a compound of the present invention (Comp. Ex. 2); Alternatively, a combination of HIL and p-CGL, wherein HIL contains the metal compound of the present invention, and wherein p-CGL does not contain the organic compound of the present invention (Comp. Ex. 3 and 4); Alternatively, a combination of HIL and p-CGL, wherein HIL contains the metal compound of the present invention, and wherein p-CGL contains the metal compound of the present invention (Comp. Ex. 5); Alternatively, a combination of HIL and p-CGL, wherein HIL contains a metal compound which is not a metal compound of the present invention, and wherein p-CGL contains an organic compound of the present invention (Comp. Ex. 6 and 7).

[0402] The use of metal compound MC-1 (Comp.Ex. 1), which is not a metal compound in this invention, in both HIL and p-CGL results in the device exhibiting an operating voltage (Vop) higher than 10 V.

[0403] In contrast, as in the inventive device, the use of the compound of formula (I) in the HIL and the use of the organic compound of formula (III) (Inv. Ex..1 to Inv. Ex. 9) in the p-CGL exhibits a significantly low operating voltage between 6.47 V and 6.99 V, a significantly high external quantum efficiency (EQE) between 31.0% and 32.0%, a significantly high current efficiency (Ceff) between 17.3 cd / A and 17.5 cd / A, and a significantly low operating voltage increase over time (ΔU) between 0.11 V and 0.52 V.

[0404] The use of metal compound MC-1 (not a metal compound in this invention) and organic compound OC-1 (Comp. Ex. 2, not an organic compound in this invention) in HIL resulted in the device exhibiting an operating voltage higher than 10 V.

[0405] In contrast, as in the inventive device, the use of the compound of formula (I) in the HIL and the use of the organic compound of formula (III) (Inv. Ex..1 to Inv. Ex. 9) in the p-CGL exhibits a significantly low operating voltage between 6.47 V and 6.99 V, a significantly high external quantum efficiency (EQE) between 31.0% and 32.0%, a significantly high current efficiency (Ceff) between 17.3 cd / A and 17.5 cd / A, and a significantly low operating voltage increase over time (ΔU) between 0.11 V and 0.52 V.

[0406] The use of metal compound A1, which is a metallization of the present invention, and organic compound OC-1 (Comp. Ex. 3), which is not an organic compound of the present invention, in HIL results in the device exhibiting an operating voltage higher than 10 V.

[0407] In contrast, as in the inventive device, the use of the compound of formula (I) in the HIL and the use of the organic compound of formula (III) (Inv. Ex..1 to Inv. Ex. 9) in the p-CGL exhibits a significantly low operating voltage between 6.47 V and 6.99 V, a significantly high external quantum efficiency (EQE) between 31.0% and 32.0%, a significantly high current efficiency (Ceff) between 17.3 cd / A and 17.5 cd / A, and a significantly low operating voltage increase over time (ΔU) between 0.11 V and 0.52 V.

[0408] The use of metal compound A5, which is a metallization of the present invention, and organic compound OC-1 (Comp. Ex. 4), which is not an organic compound of the present invention, in HIL results in the device exhibiting an operating voltage higher than 10 V.

[0409] In contrast, as in the inventive device, the use of the compound of formula (I) in the HIL and the use of the organic compound of formula (III) (Inv. Ex..1 to Inv. Ex. 9) in the p-CGL exhibits a significantly low operating voltage between 6.47 V and 6.99 V, a significantly high external quantum efficiency (EQE) between 31.0% and 32.0%, a significantly high current efficiency (Ceff) between 17.3 cd / A and 17.5 cd / A, and a significantly low operating voltage increase over time (ΔU) between 0.11 V and 0.52 V.

[0410] The use of metal compound A1, which is a metal compound of the present invention, in HIL, and the use of metal compound MC-1 (Comp. Ex. 5), which is not a metal compound of the present invention, results in the device exhibiting an operating voltage higher than 10 V.

[0411] In contrast, as in the inventive device, the use of the compound of formula (I) in the HIL and the use of the organic compound of formula (III) (Inv. Ex..1 to Inv. Ex. 9) in the p-CGL exhibits a significantly low operating voltage between 6.47 V and 6.99 V, a significantly high external quantum efficiency (EQE) between 31.0% and 32.0%, a significantly high current efficiency (Ceff) between 17.3 cd / A and 17.5 cd / A, and a significantly low operating voltage increase over time (ΔU) between 0.11 V and 0.52 V.

