Organic optoelectronic devices and display devices

Abstract

The present application provides an organic optoelectronic device and a display device. An organic optoelectronic device and a display device including the organic optoelectronic device are disclosed. The organic optoelectronic device includes an anode and a cathode opposite to each other, a light-emitting layer located between the anode and the cathode, a hole transport layer located between the anode and the light-emitting layer, and a hole transport auxiliary layer located between the light-emitting layer and the hole transport layer, wherein the light-emitting layer includes a composition comprising a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2, and the hole transport auxiliary layer includes a third compound represented by Chemical Formula 3. The detailed descriptions of Chemical Formulas 1 to 3 are the same as those described in the specification.

Description

[0001] Citations of Related Applications

[0002] This application claims the benefit of Korean Patent Application No. 10-2019-0121749 filed on October 1, 2019, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] An organic photoelectric device (organic optoelectronic device) and a display device are disclosed. Background Art

[0004] An organic photovoltaic device (organic photodiode) is a device that converts electrical energy into light energy (or vice versa).

[0005] According to their driving principles, organic optoelectronic devices can be classified as follows: one is a photoelectric device in which excitons generated by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes, respectively, and electric energy is generated, and the other is a light-emitting device that generates light energy from electric energy by supplying voltage or current to electrodes.

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

[0007] Among them, organic light emitting diodes (OLEDs) have recently attracted attention due to the increasing demand for flat panel displays. Organic light emitting diodes convert electrical energy into light by applying current to organic light emitting materials, and the performance of organic light emitting diodes may be affected by organic materials disposed between electrodes. Summary of the invention

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

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

[0010] According to one embodiment, an organic photoelectric device includes an anode and a cathode opposite to each other, a light-emitting layer located between the anode and the cathode, a hole transport layer located between the anode and the light-emitting layer, and a hole transport auxiliary layer located between the light-emitting layer and the hole transport layer, wherein the light-emitting layer includes a composition including a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2, and the hole transport auxiliary layer includes a third compound represented by Chemical Formula 3.

[0011]

[0012]

[0013] [Chemical formula 3]

[0014]

[0015] In Chemical Formulas 1 to 3,

[0016] L 1 To L 9 are 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,

[0017] R 1 To R 15 are independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C30 alkyl or substituted or unsubstituted C6 to C30 aryl, or a combination thereof,

[0018] n is an integer from 0 to 2,

[0019] Ar 1 To Ar 8 are independently substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group or a combination thereof,

[0020] Ar 1 and Ar 2 At least one of is a substituted or unsubstituted C10 to C30 aryl group or a substituted or unsubstituted C10 to C30 heterocyclic group, and

[0021] Ar 7 and Ar 8 At least one of is represented by Chemical Formula A1 or Chemical Formula A2,

[0022]

[0023] Wherein, in chemical formulas A1 and A2,

[0024] * is the connection point,

[0025] X is O or S, and

[0026] R a To R g and independently are hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl, or a combination thereof.

[0027] According to another embodiment, a display device including the organic photoelectric device is provided.

[0028] An organic photoelectric device with high efficiency and long life can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] Figure 1 is a schematic cross-sectional view of an organic photoelectric device according to one embodiment.

[0030] <Description of symbols>

[0031] 300: Organic light-emitting diode

[0032] 110: Anode

[0033] 120: cathode

[0034] 130: Luminous layer

[0035] 141: Hole transport layer

[0036] 142: Hole transport auxiliary layer

[0037] 105: Organic layer. DETAILED DESCRIPTION

[0038] 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.

[0039] 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.

[0040] In one example of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 heterocycloalkyl group, C6 to C30 aryl group or C2 to C30 heteroaryl group. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl group or C2 to C30 heteroaryl group. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl group, pyridyl group, quinolyl group, isoquinolyl group, dibenzofuranyl group, dibenzothienyl group or carbazolyl group. In addition, in the specific examples of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl group, dibenzofuranyl group or dibenzothienyl group. In addition, in the specific examples of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, naphthyl, triphenyl, dibenzofuranyl or dibenzothienyl.

[0041] In the present specification, when a definition is not otherwise provided, "hetero" means a group including 1 to 3 hetero atoms selected from N, O, S, P and Si in one functional group and the remainder being carbon.

