Organic optoelectronic element and display device

Abstract

An organic optoelectronic element includes an anode and a cathode facing each other, a light emitting layer between the anode and the cathode, a hole transport layer between the anode and the light emitting layer, and a hole transport auxiliary layer between the light emitting layer and the hole transport layer, wherein the light emitting layer includes a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2 or a combination of Chemical Formula 3 and Chemical Formula 4, and the hole transport auxiliary layer includes a third compound represented by Chemical Formula 5. Details of Chemical Formulae 1 to 5 are as defined in the specification.

Description

Technical Field

[0001] An organic optoelectronic device and a display device are disclosed. Background Technology

[0002] Organic optoelectronic devices (organic optoelectronic diodes) are devices that can convert electrical energy into light energy and vice versa.

[0003] Based on their working principles, organic optoelectronic devices can be broadly classified into two categories. One category consists of optoelectronic devices that generate electrical energy by separating excitons formed from light energy into electrons and holes and transferring the electrons and holes to different electrodes. The other category consists of light-emitting devices that generate light energy from electrical energy by providing voltage or current to the electrodes.

[0004] Examples of organic optoelectronic devices include organic photoelectric devices, organic light-emitting diodes, organic solar cells, and organic photosensitive drums.

[0005] Organic light-emitting diodes (OLEDs) have received considerable attention in recent years due to the increasing demand for flat panel display devices. OLEDs are devices that convert electrical energy into light, and their performance is greatly affected by the organic materials between the electrodes. Summary of the Invention

[0006] Technical issues

[0007] One implementation provides an organic optoelectronic device capable of achieving high efficiency characteristics.

[0008] Another embodiment provides a display device that includes an organic optoelectronic device.

[0009] Technical solution

[0010] According to one embodiment, an organic optoelectronic device includes an anode and a cathode facing each other, a light-emitting layer between the anode and the cathode, a hole transport layer between the anode and the light-emitting layer, and a hole transport auxiliary layer between the light-emitting layer and the hole transport layer, wherein the light-emitting layer contains a first compound represented by chemical formula 1 and a second compound represented by chemical formula 2 or a combination of chemical formula 3 and chemical formula 4, and the hole transport auxiliary layer contains a third compound represented by chemical formula 5.

[0011] [Chemical Formula 1]

[0012] In chemical formula 1, Z 1 To Z 3 Each is independently N or CR a , Z 1 To Z 3At least two of them are N. R 1 To R 8 and R a Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. L 1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heterocyclic group, and Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group; [Chemical Formula 2]

[0013] In chemical formula 2, Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. L 4 and L 5 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. R 9 To R 19 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. m1 and m2 are each an independent integer from 1 to 3. m3 is an integer from 1 to 4, and n is an integer between 0 and 2; [Chemical Formula 3] [Chemical Formula 4]

[0014] In chemical formulas 3 and 4, Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. a1 in chemical formula 3 up to a4 Each is independently connected to carbon (C) or CL. a -Rb , In chemical formula 4 Each is an independent linker of carbon (C). a1 in chemical formula 3 up to a4 In the middle, the two adjacent ones are each connected to the chemical formula 4. , L a L 6 and L 7 Each is independently a single bond or a substituted or unsubstituted C6 to C20 aryl group, and R b and R 20 To R 27 Each of them is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group or substituted or unsubstituted C2 to C30 heterocyclic group; [Chemical Formula 5]

[0015] In chemical formula 5, Ar 8 and Ar 9 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. Ar 10 and Ar 11 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 41 To R 45 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and m5 is an integer from 1 to 3.

[0016] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0017] Beneficial effects

[0018] It can realize organic optoelectronic devices with high efficiency. Attached Figure Description

[0019] Figure 1 This is a cross-sectional view of an organic light-emitting diode according to one embodiment.

[0020] <Explanation of Figure Markers>

[0021] 10: Anode 20: Cathode

[0022] 30: Organic layer; 31: Hole transport layer

[0023] 32: Emissive layer; 33: Hole transport auxiliary layer

[0024] 34: Electron transport layer Detailed Implementation

[0025] Embodiments of the present invention are described in detail below. However, these embodiments are exemplary, and this disclosure is not limited thereto.

[0026] In this specification, unless otherwise defined, “substituted” means that at least one hydrogen atom of a substituent or compound is replaced by a deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amino, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or combinations thereof.

[0027] In one embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0028] In this specification, "unsubstituted" means that the hydrogen atom is not replaced by another substituent and retains the hydrogen atom.

[0029] In this specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)".

[0030] In this specification, unless otherwise defined, “heterogeneous” means a functional group containing one to three heteroatoms selected from N, O, S, P and Si and the remaining carbon.

[0031] In this specification, "aryl" means a group comprising at least one aromatic hydrocarbon moiety, wherein all elements of the aromatic hydrocarbon moiety have conjugated p orbitals, such as phenyl, naphthyl, etc., and two or more aromatic hydrocarbon moiety may be linked by σ bonds and may be, for example, biphenyl, terphenyl, tetraphenyl, etc., and two or more aromatic hydrocarbon moiety may be directly or indirectly fused to provide a non-aromatic fused ring, such as fluorene.

[0032] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent carbon atom pairs) functional groups.

[0033] As used herein, "heterocyclic group" is a superordinate concept of a heteroaryl group and may include at least one heteroatom selected from N, O, S, P, and Si in place of carbon (C) in cyclic compounds such as aryl, cycloalkyl, their fused rings, or combinations thereof. When the heterocyclic group is fused, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0034] For example, "heteroaryl" can refer to an aryl group comprising at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly connected by σ bonds, or when a heteroaryl group comprises two or more rings, the two or more rings can be fused. When a heteroaryl group is a fused ring, each ring may comprise one to three heteroatoms.

[0035] More specifically, the substituted or unsubstituted C6 to C30 aryl group can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted tetraphenyl, a substituted or unsubstituted pyrene, a substituted or unsubstituted biphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted meta-terphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted trefyl, a substituted or unsubstituted benzo[a]phenanthyl, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted peryl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indene, or a combination thereof, but is not limited thereto.

[0036] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group can be a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted pyrrole group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, or a substituted or unsubstituted benzothiopheneyl group. The following are substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or combinations thereof, but not limited thereto.

[0037] As used herein, hole properties refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductivity of the highest occupied molecular orbital (HOMO) energy level, holes formed in the anode can be readily injected into and transported in the light-emitting layer.

[0038] Furthermore, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductivity of the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into and transported in the light-emitting layer.

[0039] The following describes an organic optoelectronic device according to one embodiment of the present invention.

[0040] Organic optoelectronic devices can be suitable devices that convert electrical energy into light energy and vice versa, such as organic photoelectric devices, organic light-emitting diodes, organic solar cells, or organic photosensitive drums.

[0041] This document describes an organic light-emitting diode as an example of an organic optoelectronic device, but the invention is not limited thereto and can be applied in the same manner to other organic optoelectronic devices.

[0042] In the accompanying drawings, the thicknesses of layers, films, panels, regions, etc., are enlarged for clarity. Throughout the specification, similar reference numerals denote similar elements. It will be understood that when an element such as a layer, film, region, or substrate is referred to as being "on" another element, it may be directly on the other element, or there may be intermediate elements present. Conversely, when an element is referred to as being "directly" on another element, there are no intermediate elements.

[0043] Figure 1 This is a schematic cross-sectional view of an organic optoelectronic device according to one embodiment.

