Composition for organic optoelectronic device, organic optoelectronic device and display device
By using compound compositions and dopants of specific structures in organic optoelectronic devices, the problem of insufficient luminescence efficiency and lifetime is solved, and the blue emission spectral performance with high efficiency and long lifetime is achieved.
Patent Information
- Application Number
- CN202411494489.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-01-22
- Filing Date
- 2024-10-24
- Publication Date
- 2025-07-22
AI Technical Summary
Existing organic optoelectronic devices have shortcomings in luminous efficiency and lifetime, especially in the blue emission spectrum with limited performance improvement.
The composition containing the first compound and the second compound of a specific structure is used as the host material of the luminescent layer, and the hole and electron mobility are finely controlled to achieve exciton transfer and equilibrium in the luminescent layer.
The luminescence efficiency of organic optoelectronic devices is improved and the life of the device is extended, especially in the blue emission spectrum, which shows high efficiency and long life.
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Figure CN120358916A_ABST
Abstract
Description
[0001] Citation of Related Applications
[0002] This application claims priority and the benefit of Korean Patent Application No. 10-2024-0009464, filed with the Korean Intellectual Property Office on January 22, 2014, the entire contents of which are incorporated herein by reference. Technical Field
[0003] Embodiments of the present invention disclose compositions for organic optoelectronic devices, organic optoelectronic devices, and display devices. Background Art
[0004] An organic optoelectronic device (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 mainly classified into two types. One can be 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 can be a light-emitting device that generates light energy from electrical energy by supplying voltage or current to electrodes. Summary of the Invention
[0006] Embodiments of the present invention relate to 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:
[0007] [Chemical Formula 1]
[0008]
[0009] In Chemical Formula 1, X is O or S, Z 1 to Z 3 are each independently N or CR a , Z 1 to Z 3 at least two of which 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, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C3 to C30 heterocyclic group, A is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenyl 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, R 1 to R 3 and Ra Each is independently 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, and R 1 to R 3 exist separately or two adjacent ones are linked to form a ring.
[0010] [Chemical Formula 2]
[0011]
[0012] In Chemical Formula 2, L 7 and L 8 are each independently 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 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.
[0013] L 1 and L 2 can each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group or a substituted or unsubstituted naphthylene group, and L 3 can be a single bond.
[0014] Ar 1 and Ar 2 can each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzosilolyl group or a substituted or unsubstituted dibenzosilolyl group.
[0015] The first compound can be represented by Chemical Formula 1a:
[0016] [Chemical Formula 1a]
[0017]
[0018] In Chemical Formula 1a, X and Y can each independently be O or S, and Z 1 to Z 3 can each independently be N or CR a Z 1 to Z 3 at least two of which can be N, L 1 to L 3 can each independently be a single bond, a substituted or unsubstituted C6 - C20 arylene group, or a substituted or unsubstituted divalent C2 - C20 heterocyclic group, Ar 1 can be a substituted or unsubstituted C6 - C30 aryl group or a substituted or unsubstituted C3 - C30 heterocyclic group, A and A' can each independently be a substituted or unsubstituted benzene, a substituted or unsubstituted naphthalene, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted terphenyl, a substituted or unsubstituted benzofuran, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted benzothiophene, or a substituted or unsubstituted dibenzothiophene, R 1 to R 6 and R a can each independently be 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, R 1 to R 3 can each be present separately or two adjacent ones can be connected to form a ring, and R 4 to R 6 can each be present separately or two adjacent ones can be connected to form a ring.
[0019] The second compound can be represented by one of Chemical Formulas 2a to 2d:
[0020] [Chemical Formula 2a]
[0021]
[0022] [Chemical Formula 2b]
[0023]
[0024] [Chemical Formula 2c]
[0025]
[0026] [Chemical Formula 2d]
[0027]
[0028] In 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 defined the same as those in Formula 2.
[0029] L 8 may be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted terphenylene, and Ar 7 may be 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 terrylene, 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, or a substituted or unsubstituted fluorenyl.
