Composition for organic optoelectronic device, organic optoelectronic device and display device

Abstract

Provided are a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. The composition for an organic optoelectronic device includes a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2. # imgabs0 #

Description

[0001] Citation of Related Applications

[0002] This application claims the priority and benefit of Korean Patent Application No. 10-2024-0009466, filed with the Korean Intellectual Property Office on January 22, 2024, the entire content of which is incorporated herein by reference. Technical Field

[0003] Embodiments relate to a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. Background Art

[0004] An organic optoelectronic device (e.g., an organic optoelectronic diode) is a device capable of converting electrical energy and light energy into each other.

[0005] According to the operating principle, organic optoelectronic devices can be classified into two types. One is a photoelectric 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, respectively, and the other is a light-emitting device that generates light energy from electrical energy by applying a voltage or current to the electrodes.

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

[0007] Among these, due to the increasing demand for flat panel display devices, organic light-emitting diodes (OLEDs) have received much attention in recent years. An organic light-emitting diode may be a device that converts electrical energy into light, and the performance of an organic light-emitting diode can be greatly affected by the organic material between the electrodes. Summary of the Invention

[0008] Embodiments relate to 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:

[0009] [Chemical Formula 1]

[0010]

[0011] In Chemical Formula 1, Z 1 to Z 6 are each independently N or CR a , each R a is independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted silyl group, cyano group, or halogen, and at least two of Z 1 to Z 3 are N or Z 4 to Z6 At least two of them are N, L 1 is a substituted or unsubstituted C6-C30 arylene, L 2 to L 5 are each independently a single bond, a substituted or unsubstituted C6-C30 arylene or a substituted or unsubstituted divalent C2-C30 heterocyclic group, and Ar 1 to Ar 4 are each independently a substituted or unsubstituted C6-C30 aryl or a substituted or unsubstituted C2-C30 heterocyclic group, provided that Ar 1 to Ar 4 are not substituted or unsubstituted carbazolyl groups,

[0012] [Chemical formula 2]

[0013]

[0014] In Chemical formula 2, L 7 and L 8 are each independently a single bond or a substituted or unsubstituted C6-C30 arylene, Ar 7 is a substituted or unsubstituted C6-C30 aryl or a substituted or unsubstituted C2-C30 heterocyclic group, and R 30 to R 33 、R 34’ 、R 34” 、R 34”’ and R 35 to R 42 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a cyano group or a halogen.

[0015] An embodiment can be realized 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 contains a composition for an organic optoelectronic device according to one embodiment.

[0016] An embodiment can be realized by providing a display device including an organic optoelectronic device according to one embodiment. Brief Description of the Drawings

[0017] By describing exemplary embodiments in detail with reference to the accompanying drawings, these features will become clear to those skilled in the art, wherein:

[0018] Figure 1 is a cross-sectional view showing an example of an organic light-emitting diode as an example of an organic optoelectronic device according to one embodiment, and

[0019] Figure 2 It is a cross-sectional view showing another example of an organic light-emitting diode as an example of an organic optoelectronic device according to another embodiment. Detailed Description

[0020] 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 the exemplary embodiments to those skilled in the art.

[0021] In the drawings, the dimensions of layers and regions may be exaggerated for clarity. It will 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 an intermediate layer may also be present. Further, it will 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 intermediate layers may also be present. Additionally, it will 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 intermediate layers may also be present. The same reference numerals always denote the same elements. As used herein, the term "or" is not an exclusive term, e.g., "A or B" will include A, B, or both A and B.

[0022] As used herein, when no other definition is provided, "substituted" means that at least one hydrogen of a substituent or compound is replaced with deuterium, halogen, hydroxy, amino, substituted or unsubstituted C1-C30 amino, nitro, substituted or unsubstituted C1-C40 silyl, C1-C30 alkyl, C1-C10 alkylsilyl, C6-C30 arylsilyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, C1-C20 alkoxy, C1-C10 trifluoroalkyl, cyano, or a combination thereof.

