Compound, composition, organic optoelectronic device, and display device

Abstract

The invention relates to a compound, a composition, an organic optoelectronic device, and a display device. The compound is represented by Chemical Formula 1, where X1 and X2 are each independently NRa, O, S, Se, or Te, any one of R1 to R10 is a group represented by Chemical Formula A, the remaining ones of R1 to R10 and Ra are each independently 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 amine group, a substituted or unsubstituted silyl group, a cyano group, or a halogen, and R1 to R10 and Ra are each independently present, or adjacent two of R1 to R10 and Ra are linked to form a ring.

Description

[0001] Citations of relevant applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0064779, filed with the Korean Intellectual Property Office on May 17, 2024, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This invention discloses compounds, compositions, organic optoelectronic devices, and display devices. Background Technology

[0004] Organic optoelectronic devices (such as organic photodiodes) are devices capable of converting electrical energy and light energy into each other. Based on their working principles, organic optoelectronic devices can be mainly divided into two types. One type of optoelectronic device generates electrical energy by separating excitons formed from light energy into electrons and holes, and then transferring these electrons and holes to different electrodes. The other type of optoelectronic device generates light energy from electrical energy by supplying voltage or current to electrodes.

[0005] Examples of organic optoelectronic devices include organic photoelectric devices, organic light-emitting diodes (OLEDs), organic solar cells, and organic photoconductor drums. Among these, organic light-emitting diodes (OLEDs) have received considerable attention in recent years due to the increasing demand for flat panel displays. OLEDs are devices that convert electrical energy into light, and their performance is greatly influenced by the organic materials between the electrodes. Summary of the Invention

[0006] According to some exemplary embodiments, compounds represented by chemical formula 1 are provided.

[0007] [Chemical Formula 1]

[0008]

[0009] In chemical formula 1, X 1 and X 2 Each is an independent NR a ,O,S,Se or Te,R 1 To R 10 Any one of them is a group represented by the chemical formula A, R 1 To R 10 The remaining ones and R a Each of these elements is independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted silyl, cyano, or halogen, and R 1 To R 10 and R aEach exists independently, or R 1 To R 10 and R a Two adjacent connections in the middle form a loop.

[0010] [Chemical Formula A]

[0011]

[0012] In chemical formula A, R 11 To R 18 Each of the following is independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted silyl, cyano, or halogen, provided that R 11 To R 18 Any one of them is a substituted or unsubstituted carbazole group, R 11 To R 18 Each exists independently, or R 11 To R 18 Two adjacent connections in the middle form a loop, and * is the connection point with chemical formula 1.

[0013] According to some exemplary embodiments, a composition for an organic optoelectronic device comprises a first compound and a second compound, wherein the first compound is said compound and the second compound is represented by chemical formula 2.

[0014] [Chemical Formula 2]

[0015]

[0016] In chemical formula 2, Z 1 To Z 6 Each is independently N or CL a- R e Z 1 To Z 6 At least two of them are N and L. a Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene, a substituted or unsubstituted divalent C2 to C20 heterocyclic group, or a combination thereof, R e Each of these elements is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a halogen, a cyano group, or a combination thereof, and R e Each exists independently, or R e Two adjacent links in the middle form substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic rings.

[0017] According to some exemplary embodiments, an organic optoelectronic device includes 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 compound or composition for the organic optoelectronic device.

[0018] According to some exemplary embodiments, a display device including an organic optoelectronic device is provided. Attached Figure Description

[0019] These features will become clear to those skilled in the art from a detailed description of exemplary embodiments with reference to the accompanying drawings, wherein:

[0020] Figure 1 This is a cross-sectional view showing an embodiment of an organic light-emitting diode according to some implementation schemes, and

[0021] Figure 2 This is a cross-sectional view showing another embodiment of an organic light-emitting diode according to some implementation schemes. Detailed Implementation

[0022] Exemplary embodiments will now be described more fully below with reference to the accompanying drawings; however, they may be embodied in different forms and should not be construed as being 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 practices to those skilled in the art.

[0023] In the accompanying drawings, the dimensions of layers and regions may be exaggerated for clarity. It should also be understood that when a layer or element is referred to as "on" another layer or substrate, it may be directly on that layer or substrate, or there may be intermediate layers. Furthermore, it should be understood that when a layer is referred to as "between" two layers, it may be the only layer between the two layers, or there may be one or more intermediate layers. The same reference numerals always denote the same elements.

[0024] As used herein, unless otherwise defined, “substituted” means that at least one hydrogen atom of a substituent or compound is replaced by a group consisting of: deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amino, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or combinations thereof.