[0030] Ar 7 , R 30 to R 33 , R 34’ , R 34” , R 34”’ and R 35 to R 42 at least one of may be a substituted or unsubstituted carbazolyl.
[0031] The first compound and the second compound may be included in a weight ratio of about 10:90 to about 90:10.
[0032] Embodiments may be achieved 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 may include a composition for an organic optoelectronic device according to the embodiments.
[0033] The light-emitting layer may include a fluorescent dopant, a phosphorescent sensitizer, or a combination thereof.
[0034] The phosphorescent sensitizer may be an organometallic compound, and the fluorescent dopant may be a condensed polycyclic compound containing boron, nitrogen, or a combination thereof.
[0035] The light-emitting layer may emit light in a blue emission spectrum.
[0036] The organic optoelectronic device may further include 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.
[0037] Embodiments may be implemented by providing a display device including the organic optoelectronic device according to the embodiments. BRIEF DESCRIPTION OF THE DRAWINGS
[0038] These features will become clear to those skilled in the art by describing exemplary embodiments in detail with reference to the drawings, wherein:
[0039] Figure 1 is a cross-sectional view showing an example of an organic light-emitting diode according to one embodiment, and
[0040] Figure 2 is a cross-sectional view showing another example of an organic light-emitting diode according to another embodiment. DETAILED DESCRIPTION
[0041] Exemplary embodiments will now be described more fully hereinafter with reference to the 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.
[0042] In the drawings, the dimensions of layers and regions may be exaggerated for clarity. It should also be understood that when a layer or element is referred to as being "on" another layer or substrate, it can be directly on the other layer or substrate, or an intermediate layer may also be present. In addition, 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 intermediate layers may also be present. In addition, it should also 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 indicate the same elements. As used herein, the term "or" is not an exclusive term, for example, "A or B" will include A, B, or A and B.
[0043] As used herein, when no other definition is provided, "substituted" may mean that at least one hydrogen of a substituent or compound is replaced by one of the following: deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1-C30 amino group, 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.
[0044] In one embodiment of some embodiments, "substituted" may mean that at least one hydrogen of a substituent or compound is replaced by one of the following: deuterium, C1-C30 alkyl, C1-C10 alkylsilyl, C6-C30 arylsilyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, or cyano. In a specific embodiment of some embodiments, "substituted" may mean that at least one hydrogen of a substituent or compound is replaced by one of the following: deuterium, C1-C20 alkyl, C6-C30 aryl, or cyano. In a specific embodiment of some embodiments, "substituted" may mean that at least one hydrogen of a substituent or compound is replaced by one of the following: deuterium, C1-C5 alkyl, C6-C18 aryl, or cyano. In a specific embodiment of some embodiments, "substituted" may mean that at least one hydrogen of a substituent or compound is replaced by one of the following: deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.
[0045] "Unsubstituted" may mean that a hydrogen atom is not replaced by another substituent and the hydrogen atom is retained.
[0046] 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).
[0047] 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 remaining carbon.
[0048] As used herein, "aryl" may mean a group including at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have conjugated p orbitals, such as phenyl, naphthyl, etc. Two or more hydrocarbon aromatic moieties may be connected by a σ bond and may be, for example, biphenyl, terphenyl, quaterphenyl, etc., and two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl.
[0049] An aryl group may include a monocyclic, polycyclic, or fused polycyclic (i.e., rings sharing adjacent carbon atom pairs) functional group.
[0050] As used herein, "heterocyclic group" may be a superordinate concept of heteroaryl, and may include at least one heteroatom selected from N, O, S, P, and Si substituting for carbon (C) in a cyclic compound such as an aryl group, a cycloalkyl group, their fused rings, or a combination thereof. If the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.
[0051] In one embodiment, "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 may be 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 1 to 3 heteroatoms.
[0052] In one embodiment, 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 anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fused 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 group, a substituted or unsubstituted terrylene group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted indenyl group, or a combination thereof.
[0053] In one embodiment, 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.
[0054] As used herein, hole characteristics may refer to the ability to contribute electrons to form holes if an electric field is applied, and due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported therein.