[0023] In one instance, "substituted" means that at least one hydrogen of a substituent or a compound is replaced with deuterium, a C1-C30 alkyl group, a C1-C10 alkylsilyl group, a C6-C30 arylsilyl group, a C3-C30 cycloalkyl group, a C3-C30 heterocycloalkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, or a cyano group. In a specific instance, "substituted" means that at least one hydrogen of a substituent or a compound is replaced with deuterium, a C1-C20 alkyl group, a C6-C30 aryl group, or a cyano group. In a specific instance, "substituted" means that at least one hydrogen of a substituent or a compound is replaced with deuterium, a C1-C5 alkyl group, a C6-C18 aryl group, or a cyano group. In a specific instance, "substituted" means that at least one hydrogen of a substituent or a compound is replaced with deuterium, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0024] "Unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom is retained.

[0025] In this specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)".

[0026] As used herein, when no other definition is provided, "hetero" means including one to three heteroatoms selected from N, O, S, P, and Si in a functional group 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).

[0027] As used herein, "aryl" means a group including at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p-orbitals that form conjugation, such as a phenyl group, a naphthyl group, etc.; two or more hydrocarbon aromatic moieties may be connected by a σ bond and may be, for example, a biphenyl group, a terphenyl group, a quaterphenyl group, etc.; and two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as a fluorenyl group.

[0028] An aryl may include a monocyclic, polycyclic, or fused polycyclic (i.e., rings sharing adjacent carbon atom pairs) functional group.

[0029] As used herein, "heterocyclic group" is a superordinate 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, their fused rings, or their combination. If the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0030] For example, "heteroaryl" may refer to an aryl group including at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly connected by a σ bond, or if the heteroaryl group includes two or more rings, the two or more rings may be fused. If the heteroaryl group is a fused ring, each ring may include one to three heteroatoms.

[0031] More specifically, the substituted or unsubstituted C6-C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted condensed 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 chrysenyl 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.

[0032] More specifically, the substituted or unsubstituted C2-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 benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, or a combination thereof.

[0033] As used herein, the hole property refers to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive property 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.

[0034] In addition, the electron affinity is the ability to accept electrons when an electric field is applied, and due to the conductive property according to the lowest unoccupied molecular orbital (LUMO) energy level, the electrons formed in the cathode can be easily injected into and transported in the light-emitting layer.

[0035] Hereinafter, compositions for organic optoelectronic devices according to some embodiments will be described.

[0036] The composition for an organic optoelectronic device according to some embodiments may include a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2.

[0037] [Chemical Formula 1]

[0038]

[0039] In Chemical Formula 1, Z 1 to Z 6 may each independently be, for example, N or CR a .

[0040] Each R a may independently be or include, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted silyl group, cyano group, or halogen.

[0041] In one embodiment, at least two of Z 1 to Z 3 are N or at least two of Z 4 to Z 6 are N.

[0042] L 1 may be or include, for example, substituted or unsubstituted C6 to C30 arylene.

[0043] L 2 to L 5 may each independently be or include, for example, a single bond, substituted or unsubstituted C6 to C30 arylene, or substituted or unsubstituted divalent C2 to C30 heterocyclic group.

[0044] Ar 1 to Ar 4 may each independently be or include, for example, substituted or unsubstituted C6 to C30 aryl or substituted or unsubstituted C2 to C30 heterocyclic group, provided that none of Ar 1 to Ar 4 is a substituted or unsubstituted carbazolyl group.

[0045] [Chemical Formula 2]

[0046]

[0047] In Chemical Formula 2, L 7 and L 8 can each independently be or include, for example, a single bond or a substituted or unsubstituted C6 to C30 arylene group.

[0048] Ar 7 can be or include, for example, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0049] R 30 to R 33 、R 34’ 、R 34” 、R 34”’ and R 35 to R 42 can each independently 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.

[0050] The first compound and the second compound can be bipolar compounds each having both electron-transporting properties and hole-transporting properties. The first compound can be a bipolar compound having relatively strong electron-transporting properties, and the second compound can be a bipolar compound having relatively strong hole-transporting properties. In one embodiment, the first compound and the second compound can exhibit good interfacial properties due to their structures.

[0051] The composition for an organic optoelectronic device can contain both the first compound and the second compound simultaneously to finely control the mobilities of holes and electrons, thereby balancing holes and electrons in the active layer (e.g., the light-emitting layer) of the organic optoelectronic device.

