Organic optoelectronic device and display device

Abstract

The present invention relates to an organic optoelectronic device comprising an anode and a cathode facing each other, a light-emitting layer located between the anode and the cathode, and an electron transport layer located between the light-emitting layer and the cathode, wherein the light-emitting layer comprises a first compound represented by Chemical Formula 1 and a second compound represented by a combination of Chemical Formula 2 and Chemical Formula 3, and the electron transport layer comprises a third compound represented by Chemical Formula 4. Detailed explanations of Chemical Formula 1 to Chemical Formula 4 are as defined in the specification.

Description

Technical Field

[0001] Organic optoelectronic devices and display devices have been disclosed. Background Technology

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

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

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

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

[0006] Technical issues

[0007] One embodiment provides a composition for organic optoelectronic devices that can reduce driving voltage and achieve high efficiency and long lifespan.

[0008] Another embodiment provides a composition for an organic optoelectronic device comprising a compound for an organic optoelectronic device.

[0009] Another embodiment provides an organic optoelectronic device comprising a compound for an organic optoelectronic device or a composition for an organic optoelectronic device.

[0010] Another embodiment provides a display device that includes an organic optoelectronic device.

[0011] Technical solution

[0012] According to one embodiment, an organic optoelectronic device includes an anode and a cathode facing each other, a light-emitting layer between the anode and the cathode, and an electron transport layer between the light-emitting layer and the cathode, wherein the light-emitting layer contains a first compound represented by chemical formula 1 and a second compound represented by a combination of chemical formulas 2 and 3, and the electron transport layer contains a third compound represented by chemical formula 4.

[0013] [Chemical Formula 1]

[0014] In chemical formula 1, Ar 1 To Ar 3 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and L 1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene, or a substituted or unsubstituted C2 to C30 heteroarylene; [Chemical Formula 2] [Chemical Formula 3]

[0015] In chemical formulas 2 and 3, a1 in chemical formula 2 up to a4 In the middle, the two adjacent ones are each connected to chemical formula 3. The connecting carbon (C). In chemical formula 2, a1 up to a4 In the formula, the other two not connected to chemical formula 3 are CL. a -R a , L a L 4 and L 5 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. R a R 1 and R 2 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 4 and Ar 5 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. m1 and m2 are each an independent integer from 1 to 4. When m1 is 2 or greater, each R 1 They are the same or different from each other, and When m2 is 2 or greater, each R 2 They are the same or different from each other; [Chemical Formula 4]

[0016] In chemical formula 4, X 1 Is it O or S? Z 1 To Z 6 Each is independently N or CR b , Z 1 To Z 3 At least two of them are N. Z 4 To Z 6 At least two of them are N. L 7 It is a substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene. Ar 6 To Ar 9 Each is independently a substituted or unsubstituted C6 to C30 aryl group. R b R 3 and R 4 Each of these groups 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. m3 and m4 are each an independent integer from 1 to 3. When m3 is 2 or greater, each R 3 They are the same or different from each other, and When m4 is 2 or greater, each R 4 They are the same or different from each other.

[0017] According to another embodiment, a display device including the organic optoelectronic device is provided.

[0018] Beneficial effects

[0019] It is possible to achieve organic optoelectronic devices with high efficiency and long lifespan while reducing the driving voltage. Attached Figure Description

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

[0021] <Explanation of Figure Markers>

[0022] 100: Organic Light Emitting Diode

[0023] 105: Organic layer

[0024] 110: Cathode

[0025] 120: Anode

[0026] 130: Emissive layer

[0027] 140: Hole transport region

[0028] 150: Electronic transmission area Detailed Implementation

[0029] Embodiments of the invention are described in detail below. However, these are presented by way of example and are not intended to limit the invention, which is defined only by the scope of the appended claims.

[0030] In this specification, 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.

[0031] In one embodiment of the invention, "substituted" means that at least one hydrogen atom of the 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 embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by one of the following: deuterium, C1 to C20 alkyl, C1 to C5 alkylsilyl, C6 to C20 aryl, C2 to C20 heteroaryl, or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by one of the following: deuterium, C1 to C5 alkyl, C1 to C5 alkylsilyl, C6 to C18 aryl, C2 to C18 heteroaryl, or cyano. In specific examples of the present invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by one of the following: deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trimethylsilyl, phenyl, biphenyl, terphenyl or naphthyl.

[0032] In this specification, "unsubstituted" means that the hydrogen atom is not replaced by another substituent and retains the hydrogen atom.

[0033] In this specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)".

[0034] In this specification, unless otherwise defined, “heterogeneous” means a functional group containing one to three heteroatoms selected from N, O, S, P and Si and the remaining carbon.

[0035] In this specification, "aryl" means a group comprising at least one aromatic hydrocarbon moiety, wherein all elements of the aromatic hydrocarbon moiety have conjugated p orbitals, such as phenyl, naphthyl, etc., and two or more aromatic hydrocarbon moiety may be linked by σ bonds and may be, for example, biphenyl, terphenyl, tetraphenyl, etc., and two or more aromatic hydrocarbon moiety may be directly or indirectly fused to provide a non-aromatic fused ring, such as fluorene.

[0036] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent carbon atom pairs) functional groups.

[0037] 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 replacing 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.

[0038] 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.

[0039] 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 phenanthryl, 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 benzophenanthryl, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted peryl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indene, or a combination thereof, but is not limited thereto.

[0040] 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, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, or a substituted or unsubstituted isoquinoline group. The group may contain, but is not limited to, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxolinyl, substituted or unsubstituted naphthidyl, 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 phenothiazinyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthophenyl, substituted or unsubstituted benzofuran fluorenyl, substituted or unsubstituted benzothiophenefluorenyl group, or combinations thereof.

[0041] In this specification, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductivity characteristics based on the highest occupied molecular orbital (HOMO) energy level, holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0042] 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.

[0043] The following describes an organic optoelectronic device according to one embodiment.

[0044] 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.

[0045] This document describes an organic light-emitting diode as an example of an organic optoelectronic device, but the invention is not limited thereto and can be applied in the same manner to other organic optoelectronic devices.

[0046] In the accompanying drawings, the thicknesses of layers, films, panels, regions, etc., are enlarged for clarity. Throughout the specification, the same drawing numbers denote the same elements. It will be understood that when an element such as a layer, film, region, or substrate is referred to as being "on" another element, it can be directly on the other element, or there may be intermediate elements present. Conversely, when an element is referred to as being "directly" on another element, there are no intermediate elements present.

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

[0048] refer to Figure 1 An organic light-emitting diode 100 according to one embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 disposed between the anode 120 and the cathode 110.

[0049] The anode 120 may be made of a conductor with a high work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, etc., or alloys thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; a combination of metals and oxides such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0050] The cathode 110 may be made of a conductor with a small work function to aid electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; multilayer materials such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but are not limited thereto.

[0051] The organic layer 105 includes a light-emitting layer 130, which comprises a host and a dopant, and the host may comprise a composition for an organic optoelectronic device.

[0052] The following describes compositions for use in organic optoelectronic devices.

[0053] The composition for use in organic optoelectronic devices comprises a first compound represented by chemical formula 1 and a second compound represented by a combination of chemical formulas 2 and 3.

[0054] [Chemical Formula 1]

[0055] In chemical formula 1, Ar 1 To Ar 3 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. L 1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene, or a substituted or unsubstituted C2 to C30 heteroarylene; [Chemical Formula 2] [Chemical Formula 3]

[0056] In chemical formulas 2 and 3, a1 in chemical formula 2 up to a4 In the middle, the two adjacent ones are each connected to chemical formula 3. The connecting carbon (C). In chemical formula 2, a1 up to a4 In the formula, the other two not connected to chemical formula 3 are CL. a -R a , L a L 4 and L 5 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. R a R 1 and R 2 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 4 and Ar 5 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. m1 and m2 are each an independent integer from 1 to 4.

