Organic optoelectronic device and display device

Abstract

Disclosed are an organic optoelectronic device and a display device. The 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, the light emitting layer includes a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2, and the hole transport auxiliary layer includes a third compound represented by Chemical Formula 3.

Description

[0001] Citations of relevant applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0119482, filed on September 3, 2024, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The implementation methods relate to organic optoelectronic devices and display devices. Background Technology

[0004] Organic optoelectronic devices (e.g., organic photodiodes) are devices that can convert electrical energy into light energy and vice versa.

[0005] Based on their working principles, organic optoelectronic devices can be divided into two categories. One category is optoelectronic devices that generate electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes. The other category is light-emitting devices that generate light energy from electrical energy by providing voltage or current to the electrodes.

[0006] Examples of organic optoelectronic devices can include organic photoelectric devices, organic light-emitting diodes, organic solar cells, and organic photosensitive drums.

[0007] Organic light-emitting diodes (OLEDs) have attracted 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 can be affected by the organic materials between the electrodes. Summary of the Invention

[0008] The implementation can be achieved by providing an organic optoelectronic device comprising 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 comprises a first compound represented by chemical formula 1 and a second compound represented by chemical formula 2, and the hole transport auxiliary layer comprises a third compound represented by chemical formula 3.

[0009] [Chemical Formula 1]

[0010]

[0011] In chemical formula 1, A and B are each independently a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring, L 1 and L 2 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 1It is 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, Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, provided that Ar 1 and Ar 2 At least one of them is a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenylyl, m1 is an integer from 1 to 4, and when m1 is 2, 3 or 4, each R 1 They are the same or different from each other;

[0012] [Chemical Formula 2]

[0013]

[0014] In chemical formula 2, Z 1 To Z 6 Each is independently N or CL a -R a Z 1 To Z 6 At least two of them are N, and each L a Independently, each R is a single bond, a substituted or unsubstituted C6 to C20 arylene, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof. a Independently, it is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof, and each R a They exist separately or adjacent groups are connected to each other to form substituted or unsubstituted aliphatic monocyclic or polycyclic, substituted or unsubstituted aromatic monocyclic or polycyclic, or substituted or unsubstituted heteroaromatic monocyclic or polycyclic.

[0015] [Chemical Formula 3]

[0016]

[0017] In chemical formula 3, Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl, R 2 To R 6Each 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, m2 is an integer from 1 to 3, and when m2 is 2 or 3, each R 2 They are the same or different from each other.

[0018] The implementation can be achieved by providing a display device that includes an organic optoelectronic device according to one embodiment. Attached Figure Description

[0019] The features will become apparent to those skilled in the art from the detailed description of exemplary embodiments with reference to the accompanying drawings, wherein:

[0020] Figure 1 This is a cross-sectional view of an organic light-emitting diode according to some exemplary embodiments.

[0021] <Explanation of Figure Markers>

[0022] 10: Anode

[0023] 20: Cathode

[0024] 30: Organic layer

[0025] 31: Hole transport layer

[0026] 32: Emissive layer

[0027] 33: Hole transport auxiliary layer

[0028] 34: Electron transport layer Detailed Implementation

[0029] Exemplary embodiments will now be described more fully below with reference to the accompanying drawings; however, they may be embodied in different forms and should not be construed as limited to the embodiments described herein. Rather, these embodiments are provided so that this disclosure will be exhaustive and complete to those skilled in the art, and will fully express the exemplary embodiments.

[0030] In the accompanying drawings, the dimensions of layers and regions may be enlarged for clarity. It will also be understood that when a layer or element is referred to as "on" another layer or substrate, it may be directly on the other layer or substrate, or there may be intermediate layers. Furthermore, it will be understood that when a layer is referred to as "below" another layer, it may be directly below, and one or more intermediate layers may be present. Additionally, it will be understood that when a layer is referred to as "between" two layers, it may be the only layer between the two layers, or one or more intermediate layers may be present. Throughout the specification, the same reference numerals denote the same elements.

[0031] As used herein, unless otherwise defined, “substituted” means that at least one hydrogen atom of a substituent or compound is replaced by one of the following: 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.

[0032] In one instance, "substituted" means that at least one hydrogen atom of a substituent or compound is replaced by one of the following: 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 instance, "substituted" means that at least one hydrogen atom of a substituent or compound is replaced by one of the following: deuterium, C1 to C20 alkyl, C3 to C20 cycloalkyl, C6 to C30 aryl, or cyano. In a specific instance, "substituted" means that at least one hydrogen atom of a substituent or compound is replaced by one of the following: deuterium, C1 to C5 alkyl, C3 to C10 cycloalkyl, C6 to C18 aryl, or cyano. In specific instances, "substituted" means that at least one hydrogen atom of a substituent or compound is replaced by one of the following: deuterium, cyano, methyl, ethyl, propyl, butyl, tert-butyl, cyclopropyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0033] As used in this article, "unsubstituted" means that the hydrogen atom is not replaced by another substituent and the hydrogen atom is retained.

[0034] As used herein, “hydrogen substitution (-H)” can include “deuterium substitution (-D)” or “tritium substitution (-T)”.

[0035] As used herein, unless otherwise defined, “heterogeneous” means a functional group containing one to three heteroatoms selected from N, O, S, P, and Si, and the remainder being carbon. As used herein, the term “or” is not an exclusive term; for example, “A or B” would include A, B, or A and B.

[0036] As used herein, “aryl” means a group comprising at least one aromatic hydrocarbon moiety, and all elements of the aromatic hydrocarbon moiety have conjugated p orbitals, such as phenyl, naphthyl, etc. Two or more aromatic hydrocarbon moiety moiety may be linked by σ bonds and may be, for example, biphenyl, terphenyl, tetraphenyl, etc., and two or more aromatic hydrocarbon moiety moiety may be directly or indirectly fused to provide a non-aromatic fused ring, such as fluorene.

[0037] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent carbon atom pairs) functional groups.

[0038] 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.

[0039] 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.

[0040] 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 phenanthrene, 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 triphenylene group, a substituted or unsubstituted peryl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indene, or a combination thereof.

[0041] 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 benzothiazolyl group. Fernyl, 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 naphridyl, 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 carbazoyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl or combinations thereof.

[0042] As used herein, hole properties refer to the ability to provide electrons to form holes when an electric field is applied, and holes formed in the anode can be readily injected into and transported in the emissive layer due to the conductivity of the highest occupied molecular orbital (HOMO) energy level.

[0043] 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.

[0044] The following describes an organic optoelectronic device according to some exemplary embodiments.

[0045] 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.

