Organic optoelectronic diode and display device

Abstract

The present invention relates to an organic optoelectronic diode comprising an anode and a cathode opposite each other, a light-emitting layer located between the anode and the cathode, a hole transport layer located between the anode and the light-emitting layer, and a hole transport auxiliary layer located between the light-emitting layer and the hole transport layer, wherein the hole transport auxiliary layer comprises 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 light-emitting layer comprises a first compound represented by a combination of Chemical Formula 1 and Chemical Formula 2, the first hole transport auxiliary layer comprises a second compound represented by Chemical Formula 3, the second hole transport auxiliary layer comprises a third compound represented by Chemical Formula 3, the second compound and the third compound are different from each other, the refractive index of the hole transport layer is higher than the refractive index of the first hole transport auxiliary layer, and the refractive index of the first hole transport auxiliary layer is 2.0 or less. Detailed descriptions of Chemical Formulae 1-3 are as defined in the specification.

Description

Technical Field

[0001] An organic optoelectronic device and a display device are disclosed. Background Technology

[0002] Organic optoelectronic devices (organic optoelectronic diodes) are devices that can convert electrical energy into light energy and vice versa.

[0003] Based on their working principles, organic optoelectronic devices can be broadly classified into two categories. One category consists of optoelectronic devices that generate electrical energy by separating excitons formed from light energy into electrons and holes and transferring the electrons and holes to different electrodes. The other category consists of light-emitting devices that generate light energy from electrical energy by supplying voltage or current to the electrodes.

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

[0005] Organic light-emitting diodes (OLEDs) have received considerable attention in recent years due to the increasing demand for flat panel display devices. OLEDs are devices that convert electrical energy into light, and their performance is greatly affected by the organic materials between the electrodes. Summary of the Invention

[0006] Technical issues

[0007] One implementation provides an organic optoelectronic device capable of achieving high efficiency characteristics.

[0008] Another embodiment provides a display device including an organic optoelectronic device.

[0009] Technical solution

[0010] According to one embodiment, an organic optoelectronic device is provided, including an anode and a cathode facing each other, a light-emitting layer between the anode and the cathode, a hole transport layer between the anode and the light-emitting layer, and a hole transport auxiliary layer between the light-emitting layer and the hole transport layer. 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. The light-emitting layer contains a first compound represented by a combination of chemical formulas 1 and 2. The first hole transport auxiliary layer contains a second compound represented by a chemical formula 3. The second hole transport auxiliary layer contains a third compound represented by a chemical formula 3. The second and third compounds are different from each other. The refractive index of the hole transport layer is higher than the refractive index of the first hole transport auxiliary layer, and the refractive index of the first hole transport auxiliary layer is less than or equal to 2.0.

[0011] [Chemical Formula 1] [Chemical Formula 2]

[0012] In chemical formula 1 and chemical formula 2, Z 1 To Z 3 Each is independently N or CL a -R a , Z 1 To Z 3 At least two of them are N. X 1 For NL b -R b O or S L a L b and L 1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof. R a R b R 1 and R 2 Each of these elements is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, or combinations thereof. Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof. R a Ar 1 and Ar 2 Each exists independently, or R a Ar 1 and Ar 2 Adjacent groups are linked to form substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic rings. m1 and m2 are each an independent integer from 1 to 4, and When m1 and m2 are each independently 2 or greater, R 1 and R 2 Each is the same as or different from the other; [Chemical Formula 3]

[0013] In chemical formula 3, X 2 For O, S or CR c R d , L4 To L 6 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene. Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. R c R d and R 6 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. R c and R d They exist independently or are connected to each other to form substituted or unsubstituted spirodifluorene. A is substituted or unsubstituted benzene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, or substituted or unsubstituted spirodifluorene. m6 is an integer from 1 to 3, and When m6 is 2 or greater, R 6 They are the same as or different from each other.

[0014] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0015] Beneficial effects

[0016] It can realize organic optoelectronic devices with high efficiency. Attached Figure Description

[0017] Figure 1 This is a cross-sectional view of an organic light-emitting diode according to one embodiment.

[0018] <Explanation of Figure Markers>

[0019] 10: Anode 20: Cathode

[0020] 30: Organic layer; 31: Light-emitting layer

[0021] 32: Hole transport layer 33: Hole transport auxiliary layer

[0022] 33a: First hole transport auxiliary layer; 33b: Second hole transport auxiliary layer

[0023] 34: Electron transport layer Detailed Implementation

[0024] Embodiments of the present invention are described in detail below. However, these embodiments are exemplary, and this disclosure is not limited thereto.

[0025] In this specification, unless otherwise defined, “substituted” means that at least one hydrogen atom of a substituent or compound is replaced by a deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amino, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or combinations thereof.

[0026] In one embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C20 alkyl, C3 to C20 cycloalkyl, C6 to C30 aryl, or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C5 alkyl, C3 to C10 cycloalkyl, C6 to C18 aryl, or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, tert-butyl, cyclopropyl, phenyl, biphenyl, terphenyl or naphthyl.

[0027] In this specification, "unsubstituted" means that the hydrogen atom is not replaced by another substituent and retains the hydrogen atom.

[0028] In this specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)".

[0029] In this specification, unless otherwise defined, “heterogeneous” means a functional group containing one to three heteroatoms selected from N, O, S, P and Si and the remaining carbon.

[0030] In this specification, "aryl" means a group comprising at least one aromatic hydrocarbon moiety, wherein all elements of the aromatic hydrocarbon moiety have conjugated p orbitals, such as phenyl, naphthyl, etc., and two or more aromatic hydrocarbon moiety may be linked by σ bonds and may be, for example, biphenyl, terphenyl, tetraphenyl, etc., and two or more aromatic hydrocarbon moiety may be directly or indirectly fused to provide a non-aromatic fused ring, such as fluorene.

[0031] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent carbon atom pairs) functional groups.

[0032] As used herein, "heterocyclic group" is a superordinate concept of a heteroaryl group and may include at least one heteroatom selected from N, O, S, P, and Si in place of carbon (C) in cyclic compounds such as aryl, cycloalkyl, their fused rings, or combinations thereof. When the heterocyclic group is fused, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0033] For example, "heteroaryl" can refer to an aryl group comprising at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly connected by σ bonds, or when a heteroaryl group comprises two or more rings, the two or more rings can be fused. When a heteroaryl group is a fused ring, each ring may comprise one to three heteroatoms.

[0034] More specifically, the substituted or unsubstituted C6 to C30 aryl groups can be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraxyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrene, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted meta-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted trefyl, substituted or unsubstituted triphenylene group, substituted or unsubstituted peryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indene, or combinations thereof, but are not limited thereto.

[0035] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group can be a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted pyrrole 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 benzothiopheneyl group, etc. The following are substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, or combinations thereof, but not limited thereto.

[0036] In this specification, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductivity characteristics based on the highest occupied molecular orbital (HOMO) energy level, holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0037] Furthermore, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductivity of the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into and transported in the light-emitting layer.

[0038] The following describes an organic optoelectronic device according to one embodiment.

[0039] Organic optoelectronic devices can be suitable devices that convert electrical energy into light energy and vice versa, such as organic photoelectric devices, organic light-emitting diodes, organic solar cells, or organic photosensitive drums.

[0040] This document describes an organic light-emitting diode as an example of an organic optoelectronic device, but the invention is not limited thereto, and it can be applied in the same way to other organic optoelectronic devices.

[0041] In the accompanying drawings, the thicknesses of layers, films, panels, regions, etc., are enlarged for clarity. Throughout the specification, the same reference numerals denote the same elements. It should be understood that when an element such as a layer, film, region, or substrate is referred to as being "on" another element, it may be directly on the other element, or there may be intermediate elements present. Conversely, when an element is referred to as being "directly on" another element, there are no intermediate elements present.

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

[0043] In the following text, reference will be made to Figure 1 Describe an organic light-emitting diode according to one embodiment.

[0044] refer to Figure 1 An organic light-emitting diode according to one embodiment includes an anode 10 and a cathode 20 facing each other, and an organic layer 30 between the anode 10 and the cathode 20.

[0045] The anode 10 may be made of a conductor with a high work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 10 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or alloys thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; a combination of metals and oxides such as ZnO and Al or SnO2 and Sb; a conductive polymer such as, but not limited to, poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline.

[0046] The cathode 20 may be made of a conductor with a small work function to aid electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 20 may include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; multilayer materials such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but are not limited thereto.

[0047] The organic layer 30 includes a light-emitting layer 31, a hole transport layer 32, and a hole transport auxiliary layer 33 between the hole transport layer 32 and the light-emitting layer 31.

[0048] An organic optoelectronic device according to one embodiment includes: The anode and cathode facing each other, The light-emitting layer between the anode and cathode Hole transport layer between the anode and the light-emitting layer, and A hole transport auxiliary layer between the luminescent layer and the hole transport layer. 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. The luminescent layer contains a first compound represented by a combination of chemical formulas 1 and 2. The first hole transport auxiliary layer contains a second compound represented by chemical formula 3. The second hole transport auxiliary layer contains a third compound represented by chemical formula 3. The second and third compounds are different from each other. The refractive index of the hole transport layer is higher than that of the first hole transport auxiliary layer, and The refractive index of the first hole transport auxiliary layer can be less than or equal to 2.0.

[0049] As an example, the refractive index of the first hole transport auxiliary layer can be less than or equal to 1.9.

[0050] As a specific example, the refractive index of the first hole transport auxiliary layer can be less than or equal to 1.8.

[0051] For example, the refractive index of the first hole transport auxiliary layer can be greater than or equal to 1.5 and less than or equal to 1.8.

[0052] As an example, the refractive index of the first hole transport auxiliary layer can be less than or equal to the refractive index of the second hole transport auxiliary layer.

[0053] As a specific example, the refractive index of the first hole transport auxiliary layer can be lower than that of the second hole transport auxiliary layer.

[0054] As an example, the T1 energy of the second hole transport auxiliary layer can be greater than or equal to 2.5 eV.

[0055] The light-emitting layer 31 contains at least two types of substrates and dopants, and the substrates may be, for example, phosphorescent substrates.

[0056] The phosphorescent host should facilitate the injection and transport of holes and electrons within the emissive layer, ultimately enabling holes and electrons to meet effectively and form excitons, and should be able to efficiently transfer the energy of the formed excitons to the dopant. Examples of phosphorescent hosts include organic compounds, such as carbazole, indolocarbazole, dibenzofuran, dibenzothiophene, indolodibenzofuran, indolodibenzothiophene, fluorene, indobenzocarbazole, triphenylene, pyrimidine, triazine, or combinations thereof.

