Organic optoelectronic diode and display device

Abstract

The present invention relates to an organic optoelectronic diode comprising a positive electrode and a negative electrode which face each other, an emission layer positioned between the positive electrode and the negative electrode, and an electron transport layer positioned between the emission layer and the negative electrode, wherein the emission layer includes 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 includes a third compound represented by chemical formula 4. The details of chemical formula 1 to chemical formula 4 are as defined in the specification.

Description

Organic optoelectronic devices and displays

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

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

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

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

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

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

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

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

[0009] Another embodiment provides a display device including the organic optoelectronic device.

[0010] According to one embodiment, an organic optoelectronic device is provided, which includes an anode and a cathode facing each other, a light-emitting layer positioned between the anode and the cathode, and an electron transport layer positioned between the light-emitting layer and the cathode, wherein the light-emitting layer includes a first compound represented by the following chemical formula 1 and a second compound represented by a combination of the following chemical formulas 2 and 3, and wherein the electron transport layer includes 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 Inland Ar 3 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0015] L 1 Inland L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to 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* in chemical formula 2, two adjacent ones are each a connecting carbon (C) connected to * in chemical formula 3,

[0020] Among a1* to a4* in chemical formula 2, the remaining two that are not connected to chemical formula 3 are CL a -R a And,

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

[0022] R a , R 1 and R 2 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

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

[0024] m1 and m2 are each independently an integer from 1 to 4,

[0025] If m1 is 2 or more, each R 1 are identical or different from each other,

[0026] If m2 is 2 or more, each R 2 are identical or different from each other;

[0027] [Chemical Formula 4]

[0028]

[0029] In the above chemical formula 4,

[0030] X 1 is O or S,

[0031] Z 1 Inland Z 6 are each independently N or CR b And,

[0032] Z 1 Inland Z 3 At least two of them are N,

[0033] Z 4 Inland Z 6 At least two of them are N,

[0034] L 7 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group,

[0035] Ar 6 Inland Ar 9 are each independently a substituted or unsubstituted C6 to C30 aryl group,

[0036] R b , R 3 and R 4 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0037] m3 and m4 are each independently an integer from 1 to 3,

[0038] If m3 is 2 or more, each R 3 are identical or different from each other,

[0039] If m4 is 2 or more, each R 4 are identical or different from each other.

[0040] According to another embodiment, a display device including the organic optoelectronic device is provided.

[0041] High-efficiency, long-life organic optoelectronic devices can be realized while lowering the operating voltage.

[0042] Figure 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment.

[0043] <Explanation of symbols>

[0044] 100: Organic light-emitting diode

[0045] 105: Organic layer

[0046] 110: Cathode

[0047] 120: Bipolar

[0048] 130: Emissive layer

[0049] 140: Hole transport region

[0050] 150: Electron transport region

[0051]

[0052] Hereinafter, embodiments of the present invention will be described in detail. However, these are presented as examples and are not intended to limit the present invention. The present invention is defined solely by the scope of the claims set forth below.

[0053] As used herein, “substituted” means that at least one hydrogen in a substituent or compound is substituted with deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof, unless otherwise defined.

[0054] In one embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group. In addition, in one specific embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1 to C20 alkyl group, a 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 a substituent or a compound is replaced 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 a substituent or a compound is replaced 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.

[0055] As used herein, “unsubstituted” means that a hydrogen atom remains a hydrogen atom without being replaced by another substituent.

[0056] In this specification, “hydrogen (-H)” may include “deuterium substitution (-D)” or “tritium substitution (-T)”.

[0057] In this specification, unless otherwise defined, “hetero” means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si in one functional group, and the remainder being carbon.

[0058] In this specification, "aryl group" is a concept that encompasses a group having one or more hydrocarbon aromatic moieties, and includes a form in which all elements of the hydrocarbon aromatic moieties have p-orbitals and these p-orbitals form conjugation, such as a phenyl group, a naphthyl group, etc., a form in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and a non-aromatic fused ring in which two or more hydrocarbon aromatic moieties are directly or indirectly fused, such as a fluorenyl group, etc.

[0059] Aryl groups include monocyclic, polycyclic, or fused ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.

[0060] In this specification, "heterocyclic group" is a superordinate concept including a heteroaryl group, and means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si instead of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. When the heterocyclic group is a fused ring, the heterocyclic group as a whole or each ring may contain one or more heteroatoms.

[0061] For example, a "heteroaryl group" means an aryl group containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si. Two or more heteroaryl groups may be directly connected via a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused to each other. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 of the heteroatoms.

[0062] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be, but is not limited to, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted 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.

[0063] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group is a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted It may be an isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthfuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted benzofuranofluorenyl group, a substituted or unsubstituted benzothiophenfluorenyl group, or a combination thereof, but is not limited thereto.

[0064] In this specification, the hole characteristic refers to a characteristic that can form holes by donating electrons when an electric field is applied, and has a conductive characteristic along the HOMO level, which means a characteristic that facilitates the injection of holes formed at the anode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the anode, and the movement in the light-emitting layer.

[0065] In addition, electronic properties refer to the property of being able to receive electrons when an electric field is applied, and have conductive properties along the LUMO level, which means the property of facilitating the injection of electrons formed at the cathode into the light-emitting layer, the movement of electrons formed in the light-emitting layer to the cathode, and the movement in the light-emitting layer.

[0066]

[0067] An organic optoelectronic device according to an embodiment of the present invention is described below.

[0068] Organic optoelectronic devices are not particularly limited as long as they can convert electrical energy and light energy to each other, and examples thereof include organic photoelectric devices, organic light-emitting devices, organic solar cells, and organic photosensitive drums.

[0069] Here, an organic light-emitting device, which is an example of an organic optoelectronic device, is described as an example, but the present invention is not limited thereto and can be equally applied to other organic optoelectronic devices.

[0070] To clearly illustrate various layers and regions in the drawings, the thicknesses are enlarged. Similar parts are designated by the same drawing reference numerals throughout the specification. When an element, such as a layer, film, region, or plate, is said to be "on" another element, this includes not only the case where it is "directly on" the other element, but also the case where there are other elements in between. Conversely, when an element is said to be "directly on" another element, it means that there are no other elements in between.

[0071] Figure 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment.

[0072] 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) positioned between the anode (120) and the cathode (110).

[0073] The anode (120) can be made of a conductor having a high work function, for example, to facilitate hole injection, and can be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode (120) may be, but is not limited to, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, or gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyethylenedioxythiophene: PEDOT), polypyrrole, and polyaniline.

[0074] 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 made of, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; or a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0075] 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.

[0076] Below, a composition for an organic optoelectronic device is described.

[0077] The composition for the organic optoelectronic device includes 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.

