Organic optoelectronic diode and display device

Abstract

The present invention relates to an organic optoelectronic diode comprising: an anode and a cathode, which face each other; an emissive layer positioned between the anode and the cathode; a hole transport layer positioned between the anode and the emissive layer; and a hole transport auxiliary layer positioned between the emissive layer and the hole transport layer, wherein the hole transport auxiliary layer includes a first hole transport auxiliary layer adjacent to the hole transport layer and a second hole transport auxiliary layer adjacent to the emissive layer, and the emissive layer includes a first compound represented by chemical formula 1 or chemical formula 2, the first hole transport auxiliary layer including a second compound represented by chemical formula 3 and the second hole transport auxiliary layer including a third compound represented by chemical formula 3, wherein the second compound and the third compound are different from each other, the refractive index of the hole transport layer is higher than the refractive index of the first hole transport auxiliary layer, and the refractive index of the first hole transport auxiliary layer is 2.0 or less. The detailed description of chemical formulas 1-3 is the same as that defined in the specification.

Description

Organic optoelectronic devices and display devices

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

[0002] An organic optoelectronic diode is a device capable of converting electrical energy and light energy.

[0003] Organic optoelectronic devices can be broadly divided into two types based on their operating principles. One is a photovoltaic device that generates electrical energy as excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes, and the other is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to electrodes.

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

[0005] Among these, organic light-emitting diodes (OLEDs) have recently been receiving significant attention due to the increasing demand for flat panel display devices. As an organic light-emitting diode is a device that converts electrical energy into light, its performance is greatly influenced by the organic material located between the electrodes.

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

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

[0008] According to one embodiment, an organic optoelectronic device is provided, comprising an anode and a cathode facing each other, a light-emitting layer located between the anode and the cathode, a hole transport layer located between the anode and the light-emitting layer, and a hole transport assist layer located between the light-emitting layer and the hole transport layer, wherein the hole transport assist layer comprises a first hole transport assist layer adjacent to the hole transport layer and a second hole transport assist layer adjacent to the light-emitting layer, wherein the light-emitting layer comprises a first compound represented by the following chemical formula 1 or chemical formula 2, the first hole transport assist layer comprises a second compound represented by the following chemical formula 3, and the second hole transport assist layer comprises a third compound represented by the following chemical formula 3, wherein the second compound and the third compound are different from each other, and the refractive index of the hole transport layer is higher than the refractive index of the first hole transport assist layer, and the refractive index of the first hole transport assist layer is 2.0 or less.

[0009] [Chemical Formula 1] [Chemical Formula 2]

[0010]

[0011] In the above Chemical Formulas 1 and 2,

[0012] X 1 is O or S,

[0013] Z 1 To Z 3 Each independently is N or CL a -R a And,

[0014] Z 1 To Z 3 At least two of them are N, and

[0015] L a , and L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, and

[0016] Ra , R 1 to R 5 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heterocyclic group, substituted or unsubstituted silyl group, or a combination thereof, and

[0017] R 1 and R 2 Each exists independently or adjacent groups are connected to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring, and

[0018] Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and

[0019] R a , Ar 1 and Ar 2 Each exists independently, or

[0020] R a , Ar 1 and Ar 2 Adjacent groups are connected to form a substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic ring, and

[0021] m1 and m3 are each independently one of integers from 1 to 3, and

[0022] m2, m4, and m5 are each independently one of integers 1 to 4, and

[0023] If m1 to m5 are each independently 2 or more, each R 1 to R 5 They are identical or different from each other;

[0024] [Chemical Formula 3]

[0025]

[0026] In the above chemical formula 3,

[0027] X 2 is O, S, or CR b R c And,

[0028] L 4 to L 6 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0029] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0030] R b , R c and R 6 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0031] R b and R c Each exists independently or is linked to form substituted or unsubstituted spirobifluorenes, and

[0032] A is substituted or unsubstituted benzene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene or substituted or unsubstituted spirobifluorene, and

[0033] m6 is one of integers from 1 to 3, and

[0034] If m6 is 2 or greater, each R 6 They are identical or different from each other.

[0035] According to another embodiment, a display device comprising the organic optoelectronic element is provided.

[0036] It is possible to realize organic optoelectronic devices with high efficiency characteristics.

[0037] FIG. 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment.

[0038] <Explanation of Symbols>

[0039] 10: Anode 20: Cathode

[0040] 30: Organic layer 31: Hole transport layer

[0041] 32: Emissive layer 33: Hole transport assist layer

[0042] 34: Electron transport layer

[0043]

[0044] 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, and the present invention is defined only by the scope of the claims set forth below.

[0045] In this specification, "substitution" means that, unless otherwise defined, at least one hydrogen of a substituent or compound is substituted with a 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.

[0046] In one example of the present invention, "substitution" means that at least one hydrogen in the substituent or 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 a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C3 to C20 cycloalkyl group, a C6 to C30 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C5 alkyl group, a C3 to C10 cycloalkyl 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 the substituent or compound is substituted with deuterium, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a tert-butyl group, a cyclopropyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0047] In this specification, “non-substituted” means that a hydrogen atom remains a hydrogen atom without being substituted by another substituent.

[0048] In this specification, “hydrogen (-H)” may include “deuterium substitution (-D)” or “tritium substitution (-T)”.

[0049] In this specification, "hetero" means, unless otherwise defined, that one functional group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si, and the remainder is carbon.

[0050] In this specification, "aryl group" is a collective concept for a group having one or more hydrocarbon aromatic moietys, including a form in which 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 a form in which two or more hydrocarbon aromatic moietys are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quarterphenyl group, etc., and a non-aromatic fused ring in which two or more hydrocarbon aromatic moietys are directly or indirectly fused, such as a fluorenyl group, etc.

[0051] Aryl groups include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.

[0052] In this specification, "heterocyclic group" is a superordinate concept including heteroaryl groups, meaning that a cyclic compound, such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof, contains at least one heteroatom selected from the group consisting of N, O, S, P, and Si instead of carbon (C). If the heterocyclic group is a fused ring, it may contain one or more heteroatoms in the entire heterocyclic group or in each ring.

[0053] For example, a "heteroaryl group" means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si within the aryl group. Two or more heteroaryl groups may be directly connected through sigma bonds, or if the heteroaryl group comprises two or more rings, the two or more rings may be fused together. If the heteroaryl group is a fused ring, each ring may contain one to three heteroatoms.

[0054] 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 crisenyl 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.

[0055] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic groups are 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 imidazoleyl group, a substituted or unsubstituted triazoleyl group, a substituted or unsubstituted oxazoleyl group, a substituted or unsubstituted thiazoleyl group, a substituted or unsubstituted oxadiazoleyl group, a substituted or unsubstituted thiadiazoleyl 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 benzimidazoleyl group, a substituted or unsubstituted indoleyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted It may be an isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthiridinyl group, a substituted or unsubstituted benzoxazine dil group, a substituted or unsubstituted benzthiazine dil group, a substituted or unsubstituted acrridinyl group, a substituted or unsubstituted phenazine dil group, a substituted or unsubstituted phenothiazine dil group, a substituted or unsubstituted phenoxazine dil group, a substituted or unsubstituted carbazole dil group, a substituted or unsubstituted dibenzofuran dil group, or a substituted or unsubstituted dibenzothiophen dil group, or a combination thereof, but is not limited thereto.

[0056] In this specification, the term "hole characteristic" refers to a characteristic that can form holes by donating electrons when an electric field is applied, and 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 movement within the light-emitting layer by having a conduction characteristic along the HOMO level.

[0057] In addition, electronic properties refer to the ability to receive electrons when an electric field is applied, and they refer to properties that facilitate the injection of electrons formed at the cathode into the light-emitting layer, the movement of electrons formed at the light-emitting layer to the cathode, and the movement of electrons within the light-emitting layer by having conduction properties along the LUMO level.

[0058] An organic optoelectronic device according to one embodiment is described below.

[0059] Organic optoelectronic devices are not particularly limited as long as they are devices capable of mutually converting electrical energy and light energy, and examples include organic photovoltaic devices, organic light-emitting devices, organic solar cells, and organic photosensitive drums.

[0060] Here, an organic light-emitting diode is described as an example of an organic optoelectronic device, but is not limited thereto and can be applied in the same way to other organic optoelectronic devices.

[0061] In the drawings, thicknesses have been enlarged to clearly represent various layers and regions. Throughout the specification, the same reference numerals have been used for similar parts. When a part such as a layer, film, region, or plate is described as being "on" another part, this includes not only cases where it is "immediately on" another part, but also cases where there is another part in between. Conversely, when a part is described as being "immediately on" another part, it means that there is no other part in between.

[0062] FIG. 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment.

[0063] An organic light-emitting device according to one embodiment will be described below with reference to FIG. 1.

[0064] Referring to FIG. 1, an organic light-emitting device according to one embodiment includes an anode (10) and a cathode (20) facing each other, and an organic layer (30) located between the anode (10) and the cathode (20).

[0065] The anode (10) may be made of a conductor with a high work function to facilitate hole injection, for example, and may be made of a metal, a metal oxide and / or a conductive polymer. The anode (10) may be a metal or an alloy thereof, such as nickel, platinum, vanadium, chromium, copper, zinc, gold; 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, but is not limited thereto.

[0066] The cathode (20) may be made of a conductor with a low work function to facilitate electron injection, for example, and may be made of a metal, a metal oxide and / or a conductive polymer. The cathode (20) may be a metal or an alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc.; or a multilayer material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0067] The organic layer (30) includes a light-emitting layer (31), a hole transport layer (32), and a hole transport auxiliary layer (33) located between the hole transport layer (32) and the light-emitting layer (31).

[0068] An organic optoelectronic device according to one embodiment is,

[0069] Positive and negative poles facing each other

[0070] A light-emitting layer located between the anode and the cathode,

[0071] A hole transport layer located between the anode and the light-emitting layer,

[0072] A hole transport assist layer located between the light-emitting layer and the hole transport layer.

[0073] Includes,

[0074] The above hole transport assist layer includes a first hole transport assist layer adjacent to the hole transport layer and a second hole transport assist layer adjacent to the light-emitting layer, and

[0075] The light-emitting layer comprises a first compound represented by the following chemical formula 1 or chemical formula 2, and

[0076] The first hole transport assisting layer comprises a second compound represented by the following chemical formula 3, and

[0077] The second hole transport assisting layer comprises a third compound represented by the following chemical formula 3, and

[0078] The second compound and the third compound are different from each other,

[0079] The refractive index of the hole transport layer is higher than the refractive index of the first hole transport assist layer, and

[0080] The refractive index of the first hole transport assist layer may be 2.0 or less.

[0081] For example, the refractive index of the first hole transport assist layer may be 1.9 or less.

[0082] As a specific example, the refractive index of the first hole transport assist layer mentioned above may be 1.8 or less.

[0083] For example, the refractive index of the first hole transport assist layer may be 1.5 or higher and 1.8 or lower.

[0084] For example, the refractive index of the first hole transport assist layer may be less than or equal to the refractive index of the second hole transport assist layer.

[0085] As a specific example, the refractive index of the first hole transport assist layer may be lower than the refractive index of the second hole transport assist layer.

[0086] For example, the T1 energy of the second hole transport assist layer above may be 2.5 eV or higher.

[0087] The light-emitting layer (31) includes at least two types of host and dopant, and the host may be, for example, a phosphorescent host.

[0088] The above phosphorescent host must facilitate the injection and transport of holes and electrons within the emissive layer, and ultimately enable holes and electrons to meet to form excitons effectively, and must be able to effectively transfer the formed exciton energy to the dopant. Examples of phosphorescent hosts include organic compounds comprising carbazole, indolocarbazole, dibenzofuran, dibenzothiophene, indolodibenzofuran, indolodibenzothiophene, fluorene, indenocarbazole, triphenylene, pyrimidine, triazine, or combinations thereof.

