Organic optoelectronic device and display device

Abstract

An organic optoelectronic device 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. The light-emitting layer includes a first compound represented by Chemical Formula 1 and a second compound represented by a combination of Chemical Formula 2 or Chemical Formula 3 and Chemical Formula 4, and the hole transport auxiliary layer includes a third compound represented by Chemical Formula 5. Details regarding Chemical Formulas 1 to 5 are as defined in the specification.

Description

Technical Field

[0001] Relates to an organic optoelectronic device and a display device.

Background Art

[0002] An organic optoelectronic diode is a device that can convert electrical energy and light energy into each other.

[0003] Organic optoelectronic devices can be roughly classified into two types according to their operating principles. One is a photoelectric device in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are respectively transmitted to other electrodes to generate electrical energy. The other is a light-emitting device that supplies a voltage or current to an electrode to generate light energy from electrical energy.

[0004] Examples of organic optoelectronic devices include organic photoelectric devices, organic light-emitting devices, organic solar cells, and organic photo conductor drums.

[0005] Among them, organic light emitting diodes (OLEDs) have recently attracted much attention due to the increasing demand for flat panel display devices. An organic light-emitting device is a device that converts electrical energy into light, and the performance of an organic light-emitting device is greatly affected by the organic material located between the electrodes.

Summary of the Invention

Problems to be Solved by the Invention

[0006] One embodiment provides an organic optoelectronic device capable of realizing long-life characteristics.

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

Means for Solving the Problems

[0008] According to one embodiment, there is provided an organic optoelectronic device including a positive electrode and a negative electrode facing each other, a light-emitting layer positioned between the positive electrode and the negative electrode, a hole transport layer positioned between the positive electrode 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 Formula 3 and Chemical Formula 4, and the hole transport auxiliary layer includes a third compound represented by the following Chemical Formula 5.

[0009] [Chemical Formula 1] [Chem.]

[0010] In Chemical Formula 1, Ar 1 ~Ar 3 are each independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, L 1 ~L 4 are each independently a single bond or a substituted or unsubstituted C6-C20 arylene group, R 1 ~R 3 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group, m1 and m3 are each independently one of the integers from 1 to 4, m2 is an integer of 1 or 2.

[0011] [Chemical Formula 2] [Chem.]

[0012] In Chemical Formula 2, Ar 4 and Ar5 is each independently a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, Ar 10 ~Ar 13 is each independently hydrogen or a substituted or unsubstituted C6-C30 aryl group, L 5 and L 6 is each independently a single bond or a substituted or unsubstituted C6-C20 arylene group, R 4 ~R 8 is each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, m4, m7 and m8 are each independently one of the integers from 1 to 4, m5 and m6 are each independently one of the integers from 1 to 3, n is one of the integers from 0 to 2.

[0013]

Chemical formula

[0014] In the above Chemical formula 3 and Chemical formula 4, Ar 6 and Ar 7 are each independently a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, a1 * ~a4 * in Chemical formula 3 is each independently a linking carbon (C) or C-L a -R a and, a1 * ~a4 * in Chemical formula 3, two adjacent ones of which are each linked to * in Chemical formula 4, L a 、L7 and L 8 is each independently a single bond or a substituted or unsubstituted C6-C20 arylene group, R a , R 9 and R 10 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, m9 and m10 are each independently one of the integers from 1 to 4.

[0015] [Chemical Formula 5]

Chemical Structure

[0016] In the Chemical Formula 5, X 1 is C or Si, R 11 ~R 14 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, R 15 and R 16 are each independently a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group, Ar 8 is a substituted or unsubstituted C6-C30 aryl group, Ar 9 is a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted dibenzosilyl group, L 9 ~L 11 are each independently a single bond or a substituted or unsubstituted C6-C20 arylene group, m11, m12, and m14 are each independently one of the integers from 1 to 4, m13 is one of the integers from 1 to 3.

[0017] According to another embodiment, a display device including the organic optoelectronic device is provided.

Effects of the Invention

[0018] An organic optoelectronic device with long-life characteristics can be realized.

Brief Description of the Drawings

[0019]

Figure 1

Modes for Carrying Out the Invention

[0020] Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, and the present invention is not limited thereby. The present invention is only defined by the scope of the claims described later.

[0021] In this specification, "substituted" means that, unless otherwise defined, at least one hydrogen of a substituent or a compound is substituted with deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1-C30 amine group, a nitro group, a substituted or unsubstituted C1-C40 silyl group, a C1-C30 alkyl group, a C1-C10 alkylsilyl group, a C6-C30 arylsilyl group, a C3-C30 cycloalkyl group, a C3-C30 heterocycloalkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, a C1-C20 alkoxy group, a C1-C10 trifluoroalkyl group, a cyano group, or a combination thereof.

[0022] In this specification, "unsubstituted" means that a hydrogen atom is not substituted with another substituent and remains as a hydrogen atom.