[0078] [Chemical Formula 1]

[0079]

[0080] In the above chemical formula 1,

[0081] Ar 1 Inland Ar 3 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0082] L 1 Inland L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group;

[0083] [Chemical Formula 2] [Chemical Formula 3]

[0084]

[0085] In the above chemical formulas 2 and 3,

[0086] Among a1* to a4* in chemical formula 2, two adjacent ones are each a connecting carbon (C) connected to * in chemical formula 3,

[0087] Among a1* to a4* in chemical formula 2, the remaining two that are not connected to chemical formula 3 are CL a -R a And,

[0088] L a , L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0089] R a , R 1 and R 2 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0090] Ar 4 and Ar 5are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0091] m1 and m2 are each independently an integer from 1 to 4.

[0092] In the above chemical formula 2, when m1 is 2 or more, each R 1 may be the same or different.

[0093] In the above chemical formula 3, when m2 is 2 or more, each R 2 may be the same or different.

[0094] In the above chemical formulas 2 and 3, R a If these 2 or more are substituted, each R a may be the same or different.

[0095] For example, Ar of the above chemical formula 1 1 Inland Ar 3 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted 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 carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted oxazolocarbazolyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted It may be an indolofluorenyl group, a substituted or unsubstituted benzofuranocarbazolyl group, a substituted or unsubstituted benzothienocarbazolyl group, or a substituted or unsubstituted dibenzosilolyl group.

[0096] As a specific example, Ar of the above chemical formula 1 1 Inland Ar 3 may each 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 carbazolyl group.

[0097] For example, the first compound may be represented by any one of the following chemical formulas 1-Ⅰ, 1-Ⅱ, 1-Ⅲ, and 1-Ⅳ.

[0098] [Chemical Formula 1-Ⅰ]

[0099]

[0100] In the above chemical formula 1-Ⅰ, L 1 Inland L 3 is as described above,

[0101] Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted 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,

[0102] R 17 Inland R 19 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

[0103] m17 is one of the integers 1 to 3,

[0104] m18 and m19 are each independently an integer from 1 to 4,

[0105] If m17 is 2 or more, each R 17 are identical or different from each other,

[0106] If m18 is 2 or more, each R 18 are identical or different from each other,

[0107] If m19 is 2 or more, each R 19 are identical or different from each other;

[0108] [Chemical Formula 1-Ⅱ]

[0109]

[0110] In the above chemical formula 1-Ⅱ, L 1 Inland L 3 is as described above,

[0111] X 4 is O or S,

[0112] Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted 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,

[0113] R 20 Inland R 21 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0114] m20 is one of the integers 1 to 3,

[0115] m21 is one of the integers 1 to 4,

[0116] If m20 is 2 or more, each R 20are identical or different from each other,

[0117] If m21 is 2 or more, each R 21 are identical or different from each other;

[0118] [Chemical Formula 1-Ⅲ]

[0119]

[0120] In the above chemical formula 1-Ⅲ, L 1 Inland L 3 is as described above,

[0121] Z 7 Inland Z 9 are each independently N or CR f And,

[0122] Z 7 Inland Z 9 At least two of them are N,

[0123] Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted 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 carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted oxazolocarbazolyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted indolofluorenyl group, a substituted or unsubstituted benzofuranocarbazolyl group, a substituted or unsubstituted benzothienocarbazolyl group, or a substituted or unsubstituted dibenzosilolyl group;

[0124] [Chemical Formula 1-Ⅳ]

[0125]

[0126] In the above chemical formula 1-Ⅳ, L 1 Inland L 3 is as described above,

[0127] X 5 is O or S,

[0128] Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted triphenylene group,

[0129] Ar 14 is a substituted or unsubstituted C6 to C30 aryl group,

[0130] 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,

[0131] m22 is one of the integers 1 to 4,

[0132] If m22 is 2 or more, each R 22 are identical or different from each other.

[0133] As another example, the first compound may be represented by the following chemical formula 1-V or chemical formula 1-VI.

[0134] [Chemical Formula 1-Ⅴ]

[0135]

[0136] In the above chemical formula 1-Ⅴ, L 1 Inland L 3 is as described above,

[0137] Ring A is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted benzoxazole,

[0138] Ar 1 and Ar 2are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted 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 carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted oxazolocarbazolyl group, or a substituted or unsubstituted dibenzosilolyl group,

[0139] 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,

[0140] m23 is one of the integers 1 to 4,

[0141] If m23 is 2 or more, each R 23 are identical or different from each other;

[0142] [Chemical Formula 1-Ⅵ]

[0143]

[0144] In the above chemical formula 1-Ⅵ, L 1 Inland L 3 is as described above,

[0145] Ar 15 is a substituted or unsubstituted C6 to C30 aryl group,

[0146] Ar 1 and Ar 2are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted 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 carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted oxazolocarbazolyl group, or a substituted or unsubstituted dibenzosilolyl group,

[0147] R 24 and R 25 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0148] m24 is one of the integers 1 to 3,

[0149] m25 is one of the integers 1 to 4,

[0150] If m24 is 2 or more, each R 24 are identical or different from each other,

[0151] If m25 is 2 or more, each R 25 are identical or different from each other.

[0152] As another example, the first compound may be represented by any one of the following chemical formulas 1-Ⅶ, 1-Ⅷ, 1-Ⅸ, 1-Ⅹ, 1-ⅩⅠ, and 1-ⅩⅡ.

[0153] [Chemical Formula 1-Ⅶ]

[0154]

[0155] [Chemical Formula 1-Ⅷ]

[0156]

[0157] [Chemical Formula 1-Ⅸ]

[0158]

[0159] [Chemical Formula 1-Ⅹ]

[0160]

[0161] [Chemical Formula 1-ⅩⅠ]

[0162]

[0163] [Chemical Formula 1-ⅩⅡ]

[0164]

[0165] In the above chemical formulas 1-Ⅶ, 1-Ⅷ, 1-Ⅸ, 1-Ⅹ, 1-ⅩⅠ and 1-ⅩⅡ, L 1 Inland L 3 is as described above,

[0166] X 6 are O, S, NR g or CR h R i And,

[0167] Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted 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 carbazolyl group, or a substituted or unsubstituted dibenzosilolyl group,

[0168] R g , R g , R i , and R 26 Inland R 28are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0169] m26 and m28 are each independently an integer from 1 to 4,

[0170] m27 is an integer of 1 or 2,

[0171] If m26 is 2 or more, each R 26 are identical or different from each other,

[0172] If m27 is 2 or more, each R 27 are identical or different from each other,

[0173] If m28 is 2 or more, each R 28 are identical or different from each other.

[0174] For example, the above R g , R g , R i , and R 17 Inland R 28 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, 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.

[0175] For example, the above Ar 1 Inland Ar 3 At least one of them may be a 9-carbazolyl group.

[0176] In one embodiment, the L 1 -Ar 1 , L 2 -Ar 2 and L 3 -Ar 3 Each of the substituents may be independently selected from the substituents listed in Group I below.