[0042] In the present specification, "aryl group" refers to a group including at least one hydrocarbon aromatic part, and may include a group in which all elements of the hydrocarbon aromatic part have p-orbitals forming a conjugation, for example, phenyl, naphthyl, etc., a group in which two or more hydrocarbon aromatic parts can be linked by a σ bond, for example, biphenyl, terphenyl, quaterphenyl, etc., and a group in which two or more hydrocarbon aromatic parts are directly or indirectly fused to provide a non-aromatic fused ring, for example, fluorenyl, etc.

[0043] The aryl group may include monocyclic, polycyclic or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0044] In this specification, "heterocyclic group" is a general concept (superordinate concept) of heteroaryl, 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.

[0045] For example, "heteroaryl" refers to an aryl group including at least one heteroatom selected from N, O, S, P and Si. Two or more heteroaryls are directly connected by a sigma bond, or when the heteroaryl includes two or more rings, the two or more rings may be fused. When the heteroaryl is a fused ring, each ring may include 1 to 3 heteroatoms.

[0046] 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 pyrene 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 chrysenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof, but is not limited thereto.

[0047] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted furanyl, 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 The invention also includes substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, 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 dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or a combination thereof, but is not limited thereto.

[0048] 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.

[0049] 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.

[0050] Hereinafter, an organic photoelectric device according to one embodiment is described.

[0051] The organic photoelectric device (organic optoelectronic device) may be any device that converts electrical energy into light energy (or vice versa) without particular limitation, and may be, for example, an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.

[0052] Herein, an organic light emitting diode is exemplarily described as an example of an organic photoelectric device, but the present invention is not limited thereto and may be equally applicable to other organic photoelectric devices.

[0053] In the drawings, the thickness of layers, films, panels, regions, etc., is exaggerated for clarity. Like reference numerals denote like elements throughout the specification. 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.

[0054] Figure 1 is a schematic cross-sectional view of an organic photoelectric device according to one embodiment.

[0055] refer to Figure 1 The organic light emitting diode 300 according to the embodiment includes an anode 110 and a cathode 120 facing each other, and an organic layer 105 arranged 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 .

[0056] 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.

[0057] 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, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0058] 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.

[0059] The light emitting layer 130 may include a first compound having a relatively strong electron property and a second compound having a relatively strong hole property as a host, and the host may be a composition including the first compound and the second compound.

[0060] The hole transport auxiliary layer 142 may be disposed between the light emitting layer 130 and the hole transport layer 141 described later, and may contact the light emitting layer 130, thereby precisely controlling the mobility of holes at the interface between the light emitting layer 130 and the hole transport layer 141. The hole transport auxiliary layer 142 may include a third compound, and may include a plurality of layers.

[0061] The first compound is a compound having relatively strong electronic properties and may be represented by Chemical Formula 1.

[0062] [Chemical formula 1]

[0063]

[0064] In Chemical Formula 1,

[0065] L 1 To L 4 are 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,

[0066] R 1 To R 5 are independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof,

[0067] Ar 1 To Ar 3 are independently substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, or a combination thereof, and

[0068] Ar 1 and Ar 2 At least one of is a substituted or unsubstituted C10 to C30 aryl group or a substituted or unsubstituted C10 to C30 heterocyclic group.

[0069] The second compound may be a compound having a relatively strong hole property and may be represented by Chemical Formula 2.

[0070] [Chemical formula 2]

[0071]

[0072] In chemical formula 2,

[0073] L 5 and L 6 are 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,

[0074] R 6 To R 11 are independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof,

[0075] Ar 4 and Ar 5 are independently substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, or a combination thereof, and

[0076] n is one of integers from 0 to 2.

[0077] The third compound is a compound included in the hole transport auxiliary layer 142 to precisely control hole mobility of holes at an interface between the light emitting layer 130 and the hole transport layer 141 and may be represented by Chemical Formula 3.

[0078] [Chemical formula 3]

[0079]

[0080] In chemical formula 3,

[0081] L 7 To L 9 are 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,

[0082] R 12 To R 15 are independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof,

[0083] Ar 6 To Ar 8 are independently substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, or a combination thereof, and

[0084] Ar 7 and Ar 8 At least one of is represented by Chemical Formula A1 or Chemical Formula A2,

[0085]

[0086] Wherein, in chemical formulas A1 and A2,

[0087] * is the connection point,

[0088] X is O or S, and

[0089] R a To R g and independently are hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl, or a combination thereof.