[0057] As an example, the luminescent layer may contain a first compound represented by a combination of chemical formula 1 and chemical formula 2.

[0058] [Chemical Formula 1] [Chemical Formula 2]

[0059] In chemical formula 1 and chemical formula 2, Z 1 To Z 3 Each is independently N or CL a -R a , Z 1 To Z 3 At least two of them are N. X 1 For NL b -R b O or S L a L b and L 1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof. R a R b R 1 and R 2 Each of these elements is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, or combinations thereof. Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof. R a Ar 1 and Ar 2 Each exists independently, or R a Ar 1 and Ar 2 Adjacent groups are linked to form substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic rings, and m1 and m2 are each an independent integer from 1 to 4.

[0060] Since the first compound effectively extends the LUMO band by including a nitrogen-containing hexagonal moiety, it can be included together with the fourth compound described below to improve the balance between holes and electrons, thereby significantly improving the lifetime characteristics of the device in which it is applied.

[0061] As a more specific example, the first compound can be represented by any one of the chemical formulas 1-I to 1-VI.

[0062] [Chemical Formula 1-I] [Chemical Formula 1-II]

[0063] [Chemical Formula 1-III] [Chemical Formula 1-IV]

[0064] [Chemical Formula 1-V] [Chemical Formula 1-VI]

[0065] In chemical formulas 1-I to 1-VI Z 1 To Z 3 Each is independently N or CL a -R a , Z 1 To Z 3 At least two of them are N. X 1 For NL b -R b O or S L a L b and L 1 To L 3 Each of these can be independently a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted dibenzothiopheneylene. Ar 1 and Ar 2Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted trefyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophene, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, or substituted or unsubstituted triazine. R a R b R 1 and R 2 Each of the following is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiopheneyl. m1 and m2 are each an independent integer from 1 to 4. m3 is an integer of 1 or 3, and When m1 to m3 are each independently 2 or greater, R 1 To R 3 They are the same as or different from each other.

[0066] In one specific embodiment, the first compound may be represented by chemical formula 1-I.

[0067] For example, in chemical formula 1-I, X 1 It can be NL b -R b O or S, L b and L 1 To L 3 Each can be a single bond or a substituted or unsubstituted C6 to C12 aryl group, R b And Ar 1 and Ar 2 Each can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl, and R 1 and R 2 Each can be independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl.

[0068] The first compound may be, for example, one selected from the compounds listed in Group 1, but is not limited thereto.

[0069] [Group 1]

[0070] [B-1] [B-2] [B-3] [B-4] [B-5]

[0071] [B-6] [B-7] [B-8] [B-9] [B-10]

[0072] [B-11] [B-12] [B-13] [B-14] [B-15]

[0073] [B-16] [B-17] [B-18] [B-19] [B-20]

[0074] [B-21] [B-22] [B-23] [B-24] [B-25]

[0075] [B-26] [B-27] [B-28] [B-29] [B-30]

[0076] [B-31] [B-32] [B-33] [B-34] [B-35]

[0077] [B-36] [B-37] [B-38] [B-39] [B-40]

[0078] [B-41] [B-42] [B-43] [B-44] [B-45]

[0079] [B-46] [B-47] [B-48] [B-49] [B-50]

[0080] [B-51] [B-52] [B-53] [B-54] [B-55]

[0081] [B-56] [B-57] [B-58] [B-59] [B-60]

[0082] [C-1] [C-2] [C-3] [C-4] [C-5]

[0083] [C-6] [C-7] [C-8] [C-9] [C-10]

[0084] [C-11] [C-12] [C-13] [C-14] [C-15]

[0085] (Dn refers to the number of deuterium atoms that are substituted, where n is an integer of 0 or greater, and the maximum number of n corresponds to the number of hydrogen sites that can be substituted).

[0086] Additionally, the luminescent layer may also contain a fourth compound represented by chemical formula 4, a combination of chemical formula 5 and chemical formula 6, chemical formula 7, or chemical formula 8.

[0087] [Chemical Formula 4]

[0088] In chemical formula 4, R 13 To R 17 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. L 7 and L 8 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene. m13, m16, and m17 are each an independent integer from 1 to 4. m14 and m15 are each an independent integer from 1 to 3. When m13 to m17 are 2 or greater, R 13 To R 17 Each is the same as or different from the others, and n is an integer from 0 to 2; [Chemical Formula 5] [Chemical Formula 6]

[0089] In chemical formulas 5 and 6, a1 in chemical formula 5 up to a4 The two adjacent ones in the middle are each related to the chemical formula 6. Connecting carbon (C). a1 in chemical formula 5 up to a4 The other two not connected to chemical formula 6 are CL. c -R e , L c L 9 and L 10 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene. R e R 18 and R 19 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. Ar 7 and Ar 8 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. m18 and m19 are each an independent integer from 1 to 4, and When m18 and m19 are 2 or greater, R 18 and R 19 Each is the same as or different from the other; [Chemical Formula 7]

[0090] In chemical formula 7, L 11 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene. R 20 To R 23 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. Ar 9 The substituted or unsubstituted C6 to C20 aryl group or the substituted or unsubstituted C2 to C30 heterocyclic group, m20, m22, and m23 are each an independent integer from 1 to 4. m21 is an integer from 1 to 3, and When m20 to m23 are 2 or greater, R 20 To R 23 Each is the same as or different from the other; [Chemical Formula 8]

[0091] In chemical formula 8, X 4 For O, S, NR f CR g R h or SiR i R j , R f R g R h R i R j and R 24 Each of these groups is independently hydrogen, deuterium, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group. m24 is an integer from 1 to 4, and B is any one of the rings listed in group I. [Group I]

[0092] In group I, For the connection point, X 5 For O, S, NR k CR l R m or SiR n R o , R k R l R m R n R o and R 25 To R 29 Each is independently hydrogen, deuterium, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and R k and R 24 To R 29 At least one of them is a group represented by chemical formula a. [Chemical formula a]

[0093] In chemical formula a, L 12 To L 14 Each is an independent single bond or a substituted or unsubstituted C6 to C30 arylene. Ar 10 and Ar 11 Each is independently a substituted or unsubstituted amino group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and This is the connection point.

[0094] The fourth compound, together with the first compound mentioned above, is used in the luminescent layer to improve charge mobility and stability, thereby improving luminous efficiency and lifetime characteristics.

[0095] In chemical formula 4, when m13 is 2 or greater, R 13 Each can be the same as or different from the other. In chemical formula 4, when m14 is 2 or greater, R 14 Each can be the same as or different from the other. In chemical formula 4, when m15 is 2 or greater, R 15 Each can be the same as or different from the other. In chemical formula 4, when m16 is 2 or greater, R 16 Each can be the same as or different from the other. In chemical formula 4, when m17 is 2 or greater, R 17 Each can be the same as or different from the other. In chemical formulas 5 and 6, when m18 is 2 or greater, R 18 Each can be the same as or different from the other. In chemical formulas 5 and 6, when m19 is 2 or greater, R 19 Each can be the same as or different from the other. In chemical formula 7, when m20 is 2 or greater, R 20 Each can be the same as or different from the other. In chemical formula 7, when m21 is 2 or greater, R 21 Each can be the same as or different from the other. In chemical formula 7, when m22 is 2 or greater, R 22 Each can be the same as or different from the other, and In chemical formula 7, when m23 is 2 or greater, R 23 Each can be the same as or different from the other.

[0096] In chemical formula 8, when m24 is 2 or greater, R 24 Each can be the same as or different from the other.

[0097] As an example, in chemical formula 4, Ar 5 and Ar 6 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted fluorenyl. In chemical formula 4, L 7 and L 8 Each can be independently a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene. In chemical formula 4, R 13 To R 17 Each can be independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and n can be 0 or 1.

[0098] As an example, in Formula 4, "substituted" means that at least one hydrogen atom is replaced by a deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0099] For example, in chemical formula 4, Ar 5 and Ar 6 Each can be independently substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, or substituted or unsubstituted fluorenyl.

[0100] In another specific embodiment of the present invention, chemical formula 4 may be represented by one of chemical formulas 4-1 to 4-15.

[0101] [Chemical Formula 4-1] [Chemical Formula 4-2] [Chemical Formula 4-3]

[0102] [Chemical Formula 4-4] [Chemical Formula 4-5] [Chemical Formula 4-6]

[0103] [Chemical Formula 4-7] [Chemical Formula 4-8] [Chemical Formula 4-9]

[0104] [Chemical Formula 4-10] [Chemical Formula 4-11] [Chemical Formula 4-12]

[0105] [Chemical Formula 4-13] [Chemical Formula 4-14] [Chemical Formula 4-15]

[0106] In chemical formulas 4-1 to 4-15, R 13 To R 17 Each can be independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and L 7 -Ar 5 and L 8 -Ar 6 Each can be one of the substituents listed in Group II, independently.

[0107] [Group II]

[0108] In Group II, R 30 To R 35 Each is independently hydrogen, deuterium, cyano, C1 to C10 alkyl, or C6 to C12 aryl. m30 is an integer from 1 to 5. m31 is an integer from 1 to 4. m32 is an integer from 1 to 3. m33 is an integer of 1 or 2. m34 is an integer from 1 to 7, and This is the connection point.

[0109] In group II, when m30 is 2 or greater, R 30 Each can be the same as or different from the other.

[0110] In group II, when m31 is 2 or greater, R 31 Each can be the same as or different from the other.

[0111] In group II, when m32 is 2 or greater, R 32 Each can be the same as or different from the other.

[0112] In group II, when m33 is 2, R 33 Each can be the same as or different from the other.

[0113] In group II, when m34 is 2 or greater, R 34 Each can be the same as or different from the other.

[0114] The combination of chemical formula 5 and chemical formula 6 can be represented, for example, by any one of chemical formula 5A, chemical formula 5B, chemical formula 5C, chemical formula 5D and chemical formula 5E.

[0115] [Chemical Formula 5A] [Chemical Formula 5B] [Chemical Formula 5C]

[0116] [Chemical Formula 5D] [Chemical Formula 5E]

[0117] In chemical formulas 5A to 5E, L 9 L 10 Ar 7 Ar 8 R 18 R 19 m18 and m19 are the same as described above. L c1 To L c4 Compared with the L described above 9 and L 10 The definitions are the same, and R e1 To R e4 R as described above 18 and R 19 The definitions are the same.

[0118] For example, in chemical formulas 5 and 6, Ar 7 and Ar 8 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted fluorenyl.

[0119] R e1 To R e4 R 18 and R 19 Each of them can be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0120] In another specific embodiment of the invention, in chemical formulas 5 and 6, L 9 -Ar 7 and L 10 -Ar 8Each can be independently selected from the substituents listed in Group II.