[0044] refer to Figure 1 An organic optoelectronic device according to one embodiment includes an anode 10 and a cathode 20 facing each other and an organic layer 30 between the anode 10 and the cathode 20.

[0045] The anode 10 may be made of a conductor with a high work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 10 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or alloys thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; a combination of metals and oxides such as ZnO and Al or SnO2 and Sb; a conductive polymer such as, but not limited to, poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline.

[0046] The cathode 20 may be made of a conductor with a small work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 20 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc., or alloys thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0047] The organic layer 30 includes a hole transport layer 31, a light-emitting layer 32, and a hole transport auxiliary layer 33 between the hole transport layer 31 and the light-emitting layer 32.

[0048] Hole transport layer 31 is a layer used to facilitate hole transport from anode 10 to light-emitting layer 32, and may contain, for example, amine compounds, but is not limited thereto.

[0049] Amine compounds may contain, for example, at least one aryl and / or heteroaryl group. Amine compounds may be represented by, for example, chemical formula a or chemical formula b, but are not limited thereto.

[0050] [Chemical Formula a] [Chemical Formula b]

[0051] In chemical formula a or b Ar a To Ar g Each of these elements independently consists of hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl, or combinations thereof. Ar a To Ar c At least one of them and Ar d To Ar g At least one of them is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and Ar h It is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof.

[0052] The light-emitting layer 32 includes at least two types of hosts and dopants. The hosts include a first compound with relatively strong bipolar properties and a second compound with relatively strong hole properties.

[0053] The first compound is a compound with relatively strong bipolar properties and can be represented by chemical formula 1.

[0054] [Chemical Formula 1]

[0055] In chemical formula 1, Z 1 To Z 3 Each is independently N or CR a , Z 1 To Z 3 At least two of them are N. R 1 To R 8 and R a Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. L 1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heterocyclic group, and Ar 1 and Ar 2Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0056] The first compound has a structure in which the pyrimidine or triazine ring is substituted with at least one 9-carbazole, such that it can readily accept electrons when an electric field is applied. Therefore, together with the second compound described below, it can appropriately balance excellent interfacial properties with the flow of holes and electrons, and thus it can improve the driving voltage of organic optoelectronic devices using the first compound.

[0057] In chemical formula 1, Ar 1 and Ar 2 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazoyl.

[0058] For example, Ar 1 and Ar 2 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazoyl.

[0059] In chemical formula 1, L 1 To L 3 Each can be a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0060] For example, L 1 -Ar 1 and L 2 -Ar 2 Each can be independently selected from the substituents listed in Group I.

[0061] [Group I]

[0062] In group I, R 46 To R 48 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m6 is an integer from 1 to 5. m7 is an integer from 1 to 4. m8 is an integer from 1 to 3, and It is a connection point.

[0063] In chemical formula 1, R 1 To R 8 Each of them can be hydrogen, deuterium, substituted or unsubstituted C1 to C5 alkyl, substituted or unsubstituted C6 to C12 aryl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0064] For example, R 1 To R 8 Each of them can be hydrogen, deuterium, substituted or unsubstituted C1 to C5 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophene.

[0065] In chemical formula 1, R a It can be hydrogen, deuterium, substituted or unsubstituted C1 to C5 alkyl or substituted or unsubstituted C6 to C12 aryl.

[0066] For example, R a It can be hydrogen, deuterium, substituted or unsubstituted C1 to C5 alkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted biphenyl.

[0067] The first compound may be, for example, one of the compounds selected from Group 1, but is not limited thereto.

[0068] [Group 1]

[0069] [A-1] [A-2] [A-3] [A-4] [A-5]

[0070] [A-6] [A-7] [A-8] [A-9] [A-10]

[0071] [A-11] [A-12] [A-13] [A-14] [A-15]

[0072] [A-16] [A-17] [A-18] [A-19] [A-20]

[0073] [A-21] [A-22] [A-23] [A-24] [A-25]

[0074] [A-26] [A-27] [A-28] [A-29] [A-30]

[0075] [A-31] [A-32] [A-33] [A-34] [A-35]

[0076] [A-36] [A-37] [A-38] [A-39] [A-40]

[0077] [A-41] [A-42] [A-43] [A-44] [A-45]

[0078] [A-46] [A-47] [A-48] [A-49] [A-50]

[0079] [A-51] [A-52] [A-53] [A-54] [A-55]

[0080] [A-56] [A-57] [A-58] [A-59] [A-60]

[0081] [A-61] [A-62] [A-63] [A-64] [A-65]

[0082] [A-66] [A-67] [A-68] [A-69] [A-70]

[0083] [A-71] [A-72] [A-73] [A-74] [A-75]

[0084] [A-76] [A-77] [A-78] [A-79] [A-80]

[0085] [A-81] [A-82] [A-83] [A-84] [A-85]

[0086] [A-86] [A-87] [A-88] [A-89] [A-90]

[0087] [A-91] [A-92] [A-93] [A-94] [A-95]

[0088] [A-96] [A-97] [A-98] [A-99] [A-100]

[0089] [A-101] [A-102] [A-103] [A-104]

[0090] [A-105] [A-106] [A-107] [A-108]

[0091] [A-109] [A-110] [A-111] [A-112]

[0092] [A-113] [A-114] [A-115] [A-116]

[0093] [A-117] [A-118] [A-119] [A-120]

[0094] The first compound can be used in one, two or more types.

[0095] The second compound can be used together with the first compound in the luminescent layer to improve luminous efficiency and lifetime characteristics by increasing charge mobility and improving stability.

[0096] The second compound can be represented, for example, by chemical formula 2.

[0097] [Chemical Formula 2]

[0098] In chemical formula 2, Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. L 4 and L 5 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. R 9 To R 19 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. m1 and m2 are each an independent integer from 1 to 3. m3 is an integer from 1 to 4, and n is an integer between 0 and 2.

[0099] When m1 is 2 or greater, R 13 Each can be the same as or different from the other.

[0100] When m2 is 2 or greater, R 14 Each can be the same as or different from the other.

[0101] When m3 is 2 or greater, R 19 Each can be the same as or different from the other.

[0102] For example, in chemical formula 2, Ar 3 and Ar 4 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted fluorenyl. In chemical formula 2, L 4 and L 5 Each can be a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene. In chemical formula 2, R 9 To R 19 Each can be independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and n can be 0 or 1.

[0103] For example, in Formula 2, "substituted" means that at least one hydrogen atom is substituted by a deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0104] In one specific embodiment of the present invention, chemical formula 2 may be represented by one of chemical formulas 2-1 to 2-15.

[0105] [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3]

[0106] [Chemical Formula 2-4] [Chemical Formula 2-5] [Chemical Formula 2-6]

[0107] [Chemical Formula 2-7] [Chemical Formula 2-8] [Chemical Formula 2-9]

[0108] [Chemical Formula 2-10] [Chemical Formula 2-11] [Chemical Formula 2-12]

[0109] [Chemical Formula 2-13] [Chemical Formula 2-14] [Chemical Formula 2-15]

[0110] In chemical formulas 2-1 to 2-15, R 9 To R 19 They can be hydrogen, deuterium, or substituted or unsubstituted C6 to C12 aryl groups, each independently. m1 and m2 can each be an integer from 1 to 3 independently. m3 can be any integer from 1 to 4, and L 4 -Ar 3 and L 5 -Ar 4 Each can be one of the substituents listed in Group II, and each can be independent of the others.

[0111] [Group II]

[0112] In Group II, R 49 To R 52Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m9 is an integer from 1 to 5. m10 is one of the integers from 1 to 4. m11 is an integer from 1 to 3. m12 is an integer of 1 or 2, and It is a connection point.

