Organic optoelectronic device and display device

Abstract

The present invention relates to an organic optoelectronic device comprising an anode and a cathode facing each other, a light-emitting layer located between the anode and the cathode, and an electron transport layer located between the light-emitting layer and the cathode, wherein the light-emitting layer comprises a first compound represented by Chemical Formula 1 and a second compound represented by a combination of Chemical Formula 2 and Chemical Formula 3, and the electron transport layer comprises a third compound represented by Chemical Formula 4. The contents of the above chemical formulas 1 to 4 are as defined in the specification.

Description

Technology Field

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

[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. The problem to be solved

[0006] One embodiment provides a compound for organic optoelectronic devices that can lower the driving voltage and realize high-efficiency and long-life organic optoelectronic devices.

[0007] Another embodiment provides a composition for an organic optoelectronic device comprising the above-mentioned compound for the organic optoelectronic device.

[0008] Another embodiment provides an organic optoelectronic device comprising the above-mentioned compound for the organic optoelectronic device or composition for the organic optoelectronic device.

[0009] Another embodiment provides a display device including the above-mentioned organic optoelectronic element. means of solving the problem

[0010] 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, and an electron transport layer located between the light-emitting layer and the cathode, wherein the light-emitting layer comprises a first compound represented by the following chemical formula 1 and a second compound represented by a combination of the following chemical formulas 2 and 3, and the electron transport layer comprises a third compound represented by the following chemical formula 4.

[0011] [Chemical Formula 1]

[0012]

[0013] In the above chemical formula 1,

[0014] Ar 1 or Ar 3 Each is independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0015] L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group;

[0016] [Chemical Formula 2] [Chemical Formula 3]

[0017]

[0018] In the above chemical formulas 2 and 3,

[0019] Among a1* to a4* of Chemical Formula 2, two adjacent ones are each a connecting carbon (C) connected to * of Chemical Formula 3, and

[0020] The remaining two of a1* to a4* in Chemical Formula 2 that are not connected to Chemical Formula 3 are CL a -R a And,

[0021] L a , L 4 and L 5 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and

[0022] R a , R 1 and R 2 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

[0023] Ar 4 and Ar 5 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0024] m1 and m2 are each independently one of integers from 1 to 4;

[0025] [Chemical Formula 4]

[0026]

[0027] In the above chemical formula 4,

[0028] X 1 is O or S,

[0029] Z 1 To Z 6 Each independently N or CR b And,

[0030] Z 1 To Z 3 At least two of them are N, and

[0031] Z 4 To Z 6 At least two of them are N, and

[0032] L 7 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group, and

[0033] Ar 6 or Ar 9 Each is an independently substituted or unsubstituted C6 to C30 aryl group, and

[0034] R b and R 3 to R 6 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, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0035] m3 and m4 are each independently one of integers from 1 to 3, and

[0036] m5 and m6 are each independently one of integers from 1 to 4.

[0037] According to another embodiment, a display device comprising the organic optoelectronic element is provided. Effects of the invention

[0038] It is possible to realize high-efficiency, long-life organic optoelectronic devices while lowering the driving voltage. Brief explanation of the drawing

[0039] FIG. 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment. Specific details for implementing the invention

[0040] 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.

[0041] 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.

[0042] 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. Furthermore, 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 C1 to C5 alkylsilyl group, a C6 to C20 aryl group, a C2 to C20 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 C5 alkyl group, a C1 to C5 alkylsilyl group, a C6 to C18 aryl group, a C2 to C18 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 cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a trimethylsilyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0043] In this specification, “non-substituted” means that the hydrogen atom remains as a hydrogen atom without being substituted by another substituent.

[0044] In this specification, “hydrogen (-H)” may include “deuterium substitution (-D)” or “tritium substitution (-T)”.

[0045] 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.

[0046] 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.

[0047] Aryl groups include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.

[0048] 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.

[0049] 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.

[0050] 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 benzophenanthrenyl 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.

[0051] 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, a substituted or unsubstituted dibenzothiophen dil group, a substituted or unsubstituted benzonaphtufuran dil group, a substituted or unsubstituted benzonaphthiophen dil group, a substituted or unsubstituted benzofuranofluorenyl group, a substituted or unsubstituted benzothiophenfluorenyl group, or a combination thereof, but is not limited thereto.

[0052] 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.

[0053] 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.

[0055] An organic optoelectronic device according to one embodiment is described below.

[0056] 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.

[0057] 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.

[0058] 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.

[0059] FIG. 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment.

[0060] Referring to FIG. 1, an organic light-emitting device (100) according to one embodiment includes an anode (120) and a cathode (110) facing each other, and an organic layer (105) located between the anode (120) and the cathode (110).

[0061] The anode (120) 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 (120) 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.

[0062] The cathode (110) 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 (110) 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, LiF / Al and BaF2 / Ca, but is not limited thereto.

[0063] The above organic layer (105) includes a light-emitting layer (130), and the light-emitting layer (130) includes a host and a dopant, and the host may include a composition for an organic optoelectronic device.

[0064] A composition for an organic optoelectronic device is described below.

[0065] The above composition for an organic optoelectronic device comprises a first compound represented by the following chemical formula 1 and a second compound represented by a combination of the following chemical formulas 2 and 3.

[0066] [Chemical Formula 1]

[0067]

[0068] In the above chemical formula 1,

[0069] Ar 1 or Ar 3 Each is independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0070] L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group;

[0071] [Chemical Formula 2] [Chemical Formula 3]

[0072]

[0073] In the above chemical formulas 2 and 3,

[0074] Among a1* to a4* of Chemical Formula 2, two adjacent ones are each a connecting carbon (C) connected to * of Chemical Formula 3, and

[0075] The remaining two of a1* to a4* in Chemical Formula 2 that are not connected to Chemical Formula 3 are CL a -R a And,

[0076] L a , L 4 and L 5 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and

[0077] R a , R 1 and R 2 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

[0078] Ar 4 and Ar 5Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0079] m1 and m2 are each independently one of integers from 1 to 4.

[0080] In the above Chemical Formula 2, when m1 is 2 or more, each R 1 It may be the same or different.

[0081] In the above Chemical Formula 3, when m2 is 2 or more, each R 2 It may be the same or different.

[0082] R in the above Chemical Formulas 2 and 3 a In the case where 2 or more substitutions occur, each R a It may be the same or different.

[0083] As an example, Ar of the above chemical formula 1 1 or Ar 3 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 phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted benzocarbazoleyl group, a substituted or unsubstituted oxazolocarbazoleyl group, a substituted or unsubstituted indolocarbazoleyl group, a substituted or unsubstituted indolofluorenyl group, It may be a substituted or unsubstituted benzofuranocarbazole group, a substituted or unsubstituted benzothienocarbazole group, or a substituted or unsubstituted dibenzosilol group.

[0084] As a specific example, Ar of the above chemical formula 1 1 or Ar 3 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazoleyl group.

[0085] For example, the first compound above may be represented by any one of the following chemical formulas 1-I, 1-II, 1-III, and 1-IV.

