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

Abstract

A compound for an organic optoelectronic device, an organic optoelectronic device, and a display device. The present invention relates to a compound for an organic optoelectronic device, an organic optoelectronic device comprising the compound for an organic optoelectronic device, and a display device comprising the organic optoelectronic device containing the compound for an organic optoelectronic device, the compound being a compound represented by Chemical Formula 1. [Chemical Formula 1]

Description

[0001] Citations of Related Applications

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2024-0041224, filed on March 26, 2024, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Embodiments of the present invention relate to a compound for an organic optoelectronic device, an organic optoelectronic device, and a display device. Background Art

[0004] An organic optoelectronic device (eg, an organic optoelectronic diode) is a device capable of converting electrical energy and light energy into one another.

[0005] Organic optoelectronic devices can be divided into two types based on their operating principles. One is a photovoltaic device that generates electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes, while the other is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to electrodes.

[0006] Examples of the organic optoelectronic device may include an organic photoelectric device, an organic light emitting diode, an organic solar cell, or an organic photoconductor.

[0007] Among them, organic light emitting diodes (OLEDs) have attracted much attention in recent years due to the growing demand for flat panel display devices. OLEDs are devices that convert electrical energy into light, and the performance of OLEDs is greatly affected by the organic materials between electrodes. Summary of the Invention

[0008] The embodiment may be implemented by providing a compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1:

[0009] [Chemical Formula 1]

[0010]

[0011] In Chemical Formula 1, X 1 It is O, S, CR a R b or SiR c R d , X 2 It is O or S, R a 、R b 、R c and R d are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, Ar 1is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, R 1 to R 5 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof, R 12 to R 17 are each independently hydrogen or deuterium, L 1 and L 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, m1 and m5 are each independently an integer from 1 to 4, m2 is an integer from 1 or 2, m3 and m4 are each independently an integer from 1 to 3, and when m1 is 2, 3 or 4, each R 1 The same or different from each other, when m2 is 2, each R 2 The same or different from each other, when m3 is 2 or 3, each R 3 The same or different from each other, when m4 is 2 or 3, each R 4 are the same as or different from each other, and when m5 is 2, 3 or 4, each R 5 the same as or different from each other.

[0012] The embodiment may be implemented by providing an organic optoelectronic device including an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, wherein the at least one organic layer includes the compound for an organic optoelectronic device according to one embodiment.

[0013] The embodiment may be achieved by providing a display device including the organic optoelectronic device according to one embodiment. BRIEF DESCRIPTION OF THE DRAWINGS

[0014] Features will become apparent to those skilled in the art by describing in detail exemplary embodiments with reference to the accompanying drawings, in which:

[0015] Figure 1 is a cross-sectional view illustrating an organic light emitting diode according to some embodiments. DETAILED DESCRIPTION

[0016] Exemplary embodiments will now be described more fully hereinafter with reference to the accompanying drawings; however, they may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey exemplary implementations to those skilled in the art.

[0017] In the accompanying drawings, the dimensions of layers and regions may be exaggerated for clarity. It should also be understood that when a layer or element is referred to as being "on" another layer or substrate, it can be directly on the other layer or substrate, or there may be intervening layers. Furthermore, it should be understood that when a layer is referred to as being "under" another layer, it can be directly under the other layer, and there may also be one or more intervening layers. Furthermore, it should be understood that when a layer is referred to as being "between" two layers, it can be the only layer between the two layers, or there may also be one or more intervening layers. The same reference numerals represent the same elements throughout.

[0018] 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.

[0019] In one embodiment, "substituted" refers to the replacement of at least one hydrogen of a substituent or compound 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 one embodiment, "substituted" refers to the replacement of at least one hydrogen of a substituent or compound by deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. In one embodiment, "substituted" refers to the replacement of at least one hydrogen of a substituent or compound by deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. In one embodiment, "substituted" refers to the replacement of at least one hydrogen of a substituent or compound by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0020] "Unsubstituted" means that a hydrogen atom is not replaced by another substituent and that the hydrogen atom remains.

[0021] In this specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)." For example, any hydrogen in any compound described herein may be protium, deuterium, or tritium (e.g., based on natural or artificial substitution).