[0057] In chemical formula 2, when m1 is 2 or greater, each R 1 They can be the same as or different from each other.

[0058] In chemical formula 3, when m2 is 2 or greater, each R 2 They can be the same as or different from each other.

[0059] In chemical formulas 2 and 3, when two or more Ra When replacing, each R a They can be the same as or different from each other.

[0060] As an example, in chemical formula 1, Ar 1 To Ar 3 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted benzothiophene pyrimidinyl, substituted or unsubstituted Benzofuran pyrimidinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocarbazoyl, substituted or unsubstituted oxazolocarbazoyl, substituted or unsubstituted indolocarbazoyl, substituted or unsubstituted indolofluorenyl, substituted or unsubstituted benzofuranocarbazoyl, substituted or unsubstituted benzothiophenocarbazoyl, or substituted or unsubstituted dibenzothiophenyl.

[0061] As a specific example, in chemical formula 1, Ar 1 To Ar 3 Each of them can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazoyl.

[0062] As an example, the first compound may be represented by any one of chemical formulas 1-I, 1-II, 1-III, and 1-IV.

[0063] [Chemical Formula 1-I]

[0064] In chemical formula 1-I, L 1 To L 3 Same as above, Ar 1 and Ar 2 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted dibenzothiophene. R 17 To R 19Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl or substituted or unsubstituted C6 to C30 aryl. m17 is an integer from 1 to 3. m18 and m19 are each an independent integer from 1 to 4. When m17 is 2 or greater, each R 17 Whether they are the same or different, When m18 is 2 or greater, each R 18 They are the same or different from each other, and When m19 is 2 or greater, each R 19 They are the same or different from each other; [Chemical Formula 1-II]

[0065] In chemical formula 1-II, L 1 To L 3 Same as above, X 4 Is it O or S? Ar 1 and Ar 2 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted dibenzothiophenyl. R 20 To R 21 Each of these groups 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. m20 is an integer from 1 to 3. m21 is one of the integers from 1 to 4. When m20 is 2 or greater, each R 20 They are the same or different from each other, and When m21 is 2 or greater, each R 21 They are the same or different from each other; [Chemical Formula 1-III]

[0066] In chemical formula 1-III, L 1 To L 3 Same as above, Z 7 To Z 9Each is independently N or CR f , Z 7 To Z 9 At least two of them are N, and Ar 1 and Ar 2 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocarbazoyl, substituted or unsubstituted oxazolocarbazoyl, substituted or unsubstituted indolocarbazoyl, substituted or unsubstituted indolofluorenyl, substituted or unsubstituted benzofuranocarbazoyl, substituted or unsubstituted benzothiophenocarbazoyl, or substituted or unsubstituted dibenzothiopheneyl. [Chemical Formula 1-IV]

[0067] In chemical formula 1-IV, L 1 To L 3 Same as above, X 5 Is it O or S? Ar 1 and Ar 2 Each of these can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted triphenylene. Ar 14 It is a substituted or unsubstituted C6 to C30 aryl group. R 22 It 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. m22 is an integer from 1 to 4, and When m22 is 2 or greater, each R 22 They are the same or different from each other.

[0068] As another example, the first compound may be represented by chemical formula 1-V or chemical formula 1-VI.

[0069] [Chemical Formula 1-V]

[0070] In chemical formula 1-V, L 1 To L 3 Same as above, Ring A is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, or a substituted or unsubstituted benzoxazolyl group. Ar 1 and Ar 2 Each of these compounds is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, a substituted or unsubstituted carbazoleyl, a substituted or unsubstituted benzocarbazoleyl, a substituted or unsubstituted oxazolocarbazoleyl, or a substituted or unsubstituted dibenzothiopheneyl. R 23 It 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. m23 is an integer from 1 to 4, and When m23 is 2 or greater, each R 23 They are the same or different from each other; [Chemical Formula 1-VI]

[0071] In chemical formula 1-VI, L 1 To L 3 Same as above, Ar 15 It is a substituted or unsubstituted C6 to C30 aryl group. Ar 1 and Ar 2 Each of these compounds is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, a substituted or unsubstituted carbazoleyl, a substituted or unsubstituted benzocarbazoleyl, a substituted or unsubstituted oxazolocarbazoleyl, or a substituted or unsubstituted dibenzothiopheneyl. R 24 and R 25 Each of these groups 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. m24 is an integer from 1 to 3. m25 is an integer from 1 to 4. When m24 is 2 or greater, each R 24 They are the same or different from each other, and When m25 is 2 or greater, each R 25 They are the same or different from each other.

[0072] As another example, the first compound may be represented by any one of the chemical formulas 1-VII, 1-VIII, 1-IX, 1-X, 1-XI, and 1-XII.

[0073] [Chemical Formulas 1-VII]

[0074] [Chemical Formula 1-VIII]

[0075] [Chemical Formula 1-IX]

[0076] [Chemical Formula 1-X]

[0077] [Chemical Formula 1-XI]

[0078] [Chemical Formula 1-XII]

[0079] In chemical formulas 1-VII, 1-VIII, 1-IX, 1-X, 1-XI, and 1-XII, L 1 To L 3 Same as above, X 6 It is O, S, NR g or CR h R i , Ar 1 and Ar 2 Each of these compounds is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, a substituted or unsubstituted carbazoleyl, or a substituted or unsubstituted dibenzothiopheneyl. Rg R g R i and R 26 To R 28 Each of these groups 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. m26 and m28 are each an independent integer from 1 to 4. m27 is an integer of 1 or 2. When m26 is 2 or greater, each R 26 Whether they are the same or different, When m27 is 2 or greater, each R 27 They are the same or different from each other, and When m28 is 2 or greater, each R 28 They are the same or different from each other.

[0080] For example, R g R g R i and R 17 To R 28 Each of them can be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0081] For example, Ar 1 To Ar 3 One or more of them can be 9-carbazole group.

[0082] In one implementation, L 1 -Ar 1 L 2 -Ar 2 and L 3 -Ar 3 Each can be independently selected from the substituents listed in Group I.

[0083] [Group I]

[0084] In group I, X 3 It is O, S, NR c or CR d R e , R c R d R e and R 7 To R 11Each of them is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, or substituted or unsubstituted C2 to C20 heteroaryl. Ar 10 and Ar 11 Each is independently a substituted or unsubstituted C6 to C20 aryl group. m7 is an integer from 1 to 5. m8 is an integer from 1 to 4. m9 is an integer from 1 to 3. m10 is an integer of 1 or 2. m11 is an integer from 1 to 7, and It is a connection point.

[0085] When m7 is 2 or greater, each R 7 They can be the same as or different from each other.

[0086] When m8 is 2 or greater, each R 8 They can be the same as or different from each other.

[0087] When m9 is 2 or greater, each R 9 They can be the same as or different from each other.

[0088] When m10 is 2, each R 10 They can be the same as or different from each other.

[0089] When m11 is 2 or greater, each R 11 They can be the same as or different from each other.

[0090] In the most specific embodiment, the first compound represented by chemical formula 1 may be, but is not limited to, one of the compounds listed in groups 1-1 to 1-3 below.