[0046] In this document, an organic light-emitting diode (OLED) is described as an example of an organic optoelectronic device with reference to the accompanying drawings; however, the embodiments can be applied in the same manner to other organic optoelectronic devices.

[0047] Figure 1 This is a cross-sectional view of an organic light-emitting diode according to some exemplary embodiments.

[0048] refer to Figure 1An organic optoelectronic device according to one embodiment may include, for example, an anode 10 and a cathode 20 facing each other, and an organic layer 30 between the anode 10 and the cathode 20.

[0049] The anode 10 can be made of a conductor with a high work function to facilitate hole injection, and can be, for example, a metal, a metal oxide, or a conductive polymer. The anode 10 can 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; or a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, or polyaniline.

[0050] The cathode 20 may be made of, for example, a conductor with a small work function to aid electron injection, and may be, for example, a metal, a metal oxide, 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, or alloys thereof; or a multilayer material such as LiF / Al, LiO2 / Al, LiF / Ca, or BaF2 / Ca.

[0051] The organic layer 30 may include, for example, 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.

[0052] Hole transport layer 31 may be, for example, a layer that helps holes transport from anode 10 to light-emitting layer 32, and may include, for example, an amine compound.

[0053] Amine compounds may include, for example, at least one aryl or heteroaryl group. Amine compounds may be represented, for example, by chemical formula a or chemical formula b.

[0054]

[0055] In chemical formula a or b, Ar a To Ar g Each of these can be, independently, or include, for example, 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.

[0056] Ar a To Ar c At least one of them and Ar d To Ar g At least one of them may be or include, for example, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C2 to C30 heteroaryl groups, or combinations thereof.

[0057] Ar h It may be or include, for example, single bonds, substituted or unsubstituted C1 to C20 alkylene groups, substituted or unsubstituted C6 to C30 arylene groups, substituted or unsubstituted C2 to C30 heteroarylene groups, or combinations thereof.

[0058] The light-emitting layer 32 may include, for example, at least two types of host materials and dopants. The host material may include, for example, a first compound with relatively strong hole characteristics and a second compound with relatively strong electronic characteristics and bipolar properties.

[0059] The first compound can be a compound with relatively strong hole properties and can be represented by chemical formula 1.

[0060] [Chemical Formula 1]

[0061]

[0062] In chemical formula 1, A and B can each be, or include, for example, a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring.

[0063] L 1 and L 2 Each can be, independently or include, for example, a single bond or substituted or unsubstituted C6 to C20 aryl groups.

[0064] R 1 It may be or include, for example, 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.

[0065] Ar 1 and Ar 2 Each may be, independently or include, for example, substituted or unsubstituted C6 to C20 aryl groups or substituted or unsubstituted C2 to C30 heterocyclic groups.

[0066] In one implementation, Ar 1 and Ar 2 At least one of them can be, for example, a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenylyl.

[0067] m1 can be, for example, an integer from 1 to 4.

[0068] In one implementation, m1 can be 2, 3, or 4, and each R 1 They can be the same as or different from each other.

[0069] Chemical formula 1 can be represented, for example, by chemical formula 1A to chemical formula 1E.

[0070]

[0071] In chemical formulas 1A to 1E, Ar 1 Ar 2 L 1 and L 2 It can be the same as those definitions mentioned above.

[0072] L b1 and L b2 They can be, for example, single bonds or substituted or unsubstituted C6 to C20 aryl groups.

[0073] R 7 To R 12 R b1 and R b2 Each can be independently, for example, 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.

[0074] n1 to n3 can each be an integer, for example, 0 or 1, independently.

[0075] In one implementation, n1 and n2 can each be 0, and m3 and m4 can each be an integer, for example, 1 to 4.

[0076] In one implementation, n1 and n2 can each be 1, and m3 and m4 can each be an integer, for example, 1 or 2.

[0077] In one implementation, n3 can be 0, and m5 can be an integer such as 1 or 2.

[0078] In one implementation, n3 can be 1, and m5 can be, for example, 0.

[0079] m6 to m8 can each be an integer, for example, 1 to 4.

[0080] In one implementation, m3 can be 2, 3, or 4, and each R 7 They can be the same as or different from each other.

[0081] In one implementation, m4 can be 2, 3, or 4, and each R 8 They can be the same as or different from each other.

[0082] In one implementation, m5 can be 2, and each R 9 They can be the same as or different from each other.

[0083] In one implementation, m6 can be 2, 3, or 4, and each R 10 They can be the same as or different from each other.

[0084] In one implementation, m7 can be 2, 3, or 4, and each R 11 They can be the same as or different from each other.

[0085] In one implementation, m8 can be 2, 3, or 4, and each R 12 They can be the same as or different from each other.

[0086] In one implementation, Ar 1 and Ar 2 Each of these can be independently, for example, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0087] In one implementation, Ar 1 and Ar 2 At least one of them can be, for example, a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenylyl.

[0088] In one implementation, L 1 and L 2 Each can be, independently, a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0089] In one implementation, R 1 It can be a substituted or unsubstituted C1 to C10 alkyl, a substituted or unsubstituted C6 to C20 aryl, or a substituted or unsubstituted C2 to C20 heterocyclic group.

[0090] In one embodiment, chemical formula 1 may be represented by chemical formula 1A-1.

[0091] [Chemical Formula 1A-1]

[0092]

[0093] In chemical formula 1A-1, L a1 L a2 L 1 and L 2 Each can be, independently, a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0094] Ar 1It can be, for example, a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenylyl.

[0095] Ar 2 It can be, for example, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiopheneyl.

[0096] R 7 R 8 R 11 R b1 and R b2 Each can be independently, for example, 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.

[0097] m3 can be, for example, an integer from 1 to 4.

[0098] m4' can be an integer, for example, 1 or 2.

[0099] m7 can be, for example, an integer from 1 to 4.

[0100] In one implementation, m3 can be 2, 3, or 4, and each R 7 They can be the same as or different from each other.

[0101] In one implementation, m4' can be 2, and each R 8 They can be the same as or different from each other.

[0102] In one implementation, m7 can be 2, 3, or 4, and each R 11 They can be the same as or different from each other.

[0103] The first compound can be, for example, a compound from group 1.

[0104] [Group 1]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] (Dn represents the number of deuterium atoms substituted, where n is an integer greater than or equal to 0, and the maximum value of n corresponds to the number of substituted hydrogen positions.)

[0111] Since the second compound effectively expands the LUMO band by including a nitrogen-containing hexagonal moiety, it can be included together with the first compound to improve the balance between holes and electrons, thereby helping to significantly improve the lifetime characteristics of the device used therein.

[0112] The second compound can be represented, for example, by chemical formula 2.

