Organic optoelectronic device and display device

Abstract

The present invention relates to an organic optoelectronic device and a display device, the organic optoelectronic device comprising: an anode and a cathode facing each other; a light emitting layer located between the anode and the cathode; a hole transport layer located between the anode and the light emitting layer; and a hole transport auxiliary layer located between the hole transport layer and the light emitting layer, the hole transport auxiliary layer including a first hole transport auxiliary layer adjacent to the hole transport layer and a second hole transport auxiliary layer adjacent to the light emitting layer, the first hole transport auxiliary layer includes a first compound represented by a combination of Chemical Formula 1 and Chemical Formula 2, and the second hole transport auxiliary layer includes a second compound represented by a combination of Chemical Formula 3 and Chemical Formula 4. Details of Chemical Formulae 1 to 4 are as defined in the specification.

Description

Technical Field

[0001] Organic optoelectronic devices and display devices have been 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 providing 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 attracted 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 influenced 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 long lifetime characteristics.

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

[0009] Technical solution

[0010] According to one embodiment, an organic optoelectronic device includes 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 hole transport layer and the light-emitting layer, wherein the hole transport auxiliary layer includes a first hole transport auxiliary layer adjacent to the hole transport layer and a second hole transport auxiliary layer adjacent to the light-emitting layer, the first hole transport auxiliary layer comprising a first compound represented by a combination of chemical formula 1 and chemical formula 2, the second hole transport auxiliary layer comprising a second compound represented by a combination of chemical formula 3 and chemical formula 4, and the first compound and the second compound are different from each other.

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

[0012] In chemical formula 1 and chemical formula 2, X1 and X 2 Each is independently O, S, or CR a R b , R a and R b Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. a1 of chemical formula 1 up to a4 Each is independently connected to carbon (C) or CR. c , Chemical formula 2 It is the linker carbon (C). a1 of chemical formula 1 up to a4 The two adjacent ones connected to chemical formula 2 a1 of chemical formula 1 up to a4 The other two not connected to chemical formula 2 are each independently CR. c , R c and R 1 To R 5 Each of these groups is independently hydrogen, deuterium, cyano, halogen, 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. L 1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group. Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m1 is an integer from 1 to 3; [Chemical Formula 3] [Chemical Formula 4]

[0013] In chemical formulas 3 and 4, X 3 and X 4 Each is independently O, S, or CR d R e , X 3 and X 4 At least one of them is O or S. R d and Re Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. Chemical formula 3, b1 up to b4 Each is independently connected to carbon (C) or CR. f , Chemical formula 4 It is the linker carbon (C). Chemical formula 3, b1 up to b4 The two adjacent ones in the middle are connected to chemical formula 4. B1 of chemical formula 3 up to b4 The other two not connected to chemical formula 4 are each independently CR. f , R f and R 6 To R 10 Each of these groups is independently hydrogen, deuterium, cyano, halogen, 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. L 4 To L 6 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group. 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, and m2 is an integer from 1 to 3.

[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 long lifespan characteristics. 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: Hole injection layer; 35: Electron transport layer Detailed Implementation

[0024] Embodiments of the invention are described in detail below. However, these are shown by way of example and are not intended to limit the invention, which is defined only by the scope of the appended claims.

[0025] In this specification, unless otherwise defined, “substituted” means that at least one hydrogen atom of a substituent or compound is replaced by one of the following: 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 one of the following: 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 one of the following: deuterium, C1 to C20 alkyl, 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 one of the following: deuterium, C1 to C5 alkyl, 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 one of the following: deuterium, cyano, methyl, ethyl, propyl, butyl, 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 replacing 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 group can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted tetraphenyl, a substituted or unsubstituted pyrene, a substituted or unsubstituted biphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted meta-terphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted trefyl, a substituted or unsubstituted benzo[a]phenanthyl, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted peryl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indene, or a combination thereof, but is 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 benzothiophene group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indoleyl group, or a substituted or unsubstituted group. Quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxolinyl, substituted or unsubstituted naphridyl, 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 carbazoyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthophenyl, substituted or unsubstituted benzofuran fluorenyl, substituted or unsubstituted benzothiophenenyl or combinations thereof, but not limited thereto.

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

[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] 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.

[0039] Organic light-emitting diodes (OLEDs) are described herein as an example of organic optoelectronic devices, but the invention is not limited thereto and can be applied in the same manner to other organic optoelectronic devices.

[0040] 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 will be understood that when an element such as a layer, film, region, or substrate is referred to as being "on" another element, it can 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.

[0041] Figure 1 This is a schematic cross-sectional view of an organic light-emitting diode according to one embodiment.

[0042] Reference Figure 1 Describe an organic light-emitting diode according to one embodiment.

[0043] 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.

[0044] 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.

[0045] The cathode 20 may be made of a conductor with a small work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 20 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc., or alloys thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0046] 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.

[0047] The light-emitting layer 31 comprises a host and a dopant, and the host may be, for example, a phosphorescent host.

[0048] The phosphorescent host should facilitate the injection and transport of holes and electrons within the emissive layer, ultimately enabling holes and electrons to meet and form excitons, and should be able to efficiently transfer the energy of the formed excitons to the dopant. Examples of phosphorescent hosts may include organic compounds, including carbazole, indolocarbazole, dibenzofuran, dibenzothiophene, indolodibenzopyran, indolodibenzothiophene, fluorene, indobenzocarbazole, triphenylene, pyrimidine, triazine, or combinations thereof.

[0049] Phosphorescent substrates can be used without restrictions, as long as the materials are known, and can be, for example, a single substrate or a mixture of substrates.

[0050] The dopant can be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and can be, for example, a red or green phosphorescent dopant.

[0051] 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 more states. Dopants can be, for example, inorganic, organic, or organic / inorganic compounds, and one or more of these types can be used.

[0052] 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.

[0053] [Chemical Formula Z]

[0054] L 7 MX 5

[0055] In the chemical formula Z, M is a metal, and L 7 and X 5 The same or different ligands that form a complex with M.

[0056] 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 7 and X 5 It could be, for example, a bidentate ligand.

[0057] By L 7 and X 5 Examples of ligands may be selected from, but are not limited to, the chemical formulas listed in group A.

[0058] [Group A]

[0059] 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, and R 303 To R 324 Each 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. n1 is an integer from 1 to 5. n² is an integer from 1 to 4. n3 is an integer from 1 to 3. n4 is an integer of 1 or 2, and n5 is an integer from 1 to 6.

[0060] When n1 is 2 or greater, each substituent can be the same as or different from each other.

[0061] When n2 is 2 or greater, each substituent can be the same as or different from each other.

[0062] When n3 is 2 or greater, each substituent can be the same as or different from each other.

[0063] When n4 is 2 or greater, each substituent can be the same as or different from each other.

[0064] When n5 is 2 or greater, each substituent can be the same as or different from each other.

[0065] In one embodiment, the dopant may be an iridium complex and may be represented by, for example, chemical formula 6-1 or chemical formula 6-2.

[0066] [Chemical Formula 6-1]

[0067] In chemical formula 6-1, R 101 To R 116 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 , 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 of a monovalent anion and a ligand coordinated to iridium via a lone pair of electrons from a carbon or heteroatom. m19 and m20 are each independent integers from 0 to 3, and m19 + m20 is an integer from 1 to 3. [Chemical Formula V-1]

[0068] 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.

[0069] [Chemical Formula 6-2]

[0070] In chemical formula 6-2, R 101 To R 117 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. L 100 It is a bidentate ligand of a monovalent anion and a ligand coordinated to iridium via a lone pair of electrons from a carbon or heteroatom. n1 and n2 are each independent integers from 0 to 3, and n1 + n2 is an integer from 1 to 3.

[0071] As an example, it may include dopants represented by the chemical formula Z-1.

[0072] [Chemical Formula Z-1]

[0073] In chemical formula Z-1, 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 mono-, di-, tri-, or tetra-substituted or unsubstituted; 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, aralkyl, 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.

[0074] Platinum complexes can be represented, for example, by chemical formula 7-1 or chemical formula 7-2.

[0075] [Chemical Formula 7-1]

[0076] [Chemical Formula 7-2]

[0077] In chemical formulas 7-1 and 7-2, 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 132 R 133 R 134 Or tert-butyl, and R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0078] Compositions that also contain dopants can be, for example, green light emitting compositions.

[0079] In addition to the light-emitting layer, the organic light-emitting diode may also include a hole injection layer 34.

[0080] Hole injection layer 34 is a layer that helps holes to be injected from anode 10 into hole transport layer 32, and may contain a material having a HOMO energy level between the work function of the conductor forming anode 10 and the HOMO energy level of the material forming hole transport layer 32.

[0081] For example, at least one of the hole transport layer 32 and the hole injection layer 34 may contain at least one of the compounds listed in Group B and be different from the materials of the first hole transport auxiliary layer and the second hole transport auxiliary layer described below.

[0082] [Group B]

[0083] (Dn represents the number of deuterium substitutions and the structure that is substituted by one or more deuteriums)

[0084] In addition to the compounds described above, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, and compounds with similar structures can also be used in hole transport layer 32 and hole injection layer 34.

[0085] 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.