[0055] In addition, electron characteristics may refer to the ability to accept electrons if an electric field is applied, and due to the conductive characteristics according to the lowest unoccupied molecular orbital (LUMO) energy level, the electrons formed in the cathode can be easily injected into the light-emitting layer and transported therein.
[0056] Hereinafter, compositions for organic optoelectronic devices according to some embodiments will be described.
[0057] A 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.
[0058] [Chemical Formula 1]
[0059]
[0060] In Chemical Formula 1, X may be, for example, O or S.
[0061] Z 1 to Z 3 may each independently be, for example, N or CR a .
[0062] Z1 from Z 3 at least two of which may be, for example, N.
[0063] L 1 from L 3 may each independently be, for example, a single bond, a substituted or unsubstituted C6 - C20 arylene, or a substituted or unsubstituted divalent C2 - C20 heterocyclic group.
[0064] Ar 1 and Ar 2 may each independently be, for example, a substituted or unsubstituted C6 - C30 aryl group or a substituted or unsubstituted C3 - C30 heterocyclic group.
[0065] A may be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenyl 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.
[0066] R 1 to R 3 and R a may each independently be, for example, 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.
[0067] R 1 to R 3 may each exist separately or two adjacent ones may be connected to form a ring.
[0068] [Chemical formula 2]
[0069]
[0070] In Chemical formula 2, L 7 and L 8 may each independently be, for example, a single bond or a substituted or unsubstituted C6 - C30 arylene.
[0071] Ar 7 may be, for example, a substituted or unsubstituted C6 - C30 aryl group or a substituted or unsubstituted C2 - C30 heterocyclic group.
[0072] R 30 to R 33 、R 34’ 、R 34” 、R 34”’ and R 35 to R 42Each may independently be or include, for example, hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted silyl group, cyano group or halogen.
[0073] The first compound and the second compound may be bipolar compounds each having both electron characteristics and hole characteristics. The first compound may be a bipolar compound having relatively strong electron characteristics, while the second compound may be a bipolar compound having relatively strong hole characteristics. In one embodiment, the first compound and the second compound may exhibit good interfacial characteristics due to their structures.
[0074] The composition for an organic optoelectronic device may include the first compound and the second compound together to finely control the mobilities of holes and electrons, thereby balancing holes and electrons in the active layer (e.g., light-emitting layer) of the organic optoelectronic device.
[0075] In one embodiment, the composition for an organic optoelectronic device may be used as a host of the light-emitting layer and may have good electrical matching with a blue light-emitting dopant that emits light in the blue emission spectrum, 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 may have a high triplet energy level of greater than or equal to about 2.8 eV and may promote exciton transfer to the blue light-emitting dopant, thereby realizing an organic optoelectronic device with high efficiency and long lifetime.
[0076] In one embodiment, in Chemical Formula 1, Z 1 to Z 3 may each be N.
[0077] In one embodiment, in Chemical Formula 1, Z 1 and Z 2 may each be N, and Z 3 may be CR a .
[0078] In one embodiment, in Chemical Formula 1, Z 1 and Z 3 may each be N, and Z 2 may be CR a .
[0079] In one embodiment, in Chemical Formula 1, Z 2 and Z 3 may each be N, and Z 1 may be CR a .
[0080] In one embodiment, in Chemical Formula 1, L 1 to L 3 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, a substituted or unsubstituted benzofuranylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted benzothiophenylene, a substituted or unsubstituted dibenzothiophenylene, or a substituted or unsubstituted fluorenylene.
[0081] In one embodiment, in Chemical Formula 1, L 1 and L 2 can each independently be, for example, a single bond or a substituted or unsubstituted C6 - C20 arylene, and in Chemical Formula 1, L 3 can be, for example, a single bond. In one embodiment, in Chemical Formula 1, L 1 and L 2 can each independently be, for example, a single bond or a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, or a substituted or unsubstituted naphthylene, and in Chemical Formula 1, L 3 can be, for example, a single bond.