[0113] When m9 is 2 or greater, R 49 Each can be the same as or different from the other.

[0114] When m10 is 2 or greater, R 50 Each can be the same as or different from the other.

[0115] When m11 is 2 or greater, R 51 Each can be the same as or different from the other.

[0116] When m12 is 2 or greater, R 52 Each can be the same as or different from the other.

[0117] In one embodiment, chemical formula 2 can be represented by chemical formula 2-8.

[0118] Furthermore, in chemical formula 2-8, L 4 -Ar 3 and L 5 -Ar 4 They can be selected independently from group II, and can be any of, for example, E-1, E-2, E-3, E-4, E-7, E-8 and E-9.

[0119] The second compound can be represented, for example, by a combination of chemical formulas 3 and 4.

[0120] [Chemical Formula 3] [Chemical Formula 4]

[0121] In chemical formulas 3 and 4, Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. a1 in chemical formula 3 up to a4 Each is independently connected to carbon (C) or CL. a -R b , In chemical formula 4 Each is an independent linker of carbon (C). a1 in chemical formula 3 up to a4 The two adjacent ones in the middle are each connected to the chemical formula 4. , L a L 6 and L 7 Each is independently a single bond or a substituted or unsubstituted C6 to C20 aryl group, and R b and R 20 To R 27 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group.

[0122] For example, a second compound represented by a combination of chemical formulas 3 and 4 can be represented by any one of chemical formulas 3A, 3B, 3C, 3D, and 3E.

[0123] [Chemical Formula 3A] [Chemical Formula 3B] [Chemical Formula 3C]

[0124] [Chemical Formula 3D] [Chemical Formula 3E]

[0125] In chemical formulas 3A to 3E, Ar 5 Ar 6 L 6 L 7 and R 20 To R 27 Same as above, L a1 To L a4 With L 6 and L 7 The definitions are the same, and R a1 To R a4 With R 20 To R 27 The definitions are the same.

[0126] For example, in chemical formulas 3 and 4, Ar 5 and Ar 6Each of these can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted carbazole, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl.

[0127] R a1 To R a4 and R 20 To R 27 Each of these can be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0128] In another specific embodiment of the invention, in chemical formulas 3 and 4, L 6 -Ar 5 and L 7 -Ar 6 Each can be independently selected from the substituents listed in Group II.

[0129] In one implementation, R a1 To R a4 and R 20 To R 27 Each of these can be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0130] For example, R a1 To R a4 and R 20 To R 27 Each can be independently hydrogen, deuterium, cyano, or a substituted or unsubstituted phenyl group, and

[0131] In one specific implementation, R a1 To R a4 and R 20 To R 27 Each can be hydrogen, deuterium, or phenyl, independently.

[0132] For example, the second compound used in an organic optoelectronic device may be, for example, one of the compounds selected from group 2, but is not limited thereto.

[0133] [Group 2]

[0134] [B-1] [B-2] [B-3] [B-4] [B-5]

[0135] [B-6] [B-7] [B-8] [B-9] [B-10]

[0136] [B-11] [B-12] [B-13] [B-14] [B-15]

[0137] [B-16] [B-17] [B-18] [B-19] [B-20]

[0138] [B-21] [B-22] [B-23] [B-24] [B-25]

[0139] [B-26] [B-27] [B-28] [B-29] [B-30]

[0140] [B-31] [B-32] [B-33] [B-34] [B-35]

[0141] [B-36] [B-37] [B-38] [B-39] [B-40]

[0142] [B-41] [B-42] [B-43] [B-44] [B-45]

[0143] [B-46] [B-47] [B-48] [B-49] [B-50]

[0144] [B-51] [B-52] [B-53] [B-54] [B-55]

[0145] [B-56] [B-57] [B-58] [B-59] [B-60]

[0146] [B-61] [B-62] [B-63] [B-64] [B-65]

[0147] [B-66] [B-67] [B-68] [B-69] [B-70]

[0148] [B-71] [B-72] [B-73] [B-74] [B-75]

[0149] [B-76] [B-77] [B-78] [B-79] [B-80]

[0150] [B-81] [B-82] [B-83] [B-84] [B-85]

[0151] [B-86] [B-87] [B-88] [B-89] [B-90]

[0152] [B-91] [B-92] [B-93] [B-94] [B-95]

[0153] [B-96] [B-97] [B-98] [B-99] [B-100]

[0154] [B-101] [B-102] [B-103] [B-104] [B-105]

[0155] [B-106] [B-107] [B-108] [B-109] [B-110]

[0156] [B-111] [B-112] [B-113] [B-114] [B-115]

[0157] [B-116] [B-117] [B-118] [B-119] [B-120]

[0158] [B-121] [B-122] [B-123] [B-124] [B-125]

[0159] [B-126] [B-127] [B-128] [B-129] [B-130]

[0160] [B-131] [B-132] [B-133] [B-134] [B-135]

[0161] [B-136] [B-137] [B-138] [B-139] [B-140]

[0162] [B-141] [B-142] [B-143] [B-144]

[0163] [B-145] [B-146] [B-147]

[0164] [B-148] [B-149] [B-150] [B-151] [B-152]

[0165] Additionally, examples are provided below of compounds B-1 to B-152 listed in Group 2 in which at least one hydrogen atom is replaced by deuterium, but this is not an limitation.

[0166] [B-153] [B-154] [B-155] [B-156] [B-157]

[0167] [B-158] [B-159] [B-160] [B-161] [B-162]

[0168] [B-163] [B-164] [B-165] [B-166] [B-167]

[0169] [B-168] [B-169] [B-170] [B-171] [B-172]

[0170] [B-173] [B-174] [B-175] [B-176] [B-177]

[0171] [B-178] [B-179] [B-180] [B-181] [B-182]

[0172] [B-183] [B-184] [B-185] [B-186] [B-187]

[0173] [B-188] [B-189] [B-190] [B-191] [B-192]

[0174] [B-193] [B-194] [B-195] [B-196] [B-197]

[0175] (Dn represents the number of deuterium substitutions and indicates a structure with one or more deuterium substitutions).

[0176] For compounds B-153 to B-197 of Group 2, the most specific structures are provided below as examples only, based on the deuterium substitution position and substitution rate, and these structures are not intended to limit the scope of rights of compounds not provided below.

[0177] The scope of the invention is defined by the claims, and if deuterium is substituted, the invention is not limited to the compounds illustrated below, but may include all variable ranges within the above range of compounds B-1 to B-197, depending on the deuterium substitution position and the deuterium substitution rate, etc.

[0178] [B-198] [B-199] [B-200]

[0179] [B-201] [B-202] [B-203] [B-204]

[0180] [B-205] [B-206] [B-207] [B-208]

[0181] [B-209] [B-210] [B-211] [B-212]

[0182] [B-213] [B-214] [B-215] [B-216]

[0183] [B-217] [B-218] [B-219]

[0184] [B-220] [B-221] [B-222] [B-223]

[0185] [B-224] [B-225] [B-226] [B-227]

[0186] [B-228] [B-229] [B-230] [B-231]

[0187] [B-232] [B-233] [B-234] [B-235] [B-236]

[0188] [C-1] [C-2] [C-3] [C-4]

[0189] [C-5] [C-6] [C-7] [C-8]

[0190] [C-9] [C-10] [C-11] [C-12]

[0191] [C-13] [C-14] [C-15] [C-16]

[0192] [C-17] [C-18] [C-19] [C-20]

[0193] [C-21] [C-22] [C-23] [C-24]

[0194] [C-25] [C-26] [C-27] [C-28]

[0195] [C-29] [C-30] [C-31] [C-32]

[0196] [C-33] [C-34] [C-35] [C-36]

[0197] [C-37] [C-38] [C-39] [C-40]

[0198] [C-41] [C-42] [C-43] [C-44]

[0199] [C-45] [C-46] [C-47] [C-48]

[0200] [C-49] [C-50] [C-51] [C-52]

[0201] [C-53] [C-54] [C-55] [C-56]

[0202] [C-57]

[0203] Additionally, examples are provided below of compounds C-1 to C-57 listed in Group 2 in which at least one hydrogen atom is replaced by deuterium, but this is not an end of the range.

