Organic optoelectronic device and display device

Abstract

An organic optoelectronic device and a display device are provided. The organic optoelectronic device includes an anode and a cathode facing each other; a light emitting layer between the anode and the cathode; a hole transport layer between the anode and the light emitting layer; and a hole transport auxiliary layer between the hole transport layer and the light emitting layer, in which the hole transport auxiliary layer includes a first hole transport auxiliary layer adjacent to the hole transport layer and a second hole transport auxiliary layer adjacent to the light emitting layer, the first hole transport auxiliary layer including a first compound represented by Chemical Formula 1, and the second hole transport auxiliary layer including a second compound represented by Chemical Formula 2. And the second hole transport auxiliary layer contains a second compound represented by Chemical Formula 2. # imgabs0 #

Description

[0001] Citations of Related Applications

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0076850 filed in the Korean Intellectual Property Office on June 15, 2023, and Korean Patent Application No. 10-2024-0076527 filed in the Korean Intellectual Property Office on June 12, 2024, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Embodiments relate to an organic optoelectronic device and a display device. Background Art

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

[0005] 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.

[0006] 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.

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

[0008] An embodiment relates to an organic optoelectronic device, which 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 hole transport layer and the light-emitting layer, wherein the hole transport auxiliary layer includes a first hole transport auxiliary layer adjacent to the hole transport layer and a second hole transport auxiliary layer adjacent to the light-emitting layer, the first hole transport auxiliary layer includes a first compound represented by Chemical Formula 1, and the second hole transport auxiliary layer includes a second compound represented by Chemical Formula 2,

[0009] [Chemical formula 1]

[0010]

[0011] In Chemical Formula 1, R a and R bare each independently a substituted or unsubstituted C1 to C30 alkyl group or a substituted or unsubstituted C6 to C30 aryl group, L 1 To L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group, R 1 and R 2 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C3 to C40 cycloalkyl group or a substituted or unsubstituted C6 to C20 aryl group, m1 is an integer from 1 to 4, and m2 is an integer from 1 to 3;

[0012] [Chemical formula 2]

[0013]

[0014] In chemical formula 2, X 1 It is O or S, L 4 To L 6 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group, R 3 and R 4 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, Ar 3 and Ar 4 At least one of them is a substituted or unsubstituted 9-fluorenyl group, m3 is an integer of 1 to 4, and m4 is an integer of 1 to 3.

[0015] Embodiments may be achieved by providing a display device including the organic optoelectronic device according to one embodiment. BRIEF DESCRIPTION OF THE DRAWINGS

[0016] Characteristics will become apparent to those skilled in the art by describing in detail exemplary embodiments with reference to the accompanying drawings, in which:

[0017] Figure 1 is a cross-sectional view showing an organic light emitting diode according to some embodiments. DETAILED DESCRIPTION

[0018] Exemplary embodiments will now be described more fully below with reference to the accompanying drawings; however, they may be embodied in different forms and should not be considered limited to the embodiments shown herein. However, these embodiments are provided so that this disclosure will be thorough and complete for those skilled in the art and will fully convey exemplary implementations.

[0019] In the accompanying drawings, the sizes of layers and regions may be exaggerated for clarity. It will also be understood that when a layer or element is referred to as being "on" another layer or substrate, it may be directly on the other layer or substrate, or there may also be intervening layers. In addition, it will be understood that when a layer is referred to as being "under" another layer, it may be directly below, and there may also be one or more intervening layers. In addition, it will be understood that when a layer is referred to as being "between" two layers, it may be the only layer between the two layers, or there may also be one or more intervening layers. Throughout the invention, similar reference numerals represent similar elements. As used herein, the term "or" is not necessarily an exclusive term, for example, "A or B" will include A, B, or A and B.

[0020] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or 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 C40 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.

[0021] In one embodiment, "substituted" may refer to that at least one hydrogen of a substituent or compound is replaced by the following: deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C40 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl or cyano. In addition, in one embodiment, "substituted" may refer to that at least one hydrogen of a substituent or compound is replaced by the following: deuterium, C1 to C20 alkyl, C3 to C30 cycloalkyl, C6 to C30 aryl or cyano. In addition, in one embodiment, "substituted" may refer to that at least one hydrogen of a substituent or compound is replaced by the following: deuterium, C1 to C5 alkyl, C3 to C20 cycloalkyl, C6 to C18 aryl or cyano. In addition, in one embodiment, "substituted" may mean that at least one hydrogen of the substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, cyclohexyl, bicycloheptyl, adamantyl, phenyl, biphenyl, terphenyl or naphthyl.

[0022] As used herein, "unsubstituted" means that a hydrogen atom is not replaced with another substituent and that a hydrogen atom remains.

[0023] As used herein, "hydrogen (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)". For example, any hydrogen in any compound described herein may be protium, deuterium, or tritium (e.g., based on natural or artificial substitution).

