Organic optoelectronic device and display device

Abstract

This organic optoelectronic device comprises: a positive electrode and a negative electrode facing each other; a light-emitting layer located between the positive electrode and the negative electrode; a hole transport layer located between the positive electrode and the light-emitting layer; and a hole transport auxiliary layer located between the light-emitting layer and the hole transport layer, wherein the light-emitting layer comprises a first compound represented by chemical formula 1 and a second compound represented by chemical formula 2, and the hole transport auxiliary layer comprises a third compound represented by chemical formula 2. The detailed content of chemical formula 1 and chemical formula 2 are as defined in the specification.

Description

Organic optoelectronic devices and display devices

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

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

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

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

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

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

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

[0008] According to one embodiment, an organic optoelectronic device is provided comprising an anode and a cathode facing each other, a light-emitting layer located between the anode and the cathode, a hole transport layer located between the anode and the light-emitting layer, and a hole transport assisting layer located between the light-emitting layer and the hole transport layer, wherein the light-emitting layer comprises a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2, and the hole transport assisting layer comprises a third compound represented by the following chemical formula 2.

[0009] [Chemical Formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] Z 1 To Z 3 Each independently N or CR a And,

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

[0014] L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group or a substituted or unsubstituted divalent C2 to C20 heterocyclic group, and

[0015] Ar 1 and Ar 2 One of them is a substituted or unsubstituted carbazole group, and

[0016] Ar 1 and Ar 2 The other one is a substituted or unsubstituted silyl group or a substituted or unsubstituted C6 to C30 aryl group, and

[0017] R 1 to R 8 and R aEach is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a cyano group, or a halogen group, and

[0018] R 1 to R 8 Each exists independently or two adjacent ones combine to form a ring,

[0019] [Chemical Formula 2]

[0020]

[0021] In the above chemical formula 2,

[0022] L 4 and L 5 Each is independently a single bond or a substituted or unsubstituted C6 to C30 arylene group, and

[0023] Ar 3 is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0024] R 17 to R 29 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a cyano group, or a halogen group, and

[0025] m1 is one of integers from 1 to 3, and

[0026] If m1 is 2 or greater, each R 21 They are identical or different from each other.

[0027] According to another embodiment, a display device comprising the organic optoelectronic element is provided.

[0028] Organic optoelectronic devices with high efficiency and long lifespan characteristics can be realized.

[0029] FIG. 1 is a cross-sectional view schematically illustrating an organic optoelectronic device according to one embodiment.

[0030] <Explanation of Symbols>

[0031] 100: Organic light-emitting diode

[0032] 110: Anode

[0033] 120: Cathode

[0034] 130: Emissive layer

[0035] 140: Precision Transport Layer

[0036] 150: Precision Transport Auxiliary Layer

[0037] 160: Electron transport layer

[0038]

[0039] Hereinafter, embodiments of the present invention will be described in detail. However, these are presented as examples and are not intended to limit the present invention, and the present invention is defined only by the scope of the claims set forth below.

[0040] In this specification, "substitution" means that, unless otherwise defined, at least one hydrogen of a substituent or compound is substituted with a deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.

[0041] In one example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C3 to C20 cycloalkyl group, a C6 to C30 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C5 alkyl group, a C3 to C10 cycloalkyl group, a C6 to C18 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a tert-butyl group, a cyclopropyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0042] In this specification, “non-substituted” means that a hydrogen atom remains a hydrogen atom without being substituted by another substituent.

[0043] In this specification, “hydrogen (-H)” may include “deuterium substitution (-D)” or “tritium substitution (-T)”.

[0044] In this specification, "hetero" means, unless otherwise defined, that one functional group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si, and the remainder is carbon.

[0045] In this specification, "aryl group" is a collective concept for a group having one or more hydrocarbon aromatic moietys, including a form in which all elements of the hydrocarbon aromatic moiety have p-orbitals and these p-orbitals form a conjugation, such as a phenyl group, a naphthyl group, etc., and a form in which two or more hydrocarbon aromatic moietys are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quarterphenyl group, etc., and a non-aromatic fused ring in which two or more hydrocarbon aromatic moietys are directly or indirectly fused, such as a fluorenyl group, etc.

[0046] Aryl groups include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.

[0047] In this specification, "heterocyclic group" is a superordinate concept including heteroaryl groups, meaning that a cyclic compound, such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof, contains at least one heteroatom selected from the group consisting of N, O, S, P, and Si instead of carbon (C). If the heterocyclic group is a fused ring, it may contain one or more heteroatoms in the entire heterocyclic group or in each ring.

[0048] For example, a "heteroaryl group" means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si within the aryl group. Two or more heteroaryl groups may be directly connected through sigma bonds, or if the heteroaryl group comprises two or more rings, the two or more rings may be fused together. If the heteroaryl group is a fused ring, each ring may contain one to three heteroatoms.