[0113] [Chemical Formula 2]

[0114]

[0115] In chemical formula 2, Z 1 To Z 6 Each can be, independently, or include, for example, N or CL. a -R a .

[0116] In one implementation, Z 1 To Z 6 At least two of them can be N.

[0117] Each L a It may be, independently or include, for example, a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof.

[0118] Each R a It may independently be or include, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof.

[0119] Each R a They can exist separately or adjacent groups can be connected to each other to form substituted or unsubstituted aliphatic monocyclic or polycyclic, substituted or unsubstituted aromatic monocyclic or polycyclic, or substituted or unsubstituted heteroaromatic monocyclic or polycyclic.

[0120] In one implementation, Z 1 To Z 6 Two of them can be nitrogen (N) and the rest can be CL. a -R a .

[0121] In one implementation, Z 1 and Z3 It can be nitrogen, Z 2 It can be N or CL a -R a Z 4 It can be N or CL a -R a Z 5 It can be N or CL a -R a And Z 6 It can be N or CL a -R a .

[0122] In one implementation, Z 1 To Z 6 Three of them can be nitrogen (N) and the rest can be CL. a -R a .

[0123] In one implementation, Z 1 Z 3 and Z 5 It can be nitrogen, Z 2 It can be N or CL a -R a Z 4 It can be N or CL a -R a And Z 6 It can be N or CL a -R a .

[0124] In one implementation, according to R a The specific substituents of the second compound can be represented, for example, by one of chemical formulas 2A to 2E.

[0125]

[0126]

[0127] In chemical formulas 2A to 2E, Z 1 Z 3 and Z 5 They can be, for example, N or CL, independently. a -R a .

[0128] In one implementation, Z 1 Z 3 and Z 5 At least two of them can be N.

[0129] X 1It can be, for example, O, S, or NR. c .

[0130] L a and L 3 To L 5 Each can be, independently, a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof.

[0131] R a R c and R 14 To R 29 Each of these can be, independently, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, or combinations thereof.

[0132] R 14 To R 26 They can exist separately, or adjacent groups can connect with each other to form substituted or unsubstituted aromatic monocyclic or polycyclic rings.

[0133] Ar 7 Ar 8 and Ar 11 They can be, independently, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C2 to C30 heterocyclic groups, or combinations thereof.

[0134] R a Ar 7 and Ar 8 They can exist separately, or R a Ar 7 and Ar 8 Adjacent groups in the form can be linked together to form substituted or unsubstituted aromatic monocyclic or polycyclic or substituted or unsubstituted heteroaromatic monocyclic or polycyclic.

[0135] m15 and m16 can each be an integer, for example, from 1 to 4, independently.

[0136] m13 and m14 can each be an integer, for example, from 1 to 3, independently.

[0137] In one implementation, m13 can be 2 or 3, and each R 22 They can be the same as or different from each other.

[0138] In one implementation, m14 can be 2 or 3, and each R 27 They can be the same as or different from each other.

[0139] In one implementation, m15 can be 2, 3, or 4, and each R 28 They can be the same as or different from each other.

[0140] In one implementation, m16 can be 2, 3, or 4, and each R 29 They can be the same as or different from each other.

[0141] As used herein, the expression that adjacent groups are linked together to form substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic compounds means that any two adjacent substituents can be linked together to form a ring. In one embodiment, in formula 2A, R 14 To R 21 Adjacent groups in the aromatic monocyclic ring can connect with each other to form a substituted or unsubstituted aromatic monocyclic ring. In this paper, the aromatic monocyclic ring formed can be, for example, a substituted or unsubstituted phenyl group.

[0142] In one implementation, R 14 To R 26 Adjacent groups in the aromatic polycyclic aromatic hydrocarbon can be linked together to form substituted or unsubstituted aromatic polycyclic aromatic hydrocarbons, and the formed aromatic polycyclic aromatic hydrocarbons can be, for example, substituted or unsubstituted naphthyl groups.

[0143] In one implementation, R 14 To R 26 Adjacent groups in the form can be linked together to form substituted or unsubstituted heteroaromatic polycyclic compounds, and the formed heteroaromatic polycyclic compounds can be, for example, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, etc.

[0144] In one embodiment, chemical formula 2A may be represented, for example, by one of chemical formulas 2A-I to 2A-X.

[0145]

[0146]

[0147]

[0148] In chemical formulas 2A-I to 2A-X, L 3 To L 5 Each can be independently, for example, a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group.

[0149] Ar7 and Ar 8 Each of these can be independently, for example, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted naphthobenzofuranyl, or substituted or unsubstituted naphthobenzothiophene.

[0150] R 14 To R 21 R 30 and R 31 Each of these can be, independently, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiopheneyl.

[0151] m17 and m18 can each be an integer from 1 to 4, for example, independently.

[0152] In one embodiment, chemical formula 2B may be represented, for example, by one of chemical formulas 2B-I to 2B-VII.

[0153]

[0154]

[0155] In chemical formulas 2B-I to 2B-VII, each substituent may be the same as those defined in chemical formula 2B.

[0156] R 37 It can be, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiopheneyl.

[0157] m19 can be, for example, an integer from 1 to 4.

[0158] In one embodiment, in chemical formulas 2B-I to 2B-VII, L 3 To L 5 Each can be independently, for example, a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted dibenzothiopheneylene.

[0159] X 1 It can be, for example, O or S.

[0160] Ar 7 and Ar 8Each of these can be independently, for example, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted naphthobenzofuranyl, or substituted or unsubstituted naphthobenzothiophene.

[0161] R 22 To R 26 and R 37 Each of these can be, independently, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiopheneyl.

[0162] m13 can be, for example, an integer from 1 to 3.

[0163] m19 can be, for example, an integer from 1 to 4.

[0164] In one embodiment, chemical formula 2C may be represented, for example, by chemical formula 2C-I or chemical formula 2C-II.

[0165]

[0166] In chemical formulas 2C-I and 2C-II, each substituent may be the same as those defined in chemical formula 2C.

[0167] In one embodiment, in chemical formulas 2C-I and 2C-II, L 3 To L 5 Each can be an independent, for example, a single bond or a substituted or unsubstituted phenylene.

[0168] Ar 7 and Ar 8 Each of these can be independently, for example, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted naphthobenzofuranyl, or substituted or unsubstituted naphthobenzothiophenyl.

[0169] R 27 To R 29 Each of these can be, independently, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiopheneyl.

[0170] m14 can be, for example, an integer from 1 to 3.

[0171] m15 and m16 can each be an integer, for example, from 1 to 4, independently.

[0172] In one embodiment, chemical formula 2 may be represented, for example, by chemical formula 2B-IV.

[0173] The second compound can be, for example, a compound from group 2.

