Organic optoelectronic device and display device

Abstract

Disclosed are an organic photoelectric device and a display device, the organic photoelectric 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 a combination of Chemical Formula 1 and Chemical Formula 2 and a second compound represented by Chemical Formula 3, the hole transport layer includes a third compound represented by Chemical Formula 4, and the hole transport auxiliary layer includes a fourth compound represented by Chemical Formula 5. The details of Chemical Formulas 1 to 5 are as defined in the specification.

Description

[0001] Citations of Related Applications

[0002] This application claims priority to and the benefits of Korean Patent Application No. 10-2020-0149482 filed in the Korean Intellectual Property Office on November 10, 2020, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Disclosed are an organic optoelectronic device (organic optoelectronic device, organic optoelectronic device, organic optoelectronic device, organic optoelectronic device) and a display device (display device, display device). Background Art

[0004] An organic photoelectric device (organic photodiode) is a device that can convert electrical energy into light energy and vice versa.

[0005] Organic photoelectric devices can be roughly divided into two categories based on their working principles: one is a photoelectric 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; the other is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to electrodes.

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

[0007] Among them, organic light emitting diodes (OLEDs) have attracted much attention in recent years due to the increasing demand for flat panel display devices. Organic light emitting diodes are devices that convert electrical energy into light, and the performance of organic light emitting diodes is greatly affected by organic materials between electrodes. Summary of the invention

[0008] One embodiment provides an organic photoelectric device having high efficiency, long lifespan, and low driving.

[0009] Another embodiment provides a display device including an organic optoelectronic device.

[0010] According to one embodiment, an organic photoelectric 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 a combination of Chemical Formula 1 and Chemical Formula 2 and a second compound represented by Chemical Formula 3, the hole transport layer includes a third compound represented by Chemical Formula 4, and the hole transport auxiliary layer includes a fourth compound represented by Chemical Formula 5.

[0011]

[0012] In Chemical Formula 1 and Chemical Formula 2,

[0013] L 1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heterocyclic group,

[0014] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0015] X 1 is O or S,

[0016] Adjacent two of a1* to a4* in Chemical Formula 1 are linking carbons connected at * in Chemical Formula 2,

[0017] The remaining two of a1* to a4* in Chemical Formula 1 that are not connected at * in Chemical Formula 2 are each independently CR a ,and

[0018] R a and R 1 To R 8 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl;

[0019] [Chemical formula 3]

[0020]

[0021] Wherein, in Chemical Formula 3,

[0022] Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0023] L 4 and L 5 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0024] R b and R 9 To R 18are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and

[0025] m is an integer from 0 to 2;

[0026] [Chemical formula 4]

[0027]

[0028] Among them, in chemical formula 4,

[0029] R 19 To R 25 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,

[0030] L 6 and L 7 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, and

[0031] Ar 5 To Ar 7 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group;

[0032] [Chemical formula 5]

[0033]

[0034] Among them, in chemical formula 5,

[0035] Y 1 and Y 2 are each independently a substituted or unsubstituted C1 to C30 alkyl group or a substituted or unsubstituted C6 to C30 aryl group,

[0036] R 26 To R 32 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,

[0037] L 8 and L 9 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, and

[0038] Ar 8 and Ar 9Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0039] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0040] An organic photoelectric device with low driving force, high efficiency and long life can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0041] Figure 1 is a cross-sectional view showing an organic light emitting diode according to one embodiment.

[0042] <Description of Reference Numerals>

[0043] 300: Organic light-emitting diode

[0044] 110: Anode

[0045] 120: cathode

[0046] 130: Luminous layer

[0047] 141: Hole transport layer

[0048] 142: Hole transport auxiliary layer

[0049] 105: Organic layer DETAILED DESCRIPTION

[0050] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, and the present invention is not limited thereto and is defined by the scope of claims.

[0051] In the present specification, when a definition is not otherwise provided, "substituted" means that at least one hydrogen of the substituent or the compound is replaced with deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amine, 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 a combination thereof.

[0052] In one example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl or cyano. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl or cyano. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl or cyano. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl or naphthyl.

[0053] In the present specification, when a definition is not otherwise provided, "hetero" means a group containing 1 to 3 hetero atoms selected from N, O, S, P and Si in one functional group and the rest are carbon.

[0054] In the present specification, "aryl" refers to a group including at least one hydrocarbon aromatic portion, and all elements of the hydrocarbon aromatic portion have p-orbitals forming conjugation, for example, phenyl, naphthyl, etc., two or more hydrocarbon aromatic portions may be connected by a σ bond and the hydrocarbon aromatic portion may be, for example, biphenyl, terphenyl, quaterphenyl, etc., and two or more hydrocarbon aromatic portions are directly or indirectly fused to provide a non-aromatic fused ring, for example, fluorenyl.