[0177] [Group Ⅰ]

[0178]

[0179] In the above group Ⅰ,

[0180] X 3 Silver O, S, NR c , or CR d R e And,

[0181] R c , R d , R e and R 7 Inland R 11 are each 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,

[0182] Ar 10 and Ar 11 are each independently a substituted or unsubstituted C6 to C20 aryl group,

[0183] m7 is one of the integers 1 to 5,

[0184] m8 is one of the integers 1 to 4,

[0185] m9 is one of the integers 1 to 3,

[0186] m10 is an integer of 1 or 2,

[0187] m11 is one of the integers 1 to 7,

[0188] * is a connection point.

[0189] If m7 is 2 or more, each R 7 may be identical or different.

[0190] If m8 is 2 or more, each R 8 may be identical or different.

[0191] If m9 is 2 or more, each R 9 may be identical or different.

[0192] If m10 is 2, each R 10 may be identical or different.

[0193] If m11 is 2 or more, each R 11 may be identical or different.

[0194] In the most specific embodiment, the first compound represented by the above chemical formula 1 may be one selected from the compounds listed in Groups 1-1 to 1-3 below, but is not limited thereto.

[0195] [Group 1-1]

[0196] [1-1] [1-2] [1-3] [1-4]

[0197]

[0198] [1-5] [1-6] [1-7] [1-8]

[0199]

[0200] [1-9] [1-10] [1-11] [1-12]

[0201]

[0202] [1-13] [1-14] [1-15] [1-16]

[0203]

[0204] [1-17] [1-18] [1-19] [1-20]

[0205]

[0206] [1-21] [1-22] [1-23] [1-24]

[0207]

[0208] [1-25] [1-26] [1-27] [1-28]

[0209]

[0210] [1-29] [1-30] [1-31] ​​[1-32]

[0211]

[0212] [1-33] [1-34] [1-35] [1-36]

[0213]

[0214] [1-37] [1-38] [1-39] [1-40]

[0215]

[0216] [1-41] [1-42] [1-43] [1-44]

[0217]

[0218] [1-45] [1-46] [1-47] [1-48]

[0219]

[0220] [1-49] [1-50] [1-51] [1-52]

[0221]

[0222] [1-53] [1-54] [1-55] [1-56]

[0223]

[0224] [Group 1-2]

[0225] [1-57] [1-58] [1-59] [1-60]

[0226]

[0227] [1-61] [1-62] [1-63] [1-64]

[0228]

[0229] [1-65] [1-66] [1-67] [1-68]

[0230]

[0231] [1-69] [1-70] [1-71] [1-72]

[0232]

[0233] [1-73] [1-74] [1-75] [1-76]

[0234]

[0235] [1-77] [1-78] [1-79] [1-80]

[0236]

[0237] [1-81] [1-82] [1-83] [1-84]

[0238]

[0239] [1-85] [1-86] [1-87] [1-88]

[0240]

[0241] [1-89] [1-90] [1-91] [1-92]

[0242]

[0243] [1-93] [1-94] [1-95] [1-96]

[0244]

[0245] [1-97] [1-98] [1-99] [1-100]

[0246]

[0247] [1-101] [1-102] [1-103] [1-104]

[0248]

[0249] [1-105] [1-106] [1-107] [1-108]

[0250]

[0251] [1-109] [1-110] [1-111] [1-112]

[0252]

[0253] [1-113] [1-114] [1-115] [1-116]

[0254]

[0255] [1-117] [1-118] [1-119] [1-120]

[0256]

[0257] [1-121] [1-122] [1-123] [1-124]

[0258]

[0259] [1-125] [1-126] [1-127] [1-128]

[0260]

[0261] [1-129] [1-130] [1-131] [1-132]

[0262]

[0263] [1-133] [1-134] [1-135] [1-136]

[0264]

[0265] [1-137] [1-138] [1-139] [1-140]

[0266]

[0267] [Group 1-3]

[0268] [1-141] [1-142] [1-143] [1-144] [1-145]

[0269]

[0270] [1-146] [1-147] [1-148] [1-149] [1-150]

[0271]

[0272] [1-151] [1-152] [1-153] [1-154] [1-155]

[0273]

[0274] [1-156] [1-157] [1-158] [1-159] [1-160]

[0275]

[0276] [1-161] [1-162] [1-163] [1-164] [1-165]

[0277]

[0278] [1-166] [1-167] [1-168] [1-169] [1-170]

[0279]

[0280] [1-171] [1-172] [1-173] [1-174] [1-175]

[0281]

[0282] [1-176] [1-177] [1-178] [1-179] [1-180]

[0283]

[0284] [1-181] [1-182] [1-183] [1-184] [1-185]

[0285]

[0286] [1-186] [1-187] [1-188] [1-189] [1-190]

[0287]

[0288] [1-191] [1-192] [1-193] [1-194] [1-195]

[0289]

[0290] [1-196] [1-197] [1-198] [1-199] [1-200]

[0291]

[0292] [1-201] [1-202] [1-203] [1-204] [1-205]

[0293]

[0294] [1-206] [1-207] [1-208] [1-209] [1-210]

[0295]

[0296] [1-211] [1-212] [1-213] [1-214] [1-215]

[0297]

[0298] [1-216] [1-217] [1-218] [1-219] [1-220]

[0299]

[0300] [1-221] [1-222] [1-223] [1-224] [1-225]

[0301]

[0302] [1-226] [1-227] [1-228] [1-229] [1-230]

[0303]

[0304] [1-231] [1-232] [1-233] [1-234] [1-235]

[0305]

[0306] [1-236] [1-237] [1-238] [1-239]

[0307]

[0308] [1-240] [1-241] [1-242] [1-243]

[0309]

[0310] [1-244] [1-245] [1-246] [1-247]

[0311]

[0312] [1-248] [1-249] [1-250] [1-251]

[0313]

[0314] [1-252] [1-253] [1-254] [1-255]

[0315]

[0316] [1-256] [1-257] [1-258] [1-259]

[0317]

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

[0319] The second compound can be used in the light-emitting layer together with the first compound to improve the light-emitting efficiency and lifespan characteristics by increasing the mobility of charges and enhancing stability.

[0320] For example, the second compound may be represented by one of the following chemical formulas 2A, 2B, 2C, 2D, and 2E.

[0321] [Formula 2A] [Formula 2B] [Formula 2C]

[0322]

[0323] [Chemical Formula 2D] [Chemical Formula 2E]

[0324]

[0325] In the above chemical formulas 2A, 2B, 2C, 2D, and 2E,

[0326] L a1 Inland L a4 , L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0327] R a1Inland R a4 , R 1 and R 2 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0328] Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0329] m1 and m2 are each independently an integer from 1 to 4.

