Organic optoelectronic element and display device

Abstract

The present invention relates to an organic optoelectronic element comprising: a positive electrode and a negative electrode facing each other; a light-emitting layer positioned between the positive electrode and negative electrodes; a hole transport layer positioned between the positive electrode and light-emitting layer; and an auxiliary hole transport layer positioned between the light-emitting layer and hole transport layer, wherein the light-emitting layer comprises a first compound represented by chemical formula 1, and a second compound represented by chemical formula 2 or a combination of chemical formulae 3 and 4, and the auxiliary hole transport layer comprises a third compound represented by chemical formula 5. The details of chemical formulae 1 to 5 are as defined in the specification.

Description

Organic optoelectronic devices and displays

[0001] It relates to organic optoelectronic devices and display devices.

[0002] Organic optoelectronic diodes are devices that can convert electrical energy and light energy to each other.

[0003] Organic optoelectronic devices can be broadly divided into two types based on their operating principles. One type is a photoelectric device, in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to generate electrical energy. The other type is a light-emitting device, in which light energy is generated from electrical energy by supplying voltage or current to an electrode.

[0004] Examples of organic optoelectronic devices include organic photovoltaic devices, organic light-emitting devices, organic solar cells, and organic photoconductor drums.

[0005] Among these, organic light-emitting diodes (OLEDs) have recently attracted significant attention due to the increasing demand for flat panel display devices. OLEDs are devices that convert electrical energy into light, and their performance is significantly influenced by the organic materials located between the electrodes.

[0006] One embodiment provides an organic optoelectronic device capable of implementing high-efficiency characteristics.

[0007] Another embodiment provides a display device including the organic optoelectronic device.

[0008] According to one embodiment, an organic optoelectronic device is provided, including an anode and a cathode facing each other, a light-emitting layer positioned between the anode and the cathode, a hole transport layer positioned between the anode and the light-emitting layer, and a hole transport auxiliary layer positioned between the light-emitting layer and the hole transport layer, wherein the light-emitting layer includes a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2 or a combination of the following chemical formulas 3 and 4, and the hole transport auxiliary layer includes a third compound represented by the following chemical formula 5.

[0009] [Chemical Formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] Z 1 Inland Z 3 are each independently N or CR a And,

[0013] Z 1 Inland Z 3 At least two of them are N,

[0014] R 1 Inland R 8 and R a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0015] L 1 Inland L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heterocyclic group,

[0016] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group;

[0017] [Chemical Formula 2]

[0018]

[0019] In the above chemical formula 2,

[0020] 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,

[0021] L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0022] R 9 Inland R 19 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0023] m1 and m2 are each independently an integer from 1 to 3,

[0024] m3 is one of the integers 1 to 4,

[0025] n is an integer between 0 and 2;

[0026] [Chemical Formula 3] [Chemical Formula 4]

[0027]

[0028] In the above chemical formulas 3 and 4,

[0029] Ar 5 and Ar 6 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0030] In chemical formula 3, a1* to a4* are each independently a connecting carbon (C) or CLa -R b And,

[0031] In chemical formula 4, * each independently represents a connecting carbon (C),

[0032] Among a1* to a4* in chemical formula 3, two adjacent ones are each connected to * in chemical formula 4,

[0033] L a , L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0034] R b and R 20 Inland R 27 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group;

[0035] [Chemical Formula 5]

[0036]

[0037] In the above chemical formula 5,

[0038] Ar 8 and Ar 9 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0039] The above Ar 10 and Ar 11 are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

[0040] R 41 Inland R 45are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0041] m5 is an integer between 1 and 3.

[0042] According to another embodiment, a display device including the organic optoelectronic device is provided.

[0043] High-efficiency organic optoelectronic devices can be realized.

[0044] Figure 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment.

[0045] <Explanation of symbols>

[0046] 10: Anode 20: Cathode

[0047] 30: Organic layer 31: Hole transport layer

[0048] 32: Light-emitting layer 33: Hole transport auxiliary layer

[0049] 34: Electron transport layer

[0050]

[0051] Hereinafter, embodiments of the present invention will be described in detail. However, these are presented as examples and are not intended to limit the present invention. The present invention is defined solely by the scope of the claims set forth below.

[0052] As used herein, “substituted” means that at least one hydrogen in a substituent or compound is substituted with deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof, unless otherwise defined.

[0053] In one embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group. In addition, in one specific embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group. In addition, in one specific embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is replaced with a deuterium group, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0054] As used herein, “unsubstituted” means that a hydrogen atom remains a hydrogen atom without being replaced by another substituent.

[0055] In this specification, “hydrogen (-H)” may include “deuterium substitution (-D)” or “tritium substitution (-T)”.

[0056] In this specification, unless otherwise defined, “hetero” means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si in one functional group, and the remainder being carbon.

[0057] In this specification, "aryl group" is a concept that encompasses a group having one or more hydrocarbon aromatic moieties, and includes a form in which all elements of the hydrocarbon aromatic moieties have p-orbitals and these p-orbitals form conjugation, such as a phenyl group, a naphthyl group, etc., a form in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and a non-aromatic fused ring in which two or more hydrocarbon aromatic moieties are directly or indirectly fused, such as a fluorenyl group, etc.

[0058] Aryl groups include monocyclic, polycyclic, or fused ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.

[0059] In this specification, "heterocyclic group" is a superordinate concept including a heteroaryl group, and means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si instead of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. When the heterocyclic group is a fused ring, the heterocyclic group as a whole or each ring may contain one or more heteroatoms.

[0060] For example, a "heteroaryl group" means an aryl group containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si. Two or more heteroaryl groups may be directly connected via a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused to each other. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 of the heteroatoms.

[0061] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be, but is not limited to, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0062] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group is a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted It may be, but is not limited to, an isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof.

[0063] In this specification, the hole characteristic refers to a characteristic that can form holes by donating electrons when an electric field is applied, and has a conductive characteristic along the HOMO level, which means a characteristic that facilitates the injection of holes formed at the anode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the anode, and the movement in the light-emitting layer.

[0064] In addition, electronic properties refer to the property of being able to receive electrons when an electric field is applied, and have conductive properties along the LUMO level, which means the property of facilitating the injection of electrons formed at the cathode into the light-emitting layer, the movement of electrons formed in the light-emitting layer to the cathode, and the movement in the light-emitting layer.

[0065] An organic optoelectronic device according to an embodiment of the present invention is described below.

[0066] Organic optoelectronic devices are not particularly limited as long as they can convert electrical energy and light energy to each other, and examples thereof include organic photoelectric devices, organic light-emitting devices, organic solar cells, and organic photosensitive drums.

[0067] Here, an organic light-emitting device, which is an example of an organic optoelectronic device, is described as an example, but the present invention is not limited thereto and can be equally applied to other organic optoelectronic devices.

[0068] To clearly illustrate various layers and regions in the drawings, the thicknesses are enlarged. Similar parts are designated by the same drawing reference numerals throughout the specification. When an element, such as a layer, film, region, or plate, is said to be "on" another element, this includes not only the case where it is "directly on" the other element, but also the case where there are other elements in between. Conversely, when an element is said to be "directly on" another element, it means that there are no other elements in between.

[0069] Figure 1 is a cross-sectional view schematically illustrating an organic optoelectronic device according to one embodiment.

[0070] Referring to FIG. 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) positioned between the anode (10) and the cathode (20).

[0071] The anode (10) can be made of a conductor with a high work function, for example, to facilitate hole injection, and can be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode (10) may be, but is not limited to, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, or gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); 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) (polyethylenedioxythiophene: PEDOT), polypyrrole, and polyaniline.