[0023] In this specification, "deuterium substitution (-D)" can include "tritium substitution (-T)".

[0024] In an example of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1-C30 alkyl group, a C1-C10 alkylsilyl group, a C6-C30 arylsilyl group, a C3-C30 cycloalkyl group, a C3-C30 heterocycloalkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, or a cyano group. Also, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1-C20 alkyl group, a C6-C30 aryl group, or a cyano group. Further, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1-C5 alkyl group, a C6-C18 aryl group, or a cyano group.

[0025] Also, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, 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.

[0026] In this specification, "hetero" means, unless otherwise defined, containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, P, and Si in one functional group, and the rest being carbon.

[0027] As used herein, the term "aryl group" is a general concept encompassing groups having one or more hydrocarbon aromatic moieties, where all elements of the hydrocarbon aromatic moiety have p-orbitals and these p-orbitals form a conjugation, such as a phenyl group, a naphthyl group, etc., and forms in which two or more hydrocarbon aromatic moieties are linked via a sigma bond, such as a biphenyl group, a terphenyl group, a quarterphenyl group, etc., and can include non-aromatic fused rings in which two or more hydrocarbon aromatic moieties are directly or indirectly fused, such as a fluorenyl group, etc.

[0028] An aryl group includes monocyclic, polycyclic or fused-ring polycyclic (i.e., rings sharing adjacent pairs of carbon atoms) functional groups.

[0029] As used herein, the term "heterocyclic group" is a superordinate concept including heteroaryl groups, and means containing at least one heteroatom selected from the group consisting of N, O, S, P and Si in place 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, it can contain one or more heteroatoms in the whole heterocyclic group or in each ring thereof.

[0030] As an example, the term "heteroaryl group" means containing at least one heteroatom selected from the group consisting of N, O, S, P and Si in an aryl group. Two or more heteroaryl groups can be directly linked via a sigma bond, or when the heteroaryl group contains two or more rings, the two or more rings can be fused to each other. When the heteroaryl group is a fused ring, each ring can contain 1 to 3 of the heteroatoms.

[0031] More specifically, the substituted or unsubstituted C6-C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof, but is not limited thereto.

[0032] More specifically, the substituted or unsubstituted C2-C30 heterocyclic group may be 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 indole group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted 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, or an unsubstituted benzothiazinyl 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, but is not limited thereto.

[0033] In this specification, the hole property refers to the property that can donate electrons to form holes when an electric field is applied, has a conduction property along the HOMO level, and means the property that facilitates the injection of holes formed from the positive electrode into the light-emitting layer, the movement of holes formed from the light-emitting layer to the positive electrode, and the movement to the light-emitting layer.

[0034] Also, the electron property means the property that can accept electrons when an electric field is applied, has a conduction property along the LUMO level, and means the property that facilitates the injection of electrons formed from the negative electrode into the light-emitting layer, the movement of electrons formed from the light-emitting layer to the negative electrode, and the movement to the light-emitting layer.

[0035] Hereinafter, an organic optoelectronic device according to an embodiment will be described.

[0036] The organic optoelectronic device is not particularly limited as long as it is a device capable of converting electrical energy and optical energy into each other, and examples thereof include an organic optoelectronic device, an organic light-emitting device, an organic solar cell, and an organic photoreceptor drum.

[0037] Here, an organic light-emitting device, which is an example of an organic optoelectronic device, will be described as an example, but it is not limited thereto, and the same can be similarly applied to other organic optoelectronic devices.

[0038] In the drawings, for the purpose of clearly showing a plurality of layers and regions, the thickness is shown enlarged. Throughout the specification, the same reference numerals are given to the same parts. When a part such as a layer, a film, a region, or a plate is "on" another part, this includes not only the case where it is "directly on" another part, but also the case where there is another part in the middle. Conversely, when a part is "directly above" another part, it means that there is no other part in between.

[0039] FIG. 1 is a cross-sectional view schematically showing an organic optoelectronic device according to an embodiment.

[0040] Referring to FIG. 1, an organic optoelectronic device according to an embodiment includes a positive electrode 10 and a negative electrode 20 facing each other, and an organic layer 30 located between the positive electrode 10 and the negative electrode 20.

[0041] The positive electrode 10 can be made of a conductor with a high work function, for example, to facilitate hole injection. It can be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The positive electrode 10 can be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof, a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb, and a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0042] The negative electrode 20 can be made of a conductor with a low work function, for example, to facilitate electron injection. It can be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The negative electrode 20 can be, 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, and a multilayer structured material such as LiF / Al, LiO2 / Al, LiF / Ca, BaF2 / Ca, but is not limited thereto.

[0043] 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.

[0044] The hole transport layer 31 is a layer for facilitating the transfer of holes from the positive electrode 10 to the light-emitting layer 32. It may be, for example, an amine compound, but is not limited thereto.

