Composition for organic optoelectronic device, organic optoelectronic device and display device
By using the bipolar compounds of Chemical Formula 1 and Chemical Formula 2 as the main materials of the light-emitting layer in an organic optoelectronic device and combining them with a blue light-emitting dopant, the problem of the influence of organic materials between electrodes is solved, and a high-efficiency and long-life blue light-emitting effect is achieved.
Patent Information
- Application Number
- CN202510191121.7
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-03-04
- Filing Date
- 2025-02-20
- Publication Date
- 2025-09-05
AI Technical Summary
The performance of existing organic optoelectronic devices is affected by the organic materials between the electrodes. Especially in flat panel display devices, it is difficult to achieve a high-efficiency and long-life blue light-emitting effect.
The bipolar compound comprising Chemical Formula 1 and Chemical Formula 2 is used as the main material of the light-emitting layer, combined with a blue light-emitting dopant, and by finely controlling the mobility of holes and electrons, a composition with good interface characteristics is achieved, the balance of electrons and holes is improved, and exciton transfer is promoted.
High-efficiency and long-life organic optoelectronic devices are achieved, especially efficient exciton transfer in the blue emission spectrum, which improves the luminous efficiency of the device and reduces degradation.
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Figure CN120603469A_ABST
Abstract
Description
[0001] Citations of Related Applications
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2024-0030868, filed on March 4, 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 composition 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, and 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.
[0008] An organic light emitting diode may be a device that converts electrical energy into light, and performance of the organic light emitting diode may be greatly affected by an organic material between electrodes. Summary of the Invention
[0009] The embodiment may be achieved by providing a composition for an organic optoelectronic device, the composition including a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2:
[0010] [Chemical Formula 1]
[0011]
[0012] In Chemical Formula 1, Z 1 to Z 3 Each independently is N or CR a , where R a is hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, cyano or halogen, provided that Z 1 to Z 3At least two of them are N, L 1 To L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted divalent C2 to C20 heterocyclic group, and Ar 1 to Ar 3 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, provided that Ar 1 to Ar 3 At least one of them is a group represented by chemical formula A,
[0013] [Chemical Formula A]
[0014]
[0015] In chemical formula A, R 1 to R 4 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a cyano group, a halogen group, or a connection point to Chemical Formula 1, and R 1 to R 4 Each exists separately or R 1 to R 4 Two adjacent ones are connected to each other to form a ring,
[0016] [Chemical Formula 2]
[0017]
[0018] In Chemical Formula 2, L 7 and L 8 are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group, Ar 7 is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and R 30 to R 33 、R 34’ 、R 34” 、R 34”’ and R 35 to R 42 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a cyano group or a halogen group.
[0019] The embodiment can be implemented by providing an organic optoelectronic device including an anode and a cathode facing each other and a light-emitting layer between the anode and the cathode, wherein the light-emitting layer includes the composition for an organic optoelectronic device according to the embodiment.
[0020] The embodiment may be achieved by providing a display device including the organic optoelectronic device according to the embodiment. BRIEF DESCRIPTION OF THE DRAWINGS
[0021] These features will become apparent to those skilled in the art by describing in detail exemplary embodiments with reference to the accompanying drawings, in which:
[0022] Figure 1 is a cross-sectional view showing an example of an organic light emitting diode according to some embodiments, and
[0023] Figure 2 is a cross-sectional view illustrating another example of an organic light emitting diode according to some embodiments. DETAILED DESCRIPTION
[0024] 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 embodiments to those skilled in the art.
[0025] In the accompanying drawings, the dimensions of layers and regions may be exaggerated for clarity of illustration. 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 intervening layers may also be present. 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 one or more intervening layers may also be present. 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 one or more intervening layers may also be present. Like reference numerals refer to like elements throughout.
[0026] 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.
[0027] In one embodiment, "substituted" refers to 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 one embodiment, "substituted" refers to 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 one embodiment, "substituted" refers to 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 one embodiment, "substituted" refers to that at least one hydrogen of a substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.
[0028] "Unsubstituted" means that a hydrogen atom is not replaced by another substituent and that a hydrogen atom remains.
[0029] 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).
[0030] As used herein, when no definition is otherwise provided, "hetero" refers to a functional group comprising one to three heteroatoms selected from N, O, S, P, and Si, and the remainder being carbon. For example, any hydrogen in any compound described herein may be protium, deuterium, or tritium (e.g., based on natural or artificial substitution).
[0031] 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 may be fused directly or indirectly to provide a non-aromatic fused ring, such as fluorenyl.
[0032] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.
[0033] 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 a cyclic compound such as an aryl group, a cycloalkyl group, a condensed ring thereof or a combination thereof, replacing carbon (C). When the heterocyclyl is a condensed ring, the entire ring or each ring of the heterocyclyl may contain one or more heteroatoms.
[0034] By way of 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 from 1 to 3 heteroatoms.
[0035] 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 substituted or unsubstituted triphenylene, substituted or unsubstituted perylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indenyl, or a combination thereof.
[0036] 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 benzofuran ... 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, substituted or unsubstituted dibenzothiophenyl, or a combination thereof.
[0037] 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 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.