[0072] The cathode (20) can be made of a conductor with a low work function to facilitate electron injection, for example, and can be made of a metal, a metal oxide, and / or a conductive polymer. The cathode (20) can be made of, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0073] The organic layer (30) includes a hole transport layer (31), a light-emitting layer (32), and a hole transport auxiliary layer (33) located between the hole transport layer (31) and the light-emitting layer (32).

[0074] The hole transport layer (31) is a layer for facilitating hole transfer from the anode (10) to the light-emitting layer (32), and may be, for example, an amine compound, but is not limited thereto.

[0075] The above amine compound may include, for example, at least one aryl group and / or heteroaryl group. The above amine compound may be represented by, for example, the following chemical formula a or chemical formula b, but is not limited thereto.

[0076] [chemical formula a] [chemical formula b]

[0077]

[0078] In the above chemical formula a or b,

[0079] Ar a Inland Ar g are each independently 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,

[0080] Ar a Inland Ar c At least one of and Ar d Inland Ar g At least one of them is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,

[0081] 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.

[0082] The light-emitting layer (32) includes at least two types of hosts and dopants, and the host includes a first compound having relatively strong bipolar characteristics and a second compound having relatively strong hole characteristics.

[0083] The above first compound is a compound having relatively strong bipolar electronic properties, and can be represented by the following chemical formula 1.

[0084] [Chemical Formula 1]

[0085]

[0086] In the above chemical formula 1,

[0087] Z 1 Inland Z 3 are each independently N or CR a And,

[0088] Z 1 Inland Z 3 At least two of them are N,

[0089] R 1 Inland R 8 and R a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0090] L 1 Inland L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heterocyclic group,

[0091] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group.

[0092] The first compound has a structure in which at least one 9-carbazole is substituted on a pyrimidine or triazine ring, so that it can easily receive electrons when an electric field is applied, and accordingly, together with the second compound described below, it can appropriately balance good interface properties and the flow of holes and electrons, and thus, it can improve the operating voltage of an organic optoelectronic device to which the first compound is applied.

[0093] In the above chemical formula 1, Ar 1 and Ar 2may 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 naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzosilolyl group, or a substituted or unsubstituted carbazolyl group.

[0094] For example, the above Ar 1 and Ar 2 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 triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzosilolyl group, or a substituted or unsubstituted carbazolyl group.

[0095] In the above chemical formula 1, L 1 Inland L 3 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0096] For example, L 1 -Ar 1 and L 2 -Ar 2 Each of the substituents may be independently selected from among the substituents listed in Group I below.

[0097] [Group Ⅰ]

[0098]

[0099] In the above group Ⅰ,

[0100] R 46 Inland R 48 are each independently hydrogen, deuterium, cyano, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,

[0101] m6 is one of the integers 1 to 5,

[0102] m7 is one of the integers 1 to 4,

[0103] m8 is one of the integers 1 to 3,

[0104] * is a connection point.

[0105] In the above chemical formula 1, R 1 Inland R 8 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0106] For example, the above R 1 Inland R 8 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0107] In the above chemical formula 1, R a may be hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0108] For example, the above R a may be hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0109] The first compound may be, for example, but is not limited to, one selected from the compounds listed in Group 1 below.

[0110] [Group 1]

[0111] [A-1] [A-2] [A-3] [A-4] [A-5]

[0112]

[0113] [A-6] [A-7] [A-8] [A-9] [A-10]

[0114]

[0115] [A-11] [A-12] [A-13] [A-14] [A-15]

[0116]

[0117] [A-16] [A-17] [A-18] [A-19] [A-20]

[0118]

[0119] [A-21] [A-22] [A-23] [A-24] [A-25]

[0120]

[0121] [A-26] [A-27] [A-28] [A-29] [A-30]

[0122]

[0123] [A-31] [A-32] [A-33] [A-34] [A-35]

[0124]

[0125] [A-36] [A-37] [A-38] [A-39] [A-40]

[0126]

[0127] [A-41] [A-42] [A-43] [A-44] [A-45]

[0128]

[0129] [A-46] [A-47] [A-48] [A-49] [A-50]

[0130]

[0131] [A-51] [A-52] [A-53] [A-54] [A-55]

[0132]

[0133] [A-56] [A-57] [A-58] [A-59] [A-60]

[0134]

[0135] [A-61] [A-62] [A-63] [A-64] [A-65]

[0136]

[0137] [A-66] [A-67] [A-68] [A-69] [A-70]

[0138]

[0139] [A-71] [A-72] [A-73] [A-74] [A-75]

[0140]

[0141] [A-76] [A-77] [A-78] [A-79] [A-80]

[0142]

[0143] [A-81] [A-82] [A-83] [A-84] [A-85]

[0144]

[0145] [A-86] [A-87] [A-88] [A-89] [A-90]

[0146]

[0147] [A-91] [A-92] [A-93] [A-94] [A-95]

[0148]

[0149] [A-96] [A-97] [A-98] [A-99] [A-100]

[0150]

[0151] [A-101] [A-102] [A-103] [A-104]

[0152]

[0153] [A-105] [A-106] [A-107] [A-108]

[0154]

[0155] [A-109] [A-110] [A-111] [A-112]

[0156]

[0157] [A-113] [A-114] [A-115] [A-116]

[0158]

[0159] [A-117] [A-118] [A-119] [A-120]

[0160]

[0161] The above first compound may be used in one or two or more types.

[0162] The above second compound can be used in a light-emitting layer together with the above first compound to improve light-emitting efficiency and lifespan characteristics by increasing charge mobility and increasing stability.

[0163] The second compound may be represented, for example, by the following chemical formula 2.

[0164] [Chemical Formula 2]

[0165]

[0166] In the above chemical formula 2,

[0167] 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,

[0168] L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0169] R 9 Inland R 19 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0170] m1 and m2 are each independently an integer from 1 to 3,

[0171] m3 is one of the integers 1 to 4,

[0172] n is an integer between 0 and 2.

[0173] If m1 is 2 or more, each R 13 may be identical or different.

[0174] If m2 is 2 or more, each R 14 may be identical or different.

[0175] If m3 is 2 or more, each R 19 may be identical or different.

[0176] For example, Ar of the above chemical formula 2 3 and Ar 4 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 naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group,

[0177] L of the above chemical formula 2 4 and L 5 are each independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,

[0178] R of the above chemical formula 2 9 Inland R 19 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group,

[0179] n can be 0 or 1.

[0180] For example, “substitution” in the above 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.

[0181] In a specific embodiment of the present invention, the chemical formula 2 can be expressed as one of the following chemical formulas 2-1 to 2-15.

[0182] [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3]

[0183]

[0184] [Chemical Formula 2-4] [Chemical Formula 2-5] [Chemical Formula 2-6]

[0185]

[0186] [Chemical Formula 2-7] [Chemical Formula 2-8] [Chemical Formula 2-9]

[0187]

[0188] [Chemical Formula 2-10] [Chemical Formula 2-11] [Chemical Formula 2-12]

[0189]

[0190] [Chemical Formula 2-13] [Chemical Formula 2-14] [Chemical Formula 2-15]

[0191]

[0192] In the above chemical formulas 2-1 to 2-15, R 9 Inland R 19 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group,

[0193] m1 and m2 are each independently an integer from 1 to 3,

[0194] m3 is one of the integers 1 to 4,

[0195] L 4 -Ar 3 and L 5 -Ar 4 Each may independently be one of the substituents listed in Group II below.

