Compound for organic optoelectronic device, organic optoelectronic device, and display device

Abstract

The present invention relates to: a compound for an organic optoelectronic device represented by chemical formula 1; and an organic optoelectronic device and a display device comprising the compound. The detailed description of the chemical formula 1 is defined in the specification.

Description

Technical Field

[0001] Disclosed are a compound for an organic optoelectronic device, an organic optoelectronic device, and a display device. Background Art

[0002] An organic optoelectronic device (organic optoelectronic diode) is a device that can convert electrical energy into light energy and vice versa.

[0003] Organic optoelectronic devices can be broadly divided into two categories based on their operating principles: photovoltaic devices that generate electrical energy by separating excitons formed from light energy into electrons and holes and transferring these electrons and holes to different electrodes; and light-emitting devices that generate light energy from electrical energy by applying voltage or current to electrodes.

[0004] Examples of the organic optoelectronic device include an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.

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

[0006] Technical issues

[0007] One embodiment provides a compound for an organic optoelectronic device capable of realizing an organic optoelectronic device with high efficiency and a long lifespan.

[0008] Another embodiment provides an organic optoelectronic device including the compound for an organic optoelectronic device.

[0009] Another embodiment provides a display device including an organic optoelectronic device.

[0010] Technical Solution

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

[0012] [Chemical Formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group,

[0016] R1 to R 5 each independently is hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl,

[0017] m1and m3to m5are each independently one of integers from 1 to 4,

[0018] m2is one of integers from 1 to 3, and

[0019] Chemical Formula 1 satisfies at least one of the following (i) to (iii).

[0020] (i) R 1 to R 5 at least one is deuterium, C1 to C10 alkyl substituted with one or more deuteriums, or C6 to C12 aryl substituted with one or more deuteriums;

[0021] (ii) Ar 1 is C6 to C20 aryl substituted with one or more deuteriums, or C2 to C30 heterocyclic group substituted with one or more deuteriums; and

[0022] (iii) Ar 2 is C6 to C20 aryl substituted with one or more deuteriums, or C2 to C30 heterocyclic group substituted with one or more deuteriums.

[0023] According to another embodiment, an 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 comprises a compound for an organic optoelectronic device.

[0024] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0025] Advantageous Effects

[0026] An organic optoelectronic device having high efficiency and long lifespan can be implemented. BRIEF DESCRIPTION OF DRAWINGS

[0027] Figure 1 is a cross-sectional view illustrating an organic light emitting diode according to one embodiment.

[0028] <REFERENCE NUMERALS>

[0029] 100: organic light emitting diode

[0030] 105: organic layer

[0031] 110: cathode

[0032] 120: anode

[0033] 130: Luminous layer

[0034] 140: Hole transport zone

[0035] 150: Electron transport region DETAILED DESCRIPTION

[0036] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, and the present disclosure is not limited thereto.

[0037] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, halogen, hydroxy, amino, substituted or unsubstituted C1 to C30 amine, 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 a combination thereof.

[0038] In one embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, or cyano. In a specific embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. In a specific embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. In a specific embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0039] In the present specification, "unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom remains.

[0040] In the present specification, "hydrogen substitution (—H)" may include "deuterium substitution (—D)" or "tritium substitution (—T)".

[0041] As used herein, when no definition is otherwise provided, "hetero" means containing one to three heteroatoms selected from N, O, S, P and Si and the remaining carbon in one functional group.

[0042] As used herein, "aryl" refers to a group including at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p orbitals forming conjugation, such as phenyl, naphthyl, etc.; two or more hydrocarbon aromatic moieties may be linked by a σ bond, and may be, for example, biphenyl, terphenyl, quaterphenyl, etc.; and two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl.

[0043] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings that share adjacent pairs of carbon atoms) functional groups.

[0044] As used herein, "heterocyclyl" is a general concept of heteroaryl and may include at least one heteroatom selected from N, O, S, P and Si in place of carbon (C) in a cyclic compound such as an aryl, a cycloalkyl, a fused ring thereof or a combination thereof. When the heterocyclyl is a fused ring, the entire ring or each ring of the heterocyclyl may include one or more heteroatoms.

[0045] As an example, "heteroaryl" may refer to an aryl group comprising at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups may be directly linked by a sigma bond, or when the heteroaryl group comprises two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may comprise one to three heteroatoms.

[0046] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof, but is not limited thereto.

[0047] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted The present invention may include, but is not limited to, quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzofuranofluorenyl, substituted or unsubstituted benzothiophenefluorenyl, or a combination thereof, but is not limited thereto.

[0048] As used herein, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive properties according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0049] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductive properties according to the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0050] Hereinafter, a compound for an organic optoelectronic device according to one embodiment is described.

