Organic optoelectronic device and display device

Abstract

An organic optoelectronic device includes a positive electrode and a negative electrode facing each other, a light emitting layer between the positive electrode and the negative electrode, a hole transport layer between the positive electrode and the light emitting layer, and a hole transport auxiliary layer between the light emitting layer and the hole transport layer, the light emitting layer includes a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2 or a combination of Chemical Formula 3 and Chemical Formula 4, and the hole transport auxiliary layer includes a third compound represented by Chemical Formula 5. Details of Chemical Formulae 1 to 5 are as defined in the specification.

Description

Technical Field

[0001] An organic optoelectronic device and a display device are disclosed. Background Art

[0002] Organic optoelectronic devices (organic optoelectronic diodes) are devices that are able to convert electrical energy and light energy into one another.

[0003] Organic optoelectronic 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.

[0004] Examples of the organic optoelectronic device include an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.

[0005] 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

[0006] Technical issues

[0007] One embodiment provides an organic optoelectronic device capable of achieving long life characteristics.

[0008] Another embodiment provides a display device including the organic optoelectronic device.

[0009] Technical Solution

[0010] According to one embodiment, an organic optoelectronic device includes an anode and a cathode facing each other, a light-emitting layer between the anode and the cathode, 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 composition including a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2 or a combination of Chemical Formula 3 and Chemical Formula 4, and the hole transport auxiliary layer includes a third compound represented by Chemical Formula 5.

[0011] [Chemical formula 1]

[0012]

[0013] In Chemical Formula 1,

[0014] Ar 1 To Ar 3are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0015] L 1 To L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0016] R 1 To R 3 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,

[0017] m1 and m3 are each independently one of integers from 1 to 4, and

[0018] m2 is an integer of 1 or 2;

[0019] [Chemical formula 2]

[0020]

[0021] In chemical formula 2,

[0022] Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0023] Ar 10 To Ar 13 are each independently hydrogen or a substituted or unsubstituted C6 to C30 aryl group,

[0024] L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0025] R 4 To R 8 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,

[0026] m4, m7 and m8 are each independently one of integers from 1 to 4,

[0027] m5 and m6 are each independently one of integers from 1 to 3, and

[0028] n is an integer from 0 to 2;

[0029]

[0030] In Chemical Formula 3 and Chemical Formula 4,

[0031] Ar 6 and Ar 7 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0032] a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or CL a -R a ,

[0033] Among a1* to a4* in Chemical Formula 3, two adjacent ones are each connected to * in Chemical Formula 4, L a , L 7 and L 8 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0034] R a , R 9 and R 10 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

[0035] m9 and m10 are each independently an integer from 1 to 4;

[0036] [Chemical formula 5]

[0037]

[0038] In Chemical Formula 5,

[0039] X 1 is C or Si,

[0040] R 11 To R 14 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,

[0041] R 15 and R 16 are each independently a substituted or unsubstituted C1 to C30 alkyl group or a substituted or unsubstituted C6 to C30 aryl group,

[0042] Ar 8 is a substituted or unsubstituted C6 to C30 aryl group,

[0043] Ar 9is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted dibenzothioyl group,

[0044] L 9 To L 11 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, m11, m12 and m14 are each independently an integer from 1 to 4, and

[0045] m13 is an integer between 1 and 3.

[0046] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0047] Beneficial Effects

[0048] An organic optoelectronic device having a long lifespan characteristic can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0049] Figure 1 is a cross-sectional view showing an organic light emitting diode according to one embodiment.

[0050] <Description of Reference Numerals>

[0051] 10: Anode 20: Cathode

[0052] 30: Organic layer 31: Hole transport layer

[0053] 32: Light-emitting layer 33: Hole transport auxiliary layer

[0054] 34: Electron transport layer DETAILED DESCRIPTION

[0055] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, and the present disclosure is not limited thereto.

[0056] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by 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.

[0057] In the present specification, "unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom remains.

[0058] In the present specification, "deuterium substitution (-D)" may include "tritium substitution (-T)".

[0059] In one example of the present invention, "substituted" means that at least one hydrogen of a substituent or 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 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 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 compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl or naphthyl.