[0049] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be, but is not limited to, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted crisenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0050] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic groups are a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazoleyl group, a substituted or unsubstituted triazoleyl group, a substituted or unsubstituted oxazoleyl group, a substituted or unsubstituted thiazoleyl group, a substituted or unsubstituted oxadiazoleyl group, a substituted or unsubstituted thiadiazoleyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazoleyl group, a substituted or unsubstituted indoleyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted It may be an isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthiridinyl group, a substituted or unsubstituted benzoxazine dil group, a substituted or unsubstituted benzthiazine dil group, a substituted or unsubstituted acrridinyl group, a substituted or unsubstituted phenazine dil group, a substituted or unsubstituted phenothiazine dil group, a substituted or unsubstituted phenoxazine dil group, a substituted or unsubstituted carbazole dil group, a substituted or unsubstituted dibenzofuran dil group, or a substituted or unsubstituted dibenzothiophen dil group, or a combination thereof, but is not limited thereto.

[0051] In this specification, the term "hole characteristic" refers to a characteristic that can form holes by donating electrons when an electric field is applied, and means a characteristic that facilitates the injection of holes formed at the anode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the anode, and movement within the light-emitting layer by having a conduction characteristic along the HOMO level.

[0052] In addition, electronic properties refer to the ability to receive electrons when an electric field is applied, and they refer to properties that facilitate the injection of electrons formed at the cathode into the light-emitting layer, the movement of electrons formed at the light-emitting layer to the cathode, and the movement of electrons within the light-emitting layer by having conduction properties along the LUMO level.

[0053] An organic optoelectronic device according to one embodiment is described below.

[0054] Organic optoelectronic devices are not particularly limited as long as they are devices capable of mutually converting electrical energy and light energy, and examples include organic photovoltaic devices, organic light-emitting devices, organic solar cells, and organic photosensitive drums.

[0055] Here, an organic light-emitting diode is described as an example of an organic optoelectronic device, but is not limited thereto and can be applied in the same way to other organic optoelectronic devices.

[0056] In the drawings, thicknesses have been enlarged to clearly represent various layers and regions. Throughout the specification, the same reference numerals have been used for similar parts. When a part such as a layer, film, region, or plate is described as being "on" another part, this includes not only cases where it is "immediately on" another part, but also cases where there is another part in between. Conversely, when a part is described as being "immediately on" another part, it means that there is no other part in between.

[0057] FIG. 1 is a cross-sectional view schematically illustrating an organic optoelectronic device according to one embodiment.

[0058] Referring to FIG. 1, an organic light-emitting device (100) according to one embodiment comprises an anode (110) and a cathode (120) facing each other, a light-emitting layer (130) located between the anode (110) and the cathode (120), a hole transport layer (140) located between the anode (110) and the light-emitting layer (130), and a hole transport assist layer (150) located between the light-emitting layer (130) and the hole transport layer (140), and further comprises an electron transport layer (160).

[0059] The anode (110) may be made of a conductor with a high work function to facilitate hole injection, for example, and may be made of a metal, a metal oxide and / or a conductive polymer. The anode (10) may be a metal or an alloy thereof, such as nickel, platinum, vanadium, chromium, copper, zinc, gold; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyethylenedioxythiophene: PEDOT), polypyrrole and polyaniline, but is not limited thereto.

[0060] The cathode (120) may be made of a conductor with a low work function to facilitate electron injection, for example, and may be made of a metal, a metal oxide and / or a conductive polymer. The cathode (20) may be a metal or an alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc.; or a multilayer material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0061] The light-emitting layer (130) comprises at least two types of hosts and dopants, and the light-emitting layer (130) may further comprise another organic compound as a mixed host. The host comprises a first compound, which is a bipolar compound with relatively strong electron transport characteristics, and a second compound, which is a compound with relatively strong hole transport characteristics.

[0062] In one embodiment, the light-emitting layer comprises a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2.

[0063] [Chemical Formula 1]

[0064]

[0065] In the above chemical formula 1,

[0066] Z 1 To Z 3 Each independently N or CR a And,

[0067] Z 1 To Z 3 At least two of them are N, and

[0068] L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group or a substituted or unsubstituted divalent C2 to C20 heterocyclic group, and

[0069] Ar 1 and Ar 2 One of them is a substituted or unsubstituted carbazole group, and

[0070] Ar 1 and Ar 2 The other one is a substituted or unsubstituted silyl group or a substituted or unsubstituted C6 to C30 aryl group, and

[0071] R 1 to R 8 and R aEach is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a cyano group, or a halogen group, and

[0072] R 1 to R 8 Each exists independently or two adjacent ones combine to form a ring,

[0073] [Chemical Formula 2]

[0074]

[0075] In the above chemical formula 2,

[0076] L 4 and L 5 Each is independently a single bond or a substituted or unsubstituted C6 to C30 arylene group, and

[0077] Ar 3 is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0078] R 17 to R 29 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a cyano group, or a halogen group, and

[0079] m1 is one of integers from 1 to 3, and

[0080] If m1 is 2 or greater, each R 21 They are identical or different from each other.

[0081] By including the first compound and the second compound together, good interfacial characteristics can be exhibited, and compared to the case where the first compound or the second compound is used alone, the mobility of holes and electrons can be finely controlled to increase the balance of electrons and holes within the active layer (e.g., light-emitting layer, 130) of the organic optoelectronic device, thereby increasing luminous efficiency, while simultaneously reducing non-bonding charges caused by the imbalance of electron and hole mobility, thereby improving the lifespan.