[0204] [C-58] [C-59] [C-60] [C-61] [C-62]

[0205] [C-63] [C-64] [C-65] [C-66] [C-67]

[0206] [C-68] [C-69] [C-70] [C-71] [C-72]

[0207] (Dn represents the number of deuterium substitutions and indicates a structure with one or more deuterium substitutions).

[0208] For compounds C-58 to C-72 of Group 2, the most specific structures are provided below as examples only, based on the deuterium substitution position and substitution rate, and these structures are not intended to limit the scope of rights of compounds not provided below.

[0209] The scope of the invention is defined by the claims, and if deuterium is substituted, the invention is not limited to the compounds illustrated below, but may include all variable ranges within the range described above for compounds C-1 to C-72, depending on the deuterium substitution position and the deuterium substitution rate, etc.

[0210] [C-73] [C-74]

[0211] [C-75] [C-76] [C-77] [C-78]

[0212] [C-79] [C-80] [C-81] [C-82]

[0213] [C-83] [C-84] [C-85] [C-86]

[0214] [C-87] [C-88] [C-89] [C-90]

[0215] [C-91] [C-92] [C-93] [C-94]

[0216] [C-95] [C-96] [C-97] [C-98]

[0217] [C-99] [C-100] [C-101] [C-102]

[0218] One type or two or more types of second compounds may be used.

[0219] In the light-emitting layer 32, a first compound and a second compound may be included as the main components, and the first compound and the second compound may be included in a weight ratio of, for example, about 1:99 to 99:1. Within the above range, the electron transport capability of the first compound and the hole transport capability of the second compound can be utilized to achieve bipolar characteristics by matching an appropriate weight ratio to improve efficiency and lifetime. Within this range, for example, they may be included in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20 (e.g., about 20:80 to about 70:30, about 20:80 to about 60:40, and about 20:80 to about 50:50). As a specific example, they may be included in a weight ratio of about 20:80, 30:70, or 40:60.

[0220] In addition to the first and second compounds mentioned above, the luminescent layer 32 may also contain one or more compounds as the main body.

[0221] The light-emitting layer 32 may also contain dopants.

[0222] The dopant can be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and can be, for example, a red or green phosphorescent dopant.

[0223] A dopant is a material that is mixed in small amounts with a compound used in organic optoelectronic devices to induce luminescence, and is typically a material such as a metal complex that emits light by being excited multiple times to a triplet or more states. Dopants can be, for example, inorganic, organic, or organic / inorganic compounds, and one or more of these types can be used.

[0224] Examples of dopants can be phosphorescent dopants, and examples of phosphorescent dopants can be organometallic compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants can be, for example, compounds represented by the chemical formula Z, but are not limited thereto.

[0225] [Chemical Formula Z]

[0226] L 9 MX 1

[0227] In the chemical formula Z, M is a metal, and L 9 and X 1The same or different, and is a ligand to form a complex with M.

[0228] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L 9 and X 1 It could be, for example, a bidentate ligand.

[0229] By L 9 and X 1 Examples of ligands may be selected from, but are not limited to, the chemical formulas listed in group A.

[0230] [Group A]

[0231] In group A, R 300 To R 302 Each is independently hydrogen, deuterium, a C1 to C30 alkyl group substituted or unsubstituted with a halogen, a C6 to C30 aryl group substituted or unsubstituted with a C1 to C30 alkyl group, or a halogen, and R 303 To R 324 Each of the following is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF5, trialkylsilyl having substituted or unsubstituted C1 to C30 alkyl, dialkylarylsilyl having substituted or unsubstituted C1 to C30 alkyl and C6 to C30 aryl, or triarylsilyl having substituted or unsubstituted C6 to C30 aryl.

[0232] In one embodiment, the dopant may be an iridium complex and may be represented by, for example, chemical formula V-1 or chemical formula V-2.

[0233] [Chemical Formula V-1]

[0234] In chemical formula V-1, R 101 To R 116 Each of these elements is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 132 R 133 R 134 , R 132 To R 134 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. R 101 To R 116 At least one of them is a functional group represented by chemical formula 6. L 100 It is a bidentate ligand for monovalent anions, and is a ligand coordinated to iridium via the lone pair electrons of carbon or heteroatoms. n5 and n6 are each independent integers from 0 to 3, and n5 + n6 is an integer from 1 to 3. [Chemical Formula 6]

[0235] In chemical formula 6, R 135 To R 139 Each of these elements is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 132 R 133 R 134 ,and It refers to the part that is attached to a carbon atom.

[0236] [Chemical formula V-2]

[0237] In chemical formula V-2, R 101 To R 117 Each of these elements is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 133 R 134 R 135 , R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. L 100 It is a bidentate ligand for monovalent anions, and is a ligand coordinated to iridium via the lone pair electrons of carbon or heteroatoms. n1 and n2 are each independent integers from 0 to 3, and n1 + n2 is an integer from 1 to 3.

[0238] In another embodiment, the dopant may be a platinum complex, such as a platinum complex represented by the chemical formula Z-1.

[0239] [Chemical Formula Z-1]

[0240] In chemical formula Z-1, rings A, B, C, and D independently represent 5- or 6-membered carbon rings or heterocycles; R A R B R C and R D Independently indicates mono-, di-, tri-, or tetra-substituted or unsubstituted; L B L C and L D Each is independently selected from direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; When nA is 1, L E Selected from direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and their combinations; when nA is 0, L E It does not exist; and R A R B R C R D R and R' are each independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; any adjacent R A R B R C R D R and R' are optionally connected to each other to provide a loop; X B X C X D and X E Each is independently selected from carbon and nitrogen; and Q 1 Q 2 Q 3 and Q 4 Each represents oxygen or a direct bond.

[0241] According to one embodiment, the dopant may be a platinum complex and may be represented, for example, by chemical formula VI-1 or chemical formula VI-2.

[0242] [Chemical Formula VI-1] [Chemical Formula VI-2]

[0243] In chemical formulas VI-1 and VI-2, X 100 Selected from O, S and NR 131 , R 118 To R 132 Each of these elements is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 133 R 134 R 135 , R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group, and R 118 To R 132 At least one of them is -SiR 133 R 134 R 135 Or tert-butyl.

[0244] The hole transport auxiliary layer 33 contains a third compound with relatively strong bipolar properties and hole characteristics.

[0245] As described above, the light-emitting layer 32 comprises a first compound having relatively strong bipolar properties and a second compound having relatively strong hole properties, thus improving the mobility of electrons and holes and significantly improving luminous efficiency compared to the compounds alone.

[0246] When materials with biased electron or hole properties are used to form the luminescent layer, in devices including the luminescent layer, excitons are generated relatively more frequently at the interface between the luminescent layer and the electron transport layer or hole transport layer due to the recombination of charge carriers. Therefore, the interaction of charges at the interface between molecular excitons in the luminescent layer and the hole transport layer causes a sharp roll-off in efficiency and also drastically degrades the luminescence lifetime characteristics.