[0025] In one embodiment of the implementation, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by a group consisting of: deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, or cyano. For example, "substituted" may mean that at least one hydrogen atom of the substituent or compound is replaced by a group consisting of: deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. For example, "substituted" may mean that at least one hydrogen atom of the substituent or compound is replaced by a group consisting of: deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. For example, "substituted" may mean that at least one hydrogen atom of the substituent or compound is replaced by a group consisting of: deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0026] "Unsubstituted" means that the hydrogen atom is not replaced by another substituent and the hydrogen atom is retained.

[0027] In this specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)".

[0028] As used herein, unless otherwise defined, “heterogeneous” means a functional group comprising one to three heteroatoms selected from N, O, S, P and Si, and the remaining carbon.

[0029] As used herein, “aryl” means a group comprising at least one aromatic hydrocarbon moiety, wherein all elements of the aromatic hydrocarbon moiety have conjugated p orbitals, such as phenyl, naphthyl, etc., and two or more aromatic hydrocarbon moiety moiety may be linked by σ bonds and may be, for example, biphenyl, terphenyl, tetraphenyl, etc., and two or more aromatic hydrocarbon moiety moiety may be fused directly or indirectly to provide a non-aromatic fused ring, such as fluorene.

[0030] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent carbon atom pairs) functional groups.

[0031] As used herein, "heterocyclic group" is a superordinate concept of a heteroaryl group and may include at least one heteroatom selected from N, O, S, P, and Si replacing a carbon (C) in a cyclic compound (such as an aryl, cycloalkyl, its fused ring, or a combination thereof). When the heterocyclic group is fused, the entire ring or each ring of the heterocyclic group may contain one or more heteroatoms.

[0032] As an example, "heteroaryl" can refer to an aryl group comprising at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly connected by σ bonds, or when the heteroaryl group comprises two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may comprise 1 to 3 heteroatoms.

[0033] More specifically, the substituted or unsubstituted C6 to C30 aryl group can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted tetraphenyl, a substituted or unsubstituted pyrene, a substituted or unsubstituted biphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted o-terphenyl, or a substituted or unsubstituted phenyl group. The radical, substituted or unsubstituted triphenylene, substituted or unsubstituted perylene, substituted or unsubstituted fluorene, substituted or unsubstituted indole, or combinations thereof, but not limited thereto.

[0034] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group can be a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted pyrrole 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 benzofuranyl group, or a substituted or unsubstituted benzothiopheneyl group. The following are substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or combinations thereof, but not limited thereto.

[0035] As used herein, hole characteristics refer to the ability to contribute electrons to form holes when an electric field is applied, and holes formed in the anode can be readily injected into and transported in the emissive layer due to the conductivity of the highest occupied molecular orbital (HOMO) energy level.

[0036] Furthermore, electronic properties refer to the ability to receive electrons when an electric field is applied, and due to the conductivity of the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into and transported in the light-emitting layer.

[0037] The following describes compounds according to some exemplary embodiments.

[0038] The compounds according to some exemplary embodiments are represented by chemical formula 1.

[0039] [Chemical Formula 1]

[0040]

[0041] In chemical formula 1, X 1 and X 2 They can be NR independently. a ,O,S,Se or Te,R 1 To R 10 Any one of them can be a group represented by the chemical formula A, R 1 To R 10 The remaining ones and R a Each of these can be independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted silyl, cyano, or halogen, and R 1 To R 10 and R a They can exist independently, or R 1 To R 10 and R a Two adjacent elements can be connected to form a loop.

[0042] [Chemical Formula A]

[0043]

[0044] In chemical formula A, R 11 To R 18 Each of these can be independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted silyl, cyano, or halogen, provided that R 11 To R 18 Each of the groups can be a substituted or unsubstituted carbazole group, R 11 To R 18 They can exist independently, or R 11 To R 18Two adjacent elements can be connected to form a ring, and * is the connection point with chemical formula 1.

[0045] This compound comprises a fused ring consisting of multiple five-membered rings containing heteroatoms and multiple benzene rings, and also contains substituted or unsubstituted biscarbazoyl groups as substituents for the benzene rings of this fused ring, thereby increasing the HOMO energy level, increasing electron delocalization, and enhancing molecular stability. Therefore, this compound can be used in organic optoelectronic devices (such as organic light-emitting diodes), and can exhibit improved lifetime characteristics in organic optoelectronic devices while increasing hole mobility and reducing operating voltage.

[0046] For example, X in chemical formula 1 1 and X 2 They can be the same.