[0024] As used herein, when a definition is not otherwise provided, "hetero" means containing one to three heteroatoms selected from N, O, S, P and Si and the remaining carbons in one functional group.

[0025] As used herein, "aryl" refers to a group including at least one hydrocarbon aromatic portion, and may include a group in which all elements of the hydrocarbon aromatic portion have p orbitals forming a conjugation, such as phenyl, naphthyl, etc., a group in which two or more hydrocarbon aromatic portions may be linked by a σ bond, such as biphenyl, terphenyl, quaterphenyl, etc., and a group in which two or more hydrocarbon aromatic portions are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl, etc.

[0026] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0027] As used in this article, "heterocyclic group" has the general concept of heteroaryl, and can include at least one heteroatom such as N, O, S, P and Si in the cyclic compound instead of carbon (C), the cyclic compound such as aryl, cycloalkyl, their condensed ring or their combination. In one embodiment, the heterocyclic group can be a condensed ring, and the entire ring or each ring of the heterocyclic group can include one or more heteroatoms.

[0028] 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 can be fused. When the heteroaryl is a fused ring, each ring can include one to three heteroatoms.

[0029] For example, 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 pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted 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.

[0030] For example, 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 benzothienyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, 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 carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzofuranofluorenyl, substituted or unsubstituted benzothienofluorenyl, or a combination thereof.

[0031] 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.

[0032] 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.

[0033] An organic optoelectronic device may be any device that converts electrical energy into light energy, or vice versa, and may be, for example, an organic photovoltaic device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum, among others.

[0034] Herein, an organic light emitting diode is exemplarily described as one example of an organic optoelectronic device.

[0035] Figure 1 is a cross-sectional view showing an organic light emitting diode according to some embodiments. Figure 1 An organic light emitting diode according to some embodiments is described.

[0036] Reference Figure 1 , an organic light emitting diode according to some embodiments may include, for example, an anode 10 and a cathode 20 facing each other and an organic layer 30 between the anode 10 and the cathode 20 .

[0037] 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, or a conductive polymer. The anode 10 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, or polyaniline.

[0038] 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, 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, or BaF2 / Ca.

[0039] The organic layer 30 may include a light-emitting layer 31, a hole transport layer 32, and a hole transport auxiliary layer 33 between the hole transport layer 32 and the light-emitting layer 31. The light-emitting layer 31 may include at least two types of hosts and dopants, and the host may be, for example, a phosphorescent host. 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.

[0040] The dopant may be a material mixed with a host in a small amount to cause luminescence, and is generally a material such as a metal complex that emits light by multiple excitations to a triplet state or more. The dopant may be, for example, an inorganic, organic, or organic / inorganic compound, and one or more types thereof may be used.

[0041] In one embodiment, the dopant may be a phosphorescent dopant, and an example 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 or may include, for example, a compound represented by the chemical formula Z.

[0042] [Chemical formula Z]

[0043] L 7 MX 3

[0044] In the chemical formula Z, M may be a metal, and L 7 and X 3 Each of them can independently be a ligand that forms a complex compound with M.

[0045] 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 7 and X 3 This may be, for example, a bidentate ligand.

[0046] In one embodiment, L 7 and X 3 The ligand represented may be a ligand of Group A.

[0047] [Group A]

[0048]

[0049] In group A, R 300 To R 302 Each independently may be, for example, hydrogen, deuterium, a C1 to C30 alkyl group which may be substituted by a halogen or not, a C6 to C30 aryl group which may be substituted by a C1 to C30 alkyl group or a halogen.

[0050] R 303 To R 324Each of them may independently be, for example, hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF5, 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.

[0051] n1 may be an integer from 1 to 5, for example.

[0052] n2 may be an integer from 1 to 4, for example.

[0053] n3 may be an integer from 1 to 3, for example.

[0054] n4 may be an integer such as 1 or 2.

[0055] n5 may be an integer of 1 to 6, for example.

[0056] In one embodiment, n1 may be 2, 3, 4 or 5, and each substituent may be the same as or different from each other.

[0057] In one embodiment, n2 may be 2, 3 or 4, and each substituent may be the same as or different from each other.

[0058] In one embodiment, n3 may be 2 or 3, and each substituent may be the same as or different from each other.

[0059] In one embodiment, n4 may be 2, and each substituent may be the same as or different from each other.

[0060] In one embodiment, n5 may be 2, 3, 4, 5 or 6, and each substituent may be the same as or different from each other.

[0061] In one embodiment, the dopant may be represented by Chemical Formula V.

[0062] [Chemical Formula V]

[0063]

[0064] In chemical formula V, R 101 To R 116 can each independently be, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132R 133 R 134 .

[0065] R 132 To R 134 Each independently may be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0066] R 101 To R 116 At least one of may be a functional group represented by Chemical Formula V-1.

[0067] L 100 The bidentate ligand may be a monovalent anion and may be a ligand coordinated to iridium via a lone electron pair of carbon or a heteroatom.