[0121] In one implementation, R e1 To R e4 R 18 and R 19 Each of them can be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0122] For example, R e1 To R e4 R 18 and R 19 Each can be independently hydrogen, deuterium, cyano, or substituted or unsubstituted phenyl groups, and

[0123] In one specific implementation, R e1 To R e4 R 18 and R 19 Each can be hydrogen, deuterium, or substituted or unsubstituted phenyl groups, independently.

[0124] L c1 To L c4 It can be a single key, L 9 and L 10 Each can be a single bond or a substituted or unsubstituted C6 to C12 aryl group, R 18 R 19 R e3 and R e4 Each can be hydrogen, deuterium, or a substituted or unsubstituted phenyl group, and Ar 7 and Ar 8 Each of them can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0125] Chemical formula 7 can be represented, for example, by any one of chemical formulas 7-1 to 7-4.

[0126] [Chemical Formula 7-1] [Chemical Formula 7-2]

[0127] [Chemical Formula 7-3] [Chemical Formula 7-4]

[0128] In chemical formulas 7-1 to 7-4, L 11 Ar9 R 20 To R 23 And m20 to m23 are the same as described above.

[0129] For example, in chemical formula 7, Ar 9 It can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted triphenylene, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted fluorene.

[0130] R 20 To R 23 Each of them can be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0131] In another specific embodiment of the invention, in chemical formula 7, L 11 -Ar 9 Each can be independently selected from the substituents listed in Group II.

[0132] For example, R 20 To R 23 Each can be independently hydrogen, deuterium, cyano, or substituted or unsubstituted phenyl groups.

[0133] Chemical formula 8 can be represented, for example, by any one of chemical formulas 8-I to 8-IX.

[0134] [Chemical Formula 8-I] [Chemical Formula 8-II]

[0135] [Chemical Formula 8-III] [Chemical Formula 8-IV]

[0136] [Chemical Formula 8-V] [Chemical Formula 8-VI]

[0137] [Chemical Formula 8-VII] [Chemical Formula 8-VIII]

[0138] [Chemical Formula 8-IX]

[0139] In chemical formulas 8-I to 8-IX X 4 X 5 and R 24 To R 29 Same as described above.

[0140] Furthermore, depending on the direction of amino group substitution, chemical formula 8 can be represented by any one of chemical formulas 8-IA to 8-IXA, 8-IB to 8-IXB, and 8-IC to 8-IIIC.

[0141] [Chemical Formula 8-IA] [Chemical Formula 8-IIA]

[0142] [Chemical Formula 8-IIIA] [Chemical Formula 8-IVA]

[0143] [Chemical Formula 8-VA] [Chemical Formula 8-VIA]

[0144] [Chemical Formula 8-VIIA] [Chemical Formula 8-VIIIA]

[0145] [Chemical Formula 8-IXA]

[0146] [Chemical Formula 8-IB] [Chemical Formula 8-IIB]

[0147] [Chemical Formula 8-IIIB] [Chemical Formula 8-IVB]

[0148] [Chemical Formula 8-VB] [Chemical Formula 8-VIB]

[0149] [Chemical Formula 8-VIIB] [Chemical Formula 8-VIIIB]

[0150] [Chemical Formula 8-IXB] [Chemical Formula 8-IC]

[0151] [Chemical Formula 8-IIC] [Chemical Formula 8-IIIC]

[0152] In chemical formulas 8-IA to 8-IXA, 8-IB to 8-IXB, and 8-IC to 8-IIIC... X 4 X 5 L 12 To L 14 Ar 10 and Ar 11 Same as described above, R 24 To R 29 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl or substituted or unsubstituted C6 to C30 aryl, and m24', m25', m27', and m29' are each an integer in the range of 1 to 3.

[0153] In one embodiment, chemical formula 8 may be represented by chemical formula 8-IVB or chemical formula 8-VIIIB.

[0154] As an example, in chemical formula 8-IVB, X 4 It can be NR f .

[0155] As an example, in chemical formula 8-VIIIB, X 4 It can be O or S, and X 5 For CR g R h or SiR i R j .

[0156] In this article, R f R g R h R i and R j Each can be independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C20 aryl.

[0157] In one embodiment, chemical formula 8 may be represented by chemical formula 8-IVB-2 or chemical formula 8-VIIIB-2.

[0158] [Chemical Formula 8-IVB-2] [Chemical Formula 8-VIIIB-2]

[0159] In chemical formulas 8-IVB-2 and 8-VIIIB-2, m24, m26, and m28 are the same as described above. L 12 To L 14 Each is an independent single bond or a substituted or unsubstituted phenylene group. Ar 10 and Ar 11 Each can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl. X 4 For NR f O or S X 5 For CR g R h or SiR i R j , R f R g R h R i and R j Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 24 and R 26 To R 29 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl or substituted or unsubstituted C6 to C30 aryl, and m27' and m29' are each independent integers in the range of 1 to 3.

[0160] For example, L 12 To L 14 Each can be a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0161] For example, Ar 10 and Ar 11 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzofuran-fluorenyl, or substituted or unsubstituted benzothiophene-fluorenyl.

[0162] For example, the fourth compound may be selected from, but is not limited to, one of the compounds listed in Group 2.

[0163] [Group 2]

[0164] [D-1] [D-2] [D-3] [D-4] [D-5]

[0165] [D-6] [D-7] [D-8] [D-9] [D-10]

[0166] [D-11] [D-12] [D-13] [D-14] [D-15]

[0167] [D-16] [D-17] [D-18] [D-19] [D-20]

[0168] [D-21] [D-22] [D-23] [D-24] [D-25]

[0169] [D-26] [D-27] [D-28] [D-29] [D-30]

[0170] [D-31] [D-32] [D-33] [D-34] [D-35]

[0171] [D-36] [D-37] [D-38] [D-39] [D-40]

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

[0173] [D-46] [D-47] [D-48] [D-49] [D-50]

[0174] [D-51] [D-52] [D-53] [D-54] [D-55]

[0175] [D-56] [D-57] [D-58] [D-59] [D-60]

[0176] [D-61] [D-62] [D-63] [D-64] [D-65]

[0177] [D-66] [D-67] [D-68] [D-69] [D-70]

[0178] [D-71] [D-72] [D-73] [D-74] [D-75]

[0179] [D-76] [D-77] [D-78] [D-79] [D-80]

[0180] [D-81] [D-82] [D-83] [D-84] [D-85]

[0181] [D-86] [D-87] [D-88] [D-89] [D-90]

[0182] [D-91] [D-92] [D-93] [D-94] [D-95]

[0183] [D-96] [D-97] [D-98] [D-99] [D-100]

[0184] [D-101] [D-102] [D-103] [D-104] [D-105]

[0185] [D-106] [D-107] [D-108] [D-109] [D-110]

[0186] [D-111] [D-112] [D-113] [D-114]

[0187] [D-115] [D-116] [D-117] [D-118]

[0188] [D-119] [D-120] [D-121] [D-122]

[0189] [D-123] [D-124] [D-125] [D-126] [D-127]

[0190] [E-1] [E-2] [E-3] [E-4]

[0191] [E-5] [E-6] [E-7] [E-8]

[0192] [E-9] [E-10] [E-11] [E-12]

[0193] [E-13] [E-14] [E-15] [E-16]

[0194] [E-17] [E-18] [E-19] [E-20]

[0195] [E-21] [E-22] [E-23] [E-24]

[0196] [E-25] [E-26] [E-27] [E-28]

[0197] [E-29] [E-30] [E-31] [E-32]

[0198] [E-33] [E-34] [E-35] [E-36]

[0199] [E-37] [E-38] [E-39] [E-40]

[0200] [E-41] [E-42] [E-43] [E-44]

[0201] [E-45] [E-46] [E-47] [E-48]

[0202] [E-49] [E-50] [E-51] [E-52]

[0203] [E-53] [E-54] [E-55] [E-56] [E-57]

[0204] [E-58] [E-59] [E-60] [E-61] [E-62]

[0205] [E-63] [E-64] [E-65] [E-66] [E-67]

[0206] [E-68] [E-69]

[0207] [E-70] [E-71] [E-72] [E-73]

[0208] [E-74] [E-75] [E-76] [E-77]

[0209] [E-78] [E-79] [E-80] [E-81]

[0210] [E-82] [E-83] [E-84] [E-85]

[0211] [E-86] [E-87] [E-88] [E-89]

[0212] [E-90] [E-91] [E-92] [E-93]

[0213] [E-94] [E-95] [E-96] [E-97]

[0214] [F-1] [F-2] [F-3] [F-4] [F-5]

[0215] [F-6] [F-7] [F-8] [F-9] [F-10]

[0216] [F-11] [F-12] [F-13] [F-14] [F-15]

[0217] [F-16] [F-17] [F-18] [F-19] [F-20]

[0218] [F-21] [F-22] [F-23] [F-24] [F-25]

[0219] [F-26] [F-27] [F-28] [F-29] [F-30]

[0220] [F-31] [F-32] [F-33] [F-34] [F-35]

[0221] [F-36] [F-37] [F-38] [F-39] [F-40]

[0222] [F-41] [F-42] [F-43] [F-44] [F-45]

[0223] [F-46] [F-47] [F-48] [F-49] [F-50]

[0224] [F-51] [F-52] [F-53] [F-54] [F-55]

[0225] [F-56] [F-57] [F-58] [F-59] [F-60]

[0226] [F-61] [F-62] [F-63] [F-64] [F-65]

[0227] [F-66] [F-67] [F-68] [F-69] [F-70]

[0228] [G-1] [G-2] [G-3] [G-4]

[0229] [G-5] [G-6] [G-7] [G-8]

[0230] [G-9] [G-10] [G-11] [G-12]

[0231] [G-13] [G-14] [G-15] [G-16]

[0232] [G-17] [G-18] [G-19] [G-20]

[0233] [G-21] [G-22] [G-23] [G-24]

[0234] [G-25] [G-26] [G-27] [G-28]

[0235] [G-29] [G-30] [G-31] [G-32]

[0236] [G-33] [G-34] [G-35] [G-36]

[0237] [G-37] [G-38] [G-39] [G-40]

[0238] [G-41] [G-42] [G-43] [G-44]

[0239] [G-45] [G-46] [G-47] [G-48]

[0240] (Dn refers to the number of deuterium atoms substituted, and n is an integer of 0 or greater).

[0241] As the fourth compound represented by chemical formula 7, in addition to the compounds mentioned above, 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, and KR10-2019-0034074A may also be used.