[0090] The first compound has at least one substituted or unsubstituted C10 to C30 aryl group or substituted or unsubstituted C10 to C30 heterocyclic group as an additional substituent of the triazine substituted at the N position of the indolocarbazole group, thereby expanding the LUMO electron cloud and showing smooth electron injection and transport characteristics, which leads to the balance of holes and electrons in the molecule. In the case of applying it to an organic light emitting diode, the driving voltage of the diode can be reduced and the life characteristics can be improved due to the stability caused by the balance of holes and electrons.

[0091] In addition, the second compound is a compound having improved hole injection and transport properties and is used together with the first compound to achieve a proper charge balance between holes and electrons, thereby ensuring high efficiency, long life, and low-voltage driving characteristics of an organic light emitting diode including the second compound.

[0092] In addition, by applying a compound such as the third compound to the hole transport auxiliary layer, it is possible to prevent holes or electrons from accumulating at the interface between the hole transport layer and the light emitting layer and improve charge balance. Therefore, the driving voltage and lifespan characteristics of the organic photoelectric device can be greatly improved.

[0093] For example, in Formula 1, Ar 1 To Ar 3 may independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl, and

[0094] Ar 1 and Ar 2 At least one of the groups may be a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0095] In addition, Ar 3 It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0096] In addition, in Chemical Formula 1, L 1 To L 4 and may independently be a single bond or a substituted or unsubstituted phenylene group.

[0097] In addition, in Chemical Formula 1, R 1 To R 5 may independently be hydrogen or phenyl.

[0098] As a specific example, R 1 To R 5 One of them can be phenyl or all R 1 To R 5 It may be hydrogen.

[0099] For example, all R 1 To R 5 It may be hydrogen, but is not limited thereto.

[0100] The first compound may be, for example, one compound selected from the compounds of Group 1, but is not limited thereto.

[0101] [Group 1]

[0102]

[0103]

[0104] [A-31]

[0105]

[0106]

[0107] By including the second compound together with the first compound, the balance between holes and electrons can be improved and thus the driving or lifespan characteristics of a device including the compound can be greatly improved.

[0108] For example, in Formula 2, Ar 4 and Ar 5 The radicals may independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl or substituted or unsubstituted fluorenyl.

[0109] As a specific example, Chemical Formula 2 can be represented by Chemical Formula 2-1.

[0110] [Chemical formula 2-1]

[0111]

[0112] In chemical formula 2-1, Ar 4 ,Ar 5 , L 5 , L 6 and R 6 To R 11 Same as above.

[0113] In one embodiment, the second compound can be represented by Chemical Formula 2-1, where R 6 To R 11 May be all hydrogen, and *-L 5 -Ar 4 and *-L 6 -Ar 5and may independently be one of the substituents in Group I.

[0114] [Group I]

[0115]

[0116] In Group I, * is the connection point.

[0117] For example, Ar 4 and Ar 5 The groups may independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl or substituted or unsubstituted terphenyl.

[0118] In addition, L 5 and L 6 and may independently be a single bond or a substituted or unsubstituted phenylene group.

[0119] In addition, R 6 To R 11 May independently be hydrogen or C6 aryl.

[0120] The second compound may be, for example, one of compounds selected from the following Group 2, but is not limited thereto.

[0121] [Group 2]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127] 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 electron transporting ability of the first compound and the hole transporting ability of the second compound may be utilized to achieve bipolar properties by matching an appropriate weight ratio to improve efficiency and lifespan. Within this range, for example, they may be included in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20, about 20:80 to 70:30, about 20:80 to 60:40. For example, they may be included in a weight ratio of 30:70 to 50:50, for example, 30:70.

[0128] In addition to the above-mentioned host, the light-emitting layer may further include one or more compounds.

[0129] The light emitting layer may further comprise a dopant. 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.

[0130] The dopant is a material mixed with the above-mentioned host in a small amount to cause light emission, and the dopant is generally a material that emits light by multiple excitations to triplet or more, such as a metal complex. The dopant may be, for example, an inorganic, organic, or organic / inorganic compound, and one or more types thereof may be used.

[0131] 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.

[0132] [Chemical formula Z]

[0133] L 10 MX'

[0134] In the chemical formula Z, M is a metal, L is 10 and X' are the same or different and are ligands that form a complex with M.