[0082] Specifically, the first compound and the second compound may be included as hosts, and the organic optoelectronic device (100) including the light-emitting layer (130) to which the same is applied can increase the light-emitting efficiency in the light-emitting layer (130) by finely controlling the holes and electrons injected from the anode (110) and the cathode (120), respectively, so that they have appropriate mobility within the light-emitting layer (130), thereby strongly inducing exciton generation within the light-emitting layer (130).

[0083] In addition, the difference in mobility of holes and electrons injected from the positive electrode (110) and the negative electrode (120), respectively, within the light-emitting layer (130) can reduce or prevent exciton generation at inappropriate locations, such as the interface between the light-emitting layer (130) and adjacent layers, and / or the accumulation of uncoupled charges at the interface between the light-emitting layer (130) and adjacent layers.

[0084] Accordingly, the roll-off phenomenon in which the luminous efficiency of the organic light-emitting device (100) drops rapidly due to non-luminous excitons and / or uncoupled charges can be reduced or prevented, and thereby the lifespan of the organic light-emitting device (100) can ultimately be improved.

[0085] In addition, the aforementioned host has good electrical matching with a blue-emitting dopant that emits light of the blue emission spectrum described below, thereby increasing the efficiency of the organic optoelectronic device and suppressing degradation. For example, at least one of the first compound and the second compound has a high triplet energy level of about 2.8 eV or higher, which facilitates exciton transfer to the blue-emitting dopant, and accordingly, a high-efficiency, long-life organic optoelectronic device can be realized.

[0086] For example, Z of Chemical Formula 1 1 To Z 3 Each can be N.

[0087] For example, Z of Chemical Formula 1 1 and Z 2 are respectively N, and Z 3 is CR a It could be.

[0088] For example, Z of Chemical Formula 1 1 and Z 3 are respectively N, and Z 2 is CR a It could be.

[0089] For example, Z of Chemical Formula 1 2 Wow Z 3 are respectively N, and Z 1 is CR a It could be.

[0090] For example, L of Chemical Formula 1 1 to L 3 Each may independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted benzofuranilene group, a substituted or unsubstituted dibenzofuranilene group, a substituted or unsubstituted benzothiophenylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted triphenylenylene group, or a substituted or unsubstituted fluorenylene group.

[0091] For example, L of Chemical Formula 1 1 and L 2 Each may independently be a single bond or a substituted or unsubstituted C6 to C20 arylene group, and L of Formula 1 3 can be a single bond. For example, L of Chemical Formula 1 1 and L 2 Each may independently be a single bond or a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted naphthylene group, and L of Formula 1 3 It can be a single bond.

[0092] For example, Ar of Chemical Formula 1 1 can be a substituted or unsubstituted C6 to C30 aryl group, and Ar 2 can be a substituted or unsubstituted carbazole group. For example, Ar 1 It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group or a substituted or unsubstituted triphenylene group.

[0093] For example, Ar of Chemical Formula 1 2 When is a substituted or unsubstituted carbazole group, L 2 and L 3 They can be different from each other. For example, L 2 and L 3 One of them can be a single bond and L 2 and L 3 The other one may be a substituted or unsubstituted C6 to C20 arylene group, for example, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted naphthylene group.

[0094] For example, R of Chemical Formula 1 aIt may be hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted phenyl group, or a cyano group.

[0095] The first compound can be represented, for example, by the following chemical formula 1a.

[0096] [Chemical Formula 1a]

[0097]

[0098] In the above chemical formula 1a,

[0099] Z 1 To Z 3 , L 1 to L 3 and R 1 to R 8 It is as previously stated, and

[0100] Ar 1 It may be a substituted or unsubstituted phenylsilyl group or a substituted or unsubstituted C6 to C30 aryl group, for example, a substituted or unsubstituted triphenylsilyl group, 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 or a substituted or unsubstituted triphenylene group, and

[0101] R 9 to R 16 Each may independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a cyano group, or a halogen group, and R 9 to R 16 Each can exist independently or two adjacent ones can combine to form a ring.

[0102] For example, L of chemical formula 1a 2 and L 3 can be different from each other, for example, L2 may be a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted naphthylene group, and L 3 It can be a single bond.

[0103] For example, at least one of each substituent of chemical formulas 1 and 1a may be substituted with deuterium. The number of substituted deuteriums may be from 1 to the maximum number of hydrogens in the chemical formula, for example, from 1 to 40 or from 1 to 30, but is not limited thereto.

[0104] For example, the second compound can be represented by any one of the following chemical formulas 2a to 2d.

[0105] [Chemical Formula 2a]

[0106]

[0107] [Chemical Formula 2b]

[0108]

[0109] [Chemical Formula 2c]

[0110]

[0111] [Chemical Formula 2d]

[0112]

[0113] In the above chemical formulas 2a to 2d, L 4 , L 5 , Ar 3 , R 17 to R 20 , and R 22 to R 29 is as previously stated,

[0114] R 21a , R 21b and R 21c are each independently the aforementioned R 21 It is the same as the definition of.