[0051] The compound for an organic optoelectronic device according to one embodiment may be represented by Chemical Formula 1.

[0052] [Chemical Formula 1]

[0053]

[0054] In Chemical Formula 1,

[0055] Ar 1 and Ar 2are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group,

[0056] R 1 to R 5 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl,

[0057] m1 and m3 to m5 are each independently one of integers from 1 to 4,

[0058] m2 is an integer from 1 to 3,

[0059] Chemical Formula 1 satisfies at least one of the following (i) to (iii).

[0060] (i)R 1 to R 5 At least one of the following is deuterium, a C1 to C10 alkyl group substituted with one or more deuteriums, or a C6 to C12 aryl group substituted with one or more deuteriums;

[0061] (ii)Ar 1 is a C6 to C20 aryl group substituted by one or more deuterium groups or a C2 to C30 heterocyclic group substituted by one or more deuterium groups;

[0062] (iii)Ar 2 is a C6 to C20 aryl group substituted by one or more deuterium groups or a C2 to C30 heterocyclic group substituted by one or more deuterium groups.

[0063] The compound for an organic optoelectronic device represented by Chemical Formula 1 has a structure in which triazine is substituted with two or more carbazolyl groups, and at least one of the carbazolyl groups substitutes the triazine at the 9-position via an o-phenylene group.

[0064] Thus, the first compound has a structure containing an o-carbazole in addition to a triazine, resulting in particularly excellent energy transfer efficiency for phosphorescent dopants, making it a favorable material for use as a phosphorescent host. When used as a host, the substitution of two or more carbazole groups on the triazine helps expand the resonant structure of the carbazole moiety, which helps stabilize the hole-transporting portion within the molecule. This optimizes the charge balance between the electron-transporting and hole-transporting portions within the molecule, further contributing to improved lifetime.

[0065] Furthermore, when carbazole is substituted at the ortho position of triazine, the dihedral angle increases due to steric hindrance between the triazine and carbazole, and the triazine and carbazole moieties twist relative to each other, thereby increasing the dihedral angle. This means that the electron clouds at the HOMO and LUMO levels are largely separated without overlap. Due to its low ΔEst, it enables rapid energy transfer and exhibits high efficiency, particularly when used as a phosphorescent host. Furthermore, side reaction pathways in the excited state are reduced, further enhancing the lifetime.

[0066] Furthermore, the inclusion of at least one deuterium can further reduce the compound's zero-point energy and vibrational energy. This further lowers the ground state energy, weakens intermolecular interactions, and can render the resulting film amorphous, improving heat resistance and effectively extending its lifespan. This can, when used, provide highly efficient, and particularly long-lived, organic light-emitting diodes.

[0067] When m1 is 2 or greater, each R 1 They may be the same as or different from each other.

[0068] When m2 is 2 or greater, each R 2 They may be the same as or different from each other.

[0069] When m3 is 2 or greater, each R 3 They may be the same as or different from each other.

[0070] When m4 is 2 or greater, each R 4 They may be the same as or different from each other.

[0071] When m5 is 2 or greater, each R 5 They may be the same as or different from each other.

[0072] For example, R 1 to R 5 At least one of may be deuterium, a C1 to C10 alkyl group substituted by one or more deuteriums, or a C6 to C12 aryl group substituted by one or more deuteriums, and

[0073] Ar 1 It may be a C6 to C20 aryl group substituted by one or more deuterium groups or a C2 to C30 heterocyclic group substituted by one or more deuterium groups.

[0074] As another example, R 1 to R 5 At least one of may be deuterium, a C1 to C10 alkyl group substituted by one or more deuteriums, or a C6 to C12 aryl group substituted by one or more deuteriums, and

[0075] Ar 2 It may be a C6 to C20 aryl group substituted by one or more deuterium groups or a C2 to C30 heterocyclic group substituted by one or more deuterium groups.

[0076] As another example, R 1 to R 5 At least one of may be deuterium, a C1 to C10 alkyl group substituted by one or more deuteriums, or a C6 to C12 aryl group substituted by one or more deuteriums,

[0077] Ar 1 may be a C6 to C20 aryl group substituted by one or more deuterium groups or a C2 to C30 heterocyclic group substituted by one or more deuterium groups, and

[0078] Ar 2 It may be a C6 to C20 aryl group substituted by one or more deuterium groups or a C2 to C30 heterocyclic group substituted by one or more deuterium groups.

[0079] In one embodiment, the deuterium substitution ratio of Chemical Formula 1 may be 30% to 100%.

[0080] The deuterium substitution ratio refers to the percentage of deuterium substitution relative to the total number of hydrogen atoms.

