Organic optoelectronic diode and display device
By employing a tailored hole transport auxiliary layer configuration and balanced host-dopant system, the efficiency and longevity of organic optoelectronic devices, particularly OLEDs, are enhanced, addressing the limitations of existing technologies.
Patent Information
- Application Number
- PCT/KR2025/011960
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-08-13
- Filing Date
- 2025-08-07
- Publication Date
- 2026-02-19
AI Technical Summary
Existing organic optoelectronic devices face challenges in achieving high efficiency, low driving voltage, and long lifespan, particularly in organic light-emitting diodes (OLEDs) used in flat panel display devices.
Incorporating a specific configuration of hole transport auxiliary layers with compounds represented by Chemical Formulas 1 and 2, enhancing the hole transport properties between the anode and the light-emitting layer, and utilizing a balanced host-dopant system in the light-emitting layer to improve electron-hole balance.
The solution results in high-efficiency, low-driving-voltage, and long-life organic optoelectronic devices, specifically improving the performance of OLEDs in display devices.
Smart Images

Figure KR2025011960_19022026_PF_FP_ABST
Abstract
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 high-efficiency, low-driving-voltage, and long-life organic optoelectronic device.
[0007] Another embodiment provides a display device including the organic optoelectronic device.
[0008] 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, a hole transport layer positioned between the anode and the light-emitting layer, and a hole transport auxiliary layer positioned between the hole transport layer and the light-emitting layer, wherein the hole transport auxiliary layer includes a first hole transport auxiliary layer adjacent to the hole transport layer and a second hole transport auxiliary layer adjacent to the light-emitting layer, wherein the first hole transport auxiliary layer includes a first compound represented by the following chemical formula 1, and the second hole transport auxiliary layer includes a second compound represented by the following chemical formula 2.
[0009] [Chemical Formula 1]
[0010]
[0011] In the above chemical formula 1,
[0012] X 1 is O, S or CR a R b And,
[0013] R a and R b are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
[0014] 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 heterocyclic group,
[0015] R 1 and R 2 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
[0016] Ar1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
[0017] m1 is one of the integers 1 to 4,
[0018] m2 is an integer between 1 and 3;
[0019] [Chemical Formula 2]
[0020]
[0021] In the above chemical formula 2,
[0022] X 2 and X 3 are each independently O or S,
[0023] L 4 Inland L 6 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
[0024] R 3 Inland R 6 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
[0025] Ar 3 is a substituted or unsubstituted C6 to C20 aryl group,
[0026] m3 and m6 are each independently an integer from 1 to 4,
[0027] m4 and m5 are each independently an integer from 1 to 3.
[0028] According to another embodiment, a display device including the above-described organic optoelectronic device is provided.
[0029] High-efficiency, low-driving voltage, and long-life organic optoelectronic devices can be realized.
[0030] Figure 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment.
[0031] <Explanation of symbols>
[0032] 10: Anode 20: Cathode
[0033] 30: Organic layer 31: Emissive layer
[0034] 32: Hole transport layer 33: Hole transport auxiliary layer
[0035] 33a: First hole transport auxiliary layer 33b: Second hole transport auxiliary layer
[0036] 34: Hole injection layer 35: Electron transport layer
[0037]
[0038] 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.
[0039] 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.
[0040] In one embodiment of the present invention, "substitution" means that at least one hydrogen in a 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 C40 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 compound is substituted with deuterium, a C1 to C20 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 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 a substituent or a compound is substituted with deuterium, a C1 to C5 alkyl group, a C1 to C6 alkylsilyl group, a C3 to C20 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 a substituent or a compound is substituted with deuterium, a cyano group, a methyl group, an ethyl group, a propyl group, an iso-propyl group, a butyl group, a tert-butyl group, a trimethylsilyl group, a hexyl group, a bicycloheptyl group, an adamantyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.
[0041] As used herein, “unsubstituted” means that a hydrogen atom remains a hydrogen atom without being replaced by another substituent.
[0042] In this specification, "deuterium substitution (-D)" or "tritium substitution (-T)" may be included.
[0043] 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.
[0044] 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.
[0045] Aryl groups include monocyclic, polycyclic, or fused ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.
[0046] 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.
[0047] 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.
[0048] 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.
[0049] 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 benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, 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.
[0050] 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.
[0051] 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.
[0052] 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.
[0053] 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.
[0054] 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.
[0055] Figure 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment.
[0056] An organic light-emitting device according to an embodiment will be described with reference to FIG. 1 below.
[0057] Referring to FIG. 1, an organic light-emitting device according to one embodiment includes an anode (10) and a cathode (20) facing each other, and an organic layer (30) positioned between the anode (10) and the cathode (20).
[0058] The anode (10) can be made of a conductor with 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 (10) 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.
[0059] The cathode (20) can be made of a conductor with a low work function to facilitate electron injection, for example, and can be made of a metal, a metal oxide, and / or a conductive polymer. The cathode (20) can 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; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.
[0060] The organic layer (30) includes a light-emitting layer (31), a hole transport layer (32), and a hole transport auxiliary layer (33) located between the hole transport layer (32) and the light-emitting layer (31).
[0061] The light-emitting layer (31) includes at least two types of hosts and dopants, and the hosts may be, for example, phosphorescent hosts.
[0062] The above phosphorescent host should facilitate the injection and transport of holes and electrons within the light-emitting layer, ultimately enable holes and electrons to meet to form excitons, and be able to transfer the energy of the formed excitons to the dopant. Examples of the phosphorescent host include organic compounds including carbazole, indolocarbazole, dibenzofuran, dibenzothiophene, indolodibenzofuran, indolodibenzothiophene, fluorene, indenocarbazole, triphenylene, pyrimidine, triazine, or a combination thereof.
[0063] The above phosphorescent host can be used without limitation as long as it is a known material, and may be, for example, a single host or a mixed host.
[0064] For example, the light-emitting layer may include a first host represented by the following chemical formula 3.
[0065] [Chemical Formula 3]
[0066]
[0067] In the above chemical formula 3,
[0068] Z 1 Inland Z 6 are each independently N or CL a -R c And,
[0069] Z 1 Inland Z 6 At least two of them are N,
[0070] L a are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
[0071] R care each 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 silyl group, a substituted or unsubstituted amine group, halogen, cyano group, or a combination thereof,
[0072] R c are each independently present or adjacent groups are linked to form a substituted or substituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring.
[0073] The first host effectively expands the LUMO energy band by including a nitrogen-containing hexagonal moiety, and thus, when included with the second host described below, it can significantly improve the lifetime characteristics of a device to which it is applied by increasing the balance between holes and electrons.
[0074] For example, Z 1 Inland Z 6 Two of them are nitrogen (N) and the rest are CL a -R c It could be.
[0075] For example Z 1 and Z 3 is nitrogen and Z 2 is N or CL a -R c And Z 4 is N or CL a -R c And Z 5 is N or CL a -R c And Z 6 is N or CL a -R c It could be.
[0076] For example, Z 1 Inland Z 6 Three of them are nitrogen (N) and the rest are CL a -R c It could be.
[0077] For example Z 1, Z 3 and Z 5 is nitrogen and Z 2 is N or CL a -R c And Z 4 is N or CL a -R c And Z 6 is N or CL a -R c It could be.
[0078] As a specific example, the above R c Depending on the specific substituent, the first host may be represented by, for example, any one of the following chemical formulas 3A to 3C.
[0079] [Chemical Formula 3A] [Chemical Formula 3B]
[0080]
[0081] [Chemical Formula 3C]
[0082]
[0083] In the above chemical formulas 3A to 3C,
[0084] Z 1 , Z 3 and Z 5 are each independently N or CL a -R c And,
[0085] Z 1 , Z 3 and Z 5 At least two of them are N,
[0086] X 5 is O, S or NR d And,
[0087] L a , and L 1 Inland L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
[0088] R c , R d and R 43 Inland R 49 are each 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 silyl group, a substituted or unsubstituted amine group, halogen, cyano group, or a combination thereof,
[0089] R 43 Inland R 46 are each independently present or adjacent groups are connected to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring,
[0090] Ar 9 and Ar 10 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
[0091] m30, m31, m33, m35 and m36 are each independently an integer from 1 to 4,
[0092] m32 and m34 are each independently an integer from 1 to 3.
[0093] In the above chemical formula 3A, when m30 is 2 or more, each R 43 may be the same or different.
[0094] In the above chemical formula 3A, when m31 is 2 or more, each R 44 may be the same or different.
[0095] In the above chemical formula 3B, when m32 is 2 or more, each R 45 may be the same or different.
[0096] In the above chemical formula 3B, when m33 is 2 or more, each R 46 may be the same or different.
[0097] In the above chemical formula 3C, when m34 is 2 or more, each R 47 may be the same or different.
[0098] In the above chemical formula 3C, when m35 is 2 or more, each R 48 may be the same or different.
[0099] In the above chemical formula 3C, when m36 is 2 or more, each R 49 may be the same or different.
[0100] In this specification, "adjacent groups are linked to form a substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic ring" means that any two adjacent substituents are linked to each other to form a ring. For example, in Chemical Formula 3A, R 44 Adjacent group or R 45 Adjacent groups among them can be linked to each other to form a substituted or unsubstituted aromatic monocyclic ring. The aromatic monocyclic ring formed at this time can be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, etc., and the heteroaromatic polycyclic ring can be, for example, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, etc.
[0101] As a more specific example, the chemical formula 3A can be expressed by any one of the following chemical formulas 3A-Ⅰ to 3A-ⅩⅥ.
[0102] [Chemical Formula 3A-Ⅰ] [Chemical Formula 3A-Ⅱ]
[0103]
[0104] [Chemical Formula 3A-Ⅲ] [Chemical Formula 3A-Ⅳ]
[0105]
[0106] [Chemical Formula 3A-Ⅴ] [Chemical Formula 3A-Ⅵ]
[0107]
[0108] [Chemical Formula 3A-Ⅶ] [Chemical Formula 3A-Ⅷ]
[0109]
[0110] [Chemical Formula 3A-Ⅸ] [Chemical Formula 3A-Ⅹ]
[0111]
[0112] [Chemical Formula 3A-ⅩⅠ] [Chemical Formula 3A-ⅩⅡ]
[0113]
[0114] [Chemical Formula 3A-ⅩⅢ] [Chemical Formula 3A-ⅩⅣ]
[0115]
[0116] [Chemical Formula 3A-ⅩⅤ] [Chemical Formula 3A-ⅩⅥ]
[0117]
[0118] In the above chemical formulas 3A-Ⅰ to 3A-ⅩⅥ,
[0119] m30 is as mentioned above,
[0120] X 6 is O or S,
[0121] L 11 Inland L 13 are each independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group,
[0122] Ar 9 and Ar 10 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 triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,
[0123] R 43 , R 44 , R 50 Inland R 54 , R 43a , R 43b , R 43c , R 43d , R 44a , R 44b , R 44c and R 44d are each independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,
[0124] m30' and m31' are each independently an integer of 1 or 2,
[0125] m37, m38 and m39 are each independently an integer from 1 to 4.
[0126] For example, the above chemical formula 3B can be expressed by any one of the following chemical formulas 3B-Ⅰ to 3B-IV.
[0127] [Chemical Formula 3B-Ⅰ] [Chemical Formula 3B-Ⅱ]
[0128]
[0129] [Chemical Formula 3B-Ⅲ] [Chemical Formula 3B-Ⅳ]
[0130]
[0131] In the above chemical formulas 3B-Ⅰ to 3B-IV, the definition of each substituent is as defined in the above chemical formula 2B.
[0132] For example, the above chemical formula 3C can be expressed as the following chemical formula 3C-Ⅰ or chemical formula 3C-Ⅱ.
[0133] [Chemical Formula 3C-Ⅰ] [Chemical Formula 3C-Ⅱ]
[0134]
[0135] In the above chemical formulas 3C-Ⅰ and 3C-Ⅱ, the definition of each substituent is as defined in the above chemical formula 3C.
[0136] In a specific embodiment, the first host can be represented by the chemical formula 3A-I.
[0137] For example, in the above chemical formula 3A-Ⅰ, L 11 Inland L 13 are each independently a single bond or a substituted or unsubstituted C6 to C12 aryl group, and Ar 9 and Ar 10 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group, and R 43a , R 43b , R 43c , R 43d , R 44a , R 44b , R 44c and R 44d Each may independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.
[0138] The first host may be, for example, one selected from the compounds listed in Group 3 below, but is not limited thereto.