[0089] For example, the light-emitting layer may include a first compound represented by the following chemical formula 1 or chemical formula 2.

[0090] [Chemical Formula 1] [Chemical Formula 2]

[0091]

[0092] In the above Chemical Formulas 1 and 2,

[0093] X 1 is O or S,

[0094] Z 1 To Z 3 Each independently is N or CL a -R a And,

[0095] Z 1 To Z 3 At least two of them are N, and

[0096] L a , and L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, and

[0097] R a, R 1 to R 5 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heterocyclic group, substituted or unsubstituted silyl group, or a combination thereof, and

[0098] R 1 and R 2 Each exists independently or adjacent groups are connected to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring, and

[0099] Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and

[0100] R a , Ar 1 and Ar 2 Each exists independently, or

[0101] R a , Ar 1 and Ar 2 Adjacent groups are connected to form a substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic ring.

[0102] The first compound effectively extends the LUMO energy band by including a nitrogen-containing hexagonal ring moiety, so it can be included together with the fourth compound described later to increase the balance of holes and electrons, thereby significantly improving the lifespan characteristics of the device to which it is applied.

[0103] In this specification, "adjacent groups connected to form a substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic ring" means that any two adjacent substituents are connected to each other to form a ring. For example, R in Formula 1 1 to R 8Among them, adjacent groups may be connected to each other to form a substituted or unsubstituted aromatic monocyclic ring. The aromatic monocyclic ring formed therein may be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, etc., and the heteroaromatic polycyclic ring may be, for example, a substituted or unsubstituted indole group, a substituted or unsubstituted benzofuran group, a substituted or unsubstituted benzothiophenic group, etc.

[0104] As a more specific example, the above chemical formula 1 can be expressed as any one of the following chemical formulas 1-I to 1-IV.

[0105] [Chemical Formula 1-I] [Chemical Formula 1-II]

[0106]

[0107] [Chemical Formula 1-III] [Chemical Formula 1-IV]

[0108]

[0109] In the above Chemical Formulas 1-I to 1-IV,

[0110] X 1 is O or S,

[0111] L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group, and

[0112] Ar 1 and Ar 2Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quadrphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted crisenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthiophenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group, and

[0113] R 1 and R 2 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

[0114] m1 is one of integers from 1 to 3, and

[0115] m2 is one of integers from 1 to 4, and

[0116] If m1 and m2 are each independently 2 or more, then each R 1 and R 2 They are identical or different from each other.

[0117] In a specific embodiment, Chemical Formula 1 can be represented by Chemical Formula 1-IV.

[0118] For example, in the above chemical formula 1-IV, L 1 to L 3 Each is independently a single bond, or a substituted or unsubstituted phenylene group, and Ar 1 and Ar 2 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and R 1and R 2 Each may independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0119] As a more specific example, the above chemical formula 2 can be expressed as the following chemical formula 2-I or chemical formula 2-II.

[0120] [Chemical Formula 2-I] [Chemical Formula 2-II]

[0121]

[0122] In the above chemical formulas 2-I and 2-II,

[0123] Z 1 To Z 3 Each independently is N or CL a -R a And,

[0124] Z 1 To Z 3 At least two of them are N, and

[0125] L a , and L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group, and

[0126] Ar 1 and Ar 2 Each is 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 triphenylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

[0127] R a , R 3 to R 5Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

[0128] m3 is one of integers from 1 to 3, and

[0129] m4 and m5 are each independently one of integers 1 to 4, and

[0130] If m3 to m5 are each independently 2 or more, each R 3 to R 5 They are identical or different from each other.

[0131] In a specific embodiment, Chemical Formula 2 can be represented by Chemical Formula 2-I.

[0132] For example, in the above chemical formula 2-I, L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, and Ar 1 and Ar 2 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and R 3 to R 5 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted phenyl group.

[0133] The first compound mentioned above may be, for example, one selected from the compounds listed in Group 1 below, but is not limited thereto.

[0134] [Group 1]

[0135] [B-1] [B-2] [B-3] [B-4]

[0136]

[0137] [B-5] [B-6] [B-7] [B-8]

[0138]

[0139] [B-9] [B-10] [B-11] [B-12]

[0140]

[0141] [B-13] [B-14] [B-15] [B-16]

[0142]

[0143] [B-17] [B-18] [B-19] [B-20]

[0144]

[0145] [B-21] [B-22] [B-23] [B-24]

[0146]

[0147] [B-25] [B-26] [B-27] [B-28]

[0148]

[0149] [B-29] [B-30] [B-31] [B-32]

[0150]

[0151] [B-33] [B-34] [B-35] [B-36]

[0152]

[0153] [B-37] [B-38] [B-39] [B-40]

[0154]

[0155] [B-41] [B-42] [B-43] [B-44]

[0156]

[0157] [B-45] [B-46] [B-47] [B-48]

[0158]

[0159] [B-49] [B-50] [B-51] [B-52]

[0160]

[0161] [B-53] [B-54] [B-55] [B-56]

[0162]

[0163] [B-57] [B-58] [B-59] [B-60]

[0164]

[0165] [B-61] [B-62] [B-63] [B-64]

[0166]

[0167] [B-65] [B-66] [B-67] [B-68]

[0168]

[0169] [B-69] [B-70] [B-71] [B-72]

[0170]

[0171] [B-73] [B-74] [B-75] [B-76]

[0172]

[0173] [B-77] [B-78] [B-79] [B-80]

[0174]

[0175] [B-81] [B-82] [B-83] [B-84]

[0176]

[0177] [B-85] [B-86] [B-87] [B-88]

[0178]

[0179] [B-89] [B-90] [B-91] [B-92]

[0180]

[0181] [B-93] [B-94] [B-95] [B-96]

[0182]

[0183] [B-97] [B-98] [B-99] [B-100]

[0184]

[0185] [B-101] [B-102] [B-103] [B-104]

[0186]

[0187] [B-105] [B-106] [B-107] [B-108]

[0188]

[0189] [B-109] [B-110] [B-111] [B-112]

[0190]

[0191] [B-113] [B-114] [B-115] [B-116]

[0192]

[0193] [B-117] [B-118] [B-119] [B-120]

[0194]

[0195] [B-121] [B-122] [B-123] [B-124]

[0196]

[0197] [B-125] [B-126] [B-127] [B-128]

[0198]

[0199] [B-129] [B-130] [B-131] [B-132]

[0200]

[0201] [B-133] [B-134] [B-135] [B-136]

[0202]

[0203] [B-137] [B-138] [B-139] [B-140]

[0204]

[0205] [B-141] [B-142] [B-143] [B-144]

[0206]

[0207] [B-145] [B-146] [B-147] [B-148]

[0208]

[0209] [B-149] [B-150] [B-151] [B-152]

[0210]

[0211] [B-153] [B-154] [B-155] [B-156]

[0212]

[0213] [B-157] [B-158] [B-159] [B-160]

[0214]

[0215] [B-161] [B-162] [B-163] [B-164]

[0216]

[0217] [B-165] [B-166] [B-167] [B-168]

[0218]

[0219] [B-169] [B-170] [B-171] [B-172]

[0220]

[0221] [B-173] [B-174] [B-175] [B-176]

[0222]

[0223] [B-177] [B-178] [B-179] [B-180]

[0224]

[0225] [B-181] [B-182] [B-183] [B-184]

[0226]

[0227] [B-185] [B-186] [B-187] [B-188] [B-189]

[0228]

[0229] [B-190] [B-191] [B-192] [B-193] [B-194]

[0230]

[0231] [B-195] [B-196] [B-197] [B-198] [B-199]

[0232]

[0233] [B-200] [B-201] [B-202] [B-203] [B-204]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251] (Dn represents the number of deuterium substitutions, n is an integer greater than or equal to 0, and the maximum value of n corresponds to the number of substitutable hydrogen positions.)

[0252] Meanwhile, the light-emitting layer may further include a fourth compound represented by the following chemical formula 4; a combination of the following chemical formulas 5 and 6; the following chemical formula 7; or chemical formula 8.

[0253] [Chemical Formula 4]

[0254]

[0255] In the above chemical formula 4,

[0256] R 13 to R 17 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0257] Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0258] L7 and L 8 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and

[0259] m13, m16, and m17 are each independently one of integers 1 to 4, and

[0260] m14 and m15 are each independently one of integers 1 to 3, and

[0261] If m13 to m17 are 2 or more, each R 13 to R 17 are identical or different from each other,

[0262] n is one of integers from 0 to 2;

[0263] [Chemical Formula 5] [Chemical Formula 6]

[0264]

[0265] In the above chemical formulas 5 and 6,

[0266] Among a1* to a4* of Chemical Formula 5, two adjacent ones are each a connecting carbon (C) connected to * of Chemical Formula 6, and

[0267] The remaining two of a1* to a4* in Chemical Formula 5 that are not connected to Chemical Formula 6 are CL b -R d And,

[0268] L b , L 9 and L 10 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and

[0269] R d , R 18 and R 19 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0270] Ar 7 and Ar 8 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0271] m18 and m19 are each independently one of integers 1 to 4, and

[0272] If m18 and m19 are 2 or more, respectively R 18 and R 19 are identical or different from each other;

[0273] [Chemical Formula 7]

[0274]

[0275] In the above chemical formula 7,

[0276] L 11 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0277] R 20 to R 23 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0278] Ar 9 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0279] m20, m22, and m23 are each independently one of integers 1 to 4, and

[0280] m21 is one of integers from 1 to 3, and

[0281] If m20 to m23 are 2 or more, each R 20 to R 23 They are identical or different from each other;

[0282] [Chemical Formula 8]

[0283]

[0284] In the above chemical formula 8,

[0285] X 4 은 O, S, NR e , CR f R g or SiR h R i And,

[0286] R e , R f , R g , R h , R i and R 24 Each is independently hydrogen, deuterium, 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, and

[0287] m24 is one of integers from 1 to 4, and

[0288] B is any one selected from the rings listed in Group I below, and

[0289] [Group I]

[0290]

[0291] In the above Group I,

[0292] * is a connection point,

[0293] X 5 은 O, S, NR j , CR k R l or SiR m R n And,

[0294] R j , R k , R l , R m , R n and R 25 to R 29Each is independently hydrogen, deuterium, 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, and

[0295] R j and R 24 to R 29 At least one of them is a group represented by the following chemical formula a, and

[0296] [Chemical formula a]

[0297]

[0298] In the above chemical formula a,

[0299] L 12 to L 14 Each is independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group, and

[0300] Ar 10 and Ar 11 Each is independently a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0301] * is a connection point.

[0302] The above-mentioned fourth compound can be used in the light-emitting layer together with the aforementioned first compound to increase charge mobility and stability, thereby improving luminous efficiency and lifespan characteristics.

[0303] In the above Chemical Formula 4, when m13 is 2 or more, each R 13 They may be identical or different from each other,

[0304] In the above Chemical Formula 4, when m14 is 2 or more, each R 14 They may be identical or different from each other,

[0305] In the above Chemical Formula 4, when m15 is 2 or more, each R 15 They may be identical or different from each other,

[0306] In the above Chemical Formula 4, when m16 is 2 or more, each R 16 They may be identical or different from each other,

[0307] In the above Chemical Formula 4, when m17 is 2 or more, each R 17 They may be identical or different from each other,

[0308] In the above Chemical Formulas 5 and 6, when m18 is 2 or more, each R 18 are identical or different from each other,

[0309] In the above Chemical Formulas 5 and 6, when m19 is 2 or more, each R 19 They are identical or different from each other,

[0310] In the above Chemical Formula 7, when m20 is 2 or more, each R 20 are identical or different from each other,

[0311] In the above Chemical Formula 7, when m21 is 2 or more, each R 21 are identical or different from each other,

[0312] In the above Chemical Formula 7, when m22 is 2 or more, each R 22 They are identical or different from each other,

[0313] In the above Chemical Formula 7, when m23 is 2 or more, each R 23 They are identical or different from each other.