[0412] The use of a metal compound MC-1, which is not a metallization in this invention, and an organic compound B1 (Comp. Ex. 6), which is an organic compound in this invention, in HIL results in the device exhibiting an operating voltage higher than 10 V.

[0413] In contrast, as in the inventive device, the use of the compound of formula (I) in the HIL and the use of the organic compound of formula (III) (Inv. Ex..1 to Inv. Ex. 9) in the p-CGL exhibits a significantly low operating voltage between 6.47 V and 6.99 V, a significantly high external quantum efficiency (EQE) between 31.0% and 32.0%, a significantly high current efficiency (Ceff) between 17.3 cd / A and 17.5 cd / A, and a significantly low operating voltage increase over time (ΔU) between 0.11 V and 0.52 V.

[0414] The use of a metal compound MC-1, which is not a metallization in this invention, and an organic compound C1 (Comp. Ex. 7), which is an organic compound in this invention, in HIL results in the device exhibiting an operating voltage higher than 10 V.

[0415] In contrast, as in the inventive device, the use of the compound of formula (I) in the HIL and the use of the organic compound of formula (III) (Inv. Ex..1 to Inv. Ex. 9) in the p-CGL exhibits a significantly low operating voltage between 6.47 V and 6.99 V, a significantly high external quantum efficiency (EQE) between 31.0% and 32.0%, a significantly high current efficiency (Ceff) between 17.3 cd / A and 17.5 cd / A, and a significantly low operating voltage increase over time (ΔU) between 0.11 V and 0.52 V.

[0416] The specific combinations of elements and features in the detailed embodiments described above are merely exemplary; these teachings are also explicitly considered in exchange for and substitution with other teachings herein and in the series / applications incorporated herein by reference. As those skilled in the art will recognize, variations, modifications, and other embodiments described herein can be conceived without departing from the spirit and scope of the claimed invention. Therefore, the above 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 singular forms “a” or “an” do not exclude plural indicators. The fact that specific measures are recited in dissimilar dependent claims does not imply that combinations of these measures cannot be advantageously chosen. The scope of the invention is defined by the claims and their equivalents. Furthermore, the reference numerals used in the specification and claims are not intended to limit the scope of the claimed invention.