[0091] [Group 1-1]

[0092] [1-1] [1-2] [1-3] [1-4]

[0093] [1-5] [1-6] [1-7] [1-8]

[0094] [1-9] [1-10] [1-11] [1-12]

[0095] [1-13] [1-14] [1-15] [1-16]

[0096] [1-17] [1-18] [1-19] [1-20]

[0097] [1-21] [1-22] [1-23] [1-24]

[0098] [1-25] [1-26] [1-27] [1-28]

[0099] [1-29] [1-30] [1-31] ​​[1-32]

[0100] [1-33] [1-34] [1-35] [1-36]

[0101] [1-37] [1-38] [1-39] [1-40]

[0102] [1-41] [1-42] [1-43] [1-44]

[0103] [1-45] [1-46] [1-47] [1-48]

[0104] [1-49] [1-50] [1-51] [1-52]

[0105] [1-53] [1-54] [1-55] [1-56]

[0106] [Group 1-2]

[0107] [1-57] [1-58] [1-59] [1-60]

[0108] [1-61] [1-62] [1-63] [1-64]

[0109] [1-65] [1-66] [1-67] [1-68]

[0110] [1-69] [1-70] [1-71] [1-72]

[0111] [1-73] [1-74] [1-75] [1-76]

[0112] [1-77] [1-78] [1-79] [1-80]

[0113] [1-81] [1-82] [1-83] [1-84]

[0114] [1-85] [1-86] [1-87] [1-88]

[0115] [1-89] [1-90] [1-91] [1-92]

[0116] [1-93] [1-94] [1-95] [1-96]

[0117] [1-97] [1-98] [1-99] [1-100]

[0118] [1-101] [1-102] [1-103] [1-104]

[0119] [1-105] [1-106] [1-107] [1-108]

[0120] [1-109] [1-110] [1-111] [1-112]

[0121] [1-113] [1-114] [1-115] [1-116]

[0122] [1-117] [1-118] [1-119] [1-120]

[0123] [1-121] [1-122] [1-123] [1-124]

[0124] [1-125] [1-126] [1-127] [1-128]

[0125] [1-129] [1-130] [1-131] [1-132]

[0126] [1-133] [1-134] [1-135] [1-136]

[0127] [1-137] [1-138] [1-139] [1-140]

[0128] [Groups 1-3]

[0129] [1-141] [1-142] [1-143] [1-144] [1-145]

[0130] [1-146] [1-147] [1-148] [1-149] [1-150]

[0131] [1-151] [1-152] [1-153] [1-154] [1-155]

[0132] [1-156] [1-157] [1-158] [1-159] [1-160]

[0133] [1-161] [1-162] [1-163] [1-164] [1-165]

[0134] [1-166] [1-167] [1-168] [1-169] [1-170]

[0135] [1-171] [1-172] [1-173] [1-174] [1-175]

[0136] [1-176] [1-177] [1-178] [1-179] [1-180]

[0137] [1-181] [1-182] [1-183] [1-184] [1-185]

[0138] [1-186] [1-187] [1-188] [1-189] [1-190]

[0139] [1-191] [1-192] [1-193] [1-194] [1-195]

[0140] [1-196] [1-197] [1-198] [1-199] [1-200]

[0141] [1-201] [1-202] [1-203] [1-204] [1-205]

[0142] [1-206] [1-207] [1-208] [1-209] [1-210]

[0143] [1-211] [1-212] [1-213] [1-214] [1-215]

[0144] [1-216] [1-217] [1-218] [1-219] [1-220]

[0145] [1-221] [1-222] [1-223] [1-224] [1-225]

[0146] [1-226] [1-227] [1-228] [1-229] [1-230]

[0147] [1-231] [1-232] [1-233] [1-234] [1-235]

[0148] [1-236] [1-237] [1-238] [1-239]

[0149] [1-240] [1-241] [1-242] [1-243]

[0150] [1-244] [1-245] [1-246] [1-247]

[0151] [1-248] [1-249] [1-250] [1-251]

[0152] [1-252] [1-253] [1-254] [1-255]

[0153] [1-256] [1-257] [1-258] [1-259]

[0154] (Dn represents the number of deuterium substitutions and the structure of one or more of the deuterium substitutions).

[0155] The second compound can be used together with the first compound in the luminescent layer to improve charge mobility and stability, thereby improving luminous efficiency and lifetime characteristics.

[0156] As an example, the second compound can be represented by any one of chemical formulas 2A, 2B, 2C, 2D, and 2E.

[0157] [Chemical Formula 2A] [Chemical Formula 2B] [Chemical Formula 2C]

[0158] [Chemical Formula 2D] [Chemical Formula 2E]

[0159] In chemical formulas 2A, 2B, 2C, 2D, and 2E, L a1 To L a4 L 4 and L 5 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. R a1 To R a4 R 1 and R 2 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 4 and Ar 5 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m1 and m2 are each an independent integer from 1 to 4.

[0160] For example, in chemical formulas 2 and 3, Ar 4 and Ar 5 Each of these can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted triphenylene, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted fluorenyl.

[0161] R a1 To R a4 R 1 and R 2 Each of these can be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0162] In one implementation, R a1 To R a4 R 1 and R 2 Each of these can be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0163] For example, R a1 To R a4 R 1 and R 2 Each can be independently hydrogen, deuterium, cyano, or a substituted or unsubstituted phenyl group, and

[0164] In a specific implementation, R a1 To R a4 R 1 and R 2 Each can be hydrogen, deuterium, or a substituted or unsubstituted phenyl group, independently.

[0165] As a specific example, the second compound can be represented by the chemical formula 2C.

[0166] In one implementation, L 4 -Ar 4 and L 5 -Ar 5 Each can be one of the substituents listed in Group II, and each can be independent of the others.

[0167] [Group II]

[0168] In Group II, R 12 To R 16 Each is independently hydrogen, deuterium, cyano, C1 to C10 alkyl, or C6 to C12 aryl. m12 is an integer from 1 to 5. m13 is an integer from 1 to 4. m14 is an integer from 1 to 3. m15 is an integer of 1 or 2. m16 is an integer from 1 to 7, and It is a connection point.

[0169] When m12 is 2 or greater, each R 12 They can be the same as or different from each other.

[0170] When m13 is 2 or greater, each R 13 They can be the same as or different from each other.

[0171] When m14 is 2 or greater, each R 14 They can be the same as or different from each other.

[0172] When m15 is 2, each R 15 They can be the same as or different from each other.

[0173] When m16 is 2 or greater, each R 16 They can be the same as or different from each other.

[0174] For example, the second compound can be represented by the chemical formula 2C.

[0175] In another specific embodiment of the present invention, L a1 To L a4 Each can be a single key, L 4 and L 5 Each can be a single bond or a substituted or unsubstituted C6 to C12 aryl group, R 1 R 2 and R a1 To R a4 Each can be hydrogen, deuterium, or phenyl, and Ar 4 and Ar 5 Each of them can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0176] For example, L a1 To L a4 It can be a single key, R 1 R 2 and R a1 To R a4 Each can be independently hydrogen, deuterium, or C6 to C12 aryl, and L 4 -Ar 4 and L 5 -Ar 5 Each can be one of the substituents listed in Group II, and each can be independent of the others.

[0177] In the most specific embodiment, the second compound represented by the combination of chemical formula 2 and chemical formula 3 may be selected from, but is not limited to, one of the compounds listed in group 2.