[0045] The amine compound can contain, for example, at least one aryl group and / or heteroaryl group. The amine compound is represented by, for example, the following Chemical Formula a or Chemical Formula b, but is not limited thereto.

[0046] [Chemical Formula]

[0047] In the above Chemical Formula a or b, Ar a ~Ar g each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, or a combination thereof, Ar a ~Ar c at least one of and Ar d ~Ar g at least one of is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, or a combination thereof, Ar h is a single bond, a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, or a combination thereof.

[0048] The light-emitting layer 32 contains at least two types of host and dopant, and the host contains a first compound having a bipolar characteristic with relatively strong electron characteristics and a second compound having a bipolar characteristic with relatively strong hole characteristics.

[0049] The first compound is represented by the following Chemical Formula 1.

[0050] [Chemical Formula 1] [Chemical Formula]

[0051] In the above Chemical Formula 1, Ar 1 ~Ar 3 each independently represents a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group; L 1 ~L 4 each independently represents a single bond or a substituted or unsubstituted C6-C20 arylene group; R 1 ~R 3 each independently represents hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group; m1 and m3 each independently represent one of the integers from 1 to 4; m2 represents an integer of 1 or 2.

[0052] The first compound has at least one substituted or unsubstituted C10-C30 aryl group or substituted or unsubstituted C10-C30 heterocyclic group as an additional substituent of triazine substituted at the N position of the indolocarbazole group, thereby expanding the LUMO electron cloud and showing smooth electron injection and transfer characteristics. As a result, hole and electron balance within the molecule is achieved. In the case of an organic light-emitting device to which this is applied, the driving voltage of the device can be lowered, and the lifetime characteristics can be improved due to the stability brought about by hole and electron balance.

[0053] As an example, the Ar 1 ~Ar 3 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 carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group; Ar 2 and Ar 3At least one of them may be a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0054] The first compound may be one selected from the compounds listed in Group 1 below, but is not limited thereto.

[0055] [Group 1] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula]

[0056] One or more of the first compounds can be used.

[0057] The second compound is used in the light-emitting layer together with the first compound, and can improve the light-emitting efficiency and lifetime characteristics by enhancing the charge mobility and safety.

[0058] The second compound is represented by, for example, the following Chemical Formula 2.

[0059] [Chemical Formula 2] [Chem.]

[0060] In Chemical Formula 2, Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, Ar 10 ~Ar 13 are each independently hydrogen, or a substituted or unsubstituted C6-C30 aryl group, L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6-C20 arylene group, R 4 ~R 8 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, m4, m7 and m8 are each independently one of the integers from 1 to 4, m5 and m6 are each independently one of the integers from 1 to 3, n is one of the integers from 0 to 2.

[0061] R 4 When there are two or more Rs, each R 4 may be the same or different.

[0062] R 5 When there are two or more Rs, each R 5 may be the same or different.

[0063] R 6 When there are two or more Rs, each R 6 may be the same or different.

[0064] R 7 When there are two or more Rs, each R 7 may be the same or different.

[0065] As an example, Ar in Chemical Formula 2 4 and Ar 5 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 carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group, L in Chemical Formula 2 5 and L 6 are each independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, R in Chemical Formula 2 4 ~R 8 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6 - C12 aryl group, n may be 0 or 1.

[0066] As an example, Ar in Chemical Formula 1 10 ~Ar 13 may each independently be hydrogen, or a substituted or unsubstituted C6 - C12 aryl group.

[0067] For example, Ar in Chemical Formula 1 10 ~Ar13 may each independently be hydrogen or a phenyl group which may be substituted or unsubstituted.

[0068] As an example, "substituted" in Chemical Formula 2 means that at least one hydrogen is substituted with deuterium, a C1-C4 alkyl group, a C6-C18 aryl group, or a C2-C30 heteroaryl group.

[0069] In a specific embodiment of the present invention, Chemical Formula 2 is represented by one of the following Chemical Formulas 2-1 to 2-15.

[0070]

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

Chemical Formula

[0071] In Chemical Formulas 2-1 to 2-15, R 4 ~R 8 may each independently be hydrogen, deuterium or a substituted or unsubstituted C6-C12 aryl group, * -L 5 -Ar 4 and * -L 6 -Ar 5 may each independently be one of the substituents listed in Group II below.

[0072] [Group II]

Chemical Formula

[0073] Among said Group II, D is deuterium, m19 is one of the integers from 1 to 5, m20 is one of the integers from 1 to 4, m21 is one of the integers from 1 to 3, m22 is the integer 1 or 2, * is a linking point.

[0074] In one embodiment, said Chemical Formula 2 is represented by said Chemical Formula 2-8.

[0075] Also, the * -L 5 -Ar 4 and * -L 6 -Ar 5 can each independently be selected from said Group II and may be, for example, any one of C-1, C-2, C-3, C-4, C-7, C-8, and C-9.

[0076] Said second compound is represented by, for example, a combination of the following Chemical Formula 3 and Chemical Formula 4.