[0139] [Group 3]
[0140] [A-1] [A-2] [A-3] [A-4] [A-5]
[0141]
[0142] [A-6] [A-7] [A-8] [A-9] [A-10]
[0143]
[0144] [A-11] [A-12] [A-13] [A-14] [A-15]
[0145]
[0146] [A-16] [A-17] [A-18] [A-19] [A-20]
[0147]
[0148] [A-21] [A-22] [A-23] [A-24] [A-25]
[0149]
[0150] [A-26] [A-27] [A-28] [A-29] [A-30]
[0151]
[0152] [A-31] [A-32] [A-33] [A-34] [A-35]
[0153]
[0154] [A-36] [A-37] [A-38] [A-39] [A-40]
[0155]
[0156] [A-41] [A-42] [A-43] [A-44] [A-45]
[0157]
[0158] [A-46] [A-47] [A-48] [A-49] [A-50]
[0159]
[0160] [A-51] [A-52] [A-53] [A-54] [A-55]
[0161]
[0162] [A-56] [A-57] [A-58] [A-59] [A-60]
[0163]
[0164] [A-61] [A-62] [A-63] [A-64] [A-65]
[0165]
[0166] [A-66] [A-67] [A-68] [A-69] [A-70]
[0167]
[0168] [A-71] [A-72] [A-73] [A-74] [A-75]
[0169]
[0170] [A-76] [A-77] [A-78] [A-79] [A-80]
[0171]
[0172] [A-81] [A-82] [A-83] [A-84] [A-85]
[0173]
[0174] [A-86]
[0175]
[0176] [A-87] [A-88] [A-89] [A-90] [A-91]
[0177]
[0178] [A-92] [A-93] [A-94] [A-95] [A-96]
[0179]
[0180] [A-97] [A-98] [A-99] [A-100]
[0181]
[0182] [A-101] [A-102] [A-103] [A-104]
[0183]
[0184] [A-105] [A-106] [A-107] [A-108]
[0185]
[0186] [A-109] [A-110] [A-111] [A-112]
[0187]
[0188] [A-113] [A-114] [A-115] [A-116]
[0189]
[0190] [A-117] [A-118] [A-119] [A-120]
[0191]
[0192] [A-121] [A-122] [A-123] [A-124] [A-125]
[0193]
[0194] [A-126] [A-127] [A-128] [A-129] [A-130]
[0195]
[0196] [A-131] [A-132] [A-133] [A-134] [A-135]
[0197]
[0198] [A-136] [A-137] [A-138] [A-139] [A-140]
[0199]
[0200] [A-141] [A-142] [A-143] [A-144] [A-145]
[0201]
[0202] [A-146] [A-147] [A-148] [A-149] [A-150]
[0203]
[0204] [A-151] [A-152] [A-153] [A-154] [A-155]
[0205]
[0206] [A-156] [A-157] [A-158] [A-159] [A-160]
[0207]
[0208] [A-161] [A-162] [A-163] [A-164] [A-165]
[0209]
[0210] [A-166] [A-167] [A-168] [A-169] [A-170]
[0211]
[0212] [A-171] [A-172] [A-173] [A-174] [A-175]
[0213]
[0214] [A-176] [A-177] [A-178] [A-179] [A-180]
[0215]
[0216] [A-181] [A-182] [A-183] [A-184] [A-185]
[0217]
[0218] [A-186] [A-187] [A-188] [A-189] [A-190]
[0219]
[0220] [A-191] [A-192] [A-193] [A-194] [A-195]
[0221]
[0222] [A-196] [A-197] [A-198] [A-199] [A-200]
[0223]
[0224] [A-201] [A-202] [A-203] [A-204] [A-205]
[0225]
[0226] [A-206] [A-207] [A-208] [A-209] [A-210]
[0227]
[0228] [A-211] [A-212] [A-213] [A-214] [A-215]
[0229]
[0230] [A-216] [A-217] [A-218] [A-219] [A-220]
[0231]
[0232] [A-221] [A-222] [A-223] [A-224] [A-225]
[0233]
[0234] [B-1] [B-2] [B-3] [B-4]
[0235]
[0236] [B-5] [B-6] [B-7] [B-8]
[0237]
[0238] [B-9] [B-10] [B-11] [B-12]
[0239]
[0240] [B-13] [B-14] [B-15] [B-16]
[0241]
[0242] [B-17] [B-18] [B-19] [B-20]
[0243]
[0244] [B-21] [B-22] [B-23] [B-24]
[0245]
[0246] [B-25] [B-26] [B-27] [B-28]
[0247]
[0248] [B-29] [B-30] [B-31] [B-32]
[0249]
[0250] [B-33] [B-34] [B-35] [B-36]
[0251]
[0252] [B-37] [B-38] [B-39] [B-40]
[0253]
[0254] [B-41] [B-42] [B-43] [B-44]
[0255]
[0256] [A-45] [B-46] [B-47] [B-48]
[0257]
[0258] [B-49] [B-50] [B-51] [B-52]
[0259]
[0260] [B-53] [B-54] [B-55] [B-56]
[0261]
[0262] [B-57] [B-58] [B-59] [B-60]
[0263]
[0264] [B-61] [B-62] [B-63] [B-64]
[0265]
[0266] [B-65] [B-66] [B-67] [B-68]
[0267]
[0268] [B-69] [B-70] [B-71] [B-72]
[0269]
[0270] [B-73] [B-74] [B-75] [B-76]
[0271]
[0272] [B-77] [B-78] [B-79] [B-80]
[0273]
[0274] [B-81] [B-82] [B-83] [B-84]
[0275]
[0276] [B-85] [B-86] [B-87] [B-88]
[0277]
[0278] [B-89] [B-90] [B-91] [B-92]
[0279]
[0280] [B-93] [B-94] [B-95] [B-96]
[0281]
[0282] [B-97] [B-98] [B-99] [B-100]
[0283]
[0284] [B-101] [B-102] [B-103] [B-104]
[0285]
[0286] [B-105] [B-106] [B-107] [B-108]
[0287]
[0288] [B-109] [B-110] [B-111] [B-112]
[0289]
[0290] [B-113] [B-114] [B-115] [B-116]
[0291]
[0292] [B-117] [B-118] [B-119] [B-120]
[0293]
[0294] [B-121] [B-122] [B-123] [B-124]
[0295]
[0296] [B-125] [B-126] [B-127] [B-128]
[0297]
[0298] [B-129] [B-130] [B-131] [B-132]
[0299]
[0300] [B-133] [B-134] [B-135] [B-136]
[0301]
[0302] [B-137] [B-138] [B-139] [B-140]
[0303]
[0304] [B-141] [B-142] [B-143] [B-144]
[0305]
[0306] [B-145] [B-146] [B-147] [B-148]
[0307]
[0308] [B-149] [B-150] [B-151] [B-152]
[0309]
[0310] [B-153] [B-154] [B-155] [B-156]
[0311]
[0312] [B-157] [B-158] [B-159] [B-160]
[0313]
[0314] [B-161] [B-162] [B-163] [B-164]
[0315]
[0316] [B-165] [B-166] [B-167] [B-168]
[0317]
[0318] [B-169] [B-170] [B-171] [B-172]
[0319]
[0320] [B-173] [B-174] [B-175] [B-176]
[0321]
[0322] [B-177] [B-178] [B-179] [B-180]
[0323]
[0324] [B-181] [B-182] [B-183] [B-184]
[0325]
[0326] [B-185] [B-186] [B-187] [B-188]
[0327]
[0328] [B-189]
[0329]
[0330] [B-190] [B-191] [B-192] [B-193] [B-194]
[0331]
[0332] [B-195] [B-196] [B-197] [B-198] [B-199]
[0333]
[0334] [B-200] [B-201] [B-202] [B-203] [B-204]
[0335]
[0336]
[0337]
[0338]
[0339]
[0340]
[0341]
[0342]
[0343]
[0344]
[0345]
[0346]
[0347]
[0348]
[0349]
[0350]
[0351]
[0352] Dn refers to the number of deuterium atoms substituted, and n is an integer greater than or equal to 0.
[0353] For example, the light-emitting layer may further include a second host represented by the following chemical formula 4; a combination of the following chemical formulas 5 and 6; the following chemical formula 7; or the following chemical formula 8.
[0354] [Chemical Formula 4]
[0355]
[0356] In the above chemical formula 4,
[0357] R 26 Inland R 30 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,
[0358] 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,
[0359] L 7 and L 8 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
[0360] m8, m11 and m12 are each independently an integer from 1 to 4,
[0361] m9 and m10 are each independently an integer from 1 to 3,
[0362] If m8 to m12 are 2 or more, each R 26 Inland R 30 are identical or different from each other,
[0363] n is an integer between 0 and 2;
[0364] [Chemical Formula 5] [Chemical Formula 6]
[0365]
[0366] In the above chemical formulas 5 and 6,
[0367] Among a1* to a4* in chemical formula 5, two adjacent ones are each a connecting carbon (C) connected to * in chemical formula 6,
[0368] Among a1* to a4* in chemical formula 5, the remaining two that are not connected to chemical formula 6 are CL b -R e And,
[0369] L b , L 9 and L 10 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
[0370] R e , R 31 and R 32 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,
[0371] Ar 6 and Ar 7 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
[0372] m13 and m14 are each independently an integer from 1 to 4,
[0373] If m13 and m14 are 2 or more, each R 31 and R 32 are identical or different from each other;
[0374] [Chemical Formula 7]
[0375]
[0376] In the above chemical formula 7,
[0377] L 14 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
[0378] R 33 Inland R 36 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,
[0379] Ar 8 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
[0380] m15, m17 and m18 are each independently an integer from 1 to 4,
[0381] m16 is an integer between 1 and 3,
[0382] If m15 to m18 are 2 or more, each R 33 Inland R 36 are identical or different from each other;
[0383] [Chemical Formula 8]
[0384]
[0385] In the above chemical formula 8,
[0386] X 7 Silver O, S, NR f , CR g R h or SiR i R j And,
[0387] R f , R g , R h , R i , R j , and R 37are each independently hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
[0388] m19 is an integer between 1 and 4,
[0389] Ring A is any one selected from the rings listed in Group I below,
[0390] [Group Ⅰ]
[0391]
[0392] In the above group Ⅰ,
[0393] * is the connection point,
[0394] X 8 Silver O, S, NR g , CR h R i or SiR j R k And,
[0395] R g , R h , R i , R j , R k and R 38 Inland R 42 are each independently hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
[0396] R g , and R 37 Inland R 42 At least one of them is a group represented by the following chemical formula a,
[0397] [chemical formula a]
[0398]
[0399] In the above chemical formula a,
[0400] L 15 Inland L 17 are each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group,
[0401] Ar 11 and Ar 12 are each independently a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
[0402] * is a connection point.
[0403] The above second host can be used in the light-emitting layer together with the above-described first host to improve the light-emitting efficiency and lifespan characteristics by increasing the mobility of charges and enhancing stability.
[0404] In the above chemical formula 4, when m8 is 2 or more, each R 26 may be identical or different from each other,
[0405] In the above chemical formula 4, when m9 is 2 or more, each R 27 may be identical or different from each other,
[0406] In the above chemical formula 4, when m10 is 2 or more, each R 28 may be identical or different from each other,
[0407] In the above chemical formula 4, when m11 is 2 or more, each R 29 may be identical or different from each other,
[0408] In the above chemical formula 4, when m12 is 2 or more, each R 30 may be identical or different from each other,
[0409] In the above chemical formulas 5 and 6, when m13 is 2 or more, each R 31 are identical or different from each other,
[0410] In the above chemical formulas 5 and 6, when m14 is 2 or more, each R32 are identical or different from each other,
[0411] In the above chemical formula 7, when m15 is 2 or more, each R 33 are identical or different from each other,
[0412] In the above chemical formula 7, when m16 is 2 or more, each R 34 are identical or different from each other,
[0413] In the above chemical formula 7, when m17 is 2 or more, each R 35 are identical or different from each other,
[0414] In the above chemical formula 7, when m18 is 2 or more, each R 36 are identical or different from each other.
[0415] In the above chemical formula 8, when m19 is 2 or more, each R 37 are identical or different from each other.
[0416] For example, Ar of the above chemical formula 4 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,
[0417] L of the above chemical formula 4 7 and L 8 are each independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,
[0418] R of the above chemical formula 4 26 Inland R 30 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group,
[0419] n can be 0 or 1.
[0420] For example, “substitution” in the above chemical formula 4 means that at least one hydrogen is substituted with deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.
[0421] For example, Ar of the above chemical formula 4 7 and Ar 8 may each independently be 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.
[0422] In a specific embodiment of the present invention, the chemical formula 4 can be expressed as one of the following chemical formulas 4-1 to 4-15.
[0423] [Chemical Formula 4-1] [Chemical Formula 4-2] [Chemical Formula 4-3]
[0424]
[0425] [Chemical Formula 4-4] [Chemical Formula 4-5] [Chemical Formula 4-6]
[0426]
[0427] [Chemical Formula 4-7] [Chemical Formula 4-8] [Chemical Formula 4-9]
[0428]
[0429] [Chemical Formula 4-10] [Chemical Formula 4-11] [Chemical Formula 4-12]
[0430]
[0431] [Chemical Formula 4-13] [Chemical Formula 4-14] [Chemical Formula 4-15]
[0432]
[0433] In the above chemical formulas 4-1 to 4-15, R 26 Inland R 30are each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and L 7 -Ar 4 and L 8 -Ar 5 Each of may independently be one of the substituents listed in Group II below.
[0434] [Group II]
[0435]
[0436] In the above group II,
[0437] R 55 Inland R 61 are each independently hydrogen, deuterium, cyano group, C1 to C10 alkyl group or C6 to C12 aryl group,
[0438] m41 is an integer between 1 and 5,
[0439] m42 is one of the integers 1 to 4,
[0440] m43 is one of the integers 1 to 3,
[0441] m44 is an integer of 1 or 2,
[0442] m45 is one of the integers 1 to 7,
[0443] * is a connection point.
[0444] In the above group Ⅱ, if m41 is 2 or more, each R 55 may be identical or different.
[0445] In the above group Ⅱ, if m42 is 2 or more, each R 56 may be identical or different.
[0446] In the above group Ⅱ, if m43 is 2 or more, each R 57 may be the same or different.
[0447] In the above group Ⅱ, when m44 is 2, each R 58may be the same or different.
[0448] In the above group Ⅱ, if m45 is 2 or more, each R 59 may be the same or different.