[0178] [Group 2]

[0179] [2-1] [2-2] [2-3] [2-4]

[0180] [2-5] [2-6] [2-7] [2-8]

[0181] [2-9] [2-10] [2-11] [2-12]

[0182] [2-13] [2-14] [2-15] [2-16]

[0183] [2-17] [2-18] [2-19] [2-20]

[0184] [2-21] [2-22] [2-23] [2-24]

[0185] [2-25] [2-26] [2-27] [2-28]

[0186] [2-29] [2-30] [2-31] [2-32]

[0187] [2-33] [2-34] [2-35] [2-36]

[0188] [2-37] [2-38] [2-39] [2-40]

[0189] [2-41] [2-42] [2-43] [2-44]

[0190] [2-45] [2-46] [2-47] [2-48]

[0191] [2-49] [2-50] [2-51] [2-52]

[0192] [2-53] [2-54] [2-55] [2-56]

[0193] [2-57] [2-58] [2-59] [2-60]

[0194] [2-61] [2-62] [2-63] [2-64]

[0195] [2-65] [2-66] [2-67] [2-68]

[0196] [2-69] [2-70] [2-71] [2-72]

[0197] [2-73] [2-74] [2-75] [2-76]

[0198] [2-77] [2-78] [2-79] [2-80]

[0199] [2-81] [2-82] [2-83] [2-84]

[0200] [2-85] [2-86] [2-87] [2-88]

[0201] [2-89] [2-90] [2-91] [2-92]

[0202] [2-93] [2-94] [2-95] [2-96]

[0203] [2-97] [2-98] [2-99] [2-100]

[0204] For example, the first compound and the second compound may be contained in a weight ratio of 1:99 to 99:1. Within this range, the appropriate weight ratio can be adjusted using the electron transport capability of the first compound and the hole transport capability of the second compound to achieve bipolar characteristics, thereby improving efficiency and lifetime. Within this range, they may be contained in weight ratios of, for example, about 10:90 to 90:10, about 20:80 to 80:20, and, for example, in weight ratios of, for example, about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40. As a specific example, they may be contained in weight ratios of 40:60, 50:50, or 60:40.

[0205] The dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, such as a red or green phosphorescent dopant.

[0206] The dopant is a material that is mixed in small amounts with a compound or composition for 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. The dopant can be, for example, an inorganic, organic, or organic / inorganic compound, and one or more of these types can be used.

[0207] Examples of dopants can be phosphorescent dopants, and examples of phosphorescent dopants can be organometallic compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants can be, for example, compounds represented by the chemical formula Z, but are not limited thereto.

[0208] [Chemical Formula Z]

[0209] L 6 MX 2

[0210] In the chemical formula Z, M is a metal, and L 6 and X 2 The same or different ligands that form a complex with M.

[0211] 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.

[0212] By L 6 and X 2Examples of ligands may be selected from, but are not limited to, the chemical formulas listed in group A.

[0213] [Group A]

[0214] In group A, R 300 To R 302 Each is independently hydrogen, deuterium, a C1 to C30 alkyl group substituted or unsubstituted with a halogen, a C6 to C30 aryl group substituted or unsubstituted with a C1 to C30 alkyl group, or a halogen, and R 303 To R 324 Each of the following is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF5, trialkylsilyl having substituted or unsubstituted C1 to C30 alkyl, dialkylarylsilyl having substituted or unsubstituted C1 to C30 alkyl and C6 to C30 aryl, or triarylsilyl having substituted or unsubstituted C6 to C30 aryl.

[0215] In one embodiment, the dopant may be an iridium complex and may be represented by chemical formula 6-1 or chemical formula 6-2.

[0216] [Chemical Formula 6-1]

[0217] In chemical formula 6-1, R 101 To R 116 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 132 R 133 R 134 , R 132 To R 134 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. R 101 To R 116 One or more of them are functional groups represented by the chemical formula V-1. L 100 It is a bidentate ligand of a monovalent anion and a ligand coordinated to iridium via a lone pair of electrons from a carbon or heteroatom. m21 and m22 are each independent integers from 0 to 3, and m21 + m22 is an integer from 1 to 3. [Chemical Formula V-1]

[0218] In chemical formula V-1, R 135 To R 139 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 132 R 133 R 134 ,and It refers to the part that is attached to a carbon atom.

[0219] [Chemical Formula 6-2]

[0220] In chemical formula 6-2, R 101 To R 117 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 133 R 134 R 135 , R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. L 100 It is a bidentate ligand of a monovalent anion and a ligand coordinated to iridium via a lone pair of electrons from a carbon or heteroatom. n1 and n2 are independent integers from 0 to 3, and n1 + n2 is any integer from 1 to 3.

[0221] In another embodiment, the dopant may be a platinum complex and may be represented, for example, by the chemical formula Z-1.

[0222] [Chemical Formula Z-1]

[0223] In chemical formula Z-1, rings A, B, C, and D independently represent 5- or 6-membered carbon rings or heterocycles; R A R B R C and R D Independently indicates mono-, di-, tri-, or tetra-substituted or unsubstituted; LB L C and L D Each is independently selected from direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and combinations thereof; When nA is 1, L E Selected from direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and their combinations; when nA is 0, L E It does not exist; and R A R B R C R D R and R' are each independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; any adjacent R A R B R C R D R and R' are optionally connected to each other to provide a loop; X B X C X D and X E Each is independently selected from carbon and nitrogen; and Q 1 Q 2 Q 3 and Q 4 Each represents oxygen or a direct bond.

[0224] Platinum complexes can be represented, for example, by chemical formula 7-1 or chemical formula 7-2.

[0225] [Chemical Formula 7-1]

[0226] [Chemical Formula 7-2]

[0227] In chemical formulas 7-1 and 7-2, X 100 Selected from O, S and NR 132 , R 118 To R 132 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 133 R134 R 135 , R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. R 118 To R 132 One or more of them are -SiR 133 R 134 R 135 Or tert-butyl, and R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0228] In addition to the light-emitting layer, the organic layer may also include a charge transport region.

[0229] The charge transport region can be, for example, the hole transport region 140.

[0230] The hole transport region 140 can further improve hole injection and / or hole mobility between the anode 120 and the light-emitting layer 130 and block electrons.

[0231] Specifically, the hole transport region 140 may include a hole transport layer between the anode 120 and the light-emitting layer 130 and a hole transport auxiliary layer between the light-emitting layer 130 and the hole transport layer, and at least one of the hole transport layer and the hole transport auxiliary layer may contain one or more of the compounds listed in Group B.

[0232] [Group B]

[0233] (Dn refers to the number of deuterium substitutions and represents the structure that is substituted by one or more deuteriums.)

[0234] In the hole transport region 140, in addition to the compounds described above, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A and compounds with similar structures may also be used.

[0235] In addition, the charge transport region can be, for example, the electron transport region 150.

[0236] The electron transport region 150 can also improve electron injection and / or electron mobility between the cathode 110 and the light-emitting layer 130 and block holes.

[0237] Specifically, the electron transport region 150 may include an electron transport layer between the cathode 110 and the light-emitting layer 130, and an electron transport auxiliary layer between the light-emitting layer 130 and the electron transport layer.

[0238] The electron transport layer may contain a third compound represented by chemical formula 4.

[0239] [Chemical Formula 4]

[0240] In chemical formula 4, X 1 Is it O or S? Z 1 To Z 6 Each is independently N or CR b , Z 1 To Z 3 At least two of them are N. Z 4 To Z 6 At least two of them are N. L 7 It is a substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene. Ar 6 To Ar 9 Each is independently a substituted or unsubstituted C6 to C30 aryl group. R b and R 3 To R 6 Each of these groups 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. m3 and m4 are each an independent integer from 1 to 3, and m5 and m6 are each an integer from 1 to 4.

[0241] For example, Ar 6 It can be a substituted or unsubstituted phenyl group, and Ar 7 To Ar 9 Each can be a substituted or unsubstituted C6 to C12 aryl group, independently.

[0242] L 7 It can be one of the linking groups listed in Group III.

[0243] Group III

[0244] In Group III, R 29 It is hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, or substituted or unsubstituted C2 to C20 heteroaryl. m29 is an integer from 1 to 4. It is a connection point.

[0245] When m29 is 2 or greater, each R 29 They can be the same as or different from each other.

[0246] In the most specific embodiment, the third compound represented by chemical formula 4 may be selected from, but is not limited to, one of the compounds listed in group 3.