[0135] 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 X' may be, for example, a bidentate ligand.

[0136] The hole transport auxiliary layer 142 may include the third compound.

[0137] The third compound may be a compound having a high HOMO energy level and may have excellent hole injection characteristics. Therefore, the third 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.

[0138] For example, the third compound may include a third compound represented by one of Chemical Formulas 3-1 to 3-3.

[0139]

[0140] [Chemical formula 3-3]

[0141]

[0142] In chemical formulae 3-1 to 3-3, X, R a To R g , R 12 To R 15 , L 7 To L 9 ,Ar 6 and Ar 7 Same as above.

[0143] As a specific example, in Chemical Formulae 3-1 to 3-3, Ar 6 may be substituted or unsubstituted phenyl or substituted or unsubstituted biphenyl, and Ar 7 It 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 phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group or a substituted or unsubstituted carbazolyl group.

[0144] As a more specific example, in Chemical Formulae 3-1 to 3-3, Ar 7 It may be one of the substituents selected from Group II.

[0145] [Group II]

[0146]

[0147] In Group II, * is the connection point.

[0148] In one embodiment, the third compound may be represented by Chemical Formula 3-1, and in this context, Ar 6 It can be phenyl, Ar 7 may be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl or substituted or unsubstituted terphenyl, R 12 To R 15 may be independently hydrogen or C6 to C12 aryl, R a To R g X may be hydrogen, and X may be O or S.

[0149] The third compound may be, for example, one of the compounds selected from Group 3, but is not limited thereto.

[0150] [Group 3]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161] In a more specific embodiment, the first compound may be represented by Chemical Formula 1, the second compound may be represented by Chemical Formula 2-1, and the third compound may be represented by Chemical Formula 3-1.

[0162] In this paper, Ar in Chemical Formula 1 1 To Ar 3 may independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl, and Ar 1 and Ar 2 At least one of the groups may be a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0163] L shown in chemical formula 2-1 5 and L 6 may independently be a single bond or a substituted or unsubstituted C6 to C12 arylene group,

[0164] Ar 4 and Ar 5 may independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl or substituted or unsubstituted terphenyl, and

[0165] R 6 To R 11 may independently be hydrogen or phenyl.

[0166] In chemical formula 3-1, Ar 6 It can be phenyl, Ar7 may be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl or substituted or unsubstituted terphenyl, L 7 and L 9 can be independently phenylene, R 12 To R 15 may be independently hydrogen or C6 to C12 aryl, R a To R g X may be hydrogen, and X may be O or S.

[0167] 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 constituting the anode 110 and the HOMO energy level of the material constituting the light emitting layer 130.

[0168] The hole transport layer 141 may include, for example, an amine derivative.

[0169] The hole transport layer 141 may include, for example, a compound represented by Chemical Formula 4, but is not limited thereto.

[0170] [Chemical formula 4]

[0171]

[0172] In chemical formula 4,

[0173] R 16 To R 22 are independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

[0174] R 16 and R 17 exist independently or bond to each other to form a ring,

[0175] R 18 and R 19 exist independently or bond to each other to form a ring,

[0176] R 20 To R 22 are independently substituted or unsubstituted C6 to C30 aryl or substituted or unsubstituted C2 to C30 heterocyclic, and

[0177] L 10 To L 13 and R is independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0178] For example, R 20 may be a substituted or unsubstituted C6 to C30 aryl group, and for example, R 20 It may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

[0179] For example, R 21 and R 22 The groups may independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted bisfluorene, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or a combination thereof.

[0180] The compound represented by Chemical Formula 4 may be, for example, one of the compounds of Group 4, but is not limited thereto.

[0181] [Group 4]

[0182]

[0183]

[0184] In addition to the above-mentioned light emitting layer 130, hole transport auxiliary layer 142 and hole transport layer 141, the organic layer 105 may further include a hole injection layer, an electron blocking layer, an electron transport layer, an electron injection layer and / or a hole blocking layer (not shown).

[0185] The organic light-emitting device 300 may be produced by forming an anode or a cathode on a substrate, forming an organic layer by dry film formation such as evaporation, sputtering, plasma plating, and ion plating or a solution method, and then forming a cathode or an anode thereon.

[0186] The organic optoelectronic device may be applied to a display device, for example, an organic light emitting diode may be applied to an organic light emitting diode (OLED) display.