[0052] In one embodiment, the composition for an organic optoelectronic device can be used as a host of the light-emitting layer and can have good electrical matching with a blue light-emitting dopant that emits light in a blue emission spectrum described hereinafter, thereby improving the efficiency of the organic optoelectronic device and suppressing the deterioration 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 of greater than or equal to about 2.8 eV, such that exciton transfer to the blue light-emitting dopant can be promoted, thereby realizing an organic optoelectronic device having high efficiency and long lifetime.

[0053] In one embodiment, in Chemical Formula 1, Z 1 to Z 3 can each be, for example, N.

[0054] In one embodiment, in Chemical Formula 1, Z 4 to Z 6 can each be, for example, N.

[0055] In one embodiment, in Chemical Formula 1, Z 1 to Z 6 can each be, for example, N.

[0056] In one embodiment, in Chemical Formula 1, any two of Z 1 to Z 3 can be, for example, N and Z 4 to Z 6 can each be, for example, N.

[0057] In one embodiment, in Chemical Formula 1, any two of Z 1 to Z 3 can be, for example, N and any two of Z 4 to Z 6 can be, for example, N.

[0058] In one embodiment, in Chemical Formula 1, L 1 can be, for example, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, or a combination thereof, such as a substituted or unsubstituted m-phenylene, a substituted or unsubstituted o-phenylene, a substituted or unsubstituted p-phenylene, a substituted or unsubstituted m-biphenylene, a substituted or unsubstituted o-biphenylene, a substituted or unsubstituted p-biphenylene, a substituted or unsubstituted m-terphenylene, a substituted or unsubstituted o-terphenylene, or a substituted or unsubstituted p-terphenylene.

[0059] In one embodiment, in Chemical Formula 1, L 2 to L 5 can each independently be, for example, a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, or a combination thereof.

[0060] In one embodiment, in Chemical Formula 1, Ar 1 to Ar 4Each may independently 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 phenanthryl group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiophenyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0061] In one embodiment, in Chemical Formula 1, Ar 1 and Ar 2 Any one of them may be, for example, a substituted or unsubstituted phenyl group.

[0062] In one embodiment, in Chemical Formula 1, Ar 1 and Ar 2 Any one of them and Ar 3 and Ar 4 Any one of them may be, for example, a substituted or unsubstituted phenyl group.

[0063] In one embodiment, in Chemical Formula 1, Ar 1 to Ar 4 At least one of them may be, for example, a substituted or unsubstituted C2-C30 heterocyclic group, provided that Ar 1 to Ar 4 Are not substituted or unsubstituted carbazolyl groups, for example, substituted or unsubstituted benzofuranyl groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted benzothiophenyl groups, or substituted or unsubstituted dibenzothiophenyl groups.

[0064] In one embodiment, at least one of each substituent in Chemical Formula 1 may be substituted with deuterium. The number of substituted deuterium atoms may be from 1 to the maximum number of hydrogens in the chemical formula, for example, from 1 to 40 or from 1 to 30.

[0065] The second compound may be represented by, for example, one of Chemical Formulas 2a to 2d.

[0066] [Chemical Formula 2a]

[0067]

[0068] [Chemical Formula 2b]

[0069]

[0070] [Chemical Formula 2c]

[0071]

[0072] [Chemical Formula 2d]

[0073]

[0074] 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 may be the same as those described above.

[0075] In one embodiment, in Chemical Formulas 2 and 2a to 2d, L 8 may be, for example, a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted terphenylene.

[0076] In one embodiment, in Chemical Formulas 2 and 2a to 2d, Ar 7 may be, for example, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthryl, a substituted or unsubstituted terphenylene, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted dibenzothienyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted benzosilolyl, a substituted or unsubstituted dibenzosilolyl, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted silyl.

[0077] In one embodiment, in Chemical Formulas 2 and 2a to 2d, R 30 to R 33 , R 34’ , R 34” , R 34”’ and R 35 to R 42 may each independently be, for example, hydrogen, deuterium, a substituted or unsubstituted methyl, a substituted or unsubstituted ethyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted dibenzothienyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted benzosilolyl, a substituted or unsubstituted dibenzosilolyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted silyl, or a cyano group.