[0314] In the above chemical formula 8, when m24 is 2 or more, each R 24 They are identical or different from each other.

[0315] As an example, Ar of the above chemical formula 4 5 and Ar 6Each is 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 carbazoleyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group, and

[0316] L of the above chemical formula 4 7 and L 8 Each is independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, and

[0317] R of the above chemical formula 4 13 to R 17 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and

[0318] n can be 0 or 1.

[0319] For example, the term "substitution" in the above chemical formula 4 means that at least one hydrogen is substituted with a deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0320] In a specific embodiment of the present invention, the formula 4 may be represented by one of the following formulas 4-1 to 4-15.

[0321] [Chemical Formula 4-1] [Chemical Formula 4-2] [Chemical Formula 4-3]

[0322]

[0323] [Chemical Formula 4-4] [Chemical Formula 4-5] [Chemical Formula 4-6]

[0324]

[0325] [Chemical Formula 4-7] [Chemical Formula 4-8] [Chemical Formula 4-9]

[0326]

[0327] [Chemical Formula 4-10] [Chemical Formula 4-11] [Chemical Formula 4-12]

[0328]

[0329] [Chemical Formula 4-13] [Chemical Formula 4-14] [Chemical Formula 4-15]

[0330]

[0331] In the above chemical formulas 4-1 to 4-15, R 13 to R 17 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and L 7 -Ar 5 and L 8 -Ar 6 Each can be independently one of the substituents listed in Group II below.

[0332] [Group II]

[0333]

[0334] In the above Group II,

[0335] R 30 to R 35 Each is independently hydrogen, deuterium, a cyano group, a C1 to C10 alkyl group, or a C6 to C12 aryl group, and

[0336] m30 is one of integers from 1 to 5, and

[0337] m31 is one of integers 1 to 4, and

[0338] m32 is one of integers from 1 to 3, and

[0339] m33 is an integer of 1 or 2, and

[0340] m34 is one of integers from 1 to 7, and

[0341] * is a connection point.

[0342] In the above Group II, when m30 is 2 or more, each R 30They may be the same or different from each other.

[0343] In the above Group II, if m31 is 2 or more, each R 31 They may be the same or different from each other.

[0344] In the above Group II, if m32 is 2 or more, each R 32 It may be the same or different.

[0345] In the above Group II, when m33 is 2, each R 33 It may be the same or different.

[0346] In the above Group II, if m34 is 2 or more, each R 34 It may be the same or different.

[0347] The combination of the above chemical formulas 5 and 6 can be expressed, for example, as any one of the following chemical formulas 5A, 5B, 5C, 5D, and 5E.

[0348] [Chemical Formula 5A] [Chemical Formula 5B] [Chemical Formula 5C]

[0349]

[0350] [Chemical Formula 5D] [Chemical Formula 5E]

[0351]

[0352] In the above chemical formulas 5A to 5E, L 9 , L 10 , Ar 7 , Ar 8 , R 18 , R 19 , m18 and m19 are as previously stated, and

[0353] L b1 to L b4 is the aforementioned L 9 and L 10 It is the same as the definition of,

[0354] R d1 to R d4 is the aforementioned R18 and R 19 It is the same as the definition of.

[0355] For example, Ar of the above Chemical Formulas 5 and 6 7 and Ar 8 Each is 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 carbazoleyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group, and

[0356] R d1 to R d4 , R 18 and R 19 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.

[0357] In a specific embodiment of the present invention, L of Formulas 5 and 6 9 -Ar 7 and L 10 -Ar 8 Each can be independently selected from the substituents listed in Group II above.

[0358] In one embodiment, the R d1 to R d4 , R 18 and R 19 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.

[0359] For example, the above Rd1 to R d4 , R 18 and R 19 Each can independently be a hydrogen, deuterium, cyano group, or a substituted or unsubstituted phenyl group, and

[0360] In a specific embodiment, the R d1 to R d4 , R 18 and R 19 Each can independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0361] The above L b1 to L b4 is a single bond, and L 9 and L 10 Each is independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, and R 18 , R 19 , R d3 and R d4 are each hydrogen, deuterium, or a substituted or unsubstituted phenyl group, and Ar 7 and Ar 8 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0362] The above chemical formula 7 can be expressed, for example, by any one of the following chemical formulas 7-1 to 7-4.

[0363] [Chemical Formula 7-1] [Chemical Formula 7-2]

[0364]

[0365] [Chemical Formula 7-3] [Chemical Formula 7-4]

[0366]

[0367] In the above chemical formulas 7-1 to 7-4, L 11 , Ar 9 , R20 to R 23 and m20 to m23 are as described above.

[0368] For example, Ar of the above chemical formula 7 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 triphenylenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group, and

[0369] R 20 to R 23 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.

[0370] In a specific embodiment of the present invention, L of Formula 7 11 -Ar 9 It can be selected from the substituents listed in Group II above.

[0371] For example, the above R 20 to R 23 Each can independently be a hydrogen, deuterium, cyano group, or a substituted or unsubstituted phenyl group.

[0372] The above chemical formula 8 can be expressed, for example, as any one of the following chemical formulas 8-I to 8-IX.

[0373] [Chemical Formula 8-I] [Chemical Formula 8-II]

[0374]

[0375] [Chemical Formula 8-III] [Chemical Formula 8-IV]

[0376]

[0377] [Chemical Formula 8-V] [Chemical Formula 8-VI]

[0378]

[0379] [Chemical Formula 8-VII] [Chemical Formula 8-VIII]

[0380]

[0381] [Chemical Formula 8-IX]

[0382]

[0383] In the above chemical formulas 8-I to 8-IX,

[0384] X 4 , X 5 , R 24 to R 29 It is as previously stated.

[0385] In addition, depending on the direction of substitution of the amine group, the above formula 8 can be expressed as any one of the following formulas 8-ⅠA to 8-ⅨA, formulas 8-ⅠB to 8-ⅨB, and formulas 8-ⅠC to 8-ⅢC.

[0386] [Chemical Formula 8-ⅠA] [Chemical Formula 8-ⅡA]

[0387]

[0388] [Chemical Formula 8-IIIA] [Chemical Formula 8-IVA]

[0389]

[0390] [Chemical Formula 8-ⅤA] [Chemical Formula 8-ⅥA]

[0391]

[0392] [Chemical Formula 8-VIIA] [Chemical Formula 8-VIIIA]

[0393]

[0394] [Chemical Formula 8-IXA]

[0395]

[0396] [Chemical Formula 8-ⅠB] [Chemical Formula 8-ⅡB]

[0397]

[0398] [Chemical Formula 8-IIIB] [Chemical Formula 8-IVB]

[0399]

[0400] [Chemical Formula 8-ⅤB] [Chemical Formula 8-ⅥB]

[0401]

[0402] [Chemical Formula 8-ⅦB] [Chemical Formula 8-ⅧB]

[0403]

[0404] [Chemical Formula 8-IXB] [Chemical Formula 8-IC]

[0405]

[0406] [Chemical Formula 8-IIC] [Chemical Formula 8-IIIC]

[0407]

[0408] In the above formulas 8-ⅠA to 8-ⅨA, formulas 8-ⅠB to 8-ⅨB, and formulas 8-ⅠC to 8-ⅢC,

[0409] X 4 , X 5 , L 12 to L 14 , Ar 10 and Ar 11 It is as previously stated, and

[0410] R 24 to R 29 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and

[0411] m24', m25', m27' and m29' are each independently integers from 1 to 3.

[0412] In one embodiment, the above formula 8 may be represented as formula 8-IVB or formula 8-VIIIB.

[0413] As an example, X of the above chemical formula 8-IVB 4 is NR e It could be.

[0414] As an example, X of the above chemical formula 8-VIIIB 4 is O or S, and X 5 is CR k R l or SiR m R n It could be.

[0415] Here, R e , R k , R l , R m and R n Each may be an independently substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.

[0416] In one embodiment, the above formula 8 may be represented by the following formula 8-IVB-2 or formula 8-VIIIB-2.

[0417] [Chemical Formula 8-IVB-2] [Chemical Formula 8-VIIIB-2]

[0418]

[0419] In the above chemical formulas 8-IVB-2 and 8-VIIIB-2,

[0420] m24, m26, and m28 are as described above, and

[0421] L 12 to L 14 Each is independently a single bond or a substituted or unsubstituted phenylene group, and

[0422] The above Ar 10 and Ar 11 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group, and

[0423] X 4 is NR e , O or S and,

[0424] X5 is CR k R l or SiR m R n And,

[0425] R e , R k , R l , R m and R n Each is independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and

[0426] R 24 , R 26 to R 29 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group or a substituted or unsubstituted C6 to C30 aryl group, and

[0427] m27' and m29' are each independently integers from 1 to 3.

[0428] For example, the above L 12 to L 14 Each may independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0429] For example, the above Ar 10 and Ar 11 Each may 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 carbazoleyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzofuranofluorenyl group, or a substituted or unsubstituted benzothiophenfluorenyl group.

[0430] For example, the fourth compound may be one selected from the compounds listed in Group 2 below, but is not limited thereto.

[0431] [그룹 2]

[0432] [D-1] [D-2] [D-3] [D-4] [D-5]

[0433]

[0434] [D-6] [D-7] [D-8] [D-9] [D-10]

[0435]

[0436] [D-11] [D-12] [D-13] [D-14] [D-15]

[0437]

[0438] [D-16] [D-17] [D-18] [D-19] [D-20]

[0439]

[0440] [D-21] [D-22] [D-23] [D-24] [D-25]

[0441]

[0442] [D-26] [D-27] [D-28] [D-29] [D-30]

[0443]

[0444] [D-31] [D-32] [D-33] [D-34] [D-35]

[0445]

[0446] [D-36] [D-37] [D-38] [D-39] [D-40]

[0447]

[0448] [D-41] [D-42] [D-43] [D-44] [D-45]

[0449]

[0450] [D-46] [D-47] [D-48] [D-49] [D-50]

[0451]

[0452] [D-51] [D-52] [D-53] [D-54] [D-55]

[0453]

[0454] [D-56] [D-57] [D-58] [D-59] [D-60]

[0455]

[0456] [D-61] [D-62] [D-63] [D-64] [D-65]

[0457]

[0458] [D-66] [D-67] [D-68] [D-69] [D-70]

[0459]

[0460] [D-71] [D-72] [D-73] [D-74] [D-75]

[0461]

[0462] [D-76] [D-77] [D-78] [D-79] [D-80]

[0463]

[0464] [D-81] [D-82] [D-83] [D-84] [D-85]

[0465]

[0466] [D-86] [D-87] [D-88] [D-89] [D-90]

[0467]

[0468] [D-91] [D-92] [D-93] [D-94] [D-95]

[0469]

[0470] [D-96] [D-97] [D-98] [D-99] [D-100]

[0471]

[0472] [D-101] [D-102] [D-103] [D-104] [D-105]

[0473]

[0474] [D-106] [D-107] [D-108] [D-109] [D-110]

[0475]

[0476] [D-111] [D-112] [D-113] [D-114]

[0477]

[0478] [D-115] [D-116] [D-117] [D-118]

[0479]

[0480] [D-119] [D-120] [D-121] [D-122]

[0481]

[0482] [D-123] [D-124] [D-125] [D-126] [D-127]

[0483]

[0484] [E-1] [E-2] [E-3] [E-4]

[0485]

[0486] [E-5] [E-6] [E-7] [E-8]

[0487]

[0488] [E-9] [E-10] [E-11] [E-12]

[0489]

[0490] [E-13] [E-14] [E-15] [E-16]

[0491]

[0492] [E-17] [E-18] [E-19] [E-20]

[0493]

[0494] [E-21] [E-22] [E-23] [E-24]

[0495]

[0496] [E-25] [E-26] [E-27] [E-28]

[0497]

[0498] [E-29] [E-30] [E-31] [E-32]

[0499]

[0500] [E-33] [E-34] [E-35] [E-36]