[0055] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0056] In the present specification, "heterocyclic group" is a general concept of heteroaryl group, and may include at least one heteroatom selected from N, O, S, P and Si to replace carbon (C) in a cyclic compound such as an aryl group, a cycloalkyl group, a condensed ring thereof or a combination thereof. When the heterocyclic group is a condensed ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0057] For example, "heteroaryl" may refer to an aryl group including at least one heteroatom selected from N, O, S, P and Si. Two or more heteroaryls may be directly connected by a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.

[0058] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl 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 The invention may include chrysenyl, substituted or unsubstituted triphenylene group (triphenylene group), substituted or unsubstituted perylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indenyl, substituted or unsubstituted furanyl or a combination thereof, but is not limited thereto.

[0059] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted oxadiazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothiophenyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted indolyl, or a substituted or unsubstituted quinolyl. , substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazoline, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzofuranpyrimidinyl, substituted or unsubstituted benzothiophenepyrimidinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene, or a combination thereof, but are not limited thereto.

[0060] In this specification, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and according to the highest occupied molecular orbital (HOMO) level, holes formed in the anode can be easily injected into the light-emitting layer due to the conductive characteristics and transported in the light-emitting layer.

[0061] In addition, the electronic property refers to the ability to accept electrons when an electric field is applied, and according to the lowest unoccupied molecular orbital (LUMO) level, electrons formed in the cathode can be easily injected into the light-emitting layer due to the conductive property and transported in the light-emitting layer.

[0062] Hereinafter, an organic photoelectric device according to one embodiment is described.

[0063] The organic photoelectric device may be any device that converts electrical energy into light energy and vice versa without particular limitation, and it may be, for example, an organic optoelectronic device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.

[0064] Herein, an organic light emitting diode is described as an example of an organic photoelectric device. However, the present invention is not limited thereto and may be equally applicable to other organic photoelectric devices.

[0065] In the accompanying drawings, the thickness of layers, films, panels, regions, etc., is exaggerated for clarity. Throughout the specification, similar figure numbers represent similar elements. It will be understood that when an element, such as a layer, film, region, or substrate is referred to as being "on" another element, it can be directly on the other element, or there can also be intervening elements. Conversely, when an element is referred to as being "directly" "on" another element, there are no intervening elements.

[0066] Figure 1 is a cross-sectional view schematically showing an organic light emitting diode according to one embodiment.

[0067] refer to Figure 1 The organic light emitting diode 300 according to the exemplary embodiment includes an anode 110 and a cathode 120 facing each other, and an organic layer 105 located between the anode 110 and the cathode 120 , wherein the organic layer 105 includes a light emitting layer 130 , a hole transport auxiliary layer 142 , and a hole transport layer 141 .

[0068] The anode 110 may be made of a conductor having a large work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 110 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, etc., or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; a combination of a metal and an oxide 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.

[0069] The cathode 120 may be made of a conductor having a small work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 120 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc., or an alloy thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0070] The light emitting layer 130 is disposed between the anode 110 and the cathode 120 and includes a plurality of hosts and at least one type of dopant.

[0071] The light emitting layer 130 may include a first compound having a relatively strong hole characteristic and a second compound having a relatively strong electron characteristic together as a host.

[0072] The first compound is a compound having relatively strong electronic characteristics and may be represented by a combination of Chemical Formula 1 and Chemical Formula 2.

[0073]

[0074]

[0075] In Chemical Formula 1 and Chemical Formula 2,

[0076] L 1 To L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heterocyclic group,

[0077] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0078] X 1 is O or S,

[0079] Adjacent two of a1* to a4* in Chemical Formula 1 are connecting carbon atoms connected at * in Chemical Formula 2,

[0080] The remaining two of a1* to a4* in Chemical Formula 1 that are not connected at * in Chemical Formula 2 are each independently CR a ,and

[0081] R a and R 1 To R 8 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic.

[0082] The first compound has a form in which benzofuranocarbazole or benzothiophenocarbazole is substituted with a substituted or unsubstituted triazine, and since benzofuran or benzothiophene is fused to the carbazole part, the HOMO electron cloud expands to assist hole injection and transport properties. In the case where an organic light emitting diode includes it, the driving voltage of the device can be reduced and the lifespan characteristics can be improved due to the stability caused by the balance of holes and electrons.

[0083] Specifically, since it is substituted with triazine in the N-direction of the carbazole moiety, electrons and holes are well separated in the molecule, thereby further improving charge injection and transport characteristics.

[0084] On the other hand, it is included together with the second compound to exhibit excellent interface properties and hole and electron transporting capabilities, thereby reducing the driving voltage of a device including it.

[0085] For example, L 2 and L 3 Each independently may be a single bond or a substituted or unsubstituted phenylene group.