[0115] For example, L of chemical formulas 2, 2a to 2d4 It may be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

[0116] For example, Ar of chemical formulas 2 and 2a to 2d 3 It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzosylolyl group, a substituted or unsubstituted dibenzosylolyl group, a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted silyl group.

[0117] For example, R of chemical formulas 2 and 2a to 2d 17 to R 29 , R 21a , R 21b and R 21c Each may independently be hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzosylolyl group, a substituted or unsubstituted dibenzosylolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted silyl group, or a cyano group.

[0118] For example, Ar 3 , R 17 to R 20 , R 22 to R 29 , R 21a , R 21b and R 21cAt least one of them may be a substituted or unsubstituted carbazole group.

[0119] For example, at least one of each substituent of chemical formulas 2, 2a to 2d may be substituted with deuterium. The number of substituted deuteriums may be 1 to the maximum number of hydrogens in the chemical formula, for example, 1 to 40 or 1 to 30, but is not limited thereto.

[0120] For example, the first compound may include one or more selected from the compounds listed in Group 1 below, but is not limited thereto.

[0121] [Group 1]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152] (Dn is the number of hydrogen atoms substituted with deuterium, indicating a structure with one or more deuterium substitutions)

[0153] For example, the second compound may include one or more selected from the compounds listed in Group 2 below, but is not limited thereto.

[0154] [Group 2]

[0155]

[0156] [D-1] [D-2] [D-3] [D-4] [D-5]

[0157]

[0158] [D-6] [D-7] [D-8] [D-9] [D-10]

[0159]

[0160] [D-11] [D-12] [D-13] [D-14] [D-15]

[0161]

[0162] [D-16] [D-17] [D-18] [D-19] [D-20]

[0163]

[0164] [D-21] [D-22] [D-23] [D-24] [D-25]

[0165]

[0166] [D-26] [D-27] [D-28] [D-29] [D-30]

[0167]

[0168] [D-31] [D-32] [D-33] [D-34] [D-35]

[0169]

[0170] [D-36] [D-37] [D-38] [D-39] [D-40]

[0171]

[0172] [D-41] [D-42] [D-43] [D-44] [D-45]

[0173]

[0174] [D-46] [D-47] [D-48] [D-49] [D-50]

[0175]

[0176] [D-51] [D-52] [D-53] [D-54] [D-55]

[0177]

[0178] [D-56] [D-57] [D-58] [D-59] [D-60]

[0179]

[0180] [D-61] [D-62] [D-63] [D-64] [D-65]

[0181]

[0182] [D-66] [D-67] [D-68] [D-69] [D-70]

[0183]

[0184] [D-71] [D-72] [D-73] [D-74] [D-75]

[0185]

[0186] [D-76] [D-77] [D-78] [D-79] [D-80]

[0187]

[0188] [D-81] [D-82] [D-83] [D-84] [D-85]

[0189]

[0190] [D-86] [D-87] [D-88] [D-89] [D-90]

[0191]

[0192] [D-91] [D-92] [D-93] [D-94] [D-95]

[0193]

[0194] [D-96] [D-97] [D-98] [D-99] [D-100]

[0195]

[0196] [D-101] [D-102] [D-103] [D-104] [D-105]

[0197] (Dn is the number of hydrogen atoms substituted with deuterium, indicating a structure with one or more deuterium substitutions)

[0198] The above mixed host may contain the first compound and the second compound in various proportions.

[0199] For example, the mixed host may contain the first compound and the second compound in a weight ratio of about 10:90 to about 90:10, and within the above range may contain them in a weight ratio of about 20:80 to about 80:20, about 30:70 to about 70:30, about 40:60 to about 60:40, or about 50:50.

[0200] For example, the first compound may be included in an amount greater than or equal to the second compound, and for example, the first compound may be included in an amount of about 50 to 90 weight percent with respect to the total content of the first compound and the second compound.

[0201] For example, the first compound may be included in an amount less than or equal to the second compound, and for example, the first compound may be included in an amount of about 10 to 50 weight percent with respect to the total content of the first compound and the second compound.

[0202] The light-emitting layer (130) may further include a light-emitting dopant in addition to the first compound and the second compound.

[0203] A luminescent dopant is a substance that is mixed in trace amounts into a composition for an organic optoelectronic device to produce luminescence, and generally, a substance such as a metal complex that emits light through multiple excitation, which excites it to a triplet state or higher, may be used. The luminescent dopant may be, for example, inorganic, organic, or organic-inorganic compounds, and may include one or more types.

[0204] The luminescent dopant may be, for example, a phosphorescent sensitizer, a fluorescent dopant, or a combination thereof.

[0205] Phosphorescent photosensitive materials can be organometallic compounds and can effectively transfer energy received from a host to a fluorescent dopant. Since the energy transfer to the fluorescent dopant is increased, excitons formed in the emissive layer emit light rapidly within the emissive layer, thereby reducing the degradation of the light-emitting device.

