Organic optoelectronic device and display device

Abstract

The invention relates to 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, wherein 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. [Chemical Formula 3]

Description

[0001] CITATION OF RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2024-0119481, filed on September 3, 2024, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. TECHNICAL FIELD

[0003] Embodiments of the present application relate to organic optoelectronic devices and display devices. BACKGROUND

[0004] An organic optoelectronic device (e.g., an organic photodiode) is a device capable of converting electrical energy and light energy into each other.

[0005] According to the working principle, an organic optoelectronic device can be classified into two types. One is a photovoltaic device that generates electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes, respectively, and the other is a light emitting device that generates light energy from electrical energy by supplying a voltage or a current to an electrode.

[0006] Examples of the organic optoelectronic device can include an organic photovoltaic device, an organic light emitting diode, an organic solar cell, and an organic photoconductor drum.

[0007] Among them, in recent years, an organic light emitting diode (OLED) has attracted much attention due to an increase in demand for flat panel display devices. The organic light emitting diode is a device that converts electrical energy into light, and the performance of the organic light emitting diode can be affected by an organic material between electrodes. SUMMARY

[0008] Embodiments can be implemented by providing an organic optoelectronic device including 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, and the hole transport auxiliary layer includes a third compound represented by Chemical Formula 3:

[0009] [Chemical Formula 1]

[0010]

[0011] In Chemical Formula 1, Ring A is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted group, or a substituted or unsubstituted triphenylene group, X 1 and X 2each independently O, S, or N, provided that X 1 and X 2 one of X 1 and X 2 each independently substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C2 to C30 heterocyclyl, L 1 is a single bond or substituted or unsubstituted C6 to C20 arylene, and R 1 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;

[0012] [Chemical Formula 2]

[0013]

[0014] In Chemical Formula 2, Z 1 to Z 6 each independently N or C-L a -R a , provided that at least two of Z 1 to Z 6 are N, each L a is independently a single bond, substituted or unsubstituted C6 to C20 arylene, substituted or unsubstituted C2 to C20 heterocyclyl, or a combination thereof, each R a is independently hydrogen, deuterium, 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, substituted or unsubstituted amine, halogen, cyano, or a combination thereof, and each R a is present separately or adjacent groups among them are connected to each other to form a substituted or unsubstituted aliphatic monocyclic or polycyclic ring, a substituted or unsubstituted aromatic monocyclic or polycyclic ring, or a substituted or unsubstituted heteroaromatic monocyclic or polycyclic ring;

[0015] [Chemical Formula 3]

[0016]

[0017] In Chemical Formula 3, Ar 3 and Ar 4 each independently substituted or unsubstituted C6 to C30 aryl or substituted or unsubstituted C2 to C30 heterocyclyl, Ar 5 and Ar 6 each independently substituted or unsubstituted C1 to C30 alkyl or substituted or unsubstituted C6 to C30 aryl, R 32 to R 36each 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 heterocyclic group, and m1 is an integer of 1 to 3.

[0018] Embodiments can be realized by providing a display device including an organic optoelectronic device according to an embodiment. BRIEF DESCRIPTION OF DRAWINGS

[0019] Exemplary embodiments will be described in detail with reference to the attached drawings, of which:

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

[0021] Exemplary embodiments will be described in detail with reference to the attached drawings, of which:

[0022] In the drawings, the sizes of layers and regions can be exaggerated for clarity. It will also be understood that when a layer or element is referred to as being "on" another layer or substrate, it can be directly on the other layer or substrate, or intervening layers can also be present. Furthermore, it will be understood that when a layer is referred to as being "under" another layer, it can be directly under the other layer, and one or more intervening layers can also be present. In addition, it will be understood that when a layer is referred to as being "between" two layers, it can be the only layer between the two layers, or one or more intervening layers can also be present. Like reference numerals refer to like elements throughout.

[0023] As used herein, "substituted" means that at least one hydrogen is replaced by deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amine group, nitro, substituted or unsubstituted C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 heteroaryl group, C1 to C20 alkoxy group, C1 to C10 trifluoroalkyl group, cyano, or a combination thereof, unless otherwise provided.

[0024] In one example, “substituted” means that at least one hydrogen of a substituent or compound is replaced with deuterium, C1to C30alkyl, C1to C10alkylsilyl, C6to C30arylsilyl, C3to C30cycloalkyl, C3to C30heterocycloalkyl, C6to C30aryl, C2to C30heteroaryl, or cyano. In one specific example, “substituted” means that at least one hydrogen of a substituent or compound is replaced with deuterium, C1to C20alkyl, C3to C20cycloalkyl, C6to C30aryl, or cyano. In one specific example, “substituted” means that at least one hydrogen of a substituent or compound is replaced with deuterium, C1to C5alkyl, C3to C10cycloalkyl, C6to C18aryl, or cyano. In one specific example, “substituted” means that at least one hydrogen of a substituent or compound is replaced with deuterium, cyano, methyl, ethyl, propyl, butyl, t-butyl, cyclopropyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0025] As used herein, “unsubstituted” means that a hydrogen atom is not replaced with another substituent and the hydrogen atom is retained.

[0026] As used herein, “hydrogen substitution (-H)” can include “deuterium substitution (-D)” or “tritium substitution (-T)”.

[0027] As used herein, “hetero” means a group comprising 1 to 3 heteroatoms selected from N, O, S, P, and Si in one functional group and the remainder is carbon, when a definition is not otherwise provided. As used herein, the term “or” is not an exclusive term, for example, “A or B” will include A, B, or A and B.