[0077] [Chemical Formula]

[0078] In said Chemical Formula 3 and Chemical Formula 4, Ar 6 and Ar 7 are each independently a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, a1 of Chemical Formula 3 * ~a4 * are each independently a linking carbon (C) or C-L a -R a and a1 of Chemical Formula 3* ~a4 * Of these, two adjacent ones are each of the chemical formula 4 * and are linked to L a 、L 7 and L 8 are each independently a single bond or a substituted or unsubstituted C6-C20 arylene group, R a 、R 9 and R 10 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, m9 and m10 are each independently one of the integers from 1 to 4.

[0079] As an example, the second compound represented by the combination of the chemical formula 3 and the chemical formula 4 is represented by any one of the following chemical formula 3A, chemical formula 3B, chemical formula 3C, chemical formula 3D, and chemical formula 3E.

[0080]

Chemical formula

Chemical formula

[0081] Among the chemical formula 3A to chemical formula 3E, Ar 6 、Ar 7 、L 7 、L 8 、R 9 and R 10 are the same as described above, La 1 ~La 4 is the same as the definition of L 7 and L 8 described above, R a1 ~R a4 is the same as the R 9 and R 10is the same as the definition.

[0082] For example, Ar in Chemical Formulas 3 and 4 6 and Ar 7 are 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, R a1 ~R a4 、R 9 and R 10 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.

[0083] In a specific embodiment of the present invention, Ar in Chemical Formulas 3 and 4 6 and Ar 7 can each independently be selected from among the substituents listed in Group II.

[0084] In one embodiment, the above R a1 ~R a4 、R 9 and R 10 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.

[0085] For example, the above R a1 ~R a4 、R 9 and R 10 may each independently be hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group.

[0086] In a specific embodiment, the R a1 ~R a4 , R 9 and R 10 may each independently be hydrogen, deuterium or a phenyl group.

[0087] In a specific embodiment of the present invention, the second compound is represented by the chemical formula 2-8, and Ar 4 and Ar 5 are 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, and L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6-C20 arylene group, and R 4 ~R 8 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.

[0088] In another specific embodiment of the present invention, the second compound is represented by the chemical formula 3C, L a3 and L a4 are single bonds, L 7 and L 8 are each independently a single bond or a substituted or unsubstituted C6-C12 arylene group, R9, R 10 , R a3 and R a4 are each hydrogen, deuterium or a phenyl group, and Ar 6 and Ar 7 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0089] For example, the second compound can also be one selected from among the compounds listed in Group 2 below, but is not limited thereto.

[0090] [Group 2] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula]

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[0091] One or more of the second compounds can be used.

[0092] In the light-emitting layer 32, the first compound and the second compound can be included as hosts, for example, in a weight ratio of about 1:99 to 99:1. By being included within the above range, the electron transport ability of the first compound and the hole transport ability of the second compound are utilized to adjust an appropriate weight ratio to realize bipolar characteristics, thereby improving efficiency and lifetime. Within the above range, for example, they can be included in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20, 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, they can be included in a weight ratio of 20:80, 30:70, or 40:60.

[0093] In addition to the first compound and the second compound described above as hosts, the light-emitting layer 32 can further include one or more compounds.

[0094] The light-emitting layer 32 can further include a dopant.

[0095] The dopant may be, for example, a phosphorescent dopant, and may be, for example, a red, green, or blue phosphorescent dopant, or may be, for example, a red or green phosphorescent dopant.

[0096] The dopant is a substance that is mixed in trace amounts with a compound for an organic optoelectronic device to cause light emission, and substances such as metal complexes that emit light by multiple excitation that generally excites to a triplet state or higher can be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may contain one or more types.

[0097] As an example of the dopant, a phosphorescent dopant can be mentioned. Examples of the phosphorescent dopant include organometallic compounds containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. As the phosphorescent dopant, for example, a compound represented by the following chemical formula Z can be used, but is not limited thereto.

[0098] [Chemical formula Z] L 9 MX 2

[0099] In the chemical formula Z, M is a metal, and L 9 and X 2 are the same as or different from each other, and are ligands that form a complex compound with M.

[0100] The M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and the L 9 and X 2 may be, for example, bidentate ligands.

[0101] L 9 and X 2Examples of ligands represented by [ligand formula] include, but are not limited to, those selected from the chemical formulas listed in Group A below.

[0102] [Group A] [Chemical formula]

[0103] Among the above Group A, R 300 ~R 302 each independently represents hydrogen, deuterium, a halogen-substituted or unsubstituted C1-C30 alkyl group, a C6-C30 aryl group substituted or unsubstituted with C1-C30 alkyl, or a halogen. R 303 ~R 324 each independently represents hydrogen, deuterium, a halogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C1-C30 heteroaryl group, a substituted or unsubstituted C1-C30 amino group, a substituted or unsubstituted C6-C30 arylamino group, SF5, a trialkylsilyl group having a substituted or unsubstituted C1-C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1-C30 alkyl group and a C6-C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6-C30 aryl group.