[0206] The phosphorescent photosensitive agent may be an organo-metal compound comprising, for example, iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), rhodium (Rh), or a combination thereof, or an organo-metal compound comprising, for example, an organic ligand comprising a nitrogen-containing ring. The nitrogen-containing ring may be, for example, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted triazine, substituted or unsubstituted carbazole, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, or a combination thereof, but is not limited thereto.

[0207] The phosphorescent photosensitive agent may be, for example, any one of the following compounds P1 to P52, but is not limited thereto:

[0208]

[0209]

[0210]

[0211]

[0212]

[0213] The fluorescent dopant can be, for example, a polycyclic compound, and can improve the luminous efficiency and lifespan characteristics of the light-emitting device by receiving energy transfer within the emissive layer through high absorbance.

[0214] The fluorescent dopant may be a condensed polycyclic compound including, for example, bromine (B), nitrogen (N), or a combination thereof, and may be selected from, for example, compounds D1 to D30 below, but is not limited thereto.

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223] The phosphorescent photosensitive agent and the fluorescent dopant may each be included in an amount of about 20% by weight or less with respect to the total content of the composition for organic optoelectronic devices, and within the above range, they may each be included in an amount of about 0.1 to 20% by weight, about 0.1 to 15% by weight, about 0.1 to 10% by weight, about 0.1 to 7% by weight, about 0.1 to 5% by weight, about 0.1 to 4% by weight, about 1 to 20% by weight, about 1 to 15% by weight, about 1 to 10% by weight, about 1 to 7% by weight, about 1 to 5% by weight, or about 1 to 4% by weight.

[0224] For descriptions regarding luminescent dopants, refer to Korean Patent Publication No. 2023-0155972 and No. 2023-0155982.

[0225] The composition for organic optoelectronic devices may additionally include additives, and the additives may be organic, inorganic, organic-inorganic, or a combination thereof.

[0226] Meanwhile, the light-emitting layer (130) can emit light of a blue light emission spectrum by the combination of the aforementioned mixed host and the light-emitting dopant. At least one of the aforementioned first compound and second compound has a high triplet energy level of about 2.8 eV or higher, thereby facilitating exciton transfer to the blue light-emitting dopant and thereby enabling the realization of a high-efficiency, long-life organic optoelectronic device. The peak wavelength of the blue light emission spectrum may, for example, be in the range of about 410 nm to 480 nm, and within the above range, may be in the range of about 420 nm to 470 nm or about 430 nm to 470 nm.

[0227] The hole transport layer (140) is located between the anode (110) and the light-emitting layer (130), and the hole transport assist layer (150) is located between the light-emitting layer (130) and the hole transport layer (140). The electron transport layer (160) is located between the cathode (120) and the light-emitting layer (130).

[0228] The hole transport layer (140) can facilitate hole transfer from the anode (110) to the light-emitting layer (130) and may include, for example, an amine compound, but is not limited thereto. For example, the amine compound may have at least one aryl group and / or heteroaryl group having hole characteristics. For example, the amine compound may be represented by the following chemical formula 6a or 6b, but is not limited thereto.

[0229] [Chemical Formula 6a] [Chemical Formula 6b]

[0230]

[0231] In chemical formula 6a or 6b,

[0232] Ar a or Ar gEach is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and

[0233] Ar a or Ar c At least one of and Ar d or Ar g At least one of them is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and

[0234] Ar h is a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof.

[0235] The hole transport assist layer (150) can form an interface with the light-emitting layer (130) by being positioned between the hole transport layer (140) and the light-emitting layer (130) so as to be in contact with the light-emitting layer (130).

[0236] The hole transport assist layer (150) includes a third compound having bipolar characteristics with relatively strong hole characteristics.

[0237] As described above, the light-emitting layer (130) can significantly improve the luminous efficiency by increasing the mobility of electrons and holes compared to when used alone, by including a first compound with relatively strong electronic properties and a second compound with relatively strong hole properties together.

[0238] In devices that introduce a material with skewed electronic or hole characteristics as the emissive layer, carrier recombination occurs at the interface between the emissive layer and the electron or charge transport layer, resulting in a relatively large formation of excitons. Consequently, due to the interaction between molecular excitons within the emissive layer and charges at the interface of the hole transport layer, a roll-off phenomenon occurs in which efficiency drops sharply, and the luminescence lifetime characteristics also drop sharply.

[0239] To solve these problems, the first and second compounds are introduced simultaneously into the light-emitting layer so that the light-emitting region is not biased toward either the electron transport layer or the hole transport layer. Additionally, by adding a hole transport auxiliary layer containing a third compound with relatively strong hole characteristics between the hole transport layer (140) and the light-emitting layer (130), the accumulation of non-bonding charges at the interface between the light-emitting layer (130) and adjacent layers can be further reduced or prevented. Accordingly, the roll-off phenomenon, in which the light-emitting efficiency of the organic light-emitting device (100) drops sharply due to non-luminous excitons and / or non-bonding charges, can be further reduced or prevented, and consequently, the lifespan of the organic optoelectronic device (100) can be ultimately further improved.

[0240] The above third compound can be represented by the above chemical formula 2.

