Compounds for organic optoelectronic devices, organic optoelectronic devices and display devices

Abstract

Disclosed are a compound for an organic optoelectronic device represented by Chemical Formula 1, an organic optoelectronic device including the compound for an organic optoelectronic device, and a display device.

Description

[0001] Citations of relevant applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2025-0044237, filed on April 4, 2025, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Compounds for use in organic optoelectronic devices, organic optoelectronic devices, and display devices are disclosed. Background Technology

[0004] Organic optoelectronic devices (organic optoelectronic diodes) are devices that can convert electrical energy into light energy and vice versa.

[0005] 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.

[0006] Examples of organic optoelectronic devices include organic photoelectric devices, organic light-emitting diodes, organic solar cells, and organic photosensitive drums.

[0007] 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

[0008] One embodiment provides a compound for organic optoelectronic devices that enables long-cycle-life organic optoelectronic devices to operate efficiently even at low voltages.

[0009] Another embodiment provides an organic optoelectronic device comprising a compound for an organic optoelectronic device.

[0010] Another embodiment provides a display device that includes an organic optoelectronic device.

[0011] According to one embodiment, a compound for an organic optoelectronic device, represented by chemical formula 1, is provided.

[0012] [Chemical Formula 1]

[0013] In chemical formula 1, X 1 Is it O or S? R 1 To R4 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. R 5 and R 6 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 7 To R 9 Each is independently either an unsubstituted methyl group or a deuterated methyl group. L 1 It is a single bond or a substituted or unsubstituted phenylene. Ar 1 It is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted 1-fluorenyl, a substituted or unsubstituted 2-fluorenyl, a substituted or unsubstituted 3-fluorenyl, a substituted or unsubstituted 4-fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl. m1 to m3 are each an independent integer from 1 to 3. m4 is an integer from 1 to 4, and When m1 to m4 are 2 or greater, R 1 To R 4 They are the same as or different from each other.

[0014] According to another embodiment, the organic optoelectronic device includes an anode and a cathode facing each other and at least one organic layer between the anode and the cathode, wherein the organic layer contains a compound for the organic optoelectronic device.

[0015] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0016] It can realize long-life organic optoelectronic devices that can operate effectively even at low voltages. 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: Hole transport layer

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

[0022] 34: Electronic transmission area Detailed Implementation

[0023] Embodiments of the invention are described in detail below. However, these embodiments are exemplary and the disclosure is not limited thereto.

[0024] As used herein, 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.

[0025] 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.

[0026] As used in this article, "unsubstituted" means that the hydrogen atom is not replaced by another substituent and the hydrogen atom is retained.

[0027] As used herein, “hydrogen substitution (-H)” can include “deuterium substitution (-D)” or “tritium substitution (-T)”.

[0028] As used herein, 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.

[0029] As used herein, “aryl” means a group comprising at least one aromatic hydrocarbon moiety, and all elements of the aromatic hydrocarbon moiety have conjugated p orbitals, such as phenyl, naphthyl, etc., 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.

[0030] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent carbon atom pairs) functional groups.

[0031] 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.

[0032] As an 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.

[0033] 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.

[0034] 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 thiazolyl group, a substituted or unsubstituted pyridyl 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, a substituted or unsubstituted quinolinyl group, or a substituted or unsubstituted group. The following are included: isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxolinyl, substituted or unsubstituted naphthinyl, 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, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted xanthanyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthophenyl, substituted or unsubstituted benzofuran fluorenyl, substituted or unsubstituted benzothiophenenyl, or combinations thereof, but not limited thereto.

[0035] 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.

[0036] 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.

[0037] The following describes a compound for an organic optoelectronic device according to one embodiment.

[0038] According to one embodiment, a compound for an organic optoelectronic device is represented by chemical formula 1.

[0039] [Chemical Formula 1]

[0040] In chemical formula 1, X 1 Is it O or S? R 1 To R 4Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. R 5 and R 6 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 7 To R 9 Each is independently either an unsubstituted methyl group or a deuterated methyl group. L 1 It is a single bond or a substituted or unsubstituted phenylene. Ar 1 It is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted 1-fluorenyl, a substituted or unsubstituted 2-fluorenyl, a substituted or unsubstituted 3-fluorenyl, a substituted or unsubstituted 4-fluorenyl, a substituted or unsubstituted 9-fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl. m1 to m3 are each an independent integer from 1 to 3. m4 is an integer from 1 to 4, and When m1 is 2 or greater, each R 1 They are the same or different from each other.

[0041] When m2 is 2 or greater, each R 2 They are the same or different from each other.

[0042] When m3 is 2 or greater, each R 3 They are the same or different from each other.

[0043] When m4 is 2 or greater, each R 4 They are the same or different from each other.

[0044] In compounds represented by Formula 1 for organic optoelectronic devices, the 6-position of dibenzofuran (or dibenzothiophene) is a highly reactive site that can affect molecular stability during hole injection and electron leakage. Therefore, a tert-butyl group with large steric hindrance has been introduced at the 6-position to improve the lifetime of organic light-emitting diodes (OLEDs) using it.

[0045] Meanwhile, by directly substituting the amino group at the 1-position of dibenzofuran (or dibenzothiophene), the HOMO energy level can be shallowed, so that organic light-emitting diodes containing it can operate effectively even at low driving voltages.

[0046] In addition, the fluorene group substituted on the amine group helps improve hole transport, which is effective in reducing driving voltage and improving efficiency.

[0047] For example, based on the specific substitution position of the fluorenyl group on the amino group, chemical formula 1 can be represented by any one of chemical formulas 1-1 to 1-4.

[0048] [Chemical Formula 1-1] [Chemical Formula 1-2]

[0049] [Chemical Formula 1-3] [Chemical Formula 1-4]

[0050] In chemical formulas 1-1 to 1-4 X 1 R 1 To R 9 L 1 Ar 1 The same applies to m1 to m4 as described above.

[0051] For example, R 1 To R 4 Each can be hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl, independently.

[0052] As a specific example, R 1 To R 4 Each of these can be hydrogen, deuterium, cyano, halogen, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, or substituted or unsubstituted biphenyl.

[0053] For example, R 5 and R 6 Each can be independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C12 aryl.