Claims

1. An organic electronic device, the organic electronic device comprising a substrate, an anode layer, a cathode layer, a first photoactive layer, a second photoactive layer, a hole injection layer, and a charge generation layer. The charge generation layer comprises a p-type charge generation layer and an n-type charge generation layer. The hole injection layer, the charge generation layer, the first photoactive layer, and the second photoactive layer are disposed between the anode layer and the cathode layer. The hole injection layer is positioned closer to the anode layer than the p-type charge generation layer. The p-type charge generation layer is arranged closer to the cathode layer than the n-type charge generation layer, and the n-type charge generation layer is arranged closer to the anode layer than the p-type charge generation layer. The hole injection layer is in direct contact with the anode layer. The charge-generating layer is disposed between the first photoactive layer and the second photoactive layer. The hole injection layer comprises a compound of formula (I): (I)， in: M is a metal ion; n is the valence of M and is selected from 1 to 4; L is a ligand independently selected from formula (II). (II), in A 1 Selected from C=O or SO2; X 1 Selected from CR 1 Or N; X 2 Selected from CR 2 Or N; X 3 Selected from CR 3 Or N; X 4 Selected from CR 4 Or N; Where X 1 X 2 X 3 X 4 The 0, 1, or 2 elements are selected from N; R 1 To R 4 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl groups, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated or perfluorinated C1 to C8 alkoxy, OCF3, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Heteroaryl, substituted or unsubstituted 6-membered heteroaryl, substituted or unsubstituted 6-membered C3 to C5 heteroaryl; substituted or unsubstituted 6-membered C4 to C5 heteroaryl; halogen, F, Cl or CN, and wherein any R k To R k+1 They can form a ring, where k is an integer selected from 1 to 3; R 5 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, partially fluorinated or perfluorinated C1 to C2 groups. 12 Alkyl, CF3, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Heteroaryl, substituted or unsubstituted 6-membered heteroaryl, substituted or unsubstituted 6-membered C3 to C5 heteroaryl; substituted or unsubstituted 6-membered C4 to C5 heteroaryl; Where R 1 To R 5 The replacement of C1 to C 12 Alkyl, substituted C1 to C8 alkoxy, substituted C6 to C 19 Aryl, substituted C2 to C 20 One or more substituents of a heteroaryl, a substituted 6-membered heteroaryl, a substituted 6-membered C3 to C5 heteroaryl, or a substituted 6-membered C4 to C5 heteroaryl are independently selected from D, an electron-withdrawing group, a halogen, Cl, F, CN, a partially fluorinated or perfluorinated C1 to C8 alkyl, or a partially or perfluorinated C1 to C8 alkoxy. AL is an auxiliary ligand that coordinates with metal M; m is an integer selected from 0 to 2; The p-type charge-generating layer comprises an organic compound of formula (III). (III), in n is an integer selected from 0, 1, 2, 3, 4, 5 or 6, preferably 0, 2 or 4; m is an integer selected from 0 or 1; preferably 1; Y 1 Y 2 and Y 3 Independently selected from O, S, CR 1a R 2a CR 1b R 2b NR 3a NR 3b , or Y 1 Y 2 and Y 3 At least one of them forms a fused ring with A, wherein each Y 2 The choice is either the same or different, with a preference for the same, and each Y... 3 Choose between "same" or "different", with "same" being the preferred choice. R 1a R 2a R 1b and R 2b Independently selected from electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C8 alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 40 Aryl, substituted or unsubstituted C2 to C 40 Mixed aromatics, Where R 1a R 2a R 1b and R 2b One or more substituents are independently selected from D, electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 30 aryl groups, and substituted or unsubstituted C6 to C6 groups. 30 Mixed aromatics; Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, isocyanate, SCN, OCN, SF5, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, and perfluorinated C1 to C8 alkoxy. R 3a and R 3b Selected from electron-withdrawing groups, CN, partially fluorinated C1 to C6 alkyl groups, perfluorinated C1 to C6 alkyl groups, CF3, substituted or unsubstituted C6 to C6 alkyl groups. 30 aryl, or substituted or unsubstituted C3 to C4 30 Mixed aromatics, Where R 3a and R 3b One or more substituents are independently selected from D, electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C8 alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 30 aryl groups, and substituted or unsubstituted C6 to C6 groups. 30 Mixed aromatics; Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, isocyanate, SCN, OCN, SF5, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, and perfluorinated C1 to C8 alkoxy. A is selected from C3 to C4, whether substituted or unsubstituted. 40 Cyclic hydrocarbon group, substituted or unsubstituted C3 to C4 40 Cycloalkyl groups, containing one or more double bonds, substituted or unsubstituted C3 to C4 groups. 40 Cycloalkyl groups, substituted or unsubstituted C3 to C4 40 Cycloalkenyl groups, substituted or unsubstituted C2 to C3 40 Heterocyclic alkyl groups, containing one or more double bonds, substituted or unsubstituted C2 to C3 groups. 40 Heterocyclic alkyl groups, substituted or unsubstituted C2 to C3 40 Heterocyclic olefinic groups, substituted or unsubstituted C6 to C6 40 Aromatic groups, substituted or unsubstituted C2 to C3 40 heteroaromatic groups, One or more substituents on A are independently selected from D, electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C8 alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Mixed aromatics, Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, isocyanate, SCN, OCN, SF5, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, and OCF3.

2. The organic electronic device according to claim 1, wherein the atomic mass of M of the metal compound of formula (I) is selected in the range of ≥20 Da but ≤200 Da.

3. The organic electronic device according to claim 1 or 2, wherein in formula (I), the molecular mass of L is selected in the range of ≤600 Da but ≥240 Da.

4. The organic electronic device according to any one of claims 1 to 3, wherein formula (II) contains at least one fluorine atom, preferably at least two fluorine atoms, more preferably at least three fluorine atoms.

