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

Abstract

The present invention relates to a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. The organic optoelectronic device comprises the composition for an organic optoelectronic device, the composition for an organic optoelectronic device comprising 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. 10-2024-0009468, 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 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 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, while the other can be a light-emitting device that generates light energy from electrical energy by supplying a voltage or current to an electrode. 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, Z 1 to Z 3 are each independently N or CR a , provided that at least two of Z 1 to Z 3 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, one of Ar 1 and Ar 2 is a substituted or unsubstituted carbazolyl group, and the other of Ar 1 and Ar 2 is a substituted or unsubstituted C6 to C30 aryl group, R 1 to R 8 and R aEach 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 8 each exist separately or two adjacent ones are connected to form a ring,

[0010] [Chemical formula 2]

[0011]

[0012] In Chemical formula 2, L 7 and L 8 each independently is 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.

[0013] 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 the embodiment.

[0014] An embodiment can be realized by providing a display device including the organic optoelectronic device according to the embodiment. Description of the Drawings

[0015] By describing exemplary embodiments in detail with reference to the drawings, these features will become clear to those skilled in the art, wherein:

[0016] 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

[0017] Figure 2 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

[0018] 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.

[0019] 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. Further, 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. Additionally, it should be understood that when a layer is referred to as being “between” two layers, it can be the only layer between the two layers, or one or more intermediate layers may also be present. Like reference numerals always indicate like elements. As used herein, the term “or” is not an exclusive term, e.g., “A or B” will include A, B, or A and B.

[0020] As used herein, when no definition is otherwise provided, “substituted” means 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, 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.

[0021] In some embodiments, “substituted” means 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 some embodiments, “substituted” means 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 some embodiments, “substituted” means 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 some embodiments, “substituted” means 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.

[0022] “Unsubstituted” means that a hydrogen atom is not replaced by another substituent and retains that hydrogen atom.

[0023] 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).

[0024] 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.

[0025] As used herein, "aryl" means a group including at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have conjugated p-orbitals formed, such as phenyl, naphthyl, etc. Two or more hydrocarbon aromatic moieties may be connected by a σ bond and may be, for example, biphenyl, terphenyl, quaterphenyl, etc., and two or more hydrocarbon aromatic moieties may be directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl.

[0026] Aryl may include monocyclic, polycyclic, or fused polycyclic (i.e., rings sharing adjacent carbon atom pairs) functional groups.

[0027] 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 replacing a carbon (C) in a cyclic compound (e.g., aryl, cycloalkyl, 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 contain one or more heteroatoms.

[0028] In one embodiment, "heteroaryl" may refer to an aryl 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 includes two or more rings, the two or more rings may be fused. If the heteroaryl is a fused ring, each ring may include 1 to 3 heteroatoms.

[0029] In one embodiment, the substituted or unsubstituted C6-C30 aryl may be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fused tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted group, substituted or unsubstituted dianthryl, substituted or unsubstituted perylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indenyl, or a combination thereof.

[0030] 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 or a substituted or unsubstituted dibenzothienyl group or a combination thereof.

[0031] As used herein, hole characteristics 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 in the light-emitting layer.

[0032] In addition, electron characteristics 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 in the light-emitting layer.

[0033] Hereinafter, compositions for organic optoelectronic devices according to some embodiments will be described.

[0034] The composition for an organic optoelectronic device according to some embodiments may include, for example, a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2.

[0035] [Chemical Formula 1]

[0036]

[0037] In Chemical Formula 1, Z 1 to Z 3 may each independently be, for example, N or CR a .

[0038] In one embodiment, Z 1 to Z 3At least two of them can be, for example, N.

[0039] L 1 to L 3 can each independently be or include, for example, a single bond, a substituted or unsubstituted C6 - C20 arylene, or a substituted or unsubstituted divalent C2 - C20 heterocyclic group.

[0040] Ar 1 and Ar 2 one of them can be or contain, for example, a substituted or unsubstituted carbazolyl group.