[0028] As used herein, “aryl” means a group comprising at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p-orbitals that form a conjugated pi system, for example, phenyl, naphthyl, and the like, two or more hydrocarbon aromatic moieties can be connected by a sigma bond and the hydrocarbon aromatic moieties can be, for example, biphenyl, terphenyl, quaterphenyl, and the like, and two or more hydrocarbon aromatic moieties can be directly or indirectly fused to provide non-aromatic fused rings, for example, fluorenyl.

[0029] An aryl group can include a monocyclic, polycyclic, or fused ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional group.

[0030] As used herein, “heterocyclyl” is a superordinate concept of heteroaryl and can comprise at least one heteroatom selected from N, O, S, P, and Si in a ring compound, such as aryl, cycloalkyl, a fused ring thereof, or a combination thereof, in place of carbon (C). When the heterocyclyl is a fused ring, the entire ring or each ring of the heterocyclyl can comprise one or more heteroatoms.

[0031] For example, "heteroaryl" can mean an aryl group containing at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryls are directly connected by a sigma bond, or when a heteroaryl includes two or more rings, the two or more rings can be fused. When the heteroaryl is a fused ring, each ring can contain 1 to 3 heteroatoms.

[0032] More specifically, the substituted or unsubstituted C6to C30aryl group can be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted More specifically, the substituted or unsubstituted C2to C30heterocyclic group can be a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl 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, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolyl group, a substituted or unsubstituted quinoxalyl group, a substituted or unsubstituted naphthylidinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group, or a combination thereof.

[0033] More specifically, the substituted or unsubstituted C2to C30heterocyclic group can be a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl 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, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolyl group, a substituted or unsubstituted quinoxalyl group, a substituted or unsubstituted naphthylidinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group, or a combination thereof.

[0034] As used herein, hole-transporting property refers to the ability to contribute electrons to form holes when an electric field is applied, and the holes formed in the anode can be easily injected into and transported in the light-emitting layer due to the conductive property according to the highest occupied molecular orbital (HOMO) level.

[0035] 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.

[0036] The following describes an organic optoelectronic device according to some exemplary embodiments.

[0037] 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 photoconductor drums.

[0038] This document describes an organic light-emitting diode as an example of an organic optoelectronic device, but the implementation can be applied to other organic optoelectronic devices in the same way.

[0039] Figure 1 This is a cross-sectional view showing an organic optoelectronic device according to some exemplary embodiments.

[0040] Referring to the accompanying drawings, an 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 located between the anode 10 and the cathode 20.

[0041] 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-dioxo)thiophene) (PEDOT), polypyrrole, and polyaniline.

[0042] The cathode 20 can be made of a conductor with a small work function to facilitate electron injection, and can be, for example, a metal, a metal oxide, or a conductive polymer. The cathode 20 can 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.

[0043] 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 located between the hole transport layer 31 and the light-emitting layer 32.

[0044] Hole transport layer 31 may be a layer that helps holes to be transported from anode 10 to light-emitting layer 32, and may contain, for example, amine compounds.

[0045] Amine compounds may contain, for example, at least one aryl or heteroaryl group. Amine compounds may be represented, for example, by chemical formula a or chemical formula b.

[0046]

[0047] In chemical formula a or b, Ar a To Ar g Each can be, independently, 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 a combination thereof.

[0048] In one implementation, Ar a To Ar c At least one of them and Ar d To Ar g At least one of them may be, for example, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, or a combination thereof.

[0049] Ar h It can be, for example, 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.

[0050] The light-emitting layer 32 may comprise, for example, at least two types of host and dopant. The host may comprise, for example, a first compound with relatively strong hole characteristics and a second compound with relatively strong electronic characteristics and bipolar characteristics.

[0051] The first compound is a compound with relatively strong bipolar properties and can be represented by chemical formula 1.

[0052] [Chemical Formula 1]

[0053]

[0054] In Formula 1, ring A may be or include, for example, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzo[a]phenanthryl group, or a substituted or unsubstituted [b] group. Triphenylene oxide, either substituted or unsubstituted.

[0055] X 1 and X 2 They can be, for example, O, S, or N, each independently.

[0056] In one implementation, X 1 and X 2 One of them can be, for example, N.

[0057] Ar 1 and Ar 2 Each may be, or include, for example, substituted or unsubstituted C6 to C20 aryl groups or substituted or unsubstituted C2 to C30 heterocyclic groups, independently.

[0058] L 1 It can be, for example, a single bond or a substituted or unsubstituted C6 to C20 aryl group.

[0059] R 1 It may 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.

[0060] In one implementation, ring A can be, for example, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted benzo[a]phenanthrene group, or a substituted or unsubstituted group. base.

[0061] In one implementation, chemical formula 1 can be represented, for example, by one of chemical formulas 1A to 1C.

[0062] [Chemical Formula 1A]

[0063]

[0064] [Chemical Formula 1B]

[0065]

[0066] [Chemical Formula 1C]

[0067]

[0068] In chemical formulas 1A to 1C, X 1 X 2 and R 1 It can be defined as those described above.

[0069] m4, m8, and m12 can each be an integer from 1 to 4, for example, independently.

[0070] m2, m3, m5 to m7 and m9 to m11 can each be an integer, for example, 1 or 2, independently.

[0071] R 3 To R 13Each of these can be, independently, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted alkylamine, substituted or unsubstituted arylamine, substituted or unsubstituted heteroarylamine, substituted or unsubstituted alkylarylamine, substituted or unsubstituted alkylheteroarylamine, substituted or unsubstituted arylheteroarylamine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic.

[0072] In one implementation, R 3 To R 5 One of them, R 6 To R 9 One of them or R 10 To R 13 One of them can be, for example, a group represented by the chemical formula a.