[0086] For example, Ar 1 and Ar 2 Each of them independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group.

[0087] For example, *-L 2 -Ar 1 and *-L 3 -Ar 2 The substituents may be each independently selected from Group I.

[0088] [Group I]

[0089]

[0090] In Group I, * is the connection point.

[0091] In one embodiment, Ar 1 and Ar 2 At least one of the groups may be a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0092] For example, L 1 It may be a single bond or a substituted or unsubstituted phenylene group.

[0093] For example, L 1 Can be a single bond.

[0094] For example, R a and R 1 To R 8 Each independently may be hydrogen or a substituted or unsubstituted phenyl.

[0095] For example, R a and R 1 To R 8 Each of may be hydrogen.

[0096] For example, according to the fusion position of Chemical Formula 1 and Chemical Formula 2, the first compound may be represented by, for example, one of Chemical Formula 1A to Chemical Formula 1F.

[0097]

[0098]

[0099] In Chemical Formulae 1A to 1F,

[0100] L 1 To L 3 ,Ar 1 ,Ar 2 , X 1 and R 1 To R 8 Same as above, and R a1 To R a4 Independently with R a The definition is the same.

[0101] As a specific example, the first compound may be represented by one of Chemical Formula 1A, Chemical Formula 1B, Chemical Formula 1C, Chemical Formula 1D, and Chemical Formula 1F.

[0102] As a more specific example, the first compound may be represented by Chemical Formula 1A or Chemical Formula 1F.

[0103] The first compound may be, for example, one of the compounds selected from Group 1, but is not limited thereto.

[0104] [Group 1]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116] The second compound may be a compound having relatively strong hole characteristics and may be represented by Chemical Formula 3.

[0117] [Chemical formula 3]

[0118]

[0119] In chemical formula 3,

[0120] Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0121] L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0122] R b and R 9 To R 18 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and

[0123] m is an integer from 0 to 2.

[0124] The second compound may be used together with the first compound in the light emitting layer to improve light emitting efficiency and lifespan characteristics by increasing charge mobility and improving stability.

[0125] For example, Ar in formula 3 3 and Ar 4each independently may be 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 anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted pyridyl group,

[0126] L in chemical formula 3 4 and L 5 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,

[0127] R in chemical formula 3 9 To R 18 may each independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, and

[0128] m can be 0 or 1.

[0129] For example, “substituted” of Chemical Formula 3 means that at least one hydrogen is replaced with deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0130] In certain embodiments of the present invention, Chemical Formula 3 may be represented by one of Chemical Formula 3-1 to Chemical Formula 3-15.

[0131]

[0132]

[0133] In Chemical Formulae 3-1 to 3-15, R 9 To R 18 may each independently be hydrogen or a substituted or unsubstituted C6 to C12 aryl group, and *-L 4 -Ar 3 and *-L 5 -Ar 4 Each may independently be one of the substituents of Group II.

[0134] [Group II]

[0135]

[0136] In Group II, * is the connection point.

[0137] In one embodiment, Chemical Formula 3 may be represented by Chemical Formula 3-8.

[0138] In addition, *-L in Chemical Formula 3-8 4 -Ar 3and *-L 5 -Ar 4 Each may be independently selected from Group II, for example, any one of C-1, C-2, C-3, C-16 and C-23.

[0139] In a more specific embodiment, all *-L 4 -Ar 3 and *-L 5 -Ar 4 It may be represented by C-1, C-2, or C-3 of Group II, but is not limited thereto.

[0140] In a specific embodiment of the present invention, the second compound can be represented by Chemical Formula 3-8, wherein in Chemical Formula 3-8, Ar 3 and Ar 4 may be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, L 4 and L 5 may each independently be a single bond or a substituted or unsubstituted C6 to C12 arylene group, and R 9 To R 18 Each of them may independently 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 dibenzothiophenyl.

[0141] For example, the second compound may be one of the compounds selected from Group 2, but is not limited thereto.

[0142] [Group 2]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148] For example, the first compound and the second compound may be included in a weight ratio of 1:99 to 99:1. Within the above range, the hole transport capability of the first compound for the organic optoelectronic device and the electron transport capability of the second compound for the organic optoelectronic device may be used to adjust the appropriate weight ratio to achieve bipolar characteristics and improve efficiency and lifespan. Within the above range, for example, they may be included in a weight ratio of about 10:90 to 90:10, about 10:90 to 80:20, about 10:90 to 70:30, about 10:90 to 60:40, or about 20:80 to 50:50. For example, they may be included in a weight ratio of 40:60 or 30:70.

[0149] In one embodiment of the present invention, the first compound and the second compound may each be included as a host of the light-emitting layer, for example, a phosphorescent host.

[0150] The light-emitting layer may further include one or more compounds in addition to the above-mentioned host.