[0038] 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.
[0039] Hereinafter, a composition for an organic optoelectronic device according to some embodiments will be described.
[0040] The composition for an organic optoelectronic device according to some embodiments may include, for example, a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2.
[0041] [Chemical Formula 1]
[0042]
[0043] In Chemical Formula 1, Z 1 to Z 3 may each independently be or include, for example, N or CR a , where R a It may be, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a cyano group, or a halogen group.
[0044] In one embodiment, Z 1 to Z 3 At least two of them are N.
[0045] L 1 To L 3 Each independently may be, for example, a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted divalent C2 to C20 heterocyclic group.
[0046] Ar 1 to Ar 3 may each independently be, for example, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, provided that Ar 1 to Ar 3 At least one of them is a group represented by Chemical Formula A.
[0047] [Chemical Formula A]
[0048]
[0049] In chemical formula A, R 1 to R 4 Each independently may be or include, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a cyano group, a halogen group, or a connection point to Chemical Formula 1.
[0050] R 1 to R4 Can exist alone, or R 1 to R 4 Two adjacent groups in may be linked to each other to form a ring.
[0051] [Chemical Formula 2]
[0052]
[0053] In Chemical Formula 2, L 7 and L 8 Each independently may be or include, for example, a single bond or a substituted or unsubstituted C6 to C30 arylene group.
[0054] Ar 7 It may be or include, for example, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.
[0055] R 30 to R 33 、R 34’ 、R 34” 、R 34”’ and R 35 to R 42 Each independently may be or include, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a cyano group or a halogen group.
[0056] The first compound and the second compound can be bipolar compounds having both electron properties and hole properties, respectively. The first compound can be a bipolar compound with relatively strong electron properties, and the second compound can be a bipolar compound with relatively strong hole properties. In one embodiment, the first compound and the second compound can exhibit good interface properties due to their structures.
[0057] The composition for an organic optoelectronic device may include the first compound and the second compound together to finely control the mobility of holes and electrons to balance holes and electrons in an active layer (eg, a light emitting layer) of the organic optoelectronic device.
[0058] In one embodiment, the composition for an organic optoelectronic device can be used as a host for an emission layer and can have a good electrical match with a blue-emitting dopant that emits light in the blue emission spectrum, as described below, thereby improving the efficiency of the organic optoelectronic device and suppressing degradation of the organic optoelectronic device. In one embodiment, at least one of the first compound and the second compound can have a high triplet energy level greater than or equal to about 2.8 eV, so that exciton transfer to the blue-emitting dopant can be promoted, thereby realizing an organic optoelectronic device with high efficiency and a long life.
[0059] In one embodiment, in Chemical Formula 1, Z 1 to Z 3 Each can be, for example, N.
[0060] In one embodiment, in Chemical Formula 1, Z 1 and Z 2 can each be, for example, N, and Z 3 Can be CR a .
[0061] In one embodiment, in Chemical Formula 1, Z 1 and Z 3 can each be, for example, N, and Z 2 Can be CR a .
[0062] In one embodiment, in Chemical Formula 1, Z 2 and Z 3 can each be, for example, N, and Z 1 Can be CR a .
[0063] In one embodiment, in Chemical Formula 1, L 1 To L 3 Each of them may independently be, for example, a single bond, a substituted or unsubstituted o-phenylene group, a substituted or unsubstituted m-phenylene group, a substituted or unsubstituted p-phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted naphthylene group, a substituted or unsubstituted benzofuranylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted benzothienylene group, a substituted or unsubstituted dibenzothienylene group, or a substituted or unsubstituted fluorenylene group.
[0064] In one embodiment, in Chemical Formula 1, L 1 To L 3Each may independently be, for example, a single bond or a substituted or unsubstituted C6 to C20 arylene group, or may independently be a single bond, a substituted or unsubstituted o-phenylene group, a substituted or unsubstituted m-phenylene group, a substituted or unsubstituted p-phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted naphthylene group.
[0065] In one embodiment, L in Chemical Formula 1 1 To L 3 One of them may be, for example, a substituted or unsubstituted C6 to C20 arylene group, and L in Chemical Formula 1 1 To L 3 The other two of L in Chemical Formula 1 may be single bonds. 1 To L 3 One of them may be, for example, a substituted or unsubstituted o-phenylene, a substituted or unsubstituted m-phenylene, or a substituted or unsubstituted p-phenylene, and L in Chemical Formula 1 1 To L 3 The other two of can be, for example, single bonds.
[0066] In one embodiment, L in Chemical Formula 1 1 To L 3 One of them may be, for example, a single bond, and L in Chemical Formula 1 1 To L 3 The other two of the groups may each independently be, for example, a substituted or unsubstituted o-phenylene group, a substituted or unsubstituted m-phenylene group, or a substituted or unsubstituted p-phenylene group.
[0067] In one embodiment, Ar in Chemical Formula 1 1 to Ar 3 One of them may be, for example, a group represented by Chemical Formula A. In one embodiment, Ar in Chemical Formula 1 1 to Ar 3 Any two groups in may be, for example, groups represented by Chemical Formula A.