[0086] The first hole transport auxiliary layer comprises a first compound represented by a combination of chemical formula 1 and chemical formula 2. The second hole transport auxiliary layer comprises a second compound represented by a combination of chemical formulas 3 and 4, and The first compound and the second compound are different from each other.

[0087] [Chemical Formula 1] [Chemical Formula 2]

[0088] In chemical formula 1 and chemical formula 2, X 1 and X 2 Each is independently O, S, or CR a R b , R a and R b Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. a1 of chemical formula 1 up to a4 Each is independently connected to carbon (C) or CR. c , Chemical formula 2 It is the linker carbon (C). a1 of chemical formula 1 up to a4 The two adjacent ones connected to chemical formula 2 a1 of chemical formula 1 up to a4 The other two not connected to chemical formula 2 are each independently CR. c , R c and R 1 To R 5Each of these groups is independently hydrogen, deuterium, cyano, halogen, 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. L 1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group. Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m1 is an integer from 1 to 3; [Chemical Formula 3] [Chemical Formula 4]

[0089] In chemical formulas 3 and 4, X 3 and X 4 Each is independently O, S, or CR d R e , X 3 and X 4 At least one of them is O or S. R d and R e Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. Chemical formula 3, b1 up to b4 Each is independently connected to carbon (C) or CR. f , Chemical formula 4 It is the linker carbon (C). Chemical formula 3, b1 up to b4 The two adjacent ones in the middle are connected to chemical formula 4. B1 of chemical formula 3 up to b4 The other two not connected to chemical formula 4 are each independently CR. f , R f and R 6 To R 10 Each of these groups is independently hydrogen, deuterium, cyano, halogen, 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. L4 To L 6 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group. 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, and m2 is an integer from 1 to 3.

[0090] An organic light-emitting diode according to one embodiment includes a combination of two hole transport auxiliary layers at the interface between a hole transport layer and a light-emitting layer, thereby adjusting the hole injection capability of the first hole transport auxiliary layer to balance the charge in the light-emitting layer, and balancing the hole and electron densities by blocking electrons in the second hole transport auxiliary layer, thereby producing improved lifetime characteristics.

[0091] When m1 is 2 or greater, each R 5 They can be the same as or different from each other.

[0092] When m2 is 2 or greater, each R 10 They can be the same as or different from each other.

[0093] For example, the first compound above can be represented by any one of chemical formulas 1A, 1B, 1C, 1D, 1E, and 1F.

[0094] [Chemical Formula 1A] [Chemical Formula 1B]

[0095] [Chemical Formula 1C] [Chemical Formula 1D]

[0096] [Chemical Formula 1E] [Chemical Formula 1F]

[0097] In chemical formulas 1A, 1B, 1C, 1D, 1E, and 1F, X 1 X 2 R 1 To R 5 L 1 To L 3 Ar 1 and Ar 2 m1 is as defined in chemical formulas 1 and 2. R c1 To R c4Each is independently hydrogen, deuterium, cyano, halogen, 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.

[0098] Depending on the substitution site of the amino group, chemical formula 1A can be represented by any of the following, for example, chemical formulas 1A-1 to 1A-4.

[0099] [Chemical Formula 1A-1] [Chemical Formula 1A-2]

[0100] [Chemical Formula 1A-3] [Chemical Formula 1A-4]

[0101] In chemical formulas 1A-1 to 1A-4 X 1 X 2 R 1 To R 5 L 1 To L 3 Ar 1 Ar 2 m1, R c1 and R c4 Same as above.

[0102] Depending on the substitution site of the amino group, chemical formula 1B can be represented by any of, for example, chemical formulas 1B-1 to 1B-4.

[0103] [Chemical Formula 1B-1] [Chemical Formula 1B-2]

[0104] [Chemical Formula 1B-3] [Chemical Formula 1B-4]

[0105] In chemical formulas 1B-1 to 1B-4 X 1 X 2 R 1 To R 5 L 1 To L 3 Ar 1 Ar 2 m1, R c1 and R c2 Same as above.

[0106] Depending on the substitution site of the amino group, chemical formula 1C can be represented by any of the following formulas, for example, 1C-1 to 1C-4.

[0107] [Chemical Formula 1C-1] [Chemical Formula 1C-2]

[0108] [Chemical Formula 1C-3] [Chemical Formula 1C-4]

[0109] In chemical formulas 1C-1 to 1C-4 X 1 X 2 R 1 To R 5 L 1 To L 3 Ar 1 Ar 2 m1, R c3 and R c4 Same as above.

[0110] Depending on the substitution site of the amino group, chemical formula 1D can be represented by any of the following, for example, chemical formulas 1D-1 to 1D-4.

[0111] [Chemical Formula 1D-1] [Chemical Formula 1D-2]

[0112] [Chemical Formula 1D-3] [Chemical Formula 1D-4]

[0113] In chemical formulas 1D-1 to 1D-4 X 1 X 2 R 1 To R 5 L 1 To L 3 Ar 1 Ar 2 m1, R c1 and R c4 Same as above.

[0114] Depending on the substitution site of the amino group, chemical formula 1E can be represented by any of the following formulas, for example, 1E-1 to 1E-4.

[0115] [Chemical Formula 1E-1] [Chemical Formula 1E-2]

[0116] [Chemical Formula 1E-3] [Chemical Formula 1E-4]

[0117] In chemical formulas 1E-1 to 1E-4 X 1 X 2 R 1 To R 5 L 1 To L 3 Ar 1 Ar 2 m1, R c3 and R c4 Same as above.

[0118] Depending on the substitution site of the amino group, chemical formula 1F can be represented by any of the following, for example, chemical formulas 1F-1 to 1F-4.

[0119] [Chemical Formula 1F-1] [Chemical Formula 1F-2]

[0120] [Chemical Formula 1F-3] [Chemical Formula 1F-4]

[0121] In chemical formulas 1F-1 to 1F-4 X 1 X 2 R 1 To R 5 L 1 To L 3 Ar 1 Ar 2 m1, R c1 and R c2 Same as above.

[0122] The structures of the second compound, depending on its fusion form, can be disclosed in the same manner as described above, and will not be repeated hereafter; those skilled in the art will be able to understand the structures of the second compound as variants of the first compound, depending on its specific fusion form.

[0123] For example, the first compound can be represented by the chemical formula 1F.

[0124] As a specific example, X of chemical formula 1F 1 and X 2 One of them could be CR a R b And the other can be O or S.

[0125] As another concrete example, X of chemical formula 1F 1 and X 2 Each can be O.

[0126] As a more specific example, chemical formula 1F can be represented as one of chemical formulas 1F-(i)-1 to 1F-(i)-4 and chemical formulas 1F-(ii)-1 to 1F-(ii)-4.

[0127] [Chemical Formula 1F-(i)-1] [Chemical Formula 1F-(i)-2]

[0128] [Chemical Formula 1F-(i)-3] [Chemical Formula 1F-(i)-4]

[0129] [Chemical Formula 1F-(ii)-1] [Chemical Formula 1F-(ii)-2]

[0130] [Chemical Formula 1F-(ii)-3] [Chemical Formula 1F-(ii)-4]

[0131] In chemical formulas 1F-(i)-1 to 1F-(i)-4 and 1F-(ii)-1 to 1F-(ii)-4, X 1 and X 2 Each is independently O or S, R c1 and R c2 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.

[0132] R a R b R 1 To R 5 L 1 To L 3 Ar 1 and Ar 2 And m1 as defined in chemical formula 1 and chemical formula 2.

[0133] As a most concrete example, the first compound can be represented by the chemical formula 1F-(ii)-1.

[0134] For example, the second compound can be represented by any one of the chemical formulas 2A, 2B, 2C, 2D, 2E, and 2F.

[0135] [Chemical Formula 2A] [Chemical Formula 2B]

[0136] [Chemical Formula 2C] [Chemical Formula 2D]

[0137] [Chemical Formula 2E] [Chemical Formula 2F]

[0138] In chemical formulas 2A, 2B, 2C, 2D, 2E, and 2F, X 3 X 4 R 6 To R 10 L 4 To L 6 Ar 3 and Ar 4 And m2 as defined in chemical formulas 3 and 4, and R f1 To R f4 Each is independently hydrogen, deuterium, cyano, halogen, 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.

[0139] As a specific example, the second compound can be represented by chemical formula 2A or chemical formula 2F.

[0140] As a more specific example, X in chemical formula 2A 3 It can be CR d R e And X 4 It can be O or S.

[0141] As a more specific example, X of chemical formula 2F 3 and X 4 Each can be either O or S independently.

[0142] As a more specific example, chemical formula 2A can be represented as one of chemical formulas 2A-(i)-1 to 2A-(i)-4 and chemical formulas 2A-(ii)-1 to 2A-(ii)-4.

[0143] [Chemical Formula 2A-(i)-1] [Chemical Formula 2A-(i)-2]

[0144] [Chemical Formula 2A-(i)-3] [Chemical Formula 2A-(i)-4]

[0145] [Chemical Formula 2A-(ii)-1] [Chemical Formula 2A-(ii)-2]

[0146] [Chemical Formula 2A-(ii)-3] [Chemical Formula 2A-(ii)-4]

[0147] In chemical formulas 2A-(i)-1 to 2A-(i)-4 and 2A-(ii)-1 to 2A-(ii)-4, X 3 and X 4 Each is independently O or S, R f1 and R f4 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.