[0060] In the present specification, when a definition is not otherwise provided, "hetero" means including one to three hetero atoms selected from N, O, S, P and Si and the remaining carbon in one functional group.

[0061] 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, such as phenyl, naphthyl, etc., two or more hydrocarbon aromatic portions may be connected by a σ bond and 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, such as fluorenyl.

[0062] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0063] As used herein, "heterocyclic group" is a general concept of heteroaryl, and may include at least one heteroatom selected from N, O, S, P and Si in place of carbon (C) in a cyclic compound such as an aryl, a cycloalkyl, 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.

[0064] 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 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 one to three heteroatoms.

[0065] 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 tetraphenyl group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted para-terphenyl group, a substituted or unsubstituted meta-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted peryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof, but is not limited thereto.

[0066] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted furyl, 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, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazoline, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted benzoxazinyl, a substituted or unsubstituted benzothiazinyl, a substituted or unsubstituted acridinyl, a substituted or unsubstituted phenazinyl, a substituted or unsubstituted phenothiazinyl, a substituted or unsubstituted phenoxazinyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof, but not limited thereto.

[0067] As used herein, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0068] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to conductive properties according to the lowest unoccupied molecular orbital (LUMO) energy level.

[0069] An organic optoelectronic device according to one embodiment of the present invention is described below.

[0070] The organic optoelectronic device may be a suitable device that converts electrical energy into light energy and vice versa, such as an organic photovoltaic device, an organic light emitting diode, an organic solar cell, or an organic photosensitive drum.

[0071] Herein, an organic light emitting diode is described as an example of an organic optoelectronic device, but the present invention is not limited thereto and may be applied to other organic optoelectronic devices in the same manner.

[0072] In the accompanying drawings, the thickness of layers, films, panels, regions, etc., is exaggerated for clarity. Throughout the specification, the same reference numerals represent the same elements. It should 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 be intermediate elements. In contrast, when an element is referred to as being "directly on" another element, there are no intermediate elements.

[0073] Figure 1 is a schematic cross-sectional view of an organic optoelectronic device according to one embodiment.

[0074] Reference Figure 1 , an organic optoelectronic device according to one embodiment includes an anode 10 and a cathode 20 facing each other and an organic layer 30 between the anode 10 and the cathode 20 .

[0075] The anode 10 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 10 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or the like; 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.

[0076] The cathode 20 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 20 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.

[0077] The organic layer 30 includes a hole transport layer 31 , a light emitting layer 32 , and a hole transport auxiliary layer 33 between the hole transport layer 31 and the light emitting layer 32 .

[0078] The hole transport layer 31 is a layer for promoting the transfer of holes from the anode 10 to the light emitting layer 32 , and may include, for example, an amine compound, but is not limited thereto.

[0079] The amine compound may include, for example, at least one aryl group and / or heteroaryl group. The amine compound may be represented by, for example, Chemical Formula a or Chemical Formula b, but is not limited thereto.

[0080]

[0081] In chemical formula a or b,

[0082] Ar a To Ar g are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl, or a combination thereof,

[0083] Ar a To Ar c At least one of Ar d To Ar g At least one of is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and

[0084] Ar h is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof.

[0085] The light emitting layer 32 includes at least two types of hosts and dopants. The hosts include a first compound having bipolar characteristics in which electron characteristics are relatively strong and a second compound having bipolar characteristics in which hole characteristics are relatively strong.

[0086] The first compound may be represented by Chemical Formula 1.

[0087] [Chemical formula 1]

[0088]

[0089] In Chemical Formula 1,

[0090] Ar 1 To Ar 3 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0091] L 1 To L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0092] R 1 To R 3 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,

[0093] m1 and m3 are each independently one of integers from 1 to 4, and

[0094] m2 is an integer of 1 or 2.

[0095] The first compound has at least one substituted or unsubstituted C10 to C30 aryl group or a substituted or unsubstituted C10 to C30 heterocyclic group as an additional substituent of the triazine substituted at the N position of the indolocarbazolyl group, and thereby expands the LUMO electron cloud and exhibits smooth electron injection and transport characteristics, which leads to a balance of holes and electrons in the molecule. In the case of an organic light-emitting diode to which such a compound is applied, the driving voltage of the diode can be reduced, and the life characteristics can be improved due to the stability brought about by the balance of holes and electrons.