[0247] To address these issues, a first and a second compound can be simultaneously incorporated into the emissive layer to prevent the luminescent region from being biased toward either the electron transport layer or the hole transport layer. Furthermore, a hole transport auxiliary layer comprising a third compound with relatively strong hole properties is placed between the hole transport layer and the emissive layer, thereby preventing charge accumulation at the interface between the hole transport layer and the emissive layer and providing a means to adjust the carrier balance in the emissive layer. Therefore, the roll-off characteristics of organic optoelectronic devices can be improved, and lifetime characteristics can be significantly enhanced simultaneously.

[0248] The third compound can be represented by chemical formula 5.

[0249] [Chemical Formula 5]

[0250] In chemical formula 5, Ar 8 and Ar 9 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. Ar 10 and Ar 11 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 41 To R 45 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and m5 is an integer from 1 to 3.

[0251] When m5 is 2 or greater, R 41 Each can be the same as or different from the other.

[0252] The third compound has a structure in which the amine core is substituted by at least one fluorene group.

[0253] By replacing the amine core with at least one fluorene group, steric hindrance can be used to minimize thermal degradation by lowering the deposition temperature, thereby further improving lifetime characteristics.

[0254] For example, depending on the substitution position of fluorene, the third compound can be represented by any of the chemical formulas 5-1 to 5-4.

[0255] [Chemical Formula 5-1] [Chemical Formula 5-2]

[0256] [Chemical Formula 5-3] [Chemical Formula 5-4]

[0257] In chemical formulas 5-1 to 5-4 Ar 8 To Ar 11 R 41 To R 45 The same applies to m5 as described above.

[0258] For example, the third compound can be represented by chemical formula 5-4.

[0259] In chemical formula 5, Ar 8 and Ar 9Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl (spirobifluorenyl group), substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0260] For example, Ar 8 and Ar 9 Each can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted fluorene group.

[0261] In chemical formula 5, Ar 10 and Ar 11 They can be substituted or unsubstituted C1 to C5 alkyl groups, or substituted or unsubstituted C6 to C12 aryl groups, each independently.

[0262] For example, Ar 10 and Ar 11 Each can be independently a substituted or unsubstituted C1 to C5 alkyl, a substituted or unsubstituted phenyl, or a substituted or unsubstituted biphenyl.

[0263] In chemical formula 5, R 41 To R 45 Each can be hydrogen, deuterium, or substituted or unsubstituted C1 to C5 alkyl groups, independently.

[0264] For example, R 41 To R 45 They can be hydrogen, deuterium, or tert-butyl, each independently.

[0265] Ar 8 and Ar 9 At least one of them can be a substituted or unsubstituted fluorene group, and can be represented by, for example, chemical formula 5-4-1.

[0266] [Chemical Formula 5-4-1]

[0267] In chemical formula 5-4-1, Ar 9 To Ar 11 R 41 To R 45 The same applies to m5 as described above. Ar 12 and Ar 13 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 53 To R57 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and m13 is an integer from 1 to 3.

[0268] In chemical formula 5-4-1, when m13 is 2 or greater, R 53 Each can be the same as or different from the other.

[0269] In chemical formula 5-4-1, Ar 12 and Ar 13 Each can be independently a substituted or unsubstituted C1 to C5 alkyl or a substituted or unsubstituted C6 to C12 aryl.

[0270] For example, Ar 12 and Ar 13 Each can be independently a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0271] In chemical formula 5-4-1, R 53 To R 57 Each can be hydrogen, deuterium, or substituted or unsubstituted C1 to C5 alkyl groups, independently.

[0272] For example, R 53 To R 57 They can be hydrogen, deuterium, or tert-butyl, each independently.

[0273] As a more specific example, chemical formula 5-4-1 can be selected from chemical formula 5-4-1a, chemical formula 5-4-1b, chemical formula 5-4-1c and chemical formula 5-4-1d.

[0274] [Chemical Formula 5-4-1a] [Chemical Formula 5-4-1b]

[0275] [Chemical Formula 5-4-1c] [Chemical Formula 5-4-1d]

[0276] In chemical formulas 5-4-1a, 5-4-1b, 5-4-1c, and 5-4-1d, Ar 9 To Ar 13 R 41 To R 45 R 53 To R 57 m5 and m13 are the same as above.

[0277] As a most concrete example, the third compound can be represented by chemical formula 5-4-1b.

[0278] For example, in chemical formula 5, R 42 To R 45 At least two of them can be tert-butyl.

[0279] Alkyl groups that can improve the glass transition temperature can be introduced to improve heat resistance.

[0280] As a specific example, in chemical formula 5-4-1, R 42 To R 45 At least two of them or R 54 To R 57 At least two of them can be tert-butyl.

[0281] For example, in chemical formula 5, R 43 and R 45 Each can be a tert-butyl.

[0282] For example, in chemical formula 5-4-1, R 43 and R 45 Each can be a tert-butyl.

[0283] For example, in chemical formula 5-4-1, R 54 and R 56 Each can be a tert-butyl.

[0284] For example, the third compound may be, for example, one of the compounds selected from group 3, but is not limited thereto.

[0285] [Group 3]

[0286] [E-1] [E-2] [E-3] [E-4]

[0287] [E-5] [E-6] [E-7] [E-8]

[0288] [E-9] [E-10] [E-11] [E-12]

[0289] [E-13] [E-14] [E-15] [E-16]

[0290] [E-17] [E-18] [E-19] [E-20]

[0291] [E-21] [E-22] [E-23] [E-24]

[0292] [E-25] [E-26] [E-27] [E-28]

[0293] [E-29] [E-30] [E-31] [E-32]

[0294] [E-33] [E-34] [E-35] [E-36]

[0295] [E-37] [E-38] [E-39] [E-40]

[0296] [E-41] [E-42] [E-43] [E-44]

[0297] [E-45] [E-46] [E-47] [E-48]

[0298] [E-49] [E-50] [E-51] [E-52]

[0299] [E-53] [E-54] [E-55] [E-56]

[0300] [E-57] [E-58] [E-59] [E-60]

[0301] [E-61] [E-62] [E-63] [E-64]

[0302] [E-65] [E-66] [E-67] [E-68]

[0303] [E-69] [E-70] [E-71] [E-72]

[0304] In the most specific embodiment of the present invention, the first compound may be represented by chemical formula 1, the second compound may be represented by chemical formula 2-8 or chemical formula 3C, and the third compound may be represented by chemical formula 5-4-1b.

[0305] In addition, the organic layer 30 may also include an electron transport region.

[0306] The electron transport region can further improve the electron injection and / or electron mobility between the cathode 20 and the light-emitting layer 32, but blocks holes.

[0307] Specifically, the electron transport region may include an electron transport layer 34 between the cathode 20 and the light-emitting layer 32 and an electron transport auxiliary layer between the light-emitting layer 32 and the electron transport layer 34, and at least one of the electron transport layer and the electron transport auxiliary layer may contain at least one of the compounds listed in Group B.

[0308] [Group B]

[0309] In addition to the light-emitting layer, the organic light-emitting diode may also include an electron injection layer (not shown), a hole injection layer (not shown), etc., as the aforementioned organic layer.

[0310] Organic light-emitting diodes (OLEDs) can be manufactured by forming an organic layer on a substrate using dry film methods (such as evaporation, sputtering, plasma plating, and ion plating) and then forming a cathode or anode thereon.