[0054] For example, a compound represented by chemical formula 1 for an organic optoelectronic device may be selected from, but is not limited to, one of the compounds listed in group 1.

[0055] [Group 1]

[0056] [1-1] [1-2] [1-3] [1-4] [1-5]

[0057] [1-6] [1-7] [1-8] [1-9] [1-10]

[0058] [1-11] [1-12] [1-13] [1-14] [1-15]

[0059] [1-16] [1-17] [1-18] [1-19] [1-20]

[0060] [1-21] [1-22] [1-22] [1-24] [1-25]

[0061] [1-26] [1-27] [1-28] [1-29] [1-30]

[0062] [1-31] ​​[1-32] [1-33] [1-34] [1-35]

[0063] [1-36] [1-37] [1-38] [1-39] [1-40]

[0064] [1-41] [1-42] [1-43] [1-44] [1-45]

[0065] [1-46] [1-47] [1-48] [1-49] [1-50]

[0066] [1-51] [1-52] [1-53] [1-54] [1-55]

[0067] [1-56] [1-57] [1-58] [1-59] [1-60]

[0068] Dn refers to the number of deuterium substitutions, where n is 1 or greater, and the maximum value of n corresponds to the number of substituted hydrogen positions.

[0069] More specific examples of deuterium-substituted structures include the compounds listed in Group 1-1.

[0070] [Group 1-1]

[0071] [1-61] [1-62] [1-63] [1-64] [1-65]

[0072] An organic optoelectronic device using the above-described compound for organic optoelectronic devices is described.

[0073] 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.

[0074] Here, an organic light-emitting diode (OLED) is described as an example of an organic optoelectronic device with reference to the accompanying drawings.

[0075] Figure 1 This is a schematic cross-sectional view of an organic light-emitting diode according to one embodiment.

[0076] refer to Figure 1 An organic light-emitting diode according to one embodiment includes an anode 10, a cathode 20, and an organic layer 30 between the anode 10 and the cathode 20.

[0077] The anode 10 may be made of a conductor with a high work function to facilitate hole injection, and may be made of, for example, metals, metal oxides, and / or conductive polymers. The anode 10 may be made of: metals such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO and Al or SnO2 and Sb; conductive polymers such as, but not limited to, poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline.

[0078] The cathode 20 may be made of a conductor with a small work function to aid electron injection, and may be made of, for example, metals, metal oxides, and / or conductive polymers. The cathode 20 may be made of: 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 not limited to these.

[0079] The organic layer 30 includes a hole transport layer 31, a light-emitting layer 32, and a hole transport auxiliary layer 33 between the hole transport layer 31 and the light-emitting layer 32.

[0080] The organic layer 30 may contain the compounds described above for organic optoelectronic devices.

[0081] For example, the light-emitting layer 32 may contain the compounds described above for organic optoelectronic devices.

[0082] At this time, the light-emitting layer 32 may contain, for example, the compound used in organic optoelectronic devices described above as a host, and the host may be, for example, a phosphorescent host.

[0083] The phosphorescent host should facilitate the injection and transport of holes and electrons within the luminescent 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.

[0084] The light-emitting layer 32 may also contain dopants, and the composition containing the phosphorescent host and dopants may be, for example, a red light-emitting composition or a green light-emitting composition.

[0085] The dopant can be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0086] 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.

[0087] 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.

[0088] [Chemical Formula Z]

[0089] L 5 MX 3

[0090] In the chemical formula Z, M is a metal, and L 5 and X 3 The same or different ligands that form a complex with M.

[0091] 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 5 and X 3 It could be, for example, a bidentate ligand.

[0092] By L 5 and X3 The ligands represented can be selected from chemical formulas Z-1 to Z-8, but are not limited to these.

[0093] [Chemical Formula Z-1] [Chemical Formula Z-2] [Chemical Formula Z-3]

[0094] [Chemical Formula Z-4] [Chemical Formula Z-5]

[0095] [Chemical Formula Z-6] [Chemical Formula Z-7]

[0096] [Chemical Formula Z-8]

[0097] In chemical formulas Z-1 to Z-8 X 14 Selected from carbon and nitrogen, Y 100 Is it 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, or -SiR. 133 R 134 R 135 Or -GeR 133 R 134 R 135 Alternatively, it can be attached to an adjacent substituent to form a substituted or unsubstituted ring, and, for example, together with pyridine, can be a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuranopyridine, a substituted or unsubstituted benzothiophenopyridine, a substituted or unsubstituted indenepyridine, a substituted or unsubstituted benzofuranoquinoline, a substituted or unsubstituted benzothiophenoquinoline, or a substituted or unsubstituted indenequinoline; R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. m111 is an integer of 1 or 2. m18 is an integer from 1 to 4, and m19 is an integer from 1 to 5.

[0098] By L 5 and X 3Specific examples of the ligands represented may be selected from, but are not limited to, the chemical formulas listed in group A.

[0099] [Group A]

[0100] 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 308 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. 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 m27 and m29 are 2 or greater and m28 is 2, R 303 To R 307 They are the same as or different from each other.

[0101] In one embodiment, the phosphorescent dopant may be an iridium complex and may be represented by, for example, any of the chemical formulas 9 to 11.

[0102] [Chemical Formula 9]

[0103] In chemical formula 9, Ring A is a monocyclic or polycyclic fused ring. In both monocyclic and polycyclic fused ring systems, each ring is a 5- or 6-membered carbon ring or a heterocyclic ring. R 100Indicates one to a maximum number of monovalent substituents. When R 100 When there are 2 or more, each R 100 Whether they are the same or different, R 101 To R 104 Each of these elements 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 10 and X 11 Each is independently selected from carbon and nitrogen. L 100 It is a ligand or bidentate ligand for a monovalent anion, which coordinates with iridium via a non-shared electron pair of a carbon or heteroatom, and m21 is any integer from 0 to 3.