[0174] [Group 2]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184] (Dn represents the number of deuterium atoms substituted, where n is an integer greater than or equal to 0, and the maximum value of n corresponds to the number of substituted hydrogen positions.)

[0185] 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, from about 1:99 to about 99:1. By including them in the above range, the hole transport capability of the first compound and the electron transport capability of the second compound can be used to achieve an appropriate weight ratio to realize bipolar characteristics, thereby improving efficiency and lifetime. Within the above range, they may be included in weight ratios of, for example, from about 90:10 to about 10:90, from about 80:20 to about 20:80 (e.g., from about 80:20 to about 30:70, from about 80:20 to about 40:60, and from about 80:20 to about 50:50). In one embodiment, they may be included in weight ratios of about 80:20, about 70:30, or about 60:40.

[0186] In one implementation, by introducing fused-ring polycyclic functional groups, the T1 energy level can be lowered, which helps to promote exciton transfer to the red emitting dopant, thereby helping to improve the efficiency of the device.

[0187] In addition to the first and second compounds mentioned above, the luminescent layer 32 may also include, for example, one or more compounds as the main body.

[0188] The light-emitting layer 32 may also include, for example, dopants.

[0189] 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.

[0190] 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.

[0191] Examples of dopants may be or include phosphorescent dopants, and examples of phosphorescent dopants may be or include organometallic compounds comprising Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants may be, for example, compounds represented by the chemical formula Z.

[0192] [Chemical Formula Z]

[0193] L 6 MX 2

[0194] In the chemical formula Z, M can be, for example, a metal, and L 6 and X 2 They can be the same or different, and can be, for example, ligands that form complexes with M.

[0195] 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 6 and X 2 It could be, for example, a bidentate ligand.

[0196] By L 6 and X 2 The ligand represented can be, for example, one of the chemical formulas Z-1 to Z-8.

[0197]

[0198]

[0199] In chemical formulas Z-1 to Z-8, X 14 It can be, for example, carbon or nitrogen.

[0200] Y 100 It can be, for example, O or S.

[0201] R 101 To R 122 Each of these can be independently, for example, hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, -SiR 133 R 134 R 135 or -GeR 133 R 134 R 135 Alternatively, it can be attached to an adjacent substituent to form a substituted or unsubstituted ring, and for example, together with pyridine, it can form a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuranopyridine, a substituted or unsubstituted benzothiophenopyridine, a substituted or unsubstituted indenepyridine, a substituted or unsubstituted benzofuranoquinoline, a substituted or unsubstituted benzothiophenoquinoline, or a substituted or unsubstituted indenequinoline.

[0202] m18 can be, for example, an integer from 1 to 4.

[0203] m19 can be, for example, an integer from 1 to 5.

[0204] m111 can be an integer such as 1 or 2.

[0205] By L 6 and X 2 Examples of ligands can be, for example, chemical formulas of group A.

[0206] [Group A]

[0207]

[0208]

[0209] In group A, R 300 To R 302 Each of these can be, independently, for example, hydrogen, deuterium, halogen-substituted or unsubstituted C1 to C30 alkyl groups, halogen-substituted or unsubstituted C6 to C30 aryl groups, or halogens.

[0210] R 303 To R 308Each of these can be, independently, for example, 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 or substituted or unsubstituted C6 to C30 aryl or triarylsilyl having substituted or unsubstituted C6 to C30 aryl.

[0211] m25 can be, for example, an integer from 1 to 5.

[0212] m26 can be, for example, an integer from 1 to 4.

[0213] m27 can be, for example, an integer from 1 to 3.

[0214] m28 can be an integer such as 1 or 2.

[0215] m29 can be, for example, an integer from 1 to 6.

[0216] In one implementation, one of m25 to m27 and m29 can be an integer of 2 or greater, and m28 can be 2, and R 303 To R 307 Each can be the same as or different from the other.

[0217] In some exemplary embodiments, the phosphorescent dopant may be an iridium complex and may be represented, for example, by one of chemical formulas 6 to 8.

[0218] [Chemical Formula 6]

[0219]

[0220] In chemical formula 6, ring A can be, for example, a monocyclic or polycyclic fused ring, wherein each ring in the monocyclic or polycyclic fused ring can be, for example, a 5- or 6-membered carbon ring or a heterocyclic ring.

[0221] R 100 It can represent, for example, one to a maximum number of monovalent substituents.

[0222] In one implementation, there may be two or more Rs. 100 Groups, and each R 100 They can be the same as or different from each other.

[0223] R 101 To R 104Each of these can be independently, for example, hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 114 R 115 R 116 -GeR 114 R 115 R 116 Or a combination of them.

[0224] R 114 To R 116 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0225] X 10 and X 11 They can be, for example, carbon or nitrogen, each independently.

[0226] L 100 It can be, for example, a monovalent anion ligand or a bidentate ligand that coordinates to iridium via a non-shared electron pair of a carbon or heteroatom.

[0227] m21 can be, for example, an integer from 0 to 3.

[0228] [Chemical Formula 7]

[0229]

[0230] In Formula 7, ring B can be, for example, a monocyclic or polycyclic fused ring, wherein each ring in the monocyclic or polycyclic fused ring can be, for example, a 5- or 6-membered carbon ring or a heterocyclic ring.

[0231] Y 100 It can be, for example, O or S.

[0232] R 201 It can represent, for example, one to a maximum number of monovalent substituents.

[0233] In one implementation, there may be two or more Rs. 201 Groups, and each R 201 They can be the same as or different from each other.

[0234] R 206 To R 213 Each of these can be independently, for example, hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 114 R 115 R 116 -GeR 114 R 115 R 116 Or a combination of them.

[0235] R114 To R 116 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0236] X 12 and X 13 They can be, for example, carbon or nitrogen, each independently.

[0237] L 100 It can be, for example, a monovalent anion ligand or a bidentate ligand that coordinates to iridium via a non-shared electron pair of a carbon or heteroatom.

[0238] m21 can be, for example, an integer from 0 to 3.

[0239] m100 can be, for example, an integer from 1 to 3.

[0240] m101 can be an integer such as 1 or 2.

[0241] n100 can be an integer, for example, 0 or 1.

[0242] [Chemical Formula 8]

[0243]

[0244] In chemical formula 8, Y 100 It can be, for example, O or S.

[0245] R 101 To R 111 Each of these can be independently, for example, hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 114 R 115 R 116 -GeR 114 R 115 R 116 Or a combination of them.

[0246] R 114 To R 116 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0247] L 100 It can be, for example, a monovalent anion ligand or a bidentate ligand that coordinates to iridium via a non-shared electron pair of a carbon or heteroatom.