[0501]

[0502] [E-37] [E-38] [E-39] [E-40]

[0503]

[0504] [E-41] [E-42] [E-43] [E-44]

[0505]

[0506] [E-45] [E-46] [E-47] [E-48]

[0507]

[0508] [E-49] [E-50] [E-51] [E-52]

[0509]

[0510] [E-53] [E-54] [E-55] [E-56] [E-57]

[0511]

[0512] [E-58] [E-59] [E-60] [E-61] [E-62]

[0513]

[0514] [E-63] [E-64] [E-65] [E-66] [E-67]

[0515]

[0516] [E-68] [E-69]

[0517]

[0518] [E-70] [E-71] [E-72] [E-73]

[0519]

[0520] [E-74] [E-75] [E-76] [E-77]

[0521]

[0522] [E-78] [E-79] [E-80] [E-81]

[0523]

[0524] [E-82] [E-83] [E-84] [E-85]

[0525]

[0526] [E-86] [E-87] [E-88] [E-89]

[0527]

[0528] [E-90] [E-91] [E-92] [E-93]

[0529]

[0530] [E-94] [E-95] [E-96] [E-97]

[0531]

[0532] [F-1] [F-2] [F-3] [F-4] [F-5]

[0533]

[0534] [F-6] [F-7] [F-8] [F-9] [F-10]

[0535]

[0536] [F-11] [F-12] [F-13] [F-14] [F-15]

[0537]

[0538] [F-16] [F-17] [F-18] [F-19] [F-20]

[0539]

[0540] [F-21] [F-22] [F-23] [F-24] [F-25]

[0541]

[0542] [F-26] [F-27] [F-28] [F-29] [F-30]

[0543]

[0544] [F-31] [F-32] [F-33] [F-34] [F-35]

[0545]

[0546] [F-36] [F-37] [F-38] [F-39] [F-40]

[0547]

[0548] [F-41] [F-42] [F-43] [F-44] [F-45]

[0549]

[0550] [F-46] [F-47] [F-48] [F-49] [F-50]

[0551]

[0552] [F-51] [F-52] [F-53] [F-54] [F-55]

[0553]

[0554] [F-56] [F-57] [F-58] [F-59] [F-60]

[0555]

[0556] [F-61] [F-62] [F-63] [F-64] [F-65]

[0557]

[0558] [F-66] [F-67] [F-68] [F-69] [F-70]

[0559]

[0560] [G-1] [G-2] [G-3] [G-4]

[0561]

[0562] [G-5] [G-6] [G-7] [G-8]

[0563]

[0564] [G-9] [G-10] [G-11] [G-12]

[0565]

[0566] [G-13] [G-14] [G-15] [G-16]

[0567]

[0568] [G-17] [G-18] [G-19] [G-20]

[0569]

[0570] [G-21] [G-22] [G-23] [G-24]

[0571]

[0572] [G-25] [G-26] [G-27] [G-28]

[0573]

[0574] [G-29] [G-30] [G-31] [G-32]

[0575]

[0576] [G-33] [G-34] [G-35] [G-36]

[0577]

[0578] [G-37] [G-38] [G-39] [G-40]

[0579]

[0580] [G-41] [G-42] [G-43] [G-44]

[0581]

[0582] [G-45] [G-46] [G-47] [G-48]

[0583]

[0584] (Dn represents the number of deuterium substitutions, where n is an integer greater than or equal to 0).

[0585] As the fourth compound represented by Chemical Formula 7, in addition to the aforementioned compound, compounds listed in KR10-2019-0123138A, KR10-2219645B1, KR10-2217250B1, KR10-2207892B1, KR10-2671849B1, KR10-2022-0033348A, KR10-2306966B1, KR10-2023-0132367A, KR10-2021-0080183A, KR10-2021-0116214A, KR10-2019-0034074A, etc. may be applied.

[0586] The first compound and the fourth compound may be included in a weight ratio of, for example, 1:99 to 99:1. By including them within the above range, bipolar characteristics can be realized by adjusting the weight ratio appropriately using the electron transport ability of the first compound and the hole transport ability of the fourth compound, thereby improving efficiency and lifespan. Within the above range, they may be included in a weight ratio of, for example, about 10:90 to 90:10 or about 20:80 to 80:20, and for example, about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40. As a specific example, they may be included in a weight ratio of 40:60, 50:50, or 60:40.

[0587] The dopant can be, for example, a phosphorescent dopant, for example, a red, green, or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0588] A dopant is a substance that is mixed in trace amounts into a host to produce luminescence, and generally, substances such as metal complexes that emit light through multiple excitation, which excites the host to a triplet state or higher, may be used. The dopant may be, for example, inorganic, organic, or organic-inorganic compounds, and may include one or more types.

[0589] Phosphorescent dopants are an example of a dopant, and examples of phosphorescent dopants include organometallic compounds containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants may include, for example, compounds represented by the following chemical formula Z, but are not limited thereto.

[0590] [Chemical Formula Z]

[0591] L 15 MX 6

[0592] In the above chemical formula Z, M is a metal, and L 15 and X 6 is a ligand that is the same or different from each other and forms a complex with M.

[0593] 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 15 and X 6 It can be, for example, a bitentate ligand.

[0594] L 15 and X 6 The ligand represented by may be one selected from the following chemical formulas Z-1 to Z-8.

[0595] [Z-1] [Z-2] [Z-3]

[0596]

[0597] [Z-4] [Z-5]

[0598]

[0599] [Chemical Formula Z-6] [Chemical Formula Z-7]

[0600]

[0601] [Z-8]

[0602]

[0603] In the above chemical formulas Z-1 to Z-8,

[0604] X 14 is selected from the group consisting of carbon and nitrogen, and

[0605] Y 100 is O or S,

[0606] R 101 to R 122Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 133 R 134 R 135 or -GeR 133 R 134 R 135 Or; or may be connected to adjacent substituents to form a substituted or unsubstituted ring, for example, together with pyridine, may form a substituted or unsubstituted quinoline, substituted or unsubstituted benzopropyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzopropynoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenopyridine;

[0607] m18 is an integer from 1 to 4, and

[0608] m19 is an integer from 1 to 5.

[0609] L 15 and X 6 Specific examples of ligands represented by may be selected from the chemical formulas listed in Group A below, but are not limited thereto.

[0610] [Group A]

[0611]

[0612]

[0613] In the above group A,

[0614] R 300 to R 302 Each is independently hydrogen, deuterium, a C1 to C30 alkyl group substituted or unsubstituted with a halogen, a C6 to C30 aryl group substituted or unsubstituted with a C1 to C30 alkyl group, or a halogen.

[0615] R 303 to R 308Each is 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.

[0616] m25 is one of the integers 1 to 5, and

[0617] m26 is one of integers from 1 to 4, and

[0618] m27 is one of integers from 1 to 3, and

[0619] m28 is an integer of 1 or 2, and

[0620] m29 is one of integers from 1 to 6, and

[0621] If m25 to m29 are 2 or more, each R 303 to R 307 They are identical or different from each other.

[0622] A phosphorescent dopant according to one embodiment may be an iridium complex and may be represented, for example, by any one of the following chemical formulas 9 to 11.

[0623] [Chemical Formula 9]

[0624]

[0625] In the above chemical formula 9,

[0626] Ring A is a monocyclic ring or a polycyclic fused ring, and

[0627] Here, each of the monocyclic ring and the polycyclic fused ring is a pentagonal or hexacyclic carbocyclic or heterocyclic, and

[0628] R 100 ...represents one to a maximum number of monovalent substituents,

[0629] R 100 If there are 2 or more of these, each R 100 They are identical or different from each other,

[0630] R 101 to R 104 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 114 R 115 R 116 , -GeR 114 R 115 R 116 or a combination of these,

[0631] The above R 114 to R 116 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0632] X 10 and X 11 Each is independently selected from the group consisting of carbon and nitrogen, and

[0633] L 100 It is a monovalent anion ligand or bitentate ligand that coordinates to iridium through non-covalent electron pairs of carbon or heteroatoms, and

[0634] m21 is any one of integers from 0 to 3.

[0635] [Chemical Formula 10]

[0636]

[0637] In the above chemical formula 10,

[0638] Ring B is a monocyclic ring or a polycyclic fused ring, and

[0639] Here, each of the monocyclic ring and the polycyclic fused ring is a pentagonal or hexacyclic carbocyclic or heterocyclic, and

[0640] Y 100 is O or S,

[0641] R 201 ...represents one to a maximum number of monovalent substituents,

[0642] R 201 If there are 2 or more of these, each R 201 They are identical or different from each other,

[0643] R 206 to R 213 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 114 R 115 R 116 , -GeR 114 R 115 R 116 or a combination of these,

[0644] The above R 114 to R 116 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0645] X 12 and X 13 Each is independently selected from the group consisting of carbon and nitrogen, and

[0646] L 100 It is a monovalent anion ligand or bitentate ligand that coordinates to iridium through non-covalent electron pairs of carbon or heteroatoms, and

[0647] m21 is any one of integers from 0 to 3.

[0648] [Chemical Formula 11]

[0649]

[0650] In the above chemical formula 11,

[0651] Y 100 is O or S,

[0652] R 101 to R 111 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 114 R 115 R 116 , -GeR 114 R 115 R 116 or a combination of these,

[0653] The above R 114 to R 116 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0654] L 100 It is a monovalent anion ligand or bitentate ligand that coordinates to iridium through non-covalent electron pairs of carbon or heteroatoms, and

[0655] m21 is any one of integers from 0 to 3.

[0656] As a more specific example, the above iridium complex can be represented by one of the following chemical formulas 9-1 to 9-6.

[0657] [Chemical Formula 9-1]

[0658]

[0659] In the above chemical formula 9-1,

[0660] R 101 to R 116 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 132 R 133 R 134 or -GeR 132 R 133 R 134 And,

[0661] The above R 132to R 134 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0662] R 101 to R 116 At least one of them is a functional group represented by the following chemical formula V-1, and

[0663] L 100 It is a bidentate ligand of a monovalent anion that coordinates to iridium through lone pairs of electrons on carbon or heteroatoms, and

[0664] m21 and m22 are independently any one of integers from 0 to 3, and m21 + m22 is any one of integers from 1 to 3, and

[0665] [Chemical Formula V-1]

[0666]

[0667] In the above chemical formula V-1,

[0668] R 135 to R 139 Each is 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,

[0669] * represents the part connected to the carbon atom.

[0670] [Chemical Formula 9-2]

[0671]

[0672] [Chemical Formula 9-3]

[0673]

[0674] [Chemical Formula 9-4]

[0675]

[0676] [Chemical Formula 9-5]

[0677]

[0678] [Chemical Formula 9-6]

[0679]

[0680] In the above chemical formulas 9-2 to 9-6,

[0681] X 14 is selected from the group consisting of carbon and nitrogen, and

[0682] Y 100 is O or S,

[0683] R 101 to R 122 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 133 R 134 R 135 or -GeR 133 R 134 R 135 And,

[0684] The above R 133 to R 135 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0685] L 100 It is a bidentate ligand of a monovalent anion that coordinates to iridium through lone pairs of electrons on carbon or heteroatoms, and

[0686] m111 is an integer from 1 to 2, and

[0687] n1 and n2 are independently any one of integers from 0 to 3, and n1 + n2 is any one of integers from 1 to 3.

[0688] A dopant according to another embodiment may be a platinum complex, for example, represented by the chemical formula Z-3.

[0689] [Chemical Formula Z-3]

[0690]

[0691] In the above chemical formula Z-3, rings A, B, C, and D each independently represent a pentagonal or hexagonal carbocyclic or heterocyclic ring;

[0692] R A , R B , R C , and R D Each independently represents a uniform, bisubstitution, trisubstitution, or quadruple substitution, or no substitution;

[0693] nA is an integer of 0 or 1;

[0694] L B , L C , and L D Each is independently selected from the group consisting of direct bonding, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof;

[0695] If nA is 1, L E is selected from the group consisting of direct bonding, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; and when nA is 0, L E is not present;

[0696] 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 arbitrarily connected to form a ring; X B , X C , X D , and X E are each independently selected from the group consisting of carbon and nitrogen; Q 1 , Q 2 , Q 3 , and Q 4 Each represents oxygen or direct bonding.