[0104] [Chemical Formula 10]

[0105] In chemical formula 10, Ring B is a monocyclic or polycyclic fused ring. In both monocyclic and polycyclic fused ring systems, each ring is a 5- or 6-membered carbon ring or a heterocyclic ring. Y 100 Is it O or S? R 201 Indicates one to a maximum number of monovalent substituents. When R 201 When there are 2 or more, each R 201 Whether they are the same or different, R 206 To R 213 Each of these elements 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 12 and X 13 Each is independently selected from carbon and nitrogen. L 100 It is a ligand or bidentate ligand for a monovalent anion, which coordinates with iridium through non-shared electron pairs of carbon or heteroatoms. m100 is an integer of 1 or 2. m101 is an integer of 1 or 2. n100 is an integer that is either 0 or 1, and m21 is any integer from 0 to 3.

[0106] [Chemical Formula 11]

[0107] In chemical formula 11, Y 100 Is it O or S? R 101 To R 111 Each of these elements 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 ligand or bidentate ligand for a monovalent anion, which coordinates with iridium via a non-shared electron pair of a carbon or heteroatom, and m21 is any integer from 0 to 3.

[0108] As a more specific example, iridium complexes can be represented by one of chemical formulas 9-1 to 9-6.

[0109] [Chemical Formula 9-1]

[0110] In chemical formula 9-1, R 101 To R 116 Each of these elements 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 -GeR132 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. 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]

[0111] 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.

[0112] [Chemical Formula 9-2]

[0113] [Chemical Formula 9-3]

[0114] [Chemical Formula 9-4]

[0115] [Chemical Formula 9-5]

[0116] [Chemical Formula 9-6]

[0117] In chemical formulas 9-2 to 9-6 X 14 Selected from carbon and nitrogen, Y 100 Is it O or S? R 101 To R 122Each of these elements 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 of a monovalent anion and is a ligand coordinated to iridium through the lone pair of electrons of a carbon or heteroatom. m111 is an integer of 1 or 2, and n1 and n2 are each independent integers from 0 to 3, and n1 + n2 is an integer from 1 to 3. In another embodiment, the dopant may be a platinum complex, such as a platinum complex represented by the chemical formula Z-3.

[0118] [Chemical Formula Z-3]

[0119] In chemical formula Z-3, rings A, B, C, and D are each independently a 5- or 6-membered carbon ring or a heterocycle; R A R B R C and R D Each can be independently mono-, di-, tri-, or tetra-substituted or unsubstituted; nA is an integer that is either 0 or 1; L B L C and L D Each of these can be independently a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', or a combination thereof. When nA is 1, L E It can be a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', or a combination thereof; and when nA is 0, L E It does not exist; R A R B R C R DR and R' are each independently 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, or 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.

[0120] Platinum complexes can be represented, for example, by chemical formula 12-1 or chemical formula 12-2.

[0121] [Chemical Formula 12-1]

[0122] [Chemical Formula 12-2]

[0123] In chemical formulas 12-1 and 12-2, X 100 Selected from O, S and NR 132 , R 118 To R 132 Each of these elements 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.

[0124] In addition, the compounds described above for organic optoelectronic devices may be included in the light-emitting layer 32, and at least one of the compounds listed in Group B may be included in the hole transport layer 31.

[0125] [Group B]

[0126] (Dn refers to the number of hydrogen atoms replaced by deuterium and indicates the structure in which one or more deuterium atoms are substituted.)

[0127] In the hole transport layer 31, in addition to the compounds mentioned above, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A and compounds with similar structures may also be used.

[0128] For example, hole transport auxiliary layer 33 may contain the compounds described above for organic optoelectronic devices.

[0129] At this time, examples of phosphorescent subjects included in the light-emitting layer 32 may include organic compounds, including carbazole, indolocarbazole, dibenzofuran, dibenzothiophene, indolodibenzopyran, indolodibenzothiophene, fluorene, indobenzocarbazole, triphenylene, pyrimidine, triazine, or combinations thereof.

[0130] 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.

[0131] In addition, the dopants contained in the light-emitting layer 32 are as described above.

[0132] Meanwhile, the hole transport layer 31 is a layer that helps holes to be transported from the anode 10 to the light-emitting layer 32, and may be, for example, an amine compound, but is not limited thereto.

[0133] Amine compounds may include, for example, at least one aryl and / or heteroaryl group. The amine compound may be represented by, for example, chemical formula a or chemical formula b, but is not limited thereto.

[0134] [Chemical Formula a] [Chemical Formula b]

[0135] In chemical formula a or b Ar a To Ar g Each of these elements independently consists of 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. Ar a 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.

[0136] For example, the hole transport auxiliary layer 33 contains the compound described above for organic optoelectronic devices, and the organic light-emitting diode further includes a second hole transport auxiliary layer located between the light-emitting layer and the hole transport auxiliary layer, and the second hole transport auxiliary layer may include a compound represented by chemical formula 2 that is different from the compound for organic optoelectronic devices contained in the hole transport auxiliary layer.

[0137] [Chemical Formula 2]

[0138] In chemical formula 2, X 2 Is it O, S, or CR? 20 R 21 , Ar 2 and Ar 3 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. L 2 To L 4 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. R 20 and R 21 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 10 To R 14 Each of these groups is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C30 alkylsilyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. m5 is an integer from 1 to 3, and When m5 is 2 or greater, each R 10 They are the same or different from each other.

[0139] Since the amine core is replaced by at least one dibenzofuran (or dibenzothiophene or fluorene), steric hindrance can be minimized by reducing the deposition temperature, thereby further improving lifetime characteristics.

[0140] For example, chemical formula 2 can be represented by any one of chemical formulas 2-1 to 2-4.

[0141] [Chemical Formula 2-1] [Chemical Formula 2-2]

[0142] [Chemical Formula 2-3] [Chemical Formula 2-4]

[0143] In chemical formulas 2-1 to 2-4 L 2 To L 4 X 2 R 10 To R 14 Ar 2 Ar 3 The same applies to m5 as described above.

[0144] For example, the compound contained in the second hole transport auxiliary layer can be represented by chemical formula 2-1.

[0145] For example, Ar 2 and Ar 3 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, or 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.

[0146] As a specific example, Ar 2 and Ar 3 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.

[0147] For example, R 10 To R 14 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.

[0148] For example, R 10 To R 14 Each can be hydrogen, deuterium, cyano, substituted or unsubstituted tert-butyl, or substituted or unsubstituted phenyl, independently.

[0149] For example, in chemical formula 2, L 2 To L 4 Each can be a single bond or a substituted or unsubstituted phenylene group, and each can be independent of the others.