[0449] The combination of the above chemical formulas 5 and 6 can be expressed, for example, by any one of the following chemical formulas 5A, 5B, 5C, 5D, and 5E.
[0450] [Formula 5A] [Formula 5B] [Formula 5C]
[0451]
[0452] [Chemical Formula 5D] [Chemical Formula 5E]
[0453]
[0454] In the above chemical formulas 5A to 5E, L 9 , L 10 , Ar 6 , Ar 7 , R 31 , R 32 , m13 and m14 are as described above,
[0455] L b1 Inland L b4 is the aforementioned L 9 and L 10 is the same as the definition of
[0456] R e1 Inland R e4 is the aforementioned R 31 and R 32 It is the same as the definition of .
[0457] For example, Ar of the chemical formulas 5 and 6 6 and Ar 7are 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,
[0458] R e1 Inland R e4 , R 31 and R 32 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.
[0459] In a specific embodiment of the present invention, L of the chemical formula 5 and chemical formula 6 9 -Ar 6 and L 10 -Ar 7 Each of can be independently selected from the substituents listed in Group II above.
[0460] In one embodiment, the R e1 Inland R e4 , R 31 and R 32 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.
[0461] For example, the above R e1 Inland R e4 , R 31 and R 32 may each independently be hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group,
[0462] In a specific embodiment, the R e1 Inland R e4 , R 31 and R 32 may each independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.
[0463] Above L b1 Inland L b4 is a single bond, and L 9 and L 10 are each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, and R 31 , R 32 , R e3 and R e4 are hydrogen, deuterium, or a substituted or unsubstituted phenyl group, respectively, and Ar 6 and Ar 7 may 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.
[0464] The above chemical formula 7 can be expressed, for example, as any one of the following chemical formulas 7-1 to 7-4.
[0465] [Chemical Formula 7-1] [Chemical Formula 7-2]
[0466]
[0467] [Chemical Formula 7-3] [Chemical Formula 7-4]
[0468]
[0469] In the above chemical formulas 7-1 to 7-4, L 14 , Ar 8 , R 33 Inland R 36 And m15 to m18 are as described above.
[0470] For example, Ar of the above chemical formula 7 8is 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,
[0471] R 33 Inland R 36 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.
[0472] In a specific embodiment of the present invention, L of the chemical formula 7 14 -Ar 8 may be selected from the substituents listed in Group II above.
[0473] For example, the above R 33 Inland R 36 may each independently be hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group.
[0474] The above chemical formula 8 can be expressed, for example, as any one of the following chemical formulas 8-Ⅰ to 8-IX.
[0475] [Chemical Formula 8-Ⅰ] [Chemical Formula 8-Ⅱ]
[0476]
[0477] [Chemical Formula 8-Ⅲ] [Chemical Formula 8-Ⅳ]
[0478]
[0479] [Chemical Formula 8-Ⅴ] [Chemical Formula 8-Ⅵ]
[0480]
[0481] [Chemical Formula 8-Ⅶ] [Chemical Formula 8-Ⅷ]
[0482]
[0483] [Chemical Formula 8-Ⅸ]
[0484]
[0485] In the above chemical formulas 8-Ⅰ to 8-IX,
[0486] X 7 , X 8 , R 37 Inland R 42 is as described above.
[0487] In addition, depending on the substitution direction of the amine group, the chemical formula 8 can be expressed as any one of the following chemical formulas 8-ⅠA to 8-ⅨA, 8-ⅠB to 8-ⅨB, and 8-ⅠC to 8-ⅢC.
[0488] [Chemical Formula 8-ⅠA] [Chemical Formula 8-ⅡA]
[0489]
[0490] [Chemical Formula 8-ⅢA] [Chemical Formula 8-ⅣA]
[0491]
[0492] [Chemical Formula 8-ⅤA] [Chemical Formula 8-ⅥA]
[0493]
[0494] [Chemical Formula 8-ⅦA] [Chemical Formula 8-ⅧA]
[0495]
[0496] [Chemical Formula 8-ⅨA]
[0497]
[0498] [Chemical Formula 8-ⅠB] [Chemical Formula 8-ⅡB]
[0499]
[0500] [Chemical Formula 8-ⅢB] [Chemical Formula 8-ⅣB]
[0501]
[0502] [Chemical Formula 8-ⅤB] [Chemical Formula 8-ⅥB]
[0503]
[0504] [Chemical Formula 8-ⅦB] [Chemical Formula 8-ⅧB]
[0505]
[0506] [Chemical Formula 8-ⅨB] [Chemical Formula 8-ⅠC]
[0507]
[0508] [Chemical Formula 8-ⅡC] [Chemical Formula 8-ⅢC]
[0509]
[0510] In the chemical formulas 8-ⅠA to 8-ⅨA, 8-ⅠB to 8-ⅨB, and 8-ⅠC to 8-ⅢC,
[0511] X 7 , X 8 , L 15 Inland L 17 , Ar 11 and Ar 12 is as described above,
[0512] R 37 Inland R 42 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
[0513] m19', m20', m22' and m24' are each independently an integer from 1 to 3.
[0514] In one embodiment, the chemical formula 8 can be expressed as the chemical formula 8-ⅣB or the chemical formula 8-ⅧB.
[0515] For example, X of the above chemical formula 8-ⅣB 7 is NR f It could be.
[0516] For example, X of the above chemical formula 8-ⅧB 7 is O or S, and X 8 Silver CR g R h or SiR i R j It could be.
[0517] Here R f , R g , R h , R i and R j Each may independently be a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.
[0518] In one embodiment, the chemical formula 8 may be expressed as the following chemical formula 8-ⅣB-2 or chemical formula 8-ⅧB-2.
[0519] [Chemical Formula 8-ⅣB-2] [Chemical Formula 8-ⅧB-2]
[0520]
[0521] In the above chemical formula 8-ⅣB-2 and chemical formula 8-ⅧB-2,
[0522] m19, m21 and m23 are as described above,
[0523] L 15 Inland L 17 are each independently a single bond or a substituted or unsubstituted phenylene group,
[0524] The above Ar 11 and Ar 12are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group,
[0525] X 7 is NR f , O or S,
[0526] X 8 Silver CR g R h or SiR i R j And,
[0527] R f , R g , R h , R i and R j are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
[0528] R 37 , R 39 Inland R 42 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
[0529] m22' and m24' are each independently an integer from 1 to 3.
[0530] For example, the above L 15 Inland L 17 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
[0531] For example, the above Ar 11 and Ar 12may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzofuranofluorenyl group, or a substituted or unsubstituted benzothiophenefluorenyl group.
[0532] For example, the second host may be, but is not limited to, one selected from the compounds listed in Group 4 below.
[0533] [Group 4]
[0534] [D-1] [D-2] [D-3] [D-4] [D-5]
[0535]
[0536] [D-6] [D-7] [D-8] [D-9] [D-10]
[0537]
[0538] [D-11] [D-12] [D-13] [D-14] [D-15]
[0539]
[0540] [D-16] [D-17] [D-18] [D-19] [D-20]
[0541]
[0542] [D-21] [D-22] [D-23] [D-24] [D-25]
[0543]
[0544] [D-26] [D-27] [D-28] [D-29] [D-30]
[0545]
[0546] [D-31] [D-32] [D-33] [D-34] [D-35]
[0547]
[0548] [D-36] [D-37] [D-38] [D-39] [D-40]
[0549]
[0550] [D-41] [D-42] [D-43] [D-44] [D-45]
[0551]
[0552] [D-46] [D-47] [D-48] [D-49] [D-50]
[0553]
[0554] [D-51] [D-52] [D-53] [D-54] [D-55]
[0555]
[0556] [D-56] [D-57] [D-58] [D-59] [D-60]
[0557]
[0558] [D-61] [D-62] [D-63] [D-64] [D-65]
[0559]
[0560] [D-66] [D-67] [D-68] [D-69] [D-70]
[0561]
[0562] [D-71] [D-72] [D-73] [D-74] [D-75]
[0563]
[0564] [D-76] [D-77] [D-78] [D-79] [D-80]
[0565]
[0566] [D-81] [D-82] [D-83] [D-84] [D-85]
[0567]
[0568] [D-86] [D-87] [D-88] [D-89] [D-90]
[0569]
[0570] [D-91] [D-92] [D-93] [D-94] [D-95]
[0571]
[0572] [D-96] [D-97] [D-98] [D-99] [D-100]
[0573]
[0574] [D-101] [D-102] [D-103] [D-104] [D-105]
[0575]
[0576] [D-106] [D-107] [D-108] [D-109] [D-110]
[0577]
[0578] [D-111] [D-112] [D-113] [D-114] [D-115]
[0579]
[0580] [D-116] [D-117] [D-118] [D-119] [D-120]
[0581]
[0582] [D-121] [D-122] [D-123] [D-124]
[0583]
[0584] [D-125] [D-126] [D-127] [D-128] [D-129]
[0585]
[0586] [D-130] [D-131] [D-132]
[0587]
[0588] [D-133] [D-134] [D-135]
[0589]
[0590] [D-136] [D-137] [D-138] [D-139] [D-140]
[0591]
[0592] [D-141] [D-142] [D-143] [D-144]
[0593]
[0594] [D-145] [D-146] [D-147] [D-148] [D-149]
[0595]
[0596] [D-150] [D-151] [D-152] [D-153] [D-154]
[0597]
[0598] [D-155] [D-156] [D-157] [D-158] [D-159]
[0599]
[0600] [D-160] [D-161] [D-162][D-163] [D-164]
[0601]
[0602] [D-165] [D-166] [D-167] [D-168] [D-169]
[0603]
[0604] [D-170] [D-171] [D-172] [D-173] [D-174]
[0605]
[0606] [D-175] [D-176] [D-177] [D-178] [D-179]
[0607]
[0608] [D-180] [D-181] [D-182]
[0609]
[0610] [D-183] [D-184] [D-185] [D-186]
[0611]
[0612] [D-187] [D-188] [D-189] [D-190]
[0613]
[0614] [D-191] [D-192][D-194] [D-195]
[0615]
[0616] [D-196] [D-197] [D-198][D-199]
[0617]
[0618] [D-200] [D-201] [D-202]
[0619]
[0620] [D-203] [D-204] [D-205][D-206]
[0621]
[0622] [D-207] [D-208] [D-209][D-210]
[0623]
[0624] [D-211] [D-212] [D-213][D-214]
[0625]
[0626] [D-215] [D-216] [D-217][D-218] [D-219]
[0627]
[0628] [E-1] [E-2] [E-3] [E-4]
[0629]
[0630] [E-5] [E-6] [E-7] [E-8]
[0631]
[0632] [E-9] [E-10] [E-11] [E-12]
[0633]
[0634] [E-13] [E-14] [E-15] [E-16]
[0635]
[0636] [E-17] [E-18] [E-19] [E-20]
[0637]
[0638] [E-21] [E-22] [E-23] [E-24]
[0639]
[0640] [E-25] [E-26] [E-27] [E-28]
[0641]
[0642] [E-29] [E-30] [E-31] [E-32]
[0643]
[0644] [E-33] [E-34] [E-35] [E-36]
[0645]
[0646] [E-37] [E-38] [E-39] [E-40]
[0647]
[0648] [E-41] [E-42] [E-43] [E-44]
[0649]
[0650] [E-45] [E-46] [E-47] [E-48]
[0651]
[0652] [E-49] [E-50] [E-51] [E-52]
[0653]
[0654] [E-53] [E-54] [E-55] [E-56] [E-57]
[0655]
[0656] [E-58] [E-59] [E-60] [E-61] [E-62]
[0657]
[0658] [E-63] [E-64] [E-65] [E-66] [E-67]
[0659]
[0660] [E-68] [E-69]
[0661]
[0662] [E-70] [E-71] [E-72] [E-73]
[0663]
[0664] [E-74] [E-75] [E-76] [E-77]
[0665]
[0666] [E-78] [E-79] [E-80] [E-81]
[0667]
[0668] [E-82] [E-83] [E-84] [E-85]
[0669]
[0670] [E-86] [E-87] [E-88] [E-89]
[0671]
[0672] [E-90] [E-91] [E-92] [E-93]
[0673]
[0674] [E-94] [E-95] [E-96] [E-97]
[0675]
[0676] [F-1] [F-2] [F-3] [F-4] [F-5]
[0677]
[0678] [F-6] [F-7] [F-8] [F-9] [F-10]
[0679]
[0680] [F-11] [F-12] [F-13] [F-14] [F-15]
[0681]
[0682] [F-16] [F-17] [F-18] [F-19] [F-20]
[0683]
[0684] [F-21] [F-22] [F-23] [F-24] [F-25]
[0685]
[0686] [F-26] [F-27] [F-28] [F-29] [F-30]
[0687]
[0688] [F-31] [F-32] [F-33] [F-34] [F-35]
[0689]
[0690] [F-36] [F-37] [F-38] [F-39] [F-40]
[0691]
[0692] [F-41] [F-42] [F-43] [F-44] [F-45]
[0693]
[0694] [F-46] [F-47] [F-48] [F-49] [F-50]
[0695]
[0696] [F-51] [F-52] [F-53] [F-54] [F-55]
[0697]
[0698] [F-56] [F-57] [F-58] [F-59] [F-60]
[0699]
[0700] [F-61] [F-62] [F-63] [F-64] [F-65]
[0701]
[0702] [F-66] [F-67] [F-68] [F-69] [F-70]
[0703]
[0704] [G-1] [G-2] [G-3] [G-4]
[0705]
[0706] [G-5] [G-6] [G-7] [G-8]
[0707]
[0708] [G-9] [G-10] [G-11] [G-12]
[0709]
[0710] [G-13] [G-14] [G-15] [G-16]
[0711]
[0712] [G-17] [G-18] [G-19] [G-20]
[0713]
[0714] [G-21] [G-22] [G-23] [G-24]
[0715]
[0716] [G-25] [G-26] [G-27] [G-28]
[0717]
[0718] [G-29] [G-30] [G-31] [G-32]
[0719]
[0720] [G-33] [G-34] [G-35] [G-36]
[0721]
[0722] [G-37] [G-38] [G-39] [G-40]
[0723]
[0724] [G-41] [G-42] [G-43] [G-44]
[0725]
[0726] [G-45] [G-46] [G-47] [G-48]
[0727]
[0728] Dn refers to the number of deuterium atoms substituted, and n is an integer greater than or equal to 0.