[0068] m14 and m15 may each independently be an integer of, for example, 0 to 3, and m14+m15 may be an integer of, for example, 1 to 3.

[0069] [Chemical formula V-1]

[0070]

[0071] In chemical formula V-1, R 135 To R 139 can each independently be, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 .

[0072] * indicates a moiety attached to a carbon atom.

[0073] As an example, a dopant represented by Chemical Formula Z-1 may be included.

[0074] [Chemical formula Z-1]

[0075]

[0076] In the chemical formula Z-1, the rings A, B, C and D may each independently be, for example, a 5-membered or 6-membered carbocyclic ring or a heterocyclic ring.

[0077] R A , R B , R C and R D Each may independently be mono-, di-, tri- or tetra-substituted or unsubstituted.

[0078] L B , L C and L DEach may independently be, for example, a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' or a combination thereof;

[0079] In one embodiment, nA may be 1, L E It can be, for example, a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', or a combination thereof. In one embodiment, nA can be 0 and L E Does not exist.

[0080] R A , R B , R C , R D R, R and R' can each independently be, for example, 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 or a combination thereof. In one embodiment, R A , R B , R C , R D Any adjacent ones of X, R and R' may be alone or may be linked to each other to provide a ring. B , X C , X D and X E can each independently be, for example, carbon and nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 can each independently be, for example, oxygen or a direct bond.

[0081] The dopant according to some embodiments may be a platinum complex, and may be represented, for example, by Chemical Formula VI.

[0082] [Chemical Formula VI]

[0083]

[0084] In Formula VI, X 100 Can be, for example, O, S or NR 131 .

[0085] R 117 To R 131 can each independently be, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR132 R 133 R 134 .

[0086] R 132 To R 134 Each independently may be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0087] In one embodiment, R 117 To R 131 At least one of them may be -SiR 132 R 133 R 134 or tert-butyl.

[0088] R 132 To R 134 Each independently may be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0089] The composition further comprising a dopant may be, for example, a green light emitting composition.

[0090] The hole transport layer 32 may be a layer that promotes the transfer of holes from the anode 10 to the light emitting layer 31 and blocks electrons, and may be, for example, an amine compound.

[0091] The amine compound may include, for example, at least one aryl group or heteroaryl group. The amine compound may be represented, for example, by Chemical Formula a or Chemical Formula b.

[0092]

[0093] In chemical formula a or b, Ar a To Ar g Each independently may be, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof.

[0094] Ar a To Ar c At least one of Ar d To Ar g At least one of may be, for example, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof.

[0095] Ar h It may be, for example, a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof.

[0096] In addition to the light emitting layer, the organic light emitting diode may further include a hole injection layer 34 .

[0097] The hole injection layer 34 may be a layer for promoting injection of holes from the anode 10 to the light emitting layer 31 and blocking electrons, and may be between the anode 10 and the hole transport layer 32 .

[0098] In one embodiment, at least one of the hole transport layer 32 and the hole injection layer 34 may include the compounds listed in Group B, which may be different from materials of the first hole transport auxiliary layer and the second hole transport auxiliary layer described later.

[0099] [Group B]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106] (Dn refers to the number of hydrogens replaced by deuterium and represents a structure having one or more deuterium substitutions)

[0107] In addition to the above-mentioned compounds, other suitable compounds may also be used in the hole transport layer 32 and the hole injection layer 34 .

[0108] The hole transport auxiliary layer 33 may include a first hole transport auxiliary layer 33 a adjacent to the hole transport layer 32 and a second hole transport auxiliary layer 33 b adjacent to the light emitting layer 31 .

[0109] The first hole transport auxiliary layer 33 a may include a first compound represented by Chemical Formula 1, and the second hole transport auxiliary layer 33 b may include a second compound represented by Chemical Formula 2.

[0110] [Chemical formula 1]

[0111]

[0112] In Chemical Formula 1, R a and R b Each may independently be, for example, a substituted or unsubstituted C1 to C30 alkyl group or a substituted or unsubstituted C6 to C30 aryl group.

[0113] L1 To L 3 Each may independently be, for example, a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0114] R 1 and R 2 Each may independently be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic.

[0115] Ar 1 and Ar 2 Each may independently be, for example, a substituted or unsubstituted C3 to C40 cycloalkyl group or a substituted or unsubstituted C6 to C20 aryl group.

[0116] m1 may be an integer of 1 to 4, for example.

[0117] m2 may be an integer from 1 to 3, for example.

[0118] [Chemical formula 2]

[0119]

[0120] In chemical formula 2, X 1 It can be O or S, for example.

[0121] L 4 To L 6 Each may independently be, for example, a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0122] R 3 and R 4 Each may independently be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic.

[0123] Ar 3 and Ar 4 Each may independently be, for example, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0124] Ar 3 and Ar 4 At least one of the groups may be, for example, a substituted or unsubstituted 9-fluorenyl group.

[0125] m3 may be an integer of 1 to 4, for example.