[0086] [Chemical Formula 1-I]

[0087]

[0088] In the above chemical formula 1-I, L 1 to L 3 It is as previously stated, and

[0089] 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group or a substituted or unsubstituted dibenzosilolyl group, and

[0090] R 17 to R 19 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted C1 to C30 alkyl group, or substituted or unsubstituted C6 to C30 aryl group, and

[0091] m17 is one of integers from 1 to 3, and

[0092] m18 and m19 are each independently one of integers 1 to 4;

[0093] [Chemical Formula 1-II]

[0094]

[0095] In the above chemical formula 1-II, L 1 to L 3 It is as previously stated, and

[0096] X 4 is O or S,

[0097] 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group, and

[0098] R 20 to R 21 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, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0099] m20 is one of integers from 1 to 3, and

[0100] m21 is one of integers from 1 to 4;

[0101] [Chemical Formula 1-III]

[0102]

[0103] In the above chemical formula 1-III, L 1 to L 3 It is as previously stated, and

[0104] Z 7 To Z 9 Each independently N or CR f And,

[0105] Z 7 To Z9 At least two of them are N, and

[0106] 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted benzocarbazoleyl group, a substituted or unsubstituted oxazolocarbazoleyl group, a substituted or unsubstituted indolocarbazoleyl group, a substituted or unsubstituted indolofluorenyl group, a substituted or unsubstituted benzofuranocarbazoleyl group, a substituted or unsubstituted benzothienocarbazoleyl group or a substituted or unsubstituted dibenzosilolyl group;

[0107] [Chemical Formula 1-IV]

[0108]

[0109] In the above chemical formula 1-IV, L 1 to L 3 It is as previously stated, and

[0110] X 5 is O or S,

[0111] 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted triphenylene group, and

[0112] Ar 14 is a substituted or unsubstituted C6 to C30 aryl group, and

[0113] R 22is hydrogen, deuterium, cyano group, halogen 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

[0114] m22 is one of the integers 1 to 4.

[0115] As another example, the above-mentioned first compound may be represented by the following chemical formula 1-V or chemical formula 1-VI.

[0116] [Chemical Formula 1-V]

[0117]

[0118] In the above chemical formula 1-V, L 1 to L 3 It is as previously stated, and

[0119] Ring A is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted benzoxazole, and

[0120] 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted benzocarbazoleyl group, a substituted or unsubstituted oxazolocarbazoleyl group, or a substituted or unsubstituted dibenzosilolyl group, and

[0121] R 23 is hydrogen, deuterium, cyano group, halogen 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

[0122] m23 is one of integers from 1 to 4;

[0123] [Chemical Formula 1-VI]

[0124]

[0125] In the above chemical formula 1-VI, L 1 to L 3 It is as previously stated, and

[0126] Ar 15 is a substituted or unsubstituted C6 to C30 aryl group, and

[0127] 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted benzocarbazoleyl group, a substituted or unsubstituted oxazolocarbazoleyl group, or a substituted or unsubstituted dibenzosilolyl group, and

[0128] R 24 and R 25 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, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0129] m24 is one of integers from 1 to 3, and

[0130] m25 is one of the integers 1 to 4.

[0131] As another example, the first compound above may be represented by any one of the following formulas: 1-VII, 1-VIII, 1-IX, 1-X, 1-XI, and 1-XII.

[0132] [Chemical Formula 1-VII]

[0133]

[0134] [Chemical Formula 1-VIII]

[0135]

[0136] [Chemical Formula 1-IX]

[0137]

[0138] [Chemical Formula 1-X]

[0139]

[0140] [Chemical Formula 1-XI]

[0141]

[0142] [Chemical Formula 1-XII]

[0143]

[0144] In the above chemical formulas 1-VII, 1-VIII, 1-IX, 1-X, 1-XI, and 1-XII, L 1 to L 3 It is as previously stated, and

[0145] X 6 is O, S, NR g or CR h R i And,

[0146] 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazoleyl group, or a substituted or unsubstituted dibenzosilolyl group, and

[0147] R g , Rg , R i , and R 26 to R 28 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, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0148] m26 and m28 are each independently one of integers 1 to 4, and

[0149] m27 is an integer of 1 or 2.

[0150] For example, the above R g , R g , R i , and R 17 to R 28 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.

[0151] For example, the above Ar 1 or Ar 3 At least one of them may be a 9-carbazole group.

[0152] In one embodiment, the L 1 -Ar 1 , L 2 -Ar 2 and L 3 -Ar 3 Each can be independently selected from the substituents listed in Group I below.

[0153] [Group I]

[0154]

[0155] In the above Group I,

[0156] X 3 은 O, S, NR c , or CR d R eAnd,

[0157] R c , R d , R e and R 7 to R 11 Each is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a substituted or unsubstituted C2 to C20 heteroaryl group, and

[0158] Ar 10 and Ar 11 Each is an independently substituted or unsubstituted C6 to C20 aryl group, and

[0159] m7 is one of integers from 1 to 5, and

[0160] m8 is one of integers from 1 to 4, and

[0161] m9 is one of integers from 1 to 3, and

[0162] m10 is an integer of 1 or 2, and

[0163] m11 is one of integers from 1 to 7, and

[0164] * is a connection point.

[0165] If m7 is 2 or greater, each R 7 They may be the same or different from each other.

[0166] If m8 is 2 or greater, each R 8 They may be the same or different from each other.

[0167] If m9 is 2 or greater, each R 9 They may be the same or different from each other.

[0168] When m10 is 2, each R 10 They may be the same or different from each other.

[0169] If m11 is 2 or greater, each R 11 They may be the same or different from each other.

[0170] In the most specific embodiment, the first compound represented by the above chemical formula 1 may be one selected from the compounds listed in the following groups 1-1 to 1-3, but is not limited thereto.

[0171] [Group 1-1]

[0172] [1-1] [1-2] [1-3] [1-4]

[0173]

[0174] [1-5] [1-6] [1-7] [1-8]

[0175]

[0176] [1-9] [1-10] [1-11] [1-12]

[0177]

[0178] [1-13] [1-14] [1-15] [1-16]

[0179]

[0180] [1-17] [1-18] [1-19] [1-20]

[0181]

[0182] [1-21] [1-22] [1-23] [1-24]

[0183]

[0184] [1-25] [1-26] [1-27] [1-28]

[0185]

[0186] [1-29] [1-30] [1-31] ​​[1-32]

[0187]

[0188] [1-33] [1-34] [1-35] [1-36]

[0189]

[0190] [1-37] [1-38] [1-39] [1-40]

[0191]

[0192] [1-41] [1-42] [1-43] [1-44]

[0193]

[0194] [1-45] [1-46] [1-47] [1-48]

[0195]

[0196] [1-49] [1-50] [1-51] [1-52]

[0197]

[0198] [1-53] [1-54] [1-55] [1-56]

[0199]

[0200] [Group 1-2]

[0201] [1-57] [1-58] [1-59] [1-60]

[0202]

[0203] [1-61] [1-62] [1-63] [1-64]

[0204]

[0205] [1-65] [1-66] [1-67] [1-68]

[0206]

[0207] [1-69] [1-70] [1-71] [1-72]

[0208]

[0209] [1-73] [1-74] [1-75] [1-76]

[0210]

[0211] [1-77] [1-78] [1-79] [1-80]

[0212]

[0213] [1-81] [1-82] [1-83] [1-84]

[0214]

[0215] [1-85] [1-86] [1-87] [1-88]

[0216]

[0217] [1-89] [1-90] [1-91] [1-92]

[0218]

[0219] [1-93] [1-94] [1-95] [1-96]

[0220]

[0221] [1-97] [1-98] [1-99] [1-100]

[0222]

[0223] [1-101] [1-102] [1-103] [1-104]

[0224]

[0225] [1-105] [1-106] [1-107] [1-108]

[0226]

[0227] [1-109] [1-110] [1-111] [1-112]

[0228]

[0229] [1-113] [1-114] [1-115] [1-116]

[0230]

[0231] [1-117] [1-118] [1-119] [1-120]