[0151] The light emitting layer may further include a dopant. The dopant may be, for example, a phosphorescent dopant, for example, a red, green or blue phosphorescent dopant, and may be, for example, a red phosphorescent dopant.

[0152] The dopant is a material mixed with the above-mentioned host in a small amount to cause luminescence, and can generally be a material such as a metal complex that emits light by multiple excitations to triplet or more. The dopant can be, for example, an inorganic, organic or organic-inorganic compound, and one or more types thereof can be used.

[0153] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be an organic metal compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the chemical formula Z, but is not limited thereto.

[0154] [Chemical formula Z]

[0155] L 10 MX 3

[0156] In the chemical formula Z, M is a metal and L 10 and X 3 are the same as or different from each other, and are ligands that form a complex with M.

[0157] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L 10 and X3 This may be, for example, a bidentate ligand.

[0158] The hole transport layer 141 may be disposed between the anode 110 and the light emitting layer 130 and may facilitate hole transport from the anode 110 to the light emitting layer 130. For example, the hole transport layer 141 may include a material having a HOMO energy level between the work function of the conductor forming the anode 110 and the HOMO energy level of the material forming the light emitting layer 130.

[0159] The hole transport layer 141 may include, for example, a third compound represented by Chemical Formula 4.

[0160] [Chemical formula 4]

[0161]

[0162] In chemical formula 4,

[0163] R 19 To R 25 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,

[0164] L 6 and L 7 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, and

[0165] Ar 5 To Ar 7 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0166] For example, L 6 and L 7 Each independently may be a single bond or a substituted or unsubstituted phenylene group.

[0167] For example, L 6 and L 7 may each independently be a single bond.

[0168] For example, Ar 5 and Ar 6 Each of the above groups may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted bisfluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof.

[0169] For example, Ar5 and Ar 6 Each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted fluorenyl group.

[0170] As a specific example, *-L 6 -Ar 5 and *-L 7 -Ar 6 The substituents may be each independently selected from group III.

[0171] [Group III]

[0172]

[0173] In Group III, * is the connection point.

[0174] For example, Ar 7 It may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

[0175] For example, R 19 To R 25 Each independently may be hydrogen or a substituted or unsubstituted phenyl.

[0176] For example, R 19 To R 25 Each may be hydrogen.

[0177] The third compound may be, for example, one of the compounds of Group 3, but is not limited thereto.

[0178] [Group 3]

[0179]

[0180]

[0181]

[0182]

[0183] The hole transport auxiliary layer 142 may be disposed between the above-mentioned light emitting layer 130 and the hole transport layer 141, and specifically, may be disposed in contact with the light emitting layer 130. Since the hole transport auxiliary layer 142 is disposed in contact with the light emitting layer 130, the hole mobility at the interface between the light emitting layer 130 and the hole transport layer 141 may be accurately controlled. The hole transport auxiliary layer 142 may include a plurality of layers.

[0184] The hole transport auxiliary layer 142 may include, for example, a fourth compound represented by Chemical Formula 5.

[0185] [Chemical formula 5]

[0186]

[0187] In Chemical Formula 5,

[0188] Y 1 and Y 2 are each independently a substituted or unsubstituted C1 to C30 alkyl group or a substituted or unsubstituted C6 to C30 aryl group,

[0189] R 26 To R 32 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,

[0190] L 8 and L 9 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, and

[0191] Ar 8 and Ar 9 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0192] The fourth compound is a compound having a high HOMO energy level and can have excellent hole injection characteristics. Therefore, the fourth compound is applied to the hole transport auxiliary layer 142 to effectively improve the hole mobility at the interface between the light emitting layer 130 and the hole transport layer 141, thereby effectively reducing the driving voltage of the organic photoelectric device.

[0193] For example, L 8 and L 9 Each independently may be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0194] For example, L 8 and L 9 Each independently may be a single bond or a substituted or unsubstituted phenylene group.

[0195] For example, Ar 8 and Ar 9 Each of them independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group.

[0196] For example, Ar 8 and Ar 9Each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted fluorenyl group.

[0197] In an exemplary embodiment, *-L 8 -Ar 8 and *-L 9 -Ar 9 The substituents may be each independently selected from Group IV.

[0198] [Group IV]

[0199]

[0200] In group IV, * is the connection point.

[0201] For example, Y 1 and Y 2 Each may independently be a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group.

[0202] For example, Y 1 and Y 2 Each may independently be a substituted or unsubstituted C1 to C5 alkyl group or a substituted or unsubstituted phenyl group.

[0203] For example, R 26 To R 32 Each independently may be hydrogen or a substituted or unsubstituted phenyl.

[0204] For example, R 26 To R 32 Each may be hydrogen.