[0148] R d R e R 6 To R 10 L 4 To L 6 Ar 3 and Ar 4 And m2 as defined in chemical formulas 3 and 4.

[0149] As a more specific example, chemical formula 2F can be represented by chemical formula 2F-1.

[0150] [Chemical formula 2F-1]

[0151] In chemical formula 2F-1, X 3 and X 4 Each is independently O or S, R f1 and R f2Each of these groups is independently hydrogen, deuterium, cyano, halogen, 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. R 6 To R 10 L 4 To L 6 Ar 3 and Ar 4 And m2 as defined in chemical formulas 3 and 4.

[0152] As a most specific example, the second compound can be represented by the chemical formula 2A-(i)-1 or the chemical formula 2F-1.

[0153] As a specific example, Ar 1 To 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 fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted dibenzothiophene.

[0154] For example, Ar 1 To Ar 4 Each of them can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted dibenzothiophene.

[0155] For example, R 1 To R 10 Each of them can be hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl or substituted or unsubstituted C6 to C12 aryl.

[0156] As a specific example, R 1 To R 10 Each of them can be hydrogen, deuterium, substituted or unsubstituted C1 to C5 alkyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0157] For example, R a R b R d and R e Each can be independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C12 aryl.

[0158] As a specific example, R a R b R d and R e Each can be independently a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0159] For example, L 1 To L 6 Each can be a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0160] In one implementation, L 2 -Ar 1 L 3 -Ar 2 L 5 -Ar 3 and L 6 -Ar 4 Each can be independently selected from the substituents listed in Group I.

[0161] [Group I]

[0162] In group I, R 11 To R 14 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. R 15 and R 16 Each is independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C12 aryl. m3 is an integer from 1 to 5. m4 is an integer from 1 to 4. m5 is an integer from 1 to 3. m6 is an integer of 1 or 2, and It is a connection point.

[0163] When m3 is 2 or greater, each R 11 They can be the same as or different from each other.

[0164] When m4 is 2 or greater, each R 12 They can be the same as or different from each other.

[0165] When m5 is 2 or greater, each R 13 They can be the same as or different from each other.

[0166] When m6 is 2, each R 14 They can be the same as or different from each other.

[0167] For example, the first compound and the second compound may each be independently selected from the compounds listed in Group 1, and the first compound and the second compound contained in the composition are different from each other.

[0168] [Group 1]

[0169] [A-1] [A-2] [A-3] [A-4] [A-5]

[0170] [A-6] [A-7] [A-8] [A-9] [A-10]

[0171] [A-11] [A-12] [A-13] [A-14] [A-15]

[0172] [A-16] [A-17] [A-18] [A-19] [A-20]

[0173] [A-21] [A-22] [A-23] [A-24] [A-25]

[0174] [A-26] [A-27] [A-28] [A-29] [A-30]

[0175] [A-31] [A-32] [A-33] [A-34] [A-35]

[0176] [A-36] [A-37] [A-38] [A-39] [A-40]

[0177] [A-41] [A-42] [A-43] [A-44] [A-45]

[0178] [A-46] [A-47] [A-48] [A-49] [A-50]

[0179] [A-51] [A-52] [A-53] [A-54] [A-55]

[0180] [A-56] [A-57] [A-58] [A-59] [A-60]

[0181] [A-61] [A-62] [A-63] [A-64] [A-65]

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

[0183] [A-71] [A-72] [A-73] [A-74] [A-75]

[0184] [A-76] [A-77] [A-78] [A-79] [A-80]

[0185] [A-81] [A-82] [A-83] [A-84] [A-85]

[0186] [A-86] [A-87] [A-88] [A-89] [A-90]

[0187] [A-91] [A-92] [A-93] [A-94] [A-95]

[0188] [A-96] [A-97] [A-98] [A-99] [A-100]

[0189] [A-101] [A-102] [A-103] [A-104] [A-105]

[0190] [A-106] [A-107] [A-108] [A-109] [A-110]

[0191] [A-111] [A-112] [A-113] [A-114] [A-115]

[0192] [A-116] [A-117] [A-118] [A-119] [A-120]

[0193] [A-121] [A-122] [A-123] [A-124] [A-125]

[0194] [A-126] [A-127] [A-128] [A-129] [A-130]

[0195] [A-131] [A-132] [A-133] [A-134] [A-135]

[0196] [A-136] [A-137] [A-138] [A-139] [A-140]

[0197] [A-141] [A-142] [A-143] [A-144] [A-145]

[0198] [A-146] [A-147] [A-148] [A-149] [A-150]

[0199] [A-151] [A-152] [A-153] [A-154] [A-155]

[0200] [A-156] [A-157] [A-158] [A-159] [A-160]

[0201] [A-161] [A-162] [A-163] [A-164] [A-165]

[0202] [A-166] [A-167] [A-168] [A-169] [A-170]

[0203] [A-171] [A-172] [A-173] [A-174] [A-175]

[0204] [A-176] [A-177] [A-178] [A-179] [A-180]

[0205] [A-181] [A-182] [A-183] [A-184] [A-185]

[0206] [A-186] [A-187] [A-188] [A-189] [A-190]

[0207] [A-191] [A-192] [A-193] [A-194] [A-195]

[0208] [A-196] [A-197] [A-198] [A-199] [A-200]

[0209] [B-1] [B-2] [B-3] [B-4] [B-5]

[0210] [B-6] [B-7] [B-8] [B-9] [B-10]

[0211] [B-11] [B-12] [B-13] [B-14] [B-15]

[0212] [B-16] [B-17] [B-18] [B-19] [B-20]

[0213] [B-21] [B-22] [B-23] [B-24] [B-25]

[0214] [B-26] [B-27] [B-28] [B-29] [B-30]

[0215] [B-31] [B-32] [B-33] [B-34] [B-35]

[0216] [B-36] [B-37] [B-38] [B-39] [B-40]

[0217] [B-41] [B-42] [B-43] [B-44] [B-45]

[0218] [B-46] [B-47] [B-48] [B-49] [B-50]

[0219] [B-51] [B-52] [B-53] [B-54] [B-55]

[0220] [B-56] [B-57] [B-58] [B-59] [B-60]

[0221] [B-61] [B-62] [B-63] [B-64] [B-65]

[0222] [B-66] [B-67] [B-68] [B-69] [B-70]

[0223] [B-71] [B-72] [B-73] [B-74] [B-75]

[0224] [B-76] [B-77] [B-78] [B-79] [B-80]

[0225] [B-81] [B-82] [B-83] [B-84] [B-85]

[0226] [B-86] [B-87] [B-88] [B-89] [B-90]

[0227] [B-91] [B-92] [B-93] [B-94] [B-95]

[0228] [B-96] [B-97] [B-98] [B-99] [B-100]

[0229] [B-101] [B-102] [B-103] [B-104] [B-105]

[0230] [B-106] [B-107] [B-108] [B-109] [B-110]

[0231] [B-111] [B-112] [B-113] [B-114] [B-115]

[0232] [B-116] [B-117] [B-118] [B-119] [B-120]

[0233] [B-121] [B-122] [B-123] [B-124] [B-125]

[0234] [B-126] [B-127] [B-128] [B-129] [B-130]

[0235] [B-131] [B-132] [B-133] [B-134] [B-135]

[0236] [B-136] [B-137] [B-138] [B-139] [B-140]

[0237] [B-141] [B-142] [B-143] [B-144] [B-145]

[0238] [B-146] [B-147] [B-148] [B-149] [B-150]

[0239] [B-151] [B-152] [B-153] [B-154] [B-155]

[0240] [B-156] [B-157] [B-158] [B-159] [B-160]

[0241] [B-161] [B-162] [B-163] [B-164] [B-165]

[0242] [B-166] [B-167] [B-168] [B-169] [B-170]

[0243] [B-171] [B-172] [B-173] [B-174] [B-175]

[0244] [B-176] [B-177] [B-178] [B-179] [B-180]

[0245] [B-181] [B-182] [B-183] [B-184] [B-185]

[0246] [B-186] [B-187] [B-188] [B-189] [B-190]

[0247] [B-191] [B-192] [B-193] [B-194] [B-195]

[0248] [B-196] [B-197] [B-198] [B-199] [B-200]

[0249] [C-1] [C-2] [C-3] [C-4] [C-5]

[0250] [C-6] [C-7] [C-8] [C-9] [C-10]

[0251] [C-11] [C-12] [C-13] [C-14] [C-15]

[0252] [C-16] [C-17] [C-18] [C-19] [C-20]

[0253] [C-21] [C-22] [C-23] [C-24] [C-25]

[0254] [C-26] [C-27] [C-28] [C-29] [C-30]

[0255] [C-31] [C-32] [C-33] [C-34] [C-35]

[0256] [C-36] [C-37] [C-38] [C-39] [C-40]

[0257] [C-41] [C-42] [C-43] [C-44] [C-45]

[0258] [C-46] [C-47] [C-48] [C-49] [C-50]