[0073] [Chemical formula a]

[0074]

[0075] Ar 1 Ar 2 and L 1 It can be defined as those described above.

[0076] * indicates a connection point.

[0077] 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 anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted dibenzothiophene.

[0078] In one implementation, L 1 It can be, for example, a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0079] In one implementation, R 1 It can be, for example, 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.

[0080] In one implementation, R 1It can be, for example, a substituted or unsubstituted C6 to C12 aryl group.

[0081] In one implementation, R 1 It can be, for example, a substituted or unsubstituted phenyl group.

[0082] In one implementation, R 3 To R 13 Each can be independently, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, or substituted or unsubstituted C2 to C20 heterocyclic.

[0083] In one implementation, chemical formula 1 may be represented, for example, by one of chemical formula 1A-I-(1), chemical formula 1A-I-(2), chemical formula 1B-I-(1), chemical formula 1B-I-(2), chemical formula 1B-II-(1), chemical formula 1B-II-(2), chemical formula 1C-I-(1), chemical formula 1C-I-(2), chemical formula 1C-II-(1) or chemical formula 1C-II-(2).

[0084]

[0085]

[0086] In the chemical formulas 1A-I-(1), 1A-I-(2), 1B-I-(1), 1B-I-(2), 1B-II-(1), 1B-II-(2), 1C-I-(1), 1C-I-(2), 1C-II-(1), and 1C-II-(2), R 1 R 3 To R 13 L 1 Ar 1 Ar 2 m2 to m12 can be defined as those described above.

[0087] X 1 and X 2 They can be, for example, O or S, independently.

[0088] In one implementation, m2 is 2, and each R 3 They can be the same as or different from each other.

[0089] In one implementation, m3 can be 2, and each R 4 They can be the same as or different from each other.

[0090] In one implementation, m4 can be 2, 3, or 4, and each R 5 They can be the same as or different from each other.

[0091] In one implementation, m5 can be 2, and each R 6 They can be the same as or different from each other.

[0092] In one implementation, m6 can be 2, and each R 7 They can be the same as or different from each other.

[0093] In one implementation, m7 can be 2, and each R 8 They can be the same as or different from each other.

[0094] In one implementation, m8 can be 2, 3, or 4, and each R 9 They can be the same as or different from each other.

[0095] In one implementation, m9 can be 2, and each R 10 They can be the same as or different from each other.

[0096] In one implementation, m10 can be 2, and each R 11 They can be the same as or different from each other.

[0097] In one implementation, m11 can be 2, and each R 12 They can be the same as or different from each other.

[0098] In one implementation, m12 can be 2, 3, or 4, and each R 13 They can be the same as or different from each other.

[0099] In one implementation, the first compound may be represented, for example, by chemical formula 1A. In another implementation, the first compound may be represented, for example, by chemical formula 1A-I-(1).

[0100] The first compound can be, for example, a compound from group 1.

[0101] [Group 1]

[0102]

[0103]

[0104]

[0105]

[0106] (Dn represents the number of deuterium atoms that are substituted, where n is an integer greater than or equal to 0, and the maximum value of n corresponds to the number of hydrogen positions that can be substituted.)

[0107] Since the second compound can help to effectively expand the LUMO band by including a nitrogen-containing hexagonal portion, it can be included together with the first compound to help improve the balance between holes and electrons, thereby helping to significantly improve the efficiency characteristics of the device using it.

[0108] The second compound can be represented, for example, by chemical formula 2.

[0109] [Chemical Formula 2]

[0110]

[0111] In chemical formula 2, Z 1 To Z 6 Each can be independently or include, for example, N or CL. a -R a .

[0112] In one implementation, Z 1 To Z 6 At least two of them can be N.

[0113] Each L a It may be, independently or include, for example, single bonds, substituted or unsubstituted C6 to C20 arylene groups, substituted or unsubstituted C2 to C20 heterocyclic groups, or combinations thereof.

[0114] 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.

[0115] Each R a They can exist separately, or adjacent groups can connect with 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.

[0116] In one implementation, Z 1 To Z 6 Two of them can be nitrogen (N) and the others can be CL. a -R a .

[0117] In one implementation, Z 1 and Z 3It 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 .

[0118] In one implementation, Z 1 To Z 6 The three elements in the equation can be nitrogen (N) and the others can be CL. a -R a .

[0119] 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 .

[0120] 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.

[0121]

[0122] 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 .

[0123] In one implementation, Z 1 Z 3 and Z 5 At least two of them can be N.

[0124] X 3 It can be, for example, O, S, or NR. b .

[0125] La and L 2 To L 4 Each can be, independently, 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.

[0126] R a R b 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.

[0127] 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.

[0128] Ar 7 Ar 8 and Ar 11 They can be, independently, for example, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C2 to C30 heterocyclic groups, or combinations thereof.

[0129] R a Ar 7 and Ar 8 They can exist separately or R a Ar 7 and Ar 8 Adjacent groups in the aromatic or heteroaromatic compounds can connect with each other to form substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic compounds.

[0130] m15 and m16 can each be an integer, for example, from 1 to 4, independently.

[0131] m13 and m14 can each be an integer, for example, from 1 to 3, independently.

[0132] In one implementation, m13 can be 2 or 3, and each R 22 They can be the same as or different from each other.

[0133] In one implementation, m14 can be 2 or 3, and each R 27 They can be the same as or different from each other.

[0134] 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.

[0135] 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.