[0022] As used herein, when no definition is otherwise provided, "hetero" means including one to three heteroatoms selected from N, O, S, P and Si and the remaining carbon in one functional group.

[0023] 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 connected by a σ bond and may be, for example, biphenyl, terphenyl, quaterphenyl, etc., and two or more hydrocarbon aromatic moieties may be fused directly or indirectly to provide a non-aromatic fused ring, such as fluorenyl.

[0024] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0025] 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 group, a cycloalkyl group, 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 contain one or more heteroatoms.

[0026] For 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 1 to 3 heteroatoms.

[0027] 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 The present invention may include, but is not limited to, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0028] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted furyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted oxadiazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted The present invention also includes, but is not limited to, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted isoquinolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted benzoxazinyl, a substituted or unsubstituted benzothiazinyl, a substituted or unsubstituted acridinyl, a substituted or unsubstituted phenazinyl, a substituted or unsubstituted phenothiazinyl, a substituted or unsubstituted phenoxazinyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthofuranyl, a substituted or unsubstituted benzonaphthothiophenyl, a substituted or unsubstituted benzofuranofluorenyl, a substituted or unsubstituted benzothiophenefluorenyl, or a combination thereof, but is not limited thereto.

[0029] As used herein, hole characteristics refer to the ability to donate electrons to form holes when an electric field is applied, and due to the conductive characteristics 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.

[0030] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to 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.

[0031] Hereinafter, compounds for an organic optoelectronic device according to some embodiments are described.

[0032] The compound for an organic optoelectronic device according to some embodiments may be represented by Chemical Formula 1.

[0033] [Chemical Formula 1]

[0034]

[0035] In Chemical Formula 1, X 1 Can be, for example, O, S, CR a R b or SiR c R d .

[0036] X 2 It can be O or S, for example.

[0037] R a 、R b 、R c and R d Each may independently be, for example, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof.

[0038] Ar 1 It may be, for example, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0039] R 1 to R 5 Each independently may be, for example, hydrogen, deuterium, cyano, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof.

[0040] R 12 to R 17 Each independently may be, for example, hydrogen or deuterium.

[0041] L 1 and L 2 Each independently may be, for example, a single bond or a substituted or unsubstituted C6 to C20 arylene group.

[0042] m1 and m5 may each independently be an integer of 1 to 4, for example.

[0043] m2 may be an integer such as 1 or 2.

[0044] m3 and m4 may each independently be an integer from 1 to 3.

[0045] In one implementation, m1 can be 2, 3, or 4, and each R 1 They may be the same as or different from each other.

[0046] In one implementation, m2 may be 2, and each R 2 They may be the same as or different from each other.

[0047] In one implementation, m3 can be 2 or 3, and each R 3 They may be the same as or different from each other.

[0048] In one implementation, m4 can be 2 or 3, and each R 4 They may, for example, be the same as or different from each other.

[0049] In one implementation, m5 can be 2, 3, or 4, and each R 5 They may be the same as or different from each other.

[0050] The compound represented by Chemical Formula 1 may have a structure in which dimethylfluorene may be substituted in a 6-5-6-5-6 fused ring. In the case of the corresponding substitution position of the fused ring, when the distance between N and O or S at the end becomes smaller, the lone pair of electrons of O or S may help to increase the radical cation stability of N. Therefore, compared with other fused ring structures or other substitution positions, it may have a shallow HOMO energy level. Therefore, the hole mobility may be increased and the charge balance may be improved. In addition, due to the high hole mobility of dimethylfluorene, the organic light emitting diode using it may exhibit low driving voltage and long life.

[0051] In one implementation, Chemical Formula 1 may be represented by one of Chemical Formula 1-1 to Chemical Formula 1-4.

[0052]

[0053] In Chemical Formulas 1-1 to 1-4, X 1 、X 2 、R 1 to R 5 、R 12 to R 17 , L 1 , L 2 、Ar 1 and m1 to m5 may be defined the same as those of Chemical Formula 1.

[0054] In one implementation, Chemical Formula 1 may be represented by Chemical Formula 1-2.