[0247] [Group 3]

[0248] [3-1] [3-2] [3-3] [3-4]

[0249] [3-5] [3-6] [3-7] [3-8]

[0250] [3-9] [3-10] [3-11] [3-12]

[0251] [3-13] [3-14] [3-15] [3-16]

[0252] [3-17] [3-18] [3-19] [3-20]

[0253] [3-21] [3-22] [3-23] [3-24]

[0254] [3-25] [3-26] [3-27] [3-28]

[0255] [3-29] [3-30] [3-31] [3-32]

[0256] [3-33] [3-34] [3-35] [3-36]

[0257] [3-37] [3-38] [3-39] [3-40]

[0258] [3-41] [3-42] [3-43] [3-44]

[0259] [3-45] [3-46] [3-47] [3-48]

[0260] [3-49] [3-50] [3-51] [3-52]

[0261] [3-53] [3-54] [3-55] [3-56]

[0262] [3-57] [3-58] [3-59] [3-60]

[0263] [3-61] [3-62] [3-63] [3-64]

[0264] [3-65] [3-66] [3-67] [3-68]

[0265] [3-69] [3-70] [3-71] [3-72]

[0266] [3-73] [3-74] [3-75] [3-76]

[0267] Because the third compound, represented by chemical formula 4, possesses a relatively high T1 energy, when included in an electron transport layer, it can effectively prevent back-energy transfer, thereby effectively suppressing excitons formed in the emissive layer. Furthermore, the LUMO electron cloud is stably distributed due to the presence of the DBX substituent, thus improving molecular stability when used as an electron transport layer. When this compound is used as an electron transport layer, electron transport occurs efficiently, thereby improving device characteristics. Specifically, the molecular structure itself is stable and can effectively suppress excitons in the emissive layer, thus improving lifetime characteristics.

[0268] Meanwhile, the second compound, represented by the combination of chemical formulas 2 and 3, possesses a shallow HOMO energy level, thus enhancing hole injection and transport capabilities. This, in turn, improves device characteristics when used together with the first compound in the emissive layer. Because the second compound exhibits excellent hole injection and transport capabilities, the emission zone tends to migrate towards the electron transport layer. Therefore, there is a possibility that device lifetime may be reduced due to interface degradation between the emissive and electron transport layers. When combined with the third compound in the electron transport layer, interface degradation can be effectively prevented to avoid lifetime reduction, while simultaneously improving low-drive and high-efficiency characteristics.

[0269] In the most specific embodiment, the first compound is represented by chemical formula 1-V, and the second compound may be represented by chemical formula 3C.

[0270] The electron transport auxiliary layer may contain one or more compounds listed in group C below.

[0271] [Group C]

[0272] Another embodiment of the present invention can provide an organic light-emitting diode that, in addition to the light-emitting layer 130, also includes a hole transport region 140 and an electron transport region 150 as an organic layer 105, such as... Figure 1 As shown.

[0273] In addition to the light-emitting layer, an organic light-emitting diode may also include an electron injection layer (not shown), a hole injection layer (not shown), etc., as organic layers.

[0274] An organic light-emitting diode 100 can be manufactured by forming an anode or cathode on a substrate, then forming an organic layer by a dry film method (such as vacuum deposition, sputtering, plasma electroplating and ion electroplating), and forming a cathode or anode thereon.

[0275] Organic light-emitting diodes (OLEDs) can be used in organic light-emitting display devices.

[0276] Invention Model

[0277] In the following description, implementation methods are illustrated in more detail with reference to embodiments. However, these embodiments are exemplary, and the scope of the invention is not limited thereto.

[0278] In the following examples and synthesis examples, the starting materials and reactants used were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry, or P & H Tech, or synthesized by known methods, unless otherwise specified.

[0279] (Synthesis of compounds for organic optoelectronic devices)

[0280] Synthesis of the first compound

[0281] Synthesis Example 1: Synthesis of Compounds 1-98

[0282] [Reaction Formula 1]

[0283] Step 1: Synthesis of intermediate I-1

[0284] Under nitrogen atmosphere, 2,4-dichloro-6-(phenyl-2,3,4,5,6-d5)-1,3,5-triazine (59.3 g, 256 mmol) and 9H-carbazole-1,2,3,4,5,6,7,8-d8 (30 g, 171 mmol) were dissolved in 500 mL of tetrahydrofuran, and then sodium tert-butoxide (18.1 g, 188 mmol) was slowly added at 0°C with stirring. After 12 hours, water was added to the reaction solution and the mixture was filtered. The resulting residue was separated and purified by rapid column chromatography to obtain intermediate I-1 (50 g, 79%).

[0285] Step 2: Synthesis of intermediate I-2

[0286] Under nitrogen atmosphere, (3-(9H-carbazole-9-yl-d8)phenyl-2,4,5,6-d4)boronic acid (30.6 g, 102 mmol) and 1-bromo-4-chlorobenzene-2,3,5,6-d4 (20 g, 102 mmol) were added and dissolved by adding 300 mL of tetrahydrofuran, followed by adding 150 mL of an aqueous solution containing potassium carbonate (28.2 g, 204 mmol) and stirring. After adding tetra(triphenylphosphine)palladium (3.54 g, 3.06 mmol), the mixture was heated and refluxed at 80°C for 12 hours. Upon completion of the reaction, the organic layer was extracted, water was removed with anhydrous magnesium sulfate, and the residue was filtered and concentrated under reduced pressure. The resulting residue was separated and purified by rapid column chromatography to obtain intermediate I-2 (35 g, 93%).

[0287] Step 3: Synthesis of intermediate I-3

[0288] Under nitrogen atmosphere, intermediate I-2 (35 g, 94.6 mmol) was dissolved in 500 mL xylene, followed by the addition of pinacol diborate (28.8 g, 113 mmol), tris(dibenzylacetone)palladium(0) (0.87 g, 0.95 mmol), tricyclohexylphosphine (1.1 g, 3.8 mmol), and potassium acetate (27.8 g, 284 mmol). The mixture was heated and refluxed with stirring for 8 hours. After the reaction was complete, water was added to the reaction solution, and the mixture was extracted with dichloromethane. The water was removed with anhydrous magnesium sulfate, and the residue was filtered and concentrated under reduced pressure. The resulting residue was separated and purified by rapid column chromatography to obtain intermediate I-3 (30 g, 69%).

[0289] Step 4: Synthesis of intermediate I-4

[0290] Compound 1-98 (15 g, 83%) was obtained in the same manner as in step 2 using intermediates I-1 (10 g, 27 mmol) and I-3 (12.5 g, 27 mmol).

[0291] Synthetic Example 2: Synthesis of Compound 1-119

[0292] [Reaction 2]

[0293] Step 1: Synthesis of intermediate I-4

[0294] Under nitrogen atmosphere, 2-bromo-1-fluoro-3-iodobenzene (50.0 g, 166.2 mmol), phenylboronic acid (22.3 g, 182.8 mmol), K₂CO₃ (45.9 g, 332.4 mmol), and Pd(PPh₃)₄ (9.6 g, 8.3 mmol) were dissolved in THF (350 ml) and distilled water (160 ml) and stirred under reflux at 70°C for 6 hours. After the reaction was complete, the aqueous layer was removed and intermediate I-4 (28.9 g, 69%) was obtained by column chromatography (hexane: DCM (30%)).

[0295] Step 2: Synthesis of intermediate I-5

[0296] Under nitrogen atmosphere, intermediate I-4 (21.7 g, 105.0 mmol), pinacol diborate (35.1 g, 138.1 mmol), potassium acetate (22.6 g, 230.2 mmol), and Pd(dppf)Cl2 (4.7 g, 5.8 mmol) were placed in a round-bottom flask and dissolved in 380 mL of xylene. The mixture was stirred and refluxed at 140°C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered to remove salts, and then excess DCM and distilled water were added, followed by extraction. Intermediate I-5 (20.6 g, 60%) was obtained by column chromatography (hexane:DCM (30% to 50%)).