[0096] For example, in Formula 1, Ar 1 To Ar 3 may each independently 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, and

[0097] Ar 2 and Ar 3 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.

[0098] The first compound may be, for example, one of the compounds selected from Group 1, but is not limited thereto.

[0099] [Group 1]

[0100]

[0101]

[0102]

[0103] The first compound may be used each type alone or as a mixture of two or more types.

[0104] The second compound may be used together with the first compound in the light emitting layer to increase charge mobility and stability, thereby improving light emitting efficiency and lifespan characteristics.

[0105] The second compound may be represented by Chemical Formula 2, for example.

[0106] [Chemical formula 2]

[0107]

[0108] In chemical formula 2,

[0109] Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0110] Ar 10 To Ar 13 are each independently hydrogen or a substituted or unsubstituted C6 to C30 aryl group,

[0111] L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0112] R 4 To R 8 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,

[0113] m4, m7 and m8 are each independently one of integers from 1 to 4,

[0114] m5 and m6 are each independently one of integers from 1 to 3, and

[0115] n is one of integers from 0 to 2.

[0116] When R 4 When the value is 2 or greater, each R 4 May be the same as or different from each other.

[0117] When R 5 When the value is 2 or greater, each R 5 May be the same as or different from each other.

[0118] When R 6 When the value is 2 or greater, each R 6 May be the same as or different from each other.

[0119] When R 7 When the value is 2 or greater, each R 7 May be the same as or different from each other.

[0120] For example, Ar in Formula 24 and Ar 5 may be each independently 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 triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted fluorenyl group,

[0121] L in Formula 2 5 and L 6 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,

[0122] R in Formula 2 4 To R 8 may each independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, and

[0123] n can be 0 or 1.

[0124] For example, Ar in Formula 1 10 To Ar 13 Each may independently be hydrogen or a substituted or unsubstituted C6 to C12 aryl group.

[0125] For example, Ar in Formula 1 10 To Ar 13 Each independently may be hydrogen or substituted or unsubstituted phenyl.

[0126] For example, “substituted” in Chemical Formula 2 means that at least one hydrogen is substituted with deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0127] In a specific embodiment of the present invention, Chemical Formula 2 can be represented by one of Chemical Formulas 2-1 to 2-15.

[0128]

[0129]

[0130] In Chemical Formulae 2-1 to 2-15, R 4 To R 8 are each independently hydrogen, deuterium or substituted or unsubstituted C6 to C12 aryl, and *-L 5 -Ar 4 and *-L 6 -Ar 5 Each may independently be one of the substituents listed in Group II.

[0131] [Group II]

[0132]

[0133] In Group II,

[0134] D is deuterium,

[0135] m19 is an integer from 1 to 5,

[0136] m20 is an integer from 1 to 4,

[0137] m21 is an integer from 1 to 3,

[0138] m22 is an integer of 1 or 2, and

[0139] * is the connection point.

[0140] In one embodiment, Chemical Formula 2 may be represented by Chemical Formula 2-8.

[0141] In addition, *-L in Chemical Formula 2-8 5 -Ar 4 and *-L 6 -Ar 5 Each may be independently selected from Group II, such as C-1, C-2, C-3, C-4, C-7, C-8 and C-9.

[0142] The second compound may be represented by a combination of Chemical Formula 3 and Chemical Formula 4, for example.

[0143]

[0144]

[0145] In Chemical Formula 3 and Chemical Formula 4,

[0146] Ar 6 and Ar 7 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0147] a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or CL a -R a ,

[0148] Adjacent two of a1* to a4* in Chemical Formula 3 are each connected to * in Chemical Formula 4,

[0149] L a , L 7 and L 8 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0150] R a , R 9 and R 10 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

[0151] m9 and m10 are each independently one of integers from 1 to 4.

[0152] For example, the second compound represented by the combination of Chemical Formula 3 and Chemical Formula 4 may be represented by any one of Chemical Formula 3A, Chemical Formula 3B, Chemical Formula 3C, Chemical Formula 3D, and Chemical Formula 3E.