[0126] m4 may be an integer from 1 to 3, for example.

[0127] According to some embodiments, an organic light-emitting diode can apply a combination of two hole transport auxiliary layers at the interface between the hole transport layer and the light-emitting layer, thereby adjusting the hole injection ability in the first hole transport auxiliary layer to balance the charge in the light-emitting layer, and can block electrons in the second hole transport auxiliary layer and can balance the hole and electron density, thereby achieving low driving voltage, high efficiency and improved lifespan characteristics.

[0128] In one embodiment, m1 may be, for example, 2, 3 or 4 and each R 1 May be the same as or different from each other.

[0129] In one embodiment, m2 may be, for example, 2 or 3 and each R 2 May be the same as or different from each other.

[0130] In one embodiment, Chemical Formula 1 may be represented, for example, by one of Chemical Formulas 1-1 to 1-4.

[0131]

[0132] In Chemical Formulae 1-1 to 1-4, L 1 To L 3 , R a , R b , R 1 , R 2 ,Ar 1 ,Ar 2 The definitions of m1, m2 and m3 may be the same as those in Chemical Formula 1.

[0133] In one embodiment, Ar in Chemical Formula 1 1 and Ar 2 Each of them independently may be, for example, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted bicyclo[2,2,1]heptyl group, a substituted or unsubstituted adamantyl group, 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.

[0134] In one embodiment, Ar in Chemical Formula 1 1 and Ar 2Each independently may be, for example, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted bicyclo[2,2,1]heptyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted dibenzosilyl group.

[0135] In one embodiment, R in Chemical Formula 1 1 and R 2 Each independently may be, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0136] In one embodiment, R in Chemical Formula 1 1 and R 2 Each independently may be, for example, hydrogen, deuterium, substituted or unsubstituted tert-butyl, or substituted or unsubstituted phenyl.

[0137] In one embodiment, L in Chemical Formula 1 1 To L 3 Each independently may be, for example, a single bond or a substituted or unsubstituted phenylene group.

[0138] In one embodiment, part L 2 -Ar 1 and L 3 -Ar 2 Can each independently be part of Group I.

[0139] [Group I]

[0140]

[0141] In Group I, R 8 To R 12 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl.

[0142] m8 may be an integer from 1 to 5, for example.

[0143] m9 may be an integer from 1 to 4, for example.

[0144] m10 may be an integer from 1 to 7, for example.

[0145] m11 may be an integer from 1 to 3, for example.

[0146] m12 may be an integer such as 1 or 2.

[0147] * is the connection point.

[0148] In one embodiment, m8 may be, for example, 2, 3, 4 or 5 and each R 8 May be the same as or different from each other.

[0149] In one embodiment, m9 may be, for example, 2, 3 or 4 and each R 9 May be the same as or different from each other.

[0150] In one embodiment, m10 may be, for example, 2, 3, 4, 5, 6 or 7 and each R 10 May be the same as or different from each other.

[0151] In one embodiment, m11 may be, for example, 2 or 3 and each R 11 May be the same as or different from each other.

[0152] In one embodiment, m12 may be, for example, 2 and each R 12 May be the same as or different from each other.

[0153] In one embodiment, the first compound may be, for example, a compound of Group 1.

[0154] [Group 1]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162] In one embodiment, m3 may be, for example, 2, 3 or 4 and each R 3 May be the same as or different from each other.

[0163] In one embodiment, m4 may be, for example, 2 or 3 and each R 4 May be the same as or different from each other.

[0164] In one embodiment, Ar in Chemical Formula 2 3 and Ar 4Each of them may independently be, for example, 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 phenanthryl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilyl group.

[0165] In one embodiment, Ar 3 and Ar 4 At least one of the groups may be, for example, a substituted or unsubstituted 9-fluorenyl group.

[0166] In one embodiment, Ar in Chemical Formula 2 3 and Ar 4 may be each independently, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group, and Ar 3 and Ar 4 At least one of the groups may be a substituted or unsubstituted 9-fluorenyl group.

[0167] In one embodiment, L 4 To L 6 Each independently may be, for example, a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0168] In one embodiment, L 4 can be a single bond, and L 5 and L 6 At least one of the groups may be, for example, a substituted or unsubstituted phenylene group.

[0169] In one embodiment, R 3 and R 4 Each independently may be, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0170] In one embodiment, the moiety -L 5 -Ar 3 and -L 6 -Ar 4 may each independently be part of Group II, and Ar 3 and Ar 4 At least one of the groups may be a substituted or unsubstituted 9-fluorenyl group.

[0171] [Group II]

[0172]

[0173] In Group II, R 8 To R 12 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl.

[0174] m8 may be an integer from 1 to 5, for example.

[0175] m9 may be an integer from 1 to 4, for example.

[0176] m10 may be an integer from 1 to 7, for example.

[0177] m11 may be an integer from 1 to 3, for example.

[0178] m12 may be an integer such as 1 or 2.