[0196] [Group II]

[0197]

[0198] In the above group II,

[0199] R 49 Inland R 52 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,

[0200] m9 is one of the integers 1 to 5,

[0201] m10 is one of the integers 1 to 4,

[0202] m11 is one of the integers 1 to 3,

[0203] m12 is an integer of 1 or 2,

[0204] * is a connection point.

[0205] If m9 is 2 or more, each R 49 may be identical or different.

[0206] If m10 is 2 or more, each R 50 may be identical or different.

[0207] If m11 is 2 or more, each R 51 may be identical or different.

[0208] If m12 is 2 or more, each R 52may be identical or different.

[0209] In one embodiment, the above chemical formula 2 can be expressed as the above chemical formula 2-8.

[0210] In addition, L of the above chemical formula 2-8 4 -Ar 3 and L 5 -Ar 4 Each may be independently selected from the above group II, and may be, for example, any one of E-1, E-2, E-3, E-4, E-7, E-8, and E-9.

[0211] The second compound may be represented by, for example, a combination of the following chemical formulas 3 and 4.

[0212] [Chemical Formula 3] [Chemical Formula 4]

[0213]

[0214] In the above chemical formulas 3 and 4,

[0215] Ar 5 and Ar 6 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0216] In chemical formula 3, a1* to a4* are each independently a connecting carbon (C) or CL a -R b And,

[0217] In chemical formula 4, * each independently represents a connecting carbon (C),

[0218] Among a1* to a4* in chemical formula 3, two adjacent ones are each connected to * in chemical formula 4,

[0219] L a , L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0220] R b and R 20Inland R 27 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0221] For example, the second compound represented by the combination of the above chemical formulas 3 and 4 can be expressed by any one of the following chemical formulas 3A, 3B, 3C, 3D, and 3E.

[0222] [Formula 3A] [Formula 3B] [Formula 3C]

[0223]

[0224] [Chemical Formula 3D] [Chemical Formula 3E]

[0225]

[0226] In the above chemical formulas 3A to 3E, Ar 5 , Ar 6 , L 6 , L 7 , and R 20 Inland R 27 is as described above,

[0227] L a1 Inland L a4 is the aforementioned L 6 and L 7 is the same as the definition of

[0228] R a1 Inland R a4 is the aforementioned R 20 Inland R 27 It is the same as the definition of .

[0229] For example, Ar of the above chemical formulas 3 and 4 5 and Ar 6are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,

[0230] R a1 Inland R a4 and R 20 Inland R 27 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0231] In a specific embodiment of the present invention, L of the chemical formulas 3 and 4 6 -Ar 5 and L 7 -Ar 6 Each of the substituents may be independently selected from the substituents listed in Group II above.

[0232] In one embodiment, the R a1 Inland R a4 and R 20 Inland R 27 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0233] For example, the above R a1 Inland R a4 and R 20 Inland R 27 may each independently be hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group,

[0234] In a specific embodiment, the R a1 Inland R a4 , and R20 Inland R 27 Each of which can independently be a hydrogen, deuterium or phenyl group.

[0235] For example, the compound for the second organic optoelectronic device may be one selected from the compounds listed in Group 2 below, but is not limited thereto.

[0236] [Group 2]

[0237] [B-1] [B-2] [B-3] [B-4] [B-5]

[0238]

[0239] [B-6] [B-7] [B-8] [B-9] [B-10]

[0240]

[0241] [B-11] [B-12] [B-13] [B-14] [B-15]

[0242]

[0243] [B-16] [B-17] [B-18] [B-19] [B-20]

[0244]

[0245] [B-21] [B-22] [B-23] [B-24] [B-25]

[0246]

[0247] [B-26] [B-27] [B-28] [B-29] [B-30]

[0248]

[0249] [B-31] [B-32] [B-33] [B-34] [B-35]

[0250]

[0251] [B-36] [B-37] [B-38] [B-39] [B-40]

[0252]

[0253] [B-41] [B-42] [B-43] [B-44] [B-45]

[0254]

[0255] [B-46] [B-47] [B-48] [B-49] [B-50]

[0256]

[0257] [B-51] [B-52] [B-53] [B-54] [B-55]

[0258]

[0259] [B-56] [B-57] [B-58] [B-59] [B-60]

[0260]

[0261] [B-61] [B-62] [B-63] [B-64] [B-65]

[0262]

[0263] [B-66] [B-67] [B-68] [B-69] [B-70]

[0264]

[0265] [B-71] [B-72] [B-73] [B-74] [B-75]

[0266]

[0267] [B-76] [B-77] [B-78] [B-79] [B-80]

[0268]

[0269] [B-81] [B-82] [B-83] [B-84] [B-85]

[0270]

[0271] [B-86] [B-87] [B-88] [B-89] [B-90]

[0272]

[0273] [B-91] [B-92] [B-93] [B-94] [B-95]

[0274]

[0275] [B-96] [B-97] [B-98] [B-99] [B-100]

[0276]

[0277] [B-101] [B-102] [B-103] [B-104] [B-105]

[0278]

[0279] [B-106] [B-107] [B-108] [B-109] [B-110]

[0280]

[0281] [B-111] [B-112] [B-113] [B-114] [B-115]

[0282]

[0283] [B-116] [B-117] [B-118] [B-119] [B-120]

[0284]

[0285] [B-121] [B-122] [B-123] [B-124] [B-125]

[0286]

[0287] [B-126] [B-127] [B-128] [B-129] [B-130]

[0288]

[0289] [B-131] [B-132] [B-133] [B-134] [B-135]

[0290]

[0291] [B-136] [B-137] [B-138] [B-139] [B-140]

[0292]

[0293] [B-141] [B-142] [B-143] [B-144]

[0294]

[0295] [B-145] [B-146] [B-147]

[0296]

[0297] [B-148] [B-149] [B-150] [B-151] [B-152]

[0298]

[0299] Additionally, examples of compounds B-1 to B-152 listed in Group 2 above in which at least one hydrogen is replaced with deuterium are presented below, but are not limited thereto.

[0300] [B-153] [B-154] [B-155] [B-156] [B-157]

[0301]

[0302] [B-158] [B-159] [B-160] [B-161] [B-162]

[0303]

[0304] [B-163] [B-164] [B-165] [B-166] [B-167]

[0305]

[0306] [B-168] [B-169] [B-170] [B-171] [B-172]

[0307]

[0308] [B-173] [B-174] [B-175] [B-176] [B-177]

[0309]

[0310] [B-178] [B-179] [B-180] [B-181] [B-182]

[0311]

[0312] [B-183] [B-184] [B-185] [B-186] [B-187]

[0313]

[0314] [B-188] [B-189] [B-190] [B-191] [B-192]

[0315]

[0316] [B-193] [B-194] [B-195] [B-196] [B-197]

[0317]

[0318] (Dn refers to the number of deuterium atoms substituted, and indicates a structure in which one or more deuterium atoms are substituted)

[0319] The most specific structures according to the deuterium substitution position and substitution rate for compounds B-153 to B-197 of the above group 2 are presented as examples only, and there is no intention to limit the scope of rights to compounds not presented below.

[0320] The scope of the present invention is determined by the claims, and when deuterium is substituted, it is not limited to the compounds exemplified below, and the deuterium substitution position and deuterium substitution rate, etc. may include all ranges that can be changed within the range of Compound B-1 to Compound B-197.