[0150] For example, R 10 To R 14 They can be hydrogen, deuterium, or tert-butyl, each independently.

[0151] For example, R 20 To R 21 Each can be independently a substituted or unsubstituted C1 to C5 alkyl or a substituted or unsubstituted C6 to C12 aryl.

[0152] For example, R 20 To R 21 Each can be independently a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0153] For example, L 2 -Ar 2 and L 3 -Ar 3 Each can be independently selected from the substituents listed in Group I.

[0154] [Group I]

[0155] In group I, R 15 To R 19 Each of these groups is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, or substituted or unsubstituted C6 to C12 aryl. m6 is an integer from 1 to 5. m7 is an integer from 1 to 4. m8 is an integer from 1 to 7. m9 is an integer from 1 to 3. m10 is an integer of 1 or 2, and It is a connection point.

[0156] For example, Ar 2 and Ar 3At least one of them can be a substituted or unsubstituted fluorene group, and can be represented by, for example, chemical formula 2-1-1.

[0157] [Chemical Formula 2-1-1]

[0158] In chemical formula 2-1-1, X 2 Ar 3 L 2 To L 4 R 10 To R 14 The same applies to m5 as described above. X 4 Is it O, S, or CR? 22 R 23 , R 22 and R 23 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 15 To R 19 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and m6 is an integer from 1 to 3.

[0159] In chemical formula 2-1-1, when m6 is 2 or greater, each R 15 They can be the same as or different from each other.

[0160] In chemical formula 2-1-1, R 22 and R 23 Each can be independently a substituted or unsubstituted C1 to C5 alkyl or a substituted or unsubstituted C6 to C12 aryl.

[0161] For example, R 22 and R 23 Each can be independently a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0162] In chemical formula 2-1-1, R 15 To R 19 Each can be hydrogen, deuterium, or substituted or unsubstituted C1 to C5 alkyl groups, independently.

[0163] For example, R 15 To R 19 They can be hydrogen, deuterium, or tert-butyl, each independently.

[0164] As a specific example, in chemical formula 2-1-1, L 2 and L 3 Each can be a single key.

[0165] As a more specific example, chemical formula 2-1-1 can be selected from chemical formula 2-1-1a, chemical formula 2-1-1b, chemical formula 2-1-1c and chemical formula 2-1-1d.

[0166] [Chemical Formula 2-1-1a] [Chemical Formula 2-1-1b]

[0167] [Chemical Formula 2-1-1c] [Chemical Formula 2-1-1d]

[0168] In chemical formulas 2-1-1a, 2-1-1b, 2-1-1c, and 2-1-1d, Ar 3 X 2 X 4 R 10 To R 19 The definitions of m5 and m6 are as described above.

[0169] As a most concrete example, the second hole transport auxiliary layer may contain a compound represented by the chemical formula 2-1-1b.

[0170] For example, a compound represented by chemical formula 2 may be selected from, but is not limited to, one of the compounds listed in group 2.

[0171] [Group 2]

[0172] [F-1] [F-2] [F-3] [F-4] [F-5]

[0173] [F-6] [F-7] [F-8] [F-9] [F-10]

[0174] [F-11] [F-12] [F-13] [F-14] [F-15]

[0175] [F-16] [F-17] [F-18] [F-19] [F-20]

[0176] [F-21] [F-22] [F-23] [F-24] [F-25]

[0177] [F-26] [F-27] [F-28] [F-29] [F-30]

[0178] [F-31] [F-32] [F-33] [F-34] [F-35]

[0179] [F-36] [F-37] [F-38] [F-39] [F-40]

[0180] [F-41] [F-42] [F-43] [F-44] [F-45]

[0181] [F-46] [F-47] [F-48] [F-49] [F-50]

[0182] [F-51] [F-52] [F-53] [F-54] [F-55]

[0183] [F-56] [F-57] [F-58] [F-59] [F-60]

[0184] [F-61] [F-62] [F-63] [F-64] [F-65]

[0185] [F-66] [F-67] [F-68] [F-69] [F-70]

[0186] [F-71] [F-72] [F-73] [F-74] [F-75]

[0187] [F-76] [F-77] [F-78] [F-79] [F-80]

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

[0189] [F-86] [F-87] [F-88] [F-89] [F-90]

[0190] [F-91] [F-92] [F-93] [F-94] [F-95]

[0191] [F-96] [F-97] [F-98] [F-99] [F-100]

[0192] [F-101] [F-102] [F-103] [F-104] [F-105]

[0193] [F-106] [F-107] [F-108] [F-109] [F-110]

[0194] [F-111] [F-112] [F-113] [F-114] [F-115]

[0195] [F-116] [F-117] [F-118] [F-119] [F-120]

[0196] [F-121] [F-122] [F-123] [F-124] [F-125]

[0197] [F-126] [F-127] [F-128] [F-129] [F-130]

[0198] [F-131] [F-132] [F-133] [F-134] [F-135]

[0199] [F-136] [F-137] [F-138] [F-139] [F-140]

[0200] [F-141] [F-142] [F-143] [F-144] [F-145]

[0201] [F-146] [F-147] [F-148] [F-149] [F-150]

[0202] [F-151] [F-152] [F-153] [F-154] [F-155]

[0203] [F-156] [F-157] [F-158] [F-159] [F-160]

[0204] [F-161] [F-162] [F-163] [F-164] [F-165]

[0205] [F-166] [F-167] [F-168] [F-169] [F-170]

[0206] [F-171] [F-172] [F-173] [F-174] [F-175]

[0207] [F-176] [F-177] [F-178] [F-179] [F-180]

[0208] [F-181] [F-182] [F-183] [F-184] [F-185]

[0209] [F-186] [F-187] [F-188] [F-189] [F-190]

[0210] [F-191] [F-192] [F-193] [F-194] [F-195]

[0211] [F-196] [F-197] [F-198] [F-199] [F-200]

[0212] [F-201] [F-202] [F-203] [F-204] [F-205]

[0213] [F-206] [F-207] [F-208] [F-209] [F-210]

[0214] [F-211] [F-212] [F-213] [F-214] [F-215]

[0215] [F-216] [F-217] [F-218] [F-219] [F-220]

[0216] [F-221] [F-222] [F-223] [F-224] [F-225]