[0081] For example, if 8 of 10 hydrogen positions are substituted with deuterium, the deuterium substitution ratio may be 80%.

[0082] For example, Chemical Formula 1 may be represented by any one of Chemical Formula 1A to Chemical Formula 1D.

[0083] [Chemical Formula 1A]

[0084]

[0085] [Chemical Formula 1B]

[0086]

[0087] [Chemical Formula 1C]

[0088]

[0089] [Chemical Formula 1D]

[0090]

[0091] In Chemical Formulas 1A to 1D,

[0092] R 1 to R 5 、Ar 1 、Ar 2 The definitions of and m1 to m5 are the same as above.

[0093] For example, in Chemical Formula 1, Ar 1 It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted dibenzosilyl group.

[0094] For example, in Chemical Formula 1, Ar 2 It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0095] For example, in Chemical Formula 1, R 1 to R 5 Each of them may independently be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C5 alkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted biphenyl.

[0096] In this case, Chemical Formula 1 satisfies at least one of the following (iv) to (vi).

[0097] (iv)R 1 to R 5 At least one of the following is deuterium, a C1 to C5 alkyl group substituted with one or more deuterium groups, a phenyl group substituted with one or more deuterium groups, or a biphenyl group substituted with one or more deuterium groups;

[0098] (v)Ar 1 is phenyl substituted by one or more deuterium groups, biphenyl substituted by one or more deuterium groups, terphenyl substituted by one or more deuterium groups, naphthyl substituted by one or more deuterium groups, anthracenyl substituted by one or more deuterium groups, phenanthrenyl substituted by one or more deuterium groups, fluorenyl substituted by one or more deuterium groups, dibenzofuranyl substituted by one or more deuterium groups, dibenzothienyl substituted by one or more deuterium groups, or dibenzosilyl substituted by one or more deuterium groups; and

[0099] (vi)Ar 2 is phenyl substituted by one or more deuterium groups, biphenyl substituted by one or more deuterium groups, or naphthyl substituted by one or more deuterium groups.

[0100] As a specific example, Chemical Formula 1 may be represented by Chemical Formula 1B or Chemical Formula 1C.

[0101] For example, the first compound represented by Chemical Formula 1 may be one selected from the compounds listed in Group 1, but is not limited thereto.

[0102] [Group 1]

[0103]

[0104]

[0105]

[0106]

[0107] In the compounds A-1 to A-85 of Group 1,

[0108] D represents a structure in which deuterium is substituted, and

[0109] The substitution ratio of D can be 10% to 100%, preferably 30% to 100%, and more preferably 50% to 100%.

[0110] According to the position and substitution ratio of deuterium substitution, the most specific structures of the compounds A-1 to A-85 are provided as examples below, which do not limit the scope of rights of the compounds not shown below. The scope of the present application is determined by the claims.

[0111] Examples of the compound A-2 can include compounds A-86 to A-90, but are not limited thereto.

[0112]

[0113] Examples of the compound A-22 can include compounds A-91 to A-95, but are not limited thereto.

[0114]

[0115]

[0116] Examples of the compound A-47 can include compounds A-96 to A-100, but are not limited thereto.

[0117]

[0118] Examples of the compound A-67 can include compounds A-101 to A-105, but are not limited thereto.

[0119]

[0120] Examples of the compound A-12 can include compounds A-106 to A-110, but are not limited thereto.

[0121]

[0122] Examples of the compound A-32 can include compounds A-111 to A-115, but are not limited thereto.

[0123]

[0124]

[0125] Examples of compound A-57 may include compounds A-116 to A-120, but are not limited thereto.

[0126]

[0127] Examples of compound A-77 may include compounds A-121 to A-125, but are not limited thereto.

[0128]

[0129] In addition to the above-mentioned compounds for an organic optoelectronic device, one or more other compounds may be included.

[0130] For example, a dopant may be further contained.

[0131] The dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and may be, for example, a red or green phosphorescent dopant.

[0132] A dopant is a material mixed in a small amount with a compound used in an organic optoelectronic device to induce light emission, and is generally a material such as a metal complex that emits light by being excited multiple times to a triplet state or more. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof may be used.

[0133] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be an organometallic compound containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the chemical formula Z, but is not limited thereto.

[0134] [Chemical formula Z]

[0135] L 4 MX 3

[0136] In the chemical formula Z, M is a metal, and L 4 and X 3 The same or different ligands that form a complex with M.

[0137] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L 4 and X 3 This may be, for example, a bidentate ligand.

[0138] By L 4 and X 3 Examples of the ligand represented by may be selected from the chemical formulae listed in Group A, but are not limited thereto.