[0179] * is the connection point.

[0180] In one embodiment, Ar 3 and Ar 4 At least one of may be represented by Chemical Formula II-1.

[0181] [Chemical formula II-1]

[0182]

[0183] In Chemical Formula II-1, R 8 , R 9 , m8 and m9 may be defined the same as those described above.

[0184] In one embodiment, the second compound may be, for example, a compound of Group 2.

[0185] [Group 2]

[0186]

[0187]

[0188]

[0189] The organic layer 30 may include an electron transport region, which may help to further increase electron injection or electron mobility between the cathode 20 and the light emitting layer 31 and block holes.

[0190] In one embodiment, the electron transport region may include an electron transport layer 35 between the cathode 20 and the light emitting layer 31 and an electron transport auxiliary layer between the light emitting layer 31 and the electron transport layer 35, and a compound of group C may be included in at least one layer of the electron transport layer 35 and the electron transport auxiliary layer.

[0191] [Group C]

[0192]

[0193]

[0194]

[0195]

[0196] In some embodiments, the organic light emitting diode may include a light emitting layer 31 , a hole transport layer 32 , a first hole transport auxiliary layer 33 a , and a second hole transport auxiliary layer 33 b as organic layers.

[0197] In some embodiments, the organic light emitting diode may further include a hole injection layer 34 as an organic layer.

[0198] In some embodiments, the organic light emitting diode may further include an electron transport region as an organic layer.

[0199] In one embodiment, the organic light emitting diode may further include an electron injection layer as the organic layer in addition to the light emitting layer.

[0200] The organic light emitting diode can be produced by forming an anode or a cathode on a substrate, then forming an organic layer by a dry film method such as evaporation, sputtering, plasma plating, or ion plating, and then forming a cathode or an anode thereon.

[0201] The organic light emitting diode may be applied to an organic light emitting display device.

[0202] The following examples and comparative examples are provided to highlight the characteristics of one or more embodiments, but it will be understood that the examples and comparative examples should not be considered as limiting the scope of the embodiments, and the comparative examples should not be considered as being outside the scope of the embodiments. In addition, it will be understood that the embodiments are not limited to the specific details described in the examples and comparative examples.

[0203] 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 appropriate methods unless otherwise specified.

[0204] (Preparation of the First Compound)

[0205] Synthesis Example 1: Synthesis of Compound 1-21

[0206]

[0207] 10.0g (29.33mmol) of 1,3-di-tert-butyl-5-chloro-9,9-dimethyl-9H-fluorene intermediate, 15.67g (32.26mmol) of N-(4-(9-phenyl-9H-fluorene-9-yl)phenyl)-[1,1'-biphenyl]-4-amine intermediate, 5.64g (58.66mmol) of sodium tert-butoxide and 0.7g (1.76mmol) of tri-tert-butylphosphine were dissolved in 293ml of toluene, and 0.8g (0.88mmol) of Pd2(dba)3 was added thereto, and then stirred and refluxed for 12 hours under a nitrogen atmosphere. After the reaction was completed, the organic layer extracted therefrom with ethyl acetate and distilled water was dried over anhydrous magnesium sulfate and filtered, and the filtrate obtained therefrom was concentrated under reduced pressure. The product obtained therefrom was purified by silica gel column chromatography with n-hexane / dichloromethane (volume ratio of 3:1) to obtain 17.9 g (yield: 77%) of Compound 1-21 as a white solid.

[0208] Calculated: C, 91.21; H, 7.02; N, 1.77

[0209] Analytical values: C, 91.21; H, 7.02; N, 1.77

[0210] Synthesis Example 2: Synthesis of Compound 1-25

[0211]

[0212] Compound 1-25 (16.8 g, yield: 81%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of an intermediate of 1,3-di-tert-butyl-5-chloro-9,9-dimethyl-9H-fluorene and 12.96 g of an intermediate of bis(9,9-dimethyl-9H-fluorene-2-yl)amine were used in an equivalent ratio of 1:1.1.

[0213] Calculated: C, 90.16; H, 7.85; N, 1.98

[0214] Analytical values: C, 90.16; H, 7.85; N, 1.98

[0215] Synthesis Example 3: Synthesis of Compound 1-28

[0216]

[0217] Compound 1-28 (17.5 g, yield: 72%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of an intermediate of 1,3-di-tert-butyl-5-chloro-9,9-dimethyl-9H-fluorene and 16.96 g of an intermediate of 9,9-dimethyl-N-(3-(9-phenyl-9H-fluorene-9-yl)phenyl)-9H-fluorene-2-amine were used in an equivalent ratio of 1:1.1.

[0218] Calculated: C, 91.15; H, 7.16; N, 1.69

[0219] Analytical values: C, 91.15; H, 7.16; N, 1.69

[0220] Synthesis Example 4: Synthesis of Compound 1-63

[0221]

[0222] Compound 1-63 (17.0 g, yield: 83%) was synthesized in the same manner as in Synthesis Example 1, except that 8.0 g of the intermediate of 2-chloro-9,9-dimethyl-9H-fluorene and 15.22 g of the intermediate of N-([1,1'-biphenyl]-4-yl)triphenyl-2-amine were used in an equivalent ratio of 1:1.1.