[0041] Ar 1 and Ar 2 the other one can be or contain, for example, a substituted or unsubstituted C6 - C30 aryl group.

[0042] R 1 to R 8 and R a can 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 substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a cyano group, or a halogen.

[0043] R 1 to R 8 can each exist separately or two adjacent ones can be connected to form a ring.

[0044] [Chemical formula 2]

[0045]

[0046] 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 - C30 arylene.

[0047] Ar 7 can be or include, for example, a substituted or unsubstituted C6 - C30 aryl group or a substituted or unsubstituted C2 - C30 heterocyclic group.

[0048] 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, 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.

[0049] The first compound and the second compound may be bipolar compounds each having both electron transport characteristics and hole transport characteristics. The first compound may be a bipolar compound having relatively strong electron transport characteristics, while the second compound may be a bipolar compound having relatively strong hole transport characteristics. In one embodiment, the first compound and the second compound may exhibit good interfacial characteristics due to their structures.

[0050] The composition for an organic optoelectronic device may contain 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., the light-emitting layer) of the organic optoelectronic device.

[0051] 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 described later, 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, 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.

[0052] In one embodiment, in Chemical Formula 1, Z 1 to Z 3 may each be N.

[0053] In one embodiment, in Chemical Formula 1, Z 1 and Z 2 may each be N and Z 3 may be CR a .

[0054] In one embodiment, in Chemical Formula 1, Z 1 and Z 3 may each be N and Z 2 may be CR a .

[0055] In one embodiment, in Chemical Formula 1, Z 2 and Z 3 may each be N and Z 1 may be CR a .

[0056] 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, or a substituted or unsubstituted naphthylene, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted dibenzothienyl, or a substituted or unsubstituted fluorenyl.

[0057] 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 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.

[0058] In one embodiment, in Chemical Formula 1, Ar 1 can be, for example, a substituted or unsubstituted C6 - C30 aryl, and Ar 2 can be a substituted or unsubstituted carbazolyl. In one embodiment, Ar 1 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, or a substituted or unsubstituted terryphenyl.

[0059] In one embodiment, in Chemical Formula 1, if Ar 2 is a substituted or unsubstituted carbazolyl, then L 2 and L 3 can be different from each other. In one embodiment, one of L 2 and L 3 can be, for example, a single bond, and the other of L 2 and L 3 can be, for example, a substituted or unsubstituted C6 - C20 arylene, such as a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, or a substituted or unsubstituted naphthylene.

[0060] In one embodiment, in Chemical Formula 1, Ra 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.

[0061] The first compound may be represented, for example, by Chemical Formula 1a.

[0062] [Chemical Formula 1a]

[0063]

[0064] In Chemical Formula 1a, Z 1 to Z 3 , L 1 to L 3 and R 1 to R 8 may be defined the same as those in Chemical Formula 1.

[0065] Ar 1 may be, for example, a substituted or unsubstituted C6 - C30 aryl group, such as 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, or a substituted or unsubstituted terphenylene group.

[0066] R 9 to R 16 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 substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a cyano group, or a halogen, and R 9 to R 16 may each exist separately or two adjacent ones may be connected to form a ring.

[0067] In one embodiment, in Chemical Formula 1a, L 2 and L 3 may be different from each other. For example, L 2 may be 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 may be a single bond.

[0068] In one embodiment, at least one of each substituent in Chemical Formulas 1 and 1a 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.

[0069] In one embodiment, the second compound may be represented by one of Chemical Formulas 2a to 2d.

[0070] [Chemical Formula 2a]

[0071]

[0072] [Chemical Formula 2b]

[0073]

[0074] [Chemical Formula 2c]

[0075]

[0076] [Chemical Formula 2d]

[0077]

[0078] 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 defined the same as those in Chemical Formula 2.

[0079] 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.

[0080] 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.

[0081] 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 42Each may independently be, for example, hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzosilole group, a substituted or unsubstituted dibenzosilole group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted silyl group or a cyano group.