[0232]

[0233] [1-121] [1-122] [1-123] [1-124]

[0234]

[0235] [1-125] [1-126] [1-127] [1-128]

[0236]

[0237] [1-129] [1-130] [1-131] [1-132]

[0238]

[0239] [1-133] [1-134] [1-135] [1-136]

[0240]

[0241] [1-137] [1-138] [1-139] [1-140]

[0242]

[0243] [Groups 1-3]

[0244] [1-141] [1-142] [1-143] [1-144] [1-145]

[0245]

[0246] [1-146] [1-147] [1-148] [1-149] [1-150]

[0247]

[0248] [1-151] [1-152] [1-153] [1-154] [1-155]

[0249]

[0250] [1-156] [1-157] [1-158] [1-159] [1-160]

[0251]

[0252] [1-161] [1-162] [1-163] [1-164] [1-165]

[0253]

[0254] [1-166] [1-167] [1-168] [1-169] [1-170]

[0255]

[0256] [1-171] [1-172] [1-173] [1-174] [1-175]

[0257]

[0258] [1-176] [1-177] [1-178] [1-179] [1-180]

[0259]

[0260] [1-181] [1-182] [1-183] [1-184] [1-185]

[0261]

[0262] [1-186] [1-187] [1-188] [1-189] [1-190]

[0263]

[0264] [1-191] [1-192] [1-193] [1-194] [1-195]

[0265]

[0266] [1-196] [1-197] [1-198] [1-199] [1-200]

[0267]

[0268] [1-201] [1-202] [1-203] [1-204] [1-205]

[0269]

[0270] [1-206] [1-207] [1-208] [1-209] [1-210]

[0271]

[0272] [1-211] [1-212] [1-213] [1-214] [1-215]

[0273]

[0274] [1-216] [1-217] [1-218] [1-219] [1-220]

[0275]

[0276] [1-221] [1-222] [1-223] [1-224] [1-225]

[0277]

[0278] [1-226] [1-227] [1-228] [1-229] [1-230]

[0279]

[0280] [1-231] [1-232] [1-233] [1-234] [1-235]

[0281]

[0282] [1-236] [1-237] [1-238] [1-239]

[0283]

[0284] [1-240] [1-241] [1-242] [1-243]

[0285]

[0286] [1-244] [1-245] [1-246] [1-247]

[0287]

[0288] [1-248] [1-249] [1-250] [1-251]

[0289]

[0290] [1-252] [1-253] [1-254] [1-255]

[0291]

[0292] [1-256] [1-257] [1-258] [1-259]

[0293]

[0294] (Dn refers to the number of deuterium substitutions and indicates a structure with one or more deuterium substitutions.)

[0295] The second compound mentioned above can be used in the light-emitting layer together with the first compound to increase charge mobility and stability, thereby improving luminous efficiency and lifespan characteristics.

[0296] For example, the second compound above may be represented by one of the following formulas: 2A, 2B, 2C, 2D, and 2E.

[0297] [Chemical Formula 2A] [Chemical Formula 2B] [Chemical Formula 2C]

[0298]

[0299] [Chemical Formula 2D] [Chemical Formula 2E]

[0300]

[0301] In the above chemical formulas 2A, 2B, 2C, 2D, and 2E,

[0302] L a1 to L a4 , L 4 and L 5 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and

[0303] R a1 to R a4 , R 1 and R 2 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

[0304] Ar 4and Ar 5 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0305] m1 and m2 are each independently one of integers from 1 to 4.

[0306] For example, Ar of the above chemical formulas 2 and 3 4 and Ar 5 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

[0307] R a1 to R a4 , R 1 and R 2 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.

[0308] In one embodiment, the R a1 to R a4 , R 1 and R 2 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.

[0309] For example, the above R a1 to R a4 , R 1 and R 2Each can independently be a hydrogen, deuterium, cyano group, or a substituted or unsubstituted phenyl group, and

[0310] In a specific embodiment, the R a1 to R a4 , R 1 and R 2 Each can independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0311] As a specific example, the above second compound can be represented by the above chemical formula 2C.

[0312] In one embodiment, the L 4 -Ar 4 and L 5 -Ar 5 Each can be independently one of the substituents listed in Group II below.

[0313] [Group II]

[0314]

[0315] In the above Group II,

[0316] R 12 to R 16 Each is independently hydrogen, deuterium, a cyano group, a C1 to C10 alkyl group, or a C6 to C12 aryl group, and

[0317] m12 is one of integers from 1 to 5, and

[0318] m13 is one of integers from 1 to 4, and

[0319] m14 is one of integers from 1 to 3, and

[0320] m15 is an integer of 1 or 2, and

[0321] m16 is one of integers from 1 to 7, and

[0322] * is a connection point.

[0323] If m12 is 2 or greater, each R 12 They may be the same or different from each other.

[0324] If m13 is 2 or greater, each R 13 They may be the same or different from each other.

[0325] If m14 is 2 or greater, each R 14 They may be the same or different from each other.

[0326] When m15 is 2, each R 15 They may be the same or different from each other.

[0327] If m16 is 2 or greater, each R 16 They may be the same or different from each other.

[0328] For example, the second compound above can be represented by the chemical formula 2c.

[0329] In a specific embodiment of the present invention, the L a1 to L a4 are each single bonds, and L 4 and L 5 Each is independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, and R 1 , R 2 , and R a1 to R a4 are hydrogen, deuterium, or a phenyl group, respectively, and Ar 4 and Ar 5 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.

[0330] For example, the above L a1 to L a4 is a single bond, and R 1 , R 2 , and R a1 to R a4 Each is independently hydrogen, deuterium, or a C6 to C12 aryl group, and L 4 -Ar 4 and L5 -Ar 5 Each may independently be one of the substituents listed in Group II above.

[0331] In the most specific embodiment, the second compound represented by the combination of Formula 2 and Formula 3 may be one selected from the compounds listed in Group 2 below, but is not limited thereto.

[0332] [Group 2]

[0333] [2-1] [2-2] [2-3] [2-4]

[0334]

[0335] [2-5] [2-6] [2-7] [2-8]

[0336]

[0337] [2-9] [2-10] [2-11] [2-12]

[0338]

[0339] [2-13] [2-14] [2-15] [2-16]

[0340]

[0341] [2-17] [2-18] [2-19] [2-20]

[0342]

[0343] [2-21] [2-22] [2-23] [2-24]

[0344]

[0345] [2-25] [2-26] [2-27] [2-28]

[0346]

[0347] [2-29] [2-30] [2-31] [2-32]

[0348]

[0349] [2-33] [2-34] [2-35] [2-36]

[0350]

[0351] [2-37] [2-38] [2-39] [2-40]

[0352]

[0353] [2-41] [2-42] [2-43] [2-44]

[0354]

[0355] [2-45] [2-46] [2-47] [2-48]

[0356]

[0357] [2-49] [2-50] [2-51] [2-52]

[0358]

[0359] [2-53] [2-54] [2-55] [2-56]

[0360]

[0361] [2-57] [2-58] [2-59] [2-60]

[0362]

[0363] [2-61] [2-62] [2-63] [2-64]

[0364]

[0365] [2-65] [2-66] [2-67] [2-68]

[0366]

[0367] [2-69] [2-70] [2-71] [2-72]

[0368]

[0369] [2-73] [2-74] [2-75] [2-76]

[0370]

[0371] [2-77] [2-78] [2-79] [2-80]

[0372]

[0373] [2-81] [2-82] [2-83] [2-84]

[0374]

[0375] [2-85] [2-86] [2-87] [2-88]

[0376]

[0377] [2-89] [2-90] [2-91] [2-92]

[0378]

[0379] [2-93] [2-94] [2-95] [2-96]

[0380]

[0381] [2-97] [2-98] [2-99] [2-100]

[0382]

[0383] The first compound and the second 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 second 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.