[0242] The first and fourth compounds may be included in a weight ratio of, for example, 1:99 to 99:1. Within this range, the electron transport capability of the first compound and the hole transport capability of the fourth compound can be used to adjust the appropriate weight ratio to achieve bipolar characteristics, thereby improving efficiency and lifetime. Within this range, they may be included in weight ratios of, for example, about 10:90 to 90:10, about 20:80 to 80:20, and, for example, about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40. As a specific example, they may be included in weight ratios of 40:60, 50:50, or 60:40.

[0243] The dopant can be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, such as a red or green phosphorescent dopant.

[0244] A dopant is a material that is mixed in small amounts with the host to induce luminescence, and is typically a material such as a metal complex that emits light by being excited multiple times to a triplet or higher state. Dopants can be, for example, inorganic, organic, or organic / inorganic compounds, and one or more of these types can be used.

[0245] Examples of dopants can be phosphorescent dopants, and examples of phosphorescent dopants can be organometallic compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants can be, for example, compounds represented by the chemical formula Z, but are not limited thereto.

[0246] [Chemical Formula Z]

[0247] L 15 MX 6

[0248] In the chemical formula Z, M is a metal, and L 15 and X 6 The same or different, and is a ligand that forms a complex with M.

[0249] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L 15 and X 6 For example, it could be a bidentate ligand.

[0250] By L 15 and X 6 The ligands represented can be any one selected from chemical formulas Z-1 to Z-8.

[0251] [Z-1] [Z-2] [Z-3]

[0252] [Z-4] [Z-5]

[0253] [Chemical Formula Z-6] [Chemical Formula Z-7]

[0254] [Z-8]

[0255] In chemical formulas Z-1 to Z-8 X 14Selected from carbon and nitrogen, Y 100 For O or S, R 101 To R 122 Each of these elements is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 133 R 134 R 135 or -GeR 133 R 134 R 135 Alternatively, it can be linked with adjacent substituents to form substituted or unsubstituted rings, and for example, it can be combined with pyridine to form substituted or unsubstituted quinolines, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothiophenopyridine, substituted or unsubstituted indenepyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothiophenoquinoline, or substituted or unsubstituted indenequinoline; m18 is an integer in the range of 1 to 4, and m19 is an integer in the range of 1 to 5.

[0256] By L 15 and X 6 Specific examples of the ligands represented may be selected from the chemical formulas listed in Group A, but are not limited thereto.

[0257] [Group A]

[0258] In group A, R 300 To R 302 Each is independently hydrogen, deuterium, a C1 to C30 alkyl group substituted or unsubstituted with a halogen, a C6 to C30 aryl group substituted or unsubstituted with a C1 to C30 alkyl group, or a halogen. R 303 To R 308Each of the following is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF5, trialkylsilyl having substituted or unsubstituted C1 to C30 alkyl, dialkylarylsilyl having substituted or unsubstituted C1 to C30 alkyl and C6 to C30 aryl, or triarylsilyl having substituted or unsubstituted C6 to C30 aryl. m25 is an integer from 1 to 5. m26 is an integer from 1 to 4. m27 is an integer from 1 to 3. m28 is an integer of 1 or 2. m29 is an integer from 1 to 6, and When m25 to m29 are 2 or greater, R 303 To R 307 They are the same as or different from each other.

[0259] According to one embodiment, the phosphorescent dopant can be an iridium complex and can be represented, for example, by any one of chemical formulas 9 to 11.

[0260] [Chemical Formula 9]

[0261] In chemical formula 9, Ring A is a monocyclic or polycyclic fused ring. In both monocyclic and polycyclic fused rings, each ring is a 5- or 6-membered carbon ring or a heterocyclic ring. R 100 Indicates one to a maximum number of monovalent substituents. When R 100 When there are 2 or more, R 100 Each is the same as or different from the other. R 101 To R 104 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR 114 R 115 R 116 -GeR 114 R 115 R 116 Or a combination of them, R 114 To R 116Each is independently a substituted or unsubstituted C1 to C6 alkyl group. X 10 and X 11 Each is independently selected from carbon and nitrogen. L 100 It is a monovalent anionic ligand or a bidentate ligand, and is a ligand coordinated with iridium via the lone pair electrons of a carbon or heteroatom. m21 is any integer from 0 to 3.

[0262] [Chemical Formula 10]

[0263] In chemical formula 10, Ring B is a monocyclic or polycyclic fused ring. In both monocyclic and polycyclic fused rings, each ring is a 5- or 6-membered carbon ring or a heterocyclic ring. Y 100 For O or S, R 201 Indicates one to a maximum number of monovalent substituents. When R 201 When there are 2 or more, R 201 Each is the same as or different from the other. R 206 To R 213 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR 114 R 115 R 116 -GeR 114 R 115 R 116 Or a combination of them, R 114 To R 116 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. X 12 and X 13 Each is independently selected from carbon and nitrogen. L 100 It is a monovalent anionic ligand or a bidentate ligand, and is a ligand coordinated with iridium via the lone pair electrons of a carbon or heteroatom. m21 is any integer from 0 to 3.

[0264] [Chemical Formula 11]

[0265] In chemical formula 11, Y 100 For O or S, R101 To R 111 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR 114 R 115 R 116 -GeR 114 R 115 R 116 Or a combination of them, R 114 To R 116 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. L 100 It is a monovalent anionic ligand or a bidentate ligand, and is a ligand coordinated with iridium via the lone pair electrons of a carbon or heteroatom. m21 is any integer from 0 to 3.

[0266] As a more specific example, iridium complexes can be represented by any of the chemical formulas 9-1 to 9-6.

[0267] [Chemical Formula 9-1]

[0268] In chemical formula 9-1, R 101 To R 116 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR 132 R 133 R 134 or -GeR 132 R 133 R 134 , R 132 To R 134 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. R 101 To R 116 At least one of them is a functional group represented by the chemical formula V-1. L 100 It is a bidentate ligand for monovalent anions, and is a ligand coordinated with iridium via the lone pair electrons of carbon or heteroatoms. m21 and m22 are each independent integers from 0 to 3, and m21 + m22 is an integer from 1 to 3. [Chemical Formula V-1]

[0269] In chemical formula V-1, R 135 To R 139 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 132 R 133 R 134 ,and It refers to the part that is attached to a carbon atom.

[0270] [Chemical Formula 9-2]

[0271] [Chemical Formula 9-3]

[0272] [Chemical Formula 9-4]

[0273] [Chemical Formula 9-5]

[0274] [Chemical Formula 9-6]

[0275] In chemical formulas 9-2 to 9-6 X 14 Selected from carbon and nitrogen, Y 100 For O or S, R 101 To R 122 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR 133 R 134 R 135 or -GeR 133 R 134 R 135 , R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. L 100 It is a bidentate ligand for monovalent anions, and is a ligand coordinated with iridium via the lone pair electrons of carbon or heteroatoms. m111 is an integer from 1 to 2. n1 and n2 are each independent integers from 0 to 3, and n1 + n2 is an integer from 1 to 3.

[0276] In another embodiment, the dopant may be a platinum complex, for example, represented by the chemical formula Z-3.

[0277] [Chemical Formula Z-3]

[0278] In chemical formula Z-3, rings A, B, C, and D independently represent 5- or 6-membered carbon rings or heterocycles; R A R B R C and R D Independently indicates monosubstituted, disubstituted, trisubstituted, tetrasubstituted, or unsubstituted; nA is an integer that is either 0 or 1; L B L C and L D Each is independently selected from direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; When nA is 1, L E Selected from direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and their combinations; when nA is 0, L E It does not exist; and R A R B R C R D R and R' are each independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; any adjacent R A R B R C R D R and R' are optionally connected to each other to provide a loop; X B X C X D and X E Each is independently selected from carbon and nitrogen; and Q 1 Q 2 Q 3 and Q 4 Each represents oxygen or a direct bond.

[0279] Platinum complexes can be represented, for example, by chemical formula 12-1 or chemical formula 12-2.

[0280] [Chemical Formula 12-1]

[0281] [Chemical Formula 12-2]

[0282] In chemical formulas 12-1 and 12-2, X 100 Selected from O, S and NR 132 , R 118 To R 132 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 133 R 134 R 135 , R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. R 118 To R 132 At least one of them is -SiR 133 R 134 R 135 Or tert-butyl, and R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0283] The composition also contains a dopant, which may be, for example, a composition that emits red or green light.

[0284] Hole transport layer 32 is a layer used to facilitate the transfer of holes from anode 10 to light-emitting layer 31 and to block electrons, and may be, for example, an amine compound, but is not limited thereto.

[0285] Amine compounds may include, for example, at least one aryl and / or heteroaryl group. Amine compounds may be represented, for example, by chemical formula a or chemical formula b, but are not limited thereto.

[0286] [Chemical Formula a] [Chemical Formula b]

[0287] In chemical formula a or b Ar a To Ar g Each of these elements is independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl, or a combination thereof. Ara To Ar c At least one of them and Ar d To Ar g At least one of them is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and Ar h It 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.

[0288] In addition to the light-emitting layer, an organic light-emitting diode may also include a hole injection layer 34.

[0289] Hole injection layer 34 is a layer used to facilitate the injection of holes from anode 10 into light-emitting layer 31 and to block electrons, and can be disposed between anode 10 and hole transport layer 32.

[0290] For example, at least one of the compounds listed in Group B may be included in at least one of the hole transport layer 32 and the hole injection layer 34, and may be made of a different material than the first hole transport auxiliary layer and the second hole transport auxiliary layer described below.

[0291] [Group B]

[0292] (Dn refers to the number of hydrogens replaced by deuterium and indicates the structure in which one or more hydrogens are replaced.)

[0293] In addition to the compounds described above, known compounds and compounds with similar structures described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A may also be used in the hole transport layer 32 and the hole injection layer 34.

[0294] The 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.

[0295] The first hole transport auxiliary layer contains a second compound represented by chemical formula 3, the second hole transport auxiliary layer contains a third compound represented by chemical formula 3, and the second compound and the third compound are different from each other.

[0296] [Chemical Formula 3]

[0297] In chemical formula 3, X 2 For O, S or CR b R c , L 4 To L 6 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene. Ar 3 and Ar 4Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. R b R c and R 6 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. R b and R c They exist independently or are connected to each other to form substituted or unsubstituted spirodifluorene. A is substituted or unsubstituted benzene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, or substituted or unsubstituted spirodifluorene. m6 is an integer from 1 to 3, and When m6 is 2 or greater, R 6 They are the same as or different from each other.

[0298] An organic light-emitting diode according to one embodiment is applied by combining two hole transport auxiliary layers at the interface between the hole transport layer and the light-emitting layer. The hole injection capability in the first hole transport auxiliary layer is adjusted to match the charge balance in the light-emitting layer, and improved lifetime characteristics can be achieved by introducing a compound with high exciton stability into the second hole transport auxiliary layer.