5. The organic electronic device according to any one of claims 1 to 4, wherein M in formula (I) is selected from Li(I), Na(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(II), Mn(III), Ru(III), In(III), Fe(II), Fe(III), Ce(IV).

6. The organic electronic device according to any one of claims 1 to 5, wherein M in formula (I) is selected from Li(I), Na(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(II), Mn(III), Ru(III), In(III), Fe(II), Fe(III).

7. The organic electronic device according to any one of claims 1 to 6, wherein L is selected from C1 to C141: (C1)、 (C2)、 (C3)、 (C4)、 (C5)、 (C6)、 (C7)、 (C8)、 (C9)、 (C10)、 (C11)、 (C12)、 (C13)、 (C14)、 (C15)、 (C16)、 (C17)、 (C18)、 (C19)、 (C20)、 (C21)、 (C23)、 (C24)、 (C25)、 (C26)、 (C27)、 (C28)； C141。 8. The organic electronic device according to any one of claims 1 to 7, wherein the organic compound of formula (III) has a LUMO energy level equal to or less than -4.30 eV. This involves applying hybrid functionals B3LYP and 6-31G in the gas phase. The basis set was used to calculate the LUMO levels using the package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany).

9. The organic electronic device according to any one of claims 1 to 8, wherein in formula (III), A is selected from H1 to H72: (H1)、 (H2)、 (H3)、 (H4)、 (H5)、 (H6)、 (H7)、 (H8)、 (H9)、 (H10)、 (H11)、 (H12)ぁ (H13)、 (H14)、 (H15)ぁ (H16)、 (H17)、 (H18)、 (H19)、 (H20)、 (H21)ぁ (H22)、 (H23)、 (H24)、 (H25)ぁ (H26)、 (H27)、 (H28)、 (H29)、 (H30)、 (H31)、 (H32)、 (H33)、 (H34)、 (H35)、 (H36)、 (H37)、 (H38)、 (H39)、 (H40)、 (H41)ぁ (H42)、 (H43)、 (H44)、 (H45)ぁ (H46)、 (E47)、 (E48)ぁ (H49)、 (H50) (H51)ぁ (H52)ぁ (H53)、 (H54)、 (H55)、 (H56)、 (H57)、 (H58)、 (H59)、 (H60)、 (H61)ぁ (H62)、 (H63)、 (H64)、 (H65)、 (H66)、 (H67)、 (H68)、 (H69) (H70)、 (H71)、 (H72) Among them, the asterisk " "Indicates the position of combination; R 1 R 2 R 3 R 4 R 5 R 6 R 7 and R 8 Independently selected from H, D, halogens, Cl, F, substituted or unsubstituted C1 to C6 alkyl groups, partially fluorinated C1 to C6 alkyl groups, perfluorinated C1 to C6 alkyl groups, CF3, substituted or unsubstituted C1 to C6 alkoxy groups, partially fluorinated C1 to C6 alkoxy groups, perfluorinated C1 to C6 alkoxy groups, OCF3, substituted or unsubstituted C6 to C 30 Aryloxy groups, partially fluorinated C6 to C6 30 Aryloxy groups, perfluorinated C6 to C6 groups 30 Aryloxy group, substituted or unsubstituted C6 to C6 30 Aryl, substituted or unsubstituted C3 to C4 30 Heteroaryl, CN, isocyanate, SCN, OCN, NO2, SF5 The substituents are selected from D, halogens, Cl, F, partially fluorinated C1 to C6 alkyl groups, perfluorinated C1 to C6 alkyl groups, CF3, partially fluorinated C1 to C6 alkoxy groups, perfluorinated C1 to C6 alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5. B 1 and B 2 They are selected independently from N and CR. 5A’ or CR 6A’ ,in CR 5A’ or CR 6A’ Each is independently selected from H, D, F, substituted or unsubstituted C6 to C6. 12 Aryl group, substituted or unsubstituted C1 to C2 groups having one to four heteroatoms selected from O, N, S and Si. 12 heteroaryl, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C1 to C2 12 Alkoxy, substituted or unsubstituted C1 to C 12 Ether groups, CN, CF3, OCF3, halogens, Cl, F, Si(CH3)3, preferably R 1 To R 6 At least one of them contains CN, wherein CR 5A’ or CR 6A’ One or more substituents are independently selected from D, electron-withdrawing groups, halogens, Cl, F, substituted or unsubstituted C1 to C8 alkyl groups, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, substituted or unsubstituted C1 to C8 alkoxy groups, partially fluorinated C1 to C8 alkoxy groups, perfluorinated C1 to C alkoxy groups, OCF3, CN, isocyanate, SCN, OCN, NO2, SF5, substituted or unsubstituted C6 to C 30 aryl groups, and substituted or unsubstituted C6 to C6 groups. 30 Mixed aromatics, Among them, C6 to C 30 Aryl, C6 to C 30 One or more substituents of heteroaryl, C1 to C8 alkyl, and C1 to C8 alkoxy, if present, are independently selected from D, electron-withdrawing groups, halogens, Cl, F, CN, -NO2, isocyanate, SCN, OCN, SF5, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, and perfluorinated C1 to C8 alkoxy.