[0384] The above dopant may be, for example, a phosphorescent dopant, for example, a red, green, or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0385] A dopant is a substance that is mixed in trace amounts into a compound or composition for an organic optoelectronic device to produce light emission, and generally, a substance such as a metal complex that emits light through multiple excitation, which excites it to a triplet state or higher, may be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one or more types.

[0386] 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.

[0387] [Chemical Formula Z]

[0388] L 6 MX 2

[0389] In the above chemical formula Z, M is a metal, and L 6 and X 2 is a ligand that is the same or different from each other and forms a complex with M.

[0390] 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 6 and X 2 It can be, for example, a bitentate ligand.

[0391] L 6 and X 2Examples of ligands represented by may be selected from the chemical formulas listed in Group A below, but are not limited thereto.

[0392] [Group A]

[0393]

[0394] In the above group A,

[0395] 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.

[0396] R 303 to R 324 Each 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.

[0397] The dopant according to one embodiment may be an iridium complex and may be represented, for example, by the following chemical formula 6-1 or chemical formula 6-2.

[0398] [Chemical Formula 6-1]

[0399]

[0400] In the above chemical formula 6-1,

[0401] R 101 to R 116 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,

[0402] The above R 132 to R 134 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0403] R 101 to R 116 At least one of them is a functional group represented by the following chemical formula V-1, and

[0404] 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

[0405] 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

[0406] [Chemical Formula V-1]

[0407]

[0408] In the above chemical formula V-1,

[0409] 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,

[0410] * represents the part connected to the carbon atom.

[0411] [Chemical Formula 6-2]

[0412]

[0413] In the above chemical formula 6-2,

[0414] R 101 to R 117 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -Si R 133 R 134 R 135 And,

[0415] The above R 133 to R 135 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0416] 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

[0417] 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.

[0418] A dopant according to another embodiment may be a platinum complex, for example, represented by the chemical formula Z-1.

[0419] [Chemical Formula Z-1]

[0420]

[0421] In the above chemical formula Z-1, rings A, B, C, and D each independently represent a pentagonal or hexagonal carbocyclic or heterocyclic ring;

[0422] R A , R B , R C , and R D Each independently represents a uniform, bisubstitution, trisubstitution, or quadruple substitution, or no substitution;

[0423] L B , L C , and L DEach 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;

[0424] 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;

[0425] 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.

[0426] The above platinum complex can be represented, for example, by the following chemical formula 7-1 or chemical formula 7-2.

[0427] [Chemical Formula 7-1]

[0428]

[0429] [Chemical Formula 7-2]

[0430]

[0431] In the above chemical formulas 7-1 and 7-2,

[0432] X 100 It contains O, S, and NR 132 Selected from among,

[0433] 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,

[0434] The above R 133 to R 135 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0435] R 118 to R 132 At least one of them is -SiR 133 R 134 R 135 or is a tert-butyl group, and

[0436] The above R 133 to R 135 Each is an independently substituted or unsubstituted C1 to C6 alkyl group.

[0437] The organic layer may include additional charge transport regions in addition to the light-emitting layer.

[0438] The above charge transport region may be, for example, a hole transport region (140).

[0439] The hole transport region (140) can further increase hole injection and / or hole mobility between the anode (120) and the light-emitting layer (130) and block electrons.

[0440] Specifically, the hole transport region (140) may include a hole transport layer between the anode (120) and the light-emitting layer (130), and a hole transport auxiliary layer between the light-emitting layer (130) and the hole transport layer, and at least one of the compounds listed in Group B below may be included in at least one layer of the hole transport layer and the hole transport auxiliary layer.

[0441] [Group B]

[0442]

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475] (Dn refers to the number of deuterium substitutions and indicates a structure with one or more deuterium substitutions)

[0476] In addition to the aforementioned compound, 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 region (140).

[0477] In addition, the charge transport region may be, for example, an electron transport region (150).

[0478] The above electron transport region (150) can further increase electron injection and / or electron mobility between the cathode (110) and the light-emitting layer (130) and block holes.

[0479] Specifically, the electron transport region (150) may include an electron transport layer between the cathode (110) and the light-emitting layer (130), and an electron transport auxiliary layer between the light-emitting layer (130) and the electron transport layer.

[0480] The electron transport layer may include a third compound represented by the following chemical formula 4.

[0481] [Chemical Formula 4]

[0482]

[0483] In the above chemical formula 4,

[0484] X 1 is O or S,

[0485] Z 1 To Z 6 Each independently N or CR b And,

[0486] Z 1 To Z 3 At least two of them are N, and

[0487] Z 4 To Z 6 At least two of them are N, and

[0488] L 7 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group, and

[0489] Ar 6 or Ar 9 Each is an independently substituted or unsubstituted C6 to C30 aryl group, and

[0490] R b and R 3 to R 6 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, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0491] m3 and m4 are each independently one of integers from 1 to 3, and

[0492] m5 and m6 are each independently one of integers from 1 to 4.

[0493] For example, the above Ar 6 is a substituted or unsubstituted phenyl group, and the Ar 7 or Ar 9 Each can be an independently substituted or unsubstituted C6 to C12 aryl group.

[0494] The above L 7 It may be one selected from the connectors listed in Group III below.

[0495] [Group III]

[0496]

[0497] In the above Group III,

[0498] R 29 is hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C12 aryl group or substituted or unsubstituted C2 to C20 heteroaryl group, and

[0499] m29 is one of integers from 1 to 4, and

[0500] * is a connection point.

[0501] If m29 is 2 or greater, each R 29 It may be the same or different.

[0502] In the most specific embodiment, the third compound represented by the above chemical formula 4 may be one selected from the compounds listed in Group 3 below, but is not limited thereto.

[0503] [Group 3]

[0504] [3-1] [3-2] [3-3] [3-4]

[0505]

[0506] [3-5] [3-6] [3-7] [3-8]

[0507]

[0508] [3-9] [3-10] [3-11] [3-12]

[0509]

[0510] [3-13] [3-14] [3-15] [3-16]

[0511]

[0512] [3-17] [3-18] [3-19] [3-20]

[0513]

[0514] [3-21] [3-22] [3-23] [3-24]

[0515]

[0516] [3-25] [3-26] [3-27] [3-28]

[0517]

[0518] [3-29] [3-30] [3-31] [3-32]

[0519]

[0520] [3-33] [3-34] [3-35] [3-36]

[0521]

[0522] [3-37] [3-38] [3-39] [3-40]

[0523]

[0524] [3-41] [3-42] [3-43] [3-44]

[0525]

[0526] [3-45] [3-46] [3-47] [3-48]

[0527]

[0528] [3-49] [3-50] [3-51] [3-52]

[0529]

[0530] [3-53] [3-54] [3-55] [3-56]

[0531]

[0532] [3-57] [3-58] [3-59] [3-60]

[0533]

[0534] [3-61] [3-62] [3-63] [3-64]

[0535]

[0536] [3-65] [3-66] [3-67] [3-68]

[0537]

[0538] [3-69] [3-70] [3-71] [3-72]

[0539]

[0540] [3-73] [3-74] [3-75] [3-76]

[0541]

[0542] The third compound represented by Chemical Formula 4 above has a relatively high T1 energy, so when included in the electron transport layer, it effectively prevents back-energy transfer and can effectively inhibit excitons formed in the emissive layer. In addition, the presence of DBX substituents allows for the stable distribution of the LUMO electron cloud, thereby enhancing molecular stability when used as an electron transport layer. When such a compound is used as an electron transport layer, electron transport occurs effectively, which can improve device characteristics. In particular, since the molecular structure itself is stable and it can effectively inhibit excitons in the emissive layer, lifetime characteristics can be improved.