[0311] Organic light-emitting diodes (OLEDs) can be used in organic light-emitting display devices.

[0312] Invention Model

[0313] In the following description, implementation methods are illustrated in more detail with reference to embodiments. However, these embodiments are exemplary, and the scope of the invention is not limited thereto.

[0314] In the following text, the starting materials and reactants used in the examples and synthesis examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry, or P&H Tech, or synthesized by known methods, unless otherwise specified.

[0315] As a more specific example of the compounds of the present invention, the provided compounds are synthesized by the following steps.

[0316] Synthesis of the first compound

[0317] Synthesis Example 1: Synthesis of Compound A-43

[0318] [Reaction Formula 1]

[0319] Step 1: Synthesis of intermediate Int-1

[0320] 2,4-Dichloro-6-phenyl-1,3,5-triazine (20.0 g, 88.5 mmol), 3-dibenzofuranylboronic acid (17.8 g, 84.1 mmol), K₂CO₃ (24.5 g, 176.9 mmol), and Pd(dppf)Cl₂ (3.6 g, 4.4 mmol) were added to a round-bottom flask and dissolved in 250 mL of toluene and 90 mL of distilled water. The solution was stirred at 60°C for 6 hours. When the reaction was complete, the resulting organic layer was distilled under reduced pressure after separating the aqueous layer using a separatory funnel. The product obtained was dissolved by heating in monochlorobenzene, then filtered through silica and recrystallized to give 14.4 g (48%) of intermediate Int-1.

[0321] Step 2: Synthesis of intermediate Int-2

[0322] Intermediate Int-1 (14.4 g, 40.2 mmol), 5-chloro-2-fluorophenylboronic acid (6.8 g, 39.0 mmol), K₂CO₃ (10.8 g, 78.0 mmol), and Pd(PPh₃)₄ (2.25 g, 1.95 mmol) were added to a round-bottom flask, dissolved in 180 mL THF and 40 mL distilled water, and the solution was stirred and refluxed at 55°C for 6 hours. When the reaction was complete, after removing the aqueous layer, the residue was treated by column chromatography (hexane: DCM (30%)) to obtain 13.2 g (75%) of intermediate Int-2.

[0323] Step 3: Synthesis of intermediate Int-3

[0324] Intermediate Int-2 (13.2 g, 29.2 mmol), phenylboronic acid (10.7 g, 86.6 mmol), Cs₂CO₃ (19.0 g, 58.4 mmol), tri-tert-butylphosphine (2.9 ml, 5.8 mmol), and Pd₂(dba)₃ (1.3 g, 1.5 mmol) were added to a round-bottom flask and dissolved in 120 ml of 1,4-dioxane. The solution was stirred and refluxed at 100°C for 8 hours. When the reaction was complete, the reactants were cooled to room temperature and then poured into excess methanol to precipitate the solid. The solid was filtered and recrystallized from monochlorobenzene to obtain 10.8 g (75%) of intermediate Int-3.

[0325] Step 4: Synthesis of compound A-43

[0326] Intermediate Int-3 (10.8 g, 21.9 mmol), 2-phenyl-9H-carbazole (6.4 g, 26.3 mmol), and K3PO4 (9.3 g, 43.8 mmol) were added to a round-bottom flask and dissolved in 100 mL of DMF. The solution was stirred and refluxed at 150°C for 4 hours. When the reaction was complete, the reactants were slowly added dropwise to excess water to precipitate the solid. The solid was filtered and recrystallized from toluene to give 12.6 g (80%) of compound A-43.

[0327] Synthesis Example 2: Synthesis of Compound A-44

[0328] [Reaction 2]

[0329] Step 1: Synthesis of intermediate Int-5

[0330] In the same manner as in step 1 of Synthesis Example 1, 2,4-dichloro-6-phenyl-1,3,5-triazine (30.0 g, 132.7 mmol), intermediate Int-4 (46.7 g, 126.1 mmol), K2CO3 (36.7 g, 265.4 mmol) and Pd(dppf)Cl2 (5.42 g, 6.64 mmol) were used to obtain 45.6 g (83%) of intermediate Int-5.

[0331] Step 2: Synthesis of intermediate Int-6

[0332] 1-Bromo-3-chloro-2-fluorobenzene (25.0 g, 119.4 mmol), phenylboronic acid (16.0 g, 131.3 mmol), K₂CO₃ (33.0 g, 238.7 mmol), and Pd(PPh₃)₄ (6.9 g, 6.0 mmol) were added to a round-bottom flask, dissolved in 350 mL THF and 120 mL distilled water, and the solution was stirred and refluxed at 65°C for 6 hours. When the reaction was complete, after removing the aqueous layer, the residue was treated by column chromatography (hexane: DCM (20%)) to obtain 21.7 g (88%) of intermediate Int-6.

[0333] Step 3: Synthesis of intermediate Int-7

[0334] Intermediate Int-6 (21.7 g, 105.0 mmol), bis(pinacol)diboron (32.0 g, 126.0 mmol), tricyclohexylphosphine (5.1 g, 21.0 mmol), potassium acetate (20.6 g, 210.0 mmol), and Pd(dppf)Cl2 (4.29 g, 5.25 mmol) were added to a round-bottom flask and dissolved in 250 mL of DMF. The mixture was stirred and refluxed at 140°C for 8 hours. When the reaction was complete, after cooling to room temperature and then removing the resulting salt by filtration, excess DCM and distilled water were added to precipitate the mixture. Subsequently, column chromatography (hexane:DCM (30% to 50%) was performed to obtain 25.1 g (80%) of intermediate Int-7.

[0335] Step 4: Synthesis of intermediate Int-8

[0336] Intermediates Int-5 (14.5 g, 33.4 mmol), Int-7 (11.0 g, 36.8 mmol), K₂CO₃ (9.2 g, 66.8 mmol), and Pd(PPh₃)₄ (1.93 g, 1.67 mmol) were added to a round-bottom flask, dissolved in 170 ml THF and 40 ml distilled water, and the solution was stirred and refluxed at 70°C for 6 hours. When the reaction was complete, the resulting aqueous layer was removed and subjected to column chromatography (hexane: DCM (30%)) to obtain 13.3 g (70%) of intermediate Int-8.

[0337] Step 5: Synthesis of compound A-44

[0338] Intermediate Int-8 (13.3 g, 23.4 mmol), 9H-carbazole (4.7 g, 28.0 mmol), and K3PO4 (9.9 g, 46.7 mmol) were added to a round-bottom flask and dissolved in 100 mL of DMF. The solution was stirred and refluxed at 150°C for 4 hours. When the reaction was complete, the reactants were slowly added dropwise to excess water to precipitate the solid. The solid was filtered and recrystallized from monochlorobenzene to give 14.1 g (84%) of compound A-44.

[0339] Synthesis Example 3: Synthesis of Compound A-77

[0340] [Reaction 3]

[0341] Compound A-77 was synthesized in the same manner as in step 4 of Synthesis Example 1 by using intermediate Int-9 (CAS No. 1642330-72-0) and 2-phenyl-9H-carbazole.

[0342] Synthesis Example 4: Synthesis of Compound A-90

[0343] [Reaction 4]

[0344] Compound A-90 was synthesized in the same manner as in step 1 of Synthesis Example 1 by using intermediates Int-10 (CAS No. 2745196-22-7) and Int-11 (CAS No. 1189047-28-6).

[0345] Comparative Synthesis Example 1: Synthesis of Compound Main Body-1

[0346] The main compound, compound-1, was synthesized by referring to the synthesis method disclosed in the publicly available patent publication WO2023 / 072977.