[0248] m21 can be, for example, an integer from 0 to 3.

[0249] In one embodiment, the iridium complex may be represented, for example, by one of chemical formulas 6-1 to 6-6.

[0250] [Chemical Formula 6-1]

[0251]

[0252] In chemical formula 6-1, R 101 To R 116 Each of these can be independently, for example, hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 132 R 133 R 134 Or -GeR 132 R 133 R 134 .

[0253] R 132 To R 134 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0254] R 101 To R 116 At least one of them can be a functional group, for example, represented by the chemical formula V-1.

[0255] L 100 It can be, for example, a bidentate ligand of a monovalent anion, and can be, for example, a ligand coordinated to iridium via a lone pair of electrons of a carbon or heteroatom.

[0256] m21 and m22 can each be an integer from 0 to 3 independently, for example, and m21+m22 can be an integer from 1 to 3, for example.

[0257] [Chemical Formula V-1]

[0258]

[0259] In chemical formula V-1, R 135 To R 139 Each of these can be independently, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 132 R 133 R 134 .

[0260] * refers to the part that is attached to a carbon atom.

[0261] [Chemical Formula 6-2]

[0262]

[0263] [Chemical Formula 6-3]

[0264]

[0265] [Chemical Formula 6-4]

[0266]

[0267] [Chemical Formula 6-5]

[0268]

[0269] [Chemical Formula 6-6]

[0270]

[0271] In chemical formulas 6-2 to 6-6, X 14 It can be, for example, carbon or nitrogen.

[0272] Y 100 It can be, for example, O or S.

[0273] R 101 To R 122 Each of these can be independently, for example, hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 133 R 134 R 135 Or -GeR 133 R 134 R 135 .

[0274] R 133 To R 135 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0275] L 100 It can be a bidentate ligand of a monovalent anion, and can be a ligand coordinated to iridium, for example, through a lone pair of electrons of a carbon or heteroatom.

[0276] m111 can be an integer such as 1 or 2.

[0277] n1 and n2 can each be an integer from 0 to 3 independently, and n1+n2 can be an integer from 1 to 3.

[0278] The hole transport auxiliary layer 33 may include a third compound having relatively strong hole properties.

[0279] As described above, compared to when used alone, by including a first compound with relatively strong hole properties and a second compound with relatively strong electronic properties together, the luminescent layer 32 can significantly improve luminous efficiency by increasing the mobility of electrons and holes.

[0280] When materials with biased electron or hole properties are used to form the luminescent layer, a relatively larger number of excitons are generated in the device including the luminescent layer due to the recombination of charge carriers at the interface between the luminescent layer and the electron or hole transport layer. Consequently, the molecular excitons in the luminescent layer interact with the charges at the interface of the hole transport layer, thus causing a sharp decline in efficiency (roll-off) and a drastic deterioration in luminescence lifetime characteristics.

[0281] To address these issues, the first and second compounds can be simultaneously included in the emissive layer to prevent the luminescent region from being biased towards either the electron transport layer or the hole transport layer. Furthermore, a hole transport auxiliary layer comprising a third compound with relatively strong hole characteristics can be located 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 improved simultaneously.

[0282] The third compound can be represented by chemical formula 3.

[0283] [Chemical Formula 3]

[0284]

[0285] In chemical formula 3, Ar 3 and Ar 4 Each may be, independently or include, for example, substituted or unsubstituted C6 to C30 aryl groups or substituted or unsubstituted C2 to C30 heterocyclic groups.

[0286] Ar 5 and Ar 6 Each is independently or includes, for example, a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl.

[0287] R 2 To R 6 Each of these can be, independently or include, for example, 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 groups.

[0288] m2 can be, for example, an integer from 1 to 3.

[0289] In one implementation, m2 can be 2 or 3, and each R 2 They can be the same as or different from each other.

[0290] The third compound may have a structure in which at least one fluorene group is substituted on the amine core.

[0291] If at least one fluorene group is substituted on the amine core, steric hindrance can help minimize degradation by lowering the deposition temperature, thereby helping to further improve lifetime characteristics.

[0292] In one embodiment, the third compound can be, for example, derived from chemical...

[0293] One of the formulas 3-1 to 3-4.

[0294]

[0295]

[0296] In chemical formulas 3-1 to 3-4, Ar 3 To Ar 6 R 2 To R 6 m2 can be the same as those defined above.

[0297] In one embodiment, the third compound may be represented, for example, by chemical formulas 3-4.

[0298] In chemical formula 3, Ar 3 and Ar 4 Each of these can be independently, for example, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene.

[0299] In one implementation, Ar 3 and Ar 4 Each can be independently, for example, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted fluorene group.

[0300] In chemical formula 3, Ar 5 and Ar 6 Each can be, for example, a substituted or unsubstituted C1 to C5 alkyl or a substituted or unsubstituted C6 to C12 aryl.

[0301] In one implementation, Ar 5 and Ar 6 Each of these can be, independently, for example, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0302] In chemical formula 3, R 2To R 6 Each can be, independently, for example, hydrogen, deuterium, or substituted or unsubstituted C1 to C5 alkyl groups.

[0303] In one implementation, R 2 To R 6 They can be, for example, hydrogen, deuterium, or tert-butyl.

[0304] In one implementation, Ar 3 and Ar 4 At least one of them can be, for example, a substituted or unsubstituted fluorene group, and can be represented, for example, by chemical formula 3-4-1.

[0305] [Chemical Formula 3-4-1]

[0306]

[0307] In chemical formula 3-4-1, Ar 4 To Ar 6 R 2 To R 6 m2 can be the same as those defined above.

[0308] Ar 9 and Ar 10 Each can be, independently, for example, a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl.

[0309] R 32 To R 36 Each can be independently, for example, 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.

[0310] m18 can be, for example, an integer from 1 to 3.

[0311] In one implementation, m18 can be 2 or 3, and each R 32 They can be the same as or different from each other.

[0312] In chemical formula 3-4-1, Ar 9 and Ar 10 Each can be, for example, a substituted or unsubstituted C1 to C5 alkyl or a substituted or unsubstituted C6 to C12 aryl.

[0313] In one implementation, Ar 9 and Ar 10 Each can be, independently, for example, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0314] In chemical formula 3-4-1, R 2 To R 6 Each can be, independently, for example, hydrogen, deuterium, or substituted or unsubstituted C1 to C5 alkyl groups.

[0315] In one implementation, R 2 To R 6 They can be, for example, hydrogen, deuterium, or tert-butyl.

[0316] In one embodiment, chemical formula 3-4-1 can be, for example, chemical formula 3-4-1a, chemical formula 3-4-1b, chemical formula 3-4-1c or chemical formula 3-4-1d.