[0697] The above platinum complex can be represented, for example, by the following chemical formula 12-1 or chemical formula 12-2.

[0698] [Chemical Formula 12-1]

[0699]

[0700] [Chemical Formula 12-2]

[0701]

[0702] In the above chemical formulas 12-1 and 12-2,

[0703] X 100 It contains O, S, and NR 132 Selected from among,

[0704] R 118 to R 132 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 133 R 134 R 135 And,

[0705] The above R 133 to R 135 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0706] R 118 to R 132 At least one of them is -SiR 133 R 134 R 135 or is a tert-butyl group, and

[0707] The above R133 to R 135 Each is an independently substituted or unsubstituted C1 to C6 alkyl group.

[0708] A composition further comprising a dopant may be, for example, a red or green emitting composition.

[0709] The hole transport layer (32) is a layer for facilitating hole transfer from the anode (10) to the light-emitting layer (31) and blocking electrons, and may be, for example, an amine compound, but is not limited thereto.

[0710] The above amine compound may include, for example, at least one aryl group and / or heteroaryl group. The above amine compound may be represented, for example, by the following formula a or formula b, but is not limited thereto.

[0711] [Chemical formula a] [Chemical formula b]

[0712]

[0713] In the above chemical formula a or b,

[0714] Ar a or Ar g Each is 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, and

[0715] Ar a or Ar c At least one of and Ar d or 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, and

[0716] Ar his 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.

[0717] The above organic light-emitting device may additionally include a hole injection layer (34) in addition to the light-emitting layer.

[0718] The hole injection layer (34) is a layer for facilitating hole injection from the anode (10) to the light-emitting layer (31) and blocking electrons, and can be located between the anode (10) and the hole transport layer (32).

[0719] For example, at least one of the above hole transport layer (32) and hole injection layer (34) may contain at least one of the compounds listed in Group B below, and is different from the first hole transport assist layer and second hole transport assist layer materials described later.

[0720] [Group B]

[0721]

[0722]

[0723]

[0724]

[0725]

[0726]

[0727]

[0728]

[0729]

[0730]

[0731]

[0732]

[0733]

[0734]

[0735]

[0736]

[0737]

[0738]

[0739]

[0740]

[0741]

[0742]

[0743]

[0744]

[0745]

[0746]

[0747]

[0748]

[0749]

[0750]

[0751]

[0752]

[0753]

[0754] (Dn refers to the number of hydrogen atoms substituted with deuterium, indicating a structure with one or more deuterium substitutions.)

[0755] In addition to the aforementioned compounds, known compounds and compounds with similar structures described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. may also be used in the hole transport layer (32) and hole injection layer (34).

[0756] The above hole transport assist layer (33) includes a first hole transport assist layer (33a) adjacent to the hole transport layer and a second hole transport assist layer (33b) adjacent to the light-emitting layer.

[0757] The first hole transport assist layer comprises a second compound represented by the following chemical formula 3, and the second hole transport assist layer comprises a third compound represented by the following chemical formula 3, wherein the second compound and the third compound are different from each other.

[0758] [Chemical Formula 3]

[0759]

[0760] In the above chemical formula 3,

[0761] X 2 is O, S, or CR b R c And,

[0762] L 4 to L 6 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0763] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0764] R b , R c and R 6Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0765] R b and R c Each exists independently or is linked to form substituted or unsubstituted spirobifluorenes, and

[0766] A is substituted or unsubstituted benzene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene or substituted or unsubstituted spirobifluorene, and

[0767] m6 is one of integers from 1 to 3, and

[0768] If m6 is 2 or greater, each R 6 They are identical or different from each other.

[0769] An organic light-emitting device according to one embodiment can have improved lifetime characteristics by applying a combination of two hole transport assisting layers at the interface between a hole transport layer and a light-emitting layer, thereby adjusting the charge balance within the light-emitting layer by controlling the hole injection ability in the first hole transport assisting layer, and introducing a compound with high stability against excitons in the second hole transport assisting layer.

[0770] For example, the above chemical formula 3 can be represented by any one of the following chemical formulas 3-I to 3-VIII.

[0771] [Chemical Formula 3-I] [Chemical Formula 3-II]

[0772]

[0773] [Chemical Formula 3-III] [Chemical Formula 3-IV]

[0774]

[0775] [Chemical Formula 3-V] [Chemical Formula 3-VI]

[0776]

[0777] [Chemical Formula 3-VII] [Chemical Formula 3-VIII]

[0778]

[0779] In the above chemical formulas 3-I to 3-VIII,

[0780] X 2 and X 3 Each independently O, S, or CR b R c And,

[0781] L 4 to L 6 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0782] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0783] R b , R c , R 6 to R 11 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0784] m6 is one of integers from 1 to 3, and

[0785] m7, and m9 to m11 are each independently one of integers 1 to 4, and

[0786] m8 is an integer of 1 or 2, and

[0787] If m6 to m11 are each independently 2 or more, each R 6 to R 11 They are identical or different from each other.

[0788] As a specific example, Ar of the above chemical formula 3 3 and Ar 4 Each may 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted 1-fluorenyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted 9-fluorenyl group, a substituted or unsubstituted 9,9-spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosylolyl group.

[0789] For example, Ar of the above chemical formula 3 3 and Ar 4 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted 1-fluorenyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted 9-fluorenyl group, a substituted or unsubstituted 9,9-spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosylolyl group.

[0790] As an example, R of the above Chemical Formula 3 and Chemical Formulas 3-I to 3-VIII 6 to R 11 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C3 to C10 cycloalkyl group, substituted or unsubstituted C1 to C10 alkylsilyl group, or substituted or unsubstituted C6 to C12 aryl group.

[0791] For example, R of the above Chemical Formula 3 and Chemical Formulas 3-I to 3-VIII 6 to R 11 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted or substituted or unsubstituted phenyl group.

[0792] As an example, L of the above chemical formula 3 4 to L 6 Each can independently be a single bond, or a substituted or unsubstituted phenylene group.

[0793] For example, the above L 4 -Ar 3 and L 5 -Ar 4 Each can be independently selected from the substituents listed in Group III below.

[0794] [Group III]

[0795]

[0796] In the above Group III,

[0797] R 36 to R 41 Each is 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, and

[0798] m36 is one of integers from 1 to 5, and

[0799] m37 is one of integers 1 to 4, and

[0800] m38 is one of integers from 1 to 7, and

[0801] m39 is one of integers 1 to 3, and

[0802] m40 is an integer of 1 or 2, and

[0803] * is a connection point.

[0804] If the above m36 is 2 or more, each R 36They may be the same or different from each other.

[0805] If the above m37 is 2 or more, each R 37 They may be the same or different from each other.

[0806] If the above m38 is 2 or more, each R 38 They may be the same or different from each other.

[0807] If the above m39 is 2 or more, each R 39 They may be the same or different from each other.

[0808] In the case where the above m40 is 2, each R 40 They may be the same or different from each other.

[0809] As a specific example, the second compound and the third compound can each be independently represented by the above chemical formula 3-I.

[0810] For example, in the second compound, X of the above formula 3-I 1 is O, S, or CR b R c And,

[0811] R b and R c Each is independently a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, and

[0812] L 4 to L 6 Each is independently a single bond, and

[0813] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted 1-fluorenyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group or a substituted or unsubstituted dibenzosilolyl group, and

[0814] R 6 and R 7 Each is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, or a substituted or unsubstituted C6 to C12 aryl group, and

[0815] m6 is one of integers from 1 to 3, and

[0816] m7 is one of the integers 1 to 4.

[0817] For example, in the third compound, X of the above formula 3-I 1 is O, S, or CR b R c And,

[0818] R b and R c They are linked together to form substituted or unsubstituted spirobifluorenes, and

[0819] L 4 and L 5 Each is independently a single bond or a substituted or unsubstituted phenylene group, and

[0820] L 6 is a single bond or a substituted or unsubstituted phenylene group, and

[0821] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted 1-fluorenyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted 9-fluorenyl group, a substituted or unsubstituted 9,9-spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group or a substituted or unsubstituted dibenzosilolyl group, and

[0822] R 6 and R 7Each is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, or a substituted or unsubstituted C6 to C12 aryl group, and

[0823] m6 is one of integers from 1 to 3, and

[0824] m7 is one of the integers 1 to 4.

[0825] For example, the second compound and the third compound may each be one selected from the compounds listed in Group 3 below, but are not limited thereto.

[0826] [Group 3]

[0827] [1-1] [1-2] [1-3] [1-4] [1-5]

[0828]

[0829] [1-6] [1-7] [1-8] [1-9] [1-10]

[0830]

[0831] [1-11] [1-12] [1-13] [1-14] [1-15]

[0832]

[0833] [1-16] [1-17] [1-18] [1-19] [1-20]

[0834]

[0835] [1-21] [1-22] [1-23] [1-24] [1-25]

[0836]

[0837] [1-26] [1-27] [1-28] [1-29] [1-30]

[0838]

[0839] [1-31] ​​[1-32] [1-33] [1-34] [1-35]

[0840]

[0841] [1-36] [1-37] [1-38] [1-39] [1-40]

[0842]

[0843] [1-41] [1-42] [1-43] [1-44] [1-45]

[0844]

[0845] [1-46] [1-47] [1-48] [1-49] [1-50]

[0846]

[0847] [1-51] [1-52] [1-53] [1-54] [1-55]

[0848]

[0849] [1-56] [1-57] [1-58] [1-59] [1-60]

[0850]

[0851] [1-61] [1-62] [1-63] [1-64] [1-65]

[0852]

[0853] [1-66] [1-67] [1-68] [1-69] [1-70]

[0854]

[0855] [1-71] [1-72] [1-73] [1-74] [1-75]

[0856]

[0857] [1-76] [1-77] [1-78] [1-79] [1-80]

[0858]

[0859] [1-81] [1-82] [1-83] [1-84] [1-85]

[0860]

[0861] [1-86] [1-87] [1-88] [1-89] [1-90]

[0862]

[0863] [1-91] [1-92] [1-93] [1-94] [1-95]

[0864]

[0865] [1-96] [1-97] [1-98] [1-99] [1-100]

[0866]

[0867] [1-101] [1-102] [1-103] [1-104] [1-105]

[0868]

[0869] [1-106] [1-107] [1-108] [1-109] [1-110]

[0870]

[0871] [1-111] [1-112] [1-113] [1-114] [1-115]

[0872]

[0873] [1-116] [1-117] [1-118] [1-119] [1-120]

[0874]

[0875] [1-121] [1-122] [1-123] [1-124] [1-125]

[0876]

[0877] [1-126] [1-127] [1-128] [1-129] [1-130]

[0878]

[0879] [1-131] [1-132] [1-133] [1-134] [1-135]

[0880]

[0881] [1-136] [1-137] [1-138] [1-139] [1-140]

[0882]

[0883] [1-141] [1-142] [1-143] [1-144] [1-145]

[0884]

[0885] [1-146] [1-147] [1-148] [1-149] [1-150]

[0886]

[0887] [1-151] [1-152] [1-153] [1-154] [1-155]

[0888]

[0889] [1-156] [1-157] [1-158] [1-159] [1-160]

[0890]

[0891] [1-161] [1-162] [1-163] [1-164] [1-165]

[0892]

[0893] [1-166] [1-167] [1-168] [1-169] [1-170]

[0894]

[0895] [1-171] [1-172] [1-173] [1-174] [1-175]

[0896]

[0897] [1-176] [1-177] [1-178] [1-179] [1-180]

[0898]

[0899] [1-181] [1-182] [1-183] [1-184] [1-185]