[0139] [Group A]

[0140]

[0141] In Group A,

[0142] R 300 to R 302 are each independently hydrogen, deuterium, C1 to C30 alkyl which may be substituted by halogen, C6 to C30 aryl which may be substituted by C1 to C30 alkyl, or halogen, and

[0143] R 303 to R 324 Each 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, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

[0144] The dopant according to one embodiment may be an iridium complex, and may be represented, for example, by Chemical Formula 5-1 or Chemical Formula 5-2.

[0145] [Chemical Formula 5-1]

[0146]

[0147] In Chemical Formula 5-1,

[0148] R 101 to R 116 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0149] R 132 to R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0150] R 101 to R 116 At least one of them is a functional group represented by Chemical Formula V-1,

[0151] L 100 is a bidentate ligand for a monovalent anion and is coordinated to iridium via a lone electron pair of carbon or a heteroatom, and

[0152] m14 and m15 are each independently any one of integers from 0 to 3, and m14+m15 is any one of integers from 1 to 3,

[0153] [Chemical Formula V-1]

[0154]

[0155] In Chemical Formula V-1,

[0156] R 135 to R 139 are each 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

[0157] * refers to the moiety attached to the carbon atom.

[0158] [Chemical Formula 5-2]

[0159]

[0160] In Chemical Formula 5-2,

[0161] R 101 to R 117 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 133 R 134 R 135 ,

[0162] R 133 to R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0163] L 100 is a bidentate ligand for a monovalent anion and is coordinated to iridium via a lone electron pair of carbon or a heteroatom, and

[0164] n1 and n2 are each independently any one of integers from 0 to 3, and n1+n2 is any one of integers from 1 to 3.

[0165] In another embodiment, the dopant may be, for example, a platinum complex represented by Chemical Formula Z-1.

[0166] [Chemical Formula Z-1]

[0167]

[0168] In formula Z-1, rings A, B, C, and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0169] R A 、R B 、R C and R D Each is independently mono-, di-, tri- or tetra-substituted or unsubstituted.

[0170] L B , L C and L D are each independently a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' or a combination thereof,

[0171] 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 does not exist;

[0172] R A 、R B 、R C 、R D R 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, sulfanyl, sulfinyl, sulfonyl, phosphino, or a combination thereof; any adjacent R A 、R B 、R C 、R D , R and R' are optionally linked to each other to provide a ring; X B 、X C 、X D and X E are each independently selected from carbon and nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 Each represents oxygen or a direct bond.

[0173] The platinum complex may be represented by, for example, Chemical Formula 6-1 or Chemical Formula 6-2.

[0174] [Chemical Formula 6-1]

[0175]

[0176] [Chemical Formula 6-2]

[0177]

[0178] In Chemical Formula 6-1 and Chemical Formula 6-2,

[0179] X 100 Selected from O, S and NR 132 ,

[0180] R 118 to R 132 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 133 R 134 R 135 ,

[0181] R 133 to R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0182] R 118 to R 132 At least one of them is -SiR 133 R 134 R 135 or tert-butyl, and

[0183] R 133 to R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0184] Hereinafter, an organic optoelectronic device including the above-mentioned compound for an organic optoelectronic device is described.

[0185] The organic optoelectronic device may be a suitable device that converts electrical energy into light energy and vice versa, such as an organic photovoltaic device, an organic light emitting diode, an organic solar cell, or an organic photosensitive drum.

[0186] Herein, an organic light emitting diode as one example of an organic optoelectronic device is described with reference to the accompanying drawings.

[0187] Figure 1 is a cross-sectional view showing an organic light emitting diode according to one embodiment.

[0188] refer to Figure 1, the organic light emitting diode 100 according to one embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 disposed between the anode 120 and the cathode 110 .

[0189] The anode 120 may be made of a conductor having a large work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0190] The cathode 110 may be made of a conductor having 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 110 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; or a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0191] The organic layer 105 may include the above-described compound for an organic optoelectronic device.

[0192] The compound for an organic optoelectronic device further including a dopant may be, for example, a green light emitting composition.

[0193] The light emitting layer 130 may include, for example, the above-described compound for an organic optoelectronic device as a phosphorescent host.

[0194] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0195] The charge transport region may be, for example, a hole transport region 140 .

[0196] The hole transport region 140 may further improve hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.

[0197] Specifically, the hole transport region 140 may include a hole transport layer between the anode 120 and the light-emitting layer 130 and a hole transport auxiliary layer between the light-emitting layer 130 and the hole transport layer, and at least one of the compounds listed in group B may be included in at least one layer of the hole transport layer and the hole transport auxiliary layer.