[0047] For example, X in chemical formula 1 1 and X 2 They can be different from each other. For example, X 1 and X 2 One of them could be NR a And X 1 and X 2 The other one can be O, S, Se, or Te. For example, X 1 and X 2 One of them can be O or S, and X 1 and X 2 The other one can be Se or Te. For example, X 1 and X 2 One of them can be O, and X 1 and X 2 The other one can be S. For example, X 1 and X 2 Each can have NR a However, R a They can be different from each other.

[0048] For example, X in chemical formula 1 1 and X 2 At least one of them can be NR a , where R aEach of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzoselenyl, substituted or unsubstituted dibenzoselenyl, substituted or unsubstituted benzothiophene, or substituted or unsubstituted dibenzothiophene.

[0049] For example, R in chemical formula 1 1 To R 4 and R 7 To R 10 Any one of them can be a group represented by the chemical formula A.

[0050] For example, R of chemical formula A 11 To R 18 Any one of them can be a group represented by the chemical formula Aa.

[0051] [Chemical formula Aa]

[0052]

[0053] In the chemical formula Aa, R 19 To R 26 Each of these can be independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted silyl, cyano, or halogen, R 19 To R 26 They can exist independently, or R 11 To R 18 Two adjacent elements can be connected to form a ring, and * is the connection point with chemical formula A.

[0054] For example, R in the chemical formula Aa 19 To R 26 At least one of them can be deuterium. For example, R of chemical formula Aa 19 To R 26 At least two of them can be deuterium, R of chemical formula Aa 19 To R 26 At least four of them can be deuterium, R of chemical formula Aa 19 To R 26 At least six of them can be deuterium, and the R of the chemical formula Aa 19 To R 26 Each of them can be deuterium.

[0055] For example, chemical formula A can be represented by the following chemical formula A-1.

[0056] [Chemical Formula A-1]

[0057]

[0058] In chemical formula A-1, R 11 To R 15 and R 17 To R 26 Each of these can be independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted silyl, cyano, or halogen, R 11 To R 15 and R 17 To R 26 They can exist independently, or R 11 To R 15 and R 17 To R 26 Two adjacent elements can be connected to form a ring, and * is the connection point with chemical formula 1.

[0059] For example, a compound can be substituted with at least one deuterium atom, such as R in chemical formula 1 or chemical formula A. 1 To R 18 At least one of them can be deuterium, and R of, for example, chemical formula 1, chemical formula A, or chemical formula Aa. 1 To R 18 and R 19 To R 26 At least one of them can be deuterium.

[0060] For example, R 19 To R 22 Each can be deuterium.

[0061] For example, R 19 To R 26 Each can be deuterium.

[0062] For example, besides the group represented by the chemical formula Aa, R 11 To R 18 Each of them can be deuterium.

[0063] For example, besides the group represented by the chemical formula Aa, R 11 To R 26 Each of them can be deuterium.

[0064] For example, in addition to the group represented by the chemical formula A, R 1To R 10 Each of them can be deuterium.

[0065] For example, each substituent in Formula 1 can be deuterium or be substituted with deuterium.

[0066] For example, the compound may be selected from the compounds listed in Group 1 below.

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109] The above compounds can be used together with other compounds as compositions to exhibit synergistic effects in improving the performance of organic optoelectronic devices such as organic light-emitting diodes.

[0110] A composition for an organic optoelectronic device according to some exemplary embodiments may include the above-described compound (first compound) and a second compound different from the first compound. The second compound may include a substituted or unsubstituted nitrogen-containing six-membered ring moiety and may be represented, for example, by chemical formula 2.

[0111] [Chemical Formula 2]

[0112]

[0113] In chemical formula 2, Z 1 To Z 6 Each can be N or CL independently. a -R e Z 1 To Z 6 At least two of them can be N, L a Each of these can be a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted divalent C2 to C20 heterocyclic group, or a combination thereof, R. e Each of these can be independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof, and R. e They can exist independently, or R e Two adjacent rings can connect to form substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic rings.

[0114] The first and second compounds can be bipolar compounds possessing both electronic and hole properties, respectively. The first compound can be a bipolar compound with relatively strong hole properties, and the second compound can be a bipolar compound with relatively strong electronic properties. Furthermore, the first and second compounds can exhibit good interfacial properties due to their structures.

[0115] The composition for organic optoelectronic devices comprises a first compound and a second compound together to finely control the mobility of holes and electrons, thereby balancing holes and electrons in the active layer (e.g., the light-emitting layer) of the organic optoelectronic device.

[0116] Furthermore, the composition for organic optoelectronic devices can be used as a host for the light-emitting layer and has good electrical matching with the 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 its degradation. As an example, at least one of the first and second compounds has a high triplet energy level greater than or equal to about 2.8 eV, which facilitates exciton transfer to the blue light-emitting dopant, thereby realizing an organic optoelectronic device with high efficiency and long lifetime.