[0082] In one embodiment, in Chemical Formula 1, Ar 1 and Ar 2 can each independently be, for example, a substituted or unsubstituted C6 - C30 aryl, and can each independently 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 phenanthryl, a substituted or unsubstituted terphenylene, or a substituted or unsubstituted fluorenyl.
[0083] In one embodiment, any one of Ar 1 and Ar 2 can be, for example, a substituted or unsubstituted C6 - C30 aryl, and the other of Ar 1 and Ar 2 can be, for example, a substituted or unsubstituted C3 - C30 heterocyclic group. In one embodiment, either of Ar 1 and Ar 2 can 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 phenanthryl, a substituted or unsubstituted terphenylene, or a substituted or unsubstituted fluorenyl, and Ar 1 and Ar 2Another one in it may be, for example, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzosilolyl group or a substituted or unsubstituted dibenzosilolyl group.
[0084] In one embodiment, if A in Chemical Formula 1 is a substituted or unsubstituted benzofuran or a substituted or unsubstituted benzothiophene, the bonding point to the adjacent ring may be a heterocyclic ring, such as furan or thiophene, or a benzene ring.
[0085] In one embodiment, A may be, for example, a substituted or unsubstituted benzene ring.
[0086] In one embodiment, R a may be, for example, hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted phenyl group or a cyano group.
[0087] The first compound may be represented, for example, by Chemical Formula 1a.
[0088] [Chemical Formula 1a]
[0089]
[0090] In Chemical Formula 1a, X, Z 1 to Z 3 、L 1 to L 3 、Ar 1 、A and R 1 to R 3 may be defined the same as those in Chemical Formula 1.
[0091] Y may be, for example, O or S.
[0092] A' may be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenyl 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.
[0093] R 4 to R 6 may each independently be or include, for example, 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 cyano group or a halogen.
[0094] R 4 to R 6Two that can exist separately or adjacent to each other can be connected to form a ring.
[0095] In one embodiment, X and Y in Formula 1a can be the same.
[0096] In one embodiment, X and Y in Formula 1a can be different from each other.
[0097] In one embodiment, A and A' in Formula 1a can be the same.
[0098] In one embodiment, A and A' in Formula 1a can be different from each other.
[0099] In one embodiment, at least one of each substituent in Formula 1 or 1a can be replaced by deuterium. The number of deuterium atoms replaced can be from 1 to the maximum number of hydrogens in the formula, such as from 1 to 40 or from 1 to 30.
[0100] In one embodiment, the second compound can be represented by one of Formulas 2a to 2d.
[0101] [Formula 2a]
[0102]
[0103] [Formula 2b]
[0104]
[0105] [Formula 2c]
[0106]
[0107] [Formula 2d]
[0108]
[0109] In 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 can be the same as defined in Formula 2.
[0110] In one embodiment, in Formulas 2 and 2a to 2d, L 8 can be, for example, a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted terphenylene.
[0111] In one embodiment, in 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, or a substituted or unsubstituted fluorenyl.
[0112] In one embodiment, in 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.
[0113] In one embodiment, in Formulas 2 and 2a to 2d, at least one of Ar 7 、R 30 to R 33 、R 34’ 、R 34” 、R 34”’ and R 35 to R 42 may be a substituted or unsubstituted carbazolyl.
[0114] In one embodiment, in Formulas 2 and 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 formula, for example, from 1 to 40 or from 1 to 30.
[0115] In one embodiment, the first compound may include, for example, a compound of Group 1.
[0116] [Group 1]
[0117]
[0118]
[0119]
[0120]
[0121]
[0122]
[0123]
[0124]
[0125] (Dn represents the number of hydrogen atoms replaced by deuterium and represents a structure in which one or more deuterium atoms are substituted). However, as described above, based on natural or artificial substitution, any hydrogen in any compound can be protium, deuterium or tritium.)
[0126] In one embodiment, the second compound can include, for example, a compound of Group 2.
[0127] [Group 2]
[0128]
[0129]
[0130]
[0131]
[0132]
[0133] (Dn represents the number of hydrogen atoms replaced by deuterium and represents a structure in which one or more deuterium atoms are substituted). However, as described above, based on natural or artificial substitution, any hydrogen in any compound can be protium, deuterium or tritium.)