[0198] [Group B]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205] (Dn refers to the number of deuterium atoms substituted and indicates a structure in which one or more deuterium atoms are substituted)

[0206] In the hole transport zone 140, in addition to the above-mentioned compounds, known compounds and compounds having a similar structure disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, and the like can be used.

[0207] In addition, the charge transport zone can be, for example, the electron transport zone 150.

[0208] The electron transport zone 150 can further improve electron injection and / or electron mobility between the cathode 110 and the light-emitting layer 130 and block holes.

[0209] Specifically, the electron transport zone 150 can include an electron transport layer between the cathode 110 and the light-emitting layer 130 and an electron transport auxiliary layer between the light-emitting layer 130 and the electron transport layer, and at least one of the electron transport layer and the electron transport auxiliary layer can contain at least one of the compounds of Group C.

[0210] [Group C]

[0211]

[0212]

[0213]

[0214] One embodiment can be an organic light-emitting diode including a light-emitting layer as an organic layer.

[0215] Another embodiment can be an organic light-emitting diode including a light-emitting layer and a hole transport zone as organic layers.

[0216] Another embodiment may be an organic light emitting diode including a light emitting layer and an electron transport region as organic layers.

[0217] In addition to the light emitting layer 130, the organic light emitting diode according to one embodiment further includes a hole transport region 140 and an electron transport region 150 as the organic layer 105. Figure 1 shown.

[0218] On the other hand, the organic light emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. as organic layers in addition to the light emitting layer.

[0219] The organic light emitting diode 100 may be manufactured by forming an anode or a cathode on a substrate, then forming an organic layer by a dry film method such as vacuum deposition, sputtering, plasma plating, and ion plating, and forming a cathode or an anode thereon.

[0220] Organic light emitting diodes can be applied to organic light emitting display devices.

[0221] Hereinafter, the embodiments are described in more detail with reference to Examples. However, these Examples are exemplary, and the scope of the present invention is not limited thereto.

[0222] Invention Mode

[0223] Hereinafter, starting materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry, or P&H Tech, or synthesized by known methods unless otherwise specified.

[0224] (Preparation of Compounds for Organic Optoelectronic Devices)

[0225] Synthesis Example 1: Synthesis of Intermediate Int-01

[0226] [Reaction formula 1]

[0227]

[0228] 2,4-dichloro-6-(biphenyl-4-yl)-1,3,5-triazine (61.37 g, 203.11 mmol), 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (50 g, 135.41 mmol), K2CO3 (46.79 g, 338.51 mmol) and Pd(dppf)Cl2 (5.53 g, 6.77 mmol) were added to a round-bottom flask and dissolved in toluene (500 ml) and distilled water (200 ml), and then stirred and refluxed at 60°C for 12 hours. When the reaction was complete, after removing the aqueous layer, the solid obtained by filtration was dissolved in monochlorobenzene, filtered with silica gel / celite, and after removing an appropriate amount of the organic solvent, recrystallized with methanol to obtain 53.07 g (77%) of Intermediate Int-01.

[0229] Synthesis Example 2: Synthesis of Compound A-22-a

[0230] [Reaction formula 2]

[0231]

[0232] (2-(9H-carbazol-9-yl)phenyl)boronic acid (8.88 g, 30.94 mmol), intermediate Int-01 (15 g, 29.47 mmol), K2CO3 (10.18 g, 73.67 mmol) and Pd(PPh3)4 (1.7 g, 1.47 mmol) were added to a round-bottom flask and dissolved in THF (100 ml) and distilled water (40 ml), and then stirred and refluxed at 70°C for 12 hours. When the reaction was complete, the mixture was added to methanol (500 mL) to crystallize a solid, which was filtered and dissolved in monochlorobenzene, then filtered with silica gel / celite, and after removing an appropriate amount of the organic solvent, recrystallized with methanol to obtain 18.4 g (87%) of compound A-22-a.

[0233] Synthesis Example 3: Synthesis of Intermediate Int-02

[0234] [Reaction formula 3]

[0235]

[0236] 2-Bromocarbazole (15 g, 60.95 mmol), phenylboronic acid (11.44 g, 73.14 mmol), K CO (21.06 g, 152.38 mmol) and Pd (PPh) (3.52 g, 3.05 mmol) were added to a round-bottom flask and dissolved in THF (200 ml) and distilled water (75 ml), and then stirred and refluxed at 60 ° C. for 12 hours. When the reaction was completed, after removing the aqueous layer, 12.3 g (83%) of intermediate Int-02 was obtained by using column chromatography (hexane: DCM (20%)).