[0136] As used herein, the representation of adjacent groups linked together to form substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic rings means that any two adjacent substituents can link together to form a ring. In one implementation, in chemical formula 2A, R 14 To R 21 Adjacent groups can connect with each other to form substituted or unsubstituted aromatic monocyclic rings. In this document, the aromatic monocyclic ring formed can be, for example, a substituted or unsubstituted phenyl group.

[0137] In one implementation, R 14 To R 26 Adjacent groups can connect with each other to form substituted or unsubstituted aromatic polycyclic compounds, and the formed aromatic polycyclic compounds can be, for example, substituted or unsubstituted naphthyl groups.

[0138] In one implementation, R 14 To R 26 The adjacent groups 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.

[0139] In one implementation, chemical formula 2A can be represented, for example, by one of chemical formulas 2A-I to 2A-X.

[0140]

[0141]

[0142] In chemical formulas 2A-I to 2A-X, L 2 To L 4 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.

[0143] Ar 7 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, or substituted or unsubstituted dibenzothiophene.

[0144] 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.

[0145] m15 and m16 can each be an integer, for example, from 1 to 4, independently.

[0146] In one implementation, chemical formula 2B can be represented, for example, by one of chemical formulas 2B-I to 2B-VII.

[0147]

[0148]

[0149] In chemical formulas 2B-I to 2B-VII, each substituent may be defined in the same way as those in chemical formula 2B.

[0150] R 30 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.

[0151] m13 can be, for example, an integer from 1 to 3.

[0152] m14 can be, for example, an integer from 1 to 4.

[0153] In one implementation, in chemical formulas 2B-I to 2B-VII, L 2 To L 4 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.

[0154] X 3 It can be, for example, O or S.

[0155] Ar 7 and Ar 8 Each of these can be independently, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted group. The group is composed of substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted naphthobenzofuranyl, or substituted or unsubstituted naphthobenzothiophene.

[0156] R 22 To R 26 and R 30 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 dibenzothiophene.

[0157] m13 can be, for example, an integer from 1 to 3.

[0158] m16 can be, for example, an integer from 1 to 4.

[0159] In one implementation, chemical formula 2C can be represented, for example, by chemical formula 2C-I or chemical formula 2C-II.

[0160]

[0161] In chemical formulas 2C-I and 2C-II, each substituent may be defined in the same way as those in chemical formula 2C.

[0162] In one implementation, in chemical formula 2C-I and chemical formula 2C-II, L 2 To L 4 Each can be, for example, a single bond or a substituted or unsubstituted phenylene.

[0163] Ar 7 and Ar 8 Each of these can be independently, for example, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted naphthobenzofuranyl, or a substituted or unsubstituted naphthobenzothiophenyl.

[0164] 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 dibenzothiophene.

[0165] m14 can be, for example, an integer from 1 to 3.

[0166] m15 and m16 can each be an integer, for example, from 1 to 4, independently.

[0167] In one implementation, chemical formula 22 can be represented, for example, by chemical formulas 2B-IV. The second compound can be, for example, a compound from group 2.

[0168] [Group 2]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178] (Dn represents the number of deuterium atoms that are substituted, where n is an integer greater than or equal to 0, and the maximum value of n corresponds to the number of hydrogen positions that can be substituted.)

[0179] In the light-emitting layer 32, the first compound and the second compound can be included as the main components, and can be included in a weight ratio of, for example, from about 1:99 to about 99:1. By including them within the above range, the hole characteristics of the first compound and the electronic characteristics of the second compound can be used to achieve an appropriate weight ratio to achieve bipolar characteristics, thereby improving efficiency and lifetime. Within the above range, they can be included in weight ratios of, for example, from about 90:10 to about 10:90, from about 80:20 to about 20:80, and, for example, 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 implementation, they can be included in weight ratios of about 80:20, about 70:30, or about 60:40.

[0180] In one implementation, this is achieved by introducing fused-ring polycyclic functional groups, such as naphthyl, phenanthryl, benzo[a]phenanthryl, etc. The addition of methyl or triphenylene oxide can lower the T1 energy level, which helps promote exciton transfer to the red-emitting dopant, thereby improving the efficiency of the device.

[0181] The light-emitting layer 32 may also contain one or more compounds, other than the first and second compounds described above, as the main body.

[0182] The light-emitting layer 32 may also contain, for example, dopants.

[0183] 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.

[0184] A dopant is a material that is mixed in small amounts with a compound used in organic optoelectronic devices to induce luminescence, and can typically be a material that emits light by being excited to a triplet or more states multiple times, such as a metal complex. Dopants can be, for example, inorganic, organic, or organic / inorganic compounds, and one or more of these types can be used.

[0185] Examples of dopants may be or include phosphorescent dopants, and examples of phosphorescent dopants may be or include organometallic compounds, including 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.

[0186] [Chemical Formula Z]

[0187] L 5 MX 4

[0188] In the chemical formula Z, M can be, for example, a metal, and L 5 and X 4 They can be the same or different, and can be, for example, ligands that form complexes with M.

[0189] 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 5 and X 4 It could be, for example, a bidentate ligand.

[0190] By L 5 and X 4 The ligand represented can be, for example, one of the chemical formulas Z-1 to Z-8.

[0191]

[0192]

[0193] In chemical formulas Z-1 to Z-8, X 14 It can be, for example, carbon or nitrogen. 100 It can be, for example, O or S.

[0194] 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 indopyridine, a substituted or unsubstituted benzofuranoquinoline, a substituted or unsubstituted benzothiophenoquinoline, or a substituted or unsubstituted indoquinoline.

[0195] m18 can be, for example, an integer from 1 to 4.

[0196] m19 can be, for example, an integer from 1 to 5.