[0729] In addition to the compounds described above, as the second host represented by Chemical Formula 8, compounds described in KR10-2019-0123138A, KR10-2219645B1, KR10-2217250B1, KR10-2207892B1, KR10-2671849B1, KR10-2022-0033348A, KR10-2306966B1, KR10-2023-0132367A, KR10-2021-0080183A, KR10-2021-0116214A, KR10-2019-0034074A, etc. can be applied.
[0730] The first host and the second host 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 host and the hole transport ability of the second host 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.
[0731] 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.
[0732] A dopant is a substance that causes light emission when mixed in a small amount with a host. Typically, a metal complex that emits light by multiple excitation that excites beyond the triplet state can be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may contain one or more types.
[0733] 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.
[0734] [Chemical formula Z]
[0735] L 7 MX 4
[0736] In the above chemical formula Z, M is a metal, and L 7 and X 4 are ligands that are the same or different and form complexes with M.
[0737] 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 7 and X 4 may be, for example, a bidentate ligand.
[0738] The above bidentate ligand may be represented, for example, by the following chemical formula Z-1 or chemical formula Z-2.
[0739] [Chemical Formula Z-1]
[0740]
[0741] [Chemical Formula Z-2]
[0742]
[0743] In the above chemical formulas Z-1 and Z-2,
[0744] Ring A and ring B are each independently a monocyclic ring or a polycyclic fused ring,
[0745] wherein each ring among the monocyclic ring and polycyclic fused ring is a 5-membered or 6-membered carbocyclic or heterocyclic ring,
[0746] R 200 and R 201 Each independently represents one to a maximum number of monovalent substituents,
[0747] R 200 and R 201 If there are two or more, each R 200 and R 201 are identical or different from each other,
[0748] R 202 Inland R 213 are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, -SiR 214 R 215 R 216 , -GeR 214 R 215 R 216 or a combination of these,
[0749] The above R 214 Inland R 216 are each independently a substituted or unsubstituted C1 to C6 alkyl group,
[0750] X 10 , X 11 , X 12 and X 13 are each independently selected from the group consisting of carbon and nitrogen,
[0751] Y 100 is O or S,
[0752] m100 is an integer from 1 to 3,
[0753] m101 is an integer from 1 to 2,
[0754] n100 is 0 or 1,
[0755] * is a connection point.
[0756] When n100 is 0, it is formed with a monovalent substituent,
[0757] If n100 is 1, a fusion ring can be formed.
[0758] L 7 and X 4 Examples of ligands represented by may be selected from, but are not limited to, the chemical formulas listed in Group A below.
[0759] [Group A]
[0760]
[0761] In the above group A,
[0762] 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,
[0763] R 303 Inland R 308 are 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,
[0764] m25 is an integer between 1 and 5,
[0765] m26 is one of the integers 1 to 4,
[0766] m27 is one of the integers 1 to 3,
[0767] m28 is an integer of 1 or 2,
[0768] m29 is an integer between 1 and 6,
[0769] If m25 to m29 are 2 or more, each R 303 Inland R 307 are identical or different from each other.
[0770] In one embodiment, the dopant may be an iridium complex, and may be represented by one of the following chemical formulae 6-1 to 6-5.
[0771] [Chemical Formula 6-1]
[0772]
[0773] In the above chemical formula 6-1,
[0774] R 101 Inland R 116 are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, -SiR 132 R 133 R 134 or -GeR 132 R 133 R 134 And,
[0775] The above R 132 Inland R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,
[0776] R 101 Inland R 116 At least one of them is a functional group represented by the following chemical formula V-1,
[0777] L 100 is 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.
[0778] m21 and m22 are independently any integer from 0 to 3, and m21 + m22 is any integer from 1 to 3,
[0779] [Chemical Formula V-1]
[0780]
[0781] In the above chemical formula V-1,
[0782] 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,
[0783] * indicates a part connected to a carbon atom.
[0784] [Chemical Formula 6-2]
[0785]
[0786] [Chemical Formula 6-3]
[0787]
[0788] [Chemical Formula 6-4]
[0789]
[0790] [Chemical Formula 6-5]
[0791]
[0792] In the above chemical formulas 6-2 to 6-5,
[0793] X 14 is selected from the group consisting of carbon and nitrogen,
[0794] Y 100 is O or S,
[0795] R 101 Inland R 122are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, -SiR 133 R 134 R 135 or -GeR 133 R 134 R 135 And,
[0796] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,
[0797] L 100 is 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.
[0798] m111 is an integer from 1 to 2,
[0799] n1 and n2 are independently any integer from 0 to 3, and n1 + n2 is any integer from 1 to 3.
[0800] In another embodiment, the dopant may be a platinum complex, for example represented by the chemical formula Z-3.
[0801] [Chemical Formula Z-3]
[0802]
[0803] In the above chemical formula Z-3, rings A, B, C, and D each independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;
[0804] R A , R B , R C , and R D each independently represents monosubstitution, disubstitution, trisubstitution, tetrasubstitution, or no substitution;
[0805] nA is an integer of 0 or 1;
[0806] 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;
[0807] 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;
[0808] 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.
[0809] The platinum complex may be represented, for example, by the following chemical formula 9-1 or chemical formula 9-2.
[0810] [Chemical Formula 9-1]
[0811]
[0812] [Chemical Formula 9-2]
[0813]
[0814] In the above chemical formulas 9-1 and 9-2,
[0815] X 100 Silver O, S and NR 132 Selected from among,
[0816] 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 R 134 R 135 And,
[0817] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,
[0818] R 118 Inland R 132 At least one of them is -SiR 133 R 134 R 135 or tert-butyl group,
[0819] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group.
[0820] The composition further comprising a dopant may be, for example, a green luminescent composition.
[0821] The hole transport layer (32) is a layer for facilitating hole transfer from the anode (10) to the light-emitting layer (31) and blocking electrons, and may be, for example, an amine compound, but is not limited thereto.
[0822] The above amine compound may include, for example, at least one aryl group and / or heteroaryl group. The above amine compound may be represented by, for example, the following chemical formula a or chemical formula b, but is not limited thereto.
[0823] [chemical formula a] [chemical formula b]
[0824]
[0825] In the above chemical formula a or b,
[0826] Ar a Inland Ar g are each 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,
[0827] Ar a Inland Ar c At least one of and Ar d Inland 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,
[0828] 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.
[0829] The above organic light-emitting device may further include a hole injection layer (34) in addition to the light-emitting layer.
[0830] The hole injection layer (34) is a layer for facilitating hole injection from the anode (10) to the light-emitting layer (31) and blocking electrons, and may be positioned between the anode (10) and the hole transport layer (32).
[0831] For example, at least one of the hole transport layer (32) and the hole injection layer (34) may include at least one of the compounds listed in Group B below, and is different from the materials of the first hole transport auxiliary layer and the second hole transport auxiliary layer described below.
[0832] [Group B]
[0833]
[0834]
[0835]
[0836]
[0837]
[0838]
[0839]
[0840]
[0841]
[0842]
[0843]
[0844]
[0845]
[0846]
[0847]
[0848]
[0849]
[0850]
[0851]
[0852]
[0853]
[0854]
[0855]
[0856]
[0857]
[0858]
[0859]
[0860]
[0861]
[0862]
[0863]
[0864]
[0865]
[0866] (Dn refers to the number of hydrogen atoms substituted with deuterium atoms, and indicates a structure in which one or more deuterium atoms are substituted.)
[0867] In addition to the compounds described above, 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 hole transport layer (32) and hole injection layer (34).
[0868] The above hole transport auxiliary layer (33) includes a first hole transport auxiliary layer (33a) adjacent to the hole transport layer and a second hole transport auxiliary layer (33b) adjacent to the light-emitting layer.
[0869] The first hole transport auxiliary layer includes a first compound represented by the following chemical formula 1, and the second hole transport auxiliary layer includes a second compound represented by the following chemical formula 2.
[0870] [Chemical Formula 1]
[0871]
[0872] In the above chemical formula 1,
[0873] X 1 is O, S or CR a R b And,
[0874] R a and R b are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
[0875] 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 heterocyclic group,
[0876] R 1 and R 2 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
[0877] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
[0878] m1 is one of the integers 1 to 4,
[0879] m2 is an integer between 1 and 3;
[0880] [Chemical Formula 2]
[0881]
[0882] In the above chemical formula 2,
[0883] X2 and X 3 are each independently O or S,
[0884] L 4 Inland L 6 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
[0885] R 3 Inland R 6 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
[0886] Ar 3 is a substituted or unsubstituted C6 to C20 aryl group,
[0887] m3 and m6 are each independently an integer from 1 to 4,
[0888] m4 and m5 are each independently an integer from 1 to 3.
[0889] If the above m3 is 2 or more, each R 3 may be identical or different.
[0890] If the above m4 is 2 or more, each R 4 may be identical or different.
[0891] If the above m5 is 2 or more, each R 5 may be identical or different.
[0892] If the above m6 is 2 or more, each R 6 may be identical or different.
[0893] An organic light-emitting device according to one embodiment can have improved lifetime characteristics by applying a combination of two hole transport auxiliary layers at the interface between a hole transport layer and a light-emitting layer, thereby adjusting hole injection ability in the first hole transport auxiliary layer to balance charge within the light-emitting layer, and introducing a compound having high stability against excitons into the second hole transport auxiliary layer.
[0894] In particular, by including a structure in which an amine is substituted at the 4th position of dibenzofuran (or dibenzothiophene) as the second compound, the LUMO electron cloud is distributed in dibenzofuran with high electronic stability, thereby increasing the effect as an electron blocking layer, and thus the lifespan characteristics can be further improved.
[0895] If the above m1 is 2 or more, each R 1 may be identical or different.
[0896] If the above m2 is 2 or more, each R 2 may be identical or different.
[0897] For example, the above chemical formula 1 can be expressed by any one of the following chemical formulas 1-1 to 1-4.
[0898] [Chemical Formula 1-1] [Chemical Formula 1-2]
[0899]
[0900] [Chemical Formula 1-3] [Chemical Formula 1-4]
[0901]
[0902] In the above chemical formulas 1-1 to 1-4,
[0903] L 1 Inland L 3 , X 1 , R 1 , R 2 , Ar 1 , Ar 2 , m1 and m2 are defined as in Chemical Formula 1.
[0904] For example, the above chemical formula 1 can be represented by any one of the following chemical formulas 1A to 1C.
[0905] [Chemical Formula 1A] [Chemical Formula 1B]
[0906]
[0907] [Chemical Formula 1C]
[0908]
[0909] In the above chemical formulas 1A to 1C,
[0910] L 1 Inland L 3 , R 1 , R 2 , R a , R b , Ar 1 , Ar 2 , m1 and m2 are defined as in Chemical Formula 1.
[0911] As a specific example, Ar of the above chemical formula 1 1 and Ar 2 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted 1-fluorenyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted 9-fluorenyl group, a substituted or unsubstituted 9,9-spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.
[0912] For example, Ar of the above chemical formula 1 1 and Ar 2may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted 1-fluorenyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted 9-fluorenyl group, a substituted or unsubstituted 9,9-spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.
[0913] For example, R of the above chemical formula 1 1 and R 2 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, or a substituted or unsubstituted C6 to C12 aryl group.
[0914] For example, R in the above chemical formula 1 1 and R 2 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted or a substituted or unsubstituted phenyl group.
[0915] For example, L of the above chemical formula 1 1 Inland L 3 may each independently be a single bond, or a substituted or unsubstituted phenylene group.
[0916] For example, the above L 2 -Ar 1 , and L 3 -Ar 2 Each of the substituents may be independently selected from the substituents listed in Group I below.
[0917] [Group Ⅰ]
[0918]
[0919] In the above group Ⅰ,
[0920] R 8 Inland R 12 are each independently hydrogen, deuterium, cyano, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,
[0921] m8 is an integer between 1 and 5,
[0922] m9 is one of the integers 1 to 4,
[0923] m10 is one of the integers 1 to 7,
[0924] m11 is one of the integers 1 to 3,
[0925] m12 is an integer of 1 or 2,
[0926] * is a connection point.
[0927] If the above m8 is 2 or more, each R 8 may be identical or different.
[0928] If the above m9 is 2 or more, each R 9 may be identical or different.
[0929] If the above m10 is 2 or more, each R 10 may be identical or different.
[0930] If the above m11 is 2 or more, each R 11 may be identical or different.
[0931] If the above m12 is 2, each R 12 may be identical or different.
[0932] In the most specific embodiment, the first compound may be represented by the above chemical formula 1-1.
[0933] For example, the first compound may be, but is not limited to, one selected from the compounds listed in Group 1 below.