[0321] [B-198] [B-199] [B-200]

[0322]

[0323] [B-201] [B-202] [B-203] [B-204]

[0324]

[0325] [B-205] [B-206] [B-207] [B-208]

[0326]

[0327] [B-209] [B-210] [B-211] [B-212]

[0328]

[0329] [B-213] [B-214] [B-215] [B-216]

[0330]

[0331] [B-217] [B-218] [B-219]

[0332]

[0333] [B-220] [B-221] [B-222] [B-223]

[0334]

[0335] [B-224] [B-225] [B-226] [B-227]

[0336]

[0337] [B-228] [B-229] [B-230] [B-231]

[0338]

[0339] [B-232] [B-233] [B-234] [B-235] [B-236]

[0340]

[0341] [C-1] [C-2] [C-3] [C-4]

[0342]

[0343] [C-5] [C-6] [C-7] [C-8]

[0344]

[0345] [C-9] [C-10] [C-11] [C-12]

[0346]

[0347] [C-13] [C-14] [C-15] [C-16]

[0348]

[0349] [C-17] [C-18] [C-19] [C-20]

[0350]

[0351] [C-21] [C-22] [C-23] [C-24]

[0352]

[0353] [C-25] [C-26] [C-27] [C-28]

[0354]

[0355] [C-29] [C-30] [C-31] [C-32]

[0356]

[0357] [C-33] [C-34] [C-35] [C-36]

[0358]

[0359] [C-37] [C-38] [C-39] [C-40]

[0360]

[0361] [C-41] [C-42] [C-43] [C-44]

[0362]

[0363] [C-45] [C-46] [C-47] [C-48]

[0364]

[0365] [C-49] [C-50] [C-51] [C-52]

[0366]

[0367] [C-53] [C-54] [C-55] [C-56]

[0368]

[0369] [C-57]

[0370]

[0371] Additionally, examples of compounds C-1 to C-57 listed in Group 2 above in which at least one hydrogen is replaced with deuterium are provided below, but are not limited thereto.

[0372] [C-58] [C-59] [C-60] [C-61] [C-62]

[0373]

[0374] [C-63] [C-64] [C-65] [C-66] [C-67]

[0375]

[0376] [C-68] [C-69] [C-70] [C-71] [C-72]

[0377]

[0378] (Dn refers to the number of deuterium atoms substituted, and indicates a structure in which one or more deuterium atoms are substituted)

[0379] The most specific structures according to the deuterium substitution position and substitution rate for compounds C-58 to C-72 of the above group 2 are presented as examples only, and there is no intention to limit the scope of rights for compounds not presented below.

[0380] The scope of the present invention is determined by the claims, and when deuterium is substituted, it is not limited to the compounds exemplified below, and the deuterium substitution position and deuterium substitution rate, etc. may include all ranges that can be changed within the range of Compound C-1 to Compound C-72.

[0381] [C-73] [C-74]

[0382]

[0383] [C-75] [C-76] [C-77] [C-78]

[0384]

[0385] [C-79] [C-80] [C-81] [C-82]

[0386]

[0387] [C-83] [C-84] [C-85] [C-86]

[0388]

[0389] [C-87] [C-88] [C-89] [C-90]

[0390]

[0391] [C-91] [C-92] [C-93] [C-94]

[0392]

[0393] [C-95] [C-96] [C-97] [C-98]

[0394]

[0395] [C-99] [C-100] [C-101] [C-102]

[0396]

[0397] The above second compound may be used in one or two or more types.

[0398] In the light-emitting layer (32), the first compound and the second compound may be included as hosts, and may be included in a weight ratio of, for example, about 1:99 to 99:1. By being included in the above range, the electron transport ability of the first compound and the hole transport ability of the second compound can be used to achieve an appropriate weight ratio to implement bipolar characteristics, thereby improving efficiency and lifespan. Within the above range, the first compound and the second compound may be included in a weight ratio of, for example, about 10:90 to 90:10, about 20:80 to 80:20, and may be included in a weight ratio of, for example, 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, the first compound and the second compound may be included in a weight ratio of 20:80, 30:70, or 40:60.

[0399] The light-emitting layer (32) may further include one or more compounds in addition to the first compound and the second compound described above as a host.

[0400] The light-emitting layer (32) may further include a dopant.

[0401] The dopant may be, for example, a phosphorescent dopant, for example, a red, green or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0402] Dopants are substances that are mixed in trace amounts into compounds for organic optoelectronic devices to cause luminescence. Typically, a metal complex that emits light through multiple excitation, which excites the triplet state or higher, may be used. Dopants may be, for example, inorganic, organic, or organic-inorganic compounds, and may be comprised of one or more types.

[0403] An example of a dopant is a phosphorescent dopant, and examples of a phosphorescent dopant include an organometallic compound containing 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 following chemical formula Z, but is not limited thereto.

[0404] [Chemical formula Z]

[0405] L 9 MX 1

[0406] In the above chemical formula Z, M is a metal, and L 9 and X 1 are ligands that are the same or different and form complexes with M.

[0407] The above M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or a combination thereof, and the above L 9 and X 1 may be, for example, a bidentate ligand.

[0408] L 9 and X 1 Examples of ligands represented by may be selected from, but are not limited to, the chemical formulas listed in Group A below.

[0409] [Group A]

[0410]

[0411] In the above group A,

[0412] R 300 Inland R 302 are each independently a C1 to C30 alkyl group substituted or unsubstituted with hydrogen, deuterium, halogen, a C6 to C30 aryl group substituted or unsubstituted with C1 to C30 alkyl, or halogen,

[0413] R 303 Inland R 324are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, 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.

[0414] The dopant according to one embodiment may be an iridium complex, for example, represented by the following chemical formula V-1 or chemical formula V-2.

[0415] [Chemical Formula V-1]

[0416]

[0417] In the above chemical formula V-1,

[0418] R 101 Inland R 116 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0419] The above R 132 Inland R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0420] R 101 Inland R 116 At least one of them is a functional group represented by the following chemical formula 6,

[0421] L100 is a bidentate ligand of a single anion, and is a ligand that coordinates to iridium through the unshared electron pair of carbon or a heteroatom.

[0422] n5 and n6 are independently any integer from 0 to 3, and n5 + n6 is any integer from 1 to 3,

[0423] [Chemical Formula 6]

[0424]

[0425] In the above chemical formula 6,

[0426] R 135 Inland R 139 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0427] * indicates a part connected to a carbon atom.

[0428] [Chemical Formula V-2]

[0429]

[0430] In the above chemical formula V-2,

[0431] R 101 Inland R 117 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -Si R 133 R 134 R 135 And,

[0432] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0433] L 100is a bidentate ligand of a single anion, and is a ligand that coordinates to iridium through the unshared electron pair of carbon or a heteroatom.

[0434] n1 and n2 are independently any integers from 0 to 3, and n1 + n2 is any integer from 1 to 3.

[0435] In another embodiment, the dopant may be a platinum complex, for example represented by the chemical formula Z-1.

[0436] [Chemical Formula Z-1]

[0437]

[0438] In the above chemical formula Z-1, rings A, B, C, and D each independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0439] R A , R B , R C , and R D each independently represents monosubstitution, disubstitution, trisubstitution, tetrasubstitution, or no substitution;

[0440] L B , L C , and L D are independently selected from the group consisting of direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof;

[0441] If nA is 1, L E is selected from the group consisting of direct bonds, 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;

[0442] R A , R B , R C , R D, R, and R' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, heteroalkyl group, arylalkyl group, alkoxy group, aryloxy group, amino group, silyl group, alkenyl group, cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof; any adjacent R A , R B , R C , R D , R, and R' are randomly connected to form a ring; X B , X C , X D , and X E are independently selected from the group consisting of carbon and nitrogen; Q 1 , Q 2 , Q 3 , and Q 4 represent oxygen or direct bonds, respectively.