[0197] m111 can be an integer such as 1 or 2.

[0198] By L 5 and X 4 Examples of the ligands represented can be, for example, chemical formulas of group A.

[0199] [Group A]

[0200]

[0201]

[0202] In group A, R 300 To R 302 Each can be independently, for example, hydrogen, deuterium, halogen-substituted or unsubstituted C1 to C30 alkyl, halogen-substituted or unsubstituted C6 to C30 aryl, or halogen.

[0203] 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 and C6 to C30 aryl, or triarylsilyl having substituted or unsubstituted C6 to C30 aryl.

[0204] m25 can be, for example, an integer from 1 to 5.

[0205] m26 can be, for example, an integer from 1 to 4.

[0206] m27 can be, for example, an integer from 1 to 3.

[0207] m28 can be an integer such as 1 or 2.

[0208] m29 can be, for example, an integer from 1 to 6.

[0209] In one implementation, one of m25 to m29 can be an integer of 2 or greater, and R 303 To R 307 Each of them can be the same as or different from each other.

[0210] 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.

[0211] [Chemical Formula 6]

[0212]

[0213] In 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 five- or six-membered carbon ring or a heterocyclic ring.

[0214] R 100 It can represent, for example, 1 to a maximum number of monovalent substituents.

[0215] In one implementation, there can be two or more Rs. 100 Groups, and each R 100 They can be the same as or different from each other.

[0216] 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 thereof.

[0217] R 114 To R 116 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0218] X 10 and X 11 They can be, for example, carbon or nitrogen, each independently.

[0219] 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.

[0220] m21 can be, for example, an integer from 0 to 3.

[0221] [Chemical Formula 7]

[0222]

[0223] 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 five- or six-membered carbon ring or a heterocyclic ring.

[0224] Y 100 It can be, for example, O or S.

[0225] R 201 It can represent, for example, 1 to a maximum number of monovalent substituents.

[0226] In one implementation, there can be two or more Rs. 201 Groups, and each R 201 They can be the same as or different from each other.

[0227] 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 thereof.

[0228] R114 To R 116 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0229] X 12 and X 13 They can be, for example, carbon or nitrogen, each independently.

[0230] 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.

[0231] m21 can be, for example, an integer from 0 to 3.

[0232] m100 and m101 can each be an integer, for example, 1 or 2, independently.

[0233] n100 can be an integer, for example, 0 or 1, where there is no connecting key when n100 is 0.

[0234] [Chemical Formula 8]

[0235]

[0236] In chemical formula 8, Y 100 It can be, for example, O or S.

[0237] 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 thereof.

[0238] R 114 To R 116 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0239] 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.

[0240] m21 can be, for example, an integer from 0 to 3.

[0241] In one implementation, the iridium complex can be represented, for example, by one of chemical formulas 6-1 to 6-6.

[0242] [Chemical Formula 6-1]

[0243]

[0244] 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 .

[0245] R 132 To R 134 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0246] R 101 To R 116 At least one of them can be a functional group, for example, represented by the chemical formula V-1.

[0247] 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.

[0248] m21 and m22 can each be an integer from 0 to 3 independently, and m21+m22 can be an integer from 1 to 3.

[0249] [Chemical Formula V-1]

[0250]

[0251] In chemical formula V-1, R 135 To R 139 Each 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 .

[0252] R 132 To R 134 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0253] * refers to the part that is attached to a carbon atom.

[0254] [Chemical Formula 6-2]

[0255]

[0256] [Chemical Formula 6-3]

[0257]

[0258] [Chemical Formula 6-4]

[0259]

[0260] [Chemical Formula 6-5]

[0261]

[0262] [Chemical Formula 6-6]

[0263]

[0264] In chemical formulas 6-2 to 6-6, X 14 It can be, for example, carbon or nitrogen.

[0265] Y 100 It can be, for example, O or S.

[0266] 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 .

[0267] R 133 To R 135 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0268] 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.

[0269] m111 can be, for example, an integer from 1 to 2.

[0270] n1 and n2 can each be an integer from 0 to 3 independently, and n1+n2 can be an integer from 1 to 3.

[0271] The hole transport auxiliary layer 33 may contain a third compound with relatively strong hole properties.

[0272] 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 help significantly improve luminous efficiency by increasing the mobility of electrons and holes.

[0273] 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. Therefore, the molecular excitons in the luminescent layer interact with the charges at the hole transport layer interface, resulting in a sharp roll-off in efficiency and a drastic deterioration in luminescence lifetime characteristics.

[0274] To address these issues, the first and second compounds can be simultaneously incorporated into 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 containing a third compound with relatively strong hole properties can be located between the hole transport layer and the emissive layer, thereby preventing charge accumulation at the interface between the two layers 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.

[0275] The third compound can be represented by chemical formula 3.

[0276] [Chemical Formula 3]

[0277]

[0278] In chemical formula 3, Ar 3 and Ar 4 They can be, independently, for example, substituted or unsubstituted C6 to C30 aryl groups or substituted or unsubstituted C2 to C30 heterocyclic groups.

[0279] Ar 5 and Ar 6 Each can be, independently, for example, a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl.

[0280] 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.

[0281] m1 can be, for example, an integer from 1 to 3.

[0282] In one implementation, m1 can be 2 or 3, and each R32 They can be the same as or different from each other.

[0283] The third compound has a structure in which at least one fluorene group can be substituted on the amine nucleus.

[0284] Since at least one fluorene group can be substituted in the amine core, steric hindrance can help minimize degradation by lowering the deposition temperature, thereby helping to further improve lifetime characteristics.

[0285] In one implementation, the third compound can be, for example, derived from chemical...