[0104] As an example, it can contain a dopant represented by the following Chemical formula V.

[0105] [Chemical formula V] [Chemical formula]

[0106] Among the above Chemical formula V, R 101 ~R 116is, independently of each other, hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 132 R 133 R 134 wherein said R 132 ~R 134 are, independently of each other, a substituted or unsubstituted C1-C6 alkyl group, R 101 ~R 116 at least one of which is a functional group represented by the following chemical formula V-1, L 100 is a bidentate ligand of a monovalent anion and is a ligand that coordinates to iridium via a lone pair of a carbon or heteroatom, n5 and n6 are each independently any integer from 0 to 3, and n5 + n6 is any integer from 1 to 3.

[0107] [Chemical formula V-1] [Chemical formula]

[0108] In the above chemical formula V-1, R 135 ~R 139 are, independently of each other, hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 132 R 133 R 134 wherein said R 132 ~R 134 are, independently of each other, a substituted or unsubstituted C1-C6 alkyl group, * means a moiety linked to a carbon atom.

[0109] As an example, it may also contain a dopant represented by the following chemical formula Z-1.

[0110] [Chemical formula Z-1] [Chemical formula]

[0111] In the chemical formula Z-1, rings A, B, C, and D each independently represent a 5- or 6-membered carbocyclic or heterocyclic ring. R A 、R B 、R C 、and R D each independently represent mono-substituted, di-substituted, tri-substituted, or optionally substituted or unsubstituted. L B 、L C 、and L D are each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof. When nA is 1, L E is selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR'; when nA is 0, L E does not exist. 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' may optionally be linked to form a ring; X B 、X C 、X D 、and X Eis independently selected from the group consisting of carbon and nitrogen, respectively, Q 1 、Q 2 、Q 3 、and Q 4 each represents oxygen or a direct bond.

[0112] The dopant according to one embodiment may be a platinum complex, for example, represented by the following chemical formula VI.

[0113] [Chemical formula VI]

Chem.

[0114] In the chemical formula VI, X 100 is selected from O, S, and NR 131 , R 117 ~R 131 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 132 R 133 R 134 , the R 132 ~R 134 are each independently a substituted or unsubstituted C1-C6 alkyl group, R 117 ~R 131 at least one of which is -SiR 132 R 133 R 134 or a tert-butyl group, the R 132 ~R 134 are each independently a substituted or unsubstituted C1-C6 alkyl group.

[0115] The hole transport auxiliary layer 33 contains a third compound having a bipolar characteristic with relatively strong hole characteristics.

[0116] As described above, the light-emitting layer 32 contains both a first compound having relatively strong diode characteristics in terms of electron characteristics and a second compound having relatively strong hole characteristics, thereby enhancing the mobilities of electrons and holes and significantly improving the light-emitting efficiency as compared with the case of using them alone.

[0117] In an element in which a material with one-sided bias in electron characteristics or hole characteristics is introduced into the light-emitting layer, carrier recombination occurs at the interface between the light-emitting layer and the electron or charge transport layer, and relatively more excitons are formed. As a result, due to the interaction between the molecular excitons in the light-emitting layer and the charges at the interface of the hole transport layer, a roll-off phenomenon occurs in which the efficiency rapidly decreases, and the light-emitting lifetime characteristics also rapidly deteriorate.

[0118] To solve such problems, the first and second compounds are simultaneously introduced into the light-emitting layer so that the light-emitting region is not biased to either the electron transport layer or the hole transport layer. Furthermore, a hole transport auxiliary layer containing a third compound having relatively strong diode characteristics in terms of hole characteristics is included between the hole transport layer and the light-emitting layer, thereby preventing the accumulation of charges at the interface between the hole transport layer and the light-emitting layer and making it possible to fabricate an element capable of adjusting the carrier balance in the light-emitting layer. Thereby, the roll-off characteristics of the organic optoelectronic element can be improved, and at the same time, the lifetime characteristics can be significantly improved.

[0119] The third compound may be a compound represented by the following Chemical Formula 5.

[0120] [Chemical Formula 5]

Chemical Structure

[0121] In Chemical Formula 5, X 1 is C or Si, R 11 ~R 14Each independently is hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, R 15 and R 16 Each independently is a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group, Ar 8 is a substituted or unsubstituted C6-C30 aryl group, Ar 9 is a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted dibenzosilolyl group, L 9 ~L 11 Each independently is a single bond or a substituted or unsubstituted C6-C20 arylene group, m11, m12 and m14 each independently is one of the integers from 1 to 4, m13 is one of the integers from 1 to 3.

[0122] The third compound is an amine derivative that simultaneously contains a 9-substituted fluorene group and a fluorene group substituted in the phenyl direction or a dibenzosilolyl group substituted in the phenyl direction.