[0259] [C-51] [C-52] [C-53] [C-54] [C-55]

[0260] [C-56] [C-57] [C-58] [C-59] [C-60]

[0261] [C-61] [C-62] [C-63] [C-64] [C-65]

[0262] [C-66] [C-67] [C-68] [C-69] [C-70]

[0263] [C-71] [C-72] [C-73] [C-74] [C-75]

[0264] [C-76] [C-77] [C-78] [C-79] [C-80]

[0265] [C-81] [C-82] [C-83] [C-84] [C-85]

[0266] [C-86] [C-87] [C-88] [C-89] [C-90]

[0267] [C-91] [C-92] [C-93] [C-94] [C-95]

[0268] [C-96] [C-97] [C-98] [C-99] [C-100]

[0269] [C-101] [C-102] [C-103] [C-104] [C-105]

[0270] [C-106] [C-107] [C-108] [C-109] [C-110]

[0271] [C-111] [C-112] [C-113] [C-114] [C-115]

[0272] [C-116] [C-117] [C-118] [C-119] [C-120]

[0273] [C-121] [C-122] [C-123] [C-124] [C-125]

[0274] [C-126] [C-127] [C-128] [C-129] [C-130]

[0275] [C-131] [C-132] [C-133] [C-134] [C-135]

[0276] [C-136] [C-137] [C-138] [C-139] [C-140]

[0277] [C-141] [C-142] [C-143] [C-144] [C-145]

[0278] [C-146] [C-147] [C-148] [C-149] [C-150]

[0279] [C-151] [C-152] [C-153] [C-154] [C-155]

[0280] [C-156] [C-157] [C-158] [C-159] [C-160]

[0281] [C-161] [C-162] [C-163] [C-164] [C-165]

[0282] [C-166] [C-167] [C-168] [C-169] [C-170]

[0283] [C-171] [C-172] [C-173] [C-174] [C-175]

[0284] [C-176] [C-177] [C-178] [C-179] [C-180]

[0285] [C-181] [C-182] [C-183] [C-184] [C-185]

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

[0287] [C-191] [C-192] [C-193] [C-194] [C-195]

[0288] [C-196] [C-197] [C-198] [C-199] [C-200]

[0289] [D-1] [D-2] [D-3] [D-4] [D-5]

[0290] [D-6] [D-7] [D-8] [D-9] [D-10]

[0291] [D-11] [D-12] [D-13] [D-14] [D-15]

[0292] [D-16] [D-17] [D-18] [D-19] [D-20]

[0293] [D-21] [D-22] [D-23] [D-24] [D-25]

[0294] [D-26] [D-27] [D-28] [D-29] [D-30]

[0295] [D-31] [D-32] [D-33] [D-34] [D-35]

[0296] [D-36] [D-37] [D-38] [D-39] [D-40]

[0297] [D-41] [D-42] [D-43] [D-44] [D-45]

[0298] [D-46] [D-47] [D-48] [D-49] [D-50]

[0299] [D-51] [D-52] [D-53] [D-54] [D-55]

[0300] [D-56] [D-57] [D-58] [D-59] [D-60]

[0301] [D-61] [D-62] [D-63] [D-64] [D-65]

[0302] [D-66] [D-67] [D-68] [D-69] [D-70]

[0303] [D-71] [D-72] [D-73] [D-74] [D-75]

[0304] [D-76] [D-77] [D-78] [D-79] [D-80]

[0305] [D-81] [D-82] [D-83] [D-84] [D-85]

[0306] [D-86] [D-87] [D-88] [D-89] [D-90]

[0307] [D-91] [D-92] [D-93] [D-94] [D-95]

[0308] [D-96] [D-97] [D-98] [D-99] [D-100]

[0309] [D-101] [D-102] [D-103] [D-104] [D-105]

[0310] [D-106] [D-107] [D-108] [D-109] [D-110]

[0311] [D-111] [D-112] [D-113] [D-114] [D-115]

[0312] [D-116] [D-117] [D-118] [D-119] [D-120]

[0313] [D-121] [D-122] [D-123] [D-124] [D-125]

[0314] [D-126] [D-127] [D-128] [D-129] [D-130]

[0315] [D-131] [D-132] [D-133] [D-134] [D-135]

[0316] [D-136] [D-137] [D-138] [D-139] [D-140]

[0317] [D-141] [D-142] [D-143] [D-144] [D-145]

[0318] [D-146] [D-147] [D-148] [D-149] [D-150]

[0319] [D-151] [D-152] [D-153] [D-154] [D-155]

[0320] [D-156] [D-157] [D-158] [D-159] [D-160]

[0321] [D-161] [D-162] [D-163] [D-164] [D-165]

[0322] [D-166] [D-167] [D-168] [D-169] [D-170]

[0323] [D-171] [D-172] [D-173] [D-174] [D-175]

[0324] [D-176] [D-177] [D-178] [D-179] [D-180]

[0325] [D-181] [D-182] [D-183] [D-184] [D-185]

[0326] [D-186] [D-187] [D-188] [D-189] [D-190]

[0327] [D-191] [D-192] [D-193] [D-194] [D-195]

[0328] [D-196] [D-197] [D-198] [D-199] [D-200]

[0329] [E-1] [E-2] [E-3] [E-4] [E-5]

[0330] [E-6] [E-7] [E-8] [E-9] [E-10]

[0331] [E-11] [E-12] [E-13] [E-14] [E-15]

[0332] [E-16] [E-17] [E-18] [E-19] [E-20]

[0333] [E-21] [E-22] [E-23] [E-24] [E-25]

[0334] [E-26] [E-27] [E-28] [E-29] [E-30]

[0335] [E-31] [E-32] [E-33] [E-34] [E-35]

[0336] [E-36] [E-37] [E-38] [E-39] [E-40]

[0337] [E-41] [E-42] [E-43] [E-44] [E-45]

[0338] [E-46] [E-47] [E-48] [E-49] [E-50]

[0339] [E-51] [E-52] [E-53] [E-54] [E-55]

[0340] [E-56] [E-57] [E-58] [E-59] [E-60]

[0341] [E-61] [E-62] [E-63] [E-64] [E-65]

[0342] [E-66] [E-67] [E-68] [E-69] [E-70]

[0343] [E-71] [E-72] [E-73] [E-74] [E-75]

[0344] [E-76] [E-77] [E-78] [E-79] [E-80]

[0345] [E-81] [E-82] [E-83] [E-84] [E-85]

[0346] [E-86] [E-87] [E-88] [E-89] [E-90]

[0347] [E-91] [E-92] [E-93] [E-94] [E-95]

[0348] [E-96] [E-97] [E-98] [E-99] [E-100]

[0349] [E-101] [E-102] [E-103] [E-104] [E-105]

[0350] [E-106] [E-107] [E-108] [E-109] [E-110]

[0351] [E-111] [E-112] [E-113] [E-114] [E-115]

[0352] [E-116] [E-117] [E-118] [E-119] [E-120]

[0353] [E-121] [E-122] [E-123] [E-124] [E-125]

[0354] [E-126] [E-127] [E-128] [E-129] [E-130]

[0355] [E-131] [E-132] [E-133] [E-134] [E-135]

[0356] [E-136] [E-137] [E-138] [E-139] [E-140]

[0357] [E-141] [E-142] [E-143] [E-144] [E-145]

[0358] [E-146] [E-147] [E-148] [E-149] [E-150]

[0359] [E-151] [E-152] [E-153] [E-154] [E-155]

[0360] [E-156] [E-157] [E-158] [E-159] [E-160]

[0361] [E-161] [E-162] [E-163] [E-164] [E-165]

[0362] [E-166] [E-167] [E-168] [E-169] [E-170]

[0363] [E-171] [E-172] [E-173] [E-174] [E-175]

[0364] [E-176] [E-177] [E-178] [E-179] [E-180]

[0365] [E-181] [E-182] [E-183] [E-184] [E-185]

[0366] [E-186] [E-187] [E-188] [E-189] [E-190]

[0367] [E-191] [E-192] [E-193] [E-194] [E-195]

[0368] [E-196] [E-197] [E-198] [E-199] [E-200]

[0369] [F-1] [F-2] [F-3] [F-4] [F-5]

[0370] [F-6] [F-7] [F-8] [F-9] [F-10]

[0371] [F-11] [F-12] [F-13] [F-14] [F-15]

[0372] [F-16] [F-17] [F-18] [F-19] [F-20]

[0373] [F-21] [F-22] [F-23] [F-24] [F-25]

[0374] [F-26] [F-27] [F-28] [F-29] [F-30]

[0375] [F-31] [F-32] [F-33] [F-34] [F-35]

[0376] [F-36] [F-37] [F-38] [F-39] [F-40]

[0377] [F-41] [F-42] [F-43] [F-44] [F-45]

[0378] [F-46] [F-47] [F-48] [F-49] [F-50]

[0379] [F-51] [F-52] [F-53] [F-54] [F-55]

[0380] [F-56] [F-57] [F-58] [F-59] [F-60]

[0381] [F-61] [F-62] [F-63] [F-64] [F-65]

[0382] [F-66] [F-67] [F-68] [F-69] [F-70]

[0383] [F-71] [F-72] [F-73] [F-74] [F-75]