[0286] One of the formulas 3-1 to 3-4.

[0287]

[0288] In chemical formulas 3-1 to 3-4, Ar 3 To Ar 6 R 32 To R 36 m1 and m1 can be defined as described above.

[0289] In one implementation, the third compound may be represented, for example, by chemical formulas 3-4.

[0290] 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 spirodifluorenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene.

[0291] 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 fluorenyl.

[0292] In chemical formula 3, Ar 5 and Ar 6 Each can be, independently, for example, a substituted or unsubstituted C1 to C5 alkyl or a substituted or unsubstituted C6 to C12 aryl.

[0293] In one implementation, Ar 5 and Ar 6 Each of them 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.

[0294] In chemical formula 3, R 32 To R 36 Each can be, independently, for example, hydrogen, deuterium, or substituted or unsubstituted C1 to C5 alkyl groups.

[0295] In one implementation, R 32 To R 36 They can be, for example, hydrogen, deuterium, or tert-butyl.

[0296] In one implementation, Ar 3 and Ar 4 At least one of them may be, for example, a substituted or unsubstituted fluorene group, and the third compound may be represented, for example, by chemical formula 3-4-1.

[0297] [Chemical Formula 3-4-1]

[0298]

[0299] In chemical formula 3-4-1, Ar 4 To Ar 6 R 32 To R 36 m1 and m1 can be defined as described above.

[0300] Ar 9 and Ar 10 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl.

[0301] R 37 To R 41 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.

[0302] m1 and m17 can each be an integer, for example, from 1 to 3, independently.

[0303] In one implementation, m1 can be 2 or 3, and each R 32 They can be the same as or different from each other.

[0304] In one implementation, m17 can be 2 or 3, and each R 37 They can be the same as or different from each other.

[0305] In chemical formula 3-4-1, Ar 9 and Ar 10 Each can be, independently, for example, a substituted or unsubstituted C1 to C5 alkyl or a substituted or unsubstituted C6 to C12 aryl.

[0306] 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.

[0307] In chemical formula 3-4-1, R 32 To R 36 Each can be, independently, for example, hydrogen, deuterium, or substituted or unsubstituted C1 to C5 alkyl groups.

[0308] For example, R 32 To R 36 They can be, for example, hydrogen, deuterium, or tert-butyl.

[0309] In one implementation, chemical formula 3-4-1 can be, for example, chemical formula 3-4-1a, chemical formula 3-4-1b, chemical formula 3-4-1c, and chemical formula 3-4-1d.

[0310]

[0311]

[0312] 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 32 To R 36 R 37 To R 41 m1 and m17 can be defined as described above.

[0313] In one implementation, the third compound may be represented, for example, by chemical formula 3-4-1b.

[0314] In one implementation, R in chemical formula 3 33 To R 36 At least two of them can be, for example, tert-butyl.

[0315] Heat resistance can be improved by introducing alkyl groups that can improve the glass transition temperature.

[0316] In one implementation, an improvement in device efficiency can be expected by reducing the refractive index of the material.

[0317] In one implementation, by applying a third compound with a high LUMO energy level together with the above-described host composition as a hole transport auxiliary layer, electron migration can be restricted, electrons can be kept within the luminescent layer, and excitons can be formed effectively, thereby also anticipating an improvement in device efficiency.

[0318] In one implementation, R in chemical formula 3-4-1 33 To R 36 At least two of them or R 38 To R 41 At least two of them can each be, for example, tert-butyl.

[0319] In one implementation, in chemical formula 3, R 34 and R 36 Each can be, for example, tert-butyl.

[0320] In one implementation, in chemical formula 3-4-1, R 34 R 36 R 39 and R 41 Each can be, for example, tert-butyl.

[0321] In one implementation, the third compound can be, for example, a compound from group 3.

[0322] [Group 3]

[0323]

[0324]

[0325]

[0326]

[0327] (Dn represents the number of deuterium atoms that are substituted, where n is an integer greater than or equal to 0, and the maximum value of n corresponds to the number of hydrogen positions that can be substituted.)

[0328] In one implementation, the first compound may be represented, for example, by chemical formula 1A-I-(1) 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.

[0329] In one implementation, the organic layer 30 may also include, for example, an electron transport region.

[0330] The electron transport region can help further improve electron injection or electron migration, but it also helps block holes between the cathode 20 and the light-emitting layer 32.

[0331] In one implementation, the electron transport region may include an electron transport layer 34 located between the cathode 20 and the light-emitting layer 32, and an electron transport auxiliary layer located between the light-emitting layer 32 and the electron transport layer 34, and may include at least one of the compounds listed in Group B in either of the electron transport layer and the electron transport auxiliary layer.

[0332] [Group B]

[0333]

[0334]

[0335]

[0336] In one implementation, 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.

[0337] Organic light-emitting diodes can be produced, for example, by forming an organic layer on a substrate using dry film deposition methods such as evaporation, sputtering, plasma deposition, and ion deposition, and then forming a cathode or anode thereon.

[0338] The aforementioned organic light-emitting diodes can be applied to organic light-emitting diode display devices.

[0339] 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 construed as limiting the scope of the implementations, nor should the comparative examples be construed as being 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.

[0340] Unless otherwise specified, 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 suitable methods.

[0341] Synthesis of the first compound

[0342] Synthesis Example 1: Synthesis of Compounds 1-11

[0343] [Reaction Formula 1]

[0344]

[0345] Referring to the synthesis method disclosed in Korean Patent Publication No. 2021-0098316, compound 1-11 (Dn=0) was synthesized by using Int-1 (CAS No. 2085325-19-3) and Int-2 (CAS No. 1787246-74-5).