[0078] In one embodiment, in Chemical Formulas 2 and 2a to 2d, Ar 7 , R 30 to R 33, R 34’ , R 34” , R 34”’ and R 35 to R 42 at least one of which may be, for example, a substituted or unsubstituted carbazolyl group.

[0079] In one embodiment, in Chemical Formula 2 and Chemical Formulas 2a to 2d, at least one of each substituent may be substituted with deuterium. The number of substituted deuterium atoms may be from 1 to the maximum number of hydrogens in the chemical formula, for example, from 1 to 40 or from 1 to 30.

[0080] In one embodiment, the first compound may include, for example, a compound of Group 1.

[0081] [Group 1]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094] (Dn represents the number of hydrogen atoms replaced by deuterium and represents a structure substituted with one or more deuterium atoms.) However, as described above, based on natural or artificial substitution, any hydrogen in any compound may be protium, deuterium, or tritium.

[0095] In one embodiment, the second compound may include, for example, a compound of Group 2.

[0096] [Group 2]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] (Dn represents the number of hydrogen atoms replaced by deuterium and represents a structure substituted by one or more deuterium atoms.) However, as described above, based on natural or artificial substitution, any hydrogen in any compound can be protium, deuterium, or tritium.

[0104] The composition for an organic optoelectronic device may contain different ratios of a first compound and a second compound.

[0105] In one embodiment, the composition for an organic optoelectronic device may contain the first compound and the second compound in a weight ratio of about 10:90 to about 90:10, for example, in a weight ratio of 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.

[0106] In one embodiment, the first compound may be contained in an amount equal to or greater than that of the second compound. In one embodiment, based on the total amount of the first compound and the second compound, the first compound may be contained in an amount of about 50 wt% to about 90 wt%.

[0107] In one embodiment, the first compound may be contained in an amount equal to or less than that of the second compound. In one embodiment, based on the total amount of the first compound and the second compound, the first compound may be contained in an amount of about 10 wt% to about 50 wt%.

[0108] In addition to the first compound and the second compound, the composition for an organic optoelectronic device may further contain a luminescent dopant.

[0109] The luminescent dopant may be a material that is mixed with the composition for an organic optoelectronic device in a small amount to cause luminescence, and may generally be a material such as a metal complex that luminesces by being excited to a triplet state or more states multiple times. For example, the luminescent dopant may be an inorganic, organic, or organic / inorganic compound, and may contain one or two or more types.

[0110] For example, the luminescent dopant may be a phosphorescent sensitizer, a fluorescent dopant, or a combination thereof.

[0111] The phosphorescent sensitizer can be an organometallic compound and can effectively transfer the energy received from the host to the fluorescent dopant. The phosphorescent sensitizer can increase the energy transfer to the fluorescent dopant, causing the excitons formed in the light-emitting layer to emit light rapidly within the light-emitting layer, thereby reducing the degradation of the light-emitting diode.

[0112] The phosphorescent sensitizer can be, for example, an organometallic compound including 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 can be, for example, an organometallic compound including an organic ligand containing a nitrogen-containing ring. The nitrogen-containing ring can be, for example, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted triazine, substituted or unsubstituted carbazole, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, or a combination thereof.

[0113] The phosphorescent sensitizer can be, for example, one of Compounds P1 to P52.

[0114]

[0115]

[0116]

[0117] The fluorescent dopant can be, for example, a polycyclic compound, and can improve the light-emitting efficiency and lifetime characteristics of the light-emitting diode by receiving energy transfer due to high absorbance within the light-emitting layer.

[0118] The fluorescent dopant can be, for example, a condensed polycyclic compound containing boron (B), nitrogen (N), or a combination thereof, and can be, for example, one of Compounds D1 to D30.

[0119]

[0120]

[0121] Based on the total amount of the composition for the organic optoelectronic device, the phosphorescent sensitizer and the fluorescent dopant can each be included in an amount of less than or equal to about 20 wt% (e.g., 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%).

[0122] The composition for an organic optoelectronic device may further comprise an additive, and the additive may be, for example, an organic material, an inorganic material, an organic / inorganic material, or a combination thereof.

[0123] Hereinafter, an organic optoelectronic device using the above composition for an organic optoelectronic device will be described.

[0124] 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.