[0241] The details regarding the above chemical formula 2 are as described above, and the specific structure of the third compound is as described in Group 2 above.

[0242] In particular, when the difference in HOMO energy levels between the second compound and the third compound calculated by Equation 1 below is 0.02 eV or less, the amount of charge accumulated between the interfaces can be reduced, and thus improvements in the lifespan, driving voltage, and / or efficiency of the organic light-emitting diode can be expected.

[0243] Equation 1 (HOMO energy level difference): {HOMO energy level of compound 2 (measured DPV (Differential Pulse Voltammetry) value)} - {HOMO energy level of compound 3 (measured DPV value)}

[0244] <DPV: Differential Pulse Voltammetry 측정 방법>

[0245] Measuring device: Zive, SP2 (company, model name)

[0246] Measurement Condition: Calculation of Energy Levels

[0247] The energy level of the material was obtained by measuring the change in current according to voltage using Differential Pulse Voltammetry (DPV) as follows. A three-electrode cell consisting of a carbon electrode (working electrode), a Pt wire (counter electrode), Ag / AgCl (3M NaCl) (reference electrode), and a DMF electrolyte containing 0.1M Tetrabutylammonium hexafluorophosphate (TBAF) was used, and Ferrocene was dissolved in the electrolyte and used as a reference correction value. 10 mg of the sample was dissolved in 10 mL of the electrolyte and, after purging with N2 gas, the reduction current was measured by applying a voltage of +0.5 V to -2.2 V, and then the oxidation current was measured by applying a voltage of +0.5 V to +1.8 V. (When applying each voltage, pulses were applied with Step potential(V): 0.005V, Pulse height(V): 0.025V, Width(s): 0.2s, Period(s): 0.5s.) Afterwards, the LUMO and HOMO were obtained by correcting the peak voltage values ​​at the reduction current and oxidation current with Ferrocene.

[0248] For example, the second compound and the third compound may be the same.

[0249] Additionally, the electron transport layer (160) can further increase electron injection and / or electron mobility between the cathode (120) and the light-emitting layer (130) and block holes.

[0250] The electron transport layer (160) may include one or more selected from, for example, the compounds listed in Group 3 below, but is not limited thereto.

[0251] [Group 3]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269] An organic optoelectronic device including the aforementioned organic light-emitting diode can be applied to a display device.

[0270]

[0271] The above-described embodiment will be explained in more detail through the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of the claims.

[0272] Unless otherwise noted, the starting materials and reactants used in the following examples and synthesis examples were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry, or P&H Tech, or synthesized using known methods.

[0273]

[0274] Preparation of compounds for organic optoelectronic devices

[0275] A compound presented as a more specific example of the compound of the present invention was synthesized through the following steps.

[0276] (Synthesis of the first compound)

[0277] Synthesis Example 1: Synthesis of Compound A-71

[0278] [Reaction Equation 1]

[0279]

[0280] 11 g of (9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole)) (9-[2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-9H-carbazole), 12.5 g of (triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane), 41.43 g of Pd(PPh3), and 8.52 g of potassium carbonate were added to 62 ml of THF and 27 ml of distilled water and heated under reflux under a nitrogen atmosphere. After 18 hours of reaction, the mixture was cooled to room temperature, the organic layer was separated, and the product was purified by column chromatography to obtain compound A-71 (15.27 g, 20.47 mmol, yield 83%).

[0281] LC / MS [M+H]+ 746.96

[0282]

[0283] (Synthesis of the second compound / third compound)

[0284] Synthesis Example 2: Synthesis of Compound D-57

[0285] [Reaction Equation 2]

[0286]

[0287] Compound D-57 was synthesized by referring to the method disclosed in Korean Patent Publication No. 10-2023-0155972.

[0288]

[0289] Synthesis Example 3: Synthesis of Compound D-79

[0290] [Reaction Equation 3]

[0291]

[0292] Step 1: Synthesis of Compound D-24

[0293] 25 g of 9-([1,1'-biphenyl]-3-yl)-2-bromo-9H-carbazole, 35.95 g of 3,9'-bicarbazole, 33.44 g of Pd2(dba)33.44 g of sodium t-butoxide, 8.67 g of tri-t-butylphosphine solution (50% in toluene) 5.5 ml (11.28 mmol), and 250 ml of toluene were added and heated under nitrogen for 6 hours under reflux. The resulting mixture was extracted with water and methylene chloride and purified by column chromatography to obtain 38.6 g (59.4 mmol) of compound D-24.

[0294] Step 2: Synthesis of Compound D-79

[0295] Compound D-24, trifluoromethanesulfonic acid, and benzene-D6 were added and stirred for 24 hours. Purified water was added and neutralized with a saturated K3PO4 solution. The organic layer was concentrated and column purified to synthesize compound D-79.