[0346] Synthesis Example 2: Synthesis of Compounds 1-23

[0347] [Reaction 2]

[0348]

[0349] Referring to the synthesis method disclosed in Korean Patent Publication No. 2021-0098316, compound 1-23 (Dn=0) was synthesized by using Int-1 (CAS No. 2085325-19-3) and Int-3 (CAS No. 2915366-87-7).

[0350] Synthesis of the second compound

[0351] Synthesis Example 3: Synthesis of Compound B-29

[0352] [Reaction 3]

[0353]

[0354] Referring to the synthesis method disclosed in Korean Patent Publication No. 2022-0033348, compound B-29 (Dn=0) was synthesized by using Int-4 (CAS No. 1883265-32-4) and Int-5 (CAS No. 2681303-14-8).

[0355] Synthesis Example 4: Synthesis of Compound B-19

[0356] [Reaction 4]

[0357]

[0358] Referring to the synthesis method disclosed in Korean Patent Publication No. 2024-0052660, compound B-19 (Dn=0) was synthesized by using Int-6 (CAS No. 2418528-30-8) and Int-7 (CAS No. 1229235-79-3).

[0359] Synthesis of the third compound

[0360] Synthesis Example 5: Synthesis of Compound F-41

[0361] [Reaction 5]

[0362]

[0363] 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 to a round-bottom flask and dissolved in 4,000 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 refluxed and stirred for 6 hours under 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 obtain 600 g (yield: 71%) of compound F-41 (Dn = 0).

[0364] Synthesis Example 6: Synthesis of Compound F-53

[0365] [Reaction Formula 6]

[0366]

[0367] Compound F-53 was synthesized in the same manner as in Synthesis Example 5 by using intermediate F-1-1 and amine intermediate (CAS No. 500717-23-7).

[0368] Comparative Synthesis Example 1: Synthesis of Compound R-1

[0369]

[0370] Referring to Korean Patent Publication No. 2021-0098316, comparative compound R-1 was synthesized.

[0371] Comparative Synthesis Example 2: Synthesis of Compound R-2

[0372]

[0373] Referring to Korean Patent No. 10-2219645, comparative compound R-2 was synthesized.

[0374] (Production of organic light-emitting diodes)

[0375] Example 1

[0376] Glass substrates coated with ITO (indium tin oxide) films were ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrates were ultrasonically cleaned with isopropanol, acetone, or methanol and dried. They were then transferred to a plasma cleaner for cleaning with oxygen plasma for 10 minutes and then transferred 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 on the ITO substrate to form... - A thick hole injection layer, which is formed on top of which by depositing compound A. A thick hole transport layer. Compound F-53 obtained in Synthesis Example 6 was deposited onto the hole transport layer. A first hole transport auxiliary layer is formed to a thickened thickness, and compound B is deposited on the first hole transport auxiliary layer. A second hole transport auxiliary layer was formed by mixing compound 1-11 from Synthesis Example 1 and compound B-29 from Synthesis Example 3 at a weight ratio of 5:5 on the second hole transport auxiliary layer and using them as the host material. 2 wt% RD was also used as a dopant to form the 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 to create... - A thick electron transport layer. This is achieved through sequential vacuum deposition on the electron transport layer. Yb and Al is used to form the cathode to produce organic light-emitting diodes.

[0377] Organic light-emitting diodes are manufactured with 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 1-11: compound B-29 = 50: 50): RD = 98wt%: 2wt%]( ) / Compound C( Compound D: LiQ ( ) / Yb( ) / Al( ).

[0378] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine

[0379] Compound B: 4-[3-(phenanthrene-9-yl)phenyl]-N,N-bis(4-phenylphenyl)aniline

[0380] Compound C: 4-{4-[3-(9,9-dimethyl-9H-fluorene-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[0381] 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

[0382] [RD]

[0383]

[0384] Examples 2, 3, Comparative Example 1, and Comparative Example 2

[0385] Except for the changes to the main body as described in Table 1, diodes of Examples 2, 3, Comparative Example 1, and Comparative Example 2 were produced in the same manner as in Example 1.

[0386] evaluate

[0387] The driving voltage and luminous efficiency characteristics of the organic light-emitting diodes according to Examples 1 to 3 and Comparative Examples 1 and 2 were evaluated.

[0388] The specific measurement methods are described below, and the results are shown in Table 1.

[0389] (1) Measure the change in current density based on voltage change.

[0390] While increasing the voltage from 0V to 10V, the current flowing through the unit device in the obtained organic light-emitting diode was measured using a voltmeter (Keithley 2400), and the measured current value was divided by the area to provide the result.

[0391] (2) Measure the brightness change based on voltage changes

[0392] While increasing the voltage of the organic light-emitting diode from 0V to 10V, the brightness was measured using a photometer (Minolta Cs-1000A).

[0393] (3) Measurement of driving voltage

[0394] Using an ammeter-voltmeter (Keithley 2400) at 15mA / cm 2 The driving voltage of each diode is measured to obtain the results.

[0395] The relative values ​​of the driving voltage based on Example 1 are shown in Table 1.

[0396] (4) Measurement of luminous efficiency

[0397] Using the brightness and current density from (1) and (2) above, as well as the voltage, the calculation was performed at the same current density (10 mA / cm²). 2 Luminous efficiency (cd / A) at ).

[0398] The relative values ​​of luminous efficiency based on Example 1 are shown in Table 1.

[0399] (Table 1)

[0400]

[0401] Referring to Table 1, compared with the organic light-emitting diodes according to the comparative example, the organic light-emitting diodes using the compositions according to the embodiments show significantly improved driving voltage and luminous efficiency.