[0934] [Group 1]
[0935] [1-1] [1-2] [1-3] [1-4] [1-5]
[0936]
[0937] [1-6] [1-7] [1-8] [1-9] [1-10]
[0938]
[0939] [1-11] [1-12] [1-13] [1-14] [1-15]
[0940]
[0941] [1-16] [1-17] [1-18] [1-19] [1-20]
[0942]
[0943] [1-21] [1-22] [1-23] [1-24] [1-25]
[0944]
[0945] [1-26] [1-27] [1-28] [1-29] [1-30]
[0946]
[0947] [1-31] [1-32] [1-33] [1-34] [1-35]
[0948]
[0949] [1-36] [1-37] [1-38] [1-39] [1-40]
[0950]
[0951] [1-41] [1-42] [1-43] [1-44] [1-45]
[0952]
[0953] [1-46] [1-47] [1-48] [1-49] [1-50]
[0954]
[0955] [1-51] [1-52] [1-53] [1-54] [1-55]
[0956]
[0957] [1-56] [1-57] [1-58] [1-59] [1-60]
[0958]
[0959] [1-61] [1-62] [1-63] [1-64] [1-65]
[0960]
[0961] [1-66] [1-67] [1-68] [1-69] [1-70]
[0962]
[0963] [1-71] [1-72] [1-73] [1-74] [1-75]
[0964]
[0965] [1-76] [1-77] [1-78] [1-79] [1-80]
[0966]
[0967] [1-81] [1-82] [1-83] [1-84] [1-85]
[0968]
[0969] [1-86] [1-87] [1-88] [1-89] [1-90]
[0970]
[0971] [1-91] [1-92] [1-93] [1-94] [1-95]
[0972]
[0973] [1-96] [1-97] [1-98] [1-99] [1-100]
[0974]
[0975] [1-101] [1-102] [1-103] [1-104] [1-105]
[0976]
[0977] [1-106] [1-107] [1-108] [1-109] [1-110]
[0978]
[0979] [1-111] [1-112] [1-113] [1-114] [1-115]
[0980]
[0981] [1-116] [1-117] [1-118] [1-119] [1-120]
[0982]
[0983] [1-121] [1-122] [1-123] [1-124] [1-125]
[0984]
[0985] [1-126] [1-127] [1-128] [1-129] [1-130]
[0986]
[0987] [1-131] [1-132] [1-133] [1-134] [1-135]
[0988]
[0989] [1-136] [1-137] [1-138] [1-139] [1-140]
[0990]
[0991] [1-141] [1-142] [1-143] [1-144] [1-145]
[0992]
[0993] [1-146] [1-147] [1-148] [1-149] [1-150]
[0994]
[0995] [1-151] [1-152] [1-153] [1-154] [1-155]
[0996]
[0997] [1-156] [1-157] [1-158] [1-159] [1-160]
[0998]
[0999] [1-161] [1-162] [1-163] [1-164] [1-165]
[1000]
[1001] [1-166] [1-167] [1-168] [1-169] [1-170]
[1002]
[1003] [1-171] [1-172] [1-173] [1-174] [1-175]
[1004]
[1005] [1-176] [1-177] [1-178] [1-179] [1-180]
[1006]
[1007] [1-181] [1-182] [1-183] [1-184] [1-185]
[1008]
[1009] [1-186] [1-187] [1-188] [1-189] [1-190]
[1010]
[1011] [1-191] [1-192] [1-193] [1-194] [1-195]
[1012]
[1013] [1-196] [1-197] [1-198] [1-199] [1-200]
[1014]
[1015] [1-201] [1-202] [1-203] [1-204] [1-205]
[1016]
[1017] [1-206] [1-207] [1-208] [1-209] [1-210]
[1018]
[1019] [1-211] [1-212] [1-213] [1-214] [1-215]
[1020]
[1021] [1-216] [1-217] [1-218] [1-219] [1-220]
[1022]
[1023] [1-221] [1-222] [1-223] [1-224] [1-225]
[1024]
[1025] [1-226] [1-227] [1-228] [1-229] [1-230]
[1026]
[1027] [1-231] [1-232] [1-233] [1-234] [1-235]
[1028]
[1029] [1-236] [1-237] [1-238] [1-239] [1-240]
[1030]
[1031] [1-241] [1-242] [1-243] [1-244] [1-245]
[1032]
[1033] [1-246] [1-247] [1-248] [1-249] [1-250]
[1034]
[1035] [1-251] [1-252] [1-253] [1-254] [1-255]
[1036]
[1037] [1-256] [1-257] [1-258] [1-259] [1-260]
[1038]
[1039] [1-261] [1-262] [1-263] [1-264] [1-265]
[1040]
[1041] [1-266] [1-267] [1-268] [1-269] [1-270]
[1042]
[1043] [1-271] [1-272] [1-273] [1-274] [1-275]
[1044]
[1045] [1-276] [1-277] [1-278] [1-279] [1-280]
[1046]
[1047] [1-281] [1-282] [1-283] [1-284] [1-285]
[1048]
[1049] [1-286] [1-287] [1-288] [1-289] [1-290]
[1050]
[1051] [1-291] [1-292] [1-293] [1-294] [1-295]
[1052]
[1053] [1-296] [1-297] [1-298] [1-299] [1-300]
[1054]
[1055] [1-301] [1-302] [1-303] [1-304] [1-305]
[1056]
[1057] [1-306] [1-307] [1-308] [1-309] [1-310]
[1058]
[1059] [1-311] [1-312] [1-313] [1-314] [1-315]
[1060]
[1061] [1-316] [1-317] [1-318] [1-319] [1-320]
[1062]
[1063] [1-321] [1-322] [1-323] [1-324] [1-325]
[1064]
[1065] [1-326] [1-327] [1-328] [1-329] [1-330]
[1066]
[1067] [1-331] [1-332] [1-333] [1-334] [1-335]
[1068]
[1069] [1-336] [1-337] [1-338] [1-339] [1-340]
[1070]
[1071] [1-341] [1-342] [1-343] [1-344] [1-345]
[1072]
[1073] [1-346] [1-347] [1-348] [1-349] [1-350]
[1074]
[1075] [1-351] [1-352] [1-353] [1-354] [1-355]
[1076]
[1077] [1-356] [1-357] [1-358] [1-359] [1-360]
[1078]
[1079] [1-361] [1-362] [1-363] [1-364] [1-365]
[1080]
[1081] [1-366] [1-367] [1-368] [1-369] [1-370]
[1082]
[1083] [1-371] [1-372] [1-373] [1-374] [1-375]
[1084]
[1085] [1-376] [1-377] [1-378] [1-379] [1-380]
[1086]
[1087] [1-381] [1-382] [1-383] [1-384] [1-385]
[1088]
[1089] [1-386] [1-387] [1-388] [1-389] [1-390]
[1090]
[1091] [1-391] [1-392] [1-393] [1-394] [1-395]
[1092]
[1093] [1-396] [1-397] [1-398] [1-399] [1-400]
[1094]
[1095] [1-401] [1-402] [1-403] [1-404] [1-405]
[1096]
[1097] [1-406] [1-407] [1-408] [1-409] [1-410]
[1098]
[1099] [1-411] [1-412] [1-413] [1-414] [1-415]
[1100]
[1101] [1-416] [1-417] [1-418] [1-419] [1-420]
[1102]
[1103] [1-421] [1-422] [1-423] [1-424] [1-425]
[1104]
[1105] [1-426] [1-427] [1-428] [1-429] [1-430]
[1106]
[1107] [1-431] [1-432] [1-433] [1-434] [1-435]
[1108]
[1109] [1-436] [1-437] [1-438] [1-439] [1-440]
[1110]
[1111] [1-441] [1-442] [1-443] [1-444] [1-445]
[1112]
[1113] [1-446] [1-447] [1-448] [1-449] [1-450]
[1114]
[1115] [1-451] [1-452] [1-453] [1-454] [1-455]
[1116]
[1117] [1-456] [1-457] [1-458] [1-459] [1-460]
[1118]
[1119] [1-461] [1-462] [1-463] [1-464] [1-465]
[1120]
[1121] [1-466] [1-467] [1-468] [1-469] [1-470]
[1122]
[1123] [1-471] [1-472] [1-473]
[1124]
[1125] For example, the above chemical formula 2 can be represented by any one of the following chemical formulas 2-1 to 2-4.
[1126] [Chemical Formula 2-1][Chemical Formula 2-2]
[1127]
[1128] [Chemical Formula 2-3][Chemical Formula 2-4]
[1129]
[1130] In the above chemical formulas 2-1 to 2-4,
[1131] X 2 , X 3 , L 4 Inland L 6 , R 3 Inland R 6 , Ar 3 , and m3 to m6 are as defined in the above chemical formula 2.
[1132] As a specific example, the chemical formula 2 can be represented by the chemical formula 2-1 or chemical formula 2-4.
[1133] For example, the above chemical formula 2 can be represented by the above chemical formula 2-1.
[1134] For example, Ar of the above chemical formula 2 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 phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted 9,9-spirobifluorenyl group.
[1135] As a specific example, Ar of the above chemical formula 2 3 It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted 9,9-spirobifluorenyl group.
[1136] For example, the above L 4 Inland L 6may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
[1137] As a specific example, the above L 4 Inland L 6 Each may independently be a single bond or a substituted or unsubstituted phenylene group.
[1138] For example, the above R 3 Inland R 6 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, or a substituted or unsubstituted C6 to C12 aryl group.
[1139] For example, the second compound may be, but is not limited to, one selected from the compounds listed in Group 2 below.
[1140] [Group 2]
[1141] [2-1] [2-2] [2-3] [2-4] [2-5]
[1142]
[1143] [2-6] [2-7] [2-8] [2-9] [2-10]
[1144]
[1145] [2-11] [2-12] [2-13] [2-14] [2-15]
[1146]
[1147] [2-16] [2-17] [2-18] [2-19] [2-20]
[1148]
[1149] [2-21] [2-22] [2-23] [2-24] [2-25]
[1150]
[1151] [2-26] [2-27] [2-28] [2-29] [2-30]
[1152]
[1153] [2-31] [2-32] [2-33] [2-34] [2-35]
[1154]
[1155] [2-36] [2-37] [2-38] [2-39] [2-40]
[1156]
[1157] [2-41] [2-42] [2-43] [2-44] [2-45]
[1158]
[1159] [2-46] [2-47] [2-48] [2-49] [2-50]
[1160]
[1161] [2-51] [2-52] [2-53] [2-54] [2-55]
[1162]
[1163] [2-56] [2-57] [2-58] [2-59] [2-60]
[1164]
[1165] [2-61] [2-62] [2-63] [2-64] [2-65]
[1166]
[1167] [2-66] [2-67] [2-68] [2-69] [2-70]
[1168]
[1169] [2-71] [2-72] [2-73] [2-74] [2-75]
[1170]
[1171] [2-76] [2-77] [2-78] [2-79] [2-80]
[1172]
[1173] [2-81] [2-82] [2-83] [2-84] [2-85]
[1174]
[1175] [2-86] [2-87] [2-88] [2-89] [2-90]
[1176]
[1177] [2-91] [2-92] [2-93] [2-94] [2-95]
[1178]
[1179] [2-96] [2-97] [2-98] [2-99] [2-100]
[1180]
[1181] [2-101] [2-102] [2-103] [2-104] [2-105]
[1182]
[1183] [2-106] [2-107] [2-108] [2-109] [2-110]
[1184]
[1185] [2-111] [2-112] [2-113] [2-114] [2-115]
[1186]
[1187] [2-116] [2-117] [2-118] [2-119] [2-120]
[1188]
[1189] [2-121] [2-122] [2-123] [2-124] [2-125]
[1190]
[1191] [2-126] [2-127] [2-128] [2-129] [2-130]
[1192]
[1193] [2-131] [2-132] [2-133] [2-134] [2-135]
[1194]
[1195] [2-136] [2-137] [2-138] [2-139] [2-140]
[1196]
[1197] [2-141] [2-142] [2-143] [2-144] [2-145]
[1198]
[1199] [2-146] [2-147] [2-148] [2-149] [2-150]
[1200]
[1201] [2-151] [2-152] [2-153] [2-154] [2-155]
[1202]
[1203] [2-156] [2-157] [2-158] [2-159] [2-160]
[1204]
[1205] [2-161] [2-162] [2-163] [2-164] [2-165]
[1206]
[1207] [2-166] [2-167] [2-168] [2-169] [2-170]
[1208]
[1209] [2-171] [2-172] [2-173] [2-174] [2-175]
[1210]
[1211] [2-176] [2-177] [2-178] [2-179] [2-180]
[1212]
[1213] [2-181] [2-182] [2-183] [2-184] [2-185]
[1214]
[1215] [2-186] [2-187] [2-188] [2-189] [2-190]
[1216]
[1217] [2-191] [2-192] [2-193] [2-194] [2-195]
[1218]
[1219] [2-196] [2-197] [2-198] [2-199] [2-200]
[1220]
[1221] [2-201] [2-202] [2-203] [2-204] [2-205]
[1222]
[1223] [2-206] [2-207] [2-208] [2-209] [2-210]
[1224]
[1225] [2-211] [2-212] [2-213] [2-214] [2-215]
[1226]
[1227] [2-216] [2-217] [2-218] [2-219] [2-220]
[1228]
[1229] [2-221] [2-222] [2-223] [2-224] [2-225]
[1230]
[1231] [2-226] [2-227] [2-228] [2-229] [2-230]
[1232]
[1233] [2-231] [2-232] [2-233] [2-234] [2-235]
[1234]
[1235] [2-236] [2-237] [2-238] [2-239] [2-240]