[0347] Synthesis of the second compound

[0348] Synthesis Example 5: Synthesis of Compound B-136

[0349] Compound B-136 was synthesized using the synthetic method disclosed in registered patent US 10476008 B2.

[0350] HRMS (70 eV, EI+): Calculated m / z of C42H28N2: 560.2252, Measured: 560.

[0351] Elemental analysis: C, 90%; H, 5%.

[0352] Synthesis of the third compound

[0353] Synthesis Example 6: Synthesis of Compound E-1

[0354] [Reaction 5]

[0355] In a round-bottom flask, 410 g (1.203 mol) of intermediate E-1-1 (CAS No. 2924473-03-8), 435 g (1.082 mol) of amine intermediate (CAS No. 897674-69-1), and 173 g (1.804 mol) of sodium tert-butoxide were added and dissolved in 4000 ml of toluene. Then, 55 g (0.06 mol) of Pd2(dba)3 and 74 g (0.18 mol) of S-phos were added sequentially, and the mixture was stirred under reflux for 6 hours at a nitrogen atmosphere. When the reaction was complete, after removing the toluene solvent, the organic layer was extracted with toluene and distilled water, dried over magnesium sulfate, filtered, and the resulting filtrate was concentrated under reduced pressure. The product was purified by recrystallization from n-hexane / methanol to give 600 g (yield: 71%) of compound E-1.

[0356] Synthesis Example 7: Synthesis of Compound E-21

[0357] [Reaction Formula 6]

[0358] Compound E-21 was synthesized using intermediate E-1-1 and an amine intermediate (CAS No. 500717-23-7) in the same manner as in Synthesis Example 6.

[0359] (Manufacturing of organic light-emitting diodes)

[0360] Example 1

[0361] A glass substrate coated with ITO (indium tin oxide) as a thin film was washed with distilled water and ultrasonically. After washing with distilled water, the glass substrate was ultrasonically washed with solvents such as isopropanol, acetone, and methanol, and then dried. It was then transferred to a plasma cleaner and cleaned with oxygen plasma for 10 minutes before being transferred to a vacuum depositor. The ITO transparent electrode prepared in this way was used as the anode, and compound A, doped with 3% NDP-9 (commercially available from Novaled), was vacuum deposited on the ITO substrate to form a 100 Å thick hole injection layer, and a 1350 Å thick hole transport layer was formed thereon by depositing compound A. Compound E-21 obtained in Synthesis Example 8 was deposited on the hole transport layer to form a 270 Å thick first hole transport auxiliary layer, and compound B was deposited on the first hole transport auxiliary layer to form a 50 Å thick second hole transport auxiliary layer. On the second hole transport auxiliary layer, 85 wt% of compound A-43 (40%) synthesized in Synthesis Example 1 and compound B-136 (60%) synthesized in Synthesis Example 5 were used as the host, and 15 wt% of PtGD was doped as a dopant. A 380 Å thick emitting layer was formed by vacuum deposition. Subsequently, compound C was deposited on the emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compounds D and Liq were simultaneously vacuum deposited in a 1:1 weight ratio to form a 310 Å thick electron transport layer. An organic light-emitting diode was fabricated by sequentially vacuum depositing 15 Å of Yb and 1200 Å of Al on the electron transport layer to form a cathode.

[0362] The organic light-emitting diode has the following structure: ITO / compound A (3% NDP-9 doped, 100 Å) / compound A (1350 Å) / first hole transport auxiliary layer (270 Å) / compound B (50 Å) / light-emitting layer [body (compound A-43 : compound B-136 = 40 : 60): PtGD=85 wt% : 15 wt%] (380 Å) / compound C (50 Å) / compound D :Liq (310 Å) / Yb (15 Å) / Al (1200 Å).

[0363] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine

[0364] Compound B: 9,9-Dimethyl-N-[3-(9-phenyl-9H-fluorene-9-yl)phenyl]-N-(4-phenylphenyl)-9H-fluorene-2-amine

[0365] Compound C: 4-{4-[3-(9,9-dimethyl-9H-fluorene-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[0366] Compound D: 2-(4-{1-[4-(diphenyl-1,3,5-triazin-2-yl)phenyl]naphth-2-yl}phenyl)-4,6-diphenyl-1,3,5-triazine

[0367] PtGD:

[0368] Examples 2 to 4 and Comparative Example 1

[0369] The diodes of Examples 2 to 4 and Comparative Example 1 were manufactured in the same manner as in Example 1, except that the main body was changed as described in Table 1.

[0370] evaluate

[0371] The luminous efficiency characteristics of the organic light-emitting diodes according to Examples 1 to 4 and Comparative Example 1 were evaluated.

[0372] The specific measurement methods are as follows, and the results are shown in Table 1.

[0373] (1) Measure the change in current density based on the change in voltage.

[0374] While increasing the voltage from 0 V to 10 V, the current flowing through the unit diode in the obtained organic light-emitting diode was measured using a current-voltmeter (Keithley 2400), and the measured current value was divided by the area to provide the result.

[0375] (2) Measure the change in brightness based on voltage changes

[0376] The brightness was measured using a luminance meter (MinoltaCs-1000A) while the voltage of the organic light-emitting diode was increased from 0 V to 10 V.

[0377] (3) Measure luminous efficiency

[0378] Using the luminance and current density and voltage measured by (1) and (2) above, calculate the same current density (10 mA / cm²). 2 Current efficiency (cd / A) at ).

[0379] The luminous efficiency values ​​of Examples 1 to 4 and Comparative Example 1 were calculated based on the relative values ​​of Comparative Example 1 and are listed in Table 1.

[0380] [Table 1]

[0381] Referring to Table 1, compared with the organic light-emitting diodes according to the comparative example, the organic light-emitting diodes containing the composition according to the embodiments of the present invention exhibit significantly improved luminous efficiency.

[0382] Although the invention has been described in conjunction with embodiments that are now considered practical, it should be understood that the invention is not limited to the disclosed embodiments, but rather is intended to cover a variety of changes and equivalents included within the spirit and scope of the appended claims.

Claims

1. An organic optoelectronic device, comprising: The anode and cathode facing each other, The light-emitting layer between the anode and the cathode, The hole transport layer between the anode and the light-emitting layer, and A hole transport auxiliary layer between the light-emitting layer and the hole transport layer, in, The luminescent layer comprises a first compound represented by chemical formula 1 and a second compound represented by chemical formula 2 or a combination of chemical formulas 3 and 4, and The hole transport auxiliary layer contains a third compound represented by chemical formula 5: [Chemical Formula 1] In chemical formula 1, Z 1 To Z 3 Each is independently N or CR a , Z 1 To Z 3 At least two of them are N. R 1 To R 8 and R a Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. L 1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heterocyclic group, and Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group; [Chemical Formula 2] In chemical formula 2, Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. L 4 and L 5 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. R 9 To R 19 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. m1 and m2 are each an independent integer from 1 to 3. m3 is an integer from 1 to 4, and n is an integer between 0 and 2; [Chemical Formula 3] [Chemical Formula 4] In chemical formulas 3 and 4 Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. a1 in chemical formula 3 up to a4 Each is independently connected to carbon (C) or CL. a -R b , In chemical formula 4 Each is an independent linker of carbon (C). a1 in chemical formula 3 up to a4 The two adjacent ones are each connected to the chemical formula 4. , L a L 6 and L 7 Each is independently a single bond or a substituted or unsubstituted C6 to C20 aryl group, and R b and R 20 To R 27 Each of them is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group or substituted or unsubstituted C2 to C30 heterocyclic group; [Chemical Formula 5] In chemical formula 5, Ar 8 and Ar 9 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. Ar 10 and Ar 11 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 41 To R 45 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and m5 is an integer from 1 to 3.