[0068] In one embodiment, Ar in Chemical Formula 1 1 to Ar 3 At least one of may be, for example, a group represented by Chemical Formula A, and Ar in Chemical Formula 1 1 to Ar 3 At least one of them may be, for example, a substituted or unsubstituted carbazolyl group.
[0069] In one embodiment, Ar in Chemical Formula 1 1 to Ar 3 One of them may be, for example, a group represented by Chemical Formula A, and Ar in Chemical Formula 1 1to Ar 3 The other two of them may each independently be, for example, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted carbazolyl group.
[0070] In one embodiment, Ar in Chemical Formula 1 1 to Ar 3 One of them may be, for example, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted carbazolyl group, and Ar in Chemical Formula 1 1 to Ar 3 The other two groups in can be, for example, groups represented by Chemical Formula A.
[0071] In one embodiment, in Chemical Formula 1, Ar 1 It may be, for example, a group represented by the chemical formula A, L 1 may be, for example, substituted or unsubstituted o-phenylene, substituted or unsubstituted m-phenylene, substituted or unsubstituted p-phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted terphenylene, and Ar 2 and Ar 3 Each of L and L may be, for example, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted carbazolyl group. 1 may be, for example, o-phenylene, and L 2 and L 3 Each may be, for example, a single bond.
[0072] In one embodiment, the first compound may be represented by, for example, one of Chemical Formulas 1A to 1C.
[0073] [Chemical Formula 1A]
[0074]
[0075] [Chemical Formula 1B]
[0076]
[0077] [Chemical Formula 1C]
[0078]
[0079] In Chemical Formulas 1A to 1C, Z 1 to Z 3 and L 1 L to L3 may be defined the same as those in Chemical Formula 1.
[0080] Ar 1 It may be, for example, a group represented by Chemical Formula A.
[0081] R 12to R 27 Each of them can independently be, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a cyano group or a halogen group.
[0082] R 12 to R 27 Can exist separately or R 12 to R 27 Two adjacent ones of them can be connected to each other to form a ring.
[0083] In one embodiment, R in Chemical Formula 1A 12 to R 27 At least one of can be independently, for example, deuterium, substituted or unsubstituted C6 to C30 aryl, cyano or halogen. In one embodiment, R in Chemical Formula 1B 12 to R 24 At least one of can be, for example, deuterium, a substituted or unsubstituted C6 to C30 aryl group, a cyano group, or a halogen. In one embodiment, R in Formula 1C 12 to R 16 and R 20 to R 24 At least one of may be, for example, deuterium, a substituted or unsubstituted C6 to C30 aryl group, a cyano group, or a halogen group.
[0084] In one embodiment, in Formula A, R 1 or R 2 It can be, for example, a connection point with Chemical Formula 1. In one embodiment, if R 1 is the connection point with Chemical Formula 1, then R 2 It can be, for example, a substituted or unsubstituted C6 to C30 aryl group. In one embodiment, if R in Formula A 2 is the connection point with Chemical Formula 1, then R 1 It may be, for example, a substituted or unsubstituted C6 to C30 aryl group.
[0085] In one embodiment, the first compound may be represented by, for example, one of Chemical Formulas A-1 to 1A-4, 1B-1 to 1B-4, and 1C-1 to 1C-4.
[0086]
[0087]
[0088]
[0089]
[0090] In Chemical Formulas 1A-1 to 1A-4, 1B-1 to 1B-4, and 1C-1 to 1C-4, Z 1 to Z 3 and L 1 To L 3 The same definitions as those in Chemical Formula 1 may be used.
[0091] R 1 to R 4 、R 3a 、R 3b 、R 4a 、R 4b and R 12 to R 27 Each of them can independently be, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a cyano group or a halogen group.
[0092] R 1 to R 4 、R 3a 、R 3b 、R 4a 、R 4b and R 12 to R 27 Can exist separately or R 1 to R 4 、R 3a 、R 3b 、R 4a 、R 4b and R 12 to R 27 Two adjacent ones of them can be connected to each other to form a ring.
[0093] In one embodiment, L of Chemical Formulas 1A-1 to 1A-4, Chemical Formulas 1B-1 to 1B-4, and Chemical Formulas 1C-1 to 1C-4 2 and L 3 Each independently may be, for example, a single bond or a substituted or unsubstituted phenyl group, or each may be, for example, a single bond or a substituted or unsubstituted o-phenyl group, or each may be, for example, a single bond.
[0094] In one embodiment, R in Chemical Formulas 1A-1 to 1A-4 12 to R 27 At least one of can be, for example, deuterium, a substituted or unsubstituted C6 to C30 aryl group, a cyano group, or a halogen. In one embodiment, R in Formulas 1B-1 to 1B-4 12 to R 24At least one of can be, for example, deuterium, a substituted or unsubstituted C6 to C30 aryl group, a cyano group, or a halogen. In one embodiment, R in Formulas 1C-1 to 1C-4 12 to R 16 and R 20 to R 24 At least one of may be, for example, deuterium, a substituted or unsubstituted C6 to C30 aryl group, a cyano group, or a halogen group.