[1236]
[1237] [2-241] [2-242] [2-243] [2-244] [2-245]
[1238]
[1239] [2-246] [2-247] [2-248] [2-249] [2-250]
[1240]
[1241] [2-251] [2-252] [2-253] [2-254] [2-255]
[1242]
[1243] [2-256] [2-257] [2-258] [2-259] [2-260]
[1244]
[1245] [2-261] [2-262] [2-263] [2-264] [2-265]
[1246]
[1247] [2-266] [2-267] [2-268] [2-269] [2-270]
[1248]
[1249] [2-271] [2-272] [2-273] [2-274] [2-275]
[1250]
[1251] [2-276] [2-277] [2-278] [2-279] [2-280]
[1252]
[1253] [2-281] [2-282] [2-283] [2-284] [2-285]
[1254]
[1255] [2-286] [2-287] [2-288] [2-289] [2-290]
[1256]
[1257] [2-291] [2-292] [2-293] [2-294] [2-295]
[1258]
[1259] [2-296] [2-297] [2-298] [2-299] [2-300]
[1260]
[1261] [2-301] [2-302] [2-303] [2-304] [2-305]
[1262]
[1263] [2-306] [2-307] [2-308] [2-309] [2-310]
[1264]
[1265] [2-311] [2-312] [2-313] [2-314] [2-315]
[1266]
[1267] [2-316] [2-317] [2-318] [2-319] [2-320]
[1268]
[1269] [2-321] [2-322] [2-323] [2-324] [2-325]
[1270]
[1271] [2-326] [2-327] [2-328] [2-329] [2-330]
[1272]
[1273] [2-331] [2-332] [2-333] [2-334] [2-335]
[1274]
[1275] [2-336] [2-337] [2-338] [2-339] [2-340]
[1276]
[1277] [2-341] [2-342] [2-343] [2-344] [2-345]
[1278]
[1279] [2-346] [2-347] [2-348] [2-349] [2-350]
[1280]
[1281] [2-351] [2-352] [2-353] [2-354] [2-355]
[1282]
[1283] [2-356] [2-357] [2-358] [2-359] [2-360]
[1284]
[1285] [2-361] [2-362] [2-363] [2-364] [2-365]
[1286]
[1287] [2-366] [2-367] [2-368] [2-369] [2-370]
[1288]
[1289] [2-371] [2-372] [2-373] [2-374] [2-375]
[1290]
[1291] [2-376] [2-377] [2-378] [2-379] [2-380]
[1292]
[1293] [2-381] [2-382] [2-383] [2-384] [2-385]
[1294]
[1295] [2-386] [2-387] [2-388] [2-389] [2-390]
[1296]
[1297] [2-391] [2-392] [2-393] [2-394] [2-395]
[1298]
[1299] [2-396] [2-397] [2-398] [2-399] [2-400]
[1300]
[1301] [2-401] [2-402] [2-403] [2-404] [2-405]
[1302]
[1303] [2-406] [2-407] [2-408] [2-409] [2-410]
[1304]
[1305] [2-411] [2-412] [2-413] [2-414] [2-415]
[1306]
[1307] [2-416] [2-417] [2-418] [2-419] [2-420]
[1308]
[1309] [2-421] [2-422] [2-423] [2-424] [2-425]
[1310]
[1311] [2-426] [2-427] [2-428] [2-429] [2-430]
[1312]
[1313] [2-431] [2-432] [2-433] [2-434] [2-435]
[1314]
[1315] [2-436] [2-437] [2-438] [2-439] [2-440]
[1316]
[1317] [2-441] [2-442] [2-443] [2-444] [2-445]
[1318]
[1319] [2-446] [2-447] [2-448] [2-449] [2-450]
[1320]
[1321] [2-451] [2-452] [2-453] [2-454] [2-455]
[1322]
[1323] [2-456] [2-457] [2-458] [2-459] [2-460]
[1324]
[1325] [2-461] [2-462] [2-463] [2-464] [2-465]
[1326]
[1327] [2-466] [2-467] [2-468] [2-469] [2-470]
[1328]
[1329] [2-471] [2-472] [2-473] [2-474] [2-475]
[1330]
[1331] [2-476] [2-477] [2-478] [2-479] [2-480]
[1332]
[1333] [2-481] [2-482] [2-483] [2-484] [2-485]
[1334]
[1335] [2-486] [2-487] [2-488] [2-489] [2-490]
[1336]
[1337] [2-491] [2-492] [2-493] [2-494] [2-495]
[1338]
[1339] [2-496] [2-497] [2-498] [2-499] [2-500]
[1340]
[1341] [2-501] [2-502] [2-503] [2-504] [2-505]
[1342]
[1343] [2-506] [2-507] [2-508] [2-509] [2-510]
[1344]
[1345] [2-511] [2-512] [2-513] [2-514] [2-515]
[1346]
[1347] [2-516] [2-517] [2-518] [2-519] [2-520]
[1348]
[1349] [2-521] [2-522] [2-523] [2-524] [2-525]
[1350]
[1351] [2-526] [2-527] [2-528] [2-529] [2-530]
[1352]
[1353] [2-531] [2-532] [2-533] [2-534] [2-535]
[1354]
[1355] [2-536] [2-537] [2-538] [2-539] [2-540]
[1356]
[1357] [2-541] [2-542] [2-543] [2-544] [2-545]
[1358]
[1359] [2-546] [2-547] [2-548] [2-549] [2-550]
[1360]
[1361] [2-551] [2-552] [2-553] [2-554] [2-555]
[1362]
[1363] [2-556] [2-557] [2-558] [2-559] [2-560]
[1364]
[1365] [2-561] [2-562] [2-563] [2-564] [2-565]
[1366]
[1367] [2-566] [2-567] [2-568] [2-569] [2-570]
[1368]
[1369] [2-571] [2-572] [2-573] [2-574] [2-575]
[1370]
[1371] [2-576] [2-577] [2-578] [2-579] [2-580]
[1372]
[1373] [2-581] [2-582] [2-583] [2-584] [2-585]
[1374]
[1375] [2-586] [2-587] [2-588] [2-589] [2-590]
[1376]
[1377] [2-591] [2-592] [2-593] [2-594] [2-595]
[1378]
[1379] [2-596] [2-597] [2-598] [2-599] [2-600]
[1380]
[1381] [2-601] [2-602] [2-603] [2-604] [2-605]
[1382]
[1383] [2-606] [2-607] [2-608] [2-609] [2-610]
[1384]
[1385] [2-611] [2-612] [2-613] [2-614] [2-615]
[1386]
[1387] [2-616] [2-617] [2-618] [2-619] [2-620]
[1388]
[1389] [2-621] [2-622] [2-623] [2-624] [2-625]
[1390]
[1391] [2-626] [2-627] [2-628] [2-629] [2-630]
[1392]
[1393] [2-631] [2-632] [2-633] [2-634] [2-635]
[1394]
[1395] [2-636] [2-637] [2-638] [2-639] [2-640]
[1396]
[1397] [2-641] [2-642] [2-643] [2-644] [2-645]
[1398]
[1399] [2-646] [2-647] [2-648] [2-649] [2-650]
[1400]
[1401] [2-651] [2-652] [2-653] [2-654] [2-655]
[1402]
[1403] [2-656] [2-657] [2-658] [2-659] [2-660]
[1404]
[1405] [2-661] [2-662] [2-663] [2-664] [2-665]
[1406]
[1407] [2-666] [2-667] [2-668] [2-669] [2-670]
[1408]
[1409] [2-671] [2-672] [2-673] [2-674] [2-675]
[1410]
[1411] [2-676] [2-677] [2-678] [2-679] [2-680]
[1412]
[1413] [2-681] [2-682] [2-683] [2-684] [2-685]
[1414]
[1415] [2-686] [2-687] [2-688] [2-689] [2-690]
[1416]
[1417] [2-691] [2-692] [2-693] [2-694] [2-695]
[1418]
[1419] [2-696] [2-697] [2-698] [2-699] [2-700]
[1420]
[1421] [2-701] [2-702] [2-703] [2-704] [2-705]
[1422]
[1423] [2-706] [2-707] [2-708] [2-709] [2-710]
[1424]
[1425] [2-711] [2-712] [2-713] [2-714] [2-715]
[1426]
[1427] [2-716] [2-717] [2-718] [2-719] [2-720]
[1428]
[1429] [2-721] [2-722] [2-723] [2-724] [2-725]
[1430]
[1431] [2-726] [2-727] [2-728] [2-729] [2-730]
[1432]
[1433] [2-731] [2-732] [2-733] [2-734] [2-735]
[1434]
[1435] [2-736] [2-737] [2-738] [2-739] [2-740]
[1436]
[1437] [2-741] [2-742] [2-743] [2-744] [2-745]
[1438]
[1439] [2-746] [2-747] [2-748] [2-749] [2-750]
[1440]
[1441] [2-751] [2-752] [2-753] [2-754] [2-755]
[1442]
[1443] [2-756] [2-757] [2-758] [2-759] [2-760]
[1444]
[1445] [2-761] [2-762] [2-763] [2-764] [2-765]
[1446]
[1447] [2-766] [2-767] [2-768] [2-769] [2-770]
[1448]
[1449] [2-771] [2-772] [2-773] [2-774] [2-775]
[1450]
[1451] [2-776] [2-777] [2-778] [2-779] [2-780]
[1452]
[1453] [2-781] [2-782] [2-783] [2-784] [2-785]
[1454]
[1455] [2-786] [2-787] [2-788] [2-789] [2-790]
[1456]
[1457] [2-791] [2-792] [2-793] [2-794] [2-795]
[1458]
[1459] [2-796] [2-797] [2-798] [2-799] [2-800]
[1460]
[1461] [2-801] [2-802] [2-803] [2-804] [2-805]
[1462]
[1463] [2-806] [2-807] [2-808] [2-809] [2-810]
[1464]
[1465] [2-811] [2-812] [2-813] [2-814] [2-815]
[1466]
[1467] [2-816] [2-817] [2-818] [2-819] [2-820]
[1468]
[1469] [2-821] [2-822] [2-823] [2-824] [2-825]
[1470]
[1471] [2-826] [2-827] [2-828] [2-829] [2-830]
[1472]
[1473] [2-831] [2-832] [2-833] [2-834] [2-835]
[1474]
[1475] [2-836] [2-837] [2-838] [2-839] [2-840]
[1476]
[1477] [2-841] [2-842] [2-843] [2-844] [2-845]
[1478]
[1479] [2-846] [2-847] [2-848] [2-849] [2-850]
[1480]
[1481] [2-851] [2-852] [2-853] [2-854] [2-855]
[1482]
[1483] [2-856] [2-857] [2-858] [2-859] [2-860]
[1484]
[1485] [2-861] [2-862] [2-863] [2-864] [2-865]
[1486]
[1487] [2-866] [2-867] [2-868] [2-869] [2-870]
[1488]
[1489] [2-871] [2-872] [2-873] [2-874] [2-875]
[1490]
[1491] [2-876] [2-877] [2-878] [2-879] [2-880]
[1492]
[1493] [2-881] [2-882] [2-883] [2-884] [2-885]
[1494]
[1495] [2-886] [2-887] [2-888] [2-889] [2-890]
[1496]
[1497] [2-891] [2-892] [2-893] [2-894] [2-895]
[1498]
[1499] [2-896] [2-897] [2-898] [2-899] [2-900]
[1500]
[1501] [2-901] [2-902] [2-903] [2-904] [2-905]
[1502]
[1503] [2-906] [2-907] [2-908] [2-909] [2-910]
[1504]
[1505] [2-911] [2-912] [2-913] [2-914] [2-915]
[1506]
[1507] [2-916] [2-917] [2-918] [2-919] [2-920]
[1508]
[1509] [2-921] [2-922] [2-923] [2-924] [2-925]
[1510]
[1511] [2-926] [2-927] [2-928] [2-929] [2-930]
[1512]
[1513] [2-931] [2-932] [2-933] [2-934] [2-935]
[1514]
[1515] [2-936] [2-937] [2-938] [2-939] [2-940]
[1516]
[1517] [2-941] [2-942] [2-943] [2-944] [2-945]
[1518]
[1519] [2-946] [2-947] [2-948] [2-949] [2-950]
[1520]
[1521] [2-951] [2-952] [2-953] [2-954] [2-955]
[1522]
[1523] [2-956] [2-957] [2-958] [2-959] [2-960]
[1524]
[1525] [2-961] [2-962] [2-963] [2-964] [2-965]
[1526]
[1527] [2-966] [2-967] [2-968] [2-969] [2-970]
[1528]
[1529] [2-971] [2-972] [2-973] [2-974] [2-975]
[1530]
[1531] [2-976] [2-977] [2-978] [2-979] [2-980]
[1532]
[1533] [2-981] [2-982] [2-983] [2-984] [2-985]
[1534]
[1535] [2-986] [2-987] [2-988] [2-989] [2-990]
[1536]
[1537] [2-991] [2-992] [2-993] [2-994] [2-995]
[1538]
[1539] [2-996]
[1540]
[1541] (Dn refers to the number of deuterium atoms substituted, and n is an integer greater than or equal to 1).
[1542] The above organic layer (30) may include an electron transport region.
[1543] The above electron transport region can further increase electron injection and / or electron mobility between the cathode (20) and the light-emitting layer (31) and block holes.
[1544] Specifically, the electron transport region may include an electron transport layer (35) between the cathode (20) and the light-emitting layer (31), and an electron transport auxiliary layer (not shown) between the light-emitting layer (31) and the electron transport layer (35), and at least one of the compounds listed in Group C below may be included in at least one layer of the electron transport layer (35) and the electron transport auxiliary layer.