[0384] [F-76] [F-77] [F-78] [F-79] [F-80]

[0385] [F-81] [F-82] [F-83] [F-84] [F-85]

[0386] [F-86] [F-87] [F-88] [F-89] [F-90]

[0387] [F-91] [F-92] [F-93] [F-94] [F-95]

[0388] [F-96] [F-97] [F-98] [F-99] [F-100]

[0389] [F-101] [F-102] [F-103] [F-104] [F-105]

[0390] [F-106] [F-107] [F-108] [F-109] [F-110]

[0391] [F-111] [F-112] [F-113] [F-114] [F-115]

[0392] [F-116] [F-117] [F-118] [F-119] [F-120]

[0393] [F-121] [F-122] [F-123] [F-124] [F-125]

[0394] [F-126] [F-127] [F-128] [F-129] [F-130]

[0395] [F-131] [F-132] [F-133] [F-134] [F-135]

[0396] [F-136] [F-137] [F-138] [F-139] [F-140]

[0397] [F-141] [F-142] [F-143] [F-144] [F-145]

[0398] [F-146] [F-147] [F-148] [F-149] [F-150]

[0399] [F-151] [F-152] [F-153] [F-154] [F-155]

[0400] [F-156] [F-157] [F-158] [F-159] [F-160]

[0401] [F-161] [F-162] [F-163] [F-164] [F-165]

[0402] [F-166] [F-167] [F-168] [F-169] [F-170]

[0403] [F-171] [F-172] [F-173] [F-174] [F-175]

[0404] [F-176] [F-177] [F-178] [F-179] [F-180]

[0405] [F-181] [F-182] [F-183] [F-184] [F-185]

[0406] [F-186] [F-187] [F-188] [F-189] [F-190]

[0407] [F-191] [F-192] [F-193] [F-194] [F-195]

[0408] [F-196] [F-197] [F-198] [F-199] [F-200]

[0409] [F-201] [F-202] [F-203] [F-204] [F-205]

[0410] [F-206] [F-207] [F-208] [F-209] [F-210]

[0411] [F-211] [F-212] [F-213] [F-214] [F-215]

[0412] [F-216] [F-217] [F-218] [F-219] [F-220]

[0413] [F-221] [F-222] [F-223] [F-224] [F-225]

[0414] [F-226] [F-227] [F-228] [F-229] [F-230]

[0415] [F-231] [F-232] [F-233] [F-234] [F-235]

[0416] [F-236] [F-237] [F-238] [F-239] [F-240]

[0417] [F-241] [F-242] [F-243] [F-244] [F-245]

[0418] [F-246] [F-247] [F-248] [F-249] [F-250]

[0419] [F-251] [F-252] [F-253] [F-254] [F-255]

[0420] [F-256] [F-257] [F-258] [F-259] [F-260]

[0421] [F-261] [F-262] [F-263] [F-264] [F-265]

[0422] [F-266] [F-267] [F-268] [F-269] [F-270]

[0423] [F-271] [F-272] [F-273] [F-274] [F-275]

[0424] [F-276] [F-277] [F-278] [F-279] [F-280]

[0425] [F-281] [F-282] [F-283] [F-284] [F-285]

[0426] [F-286] [F-287] [F-288] [F-289] [F-290]

[0427] [F-291] [F-292] [F-293] [F-294] [F-295]

[0428] [F-296] [F-297] [F-298] [F-299] [F-300]

[0429] [F-301] [F-302] [F-303] [F-304] [F-305]

[0430] [F-306] [F-307] [F-308] [F-309] [F-310]

[0431] [F-311] [F-312] [F-313] [F-314] [F-315]

[0432] [F-316] [F-317] [F-318] [F-319] [F-320]

[0433] [F-321] [F-322] [F-323] [F-324] [F-325]

[0434] [F-326] [F-327] [F-328] [F-329] [F-330]

[0435] [F-331] [F-332] [F-333] [F-334] [F-335]

[0436] [F-336] [F-337] [F-338] [F-339] [F-340]

[0437] [F-341] [F-342] [F-343] [F-344] [F-345]

[0438] [F-346] [F-347] [F-348] [F-349] [F-350]

[0439] [F-351] [F-352] [F-353] [F-354] [F-355]

[0440] [F-356] [F-357] [F-358] [F-359] [F-360]

[0441] [F-361] [F-362] [F-363] [F-364] [F-365]

[0442] [F-366] [F-367] [F-368] [F-369] [F-370]

[0443] [F-371] [F-372] [F-373] [F-374] [F-375]

[0444] [F-376] [F-377] [F-378] [F-379] [F-380]

[0445] [F-381] [F-382] [F-383] [F-384] [F-385]

[0446] [F-386] [F-387] [F-388] [F-389] [F-390]

[0447] [F-391] [F-392] [F-393] [F-394] [F-395]

[0448] [F-396] [F-397] [F-398] [F-399] [F-400]

[0449] [F-401] [F-402] [F-403] [F-404] [F-405]

[0450] [F-406] [F-407] [F-408] [F-409] [F-410]

[0451] [F-411] [F-412] [F-413] [F-414] [F-415]

[0452] [F-416] [F-417] [F-418] [F-419] [F-420]

[0453] [F-421] [F-422] [F-423] [F-424] [F-425]

[0454] [F-426] [F-427] [F-428] [F-429] [F-430]

[0455] [F-431] [F-432] [F-433] [F-434] [F-435]

[0456] [F-436] [F-437] [F-438] [F-439] [F-440]

[0457] In the most specific embodiment of the invention, the first compound is represented by chemical formula 1F-(ii)-1, and the second compound may be represented by chemical formula 2A-(i)-1 or chemical formula 2F-1.

[0458] The organic layer 30 may include an electron transport region.

[0459] The electron transport region can further improve the electron injection and / or electron mobility between the cathode 20 and the light-emitting layer 31, but blocks holes.

[0460] 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 electron transport layer 35 and the electron transport auxiliary layer may contain at least one of the compounds listed in Group C.

[0461] [Group C]

[0462] One embodiment may provide an organic light-emitting diode comprising an organic layer including a light-emitting layer 31, a hole transport layer 32, a first hole transport layer 33a, and a second hole transport layer 33b.

[0463] Another implementation could be an organic light-emitting diode that includes a hole injection layer as an organic layer.

[0464] Another implementation could be an organic light-emitting diode that includes an electron transport region as an organic layer.

[0465] 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.

[0466] Organic light-emitting diodes (OLEDs) can be manufactured by forming an organic layer on a substrate using dry film methods such as evaporation, sputtering, plasma electroplating, and ion plating, and then forming a cathode or anode thereon.

[0467] Organic light-emitting diodes (OLEDs) can be used in organic light-emitting display devices.

[0468] Invention Model

[0469] 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.

[0470] 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.

[0471] (Preparation of compounds for organic optoelectronic devices)

[0472] Synthesis Example 1: Synthesis of Compound F-113

[0473] [Reaction Formula 1]

[0474] 10 g (27.66 mmol) of intermediate N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine, 9.7 g (30.43 mmol) of intermediate 11-chloro-7,7-dimethyl-7H-fluoren[4,3-b]benzofuran, 4.25 g (44.26 mmol) of sodium tert-butoxide, and 1.0 g (2.49 mmol) of tri-tert-butylphosphine (P(tBu)3) were dissolved in 184 ml of xylene. 0.76 g (0.83 mmol) of Pd2(dba)3 was added, and the mixture was stirred under reflux for 12 hours at a nitrogen atmosphere. After the reaction was complete, the organic layer was extracted with toluene and distilled water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with hexane / dichloromethane (3:1 volume ratio) to give 12.5 g (yield: 70%) of compound F-113 as a white solid.

[0475] Synthesis Example 2: Synthesis of Compound F-56

[0476] Compound F-56 (13.52 g, yield: 72%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of di([1,1'-biphenyl]-4-yl)amine and 10.91 g of 11-chloro-7,7-dimethyl-7H-fluorenzo[4,3-b]benzofuran were used in an equivalent ratio of 1:1.1.

[0477] Synthesis Example 3: Synthesis of Compound F-114

[0478] Compound F-114 (14.8 g, yield: 84%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine and 9.34 g of 11-chloro-7,7-dimethyl-7H-fluoren[4,3-b]benzofuran were used in an equivalent ratio of 1:1.1.

[0479] Synthesis Example 4: Synthesis of Compound F-83

[0480] Compound F-83 (12.58 g, yield: 70%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of di([1,1'-biphenyl]-4-yl)amine and 10.02 g of 1-chlorobenzo[1,2-b;3,4-b']bisbenzofuran were used in an equivalent ratio of 1:1.1.

[0481] Synthesis Example 5: Synthesis of Compound F-96

[0482] Compound F-96 (14.18 g, yield: 83%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine and 8.91 g of 1-chlorobenzo[1,2-b;3,4-b']bisbenzofuran were used in an equivalent ratio of 1:1.1.

[0483] Synthesis Example 6: Synthesis of Compound F-110

[0484] Compound F-110 (12.05 g, yield: 81%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of 9,9-dimethyl-N-(3-(9-phenyl-9H-fluorene-9-yl)phenyl)-9H-fluorene-2-amine and 6.12 g of 1-chlorobenzo[1,2-b;3,4-b']bisbenzofuran were used in an equivalent ratio of 1:1.1.