[0095] In one embodiment, in Formula 1, Formulas 1A to 1C, Formulas 1A-1 to 1A-4, Formulas 1B-1 to 1B-4, and Formulas 1C-1 to 1C-4, at least one of each substituent may be substituted, for example, with deuterium. The number of substituted deuterium atoms may be from 1 to the maximum number of hydrogen atoms in the formula, for example, from 1 to 40 or from 1 to 30.
[0096] In one embodiment, the second compound may be represented by, for example, one of Chemical Formula 2a to Chemical Formula 2d.
[0097] [Chemical Formula 2a]
[0098]
[0099] [Chemical Formula 2b]
[0100]
[0101] [Chemical Formula 2c]
[0102]
[0103] [Chemical formula 2d]
[0104]
[0105] In Chemical Formulas 2a to 2d, L 8 、Ar 7 、R 30 to R 33 、R 34’ 、R 34” 、R 34”’ and R 35 to R 42 The same definitions as those in Chemical Formula 2 can be used.
[0106] In one embodiment, L in Chemical Formula 2 and Chemical Formula 2a to Chemical Formula 2d 8 It may be, for example, a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.
[0107] In one embodiment, Ar of Chemical Formula 2 and Chemical Formula 2a to Chemical Formula 2d7 The group 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 triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted dibenzothiazolyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted silyl group.
[0108] In one embodiment, R in Chemical Formula 2 and Chemical Formulas 2a to 2d 30 to R 33 、R 34’ 、R 34” 、R 34”’ and R 35 to R 42 Each of them may independently be, for example, hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted dibenzothiazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted silyl group, or a cyano group.
[0109] In one embodiment, Ar in Formula 2 and Formulas 2a to 2d 7 、R 30 to R 33 、R 34’ 、R 34” 、R 34”’ and R 35 to R 42 At least one of them may be, for example, a substituted or unsubstituted carbazolyl group.
[0110] In one embodiment, at least one of each substituent in Formula 2 and Formulas 2a to 2d may be substituted, for example, with deuterium. The number of substituted deuterium atoms may be 1 to the maximum number of hydrogen atoms in the formula, for example, 1 to 40 or 1 to 30.
[0111] In one embodiment, the first compound may be a Group 1 compound.
[0112] [Group 1]
[0113]
[0114]
[0115]
[0116]
[0117]
[0118]
[0119] (Dn indicates the number of hydrogen atoms substituted with deuterium and indicates a structure in which one or more deuterium atoms are substituted.)
[0120] In one embodiment, the second compound may be a Group 2 compound.
[0121] [Group 2]
[0122]
[0123]
[0124]
[0125]
[0126]
[0127] (Dn indicates the number of hydrogen atoms substituted with deuterium, and indicates a structure in which one or more deuterium atoms are substituted)
[0128] The composition for an organic optoelectronic device may include the first compound and the second compound in various ratios (eg, mixed).
[0129] In one embodiment, the composition for an organic optoelectronic device may include the first compound and the second compound in a weight ratio of about 10:90 to about 90:10, for example, about 20:80 to about 80:20, about 30:70 to about 70:30, about 40:60 to about 60:40, or about 50:50.
[0130] In one embodiment, the first compound may be included in an amount equal to or greater than that of the second compound.In one embodiment, the first compound may be included in about 50 wt % to about 90 wt % based on the total weight of the first and second compounds.
[0131] In one embodiment, the first compound may be included in the same amount as or less than the second compound.In one embodiment, the first compound may be included in about 10 wt % to about 50 wt % based on the total weight of the first and second compounds.
[0132] The composition for an organic optoelectronic device may further include a light-emitting dopant in addition to the first compound and the second compound.
[0133] A luminescent dopant is a material that is mixed in a small amount with a composition for an organic optoelectronic device to induce luminescence, and can be a material such as a metal complex that emits light by being excited multiple times to a triplet state or more. The luminescent dopant can be, for example, an inorganic, organic, or organic / inorganic compound, and can contain one or two or more types.
[0134] The luminescent dopant may be, for example, a phosphorescent sensitizer, a fluorescent dopant, or a combination thereof.
[0135] The phosphorescent sensitizer can be an organometallic compound and can effectively transfer energy received from the host to the fluorescent dopant. The phosphorescent sensitizer increases the energy transfer to the fluorescent dopant, causing the excitons formed in the light-emitting layer to emit light quickly within the light-emitting layer, thereby reducing the degradation of the light-emitting diode.
[0136] The phosphorescent sensitizer may be, for example, an organometallic compound comprising iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), rhodium (Rh), or a combination thereof, and may be, for example, an organometallic compound comprising an organic ligand comprising a nitrogen-containing ring. The nitrogen-containing ring may be, for example, a substituted or unsubstituted pyridine, a substituted or unsubstituted pyrimidine, a substituted or unsubstituted triazine, a substituted or unsubstituted carbazole, a substituted or unsubstituted imidazole, a substituted or unsubstituted benzimidazole, or a combination thereof.
[0137] In one embodiment, the phosphorescence sensitizer can be, for example, one of compounds P1 to P52:
[0138]
[0139]
[0140] The fluorescent dopant may be, for example, a polycyclic compound, and may improve the luminous efficiency and lifespan characteristics of a light emitting diode by receiving energy transfer due to high absorbance within a light emitting layer.