[0296]

[0297] Manufacturing of organic light-emitting diodes

[0298] Example 1

[0299] A glass substrate coated with a thin film of ITO (Indium Tin Oxide) was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and then transferred to a vacuum deposition machine. Using the ITO transparent electrode prepared in this way as the anode, a 100 Å thick hole injection layer was formed by vacuum depositing compound A doped with 3% NDP-9 (commercially available from Novaled) on the ITO substrate, and a hole transport layer was formed by depositing compound A to a thickness of 600 Å on top of the hole injection layer. A hole transport auxiliary layer was formed by depositing compound D-57 obtained in Synthesis Example 2 to a thickness of 100 Å on top of the hole transport layer. Compound A-71 obtained in Synthesis Example 1 and Compound D-57 obtained in Synthesis Example 2 were used simultaneously as hosts on top of the hole transport assist layer, and P31 was doped at 13 wt% as a phosphorescent sensitizer and D3 was doped at 1.5 wt% as a fluorescent dopant to form a 400 Å thick emissive layer by vacuum deposition. Here, Compound A-71 and Compound D-57 were used in a weight ratio of 4:6. Subsequently, BCP was deposited to a thickness of 50 Å on top of the emissive layer to form an electron transport assist layer, and Compound B and Liq were vacuum deposited simultaneously in a weight ratio of 1:1 to form an electron transport layer of 300 Å. An organic light-emitting diode was fabricated by forming a cathode by sequentially vacuum depositing LiQ 10 Å and Al 1200 Å on top of the electron transport layer.

[0300] It was fabricated with the structure ITO / Compound A (3% NDP-9 doping, 100Å) / Compound A (600Å) / Compound D-57 (100Å) / EML [Host (Compound A-71 : Compound D-57 = 34.2wt% : 51.3wt%) : P31 : D3 = 85.5wt% : 13wt% : 1.5wt%] (400Å) / BCP(50Å) / Compound B:LiQ(300Å) / LiQ(10Å) / Al(1200Å).

[0301] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine

[0302] Compound B: 8-{4-[bis(naphthalene-2-yl)-1,3,5-triazin-2-yl]phenyl}quinoline

[0303]

[0304]

[0305] Example 2

[0306] An organic light-emitting diode was fabricated in the same manner as in Example 1, except that the emitting layer and hole transport assisting layer were formed using compound D-79 obtained in Synthesis Example 3 instead of compound D-57 obtained in Synthesis Example 2 as the host of the emitting layer.

[0307]

[0308] Comparative Example 1

[0309] An organic light-emitting diode was fabricated in the same manner as in Example 1, except that a hole transport assisting layer was formed by depositing mCP (1,3-Bis(N-carbazolyl)benzene) to a thickness of 100 Å.

[0310]

[0311] Comparative Example 2

[0312] An organic light-emitting diode was fabricated using the same method as in Example 2, except that a hole transport assisting layer was formed by depositing mCP to a thickness of 100 Å.

[0313]

[0314] evaluation

[0315] The driving voltage and lifetime characteristics of organic light-emitting devices according to Examples 1 and 2 and Comparative Examples 1 and 2 were evaluated.

[0316] The specific measurement method is as follows, and the results are shown in Table 1 and Table 2.

[0317] (1) Measurement of change in current density according to voltage change

[0318] For the fabricated organic light-emitting diode, the current flowing through the unit element was measured using a current-voltage meter (Keithley 2400) while increasing the voltage from 0V to 10V, and the result was obtained by dividing the measured current value by the area.

[0319] (2) Measurement of change in brightness according to voltage change

[0320] For the fabricated organic light-emitting diode, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V, and the results were obtained.

[0321] (3) Measurement of luminous efficiency

[0322] Using the luminance, current density, and voltage measured from (1) and (2) above, the same current density (10 mA / cm²) 2 The current efficiency (cd / A) of ) was calculated.

[0323] (4) Life measurement

[0324] Luminance (cd / m²) 2 ) 2000 cd / m 2 The result was obtained by maintaining it and measuring the time it took for the current efficiency (cd / A) to decrease to 95%.

[0325] The lifespan measurements of the organic light-emitting diodes according to Example 1 and Comparative Example 1 were calculated as relative values ​​based on Comparative Example 1 and listed in Table 1 below.

[0326] The lifespan measurements of the organic light-emitting diodes according to Example 2 and Comparative Example 2 were calculated as relative values ​​based on Comparative Example 2 and are listed in Table 2 below.

[0327] (5) Driving voltage measurement

[0328] Using a current-voltage meter (Keithley 2400) at 15 mA / cm 2 The driving voltage of each component was measured to obtain the results.

[0329] The driving voltages of Example 1 and Comparative Example 1 were calculated as relative values ​​based on Comparative Example 1 and listed in Table 1 below.

[0330] The driving voltages of Example 2 and Comparative Example 2 were calculated as relative values ​​based on Comparative Example 2 and are listed in Table 2 below.

[0331] No. Host Hole Transport Auxiliary Layer Driving Voltage Lifetime Compound 1 Compound 2 Compound 3 Compound (%) (%) Example 1A-71D-57D-5792%126% Comparative Example 1A-71D-57mCP100%100%

[0332] No. Host Hole Transport Auxiliary Layer Driving Voltage Lifetime Compound 1 Compound 2 Compound 3 Compound (%) (%) Example 2A-71D-79D-79 90% 116% Comparative Example 2A-71D-79 mCP 100% 100%

[0333] Referring to Tables 1 and 2, it can be seen that the organic light-emitting device according to the embodiment has improved driving voltage and lifespan characteristics compared to the organic light-emitting device according to the comparative example.