[0299] As an example, chemical formula 3 can be represented by any of chemical formulas 3-I to 3-VIII.

[0300] [Chemical Formula 3-I] [Chemical Formula 3-II]

[0301] [Chemical Formula 3-III] [Chemical Formula 3-IV]

[0302] [Chemical Formula 3-V] [Chemical Formula 3-VI]

[0303] [Chemical Formula 3-VII] [Chemical Formula 3-VIII]

[0304] In chemical formulas 3-I to 3-VIII X 2 and X 3 Each independently represents O, S, or CR. cR d , L 4 To L 6 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene. Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. R c R d and R 6 To R 11 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. m6 is an integer from 1 to 3. m7 and m9 through m11 are each an independent integer from 1 to 4. m8 is an integer of 1 or 2, and When m6 to m11 are each independently 2 or greater, R 6 To R 11 They are the same as or different from each other.

[0305] As a specific example, in chemical formula 3, Ar 3 and Ar 4 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted 1-fluorenyl, substituted or unsubstituted 2-fluorenyl, substituted or unsubstituted 3-fluorenyl, substituted or unsubstituted 4-fluorenyl, substituted or unsubstituted 9-fluorenyl, substituted or unsubstituted 9,9-spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted dibenzothiopheneyl.

[0306] As a specific example, in chemical formula 3, Ar 3 and Ar 4 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted 1-fluorenyl, substituted or unsubstituted 2-fluorenyl, substituted or unsubstituted 3-fluorenyl, substituted or unsubstituted 4-fluorenyl, substituted or unsubstituted 9-fluorenyl, substituted or unsubstituted 9,9-spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted dibenzothiopheneyl.

[0307] For example, in chemical formula 3 and chemical formulas 3-I to 3-VIII, R 6 To R 11 Each of them can be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, substituted or unsubstituted C1 to C10 alkylsilyl or substituted or unsubstituted C6 to C12 aryl.

[0308] As an example, in formula 3 and formulas 3-I to 3-VIII, R 6 To R 11 Each can be independently hydrogen, deuterium, cyano, substituted or unsubstituted tert-butyl, or substituted or unsubstituted phenyl.

[0309] For example, in chemical formula 3, L 4 To L 6 Each can be a single bond or a substituted or unsubstituted phenylene group.

[0310] As an example, L 4 -Ar 3 and L 5 -Ar 4 Each can be independently selected from the substituents listed in Group III.

[0311] Group III

[0312] In Group III, R 36 To R 41 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m36 is an integer from 1 to 5. m37 is an integer from 1 to 4. m38 is an integer from 1 to 7. m39 is an integer from 1 to 3. m40 is an integer of 1 or 2. This is the connection point.

[0313] When m36 is 2 or greater, R 36 Each can be the same as or different from the other.

[0314] When m37 is 2 or greater, R 37 Each can be the same as or different from the other.

[0315] When m38 is 2 or greater, R38 Each can be the same as or different from the other.

[0316] When m39 is 2 or greater, R 39 Each can be the same as or different from the other.

[0317] When m40 is 2, R 40 Each can be the same as or different from the other.

[0318] As a specific example, the second and third compounds can each be represented independently by the above chemical formula 3-I.

[0319] For example, in the second compound, in chemical formula 3-I, X 2 For O, S or CR c R d , R c and R d Each is independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C12 aryl. L 4 To L 6 Each is an independent single key. Ar 3 and Ar 4 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted 1-fluorenyl, substituted or unsubstituted 2-fluorenyl, substituted or unsubstituted 3-fluorenyl, substituted or unsubstituted 4-fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted dibenzothiophenyl. R 6 and R 7 Each of them is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, or substituted or unsubstituted C6 to C12 aryl. m6 is an integer from 1 to 3, and m7 is an integer from 1 to 4.

[0320] For example, in the third compound, in chemical formula 3-I, X 2 For O, S or CR c R d , R c and R d They connect with each other to form substituted or unsubstituted spirodifluorene. L 4 and L 5 Each is an independent single bond or a substituted or unsubstituted phenylene group. L6 It is a single bond or a substituted or unsubstituted phenylene. Ar 3 and Ar 4 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted 1-fluorenyl, substituted or unsubstituted 2-fluorenyl, substituted or unsubstituted 3-fluorenyl, substituted or unsubstituted 4-fluorenyl, substituted or unsubstituted 9-fluorenyl, substituted or unsubstituted 9,9-spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted dibenzothiopheneyl. R 6 and R 7 Each of them is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, or substituted or unsubstituted C6 to C12 aryl. m6 is an integer from 1 to 3, and m7 is an integer from 1 to 4.

[0321] In the most specific embodiment of the present invention, the first compound may be represented by chemical formula 1-I, the second compound may be represented by chemical formula 3-Ia, the third compound may be represented by any one of chemical formula 3-Ib, chemical formula 3-Ic and chemical formula 3-VIII, and the fourth compound may be represented by any one of chemical formula 4-8, chemical formula 7-2 and chemical formula 7-3.

[0322] [Chemical Formula 1-I]

[0323] In chemical formula 1-I, Z 1 To Z 3 Each is N, X 1 For NL b -R b O or S L a L b and L 1 To L 3 Each of these can be independently a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted dibenzothiopheneylene. R b Ar 1 and Ar 2Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted trefyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophene, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, or substituted or unsubstituted triazine. R 1 and R 2 Each of the following is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiopheneyl. m1 and m2 are each an independent integer from 1 to 4, and m3 is an integer of 1 or 3; [Chemical Formula 3-Ia]

[0324] In chemical formula 3-Ia, R c and R d Each is independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C12 aryl. Ar 3 and Ar 4 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted 1-fluorenyl, substituted or unsubstituted 2-fluorenyl, substituted or unsubstituted 3-fluorenyl, substituted or unsubstituted 4-fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted dibenzothiophenyl. R 6 R 7a and R 7b Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, or substituted or unsubstituted C6 to C12 aryl, and m6 is an integer from 1 to 3; [Chemical Formula 3-Ib] [Chemical Formula 3-Ic]

[0325] [Chemical Formula 3-VIII]

[0326] In chemical formulas 3-Ib, 3-Ic, and 3-VIII X 2 For O or S, R c and R d Each is independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C12 aryl. L 4 To L 6 Each is an independent single bond or a substituted or unsubstituted phenylene group. Ar 3 and Ar 4 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted 1-fluorenyl, substituted or unsubstituted 2-fluorenyl, substituted or unsubstituted 3-fluorenyl, substituted or unsubstituted 4-fluorenyl, substituted or unsubstituted 9-fluorenyl, substituted or unsubstituted 9,9-spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted dibenzothiopheneyl. R 6 R 7 R 10 and R 11 Each of them is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, or substituted or unsubstituted C6 to C12 aryl. m6 is an integer from 1 to 3. m7, m10, m11, and m42 are each an independent integer from 1 to 4, and R 42 It is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, substituted or unsubstituted silyl or combinations thereof; [Chemical Formula 4-8]

[0327] In chemical formula 4-8, R 13 To R 16 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group. L 7 and L 8 Each can be independently a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene. Ar 5 and Ar 6Each can be independently substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, or substituted or unsubstituted fluorenyl. m13 and m16 are each an independent integer from 1 to 4, and m14 and m15 are each an independent integer from 1 to 3; [Chemical Formula 7-2] [Chemical Formula 7-3]

[0328] In chemical formulas 7-2 and 7-3, Ar 9 For substituted or unsubstituted phenyl or substituted or unsubstituted biphenyl, L 11 Each is an independent single bond or a substituted or unsubstituted phenylene group. R 20 To R 23 Each can be independently hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted carbazole. R 22 and R 23 One of them is a substituted or unsubstituted carbazole group. m20, m22, and m23 are each independently an integer from 1 to 4, and m21 is an integer from 1 to 3.

[0329] For example, in chemical formula 3-Ia, R 7a and R 7b They can be substituted or unsubstituted tert-butyl groups, each independent of the other.

[0330] For example, the second and third compounds may each be selected from, but are not limited to, the compounds listed in Group 3.

[0331] [Group 3]

[0332] [1-1] [1-2] [1-3] [1-4] [1-5]

[0333] [1-6] [1-7] [1-8] [1-9] [1-10]

[0334] [1-11] [1-12] [1-13] [1-14] [1-15]

[0335] [1-16] [1-17] [1-18] [1-19] [1-20]

[0336] [1-21] [1-22] [1-23] [1-24] [1-25]

[0337] [1-26] [1-27] [1-28] [1-29] [1-30]

[0338] [1-31] [1-32] [1-33] [1-34] [1-35]

[0339] [1-36] [1-37] [1-38] [1-39] [1-40]

[0340] [1-41] [1-42] [1-43] [1-44] [1-45]

[0341] [1-46] [1-47] [1-48] [1-49] [1-50]

[0342] [1-51] [1-52] [1-53] [1-54] [1-55]

[0343] [1-56] [1-57] [1-58] [1-59] [1-60]

[0344] [1-61] [1-62] [1-63] [1-64] [1-65]

[0345] [1-66] [1-67] [1-68] [1-69] [1-70]

[0346] [1-71] [1-72] [1-73] [1-74] [1-75]

[0347] [1-76] [1-77] [1-78] [1-79] [1-80]

[0348] [1-81] [1-82] [1-83] [1-84] [1-85]

[0349] [1-86] [1-87] [1-88] [1-89] [1-90]

[0350] [1-91] [1-92] [1-93] [1-94] [1-95]

[0351] [1-96] [1-97] [1-98] [1-99] [1-100]

[0352] [1-101] [1-102] [1-103] [1-104] [1-105]

[0353] [1-106] [1-107] [1-108] [1-109] [1-110]

[0354] [1-111] [1-112] [1-113] [1-114] [1-115]

[0355] [1-116] [1-117] [1-118] [1-119] [1-120]

[0356] [1-121] [1-122] [1-123] [1-124] [1-125]

[0357] [1-126] [1-127] [1-128] [1-129] [1-130]

[0358] [1-131] [1-132] [1-133] [1-134] [1-135]

[0359] [1-136] [1-137] [1-138] [1-139] [1-140]

[0360] [1-141] [1-142] [1-143] [1-144] [1-145]

[0361] [1-146] [1-147] [1-148] [1-149] [1-150]

[0362] [1-151] [1-152] [1-153] [1-154] [1-155]

[0363] [1-156] [1-157] [1-158] [1-159] [1-160]

[0364] [1-161] [1-162] [1-163] [1-164] [1-165]