[0117] For example, in chemical formula 2, Z 1 To Z 6 Two of them can be nitrogen (N), and the rest can be CL. a -Re .

[0118] For example, in chemical formula 2, Z 1 and Z 3 It can be nitrogen, Z 2 It can be N or CL a -R e Z 4 It can be N or CL a -R e Z 5 It can be N or CL a -R e , and Z 6 It can be N or CL a -R e .

[0119] For example, in chemical formula 2, Z 1 To Z 6 Three of them can be nitrogen (N) and the rest can be CL. a -R e .

[0120] For example, in chemical formula 2, Z 1 Z 3 and Z 5 It can be nitrogen, Z 2 It can be N or CL a -R e Z 4 It can be N or CL a -R e And Z 6 It can be N or CL a -R e .

[0121] For example, depending on R e The substituents, the second compound represented by chemical formula 2, can be represented by any one of chemical formulas 2A to 2C.

[0122] [Chemical Formula 2A][Chemical Formula 2B]

[0123]

[0124] [Chemical formula 2C]

[0125]

[0126] In chemical formulas 2A to 2C, Z 1 Z 3 and Z 5 Each can be N or CL independently. a -R eZ 1 Z 3 and Z 5 At least two of them can be N, X 2 It can be O, S, or NR. f L a and L 3 To L 5 Each of these can be a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, R. e R f and R 23 To R 44 Each of these can be independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof, R 23 To R 30 They can exist independently or adjacent connections can form substituted or unsubstituted aromatic monocyclic or polycyclic rings, R 31 To R 35 Ar can exist independently or as adjacent connections forming substituted or unsubstituted aromatic monocyclic or polycyclic rings. 3 and Ar 4 Each can be an independently substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, R a Ar 3 and Ar 4 They can exist independently, or R a Ar 3 and Ar 4 Two adjacent rings can be connected to form substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic rings, and m5 and m6 are each an integer from 1 to 3.

[0127] In chemical formula 2B, when m5 is 2 or greater, each R 31 They can be the same or different. In chemical formula 2C, when m6 is 2 or greater, each R... 36 They can be the same or different.

[0128] For example, the second compound represented by chemical formula 2A can be derived from the following chemical formulas 2A-I to 2A-I.

[0129] Any one of the expressions in Equations 2A-XVIII.

[0130]

[0131]

[0132]

[0133]

[0134] In chemical formulas 2A-I to 2A-XVIII, L 2 To L 4 Ar 3 and Ar 4 and R 23 To R 30 It can be the same as above, X 3 It can be O or S, Ar 6 It can be a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, L 6 It can be a single bond, a substituted or unsubstituted C6 to C20 arylene, or a substituted or unsubstituted C2 to C20 heterocyclic group, and R 45 To R 64 Each of them can be hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted C1 to C10 alkylsilyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof.

[0135] For example, L 3 To L 6 Each can be independently a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted dibenzothiopheneylene.

[0136] For example, Ar 3 Ar 4 and Ar 6 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0137] For example, R 23 To R 30 and R 45 To R 64Each of them can be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0138] For example, a second compound represented by chemical formula 2B can be derived from the following chemical formulas 2B-I to 2B-I.

[0139] Any of the representations in Equation 2B-IV.

[0140]

[0141]

[0142] In chemical formulas 2B-I to 2B-IV, X 2 L 3 To L 5 Ar 3 and Ar 4 R 31 To R 35 And m5 is the same as above.

[0143] For example, a compound represented by chemical formula 2C can be represented by chemical formula 2C-I or chemical formula 2C-II.

[0144]

[0145]

[0146] In chemical formulas 2C-I and 2C-II, L 3 To L 5 Ar 3 and Ar 4 R 36 To R 44 The same applies to m6 as described above.

[0147] In some exemplary embodiments, chemical formula 2 may be represented by chemical formula 2A-XIV or chemical formula 2C-I.

[0148] For example, in chemical formula 2A-XIV, L 3 To L 6 Each can be a single bond or a substituted or unsubstituted C6 to C12 aryl group, Ar 3 Ar 4 and Ar 6Each of these can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, or a substituted or unsubstituted carbazoleyl, and R 23 To R 28 and R 61 To R 64 Each of them can be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl or substituted or unsubstituted C6 to C12 aryl.

[0149] For example, in the chemical formula 2C-I, L 3 To L 5 Each can be a single bond or a substituted or unsubstituted C6 to C12 aryl group, Ar 3 and Ar 4 Each of these can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, or a substituted or unsubstituted carbazoleyl, and R 36 To R 44 Each of them can be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl or substituted or unsubstituted C6 to C12 aryl.