[0141] The fluorescent dopant may be, for example, a condensed polycyclic compound including boron (B), nitrogen (N), or a combination thereof. In one embodiment, the fluorescent dopant may include, for example, one of compounds D1 to D30.
[0142]
[0143]
[0144] The phosphorescent sensitizer and the fluorescent dopant can each be included in an amount of less than or equal to about 20 wt %, and within the above range, about 0.1 wt % to about 20 wt %, about 0.1 wt % to about 15 wt %, about 0.1 wt % to about 10 wt %, about 0.1 wt % to about 7 wt %, about 0.1 wt % to about 5 wt %, about 0.1 wt % to about 4 wt %, about 1 wt % to about 20 wt %, about 1 wt % to about 15 wt %, about 1 wt % to about 10 wt %, about 1 wt % to about 7 wt %, about 1 wt % to about 5 wt %, or about 1 wt % to about 4 wt %, based on the total weight of the composition for an organic optoelectronic device.
[0145] The composition for an organic optoelectronic device may further include an additive, and the additive may include, for example, an organic material, an inorganic material, an organic / inorganic material, or a combination thereof.
[0146] Hereinafter, an organic optoelectronic device using the above-mentioned composition for an organic optoelectronic device will be described.
[0147] The organic optoelectronic device may be, for example, an organic light emitting diode, an organic optoelectronic device, or an organic solar cell. In one embodiment, the organic optoelectronic device may be an organic light emitting diode.
[0148] The organic optoelectronic device may include an anode and a cathode facing each other, and an organic layer between the anode and the cathode, and the organic layer may contain the above-mentioned composition. The organic layer may include an active layer such as a light-emitting layer or a light-absorbing layer, and the active layer may contain the above-mentioned composition. The organic layer may include an auxiliary layer between the anode and the active layer and / or between the cathode and the active layer, and the auxiliary layer may contain the above-mentioned composition.
[0149] Figure 1 is a cross-sectional view illustrating an example of an organic light emitting diode as an example of an organic optoelectronic device according to some embodiments.
[0150] refer to Figure 1 , the organic light emitting diode 100 according to some embodiments includes an anode 110 and a cathode 120 facing each other, and a light emitting layer 130 between the anode 110 and the cathode 120 .
[0151] The anode 110 may be made of a conductor having a high work function to facilitate hole injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 110 may be made of a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or alloys thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); 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.
[0152] The cathode 120 may be made of a conductor having a low work function to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 120 may be made of 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.
[0153] The light-emitting layer 130 may include the above-mentioned composition for an organic optoelectronic device as a mixed host. The light-emitting layer 130 may further include another organic compound as a mixed host. The light-emitting layer 130 may further include the above-mentioned light-emitting dopant and may include a fluorescent dopant, a phosphorescent sensitizer, or a combination thereof as described above. As an embodiment, by combining the above-mentioned composition for an organic optoelectronic device with a light-emitting dopant, the light-emitting layer 130 may emit light in a blue light emission spectrum. At least one of the first compound and the second compound of the above-mentioned composition for an organic optoelectronic device has a high triplet energy level greater than or equal to about 2.8 eV, so that exciton transfer to the blue light-emitting dopant can be easy, and thus an organic optoelectronic device with high efficiency and long life can be realized. The peak wavelength of the blue light emission spectrum can fall within, for example, about 410 nm to about 480 nm, and the range can fall within about 420 nm to about 470 nm or about 430 nm to about 470 nm.
[0154] In one embodiment, the above-mentioned composition for an organic optoelectronic device may include a first compound and a second compound, wherein the first compound is a bipolar compound having relatively strong electron transport properties, and the second compound is a compound having relatively strong hole transport properties, thereby improving the luminous efficiency by increasing the balance of electrons and holes in the light-emitting layer 130 compared to the case where the first compound is used alone or the second compound is used alone, and at the same time, improving the lifespan by reducing the unbound charges caused by the imbalance in the mobility of electrons and holes.
[0155] In one embodiment, in an organic light emitting diode 100 including a light emitting layer 130 using a composition for an organic optoelectronic device as a mixed host, holes and electrons injected from the anode 110 and the cathode 120 can be properly distributed within the light emitting layer 130, mobility can be finely controlled to an appropriate level, and exciton generation within the light emitting layer 130 can be strongly induced, thereby improving the luminous efficiency of the light emitting layer 130.
[0156] In addition, the generation of excitons at inappropriate locations such as the interface between the light-emitting layer 130 and the adjacent layer and / or the accumulation of unbound charges at the interface between the light-emitting layer 130 and the adjacent layer due to the difference in mobility of holes and electrons injected from the anode 110 and the cathode 120, respectively, within the light-emitting layer 130 can be reduced or prevented.
[0157] Therefore, a roll-off phenomenon in which the luminous efficiency of the organic light emitting diode 100 is rapidly reduced due to un-emitted excitons and / or unbound charges can be reduced or prevented, thereby ultimately improving the lifespan of the organic light emitting diode 100 .