[0217] [F-226] [F-227] [F-228] [F-229] [F-230]

[0218] [F-231] [F-232] [F-233] [F-234] [F-235]

[0219] [F-236] [F-237] [F-238] [F-239] [F-240]

[0220] [F-241] [F-242] [F-243] [F-244] [F-245]

[0221] [F-246] [F-247] [F-248] [F-249] [F-250]

[0222] [F-251] [F-252] [F-253] [F-254] [F-255]

[0223] [F-256] [F-257] [F-258] [F-259] [F-260]

[0224] [F-261] [F-262] [F-263] [F-264] [F-265]

[0225] [F-266] [F-267] [F-268] [F-269] [F-270]

[0226] [F-271] [F-272] [F-273] [F-274] [F-275]

[0227] [F-276] [F-277] [F-278] [F-279] [F-280]

[0228] [F-281] [F-282] [F-283] [F-284] [F-285]

[0229] [F-286] [F-287] [F-288] [F-289] [F-290]

[0230] [F-291] [F-292] [F-293] [F-294] [F-295]

[0231] [F-296] [F-297] [F-298] [F-299] [F-300]

[0232] [F-301] [F-302] [F-303] [F-304] [F-305]

[0233] [F-306] [F-307] [F-308] [F-309] [F-310]

[0234] [F-311] [F-312] [F-313] [F-314] [F-315]

[0235] [F-316] [F-317] [F-318] [F-319] [F-320]

[0236] [F-321] [F-322] [F-323] [F-324] [F-325]

[0237] [F-326] [F-327] [F-328] [F-329] [F-330]

[0238] [F-331] [F-332] [F-333] [F-334] [F-335]

[0239] [F-336] [F-337] [F-338] [F-339] [F-340]

[0240] [F-341] [F-342] [F-343] [F-344] [F-345]

[0241] [F-346] [F-347] [F-348] [F-349] [F-350]

[0242] [F-351] [F-352] [F-353] [F-354] [F-355]

[0243] [F-356] [F-357] [F-358] [F-359] [F-360]

[0244] [F-361] [F-362] [F-363] [F-364] [F-365]

[0245] [F-366] [F-367] [F-368] [F-369] [F-370]

[0246] [F-371] [F-372] [F-373] [F-374] [F-375]

[0247] [F-376] [F-377] [F-378] [F-379] [F-380]

[0248] [F-381] [F-382] [F-383] [F-384] [F-385]

[0249] [F-386] [F-387] [F-388] [F-389] [F-390]

[0250] [F-391] [F-392] [F-393] [F-394] [F-395]

[0251] [F-396] [F-397] [F-398] [F-399] [F-400]

[0252] [F-401] [F-402] [F-403] [F-404]

[0253] [F-405] [F-406] [F-407] [F-408]

[0254] [F-409] [F-410] [F-411] [F-412]

[0255] [F-413] [F-414] [F-415] [F-416]

[0256] [F-417] [F-418] [F-419] [F-420]

[0257] [F-421] [F-422] [F-423] [F-424] [F-425]

[0258] [F-426] [F-427] [F-428] [F-429] [F-430]

[0259] [F-431] [F-432] [F-433] [F-434] [F-435]

[0260] [F-436] [F-437] [F-438] [F-439] [F-440]

[0261] [F-441] [F-442] [F-443] [F-444] [F-445]

[0262] [F-446] [F-447] [F-448] [F-449] [F-450]

[0263] [F-451] [F-452] [F-453] [F-454] [F-455]

[0264] [F-456] [F-457] [F-458] [F-459] [F-460]

[0265] [F-461] [F-462] [F-463] [F-464] [F-465]

[0266] [F-466] [F-467] [F-468] [F-469] [F-470]

[0267] [F-471] [F-472] [F-473] [F-474] [F-475]

[0268] [F-476] [F-477] [F-478] [F-479] [F-480]

[0269] [F-481] [F-482] [F-483] [F-484] [F-485]

[0270] [F-486] [F-487] [F-488] [F-489] [F-490]

[0271] [F-491] [F-492] [F-493] [F-494] [F-495]

[0272] [F-496] [F-497] [F-498] [F-499] [F-500]

[0273] [F-501] [F-502] [F-503] [F-504] [F-505]

[0274] [F-506] [F-507] [F-508] [F-509] [F-510]

[0275] [F-511] [F-512] [F-513] [F-514] [F-515]

[0276] [F-516] [F-517] [F-518] [F-519] [F-520]

[0277] [F-521] [F-522] [F-523] [F-524] [F-525]

[0278] [F-526] [F-527] [F-528] [F-529 ] [F-530]

[0279] [F-531] [F-532] [F-533] [F-534] [F-535]

[0280] [F-536] [F-537] [F-538] [F-539] [F-540]

[0281] [F-541] [F-542] [F-543] [F-544] [F-545]

[0282] [F-546] [F-547] [F-548] [F-549] [F-550]

[0283] [F-551] [F-552] [F-553] [F-554] [F-555]

[0284] [F-556] [F-557] [F-558] [F-559] [F-560]

[0285] [F-561] [F-562] [F-563] [F-564] [F-565]

[0286] [F-566] [F-567] [F-568] [F-569] [F-570]

[0287] [F-571] [F-572] [F-573] [F-574] [F-575]

[0288] [F-576] [F-577] [F-578] [F-579] [F-580]

[0289] [F-581] [F-582] [F-583] [F-584] [F-585]

[0290] [F-586] [F-587] [F-588] [F-589] [F-590]

[0291] [F-591] [F-592] [F-593] [F-594] [F-595]

[0292] [F-596] [F-597] [F-598] [F-599] [F-600]

[0293] [F-601] [F-602] [F-603] [F-604] [F-605]

[0294] [F-606] [F-607] [F-608] [F-609] [F-610]

[0295] [F-611] [F-612] [F-613] [F-614] [F-615]

[0296] Dn refers to the number of deuterium substitutions, where n is 1 or greater, and the maximum value of n corresponds to the number of substituted hydrogen positions.

[0297] In addition, the organic layer 30 may also include an electron transport region 34.

[0298] The electron transport region 34 can further increase electron injection and / or electron mobility between the cathode 20 and the light-emitting layer 32 and block holes.