[0153]

[0154]

[0155] In Chemical Formulae 3A to 3E, Ar 6 ,Ar 7 , L 7 , L 8 , R 9 and R 10 Same as above,

[0156] L a1 To L a4 With L 7 and L 8 The definition of is the same as

[0157] R a1 To R a4 With R 9 and R 10 The definition is the same.

[0158] For example, Ar in Formulas 3 and 4 6 and Ar 7 may be each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group,

[0159] R a1 To R a4 , R 9 and R 10 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.

[0160] In a specific embodiment of the present invention, Ar in Chemical Formulas 3 and 4 6 and Ar 7 The substituents listed in Group II may be each independently selected.

[0161] In one embodiment, R a1 To R a4 , R 9 and R 10 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.

[0162] For example, R a1 To R a4 , R 9 and R 10 may each independently be hydrogen, deuterium, cyano or substituted or unsubstituted phenyl, and

[0163] In a specific embodiment, R a1 To R a4 , R 9 and R 10 can each independently be hydrogen, deuterium or phenyl.

[0164] In a specific embodiment of the present invention, the second compound can be represented by Chemical Formula 2-8, wherein in Chemical Formula 2-8, Ar 4 and Ar 5 may be each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group, L 5 and L 6 may each independently be a single bond or a substituted or unsubstituted C6 to C20 arylene group, and R 4 To R 8 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.

[0165] In another specific embodiment of the present invention, the second compound can be represented by Chemical Formula 3C, wherein in Chemical Formula 3C, L a3 and L a4 Can be a single bond, L 7 and L 8may be each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, R 9 , R 10 , R a3 and R a4 may each be hydrogen, deuterium or phenyl, and Ar 6 and Ar 7 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0166] For example, the second compound may be one of the compounds selected from Group 2, but is not limited thereto.

[0167] [Group 2]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182] One type or two or more types of the second compound may be used.

[0183] In the light-emitting layer 32, the first compound and the second compound may be included as the main body, and the first compound and the second compound may be included in a weight ratio of, for example, about 1:99 to 99:1. Within the above range, bipolar characteristics may be achieved by matching an appropriate weight ratio using the electron transport capability of the first compound and the hole transport capability of the second compound 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 (e.g., about 20:80 to about 70:30, about 20:80 to about 60:40, and about 20:80 to about 50:50). As a specific example, they may be included in a weight ratio of about 20:80, 30:70, or 40:60.

[0184] The light emitting layer 32 may further include one or more compounds other than the above-mentioned first compound and second compound as a host.

[0185] The light emitting layer 32 may further contain a dopant.

[0186] The dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and may be, for example, a red or green phosphorescent dopant.

[0187] A dopant is a material mixed in a small amount with a compound used for an organic optoelectronic device to cause light emission, and may generally be a material such as a metal complex that emits light by multiple excitations to a triplet state or higher. The dopant may be, for example, an inorganic, organic, or organic / inorganic compound, and one or more types thereof may be used.

[0188] 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.

[0189] [Chemical formula Z]

[0190] L 9 MX 2

[0191] In the chemical formula Z, M is a metal and L 9 and X 2 are the same or different and are ligands for forming a complex with M.

[0192] 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 9 and X2 This may be, for example, a bidentate ligand.

[0193] By L 9 and X 2 Examples of the ligand represented by may be selected from the chemical formulae listed in Group A, but are not limited thereto.

[0194] [Group A]

[0195]

[0196] In Group A,

[0197] R 300 To R 302 are each independently hydrogen, deuterium, C1 to C30 alkyl which may be substituted by halogen, C6 to C30 aryl which may be substituted by C1 to C30 alkyl, or halogen, and

[0198] R 303 To R 324 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

[0199] As an example, it may include a dopant represented by Chemical Formula V.

[0200] [Chemical Formula V]

[0201]

[0202] In chemical formula V,

[0203] R 101 To R 116 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0204] R 132 To R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0205] R 101 To R 116 At least one of them is a functional group represented by chemical formula V-1,

[0206] L 100 is a bidentate ligand for a monovalent anion and is coordinated to iridium via a lone electron pair of a carbon or heteroatom, and

[0207] n5 and n6 are each independently any one of integers from 0 to 3, and n5+n6 is any one of integers from 1 to 3,

[0208] [Chemical formula V-1]

[0209]

[0210] In chemical formula V-1,

[0211] R 135 To R 139 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0212] R 132 To R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group, and

[0213] * indicates a moiety attached to a carbon atom.