[0055] In one implementation, Ar 1 It may be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzothiorol group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group.

[0056] In one implementation, L 1 and L 2 Each independently may be, for example, a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0057] In one implementation, -L 1 -Ar1 The portion may be, for example, a portion of group 1.

[0058] [Group I]

[0059]

[0060] In Group I, R 6 to R 9 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl.

[0061] R 10 and R 11 Each independently may be, for example, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group.

[0062] m6 may be an integer from 1 to 5, for example.

[0063] m7 may be an integer from 1 to 4, for example.

[0064] m8 may be an integer from 1 to 3, for example.

[0065] m9 may be an integer such as 1 or 2.

[0066] In one implementation, m6 can be 2, 3, 4, or 5, and each R 6 They may be the same as or different from each other.

[0067] In one implementation, m7 can be 2, 3, or 4, and each R 7 They may be the same as or different from each other.

[0068] In one implementation, m8 can be 2 or 3, and each R 8 They may be the same as or different from each other.

[0069] In one implementation, m9 may be 2, and each R 9 They may be the same as or different from each other.

[0070] * is the connection point.

[0071] In one implementation, R 1 to R 5 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0072] In one implementation, R 1 to R 5Each of the groups may independently be, for example, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a combination thereof.

[0073] In one implementation, R a 、R b 、R c and R d Each independently may be, for example, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof.

[0074] In one implementation, R a 、R b 、R c and R d Each of the groups may independently be, for example, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a combination thereof.

[0075] In one implementation, the compound for an organic optoelectronic device represented by Chemical Formula 1 may be a compound of Group 1.

[0076] [Group 1]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] In Group 1, Dn refers to the number of deuterium replacements for hydrogen. However, as described above, any hydrogen in any compound may be protium, deuterium, or tritium based on natural or artificial substitution.

[0104] In addition to the above-mentioned compound for an organic optoelectronic device, one or more compounds may be further included.

[0105] In one implementation, a dopant may be further included.

[0106] The dopant may be, for example, a phosphorescent dopant, such as a red, green or blue phosphorescent dopant, such as a red or green phosphorescent dopant.

[0107] A dopant may be a material that is mixed in a small amount with a compound or composition used in an organic optoelectronic device to induce light emission, and is generally a material that emits light by multiple excitations to a triplet state or more, such as a metal complex. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof may be used.

[0108] Examples of the dopant include phosphorescent dopants, and examples of the phosphorescent dopant include organometallic compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. The phosphorescent dopant may be, for example, a compound represented by the chemical formula Z.

[0109] [Chemical formula Z]

[0110] L 3 MX 3

[0111] In the chemical formula Z, M may be a metal, and L 3 and X 3 M may be the same or different and may each independently be a ligand to form a complex with M.

[0112] 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 3 and X 3 This may be, for example, a bidentate ligand.

[0113] In one implementation, L 3 and X 3 The ligand represented may be a Group A ligand.

[0114] [Group A]

[0115]

[0116] In Group A, R 300 to R 302 Each independently may be, for example, hydrogen, deuterium, a C1 to C30 alkyl group which may be substituted by a halogen, a C6 to C30 aryl group which may be substituted by a C1 to C30 alkyl group, or a halogen.

[0117] R 303 to R 324 Each of them may independently be, for example, 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.

[0118] n1 may be an integer of 1 to 5, for example.

[0119] n2 may be an integer from 1 to 4, for example.

[0120] n3 may be an integer from 1 to 3, for example.

[0121] n4 can be 1 or 2, for example.

[0122] n5 may be an integer of 1 to 6, for example.

[0123] In one implementation, n1 may be 2 or greater, and each substituent may be the same as or different from each other.

[0124] In one implementation, n2 can be 2 or greater, and each substituent can be the same as or different from each other.

[0125] In one implementation, n3 can be 2 or greater, and each substituent can be the same as or different from each other.

[0126] In one implementation, n4 can be 2, and each substituent can be the same as or different from each other.

[0127] In one implementation, n5 can be 2 or greater, and each substituent can be the same as or different from each other.

[0128] The dopant according to some embodiments may be an iridium complex and may be represented by, for example, Chemical Formula 6-1 or Chemical Formula 6-2.