[0158] The organic light emitting diode 100 may be manufactured by forming the anode 110 or the cathode 120 on a substrate, forming a light emitting layer using a dry film forming method such as vacuum evaporation, sputtering, plasma plating, and ion plating, and forming the cathode 120 or the anode 110 thereon.
[0159] Figure 2 is a cross-sectional view illustrating another example of an organic light emitting diode as an example of an organic optoelectronic device according to some embodiments.
[0160] refer to Figure 2 Similar to the above embodiment, the organic light emitting diode 100 according to this embodiment includes an anode 110, a cathode 120, and a light emitting layer 130. The organic light emitting diode 100 according to this embodiment may further include a hole transport layer 140, a hole transport auxiliary layer 150, and an electron transport layer 160.
[0161] The hole transport layer 140 may be positioned between the anode 110 and the light emitting layer 130, and the hole transport auxiliary layer 150 may be positioned between the light emitting layer 130 and the hole transport layer 140. The electron transport layer 160 may be positioned between the cathode 120 and the light emitting layer 130.
[0162] The hole transport layer 140 can facilitate hole transport from the anode 110 to the light-emitting layer 130 and can include, for example, an amine compound. In one embodiment, the amine compound can have at least one aryl group and / or heteroaryl group having a hole-forming property. In one embodiment, the amine compound can be represented by Chemical Formula 6a or Chemical Formula 6b.
[0163]
[0164] In Chemical Formula 6a or Chemical Formula 6b, Ar a to Ar g Each independently may be, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof.
[0165] In one embodiment, Ar a to Ar c At least one of Ar d to Ar g At least one of may be a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof.
[0166] Ar h It may be, for example, a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof.
[0167] The hole transport auxiliary layer 150 can form an interface with the light-emitting layer 130 by being positioned between the hole transport layer 140 and the light-emitting layer 130 and in contact with the light-emitting layer 130. The hole transport auxiliary layer 150 can help further reduce or prevent the generation of excitons at inappropriate locations, such as at the interface between the light-emitting layer 130 and an adjacent layer, and / or the accumulation of unbound charges at the interface between the light-emitting layer 130 and an adjacent layer. Therefore, the roll-off phenomenon in which the luminous efficiency of the organic light-emitting diode 100 is rapidly reduced due to un-emitted excitons and / or unbound charges can be further reduced or prevented, thereby ultimately improving the lifespan of the organic light-emitting diode 100.
[0168] The electron transport layer 160 may further increase electron injection and / or electron mobility and block holes between the cathode 120 and the light emitting layer 130 .
[0169] The electron transport layer 160 may include, for example, the compound of Group 5.
[0170] [Group 5]
[0171]
[0172]
[0173]
[0174]
[0175] An organic optoelectronic device including the organic light emitting diode may be applied to a display device.
[0176] The following examples and comparative examples are provided to highlight the features of one or more embodiments, but it should be understood that these examples and comparative examples should not be interpreted as limiting the scope of the embodiments, and these comparative examples should not be interpreted as being outside the scope of the embodiments. In addition, it should be understood that the embodiments are not limited to the specific details described in these examples and comparative examples.
[0177] 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.
[0178] Preparation of compounds for organic optoelectronic devices
[0179] These compounds were synthesized by the following steps.
[0180] (Synthesis of the First Compound)
[0181] Synthesis Example 1
[0182] [Reaction formula 1]
[0183]
[0184] Step 1: Synthesis of IA-1-1
[0185] 20 g of 2-phenylbenzimidazole, 22 g of 2-bromofluorobenzene, 65 g of potassium phosphate (ternary) and 515 ml of DMF were mixed and stirred at 190° C. for 48 hours. After the mixture was cooled at ambient temperature, a solid product generated by adding 1000 ml of distilled water was filtered and column purified to synthesize compound IA-1-1.
[0186] Step 2: Synthesis of IA-1-2
[0187] 32 g of compound IA-1-1, 28 g of bis(pinacolato)diboron, 3.7 g of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), 27 g of potassium acetate, and 458 ml of toluene were mixed and then stirred at 120° C. for 10 hours. Subsequently, the mixture was concentrated and column purified to synthesize compound IA-1-2.
[0188] Step 3: Synthesis of A-1
[0189] 25 g of compound IA-1-2, 28 g of 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole), 3.6 g of tetrakis(triphenylphosphine)palladium(0), 26 g of potassium carbonate, 210 ml of tetrahydrofuran, and 100 ml of distilled water were mixed and stirred at 80° C. for 18 hours. After the mixture was cooled to ambient temperature, the solid product produced by adding 100 ml of methanol and 300 ml of distilled water was filtered and column purified to synthesize compound A-1.
[0190] (Synthesis of the Second Compound)
[0191] Synthesis Example 4: Synthesis of Compound E-72
[0192] [Reaction formula 2]
[0193]
[0194] Compound E-72 was synthesized by referring to the method disclosed in Korean Patent Publication No. 10-2023-0155972.
[0195] Comparative Synthesis Example 1: Synthesis of Compound HT-1
[0196]
[0197] Comparative compound HT-1 was synthesized by referring to the method described in Korean Patent Publication No. 10-2023-0037447.