[0214] As an example, a dopant represented by Chemical Formula Z-1 may be included.

[0215] [Chemical formula Z-1]

[0216]

[0217] In the chemical formula Z-1, rings A, B, C and D independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0218] R A , R B , R C and R D independently represents mono-, di-, tri- or tetra-substituted or unsubstituted;

[0219] L B , L C and L D Each is independently selected from a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and combinations thereof;

[0220] When nA is 1, L E is selected from the group consisting of direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and combinations thereof; when nA is 0, L E does not exist; and

[0221] R A , R B , R C , R D R, R and R' are each independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino and combinations thereof; any adjacent R A , R B , R C , R D , R and R' are optionally linked to each other to provide a ring; X B , X C , X D and X E are each independently selected from carbon and nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 Each represents oxygen or a direct bond.

[0222] The dopant according to one embodiment may be a platinum complex, and may be represented, for example, by Chemical Formula VI.

[0223] [Chemical Formula VI]

[0224]

[0225] In Chemical Formula VI,

[0226] X 100 Selected from O, S and NR 131 ,

[0227] R 117 To R 131 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0228] R 132 To R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0229] R 117 To R 131 At least one of them is -SiR 132 R 133 R 134 or tert-butyl, and

[0230] R 132 To R 134 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0231] The hole transport auxiliary layer 33 includes a third compound having a bipolar characteristic with a relatively strong hole characteristic.

[0232] As described above, the light emitting layer 32 includes the first compound having bipolar characteristics in which electron characteristics are relatively strong and the second compound having relatively strong hole characteristics, thereby increasing the mobility of electrons and holes and significantly improving light emitting efficiency compared to individual compounds.

[0233] When a light-emitting layer is formed using a material having biased electron or hole characteristics, excitons are generated relatively more in a device including the light-emitting layer due to the recombination of carriers at the interface between the light-emitting layer and the electron or hole transport layer. Therefore, molecular excitons in the light-emitting layer interact with charges at the interface of the hole transport layer, and thus cause a roll-off of sharply degraded efficiency, and also sharply degrade the light-emitting lifetime characteristics.

[0234] In order to solve these problems, the first compound and the second compound are simultaneously included in the light-emitting layer so that the light-emitting region is not biased toward either the electron transport layer or the hole transport layer, and further, a hole transport auxiliary layer including the third compound is disposed between the hole transport layer and the light-emitting layer, thereby preventing charge accumulation at the interface between the hole transport layer and the light-emitting layer, and providing a device capable of adjusting the carrier balance in the light-emitting layer. Therefore, the roll-off characteristics of the organic optoelectronic device can be improved, and at the same time, the lifespan characteristics can be significantly improved.

[0235] The third compound may be a compound represented by Chemical Formula 5.

[0236] [Chemical formula 5]

[0237]

[0238] In Chemical Formula 5,

[0239] X 1 is C or Si,

[0240] R 11 To R14 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,

[0241] R 15 and R 16 are each independently a substituted or unsubstituted C1 to C30 alkyl group or a substituted or unsubstituted C6 to C30 aryl group,

[0242] Ar 8 is a substituted or unsubstituted C6 to C30 aryl group,

[0243] Ar 9 is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted dibenzothioyl group,

[0244] L 9 To L 11 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, m11, m12 and m14 are each independently an integer from 1 to 4, and

[0245] m13 is an integer between 1 and 3.

[0246] The third compound is an amine derivative including both a fluorenyl group substituted at the 9th position and a fluorenyl group (or a dibenzosilyl group) substituted in the direction of the phenyl group.

[0247] Due to the steric hindrance of the fluorenyl group substituted at the 9th position, the deposition temperature can be lowered, minimizing degradation and thus further improving the lifespan characteristics.

[0248] Furthermore, a fluorenyl group substituted in the phenyl direction or a dibenzosilyl group substituted in the phenyl direction is simultaneously included, and thus the HOMO level can be lowered and hole injection can be thereby facilitated.

[0249] When m11 is 2 or greater, each R 11 Can be the same or different.