[0125] 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 composition. The organic layer may include an active layer, for example, a light-emitting layer or a light-absorbing layer, and the above composition may be contained in the active layer. The organic layer may include a buffer layer between the anode and the active layer or between the cathode and the active layer, and the above composition may be contained in the buffer layer.

[0126] Figure 1 is a cross-sectional view showing an example of an organic light-emitting diode that may be an example of an organic optoelectronic device according to one embodiment.

[0127] Reference Figure 1 , an organic light-emitting diode 100 according to one embodiment may include an anode 110 and a cathode 120 facing each other and a light-emitting layer 130 between the anode 110 and the cathode 120.

[0128] The anode 110 may be made of a conductor having a large work function to facilitate hole injection, and may be made of, for example, a metal, a metal oxide, or a conductive polymer. The anode 110 may be made of: 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), and indium zinc oxide (IZO); a combination of a metal and an oxide, such as ZnO and Al or SnO2 and Sb; a conductive polymer, such as poly(3-methylthiophene), poly(3,4-(ethylenedioxy)thiophene) (PEDOT), polypyrrole, and polyaniline.

[0129] The cathode 120 may be made of a conductor having a small work function to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, 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; a multilayer structure material, such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca.

[0130] The light-emitting layer 130 may include the above-described composition for an organic optoelectronic device as a host. The light-emitting layer 130 may further include another organic compound as a host. The light-emitting layer 130 may further include the above-described light-emitting dopant and may include a fluorescent dopant, a phosphorescent sensitizer, or a combination thereof as described above. In one embodiment, by combining the above-described composition for an organic optoelectronic device with a light-emitting dopant, the light-emitting layer 130 may emit light in a blue emission spectrum. At least one of the first and second compounds of the composition for an organic optoelectronic device may have a high triplet energy level of greater than or equal to about 2.8 eV, such that exciton transfer to a blue light-emitting dopant may be easy, and thus an organic optoelectronic device with high efficiency and long lifetime may be achieved. The peak wavelength of the blue emission spectrum may fall within, for example, about 410 nm to about 480 nm, such as about 420 nm to about 470 nm, or about 430 nm to about 470 nm.

[0131] In one embodiment, the above-described composition for an organic optoelectronic device may include a first compound having relatively strong electron transport characteristics and a second compound having relatively strong hole transport characteristics, so that the light-emitting efficiency may be improved by increasing the balance of electrons and holes in the light-emitting layer 130 compared to the case of using the first compound alone or the second compound alone, and the lifetime may be improved by reducing unbound charges due to the imbalance in the mobilities of electrons and holes.

[0132] In one embodiment, in the organic light-emitting diode 100 including the light-emitting layer 130 using the composition for an organic optoelectronic device as a host, holes and electrons injected from the anode 110 and the cathode 120 may be appropriately distributed within the light-emitting layer 130, the mobility may be finely controlled to an appropriate level, and exciton generation within the light-emitting layer 130 may be strongly induced, thereby improving the light-emitting efficiency of the light-emitting layer 130.

[0133] In one embodiment, the generation of excitons at inappropriate positions (e.g., the interface between the light-emitting layer 130 and an adjacent layer) or the accumulation of unbound charges at the interface between the light-emitting layer 130 and an adjacent layer due to the difference in the mobilities of holes and electrons respectively injected from the anode 110 and the cathode 120 within the light-emitting layer 130 may be reduced or prevented.

[0134] In one embodiment, the roll-off phenomenon in which the light-emitting efficiency of the organic light-emitting diode 100 rapidly decreases due to unemitted excitons or unbound charges may be reduced or prevented, thereby ultimately improving the lifetime of the organic light-emitting diode 100.

[0135] An organic light-emitting diode 100 can be manufactured by forming an anode 110 or a cathode 120 on a substrate, forming a light-emitting layer using a dry film forming method (e.g., vacuum evaporation, sputtering, plasma plating, and ion plating), and forming a cathode 120 or an anode 110 thereon.

[0136] Figure 2 FIG. is a cross-sectional view showing another example of an organic light-emitting diode that can be an example of an organic optoelectronic device according to another embodiment.

[0137] Reference Figure 2 , similar to the above-described embodiment, an organic light-emitting diode 100 according to another embodiment may include an anode 110, a cathode 120, and a light-emitting layer 130. However, different from the above-described embodiment, an organic light-emitting diode 100 according to another embodiment may further include a hole transport layer 140, a hole transport assisting layer 150, and an electron transport layer 160.