[0443] In one embodiment, the dopant may be a platinum complex, and may be represented by, for example, the following chemical formula (VI-1) or chemical formula (VI-2).

[0444] [Chemical Formula Ⅵ-1] [Chemical Formula Ⅵ-2]

[0445]

[0446] In the above chemical formulas Ⅵ-1 and Ⅵ-2,

[0447] X 100 Silver O, S and NR 131 Selected from among,

[0448] R 118 Inland R 132 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -Si R 133 R 134 R 135 And,

[0449] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0450] R 118 Inland R 132 At least one of them is -SiR 133 R 134 R 135 or tert-butyl group.

[0451] The hole transport auxiliary layer (33) includes a third compound having a bipolar characteristic with relatively strong hole characteristics.

[0452] As described above, the light-emitting layer (32) can significantly improve the light-emitting efficiency by increasing the mobility of electrons and holes compared to when used alone by including a first compound having a bipolar characteristic with relatively strong electron characteristics and a second compound having relatively strong hole characteristics.

[0453] Devices that introduce materials with biased electron or hole properties into the light-emitting layer exhibit a relatively high rate of exciton formation due to carrier recombination at the interface between the light-emitting layer and the electron or charge transport layer. As a result, the interaction between molecular excitons in the light-emitting layer and charges at the interface of the hole transport layer causes a rapid drop in efficiency, a roll-off phenomenon, and a rapid decline in luminescence lifetime characteristics.

[0454] In order to solve this problem, the first and second compounds are simultaneously introduced into 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 additionally, a hole transport auxiliary layer including a third compound having relatively strong hole characteristics is included 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 manufacturing a device capable of adjusting carrier balance within the light-emitting layer. Accordingly, the roll-off characteristics of the organic optoelectronic device can be improved while also significantly improving the lifespan characteristics.

[0455] The third compound can be represented by the following chemical formula 5.

[0456] [Chemical Formula 5]

[0457]

[0458] In the above chemical formula 5,

[0459] Ar 8 and Ar 9 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0460] The above Ar 10 and Ar 11 are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

[0461] R 41 Inland R 45 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0462] m5 is an integer between 1 and 3.

[0463] If m5 is 2 or more, each R 41may be identical or different.

[0464] The above third compound has a structure in which at least one fluorene group is substituted on the amine core.

[0465] By substituting at least one fluorene group in the amine core, the steric hindrance can be used to minimize thermal degradation by reducing the deposition temperature, thereby further improving the life characteristics.

[0466] For example, the third compound can be represented by any one of the following chemical formulas 5-1 to 5-4, depending on the substitution position of fluorene.

[0467] [Chemical Formula 5-1] [Chemical Formula 5-2]

[0468]

[0469] [Chemical Formula 5-3] [Chemical Formula 5-4]

[0470]

[0471] In the above chemical formulas 5-1 to 5-4,

[0472] Ar 8 Inland Ar 11 , R 41 Inland R 45 And the definition of m5 is as described above.

[0473] For example, the third compound can be expressed by the chemical formula 5-4.

[0474] In the above chemical formula 5, Ar 8 and Ar 9 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 fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0475] For example, the above Ar 8and Ar 9 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted fluorenyl group.

[0476] In the above chemical formula 5, Ar 10 and Ar 11 Each of may independently be a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0477] For example, the above Ar 10 and Ar 11 Each of may independently be a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0478] In the above chemical formula 5, R 41 Inland R 45 may each independently be hydrogen, deuterium, or a substituted or unsubstituted C1 to C5 alkyl group.

[0479] For example, the above R 41 Inland R 45 can each independently be hydrogen, deuterium or tert-butyl group.

[0480] The above Ar 8 and Ar 9 At least one of them may be a substituted or unsubstituted fluorenyl group, and may be represented by, for example, the following chemical formula 5-4-1.

[0481] [Chemical Formula 5-4-1]

[0482]

[0483] In the above chemical formula 5-4-1,

[0484] Ar 9 Inland Ar 11 , R 41 Inland R 45 And the definition of m5 is as described above,

[0485] Ar 12 and Ar13 are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

[0486] R 53 Inland R 57 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0487] m13 is an integer between 1 and 3.

[0488] In the above chemical formula 5-4-1, when m13 is 2 or more, each R 53 may be identical or different.

[0489] In the above chemical formula 5-4-1, Ar 12 and Ar 13 Each may independently be a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0490] For example, the above Ar 12 and Ar 13 Each of may independently be a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0491] In the above chemical formula 5-4-1, R 53 Inland R 57 may each independently be hydrogen, deuterium, or a substituted or unsubstituted C1 to C5 alkyl group.

[0492] For example, the above R 53 Inland R 57 can each independently be hydrogen, deuterium or tert-butyl group.

[0493] As a more specific example, the chemical formula 5-4-1 may be selected from the following chemical formulas 5-4-1a, 5-4-1b, 5-4-1c, and 5-4-1d.

[0494] [Chemical Formula 5-4-1a] [Chemical Formula 5-4-1b]

[0495]

[0496] [Chemical Formula 5-4-1c] [Chemical Formula 5-4-1d]

[0497]

[0498] In the above chemical formulas 5-4-1a, 5-4-1b, 5-4-1c, and 5-4-1d,

[0499] Ar 9 Inland Ar 13 , R 41 Inland R 45 , R 53 Inland R 57 , m5 and m13 are defined as described above.

[0500] As a most specific example, the third compound can be represented by the chemical formula 5-4-1b.

[0501] For example, R of the above chemical formula 5 42 Inland R 45 At least two of them can be tert-butyl groups.

[0502] Heat resistance can be improved by introducing an alkyl group that can improve the glass transition temperature.

[0503] As a specific example, R of the above chemical formula 5-4-1 42 Inland R 45 At least two of them or R 54 Inland R 57 At least two of them can be tert-butyl groups.

[0504] For example, R in the above chemical formula 5 43 and R 45 Each may be a tert-butyl group.

[0505] For example, R of the chemical formula 5-4-1 43 and R 45 Each may be a tert-butyl group.

[0506] For example, R of the chemical formula 5-4-1 54 and R 56 Each may be a tert-butyl group.

[0507] For example, the third compound may be, but is not limited to, one selected from the compounds listed in Group 3 below.

[0508] [Group 3]

[0509] [E-1] [E-2] [E-3] [E-4]

[0510]

[0511] [E-5] [E-6] [E-7] [E-8]

[0512]

[0513] [E-9] [E-10] [E-11] [E-12]

[0514]

[0515] [E-13] [E-14] [E-15] [E-16]

[0516]

[0517] [E-17] [E-18] [E-19] [E-20]

[0518]

[0519] [E-21] [E-22] [E-23] [E-24]

[0520]

[0521] [E-25] [E-26] [E-27] [E-28]

[0522]

[0523] [E-29] [E-30] [E-31] [E-32]

[0524]

[0525] [E-33] [E-34] [E-35] [E-36]

[0526]

[0527] [E-37] [E-38] [E-39] [E-40]

[0528]

[0529] [E-41] [E-42] [E-43] [E-44]

[0530]

[0531] [E-45] [E-46] [E-47] [E-48]

[0532]

[0533] [E-49] [E-50] [E-51] [E-52]

[0534]

[0535] [E-53] [E-54] [E-55] [E-56]

[0536]

[0537] [E-57] [E-58] [E-59] [E-60]

[0538]

[0539] [E-61] [E-62] [E-63] [E-64]

[0540]

[0541] [E-65] [E-66] [E-67] [E-68]

[0542]

[0543] [E-69] [E-70] [E-71] [E-72]

[0544]

[0545] In a most specific embodiment of the present invention, the first compound may be represented by the chemical formula 1, the second compound may be represented by the chemical formula 2-8 or chemical formula 3C, and the third compound may be represented by the chemical formula 5-4-1b.