[0187] Hereinafter, the embodiments are described in more detail with reference to Examples. However, these Examples are exemplary, and the scope of the present invention is not limited thereto.

[0188] (Synthesis of the Third Compound)

[0189] Synthesis Example 1: Synthesis of Compound C-1

[0190]

[0191] Referring to the method known in KR10-1931250B1, compound C-1 was synthesized.

[0192] LC quality M+H + =636.26

[0193] Synthesis Example 2: Synthesis of Compound C-2

[0194]

[0195] Referring to the method known in KR10-1931250B1, compound C-2 was synthesized.

[0196] LC quality M+H + =744.26

[0197] (Synthesis of the First Compound)

[0198] Synthesis Example 3: Synthesis of Intermediate M-1

[0199] [Reaction Scheme 1]

[0200]

[0201] 11,12-dihydroindole [2,3-a] carbazole (78.35 g, 305.69 mmol), bromobenzene (26.8 mL, 254.74 mmol), NaOt-Bu (26.93 g, 280.22 mmol) and Pd2(dba)3 (7 g, 7.64 mmol) were suspended in 1400 mL of toluene, and P(t-Bu)3 (3.64 mL, 15.28 mmol) was added thereto, followed by reflux and stirring for 12 hours. Subsequently, distilled water was added to the reaction solution to separate the mixture. The obtained product was purified by silica gel column to obtain intermediate M-1 (55.8 g, 55%). LC quality M+H + =333.13

[0202] Synthesis Example 4: Synthesis of Intermediate M-2

[0203] [Reaction Scheme 2]

[0204]

[0205] Intermediate M-2 (68.7 g, 57%) was obtained according to the same method as Synthesis Example 3 except that 11,12-dihydroindole[2,3-a]carbazole (78.35 g, 305.69 mmol) and 3-bromobiphenyl (59.38 g, 254.74 mmol) were used. LC mass M+H + =409.16

[0206] Synthesis Example 5: Synthesis of Intermediate M-3

[0207] [Reaction Scheme 3]

[0208]

[0209] 2,4-dichloro-6-phenyl-1,3,5-triazine (74.50 g, 329.56 mmol) and 4-biphenylboronic acid (55.47 g, 280.12 mmol) were dissolved in 0.7 L of a mixed solution of tetrahydrofuran (THF) and distilled water used in a ratio of 3:1, and tetrakis (triphenylphosphine) palladium (0) (11.48 g, 9.93 mmol) and potassium carbonate (68.65 g, 496.69 mmol) were added thereto, followed by reflux and stirring for 12 hours. The reaction solution was cooled to separate the layers, and the organic layer obtained therefrom was collected and concentrated. The concentrated residue was purified by a silica gel column to obtain intermediate M-3 (75.9 g, 67%). LC quality M+H + =344.09

[0210] Synthesis Example 6: Synthesis of Intermediate M-4

[0211] [Reaction Scheme 4]

[0212]

[0213] Intermediate M-4 (87.1 g, 74%) was obtained according to the same method as Synthesis Example 5, except that 2,4-dichloro-6-phenyl-1,3,5-triazine (74.50 g, 329.56 mmol) and 3-dibenzofuranylboronic acid (82.4 g, 280.12 mmol) were used.

[0214] LC quality M+H + =358.07

[0215] Synthesis Example 7: Synthesis of Intermediate M-5

[0216] [Reaction Scheme 5]

[0217]

[0218] According to the same method as Synthesis Example 5, except using 2,4-dichloro-6-biphenyl-1,3,5-triazine (74.50 g, 247.49 mmol) and 4-biphenylboronic acid (41.67 g, 210.37 mmol), Intermediate M-5 (71.6 g, 69%) was obtained.

[0219] LC quality M+H + =420.12

[0220] Synthesis Example 8: Synthesis of Compound A-1

[0221] [Reaction Scheme 6]

[0222]

[0223] Intermediate A-1 (62.4 g, 70%) was obtained according to the same method as Synthesis Example 3 except that Intermediate M-1 (46.3 g, 139.40 mmol) and Intermediate M-3 (47.8 g, 139.99 mmol) were used. LC mass M+H + =640.24

[0224] Comparative Synthesis Example 1: Synthesis of Compound R-5

[0225] [Reaction Scheme 7]

[0226]

[0227] Step 1: Synthesis of intermediate M-7

[0228] Intermediate M-7 (58.2 g, 58%) was obtained according to the same method as Synthesis Example 3 except that 5,12-dihydroindolo[3,2-a]carbazole (63 g, 246 mmol) and 3-bromobiphenyl (45.66 g, 196.81 mmol) were used.