[0900]

[0901] [1-186] [1-187] [1-188] [1-189] [1-190]

[0902]

[0903] [1-191] [1-192] [1-193] [1-194] [1-195]

[0904]

[0905] [1-196] [1-197] [1-198] [1-199] [1-200]

[0906]

[0907] [1-201] [1-202] [1-203] [1-204] [1-205]

[0908]

[0909] [1-206] [1-207] [1-208] [1-209] [1-210]

[0910]

[0911] [1-211] [1-212] [1-213] [1-214] [1-215]

[0912]

[0913] [1-216] [1-217] [1-218] [1-219] [1-220]

[0914]

[0915] [1-221] [1-222] [1-223] [1-224] [1-225]

[0916]

[0917] [1-226] [1-227] [1-228] [1-229] [1-230]

[0918]

[0919] [1-231] [1-232] [1-233] [1-234] [1-235]

[0920]

[0921] [1-236] [1-237] [1-238] [1-239] [1-240]

[0922]

[0923] [1-241] [1-242] [1-243] [1-244] [1-245]

[0924]

[0925] [1-246] [1-247] [1-248] [1-249] [1-250]

[0926]

[0927] [1-251] [1-252] [1-253] [1-254] [1-255]

[0928]

[0929] [1-256] [1-257] [1-258] [1-259] [1-260]

[0930]

[0931] [1-261] [1-262] [1-263] [1-264] [1-265]

[0932]

[0933] [1-266] [1-267] [1-268] [1-269] [1-270]

[0934]

[0935] [1-271] [1-272] [1-273] [1-274] [1-275]

[0936]

[0937] [1-276] [1-277] [1-278] [1-279] [1-280]

[0938]

[0939] [1-281] [1-282] [1-283] [1-284] [1-285]

[0940]

[0941] [1-286] [1-287] [1-288] [1-289] [1-290]

[0942]

[0943] [1-291] [1-292] [1-293] [1-294] [1-295]

[0944]

[0945] [1-296] [1-297] [1-298] [1-299] [1-300]

[0946]

[0947] [1-301] [1-302] [1-303] [1-304] [1-305]

[0948]

[0949] [1-306] [1-307] [1-308] [1-309] [1-310]

[0950]

[0951] [1-311] [1-312] [1-313] [1-314] [1-315]

[0952]

[0953] [1-316] [1-317] [1-318] [1-319] [1-320]

[0954]

[0955] [1-321] [1-322] [1-323] [1-324] [1-325]

[0956]

[0957] [1-326] [1-327] [1-328] [1-329] [1-330]

[0958]

[0959] [1-331] [1-332] [1-333] [1-334] [1-335]

[0960]

[0961] [1-336] [1-337] [1-338] [1-339] [1-340]

[0962]

[0963] [1-341] [1-342] [1-343] [1-344] [1-345]

[0964]

[0965] [1-346] [1-347] [1-348] [1-349] [1-350]

[0966]

[0967] [1-351] [1-352] [1-353] [1-354] [1-355]

[0968]

[0969] [1-356] [1-357] [1-358] [1-359] [1-360]

[0970]

[0971] [1-361] [1-362] [1-363] [1-364] [1-365]

[0972]

[0973] [1-366] [1-367] [1-368] [1-369] [1-370]

[0974]

[0975] [1-371] [1-372] [1-373] [1-374] [1-375]

[0976]

[0977] [1-376] [1-377] [1-378] [1-379] [1-380]

[0978]

[0979] [1-381] [1-382] [1-383] [1-384] [1-385]

[0980]

[0981] [1-386] [1-387] [1-388] [1-389] [1-390]

[0982]

[0983] [1-391] [1-392] [1-393] [1-394] [1-395]

[0984]

[0985] [1-396] [1-397] [1-398] [1-399] [1-400]

[0986]

[0987] [1-401] [1-402] [1-403] [1-404]

[0988]

[0989] [1-405] [1-406] [1-407] [1-408]

[0990]

[0991] [1-409] [1-410] [1-411] [1-412]

[0992]

[0993] [1-413] [1-414] [1-415] [1-416]

[0994]

[0995] [1-417] [1-418] [1-419] [1-420]

[0996]

[0997] [2-1] [2-2] [2-3] [2-4] [2-5]

[0998]

[0999] [2-6] [2-7] [2-8] [2-9] [2-10]

[1000]

[1001] [2-11] [2-12] [2-13] [2-14] [2-15]

[1002]

[1003] [2-16] [2-17] [2-18] [2-19] [2-20]

[1004]

[1005] [2-21] [2-22] [2-23] [2-24] [2-25]

[1006]

[1007] [2-26] [2-27] [2-28] [2-29] [2-30]

[1008]

[1009] [2-31] [2-32] [2-33] [2-34] [2-35]

[1010]

[1011] [2-36] [2-37] [2-38] [2-39] [2-40]

[1012]

[1013] [2-41] [2-42] [2-43] [2-44] [2-45]

[1014]

[1015] [2-46] [2-47] [2-48] [2-49] [2-50]

[1016]

[1017] [2-51] [2-52] [2-53] [2-54] [2-55]

[1018]

[1019] [2-56] [2-57] [2-58] [2-59] [2-60]

[1020]

[1021] [2-61] [2-62] [2-63] [2-64] [2-65]

[1022]

[1023] [2-66] [2-67] [2-68] [2-69] [2-70]

[1024]

[1025] [2-71] [2-72] [2-73] [2-74] [2-75]

[1026]

[1027] [2-76] [2-77] [2-78] [2-79] [2-80]

[1028]

[1029] [2-81] [2-82] [2-83] [2-84] [2-85]

[1030]

[1031] [2-86] [2-87] [2-88] [2-89] [2-90]

[1032]

[1033] [2-91] [2-92] [2-93] [2-94] [2-95]

[1034]

[1035] [2-96] [2-97] [2-98] [2-99] [2-100]

[1036]

[1037] [2-101] [2-102] [2-103] [2-104] [2-105]

[1038]

[1039] [2-106] [2-107] [2-108] [2-109] [2-110]

[1040]

[1041] [2-111] [2-112] [2-113] [2-114] [2-115]

[1042]

[1043] [2-116] [2-117] [2-118] [2-119] [2-120]

[1044]

[1045] [2-121] [2-122] [2-123] [2-124] [2-125]

[1046]

[1047] [2-126] [2-127] [2-128] [2-129] [2-130]

[1048]

[1049] [2-131] [2-132] [2-133] [2-134] [2-135]

[1050]

[1051] [2-136] [2-137] [2-138] [2-139] [2-140]

[1052]

[1053] [2-141] [2-142] [2-143] [2-144] [2-145]

[1054]

[1055] [2-146] [2-147] [2-148] [2-149] [2-150]

[1056]

[1057] [2-151] [2-152] [2-153] [2-154] [2-155]

[1058]

[1059] [2-156] [2-157] [2-158] [2-159] [2-160]

[1060]

[1061] [2-161] [2-162] [2-163] [2-164] [2-165]

[1062]

[1063] [2-166] [2-167] [2-168] [2-169] [2-170]

[1064]

[1065] [2-171] [2-172] [2-173] [2-174] [2-175]

[1066]

[1067] [2-176] [2-177] [2-178] [2-179] [2-180]

[1068]

[1069] [2-181] [2-182] [2-183] [2-184] [2-185]

[1070]

[1071] [2-186] [2-187] [2-188] [2-189] [2-190]

[1072]

[1073] [2-191] [2-192] [2-193] [2-194] [2-195]

[1074]

[1075] [2-196] [2-197] [2-198] [2-199] [2-200]

[1076]

[1077] [2-201] [2-202] [2-203] [2-204] [2-205]

[1078]

[1079] [2-206] [2-207] [2-208] [2-209] [2-210]

[1080]

[1081] [2-211] [2-212] [2-213] [2-214] [2-215]

[1082]

[1083] [2-216] [2-217] [2-218] [2-219] [2-220]

[1084]

[1085] [2-221] [2-222] [2-223] [2-224] [2-225]

[1086]

[1087] [2-226] [2-227] [2-228] [2-229] [2-230]

[1088]

[1089] [2-231] [2-232] [2-233] [2-234] [2-235]

[1090]

[1091] [2-236] [2-237] [2-238] [2-239] [2-240]

[1092]

[1093] [2-241] [2-242] [2-243] [2-244] [2-245]

[1094]

[1095] [2-246] [2-247] [2-248] [2-249] [2-250]

[1096]

[1097] [2-251] [2-252] [2-253] [2-254] [2-255]

[1098]

[1099] [2-256] [2-257] [2-258] [2-259] [2-260]

[1100]

[1101] [2-261] [2-262] [2-263] [2-264] [2-265]

[1102]

[1103] [2-266] [2-267] [2-268] [2-269] [2-270]

[1104]

[1105] In the most specific embodiment of the present invention, the first compound is represented by the formula 1-IV or the formula 2-I, and the fourth compound may be represented by any one of the formulas 4-8, 7-2, and 7-3.

[1106] In the above chemical formula 1-IV, X 1 is O or S, and L 1 and L2 Each is independently a single bond, or a substituted or unsubstituted phenylene group, and L 3 is a single bond, and Ar 1 and Ar 2 Each is independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, and R 1 and R 2 Each may independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[1107] In the above chemical formula 2-I, L 1 and L 2 Each is independently a single bond or a substituted or unsubstituted phenylene group, and L 3 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group, and Ar 1 and Ar 2 Each is independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, and R 3 to R 5 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted phenyl group.

[1108] In the above chemical formula 4-8, R 13 to R 16 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and L 7 and L 8 Each is independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, and Ar 5 and Ar 6 Each may independently be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[1109] In the above chemical formulas 7-2 and 7-3, Ar9 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, and L 11 Each is independently a single bond or a substituted or unsubstituted phenylene group, and R 20 to R 23 Each is independently hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, or substituted or unsubstituted carbazole group, and R 22 and R 23 One of them may be a substituted or unsubstituted carbazole group.

[1110] In addition, the second compound is represented by the following chemical formula 3-Ⅰa, and the third compound can be represented by the following chemical formula 3-Ⅰb or chemical formula 3-Ⅷ.

[1111] [Chemical Formula 3-Ⅰa]

[1112]

[1113] In the above chemical formula 3-Ⅰa,

[1114] R b and R c Each is independently a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, and

[1115] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted 1-fluorenyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group or a substituted or unsubstituted dibenzosilolyl group, and

[1116] R 6 , R 7a and R 7bEach is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, or a substituted or unsubstituted C6 to C12 aryl group, and

[1117] m6 is one of integers from 1 to 3;

[1118] [Chemical Formula 3-Ⅰb] [Chemical Formula 3-Ⅷ]

[1119]

[1120] In the above chemical formulas 3-Ⅰb and 3-Ⅷ,

[1121] R b and R c Each is independently a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, and

[1122] L 4 to L 6 Each is independently a single bond or a substituted or unsubstituted phenylene group, and

[1123] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted 1-fluorenyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted 9-fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group, and

[1124] R 6 , R 7 , R 10 and R 11 Each is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, or a substituted or unsubstituted C6 to C12 aryl group, and

[1125] m6 is one of integers from 1 to 3, and

[1126] m7, m10, and m11 are each independently one of integers from 1 to 4.

[1127] For example, R of the above chemical formula 3-Ⅰa 7a and R 7b Each can be an independently substituted or unsubstituted tert-butyl group.

[1128] The above electron transport region can further increase electron injection and / or electron mobility between the cathode (20) and the light-emitting layer (31) and block holes.

[1129] Specifically, the electron transport region may include an electron transport layer (35) between the cathode (20) and the light-emitting layer (31), and an electron transport auxiliary layer (not shown) between the light-emitting layer (31) and the electron transport layer (35), and at least one of the compounds listed in Group C below may be included in at least one of the electron transport layer (35) and the electron transport auxiliary layer.