[0546] Additionally, the organic layer (30) may further include an electron transport region.

[0547] The above electron transport region can further increase electron injection and / or electron mobility between the cathode (20) and the light-emitting layer (32) and block holes.

[0548] 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 below may be included in at least one layer of the electron transport layer and the electron transport auxiliary layer.

[0549] [Group B]

[0550]

[0551]

[0552]

[0553]

[0554]

[0555]

[0556]

[0557]

[0558]

[0559]

[0560]

[0561]

[0562]

[0563]

[0564]

[0565]

[0566]

[0567] Meanwhile, the organic light-emitting device may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. in addition to the light-emitting layer as the aforementioned organic layer.

[0568] An organic light-emitting device can be manufactured by forming an anode or cathode on a substrate, forming an organic layer using a dry film deposition method such as evaporation, sputtering, plasma plating, or ion plating, and then forming a cathode or anode thereon.

[0569] The above-described organic light-emitting device can be applied to an organic light-emitting display device.

[0570] The implementation examples described above are described in more detail through the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of the rights.

[0571] The starting materials and reactants used in the examples and synthesis examples below were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry or P&H Tech, or synthesized using known methods, unless otherwise specified.

[0572]

[0573] As a more specific example of the compound of the present invention, the compound presented was synthesized through the following steps.

[0574] Synthesis of the first compound

[0575] Synthesis Example 1: Synthesis of Compound A-43

[0576] [Reaction Formula 1]

[0577]

[0578] Step 1: Synthesis of intermediate Int-1

[0579] 2,4-Dichloro-6-phenyl-1,3,5-triazine (20.0 g, 88.5 mmol), 3-dibenzofuranylboronic acid (17.8 g, 84.1 mmol), K2CO3 (24.5 g, 176.9 mmol), and Pd(dppf)Cl2 (3.6 g, 4.4 mmol) were placed in a round-bottom flask, dissolved in toluene (250 ml) and distilled water (90 ml), and stirred at 60°C for 6 hours. After the reaction was completed, the aqueous layer was separated using a separatory funnel, and the organic layer was distilled under reduced pressure. The mixture was heated to dissolve with monochlorobenzene, filtered through silica, and recrystallized to obtain 14.4 g (48%) of intermediate Int-1.

[0580] Step 2: Synthesis of intermediate Int-2

[0581] Intermediate Int-1 (14.4 g, 40.2 mmol), 5-Chloro-2-fluorophenylboronic acid (6.8 g, 39.0 mmol), K2CO3 (10.8 g, 78.0 mmol), and Pd(PPh3)4 (2.25 g, 1.95 mmol) were placed in a round-bottomed flask, dissolved in THF (180 ml) and distilled water (40 ml), and stirred under reflux at 55°C for 6 hours. After the reaction was completed, the aqueous layer was removed and column chromatography (Hexane:DCM (30%)) was used to obtain 13.2 g (75%) of intermediate Int-2.

[0582] Step 3: Synthesis of intermediate Int-3

[0583] Intermediate Int-2 (13.2g, 29.2mmol), Phenylboronic acid (10.7g, 86.6mmol),

[0584] Cs2CO3 (19.0 g, 58.4 mmol), Tri-tert-butylphosphine (2.9 ml, 5.8 mmol), and Pd2(dba)3 (1.3 g, 1.5 mmol) were placed in a round-bottomed flask, dissolved in 1,4-dioxane (120 ml), and refluxed at 100°C for 8 hours. After the reaction was complete, cooled to room temperature, the reactant was poured into an excess of methanol to precipitate a solid, and then filtered to obtain the solid, which was recrystallized with monochlorobenzene to obtain 10.8 g (75%) of intermediate Int-3.

[0585] Step 4: Synthesis of compound A-43

[0586] Intermediate Int-3 (10.8 g, 21.9 mmol), 2-Phenyl-9H-carbazole (6.4 g, 26.3 mmol), and K3PO4 (9.3 g, 43.8 mmol) were placed in a round-bottomed flask, dissolved in DMF (100 ml), and stirred under reflux at 150°C for 4 hours. After the reaction was complete, the reactants were slowly added dropwise to an excess of water to precipitate a solid, which was then filtered and the obtained solid was recrystallized with toluene to obtain 12.6 g (80%) of compound A-43.

[0587]

[0588] Synthesis Example 2: Synthesis of Compound A-44

[0589] [Reaction Formula 2]

[0590]

[0591]

[0592]

[0593] Step 1: Synthesis of intermediate Int-5

[0594] Using 2,4-Dichloro-6-phenyl-1,3,5-triazine (30.0 g, 132.7 mmol), intermediate Int-4 (46.7 g, 126.1 mmol), K2CO3 (36.7 g, 265.4 mmol), and Pd(dppf)Cl2 (5.42 g, 6.64 mmol), the same method as step 1 of Synthetic Example 1 was used to obtain 45.6 g (83%) of intermediate Int-5.

[0595] Step 2: Synthesis of intermediate Int-6

[0596] 1-Bromo-3-chloro-2-fluorobenzene (25.0 g, 119.4 mmol), Phenylboronic acid (16.0 g, 131.3 mmol), K2CO3 (33.0 g, 238.7 mmol), and Pd(PPh3)4 (6.9 g, 6.0 mmol) were placed in a round-bottomed flask, dissolved in THF (350 ml) and distilled water (120 ml), and stirred under reflux at 65°C for 6 hours. After the reaction was completed, the aqueous layer was removed and column chromatography (Hexane:DCM (20%)) was used to obtain 21.7 g (88%) of intermediate Int-6.

[0597] Step 3: Synthesis of intermediate Int-7

[0598] Intermediate Int-6 (21.7 g, 105.0 mmol), Bis(pinacolato)diboron (32.0 g, 126.0 mmol), Tricyclohexylphosphine (5.1 g, 21.0 mmol), Potassium acetate (20.6 g, 210.0 mmol), and Pd(dppf)Cl2 (4.29 g, 5.25 mmol) were placed in a round-bottomed flask and dissolved in 250 ml of DMF. The mixture was refluxed and stirred at 140 °C for 8 hours. After the reaction was completed, cooled to room temperature, filtered to remove salts, and then extracted with excess DCM and distilled water. Column chromatography (Hexane:DCM (30% to 50%)) yielded 25.1 g (80%) of intermediate Int-7.

[0599] Step 4: Synthesis of intermediate Int-8

[0600] Intermediate Int-5 (14.5 g, 33.4 mmol), intermediate Int-7 (11.0 g, 36.8 mmol), K2CO3 (9.2 g, 66.8 mmol), and Pd(PPh3)4 (1.93 g, 1.67 mmol) were placed in a round-bottomed flask, dissolved in THF (170 ml) and distilled water (40 ml), and stirred under reflux at 70°C for 6 hours. After the reaction was completed, the aqueous layer was removed and column chromatography (Hexane:DCM (30%)) was used to obtain 13.3 g (70%) of intermediate Int-8.