[0365] [1-166] [1-167] [1-168] [1-169] [1-170]

[0366] [1-171] [1-172] [1-173] [1-174] [1-175]

[0367] [1-176] [1-177] [1-178] [1-179] [1-180]

[0368] [1-181] [1-182] [1-183] [1-184] [1-185]

[0369] [1-186] [1-187] [1-188] [1-189] [1-190]

[0370] [1-191] [1-192] [1-193] [1-194] [1-195]

[0371] [1-196] [1-197] [1-198] [1-199] [1-200]

[0372] [1-201] [1-202] [1-203] [1-204] [1-205]

[0373] [1-206] [1-207] [1-208] [1-209] [1-210]

[0374] [1-211] [1-212] [1-213] [1-214] [1-215]

[0375] [1-216] [1-217] [1-218] [1-219] [1-220]

[0376] [1-221] [1-222] [1-223] [1-224] [1-225]

[0377] [1-226] [1-227] [1-228] [1-229] [1-230]

[0378] [1-231] [1-232] [1-233] [1-234] [1-235]

[0379] [1-236] [1-237] [1-238] [1-239] [1-240]

[0380] [1-241] [1-242] [1-243] [1-244] [1-245]

[0381] [1-246] [1-247] [1-248] [1-249] [1-250]

[0382] [1-251] [1-252] [1-253] [1-254] [1-255]

[0383] [1-256] [1-257] [1-258] [1-259] [1-260]

[0384] [1-261] [1-262] [1-263] [1-264] [1-265]

[0385] [1-266] [1-267] [1-268] [1-269] [1-270]

[0386] [1-271] [1-272] [1-273] [1-274] [1-275]

[0387] [1-276] [1-277] [1-278] [1-279] [1-280]

[0388] [1-281] [1-282] [1-283] [1-284] [1-285]

[0389] [1-286] [1-287] [1-288] [1-289] [1-290]

[0390] [1-291] [1-292] [1-293] [1-294] [1-295]

[0391] [1-296] [1-297] [1-298] [1-299] [1-300]

[0392] [1-301] [1-302] [1-303] [1-304] [1-305]

[0393] [1-306] [1-307] [1-308] [1-309] [1-310]

[0394] [1-311] [1-312] [1-313] [1-314] [1-315]

[0395] [1-316] [1-317] [1-318] [1-319] [1-320]

[0396] [1-321] [1-322] [1-323] [1-324] [1-325]

[0397] [1-326] [1-327] [1-328] [1-329] [1-330]

[0398] [1-331] [1-332] [1-333] [1-334] [1-335]

[0399] [1-336] [1-337] [1-338] [1-339] [1-340]

[0400] [1-341] [1-342] [1-343] [1-344] [1-345]

[0401] [1-346] [1-347] [1-348] [1-349] [1-350]

[0402] [1-351] [1-352] [1-353] [1-354] [1-355]

[0403] [1-356] [1-357] [1-358] [1-359] [1-360]

[0404] [1-361] [1-362] [1-363] [1-364] [1-365]

[0405] [1-366] [1-367] [1-368] [1-369] [1-370]

[0406] [1-371] [1-372] [1-373] [1-374] [1-375]

[0407] [1-376] [1-377] [1-378] [1-379] [1-380]

[0408] [1-381] [1-382] [1-383] [1-384] [1-385]

[0409] [1-386] [1-387] [1-388] [1-389] [1-390]

[0410] [1-391] [1-392] [1-393] [1-394] [1-395]

[0411] [1-396] [1-397] [1-398] [1-399] [1-400]

[0412] [1-401] [1-402] [1-403] [1-404]

[0413] [1-405] [1-406] [1-407] [1-408]

[0414] [1-409] [1-410] [1-411] [1-412]

[0415] [1-413] [1-414] [1-415] [1-416]

[0416] [2-1] [2-2] [2-3] [2-4] [2-5]

[0417] [2-6] [2-7] [2-8] [2-9] [2-10]

[0418] [2-11] [2-12] [2-13] [2-14] [2-15]

[0419] [2-16] [2-17] [2-18] [2-19] [2-20]

[0420] [2-21] [2-22] [2-23] [2-24] [2-25]

[0421] [2-26] [2-27] [2-28] [2-29] [2-30]

[0422] [2-31] [2-32] [2-33] [2-34] [2-35]

[0423] [2-36] [2-37] [2-38] [2-39] [2-40]

[0424] [2-41] [2-42] [2-43] [2-44] [2-45]

[0425] [2-46] [2-47] [2-48] [2-49] [2-50]

[0426] [2-51] [2-52] [2-53] [2-54] [2-55]

[0427] [2-56] [2-57] [2-58] [2-59] [2-60]

[0428] [2-61] [2-62] [2-63] [2-64] [2-65]

[0429] [2-66] [2-67] [2-68] [2-69] [2-70]

[0430] [2-71] [2-72] [2-73] [2-74] [2-75]

[0431] [2-76] [2-77] [2-78] [2-79] [2-80]

[0432] [2-81] [2-82] [2-83] [2-84] [2-85]

[0433] [2-86] [2-87] [2-88] [2-89] [2-90]

[0434] [2-91] [2-92] [2-93] [2-94] [2-95]

[0435] [2-96] [2-97] [2-98] [2-99] [2-100]

[0436] [2-101] [2-102] [2-103] [2-104] [2-105]

[0437] [2-106] [2-107] [2-108] [2-109] [2-110]

[0438] [2-111] [2-112] [2-113] [2-114] [2-115]

[0439] [2-116] [2-117] [2-118] [2-119] [2-120]

[0440] [2-121] [2-122] [2-123] [2-124] [2-125]

[0441] [2-126] [2-127] [2-128] [2-129] [2-130]

[0442] [2-131] [2-132] [2-133] [2-134] [2-135]

[0443] [2-136] [2-137] [2-138] [2-139] [2-140]

[0444] [2-141] [2-142] [2-143] [2-144] [2-145]

[0445] [2-146] [2-147] [2-148] [2-149] [2-150]

[0446] [2-151] [2-152] [2-153] [2-154] [2-155]

[0447] [2-156] [2-157] [2-158] [2-159] [2-160]

[0448] [2-161] [2-162] [2-163] [2-164] [2-165]

[0449] [2-166] [2-167] [2-168] [2-169] [2-170]

[0450] [2-171] [2-172] [2-173] [2-174] [2-175]

[0451] [2-176] [2-177] [2-178] [2-179] [2-180]

[0452] [2-181] [2-182] [2-183] [2-184] [2-185]

[0453] [2-186] [2-187] [2-188] [2-189] [2-190]

[0454] [2-191] [2-192] [2-193] [2-194] [2-195]

[0455] [2-196] [2-197] [2-198] [2-199] [2-200]

[0456] [2-201] [2-202] [2-203] [2-204] [2-205]

[0457] [2-206] [2-207] [2-208] [2-209] [2-210]

[0458] [2-211] [2-212] [2-213] [2-214] [2-215]

[0459] [2-216] [2-217] [2-218] [2-219] [2-220]

[0460] [2-221] [2-222] [2-223] [2-224] [2-225]

[0461] [2-226] [2-227] [2-228] [2-229] [2-230]

[0462] [2-231] [2-232] [2-233] [2-234] [2-235]

[0463] [2-236] [2-237] [2-238] [2-239] [2-240]

[0464] [2-241] [2-242] [2-243] [2-244] [2-245]

[0465] [2-246] [2-247] [2-248] [2-249] [2-250]

[0466] [2-251] [2-252] [2-253] [2-254] [2-255]

[0467] [2-256] [2-257] [2-258] [2-259] [2-260]

[0468] [2-261] [2-262] [2-263] [2-264] [2-265]

[0469] [2-266] [2-267] [2-268] [2-269] [2-270]

[0470] The electron transport region can further improve electron injection and / or electron mobility between the cathode 20 and the light-emitting layer 31 and block holes.

[0471] Specifically, the electron transport region may include an electron transport layer 35 between the cathode 20 and the light-emitting layer 31 and an electron transport auxiliary layer (not shown) between the light-emitting layer 31 and the electron transport layer 35, and at least one of the compounds listed in group C below may be included in at least one of the electron transport layer 35 and the electron transport auxiliary layer.

[0472] [Group C]

[0473] One embodiment may provide an organic light-emitting diode, which includes an emitting layer 31, a hole transport layer 32, a first hole transport auxiliary layer 33a, and a second hole transport auxiliary layer 33b as organic layers.

[0474] Another implementation may provide an organic light-emitting diode that also includes a hole injection layer as an organic layer.

[0475] Another embodiment can provide an organic light-emitting diode that also includes an electron transport region as an organic layer.

[0476] In addition to the light-emitting layer, the organic light-emitting diode may also include an electron injection layer (not shown) as the organic layer.

[0477] Organic light-emitting diodes (OLEDs) can be fabricated by forming an anode or cathode on a substrate, then forming an organic layer using dry film methods (such as vacuum deposition, sputtering, plasma plating, and ion plating), and finally forming a cathode or anode thereon.

[0478] The aforementioned organic light-emitting diodes can be used in organic light-emitting display devices.

[0479] The best model of invention

[0480] In the following description, implementation methods are illustrated in more detail with reference to embodiments. However, these embodiments are exemplary, and the scope of the invention is not limited thereto.

[0481] In the following examples and synthesis examples, the starting materials and reactants used were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry, or P & H Tech, or synthesized by known methods, unless otherwise specified.

[0482] The compounds given as more specific examples of compounds of the present invention are synthesized by the following steps.

[0483] (Preparation of the first compound)

[0484] Synthesis Example 1: Synthesis of Compound B-56

[0485] [Reaction Formula 1]

[0486] Compound B-56 ​​(deuterium substitution number Dn=0) was synthesized from intermediate B-56-1 (CAS No.: 2799617-40-4) and 2-(4-biphenyl)-4-chloro-6-phenyl-1,3,5-triazine (CAS No.: 1472062-94-4) by referring to the known synthetic method in the published patent application KR 10-2021-0039202.

[0487] Synthesis Example 2: Synthesis of Compound B-41

[0488] [Reaction 2]

[0489] Compound B-41 (deuterium substitution number Dn=0) was synthesized from intermediate B-41-1 (CAS No.: 1024598-06-8) and intermediate B-41-2 (CAS No.: 2379718-08-6) by referring to the known synthetic method in the published patent application KR 10-2021-0039202.

[0490] Synthesis Example 3: Synthesis of Compound B-46

[0491] [Reaction 3]

[0492] Compound B-46 (deuterium substitution number Dn=0) was synthesized from intermediate B-46-1 (CAS No.: 2645414-19-1) and 2-(4-biphenyl)-4-chloro-6-phenyl-1,3,5-triazine (CAS No.: 1472062-94-4) by referring to the known synthetic method in published patent application KR 10-2021-0039202.