[0485] Synthesis Example 7: Synthesis of Compound F-137

[0486] Compound F-137 (11.80 g, yield: 76%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of 9,9-dimethyl-N-(3-(9-methyl-9H-fluorene-9-yl)phenyl)-9H-fluorene-2-amine and 6.95 g of 1-chlorobenzo[1,2-b;3,4-b']bisbenzofuran were used in an equivalent ratio of 1:1.1.

[0487] Synthesis Example 8: Synthesis of Compound F-119

[0488] Compound F-119 (13.97 g, yield: 83%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of N-(9,9-dimethyl-9H-fluorene-2-yl)dibenzo[b,d]furan-1-amine and 8.58 g of 1-chlorobenzo[1,2-b;3,4-b']bisbenzofuran were used in an equivalent ratio of 1:1.1.

[0489] Synthesis Example 9: Synthesis of Compound A-15

[0490] Compound A-15 (16.2 g, yield: 86%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of bis([1,1'-biphenyl]-4-yl) and 10.92 g of 1-chloro-7,7-dimethyl-7H-fluorenzo[2,3-b]benzofuran were used in an equivalent ratio of 1:1.1.

[0491] Comparative Synthesis Example 1: Synthesis of Compound R-1

[0492] Compound R-1 (10.7 g, yield: 75%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of 9,9-dimethyl-8-phenyl-N-(3-(9-phenyl-9H-fluorene-9-yl)phenyl)-9H-fluorene-4-amine and 5.39 g of 1-chloro-8-phenyldibenzo[b,d]thiophene were used in an equivalent ratio of 1:1.1.

[0493] (Manufacturing of organic optoelectronic devices)

[0494] Example 1

[0495] The glass substrate coated with the ITO / Ag / ITO film was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with solvents such as acetone and isopropanol and dried. Then, it was moved to a plasma cleaner and cleaned with oxygen plasma for 10 minutes, and then moved to a vacuum depositor. The ITO / Ag / ITO (reflective electrode) prepared in this way was used as the anode. Compound A, doped with 3% NDP-9 (Novaled GmbH), was vacuum deposited on the ITO / Ag / ITO substrate to form a 100 Å thick hole injection layer, and compound A was deposited on the 1350 Å thick hole injection layer to form a hole transport layer. Compound F-113 of Synthesis Example 1 was deposited on the hole transport layer to a thickness of 285 Å to form a first hole transport auxiliary layer, and compound F-83 of Synthesis Example 4 was deposited on the first hole transport auxiliary layer to a thickness of 50 Å to form a second hole transport auxiliary layer. On the second hole transport auxiliary layer, 85 wt% of host H1 (40%) and host H2 (60%) were used as the host, and 15 wt% of PtGD was doped as a dopant to form a 380 Å thick emitting layer by vacuum deposition. Then, compound C was deposited on the 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. An organic light-emitting diode was fabricated by sequentially vacuum depositing Yb and AgMg on the electron transport layer to form a cathode.

[0496] Organic light-emitting diodes are fabricated to have the following structure: ITO / Ag / ITO / hole injection layer (compound A doped with 3% NDP-9, 100 Å) / hole transport layer (compound A, 1350 Å) / first hole transport auxiliary layer (compound F-113, 285 Å) / second hole transport auxiliary layer (compound F-83, 50 Å) / light-emitting layer [body (body H1 : body H2 = 40 wt% : 60 wt%) : PtGD = 85 wt% : 15 wt%] (380 Å) / electron transport auxiliary layer (compound C, 50 Å) / electron transport layer (compound D : Liq, 310 Å) / Yb / AgMg.

[0497] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine

[0498] Compound C: 4-{4-[3-(9,9-dimethyl-9H-fluorene-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[0499] Compound D: 2-(4-{2-[4-(diphenyl-1,3,5-triazin-2-yl)phenyl]naphth-1-yl}phenyl)-4,6-diphenyl-1,3,5-triazine

[0500] Subject H1: Subject H2: PtGD:

[0501] Examples 2 to 11 and Comparative Examples 1 to 4

[0502] Organic light-emitting diodes were manufactured in the same manner as in Example 1, except that the composition was changed to those shown in Table 1.

[0503] evaluate

[0504] The lifetime characteristics of the organic light-emitting diodes according to Examples 1 to 11 and Comparative Examples 1 to 4 were evaluated.

[0505] The specific measurement methods are shown below, and the results are shown in Table 1.

[0506] (1) Measure the change in current density based on the voltage change

[0507] 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.

[0508] (2) Measure the change in brightness based on voltage changes

[0509] The luminance was measured using a luminance meter (Minolta Cs-1000A) while the voltage of the organic light-emitting diode was increased from 0 V to 10 V.

[0510] (3) Measuring lifespan

[0511] In terms of brightness (cd / m 2 Maintain at 24000 cd / m 2 Meanwhile, the results were obtained by measuring the time it took for the current efficiency (cd / A) to decrease to 97%.

[0512] The lifetime measurements from Examples 1 to 11 and Comparative Examples 2 to 4 were calculated as relative values ​​based on Comparative Example 1 and are shown in Table 1.

[0513] [Table 1]

[0514] Referring to Table 1, it can be confirmed that the lifetime characteristics of the organic light-emitting diodes according to Examples 1 to 11 are significantly improved compared with those according to Comparative Examples 1 to 4.

[0515] Although the invention has been described in conjunction with exemplary embodiments which are now considered to be practical, it should be understood that the invention is not limited to the disclosed embodiments, but rather is intended to cover a variety of changes 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, Hole transport layer between the anode and the light-emitting layer, A hole transport auxiliary layer between the hole transport layer and the light-emitting 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 first hole transport auxiliary layer comprises a first compound represented by a combination of chemical formula 1 and chemical formula 2. The second hole transport auxiliary layer comprises a second compound represented by a combination of chemical formulas 3 and 4, and The first compound and the second compound are different from each other: [Chemical Formula 1][Chemical Formula 2] In chemical formula 1 and chemical formula 2, X 1 and X 2 Each is independently O, S, or CR a R b , R a and R b Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. a1 of chemical formula 1 up to a4 Each is independently connected to carbon (C) or CR. c , Chemical formula 2 It is the linker carbon (C). a1 of chemical formula 1 up to a4 The two adjacent ones connected to chemical formula 2 a1 of chemical formula 1 up to a4 The other two not connected to chemical formula 2 are each independently CR. c , R c and R 1 To R 5 Each of these groups is independently hydrogen, deuterium, cyano, halogen, 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. L 1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group. Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m1 is an integer from 1 to 3; [Chemical Formula 3] [Chemical Formula 4] In chemical formulas 3 and 4, X 3 and X 4 Each is independently O, S, or CR d R e , X 3 and X 4 At least one of them is O or S. R d and R e Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. Chemical formula 3, b1 up to b4 Each is independently connected to carbon (C) or CR. f , Chemical formula 4 It is the linker carbon (C). Chemical formula 3, b1 up to b4 The two adjacent ones in the middle are connected to chemical formula 4. B1 of chemical formula 3 up to b4 The other two not connected to chemical formula 4 are each independently CR. f , R f and R 6 To R 10 Each of these groups is independently hydrogen, deuterium, cyano, halogen, 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. L 4 To L 6 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group. 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, and m2 is an integer from 1 to 3.

2. The organic optoelectronic device according to claim 1, wherein, The first compound is represented by any one of the following chemical formulas: 1A, 1B, 1C, 1D, 1E, and 1F. [Chemical Formula 1A][Chemical Formula 1B] [Chemical Formula 1C][Chemical Formula 1D] [Chemical Formula 1E][Chemical Formula 1F] In chemical formulas 1A, 1B, 1C, 1D, 1E, and 1F, X 1 X 2 R 1 To R 5 L 1 To L 3 Ar 1 and Ar 2 And m1 as defined in chemical formulas 1 and 2, and R c1 To R c4 Each is independently hydrogen, deuterium, cyano, halogen, 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.

3. The organic optoelectronic device according to claim 1, wherein, The first compound is represented by one of the chemical formulas 1F-(i)-1 to 1F-(i)-4 and 1F-(ii)-1 to 1F-(ii)-4: [Chemical Formula 1F-(i)-1][Chemical Formula 1F-(i)-2] [Chemical Formula 1F-(i)-3][Chemical Formula 1F-(i)-4] [Chemical Formula 1F-(ii)-1][Chemical Formula 1F-(ii)-2] [Chemical Formula 1F-(ii)-3][Chemical Formula 1F-(ii)-4] In chemical formulas 1F-(i)-1 to 1F-(i)-4 and chemical formulas 1F-(ii)-1 to 1F-(ii)-4, X 1 and X 2 Each is either O or S independently. R c1 and R c2 Each of these groups is independently hydrogen, deuterium, cyano, halogen, 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. R a R b R 1 To R 5 L 1 To L 3 Ar 1 and Ar 2 And m1 as defined in claim 1.