[0237] Synthesis Example 4: Synthesis of Intermediate Int-03

[0238] [Reaction formula 4]

[0239]

[0240] Intermediate Int-02 (15 g, 61.65 mmol), 2-fluorobromobenzene (11.33 g, 64.73 mmol) and K 2 PO 4 (28.79 g, 135.64 mmol) were added to a round-bottom flask and dissolved in DMF (200 ml), followed by stirring and reflux at 150° C. for 12 hours. When the reaction was complete, water was added thereto, followed by stirring for 30 minutes, and after removing the aqueous layer and the organic solvent, 18.2 g (74%) of intermediate Int-03 was obtained by using column chromatography (hexane:DCM (20%)).

[0241] Synthesis Example 5: Synthesis of Intermediate Int-04

[0242] [Reaction formula 5]

[0243]

[0244] Intermediate Int-03 (15 g, 37.85 mmol), bis-boronic acid pinacol ester (12.5 g, 49.21 mmol), Pd(dppf)Cl2 (1.73 g, 1.9 mmol) and potassium acetate (7.43 g, 75.7 mmol) were added to a round-bottom flask and dissolved in toluene (100 ml). The mixture was stirred and refluxed at 120°C for 10 hours. When the reaction was complete, the mixture was poured into excess distilled water and then stirred for 1 hour. The solid was thus filtered and dissolved in DCM. After removing moisture with MgSO4, the organic solvent was filtered through a silica gel pad and then removed under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to obtain 14.6 g (87%) of intermediate Int-04.

[0245] Synthesis Example 6: Synthesis of Intermediate Int-05

[0246] [Reaction formula 6]

[0247]

[0248] 15.3 g (76%) of Intermediate Int-05 was obtained in the same manner as in Synthesis Example 1, except that 2,4-dichloro-6-phenyl-1,3,5-triazine was used instead of 2,4-dichloro-6-(biphenyl-4-yl)-1,3,5-triazine.

[0249] Synthesis Example 7: Synthesis of Compound A-32-a

[0250] [Reaction formula 7]

[0251]

[0252] 17.1 g (78%) of compound A-32-a was obtained in the same manner as in Synthesis Example 2, except that Intermediate Int-04 and Intermediate Int-05 were used instead of (2-(9H-carbazol-9-yl)phenyl)boronic acid and Intermediate Int-01.

[0253] Synthesis Example 8: Synthesis of Intermediate Int-06

[0254] [Reaction formula 8]

[0255]

[0256] 11.8 g (71%) of intermediate Int-06 was obtained in the same manner as in Synthesis Example 1, except that 2,4-dichloro-6-phenyl-1,3,5-triazine and 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole were used instead of 2,4-dichloro-6-(biphenyl-4-yl)-1,3,5-triazine and 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole.

[0257] Synthesis Example 9: Synthesis of Compound A-57-a

[0258] [Reaction formula 9]

[0259]

[0260] 8.7 g (79%) of compound A-57-a was obtained in the same manner as in Synthesis Example 2, except that Intermediate Int-04 and Intermediate Int-06 were used instead of (2-(9H-carbazol-9-yl)phenyl)boronic acid and Intermediate Int-01.

[0261] Synthesis Example 10: Synthesis of Intermediate Int-07

[0262] [Reaction formula 10]

[0263]

[0264] 14.3 g (73%) of intermediate Int-07 was obtained in the same manner as in Synthesis Example 1, except that 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole was used instead of 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole.

[0265] Synthesis Example 11: Synthesis of Compound A-47-a

[0266] [Reaction formula 11]

[0267]

[0268] 7.4 g (81%) of compound A-47-a was obtained in the same manner as in Synthesis Example 2, except that Intermediate Int-04 and Intermediate Int-07 were used instead of (2-(9H-carbazol-9-yl)phenyl)boronic acid and Intermediate Int-01.

[0269] Synthesis Example 12: Synthesis of Compound A-22

[0270] [Reaction formula 12]

[0271]

[0272] 20 g of compound A-22-a, 15 ml of trifluoromethanesulfonic acid and 350 ml of D6-benzene were added to a flask and stirred at 70° C. for 24 hours. After adding pure water thereto and neutralizing the mixture with a saturated K3PO4 solution, the organic layer thus obtained was concentrated and column purified to obtain compound A-22 (yield: 14 g (70%), number of substitutions: D24).

[0273] Synthesis Example 13: Synthesis of Compound A-32

[0274] [Reaction formula 13]

[0275]

[0276] Compound A-32 was obtained in the same manner as in Synthesis Example 12 (yield: 13.2 g (68%), number of substitutions: D25), except that compound A-32-a was used instead of compound A-22-a.