[0134] The composition for an organic optoelectronic device can contain various ratios of the first compound and the second compound.
[0135] In one embodiment, the composition for an organic optoelectronic device can contain a weight ratio of the first compound and the second compound of about 10:90 to about 90:10, such as 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.
[0136] 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, based on the total amount of the first compound and the second compound, the first compound may be included in an amount of about 50 wt% to about 90 wt%.
[0137] In one embodiment, the first compound may be included 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 included in an amount of about 10 wt% to about 50 wt%.
[0138] In addition to the first compound and the second compound, the composition for an organic optoelectronic device may further include a luminescent dopant.
[0139] A luminescent dopant may be a material that is mixed in a small amount with the composition for an organic optoelectronic device 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. The luminescent dopant may be, for example, an inorganic, organic, or organic / inorganic compound, and may include one or two or more types.
[0140] The luminescent dopant may be, for example, a phosphorescent sensitizer, a fluorescent dopant, or a combination thereof.
[0141] The phosphorescent sensitizer may be an organometallic compound and may effectively transfer the energy received from the host to the fluorescent dopant. The phosphorescent sensitizer may increase the energy transfer to the fluorescent dopant, causing the excitons formed in the light-emitting layer to emit light rapidly inside the light-emitting layer, thereby reducing the degradation of the light-emitting diode.
[0142] The phosphorescent sensitizer may be, for example, an organometallic compound including the following: 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 including an organic ligand containing 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.
[0143] The phosphorescent sensitizer may be, for example, one of Compounds P1 to P52.
[0144]
[0145]
[0146]
[0147] The fluorescent dopant may be, for example, a polycyclic compound, and may improve the luminous efficiency and lifetime characteristics of a light-emitting diode by receiving energy transfer due to high absorbance within the light-emitting layer.
[0148] The fluorescent dopant may be, for example, a condensed polycyclic compound containing boron (B), nitrogen (N), or a combination thereof, and may be, for example, one of Compounds D1 to D30.
[0149]
[0150]
[0151] Based on the total amount of the composition for an organic optoelectronic device, the phosphorus photosensitizer and the fluorescent dopant may each be included in an amount of less than or equal to about 20 wt% (for example, 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%).
[0152] For the light-emitting dopant, suitable compounds may be used.
[0153] The composition for an organic optoelectronic device may further include an additive, and the additive may be, for example, an organic material, an inorganic material, an organic / inorganic material, or a combination thereof.
[0154] Hereinafter, an organic optoelectronic device using the above-described composition for an organic optoelectronic device will be described.
[0155] 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.
[0156] 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 include the above-described composition. The organic layer may include an active layer such as a light-emitting layer or a light-absorbing layer, and the above-described composition may be included in the active layer. The organic layer may include a secondary layer between the anode and the active layer or between the cathode and the active layer, and the above-described composition may be included in the secondary layer.
[0157] 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.
[0158] Reference Figure 1 According to one embodiment, the organic light-emitting diode 100 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.
[0159] The anode 110 may be made of a conductor having a high work function to facilitate hole injection, and may be made of 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, or polyaniline.
[0160] The cathode 120 may be made of a conductor having a low work function to facilitate electron injection, and may be made of 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, or BaF2 / Ca.
[0161] The light-emitting layer 130 may contain the above-described composition for an organic optoelectronic device as a host. The light-emitting layer 130 may further contain another organic compound as a host. The light-emitting layer 130 may further contain a light-emitting dopant, and the light-emitting dopant may be 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 blue 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 in the above-described 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 the 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, for example, within about 410 nm to about 480 nm, such as about 420 nm to about 470 nm, or about 430 nm to about 470 nm.
[0162] In one embodiment, the composition for an organic optoelectronic device may include a first compound and a second compound. The first compound may be a compound with relatively strong electron transport characteristics, while the second compound may be a compound with relatively strong hole transport characteristics. Thus, compared with the case of using only the first compound or only the second compound, the light emission efficiency can be improved by increasing the balance of electrons and holes in the light-emitting layer 130, and at the same time, the lifetime can be improved by reducing the unbound charges caused by the imbalance of electron and hole mobilities.