[0123] Due to the steric hindrance of the 9-substituted fluorene group, degradation decomposition can be minimized with a decrease in the vapor deposition temperature, so that the lifetime characteristics can be further improved.

[0124] Also, by simultaneously containing a fluorene group substituted in the phenyl direction or a dibenzosilolyl group substituted in the phenyl direction, the HOMO energy level can be lowered and hole injection can be facilitated.

[0125] When m11 is 2 or more, each R 11 may be the same as or different from each other.

[0126] When m12 is 2 or more, each R 12 may be the same as or different from each other.

[0127] When m13 is 2 or more, each R 13 may be the same as or different from each other.

[0128] When m14 is 2 or more, each R 14 may be the same as or different from each other.

[0129] As an example, the third compound is represented by any one of the following chemical formulas 5-1 to 5-4.

[0130]

Chem.

Chem.

[0131] In the chemical formulas 5-1 to 5-4, X 1 , R 11 ~R 16 , Ar 8 , Ar 9 , L 9 ~L 11 , m11 to m14 are the same as those described above.

[0132] For example, the third compound is represented by the chemical formula 5-2.

[0133] As an example, Ar in the chemical formula 5 8 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0134] As a specific example, Ar in the chemical formula 5 8 may be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0135] As an example, Ar in the chemical formula 5 9 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted dibenzosilolyl group.

[0136] As a specific example, Ar in the chemical formula 5 9 can be selected from among the substituents listed in Group III below.

[0137] [Group III] [Chem.]

[0138] In the above Group III, * is the connection point. For example, the third compound may be one selected from among the compounds listed in Group 3 below, but is not limited thereto.

[0139] [Group 3] [Chem.] [Chem.] [Chem.] [Chem.] [Chem.] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry]

[0140] In a most specific embodiment of the present invention, the first compound is as described above, the second compound is represented by the chemical formula 2-8, and the third compound can be represented by the chemical formula 5-2.

[0141] Also, the organic layer 30 can further include an electron transport region.

[0142] The electron transport region can further enhance the electron injection and / or electron mobility between the negative electrode 20 and the light-emitting layer 32 and block holes.

[0143] Specifically, the electron transport region can include an electron transport layer 34 between the negative electrode 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 can be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0144] [Group B] [Chemistry]

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

[0145] On the other hand, the organic light-emitting device can further include, as the above-described organic layer, an electron injection layer (not shown), a hole injection layer (not shown), etc. in addition to the light-emitting layer.

[0146] The organic light-emitting device can be manufactured by forming a positive electrode or a negative electrode on a substrate, then forming an organic layer by a dry film-forming method such as evaporation, sputtering, plasma plating, and ion plating, and then forming a negative electrode or a positive electrode thereon.

[0147] The above-described organic light-emitting device can be applied to an organic light-emitting display device.

Example

[0148] Hereinafter, the above-described embodiments will be described in more detail through examples. However, the following examples are for illustrative purposes only and do not limit the scope of the rights.

[0149] Hereinafter, the starting materials and reactants used in the examples and synthesis examples were purchased from Sigma-Aldrich, TCI, tokyo chemical industry, or P&Htech, or synthesized through known methods, unless otherwise specifically mentioned.

[0150] (Synthesis of Compounds) The compounds presented as more specific examples of the compounds of the present invention were synthesized through the following steps.

[0151] (Synthesis of the First Compound) (Synthesis Example 1: Synthesis of Compound A-22) [Reaction Scheme 1]

Chem.

[0152] Using intermediate M-1 (CAS No. 1449754-80-6) and intermediate M-2 (CAS No. 1689576-03-1), A-22 was synthesized with reference to the synthesis method known from the published patent KR10-2021-0039202.

[0153] (Comparative Synthesis Example 1: Synthesis of Compound ET-1)

Chemical Formula

[0154] Compound ET-1 was synthesized with reference to the synthesis method known from the Korean Registered Patent Publication No. 10-2275343.

[0155] (Synthesis of the Second Compound) (Synthesis Example 2: Synthesis of Compound B-136)

Chemical Formula

[0156] Compound B-136 was synthesized with reference to the synthesis method known from the specification of US Patent No. 10476008.

[0157] (Synthesis of the Third Compound) (Synthesis Example 3: Synthesis of Compound D-2) [Reaction Scheme 2]

Chemical Formula

[0158] Compound D-2 was synthesized using Int-1 and Int-3 (CAS No. 1853122-02-7).

[0159] (Synthesis Example 4: Synthesis of Compound D-30) [Reaction Scheme 3]

Chemical Formula

[0160] Compound D-30 was synthesized using Int-4 (CAS No. 1154752-04-1) and Int-3 (CAS No. 1853122-02-7).

[0161] (Comparative Synthesis Example 2: Synthesis of Compound R-1) [Chemical formula]

[0162] Compound R-1 was synthesized with reference to the synthesis method known from U.S. Patent No. 10,355,217.