[0330] For example, Ar of the above chemical formulas 2 and 3 4 and Ar 5 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group,

[0331] R a1 Inland R a4 , R 1 and R 2 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0332] In one embodiment, the R a1 Inland R a4 , R 1 and R 2may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0333] For example, the above R a1 Inland R a4 , R 1 and R 2 may each independently be hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group,

[0334] In a specific embodiment, the R a1 Inland R a4 , R 1 and R 2 may each independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0335] As a specific example, the second compound may be represented by the chemical formula 2C.

[0336] In one embodiment, the L 4 -Ar 4 and L 5 -Ar 5 Each of may independently be one of the substituents listed in Group II below.

[0337] [Group II]

[0338]

[0339] In the above group II,

[0340] R 12 Inland R 16 are each independently hydrogen, deuterium, cyano group, C1 to C10 alkyl group or C6 to C12 aryl group,

[0341] m12 is an integer between 1 and 5,

[0342] m13 is one of the integers 1 to 4,

[0343] m14 is an integer between 1 and 3,

[0344] m15 is an integer of 1 or 2,

[0345] m16 is an integer between 1 and 7,

[0346] * is a connection point.

[0347] If m12 is 2 or more, each R 12 may be identical or different.

[0348] If m13 is 2 or more, each R 13 may be identical or different.

[0349] If m14 is 2 or more, each R 14 may be identical or different.

[0350] If m15 is 2, each R 15 may be identical or different.

[0351] If m16 is 2 or more, each R 16 may be identical or different.

[0352] For example, the second compound may be represented by the chemical formula 2c.

[0353] In a specific embodiment of the present invention, the L a1 Inland L a4 are each single bonds, and L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, and R 1 , R 2 , and R a1 Inland R a4 are hydrogen, deuterium or phenyl groups, respectively, and Ar 4 and Ar 5may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0354] For example, the above L a1 Inland L a4 is a single bond, and R 1 , R 2 , and R a1 Inland R a4 are each independently hydrogen, deuterium or a C6 to C12 aryl group, and L 4 -Ar 4 and L 5 -Ar 5 Each may independently be one of the substituents listed in Group II above.

[0355] In the most specific embodiment, the second compound represented by the combination of the above chemical formulas 2 and 3 may be one selected from the compounds listed in Group 2 below, but is not limited thereto.

[0356] [Group 2]

[0357] [2-1] [2-2] [2-3] [2-4]

[0358]

[0359] [2-5] [2-6] [2-7] [2-8]

[0360]

[0361] [2-9] [2-10] [2-11] [2-12]

[0362]

[0363] [2-13] [2-14] [2-15] [2-16]

[0364]

[0365] [2-17] [2-18] [2-19] [2-20]

[0366]

[0367] [2-21] [2-22] [2-23] [2-24]

[0368]

[0369] [2-25] [2-26] [2-27] [2-28]

[0370]

[0371] [2-29] [2-30] [2-31] [2-32]

[0372]

[0373] [2-33] [2-34] [2-35] [2-36]

[0374]

[0375] [2-37] [2-38] [2-39] [2-40]

[0376]

[0377] [2-41] [2-42] [2-43] [2-44]

[0378]

[0379] [2-45] [2-46] [2-47] [2-48]

[0380]

[0381] [2-49] [2-50] [2-51] [2-52]

[0382]

[0383] [2-53] [2-54] [2-55] [2-56]

[0384]

[0385] [2-57] [2-58] [2-59] [2-60]

[0386]

[0387] [2-61] [2-62] [2-63] [2-64]

[0388]

[0389] [2-65] [2-66] [2-67] [2-68]

[0390]

[0391] [2-69] [2-70] [2-71] [2-72]

[0392]

[0393] [2-73] [2-74] [2-75] [2-76]

[0394]

[0395] [2-77] [2-78] [2-79] [2-80]

[0396]

[0397] [2-81] [2-82] [2-83] [2-84]

[0398]

[0399] [2-85] [2-86] [2-87] [2-88]

[0400]

[0401] [2-89] [2-90] [2-91] [2-92]

[0402]

[0403] [2-93] [2-94] [2-95] [2-96]

[0404]

[0405] [2-97] [2-98] [2-99] [2-100]

[0406]

[0407] The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. By being included in the above range, the electron transport ability of the first compound and the hole transport ability of the second compound can be used to achieve an appropriate weight ratio to implement bipolar characteristics, thereby improving efficiency and lifespan. Within the above range, the weight ratio may be included in a weight ratio of, for example, about 10:90 to 90:10, about 20:80 to 80:20, 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, the weight ratio may be included in a weight ratio of 40:60, 50:50, or 60:40.

[0408] The dopant may be, for example, a phosphorescent dopant, for example, a red, green or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0409] A dopant is a substance that causes light emission when mixed in trace amounts into a compound or composition for an organic optoelectronic device. Generally, a substance such as a metal complex that emits light by multiple excitation that excites to a triplet state or higher can be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may be included in one or more types.

[0410] An example of a dopant is a phosphorescent dopant, and examples of a phosphorescent dopant include an organometallic compound containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the following chemical formula Z, but is not limited thereto.

[0411] [Chemical formula Z]

[0412] L 6 MX 2

[0413] In the above chemical formula Z, M is a metal, and L 6 and X 2 are ligands that are the same or different and form complexes with M.

[0414] 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 may be, for example, a bidentate ligand.

[0415] L 6 and X 2 Examples of ligands represented by may be selected from, but are not limited to, the chemical formulas listed in Group A below.

[0416] [Group A]

[0417]

[0418] In the above group A,

[0419] R 300 Inland R 302 are each independently a C1 to C30 alkyl group substituted or unsubstituted with hydrogen, deuterium, halogen, a C6 to C30 aryl group substituted or unsubstituted with C1 to C30 alkyl, or halogen,

[0420] R 303 Inland R 324are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

[0421] The dopant according to one embodiment may be an iridium complex, for example, represented by the following chemical formula 6-1 or chemical formula 6-2.

[0422] [Chemical Formula 6-1]

[0423]

[0424] In the above chemical formula 6-1,

[0425] R 101 Inland R 116 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0426] The above R 132 Inland R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0427] R 101 Inland R 116 At least one of them is a functional group represented by the following chemical formula V-1,

[0428] L 100is a bidentate ligand of a single anion, and is a ligand that coordinates to iridium through the unshared electron pair of carbon or a heteroatom.

[0429] m21 and m22 are independently any integer from 0 to 3, and m21 + m22 is any integer from 1 to 3,

[0430] [Chemical Formula V-1]

[0431]

[0432] In the above chemical formula V-1,

[0433] R 135 Inland R 139 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0434] * indicates a part connected to a carbon atom.

[0435] [Chemical Formula 6-2]

[0436]

[0437] In the above chemical formula 6-2,

[0438] R 101 Inland R 117 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -Si R 133 R 134 R 135 And,

[0439] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0440] L 100is a bidentate ligand of a single anion, and is a ligand that coordinates to iridium through the unshared electron pair of carbon or a heteroatom.