[0402] By summarizing and reviewing, some exemplary implementations can provide organic optoelectronic devices capable of achieving low-drive and high-efficiency characteristics.

[0403] Some exemplary embodiments may provide a display device including an organic optoelectronic device.

[0404] This allows for the creation of organic optoelectronic devices with low drive requirements and high efficiency.

[0405] Exemplary embodiments have been disclosed herein, and although specific terminology has been used, it is intended to be used and interpreted in a general and descriptive sense only, and not for limiting purposes. In some instances, it will be apparent to those skilled in the art that, as of the date of filing of this application, 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 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: [Chemical Formula 1] in Chemical Formula 1, Ring A is substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyrenyl, substituted or unsubstituted substituted or unsubstituted triphenylenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzopyren X 1 and X 2 are each independently O, S or N, provided that one of X 1 and X 2 is N, Ar 1 and Ar 2 each independently is substituted or unsubstituted C6to C20aryl or substituted or unsubstituted C2to C30heterocyclyl, L 1 is a single bond or substituted or unsubstituted C6to C20arylene, and R 1 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; [Chemical Formula 2] in Chemical Formula 2, Z 1 to Z 6 each independently is N or C-L a -R a , provided that at least two of Z 1 to 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 is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heterocyclyl, a substituted or unsubstituted silyl, a substituted or unsubstituted amine group, a halogen, a cyano, or a combination thereof, and a each R is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heterocyclyl, a substituted or unsubstituted silyl, a substituted or unsubstituted amine group, a halogen, a cyano, or a combination 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 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 m1 is an integer of 1 to 3. 2.The organic optoelectronic device according to claim 1, wherein: Chemical Formula 1 is represented by Chemical Formula 1A, Chemical Formula 1B, or Chemical Formula 1C: [Chemical Formula 1A] [Chemical Formula 1B] [Chemical Formula 1C] in Chemical Formula 1A to Chemical Formula 1C, X 1 , X 2 and R 1 are defined as those of Chemical Formula 1, m4, m8, and m12 are each independently an integer of 1 to 4, m2, m3, m5 to m7, and m9 to m11 are each independently an integer of 1 or 2, R 3 to R 13 each independently is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted alkylamine group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamine group, substituted or unsubstituted alkylarylamine group, substituted or unsubstituted alkylheteroarylamine group, substituted or unsubstituted arylheteroarylamine 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, and R 3 to R 5 ; R 6 to R 9 ; and R 10 to R 13 is a group represented by formula a, [Chemical Formula a] in Chemical Formula a, Ar 1 , Ar 2 and L 1 are defined as those of Chemical Formula 1, and * is a connecting point.

3. The organic optoelectronic device according to claim 1, wherein in Chemical Formula 1, Ar 1 and Ar 2 each independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group. 4.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 3 is O, S or NR b , L a and L 2 to L 4 each independently is a single bond, substituted or unsubstituted C6to C20arylene, substituted or unsubstituted C2to C20heterocyclyl, or a combination thereof, R b and R 14 to R 29 each independently is 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 independently are present separately or adjacent ones of them are connected to each other to form a substituted or unsubstituted aromatic mono- or polycyclic ring, Ar 7 , Ar 8 , and Ar 11 each independently is substituted or unsubstituted C6to C30aryl, substituted or unsubstituted C2to C30heterocyclyl, or a combination thereof, R a , Ar 7 , and Ar 8 are each present separately, 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, m15 and m16 are each independently an integer of 1 to 4, and m13 and m14 are each independently an integer of 1 to 3. 5.The organic optoelectronic device according to claim 4, wherein: Chemical Formula 2 is represented by Chemical Formula 2B-IV: [Chemical Formula 2B-IV] in Chemical Formula 2B-IV, L 2 to L 4 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 3 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 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 naphthyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, and m13 is an integer of 1 to 3. 6.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 32 to R 36 and m1 are the same as those of Chemical Formula 3. 7.The organic optoelectronic device according to claim 6, 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 32 to R 36 and m1 are 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 37 to R 41 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 m1 and m17 are each independently an integer of 1 to 3. 8.The organic optoelectronic device according to claim 7, 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 32 to R 41 , m1 and m17 are the same as those of Chemical Formula 3-4-1. 9.The organic optoelectronic device according to claim 1, wherein: the third compound is a compound of Group 3: [Group 3] wherein, D n represents the number of substituted deuterium atoms, n is an integer greater than or equal to 0, and the maximum number of n corresponds to the number of substitutable hydrogen positions. 10.The organic optoelectronic device according to claim 1, wherein: the first compound is represented by Chemical Formula 1A-I-(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-I-(1)] in Chemical Formula 1A-I-(1), X 2 is O or S, 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 benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted dibenzosilolyl, L 1 is a single bond, substituted or unsubstituted phenylene or substituted or unsubstituted biphenylene, R 1 is substituted or unsubstituted C6to C12aryl, R 3 to R 5 each independently is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1to C10alkyl, substituted or unsubstituted C6to C12aryl, or substituted or unsubstituted C2to C20heterocyclyl, m4 is an integer of 1 to 4, and m2 and m3 are each independently an integer of 1 or 2; [Chemical Formula 2B-IV] in Chemical Formula 2B-IV, L 2 to L 4 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 3 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 spirobifluorenyl, substituted or unsubstituted 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 32 to R 36 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 37 to R 41 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 m1 and m17 are each independently an integer of 1 to 3. 11.The display device comprising the organic optoelectronic device according to any one of claims 1 to 10.

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