[0250] When m12 is 2 or greater, each R 12 Can be the same or different.

[0251] When m13 is 2 or greater, each R 13 Can be the same or different.

[0252] When m14 is 2 or greater, each R 14 Can be the same or different.

[0253] For example, the third compound may be represented by any one of Chemical Formula 5-1 to Chemical Formula 5-4.

[0254]

[0255]

[0256] In Chemical Formula 5-1 to Chemical Formula 5-4,

[0257] X 1 , R 11 To R 16 ,Ar 8 ,Ar 9 , L 9 To L 11 , m11 to m14 are the same as above.

[0258] For example, the third compound may be represented by Chemical Formula 5-2.

[0259] For example, Ar in Formula 5 8 It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0260] As a specific example, Ar in Chemical Formula 5 8 It may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

[0261] For example, Ar in Formula 5 9 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 phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted dibenzosilyl group.

[0262] As a specific example, Ar in Chemical Formula 5 9 The substituents listed in Group III may be selected.

[0263] [Group III]

[0264]

[0265] In Group III, * is the connection point.

[0266] For example, the third compound may be one of the compounds selected from Group 3, but is not limited thereto.

[0267] [Group 3]

[0268]

[0269]

[0270] In the most specific embodiment of the present invention, the first compound may be the same as described above, the second compound may be represented by Chemical Formula 2-8, and the third compound may be represented by Chemical Formula 5-2.

[0271] In addition, the organic layer 30 may further include an electron transport region.

[0272] The electron transport region may further increase electron injection and / or electron mobility between cathode 20 and light emitting layer 32, but block holes.

[0273] Specifically, the electron transport region may include an electron transport layer 34 between the cathode 20 and the light-emitting layer 32 and an electron transport auxiliary layer between the light-emitting layer 32 and the electron transport layer 34, and at least one of the compounds listed in group B may be included in at least one layer of the electron transport layer and the electron transport auxiliary layer.

[0274] [Group B]

[0275]

[0276]

[0277]

[0278] Meanwhile, in addition to the light-emitting layer, the organic light-emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. as the above-mentioned organic layer.

[0279] The organic light emitting diode may be manufactured by forming an anode or a cathode on a substrate, forming an organic layer using a dry film method such as evaporation, sputtering, plasma plating, and ion plating, and then forming the cathode or the anode thereon.

[0280] The organic light emitting diode can be applied to an organic light emitting display device.

[0281] Mode for the Invention

[0282] Hereinafter, the embodiments are described in more detail with reference to examples. However, these examples are exemplary, and the scope of claims is not limited thereto.

[0283] Hereinafter, starting materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry or P&H Tech, or synthesized by known methods unless otherwise specified.

[0284] (Synthesis of Compounds)

[0285] As a more specific example of the compound of the present invention, the presented compound was synthesized by the following steps.

[0286] Synthesis of the first compound

[0287] Synthesis Example 1: Synthesis of Compound A-22

[0288] [Reaction formula 1]

[0289]

[0290] A-22 was synthesized using intermediate M-1 (CAS No. 1449754-80-6) and intermediate M-2 (CAS No. 1689576-03-1) with reference to the synthesis method disclosed in published patent application KR 10-2021-0039202.

[0291] Comparative Synthesis Example 1: Synthesis of Compound ET-1

[0292]

[0293] Compound ET-1 was synthesized by referring to the known synthesis method in the registered patent of KR 10-2275343.

[0294] Synthesis of the second compound

[0295] Synthesis Example 2: Synthesis of Compound B-136

[0296]

[0297] Compound B-136 was synthesized by referring to the synthesis method disclosed in registered patent US10476008 B2.

[0298] Synthesis of the third compound

[0299] Synthesis Example 3: Synthesis of Compound D-2

[0300] [Reaction 2]

[0301]

[0302] Compound D-2 was synthesized using Int-1 and Int-3 (CAS No. 1853122-02-7).

[0303] Synthesis Example 4: Synthesis of Compound D-30

[0304] [Reaction 3]

[0305]

[0306] Compound D-30 was synthesized using Int-4 (CAS No. 1154752-04-1) and Int-3 (CAS No. 1853122-02-7).