[0277] Synthesis Example 14: Synthesis of Compound A-57

[0278] [Reaction formula 14]

[0279]

[0280] Compound A-57 was obtained in the same manner as in Synthesis Example 12 (yield: 17.2 g (69%), number of substitutions: D23), except that compound A-57-a was used instead of compound A-22-a.

[0281] Synthesis Example 15: Synthesis of Compound A-47

[0282] [Reaction formula 15]

[0283]

[0284] Compound A-47 was obtained in the same manner as in Synthesis Example 12 (yield: 19.2 g (83%), number of substitutions: D25), except that compound A-47-a was used instead of compound A-22-a.

[0285] Synthesis Example 16: Synthesis of Compound B-1

[0286] [Reaction formula 16]

[0287]

[0288] Compound B-1 was obtained in the same manner as in Synthesis Example 2 (yield: 5 g (67%)), except that (3-(9H-carbazol-9-yl)phenyl)boronic acid was used instead of (2-(9H-carbazol-9-yl)phenyl)boronic acid.

[0289] Synthesis Example 17: Synthesis of Compound B-2

[0290] [Reaction 17]

[0291]

[0292] Compound B-2 (yield: 15.3 g (78.1%), number of substitutions: D23) was obtained in the same manner as in Synthesis Example 12, except that Compound B-1 was used instead of Compound A-22-a.

[0293] Example 1

[0294] A glass substrate coated with ITO (indium tin oxide) was cleaned with distilled water and ultrasonic waves. After cleaning with distilled water, the glass substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned for 10 minutes using oxygen plasma, and moved to a vacuum depositor. The ITO transparent electrode thus obtained was used as an anode, and Compound A (available from Novaled) doped with 3% NDP-9 was vacuum deposited on the ITO substrate to form a thick hole injection layer, and depositing Compound A on the hole injection layer to form a thick hole transport layer. Compound B is deposited on the hole transport layer to a thickness of to form a hole transport auxiliary layer. On the hole transport auxiliary layer, Compound A-22 obtained in Synthesis Example 12 is used as a host, and 7 wt% of PhGD is doped as a dopant, to form a thick light emitting layer. Then, Compound C is deposited on the light emitting layer to a thickness of to form an electron transport auxiliary layer, and Compound D and LiQ are simultaneously vacuum-deposited at a weight ratio of 1:1 to form a thick electron transport layer. By sequentially vacuum-depositing LiQ and Al on the electron transport layer to form a cathode, an organic light emitting diode is manufactured.

[0295] The organic light emitting diode has the following structure: ITO / Compound A (3% NDP-9 doped, / Compound A / Compound B / EML [93 wt% host (Compound A-22): 7 wt% of PhGD] / Compound C / Compound D:LiQ / LiQ / Al

[0296] Compound A: N-(diphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0297] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0298] Compound C: 2,4-diphenyl-6-(4',5',6'-triphenyl[1,1':2',1 ” :3 ” ,1 ” ':3 ” ',1 ” ”-quinquephenyl]-3 ” ”-yl)-1,3,5-triazine

[0299] Compound D: 2-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0300] [PhGD]

[0301]

[0302] Examples 2 to 4 and Comparative Examples 1 to 2

[0303] Each organic light emitting diode was manufactured in the same manner as Example 1, except that the composition was changed to the compositions described in Tables 1 and 2.

[0304] evaluate

[0305] The luminous efficiency and lifetime characteristics of the organic light emitting diodes according to Examples 1 to 4 and Comparative Examples 1 to 2 were evaluated.

[0306] The specific measurement methods were as follows and the results are shown in Tables 1 and 2.

[0307] (1) Measurement of current density change according to voltage change

[0308] The current value flowing through the unit diode in the obtained organic light emitting diode was measured using a current-voltage meter (Keithley 2400) while the voltage was increased from 0 V to 10 V, and the measured current value was divided by the area to provide the result.

[0309] (2) Measurement of luminance change according to voltage change

[0310] 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.

[0311] (3) Measurement of luminous efficiency

[0312] The luminous efficiency (cd / A) at the same current density (10 mA / cm 2 ) was calculated by using the luminance and current density and voltage from above (1) and (2).

[0313] The luminous efficiency values of Examples 1 to 4 and Comparative Example 2 were calculated as relative values based on Example 1 and are listed in Table 2.

[0314] (4) Measurement of lifetime

[0315] The time when the current efficiency (cd / A) was reduced to 97% while the luminance (cd / m 2 ) was maintained at 24000 cd / m 2 ) was measured as the lifetime.

[0316] The lifetime measurement values of Example 1 and Comparative Example 1 were calculated as relative values based on Example 1 and are listed in Table 1, and

[0317] The lifetime measurement values of Examples 1 to 4 and Comparative Example 2 are calculated as relative values based on Example 1 and are listed in Table 2.