[0441] n1 and n2 are independently any integers from 0 to 3, and n1 + n2 is any integer from 1 to 3.

[0442] In another embodiment, the dopant may be a platinum complex, for example represented by the chemical formula Z-1.

[0443] [Chemical Formula Z-1]

[0444]

[0445] In the above chemical formula Z-1, rings A, B, C, and D each independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0446] R A , R B , R C , and R D each independently represents monosubstitution, disubstitution, trisubstitution, tetrasubstitution, or no substitution;

[0447] L B , L C , and L D are independently selected from the group consisting of direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof;

[0448] If nA is 1, L E is selected from the group consisting of direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; when nA is 0, L E does not exist;

[0449] R A , R B , R C , R D, R, and R' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, heteroalkyl group, arylalkyl group, alkoxy group, aryloxy group, amino group, silyl group, alkenyl group, cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof; any adjacent R A , R B , R C , R D , R, and R' are randomly connected to form a ring; X B , X C , X D , and X E are independently selected from the group consisting of carbon and nitrogen; Q 1 , Q 2 , Q 3 , and Q 4 represent oxygen or direct bonds, respectively.

[0450] The above platinum complex can be represented, for example, by the following chemical formula 7-1 or chemical formula 7-2.

[0451] [Chemical Formula 7-1]

[0452]

[0453] [Chemical Formula 7-2]

[0454]

[0455] In the above chemical formulas 7-1 and 7-2,

[0456] X 100 Silver O, S and NR 132 Selected from among,

[0457] R 118 Inland R 132 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or - SiR 133 R134 R 135 And,

[0458] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0459] R 118 Inland R 132 At least one of them is -SiR 133 R 134 R 135 or tert-butyl group,

[0460] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group.

[0461] The organic layer may further include a charge transport region in addition to the light-emitting layer.

[0462] The above charge transport region may be, for example, a hole transport region (140).

[0463] The above 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.

[0464] 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.

[0465] [Group B]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475]

[0476]

[0477]

[0478]

[0479]

[0480]

[0481]

[0482]

[0483]

[0484]

[0485]

[0486]

[0487]

[0488]

[0489]

[0490]

[0491]

[0492]

[0493]

[0494]

[0495]

[0496]

[0497]

[0498]

[0499] (Dn refers to the number of deuterium atoms substituted, and indicates a structure in which one or more deuterium atoms are substituted)

[0500] In addition to the above-described compound, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds having a similar structure thereto may also be used in the above-described hole transport region (140).

[0501] Additionally, the charge transport region may be, for example, an electron transport region (150).

[0502] 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.

[0503] 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.

[0504] The electron transport layer may include a third compound represented by the following chemical formula 4.

[0505] [Chemical Formula 4]

[0506]

[0507] In the above chemical formula 4,

[0508] X 1 is O or S,

[0509] Z 1 Inland Z 6 are each independently N or CR b And,

[0510] Z 1 Inland Z 3 At least two of them are N,

[0511] Z 4 Inland Z 6 At least two of them are N,

[0512] L 7 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group,

[0513] Ar 6 Inland Ar 9 are each independently a substituted or unsubstituted C6 to C30 aryl group,

[0514] R b and R 3 Inland R 6 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0515] m3 and m4 are each independently an integer from 1 to 3,

[0516] m5 and m6 are each independently an integer from 1 to 4.

[0517] For example, the above Ar 6 is a substituted or unsubstituted phenyl group, and the Ar 7 Inland Ar 9 Each may independently be a substituted or unsubstituted C6 to C12 aryl group.

[0518] Above L 7 may be one selected from the connectors listed in Group Ⅲ below.

[0519] [Group III]

[0520]

[0521] In the above group Ⅲ,

[0522] R 29is 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,

[0523] m29 is one of the integers 1 to 4,

[0524] * is a connection point.

[0525] If m29 is 2 or more, each R 29 may be the same or different.

[0526] 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.

[0527] [Group 3]

[0528] [3-1] [3-2] [3-3] [3-4]

[0529]

[0530] [3-5] [3-6] [3-7] [3-8]

[0531]

[0532] [3-9] [3-10] [3-11] [3-12]

[0533]

[0534] [3-13] [3-14] [3-15] [3-16]

[0535]

[0536] [3-17] [3-18] [3-19] [3-20]

[0537]

[0538] [3-21] [3-22] [3-23] [3-24]

[0539]

[0540] [3-25] [3-26] [3-27] [3-28]

[0541]

[0542] [3-29] [3-30] [3-31] [3-32]

[0543]

[0544] [3-33] [3-34] [3-35] [3-36]

[0545]

[0546] [3-37] [3-38] [3-39] [3-40]

[0547]

[0548] [3-41] [3-42] [3-43] [3-44]

[0549]

[0550] [3-45] [3-46] [3-47] [3-48]

[0551]

[0552] [3-49] [3-50] [3-51] [3-52]

[0553]

[0554] [3-53] [3-54] [3-55] [3-56]

[0555]

[0556] [3-57] [3-58] [3-59] [3-60]

[0557]

[0558] [3-61] [3-62] [3-63] [3-64]

[0559]

[0560] [3-65] [3-66] [3-67] [3-68]

[0561]

[0562] [3-69] [3-70] [3-71] [3-72]

[0563]

[0564] [3-73] [3-74] [3-75] [3-76]

[0565]

[0566] The third compound represented by the above chemical formula 4 has a relatively high T1 energy, so that when included in the electron transport layer, it can effectively prevent back-energy transfer, thereby effectively blocking excitons formed in the light-emitting layer. In addition, by having a DBX substituent, the LUMO electron cloud is stably distributed, thereby increasing molecular stability when used as an electron transport layer. When such a compound is used as an electron transport layer, electron transport occurs effectively, so that device characteristics can be improved. In particular, since the molecular structure itself is stable and can effectively block excitons in the light-emitting layer, the lifetime characteristics can be improved.

[0567] Meanwhile, the second compound represented by the combination of chemical formulas 2 and 3 has a shallow HOMO energy level, so that the hole injection and transport capabilities are increased, and thus, when used in the light-emitting layer together with the first compound, the device characteristics can be improved. Since the second compound has excellent hole injection and transport capabilities, the light-emitting zone may relatively move toward the electron transport layer, and there is a possibility that the device lifespan may be reduced due to interface deterioration between the light-emitting layer and the electron transport layer. When used in combination with the third compound in the electron transport layer, interface deterioration can be effectively prevented, thereby preventing a decrease in lifespan, and at the same time, low-driving and high-efficiency characteristics can be improved.

[0568] In the most specific embodiment, the first compound may be represented by the above chemical formula 1-V, and the second compound may be represented by the above chemical formula 3C.