[0317]

[0318] In chemical formulas 3-4-1a, 3-4-1b, 3-4-1c, and 3-4-1d, Ar 4 To Ar 6 Ar 9 Ar 10 R 2 To R 6 R 32 To R 36 m2 and m18 can be the same as those defined above.

[0319] In one embodiment, the third compound may be represented, for example, by chemical formula 3-4-1b.

[0320] In one embodiment, R in chemical formula 3 3 To R 6 At least two of them can be, for example, tert-butyl.

[0321] Heat resistance can be improved by introducing alkyl groups that can improve the glass transition temperature.

[0322] In one implementation, an improvement in device efficiency can be expected by reducing the refractive index of the material.

[0323] Specifically, by using a third compound with a high LUMO energy level as a hole transport auxiliary layer together with the above-mentioned main composition, electron migration can be restricted, thereby keeping electrons within the light-emitting layer and thus effectively forming excitons, thereby also expecting an improvement in device efficiency.

[0324] In one embodiment, R in chemical formula 3-4-1 3 To R 6 At least two of them or R 33 To R 36 At least two of them can be, for example, tert-butyl.

[0325] In one embodiment, in chemical formula 3, R 4 and R 6 Each can be, for example, tert-butyl.

[0326] In one embodiment, in chemical formula 3-4-1, R 4 R 6 R 34 and R 36 Each can be, for example, tert-butyl.

[0327] In one embodiment, the third compound may be, for example, a compound from group 3.

[0328] [Group 3]

[0329]

[0330]

[0331]

[0332] (Dn represents the number of deuterium atoms substituted, where n is an integer greater than or equal to 0, and the maximum value of n corresponds to the number of substituted hydrogen positions.)

[0333] In one embodiment, the first compound may be represented, for example, by chemical formula 1A or chemical formula 1B, the second compound may be represented, for example, by chemical formula 2B-IV, and the third compound may be represented, for example, by chemical formula 3-4-1b.

[0334] In one embodiment, the organic layer 30 may further include, for example, an electron transport region.

[0335] The electron transport region can help further improve electron injection or electron migration between the cathode 20 and the light-emitting layer 32, but also helps block holes.

[0336] In one embodiment, 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.

[0337] [Group B]

[0338]

[0339]

[0340]

[0341] In one embodiment, in addition to the light-emitting layer, the organic light-emitting diode may also include an electron injection layer, a hole injection layer, etc., as organic layers.

[0342] Organic light-emitting diodes can be manufactured, for example, 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.

[0343] The aforementioned organic light-emitting diodes can be used, for example, in organic light-emitting display devices.

[0344] The following embodiments and comparative examples are provided to highlight the characteristics of one or more implementations; however, it will be understood that the embodiments and comparative examples should not be considered as limiting the scope of the implementations, nor should the comparative examples be considered as outside the scope of the implementations. Furthermore, it will be understood that the implementations are not limited to the specific details described in the embodiments and comparative examples.

[0345] 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.

[0346] Synthesis of the first compound

[0347] Synthesis Example 1: Synthesis of Compounds 1-31

[0348] [Reaction Formula 1]

[0349]

[0350] Referring to Korean Patent Publication No. 10-2019-0034074, compound 1-31 (Dn=0) was synthesized using Int-1 (CAS No. 1800022-03-0) and Int-2 (CAS No. 162607-19-4).

[0351] Synthesis Example 2: Synthesis of Compounds 1-4

[0352] [Reaction 2]

[0353]

[0354] Referring to Korean patent registration number 10-2438159, compound 1-4 (Dn=0) was synthesized using Int-3 (CAS No. 1800022-02-9) and Int-4 (CAS No. 86-76-0).

[0355] Synthesis of the second compound

[0356] Synthesis Example 3: Synthesis of Compound B-61

[0357] [Reaction 3]

[0358]

[0359] Referring to Korean Patent Publication No. 10-2000-0007644, compound B-61 (Dn=0) was synthesized using Int-5 (CAS No. 1883265-32-4) and Int-6 (CAS No. 2085325-18-2).

[0360] Synthesis Example 4: Synthesis of Compound B-19

[0361] [Reaction 4]

[0362]

[0363] Referring to the synthesis method disclosed in Korean Patent Publication No. 10-2024-0052660, compound B-19 (Dn=0) was synthesized using Int-7 (CAS No. 2418528-30-8) and Int-8 (CAS No. 1229235-79-3).

[0364] Synthesis of the third compound

[0365] Synthesis Example 5: Synthesis of Compound F-41

[0366] [Reaction 5]

[0367]

[0368] In a round-bottom flask, 410 g (1.203 mol) of intermediate F-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. Subsequently, 55 g (0.06 mol) of Pd₂(dba)₃ and 74 g (0.18 mol) of SPhos 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 obtained was purified by recrystallization from n-hexane / methanol to give 600 g (yield: 71%) of compound F-41 (Dn = 0).

[0369] Synthesis Example 6: Synthesis of Compound F-53

[0370] [Reaction Formula 6]

[0371]

[0372] Compound F-53 was synthesized using intermediate F-1-1 and an amine intermediate (CAS No. 500717-23-7) in the same manner as in Synthesis Example 5.

[0373] Comparative Synthesis Example 1: Comparative Compound R-1

[0374]

[0375] Referring to Korean Patent Publication No. 10-2019-0034074, comparative compound R-1 was synthesized.

[0376] Comparative Synthesis Example 2: Synthesis of Compound R-2

[0377]

[0378] Referring to Korean Patent Publication No. 10-2219645, comparative compound R-2 was synthesized.

[0379] (Manufacturing of Organic Light Emitting Diodes)

[0380] Example 1

[0381] A glass substrate coated with an ITO (indium tin oxide) film was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with isopropanol, acetone, or methanol and dried. It was then transferred to a plasma cleaner for 10 minutes using oxygen plasma and then to a vacuum depositor. The prepared ITO transparent electrode was used as the anode, and compound A, doped with 3% NDP-9 (commercially available from Novaled), was vacuum deposited onto the ITO substrate to form... A thick hole injection layer is formed on top of it by depositing compound A. A thick hole transport layer. Compound F-53 obtained in Synthesis Example 6 was deposited on the hole transport layer until... The thickness is such that a first hole transport auxiliary layer is formed, and compound B is deposited on the first hole transport auxiliary layer to a thickness of [missing information]. The thickness was adjusted to form a second hole transport auxiliary layer. On the second hole transport auxiliary layer, compound 1-31 of Synthesis Example 1 and compound B-61 of Synthesis Example 3 were mixed in a 5:5 weight ratio and used as the host material, and 2 wt% RD was doped as a dopant, to form the second hole transport auxiliary layer by vacuum deposition. A thick luminescent layer. Then, compound C is deposited on the luminescent layer to form... A thick electron transport auxiliary layer was formed by simultaneously vacuum-depositing compounds D and LiQ in a 1:1 weight ratio. A thick electron transport layer. This is achieved by sequential vacuum deposition on the electron transport layer. Yb and Al is used to form the cathode, thereby manufacturing an organic light-emitting diode.