[0318] [Table 1]

[0319] serial number main body life(%) Example 1 A-22 100 Comparative Example 1 A-22-a 82

[0320] [Table 2]

[0321] serial number main body efficiency(%) life(%) Example 1 A-22 100 100 Example 2 A-32 98 110 Example 3 A-47 98 90 Example 4 A-57 97 95 Comparative Example 2 B-2 93 65

[0322] Referring to Table 1, Example 1 is a D-substituted structure of the structure of Comparative Example 1, and as can be seen from the diode data, the lifetime characteristics are improved by about 18%. It can thus be confirmed that when D is substituted, the compound stability is greatly increased, and thus the lifetime is significantly improved.

[0323] Further, referring to Table 2, the structure of Comparative Example 2 is a structure including a meta-linker instead of an ortho-linker, and the structure including an ortho-linker in the D-substituted structure in Examples 1 to 4 further improves the efficiency and lifetime characteristics. Thereby, steric hindrance of the structure is generated by the ortho-linker, which allows better flow of holes and electrons during deposition, thereby improving the efficiency and lifetime characteristics.

Claims

1. A compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group, R 1 to R 5 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, m1 and m3 to m5 are each independently one of integers from 1 to 4, m2 is an integer from 1 to 3, and Chemical formula 1 satisfies at least one of the following (i) to (iii): (i)R 1 to R 5 At least one of the following is deuterium, a C1 to C10 alkyl group substituted with one or more deuteriums, or a C6 to C12 aryl group substituted with one or more deuteriums; (ii)Ar 1 is a C6 to C20 aryl group substituted by one or more deuterium groups or a C2 to C30 heterocyclyl group substituted by one or more deuterium groups; and (iii)Ar 2 is a C6 to C20 aryl group substituted by one or more deuterium groups or a C2 to C30 heterocyclic group substituted by one or more deuterium groups.

2. The compound for an organic optoelectronic device according to claim 1, wherein R 1 to R 5 At least one of is deuterium, a C1 to C10 alkyl group substituted by one or more deuteriums, or a C6 to C12 aryl group substituted by one or more deuteriums, and Ar 1 is a C6 to C20 aryl group substituted by one or more deuterium groups or a C2 to C30 heterocyclic group substituted by one or more deuterium groups.

3. The compound for an organic optoelectronic device according to claim 1, wherein R 1 to R 5 At least one of is deuterium, a C1 to C10 alkyl group substituted by one or more deuteriums, or a C6 to C12 aryl group substituted by one or more deuteriums, and Ar 2 is a C6 to C20 aryl group substituted by one or more deuterium groups or a C2 to C30 heterocyclic group substituted by one or more deuterium groups.

4. The compound for an organic optoelectronic device according to claim 1, wherein R 1 to R 5 at least one of which is deuterium, a C1 to C10 alkyl group substituted by one or more deuteriums, or a C6 to C12 aryl group substituted by one or more deuteriums, Ar 1 is a C6 to C20 aryl group substituted by one or more deuterium groups or a C2 to C30 heterocyclic group substituted by one or more deuterium groups, and Ar 2 is a C6 to C20 aryl group substituted by one or more deuterium groups or a C2 to C30 heterocyclic group substituted by one or more deuterium groups.

5. The compound for an organic optoelectronic device according to claim 1, wherein The deuterium substitution ratio of Chemical Formula 1 is 10% to 100%.

6. The compound for an organic optoelectronic device according to claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formula 1A to Chemical Formula 1D: [Chemical Formula 1A] [Chemical Formula 1B] [Chemical Formula 1C] [Chemical Formula 1D] In Chemical Formulas 1A to 1D, R 1 to R 5 、Ar 1 、Ar 2 and m1 to m5 as defined in claim 1.

7. The compound for an organic optoelectronic device according to claim 1, wherein In Chemical Formula 1, Ar 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilyl group.

8. The compound for an organic optoelectronic device according to claim 1, wherein The first compound is selected from the compounds listed in Group 1: [Group 1] In Group 1, D represents a structure in which deuterium is substituted, The substitution ratio of D is 10% to 100%.

9. An organic optoelectronic device comprising: an anode and a cathode facing each other, and At least one organic layer between the anode and the cathode, wherein the organic layer comprises the compound for an organic optoelectronic device according to any one of claims 1 to 8.

10. The organic optoelectronic device according to claim 9, wherein The organic layer includes a light-emitting layer, and The light-emitting layer includes the compound for an organic optoelectronic device. 11 . A display device comprising the organic optoelectronic device according to claim 9 .

Images