[0082] In one embodiment, 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.

[0083] 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.

[0084] In one embodiment, the first compound may include, for example, a compound of Group 1.

[0085] [Group 1]

[0086]

[0087]

[0088]

[0089]

[0090] (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 may be protium, deuterium or tritium.

[0091] In one embodiment, the second compound may include, for example, a compound of Group 2.

[0092] [Group 2]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099] (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, any hydrogen in any compound can be protium, deuterium or tritium based on natural or artificial substitution.

[0100] The composition for an organic optoelectronic device may contain various ratios of a first compound and a second compound.

[0101] In one embodiment, the composition for an organic optoelectronic device may contain a weight ratio 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 of the first compound and the second compound.

[0102] 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%.

[0103] 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%.

[0104] In addition to the first compound and the second compound, the composition for an organic optoelectronic device may further contain, for example, a light-emitting dopant.

[0105] A light-emitting dopant is 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 emits light by being excited to a triplet state or more states multiple times. The light-emitting dopant may be, for example, an inorganic, organic or organic / inorganic compound, and may contain one or two or more types.

[0106] The light-emitting dopant may be, for example, a phosphorescent sensitizer, a fluorescent dopant, or a combination thereof.

[0107] 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.

[0108] The phosphorescent sensitizer can 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 can be, for example, an organometallic compound including an organic ligand containing a nitrogen-containing ring. The nitrogen-containing ring can 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.

[0109] The phosphorescent sensitizer can be, for example, one of Compounds P1 to P52.

[0110]

[0111]

[0112]

[0113] The fluorescent dopant can be, for example, a polycyclic compound and can improve the luminous efficiency and lifetime characteristics of the light-emitting diode by receiving energy transfer due to high absorbance within the light-emitting layer.

[0114] 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.

[0115]

[0116]

[0117]

[0118] Based on the total amount of the composition for an organic optoelectronic device, a phosphorescent photosensitizer and a fluorescent dopant can each be included in an amount less than or equal to about 20 wt% (such as 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%).

[0119] For the luminescent dopant, suitable compounds can be used.

[0120] The composition for an organic optoelectronic device can further include an additive, and the additive can be, for example, an organic material, an inorganic material, an organic / inorganic material, or a combination thereof.

[0121] Hereinafter, an organic optoelectronic device using the above composition for an organic optoelectronic device will be described.

[0122] The organic optoelectronic device can be, for example, an organic light-emitting diode, an organic optoelectronic device, or an organic solar cell. In one embodiment, the organic optoelectronic device can be an organic light-emitting diode.

[0123] The organic optoelectronic device can include an anode and a cathode facing each other, and an organic layer between the anode and the cathode, and the organic layer can include the above composition. The organic layer can include an active layer, such as a light-emitting layer or a light-absorbing layer, and the above composition can be included in the active layer. The organic layer can include a auxiliary layer between the anode and the active layer or between the cathode and the active layer, and the above composition can be included in the auxiliary layer.

[0124] Figure 1 is a cross-sectional view showing an example of an organic light-emitting diode that can be an example of an organic optoelectronic device according to one embodiment.

[0125] Reference Figure 1 , an organic light-emitting diode 100 according to one embodiment can 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.

[0126] The anode 110 can be made of a conductor having a high work function to facilitate hole injection, and can be made of, for example, a metal, a metal oxide, or a conductive polymer. The anode 110 can 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; or a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylenedioxy))thiophene) (PEDOT), polypyrrole, and polyaniline.

[0127] The cathode 120 can be made of a conductor having a low work function to facilitate electron injection, and can be made of, for example, a metal, a metal oxide, or a conductive polymer. The cathode 120 can 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.