[0229] LC quality M+H + =409.16

[0230] Step 2: Synthesis of compound R-5

[0231] Compound R-5 (48.1 g, 72%) was obtained according to the same method as Synthesis Example 3, except that Intermediate M-7 (43 g, 105.35 mmol) and 2-bromotriphenylene (32.24 g, 105.35 mmol) were used.

[0232] LC quality M+H + =635.24

[0233] Synthesis Examples 9 to 11 and Comparative Synthesis Example 2: Synthesis of Compounds A-21, A-32, A-3 and R-3

[0234] Each compound was obtained according to the same method as in Synthesis Example 8, except that Starting Materials 1 and 2 were used instead of M-1 (corresponding to Starting Material 1 in the following table) and M-3 (corresponding to Starting Material 2 in the following table), respectively.

[0235] [Table 1]

[0236]

[0237]

[0238] Comparative Synthesis Example 3: Synthesis of Compound R-1 Compound R-1 was synthesized in the same manner as known in KR10-1618683B1.

[0239]

[0240] Comparative Synthesis Example 4: Synthesis of Compound R-2

[0241] [Reaction Scheme 8]

[0242]

[0243] Step 1: Synthesis of intermediate M-6

[0244] Intermediate M-6 (27.6 g, 69%) was obtained according to the same method as Synthesis Example 5, except that 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole (33.57 g, 114.53 mmol) and 2-bromodibenzothiophene (30 g, 114.53 mmol) were used.

[0245] LC quality M+H + =350.09

[0246] Step 2: Synthesis of compound R-2

[0247] Compound R-2 (39.47 g, 84%) was obtained according to the same method as Synthesis Example 3 except that M-6 (25 g, 71.61 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (27.72 g, 71.61 mmol) were used. LC mass M+H + =657.20

[0248] Comparative Synthesis Example 5: Synthesis of Compound R-4

[0249]

[0250] Compound R-4 was synthesized in the same manner as known in KR10-1857632B1.

[0251] LC quality M+H + =658.19

[0252] (Synthesis of the Second Compound)

[0253] Synthesis Example 12: Synthesis of Compound B-99

[0254] Compound B-99 was synthesized in the same manner as known in KR10-1773363B1.

[0255] LC quality M+H + =561.23

[0256] Synthesis Example 13: Synthesis of Compound B-136

[0257] Compound B-136 was synthesized in the same manner as known in KR10-1773363B1.

[0258] LC quality M+H + =561.23

[0259] Synthesis Example 14: Synthesis of Compound B-139

[0260] Compound B-139 was synthesized in the same manner as known in KR10-1773363B1.

[0261] LC quality M+H + =637.26

[0262] (Production of organic light-emitting diodes)

[0263] Example 1

[0264] Clean the thickness with distilled water A glass substrate coated with ITO (indium tin oxide) is prepared. After cleaning with distilled water, the glass substrate is 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 obtained ITO transparent electrode is used as an anode, and N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazole-3-yl)biphenyl-4,4'-diamine (Compound A) is vacuum deposited on the ITO substrate to form - a thick hole injection layer, 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HATCN, compound B) is deposited on the injection layer to form a -thick, then N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine) (Compound C) was deposited as -thick to form a hole transport layer. Compound C-1 obtained in Synthesis Example 1 was vacuum deposited on the hole transport layer to form -thick hole transport auxiliary layer. Subsequently, using the compound A-1 obtained in Synthesis Example 8 and the compound B-99 obtained in Synthesis Example 12 as the host at the same time, and doped with 10 wt % of tris(4-methyl-2,5-diphenylpyridine)iridium(III) (compound D) as a dopant, a layer of 100 μm was formed on the hole transport auxiliary layer by vacuum evaporation. -thick light-emitting layer. Herein, compound A-1 and compound B-99 were used in a weight ratio of 3:7. Then, 8-(4-(4-(naphthalene-2-yl)-6-(naphthalene-3-yl)-1,3,5-triazine-2-yl)phenyl)quinoline (compound E) and Liq were simultaneously vacuum deposited on the light-emitting layer in a ratio of 1:1 to form -thick electron transport layer, and Liq and Al A cathode is sequentially formed by vacuum deposition on the electron transport layer, thereby producing an organic light emitting diode.