[0493] Synthesis Example 4: Synthesis of Compound C-4

[0494] [Reaction 4]

[0495] Compound C-4 (deuterium substitution number Dn=0) was synthesized from intermediate C-4-1 (CAS No.: 2744274-34-6) and 2-(4-biphenyl)-4-chloro-6-phenyl-1,3,5-triazine (CAS No.: 1472062-94-4) by referring to the known synthetic method in published patent application KR 10-2023-0154750.

[0496] (Preparation of the fourth compound)

[0497] Synthesis Example 5: Synthesis of Compound D-105

[0498] [Reaction 5]

[0499] Compound D-105 was synthesized from intermediate D-105-1 (CAS No.: 2769775-48-4) and intermediate D-105-2 (CAS No.: 3044772-66-6) by referring to known synthetic methods.

[0500] Synthesis Example 6: Synthesis of Compound D-99

[0501] [Reaction Formula 6]

[0502] Compound D-99 was synthesized from intermediate D-99-1 (CAS No.: 2861991-04-8) and intermediate D-99-2 (CAS No.: 142475-00-1) by referring to the known synthetic method in Chinese public application CN 117229193.

[0503] Synthesis Example 7: Synthesis of Compound D-121

[0504] [Reaction Formula 7]

[0505] Compound D-121 was synthesized from intermediate D-121-1 (CAS No.: 2769775-48-4) and intermediate D-121-2 (CAS No.: 3007666-38-5) by referring to the known synthetic method in Chinese public application CN 117229193 A.

[0506] (Preparation of the second compound)

[0507] Synthetic Example 8: Synthesis of Compounds 1-139

[0508] [Reaction Equation 8]

[0509] 10 g (35.88 mmol) of intermediate 1-chloro-8-phenyldibenzo[b,d]furan, 12.97 g (35.88 mmol) of intermediate N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine, 5.52 g (57.40 mmol) of sodium tert-butoxide, and 1.03 g (2.51 mmol) of 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (Sphos) were dissolved in 239 mL of xylene. After adding 0.99 g (1.08 mmol) of Pd2(dba)3, the mixture was stirred and refluxed under nitrogen atmosphere for 12 hours. After the reaction was complete, the mixture was extracted with toluene and distilled water. 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 using hexane / dichloromethane (3:1 volume ratio) to give 16.2 g (75% yield) of compound 1-139 as a white solid.

[0510] Synthesis Example 9: Synthesis of Compounds 1-399

[0511] [Reaction Formula 9]

[0512] Compound 1-399 (14.5 g, 70% yield) was synthesized in the same manner as in Synthesis Example 8, except that 10.0 g of intermediate 1,3-di-tert-butyl-5-chloro-9,9-dimethyl-9H-fluorene and 11.78 g of intermediate bis(9,9-dimethyl-9H-fluorene-2-yl)amine were used in a 1:1 equivalent ratio.

[0513] Synthesis Example 10: Synthesis of Compound 1-393

[0514] [Reaction Formula 10]

[0515] Compound 1-393 was synthesized in the same manner as in Synthesis Example 8, except that intermediates Int-3 (CAS No.: 2356108-27-3) and Int-4 (CAS No.: 1198395-24-2) were used in a 1:1 equivalent ratio.

[0516] Synthesis Example 11: Synthesis of Compound 1-1

[0517] [Reaction Formula 11]

[0518] Compound 1-1 was synthesized in the same manner as in Synthetic Example 8, except that intermediates 2-chloro-9,9-dimethyl-9H-fluorene (CAS No.: 382602-31-5) and 1-1-1 (CAS No.: 2225845-23-6) were used in a 1:1 equivalent ratio.

[0519] (Preparation of the third compound)

[0520] Synthetic Example 12: Synthesis of Compound 2-34

[0521] [Reaction 12]

[0522] Compounds 2-34 were synthesized in the same manner as in Synthesis Example 8, except that Int-7 (CAS No.: 2110512-06-4) and Int-8 (CAS No.: 1644054-07-8) were used in a 1:1 equivalent ratio.

[0523] Synthetic Example 13: Synthesis of Compound 1-418

[0524] [Reaction Formula 13]

[0525] Compound 1-418 was synthesized in the same manner as in Synthetic Example 8, except that 2-bromo-9,9'-dimethylfluorene (CAS No.: 28320-31-2) and intermediate 1-418-1 (CAS No.: 1853122-02-7) were used in a 1:1 equivalent ratio.

[0526] Synthesis Example 14: Synthesis of Compound 2-218

[0527] [Reaction Formula 14]

[0528] Compound 2-218 was synthesized in the same manner as in Synthetic Example 8, except that intermediates 2-218-1 (CAS No.: 955959-89-4) and 2-218-2 (CAS No.: 151619-19-1) were used in a 1:1 equivalent ratio.

[0529] Synthetic Example 15: Synthesis of Compound 2-245

[0530] [Reaction Formula 15]

[0531] Compound 2-245 was synthesized in the same manner as in Synthetic Example 8, except that intermediate 2-218-1 (CAS No.: 955959-89-4) and intermediate 9-(3-bromophenyl)-9-phenyl-9H-fluorene (CAS No.: 1257251-75-4) were used in a 1:1 equivalent ratio with reference to the synthetic method known in registered patent KR 10-1931250.

[0532] Synthetic Example 16: Synthesis of Compound 2-131

[0533] [Reaction Formula 16]

[0534] Compound 2-131 was synthesized in the same manner as in Synthetic Example 8, except that intermediates 1-chlorodibenzo[b,d]furan and N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-9,9-dimethyl-9H-fluorene-2-amine were used in a 1:1 equivalent ratio.

[0535] Synthesis Example 17: Synthesis of Compound 2-33

[0536] [Reaction Formula 17]

[0537] Compounds 2-33 were synthesized in the same manner as in Synthesis Example 8, except that Int-7 (CAS No.: 2110512-06-4) and bis(9,9-dimethyl-9H-fluoren-2-yl)amine (CAS No.: 500717-23-7) were used in a 1:1 equivalent ratio.

[0538] (Preparation of the comparative compound)

[0539] Comparative Synthesis Example 1: Synthesis of Comparative Compound R-1

[0540] The comparative compound R-1 was synthesized by referring to the known synthetic method in registered patent KR 10-2293436.

[0541] Comparative Synthesis Example 2: Synthesis of Comparative Compound R-2

[0542] The comparative compound R-2 was synthesized using the synthetic method disclosed in registered patent KR 10-0669716.

[0543] Comparative Synthesis Example 3: Synthesis of Comparative Compound R-3

[0544] The comparative compound R-3 was synthesized by referring to the known synthetic method in registered patent KR 10-1789998.

[0545] Examples 1 to 4 and Comparative Examples 1 to 5: Measurement of Refractive Index

[0546] Using an ellipsometer (JAWoollam Co., M-2000) ® The refractive index of the first hole transport auxiliary layer compound at a wavelength of 520 nm was measured and is shown in Table 1 below.

[0547] The refractive index was measured using a 50 nm film formed on a silicon wafer substrate by vacuum deposition.

[0548] Except for the modification of the first hole transport auxiliary layer compound as described in Table 1 below, the refractive index was measured in the same manner as in Example 1.

[0549] The refractive index of the hole transport layer compound at a wavelength of 520 nm was also measured in the same manner as described above, and its value was 1.749.

[0550] [Table 1]

[0551] Example 5

[0552] A glass substrate coated with an ITO (indium tin oxide) thin film was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with solvents such as isopropanol, acetone, and methanol, and then dried. It was then transferred to a plasma cleaner and cleaned with oxygen plasma for 10 minutes before being transferred to a vacuum depositor. The prepared ITO transparent electrode was used as the anode. Compound A, doped with 3% NDP-9 (Novaled GmbH), was vacuum deposited on the ITO substrate to form a 100 Å thick hole injection layer. Compound A was then deposited on the hole injection layer to a thickness of 1350 Å to form a hole transport layer. On the hole transport layer, the second compound 1-393 obtained in Synthesis Example 10 was deposited to a thickness of 270 Å to form a first hole transport auxiliary layer. On the first hole transport auxiliary layer, the third compound 2-34 obtained in Synthesis Example 12 was deposited to a thickness of 50 Å to form a second hole transport auxiliary layer. On the second hole transport auxiliary layer, 85 wt% of the first compound B-56 ​​(40%) synthesized in Synthesis Example 1 and the fourth compound D-105 (60%) synthesized in Synthesis Example 5 were used as the host, and 15 wt% PtGD was used as the dopant to form a 380 Å thick light-emitting layer by vacuum deposition. Subsequently, compound C was deposited on the light-emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compounds D and Liq were simultaneously vacuum deposited in a 1:1 ratio to form a 310 Å thick electron transport layer. On the electron transport layer, 15 Å of Yb and 1200 Å of Al were sequentially vacuum deposited to form a cathode, thereby fabricating an organic light-emitting diode.

[0553] Organic light-emitting diodes are fabricated to have the following structure: ITO / compound A (3% NDP-9 doped, 100 Å) / compound A (1350 Å) / first hole transport auxiliary layer (compound 1-393, 270 Å) / second hole transport auxiliary layer (compound 2-34, 50 Å) / light-emitting layer [body (compound B-56 ​​: compound D-105 = 4 : 6 ): PtGD = 85 wt% : 15 wt%] (380 Å) / compound C (50 Å) / compound D : Liq (310 Å) / Yb (15 Å) / Al (1200 Å).

[0554] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine

[0555] Compound C: 4-{4-[3-(9,9-dimethyl-9H-fluorene-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[0556] Compound D: 2-(4-{1-[4-(diphenyl-1,3,5-triazin-2-yl)phenyl]naphth-2-yl}phenyl)-4,6-diphenyl-1,3,5-triazine

[0557] PtGD:

[0558] Examples 6 to 14 and Comparative Examples 6 to 10

[0559] Except for the changes in composition described in Table 2 below, the individual organic light-emitting diodes are manufactured in the same manner as in Example 5.

[0560] Evaluation: Luminous efficiency characteristics

[0561] The luminous efficiency of the organic light-emitting diodes according to Examples 5 to 14 and Comparative Examples 6 to 10 was evaluated.

[0562] The specific measurement methods are as follows, and the results are shown in Table 2.

[0563] (1) Measure the change in current density based on the voltage change

[0564] While increasing the voltage from 0 V to 10 V, the current flowing through the unit diode in the obtained organic light-emitting diode was measured using a current-voltmeter (Keithley 2400), and the measured current value was divided by the area to provide the result.