[0297] Step 3: Synthesis of intermediate I-7

[0298] Under nitrogen atmosphere, intermediates I-5 (20.6 g, 69.1 mmol), I-6 (20.6 g, 57.6 mmol), K₂CO₃ (15.9 g, 115.2 mmol), and Pd(PPh₃)₄ (3.33 g, 2.88 mmol) were dissolved in THF (300 ml) and distilled water (60 ml), and then stirred under reflux at 70°C for 6 hours. After the reaction was complete, the aqueous layer was removed and intermediate I-7 (19.9 g, 70%) was obtained by column chromatography (hexane: DCM (30%)).

[0299] Step 4: Synthesis of Compounds 1-119

[0300] Under nitrogen atmosphere, intermediate I-7 (19.9 g, 40.3 mmol), 2-phenyl-9H-carbazole (19.6 g, 80.6 mmol), and K3PO4 (17.1 g, 80.6 mmol) were dissolved in DMF (130 ml) in a round-bottom flask and stirred under reflux at 150°C for 4 hours. After the reaction was complete, the reaction product was slowly added dropwise to excess water to precipitate a solid, which was then separated by column chromatography (hexane: DCM (30%)). The filtered solid was used to obtain compound 1-119 (17.9 g, 62%).

[0301] Synthesis of the second compound

[0302] Synthesis Example 3: Synthesis of Compound 2-32

[0303] Compound 2-32 was synthesized by referring to the method disclosed in KR10-2072208.

[0304] Synthesis Example 4: Synthesis of Compound R-1

[0305] Compound R-1 was synthesized by referring to the method disclosed in KR10-1649683.

[0306] Synthesis of the third compound

[0307] Synthesis Example 5: Synthesis of Compound 3-29

[0308] [Reaction 3]

[0309] Step 1: Synthesis of intermediate I-8

[0310] Under nitrogen atmosphere, 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (25 g, 59.54 mmol) was dissolved in 200 mL xylene, followed by the addition of pinacol diborate (18.9 g, 74.42 mmol), Pd(dppf)Cl2 (2.18 g, 2.98 mmol), tricyclohexylphosphine (3.34 g, 11.91 mmol), and potassium acetate (11.69 g, 119.07 mmol), and the mixture was heated under reflux for 8 hours. After the reaction was complete, water was added to the reaction solution, and the mixture was extracted with DCM. The water was removed with MgSO4, and the residue was filtered and concentrated under reduced pressure. The resulting residue was separated and purified by rapid column chromatography to obtain intermediate I-8 (21.21 g, 80%).

[0311] Step 2: Synthesis of Compound I-9

[0312] Intermediate I-9 was synthesized using the method disclosed in KR 10-2022-0032864.

[0313] Step 3: Synthesis of compound 3-29

[0314] Under nitrogen atmosphere, intermediates I-8 (21.21 g, 41.47 mmol), I-9 (17.99 g, 41.47 mmol), K₂CO₃ (11.46 g, 82.94 mmol), and Pd(PPh₃)₄ (2.40 g, 2.07 mmol) were dissolved in THF (200 ml) and distilled water (60 ml) and stirred under reflux at 60°C for 12 hours. After the reaction was complete, the aqueous layer was removed, and the organic solvent was removed under reduced pressure to obtain a solid. The resulting solid was dissolved in a high-temperature MCB. After removing water with MgSO₄, the organic solvent was filtered through a silica gel pad, and the filtrate was stirred. When a solid formed, it was filtered and dried under vacuum to obtain compound 3-29 (22.73 g, 70%).

[0315] Synthesis Example 6: Synthesis of Compound R-2

[0316] Compound R-2 was synthesized by referring to the method disclosed in KR 10-2086763.

[0317] Synthesis Example 7: Synthesis of Compound R-3

[0318] Compound R-3 was synthesized using intermediate I-8 and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine in the same manner as that used for the synthesis of compound 3-29.

[0319] Example 1: Manufacturing of Green Organic Light Emitting Diodes

[0320] 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 solvents such as isopropanol, acetone, and methanol, and then dried. It was then moved to a plasma cleaner and cleaned with oxygen plasma for 10 minutes before being moved to a vacuum depositor. Using this prepared ITO transparent electrode as the anode, compound E, doped with 3% NDP-9 (Novaled GmbH), was vacuum deposited on the ITO substrate to form a 100 Å thick hole injection layer, and compound A was deposited on the hole injection layer to form a 1350 Å thick hole transport layer. On the hole transport layer, compound B was deposited to a thickness of 320 Å to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compounds 1-119 and 2-32 in a 3:7 weight ratio were used simultaneously as the host, and 7 wt% IrGD was doped as a dopant to form a 330 Å thick light-emitting layer by vacuum deposition. Subsequently, compound 3-29 was deposited on the light-emitting layer to form a 50 Å thick electron transport auxiliary layer, and compound 3-29 and LiQ were simultaneously vacuum-deposited in a 1:1 weight ratio to form a 300 Å thick electron transport layer. On the electron transport layer, an organic light-emitting diode was fabricated by sequentially vacuum-depositing 15 Å of LiQ and 1200 Å of Al.

[0321] It is manufactured according to the following structure: ITO / compound A (3% NDP-9 doped, 100 Å) / compound B (1350 Å) / compound F (320 Å) / EML [body (compound 1-119 : compound 2-32 = 3 : 7 wt% / wt%) : IrGD = 93wt% : 7 wt%] (330 Å) / compound 3-29 (50 Å) / compound 3-29 : LiQ (300 Å) / LiQ (15 Å) / Al (1200 Å).

[0322] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine

[0323] Compound B: N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(3-(9-phenyl-9H-fluorene-9-yl)phenyl)-9H-fluorene-2-amine

[0324] [IrGD]

[0325] Example 2 and Comparative Examples 1 to 8

[0326] Organic light-emitting diodes were manufactured in the same manner as in Example 1, except that the composition was changed to those listed in Tables 1 to 5.

[0327] evaluate

[0328] The driving voltage and lifetime characteristics of the organic light-emitting diodes according to Examples 1, 2 and Comparative Examples 1 to 8 were evaluated.

[0329] The specific measurement methods are shown below, and the results are presented in Tables 1 to 5.

[0330] (1) Measure the change in current density based on the voltage change

[0331] While increasing the voltage from 0 V to 10 V, the current flowing through the unit diode in the resulting organic light-emitting diode was measured using a current-voltmeter (Keithley 2400), and the measured current value was divided by the area to provide the result.

[0332] (2) Measure the change in brightness based on voltage changes

[0333] The luminance was measured using a luminance meter (Minolta Cs-1000A) while the voltage of the organic light-emitting diode was increased from 0 V to 10 V.

[0334] (3) Measuring lifespan

[0335] In terms of brightness (cd / m 2 Maintain at 30000 cd / m 2 Meanwhile, the results were obtained by measuring the time it took for the current efficiency (cd / A) to decrease to 97%.

[0336] The lifetime measurements were calculated as relative values ​​based on the lifetime measurements of Example 1 or Example 2 and are listed in Tables 3 to 5.

[0337] (4) Measure the driving voltage

[0338] Each device was measured at 15 mA / cm² using a current-voltmeter (Keithley 2400). 2 The result is obtained by applying the driving voltage.

[0339] The driving voltage is calculated as a relative value based on the driving voltage of Example 1 or Example 2 and is listed in Tables 1, 2 and 5.

[0340] [Table 1]

[0341] [Table 2]

[0342] [Table 3]

[0343] [Table 4]

[0344] [Table 5]

[0345] Referring to Tables 1 and 2, it can be confirmed that the organic light-emitting diodes according to Examples 1 and 2 exhibit significantly improved driving voltages compared to those according to Comparative Examples 1 and 2. Furthermore, referring to Tables 3 and 4, it can be confirmed that the organic light-emitting diodes according to Examples 1 and 2 exhibit significantly improved lifetimes compared to those according to Comparative Examples 3 and 4.