[0205] The fourth compound may be, for example, one of the compounds of Group 4, but is not limited thereto.

[0206] [Group 4]

[0207]

[0208]

[0209] According to a more specific embodiment of the present invention, the first compound may be represented by the above Chemical Formula 1A, the second compound may be represented by the above Chemical Formulas 3-8, the third compound may be represented by the above Chemical Formula 4 and the fourth compound may be represented by the above Chemical Formula 5.

[0210] Each substituent is as defined above.

[0211] In addition to the above-mentioned light emitting layer 130 , hole transport layer 141 , and hole transport auxiliary layer 142 , the organic layer 105 may further include an electron transport region (not shown).

[0212] The electron transport region can also improve the electron injection and / or electron mobility between the cathode 120 and the light-emitting layer 130 and block holes.

[0213] Specifically, the electron transport region may include an electron transport layer between the cathode 120 and the light-emitting layer 130 and an electron transport assisting layer located between the light-emitting layer 130 and the electron transport layer, and at least one compound in Group A may be included in at least one of the electron transport layer and the electron transport assisting layer.

[0214] [Group A]

[0215]

[0216]

[0217]

[0218] In addition to the light-emitting layer 130 as the organic layer 105, another embodiment of the present invention may provide an organic light-emitting diode further including an electron injection layer, a hole injection layer, etc.

[0219] The organic light-emitting diode 300 can be produced by forming an anode or a cathode on a substrate, and then forming an organic layer by a dry film method such as vacuum deposition, sputtering, plasma plating, and ion plating, or a solution method, and forming a cathode or an anode thereon.

[0220] The above organic optoelectronic device can be applied to a display device. For example, the organic light-emitting diode can be applied to an organic light-emitting diode (OLED) display.

[0221] Hereinafter, the embodiments will be described in more detail with reference to examples. However, these examples are exemplary, and the scope of the claims is not limited thereto.

[0222] Hereinafter, unless otherwise specified, the starting materials and reactants used in the examples and synthesis examples are purchased from Sigma-Aldrich Co., Ltd., TCI Inc., Tokyo chemical industry, or P&H tech, or are synthesized by known methods.

[0223] The compound provided as a more specific example of the present invention was synthesized by the following steps.

[0224] (Preparation of the First Compound)

[0225] <Synthesis of Int-2>

[0226]

[0227] Synthesis Example 1: Synthesis of Intermediate Int-1

[0228] [Reaction Scheme 1]

[0229]

[0230] 4-Bromodibenzofuran (50 g, 202.36 mmol), 2-chloroaniline (38.72 g, 303.53 mmol), Pd2(dba)3 (9.26 g, 10.12 mmol), P(t-bu)3 (7.39 ml, 30.35 mmol) and NaO(t-Bu) (29.17 g, 303.53 mmol) were placed in a round-bottom flask, dissolved in toluene (650 ml), and then stirred and refluxed at 130° C. for 12 hours. When the reaction was completed, after removing the aqueous layer, 38 g (64%) of intermediate Int-1 was obtained by column chromatography (hexane: DCM (20%)).

[0231] Synthesis Example 2: Synthesis of Intermediate Int-2

[0232] [Reaction Scheme 2]

[0233]

[0234] Under nitrogen conditions, intermediate Int-1 (50 g, 170.21 mmol), Pd2(dba)3 (7.79 g, 8.51 mmol), Cs2CO3 (110.91 g, 340.43 mmol) and PCy3.H.BF4 (6.27 g, 17.02 mmol) were placed in a round-bottom flask, dissolved in DMAc (550 ml), and then stirred and refluxed at 160°C for 12 hours. When the reaction was completed, excess distilled water was poured into it, and then stirred for 1 hour. The solid was filtered therefrom and then dissolved in MCB at high temperature. After removing moisture therefrom with MgSO4 and filtering the organic solvent with a silica gel pad, the filtrate obtained was stirred. The solid produced therein was filtered and dried in vacuo to obtain 26.9 g (62%) of intermediate Int-2.

[0235] Intermediates Int-3, Int-4, Int-5, Int-6, Int-7 and Int-8 were synthesized according to the same method as Synthesis Examples 1 and 2 except that 4-bromodibenzofuran was changed.

[0236]

[0237]

[0238] Synthesis Example 3: Synthesis of Intermediate Int-10

[0239] [Reaction Scheme 3]

[0240]

[0241] 2,4-dichloro-6-phenyl-1,3,5-triazine (36 g, 159.25 mmol), 1,1'-biphenyl-4-ylboronic acid pinacol ester (CAS No. 144432-80-4, 42.5 g, 151.67 mmol), K2CO3 (41.92 g, 303.33 mmol) and Pd(PPh3)4 (5.26 g, 4.55 mmol) were placed in a round-bottom flask, dissolved in THF (500 ml) and distilled water (200 ml), and then stirred and refluxed at 60°C for 12 hours. When the reaction was completed, after removing the water layer therefrom, the organic solvent was removed under reduced pressure to obtain a solid. The obtained solid was dissolved in MCB at high temperature. After removing moisture therefrom with MgSO4 and then filtering the organic solvent with a silica gel pad, the filtrate thus obtained was stirred. The solid produced was filtered and dried under vacuum to obtain 28 g (52%) of Intermediate Int-10.