[0150] The second compound can be, for example, one of the compounds listed in group 2 below.

[0151] [Group 2]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180] Compositions for organic optoelectronic devices may contain a first compound and a second compound in various ratios.

[0181] For example, a composition for an organic optoelectronic device may include a first compound and a second compound in 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.

[0182] For example, the first compound may be included in an amount equal to or greater than that of the second compound. For example, based on the total amount of the first and second compounds, the first compound may be included in an amount of about 50 wt% to about 90 wt%.

[0183] In another embodiment, the first compound may be included in an amount less than or equal to that of the second compound. For example, based on the total amount of the first and second compounds, the first compound may be included in an amount of about 10 wt% to about 50 wt%.

[0184] The composition for an organic optoelectronic device may further include a luminescent dopant in addition to the first and second compounds. The luminescent dopant is a material mixed in small amounts with the composition for the organic optoelectronic device to induce luminescence, and is typically a material that emits light by being excited to triplet or more states multiple times, such as a metal complex. The luminescent dopant can be, for example, an inorganic, organic, or organic / inorganic compound, and may contain one or more of these types. The luminescent dopant can be, for example, a phosphorescent photosensitizer, a fluorescent dopant, or a combination thereof.

[0185] Phosphorus photosensitizers can be organometallic compounds and can effectively transfer energy received from the host to the fluorescent dopant. Phosphorus photosensitizers can increase energy transfer to the fluorescent dopant, causing excitons formed in the emissive layer to emit light rapidly within the emissive layer, thereby reducing the degradation of the light-emitting diode.

[0186] The phosphorus photosensitizer can be, for example, an organometallic compound comprising iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), rhodium (Rh), or combinations thereof, and can be, for example, an organometallic compound comprising an organic ligand containing a nitrogen-containing ring. The nitrogen-containing ring can be, for example, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted triazine, substituted or unsubstituted carbazole, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, or combinations thereof. The phosphorus photosensitizer can be, for example, any of the following compounds P1 to P52.

[0187]

[0188]

[0189]

[0190] Fluorescent dopants can be, for example, polycyclic compounds, and can improve the luminous efficiency and lifetime characteristics of light-emitting diodes by receiving energy transfer due to high absorbance within the emitting layer.

[0191] The fluorescent dopant can be, for example, a condensed polycyclic compound containing boron (B) or nitrogen (N), and can be selected from, for example, compounds D1 to D30.

[0192]

[0193]

[0194] Based on the total amount of the composition for organic optoelectronic devices, the phosphorescent 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 to about 20 wt%, about 1 to about 15 wt%, about 1 to about 10 wt%, about 1 to about 7 wt%, about 1 to about 5 wt%, or about 1 wt% to about 4 wt%.

[0195] The composition for organic optoelectronic devices may further include additives, and the additives may be organic materials, inorganic materials, organic / inorganic materials, or combinations thereof.

[0196] The organic optoelectronic device using the above-described composition for organic optoelectronic devices will be described below.

[0197] Organic optoelectronic devices can be, for example, organic light-emitting diodes (OLEDs), organic optoelectronic devices, or organic solar cells. For example, an organic optoelectronic device can be an organic light-emitting diode (OLED).

[0198] Organic optoelectronic devices may include an anode and a cathode facing each other, and an organic layer between the anode and the cathode, and the organic layer may contain the composition described above. The organic layer may include an active layer (e.g., a light-emitting layer or a light-absorbing layer), and the active layer may contain the composition described above. The organic layer may include an auxiliary layer between the anode and the active layer and / or between the cathode and the active layer, and the auxiliary layer may contain the composition described above.

[0199] Figure 1 This is a cross-sectional view showing an embodiment of an organic light-emitting diode as an example of an organic optoelectronic device according to some embodiments.

[0200] refer to Figure 1 According to some embodiments, an 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. The light-emitting layer 130 may contain the composition described above.

[0201] The anode 110 can be made of a conductor with a high work function to facilitate hole injection, and can be made of, for example, metals, metal oxides, and / or conductive polymers. The anode 110 can be made of metals such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO and Al or SnO2 and Sb; and / or conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline.

[0202] The cathode 120 may be made of a conductor with a low work function to facilitate electron injection, and may be made of, for example, metals, metal oxides, and / or conductive polymers. The cathode 120 may be made of metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; and / or multilayer materials such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca.