[0265] The organic light emitting diode has a structure of six organic thin layers, specifically, ITO / A / B / C / Hole transport auxiliary layer [C-1 ] / EML[A-1:B-99:D=3:7:10%] / E:Liq / Liq / Al

[0266] Example 2

[0267] An organic light emitting diode was produced according to the same method as in Example 1, except that Compound C-2 of Synthesis Example 2 was used instead of Compound C-1 to form a hole transport auxiliary layer.

[0268] Example 3

[0269] An organic light emitting diode was produced according to the same method as in Example 1, except that the compound B-136 of Synthesis Example 13 was used instead of the compound B-99 to form the light emitting layer.

[0270] Example 4

[0271] An organic light emitting diode was produced according to the same method as in Example 1, except that Compound A-21 of Synthesis Example 9 was used instead of Compound A-1 and Compound B-136 of Synthesis Example 13 was used instead of Compound B-99 to form a light emitting layer.

[0272] Example 5

[0273] An organic light emitting diode was produced according to the same method as in Example 1, except that Compound A-32 of Synthesis Example 10 was used instead of Compound A-1 to form a light emitting layer.

[0274] Example 6

[0275] An organic light emitting diode was produced according to the same method as in Example 1, except that Compound A-21 of Synthesis Example 9 was used instead of Compound A-1 to form a light emitting layer.

[0276] Comparative Example 1

[0277] An organic light emitting diode was produced according to the same method as in Example 1, except that the compound R-1 of Comparative Synthesis Example 3 was used instead of the compound A-1 to form the light emitting layer.

[0278] Comparative Example 2

[0279] An organic light emitting diode was produced according to the same method as in Example 1, except that the compound R-2 of Comparative Synthesis Example 4 was used instead of the compound A-1 and the compound B-136 of Synthesis Example 13 was used instead of the compound B-99 to form the light emitting layer.

[0280] Comparative Example 3

[0281] An organic light emitting diode was produced according to the same method as in Example 1, except that the compound R-4 of Comparative Synthesis Example 5 was used instead of the compound A-1 to form the light emitting layer.

[0282] Comparative Example 4

[0283] An organic light emitting diode was produced according to the same method as in Example 1, except that the compound R-5 of Comparative Synthesis Example 1 was used instead of the compound C-1 to form the hole transport auxiliary layer.

[0284] Example 7 and Comparative Example 5

[0285] The organic light emitting diodes of Example 7 and Comparative Example 5 were produced according to the same method as Example 1, except that the host was changed as shown in Table 4.

[0286] Evaluation: Effects of improving driving voltage and lifespan

[0287] The driving voltage and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 7 and Comparative Examples 1 to 5 were evaluated. The specific measurement method is as follows, and the results are shown in Tables 2 to 4.

[0288] (1) Lifespan measurement

[0289] The T90 lifetimes of the organic light emitting diodes according to Examples 1 to 5 and 7 and Comparative Examples 1, 2 and 5 were measured as follows: their luminance relative to the initial luminance (cd / m 2 ) drops to 90% 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.

[0290] (2) Calculation of T90 life ratio (%)

[0291] The relative T90(h) lifespans of other examples and comparative examples relative to the T90 lifespans of Examples 1 and 7 are provided in Table 2 or 4.

[0292] T90 life ratio (%) = {(T90 (h) of the comparative example and other examples) / (T90 (h) of Example 1 or 7)} × 100

[0293] (3) Measurement of driving voltage

[0294] The voltammeter (Keithley 2400) was used to measure the 2 Measure the driving voltage of the organic light emitting diode.

[0295] (4) Calculation of driving voltage ratio (%)

[0296] Table 3 shows the relative drive voltages of Comparative Examples 3 and 4 relative to the drive voltage of Example 6.

[0297] Driving voltage ratio (%) = {(driving voltage of Comparative Examples 3 and 4) (V) / (driving voltage of Example 6) (V)} × 100

[0298] [Table 2]

[0299]

[0300] [Table 3]

[0301]

[0302] [Table 4]

[0303]

[0304] Referring to Tables 2 to 4, the driving voltage of the compound for an organic photoelectric device according to the present invention is decreased, and the lifespan characteristics of the compound for an organic photoelectric device according to the present invention are improved, compared with those of the organic photoelectric device of the comparative example.