[0129] [Chemical Formula 6-1]

[0130]

[0131] In Chemical Formula 6-1, R 101 to R 116 Each independently may be, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 .

[0132] R 132 to R 134 Each may independently be, for example, a C1 to C6 alkyl group.

[0133] R 101 to R 116 At least one of may be a functional group represented by Chemical Formula V-1.

[0134] L 100 The ligand may be, for example, a bidentate ligand of a monovalent anion, and may be a ligand coordinated to iridium via a lone carbon pair or a heteroatom.

[0135] m19 and m20 may each independently be an integer of, for example, 0 to 3, and m19+m20 may be an integer of 1 to 3.

[0136] [Chemical Formula V-1]

[0137]

[0138] In chemical formula V-1, R 135 to R 139 can each independently be, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 .

[0139] R 132 to R 134 Each may independently be, for example, a C1 to C6 alkyl group.

[0140] * refers to the moiety attached to the carbon atom.

[0141] [Chemical Formula 6-2]

[0142]

[0143] In Chemical Formula 6-2, R 101 to R 117 Each independently may be, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -Si R 133 R 134 R 135 .

[0144] R 133 to R 135 Each independently may be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0145] L 100 The ligand may be, for example, a bidentate ligand of a monovalent anion, and may be a ligand coordinated to iridium via a lone carbon pair or a heteroatom.

[0146] n1 and n2 may each independently be an integer of, for example, 0 to 3, and n1+n2 may be an integer of 1 to 3.

[0147] In one implementation, the dopant according to some embodiments may be represented by, for example, Chemical Formula Z-1.

[0148] [Chemical Formula Z-1]

[0149]

[0150] In Chemical Formula Z-1, Rings A, B, C, and D may each independently be, for example, a 5-membered or 6-membered carbocyclic ring or heterocyclic ring.

[0151] R A 、R B 、R C and R D and may each independently be, for example, mono-, di-, tri- or tetra-substituted or unsubstituted.

[0152] L B , L C and L D Each independently may be, for example, a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, or a combination thereof.

[0153] In one implementation, nA may be 1, and 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. In one implementation, nA can be 0, and L E Does not exist.

[0154] R A 、R B 、R C 、R D R and R' can each independently be, for example, hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfhydryl, sulfinyl, sulfonyl, phosphino, or a combination thereof; any adjacent R A 、R B 、R C 、R D , R and R' may optionally be linked to each other to provide a ring; X B 、X C 、X D and X E can each independently be, for example, carbon or nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 Can represent oxygen or a direct bond.

[0155] The platinum complex can be represented by, for example, Chemical Formula 7-1 or Chemical Formula 7-2.

[0156] [Chemical Formula 7-1]

[0157]

[0158] [Chemical Formula 7-2]

[0159]

[0160] In Chemical Formula 7-1 and Chemical Formula 7-2, X 100 Can be, for example, O, S or NR 132 .

[0161] R 118 to R 132 Each independently may be, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 133 R 134 R 135 .

[0162] R 133 to R 135 Each independently may be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0163] In one implementation, R 118 to R 132 At least one of them may be -SiR 133 R 134 R 135 or tert-butyl.

[0164] R 133 to R 135 Each independently may be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0165] Hereinafter, an organic optoelectronic device using the above-mentioned compound for an organic optoelectronic device will be described.

[0166] 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 photoconductor.

[0167] Herein, an organic light emitting diode as one example of an organic optoelectronic device is described with reference to the accompanying drawings.

[0168] Figure 1 is a cross-sectional view illustrating an organic light emitting diode according to some embodiments.

[0169] refer to Figure 1 , the organic light emitting diode 100 according to some embodiments may include an anode 120 and a cathode 110 facing each other and an organic layer 105 between the anode 120 and the cathode 110 .

[0170] The anode 120 may be made of a conductor having a high work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 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; or a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, or polyaniline.

[0171] The cathode 110 may be made of a conductor having a low 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, and BaF2 / Ca.

[0172] The organic layer 105 may include the above-described compound for an organic optoelectronic device.

[0173] The organic layer 105 may include a light emitting layer 130 , and the light emitting layer 130 may include the above-described compound for an organic optoelectronic device.