[0138] The hole transport layer 140 may be located between the anode 110 and the light-emitting layer 130, and the hole transport assisting layer 150 may be located between the light-emitting layer 130 and the hole transport layer 140. The electron transport layer 160 may be located between the cathode 120 and the light-emitting layer 130.

[0139] The hole transport layer 140 may facilitate hole transport from the anode 110 to the light-emitting layer 130 and may include, for example, an amine compound. In one embodiment, the amine compound may have at least one aryl or heteroaryl group having hole characteristics. In one embodiment, the amine compound may be represented by Chemical

[0140] Formulas 6a or 6b.

[0141]

[0142] In Chemical Formulas 6a or 6b, Ar a to Ar g may each independently be or include, 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,

[0143] Ar a to Ar c at least one of and Ar d to Ar g at least one of may be, for example, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof.

[0144] Ar hIt may be a single bond, a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, or a combination thereof.

[0145] The hole transport auxiliary layer 150 can form an interface with the light-emitting layer 130 by being located 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 further reduce or prevent the generation of excitons at inappropriate positions (e.g., the interface between the above-mentioned light-emitting layer 130 and the adjacent layer) or the accumulation of unbound charges at the interface between the light-emitting layer 130 and the adjacent layer. In one embodiment, the roll-off phenomenon of the rapid reduction in the luminous efficiency of the organic light-emitting diode 100 due to unemitted excitons or unbound charges can be further reduced or prevented, thus ultimately improving the lifespan of the organic light-emitting diode 100.

[0146] The electron transport layer 160 can further increase electron injection or electron mobility and block holes between the cathode 120 and the light-emitting layer 130.

[0147] The electron transport layer 160 can include, for example, compounds of Group 5.

[0148] [Group 5]

[0149]

[0150]

[0151]

[0152] The organic optoelectronic device including the above-mentioned organic light-emitting diode can be applied to a display device.

[0153] The following examples and comparative examples are provided to highlight the features of one or more embodiments, but it will be understood that these examples and comparative examples should not be construed as limiting the scope of these embodiments, and these comparative examples should not be construed as being outside the scope of these embodiments. In addition, it will be understood that the embodiments are not limited to the specific details described in the examples and comparative examples.

[0154] Hereinafter, the starting materials and reactants used in the examples and synthesis examples are purchased from Sigma-Aldrich Co., Ltd., TCI Inc., Tokyo Chemical Industry, or P&Htech or synthesized by known methods unless otherwise specified.

[0155] Preparation of Compounds for Organic Optoelectronic Devices

[0156] The compound is synthesized through the following steps.

[0157] (Synthesis of the first compound)

[0158] Synthesis Example 1: Synthesis of Compound A-47

[0159] [Reaction Formula 1]

[0160]

[0161] Compound A-47 was synthesized by referring to the synthesis method described in Korean Patent No. 10-2050000 and using Int-1 (CAS No. 2173555-96-7) and Int-2 (CAS No. 1269508-31-7).

[0162] Synthesis Example 2: Synthesis of Compound A-29

[0163] [Reaction Formula 2]

[0164]

[0165] Compound A-29 was synthesized by referring to the synthesis method described in Korean Patent No. 10-2050000 and using Int-1 (CAS No. 2173555-96-7) and Int-3 (CAS No. 1696425-27-0).

[0166] Synthesis Example 3: Synthesis of Compound A-43

[0167] [Reaction Formula 3]

[0168]

[0169] Compound A-43 was synthesized by referring to the synthesis method described in Korean Patent No. 10-2050000 and using Int-4 (CAS No. 147229-25-1) and Int-2 (CAS No. 1269508-31-7).

[0170] (Synthesis of the second compound)

[0171] Synthesis Example 4: Synthesis of Compound D-72

[0172] [Reaction Formula 4]

[0173]

[0174] Compound D-72 was synthesized by referring to the synthesis method described in Korean Patent Publication No. 10-2023-0155972.

[0175] Comparative Synthesis Example 1: Synthesis of Compound HT-1

[0176]

[0177] The comparative compound HT-1 was synthesized by referring to the synthesis method described in Korean Patent Publication No. 10-2023-0037447.