[0203] The emitting layer 130 may contain the above-described composition for organic optoelectronic devices as a hybrid host. The emitting layer 130 may further contain another organic compound as a hybrid host. The emitting layer 130 may further contain the above-described luminescent dopant and may include fluorescent dopant, phosphorescent photosensitizer, or combinations thereof as described above. As an example, by combining the above-described composition for organic optoelectronic devices with a luminescent dopant, the emitting layer 130 can emit light in the blue emission spectrum. At least one of the first and second compounds in the composition for organic optoelectronic devices has a high triplet energy level greater than or equal to about 2.8 eV, making exciton transfer to the blue luminescent dopant readily possible, and thus enabling organic optoelectronic devices with high efficiency and long lifetime. For example, the peak wavelength of the blue emission spectrum may fall 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.

[0204] As described above, the composition for an organic optoelectronic device may comprise a first compound (which is a compound with relatively strong hole transport properties) and a second compound (which is a compound with relatively strong electron transport properties) such that, compared to the case where the first compound is used alone or the second compound is used alone, the luminous efficiency can be increased by increasing the balance of electrons and holes, and the lifetime can be improved by reducing unbound charge caused by the imbalance of electron and hole mobility.

[0205] In detail, in an organic light-emitting diode 100 including a light-emitting layer 130 using a composition for organic optoelectronic devices as a hybrid host, holes and electrons injected from the anode 110 and cathode 120 can be appropriately distributed within the light-emitting layer 130, the mobility can be controlled to an appropriate level, and exciton generation within the light-emitting layer 130 can be strongly induced, thereby improving the luminous efficiency of the light-emitting layer 130.

[0206] Furthermore, the generation of excitons at the interface between the light-emitting layer 130 and adjacent layers and / or the accumulation of unbound charges at the interface between the light-emitting layer 130 and adjacent layers can be reduced or prevented due to the difference in mobility of holes and electrons injected from the anode 110 and cathode 120, respectively, within the light-emitting layer 130. This can reduce or prevent the roll-off phenomenon, in which efficiency rapidly decreases due to unemitted excitons and / or unbound charges, thereby ultimately improving the lifetime of the organic light-emitting diode.

[0207] An organic light-emitting diode 100 can be manufactured by the following steps: forming an anode 110 or a cathode 120 on a substrate, forming a light-emitting layer using a dry film forming method (e.g., vacuum evaporation, sputtering, plasma electroplating, and ion electroplating), and forming a cathode 120 or anode 110 thereon.

[0208] Figure 2 This is a cross-sectional view showing another embodiment of an organic light-emitting diode as an example of an organic optoelectronic device according to some embodiments.

[0209] refer to Figure 2 Similar to the above embodiments, the organic light-emitting diode 100 according to the embodiments of this application may include an anode 110, a cathode 120, and a light-emitting layer 130. However, unlike the above embodiments, the organic light-emitting diode 100 according to the embodiments of this application may further include a hole transport layer 140, a hole transport auxiliary layer 150, and an electron transport layer 160.

[0210] Hole transport layer 140 may be located between anode 110 and light-emitting layer 130, and hole transport auxiliary layer 150 may be located between light-emitting layer 130 and hole transport layer 140. Electron transport layer 160 may be located between cathode 120 and light-emitting layer 130.

[0211] Hole transport layer 140 can facilitate the transfer of holes from anode 110 to light-emitting layer 130, and may include, for example, an amine compound. For example, the amine compound may have at least one aryl and / or heteroaryl group that has a hole characteristic. For example, the amine compound may be represented by chemical formula 6a or 6b, but is not limited thereto.

[0212]

[0213] In chemical formula 6a or 6b, Ar a To Ar g Each of these can be independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl, or a combination thereof. a To Ar c At least one of them and Ar d To Ar g At least one of them can be a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, or a combination thereof, and Ar h It can be 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.

[0214] The hole transport auxiliary layer 150 can form an interface with the light-emitting layer 130 by being located between the hole transport layer 140 and the light-emitting layer 130 and in contact with the light-emitting layer 130. The hole transport auxiliary layer 150 can further reduce or prevent the generation of excitons at the interface between the light-emitting layer 130 and the adjacent layer and / or the accumulation of unbound charges at the interface between the light-emitting layer 130 and the adjacent layer, thereby further reducing or preventing the roll-off phenomenon of rapid efficiency reduction due to the lack of exciton emission and / or unbound charges, and thus ultimately further improving the lifetime of the organic optoelectronic device 100.

[0215] The electron transport layer 160 may further increase electron injection and / or electron mobility and block holes between the cathode 120 and the light-emitting layer 130. The electron transport layer 160 may include one or more compounds selected, for example, from the group 5 listed below.