[0174] The composition for an organic optoelectronic device further including a dopant may be, for example, a green light-emitting composition.

[0175] The light emitting layer 130 may include, for example, the above-described compound for an organic optoelectronic device as a phosphorescent host.

[0176] The organic layer may further include a charge transport region in addition to the light emitting layer.

[0177] The charge transport region may be, for example, a hole transport region 140 .

[0178] The hole transport region 140 may help to further increase hole injection and / or hole mobility and block electrons between the anode 120 and the light emitting layer 130 .

[0179] In one implementation, 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 the hole transport auxiliary layer may include the above-mentioned compound for organic optoelectronic devices.

[0180] In one implementation, the light-emitting layer may include a host and a dopant, and the host may be, for example, a phosphorescent host.

[0181] The phosphorescent host can promote the injection and transport of holes and electrons within the light-emitting layer, ultimately allowing the holes and electrons to meet to form excitons, and can effectively transfer the energy of the formed excitons to the dopant. Examples of the phosphorescent host may include organic compounds comprising carbazole, indolocarbazole, dibenzofuran, dibenzothiophene, indolodibenzofuran, indolodibenzothiophene, fluorene, indenocarbazole, triphenylene, pyrimidine, triazine, or a combination thereof.

[0182] The phosphorescent host can be a suitable material. In one implementation, it can be a single host or a mixed host.

[0183] In one implementation, the above-described compound for an organic optoelectronic device may be included in the light-emitting layer, and the compound of group C may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0184] [Group C]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191] (Dn refers to the number of deuterium replacements for hydrogen and represents a structure in which one or more deuterium atoms are substituted)

[0192] However, as noted above, any hydrogen in any compound may be protium, deuterium, or tritium, based on natural or artificial substitution.

[0193] In the hole transport region 140 , in addition to the above-mentioned compounds, other suitable compounds may be used.

[0194] In one implementation, the charge transport region may be, for example, the electron transport region 150 .

[0195] The electron transport region 150 may help to further increase electron injection and / or electron mobility and block holes between the cathode 110 and the light emitting layer 130 .

[0196] In one implementation, the electron transport region 150 may 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 a compound of group D may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0197] [Group D]

[0198]

[0199]

[0200]

[0201] Some embodiments may be an organic light emitting diode including a light emitting layer as an organic layer.

[0202] Some embodiments may be an organic light emitting diode including a light emitting layer and a hole transporting region as organic layers.

[0203] Some embodiments may be an organic light emitting diode including a light emitting layer and an electron transport region as organic layers.

[0204] In addition to the light emitting layer 130, the organic light emitting diode according to some embodiments may include a hole transport region 140 and an electron transport region 150 as the organic layer 105, such as Figure 1 As shown in .

[0205] In some embodiments, the organic light emitting diode may further include an electron injection layer, a hole injection layer, etc. as organic layers in addition to the light emitting layer.

[0206] The organic light emitting diode 100 may be manufactured by forming an anode or cathode on a substrate, and then forming an organic layer by a dry film method such as vacuum deposition, sputtering, plasma plating, or ion plating, and forming the cathode or anode thereon.

[0207] Organic light emitting diodes can be applied to organic light emitting display devices.

[0208] The following examples and comparative examples are provided to emphasize the characteristics of one or more embodiments, but it should be understood that these examples and comparative examples should not be construed as limiting the scope of the embodiments, and the comparative examples should not be construed as being outside the scope of the embodiments. Furthermore, it should be understood that the embodiments are not limited to the specific details described in the examples and comparative examples.

[0209] Hereinafter, unless otherwise specified, the starting materials and reactants used in the Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry or P&H tech, or were synthesized by known methods.