[0569] The electron transport assist layer may comprise at least one of the compounds listed in Group C below.

[0570] [Group C]

[0571]

[0572]

[0573]

[0574]

[0575]

[0576]

[0577]

[0578]

[0579]

[0580]

[0581]

[0582]

[0583]

[0584]

[0585]

[0586]

[0587]

[0588] 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 a light-emitting layer (130) as an organic layer (105), as shown in FIG. 1.

[0589] Meanwhile, the organic light-emitting device may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. in addition to the light-emitting layer as the aforementioned organic layer.

[0590] An organic light-emitting device (100) can be manufactured by forming an anode or cathode on a substrate, forming an organic layer using a dry film forming method such as evaporation, sputtering, plasma plating, and ion plating, and then forming a cathode or anode thereon.

[0591] The above-described organic light-emitting device can be applied to an organic light-emitting display device.

[0592] The implementation examples described above are described in more detail through the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of the rights.

[0593] The starting materials and reactants used in the examples and synthesis examples below were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry or P&H Tech, or synthesized using known methods, unless otherwise specified.

[0594]

[0595] (Synthesis of compounds for organic optoelectronic devices)

[0596] Synthesis of the first compound

[0597] Synthesis Example 1: Synthesis of Compound 1-98

[0598] [Reaction Formula 1]

[0599]

[0600] Step 1: Synthesis of intermediate I-1

[0601] 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 at 0°C and stirred. After 12 hours, water was added to the reaction solution, and the mixture was filtered. The obtained residue was purified by flash column chromatography to obtain intermediate I-1 (50 g, 79%).

[0602] Step 2: Synthesis of intermediate I-2

[0603] 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, dissolved in 300 ml of tetrahydrofuran, and then 150 ml of an aqueous solution of potassium carbonate (28.2 g, 204 mmol) was added and stirred. After adding tetrakis(triphenylphosphine)palladium (3.54 g, 3.06 mmol), the mixture was heated at 80°C for 12 hours and stirred under reflux. After completion of the reaction, the organic layer was extracted, dried with magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain intermediate I-2 (35 g, 93%).

[0604] Step 3: Synthesis of intermediate I-3

[0605] Under nitrogen conditions, intermediate I-2 (35 g, 94.6 mmol) was dissolved in 500 ml of xylene, and 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 thereto, and the mixture was heated and stirred under reflux for 8 hours. After completion of the reaction, water was added to the reaction solution, extracted with dichloromethane, and then dried with magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The residue thus obtained was purified by flash column chromatography to obtain intermediate I-3 (30 g, 69%).

[0606] Step 4: Synthesis of intermediate I-4

[0607] Compound 1-98 (15 g, 83%) was obtained using the same method as in step 2 using intermediate I-1 (10 g, 27 mmol) and intermediate I-3 (12.5 g, 27 mmol).

[0608]

[0609] Synthesis Example 2: Synthesis of Compound 1-119

[0610] [Reaction Formula 2]

[0611]

[0612] Step 1: Synthesis of intermediate I-4

[0613] 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 completed, the aqueous layer was removed and column chromatography (Hexane:DCM (30%)) was used to obtain 28.9 g (69%) of intermediate I-4.

[0614] Step 2: Synthesis of intermediate I-5

[0615] 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 completed, cooled to room temperature, filtered to remove salts, and then extracted with excess DCM and distilled water. Column chromatography (Hexane:DCM (30% to 50%)) yielded 20.6 g (60%) of intermediate I-5.

[0616] Step 3: Synthesis of intermediate I-7

[0617] Under nitrogen conditions, intermediate I-5 (20.6 g, 69.1 mmol), intermediate I-6 (20.6 g, 57.6 mmol), K2CO3 (15.9 g, 115.2 mmol), and Pd(PPh3)4 (3.33 g, 2.88 mmol) were placed in a round-bottom flask, dissolved in THF (300 ml) and distilled water (60 ml), and stirred under reflux at 70°C for 6 hours. After the reaction was completed, the aqueous layer was removed and column chromatography (Hexane:DCM (30%)) was used to obtain 19.9 g (70%) of intermediate I-7.

[0618] Step 4: Synthesis of compound 1-119

[0619] 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 refluxed at 150°C for 4 hours. After the reaction was complete, the reactant was slowly added dropwise to an excess of water to precipitate a solid, which was then filtered and the obtained solid was separated by column chromatography (Hexane:DCM (30%)) to obtain 17.9 g (62%) of compound 1-119.

[0620]

[0621] Synthesis of the second compound

[0622] Synthesis Example 3: Synthesis of Compound 2-32

[0623]

[0624] Compound 2-32 was synthesized by referring to the method disclosed in KR10-2072208.

[0625] Synthesis Example 4: Synthesis of Compound R-1

[0626]

[0627] Compound R-1 was synthesized by referring to the method disclosed in KR10-1649683.

[0628]

[0629] Synthesis of the third compound

[0630] Synthesis Example 5: Synthesis of Compound 3-29

[0631] [Reaction Formula 3]

[0632]

[0633] Step 1: Synthesis of intermediate I-8

[0634] 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (25 g, 59.54 mmol) was dissolved in 200 ml of xylene under nitrogen conditions, and bis(pinacolato)diboron (18.9 g, 74.42 mmol), Pd(dppf)Cl2 (2.18 g, 2.98 mmol), Tricyclohexylphosphine (3.34 g, 11.91 mmol), and potassium acetate (11.69 g, 119.07 mmol) were added, and the mixture was heated and refluxed for 8 hours. After completion of the reaction, water was added to the reaction solution, extracted with DCM, and dried with MgSO4, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain intermediate I-8 (21.21 g, 80%).

[0635] Step 2: Synthesis of compound I-9

[0636] Intermediate I-9 was synthesized with reference to the method disclosed in KR 10-2022-0032864.

[0637] Step 3: Synthesis of compound 3-29

[0638] Under nitrogen conditions, intermediate I-8 (21.21 g, 41.47 mmol), intermediate 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-bottomed flask, dissolved in THF (200 ml) and distilled water (60 ml), and stirred under reflux at 60°C for 12 hours. After completion of the reaction, the aqueous layer was removed, and the organic solvent was removed under reduced pressure to obtain a solid. The obtained solid was dissolved in hot MCB. After removing moisture with MgSO4, the organic solvent was filtered using a silica gel pad, and the filtrate was stirred. When a solid was formed, it was filtered and dried under vacuum to obtain 22.73 g (70%) of compound 3-29.

[0639]

[0640] Synthesis Example 6: Synthesis of Compound R-2

[0641]

[0642] Compound R-2 was synthesized by referring to the method disclosed in KR 10-2086763.