[0543] Meanwhile, the second compound represented by the combination of Chemical Formula 2 and Chemical Formula 3 has a shallow HOMO energy level, which increases hole injection and transport capabilities, and thus can improve device characteristics when used in the emissive layer together with the first compound. Because the second compound has excellent hole injection and transport capabilities, the emission zone shifts relatively toward the electron transport layer, potentially leading to a decrease in device lifespan due to interface degradation between the emissive layer and the electron transport layer. When used in combination with the third compound in the electron transport layer, interface degradation is effectively prevented, thereby preventing a decrease in lifespan while simultaneously improving low-drive and high-efficiency characteristics.

[0544] In the most specific embodiment, the first compound may be represented by the formula 1-V, and the second compound may be represented by the formula 3C.

[0545] The electron transport assist layer may include at least one of the compounds listed in Group C below.

[0546] [Group C]

[0547]

[0548]

[0549]

[0550]

[0551]

[0552]

[0553]

[0554]

[0555]

[0556]

[0557]

[0558]

[0559]

[0560]

[0561]

[0562]

[0563]

[0564] An organic light-emitting device according to one embodiment of the present invention may include a hole transport region (140) and an electron transport region (150) in addition to the light-emitting layer (130) as an organic layer (105) as shown in FIG. 1.

[0565] Meanwhile, the organic light-emitting device may additionally include an electron injection layer (not shown), a hole injection layer (not shown), etc., in addition to the light-emitting layer as the aforementioned organic layer.

[0566] An organic light-emitting device (100) can be manufactured by forming an anode or a cathode on a substrate, then forming an organic layer using a dry film deposition method such as vacuum deposition (evaporation), sputtering, plasma plating, and ion plating, and then forming a cathode or an anode thereon.

[0567] The above-described organic light-emitting element can be applied to an organic light-emitting display device.

[0569] 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.

[0570] 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.

[0572] (Synthesis of compounds for organic optoelectronic devices)

[0573] Synthesis of the first compound

[0574] Synthesis Example 1: Synthesis of Compound 1-98

[0575] [Reaction Equation 1]

[0576]

[0577] Step 1: Synthesis of Intermediate I-1

[0578] Under nitrogen conditions, 2,4-Dichloro-6-(phenyl-2,3,4,5,6-d5)-1,3,5-triazine (59.3 g, 256 mmol) and 9H-Carbazole-1,2,3,4,5,6,7,8-d8 (30 g, 171 mmol) were dissolved in 500 ml of tetrahydrofuran, and then sodium tert-butoxide (18.1 g, 188 mmol) was slowly added and stirred at 0°C. After 12 hours, water was added to the reaction mixture and the mixture was filtered. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-1 (50 g, 79%).

[0579] Step 2: Synthesis of Intermediate I-2

[0580] Under nitrogen conditions, (3-(9H-carbazol-9-yl-d8)phenyl-2,4,5,6-d4)boronic acid (30.6 g, 102 mmol) and 1-bromo-4-chlorobenzene-2,3,5,6-d4 (20 g, 102 mmol) were added and dissolved in 300 ml of tetrahydrofuran. Then, 150 ml of an aqueous solution of potassium carbonate (28.2 g, 204 mmol) was added and stirred. Tetrakis(triphenylphosphine)palladium (3.54 g, 3.06 mmol) was added to this mixture, and the mixture was heated at 80°C for 12 hours while refluxing and stirring. After the reaction was complete, the organic layer was extracted, water was removed with magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-2 (35 g, 93%).

[0581] Step 3: Synthesis of Intermediate I-3

[0582] Under nitrogen conditions, intermediate I-2 (35 g, 94.6 mmol) was dissolved in 500 ml of xylene, then bis(pinacolato)diboron (28.8 g, 113 mmol), Tris(dibenzylideneacetone)dipalladium (0) (0.87 g, 0.95 mmol), Tricyclohexylphosphine (1.1 g, 3.8 mmol), and potassium acetate (27.8 g, 284 mmol) were added, and the mixture was heated and refluxed for 8 hours. After the reaction was complete, water was added to the reaction mixture and extracted with dichloromethane, followed by water removal with magnesium sulfate anhydrous, filtering, and vacuum concentration. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-3 (30 g, 69%).

[0583] Step 4: Synthesis of Intermediate I-4

[0584] Compound 1-98 (15 g, 83%) was obtained using intermediate I-1 (10 g, 27 mmol) and intermediate I-3 (12.5 g, 27 mmol) in the same manner as in step 2.

[0586] Synthesis Example 2: Synthesis of Compound 1-119

[0587] [Reaction Equation 2]

[0588]

[0589] Step 1: Synthesis of Intermediate I-4

[0590] Under nitrogen conditions, 2-Bromo-1-fluoro-3-iodobenzene (50.0 g, 166.2 mmol), phenylboronic acid (22.3 g, 182.8 mmol), K2CO3 (45.9 g, 332.4 mmol), and Pd(PPh3)4 (9.6 g, 8.3 mmol) were placed in a round-bottom flask, dissolved in THF (350 ml) and distilled water (160 ml), and stirred under reflux at 70°C for 6 hours. After the reaction was finished, the aqueous layer was removed, and 28.9 g (69%) of intermediate I-4 was obtained using column chromatography (Hexane:DCM (30%)).

[0591] Step 2: Synthesis of Intermediate I-5

[0592] Under nitrogen conditions, intermediate I-4 (21.7 g, 105.0 mmol), Bis(pinacolato)diboron (35.1 g, 138.1 mmol), Potassium acetate (22.6 g, 230.2 mmol), and Pd(dppf)Cl2 (4.7 g, 5.8 mmol) were placed in a round-bottom flask and dissolved in 380 ml of Xylene. The mixture was refluxed and stirred at 140°C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered to remove salts, and then extracted with excess DCM and distilled water. 20.6 g (60%) of intermediate I-5 was obtained using column chromatography (Hexane:DCM (30% to 50%)).

[0593] Step 3: Synthesis of Intermediate I-7

[0594] Under nitrogen conditions, intermediate I-5 (20.6g, 69.1mmol), intermediate I-6 (20.6g, 57.6mmol), K2CO3 (15.9g, 115.2mmol), and Pd(PPh3)4 (3.33g, 2.88mmol) were placed in a round-bottom flask, dissolved in THF (300ml) and distilled water (60ml), and refluxed and stirred at 70°C for 6 hours. After the reaction was finished, the aqueous layer was removed, and 19.9g (70%) of intermediate I-7 was obtained using column chromatography (Hexane:DCM (30%)).

[0595] Step 4: Synthesis of Compound 1-119

[0596] Under nitrogen conditions, intermediate I-7 (19.9 g, 40.3 mmol), 2-Phenyl-9H-carbazole (19.6 g, 80.6 mmol), and K3PO4 (17.1 g, 80.6 mmol) were placed in a round-bottom flask, dissolved in DMF (130 ml), and stirred under reflux at 150°C for 4 hours. After the reaction was finished, the reaction mixture was slowly added dropwise to excess water to precipitate the solid, and the solid obtained by filtration was separated by column chromatography (Hexane:DCM (30%)) to obtain 17.9 g (62%) of compound 1-119.