[0210] (Preparation of Compounds for Organic Optoelectronic Devices)

[0211] Synthesis Example 1: Synthesis of Compound 1-5

[0212] [Reaction formula 1]

[0213]

[0214] 10g (34.16mmol) of 1-chloro-benzo [1,2-b; 3,4-b'] dibenzofuran, 13.03g (32.45mmol) of bis (9,9-dimethyl-9H-fluorene-2-yl) amine, 5.25g (54.66mmol) of sodium tert-butoxide and 0.98g (2.39mmol) of 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (Sphos) were dissolved in 227ml of xylene, and 0.94g (1.03mmol) of Pd2(dba)3 was added thereto, then refluxed and stirred under nitrogen atmosphere for 12 hours. After completion of the reaction, the organic layer was extracted therefrom using toluene and distilled water, dried over anhydrous magnesium sulfate, filtered, and the filtrate obtained therefrom was concentrated under reduced pressure. The product obtained therefrom was purified by silica gel column chromatography with n-hexane / dichloromethane (volume ratio of 3:1) to obtain 17 g (yield: 76%) of compound 1-7 as a white solid.

[0215] Synthesis Example 2: Synthesis of Compound 1-8

[0216] [Reaction formula 2]

[0217]

[0218] Compound 1-8 (17.3 g, yield: 77%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of 1-chloro-benzo[1,2-b;3,4-b′]dibenzofuran and 13.03 g of N-(9,9-dimethyl-9H-fluoren-4-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:0.95.

[0219] Synthesis Example 3: Synthesis of Compound 1-49

[0220] [Reaction formula 3]

[0221]

[0222] Compound 1-49 (16 g, yield: 74%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of 1-chloro-benzo[1,2-b;3,4-b′]dibenzofuran and 12.19 g of N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine were used in an equivalent ratio of 1:0.95.

[0223] Synthesis Example 4: Synthesis of Compound 1-57

[0224] [Reaction formula 4]

[0225]

[0226] Compound 1-57 (18.2 g, yield: 86%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of 1-chloro-benzo[1,2-b;3,4-b.]dibenzofuran and 11.73 g of N-([1,1'-biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:0.95.

[0227] Synthesis Example 5: Synthesis of Compound 1-175

[0228] [Reaction formula 5]

[0229]

[0230] Compound 1-175 (16.8 g, yield: 78%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of 11-chloro-7,7-dimethyl-7H-fluoren[4,3-b]benzofuran and 11.97 g of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:0.95.

[0231] Synthesis Example 6: Synthesis of Compound 1-219

[0232] [Reaction formula 6]

[0233]

[0234] Compound 1-219 (16 g, yield: 79%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of 11-chloro-7,7-dimethyl-7H-fluoren-[4,3-b]benzofuran and 11.18 g of N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine were used in an equivalent ratio of 1:0.95.

[0235] Synthesis Example 7: Synthesis of Compound 1-227

[0236] [Reaction formula 7]

[0237]

[0238] Compound 1-227 (15.3 g, yield: 74%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of 11-chloro-7,7-dimethyl-7H-fluoren[4,3-b]benzofuran and 11.77 g of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:0.95.

[0239] Synthesis Example 8: Synthesis of Compound 1-235

[0240] [Reaction formula 8]

[0241]

[0242] Compound 1-235 (17.6 g, yield: 76%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of 11-chloro-7,7-dimethyl-7H-fluoren-[4,3-b]benzofuran and 13.46 g of N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:0.95.

[0243] Synthesis Example 9: Synthesis of Compound 1-304

[0244] [Reaction formula 9]

[0245]

[0246] Compound 1-304 (13.7 g, yield: 70%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of 1-chloro-5,5-dimethyl-5H-benzo[b]benzo[4,5]thiorrolo[2,3-g]benzofuran and 10.25 g of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-3-amine were used in an equivalent ratio of 1:0.95.

[0247] Synthesis Example 10: Synthesis of Compound 1-550

[0248] [Reaction formula 10]

[0249]

[0250] Compound 1-550 (15.7 g, yield: 70%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of 11-chloro-7,7-dimethyl-7H-benzo[b]fluoren[3,4-d]thiophene and 12.81 g of N-(9,9-dimethyl-9H-fluoren-3-yl)-6-phenyldibenzo[b,d]furan-1-amine were used in an equivalent ratio of 1:0.95.

[0251] Comparative Synthesis Example 1: Synthesis of Compound R-1

[0252] [Reaction formula 11]

[0253]

[0254] Compound R-1 (17 g, yield: 81%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of 2-chloro-benzo[1,2-b;3,4-b']dibenzofuran and 11.73 g of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:0.95.