[0643]

[0644] Synthesis Example 7: Synthesis of Compound R-3

[0645]

[0646] Compound R-3 was synthesized using the same method as for the synthesis of compound 3-29 using intermediate I-8 and 2-([1,1'-Biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0647]

[0648] Example 1: Fabrication of a green organic light-emitting device

[0649] A glass substrate coated with a thin film of ITO (Indium Tin Oxide) was ultrasonically washed in distilled water. After washing with distilled water, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned for 10 minutes using oxygen plasma and then transferred to a vacuum deposition machine. Using the ITO transparent electrode prepared in this way as an anode, Compound E doped with 3% NDP-9 (commercially available from Novaled) was vacuum-deposited on the ITO substrate to form a 100Å thick hole injection layer, and Compound A was deposited on the hole injection layer to a thickness of 1350Å to form a hole transport layer. Compound B was deposited on the hole transport layer to a thickness of 320Å to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compounds 1-119 and 2-32 were simultaneously used as hosts at a weight ratio of 3:7, and IrGD was doped at 7 wt% as a dopant, thereby forming a 330 Å thick light-emitting layer by vacuum deposition. Subsequently, compound 3-29 was deposited at a thickness of 50 Å on the light-emitting layer to form an electron transport auxiliary layer, and compound 3-29 and Liq were simultaneously vacuum-deposited at a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å. LiQ at 15 Å and Al at 1200 Å were sequentially vacuum-deposited on the electron transport layer to form a cathode, thereby manufacturing an organic light-emitting device.

[0650] It was fabricated with the structure of 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 = 93 wt%: 7 wt%](330Å) / Compound 3-29(50Å) / Compound 3-29:LiQ(300Å) / LiQ(15Å) / Al(1200Å).

[0651] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine

[0652] Compound B: N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-2-amine

[0653] [IrGD]

[0654]

[0655]

[0656] Example 2 and Comparative Examples 1 to 8

[0657] An organic light-emitting device was manufactured in the same manner as Example 1, except that the composition was changed to that described in Tables 1 to 5 below.

[0658]

[0659] evaluation

[0660] The driving voltage and lifespan characteristics of the organic light-emitting devices according to Example 1, Example 2, and Comparative Examples 1 to 8 were evaluated.

[0661] The specific measurement method is as follows, and the results are as shown in Tables 1 to 5.

[0662] (1) Measurement of changes in current density according to voltage changes

[0663] For the manufactured organic light-emitting device, the current flowing through the unit device was measured using a current-voltage meter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain the result.

[0664] (2) Measurement of luminance change according to voltage change

[0665] For the manufactured organic light-emitting device, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V, and the results were obtained.

[0666] (3) Life span measurement

[0667] Luminance (cd / m 2 ) to 30000cd / m 2 The results were obtained by maintaining the current at 97% and measuring the time until the current efficiency (cd / A) decreased to 97%.

[0668] The life measurement values ​​were calculated as relative values ​​based on the life measurement values ​​of Example 1 or Example 2 and are listed in Tables 3 to 5 below.

[0669] (4) Driving voltage measurement

[0670] 15mA / cm using a current-voltage meter (Keithley 2400) 2 The results were obtained by measuring the driving voltage of each element.

[0671] 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.

[0672] No. Host electron transport auxiliary layer and electron transport layer driving voltage (%) Compound 1 Compound 2 Compound 3 Example 1 Compound 1-119 Compound 2-32 Compound 3-29100 Comparative Example 1 Compound 1-119 Compound R-1 Compound 3-29108

[0673] No. Host electron transport auxiliary layer and electron transport layer driving voltage (%) Compound 1 Compound 2 Compound 3 Compound Example 2 Compound 1-98 Compound 2-32 Compound 3-29100 Comparative Example 2 Compound 1-98 Compound R-1 Compound 3-29109

[0674] No. Host electron transport auxiliary layer and electron transport layer lifetime (%) Compound 1 Compound 2 Compound 3 Compound Example 1 Compound 1-119 Compound 2-32 Compound 3-29 100 Comparative Example 3 Compound 1-119 Compound 2-32 Compound R-289 Comparative Example 4 Compound 1-119 Compound 2-32 Compound R-384

[0675] No. Host electron transport auxiliary layer and electron transport layer lifetime (%) Compound 1 Compound 2 Compound 3 Compound Example 2 Compound 1-98 Compound 2-32 Compound 3-29 100 Comparative Example 5 Compound 1-98 Compound 2-32 Compound R-287 Comparative Example 6 Compound 1-98 Compound 2-32 Compound R-380

[0676] No. Host Electron Transport Auxiliary Layer and Electron Transport Layer Driving Voltage (%) Lifetime (%) Compound 1 Compound 2 Compound 3 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-210921 Comparative Example 8 Compound 1-98 Compound R-1 Compound R-311321

[0677] Referring to Tables 1 and 2, it can be confirmed that the organic light-emitting devices according to Examples 1 and 2 have significantly improved driving voltages compared to the organic light-emitting devices according to Comparative Examples 1 and 2. In addition, referring to Tables 3 and 4, it can be confirmed that the organic light-emitting devices according to Examples 1 and 2 have significantly improved lifespans compared to the organic light-emitting devices according to Comparative Examples 3 and 4.

[0678] Referring to Table 5, it can be confirmed that the organic light-emitting device according to Example 1 has significantly improved driving voltage and lifespan compared to the organic light-emitting devices according to Comparative Examples 7 and 8. In particular, it can be confirmed that the lifespan characteristics are significantly improved.

[0679]

[0680] Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic concept of the present invention defined in the following claims also fall within the scope of the present invention.

Claims

1. Positive and negative poles facing each other, A light-emitting layer positioned between the anode and the cathode, Including an electron transport layer positioned between the light-emitting layer and the cathode, The above-mentioned 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, An organic optoelectronic device, wherein 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 Inland Ar 3 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, L 1 Inside L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group; [Chemical Formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, Among a1* to a4* in chemical formula 2, two adjacent ones are each a connecting carbon (C) that is connected to * in chemical formula 3, and Among a1* to a4* in chemical formula 2, the remaining two that are not connected to chemical formula 3 are CL a -R a And, L a , L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R a , R 1 and R 2 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m1 and m2 are each independently an integer from 1 to 4, If m1 is 2 or more, each R 1 are identical or different from each other, If m2 is 2 or more, each R 2 are identical or different from each other; [Chemical Formula 4] In the above chemical formula 4, X 1 is O or S, Z 1 Inland Z 6 are each independently N or CR b And, Z 1 Inland Z 3 At least two of them are N, Z 4 Inland Z 6 At least two of them are N, L 7 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group, Ar 6 Inland Ar 9 are each independently a substituted or unsubstituted C6 to C30 aryl group, R b , R 3 and R 4 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m3 and m4 are each independently an integer from 1 to 3, If m3 is 2 or more, each R 3 are identical or different from each other, If m4 is 2 or more, each R 4 are identical or different from each other.