[0242] Intermediates Int-11 and Int-12 were synthesized according to the same method as Synthesis Example 3 except that 2,4-dichloro-6-phenyl-1,3,5-triazine and 1,1′-biphenyl-4-ylboronic acid pinacol ester were changed.

[0243]

[0244] Synthesis Example 4: Synthesis of Compound 1-7

[0245] [Reaction Scheme 4]

[0246]

[0247] Under nitrogen, intermediate Int-2 (12 g, 46.7 mmol), intermediate Int-10 (17.6 g, 51.35 mmol) and NaH (3.17 g, 79.35 mmol) were placed in a round bottom flask, dissolved in 230 ml DMF, and then stirred at room temperature for 12 hours under reflux. When the reaction was complete, excess distilled water was poured into it and then stirred for 1 hour. The solid was filtered therefrom and then dissolved in MCB at high temperature. After removing moisture therefrom with MgSO4 and then filtering the organic solvent with a silica gel pad, the filtrate thus obtained was stirred. The solid produced therein was filtered and vacuum dried to obtain 23.7 g (90%) of compound 1-7.

[0248] The compounds in the following Table 1 were synthesized according to the same method as Synthesis Example 4 except that the intermediates Int-2 and Int-10 were changed.

[0249] (Table 1)

[0250]

[0251]

[0252] Comparative Synthesis Example 1: Synthesis of Compound H-1

[0253] (1) Synthesis of intermediate Int-13

[0254] [Reaction Scheme 5]

[0255]

[0256] Under nitrogen, 9H-carbazole-3-boronic acid pinacol ester (20 g, 68.22 mmol), 2-bromodibenzothiophene (17.87 g, 68.22 mmol), K2CO3 (18.86 g, 136.44 mmol) and Pd(PPh3)4 (3.94 g, 3.41 mmol) were placed in a round-bottom flask, dissolved in THF (230 ml) and distilled water (80 ml), and then stirred and refluxed at 60°C for 12 hours. When the reaction was completed, after removing the water layer therefrom, the organic solvent was removed under reduced pressure therefrom, thereby obtaining a solid. The obtained solid was dissolved in MCB at high temperature. After removing moisture therefrom with MgSO4 and then filtering the organic solvent with a silica gel pad, the filtrate thus obtained was stirred. The solid produced therein was filtered and vacuum dried, thereby obtaining 14.77 g (62%) of intermediate Int-13.

[0257] (2) Synthesis of Compound H-1

[0258] [Reaction Scheme 6]

[0259]

[0260] Under nitrogen conditions, intermediate Int-13 (14.77 g, 42.31 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (16.38 g, 42.31 mmol), NaOtBu (5.03 g, 50.77 mmol), Pd2(dba)3 (2.32 g, 2.54 mmol) and P(t-Bu)3 (1.03 ml, 4.23 mmol) were placed in a round-bottom flask, dissolved in xylene (150 ml), and then stirred and refluxed at 120°C for 12 hours. When the reaction was completed, an excess of distilled water was poured therein, followed by stirring for 1 hour. The solid was filtered and then dissolved in MCB at high temperature. After removing moisture therefrom with MgSO4 and then filtering the organic solvent with a silica gel pad, the filtrate obtained was stirred. The solid produced therein was filtered and vacuum dried to obtain 20 g (72%) of compound H-1.

[0261] (Preparation of Second Compound)

[0262] Synthesis Example 19: Synthesis of Compound 2-99

[0263]

[0264] Compound 2-99 was synthesized with reference to the known method according to KR 10-1773363 B1.

[0265] Synthesis Example 20: Synthesis of Compound 2-137

[0266]

[0267] Compound 2-137 was synthesized with reference to the known method according to KR 10-1773363 B1.

[0268] Synthesis Example 21: Synthesis of Compound 2-136

[0269]

[0270] Compound 2-136 was synthesized with reference to the known method according to KR 10-1773363 B1.

[0271] (Preparation of the Third Compound)

[0272] Synthesis Example 22: Synthesis of Compound 3-13

[0273]

[0274] Compound 3-13 was synthesized with reference to the known method according to KR 10-1848885 B1.

[0275] Comparative Synthesis Example 2: Synthesis of Compound A-1

[0276] [A-1]

[0277]

[0278] The compound was synthesized with reference to the method known from KR 10-0573137 B1.