[0216] [Group 5]

[0217]

[0218]

[0219]

[0220]

[0221] Organic optoelectronic devices, including the aforementioned organic light-emitting diodes, can be applied to display devices.

[0222] In the following description, embodiments are illustrated in more detail with reference to examples. The following examples and comparative examples are provided to highlight the characteristics of one or more embodiments; however, it should be understood that these examples and comparative examples should not be construed as limiting the scope of the embodiments, nor should the comparative examples be construed as being outside the scope of the embodiments. Furthermore, it should be understood that the embodiments are not limited to the specific details described in the examples and comparative examples.

[0223] Unless otherwise specified, the starting materials and reactants used in the examples and synthesis examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry, or P&H Tech, or synthesized by known methods.

[0224] The compound, as a specific embodiment of the implementation plan, is synthesized through the following steps.

[0225] Synthesis of the first compound

[0226] Synthesis Example 1: Synthesis of Compound H-9

[0227] [Reaction Formula 1]

[0228]

[0229] Intermediate H-9-1 (3.0 g, 8.2 mmol), 9H-3,9'-dicarbazole (3.0 g, 9.0 mmol), tris(diphenylmethyleneacetone)dipalladium(O)Pd2(dba)3 (0.4 g, 0.4 mmol), sodium tert-butoxide (NaOtBu) (1.2 g, 12.2 mmol), and tris(tert-butyl)phosphine (P(tBu)3) (0.2 g, 1.2 mmol) were added to 41 mL of xylene, and the mixture was refluxed and stirred for 12 hours. When the reaction was complete, the product was purified by column chromatography (dichloromethane: n-hexane) to give 3.4 g of compound H-9 (yield: 62.3%).

[0230] Synthesis Example 2: Synthesis of Compound H-33

[0231] [Reaction 2]

[0232]

[0233] Compound H-33 (yield: 63.5%) was synthesized in the same manner as in Synthesis Example 1, except that intermediate H-33-1 was used instead of intermediate H-9-1.

[0234] Comparative Synthesis Example 1: Synthesis of Compound F-1

[0235] [Reaction 3]

[0236]

[0237] Compound F-1 (yield: 67.2%) was synthesized in the same manner as in Synthesis Example 1, except that intermediates F-1-1 and carbazole were used instead of intermediates H-9-1 and 9H-3,9'-dicarbazole.

[0238] Comparative Synthesis Example 2: Synthesis of Compound F-2

[0239] [Reaction 4]

[0240]

[0241] Compound F-2 (yield: 83.6%) was synthesized in the same manner as in Synthesis Example 1, except that intermediates F-2-1 and F-2-2 were used instead of intermediates H-9-1 and 9H-3,9'-dicarbazole.

[0242] Manufacturing of Organic Light Emitting Diode I

[0243] Example 1

[0244] The glass substrate coated with an ITO (indium tin oxide) film was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with solvents such as isopropanol, acetone, and methanol, and then dried. It was then transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and then transferred to a vacuum deposition unit. The prepared ITO transparent electrode was used as the anode, and compound A (Novaled GmbH) doped with 3% NDP-9 was vacuum deposited on the ITO substrate to form... A thick hole injection layer, and compound A is deposited on the hole injection layer until... The thickness is adjusted to form a hole transport layer. mCP (1,3-bis(carbazole-9-yl)phenyl) is deposited on the hole transport layer to a thickness of [missing information]. The thickness is adjusted to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compounds H-9 (body) and P-31 (dopant) obtained in Synthesis Example 1 are vacuum deposited to form... A thick luminescent layer was then formed. Subsequently, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) was deposited on the luminescent layer until... The thickness is such that an electron transport auxiliary layer is formed, and compounds B and LiQ are simultaneously vacuum-deposited at a weight ratio of 1:1 to form... A thick electron transport layer. This is achieved by sequential vacuum deposition on the electron transport layer. LiQ and Al is used to form the cathode to manufacture organic light-emitting diodes.

[0245] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine

[0246] Compound B: 8-{4-[bis(naphthyl-2-yl)-1,3,5-triazin-2-yl]phenyl}quinoline

[0247] Example 2

[0248] Organic light-emitting diodes were manufactured in the same manner as in Example 1, except that compound H-33 of synthesis Example 2 was used instead of compound H-9 of synthesis Example 1 as the main body of the light-emitting layer.

[0249] Comparative Example 1

[0250] Organic light-emitting diodes were manufactured in the same manner as in Example 1, except that compound F-1 from comparative synthesis Example 1 was used instead of compound H-9 from synthesis Example 1 as the main body of the light-emitting layer.