[0128] The light-emitting layer 130 can contain the above-described composition for an organic optoelectronic device as a host. The light-emitting layer 130 can also contain another organic compound as a host. The light-emitting layer 130 can further contain the above-described light-emitting dopant and can contain 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 can emit light in a blue emission spectrum. At least one of the above-described first and second compounds in the composition for an organic optoelectronic device can have a high triplet energy level greater than or equal to about 2.8 eV, such that exciton transfer to the blue light-emitting dopant can be easy, and thus an organic optoelectronic device with high efficiency and long lifetime can be achieved. The peak wavelength of the blue emission spectrum can 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.

[0129] In one embodiment, the above-described composition for an organic optoelectronic device can contain a first compound and a second compound. The first compound can be a bipolar compound having relatively strong electron-transporting properties, while the second compound can be a compound having relatively strong hole-transporting properties. Thus, compared with the case of using the first compound alone or the second compound alone, the light-emitting 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.

[0130] In one embodiment, in an organic light-emitting diode 100 including a light-emitting layer 130 using a composition for an organic optoelectronic device as a host, holes and electrons injected from an anode 110 and a 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-emitting efficiency of the light-emitting layer 130.

[0131] 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 mobility of holes and electrons respectively injected from the anode 110 and the cathode 120 within the light-emitting layer 130.

[0132] In one embodiment, it is possible to reduce or prevent 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, thereby ultimately improving the lifespan of the organic light-emitting diode 100.

[0133] The organic light-emitting diode 100 can be manufactured through the following steps: forming the anode 110 or the cathode 120 on a substrate, forming the light-emitting layer using a dry film formation method (e.g., vacuum evaporation, sputtering, plasma plating, and ion plating), and forming the cathode 120 or the anode 110 thereon.

[0134] Figure 2 FIG. is a cross-sectional view showing another embodiment of an organic light-emitting diode that can be an example of an organic optoelectronic device according to another embodiment.

[0135] 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.

[0136] The hole transport layer 140 may be positioned between the anode 110 and the light-emitting layer 130, and the hole transport assisting layer 150 may be positioned between the light-emitting layer 130 and the hole transport layer 140. The electron transport layer 160 may be positioned between the cathode 120 and the light-emitting layer 130.

[0137] The hole transport layer 140 can facilitate hole transfer 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

[0138] Formula 6a or 6b.

[0139]

[0140] 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-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, or a combination thereof.

[0141] 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-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, or a combination thereof.

[0142] Ar h can be, for example, 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.

[0143] The hole transport auxiliary layer 150 can form an interface with the light-emitting layer 130 by being positioned between the hole transport layer 140 and the light-emitting layer 130 and in contact with the light-emitting layer 130. The hole transport auxiliary layer 150 can 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 an adjacent layer) or the accumulation of unbound charges at the interface between the light-emitting layer 130 and an 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.

[0144] 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.

[0145] The electron transport layer 160 can include, for example, a Group 5 compound.

[0146] [Group 5]

[0147]

[0148]

[0149]

[0150]

[0151] An organic optoelectronic device including the above organic light-emitting diode can be applied to a display device.

[0152] 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.

[0153] Hereinafter, unless otherwise specified, 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&H tech, or are synthesized by known methods.

[0154] Preparation of Compounds for Organic Optoelectronic Devices

[0155] The compound was synthesized through the following steps.

[0156] (Synthesis of the First Compound)

[0157] Synthesis Example 1: Synthesis of Compound A-54

[0158] [Reaction Scheme 1]

[0159]

[0160] First Step: Synthesis of Compound A-19

[0161] Compound A-19 was synthesized using Intermediate I-A-19-1 (CAS No. 292056-52-4), and 2-(dibenzofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was prepared by referring to the synthesis method described in Korean Patent Publication No. 10-2023-0037447.

[0162] Second Step: Synthesis of Compound A-54

[0163] Compound A-19, trifluoromethanesulfonic acid, and benzene-D6 were added and stirred for 24 hours. Purified water was added and neutralized with a saturated K3PO4 solution. The organic layer was concentrated and purified by column chromatography to synthesize compound A-54.