[0198] Manufacturing of organic light-emitting diodes
[0199] Example 1
[0200] A glass substrate coated with an ITO (indium tin oxide) thin film was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with isopropyl alcohol, acetone, or methanol and dried. The substrate was then moved to a plasma cleaner, cleaned for 10 minutes using oxygen plasma, and moved to a vacuum depositor. The prepared ITO transparent electrode was used as an anode, and compound A (Novaled GmbH) doped with 3% NDP-9 was vacuum deposited on the ITO substrate to form A hole injection layer is formed, and compound A is deposited on the hole injection layer. The hole transport layer is formed by depositing mCP (1,3-di(carbazol-9-yl)benzene) on the hole transport layer. On the hole transport auxiliary layer, the compound A-1 obtained in Synthesis Example 1 and the compound E-72 obtained in Synthesis Example 2 were used as the host, 13 wt% of P31 was doped as a phosphorescent sensitizer, and 1.5 wt% of D3 was doped as a fluorescent dopant, and a hole transport auxiliary layer was formed by vacuum deposition. Thick light-emitting layer. In this article, compound A-1 and compound E-72 were used in a weight ratio of 4:6. Subsequently, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) was deposited on the light-emitting layer. to form an electron transport auxiliary layer, and compound B and Liq were simultaneously vacuum deposited at a weight ratio of 1:1 to form The thick electron transport layer is formed by vacuum deposition on the electron transport layer. LiQ and Al is used to form the cathode to manufacture organic light-emitting diodes.
[0201] ITO / Compound A (3% NDP-9 doping, ) / Compound A / mCP / EML[host (Compound A-1:Compound E-72):P31:D3=85.5wt%:13wt%:1.5wt%] / BCP / Compound B:LiQ / LiQ / Al
[0202] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine
[0203] Compound B: 8-{4-[bis(naphthalen-2-yl)-1,3,5-triazin-2-yl]phenyl}quinoline
[0204]
[0205] Comparative Example 1
[0206] An organic light-emitting diode was manufactured in the same manner as in Example 1, except that the light-emitting layer was formed by using compound A-1 according to Synthesis Example 1 alone instead of compound A-1 according to Synthesis Example 1 and compound E-72 according to Synthesis Example 2 as the host of the light-emitting layer.
[0207] Comparative Example 2
[0208] An organic light-emitting diode was manufactured in the same manner as in Example 1, except that the light-emitting layer was formed by solely using Compound E-72 according to Synthesis Example 2 instead of Compound A-1 according to Synthesis Example 1 and Compound E-72 according to Synthesis Example 2 as the host of the light-emitting layer.
[0209] Comparative Example 3
[0210] An organic light-emitting diode was manufactured in the same manner as in Example 1, except that a light-emitting layer was formed by using Compound A-1 according to Synthesis Example 1 and Compound HT-1 according to Comparative Synthesis Example 1 instead of Compound A-1 according to Synthesis Example 1 and Compound E-72 according to Synthesis Example 2 as the host of the light-emitting layer.
[0211] Evaluate
[0212] The luminous efficiency characteristics of the organic light emitting diodes according to the examples and the comparative examples were evaluated.
[0213] The specific measurement method is as follows, and the results are shown in Table 1.
[0214] (1) Measuring the change in current density according to voltage change
[0215] While increasing the voltage from 0 V to 10 V, the current value flowing through the unit diode in the obtained organic light emitting diode was measured using a current-voltage meter (Keithley 2400), and the measured current value was divided by the area to provide a result.
[0216] (2) Measuring brightness changes according to voltage changes
[0217] While increasing the voltage of the organic light emitting diode from 0 V to 10 V, the luminance was measured using a luminance meter (Minolta Cs-1000A).
[0218] (3) Measurement of luminous efficiency
[0219] Using the luminance and current density and voltage measured from (1) and (2) above, calculate the 2 ) under the current efficiency (cd / A). The luminous efficiency values of the organic light emitting diodes of the examples and comparative examples were calculated as relative values based on Comparative Example 3 and are listed in Table 1.
[0220] [Table 1]
[0221]
[0222] Referring to Table 1, the organic light emitting diode according to the embodiment has improved light emitting efficiency characteristics compared to the light emitting diode according to the comparative example.
[0223] One or more embodiments may provide a composition for an organic optoelectronic device that may achieve high efficiency and long life characteristics.
[0224] Some embodiments may provide an organic optoelectronic device including the composition for an organic optoelectronic device.
[0225] An organic optoelectronic device with high efficiency and long life can be realized.
[0226] Exemplary embodiments have been disclosed herein, and although specific terms are used, these terms are used and interpreted only in a general and descriptive sense, not for limiting purposes. In some cases, it will be clear 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 alone 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 in form and detail may be made without departing from the spirit and scope of the invention as set forth in the appended claims.