[0255] Comparative Synthesis Example 2: Synthesis of Compound R-2

[0256] [Reaction formula 12]

[0257]

[0258] Compound R-2 (20.2 g, yield: 78%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of 1-chloro-benzo[1,2-b;3,4-b′]dibenzofuran and 16.21 g of N-(9,9-diphenyl-9H-fluoren-2-yl)dibenzo[b,d]furan-3-amine were used in an equivalent ratio of 1:0.95.

[0259] Comparative Synthesis Example 3: Synthesis of Compound R-3

[0260] [Reaction formula 13]

[0261]

[0262] Compound R-3 (15 g, yield: 71%) was synthesized in the same manner as in Synthesis Example 1, except that 10 g of 11-chlorobenzo[4,5-b;3,2-f]dibenzofuran and 11.72 g of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:0.95.

[0263] (Manufacturing of organic light-emitting diodes)

[0264] Example 1

[0265] A glass substrate coated with an ITO / Ag / ITO thin film was ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrate was ultrasonically cleaned with acetone or isopropyl alcohol and dried, then moved to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and moved to a vacuum depositor. The prepared ITO / Ag / ITO (reflective electrode) electrode was used as an anode, and Compound A (Novaled GmbH) doped with 3% NDP-9 was vacuum deposited on the ITO / Ag / ITO substrate to form Thick hole injection layer, and compound A is deposited on The hole transport layer is formed by depositing the compound 1-5 obtained in Synthesis Example 1 on the hole transport layer to a thickness of On the hole transport auxiliary layer, 85 wt% of host H1 (40 wt%) and host H2 (60 wt%) were used as hosts, and GD was doped at 15 wt% as a dopant to form a hole transport auxiliary layer by vacuum deposition. Then, compound C is deposited on the light emitting layer to to form an electron transport auxiliary layer, and compound D and LiQ were simultaneously vacuum deposited at a ratio of 1:1 to form The organic light-emitting diode is manufactured by sequentially vacuum-depositing Yb and AgMg on the electron transport layer to form a cathode.

[0266] ITO / Ag / ITO / Compound A (3% NDP-9 doping, ) / Compound A / Hole transport auxiliary layer: Compound 1-5 / Emitting layer [Host (Host H1, Host H2): GD = 85 wt%: 15 wt%] Compound C / Compound D: Liq / Yb / AgMg.

[0267] Compound A: N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine

[0268] Compound C: 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine

[0269] Compound D: 6,6'-(naphthalene-1,2-diylbis(4,1-phenylene))bis(2,4-diphenyl-1,3,5-triazine)

[0270] Host H1: 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(triphenyl-2-yl)phenyl)-1,3,5-triazine

[0271] Host H2: 9,9"-diphenyl-9H,9"H-3,3':9',3"-tricarbazole

[0272] GD:

[0273]

[0274] Examples 2 to 10 and Comparative Examples 1 to 3

[0275] Diodes of Examples 2 to 10 and Comparative Examples 1 to 3 were manufactured in the same manner as in Example 1, except that the composition of the hole transport auxiliary layer was changed as shown in Table 1.

[0276] Evaluate

[0277] (1) Measuring the change in current density according to voltage change

[0278] While increasing the voltage from 0 V to 10 V using a current-voltage meter (Keithley 2400), the current value flowing in the unit device of the obtained organic light emitting diode was measured, and the measured current value was divided by the area to provide a result.

[0279] (2) Measuring the brightness change according to the voltage change

[0280] While increasing the voltage of the organic light emitting diode from 0 V to 10 V, the luminance was measured by using a luminance meter (Minolta Cs-1000A).

[0281] (3) Measurement life

[0282] In the case of brightness (cd / m 2 ) maintained at 24,000cd / m 2 The time required for each current efficiency (cd / A) to drop to 97% was measured as the lifetime.

[0283] Relative values ​​based on the lifespan measurement of Comparative Example 1 as a reference are shown in Table 1.

[0284] (4) Measure the driving voltage

[0285] The current-voltage of each device was measured at 15 mA / cm using an ampere-voltmeter (Keithley 2400). 2 The driving voltage is as follows.