[0279] (Preparation of the Fourth Compound)

[0280] Synthesis Example 23: Synthesis of Compound 4-18

[0281]

[0282] Compound 4-18 was synthesized with reference to the known method according to KR 10-1772371 B1.

[0283] Comparative Synthesis Example 3: Synthesis of Compound P-1

[0284]

[0285] Compound P-1 was synthesized with reference to the known method according to KR 10-1476231 B1.

[0286] (Manufacturing of organic light-emitting diodes)

[0287] Example 1

[0288] A glass substrate coated with an indium tin oxide (ITO) thin film was cleaned with distilled water and ultrasonic waves. After cleaning with distilled water, the glass substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned for 10 minutes by using oxygen plasma, and moved to a vacuum depositor. The resulting ITO transparent electrode was used as an anode, and compound 3-13 doped with 1% NDP-9 (commercially available from Novaled) obtained in Synthesis Example 22 was vacuum deposited on the ITO substrate to form A thick hole transport layer was formed, and the compound 4-18 obtained in Synthesis Example 23 was deposited on the hole transport layer to form On the hole transport auxiliary layer, the compound 1-13 obtained in Synthesis Example 11 and the compound 2-137 obtained in Synthesis Example 20 were used as the host at the same time, and 15 wt % of PtGD was doped as a dopant to form a hole transport auxiliary layer by vacuum deposition. In this article, compound 1-13 and compound 2-137 are used in a weight ratio of 3:7. Then, compound C is deposited on the light-emitting layer to form Thick electron transport auxiliary layer, and compound D and Liq are vacuum deposited at a weight ratio of 1:1 to form Thick electron transport layer. LiQ and Al is sequentially vacuum deposited on the electron transport layer to form a cathode, thereby producing an organic light emitting diode.

[0289] ITO / compound 3-13 (1% NDP-9 doping, ) / Compound 4-18 [Compound 1-13: Compound 2-137: PtGD = 3: 7: 15 wt %] / Compound C / Compound D:LiQ

[0290] Compound C: 2-(3-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine

[0291] Compound D: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazine-2-yl)phenyl)quinolone

[0292] [PtGD]

[0293]

[0294] Examples 2 and 3 and Comparative Examples 1 to 3

[0295] By selectively changing the first compound, the second compound, the third compound and the dopant as shown in Tables 2 and 3, diodes according to Examples 2 and 3 and Comparative Examples 1 to 3 were produced in the same manner as in Example 1.

[0296] [PhGD]

[0297]

[0298] Example 4 and Comparative Example 4

[0299] Diodes according to Example 4 and Comparative Example 4 were produced in the same manner as in Example 1, except that the first compound, the second compound, and the dopant were changed as shown in Table 4 and the first compound and the second compound were mixed at a weight ratio of 4:6.

[0300] evaluate

[0301] The driving voltage and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 4 and Comparative Examples 1 to 4 were evaluated. The specific measurement method is as follows, and the results are shown in Tables 2 to 4.

[0302] (1) Measuring the change in current density based on the change in voltage

[0303] While increasing the voltage from 0 V to 10 V using a current-voltage meter (Keithley 2400), the current value flowing through the unit device in the obtained organic light emitting diode was measured, and the measured current value was divided by the area to provide a result.

[0304] (2) Measuring brightness changes based on voltage changes

[0305] While the voltage of the organic light emitting diode was increased from 0 V to 10 V, the luminance was measured using a photometer (Minolta Cs-1000A).

[0306] (3) Lifespan measurement

[0307] The T95 lifetime of the produced OLEDs was measured as the ratio of their brightness relative to the initial brightness (cd / m 2 ) drops to 95% of the time, with 24,000cd / m 2 As the initial brightness (cd / m 2 ) and measured their brightness reduction over time using the Polanonix lifetime measurement system.

[0308] (4) Measurement of driving voltage

[0309] An amperovoltmeter (Keithley 2400) was used at 15 mA / cm 2 Measure the drive voltage of each diode.

[0310] (5) Calculation of Driving Voltage Ratio (%)

[0311] In Table 2, the evaluation was performed based on the driving voltage of Comparative Example 1.

[0312] In Table 3, the evaluation was performed based on the driving voltage of Comparative Example 2.

[0313] (6) Calculation of T95 Life-span Ratio (%)

[0314] In Table 2, the evaluation was performed based on the T95 life of Comparative Example 1.

[0315] In Table 4, the evaluation was performed based on the T95 life of Comparative Example 4.

[0316] (Table 2)

[0317]

[0318] (Table 3)

[0319]

[0320] (Table 4)

[0321]

[0322] Referring to Tables 2 to 4, it is confirmed that the organic light emitting diodes according to Examples 1 to 4 show improved driving voltage and lifespan characteristics compared to the organic light emitting diodes according to Comparative Examples 1 to 4.