[0164] Synthesis Example 2: Synthesis of Compound A-55

[0165] [Reaction Formula 2]

[0166]

[0167] First Step: Synthesis of Compound A-20

[0168] By referring to the synthesis method described in Korean Patent Publication No. 10-2023-0037447, compound A-20 was synthesized using intermediate I-A-19-1 (CAS No. 292056-52-4) and 2-(dibenzofuran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

[0169] Second Step: Synthesis of Compound A-55

[0170] Compound A-20, trifluoromethanesulfonic acid, and benzene-D6 were added and stirred for 24 hours. Purified water was added and neutralized with a saturated K3PO4 solution. The organic layer was concentrated and purified by column chromatography to synthesize compound A-55.

[0171] (Synthesis of the Second Compound)

[0172] Synthesis Example 3: Synthesis of Compound D-72

[0173] [Reaction Formula 3]

[0174]

[0175] Compound D-72 was synthesized by referring to the synthesis method described in Korean Patent Publication No. 10-2023-0155972.

[0176] Comparative Synthesis Example 1: Synthesis of Compound HT-1

[0177]

[0178] Comparative compound HT-1 was synthesized by referring to the synthesis method described in Korean Patent Publication No. 10-2023-0037447.

[0179] Manufacture of Organic Light-Emitting Diodes

[0180] Example 1

[0181] The glass substrate coated with an ITO (indium tin oxide) thin film is ultrasonically washed with distilled water. After washing with distilled water, the glass substrate is ultrasonically washed with isopropyl alcohol, acetone or methanol and dried, then moved to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and moved to a vacuum depositor. The prepared ITO transparent electrode is used as the anode, and compound A (Novaled GmbH) doped with 3% NDP-9 is vacuum deposited on the ITO substrate to form a thick hole injection layer, and compound A is deposited on the hole injection layer to a thickness to form a hole transport layer. mCP (1,3-bis(carbazol-9-yl)benzene) is deposited on the hole transport layer to a thickness to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compound A-54 obtained in Synthesis Example 1 and compound D-72 synthesized in Synthesis Example 3 are used as hosts simultaneously, doped with 13 wt% of P31 as a phosphorus photosensitizer, and doped with 1.5 wt% of D3 as a fluorescent dopant, and formed by vacuum deposition a thick light-emitting layer. Here, compound A-54 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 a 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 a thick electron transport layer. By sequentially vacuum depositing of Liq and of Al on the electron transport layer to form a cathode to fabricate an organic light-emitting diode.

[0182] ITO / compound A (doped with 3% NDP-9, ) / compound A / mCP / EML [host (compound A-54:compound D-72):P31:D3 = 85.5 wt%:13 wt%:1.5 wt%] / BCP / compound B:Liq / Liq / Al

[0183]

[0184] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine Compound B: 8-{4-[bis(naphthalen-2-yl)-1,3,5-triazin-2-yl]phenyl}quinoline

[0185]

[0186] Example 2

[0187] An organic light-emitting diode was fabricated in the same manner as in Example 1, except that compound A-55 obtained in Synthesis Example 2 and compound D-72 obtained in Synthesis Example 3 were used instead of compound A-54 obtained in Synthesis Example 1 and compound D-72 synthesized in Synthesis Example 3 as the host of the light-emitting layer to form the light-emitting layer.

[0188] Comparative Example 1

[0189] An organic light-emitting diode was fabricated in the same manner as in Example 1, except that compound A-54 obtained in Synthesis Example 1 and compound HT-1 obtained in Comparative Synthesis Example 1 were used instead of compound A-54 obtained in Synthesis Example 1 and compound D-72 synthesized in Synthesis Example 3 as the host of the light-emitting layer to form the light-emitting layer.

[0190] Evaluation

[0191] The luminous efficiency and lifetime characteristics of the organic light-emitting diodes according to Example 1 and 2 and Comparative Example 1 were evaluated.

[0192] The specific measurement methods are as follows, and the results are shown in Table 1.

[0193] (1) Measuring the change in current density according to voltage change

[0194] 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.