[0601] Step 5: Synthesis of Compound A-44

[0602] Intermediate Int-8 (13.3 g, 23.4 mmol), 9H-Carbazole (4.7 g, 28.0 mmol), and K3PO4 (9.9 g, 46.7 mmol) were placed in a round-bottomed flask, dissolved in DMF (100 ml), and stirred under reflux at 150°C for 4 hours. After the reaction was complete, the reactants were slowly added dropwise to an excess of water to precipitate a solid, which was then filtered and the obtained solid was recrystallized with monochlorobenzene to obtain 14.1 g (84%) of compound A-44.

[0603]

[0604] Synthesis Example 3: Synthesis of Compound A-77

[0605] [Reaction Formula 3]

[0606]

[0607] Compound A-77 was synthesized using the same method as step 4 of Synthetic Example 1 using intermediate Int-9 (CAS No.1642330-72-0) and 2-Phenyl-9H-carbazole.

[0608]

[0609] Synthesis Example 4: Synthesis of Compound A-90

[0610] [Reaction Formula 4]

[0611]

[0612] Compound A-90 was synthesized using the same method as step 1 of Synthetic Example 1 using intermediate Int-10 (CAS No. 2745196-22-7) and intermediate Int-11 (CAS No. 1189047-28-6).

[0613]

[0614] Comparative Synthesis Example 1: Synthesis of Compound Host-1

[0615]

[0616] Compound Host-1 was synthesized with reference to the synthetic method disclosed in the published publication WO2023 / 072977.

[0617]

[0618] Synthesis of the second compound

[0619] Synthesis Example 5: Synthesis of Compound B-136

[0620]

[0621] Compound B-136 was synthesized by referring to the synthetic method disclosed in registered patent US 10476008 B2.

[0622] HRMS (70eV, EI+): m / z calcd for C42H28N2: 560.2252, found: 560.

[0623] Elemental Analysis: C, 90%; H, 5%

[0624]

[0625] Synthesis of the third compound

[0626] Synthesis Example 6: Synthesis of Compound E-1

[0627] [Reaction Formula 5]

[0628]

[0629] In a round-bottomed flask, 410 g (1.203 mol) of intermediate E-1-1 (CAS No. 2924473-03-8), 435 g (1.082 mol) of amine intermediate (CAS No. 897674-69-1), and 173 g (1.804 mol) of sodium t-butoxide were placed and dissolved in 4000 ml of toluene. To this, 55 g (0.06 mol) of Pd2(dba)3 and 74 g (0.18 mol) of S-phos were sequentially added, and the mixture was refluxed and stirred for 6 hours under a nitrogen atmosphere. After completion of the reaction, the toluene solvent was removed, extracted with toluene and distilled water, and the organic layer was dried over magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by n-hexane / methanol recrystallization to obtain 600 g (yield 71%) of compound E-1.

[0630]

[0631] Synthesis Example 7: Synthesis of Compound E-21

[0632] [Reaction Formula 6]

[0633]

[0634] Compound E-21 was synthesized using the same method as in Synthesis Example 6 using intermediate E-1-1 and amine intermediate (CAS NO. 500717-23-7).

[0635]

[0636] (Fabrication of organic light-emitting devices)

[0637] Example 1

[0638] A glass substrate coated with a thin film of ITO (Indium tin oxide) was ultrasonically washed in distilled water. After washing with distilled water, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned for 10 minutes using oxygen plasma and then transferred to a vacuum deposition machine. Using the ITO transparent electrode prepared in this way as an anode, Compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum-deposited on the ITO substrate to form a 100Å thick hole injection layer, and Compound A was deposited on the hole injection layer to a thickness of 1350Å to form a hole transport layer. Compound E-21 obtained in Synthesis Example 8 was deposited on the hole transport layer to a thickness of 270Å to form a first hole transport auxiliary layer, and Compound B was deposited on the first hole transport auxiliary layer to a thickness of 50Å to form a second hole transport auxiliary layer. On the second hole transport auxiliary layer, 85 wt% of compound A-43 (40%) synthesized in Synthesis Example 1 and compound B-136 (60%) synthesized in Synthesis Example 5 were used as hosts, and 15 wt% of PtGD was doped as a dopant to form a 380 Å thick light-emitting layer by vacuum deposition. Subsequently, compound C was deposited on the light-emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compound D and Liq were simultaneously vacuum-deposited at a weight ratio of 1:1 to form an electron transport layer to a thickness of 310 Å. On the electron transport layer, 15 Å of Yb and 1200 Å of Al were sequentially vacuum-deposited to form a cathode, thereby manufacturing an organic light-emitting device.

[0639] It was fabricated with the structure of ITO / Compound A (3% NDP-9 doping, 100Å) / Compound A (1350Å) / First hole transport auxiliary layer (270Å) / Compound B (50Å) / Emitting layer [Host (Compound A-43: Compound B-136 = 40:60) : PtGD = 85 wt% : 15 wt%] (380Å) / Compound C (50Å) / Compound D : Liq (310Å) / Yb (15Å) / Al (1200Å).

[0640] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine

[0641] Compound B: 9,9-dimethyl-N-[3-(9-phenyl-9H-fouoren-9-yl)phenyl]-N-(4-phenylphenyl)-9H-fluoren-2-amine

[0642] Compound C: 4-{4-[3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[0643] Compound D: 2-(4-{1-[4-(diphenyl-1,3,5-triazin-2-yl)phenyl]naphthalen-2-yl}phenyl)-4,6-diphenyl-1,3,5-triazine

[0644] PtGD:

[0645]

[0646]

[0647] Examples 2 to 4 and Comparative Example 1

[0648] Devices of Examples 2 to 4 and Comparative Example 1 were manufactured in the same manner as in Example 1, except that the host was changed as described in Table 1 below.

[0649]

[0650] evaluation

[0651] The luminous efficiency characteristics of the organic light-emitting devices according to Examples 1 to 4 and Comparative Example 1 were evaluated.

[0652] The specific measurement method is as follows, and the results are as shown in Table 1.

[0653] (1) Measurement of changes in current density according to voltage changes

[0654] For the manufactured organic light-emitting device, the current flowing through the unit device was measured using a current-voltage meter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain the result.

[0655] (2) Measurement of luminance change according to voltage change

[0656] For the manufactured organic light-emitting device, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V, and the results were obtained.

[0657] (3) Measurement of luminous efficiency

[0658] Using the luminance, current density, and voltage measured from the above (1) and (2), the same current density (10 mA / cm 2 ) was calculated for the current efficiency (cd / A).

[0659] The luminous efficiency values ​​of Examples 1 to 4 and Comparative Example 1 were calculated as relative values ​​based on Comparative Example 1 and are listed in Table 1 below.

[0660] No. Host hole transport auxiliary layer luminescence efficiency (%) Compound 1 Compound 2 Compound 3 Example 1A-43B-136E-21110 Example 2A-44B-136E-21109 Example 3A-77B-136E-21109 Example 4A-90B-136E-21112 Comparative Example 1 Host-1B-136E-21100

[0661] Referring to Table 1, it can be confirmed that the organic light-emitting device to which the composition according to the embodiment of the present invention is applied has a significantly improved luminous efficiency compared to the organic light-emitting device according to the comparative example.

[0662] Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic concept of the present invention defined in the following claims also fall within the scope of the present invention.