[0163] In one embodiment, in an organic light-emitting diode 100 including a light-emitting layer 130 using the composition for an organic optoelectronic device as a mixed host, the holes and electrons injected from the anode 110 and the cathode 120 can be appropriately distributed within the light-emitting layer 130, the mobility can be finely controlled to an appropriate level, and the generation of excitons within the light-emitting layer 130 can be strongly induced, thereby improving the light emission efficiency of the light-emitting layer 130.
[0164] In one embodiment, it is possible to reduce or prevent the generation of excitons at inappropriate positions (e.g., at 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 the holes and electrons respectively injected from the anode 110 and the cathode 120 within the light-emitting layer 130.
[0165] In one embodiment, it is possible to reduce or prevent the roll-off phenomenon in which the light emission efficiency of the organic light-emitting diode 100 rapidly decreases due to unemitted excitons or unbound charges, thereby ultimately improving the lifetime of the organic light-emitting diode 100.
[0166] The organic light-emitting diode 100 can be manufactured by the following steps: forming the anode 110 or the cathode 120 on a substrate, forming the light-emitting layer using a dry film forming method (e.g., vacuum evaporation, sputtering, plasma plating, or ion plating), and forming the cathode 120 or the anode 110 thereon.
[0167] Figure 2 It is a cross-sectional view showing another embodiment of an organic light-emitting diode which can be an example of an organic optoelectronic device according to another embodiment.
[0168] Reference Figure 2 , similar to the above embodiment, the 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 embodiment, the 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.
[0169] The hole transport layer 140 can be positioned between the anode 110 and the light-emitting layer 130, and the hole transport auxiliary layer 150 can be positioned between the light-emitting layer 130 and the hole transport layer 140. The electron transport layer 160 can be positioned between the cathode 120 and the light-emitting layer 130.
[0170] The hole transport layer 140 can facilitate the 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 or heteroaryl group having hole characteristics. In one embodiment, the amine compound can be represented by Chemical
[0171] Formula 6a or 6b.
[0172]
[0173] In Chemical Formula 6a or 6b, Ar a to Ar g can 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.
[0174] Ar a to Ar c at least one of and Ar d to Ar g at least one of can 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.
[0175] Ar h can 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.
[0176] 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 being 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., at 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 in which the luminous efficiency of the organic light-emitting diode 100 rapidly decreases due to unemitted excitons or unbound charges can be further reduced or prevented, and thus the lifetime of the organic light-emitting diode 100 can be ultimately improved.
[0177] 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.
[0178] The electron transport layer 160 can include, for example, a group 5 compound.
[0179] [Group 5]
[0180]
[0181]
[0182]
[0183] The organic optoelectronic device including the above organic light-emitting diode can be applied to a display device.
[0184] 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 construed as limiting the scope of the embodiments, and these comparative examples should not be construed 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 the examples and comparative examples.
[0185] Hereinafter, unless otherwise specified, the starting materials and reactants used in the examples and synthetic examples are purchased from Sigma-Aldrich Co., Ltd., TCI Inc., Tokyo Chemical Industry, or P&H tech, or are synthesized by known methods.
[0186] Preparation of Compounds for Organic Optoelectronic Devices
[0187] Compounds according to some embodiments are synthesized by the following steps.
[0188] (Synthesis of the First Compound)
[0189] Synthesis Example 1: Synthesis of Compound A-39
[0190] [Reaction Scheme 1]
[0191]
[0192] Using the synthesis method described in Korean Patent No. 10-2054276, Compound A-39 was synthesized using Int-1 (CAS No. 2412580-34-6) and Int-2 (CAS No. 912844-88-3).
[0193] Synthesis Example 2: Synthesis of Compound A-90
[0194] [Reaction Scheme 2]
[0195]
[0196] Using the synthesis method described in Korean Patent No. 10-2154083, Compound A-90 was synthesized using Int-3 (CAS No. 2305718-26-5) and Int-4 (CAS No. 2413799-01-4).