[0299] Specifically, the electron transport region 34 may include an electron transport layer between the cathode 20 and the light-emitting layer 32 and an electron transport auxiliary layer between the light-emitting layer 32 and the electron transport layer, and may contain at least one of the compounds listed in group C in at least one of the electron transport layer and the electron transport auxiliary layer.

[0300] [Group C]

[0301] On the other hand, in addition to the light-emitting layer, an organic light-emitting diode may also include an electron injection layer (not shown), a hole injection layer (not shown), etc., as organic layers.

[0302] The hole injection layer is a layer that helps holes to be injected from the anode 10 into the light-emitting layer 32 and blocks electrons, and can be located between the anode 10 and the hole transport layer 31.

[0303] For example, the hole injection layer may include at least one of the compounds listed in Group B.

[0304] Similarly, in addition to the compounds mentioned above, known compounds and compounds with similar structures described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A may also be used.

[0305] Organic light-emitting diodes (OLEDs) can be manufactured by forming an anode or cathode on a substrate, then forming an organic layer using dry film methods such as vacuum deposition, sputtering, plasma electroplating, and ion plating, and forming a cathode or anode thereon.

[0306] Organic light-emitting diodes (OLEDs) can be used in organic light-emitting display devices.

[0307] 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.

[0308] 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.

[0309] (Preparation of compounds for organic optoelectronic devices)

[0310] Synthesis Example 1: Synthesis of Compounds 1-3

[0311] [Reaction Formula 1]

[0312] 10.0 g (38.64 mmol) of an intermediate of 6-(tert-butyl)-1-chlorodibenzo[b,d]furan, 24.38 g (46.38 mmol) of an intermediate of 9,9-dimethyl-N-(3-(9-phenyl-9H-fluorene-9-yl)phenyl)-9H-fluorene-2-amine, 7.43 g (77.30 mmol) sodium tert-butoxide, and 0.938 g (2.32 mmol) tritert-butylphosphine were dissolved in 380 ml of toluene, and 1.06 g (1.16 mmol) of Pd2(dba)3 was added. The mixture was then stirred and refluxed under a nitrogen atmosphere for 12 hours. When the reaction was complete, the organic layer extracted with ethyl acetate and distilled water was dried with anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated under reduced pressure. The product obtained was purified by silica gel column chromatography with n-hexane / dichloromethane (volume ratio 3:1) to obtain compounds 1-3 as 23.6 g (yield: 82%) of white solid target compounds.

[0313] Theoretical values: C, 89.92; H, 6.06; N, 1.87; O, 2.14

[0314] Experimental values: C, 89.92; H, 6.06; N, 1.87; O, 2.14

[0315] Synthesis Example 2: Synthesis of Compounds 1-6

[0316] [Reaction 2]

[0317] Compounds 1-6 (15.7 g, yield: 81%) were synthesized in the same manner as in Synthesis Example 1, except that 8.0 g of the intermediate of 6-(tert-butyl)-1-chlorodibenzo[b,d]furan and 14.90 g of the intermediate of N-(9,9-dimethyl-9H-fluorene-4-yl)-9,9-dimethyl-9H-fluorene-2-amine were used in an equivalent ratio of 1:1.2.

[0318] Theoretical values: C, 88.57; H, 6.62; N, 2.25; O, 2.56

[0319] Experimental values: C, 88.57; H, 6.62; N, 2.25; O, 2.56

[0320] Synthesis Example 3: Synthesis of Compounds 1-9

[0321] [Reaction 3]

[0322] Compounds 1-9 (16.4 g, yield: 80%) were synthesized in the same manner as in Synthesis Example 1, except that 8.0 g of the intermediate of 6-(tert-butyl)-1-chlorodibenzo[b,d]furan and 16.24 g of the intermediate of N-([1,1':4',1''-terphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine were used in an equivalent ratio of 1:1.2.

[0323] Theoretical values: C, 89.19; H, 6.26; N, 2.12; O, 2.42

[0324] Experimental values: C, 89.19; H, 6.26; N, 2.12; O, 2.42

[0325] Synthesis Example 4: Synthesis of Compounds 1-13

[0326] [Reaction 4]

[0327] Compounds 1-13 (19.2 g, yield: 80%) were synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of an intermediate of 6-(tert-butyl)-1-chlorodibenzo[b,d]furan and 18.62 g of an intermediate of bis(9,9-dimethyl-9H-fluorene-2-yl)amine were used in an equivalent ratio of 1:1.2.

[0328] Theoretical values: C, 88.57; H, 6.62; N, 2.25; O, 2.56

[0329] Experimental values: C, 88.57; H, 6.62; N, 2.25; O, 2.56

[0330] Comparative Synthesis Example 1: Synthesis of Compound R1

[0331] Compound R1 (10.5 g, yield: 73%) was synthesized in the same manner as in Synthesis Example 1, except that 6.0 g of the intermediate of 7-(tert-butyl)-1-chlorodibenzo[b,d]furan and 11.17 g of the intermediate of bis(9,9-dimethyl-9H-fluorene-2-yl)amine were used in an equivalent ratio of 1:1.2.

[0332] Theoretical values: C, 88.57; H, 6.62; N, 2.25; O, 2.56

[0333] Experimental values: C, 88.57; H, 6.62; N, 2.25; O, 2.56

[0334] Comparative Synthesis Example 2: Synthesis of Compound R2

[0335] Compound R2 (13.6 g, yield: 78%) was synthesized in the same manner as in Synthesis Example 1, except that 7.0 g of the intermediate of 6-(tert-butyl)-1-chlorodibenzo[b,d]furan and 13.81 g of the intermediate of N-(9,9-dimethyl-9H-fluoren-2-yl)naphtho[2,3-b]benzofuran-3-amine were used in an equivalent ratio of 1:1.2.

[0336] Theoretical values: C, 87.14; H, 5.76; N, 2.16; O, 4.94

[0337] Experimental values: C, 87.14; H, 5.76; N, 2.16; O, 4.94

[0338] Comparative Synthesis Example 3: Synthesis of Compound R3

[0339] Compound R3 (9.2 g, yield: 82%) was synthesized in the same manner as in Synthesis Example 1, except that 5.0 g of the intermediate of 6-(tert-butyl)-2-chlorodibenzo[b,d]furan and 8.38 g of the intermediate of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-4-amine were used in an equivalent ratio of 1:1.2.