[1130] [Group C]

[1131]

[1132]

[1133]

[1134]

[1135]

[1136]

[1137]

[1138]

[1139]

[1140]

[1141]

[1142]

[1143]

[1144] One embodiment may be an organic light-emitting device comprising a light-emitting layer (31), a hole transport layer (32), a first hole transport layer (33a), and a second hole transport layer (33b) as organic layers.

[1145] Another embodiment may be an organic light-emitting device that additionally includes a hole injection layer as an organic layer.

[1146] Another embodiment may be an organic light-emitting device that additionally includes an electron transport region as an organic layer.

[1147] Meanwhile, the organic light-emitting device may additionally include an electron injection layer (not shown), etc., in addition to the light-emitting layer as the aforementioned organic layer.

[1148] An organic light-emitting diode can be manufactured by forming an anode or a cathode on a substrate, forming an organic layer using a dry film deposition method such as vacuum evaporation, sputtering, plasma plating, and ion plating, and then forming a cathode or anode thereon.

[1149] The above-described organic light-emitting element can be applied to an organic light-emitting display device.

[1150] The above-described embodiment will be explained in more detail through the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of the claims.

[1151] Unless otherwise noted, the starting materials and reactants used in the following examples and synthesis examples were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry, or P&H Tech, or synthesized using known methods.

[1152]

[1153] A compound presented as a more specific example of the compound of the present invention was synthesized through the following steps.

[1154] (Preparation of the first compound)

[1155] Synthesis Example 1: Synthesis of Compound C-8

[1156] [Reaction Equation 1]

[1157]

[1158] Compound C-8 was synthesized from intermediate C-8-1 (CAS No. 1346007-12-2) and 2-Chloro-4,6-diphenyl-1,3,5-triazine (CAS No. 3842-55-5) by referring to the synthesis method disclosed in registered patent KR 10-1649683.

[1159]

[1160] Synthesis Example 2: Synthesis of Compound C-32

[1161] [Reaction Equation 2]

[1162]

[1163] Compound C-32 was synthesized from intermediate C-32-1 (CAS No. 1115639-92-3) and 2-[1,1′-Biphenyl]-4-yl-4-chloro-6-phenyl-1,3,5-triazine (CAS No. 1472062-94-4) by referring to the synthesis method disclosed in registered patent KR 10-1649683.

[1164]

[1165] Synthesis Example 3: Synthesis of Compound B-182

[1166] [Reaction Equation 3]

[1167]

[1168] Compound B-182 was synthesized from intermediate B-182-1 (CAS No. 3036027-07-0) and 2-[1,1′-Biphenyl]-3-yl-4-[1,1′-biphenyl]-4-yl-6-chloro-1,3,5-triazine (CAS No. 1621467-35-3) by referring to the synthesis method disclosed in registered patent KR 10-1649683.

[1169]

[1170] (Preparation of the 4th compound)

[1171] Synthesis Example 4: Synthesis of Compound D-121

[1172] [Reaction Equation 4]

[1173]

[1174] Compound D-121 was synthesized from intermediate D-121-1 (CAS No. 2769775-48-4) and intermediate D-121-2 (CAS No. 3007666-38-5) by referring to the synthesis method disclosed in Chinese CN 117229193 A.

[1175]

[1176] Synthesis Example 5: Synthesis of Compound D-99

[1177] [Reaction Equation 5]

[1178]

[1179] Compound D-99 was synthesized from intermediate D-99-1 (CAS No. 2861991-04-8) and intermediate D-99-2 (CAS No. 142475-00-1) by referring to the synthesis method disclosed in Chinese CN 117229193 A.

[1180]

[1181] (Preparation of the second compound)

[1182] Synthesis Example 6: Synthesis of Compound 1-139

[1183] [Reaction Equation 6]

[1184]

[1185] 10 g (35.88 mmol) of the above intermediate 1-chloro-8-phenyldibenzo[b,d]furan, 12.97 g (35.88 mmol) of the intermediate N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine, 5.52 g (57.40 mmol) of sodium t-butoxide, and 1.03 g (2.51 mmol) of 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl(Sphos) were dissolved in 239 ml of xylene, 30.99 g (1.08 mmol) of Pd2(dba) was added, and the mixture was refluxed and stirred for 12 hours under a nitrogen atmosphere. After the reaction was completed, the mixture was extracted with toluene and distilled water, the organic layer was dried with anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with normal hexane / dichloromethane (3:1 volume ratio) to obtain 16.2 g (yield 75%) of compound 1-139 as a white solid.

[1186]

[1187] Synthesis Example 7: Synthesis of Compound 1-399

[1188] [Reaction Equation 7]

[1189]

[1190] Compound 1-399 was synthesized in the same manner as in Synthesis Example 7, except that 10.0 g of the intermediate 1,3-di-tert-butyl-5-chloro-9,9-dimethyl-9H-fluorene and 11.78 g of the intermediate bis(9,9-dimethyl-9H-fluoren-2-yl)amine were used in a 1:1 equivalent ratio (14.5 g, yield 70%).

[1191]

[1192] Synthesis Example 8: Synthesis of Compound 1-393

[1193] [Reaction Equation 8]

[1194]

[1195] Compound 1-393 was synthesized in the same manner as in Synthesis Example 7, except that intermediate Int-3 (CAS No. 2356108-27-3) and intermediate Int-4 (CAS No. 1198395-24-2) were used in a 1:1 equivalent ratio.

[1196]

[1197] (Preparation of the third compound)

[1198] Synthesis Example 9: Synthesis of Compound 2-34

[1199] [Reaction Equation 9]

[1200]

[1201] Compound 2-34 was synthesized in the same manner as in Synthesis Example 7, except that intermediate 2-34-1 (CAS No. 2110512-06-4) and intermediate 2-32-2 (CAS No. 1644054-07-8) were used in a 1:1 equivalent ratio.

[1202]

[1203] Synthesis Example 10: Synthesis of Compound 1-27

[1204] [Reaction Equation 10]

[1205]

[1206] Compound 1-27 was synthesized in the same manner as in Synthesis Example 7, except that 2-Bromo-9,9′-dimethylfluorene (CAS No. 28320-31-2) and intermediate 1-27-1 (CAS No. 2226748-58-7) were used in a 1:1 equivalent ratio.

[1207]

[1208] Synthesis Example 11: Synthesis of Compound 1-418

[1209] [Reaction Equation 11]

[1210]

[1211] Except for using 2-Bromo-9,9′-dimethylfluorene (CAS No. 28320-31-2) and intermediate 1-418-1 (CAS No. 1853122-02-7) in a 1:1 equivalent ratio, compound 1-418 (number of deuterium substitutions D) was used in the same manner as in Synthesis Example 7 above. n =0) was synthesized.

[1212]

[1213] Synthesis Example 12: Synthesis of Compound 2-131

[1214] [Reaction Equation 12]

[1215]

[1216] Compound 2-131 was synthesized in the same manner as in Synthesis Example 7, except that 10.0 g of the intermediate 1-chlorodibenzo[b,d]furan and 22.27 g of the intermediate N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine were used in a 1:1 equivalent ratio (24 g, yield 79%).

[1217]

[1218] Synthesis Example 13: Synthesis of Compound 2-171

[1219] [Reaction Equation 13]

[1220]

[1221] Compound 2-171 was synthesized in the same manner as in Synthesis Example 7, except that 10.0 g of the intermediate 1-chloro-8-phenyldibenzo[b,d]furan and 16.20 g of the intermediate N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine were used in a 1:1 equivalent ratio (20.5 g, yield 82%).

[1222]

[1223] (Preparation of comparative compounds)

[1224] Comparative Synthesis Example 1: Synthesis of Comparative Compound R-1

[1225]

[1226] Comparative compound R-1 was synthesized by referring to the synthesis method disclosed in registered patent KR 10-2293436.

[1227]

[1228] Comparative Synthesis Example 2: Synthesis of Comparative Compound R-2

[1229]

[1230] Comparative compound R-2 was synthesized by referring to the synthesis method disclosed in registered patent KR 10-0669716.

[1231]

[1232] Comparative Synthesis Example 3: Synthesis of Comparative Compound R-3

[1233]

[1234] Comparative compound R-3 was synthesized by referring to the synthesis method disclosed in registered patent KR 10-1789998.

[1235]

[1236] Examples 1 to 3 and Comparative Examples 1 to 3: Measurement of Refractive Index

[1237] The refractive index of the first hole transport assisting layer compound at a wavelength of 520 nm was measured using an Elisometer (JA Woollam, M-2000 ® It was measured as ) and is shown in Table 1 below.

[1238] The refractive index was measured using a film formed with a thickness of 50 nm on a silicon wafer substrate by vacuum deposition.

[1239] The first hole transport assist layer compound was modified as described in Table 1 below, and the refractive index was measured in the same manner as in Example 1.

[1240] The refractive index of the hole transport layer compound at a wavelength of 520 nm was also measured using the same method as above, and the value is 1.749.

[1241] No. 1 Hole Transport Auxiliary Layer Refractive Index Example 11-3931.66 Example 21-3991.66 Example 31-1391.733 Comparative Example 1R-11.816 Comparative Example 2R-21.812 Comparative Example 3R-31.860

[1242] Example 4

[1243] A glass substrate coated with a thin film of ITO / Ag / ITO was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as acetone or isopropyl alcohol, dried, transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and then transferred to a vacuum deposition machine. Using the prepared ITO / Ag / ITO (reflective electrode) as the anode, a 100 Å thick hole injection layer was formed by vacuum depositing compound A doped with 3% NDP-9 (commercially available from Novaled) on the ITO / Ag / ITO substrate, and a hole transport layer was formed by depositing compound A to a thickness of 1350 Å on top of the hole injection layer. A first hole transport auxiliary layer was formed by depositing the second compound 1-393 obtained in Synthesis Example 9 to a thickness of 285 Å on the above hole transport layer, and a second hole transport auxiliary layer was formed by depositing the third compound 2-34 obtained in Synthesis Example 10 to a thickness of 50 Å on the above first hole transport auxiliary layer. On the above second hole transport auxiliary layer, a 380 Å thick light-emitting layer was formed by vacuum deposition using 85 wt% of the first compound C-8 (50%) synthesized in Synthesis Example 1 and the fourth compound D-121 (50%) synthesized in Synthesis Example 4 as hosts, and doping with 15 wt% of PtGD as a dopant. Next, compound C was deposited to a thickness of 50 Å on the above-mentioned light-emitting layer to form an electron transport assist layer, and compound D and Liq were vacuum-deposited simultaneously in a 1:1 ratio to form an electron transport layer with a thickness of 310 Å. An organic light-emitting diode was fabricated by forming a cathode by sequentially vacuum-depositing Yb and AgMg on the above-mentioned electron transport layer.

[1244] It was fabricated with the structure ITO / Ag / ITO / Compound A (3% NDP-9 doping, 100Å) / Compound A (1350Å) / First hole transport assist layer (Compound 1-393, 285Å) / Second hole transport assist layer (Compound 2-34, 50Å) / Emissive layer [Host (Compound C-8: Compound D-121 = 5:5) : PtGD = 85wt% : 15wt%] (380Å) / Compound C (50Å) / Compound D : Liq (310Å) / Yb / AgMg.

[1245] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine

[1246] Compound C: 4-{4-[3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[1247] 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

[1248] PtGD:

[1249]

[1250]

[1251] Examples 5 to 11 and Comparative Examples 4 to 9

[1252] An organic light-emitting diode was fabricated in the same manner as in Example 4, except that the composition was changed to the one listed in Table 2 below.

[1253]

[1254] Evaluation: Luminous efficiency characteristics

[1255] The luminous efficiency of organic light-emitting devices according to Examples 4 to 11 and Comparative Examples 4 to 9 was evaluated.

[1256] The specific measurement method is as follows, and the results are shown in Table 2.