[0598] Synthesis of the second compound

[0599] Synthesis Example 3: Synthesis of Compound 2-32

[0600]

[0601] Compound 2-32 was synthesized by referring to the method disclosed in KR10-2072208.

[0602] Synthesis Example 4: Synthesis of Compound R-1

[0603]

[0604] Compound R-1 was synthesized by referring to the method disclosed in KR10-1649683.

[0606] Synthesis of the third compound

[0607] Synthesis Example 5: Synthesis of Compound 3-29

[0608] [Reaction Equation 3]

[0609]

[0610] Step 1: Synthesis of Intermediate I-8

[0611] Under nitrogen conditions, 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (25g, 59.54mmol) was dissolved in 200ml of xylene, then bis(pinacolato)diboron (18.9g, 74.42mmol), Pd(dppf)Cl2 (2.18g, 2.98mmol), tricyclohexylphosphine (3.34g, 11.91mmol), and potassium acetate (11.69g, 119.07mmol) were added, and the mixture was heated and refluxed for 8 hours. After the reaction was complete, water was added to the reaction solution and extracted with DCM, then water was removed with MgSO4, filtered, and concentrated under reduced pressure. The residue obtained in this way was separated and purified by flash column chromatography to obtain intermediate I-8 (21.21g, 80%).

[0612] Step 2: Synthesis of Compound I-9

[0613] Intermediate I-9 was synthesized by referring to the method disclosed in KR 10-2022-0032864.

[0614] Step 3: Synthesis of Compound 3-29

[0615] Under nitrogen conditions, intermediates I-8 (21.21 g, 41.47 mmol), I-9 (17.99 g, 41.47 mmol), K2CO3 (11.46 g, 82.94 mmol), and Pd(PPh3)4 (2.40 g, 2.07 mmol) were placed in a round-bottom flask, dissolved in THF (200 ml) and distilled water (60 ml), and stirred under reflux at 60°C for 12 hours. After the reaction was complete, the aqueous layer was removed, and the organic solvent was removed under reduced pressure to obtain a solid. The obtained solid was dissolved in a high-temperature MCB. After removing moisture with MgSO4, the organic solvent was filtered using a silica gel pad, and the filtrate was stirred. Once a solid was formed, it was filtered and vacuum dried to obtain 22.73 g (70%) of compound 3-29.

[0617] Synthesis Example 6: Synthesis of Compound R-2

[0618]

[0619] Compound R-2 was synthesized by referring to the method disclosed in KR 10-2086763.

[0621] Synthesis Example 7: Synthesis of Compound R-3

[0622]

[0623] Compound R-3 was synthesized using the intermediates I-8 and 2-([1,1'-Biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine in the same manner as the synthesis of compound 3-29.

[0625] Example 1: Fabrication of a green organic light-emitting diode

[0626] A glass substrate coated with a thin film of ITO (Indium Tin Oxide) was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, 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 transparent electrode as the anode, a 100 Å thick hole injection layer was formed by vacuum depositing compound E doped with 3% NDP-9 (commercially available from Novaled) on the 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 hole transport auxiliary layer was formed by depositing compound B to a thickness of 320 Å on top of the hole transport layer. On the above hole transport assist layer, compound 1-119 and compound 2-32 were simultaneously used as hosts in a weight ratio of 3:7, and IrGD was doped at 7 wt% as a dopant to form an emissive layer with a thickness of 330 Å by vacuum deposition. Subsequently, compound 3-29 was deposited to a thickness of 50 Å on the emissive layer to form an electron transport assist layer, and compound 3-29 and Liq were simultaneously vacuum deposited in a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å. An organic light-emitting diode was fabricated by sequentially vacuum depositing LiQ 15 Å and Al 1200 Å on the electron transport layer to form a cathode.

[0627] It was fabricated with the structure ITO / Compound A (3% NDP-9 doping, 100Å) / Compound B (1350Å) / Compound F (320Å) / EML[Host(Compound 1-119 : Compound 2-32 = 3 : 7 wt% / wt%) : IrGD = 93wt% : 7wt%](330Å) / Compound 3-29(50Å) / Compound 3-29:LiQ(300Å) / LiQ(15Å) / Al(1200Å).

[0628] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine

[0629] Compound B: N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-2-amine

[0630] [IrGD]

[0631]

[0633] Example 2 and Comparative Examples 1 to 8

[0634] An organic light-emitting diode was fabricated using the same method as in Example 1, except that the composition was changed to the one described in Tables 1 to 5 below.

[0636] evaluation

[0637] The driving voltage and lifespan characteristics of organic light-emitting diodes according to Example 1, Example 2 and Comparative Examples 1 to 8 were evaluated.

[0638] The specific measurement method is as follows, and the results are as shown in Tables 1 to 5.

[0639] (1) Measurement of change in current density according to voltage change

[0640] 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.

[0641] (2) Measurement of change in brightness according to voltage change

[0642] 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.

[0643] (3) Life measurement

[0644] Luminance (cd / m²) 2 ) 30,000 cd / m 2 The result was obtained by maintaining it and measuring the time it took for the current efficiency (cd / A) to decrease to 97%.

[0645] The life measurement values ​​were calculated as relative values ​​based on the life measurement values ​​of Example 1 or Example 2 and listed in Tables 3 to 5 below.

[0646] (4) Driving voltage measurement

[0647] Using a current-voltage meter (Keithley 2400) at 15 mA / cm 2 The driving voltage of each component was measured to obtain the results.

[0648] The driving voltage was calculated as a relative value based on the driving voltage of Example 1 or Example 2 and is listed in Tables 1, 2, and 5 below.

[0649] No. Host Electron transport auxiliary layer and electrotransport layer Driving voltage (%) 1st compound second compound Third compound Example 1 Compound 1-119 Compound 2-32 Compound 3-29 100 Comparative Example 1 Compound 1-119 Compound R-1 Compound 3-29 108

[0650] No. Host Electron transport auxiliary layer and electrotransport layer Driving voltage (%) 1st compound second compound Third compound Example 2 Compound 1-98 Compound 2-32 Compound 3-29 100 Comparative Example 2 Compound 1-98 Compound R-1 Compound 3-29 109

[0651] No. Host Electron transport auxiliary layer and electrotransport layer life(%) 1st compound second compound Third compound Example 1 Compound 1-119 Compound 2-32 Compound 3-29 100 Comparative Example 3 Compound 1-119 Compound 2-32 Compound R-2 89 Comparative Example 4 Compound 1-119 Compound 2-32 Compound R-3 84

[0652] No. Host Electron transport auxiliary layer and electrotransport layer life(%) 1st compound second compound Third compound Example 2 Compound 1-98 Compound 2-32 Compound 3-29 100 Comparative Example 5 Compound 1-98 Compound 2-32 Compound R-2 87 Comparative Example 6 Compound 1-98 Compound 2-32 Compound R-3 80

[0653] No. Host Electron transport auxiliary layer and electrotransport layer Driving voltage (%) life(%) 1st compound second compound Third compound Example 2 Compound 1-98 Compound 2-32 Compound 3-29 100 100 Comparative Example 7 Compound 1-98 Compound R-1 Compound R-2 109 21 Comparative Example 8 Compound 1-98 Compound R-1 Compound R-3 113 21

[0654] Referring to Tables 1 and 2, it can be seen that the driving voltage of the organic light-emitting diodes according to Examples 1 and 2 is significantly improved compared to the organic light-emitting diodes according to Comparative Examples 1 and 2. Additionally, referring to Tables 3 and 4, it can be seen that the lifespan of the organic light-emitting diodes according to Examples 1 and 2 is significantly improved compared to the organic light-emitting diodes according to Comparative Examples 3 and 4.