[0195] (2) Measuring the change in luminance according to voltage change

[0196] While increasing the voltage of the organic light-emitting diode from 0 V to 10 V, the luminance was measured using a luminance meter (Minolta Cs-1000A).

[0197] (3) Measurement of luminous efficiency

[0198] By using the luminance, current density, and voltage from the above (1) and (2), the current efficiency (cd / A) at the same current density (10 mA / cm 2 ) was calculated.

[0199] The luminous efficiency values of Example 1 and 2 and Comparative Example 1 were calculated as relative values based on Comparative Example 1 and are shown in Table 1.

[0200] (4) Measurement of Lifetime

[0201] By maintaining the luminance (cd / m 2 ) at 2,000 cd / m 2 and measuring the time when the current efficiency (cd / A) decreases to 95%, the result is obtained.

[0202] The measured lifetimes of the organic light-emitting diodes according to Examples 1 and 2 and Comparative Example 1 were calculated as relative values based on Comparative Example 1 and are shown in Table 1.

[0203] Table 1

[0204]

[0205] Referring to Table 1, the organic light-emitting diodes according to Examples 1 and 2 exhibited improved luminous efficiency and lifetime characteristics compared to the organic light-emitting diode according to Comparative Example 1.

[0206] By summary and review, embodiments of the organic optoelectronic device may include an organic optoelectronic device, an organic light-emitting diode, an organic solar cell, or an organic photoconductive drum.

[0207] 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 an organic light-emitting diode can be greatly affected by the organic materials between the electrodes.

[0208] Some embodiments can provide a composition for an organic optoelectronic device that can achieve high efficiency and long lifetime characteristics.

[0209] Some embodiments can provide an organic optoelectronic device including the composition for an organic optoelectronic device.

[0210] Some embodiments can provide a display device including the organic optoelectronic device.

[0211] An organic optoelectronic device with high efficiency and long lifetime can be achieved.

[0212] 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 of ordinary skill 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, Z 1 to Z 3 each independently is N or CR a provided that 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 one of which is a substituted or unsubstituted carbazolyl group, Ar 1 and Ar 2 Another one of them is a substituted or unsubstituted C6-C30 aryl group, R 1 to R 8 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, and R 1 to R 8 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-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 atom.

2. The composition for an organic optoelectronic device according to claim 1, wherein: L 1 and L 2 each independently is a single bond or a substituted or unsubstituted C6 to C20 arylene group, and L 3 is a single bond.

3. 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, Z 1 To Z 3 , L 1 To L 3 and R 1 To R 8 The definition of is the same as that in Chemical Formula 1, Ar 1 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl or substituted or unsubstituted triphenylene, R 9 to R 16 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 9 to R 16 Each separately exists or two adjacent connections form a ring.

4. The composition for an organic optoelectronic device according to claim 3, wherein: L 2 is a substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene or substituted or unsubstituted naphthylene, and L 3 is a single bond.

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 the same 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 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 benzothienyl group, a substituted or unsubstituted dibenzothienyl 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 5, wherein Ar 7 and R 30 to R 42 at least one of which is a substituted or unsubstituted carbazolyl group.

8. The composition for an organic optoelectronic device according to claim 1, wherein, at least one of the first compound represented by Chemical Formula 1 and the second compound represented by Chemical Formula 2 is substituted with at least one deuterium.

9. 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.

10. 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 to 9.

11. The organic optoelectronic device according to claim 10, wherein the light-emitting layer further comprises a fluorescent dopant, a phosphorescent sensitizer, or a combination thereof.

12. The organic optoelectronic device according to claim 11, wherein the phosphorescent sensitizer is an organometallic compound, and the fluorescent dopant is a condensed polycyclic compound comprising boron, nitrogen, or a combination thereof.

13. The organic optoelectronic device according to claim 10, wherein the light-emitting layer emits light in a blue emission spectrum.

14. The organic optoelectronic device according to claim 10, 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.

15. A display device, comprising the organic optoelectronic device according to any one of claims 10 to 14.

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