[1545] [Group C]
[1546]
[1547]
[1548]
[1549]
[1550]
[1551]
[1552]
[1553]
[1554]
[1555]
[1556]
[1557]
[1558]
[1559]
[1560]
[1561]
[1562]
[1563] An example of an embodiment may be an organic light-emitting device including an organic layer as a light-emitting layer (31), a hole transport layer (32), a first hole transport layer (33a), and a second hole transport layer (33b).
[1564] Another embodiment may be an organic light-emitting device that additionally includes a hole injection layer as an organic layer.
[1565] Another embodiment may be an organic light-emitting device that additionally includes an electron transport region as an organic layer.
[1566] Meanwhile, the organic light-emitting device may further include an electron injection layer (not shown) in addition to the light-emitting layer as the aforementioned organic layer.
[1567] An organic light-emitting device can be manufactured by forming an anode or cathode on a substrate, forming an organic layer using a dry film deposition method such as evaporation, sputtering, plasma plating, or ion plating, and then forming a cathode or anode thereon.
[1568] The above-described organic light-emitting device can be applied to an organic light-emitting display device.
[1569] 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.
[1570] 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.
[1571] (Preparation of the first compound)
[1572] Synthesis Example 1: Synthesis of Compound 1-139
[1573] [Reaction Formula 1]
[1574]
[1575] 10 g (35.88 mmol) of the intermediate 1-chloro-8-phenyldibenzo[b,d]furan, 12.97 g (35.88 mmol) of the intermediate N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine, 5.52 g (57.40 mmol) of sodium t-butoxide, and 1.03 g (2.51 mmol) of 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl(Sphos) were dissolved in 239 ml of xylene, and 30.99 g (1.08 mmol) of Pd2(dba) was added, followed by reflux stirring for 12 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was extracted with toluene and distilled water, and the organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with normal hexane / dichloromethane (3:1 volume ratio) to obtain 16.2 g (75% yield) of compound 1-139 as a white solid.
[1576]
[1577] Synthesis Example 2: Synthesis of Compound 1-399
[1578] [Reaction Formula 2]
[1579]
[1580] Compound 1-399 was synthesized in the same manner as Synthetic Example 1, except that 10.0 g of the intermediate 1,3-di-tert-butyl-5-chloro-9,9-dimethyl-9H-fluorene and 11.78 g of the intermediate bis(9,9-dimethyl-9H-fluoren-2-yl)amine were used in a 1:1 equivalent ratio (14.5 g, yield 70%).
[1581]
[1582] Synthesis Example 3: Synthesis of Compound 1-400
[1583] [Reaction Formula 3]
[1584]
[1585] Compound 1-400 was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of the intermediate 1,3-di-tert-butyl-5-chloro-9,9-dimethyl-9H-fluorene and 11.78 g of the intermediate N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in a 1:1 equivalent ratio (15 g, yield 77%).
[1586]
[1587] Synthesis Example 4: Synthesis of Compound 1-403
[1588] [Reaction Formula 4]
[1589]
[1590] Compound 1-403 was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of the intermediate 1,3-di-tert-butyl-5-chloro-9,9-dimethyl-9H-fluorene and 14.01 g of the intermediate N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-3-phenyl-9H-fluoren-2-amine were used in a 1:1 equivalent ratio (17.3 g, yield 75%).
[1591]
[1592] Synthesis Example 5: Synthesis of Compound 1-425
[1593] [Reaction Formula 5]
[1594]
[1595] Compound 1-425 was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of the intermediate 1,3-di-tert-butyl-5-chloro-9,9-dimethyl-9H-fluorene and 15.07 g of the intermediate 6,8-di-tert-butyl-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in a 1:1 equivalent ratio (17.8 g, yield 74%).
[1596]
[1597] (Preparation of the second compound)
[1598] Synthesis Example 6: Synthesis of Compound 2-344
[1599] [Reaction Formula 6]
[1600]
[1601] Compound 2-344 was synthesized in the same manner as Synthesis Example 1, except that 10.0 g of the intermediate 1-chlorodibenzo[b,d]furan and 20.37 g of the intermediate N-(3-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1'-biphenyl]-4-amine were used in a 1:1 equivalent ratio (20 g, yield 70%).
[1602]
[1603] Synthesis Example 7: Synthesis of Compound 2-531
[1604] [Reaction Formula 7]
[1605]
[1606] Compound 2-531 was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of the intermediate 1-chlorodibenzo[b,d]furan and 22.27 g of the intermediate N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine were used in a 1:1 equivalent ratio (24 g, yield 79%).
[1607]
[1608] Synthesis Example 8: Synthesis of Compound 2-571
[1609] [Reaction Formula 8]
[1610]
[1611] Compound 2-571 was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of the intermediate 1-chloro-8-phenyldibenzo[b,d]furan and 16.20 g of the intermediate N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine were used in a 1:1 equivalent ratio (20.5 g, yield 82%).
[1612]
[1613] Synthesis Example 9: Synthesis of Compound 2-934
[1614] [Reaction Formula 9]
[1615]
[1616] Compound 2-934 was synthesized in the same manner as Synthetic Example 1, except that 10.0 g of the intermediate 1-chloro-8-phenyldibenzo[b,d]furan and 29.19 g of the intermediate N-(4-(dibenzo[b,d]thiophen-4-yl)phenyl)-9,9'-spirobi[fluoren]-4-amine were used in a 1:1 equivalent ratio (31 g, yield 83%).
[1617]
[1618] (Preparation of comparative compounds)
[1619] Comparative Example 1: Synthesis of Compound R-1
[1620]
[1621] Compound R-1 was synthesized with reference to the synthetic method disclosed in registered patent KR 10-2428237.
[1622]
[1623] Comparative Example 2: Synthesis of Compound R-2
[1624]
[1625] Compound R-2 was synthesized with reference to the synthetic method disclosed in registered patent KR 10-2374470.
[1626]
[1627] Comparative Example 3: Synthesis of Compound R-3
[1628]
[1629] Compound R-3 was synthesized with reference to the synthetic method disclosed in the published publication WO2013 / 120577.
[1630]
[1631] Example 1
[1632] A glass substrate coated with a thin film of ITO / Ag / ITO was ultrasonically washed in distilled water. After washing with distilled water, it was ultrasonically washed with a solvent such as acetone or isopropyl alcohol, 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 / Ag / ITO (reflective electrode) prepared in this way as an anode, Compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum-deposited on the ITO / Ag / ITO substrate to form a hole injection layer with a thickness of 100 Å, and Compound A was deposited on the hole injection layer with a thickness of 1350 Å to form a hole transport layer. The first compound 1-399 obtained in Synthesis Example 2 was deposited on the hole transport layer to a thickness of 285 Å to form a first hole transport auxiliary layer, and the second compound 2-531 obtained in Synthesis Example 7 was deposited on the first hole transport auxiliary layer to a thickness of 50 Å to form a second hole transport auxiliary layer. On the second hole transport auxiliary layer, a host H1 (40%) and a host H2 (60%) were used at 85 wt% as a host, and PtGD was doped at 15 wt% as a dopant to form a light-emitting layer with a thickness of 380 Å by vacuum deposition. Subsequently, the compound C was deposited on the light-emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and the compound D and Liq were simultaneously vacuum-deposited at a 1:1 ratio to form an electron transport layer with a thickness of 310 Å. An organic light-emitting device was manufactured by sequentially vacuum-depositing Yb and AgMg on top of the electron transport layer to form a cathode.
[1633] It was fabricated with the structure of ITO / Ag / ITO / compound A (3% NDP-9 doping, 100Å) / compound A (1350Å) / first hole transport auxiliary layer (285Å) / second hole transport auxiliary layer (50Å) / emission layer [Host (Host H1: Host H2 = 40 wt%: 60 wt%): PtGD = 85 wt%: 15 wt%] (380Å) / compound C (50Å) / compound D: Liq (310Å) / Yb / AgMg.
[1634] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine
[1635] Compound C: 4-{4-[3-(9,9-dimethyl-9H-fluoren-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine
[1636] Compound D: 2-(4-{1-[4-(diphenyl-1,3,5-triazin-2-yl)phenyl]naphthalen-2-yl}phenyl)-4,6-diphenyl-1,3,5-triazine
[1637] Host H1: Host H2: PtGD:
[1638]
[1639]
[1640] Examples 2 to 5 and Comparative Examples 1 to 5
[1641] An organic light-emitting device was manufactured in the same manner as Example 1, except that the composition was changed to that described in Table 1 below.
[1642]
[1643] Evaluation: Life Characteristics
[1644] The life characteristics of the organic light-emitting devices according to Examples 1 to 5 and Comparative Examples 1 to 5 were measured in terms of luminance (cd / m 2) to 45000cd / m 2 The time required for the current efficiency (cd / A) to decrease to 97% was measured and evaluated.
[1645] The life measurement values of Examples 1 to 5 and Comparative Examples 1 to 5 were calculated as relative values based on Comparative Example 1 and are listed in Table 1 below.
[1646] No. 1st compound 2nd compound Lifespan (%) Example 11-3992-531132 Example 21-3992-571130 Example 31-3992-934126 Example 41-4002-531120 Example 51-1392-531124 Comparative Example 11-399R-1100 Comparative Example 21-399R-294 Comparative Example 31-399R-396 Comparative Example 4-2-53181 Comparative Example 51-399-48
[1647] Referring to Table 1, it can be confirmed that the lifespan characteristics of the organic light-emitting devices according to Examples 1 to 5 are significantly improved compared to the organic light-emitting devices according to Comparative Examples 1 to 5.
Claims
1. Positive and negative poles facing each other, A light-emitting layer positioned between the anode and the cathode, A hole transport layer positioned between the anode and the light-emitting layer, A hole transport auxiliary layer located between the above hole transport layer and the above light emitting layer Including, The above hole transport auxiliary layer includes a first hole transport auxiliary layer adjacent to the hole transport layer and a second hole transport auxiliary layer adjacent to the light-emitting layer, The first hole transport auxiliary layer includes a first compound represented by the following chemical formula 1, An organic optoelectronic device wherein the second hole transport auxiliary layer comprises a second compound represented by the following chemical formula 2: [Chemical Formula 1] In the above chemical formula 1, X 1 is O, S or CR a R b And, R a and R b are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, 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 heterocyclic group, R 1 and R 2 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m1 is one of the integers 1 to 4, m2 is an integer between 1 and 3; [Chemical Formula 2] In the above chemical formula 2, X 2 and X 3 are each independently O or S, L 4 Inland L 6 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group, R 3 Inland R 6 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, Ar 3 is a substituted or unsubstituted C6 to C20 aryl group, m3 and m6 are each independently an integer from 1 to 4, m4 and m5 are each independently one of the integers 1 to 3.
2. In paragraph 1, The above chemical formula 1 is an organic optoelectronic device expressed by any one of the following chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In the above chemical formulas 1-1 to 1-4, L 1 Inland L 3 , X 1 , R 1 , R 2 , Ar 1 , Ar 2 , m1 and m2 are as defined in paragraph 1.
3. In paragraph 1, The above chemical formula 1 is a compound for an organic optoelectronic device represented by any one of the following chemical formulas 1A to 1C: [Chemical Formula 1A] [Chemical Formula 1B] [Chemical Formula 1C] In the above chemical formulas 1A to 1C, L 1 Inland L 3 , R 1 , R 2 , R a , R b , Ar 1 , Ar 2 , m1 and m2 are as defined in paragraph 1.
4. In paragraph 1, The above Ar 1 and Ar 2 An organic optoelectronic device, wherein each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted 1-fluorenyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted 9-fluorenyl group, a substituted or unsubstituted 9,9-spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.
5. In paragraph 1, Above L 2 -Ar 1 and L 3 -Ar 2 An organic optoelectronic device wherein each of the substituents listed in Group Ⅰ is independently selected from among the following: [Group Ⅰ] In the above group Ⅰ, R 8 Inland R 12 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or a substituted or unsubstituted C6 to C12 aryl group, m8 is an integer between 1 and 5, m9 is one of the integers 1 to 4, m10 is one of the integers 1 to 7, m11 is one of the integers 1 to 3, m12 is an integer of 1 or 2, * is a connection point.