[0340] Theoretical values: C, 88.47; H, 6.39; N, 2.40; O, 2.74

[0341] Experimental values: C, 88.47; H, 6.39; N, 2.40; O, 2.74

[0342] Comparative Synthesis Example 4: Synthesis of Compound R4

[0343] Compound R4 (9.1 g, yield: 55%) was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of the intermediate of (9-chlorodibenzo[b,d]furan-4-yl)triphenylsilane and 7.21 g of the intermediate of 9H-3,9'-bicarbazole were used in a 1:1 equivalent ratio.

[0344] Theoretical values: C, 85.68; H, 4.79; N, 3.70; O, 2.11; Si, 3.71

[0345] Experimental values: C, 85.68; H, 4.79; N, 3.70; O, 2.11; Si, 3.71

[0346] Comparative Synthesis Example 5: Synthesis of Compound R5

[0347] Compound R5 (9.5 g, yield: 80%) was synthesized in the same manner as in Synthesis Example 1, except that 5.0 g of the intermediate of 6-(tert-butyl)-1-chlorodibenzo[b,d]thiophene and 8.98 g of the intermediate of N-(4-(dibenzo[b,d]furan-2-yl)phenyl)-[1,1'-biphenyl]-4-amine were used in an equivalent ratio of 1:1.2.

[0348] Theoretical values: C, 85.02; H, 5.43; N, 2.16; O, 2.46; S, 4.93

[0349] Experimental values: C, 85.02; H, 5.43; N, 2.16; O, 2.46; S, 4.93

[0350] (Manufacturing of organic light-emitting diodes)

[0351] Example 1

[0352] A glass substrate coated with an 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. It was then transferred to a plasma cleaner and cleaned with oxygen plasma for 10 minutes before being transferred to a vacuum depositor. Using this prepared ITO / Ag / ITO (reflective electrode) 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 1240 Å thick hole injection layer to form a hole transport layer. Compounds 1-3 obtained in Synthesis Example 1 were deposited on the hole transport layer to a thickness of 270 Å to form a first hole transport auxiliary layer. A second hole transport auxiliary layer was formed by depositing compound F-429 on the first hole transport auxiliary layer to a thickness of 50 Å. 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% GD was doped as a dopant to form a 350 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.

[0353] ITO / Ag / ITO / Compound A (3% NDP-9 doped, 100 Å) / Compound A (1240 Å) / First hole transport auxiliary layer (270 Å) / Second hole transport auxiliary layer (50 Å) / Emitting layer [Body (Body H1 : Body H2 = 40 wt% : 60 wt%) : GD = 85 wt% : 15 wt%] (350 Å) / Compound C (50 Å) / Compound D : Liq (310 Å) / Yb / AgMg.

[0354] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine

[0355] Compound C: 4-([1,1'-biphenyl]-4-yl)-6-(3'-(9,9-dimethyl-9H-fluorene-4-yl)-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine

[0356] Compound D: 6,6'-(naphthalene-1,2-dimethylbis(4,1-phenylene))bis(2,4-diphenyl-1,3,5-triazine)

[0357] Main component H1: 9-(3-(4-phenyl-6-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-9H-carbazole

[0358] Main component H2: 5,8-bis([1,1'-biphenyl]-4-yl)-5,8-dihydroindolo[2,3-c]carbazole

[0359] GD:

[0360] Examples 2 to 4 and Comparative Examples 1 to 5

[0361] The diodes of Examples 2 to 4 and Comparative Examples 1 to 5 were manufactured in the same manner as in Example 1, except that the composition of the hole transport auxiliary layer was changed as described in Table 1.

[0362] Evaluation: Lifetime Measurement

[0363] By using brightness (cd / m 2 Maintain at 24000 cd / m 2 The results were obtained by measuring the time it took for the current efficiency (cd / A) to drop to 97%.

[0364] The relative values ​​of lifetime based on Comparative Example 1 are shown in Table 1.

[0365] (Table 1)

[0366] Referring to Table 1, the lifespan of the organic light-emitting diodes using the compounds according to the embodiments is significantly improved compared to the organic light-emitting diodes according to the comparative examples.

[0367] Although this disclosure 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 various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. A compound for use in organic optoelectronic devices, said compound being represented by chemical formula 1: [Chemical Formula 1] In chemical formula 1, X 1 Is it O or S? R 1 To R 4 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. R 5 and R 6 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 7 To R 9 Each is independently either an unsubstituted methyl group or a deuterated methyl group. L 1 It is a single bond or a substituted or unsubstituted phenylene. Ar 1 It is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted 1-fluorenyl, a substituted or unsubstituted 2-fluorenyl, a substituted or unsubstituted 3-fluorenyl, a substituted or unsubstituted 4-fluorenyl, a substituted or unsubstituted 9-fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl. m1 to m3 are each an independent integer from 1 to 3. m4 is an integer from 1 to 4, and When m1 to m4 are 2 or greater, R 1 To R 4 They are the same as or different from each other.

2. The compound for organic optoelectronic devices according to claim 1, wherein, Chemical formula 1 can be represented by any one of chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In chemical formulas 1-1 to 1-4 X 1 R 1 To R 9 L 1 Ar 1 m1 to m4 as defined in claim 1.

3. The compound for organic optoelectronic devices according to claim 1, wherein, R 1 To R 4 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl.

4. The compound for organic optoelectronic devices according to claim 1, wherein, R 5 and R 6 Each is independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C12 aryl.

5. The compound for organic optoelectronic devices according to claim 1, wherein, The compounds for organic optoelectronic devices represented by chemical formula 1 are selected from the compounds listed in group 1: [Group 1] [1-1] [1-2] [1-3] [1-4] [1-5] [1-6] [1-7] [1-8] [1-9] [1-10] [1-11] [1-12] [1-13] [1-14] [1-15] [1-16] [1-17] [1-18] [1-19] [1-20] [1-21] [1-22] [1-22] [1-24] [1-25] [1-26] [1-27] [1-28] [1-29] [1-30] [1-31] [1-32] [1-33] [1-34] [1-35] [1-36] [1-37] [1-38] [1-39] [1-40] [1-41] [1-42] [1-43] [1-44] [1-45] [1-46] [1-47] [1-48] [1-49] [1-50] [1-51] [1-52] [1-53] [1-54] [1-55] [1-56] [1-57] [1-58] [1-59] [1-60] Dn refers to the number of deuterium substitutions, where n is 1 or greater, and the maximum value of n corresponds to the number of substituted hydrogen positions.