[0323] The combination of compound derivatives according to the present invention can control the characteristics of the hole transport auxiliary layer and the light-emitting layer in the organic light-emitting diode, thereby creating a balance between holes and electrons in the organic light-emitting diode in the light-emitting layer and showing excellent performance in driving voltage and / or life characteristics.

[0324] While the invention has been described in connection with what is presently considered to be practical embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but on the contrary, the invention 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 face 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, in, The light emitting layer includes a first compound represented by a combination of Chemical Formula 1 and Chemical Formula 2 and a second compound represented by Chemical Formula 3, and The hole transport layer includes a third compound represented by Chemical Formula 4, and The hole transport auxiliary layer includes a fourth compound represented by Chemical Formula 5: Wherein, in Chemical Formula 1 and Chemical Formula 2, L 1 To L 3 are each independently a single bond or a substituted or unsubstituted phenylene group, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, X 1 is O or S, Adjacent two of a1* to a4* in Chemical Formula 1 are connecting carbon atoms connected at * in Chemical Formula 2, The remaining two of a1* to a4* in Chemical Formula 1 that are not connected at * in Chemical Formula 2 are each independently CR a , R a is hydrogen or deuterium, and R 1 To R 8 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl; [Chemical formula 3] Wherein, in Chemical Formula 3, Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted dibenzofuranyl group, L 4 and L 5 are each independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, R b and R 9 To R 18 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and m is 0; [Chemical formula 4] Among them, in chemical formula 4, R 19 To R 25 are each independently hydrogen, deuterium or a substituted or unsubstituted C1 to C30 alkyl group, L 6 and L 7 are each independently a single bond, and Ar 5 To Ar 7 Each is independently a substituted or unsubstituted C6 to C30 aryl group; [Chemical formula 5] Among them, in chemical formula 5, Y 1 and Y 2 are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group, R 26 To R 32 are each independently hydrogen, deuterium or a substituted or unsubstituted C1 to C30 alkyl group, L 8 and L 9 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, Ar 8 and Ar 9 Each is independently a substituted or unsubstituted C6 to C30 aryl group, and "substituted" means that at least one hydrogen of the substituent is replaced by deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group or a cyano group.

2. The organic optoelectronic device according to claim 1, wherein: The first compound is represented by one of Chemical Formula 1A to Chemical Formula 1F: Wherein, in Chemical Formula 1A to Chemical Formula 1F, L 1 To L 3 ,Ar 1 ,Ar 2 , X 1 and R 1 To R 8 As defined in claim 1, and R a1 To R a4 Each independently of R in claim 1 a The same restrictions apply.

3. The organic optoelectronic device according to claim 1, wherein: Ar 1 and Ar 2 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

4. The organic optoelectronic device according to claim 1, wherein: *-L 2 -Ar 1 and *-L 3 -Ar 2 Substituents independently selected from Group I: [Group I] Where, in group I, * is the connection point.

5. The organic optoelectronic device according to claim 1, wherein: The first compound is selected from the group consisting of compounds of Group 1: [Group 1] 6. The organic optoelectronic device according to claim 1, wherein: The second compound is represented by Chemical Formula 3-8: [Chemical formula 3-8] Among them, in chemical formula 3-8, R 9 To R 18 are each independently hydrogen, or a substituted or unsubstituted C6 to C12 aryl group, and *-L 4 -Ar 3 and *-L 5 -Ar 4 are each independently one of the substituents of Group II, [Group II] Where, in Group II, * is the connection point.

7. The organic optoelectronic device according to claim 1, wherein: Ar 5 and Ar 6 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted bifluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted terphenyl group, or a combination thereof.

8. The organic optoelectronic device according to claim 1, wherein: *-L 6 -Ar 5 and *-L 7 -Ar 6 Substituents independently selected from Group III: [Group III] Where, in Group III, * is the connection point.

9. The organic optoelectronic device according to claim 1, wherein: The third compound is selected from the group consisting of compounds of Group 3: [Group 3] 10. The organic optoelectronic device according to claim 1, wherein: L 8 and L 9 Each is independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

11. The organic optoelectronic device according to claim 1, wherein: Ar 8 and Ar 9 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenylene group or a substituted or unsubstituted fluorenyl group.

12. The organic optoelectronic device according to claim 1, wherein: *-L 8 -Ar 8 and *-L 9 -Ar 9 Each substituent is independently selected from Group IV: [Group IV] Among them, in group IV, * is the connection point.

13. The organic optoelectronic device according to claim 1, wherein: The fourth compound is selected from the group consisting of compounds of Group 4: [Group 4] 14 . A display device comprising the organic optoelectronic device according to claim 1 .

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