6. In paragraph 1, The first compound is an organic optoelectronic device selected from the compounds listed in Group 1 below: [Group 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] [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] [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] [1-260] [1-261] [1-262] [1-263] [1-264] [1-265] [1-266] [1-267] [1-268] [1-269] [1-270] [1-271] [1-272] [1-273] [1-274] [1-275] [1-276] [1-277] [1-278] [1-279] [1-280] [1-281] [1-282] [1-283] [1-284] [1-285] [1-286] [1-287] [1-288] [1-289] [1-290] [1-291] [1-292] [1-293] [1-294] [1-295] [1-296] [1-297] [1-298] [1-299] [1-300] [1-301] [1-302] [1-303] [1-304] [1-305] [1-306] [1-307] [1-308] [1-309] [1-310] [1-311] [1-312] [1-313] [1-314] [1-315] [1-316] [1-317] [1-318] [1-319] [1-320] [1-321] [1-322] [1-323] [1-324] [1-325] [1-326] [1-327] [1-328] [1-329] [1-330] [1-331] [1-332] [1-333] [1-334] [1-335] [1-336] [1-337] [1-338] [1-339] [1-340] [1-341] [1-342] [1-343] [1-344] [1-345] [1-346] [1-347] [1-348] [1-349] [1-350] [1-351] [1-352] [1-353] [1-354] [1-355] [1-356] [1-357] [1-358] [1-359] [1-360] [1-361] [1-362] [1-363] [1-364] [1-365] [1-366] [1-367] [1-368] [1-369] [1-370] [1-371] [1-372] [1-373] [1-374] [1-375] [1-376] [1-377] [1-378] [1-379] [1-380] [1-381] [1-382] [1-383] [1-384] [1-385] [1-386] [1-387] [1-388] [1-389] [1-390] [1-391] [1-392] [1-393] [1-394] [1-395] [1-396] [1-397] [1-398] [1-399] [1-400] [1-401] [1-402] [1-403] [1-404] [1-405] [1-406] [1-407] [1-408] [1-409] [1-410] [1-411] [1-412] [1-413] [1-414] [1-415] [1-416] [1-417] [1-418] [1-419] [1-420] [1-421] [1-422] [1-423] [1-424] [1-425] [1-426] [1-427] [1-428] [1-429] [1-430] [1-431] [1-432] [1-433] [1-434] [1-435] [1-436] [1-437] [1-438] [1-439] [1-440] [1-441] [1-442] [1-443] [1-444] [1-445] [1-446] [1-447] [1-448] [1-449] [1-450] [1-451] [1-452] [1-453] [1-454] [1-455] [1-456] [1-457] [1-458] [1-459] [1-460] [1-461] [1-462] [1-463] [1-464] [1-465] [1-466] [1-467] [1-468] [1-469] [1-470] [1-471] [1-472] [1-473] .
7. In paragraph 1, The above chemical formula 2 is an organic optoelectronic device represented by any one of the following chemical formulas 2-1 to 2-4: [Chemical Formula 2-1][Chemical Formula 2-2] [Chemical Formula 2-3][Chemical Formula 2-4] In the above chemical formulas 2-1 to 2-4, X 2 , X 3 , L 4 Inland L 6 , R 3 Inland R 6 , Ar 3 , and m3 to m6 are as defined in paragraph 1.
8. In paragraph 7, An organic optoelectronic device, wherein the chemical formula 2 is represented by the chemical formula 2-1 or chemical formula 2-4.
9. In paragraph 1, The above Ar 3 An organic optoelectronic device, wherein the organic optoelectronic device is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted 9,9-spirobifluorenyl group.
10. 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] [2-101] [2-102] [2-103] [2-104] [2-105] [2-106] [2-107] [2-108] [2-109] [2-110] [2-111] [2-112] [2-113] [2-114] [2-115] [2-116] [2-117] [2-118] [2-119] [2-120] [2-121] [2-122] [2-123] [2-124] [2-125] [2-126] [2-127] [2-128] [2-129] [2-130] [2-131] [2-132] [2-133] [2-134] [2-135] [2-136] [2-137] [2-138] [2-139] [2-140] [2-141] [2-142] [2-143] [2-144] [2-145] [2-146] [2-147] [2-148] [2-149] [2-150] [2-151] [2-152] [2-153] [2-154] [2-155] [2-156] [2-157] [2-158] [2-159] [2-160] [2-161] [2-162] [2-163] [2-164] [2-165] [2-166] [2-167] [2-168] [2-169] [2-170] [2-171] [2-172] [2-173] [2-174] [2-175] [2-176] [2-177] [2-178] [2-179] [2-180] [2-181] [2-182] [2-183] [2-184] [2-185] [2-186] [2-187] [2-188] [2-189] [2-190] [2-191] [2-192] [2-193] [2-194] [2-195] [2-196] [2-197] [2-198] [2-199] [2-200] [2-201] [2-202] [2-203] [2-204] [2-205] [2-206] [2-207] [2-208] [2-209] [2-210] [2-211] [2-212] [2-213] [2-214] [2-215] [2-216] [2-217] [2-218] [2-219] [2-220] [2-221] [2-222] [2-223] [2-224] [2-225] [2-226] [2-227] [2-228] [2-229] [2-230] [2-231] [2-232] [2-233] [2-234] [2-235] [2-236] [2-237] [2-238] [2-239] [2-240] [2-241] [2-242] [2-243] [2-244] [2-245] [2-246] [2-247] [2-248] [2-249] [2-250] [2-251] [2-252] [2-253] [2-254] [2-255] [2-256] [2-257] [2-258] [2-259] [2-260] [2-261] [2-262] [2-263] [2-264] [2-265] [2-266] [2-267] [2-268] [2-269] [2-270] [2-271] [2-272] [2-273] [2-274] [2-275] [2-276] [2-277] [2-278] [2-279] [2-280] [2-281] [2-282] [2-283] [2-284] [2-285] [2-286] [2-287] [2-288] [2-289] [2-290] [2-291] [2-292] [2-293] [2-294] [2-295] [2-296] [2-297] [2-298] [2-299] [2-300] [2-301] [2-302] [2-303] [2-304] [2-305] [2-306] [2-307] [2-308] [2-309] [2-310] [2-311] [2-312] [2-313] [2-314] [2-315] [2-316] [2-317] [2-318] [2-319] [2-320] [2-321] [2-322] [2-323] [2-324] [2-325] [2-326] [2-327] [2-328] [2-329] [2-330] [2-331] [2-332] [2-333] [2-334] [2-335] [2-336] [2-337] [2-338] [2-339] [2-340] [2-341] [2-342] [2-343] [2-344] [2-345] [2-346] [2-347] [2-348] [2-349] [2-350] [2-351] [2-352] [2-353] [2-354] [2-355] [2-356] [2-357] [2-358] [2-359] [2-360] [2-361] [2-362] [2-363] [2-364] [2-365] [2-366] [2-367] [2-368] [2-369] [2-370] [2-371] [2-372] [2-373] [2-374] [2-375] [2-376] [2-377] [2-378] [2-379] [2-380] [2-381] [2-382] [2-383] [2-384] [2-385] [2-386] [2-387] [2-388] [2-389] [2-390] [2-391] [2-392] [2-393] [2-394] [2-395] [2-396] [2-397] [2-398] [2-399] [2-400] [2-401] [2-402] [2-403] [2-404] [2-405] [2-406] [2-407] [2-408] [2-409] [2-410] [2-411] [2-412] [2-413] [2-414] [2-415] [2-416] [2-417] [2-418] [2-419] [2-420] [2-421] [2-422] [2-423] [2-424] [2-425] [2-426] [2-427] [2-428] [2-429] [2-430] [2-431] [2-432] [2-433] [2-434] [2-435] [2-436] [2-437] [2-438] [2-439] [2-440] [2-441] [2-442] [2-443] [2-444] [2-445] [2-446] [2-447] [2-448] [2-449] [2-450] [2-451] [2-452] [2-453] [2-454] [2-455] [2-456] [2-457] [2-458] [2-459] [2-460] [2-461] [2-462] [2-463] [2-464] [2-465] [2-466] [2-467] [2-468] [2-469] [2-470] [2-471] [2-472] [2-473] [2-474] [2-475] [2-476] [2-477] [2-478] [2-479] [2-480] [2-481] [2-482] [2-483] [2-484] [2-485] [2-486] [2-487] [2-488] [2-489] [2-490] [2-491] [2-492] [2-493] [2-494] [2-495] [2-496] [2-497] [2-498] [2-499] [2-500] [2-501] [2-502] [2-503] [2-504] [2-505] [2-506] [2-507] [2-508] [2-509] [2-510] [2-511] [2-512] [2-513] [2-514] [2-515] [2-516] [2-517] [2-518] [2-519] [2-520] [2-521] [2-522] [2-523] [2-524] [2-525] [2-526] [2-527] [2-528] [2-529] [2-530] [2-531] [2-532] [2-533] [2-534] [2-535] [2-536] [2-537] [2-538] [2-539] [2-540] [2-541] [2-542] [2-543] [2-544] [2-545] [2-546] [2-547] [2-548] [2-549] [2-550] [2-551] [2-552] [2-553] [2-554] [2-555] [2-556] [2-557] [2-558] [2-559] [2-560] [2-561] [2-562] [2-563] [2-564] [2-565] [2-566] [2-567] [2-568] [2-569] [2-570] [2-571] [2-572] [2-573] [2-574] [2-575] [2-576] [2-577] [2-578] [2-579] [2-580] [2-581] [2-582] [2-583] [2-584] [2-585] [2-586] [2-587] [2-588] [2-589] [2-590] [2-591] [2-592] [2-593] [2-594] [2-595] [2-596] [2-597] [2-598] [2-599] [2-600] [2-601] [2-602] [2-603] [2-604] [2-605] [2-606] [2-607] [2-608] [2-609] [2-610] [2-611] [2-612] [2-613] [2-614] [2-615] [2-616] [2-617] [2-618] [2-619] [2-620] [2-621] [2-622] [2-623] [2-624] [2-625] [2-626] [2-627] [2-628] [2-629] [2-630] [2-631] [2-632] [2-633] [2-634] [2-635] [2-636] [2-637] [2-638] [2-639] [2-640] [2-641] [2-642] [2-643] [2-644] [2-645] [2-646] [2-647] [2-648] [2-649] [2-650] [2-651] [2-652] [2-653] [2-654] [2-655] [2-656] [2-657] [2-658] [2-659] [2-660] [2-661] [2-662] [2-663] [2-664] [2-665] [2-666] [2-667] [2-668] [2-669] [2-670] [2-671] [2-672] [2-673] [2-674] [2-675] [2-676] [2-677] [2-678] [2-679] [2-680] [2-681] [2-682] [2-683] [2-684] [2-685] [2-686] [2-687] [2-688] [2-689] [2-690] [2-691] [2-692] [2-693] [2-694] [2-695] [2-696] [2-697] [2-698] [2-699] [2-700] [2-701] [2-702] [2-703] [2-704] [2-705] [2-706] [2-707] [2-708] [2-709] [2-710] [2-711] [2-712] [2-713] [2-714] [2-715] [2-716] [2-717] [2-718] [2-719] [2-720] [2-721] [2-722] [2-723] [2-724] [2-725] [2-726] [2-727] [2-728] [2-729] [2-730] [2-731] [2-732] [2-733] [2-734] [2-735] [2-736] [2-737] [2-738] [2-739] [2-740] [2-741] [2-742] [2-743] [2-744] [2-745] [2-746] [2-747] [2-748] [2-749] [2-750] [2-751] [2-752] [2-753] [2-754] [2-755] [2-756] [2-757] [2-758] [2-759] [2-760] [2-761] [2-762] [2-763] [2-764] [2-765] [2-766] [2-767] [2-768] [2-769] [2-770] [2-771] [2-772] [2-773] [2-774] [2-775] [2-776] [2-777] [2-778] [2-779] [2-780] [2-781] [2-782] [2-783] [2-784] [2-785] [2-786] [2-787] [2-788] [2-789] [2-790] [2-791] [2-792] [2-793] [2-794] [2-795] [2-796] [2-797] [2-798] [2-799] [2-800] [2-801] [2-802] [2-803] [2-804] [2-805] [2-806] [2-807] [2-808] [2-809] [2-810] [2-811] [2-812] [2-813] [2-814] [2-815] [2-816] [2-817] [2-818] [2-819] [2-820] [2-821] [2-822] [2-823] [2-824] [2-825] [2-826] [2-827] [2-828] [2-829] [2-830] [2-831] [2-832] [2-833] [2-834] [2-835] [2-836] [2-837] [2-838] [2-839] [2-840] [2-841] [2-842] [2-843] [2-844] [2-845] [2-846] [2-847] [2-848] [2-849] [2-850] [2-851] [2-852] [2-853] [2-854] [2-855] [2-856] [2-857] [2-858] [2-859] [2-860] [2-861] [2-862] [2-863] [2-864] [2-865] [2-866] [2-867] [2-868] [2-869] [2-870] [2-871] [2-872] [2-873] [2-874] [2-875] [2-876] [2-877] [2-878] [2-879] [2-880] [2-881] [2-882] [2-883] [2-884] [2-885] [2-886] [2-887] [2-888] [2-889] [2-890] [2-891] [2-892] [2-893] [2-894] [2-895] [2-896] [2-897] [2-898] [2-899] [2-900] [2-901] [2-902] [2-903] [2-904] [2-905] [2-906] [2-907] [2-908] [2-909] [2-910] [2-911] [2-912] [2-913] [2-914] [2-915] [2-916] [2-917] [2-918] [2-919] [2-920] [2-921] [2-922] [2-923] [2-924] [2-925] [2-926] [2-927] [2-928] [2-929] [2-930] [2-931] [2-932] [2-933] [2-934] [2-935] [2-936] [2-937] [2-938] [2-939] [2-940] [2-941] [2-942] [2-943] [2-944] [2-945] [2-946] [2-947] [2-948] [2-949] [2-950] [2-951] [2-952] [2-953] [2-954] [2-955] [2-956] [2-957] [2-958] [2-959] [2-960] [2-961] [2-962] [2-963] [2-964] [2-965] [2-966] [2-967] [2-968] [2-969] [2-970] [2-971] [2-972] [2-973] [2-974] [2-975] [2-976] [2-977] [2-978] [2-979] [2-980] [2-981] [2-982] [2-983] [2-984] [2-985] [2-986] [2-987] [2-988] [2-989] [2-990] [2-991] [2-992] [2-993] [2-994] [2-995] [2-996] Dn refers to the number of deuterium atoms substituted, and n is an integer greater than or equal to 1.
11. A display device comprising an organic optoelectronic device according to any one of claims 1 to 10.
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