4. The organic optoelectronic device according to claim 1, wherein, The second compound is represented by any one of the following chemical formulas: 2A, 2B, 2C, 2D, 2E, and 2F. [Chemical Formula 2A][Chemical Formula 2B] [Chemical Formula 2C] [Chemical Formula 2D] [Chemical Formula 2E] [Chemical Formula 2F] In chemical formulas 2A, 2B, 2C, 2D, 2E, and 2F, X 3 X 4 R 6 To R 10 L 4 To L 6 Ar 3 and Ar 4 And m2 as defined in claim 1, and R f1 To R f4 Each is independently hydrogen, deuterium, cyano, halogen, 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.

5. The organic optoelectronic device according to claim 4, wherein, The second compound is represented by the chemical formula 2A-(i)-1 or the chemical formula 2F-1: [Chemical formula 2A-(i)-1] In chemical formula 2A-(i)-1, X 3 and X 4 Each is either O or S independently. R f1 and R f4 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 d R e R 6 To R 10 L 4 To L 6 Ar 3 and Ar 4 And m2 as defined in claim 4; [Chemical formula 2F-1] In chemical formula 2F-1, X 3 X 4 R 6 To R 10 L 4 To L 6 Ar 3 and Ar 4 m2, R f1 and R f2 As defined in claim 4.

6. The organic optoelectronic device according to claim 1, wherein, Ar of chemical formulas 2 and 4 1 To Ar 4 Each of these compounds is independently 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 phenanthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, or a substituted or unsubstituted dibenzothiopheneyl.

7. The organic optoelectronic device according to claim 1, wherein, L 2 -Ar 1 L 3 -Ar 2 L 5 -Ar 3 and L 6 -Ar 4 Each substituent is independently selected from those listed in Group I: [Group I] In group I, R 11 To R 14 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. R 15 and R 16 Each is independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C12 aryl. m3 is an integer from 1 to 5. m4 is an integer from 1 to 4. m5 is an integer from 1 to 3. m6 is an integer of 1 or 2, and It is a connection point.