2. The organic optoelectronic device according to claim 1, wherein... In chemical formula 1, Ar 1 and Ar 2 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazoyl.

3. The organic optoelectronic device according to claim 1, wherein... In chemical formula 1, L 1 -Ar 1 and L 2 -Ar 2 Each substituent is independently selected from those listed in Group I: [Group I] In group I, R 46 To R 48 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m6 is an integer from 1 to 5. m7 is an integer from 1 to 4. m8 is an integer from 1 to 3, and It is a connection point.

4. The organic optoelectronic device according to claim 1, wherein... The first compound is selected from one of the compounds listed in Group 1: [Group 1] [A-1] [A-2] [A-3] [A-4] [A-5] [A-6] [A-7] [A-8] [A-9] [A-10] [A-11] [A-12] [A-13] [A-14] [A-15] [A-16] [A-17] [A-18] [A-19] [A-20] [A-21] [A-22] [A-23] [A-24] [A-25] [A-26] [A-27] [A-28] [A-29] [A-30] [A-31] [A-32] [A-33] [A-34] [A-35] [A-36] [A-37] [A-38] [A-39] [A-40] [A-41] [A-42] [A-43] [A-44] [A-45] [A-46] [A-47] [A-48] [A-49] [A-50] [A-51] [A-52] [A-53] [A-54] [A-55] [A-56] [A-57] [A-58] [A-59] [A-60] [A-61] [A-62] [A-63] [A-64] [A-65] [A-66] [A-67] [A-68] [A-69] [A-70] [A-71] [A-72] [A-73] [A-74] [A-75] [A-76] [A-77] [A-78] [A-79] [A-80] [A-81] [A-82] [A-83] [A-84] [A-85] [A-86] [A-87] [A-88] [A-89] [A-90] [A-91] [A-92] [A-93] [A-94] [A-95] [A-96] [A-97] [A-98] [A-99] [A-100] [A-101] [A-102] [A-103] [A-104] [A-105] [A-106] [A-107] [A-108] [A-109] [A-110] [A-111] [A-112] [A-113] [A-114] [A-115] [A-116] [A-117] [A-118] [A-119] [A-120] 。 5. The organic optoelectronic device according to claim 1, wherein... Chemical formula 2 is represented by chemical formula 2-8: [Chemical Formula 2-8] In chemical formula 2-8, R 9 To R 18 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group. m1 and m2 are each an independent integer from 1 to 3, and L 4 -Ar 3 and L 5 -Ar 4 Each is independently one of the substituents listed in Group II. [Group II] In Group II, R 49 To R 52 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m9 is an integer from 1 to 5. m10 is one of the integers from 1 to 4. m11 is an integer from 1 to 3. m12 is an integer of 1 or 2, and It is a connection point.

6. The organic optoelectronic device according to claim 1, wherein... The combination of chemical formula 3 and chemical formula 4 is represented by chemical formula 3: [Chemical formula 3C] In the chemical formula 3C, L a3 and L a4 It's a single key. R 20 To R 27 R b3 and R b4 Each is independently hydrogen or C6 to C12 aryl, and L 6 -Ar 5 and L 7 -Ar 6 Each is independently one of the substituents listed in Group II. [Group II] In Group II, R 49 To R 52 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m9 is an integer from 1 to 5. m10 is an integer from 1 to 4. m11 is an integer from 1 to 3. m12 is an integer of 1 or 2, and It is a connection point.

7. The organic optoelectronic device according to claim 1, wherein... Chemical formula 5 is represented by chemical formula 5-4: [Chemical Formula 5-4] In chemical formula 5-4, Ar 8 To Ar 11 R 41 To R 45 m5 is defined in chemical formula 5.

8. The organic optoelectronic device according to claim 7, wherein... Chemical formula 5-4 is represented by chemical formula 5-4-1: [Chemical Formula 5-4-1] In chemical formula 5-4-1, Ar 9 To Ar 11 R 41 To R 45 m5 is defined in claim 1. Ar 12 and Ar 13 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 53 To R 57 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and m13 is an integer from 1 to 3.

9. The organic optoelectronic device according to claim 8, wherein... Chemical formula 5-4-1 is represented by chemical formula 5-4-1b: [Chemical Formula 5-4-1b] In chemical formula 5-4-1b, Ar 9 To Ar 13 R 41 To R 45 R 53 To R 57 m5 and m13 are defined in chemical formula 5-4-1.

10. The organic optoelectronic device according to claim 1, wherein... The third compound is selected from the compounds listed in Group 3: [Group 3] [E-1] [E-2] [E-3] [E-4] [E-5] [E-6] [E-7] [E-8] [E-9] [E-10] [E-11] [E-12] [E-13] [E-14] [E-15] [E-16] [E-17] [E-18] [E-19] [E-20] [E-21] [E-22] [E-23] [E-24] [E-25] [E-26] [E-27] [E-28] [E-29] [E-30] [E-31] [E-32] [E-33] [E-34] [E-35] [E-36] [E-37] [E-38] [E-39] [E-40] [E-41] [E-42] [E-43] [E-44] [E-45] [E-46] [E-47] [E-48] [E-49] [E-50] [E-51] [E-52] [E-53] [E-54] [E-55] [E-56] [E-57] [E-58] [E-59] [E-60] [E-61] [E-62] [E-63] [E-64] [E-65] [E-66] [E-67] [E-68] [E-69] [E-70] [E-71] [E-72] 。 11. The organic optoelectronic device according to claim 1, wherein... The second compound is represented by chemical formula 2-8 or chemical formula 3C, and The third compound is represented by chemical formula 5-4-1b: [Chemical Formula 2-8] In chemical formula 2-8, R 9 To R 18 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group. m1 and m2 are each an independent integer from 1 to 3, and L 4 -Ar 3 and L 5 -Ar 4 Each is independently one of the substituents listed in Group II. [Group II] In Group II, R 49 To R 52 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m9 is an integer from 1 to 5. m10 is an integer from 1 to 4. m11 is an integer from 1 to 3. m12 is an integer of 1 or 2, and It is a connection point; [Chemical formula 3C] In the chemical formula 3C, L a3 and L a4 It's a single key. R 20 To R 27 R b3 and R b4 Each is independently hydrogen or C6 to C12 aryl, and L 6 -Ar 5 and L 7 -Ar 6 Each is independently one of the substituents listed in Group II. [Group II] In Group II, R 49 To R 52 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m9 is an integer from 1 to 5. m10 is an integer from 1 to 4. m11 is an integer from 1 to 3. m12 is an integer of 1 or 2, and It is a connection point; [Chemical Formula 5-4-1b] In chemical formula 5-4-1b, Ar 10 and Ar 11 Each is independently a substituted or unsubstituted C1 to C5 alkyl group or a substituted or unsubstituted C6 to C12 aryl group. Ar 12 and Ar 13 Each is independently a substituted or unsubstituted C1 to C5 alkyl or a substituted or unsubstituted C6 to C12 aryl. R 41 To R 45 and R 53 To R 57 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C1 to C5 alkyl group. Ar 9 It is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted spirodifluorenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl. m5 and m13 are each an integer from 1 to 3.

12. A display device comprising the organic optoelectronic device according to any one of claims 1 to 11.

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