[0382] The manufactured organic light-emitting diode has the following structure: ITO / compound A (3% NDP-9 doped). Compound A / First hole transport auxiliary layer (compound F-53, Compound B / Emitting layer [Main body (compound 1-31: compound B-61 = 50:50): RD = 98wt%: 2wt%] / Compound C / Compound D:LiQ / Yb / Al

[0383] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine Compound B: 4-[3-(phenanthrene-9-yl)phenyl]-N,N-bis(4-phenylphenyl)aniline

[0384] Compound C: 4-{4-[3-(9,9-dimethyl-9H-fluorene-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[0385] Compound D: 2-(4-{2-[4-(diphenyl-1,3,5-triazin-2-yl)phenyl]naphth-1-yl}phenyl)-4,6-diphenyl-1,3,5-triazine

[0386] [RD]

[0387]

[0388] Examples 2 to 4 and Comparative Examples 1 and 2

[0389] The diodes of Examples 2 to 4 and Comparative Examples 1 and 2 were manufactured in the same manner as in Example 1, except that the first hole transport auxiliary layer and the main body were changed as described in Table 1.

[0390] evaluate

[0391] The luminous efficiency characteristics of the organic light-emitting diodes according to Examples 1 to 4 and Comparative Examples 1 and 2 were evaluated.

[0392] The specific measurement methods are shown below, and the results are shown in Table 1.

[0393] (1) Measure the change in current density based on voltage change.

[0394] While increasing the voltage from 0V to 10V, the current flowing through the unit device in the obtained organic light-emitting diode is measured using an ammeter-voltmeter (Keithley 2400), and the measured current value is divided by the area to provide the result.

[0395] (2) Measure the brightness change based on voltage changes

[0396] The brightness was measured using a luminance meter (Minolta Cs-1000A) while the voltage of the organic light-emitting diode was increased from 0V to 10V.

[0397] (3) Measuring the driving voltage

[0398] Each diode was measured at 15mA / cm using a current-voltmeter (Keithley 2400). 2 The result is obtained by applying the driving voltage.

[0399] The relative values ​​of the driving voltage based on Example 1 are shown in Table 1.

[0400] (4) Measure luminous efficiency

[0401] Using the brightness and current density from (1) and (2) above, as well as the voltage, the same current density (10 mA / cm²) was calculated. 2 Luminous efficiency (cd / A) at ).

[0402] The relative values ​​of luminous efficiency based on Example 1 are shown in Table 1.

[0403] (Table 1)

[0404]

[0405] Referring to Table 1, compared with the organic light-emitting diodes according to the comparative example, the organic light-emitting diodes using the composition according to the embodiments show significantly improved driving voltage and luminous efficiency.

[0406] By summarizing and reviewing, some exemplary implementations can provide organic optoelectronic devices capable of achieving high efficiency characteristics.

[0407] Some exemplary embodiments may provide a display device including an organic optoelectronic device.

[0408] Highly efficient organic optoelectronic devices can be realized through some exemplary implementations.

[0409] Exemplary embodiments have been disclosed herein, and although specific terminology has been used, it will be used and understood in a general and descriptive sense only and not for limiting purposes. In some instances, as will be apparent to those skilled in the art up to the time of filing of this application, unless otherwise specifically indicated, features, characteristics, and / or elements described in connection with specific embodiments may be used alone or in combination with features, characteristics, and / or elements described in connection with other embodiments. Therefore, those skilled in the art will understand that various changes in form and detail may be made without departing from the spirit and scope of the invention as set forth in the appended claims.