[0223] Calculated: C, 91.96; H, 5.66; N, 2.38

[0224] Analytical values: C, 91.96; H, 5.66; N, 2.38

[0225] Synthesis Example 5: Synthesis of Compound 1-66

[0226]

[0227] Compound 1-66 (21.8 g, yield: 82%) was synthesized in the same manner as in Synthesis Example 1, except that 9.0 g of the intermediate of 2-chloro-9,9-dimethyl-9H-fluorene and 21.0 g of the intermediate of N-(4-(9-phenyl-9H-fluorene-9-yl)phenyl)-[1,1'-biphenyl]-4-amine were used in an equivalent ratio of 1:1.1.

[0228] Calculated: C, 92.13; H, 5.80; N, 2.07

[0229] Analytical values: C, 92.13; H, 5.80; N, 2.07

[0230] Synthesis Example 6: Synthesis of Compound 1-70

[0231]

[0232] Compound 1-70 (15.8 g, yield: 76%) was synthesized in the same manner as in Synthesis Example 1, except that 7.0 g of the intermediate of 2-chloro-9,9-dimethyl-9H-fluorene and 16.35 g of the intermediate of N-(3-(9-phenyl-9H-fluorene-9-yl)phenyl)-[1,1'-biphenyl]-4-amine were used in an equivalent ratio of 1:1.1.

[0233] Calculated: C, 92.13; H, 5.80; N, 2.07

[0234] Analytical values: C, 92.13; H, 5.80; N, 2.07

[0235] Synthesis Example 7: Synthesis of Compound 1-75

[0236]

[0237] Compound 1-75 (17.7 g, yield: 62%) was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of the intermediate of 3-chloro-5,5-dimethyl-5H-dibenzo[b,d]silole and 21.82 g of the intermediate of N-(4-(9-phenyl-9H-fluoren-9-yl)phenyl)-[1,1'-biphenyl]-4-amine were used in an equivalent ratio of 1:1.1.

[0238] Calculated values: C, 88.27; H, 5.66; N, 2.02; Si, 4.05

[0239] Analytical values: C, 88.27; H, 5.66; N, 2.02; Si, 4.04

[0240] (Preparation of Second Compound)

[0241] Synthesis Example 8: Synthesis of Compound 2-6

[0242]

[0243] Compound 2-6 (15.3 g, yield 83%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of an intermediate of N-(9,9-dimethyl-9H-fluorene-2-yl)dibenzo[b,d]furan-1-amine and 11.64 g of an intermediate of 9-(3-bromophenyl)-9-phenyl-9H-fluorene were used in an equivalent ratio of 1:1.1.

[0244] Calculated values: C, 90.27; H, 5.39; N, 2.02; O, 2.31

[0245] Analytical values: C, 90.27; H, 5.39; N, 2.02; O, 2.31

[0246] Synthesis Example 9: Synthesis of Compound 2-10

[0247]

[0248] Compound 2-10 (22.4 g, yield: 81%) was synthesized in the same manner as in Synthesis Example 1, except that 15 g of an intermediate of N-(9,9-dimethyl-9H-fluorene-2-yl)dibenzo[b,d]furan-1-amine and 19.05 g of an intermediate of 9-(4-bromophenyl)-9-phenyl-9H-fluorene were used in an equivalent ratio of 1:1.2.

[0249] Calculated values: C, 90.27; H, 5.39; N, 2.02; O, 2.31

[0250] Analytical values: C, 90.27; H, 5.39; N, 2.02; O, 2.31

[0251] Synthesis Example 10: Synthesis of Compound 2-13

[0252]

[0253] Compound 2-13 (17.9 g, yield: 82%) was synthesized in the same manner as in Synthesis Example 1, except that 15 g of an intermediate of 9,9-dimethyl-N-(3-(9-phenyl-9H-fluorene-9-yl)phenyl)-9H-fluorene-2-amine and 9.54 g of an intermediate of 1-chloro-4-phenyldibenzo[b,d]furan were used in an equivalent ratio of 1:1.2.

[0254] Calculated values: C, 90.71; H, 5.38; N, 1.82; O, 2.08

[0255] Analytical values: C, 90.71; H, 5.38; N, 1.82; O, 2.07

[0256] Synthesis Example 11: Synthesis of Compound 2-30

[0257]

[0258] Compound 2-30 (23.3 g, yield: 77%) was synthesized in the same manner as in Synthesis Example 1, except that 16 g of an intermediate of N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]thiophene-1-amine and 21.71 g of an intermediate of 9-(4-bromophenyl)-9-phenyl-9H-fluorene were used in an equivalent ratio of 1:1.2.