6. The compound for organic optoelectronic devices according to claim 5, wherein, The deuterium-substituted structures are selected from the compounds listed in Group 1-1: [Group 1-1] [1-61] [1-62] [1-63] [1-64] [1-65]。 7. An organic optoelectronic device, comprising: The anode and cathode facing each other, and At least one organic layer between the anode and the cathode, The organic layer comprises the compound for an organic optoelectronic device as described in any one of claims 1 to 6.

8. The organic optoelectronic device according to claim 7, wherein, The organic layer includes a light-emitting layer, and The light-emitting layer contains the compound used in the organic optoelectronic device.

9. The organic optoelectronic device according to claim 7, wherein, The organic layer includes: Emissive layer, 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; The hole transport auxiliary layer contains the compound used in the organic optoelectronic device.

10. The organic optoelectronic device according to claim 9, wherein, The organic optoelectronic device includes a second hole transport auxiliary layer between the light-emitting layer and the hole transport auxiliary layer, and The second hole transport auxiliary layer includes a compound represented by chemical formula 2, which is different from the compound for organic optoelectronic devices contained in the hole transport auxiliary layer: [Chemical Formula 2] In chemical formula 2, X 2 Is it O, S, or CR? 20 R 21 , Ar 2 and Ar 3 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. L 2 To L 4 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. R 20 and R 21 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 10 To R 14 Each of these groups is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C1 to C30 alkylsilyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. m5 is an integer from 1 to 3, and When m5 is 2 or greater, each R 10 They are the same or different from each other.

11. The organic optoelectronic device according to claim 10, wherein, Chemical formula 2 is represented by chemical formulas 2-1 to 2-4: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] In chemical formulas 2-1 to 2-4 L 2 To L 4 X 2 R 10 To R 14 Ar 2 Ar 3 And m5 as defined in claim 10.

12. The organic optoelectronic device according to claim 10, wherein, Ar 2 and Ar 3 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 anthraquinyl, 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 dibenzothiophenyl, or substituted or unsubstituted dibenzothiophenyl.

13. The organic optoelectronic device according to claim 10, wherein, L 2 -Ar 2 and L 3 -Ar 3 Each substituent is independently selected from those listed in Group I: [Group I] In group I, R 15 To R 19 Each of these groups is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, or substituted or unsubstituted C6 to C12 aryl. m6 is an integer from 1 to 5. m7 is an integer from 1 to 4. m8 is an integer from 1 to 7. m9 is an integer from 1 to 3. m10 is an integer of 1 or 2, and It is a connection point.

14. The organic optoelectronic device according to claim 10, wherein, The second hole transport auxiliary layer comprises a compound represented by chemical formula 2-1-1: [Chemical Formula 2-1-1] In chemical formula 2-1-1, X 2 Ar 3 L 2 To L 4 R 10 To R 14 and m5 as defined in claim 10, X 4 Is it O, S, or CR? 22 R 23 , R 22 and R 23 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 15 To R 19 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and m6 is an integer from 1 to 3.

15. The organic optoelectronic device according to claim 14, wherein, The second hole transport auxiliary layer comprises a compound represented by chemical formula 2-1-1b: [Chemical Formula 2-1-1b] In chemical formula 2-1-1b, Ar 3 X 2 X 4 R 10 To R 19 m5 and m6 are as defined in claim 14.

16. The organic optoelectronic device according to claim 10, wherein, The compounds represented by chemical formula 2 are selected from the compounds listed in group 2: [Group 2] [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] [F-441] [F-442] [F-443] [F-444] [F-445] [F-446] [F-447] [F-448] [F-449] [F-450] [F-451] [F-452] [F-453] [F-454] [F-455] [F-456] [F-457] [F-458] [F-459] [F-460] [F-461] [F-462] [F-463] [F-464] [F-465] [F-466] [F-467] [F-468] [F-469] [F-470] [F-471] [F-472] [F-473] [F-474] [F-475] [F-476] [F-477] [F-478] [F-479] [F-480] [F-481] [F-482] [F-483] [F-484] [F-485] [F-486] [F-487] [F-488] [F-489] [F-490] [F-491] [F-492] [F-493] [F-494] [F-495] [F-496] [F-497] [F-498] [F-499] [F-500] [F-501] [F-502] [F-503] [F-504] [F-505] [F-506] [F-507] [F-508] [F-509] [F-510] [F-511] [F-512] [F-513] [F-514] [F-515] [F-516] [F-517] [F-518] [F-519] [F-520] [F-521] [F-522] [F-523] [F-524] [F-525] [F-526] [F-527] [F-528] [F-529] [F-530] [F-531] [F-532] [F-533] [F-534] [F-535] [F-536] [F-537] [F-538] [F-539] [F-540] [F-541] [F-542] [F-543] [F-544] [F-545] [F-546] [F-547] [F-548] [F-549] [F-550] [F-551] [F-552] [F-553] [F-554] [F-555] [F-556] [F-557] [F-558] [F-559] [F-560] [F-561] [F-562] [F-563] [F-564] [F-565] [F-566] [F-567] [F-568] [F-569] [F-570] [F-571] [F-572] [F-573] [F-574] [F-575] [F-576] [F-577] [F-578] [F-579] [F-580] [F-581] [F-582] [F-583] [F-584] [F-585] [F-586] [F-587] [F-588] [F-589] [F-590] [F-591] [F-592] [F-593] [F-594] [F-595] [F-596] [F-597] [F-598] [F-599] [F-600] [F-601] [F-602] [F-603] [F-604] [F-605] [F-606] [F-607] [F-608] [F-609] [F-610] [F-611] [F-612] [F-613] [F-614] [F-615] Dn refers to the number of deuterium substitutions, where n is 1 or greater, and the maximum value of n corresponds to the number of substituted hydrogen positions.

17. A display device comprising the organic optoelectronic device according to any one of claims 7 to 16.

Images