8. The organic optoelectronic device according to claim 1, wherein, The first compound and the second compound are each independently selected from the compounds listed in Group 1, and The first compound and the second compound are different from each other: [Group 1] [A-1][A-2][A-3][A-4][A-5] [A-6] [A-7] [A-8] [A-9] [A-10] [A-11] [A-12][A-13][A-14] [A-15] [A-16] [A-17] [A-18][A-19][A-20] [A-21] [A-22] [A-23] [A-24] [A-25] [A-26][A-27] [A-28] [A-29] [A-30] [A-31][A-32] [A-33][A-34] [A-35] [A-36][A-37] [A-38] [A-39][A-40] [A-41] [A-42] [A-43] [A-44][A-45] [A-46] [A-47] [A-48][A-49][A-50] [A-51][A-52][A-53] [A-54][A-55] [A-56][A-57] [A-58] [A-59] [A-60] [A-61][A-62][A-63][A-64][A-65] [A-66] [A-67][A-68] [A-69][A-70] [A-71][A-72] [A-73] [A-74] [A-75] [A-76] [A-77][A-78][A-79] [A-80] [A-81][A-82] [A-83][A-84][A-85] [A-86] [A-87] [A-88] [A-89] [A-90] [A-91][A-92][A-93][A-94][A-95] [A-96][A-97] [A-98] [A-99][A-100] [A-101][A-102][A-103] [A-104] [A-105] [A-106] [A-107] [A-108] [A-109] [A-110] [A-111] [A-112] [A-113][A-114] [A-115] [A-116] [A-117] [A-118] [A-119] [A-120] [A-121][A-122][A-123] [A-124][A-125] [A-126][A-127][A-128] [A-129][A-130] [A-131][A-132] [A-133] [A-134][A-135] [A-136][A-137] [A-138] [A-139][A-140] [A-141] [A-142] [A-143] [A-144][A-145] [A-146][A-147] [A-148] [A-149][A-150] [A-151] [A-152] [A-153] [A-154][A-155] [A-156] [A-157] [A-158] [A-159][A-160] [A-161] [A-162] [A-163] [A-164][A-165] [A-166][A-167] [A-168] [A-169] [A-170] [A-171] [A-172] [A-173][A-174] [A-175] [A-176] [A-177] [A-178] [A-179] [A-180] [A-181][A-182] [A-183] [A-184][A-185] [A-186][A-187] [A-188] [A-189][A-190] [A-191][A-192] [A-193] [A-194] [A-195] [A-196] [A-197][A-198] [A-199] [A-200] [B-1] [B-2][B-3][B-4] [B-5] [B-6] [B-7] [B-8] [B-9] [B-10] [B-11][B-12][B-13] [B-14][B-15] [B-16] [B-17][B-18] [B-19][B-20] [B-21] [B-22][B-23][B-24] [B-25] [B-26][B-27][B-28] [B-29] [B-30] [B-31] [B-32][B-33] [B-34][B-35] [B-36][B-37][B-38][B-39][B-40] [B-41][B-42] [B-43] [B-44][B-45] [B-46] [B-47][B-48][B-49][B-50] [B-51][B-52][B-53][B-54][B-55] [B-56] [B-57][B-58] [B-59] [B-60] [B-61] [B-62] [B-63][B-64] [B-65] [B-66] [B-67][B-68][B-69][B-70] [B-71][B-72] [B-73] [B-74][B-75] [B-76][B-77] [B-78] [B-79][B-80] [B-81] [B-82][B-83][B-84] [B-85] [B-86] [B-87][B-88] [B-89][B-90] [B-91] [B-92][B-93] [B-94][B-95] [B-96] [B-97] [B-98][B-99] [B-100] [B-101] [B-102] [B-103][B-104][B-105] [B-106][B-107][B-108] [B-109][B-110] [B-111] [B-112][B-113][B-114] [B-115] [B-116][B-117][B-118] [B-119][B-120] [B-121] [B-122] [B-123][B-124][B-125] [B-126][B-127] [B-128][B-129][B-130] [B-131][B-132][B-133] [B-134][B-135] [B-136][B-137] [B-138][B-139][B-140] [B-141][B-142] [B-143] [B-144][B-145] [B-146][B-147][B-148] [B-149] [B-150] [B-151][B-152] [B-153][B-154][B-155] [B-156][B-157][B-158] [B-159][B-160] [B-161] [B-162][B-163][B-164][B-165] [B-166] [B-167] [B-168] [B-169][B-170] [B-171][B-172] [B-173] [B-174][B-175] [B-176] [B-177][B-178][B-179][B-180] [B-181][B-182] [B-183][B-184][B-185] [B-186][B-187][B-188] [B-189] [B-190] [B-191][B-192] [B-193][B-194][B-195] [B-196][B-197] [B-198][B-199][B-200] [C-1][C-2][C-3][C-4][C-5] [C-6][C-7][C-8] [C-9][C-10] [C-11] [C-12] [C-13] [C-14][C-15] [C-16] [C-17] [C-18] [C-19][C-20] [C-21][C-22] [C-23] [C-24][C-25] [C-26][C-27][C-28][C-29] [C-30] [C-31][C-32] [C-33] [C-34][C-35] [C-36][C-37][C-38][C-39][C-40] [C-41] [C-42][C-43][C-44][C-45] [C-46] [C-47][C-48][C-49] [C-50] [C-51] [C-52][C-53] [C-54][C-55] [C-56][C-57][C-58][C-59] [C-60] [C-61][C-62] [C-63][C-64] [C-65] [C-66][C-67][C-68] [C-69][C-70] [C-71] [C-72][C-73] [C-74][C-75] [C-76][C-77][C-78] [C-79] [C-80] [C-81][C-82] [C-83] [C-84][C-85] [C-86][C-87][C-88][C-89] [C-90] [C-91][C-92] [C-93] [C-94][C-95] [C-96][C-97] [C-98][C-99] [C-100] [C-101][C-102][C-103] [C-104][C-105] [C-106] [C-107][C-108] [C-109][C-110] [C-111][C-112][C-113][C-114] [C-115] [C-116] [C-117] [C-118] [C-119] [C-120] [C-121] [C-122] [C-123] [C-124] [C-125] [C-126][C-127][C-128] [C-129][C-130] [C-131][C-132][C-133][C-134] [C-135] [C-136][C-137][C-138][C-139] [C-140] [C-141][C-142][C-143][C-144] [C-145] [C-146] [C-147] [C-148] [C-149] [C-150] [C-151] [C-152][C-153][C-154] [C-155] [C-156][C-157] [C-158] [C-159][C-160] [C-161][C-162][C-163] [C-164][C-165] [C-166][C-167] [C-168] [C-169] [C-170] [C-171][C-172] [C-173] [C-174][C-175] [C-176][C-177] [C-178] [C-179][C-180] [C-181][C-182] [C-183] [C-184][C-185] [C-186] [C-187] [C-188][C-189][C-190] [C-191] [C-192] [C-193] [C-194] [C-195] [C-196] [C-197][C-198] [C-199][C-200] [D-1] [D-2][D-3] [D-4][D-5] [D-6] [D-7] [D-8][D-9] [D-10] [D-11][D-12][D-13][D-14] [D-15] [D-16] [D-17] [D-18][D-19] [D-20] [D-21][D-22] [D-23][D-24][D-25] [D-26] [D-27][D-28] [D-29] [D-30] [D-31][D-32][D-33] [D-34] [D-35] [D-36] [D-37] [D-38] [D-39] [D-40] [D-41][D-42][D-43] [D-44][D-45] [D-46] [D-47][D-48] [D-49] [D-50] [D-51][D-52] [D-53][D-54] [D-55] [D-56][D-57] [D-58] [D-59] [D-60] [D-61][D-62][D-63] [D-64] [D-65] [D-66][D-67] [D-68][D-69][D-70] [D-71] [D-72] [D-73][D-74] [D-75] [D-76] [D-77][D-78][D-79] [D-80] [D-81] [D-82][D-83][D-84] [D-85] [D-86] [D-87][D-88][D-89][D-90] [D-91][D-92][D-93] [D-94][D-95] [D-96][D-97] [D-98][D-99] [D-100] [D-101][D-102][D-103] [D-104][D-105] [D-106][D-107] [D-108][D-109][D-110] [D-111][D-112] [D-113] [D-114][D-115] [D-116][D-117][D-118][D-119] [D-120] [D-121][D-122] [D-123] [D-124] [D-125] [D-126] [D-127][D-128][D-129][D-130] [D-131][D-132] [D-133] [D-134][D-135] [D-136][D-137] [D-138][D-139][D-140] [D-141][D-142] [D-143][D-144] [D-145] [D-146][D-147][D-148] [D-149][D-150] [D-151][D-152][D-153] [D-154][D-155] [D-156][D-157] [D-158][D-159][D-160] [D-161] [D-162][D-163] [D-164][D-165] [D-166] [D-167] [D-168][D-169] [D-170] [D-171][D-172][D-173] [D-174][D-175] [D-176][D-177][D-178] [D-179][D-180] [D-181][D-182] [D-183][D-184] [D-185] [D-186][D-187] [D-188][D-189] [D-190] [D-191][D-192] [D-193] [D-194][D-195] [D-196] [D-197] [D-198][D-199] [D-200] [E-1] [E-2] [E-3] [E-4][E-5] [E-6] [E-7] [E-8] [E-9] [E-10] [E-11] [E-12] [E-13] [E-14][E-15] [E-16][E-17][E-18][E-19][E-20] [E-21] [E-22] [E-23] [E-24][E-25] [E-26] [E-27][E-28][E-29] [E-30] [E-31][E-32] [E-33] [E-34][E-35] [E-36] [E-37][E-38] [E-39] [E-40] [E-41][E-42][E-43] [E-44][E-45] [E-46][E-47] [E-48] [E-49] [E-50] [E-51] [E-52][E-53][E-54][E-55] [E-56][E-57][E-58] [E-59][E-60] [E-61][E-62][E-63][E-64][E-65] [E-66][E-67] [E-68] [E-69][E-70] [E-71][E-72] [E-73] [E-74][E-75] [E-76][E-77] [E-78] [E-79][E-80] [E-81][E-82][E-83] [E-84][E-85] [E-86] [E-87][E-88][E-89] [E-90] [E-91][E-92][E-93] [E-94][E-95] [E-96] [E-97][E-98][E-99][E-100] [E-101][E-102] [E-103] [E-104][E-105] [E-106] [E-107][E-108] [E-109][E-110] [E-111][E-112] [E-113][E-114] [E-115] [E-116][E-117] [E-118][E-119] [E-120] [E-121][E-122] [E-123][E-124] [E-125] [E-126][E-127] [E-128] [E-129][E-130] [E-131][E-132] [E-133] [E-134][E-135] [E-136][E-137][E-138] [E-139][E-140] [E-141][E-142] [E-143][E-144] [E-145] [E-146][E-147] [E-148][E-149] [E-150] [E-151][E-152] [E-153] [E-154][E-155] [E-156][E-157] [E-158][E-159][E-160] [E-161] [E-162] [E-163][E-164][E-165] [E-166] [E-167][E-168] [E-169][E-170] [E-171] [E-172][E-173] [E-174] [E-175] [E-176][E-177] [E-178][E-179] [E-180] [E-181][E-182] [E-183] [E-184] [E-185] [E-186] [E-187] [E-188] [E-189][E-190] [E-191][E-192] [E-193][E-194] [E-195] [E-196][E-197] [E-198] [E-199] [E-200] [F-1][F-2] [F-3] [F-4] [F-5] [F-6] [F-7][F-8] [F-9] [F-10] [F-11] [F-12][F-13] [F-14][F-15] [F-16][F-17][F-18] [F-19][F-20] [F-21] [F-22][F-23][F-24][F-25] [F-26][F-27] [F-28][F-29][F-30] [F-31][F-32] [F-33] [F-34] [F-35] [F-36][F-37] [F-38][F-39] [F-40] [F-41][F-42][F-43][F-44] [F-45] [F-46][F-47][F-48][F-49][F-50] [F-51] [F-52][F-53] [F-54][F-55] [F-56] [F-57][F-58] [F-59][F-60] [F-61][F-62][F-63][F-64] [F-65] [F-66][F-67][F-68][F-69][F-70] [F-71][F-72][F-73] [F-74][F-75] [F-76] [F-77] [F-78][F-79][F-80] [F-81][F-82] [F-83][F-84][F-85] [F-86][F-87][F-88] [F-89][F-90] [F-91][F-92] [F-93] [F-94][F-95] [F-96][F-97][F-98][F-99][F-100] [F-101] [F-102] [F-103][F-104] [F-105] [F-106] [F-107][F-108][F-109] [F-110] [F-111][F-112] [F-113] [F-114][F-115] [F-116][F-117][F-118] [F-119][F-120] [F-121][F-122][F-123] [F-124][F-125] [F-126][F-127] [F-128][F-129][F-130] [F-131][F-132] [F-133] [F-134][F-135] [F-136][F-137] [F-138] [F-139][F-140] [F-141][F-142] [F-143] [F-144][F-145] [F-146] [F-147] [F-148] [F-149][F-150] [F-151] [F-152] [F-153][F-154] [F-155] [F-156][F-157][F-158][F-159] [F-160] [F-161][F-162] [F-163] [F-164][F-165] [F-166] [F-167][F-168][F-169][F-170] [F-171][F-172] [F-173][F-174][F-175] [F-176][F-177][F-178] [F-179][F-180] [F-181][F-182] [F-183] [F-184][F-185] [F-186][F-187] [F-188] [F-189][F-190] [F-191][F-192][F-193] [F-194] [F-195] [F-196][F-197] [F-198][F-199][F-200] [F-201][F-202] [F-203][F-204][F-205] [F-206][F-207][F-208][F-209][F-210] [F-211][F-212] [F-213][F-214] [F-215] [F-216][F-217] [F-218][F-219][F-220] [F-221][F-222] [F-223][F-224] [F-225] [F-226][F-227] [F-228][F-229] [F-230] [F-231][F-232] [F-233][F-234] [F-235] [F-236][F-237][F-238] [F-239][F-240] [F-241][F-242][F-243] [F-244][F-245] [F-246][F-247] [F-248] [F-249][F-250] [F-251][F-252] [F-253] [F-254][F-255] [F-256][F-257] [F-258] [F-259][F-260] [F-261] [F-262][F-263] [F-264][F-265] [F-266][F-267] [F-268][F-269] [F-270] [F-271][F-272] [F-273][F-274] [F-275] [F-276][F-277][F-278] [F-279][F-280] [F-281] [F-282] [F-283] [F-284] [F-285] [F-286][F-287] [F-288] [F-289][F-290] [F-291][F-292] [F-293][F-294][F-295] [F-296][F-297][F-298] [F-299][F-300] [F-301][F-302][F-303] [F-304][F-305] [F-306][F-307][F-308][F-309] [F-310] [F-311][F-312][F-313] [F-314][F-315] [F-316][F-317][F-318] [F-319][F-320] [F-321][F-322][F-323] [F-324][F-325] [F-326][F-327][F-328] [F-329][F-330] [F-331][F-332][F-333] [F-334][F-335] [F-336][F-337][F-338] [F-339][F-340] [F-341][F-342][F-343] [F-344][F-345] [F-346][F-347][F-348] [F-349][F-350] [F-351][F-352][F-353] [F-354][F-355] [F-356][F-357][F-358] [F-359][F-360] [F-361][F-362] [F-363][F-364][F-365] [F-366][F-367][F-368] [F-369][F-370] [F-371][F-372] [F-373][F-374][F-375] [F-376][F-377] [F-378][F-379][F-380] [F-381][F-382][F-383] [F-384][F-385] [F-386][F-387][F-388] [F-389][F-390] [F-391][F-392][F-393] [F-394][F-395] [F-396][F-397][F-398] [F-399][F-400] [F-401][F-402][F-403] [F-404][F-405] [F-406][F-407][F-408] [F-409][F-410] [F-411][F-412][F-413] [F-414][F-415] [F-416][F-417] [F-418] [F-419][F-420] [F-421][F-422] [F-423][F-424] [F-425] [F-426][F-427] [F-428][F-429] [F-430] [F-431][F-432] [F-433][F-434] [F-435] [F-436][F-437] [F-438][F-439] [F-440].

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

Images