[0307] Comparative Synthesis Example 2: Synthesis of Compound R-1

[0308]

[0309] Compound R-1 was synthesized by referring to the synthesis method known in registered patent US10355217 B2.

[0310] Comparative Synthesis Example 3: Synthesis of Compound R-2

[0311]

[0312] Compound R-2 was synthesized by referring to the method known in registered patent KR 10-1931250.

[0313] Comparative Synthesis Example 4: Synthesis of Compound R-3

[0314]

[0315] Compound R-3 was synthesized by referring to the synthesis method disclosed in published patent number KR 10-2019-0108222.

[0316] (Manufacturing of organic light-emitting diodes)

[0317] Example 1

[0318] A glass substrate coated with ITO (indium tin oxide) as a thin film was ultrasonically cleaned with distilled water. 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 by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. This prepared ITO transparent electrode was used as an anode, and Compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum deposited on the ITO substrate to form A thick hole injection layer is formed thereon by depositing compound A On the hole transport layer, compound D-2 according to Synthesis Example 3 was deposited to form A thick hole transport auxiliary layer was formed, on which the compound A-22 of Synthesis Example 1 and the compound B-136 of Synthesis Example 2 were vacuum deposited as the main body (which was doped with 10 wt % of GD as a dopant) to form Subsequently, compound B is deposited on the light-emitting layer to form A thick electron transport auxiliary layer is formed thereon by simultaneously vacuum depositing compound C and LiQ in a weight ratio of 1:1 By sequentially vacuum depositing LiQ and Al is used to form the cathode to manufacture organic light emitting diodes.

[0319] ITO / Compound A (3% NDP-9 doping, ) / Compound A / Compound D-2 / EML[host (Compound A-22:Compound B-136=35:65):GD=90wt%:10wt%] / Compound B / Compound C:LiQ / LiQ / Al

[0320] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0321] Compound B: 2-{3-[3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine

[0322] Compound C: 4-(4-{4-[4-(diphenyl-1,3,5-triazine-2-yl)phenyl]naphthalen-1-yl}phenyl)benzonitrile

[0323] [GD]

[0324]

[0325] Example 2 and Comparative Examples 1 to 3

[0326] The diodes of Example 2 and Comparative Examples 1 to 3 were manufactured in the same manner as Example 1, except that the hole transport auxiliary layer was changed as described in Table 1.

[0327] Comparative Example 4

[0328] The diode of Comparative Example 4 was manufactured in the same manner as in Example 2, except that the first host was changed as described in Table 1 and the mixing ratio of the first host and the second host was changed to 30:70 wt %.

[0329] Evaluation: Measuring life

[0330] Lifespan characteristics of the organic light emitting diodes according to Examples 1 to 2 and Comparative Examples 1 to 4 were evaluated.

[0331] The specific measurement method is as follows, and the results are shown in Table 1.

[0332] In the case of brightness (cd / m 2 ) remains at 24000cd / m 2 At the same time, the results were obtained by measuring the time it took for the current efficiency (cd / A) to drop to 95%.

[0333] The relative values ​​based on the lifespan of Comparative Example 1 are shown in Table 1.

[0334] [Table 1]

[0335]

[0336] Referring to Table 1, the organic light emitting diode including the composition according to the embodiment of the present invention exhibited significantly improved lifespan characteristics compared to the organic light emitting diode according to the comparative example.

[0337] While the invention has been described in connection with what are 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 Chemical Formula 1 and a second compound represented by Chemical Formula 2 or a combination of Chemical Formula 3 and Chemical Formula 4, and the hole transport auxiliary layer includes a third compound represented by Chemical Formula 5: [Chemical formula 1] In Chemical Formula 1, Ar 1 To Ar 3 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, L 1 To L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 1 To R 3 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl, m1 and m3 are each independently one of integers from 1 to 4, and m2 is an integer of 1 or 2; [Chemical formula 2] In chemical formula 2, Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, Ar 10 To Ar 13 are each independently hydrogen or a substituted or unsubstituted C6 to C30 aryl group, L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 4 To R 8 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, m4, m7 and m8 are each independently one of integers from 1 to 4, m5 and m6 are each independently one of integers from 1 to 3, and n is an integer from 0 to 2; In Chemical Formula 3 and Chemical Formula 4, Ar 6 and Ar 7 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or CL a -R a , among a1* to a4* in Chemical Formula 3, two adjacent ones are each connected to * in Chemical Formula 4, L a , L 7 and L 8 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R a , R 9 and R 10 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 m9 and m10 are each independently an integer from 1 to 4; [Chemical formula 5] In Chemical Formula 5, X 1 is C or Si, R 11 To R 14 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, R 15 and R 16 are each independently a substituted or unsubstituted C1 to C30 alkyl group or a substituted or unsubstituted C6 to C30 aryl group, Ar 8 is a substituted or unsubstituted C6 to C30 aryl group, Ar 9 is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted dibenzothioyl group, L 9 To L 11 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, m11, m12 and m14 are each independently one of integers from 1 to 4, and m13 is an integer between 1 and 3.