[0259] Calculated: C, 88.12; H, 4.98; N, 2.10; S, 4.80

[0260] Analytical values: C, 88.12; H, 4.98; N, 2.10; S, 4.80

[0261] Comparative Synthesis Example 1: Synthesis of Compound F-1

[0262]

[0263] Compound F-1 (16.5 g, yield: 80%) was synthesized in the same manner as in Synthesis Example 1, except that 15 g of an intermediate of N-([1,1'-biphenyl]-4-yl)-8-phenyldibenzo[b,d]furan-1-amine and 10.2 g of an intermediate of 4-bromo-1,1'-biphenyl were used in an equivalent ratio of 1:1.2.

[0264] Calculated values: C, 90.27; H, 5.39; N, 2.02; O, 2.31

[0265] Analytical values: C, 90.27; H, 5.39; N, 2.02; O, 2.31

[0266] Example 1

[0267] The glass substrate coated with the thin film of ITO / Ag / ITO was ultrasonically washed with distilled water. After washing with distilled water, the glass substrate was ultrasonically washed with acetone or isopropyl alcohol and dried, and then moved to a plasma cleaner, cleaned by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. The prepared ITO / Ag / ITO (reflective electrode) was used as an anode, and Compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO / Ag / ITO substrate to form A hole injection layer is formed on the hole injection layer to a thickness of The compound 1-21 obtained in Synthesis Example 1 was deposited on the hole transport layer to a thickness of To form a first hole transport auxiliary layer, and deposit the compound 2-6 obtained in Synthesis Example 8 on the first hole transport auxiliary layer to a thickness of On the second hole transport auxiliary layer, 85 wt % of the host H1 (40%) and the host H2 (60%) were used as the host, and 15 wt % of PtGD was doped as a dopant to form a second hole transport auxiliary layer by vacuum deposition. Subsequently, compound C is deposited to form a light-emitting layer on the light-emitting layer. The electron transport auxiliary layer is formed by vacuum depositing compound D and Liq at a weight ratio of 1:1 simultaneously. Thick electron transport layer. On the electron transport layer, Yb and AgMg are vacuum deposited in sequence to manufacture an organic light-emitting diode.

[0268] The structure is ITO / Ag / ITO / hole injection layer (compound A doped with 3% NDP-9, ) / hole transport layer (compound A, ) / first hole transport auxiliary layer (compound 1-21, ) / second hole transport auxiliary layer (compound 2-6, ) / light-emitting layer [host (host H1, host H2): PtGD = 85wt%: 15wt%] / Electron transport auxiliary layer (compound C, ) / electron transport layer (compound D: Liq, ) / Yb / AgMg.

[0269] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine

[0270] Compound C: 4-{4-[3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[0271] Compound D: 2-(4-{2-[4-(diphenyl-1,3,5-triazine-2-yl)phenyl]naphthalen-1-yl}phenyl)-4,6-diphenyl-1,3,5-triazine

[0272] Body H1:

[0273]

[0274] Body H2:

[0275]

[0276] PtGD:

[0277]

[0278] Examples 2 to 17 and Comparative Examples 1 to 5

[0279] Each organic light emitting diode was manufactured in the same manner as in Example 1, except that the composition was changed to the composition shown in Table 1.

[0280] evaluate

[0281] The driving voltage, luminous efficiency, and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 17 and Comparative Examples 1 to 5 were evaluated.

[0282] The specific measurement method is as follows, and the results are shown in Table 1.

[0283] (1) Measuring the change in current density due to voltage change

[0284] While increasing the voltage from 0 V to 10 V, the current value flowing through the unit diode in the obtained organic light emitting diode was measured using a current-voltage meter (Keithley 2400), and the measured current value was divided by the area to provide a result.

[0285] (2) Measuring the change in brightness due to voltage changes

[0286] While increasing the voltage of the organic light emitting diode from 0 V to 10 V, the luminance was measured using a luminance meter (Minolta CS-1000A).

[0287] (3) Measurement of luminous efficiency

[0288] Using the luminance and current density measured according to (1) and (2) above, calculate the same current density (10 mA / cm 2 ) under current efficiency (cd / A).

[0289] Based on Comparative Example 1, the luminous efficiency values ​​of Examples 1 to 17 and Comparative Examples 1 to 5 were calculated as relative values ​​and are listed in Table 1.

[0290] (4) Measurement life

[0291] By converting the brightness (cd / m 2 ) maintained at 24000cd / m 2 The results were obtained by measuring the time it takes for the current efficiency (cd / A) to drop to 97%.

[0292] Based on Comparative Example 1, the life measurement values ​​of Examples 1 to 17 and Comparative Examples 1 to 5 were calculated as relative values ​​and are listed in Table 1.

[0293] (5) Measure the driving voltage

[0294] Using an ammeter (Keithley 2400), the 2 The driving voltage of each device was measured to obtain the results.