10. The organic electronic device according to any one of claims 1 to 7, wherein in formula (III), A is selected from the following: 。 11. The organic electronic device according to any one of claims 1 to 8, wherein in formula (III), A is selected from the following: 。 12. The organic electronic device according to any one of claims 1 to 11, wherein the hole injection layer and / or the p-type charge generation layer comprises at least one arylamine compound, a diarylamine compound, a triarylamine compound, a compound of formula (IVa), or a compound of formula (IVb): (IVa)、 (IVb), in: T 1 T 2 T 3 T 4 and T 5 It is independently selected from single bond, phenylene group, biphenylene group, triphenylene group or naphthylene group, preferably single bond or phenylene group; T 6 It can be a benzene group, a biphenyl group, a terphenyl group, or a naphthyl group; Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 Selected independently from: substituted or unsubstituted C6 to C 20 aryl or substituted or unsubstituted C3 to C 20 Heteroarylene groups, substituted or unsubstituted biphenylidene, substituted or unsubstituted fluorene, substituted 9-fluorene, substituted 9,9-fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted triphenylidene, substituted or unsubstituted tetraphenylene, substituted or unsubstituted benzo[a]anthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthones, substituted or unsubstituted carbazole, substituted 9-phenylcarbazole, substituted or unsubstituted azaheptanyl, substituted or unsubstituted... The substituted dibenzo[b,f]azonium heterocyclic heptane, substituted or unsubstituted 9,9'-spirobis[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanton], 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 hetero 5-membered rings, substituted or unsubstituted 6-membered rings and / or substituted or unsubstituted 7-membered rings, substituted or unsubstituted fluorene, or fused-ring systems comprising 2 to 6 substituted or unsubstituted 5 to 7-membered rings, and 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; (IIIa) 6-membered aromatic non-heterocyclic rings; in Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 The substituents are selected from H, D, F, C(-O)R, either the same or different. 2 CN, Si(R) 2 3. P(-O)(R) 2 2. OR 2 S(-O)R 2 S(-O)2R 2 Substituted or unsubstituted straight-chain alkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted branched alkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms; substituted or unsubstituted alkenyl or alkynyl groups having 2 to 20 carbon atoms; substituted or unsubstituted aromatic ring systems having 6 to 40 aromatic ring atoms; and substituted or unsubstituted heteroaromatic ring systems having 5 to 40 aromatic ring atoms; unsubstituted C6 to C6... 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 heterocyclic rings, 5 to 6-membered aromatic heterocyclic rings, unsaturated 5 to 7-membered non-heterocyclic rings, and 6-membered aromatic non-heterocyclic rings. Where R 2 The following can be selected from H, D, straight-chain alkyl groups having 1 to 6 carbon atoms, branched alkyl groups having 1 to 6 carbon atoms, cyclic alkyl groups having 3 to 6 carbon atoms, alkenyl or ynyl groups having 2 to 6 carbon atoms, C6 to C 18 Aryl or C3 to C 18 Mixed aromatic compounds.

13. The organic electronic device according to any one of claims 1 to 12, wherein the hole injection layer and / or the p-type charge generation layer comprises at least one compound of formula (IVa) or formula (IVb).

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

15. A display device comprising an organic electronic device according to any one of claims 1 to 14.

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