Claims

1. Positive and negative poles facing each other, A light-emitting layer positioned between the anode and the cathode, A hole transport layer positioned between the anode and the light-emitting layer, and A hole transport auxiliary layer located between the above light-emitting layer and the above hole transport layer Including, The above light-emitting layer comprises a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2; or a combination of the following chemical formulas 3 and 4, The above hole transport auxiliary layer is an organic optoelectronic device including a third compound represented by the following chemical formula 5: [Chemical Formula 1] In the above chemical formula 1, Z 1 Inland Z 3 are each independently N or CR a And, Z 1 Inland Z 3 At least two of them are N, R 1 Inland R 8 and R a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, L 1 Inland L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heterocyclic group, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group; [Chemical Formula 2] In the above chemical formula 2, 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, L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 9 Inland R 19 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m1 and m2 are each independently an integer from 1 to 3, m3 is one of the integers 1 to 4, n is an integer between 0 and 2; [Chemical Formula 3] [Chemical Formula 4] In the above chemical formulas 3 and 4, Ar 5 and Ar 6 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, In chemical formula 3, a1* to a4* are each independently a connecting carbon (C) or CL a -R b And, In chemical formula 4, * each independently represents a connecting carbon (C), Among a1* to a4* in chemical formula 3, two adjacent ones are each connected to * in chemical formula 4, L a , L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R b and R 20 Inland R 27 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group; [Chemical Formula 5] In the above chemical formula 5, Ar 8 and Ar 9 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, The above Ar 10 and Ar 11 are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, R 41 Inland R 45 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m5 is an integer between 1 and 3.

2. In paragraph 1, Ar of the above chemical formula 1 1 and Ar 2 An organic optoelectronic device, wherein each independently represents 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 phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzosilolyl group, or a substituted or unsubstituted carbazolyl group.

3. In paragraph 1, L of the above chemical formula 1 1 -Ar 1 and L 2 -Ar 2 An organic optoelectronic device, wherein each of the substituents is independently selected from the substituents listed in Group Ⅰ below: [Group Ⅰ] In the above group Ⅰ, R 46 Inland R 48 are each independently hydrogen, deuterium, cyano, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, m6 is one of the integers 1 to 5, m7 is one of the integers 1 to 4, m8 is one of the integers 1 to 3, * is a connection point.

4. In paragraph 1, The organic optoelectronic device wherein the first compound is one selected from the compounds listed in Group 1 below: [Group 1] [A-1] [A-2] [A-3] [A-4] [A-5] [A-6] [A-7] [A-8] [A-9] [A-10] [A-11] [A-12] [A-13] [A-14] [A-15] [A-16] [A-17] [A-18] [A-19] [A-20] [A-21] [A-22] [A-23] [A-24] [A-25] [A-26] [A-27] [A-28] [A-29] [A-30] [A-31] [A-32] [A-33] [A-34] [A-35] [A-36] [A-37] [A-38] [A-39] [A-40] [A-41] [A-42] [A-43] [A-44] [A-45] [A-46] [A-47] [A-48] [A-49] [A-50] [A-51] [A-52] [A-53] [A-54] [A-55] [A-56] [A-57] [A-58] [A-59] [A-60] [A-61] [A-62] [A-63] [A-64] [A-65] [A-66] [A-67] [A-68] [A-69] [A-70] [A-71] [A-72] [A-73] [A-74] [A-75] [A-76] [A-77] [A-78] [A-79] [A-80] [A-81] [A-82] [A-83] [A-84] [A-85] [A-86] [A-87] [A-88] [A-89] [A-90] [A-91] [A-92] [A-93] [A-94] [A-95] [A-96] [A-97] [A-98] [A-99] [A-100] [A-101] [A-102] [A-103] [A-104] [A-105] [A-106] [A-107] [A-108] [A-109] [A-110] [A-111] [A-112] [A-113] [A-114] [A-115] [A-116] [A-117] [A-118] [A-119] [A-120] .

5. In paragraph 1, The above chemical formula 2 is an organic optoelectronic device represented by the following chemical formula 2-8. [Chemical Formula 2-8] In the above chemical formula 2-8, R 9 Inland R 18 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, m1 and m2 are each independently an integer from 1 to 3, L 4 -Ar 3 and L 5 -Ar 4 is independently one of the substituents listed in Group II below, [Group II] In the above group II, R 49 Inland R 52 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, m9 is one of the integers 1 to 5, m10 is one of the integers 1 to 4, m11 is one of the integers 1 to 3, m12 is an integer of 1 or 2, * is a connection point.

6. In paragraph 1, The combination of the above chemical formulas 3 and 4 is an organic optoelectronic device represented by the following chemical formula 3: [Chemical Formula 3C] In the above chemical formula 3C, L a3 and L a4 is a single bond, R 20 Inland R 27 , R b3 and R b4 are each independently hydrogen or a C6 to C12 aryl group, L 6 -Ar 5 and L 7 -Ar 6 is independently one of the substituents listed in Group II below, [Group II] In the above group II, R 49 Inland R 52 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, m9 is one of the integers 1 to 5, m10 is one of the integers 1 to 4, m11 is one of the integers 1 to 3, m12 is an integer of 1 or 2, * is a connection point.

7. In paragraph 1, The above chemical formula 5 is an organic optoelectronic device represented by the following chemical formula 5-4: [Chemical Formula 5-4] In the above chemical formula 5-4, Ar 8 Inland Ar 11 , R 41 Inland R 45 and m5 are as defined in chemical formula 5.

8. In paragraph 7, The above chemical formula 5-4 is an organic optoelectronic device represented by the following chemical formula 5-4-1: [Chemical Formula 5-4-1] In the above chemical formula 5-4-1, Ar 9 Inland Ar 11 , R 41 Inland R 45 and m5 are as defined in paragraph 1, Ar 12 and Ar 13 are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, R 53 Inland R 57 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m13 is an integer between 1 and 3.

9. In paragraph 8, The above chemical formula 5-4-1 is an organic optoelectronic device represented by the following chemical formula 5-4-1b: [Chemical Formula 5-4-1b] In the above chemical formula 5-4-1b, Ar 9 Inland Ar 13 , R 41 Inland R 45 , R 53 Inland R 57 , m5 and m13 are as defined in chemical formula 5-4-1.

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

11. In paragraph 1, The second compound is represented by the following chemical formula 2-8 or chemical formula 3C, The third compound is an organic optoelectronic device represented by the following chemical formula 5-4-1b: [Chemical Formula 2-8] In the above chemical formula 2-8, R 9 Inland R 18 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, m1 and m2 are each independently an integer from 1 to 3, L 4 -Ar 3 and L 5 -Ar 4 is independently one of the substituents listed in Group II below, [Group II] In the above group II, R 49 Inland R 52 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, m9 is one of the integers 1 to 5, m10 is one of the integers 1 to 4, m11 is one of the integers 1 to 3, m12 is an integer of 1 or 2, * is the connection point; [Chemical Formula 3C] In the above chemical formula 3C, L a3 and L a4 is a single bond, R 20 Inland R 27 , R b3 and R b4 are each independently hydrogen or a C6 to C12 aryl group, L 6 -Ar 5 and L 7 -Ar 6 is independently one of the substituents listed in Group II below, [Group II] In the above group II, R 49 Inland R 52 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, m9 is one of the integers 1 to 5, m10 is one of the integers 1 to 4, m11 is one of the integers 1 to 3, m12 is an integer of 1 or 2, * is the connection point; [Chemical Formula 5-4-1b] In the above chemical formula 5-4-1b, Ar 10 and Ar 11 are each independently a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, Ar 12 and Ar 13 are each independently a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, R 41 Inland R 45 and R 53 Inland R 57 are each independently hydrogen, deuterium, or a substituted or unsubstituted C1 to C5 alkyl group, Ar 9 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, m5 and m13 are each independently an integer from 1 to 3.

12. A display device comprising an organic optoelectronic device according to any one of claims 1 to 11.

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