2. In paragraph 1, Above Ar 1 Inland Ar 3 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted 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 carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted oxazolocarbazolyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted An organic optoelectronic device comprising an indolofluorenyl group, a substituted or unsubstituted benzofuranocarbazolyl group, a substituted or unsubstituted benzothienocarbazolyl group, or a substituted or unsubstituted dibenzosilolyl group.

3. In paragraph 1, The above first compound is an organic optoelectronic device represented by any one of the following chemical formulas 1-Ⅰ, 1-Ⅱ, 1-Ⅲ and 1-Ⅳ: [Chemical Formula 1-Ⅰ] In the above chemical formula 1-Ⅰ, L 1 Inland L 3 is as described above, Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted 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, R 17 Inland R 19 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, m17 is one of the integers 1 to 3, m18 and m19 are each independently an integer from 1 to 4, If m17 is 2 or more, each R 17 are identical or different from each other, If m18 is 2 or more, each R 18 are identical or different from each other, If m19 is 2 or more, each R 19 are identical or different from each other; [Chemical Formula 1-Ⅱ] In the above chemical formula 1-Ⅱ, L 1 Inland L 3 is as described above, X 4 is O or S, Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted 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, R 20 Inland R 21 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m20 is one of the integers 1 to 3, m21 is one of the integers 1 to 4, If m20 is 2 or more, each R 20 are identical or different from each other, If m21 is 2 or more, each R 21 are identical or different from each other; [Chemical Formula 1-Ⅲ] In the above chemical formula 1-Ⅲ, L 1 Inside L 3 is as described above, Z 7 Inland Z 9 are each independently N or CR f And, Z 7 Inland Z 9 At least two of them are N, Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted 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 carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted oxazolocarbazolyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted indolofluorenyl group, a substituted or unsubstituted benzofuranocarbazolyl group, a substituted or unsubstituted benzothienocarbazolyl group, or a substituted or unsubstituted dibenzosilolyl group; [Chemical Formula 1-Ⅳ] In the above chemical formula 1-Ⅳ, L 1 Inland L 3 is as described above, X 5 is O or S, Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted triphenylene group, Ar 14 is a substituted or unsubstituted C6 to C30 aryl group, R 22 is hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m22 is one of the integers 1 to 4, If m22 is 2 or more, each R 22 are identical or different from each other.

4. In paragraph 1, The above first compound is an organic optoelectronic device 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 Inside L 3 is as described above, Ring A is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted benzoxazole, Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted 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 carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted oxazolocarbazolyl group, or a substituted or unsubstituted dibenzosilolyl group, R 23 is hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m23 is one of the integers 1 to 4, If m23 is 2 or more, each R 23 are identical or different from each other; [Chemical Formula 1-Ⅵ] In the above chemical formula 1-Ⅵ, L 1 Inside L 3 is as described above, Ar 15 is a substituted or unsubstituted C6 to C30 aryl group, Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted 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 carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted oxazolocarbazolyl group, or a substituted or unsubstituted dibenzosilolyl group, R 24 and R 25 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m24 is one of the integers 1 to 3, m25 is one of the integers 1 to 4, If m24 is 2 or more, each R 24 are identical or different from each other, If m25 is 2 or more, each R 25 are identical or different from each other.

5. In paragraph 1, The above first compound is an organic optoelectronic device represented by any one of the following chemical formulas 1-Ⅶ, 1-Ⅷ, 1-Ⅸ, 1-Ⅹ, 1-ⅩⅠ and 1-ⅩⅡ: [Chemical 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 chemical formulas 1-Ⅶ, 1-Ⅷ, 1-Ⅸ, 1-Ⅹ, 1-ⅩⅠ and 1-ⅩⅡ, L 1 Inland L 3 is as described above, X 6 is O, S, NR g or CR h R i And, Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted 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 carbazolyl group, or a substituted or unsubstituted dibenzosilolyl group, R g , R g , R i , and R 26 Inland R 28 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m26 and m28 are each independently an integer from 1 to 4, m27 is an integer of 1 or 2, If m26 is 2 or more, each R 26 are identical or different from each other, If m27 is 2 or more, each R 27 are identical or different from each other, If m28 is 2 or more, each R 28 are identical or different from each other.

6. In paragraph 1, Above Ar 1 Inland Ar 3 An organic optoelectronic device, wherein at least one of the compounds is a 9-carbazolyl group.

7. In paragraph 1, Above L 1 -Ar 1 , L 2 -Ar 2 and L 3 -Ar 3 An organic optoelectronic device, wherein each of the substituents is independently selected from the substituents listed in Group I below: [Group I] In the above group I, X 3 Silver O, S, NR c , or CR d R e And, R c , R d , R e and R 7 Inland R 11 are each 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, Ar 10 and Ar 11 are each independently a substituted or unsubstituted C6 to C20 aryl group, m7 is one of the integers 1 to 5, m8 is one of the integers 1 to 4, m9 is one of the integers 1 to 3, m10 is an integer of 1 or 2, m11 is one of the integers 1 to 7, * is a connection point.

8. In paragraph 1, The above first compound is a compound for an organic optoelectronic device selected from the compounds listed in Group 1-1 to Group 1-3 below: [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 atoms substituted, and indicates a structure in which one or more deuterium atoms are substituted).

9. In paragraph 1, The second compound is an organic optoelectronic device represented by one of the following chemical formulas 2A, 2B, 2C, 2D, and 2E: [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 Inland L a4 , L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R a1 Inland R a4 , R 1 and R 2 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m1 and m2 are each independently an integer from 1 to 4.

10. In paragraph 9, An organic optoelectronic device, wherein the second compound is represented by the chemical formula 2C.

11. In paragraph 9, Above L 4 -Ar 4 and L 5 -Ar 5 An organic optoelectronic device, wherein each independently is one of the substituents listed in Group II below. [Group II] In the above group II, R 12 Inland R 16 are each independently hydrogen, deuterium, a cyano group, a C1 to C10 alkyl group, or a C6 to C12 aryl group, m12 is one of the integers 1 to 5, m13 is one of the integers 1 to 4, m14 is one of the integers 1 to 3, m15 is an integer of 1 or 2, m16 is one of the integers 1 to 7, * is a connection point.

12. In paragraph 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] .

13. In paragraph 1, Above Ar 6 is a substituted or unsubstituted phenyl group, Above Ar 7 Inland Ar 9 An organic optoelectronic device, wherein each independently represents a substituted or unsubstituted C6 to C12 aryl group.

14. In paragraph 1, Above L 7 An organic optoelectronic device, wherein one of the connectors listed in Group III below is selected: [Group III] In the above group Ⅲ, R 29 is 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, m29 is one of the integers 1 to 4, * is a connection point.

15. In paragraph 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] .

16. A display device comprising an organic optoelectronic device according to any one of claims 1 to 15.

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