[0655] Referring to Table 5, it can be seen that the driving voltage and lifespan of the organic light-emitting device according to Example 1 are significantly improved compared to the organic light-emitting devices according to Comparative Examples 7 and 8. In particular, it can be seen that the lifespan characteristics are significantly improved.

[0657] 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. Explanation of the symbols

[0658] 100: Organic light-emitting diode 105: Organic layer 110: Cathode 120: Anode 130: Emissive layer 140: Precision Transport Area 150: Electronic transport area

Claims

Claim 1 An organic optoelectronic device comprising an anode and a cathode facing each other, a light-emitting layer located between the anode and the cathode, and an electron transport layer located between the light-emitting layer and the cathode, wherein the light-emitting layer comprises a first compound represented by the following Chemical Formula 1 and a second compound represented by a combination of the following Chemical Formulas 2 and 3, and the electron transport layer comprises a third compound represented by the following Chemical Formula 4: [Chemical Formula 1] In the above chemical formula 1, Ar 1 or Ar 3 Each is independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group; [Chemical Formula 2] [Chemical Formula 3] In the above Chemical Formulas 2 and 3, two adjacent a1* to a4* of Chemical Formula 2 are each connecting carbons (C) connected to * of Chemical Formula 3, and the remaining two a1* to a4* of Chemical Formula 2 that are not connected to Chemical Formula 3 are CL a -R a and,L a , L 4 and L 5 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and R a , R 1 and R 2 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 4 and Ar 5 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m1 and m2 are each independently one of integers 1 to 4; [Chemical Formula 4] In the above chemical formula 4, X 1 is O or S, and Z 1 To Z 6 Each independently N or CR b Igo, Z 1 To Z 3 At least two of them are N and Z 4 To Z 6 At least two of them are N, and L 7 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group, and Ar 6 or Ar 9 Each is an independently substituted or unsubstituted C6 to C30 aryl group, and R b and R 3 to R 6 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, or substituted or unsubstituted C2 to C30 heterocyclic group, and m3 and m4 are each independently one of integers 1 to 3, and m5 and m6 are each independently one of integers 1 to 4. Claim 2 In paragraph 1, the above Ar 1 or Ar 3 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 phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted benzocarbazoleyl group, a substituted or unsubstituted oxazolocarbazoleyl group, a substituted or unsubstituted indolocarbazoleyl group, a substituted or unsubstituted indolofluorenyl group, Organic optoelectronic device comprising a substituted or unsubstituted benzofuranocarbazole group, a substituted or unsubstituted benzothienocarbazole group, or a substituted or unsubstituted dibenzosilol group. Claim 3 An organic optoelectronic device according to claim 1, wherein the first compound is represented by any one of the following formulas 1-I, 1-II, 1-III, and 1-IV: [Formula 1-I] In the above chemical formula 1-I, L 1 to L 3 is as previously stated, 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group, and R 17 to R 19 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted C1 to C30 alkyl group, or substituted or unsubstituted C6 to C30 aryl group, m17 is one of integers 1 to 3, and m18 and m19 are each independently one of integers 1 to 4; [Chemical Formula 1-II] In the above chemical formula 1-II, L 1 to L 3 is as previously stated, and X 4 is O or S, 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group, and R 20 to R 21 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, or substituted or unsubstituted C2 to C30 heterocyclic group, m20 is one of integers from 1 to 3, and m21 is one of integers from 1 to 4; [Chemical Formula 1-III] In the above chemical formula 1-III, L 1 to L 3 is as previously stated, and Z 7 To Z 9 Each independently N or CR f Igo, Z 7 To Z 9 At least two of them are N, 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted benzocarbazoleyl group, a substituted or unsubstituted oxazolocarbazoleyl group, a substituted or unsubstituted indolocarbazoleyl group, a substituted or unsubstituted indolofluorenyl group, a substituted or unsubstituted benzofuranocarbazoleyl group, a substituted or unsubstituted benzothienocarbazoleyl group or a substituted or unsubstituted dibenzosilolyl group; [Chemical Formula 1-IV] In the above chemical formula 1-IV, L 1 to L 3 is as previously stated, and X 5 is O or S, 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted triphenylene group, and Ar 14 is a substituted or unsubstituted C6 to C30 aryl group, and R 22 is hydrogen, deuterium, cyano group, halogen 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 m22 is one of integers from 1 to 4. Claim 4 An organic optoelectronic device according to claim 1, wherein the first compound is represented by the following chemical formula 1-V or chemical formula 1-VI: [Chemical formula 1-V] In the above chemical formula 1-V, L 1 to L 3 ...is as described above, and ring A is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted benzoxazole, 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted benzocarbazoleyl group, a substituted or unsubstituted oxazolocarbazoleyl group, or a substituted or unsubstituted dibenzosilolyl group, and R 23 is hydrogen, deuterium, cyano group, halogen 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 m23 is one of integers 1 to 4; [Chemical Formula 1-VI] In the above chemical formula 1-VI, L 1 to L 3 is as previously stated, and Ar 15 is a substituted or unsubstituted C6 to C30 aryl 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted benzocarbazoleyl group, a substituted or unsubstituted oxazolocarbazoleyl group, or a substituted or unsubstituted dibenzosilolyl group, and R 24 and R 25 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, or substituted or unsubstituted C2 to C30 heterocyclic group, m24 is one of integers from 1 to 3, and m25 is one of integers from 1 to 4. Claim 5 Organic optoelectronic device according to claim 1, wherein the first compound is represented by any one of the following formulas 1-VII, 1-VIII, 1-IX, 1-X, 1-XI, and 1-XII: [Formula 1-VII] [Chemical Formula 1-VIII] [Chemical Formula 1-IX] [Chemical Formula 1-X] [Chemical Formula 1-XI] [Chemical Formula 1-XII] In the above chemical formulas 1-VII, 1-VIII, 1-IX, 1-X, 1-XI, and 1-XII, L 1 to L 3 is as previously stated, and X 6 is O, S, NR g or CR h R i 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazoleyl group, or a