Claims

1.An organic optoelectronic device comprising: an anode and a cathode facing each other, a light-emitting layer between the anode and the cathode, a hole-transporting layer between the anode and the light-emitting layer, and a hole-transporting auxiliary layer between the light-emitting layer and the hole-transporting layer; wherein the light-emitting layer comprises a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2, and the hole-transporting auxiliary layer comprises a third compound represented by Chemical Formula 3: [Chemical Formula 1] in Chemical Formula 1, A and B are each independently a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring, L 1 and L 2 each independently is a single bond or a substituted or unsubstituted C6to C20arylene, R 1 is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted aminyl, substituted or unsubstituted Ci to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl, Ar 1 and Ar 2 each independently is substituted or unsubstituted C6to C20aryl or substituted or unsubstituted C2to C30heterocyclyl, provided that at least one of Ar 1 and Ar 2 is substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl, m1 is an integer from 1 to 4, and when m1 is 2, 3 or 4, each R 1 are the same or different from each other; [Chemical Formula 2] in Chemical Formula 2, Z 1 to Z 6 each independently is N or C-L a -R a , Z 1 at least two of Z 6 are N, each L is independently a single bond, substituted or unsubstituted C6to C20arylene, substituted or unsubstituted C2to C20heterocyclyl, or a combination thereof, a is independently a single bond, substituted or unsubstituted C6to C20arylene, substituted or unsubstituted C2to C20heterocyclyl, or a combination thereof, Each R a Independently, it is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof, and each R a are present separately or adjacent ones of them are connected to each other to form a substituted or unsubstituted aliphatic mono- or polycyclic ring, a substituted or unsubstituted aromatic mono- or polycyclic ring or a substituted or unsubstituted heteroaromatic mono- or polycyclic ring; [Chemical Formula 3] in Chemical Formula 3, Ar 3 and Ar 4 each independently is substituted or unsubstituted C6to C30aryl or substituted or unsubstituted C2to C30heterocyclyl, Ar 5 and Ar 6 each independently is substituted or unsubstituted C1to C30alkyl or substituted or unsubstituted C6to C30aryl, R 2 to R 6 each independently is 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 heterocyclyl, m 2 is an integer of 1 to 3, and when m2 is 2 or 3, each R 2 are the same or different from each other. 2.The organic optoelectronic device according to claim 1, wherein, Chemical Formula 1 is represented by one of Chemical Formula 1A to Chemical Formula 1E: in Chemical Formula 1A to Chemical Formula 1E, Ar 1 , Ar 2 , L 1 and L 2 are defined as those of Chemical Formula 1, L b1 and L b2 each independently is a single bond or a substituted or unsubstituted C6to C20arylene, R 7 to R 12 , R b1 and R b2 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted aminyl, substituted or unsubstituted C1to C30alkyl, substituted or unsubstituted C6to C30aryl, or substituted or unsubstituted C2to C30heterocyclyl, n 1 to n 3 are each independently an integer of 0 or 1, when n 1 and n 2 are 0, m 3 and m 4 are each independently an integer of 1 to 4, when n 1 and n 2 are 1, m 3 and m 4 are each independently an integer of 1 or 2, when n 3 is 0, m 5 is an integer of 1 or 2, when n 3 is 1, m 5 is 0, and m 6 to m 8 are each independently one of an integer of 1 to 4. 3.The organic optoelectronic device according to claim 1, wherein, Chemical Formula 1 is represented by Chemical Formula 1A-1: [Chemical Formula 1A-1] in Chemical Formula 1A-1, L a1 , L a2 , L 1 and L 2 are each independently a single bond, substituted or unsubstituted phenylene, or substituted or unsubstituted biphenylene, Ar 1 is substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl, Ar 2 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, R 7 , R 8 , R 11 , R b1 , and R b2 are each independently hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted aminyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m 3 is an integer of 1 to 4, m 4' is an integer of 1 or 2, and m 7 is an integer of 1 to 4. 4.The organic optoelectronic device according to claim 1, wherein, Ar 1 and Ar 2 each independently is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenlenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, and Ar 1 and at least one of Ar 2 is substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl. 5.The organic optoelectronic device according to claim 1, wherein, Chemical Formula 2 is represented by one of Chemical Formula 2A to Chemical Formula 2E: [Chemical Formula 2E] in Chemical Formula 2A to Chemical Formula 2E, Z 1 , Z 3 , and Z 5 are each independently N or C-L a -R a , provided that at least two of Z 1 , Z 3 , and Z 5 are N, X 1 is O, S or NR c , L a and L 3 to L 5 each independently is a single bond, substituted or unsubstituted C6to C20arylene, substituted or unsubstituted C2to C20heterocyclylene, or a combination thereof, R a , R c , and R 14 to R 29 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, substituted or unsubstituted silyl, or a combination thereof, R 14 to R 26 each individually are present, or adjacent ones of them are connected to each other to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring, Ar 7 , Ar 8 , and Ar 11 each independently is a substituted or unsubstituted C6to C30aryl, a substituted or unsubstituted C2to C30heterocyclyl, or a combination thereof, R a , Ar 7 , and Ar 8 are each present individually, or adjacent groups of R a , Ar 7 , and Ar 8 are connected to each other to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring or a substituted or unsubstituted heteroaromatic monocyclic or polycyclic ring, m 15 and m 16 are each independently an integer of 1 to 4, and m 13 and m 14 are each independently an integer of 1 to 3. 6.The organic optoelectronic device according to claim 5, wherein, Chemical Formula 2 is represented by Chemical Formula 2B-IV: [Chemical Formula 2B-IV] in Chemical Formula 2B-IV, L 3 to L 5 each independently is a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted dibenzofuranylene, or substituted or unsubstituted dibenzothiophenylene, X 1 is O or S, Ar 7 and Ar 8 each independently is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted naphthobenzofuranyl, or substituted or unsubstituted naphthobenzothiophenyl, R 22 to R 26 each independently is hydrogen, deuterium, substituted or unsubstituted C1to C10alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, and m 13 is an integer of 1 to 3. 7.The organic optoelectronic device according to claim 1, wherein, Chemical Formula 3 is represented by Chemical Formula 3-4: [Chemical Formula 3-4] In Chemical Formula 3-4, Ar 3 to Ar 6 , R 2 to R 6 and m2 is the same as those of Chemical Formula 3. 8.The organic optoelectronic device according to claim 7, wherein, Chemical Formula 3-4 is represented by Chemical Formula 3-4-1: [Chemical Formula 3-4-1] in Chemical Formula 3-4-1, Ar 4 to Ar 6 , R 2 to R 6 and m2 is the same as those of formula 3, Ar 9 and Ar 10 each independently is substituted or unsubstituted C1to C30alkyl or substituted or unsubstituted C6to C30aryl, R 32 to R 36 each independently is 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 heterocyclyl, and m 18 is an integer of 1 to 3. 9.The organic optoelectronic device according to claim 8, wherein, Chemical Formula 3-4-1 is represented by Chemical Formula 3-4-1b: [Chemical Formula 3-4-1b] In Chemical Formula 3-4-1b, Ar 4 to Ar 6 , Ar 9 , Ar 10 , R 2 to R 6 , R 32 to R 36 , m2 and m18 are the same as those of Chemical Formula 3-4-1. 10.The organic optoelectronic device according to claim 1, wherein, the third compound is a compound of Group 3: [Group 3] D n represents the number of deuterium atom substitution, n is an integer greater than or equal to 0, and the maximum value of n corresponds to the number of substitutable hydrogen positions. 11.The organic optoelectronic device according to claim 1, wherein, the first compound is represented by Chemical Formula 1A-1, the second compound is represented by Chemical Formula 2B-IV, and the third compound is represented by Chemical Formula 3-4-1b: [Chemical Formula 1A-1] in Chemical Formula 1A-1, L a1 , L a2 , L 1 and L 2 are each independently a single bond, substituted or unsubstituted phenylene, or substituted or unsubstituted biphenylene, Ar 1 is substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl, Ar 2 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, R 7 , R 8 , R 11 , R b1 , and R b2 are each independently hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted aminyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m3 is an integer of 1 to 4, m4' is an integer of 1 or 2, and m7 is an integer of 1 to 4; [Chemical Formula 2B-IV] in Chemical Formula 2B-IV, L 3 to L 5 each independently is a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted dibenzofuranylene, or substituted or unsubstituted dibenzothiophenylene, X 1 is O or S, Ar 7 and Ar 8 each independently is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted naphthobenzofuranyl, or substituted or unsubstituted naphthobenzothiophenyl, R 22 to R 26 each independently is hydrogen, deuterium, substituted or unsubstituted C1to C10alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, and m13 is an integer of 1 to 3; [Chemical Formula 3-4-1b] in Chemical Formula 3-4-1b, Ar 4 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spiro-bifluorenyl, substituted or unsubstituted bi- triphenylenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, Ar 5 and Ar 6 each independently is substituted or unsubstituted C1to C5alkyl or substituted or unsubstituted C6to C12aryl, R 2 to R 6 each independently is hydrogen, deuterium or tert-butyl, Ar 9 and Ar 10 each independently is substituted or unsubstituted C1to C30alkyl or substituted or unsubstituted C6to C30aryl, R 32 to R 36 each independently is 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 heterocyclyl, and m2 and m18 are each independently an integer of 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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