[0346] Referring to Table 5, it can be confirmed that the organic light-emitting diode according to Example 1 has significantly improved driving voltage and lifetime compared to the organic light-emitting diodes according to Comparative Examples 7 and 8. In particular, it can be confirmed that the lifetime characteristics are significantly improved.

[0347] Although the invention has been described in conjunction with exemplary embodiments now considered practical, it should be understood that the invention is not limited to the disclosed embodiments. Rather, it is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. An organic optoelectronic device, comprising: The anode and cathode facing each other, The light-emitting layer between the anode and the cathode, and An electron transport layer between the light-emitting layer and the cathode; The light-emitting layer comprises a first compound represented by chemical formula 1 and a second compound represented by a combination of chemical formulas 2 and 3, and The electron transport layer contains a third compound represented by chemical formula 4: [Chemical Formula 1] In chemical formula 1, Ar 1 To Ar 3 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and L 1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene, or a substituted or unsubstituted C2 to C30 heteroarylene; [Chemical Formula 2][Chemical Formula 3] In chemical formulas 2 and 3, a1 in chemical formula 2 up to a4 In the middle, the two adjacent ones are each connected to chemical formula 3. The connecting carbon (C). In chemical formula 2, a1 up to a4 In the formula, the other two not connected to chemical formula 3 are CL. a -R a , L a L 4 and L 5 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. R a R 1 and R 2 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 4 and Ar 5 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. m1 and m2 are each an independent integer from 1 to 4. When m1 is 2 or greater, each R 1 They are the same or different from each other, and When m2 is 2 or greater, each R 2 They are the same or different from each other; [Chemical Formula 4] In chemical formula 4, X 1 Is it O or S? Z 1 To Z 6 Each is independently N or CR b , Z 1 To Z 3 At least two of them are N. Z 4 To Z 6 At least two of them are N. L 7 It is a substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene. Ar 6 To Ar 9 Each is independently a substituted or unsubstituted C6 to C30 aryl group. R b R 3 and R 4 Each of these groups 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. m3 and m4 are each an independent integer from 1 to 3. When m3 is 2 or greater, each R 3 They are the same or different from each other, and When m4 is 2 or greater, each R 4 They are the same or different from each other.

2. The organic optoelectronic device according to claim 1, wherein, Ar 1 To Ar 3 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted benzothiophene pyrimidinyl, substituted or unsubstituted Benzofuran pyrimidinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocarbazoyl, substituted or unsubstituted oxazolocarbazoyl, substituted or unsubstituted indolocarbazoyl, substituted or unsubstituted indolofluorenyl, substituted or unsubstituted benzofuranocarbazoyl, substituted or unsubstituted benzothiophenocarbazoyl, or substituted or unsubstituted dibenzothiophenyl.

3. The organic optoelectronic device according to claim 1, wherein, The first compound is represented by any one of chemical formulas 1-I, 1-II, 1-III, and 1-IV: [Chemical Formula 1-I] In chemical formula 1-I, L 1 To L 3 Same as above, Ar 1 and Ar 2 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted dibenzothiophene. R 17 To R 19 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl or substituted or unsubstituted C6 to C30 aryl. m17 is an integer from 1 to 3. m18 and m19 are each an independent integer from 1 to 4. When m17 is 2 or greater, each R 17 Whether they are the same or different, When m18 is 2 or greater, each R 18 They are the same or different from each other, and When m19 is 2 or greater, each R 19 They are the same or different from each other; [Chemical Formula 1-II] In chemical formula 1-II, L 1 To L 3 Same as above, X 4 Is it O or S? Ar 1 and Ar 2 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted dibenzothiophenyl. R 20 To R 21 Each of these groups 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. m20 is an integer from 1 to 3. m21 is one of the integers from 1 to 4. When m20 is 2 or greater, each R 20 They are the same or different from each other, and When m21 is 2 or greater, each R 21 They are the same or different from each other; [Chemical Formula 1-III] In chemical formula 1-III, L 1 To L 3 Same as above, Z 7 To Z 9 Each is independently N or CR f , Z 7 To Z 9 At least two of them are N, and Ar 1 and Ar 2 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocarbazoyl, substituted or unsubstituted oxazolocarbazoyl, substituted or unsubstituted indolocarbazoyl, substituted or unsubstituted indolofluorenyl, substituted or unsubstituted benzofuranocarbazoyl, substituted or unsubstituted benzothiophenocarbazoyl, or substituted or unsubstituted dibenzothiopheneyl. [Chemical Formula 1-IV] In chemical formula 1-IV, L 1 To L 3 Same as above, X 5 Is it O or S? Ar 1 and Ar 2 Each of these can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted triphenylene. Ar 14 It is a substituted or unsubstituted C6 to C30 aryl group. R 22 It 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. m22 is an integer from 1 to 4, and When m22 is 2 or greater, each R 22 They are the same or different from each other.

4. The organic optoelectronic device according to claim 1, wherein, The first compound is represented by chemical formula 1-V or chemical formula 1-VI: [Chemical Formula 1-V] In chemical formula 1-V, L 1 To L 3 Same as above, Ring A is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, or a substituted or unsubstituted benzoxazolyl group. Ar 1 and Ar 2 Each of these compounds is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, a substituted or unsubstituted carbazoleyl, a substituted or unsubstituted benzocarbazoleyl, a substituted or unsubstituted oxazolocarbazoleyl, or a substituted or unsubstituted dibenzothiopheneyl. R 23 It 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. m23 is an integer from 1 to 4, and When m23 is 2 or greater, each R 23 They are the same or different from each other; [Chemical Formula 1-VI] In chemical formula 1-VI, L 1 To L 3 Same as above, Ar 15 It is a substituted or unsubstituted C6 to C30 aryl group. Ar 1 and Ar 2 Each of these compounds is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, a substituted or unsubstituted carbazoleyl, a substituted or unsubstituted benzocarbazoleyl, a substituted or unsubstituted oxazolocarbazoleyl, or a substituted or unsubstituted dibenzothiopheneyl. R 24 and R 25 Each of these groups 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. m24 is an integer from 1 to 3. m25 is an integer from 1 to 4. When m24 is 2 or greater, each R 24 They are the same or different from each other, and When m25 is 2 or greater, each R 25 They are the same or different from each other.

5. The organic optoelectronic device according to claim 1, wherein, The first compound is represented by any one of the following chemical formulas: 1-VII, 1-VIII, 1-IX, 1-X, 1-XI, and 1-XII. [Chemical Formulas 1-VII] [Chemical Formula 1-VIII] [Chemical Formula 1-IX] [Chemical Formula 1-X] [Chemical Formula 1-XI] [Chemical Formula 1-XII] In chemical formulas 1-VII, 1-VIII, 1-IX, 1-X, 1-XI, and 1-XII, L 1 To L 3 Same as above, X 6 It is O, S, NR g or CR h R i , Ar 1 and Ar 2 Each of these compounds is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, a substituted or unsubstituted carbazoleyl, or a substituted or unsubstituted dibenzothiopheneyl. R g R g R i and R 26 To R 28 Each of these groups 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. m26 and m28 are each an independent integer from 1 to 4. m27 is an integer of 1 or 2. When m26 is 2 or greater, each R 26 Whether they are the same or different, When m27 is 2 or greater, each R 27 They are the same or different from each other, and When m28 is 2 or greater, each R 28 They are the same or different from each other.

6. The organic optoelectronic device according to claim 1, wherein, Ar 1 To Ar 3 One or more of them are 9-carbazole groups.