[0286] Relative values ​​based on the driving voltage of Comparative Example 1 as a reference are shown in Table 1.

[0287] (Table 1)

[0288]

[0289] Referring to Table 1, the driving characteristics and lifespan characteristics of the organic light emitting diode using the compound according to the embodiment are significantly improved compared to the organic light emitting diode according to the comparative embodiment.

[0290] One or more embodiments may provide a compound for an organic optoelectronic device, which may realize a low-driving and long-life organic optoelectronic device.

[0291] An organic optoelectronic device with high efficiency and long life can be realized.

[0292] Exemplary embodiments are disclosed herein, and although specific terms are employed, these terms are used and interpreted in their superior and descriptive sense only, and not for purposes of limitation. In some cases, it will be apparent to those skilled in the art that, as of the date of filing this application, the features, characteristics, and / or elements described in conjunction with the specific embodiments may be used individually or in combination with the features, characteristics, and / or elements described in conjunction with other embodiments, unless otherwise expressly indicated. Therefore, it will be understood by those skilled in the art that various changes may be made to form and detail without departing from the spirit and scope of the invention as set forth in the appended claims.

Claims

1. A compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, X 1 It is O, S, CR a R b or SiR c R d , X 2 It is O or S, R a 、R b 、R c and R d are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, Ar 1 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, R 1 to R 5 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof, R 12 to R 17 are each independently hydrogen or deuterium, L 1 and L 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, m1 and m5 are each independently an integer from 1 to 4, m2 is an integer of 1 or 2, m3 and m4 are each independently an integer from 1 to 3, When m1 is 2, 3, or 4, each R 1 Same or different from each other, When m2 is 2, each R 2 Same or different from each other, When m3 is 2 or 3, each R 3 Same or different from each other, When m4 is 2 or 3, each R 4 are the same as or different from each other, and When m5 is 2, 3, or 4, each R 5 the same as or different from each other.

2. The compound for an organic optoelectronic device according to claim 1, wherein Chemical Formula 1 is represented by one of Chemical Formulas 1-1 to 1-4: In Chemical Formulas 1-1 to 1-4, X 1 、X 2 、R 1 to R 5 、R 12 to R 17 , L 1 , L 2 、Ar 1 The definitions of m1 to m5 are the same as those of Chemical Formula 1.

3. The compound for an organic optoelectronic device according to claim 1, wherein 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 triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzothiorolyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group.

4. The compound for an organic optoelectronic device according to claim 1, wherein: -L 1 -Ar 1 Parts are part of Group I: [Group I] In Group I, R 6 to R 9 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, R 10 and R 11 are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group, m6 is an integer from 1 to 5, m7 is an integer from 1 to 4, m8 is an integer from 1 to 3, m9 is an integer of 1 or 2, When m6 is 2, 3, 4, or 5, each R 6 Same or different from each other, When m7 is 2, 3, or 4, each R 7 Same or different from each other, When m8 is 2 or 3, each R 8 Same or different from each other, When m9 is 2, each R 9 are the same as or different from each other, and * is the connection point.

5. The compound for an organic optoelectronic device according to claim 1, wherein X 1 and X 2 Each is O.

6. The compound for an organic optoelectronic device according to claim 1, wherein The compound is a compound of Group 1: [Group 1] wherein Dn refers to the number of deuterium replacements for hydrogen and represents a structure having one or more deuterium atoms substituted.

7. 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, The at least one organic layer comprises the compound for an organic optoelectronic device according to any one of claims 1 to 6.

8. The organic optoelectronic device according to claim 7, wherein: The at least one organic layer includes a light emitting layer, and The light-emitting layer includes the compound for an organic optoelectronic device.

9. The organic optoelectronic device according to claim 7, wherein: The at least one organic layer comprises: luminescent layer, a hole transport layer between the anode and the light-emitting layer, and A hole transport auxiliary layer is provided between the light emitting layer and the hole transport layer, and the hole transport auxiliary layer includes the compound for an organic optoelectronic device. 10 . A display device comprising the organic optoelectronic device according to claim 7 .

Images