substituted or unsubstituted dibenzosilolyl group, and R g , R g , R i , and R 26 to R 28 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 or substituted or unsubstituted C2 to C30 heterocyclic group, m26 and m28 are each independently one of integers 1 to 4, and m27 is an integer 1 or 2. Claim 6 In paragraph 1, the above Ar 1 or Ar 3 An organic optoelectronic device in which at least one of the groups is a 9-carbazole group. Claim 7 In paragraph 1, the above L 1 -Ar 1 , L 2 -Ar 2 and L 3 -Ar 3 Organic optoelectronic device, each independently selected from the substituents listed in Group I below: [Group I] In the above Group I, X 3 은 O, S, NR c , or CR d R e and, R c , R d , R e and R 7 to R 11 Each is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a substituted or unsubstituted C2 to C20 heteroaryl group, and Ar 10 and Ar 11 Each is an independently substituted or unsubstituted C6 to C20 aryl group, m7 is one of integers 1 to 5, m8 is one of integers 1 to 4, m9 is one of integers 1 to 3, m10 is an integer 1 or 2, m11 is one of integers 1 to 7, and * is a link point. Claim 8 In claim 1, the first compound is a compound for an organic optoelectronic device selected from the compounds listed in the following groups 1-1 to 1-3: [Group 1-1] [1-1] [1-2] [1-3] [1-4] [1-5] [1-6] [1-7] [1-8] [1-9] [1-10] [1-11] [1-12] [1-13] [1-14] [1-15] [1-16] [1-17] [1-18] [1-19] [1-20] [1-21] [1-22] [1-23] [1-24] [1-25] [1-26] [1-27] [1-28] [1-29] [1-30] [1-31] ​​[1-32] [1-33] [1-34] [1-35] [1-36] [1-37] [1-38] [1-39] [1-40] [1-41] [1-42] [1-43] [1-44] [1-45] [1-46] [1-47] [1-48] [1-49] [1-50] [1-51] [1-52] [1-53] [1-54] [1-55] [1-56] [Group 1-2] [1-57] [1-58] [1-59] [1-60] [1-61] [1-62] [1-63] [1-64] [1-65] [1-66] [1-67] [1-68] [1-69] [1-70] [1-71] [1-72] [1-73] [1-74] [1-75] [1-76] [1-77] [1-78] [1-79] [1-80] [1-81] [1-82] [1-83] [1-84] [1-85] [1-86] [1-87] [1-88] [1-89] [1-90] [1-91] [1-92] [1-93] [1-94] [1-95] [1-96] [1-97] [1-98] [1-99] [1-100] [1-101] [1-102] [1-103] [1-104] [1-105] [1-106] [1-107] [1-108] [1-109] [1-110] [1-111] [1-112] [1-113] [1-114] [1-115] [1-116] [1-117] [1-118] [1-119] [1-120] [1-121] [1-122] [1-123] [1-124] [1-125] [1-126] [1-127] [1-128] [1-129] [1-130] [1-131] [1-132] [1-133] [1-134] [1-135] [1-136] [1-137] [1-138] [1-139] [1-140] [Group 1-3] [1-141] [1-142] [1-143] [1-144] [1-145] [1-146] [1-147] [1-148] [1-149] [1-150] [1-151] [1-152] [1-153] [1-154] [1-155] [1-156] [1-157] [1-158] [1-159] [1-160] [1-161] [1-162] [1-163] [1-164] [1-165] [1-166] [1-167] [1-168] [1-169] [1-170] [1-171] [1-172] [1-173] [1-174] [1-175] [1-176] [1-177] [1-178] [1-179] [1-180] [1-181] [1-182] [1-183] [1-184] [1-185] [1-186] [1-187] [1-188] [1-189] [1-190] [1-191] [1-192] [1-193] [1-194] [1-195] [1-196] [1-197] [1-198] [1-199] [1-200] [1-201] [1-202] [1-203] [1-204] [1-205] [1-206] [1-207] [1-208] [1-209] [1-210] [1-211] [1-212] [1-213] [1-214] [1-215] [1-216] [1-217] [1-218] [1-219] [1-220] [1-221] [1-222] [1-223] [1-224] [1-225] [1-226] [1-227] [1-228] [1-229] [1-230] [1-231] [1-232] [1-233] [1-234] [1-235] [1-236] [1-237] [1-238] [1-239] [1-240] [1-241] [1-242] [1-243] [1-244] [1-245] [1-246] [1-247] [1-248] [1-249] [1-250] [1-251] [1-252] [1-253] [1-254] [1-255] [1-256] [1-257] [1-258] [1-259] (Dn refers to the number of deuterium substitutions and indicates a structure with one or more deuterium substitutions.) Claim 9 An organic optoelectronic device according to claim 1, wherein the second compound is represented by one of the following formulas: [Formula 2A] [Formula 2B] [Formula 2C] [Chemical Formula 2D] [Chemical Formula 2E] In the above chemical formulas 2A, 2B, 2C, 2D, and 2E, L a1 to L a4 , L 4 and L 5 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and R a1 to R a4 , R 1 and R 2 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 4 and Ar 5 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m1 and m2 are each independently one of integers from 1 to 4. Claim 10 An organic optoelectronic device according to claim 9, wherein the second compound is represented by the chemical formula 2C. Claim 11 In Clause 9, the above L 4 -Ar 4 and L 5 -Ar 5 An organic optoelectronic device, each independently one of the substituents listed in Group II below.[Group II] In the above Group II, R 12 to R 16 Each is independently hydrogen, deuterium, cyano group, C1 to C10 alkyl group, or C6 to C12 aryl group, m12 is one of integers from 1 to 5, m13 is one of integers from 1 to 4, m14 is one of integers from 1 to 3, m15 is one or 2 integers, m16 is one of integers from 1 to 7, and * is a connecting point. Claim 12 In claim 1, the second compound is an organic optoelectronic device selected from the compounds listed in Group 2 below: [Group 2][2-1] [2-2] [2-3] [2-4] [2-5] [2-6] [2-7] [2-8] [2-9] [2-10] [2-11] [2-12] [2-13] [2-14] [2-15] [2-16] [2-17] [2-18] [2-19] [2-20] [2-21] [2-22] [2-23] [2-24] [2-25] [2-26] [2-27] [2-28] [2-29] [2-30] [2-31] [2-32] [2-33] [2-34] [2-35] [2-36] [2-37] [2-38] [2-39] [2-40] [2-41] [2-42] [2-43] [2-44] [2-45] [2-46] [2-47] [2-48] [2-49] [2-50] [2-51] [2-52] [2-53] [2-54] [2-55] [2-56] [2-57] [2-58] [2-59] [2-60] [2-61] [2-62] [2-63] [2-64] [2-65] [2-66] [2-67] [2-68] [2-69] [2-70] [2-71] [2-72] [2-73] [2-74] [2-75] [2-76] [2-77] [2-78] [2-79] [2-80] [2-81] [2-82] [2-83] [2-84] [2-85] [2-86] [2-87] [2-88] [2-89] [2-90] [2-91] [2-92] [2-93] [2-94] [2-95] [2-96] [2-97] [2-98] [2-99] [2-100] . Claim 13 In paragraph 1, the above Ar 6 is a substituted or unsubstituted phenyl group, and the Ar 7 or Ar 9 An organic optoelectronic device, each having an independently substituted or unsubstituted C6 to C12 aryl group. Claim 14 In paragraph 1, the above L 7 An organic optoelectronic device selected from the connectors listed in Group III below: [Group III] In the above Group III, R 29 is hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C12 aryl group or substituted or unsubstituted C2 to C20 heteroaryl group, m29 is one of integers 1 to 4, and * is a connecting point. Claim 15 In claim 1, the third compound is an organic optoelectronic device selected from the compounds listed in Group 3 below: [Group 3][3-1] [3-2] [3-3] [3-4] [3-5] [3-6] [3-7] [3-8] [3-9] [3-10] [3-11] [3-12] [3-13] [3-14] [3-15] [3-16] [3-17] [3-18] [3-19] [3-20] [3-21] [3-22] [3-23] [3-24] [3-25] [3-26] [3-27] [3-28] [3-29] [3-30] [3-31] [3-32] [3-33] [3-34] [3-35] [3-36] [3-37] [3-38] [3-39] [3-40] [3-41] [3-42] [3-43] [3-44] [3-45] [3-46] [3-47] [3-48] [3-49] [3-50] [3-51] [3-52] [3-53] [3-54] [3-55] [3-56] [3-57] [3-58] [3-59] [3-60] [3-61] [3-62] [3-63] [3-64] [3-65] [3-66] [3-67] [3-68] [3-69] [3-70] [3-71] [3-72] [3-73] [3-74] [3-75] [3-76] . Claim 16 A display device comprising an organic optoelectronic element according to any one of claims 1 to 15.

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