[0163] (Comparative Synthesis Example 3: Synthesis of Compound R-2) [Chemical formula]

[0164] Compound R-2 was synthesized with reference to the method known from Korean Registered Patent Publication No. 10-1931250.

[0165] (Comparative Synthesis Example 4: Synthesis of Compound R-3) [Chemical formula]

[0166] Compound R-3 was synthesized with reference to the synthesis method known from Korean Patent Publication No. 10-2019-0108222.

[0167] (Fabrication of Organic Light-Emitting Device) (Example 1) A glass substrate coated with ITO (Indium tin oxide) was cleaned by ultrasonic cleaning with distilled water. After the distilled water cleaning was completed, ultrasonic cleaning was performed in solvents such as isopropyl alcohol, acetone, and methanol, and after drying, it was transferred to a plasma cleaner, and the substrate was cleaned using oxygen plasma for 10 minutes, and then the substrate was transferred to a vacuum evaporator. Using the thus-prepared ITO transparent electrode as the positive electrode, compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum-deposited on the ITO substrate to form a hole injection layer with a thickness of 100 Å, and compound A was deposited on the hole injection layer to a thickness of 1350 Å to form a hole transport layer. Compound D-2 obtained in Synthesis Example 3 was deposited on the hole transport layer to a thickness of 320 Å to form a hole transport auxiliary layer. Compound A-22 of Synthesis Example 1 and compound B-136 of Synthesis Example 2 were simultaneously used as hosts on the hole transport auxiliary layer, and GD was doped at 10 wt% as a dopant, and a light-emitting layer with a thickness of 330 Å was formed by vacuum deposition. Subsequently, compound B was deposited on the light-emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compound C and LiQ were simultaneously vacuum-deposited at a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å. LiQ 15 Å and Al 1200 Å were sequentially vacuum-deposited on the electron transport layer to form a negative electrode, and an organic light-emitting device was fabricated.

[0168] It was fabricated with a structure of ITO / compound A (3% NDP-9 doping, 100 Å) / compound A (1350 Å) / compound D-2 (320 Å) / EML [host (compound A-22:compound B-136 = 35:65):GD = 90 wt%:10 wt%] (330 Å) / compound B (50 Å) / compound C:LiQ (300 Å) / LiQ (15 Å) / Al (1200 Å).

[0169] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine Compound B: 2-{3-[3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl]phenyl}-4,6-diphenyl-1,3,5-triazine Compound C: 4-{4-[4-(diphenyl-1,3,5-triazin-2-yl)phenyl]naphthalen-1-yl}phenyl benzonitrile [GD]

Chem.

[0170] (Example 2 and Comparative Examples 1 - 3) Devices of Example 2 and Comparative Examples 1 - 3 were fabricated in the same manner as in Example 1, except that the hole transport auxiliary layer was changed as described in Table 1 below.

[0171] (Comparative Example 4) A device of Comparative Example 4 was fabricated in the same manner as in Example 2, except that the first host was changed and the mixing ratio of the first host and the second host was changed to 30:70 wt% as described in Table 1 below.

[0172] (Evaluation: Lifetime Measurement) The lifetime characteristics of the organic light-emitting devices according to Examples 1 - 2 and Comparative Examples 1 - 4 were evaluated.

[0173] The specific measurement method is as follows, and the results are shown in Table 1.

[0174] Luminance (cd / m 2 ) was maintained at 24000 cd / m 2 , and the time when the current efficiency (cd / A) decreased to 95% was measured to obtain the results.

[0175] Relative values based on the lifetime of Comparative Example 1 are shown in Table 1 below.

[0176]

Table 1

[0177] 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 very improved contrast life characteristic compared to the organic light-emitting device according to the comparative example.

[0178] Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements by those skilled in the art using the basic concept of the present invention defined in the following claims also belong to the scope of the present invention.

Explanation of Reference Numerals

[0179] 10 Anode 20 Cathode 30 Organic layer 31 Hole transport layer 32 Light-emitting layer 33 Hole transport auxiliary layer 34 Electron transport layer