Claims
1. A composition for an organic optoelectronic device, comprising: a first compound represented by Chemical Formula 1; and The second compound represented by Chemical Formula 2: [Chemical Formula 1] In Chemical Formula 1, Z 1 to Z 3 Each independently is N or CR a , where R a is hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, cyano or halogen, provided that Z 1 to Z 3 At least two of them are N, L 1 To L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted divalent C2 to C20 heterocyclic group, and Ar 1 to Ar 3 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, provided that Ar 1 to Ar 3 At least one of them is a group represented by chemical formula A, [Chemical Formula A] In chemical formula A, R 1 to R 4 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a cyano group, a halogen group, or a connection point to Chemical Formula 1, and R 1 to R 4 Separate existence or R 1 to R 4 Two adjacent ones are connected to each other to form a ring, [Chemical Formula 2] In Chemical Formula 2, L 7 and L 8 are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group, Ar 7 is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and R 30 to R 33 、R 34’ 、R 34” 、R 34”’ and R 35 to R 42 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a cyano group or a halogen group.
2. The composition for an organic optoelectronic device according to claim 1, wherein Ar 1 to Ar 3 At least one of them is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted carbazolyl group.
3. The composition for an organic optoelectronic device according to claim 2, wherein: Ar 1 to Ar 3 One of the groups is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted carbazolyl group, and Ar 1 to Ar 3 The remaining two groups in are groups represented by Chemical Formula A.
4. The composition for an organic optoelectronic device according to claim 2, wherein: Ar 1 to Ar 3 One of them is a group represented by chemical formula A, and Ar 1 to Ar 3 The remaining two groups in are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted carbazolyl group.
5. The composition for an organic optoelectronic device according to claim 4, wherein: Ar 1 is a group represented by chemical formula A, L 1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group, and Ar 2 and Ar 3 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted carbazolyl group.
6. The composition for an organic optoelectronic device according to claim 5, wherein L 1 is a substituted or unsubstituted o-phenylene group.
7. The composition for an organic optoelectronic device according to claim 1, wherein The first compound is represented by one of Chemical Formulas 1A to 1C: [Chemical Formula 1A] [Chemical Formula 1B] [Chemical Formula 1C] In Chemical Formulas 1A to 1C, Z 1 to Z 3 and L 1 To L 3 The definition of is the same as that in Chemical Formula 1, Ar 1 is a group represented by chemical formula A, R 12 to R 27 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, substituted or unsubstituted amino, substituted or unsubstituted silyl, cyano or halogen, and R 12 to R 27 Separate existence or R 12 to R 27 Two adjacent ones are connected to each other to form a ring.
8. The composition for an organic optoelectronic device according to claim 1, wherein The first compound is represented by one of Chemical Formulas 1A-1 to 1A-4, 1B-1 to 1B-4, and 1C-1 to 1C-4: In Chemical Formulas 1A-1 to 1A-4, 1B-1 to 1B-4, and 1C-1 to 1C-4, Z 1 to Z 3 and L 1 To L 3 The definition of is the same as that in Chemical Formula 1, R 1 to R 4 、R 3a 、R 3b 、R 4a 、R 4b and R 12 to R 27 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, substituted or unsubstituted amino, substituted or unsubstituted silyl, cyano or halogen, and R 1 to R 4 、R 3a 、R 3b 、R 4a 、R 4b and R 12 to R 27 Separate existence or R 1 to R 4 、R 3a 、R 3b 、R 4a 、R 4b and R 12 to R 27 Two adjacent ones are connected to each other to form a ring.
9. The composition for an organic optoelectronic device according to claim 1, wherein Chemical Formula 2 is represented by one of Chemical Formulas 2a to 2d: [Chemical Formula 2a] [Chemical Formula 2b] [Chemical Formula 2c] [Chemical formula 2d] In Chemical Formulas 2a to 2d, L 8 、Ar 7 、R 30 to R 33 、R 34’ 、R 34” 、R 34”’ and R 35 to R 42 The definition of is the same as that in Chemical Formula 2.
10. The composition for an organic optoelectronic device according to claim 9, wherein: L 8 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group, and Ar 7 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 triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted dibenzothiazolyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted silyl group.
11. The composition for an organic optoelectronic device according to claim 9, wherein Ar 7 、R 30 to R 33 、R 34’ 、R 34” 、R 34”’ and R 35 to R 42 At least one of them is a substituted or unsubstituted carbazolyl group.
12. The composition for an organic optoelectronic device according to claim 1, wherein The first compound and the second compound are included in a weight ratio of 10:90 to 90:
10.
13. An organic optoelectronic device comprising: an anode and a cathode facing each other, and a light-emitting layer between the anode and the cathode, The light-emitting layer comprises the composition for an organic optoelectronic device according to any one of claims 1 to 12. The organic optoelectronic device according to claim 13 , wherein the light-emitting layer further comprises a fluorescent dopant, a phosphorescent sensitizer, or a combination thereof.
15. The organic optoelectronic device according to claim 14, wherein: The fluorescent dopant is a condensed polycyclic compound containing boron, nitrogen or a combination thereof, and The phosphorescence sensitizer is an organometallic compound. The organic optoelectronic device according to claim 13 , wherein the light emitting layer emits light in a blue emission spectrum.
17. The organic optoelectronic device according to claim 13, further comprising: 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. 18 . A display device comprising the organic optoelectronic device according to claim 13 .
Citation Information
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