2. The organic optoelectronic device according to claim 1, wherein Ar 1 To Ar 3 are each independently 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, and Ar 2 and Ar 3 At least one of the groups is 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.

3. The organic optoelectronic device according to claim 1, wherein The second compound is represented by Chemical Formula 2-8 or Chemical Formula 3C: [Chemical formula 2-8] In Chemical Formula 2-8, R 4 To R 7 are each independently hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, Ar 10 To Ar 13 are each independently hydrogen or substituted or unsubstituted C6 to C12 aryl, and *-L 5 -Ar 4 and *-L 6 -Ar 5 are each independently one of the substituents listed in Group II, [Group II] In Group II, * is the connection point, D is deuterium, m19 is one of integers from 1 to 5, m20 is one of integers from 1 to 4, m21 is one of integers from 1 to 3, m22 is an integer from 1 or 2, and * is a connection point, [Chemical formula 3C] In chemical formula 3C, L a3 and L a4 is a single key, L 7 and L 8 are each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, R 9 , R 10 , R a3 and R a4 are each independently hydrogen, deuterium or C6 to C12 aryl, Ar 6 and Ar 7 are each independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted biphenyl, and m9 and m10 are each independently one of integers from 1 to 4.

4. The organic optoelectronic device according to claim 1, wherein The third compound is represented by any one of Chemical Formula 5-1 to Chemical Formula 5-4: In Chemical Formula 5-1 to Chemical Formula 5-4, X 1 , R 11 To R 16 ,Ar 8 ,Ar 9 , L 9 To L 11 and m11 to m14 are defined in claim 1.

5. The organic optoelectronic device according to claim 1, wherein Ar in chemical formula 5 8 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

6. The organic optoelectronic device according to claim 1, wherein Ar in chemical formula 5 9 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl or substituted or unsubstituted dibenzosilyl.

7. The organic optoelectronic device according to claim 1, wherein Ar in chemical formula 5 9 A substituent selected from the group consisting of: [Group III] In Group III, * is the connection point.

8. The third compound is selected from the compounds listed in Group 3: [Group 3] 9. The organic optoelectronic device according to claim 1, wherein the second compound is represented by Chemical Formula 2-8, and the third compound is represented by Chemical Formula 5-2: [Chemical formula 2-8] In Chemical Formula 2-8, R 4 To R 7 are each independently hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, Ar 10 To Ar 13 are each independently hydrogen or a substituted or unsubstituted C6 to C12 aryl group, m4 and m7 are each independently an integer from 1 to 4, m5 and m6 are each independently one of integers from 1 to 3, and *-L 5 -Ar 4 and *-L 6 -Ar 5 are each independently selected from the substituents listed in Group II, [Group II] In Group II, D is deuterium, m19 is one of integers from 1 to 5, m20 is one of integers from 1 to 4, m21 is one of integers from 1 to 3, m22 is an integer from 1 or 2, and * is a connection point; [Chemical formula 5-2] In chemical formula 5-2, X 1 is C or Si, R 11 To R 14 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C30 aryl, R 15 and R 16 are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, Ar 8 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group or a substituted or unsubstituted terphenyl group, Ar 9 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl or substituted or unsubstituted dibenzothiaryl, L 9 To L 11 are each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, m11, m12 and m14 are each independently one of integers from 1 to 4, and m13 is an integer between 1 and 3. 10 . A display device comprising the organic optoelectronic device according to claim 1 .

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