[0197] (Synthesis of the Second Compound)
[0198] Synthesis Example 3: Synthesis of Compound D-72
[0199] [Reaction Scheme 3]
[0200]
[0201] Compound D-72 was synthesized by referring to the synthesis method described in Korean Patent Publication No. 10-2023-0155972.
[0202] Comparative Synthesis Example 1: Synthesis of Compound HT-1
[0203]
[0204] Comparative Compound HT-1 was synthesized by referring to the synthesis method described in Korean Patent Publication No. 10-2023-0037447.
[0205] Manufacture of Organic Light-Emitting Diodes
[0206] Example 1
[0207] The glass substrate coated with an ITO (indium tin oxide) film was ultrasonically washed with distilled water. After washing with distilled water, the glass substrate was ultrasonically washed with isopropyl alcohol, acetone or methanol and dried, then transferred to a plasma cleaner and cleaned with oxygen plasma for 10 minutes, and then transferred 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 (1,3-bis(carbazol-9-yl)benzene) was deposited on the hole transport layer to The thickness is used to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compound A-39 obtained in Synthesis Example 1 and compound D-72 synthesized in Synthesis Example 3 are used as hosts simultaneously, 13 wt% of P31 is doped as a phosphorus photosensitizer, and 1.5 wt% of doped D3 is doped as a fluorescent dopant, and it is formed by vacuum deposition thick light-emitting layer. Herein, compound A-39 and compound D-72 are used in a weight ratio of 4:6. Subsequently, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) is deposited on the light-emitting layer to the thickness to form an electron transport auxiliary layer, and compound B and Liq are vacuum deposited simultaneously in a weight ratio of 1:1 to form thick electron transport layer. An organic light-emitting diode is fabricated by sequentially vacuum depositing of Liq and of Al on the electron transport layer to form a cathode.
[0208] ITO / compound A (doped with 3% NDP-9, ) / compound A / mCP / EML [host (compound A-39:compound D-72):P31:D3 = 85.5 wt%:13 wt%:1.5 wt%] / BCP / compound B:Liq / Liq / Al
[0209] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine
[0210] B: 8-{4-[bis(naphthalen-2-yl)-1,3,5-triazin-2-yl]phenyl}quinoline
[0211]
[0212] Example 2
[0213] An organic light-emitting diode is fabricated in the same manner as in Example 1, except that: compound A-90 obtained in Synthesis Example 2 and compound D-72 obtained in Synthesis Example 3 are used instead of compound A-39 obtained in Synthesis Example 1 and compound D-72 obtained in Synthesis Example 3 as hosts of the light-emitting layer to form the light-emitting layer.
[0214] Comparative Example 1
[0215] An organic light-emitting diode was fabricated in the same manner as in Example 1, except that compound A-39 obtained in Synthesis Example 1 and compound HT-1 obtained in Comparative Synthesis Example 1 were used instead of compound A-39 obtained in Synthesis Example 1 and compound D-72 obtained in Synthesis Example 3 as the host of the light-emitting layer to form the light-emitting layer.
[0216] Evaluation
[0217] The lifetime characteristics of the organic light-emitting diodes according to Example 1 and 2 and Comparative Example 1 were evaluated.
[0218] The lifetime was evaluated by the time when the luminance (cd / m 2 ) was maintained at 2000 cd / m 2 and the current efficiency (cd / A) was reduced to 95%.
[0219] Based on the measured lifetime of the organic light-emitting diode according to Comparative Example 1, the measured lifetimes of the organic light-emitting diodes according to Example 1 and 2 and Comparative Example 1 were calculated as relative values and shown in Table 1.
[0220] Table 1
[0221]
[0222] Referring to Table 1, the lifetime characteristics of the organic light-emitting diodes according to Example 1 and 2 were improved compared to the organic light-emitting diode according to Comparative Example 1.
[0223] By summarizing and reviewing, embodiments of the organic optoelectronic device may include an organic optoelectronic device, an organic light-emitting diode, an organic solar cell, and an organic photoreceptor drum.