[0178] Manufacture of Organic Light-Emitting Diodes

[0179] Example 1

[0180] A glass substrate coated with an ITO (indium tin oxide) film was ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrate was ultrasonically cleaned with isopropyl alcohol, acetone, or methanol and dried, then transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and moved to a vacuum depositor. The prepared ITO transparent electrode was used as the anode, and compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum-deposited on the ITO substrate to form a thick hole injection layer, and compound A was deposited on the hole injection layer to a thickness to form a hole transport layer. mCP was deposited on the hole transport layer to a thickness to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compound A-47 obtained in Synthesis Example 1 and compound D-72 obtained in Synthesis Example 4 were used as hosts simultaneously, doped with 13 wt% of P31 as a phosphorescent sensitizer, and doped with 1.5 wt% of D3 as a fluorescent dopant to form a thick light-emitting layer by vacuum deposition. Here, compound A-47 and compound D-72 were used in a weight ratio of 4:6. Subsequently, BCP was deposited on the light-emitting layer to a thickness to form an electron transport auxiliary layer, and compound B and Liq were vacuum-deposited simultaneously in a weight ratio of 1:1 to form a thick electron transport layer. By sequentially vacuum-depositing LiQ of and

[0181] Al of on the electron transport layer to form a cathode, thereby manufacturing an organic light-emitting diode. / compound A (doped with 3% NDP-9, / compound A / mCP / EML [host (compound A-47: compound D-72): P31: D3 = 85.5 wt%: 13 wt%: 1.5 wt%] / BCP / Al

[0182] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine

[0183] Compound B: 8-{4-[bis(naphthalen-2-yl)-1,3,5-triazin-2-yl]phenyl}quinoline

[0184]

[0185] Example 2

[0186] An organic light-emitting diode was fabricated in the same manner as in Example 1, except that Compound A-29 obtained in Synthesis Example 2 and Compound D-72 obtained in Synthesis Example 4 were used as the host of the light-emitting layer to form the light-emitting layer instead of Compound A-47 obtained in Synthesis Example 1 and Compound D-72 obtained in Synthesis Example 4.

[0187] Example 3

[0188] An organic light-emitting diode was fabricated in the same manner as in Example 1, except that Compound A-43 obtained in Synthesis Example 3 and Compound D-72 obtained in Synthesis Example 4 were used as the host of the light-emitting layer to form the light-emitting layer instead of Compound A-47 obtained in Synthesis Example 1 and Compound D-72 obtained in Synthesis Example 4.

[0189] Comparative Example 1

[0190] An organic light-emitting diode was fabricated in the same manner as in Example 1, except that Compound A-47 obtained in Synthesis Example 1 and Compound HT-1 obtained in Comparative Synthesis Example 1 were used as the host of the light-emitting layer instead of Compound A-47 obtained in Synthesis Example 1 and Compound D-72 synthesized in Synthesis Example 4.

[0191] Evaluation

[0192] The luminous efficiency and lifetime characteristics of the organic light-emitting diodes according to Examples 1 to 3 and Comparative Example 1 were evaluated.

[0193] The specific measurement method is as follows, and the results are shown in Table 1.

[0194] (1) Measuring the change in current density according to the voltage change

[0195] While increasing the voltage from 0 V to 10 V, the current value flowing through the unit device 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 the result.

[0196] (2) Measure the change in luminance according to the change in voltage

[0197] While increasing the voltage of the organic light-emitting diode from 0 V to 10 V, measure the luminance using a luminance meter (Minolta Cs-1000A).

[0198] (3) Measurement of luminous efficiency

[0199] By using the luminance and current density from the above (1) and (2), calculate the luminous efficiency (cd / A) at the same current density (10 mA / cm 2 ).

[0200] Calculate the luminous efficiency values of Examples 1 to 3 and Comparative Example 1 as relative values based on Comparative Example 1 and show them in Table 1.

[0201] (4) Measurement of lifetime

[0202] By keeping the luminance (cd / m 2 ) at 2,000 cd / m 2 and measuring the time when the luminous efficiency (cd / A) decreases to 95% to obtain the result.