Claims

1. A positive electrode and a negative electrode facing each other, a light-emitting layer positioned between the positive electrode and the negative electrode, a hole transport layer positioned between the positive electrode and the light-emitting layer, and a hole transport auxiliary layer positioned between the light-emitting layer and the hole transport layer, comprising: The light-emitting layer includes a first compound represented by the following Chemical Formula 1 and a second compound represented by a combination of the following Chemical Formula 2 or the following Chemical Formulas 3 and 4, The hole transport auxiliary layer is an organic optoelectronic device including a third compound represented by the following Chemical Formula 5: [Chemical Formula 1] 【Chemical 1】 In the Chemical Formula 1, Ar １ to Ar ３ each independently represents a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, L １ ~L ４ are each independently a single bond or a substituted or unsubstituted C6-C20 arylene group, R １ ~R ３ are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group, m1 and m3 are each independently one of the integers from 1 to 4, m2 is an integer of 1 or 2, [Chemical Formula 2] 【Chemical 2】 In the Chemical Formula 2, Ar ４ and Ar ５ each independently is a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, Ar １０ ~Ar １３ are each independently hydrogen or a substituted or unsubstituted C6-C30 aryl group, L ５ and L ６ are each independently a single bond or a substituted or unsubstituted C6-C20 arylene group, R ４ ~R ８ each independently represents hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, m4, m7, and m8 are each independently one of the integers from 1 to 4, m5 and m6 are each independently one of the integers from 1 to 3, n is one of the integers from 0 to 2, [Chemical Formula 3] In the Chemical Formulas 3 and 4, Ar ６ and Ar ７ are each independently a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, a of Chemical Formula 3 １ ＊ ~a ４ ＊ are each independently a linking carbon (C) or C-L ａ -R ａ and a of Chemical Formula 3 １ ＊ ~a ４ ＊ Among them, two adjacent ones are each connected to ＊ of Chemical Formula 4 and L ａ 、L ７ and L ８ are each independently a single bond or a substituted or unsubstituted C6-C20 arylene group, R ａ 、 R ９ and R １０ are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, m9 and m10 are each independently one of the integers from 1 to 4, [Chemical Formula 5] 【Chemical Formula 4】 In the Chemical Formula 5, X １ is C or Si, R １１ to R １４ each independently represents hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, R １５ and R １６ are each independently a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group, Ar ８ is a substituted or unsubstituted C6-C30 aryl group, Ar ９ is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted dibenzosilolyl group, L ９ ~L １１ each independently represents a single bond or a substituted or unsubstituted C6-C20 arylene group, m11, m12, and m14 are each independently one of the integers from 1 to 4, m13 is one of the integers from 1 to 3.

2. Said Ar １ to Ar ３ 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 carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, Ar ２ and Ar ３ At least one of which is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, the organic optoelectronic device according to claim 1.

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

4. The organic optoelectronic device according to Claim 1, wherein the third compound is represented by any one of the following Chemical Formulas 5-1 to 5-4: 【Chemical 8】 【Chemical Formula 9】 In the Chemical Formulas 5-1 to 5-4, X １ 、R １１ ~R １６ 、Ar ８ 、Ar ９ 、L ９ ~L １１ 、m11 to m14 are as defined in claim 1.

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

6. Ar of the chemical formula 5 ９ The organic optoelectronic device according to claim 1, wherein ９ is 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 dibenzosilolyl group.

7. Ar of the chemical formula 5 ９ The organic optoelectronic device according to claim 1, wherein ９ is one selected from the substituents listed in Group III below: [Group III] 【Chemical Formula 10】 Among Group III, ＊ is a connection point.

8. The organic optoelectronic device according to Claim 1, wherein the third compound is one selected from the compounds listed in the following Group 3. [Group 3] 【Chemical 11】 【Chemical Formula 12】 【Chemical 13】 【Chemical 14】 【Chemical Formula 15】 【Chemical 16】 【Chemical 17】 【Chemical 18】 【Chemical 19】 【Chemical 20】 【Chemical 21】

9. The organic optoelectronic device according to Claim 1, wherein the second compound is represented by the following Chemical Formula 2-8, and the third compound is represented by the following Chemical Formula 5-2: [Chemical Formula 2-8] 【Chemical 22】 In the Chemical Formula 2-8, R ４ ~R ７ each independently represents hydrogen, deuterium, or a substituted or unsubstituted C6-C12 aryl group, Ar １０ ~Ar １３ each independently represents hydrogen or a substituted or unsubstituted C6-C12 aryl group, m4 and m7 are each independently one of the integers from 1 to 4, m5 and m6 are each independently one of the integers from 1 to 3, ＊ -L ５ -Ar ４ and ＊ -L ６ -Ar ５ is each independently one selected from among the substituents listed in Group II below, [Group II] 【Chemical 23】 Among said Group II, D is deuterium, m19 is one of the integers from 1 to 5, m20 is one of the integers from 1 to 4, m21 is one of the integers from 1 to 3, m22 is an integer of 1 or 2, ＊ is the connection point, [Chemical Formula 5-2] 【Chemical 24】 In said Chemical Formula 5-2, X １ is C or Si, R １１ ~R １４ each independently represents hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C30 aryl group, R １５ and R １６ are each independently a substituted or unsubstituted C1-C10 alkyl group or a substituted or unsubstituted C6-C20 aryl group, Ar ８ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, and 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 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 dibenzosilolyl group, L ９ ~L １１ each independently represents a single bond or a substituted or unsubstituted C6-C12 arylene group, m11, m12 and m14 are each independently one of the integers from 1 to 4, m13 is one of the integers from 1 to 3.

10. A display device including the organic optoelectronic device according to any one of Claims 1 to 9.

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