7. The organic optoelectronic device according to claim 1, wherein, L 1 -Ar 1 L 2 -Ar 2 and L 3 -Ar 3 Each substituent is independently selected from those listed in Group I: [Group I] In group I, X 3 It is O, S, NR c or CR d R e , R c R d R e and R 7 To R 11 Each of them is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, or substituted or unsubstituted C2 to C20 heteroaryl. Ar 10 and Ar 11 Each is independently a substituted or unsubstituted C6 to C20 aryl group. m7 is an integer from 1 to 5. m8 is an integer from 1 to 4. m9 is an integer from 1 to 3. m10 is an integer of 1 or 2. m11 is an integer from 1 to 7, and It is a connection point.

8. The organic optoelectronic device according to claim 1, wherein, The first compound is selected from one of the compounds listed in Groups 1-1 to 1-3: [Group 1-1] [1-1] [1-2][1-3][1-4] [1-5][1-6] [1-7][1-8] [1-9] [1-10] [1-11][1-12] [1-13][1-14] [1-15][1-16] [1-17] [1-18][1-19] [1-20] [1-21] [1-22][1-23][1-24] [1-25][1-26][1-27] [1-28] [1-29] [1-30][1-31] [1-32] [1-33][1-34][1-35] [1-36] [1-37] [1-38][1-39] [1-40] [1-41][1-42][1-43] [1-44] [1-45][1-46][1-47] [1-48] [1-49][1-50][1-51][1-52] [1-53] [1-54] [1-55][1-56] [Group 1-2] [1-57][1-58][1-59] [1-60] [1-61][1-62][1-63][1-64] [1-65] [1-66][1-67] [1-68] [1-69][1-70][1-71] [1-72] [1-73][1-74][1-75] [1-76] [1-77][1-78] [1-79][1-80] [1-81] [1-82][1-83][1-84] [1-85][1-86][1-87] [1-88] [1-89][1-90][1-91][1-92] [1-93][1-94][1-95][1-96] [1-97] [1-98] [1-99] [1-100] [1-101][1-102][1-103][1-104] [1-105] [1-106][1-107][1-108] [1-109][1-110] [1-111][1-112] [1-113] [1-114][1-115][1-116] [1-117][1-118] [1-119][1-120] [1-121][1-122] [1-123][1-124] [1-125] [1-126] [1-127][1-128] [1-129][1-130] [1-131][1-132] [1-133] [1-134][1-135][1-136] [1-137][1-138][1-139][1-140] [Groups 1-3] [1-141] [1-142][1-143][1-144] [1-145] [1-146] [1-147] [1-148][1-149] [1-150] [1-151] [1-152][1-153][1-154][1-155] [1-156][1-157][1-158][1-159] [1-160] [1-161] [1-162] [1-163] [1-164] [1-165] [1-166] [1-167][1-168] [1-169][1-170] [1-171] [1-172] [1-173][1-174] [1-175] [1-176][1-177] [1-178][1-179] [1-180] [1-181] [1-182][1-183] [1-184][1-185] [1-186] [1-187][1-188] [1-189] [1-190] [1-191][1-192] [1-193][1-194][1-195] [1-196][1-197][1-198][1-199] [1-200] [1-201][1-202] [1-203][1-204][1-205] [1-206] [1-207] [1-208] [1-209] [1-210] [1-211][1-212] [1-213][1-214] [1-215] [1-216] [1-217] [1-218] [1-219][1-220] [1-221] [1-222][1-223][1-224][1-225] [1-226] [1-227][1-228] [1-229][1-230] [1-231] [1-232] [1-233] [1-234][1-235] [1-236][1-237] [1-238][1-239] [1-240][1-241][1-242] [1-243] [1-244][1-245][1-246][1-247] [1-248][1-249][1-250][1-251] [1-252][1-253][1-254][1-255] [1-256][1-257][1-258] [1-259] (Dn represents the number of deuterium substitutions and the structure of one or more of the deuterium substitutions).

9. The organic optoelectronic device according to claim 1, wherein, The second compound is represented by any one of chemical formulas 2A, 2B, 2C, 2D, and 2E: [Chemical Formula 2A] [Chemical Formula 2B] [Chemical Formula 2C] [Chemical Formula 2D][Chemical Formula 2E] In chemical formulas 2A, 2B, 2C, 2D, and 2E, L a1 To L a4 L 4 and L 5 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. R a1 To R a4 R 1 and R 2 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 4 and Ar 5 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m1 and m2 are each an independent integer from 1 to 4.

10. The organic optoelectronic device according to claim 9, wherein, The second compound is represented by the chemical formula 2C.

11. The organic optoelectronic device according to claim 9, wherein, L 4 -Ar 4 and L 5 -Ar 5 Each is independently one of the substituents listed in Group II: [Group II] In Group II, R 12 To R 16 Each is independently hydrogen, deuterium, cyano, C1 to C10 alkyl, or C6 to C12 aryl. m12 is an integer from 1 to 5. m13 is one of the integers from 1 to 4. m14 is an integer from 1 to 3. m15 is an integer of 1 or 2. m16 is an integer from 1 to 7, and It is a connection point.

12. The organic optoelectronic device according to claim 1, wherein, The second compound is selected from one of the compounds listed in Group 2: [Group 2] [2-1] [2-2][2-3] [2-4] [2-5] [2-6] [2-7] [2-8] [2-9][2-10] [2-11][2-12] [2-13][2-14][2-15][2-16] [2-17][2-18][2-19][2-20] [2-21][2-22] [2-23] [2-24] [2-25][2-26][2-27][2-28] [2-29][2-30] [2-31][2-32] [2-33][2-34][2-35][2-36] [2-37][2-38][2-39] [2-40] [2-41][2-42] [2-43][2-44] [2-45] [2-46][2-47][2-48] [2-49][2-50] [2-51] [2-52] [2-53][2-54] [2-55] [2-56] [2-57] [2-58][2-59] [2-60] [2-61] [2-62][2-63] [2-64] [2-65][2-66] [2-67] [2-68] [2-69][2-70] [2-71] [2-72] [2-73] [2-74] [2-75][2-76] [2-77] [2-78] [2-79][2-80] [2-81] [2-82] [2-83] [2-84] [2-85][2-86] [2-87] [2-88] [2-89] [2-90][2-91][2-92] [2-93] [2-94][2-95] [2-96] [2-97] [2-98][2-99][2-100] 。 13. The organic optoelectronic device according to claim 1, wherein, Ar 6 It is a substituted or unsubstituted phenyl group, and Ar 7 To Ar 9 Each is independently a substituted or unsubstituted C6 to C12 aryl group.

14. The organic optoelectronic device according to claim 1, wherein, L 7 It is selected from one of the linking groups listed in Group III: Group III In Group III, R 29 It is hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, or substituted or unsubstituted C2 to C20 heteroaryl. m29 is an integer from 1 to 4, and It is a connection point.

15. The organic optoelectronic device according to claim 1, wherein, The third compound is selected from one of the compounds listed in Group 3: [Group 3] [3-1][3-2][3-3] [3-4] [3-5][3-6][3-7] [3-8] [3-9][3-10][3-11][3-12] [3-13][3-14] [3-15][3-16] [3-17][3-18][3-19][3-20] [3-21][3-22][3-23][3-24] [3-25][3-26] [3-27][3-28] [3-29][3-30] [3-31][3-32] [3-33] [3-34][3-35] [3-36] [3-37] [3-38][3-39][3-40] [3-41] [3-42] [3-43] [3-44] [3-45][3-46][3-47] [3-48] [3-49] [3-50][3-51] [3-52] [3-53] [3-54][3-55][3-56] [3-57][3-58][3-59] [3-60] [3-61] [3-62] [3-63] [3-64] [3-65] [3-66] [3-67][3-68] [3-69] [3-70][3-71][3-72] [3-73][3-74][3-75] [3-76] 。 16. A display device comprising the organic optoelectronic device according to any one of claims 1 to 15.

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