[0565] (2) Measure the change in brightness based on voltage changes

[0566] The brightness was measured using a luminance meter (MinoltaCs-1000A) while the voltage of the organic light-emitting diode was increased from 0 V to 10 V.

[0567] (3) Measure luminous efficiency

[0568] Using the brightness and current density and voltage measured according to (1) and (2) above, calculate the voltage at the same current density (10 mA / cm²). 2 Current efficiency (cd / A) at ).

[0569] The relative values ​​of luminous efficiency based on Example 5 are shown in Table 2 below.

[0570] [Table 2]

[0571] Referring to Table 2, it can be confirmed that the organic light-emitting diodes according to Examples 5 to 14 exhibit significantly improved efficiency characteristics compared to the organic light-emitting diodes according to Comparative Examples 6 to 10.

[0572] Although this disclosure has been described in conjunction with exemplary embodiments that are now considered practical, it should be understood that the invention is not limited to the disclosed embodiments, but rather is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. An organic optoelectronic device, comprising: The anode and cathode facing each other, The light-emitting layer between the anode and the cathode, The hole transport layer between the anode and the light-emitting layer, and A hole transport auxiliary layer between the light-emitting layer and the hole transport layer, in, 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. The light-emitting layer contains a first compound represented by a combination of chemical formula 1 and chemical formula 2. The first hole transport auxiliary layer contains a second compound represented by chemical formula 3. The second hole transport auxiliary layer contains a third compound represented by chemical formula 3. The second compound and the third compound are different from each other. The refractive index of the hole transport layer is higher than that of the first hole transport auxiliary layer, and The refractive index of the first hole transport auxiliary layer is less than or equal to 2.

0. [Chemical Formula 1] [Chemical Formula 2] In chemical formula 1 and chemical formula 2, Z 1 To Z 3 Each is independently N or CL a -R a , Z 1 To Z 3 At least two of them are N. X 1 For NL b -R b O or S L a L b and L 1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof. R a R b R 1 and R 2 Each of these elements is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, or combinations thereof. Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof. R a Ar 1 and Ar 2 Each exists independently, or R a Ar 1 and Ar 2 Adjacent groups are linked to form substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic rings. m1 and m2 are each an independent integer from 1 to 4, and When m1 and m2 are each independently 2 or greater, R 1 and R 2 Each is the same as or different from the other; [Chemical Formula 3] In chemical formula 3, X 2 For O, S or CR c R d , L 4 To L 6 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene. Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. R c R d and R 6 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. R c and R d They exist independently or are connected to each other to form substituted or unsubstituted spirodifluorene. A is substituted or unsubstituted benzene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, or substituted or unsubstituted spirodifluorene. m6 is an integer from 1 to 3, and When m6 is 2 or greater, R 6 They are the same as or different from each other.

2. The organic optoelectronic device according to claim 1, wherein... The refractive index of the first hole transport auxiliary layer is less than or equal to about 1.

8.

3. The organic optoelectronic device according to claim 1, wherein... The refractive index of the first hole transport auxiliary layer is less than or equal to the refractive index of the second hole transport auxiliary layer.

4. The organic optoelectronic device according to claim 1, wherein... The T1 energy of the second hole transport auxiliary layer is greater than or equal to 2.5 eV.

5. The organic optoelectronic device according to claim 1, wherein... The first compound is represented by any one of chemical formulas 1-I to 1-VI: [Chemical Formula 1-I] [Chemical Formula 1-II] [Chemical Formula 1-III] [Chemical Formula 1-IV] [Chemical Formula 1-V] [Chemical Formula 1-VI] In chemical formulas 1-I to 1-VI Z 1 To Z 3 Each is independently N or CL a -R a , Z 1 To Z 3 At least two of them are N. X 1 For NL b -R b O or S L a L b and L 1 To L 3 Each of these can be independently a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted dibenzothiopheneylene. Ar 1 and Ar 2 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted trefyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophene, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, or substituted or unsubstituted triazine. R a R b R 1 and R 2 Each of the following is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiopheneyl. m1 and m2 are each an independent integer from 1 to 4. m3 is an integer of 1 or 3, and When m1 to m3 are each independently 2 or greater, R 1 To R 3 They are the same as or different from each other.

6. The organic optoelectronic device according to claim 1, wherein... Chemical formula 3 can be represented by any one of chemical formulas 3-I to 3-VIII: [Chemical Formula 3-I] [Chemical Formula 3-II] [Chemical Formula 3-III] [Chemical Formula 3-IV] [Chemical Formula 3-V] [Chemical Formula 3-VI] [Chemical Formula 3-VII] [Chemical Formula 3-VIII] In chemical formulas 3-I to 3-VIII X 2 and X 3 Each independently represents O, S, or CR. b R c , L 4 To L 6 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene. Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. R b R c and R 6 To R 12 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. m6 is an integer from 1 to 3. m7, m9, and m10 to m12 are each an independent integer from 1 to 4. m8 is an integer of 1 or 2, and When m6 to m12 are each independently 2 or greater, R 6 To R 12 They are the same as or different from each other.

7. The organic optoelectronic device according to claim 1, wherein... The luminescent layer also contains a fourth compound represented by chemical formula 4, a combination of chemical formulas 5 and 6, chemical formula 7, or chemical formula 8: [Chemical Formula 4] In chemical formula 4, R 13 To R 17 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. L 7 and L 8 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene. m13, m16, and m17 are each an independent integer from 1 to 4. m14 and m15 are each an independent integer from 1 to 3. When m13 to m17 are 2 or greater, R 13 To R 17 Each is the same as or different from the others, and n is an integer from 0 to 2; [Chemical Formula 5] [Chemical Formula 6] In chemical formulas 5 and 6, a1 in chemical formula 5 up to a4 The two adjacent ones in the middle are each related to the chemical formula 6. Connecting carbon (C). a1 in chemical formula 5 up to a4 The other two not connected to chemical formula 6 are CL. c -R e , L c L 9 and L 10 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene. R e R 18 and R 19 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. Ar 7 and Ar 8 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. m18 and m19 are each an independent integer from 1 to 4, and When m18 and m19 are 2 or greater, R 18 and R 19 Each is the same as or different from the other; [Chemical Formula 7] In chemical formula 7, L 11 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene. R 20 To R 23 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. Ar 9 The substituted or unsubstituted C6 to C20 aryl group or the substituted or unsubstituted C2 to C30 heterocyclic group, m20, m22, and m23 are each an independent integer from 1 to 4. m21 is an integer from 1 to 3, and When m20 to m23 are 2 or greater, R 20 To R 23 Each is the same as or different from the other; [Chemical Formula 8] In chemical formula 8, X 4 For O, S, NR f CR g R h or SiR i R j , R f R g R h R i R j and R 24 Each of these groups is independently hydrogen, deuterium, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group. m24 is an integer from 1 to 4, and B is any one of the rings listed in group I. [Group I] In group I, For the connection point, X 5 For O, S, NR k CR l R m or SiR n R o , R k R l R m R n R o and R 25 To R 29 Each is independently hydrogen, deuterium, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and R k and R 24 To R 29 At least one of them is a group represented by chemical formula a. [Chemical formula a] In chemical formula a, L 12 To L 14 Each is an independent single bond or a substituted or unsubstituted C6 to C30 arylene. Ar 10 and Ar 11 Each is independently a substituted or unsubstituted amino group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and This is the connection point.

8. The organic optoelectronic device according to claim 7, wherein... The first compound is represented by chemical formula 1-I. The second compound is represented by the chemical formula 3-Ia. The third compound is represented by any one of the chemical formulas 3-Ib, 3-Ic, and 3-VIII, and The fourth compound is represented by any one of chemical formulas 4-8, 7-2, and 7-3: [Chemical Formula 1-I] In chemical formula 1-I, Z 1 To Z 3 Each is N, X 1 For NL b -R b O or S L a L b and L 1 To L 3 Each of these can be independently a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted dibenzothiopheneylene. R b Ar 1 and Ar 2 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted trefyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophene, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, or substituted or unsubstituted triazine. R 1 and R 2 Each of the following is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiopheneyl. m1 and m2 are each an independent integer from 1 to 4, and m3 is an integer of 1 or 3; [Chemical Formula 3-Ia] In chemical formula 3-Ia, R c and R d Each is independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C12 aryl. Ar 3 and Ar 4 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted 1-fluorenyl, substituted or unsubstituted 2-fluorenyl, substituted or unsubstituted 3-fluorenyl, substituted or unsubstituted 4-fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted dibenzothiophenyl. R 6 R 7a and R 7b Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, or substituted or unsubstituted C6 to C12 aryl, and m6 is an integer from 1 to 3; [Chemical Formula 3-Ib] [Chemical Formula 3-Ic] [Chemical Formula 3-VIII] In chemical formulas 3-Ib, 3-Ic, and 3-VIII X 2 For O or S, R c and R d Each is independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C12 aryl. L 4 To L 6 Each is an independent single bond or a substituted or unsubstituted phenylene group. Ar 3 and Ar 4 Each of these compounds is independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted 1-fluorenyl, substituted or unsubstituted 2-fluorenyl, substituted or unsubstituted 3-fluorenyl, substituted or unsubstituted 4-fluorenyl, substituted or unsubstituted 9-fluorenyl, substituted or unsubstituted 9,9-spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted dibenzothiopheneyl. R 6 R 7 R 10 and R 11 Each of them is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, or substituted or unsubstituted C6 to C12 aryl. m6 is an integer from 1 to 3. m7, m10, m11, and m42 are each an independent integer from 1 to 4, and R 42 It is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, substituted or unsubstituted silyl or combinations thereof; [Chemical Formula 4-8] In chemical formula 4-8, R 13 To R 16 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group. L 7 and L 8 Each can be independently a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene. Ar 5 and Ar 6 Each can be independently substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, or substituted or unsubstituted fluorenyl. m13 and m16 are each an independent integer from 1 to 4, and m14 and m15 are each an independent integer from 1 to 3; [Chemical Formula 7-2] [Chemical Formula 7-3] In chemical formulas 7-2 and 7-3, Ar 9 For substituted or unsubstituted phenyl or substituted or unsubstituted biphenyl, L 11 Each is an independent single bond or a substituted or unsubstituted phenylene group. R 20 To R 23 Each can be independently hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted carbazole. R 22 and R 23 One of them is a substituted or unsubstituted carbazole group. m20, m22, and m23 are each independently an integer from 1 to 4, and m21 is an integer from 1 to 3.

9. A display device comprising the organic optoelectronic device according to any one of claims 1 to 8.

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