[0203] Calculate the measured lifetimes of Examples 1 to 3 and Comparative Example 1 as relative values based on Comparative Example 1 and show them in Table 1.

[0204] Table 1

[0205]

[0206] Referring to Table 1, compared with the organic light-emitting diode according to Comparative Example 1, the organic light-emitting diodes according to Examples 1, 2, and 3 exhibit improved luminous efficiency and lifetime characteristics.

[0207] By summarizing and reviewing, one or more embodiments can provide a composition for an organic optoelectronic device that can achieve high efficiency and long lifetime characteristics.

[0208] An organic optoelectronic device with high efficiency and long lifetime can be realized.

[0209] Exemplary embodiments are disclosed herein, and although specific terms are employed, they are used and interpreted in a generic and descriptive sense only and not for purposes of limitation. In some instances, it will be apparent to those skilled in the art that, unless otherwise explicitly specified, features, characteristics, and / or elements described in connection with a particular embodiment may be used singly or in combination with features, characteristics, and / or elements described in connection with other embodiments. Accordingly, those skilled in the art will appreciate that various changes may be made in form and detail 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, the composition comprising: a first compound represented by Chemical Formula 1; and a second compound represented by Chemical Formula 2: [Chemical Formula 1] In Chemical Formula 1, Z 1 to Z 6 each independently is N or CR a , Each R a independently is hydrogen, deuterium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a cyano group or a halogen, Z 1 from Z 3 at least two of which are N or Z 4 to Z 6 at least two of which are N L 1 is a substituted or unsubstituted C6-C30 arylene group, L 2 to L 5 each independently is a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted divalent C2-C30 heterocyclic group, and Ar 1 to Ar 4 each independently is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, provided that Ar 1 to Ar 4 is not a substituted or unsubstituted carbazolyl group [Chemical Formula 2] In Chemical Formula 2, L 7 and L 8 each independently represents a single bond or a substituted or unsubstituted C6-C30 arylene group, Ar 7 is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, and R 30 to R 33 、R 34’ 、R 34” 、R 34”’ and R 35 to R 42 Each independently is hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a cyano group or a halogen.

2. The composition for an organic optoelectronic device according to claim 1, wherein in Chemical Formula 1, Ar 1 to Ar 4 are each independently 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 terphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiophenyl group, or a substituted or unsubstituted dibenzothiophenyl group.

3. The composition for an organic optoelectronic device according to claim 1, wherein in Chemical Formula 1, L 1 is a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, or a combination thereof.

4. The composition for an organic optoelectronic device according to claim 1, wherein in Chemical Formula 1, Z 1 to Z 6 are each N.

5. The composition for an organic optoelectronic device according to claim 1, wherein the second compound is represented by one of Chemical Formulas 2a to 2d: In Chemical Formulas 2a to 2d, L 8 and Ar 7 and R 30 to R 33 and R 34’ and R 34” and R 34”’ and R 35 to R 42 are the same as those defined in Chemical Formula 2.

6. The composition for an organic optoelectronic device according to claim 5, In Chemical Formulas 2a to 2d, L 8 is a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene or a substituted or unsubstituted terphenylene, and In Chemical Formulas 2a to 2d, 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 anthryl group, a substituted or unsubstituted terphenylene 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 benzosilolyl group, a substituted or unsubstituted dibenzosilolyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted silyl group.

7. 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.

8. An organic optoelectronic device, comprising: an anode and a cathode facing each other, and a light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises the composition for an organic optoelectronic device according to any one of claims 1-7.

9. The organic optoelectronic device according to claim 8, wherein the light-emitting layer further comprises a fluorescent dopant, a phosphorescent sensitizer, or a combination thereof.

10. The organic optoelectronic device according to claim 9, wherein the phosphorescent sensitizer is an organometallic compound, and the fluorescent dopant is a condensed polycyclic compound containing boron, nitrogen, or a combination thereof.

11. The organic optoelectronic device according to claim 8, wherein the light-emitting layer emits light in a blue emission spectrum.

12. The organic optoelectronic device according to claim 8, further comprising: a hole transport layer between the anode and the light-emitting layer, and a hole transport assisting layer between the light-emitting layer and the hole transport layer.

13. A display device, comprising the organic optoelectronic device according to any one of claims 8-12.

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