[0334] Although the embodiments have been described in detail above, the scope of the rights is not limited thereto, and various modifications and improvements by those skilled in the art using the basic concepts defined in the following claims are also included within the scope of the rights.

Claims

1. Positive and negative poles facing each other, A light-emitting layer located between the anode and the cathode, A hole transport layer located between the anode and the light-emitting layer, and A hole transport assist layer located between the light-emitting layer and the hole transport layer. Includes, The light-emitting layer comprises a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2, and The above hole transport assisting layer is an organic optoelectronic device comprising a third compound represented by the following chemical formula 2: [Chemical Formula 1] In the above chemical formula 1, Z 1 To Z 3 Each independently N or CR a And, Z 1 To Z 3 At least two of them are N, and L 1 to L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group or a substituted or unsubstituted divalent C2 to C20 heterocyclic group, and Ar 1 and Ar 2 One of them is a substituted or unsubstituted carbazole group, and Ar 1 and Ar 2 The other one is a substituted or unsubstituted silyl group or a substituted or unsubstituted C6 to C30 aryl group, and R 1 to R 8 and R a Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a cyano group, or a halogen group, and R 1 to R 8 Each exists independently or two adjacent ones combine to form a ring, [Chemical Formula 2] In the above chemical formula 2, L 4 and L 5 Each is independently a single-bonded, substituted, or unsubstituted C6 to C30 arylene group, and Ar 3 is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and R 17 to R 29 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a cyano group, or a halogen group, and m1 is one of integers from 1 to 3, and If m1 is 2 or greater, each R 21 They are identical or different from each other.

2. In Paragraph 1, L of the above chemical formula 1 1 and L 2 Each is independently a single bonded, substituted, or unsubstituted C6 to C20 arylene group, and L of the above chemical formula 1 3 is a single bond Organic optoelectronic device.

3. In Paragraph 1, The above first compound is an organic optoelectronic device represented by the following chemical formula 1a: [Chemical Formula 1a] In the above chemical formula 1a, Z 1 To Z 3 , L 1 to L 3 and R 1 to R 8 ...is as defined in Paragraph 1, and Ar 1 ... is a substituted or unsubstituted triphenylsilyl group, 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 or a substituted or unsubstituted triphenylene group, and R 9 to R 16 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a cyano group, or a halogen group, and R 9 to R 16 Each exists independently or two adjacent ones combine to form a ring.

4. In Paragraph 3, L of the above chemical formula 1a 2 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted naphthylene group, and L of the above chemical formula 1a 3 is a single-bond organic optoelectronic device.

5. In Paragraph 1, The above chemical formula 2 is an organic optoelectronic device represented by any one of the following chemical formulas 2a to 2d: [Chemical Formula 2a] [Chemical Formula 2b] [Chemical Formula 2c] [Chemical Formula 2d] In the above chemical formulas 2a to 2d, L 4 , L 5 , Ar 3 , R 17 to R 20 , and R 22 to R 29 ...is as defined in Paragraph 1, and R 21a , R 21b and R 21c R defined in Paragraph 1, each independently 21 It is the same as the definition of.

6. In Paragraph 5, The above L 4 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group, and The above Ar 3 An organic optoelectronic device comprising 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 triphenylene group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzosylolyl group, a substituted or unsubstituted dibenzosylolyl group or a substituted or unsubstituted fluorenyl group.

7. In Paragraph 5, The above Ar 3 , R 17 to R 20 , R 22 to R 29 , R 21a , R 21b and R 21c An organic optoelectronic device in which at least one of the groups is a substituted or unsubstituted carbazole group.

8. In Paragraph 1, An organic optoelectronic device wherein the HOMO energy level difference between the second compound and the third compound calculated by the following Equation 1 is 0.02 eV or less: Equation 1 (HOMO energy level difference): {HOMO energy level of the second compound (DPV (Differential Pulse Voltammetry) measured value)} - {HOMO energy level of the third compound (DPV measured value)}.

9. In Paragraph 1, An organic optoelectronic device in which the second compound and the third compound are identical to each other.

10. In Paragraph 1, An organic optoelectronic device in which at least one of the first compound, the second compound, and the third compound is substituted with one or more deuterium atoms.

11. In Paragraph 1, The above-mentioned light-emitting layer is an organic optoelectronic device further comprising a fluorescent dopant, a phosphorescent photosensitive agent, or a combination thereof.

12. In Paragraph 11, An organic optoelectronic device in which the phosphorescent photosensitive agent is an organometallic compound and the fluorescent dopant is a condensed polycyclic compound comprising bromine (B), nitrogen (N), or a combination thereof.

13. In Paragraph 1, The above-mentioned light-emitting layer is an organic optoelectronic device that emits light of a blue light emission spectrum.

14. A display device comprising an organic optoelectronic element according to any one of claims 1 to 13.

Images