[0224] Among them, due to the increasing demand for flat panel display devices, organic light-emitting diodes (OLEDs) have attracted much attention in recent years. An organic light-emitting diode can be a device that converts electrical energy into light, and the performance of the organic light-emitting diode is greatly affected by the organic materials between the electrodes.
[0225] Some embodiments may provide a composition for an organic optoelectronic device that can achieve high efficiency and long lifetime characteristics.
[0226] Some embodiments may provide an organic optoelectronic device including the composition for an organic optoelectronic device.
[0227] Some embodiments may provide a display device including an organic optoelectronic device.
[0228] An organic optoelectronic device with high efficiency and long lifetime can be achieved.
[0229] 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, since the filing of the present application, features, characteristics, and / or elements described in connection with a particular embodiment may be used alone or in combination with features, characteristics, and / or elements described in connection with other embodiments, unless otherwise expressly indicated. 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, X is O or S, Z 1 to Z 3 each independently is N or CR a , Z 1 to Z 3 at least two of which are N, L 1 to L 3 each independently is a single bond, a substituted or unsubstituted C6-C20 arylene group or a substituted or unsubstituted divalent C2-C20 heterocyclic group, Ar 1 and Ar 2 each independently is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heterocyclic group, A is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenyl 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, R 1 to R 3 and R a each 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, and R 1 to R 3 each exist separately or two adjacent connections form a ring [Chemical Formula 2] In Chemical Formula 2, L 7 and L 8 each independently is a single bond or a substituted or unsubstituted C6 to 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: L 1 and L 2 each independently is a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, or a substituted or unsubstituted naphthylene, and L 3 is a single bond.
3. The composition for an organic optoelectronic device according to claim 1, wherein, Ar 1 and Ar 2 each independently is a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted terphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzosilolyl or substituted or unsubstituted dibenzosilolyl.
4. The composition for an organic optoelectronic device according to claim 1, wherein, the first compound is represented by Chemical Formula 1a: [Chemical Formula 1a] In Chemical Formula 1a, X and Y are each independently O or S, Z 1 from Z 3 each independently is N or CR a , Z 1 from Z 3 at least two of which are N, L 1 to L 3 each independently is a single bond, a substituted or unsubstituted C6-C20 arylene group or a substituted or unsubstituted divalent C2-C20 heterocyclic group, Ar 1 is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heterocyclic group, A and A' are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenyl 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, R 1 to R 6 and R a each independently is 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 substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a cyano group or a halogen, R 1 to R 3 each exist separately or two adjacent connections form a ring, and R 4 to R 6 Each exists separately or two adjacent connections form a ring.
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: [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 are defined in the same manner as in Chemical Formula 2.
6. The composition for an organic optoelectronic device according to claim 5, wherein: L 8 is a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene or a substituted or unsubstituted terphenylene, and Ar 7 is a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted terphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzosilolyl, substituted or unsubstituted dibenzosilolyl, or substituted or unsubstituted fluorenyl.
7. The composition for an organic optoelectronic device according to claim 5, wherein Ar 7 , R 30 to R 33 , R 34’ , R 34” , R 34”’ and R 35 to R 42 is at least one of a substituted or unsubstituted carbazolyl group.
8. 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.
9. 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 contains the composition for an organic optoelectronic device according to any one of claims 1 to 8.
10. The organic optoelectronic device according to claim 9, wherein the light-emitting layer further contains a fluorescent dopant, a phosphorescent sensitizer, or a combination thereof.
11. The organic optoelectronic device according to claim 10, wherein the phosphorescent sensitizer is an organometallic compound, and the fluorescent dopant is a condensed polycyclic compound containing boron, nitrogen, or a combination thereof.
12. The organic optoelectronic device according to claim 9, wherein the light-emitting layer emits light in a blue emission spectrum.
13. The organic optoelectronic device according to claim 9, further comprising: a hole transport layer between the anode and the light-emitting layer, and a hole transport auxiliary layer between the light-emitting layer and the hole transport layer.
14. A display device, comprising the organic optoelectronic device according to any one of claims 9 to 13.
Citation Information
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