[0295] Based on Comparative Example 1, the driving voltages of Examples 1 to 17 and Comparative Examples 1 to 5 were calculated as relative values ​​and are listed in Table 1.

[0296] (Table 1)

[0297]

[0298]

[0299] Referring to Table 1, the driving voltage, luminous efficiency, and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 17 are significantly improved compared to those of the organic light emitting diodes according to Comparative Examples 1 to 5.

[0300] One or more embodiments may provide an organic optoelectronic device having high efficiency, low driving voltage, and long lifespan.

[0301] One or more embodiments may provide a display device including the organic optoelectronic device.

[0302] An organic optoelectronic device with high efficiency, low driving voltage, and long lifespan can be realized.

[0303] Exemplary embodiments have been disclosed herein, and although specific terms are used, these terms are used and understood only in a general and descriptive sense and not for limiting purposes. In some cases, as will be apparent to those skilled in the art upon filing this application, unless otherwise specifically indicated, the characteristics, features, and / or elements described in conjunction with a specific embodiment may be used alone or in combination with the characteristics, features, and / or elements described in conjunction with other embodiments. Therefore, those skilled in the art will appreciate that changes in various forms and details may be made without departing from the spirit and scope of the invention as set forth in the appended claims.

Claims

1. An organic optoelectronic device, include: 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; as well as a hole transport auxiliary layer between the hole transport layer and the light emitting layer, in, The hole transport auxiliary layer includes a first hole transport auxiliary layer adjacent to the hole transport layer and a second hole transport auxiliary layer adjacent to the light emitting layer, The first hole transport auxiliary layer includes a first compound represented by Chemical Formula 1, and The second hole transport auxiliary layer includes a second compound represented by Chemical Formula 2, [Chemical formula 1] In Chemical Formula 1, R a and R b are each independently a substituted or unsubstituted C1 to C30 alkyl group or a substituted or unsubstituted C6 to C30 aryl group, L 1 To L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group, R 1 and R 2 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C3 to C40 cycloalkyl group or a substituted or unsubstituted C6 to C20 aryl group, m1 is an integer from 1 to 4, and m2 is an integer from 1 to 3; [Chemical formula 2] In chemical formula 2, X 1 is O or S, L 4 To L 6 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group, R 3 and R 4 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, Ar 3 and Ar 4 At least one of them is a substituted or unsubstituted 9-fluorenyl group, m3 is an integer from 1 to 4, and m4 is an integer from 1 to 3.

2. The organic optoelectronic device according to claim 1, in, Chemical Formula 1 is represented by one of Chemical Formula 1-1 to Chemical Formula 1-4, and In Chemical Formulae 1-1 to 1-4, L 1 To L 3 , R a , R b , R 1 , R 2 ,Ar 1 ,Ar 2 , m1 and m2 are the same as those defined in Chemical Formula 1.

3. The organic optoelectronic device according to claim 1, wherein Ar 1 and Ar 2 each is independently a substituted or unsubstituted cyclopentyl, a substituted or unsubstituted cyclohexyl, a substituted or unsubstituted bicyclo[2,2,1]heptyl, a substituted or unsubstituted adamantyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenylyl, a substituted or unsubstituted terphenylyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluorenyl or a substituted or unsubstituted dibenzosilyl.

4. The organic optoelectronic device according to claim 1, in, Part L 2 -Ar 1 and L 3 -Ar 2 each independently being part of Group I, [Group I] In Group I, R 8 To R 12 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, m8 is an integer from 1 to 5, m9 is an integer from 1 to 4, m10 is an integer from 1 to 7, m11 is an integer from 1 to 3, m12 is an integer of 1 or 2, and * is the connection point.

5. The organic optoelectronic device according to claim 1, wherein the first compound is a compound of Group 1: [Group 1] 6. The organic optoelectronic device according to claim 1, in, Ar 3 and Ar 4 are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl or substituted or unsubstituted dibenzosilyl, and Ar 3 and Ar 4 At least one of the groups is a substituted or unsubstituted 9-fluorenyl group.

7. The organic optoelectronic device according to claim 1, in, Part L 5 -Ar 3 and L 6 -Ar 4 each independently being part of Group II, Ar 3 and Ar 4 At least one of them is a substituted or unsubstituted 9-fluorenyl group, [Group II] In Group II, R 8 To R 12 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, m8 is an integer from 1 to 5, m9 is an integer from 1 to 4, m10 is an integer from 1 to 7, m11 is an integer from 1 to 3, m12 is an integer of 1 or 2, and * is the connection point.

8. The organic optoelectronic device according to claim 7, in, Ar 3 and Ar 4 At least one of them is a group represented by Chemical Formula II-1, and [Chemical formula II-1] In Chemical Formula II-1, R 8 , R 9 , m8 and m9 are defined the same as those of Group II.

9. The organic optoelectronic device according to claim 1, wherein the second compound is a compound of Group 2: [Group 2] 10 . A display device comprising the organic optoelectronic device according to claim 1 .

Images