[0305] While the invention has been described in connection with what are presently considered to be practical exemplary 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 are opposite to each other. a light-emitting layer located between the anode and the cathode, a hole transport layer located between the anode and the light-emitting layer, and a hole transport auxiliary layer located between the light emitting layer and the hole transport layer, wherein the light-emitting layer comprises a composition comprising a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2, and The hole transport auxiliary layer includes a third compound represented by Chemical Formula 3: Wherein, in Chemical Formulas 1 and 2, L 1 To L 6 are independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 1 To R 11 are independently hydrogen, deuterium or substituted or unsubstituted C6 to C12 aryl, n is an integer from 0 to 2, Ar 1 and Ar 2 are independently substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group or a combination thereof, Ar 1 and Ar 2 At least one of is a substituted or unsubstituted C10 to C30 aryl group or a substituted or unsubstituted C10 to C30 heterocyclic group, Ar 3 To Ar 5 are independently substituted or unsubstituted C6 to C30 aryl, [Chemical formula 3] Among them, in chemical formula 3, L 7 To L 9 are independently phenylene, R 12 To R 15 are independently hydrogen, deuterium or C6 to C12 aryl, Ar 6 is a substituted or unsubstituted phenyl group, Ar 7 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group or a substituted or unsubstituted terphenyl group, Ar 8 Represented by chemical formula A1, [Chemical formula A1] Wherein, in chemical formula A1, * is the connection point, X is O or S, R a To R c is hydrogen or deuterium, and "Substituted" means that at least one hydrogen of the substituent is replaced with deuterium, a C1 to C5 alkyl group, or a C6 to C18 aryl group.

2. The organic optoelectronic device according to claim 1, wherein Ar 1 and Ar 2 are independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl, Ar 1 and Ar 2At least one of is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group, and Ar 3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group or a substituted or unsubstituted terphenyl group.

3. The organic optoelectronic device according to claim 1, wherein Ar 4 and Ar 5 and wherein the at least one substituted or unsubstituted phenyl group is independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylene or substituted or unsubstituted fluorenyl.

4. The organic optoelectronic device according to claim 1, wherein Chemical Formula 2 is represented by Chemical Formula 2-1: [Chemical formula 2-1] in, In chemical formula 2-1, R 6 To R 11 As defined in claim 1, and *-L 5 -Ar 4 and *-L 6 -Ar 5 is independently one of the substituents of Group I, [Group I] Where, in group I, * is the connection point.

5. The organic photoelectric device according to claim 1, wherein the third compound is represented by Chemical Formula 3-1 or 3-2: in, In chemical formulas 3-1 and 3-2, X, R a To R c , R 12 To R 15 , L 7 To L 9 ,Ar 6 and Ar 7 Same as defined in claim 1.

6. The organic optoelectronic device according to claim 1, wherein Ar 7 is one of the substituents of Group II: [Group II] in, In Group II, * is the connection point.

7. The organic optoelectronic device according to claim 1, wherein The second compound is represented by Chemical Formula 2-1, and The third compound is represented by Chemical Formula 3-1: [Chemical formula 2-1] in, In chemical formula 2-1, L 5 and L 6 is independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, Ar 4 and Ar 5 are independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl or substituted or unsubstituted terphenyl, and R 6 To R 11 are independently hydrogen or phenyl; [Chemical formula 3-1] Among them, in chemical formula 3-1, Ar 6 It is phenyl. Ar 7 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group or a substituted or unsubstituted terphenyl group, L 7 To L 9 are independently phenylene, R 12 To R 15 are independently hydrogen or C6 to C12 aryl, R a To R c is hydrogen, and X is O or S.

8. The organic optoelectronic device according to claim 7, wherein Ar in Formula 1 1 and Ar 2 are independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothienyl, Ar in Formula 1 3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group or a substituted or unsubstituted terphenyl group, Among them, Ar 1 and Ar 2 At least one of the groups is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

9. The organic optoelectronic device according to claim 1, wherein The light emitting layer further includes a dopant. 10 . A display device comprising the organic optoelectronic device according to claim 1 .

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