[1257] (1) Measurement of change in current density according to voltage change

[1258] For the fabricated organic light-emitting diode, the current flowing through the unit element was measured using a current-voltage meter (Keithley 2400) while increasing the voltage from 0V to 10V, and the result was obtained by dividing the measured current value by the area.

[1259] (2) Measurement of change in brightness according to voltage change

[1260] For the fabricated organic light-emitting diode, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V, and the results were obtained.

[1261] (3) Measurement of luminous efficiency

[1262] Using the luminance, current density, and voltage measured from (1) and (2) above, the same current density (10 mA / cm²) 2 The luminous efficiency (cd / A) of ) was calculated.

[1263] Relative values ​​based on the luminous efficiency of Example 5 are shown in Table 2 below.

[1264] Emitting Layer Hole Transport Auxiliary Layer Luminous Efficiency No. 1 Compound 4 Compound 2 Compound 3 Compound (%) Example 4 C-8D-1211-3932-34101 Example 5 C-8D-1211-3991-27100 Example 6 C-8D-1211-3932-131103 Example 7 C-8D-1211-3932-171102 Example 8 C-8D-1211-1391-418100 Example 9 B-182D-991-1391-418104 Example 10 B-182D-991-3932-34101 Example 11B-182D-991-3932-131103 Comparative Example 4C-8D-121R-12-3493 Comparative Example 5C-8D-121R-22-3487 Comparative Example 6C-8D-121R-32-3491 Comparative Example 7B-182D-99R-12-3490 Comparative Example 8B-182D-99R-22-3486 Comparative Example 9B-182D-99R-32-3492

[1265] Referring to Table 2, it can be seen that the efficiency characteristics of the organic light-emitting devices according to Examples 4 to 11 are significantly improved compared to the organic light-emitting devices according to Comparative Examples 4 to 9.

[1266]

[1267] 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 as defined in the following claims are also included within the scope of the present invention.

Claims

1. Positive and negative poles facing each other, A light-emitting layer located between the anode and the cathode, A hole transport layer located between the anode and the light-emitting layer, A hole transport assist layer located between the light-emitting layer and the hole transport layer. Includes, The above hole transport assist layer includes a first hole transport assist layer adjacent to the hole transport layer and a second hole transport assist layer adjacent to the light-emitting layer, and The light-emitting layer comprises a first compound represented by the following chemical formula 1 or chemical formula 2, and The first hole transport assisting layer comprises a second compound represented by the following chemical formula 3, and The second hole transport assisting layer comprises a third compound represented by the following chemical formula 3, and The second compound and the third compound are different from each other, The refractive index of the hole transport layer is higher than the refractive index of the first hole transport assist layer, and An organic optoelectronic device in which the refractive index of the first hole transport assisting layer is 2.0 or less: [Chemical Formula 1] [Chemical Formula 2] In the above Chemical Formulas 1 and 2, X 1 is O or S, Z 1 To Z 3 Each independently is N or CL a -R a And, Z 1 To Z 3 At least two of them are N, and L a , and L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, and R a , R 1 to R 5 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heterocyclic group, substituted or unsubstituted silyl group, or a combination thereof, and R 1 and R 2 Each exists independently or adjacent groups are connected to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring, and Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and R a , Ar 1 and Ar 2 Each exists independently, or R a , Ar 1 and Ar 2 Adjacent groups are connected to form a substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic ring, and m1 and m3 are each independently one of integers from 1 to 3, and m2, m4, and m5 are each independently one of integers 1 to 4, and If m1 to m5 are each independently 2 or more, each R 1 to R 5 They are identical or different from each other; [Chemical Formula 3] In the above chemical formula 3, X 2 is O, S, or CR b R c And, L 4 to L 6 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and R b , R c and R 6 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and R b and R c Each exists independently or is linked to form substituted or unsubstituted spirobifluorenes, and A is substituted or unsubstituted benzene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene or substituted or unsubstituted spirobifluorene, and m6 is one of integers from 1 to 3, and If m6 is 2 or greater, each R 6 They are identical or different from each other.

2. In Paragraph 1, An organic optoelectronic device in which the refractive index of the first hole transport assisting layer is 1.8 or less.

3. In Paragraph 1, An organic optoelectronic device in which the refractive index of the first hole transport assist layer is less than or equal to the refractive index of the second hole transport assist layer.

4. In Paragraph 1, An organic optoelectronic device in which the T1 energy of the second hole transport assisting layer is 2.5 eV or higher.

5. In Paragraph 1, The above chemical formula 1 is an organic optoelectronic device represented by any one of the following chemical formulas 1-I to 1-IV: [Chemical Formula 1-I] [Chemical Formula 1-II] [Chemical Formula 1-III] [Chemical Formula 1-IV] In the above Chemical Formulas 1-I to 1-IV, X 1 is O or S, Z 1 To Z 3 Each independently is N or CL a -R a And, Z 1 To Z 3 At least two of them are N, and L a , and L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group, and Ar 1 and Ar 2 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quadrphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted crisenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthiophenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group, and R a , and R 1 and R 2 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and m1 is one of integers from 1 to 3, and m2 is one of integers from 1 to 4, and If m1 and m2 are each independently 2 or more, then each R 1 and R 2 They are identical or different from each other.

6. In Paragraph 1, An organic optoelectronic device wherein the above chemical formula 2 is represented by the following chemical formula 2-I or chemical formula 2-II: [Chemical Formula 2-I] [Chemical Formula 2-II] In the above chemical formulas 2-I and 2-II, Z 1 To Z 3 Each independently is N or CL a -R a And, Z 1 To Z 3 At least two of them are N, and L a , and L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group, and Ar 1 and Ar 2 Each is 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 triphenylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and R a , R 3 to R 5 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and m3 is one of integers from 1 to 3, and m4 and m5 are each independently one of integers 1 to 4, and If m3 to m5 are each independently 2 or more, each R 3 to R 5 They are identical or different from each other.

7. In Paragraph 1, The above chemical formula 3 is an organic optoelectronic device represented by any one of the following chemical formulas 3-I to 3-VIII: [Chemical Formula 3-I] [Chemical Formula 3-II] [Chemical Formula 3-III] [Chemical Formula 3-IV] [Chemical Formula 3-V] [Chemical Formula 3-VI] [Chemical Formula 3-VII] [Chemical Formula 3-VIII] In the above chemical formulas 3-I to 3-VIII, X 2 and X 3 Each independently O, S, or CR b R c And, L 4 to L 6 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and R b , R c , R 6 to R 12 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and m6 is one of integers from 1 to 3, and m7, m9, and m10 to m12 are each independently one of integers 1 to 4, and m8 is an integer of 1 or 2, and If m6 to m12 are each independently 2 or more, each R 6 to R 12 They are identical or different from each other.

8. In Paragraph 1, An organic optoelectronic device wherein the light-emitting layer further comprises a fourth compound represented by the following chemical formula 4; a combination of the following chemical formulas 5 and 6; the following chemical formula 7; or chemical formula 8: [Chemical Formula 4] In the above chemical formula 4, R 13 to R 17 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and L 7 and L 8 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and m13, m16, and m17 are each independently one of integers 1 to 4, and m14 and m15 are each independently one of integers 1 to 3, and If m13 to m17 are 2 or more, each R 13 to R 17 are identical or different from each other, n is one of integers from 0 to 2; [Chemical Formula 5] [Chemical Formula 6] In the above chemical formulas 5 and 6, Among a1* to a4* of Chemical Formula 5, two adjacent ones are each a connecting carbon (C) connected to * of Chemical Formula 6, and The remaining two of a1* to a4* in Chemical Formula 5 that are not connected to Chemical Formula 6 are CL b -R d And, L b , L 9 and L 10 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and R d , R 18 and R 19 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and Ar 7 and Ar 8 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m18 and m19 are each independently one of integers 1 to 4, and If m18 and m19 are 2 or more, respectively R 18 and R 19 are identical or different from each other; [Chemical Formula 7] In the above chemical formula 7, L 11 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and R 20 to R 23 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and Ar 9 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m20, m22, and m23 are each independently one of integers 1 to 4, and m21 is one of integers from 1 to 3, and If m20 to m23 are 2 or more, each R 20 to R 23 They are identical or different from each other; [Chemical Formula 8] In the above chemical formula 8, X 4 은 O, S, NR e , CR f R g or SiR h R i And, R e , R f , R g , R h , R i and R 24 Each is independently hydrogen, deuterium, 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, and m24 is one of integers from 1 to 4, and B is any one selected from the rings listed in Group I below, and [Group I] In the above Group I, * is a connection point, and X 5 은 O, S, NR j , CR k R l or SiR m R n And, R j , R k , R l , R m , R n and R 25 to R 29 Each is independently hydrogen, deuterium, 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, and R j and R 24 to R 29 At least one of them is a group represented by the following chemical formula a, and [Chemical formula a] In the above chemical formula a, L 12 to L 14 Each is independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group, and Ar 10 and Ar 11 Each is independently a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and * is a connection point.

9. In Paragraph 8, The above first compound is represented by the following chemical formula 1-IV or chemical formula 2-I, and The above second compound is represented by the following chemical formula 3-Ⅰa, and The above third compound is represented by the following chemical formula 3-Ⅰb or chemical formula 3-Ⅷ, and An organic optoelectronic device wherein the above-mentioned fourth compound is represented by any one of the following chemical formulas 4-8, 7-2, and 7-3: [Chemical Formula 1-IV] [Chemical Formula 2-I] In the above chemical formula 1-IV, X 1 is O or S, L 1 and L 2 Each is independently a single bond, or a substituted or unsubstituted phenylene group, and L 3 is a single bond, and Ar 1 and Ar 2 Each is independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, and R 1 and R 2 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and m1 is one of integers from 1 to 3, and m2 is one of integers from 1 to 4; In the above chemical formula 2-I, Z 1 To Z 3 are each N, and L 1 and L 2 Each is independently a single bond or a substituted or unsubstituted phenylene group, and L 3 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group, and Ar 1 and Ar 2 Each is independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, and R 3 to R 5 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted phenyl group, and m3 is one of integers from 1 to 3, and m4 and m5 are each independently one of integers 1 to 4; [Chemical Formula 3-Ⅰa] In the above chemical formula 3-Ⅰa, R b and R c Each is independently a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, and Ar 3 and Ar 4 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted 1-fluorenyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group or a substituted or unsubstituted dibenzosilolyl group, and R 6 , R 7a and R 7b Each is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, or a substituted or unsubstituted C6 to C12 aryl group, and m6 is one of integers from 1 to 3; [Chemical Formula 3-Ⅰb] [Chemical Formula 3-Ⅷ] In the above chemical formulas 3-Ⅰb and 3-Ⅷ, R b and R c Each is independently a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, and L 4 to L 6 Each is independently a single bond or a substituted or unsubstituted phenylene group, and Ar 3 and Ar 4 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted 1-fluorenyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted 9-fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group, and R 6 , R 7 , R 10 and R 11 Each is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, or a substituted or unsubstituted C6 to C12 aryl group, and m6 is one of integers from 1 to 3, and m7, m10, and m11 are each independently one of integers 1 to 4; [Chemical Formula 4-8] In the above chemical formula 4-8, R 13 to R 16 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and L 7 and L 8 Each is independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, and Ar 5 and Ar 6 Each is independently a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, and m13 and m16 are each independently one of integers 1 to 4, and m14 and m15 are each independently one of integers from 1 to 3; [Chemical Formula 7-2] [Chemical Formula 7-3] In the above chemical formulas 7-2 and 7-3, Ar 9 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, and L 11 Each is independently a single bond or a substituted or unsubstituted phenylene group, and R 20 to R 23 Each is independently hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group or substituted or unsubstituted carbazole group, and R 22 and R 23 One of them is a substituted or unsubstituted carbazole group, and m20, m22, and m23 are each independently one of integers from 1 to 4, and m21 is one of the integers 1 to 3.

10. A display device comprising an organic optoelectronic element according to any one of claims 1 to 9.

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