[0251] Comparative Example 2

[0252] Organic light-emitting diodes were manufactured in the same manner as in Example 1, except that compound F-2 from comparative synthesis Example 2 was used instead of compound H-9 from synthesis Example 1 as the main body of the light-emitting layer.

[0253] Assessment I

[0254] The luminous efficiency and lifetime characteristics of the organic light-emitting diodes according to the embodiments and comparative examples were evaluated.

[0255] The specific measurement methods are as follows, and the results are shown in Table 1.

[0256] (1) Measure the change in current density based on voltage change.

[0257] While increasing the voltage from 0V to 10V, the current flowing through the unit diode in the obtained organic light-emitting diode was measured using a current-voltmeter (Keithley 2400), and the measured current value was divided by the area to provide the result.

[0258] (2) Measure the brightness change based on voltage changes

[0259] While increasing the voltage of the organic light-emitting diode from 0V to 10V, the brightness was measured using a luminance meter (Minolta Cs-1000A).

[0260] (3) Measurement of luminous efficiency

[0261] Using the brightness, current density, and voltage measured from (1) and (2) above, calculate the voltage at the same current density (10 mA / cm²). 2 The luminous efficiency (cd / A) of the organic light-emitting diodes in the examples was calculated as a relative value based on the luminous efficiency of Comparative Example 1, and the results are shown in Table 1.

[0262] (4) Measurement of lifespan

[0263] In terms of brightness (cd / m 2 Maintain at 2000 cd / m 2 The time it took for the current efficiency (cd / A) of the organic light-emitting diodes according to the embodiments and comparative examples to decrease to 95% was measured. The measured lifetimes of the organic light-emitting diodes according to the embodiments and comparative examples were calculated as relative values ​​based on Comparative Example 1 and are shown in Table 1.

[0264] [Table 1]

[0265] Drive voltage (V) life(%) Example 1 4.2V 270％ Example 2 4.4V 130％ Comparative Example 1 4.6V 100％ Comparative Example 2 4.2V 91％

[0266] Referring to Table 1, compared with the organic light-emitting diode of Comparative Example 1, the organic light-emitting diode of the embodiment exhibits improved driving voltage and lifetime characteristics, and compared with the organic light-emitting diode of Comparative Example 2, it exhibits equivalent driving voltage and improved lifetime characteristics.

[0267] Synthesis of the second compound

[0268] Synthesis Example 3: Synthesis of Compound E-284

[0269] [Reaction 5]

[0270]

[0271] Step 1: Synthesis of intermediate E-284-1

[0272] (3-Bromophenyl)triphenylsilane (3.0 g, 7.2 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborane)pyrocyclopentane (B2Pin2) (2.4 g, 9.4 mmol), [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloro(II) (Pd(dppf)Cl2) (0.3 g, 0.4 mmol), and potassium acetate (KOAc) (2.1 g, 21.7 mmol) were added to 36 mL of xylene, and the mixture was refluxed and stirred for 12 hours. When the reaction was complete, the product was purified by column chromatography (dichloromethane:n-hexane) to obtain 2.4 g of intermediate E-284-1 (yield: 73.2%).

[0273] Step 2: Synthesis of compound E-284

[0274] Intermediate E-284-1 (2.4 g, 5.2 mmol), 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) (2.3 g, 5.2 mmol), Pd(PPh3)4 (0.3 g, 0.3 mmol), and potassium carbonate (K2CO3) (2.2 g, 15.6 mmol) were added to 17 mL of THF and 8.7 mL of DIW, and then refluxed and stirred for 12 hours. When the reaction was complete, the product was purified by column chromatography (dichloromethane:n-hexane) to obtain 3.5 g of compound E-284 (yield: 89.9%).

[0275] Manufacturing of Organic Light Emitting Diode II

[0276] Example 3

[0277] The glass substrate coated with an ITO (indium tin oxide) film was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with solvents such as isopropanol, acetone, and methanol, and then dried. It was then transferred to a plasma cleaner, 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 (Novaled GmbH) doped with 3% NDP-9 was vacuum deposited onto the ITO substrate to form... A thick hole injection layer, and compound A is deposited on the hole injection layer until... The thickness is increased to form a hole transport layer. mCP is deposited on the hole transport layer to... The thickness is adjusted to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compound H-9 obtained in Synthesis Example 1 and compound E-284 obtained in Synthesis Example 3 are used as the host compounds, with 13 wt% P31 doped as a phosphorescent photosensitizer and 1.5 wt% D3 doped as a fluorescent dopant, to form the layer by vacuum deposition. A thick luminescent layer was formed. In this paper, compounds A-54 and D-72 were used in a weight ratio of 4:6. Subsequently, BCP was deposited on the luminescent layer to... The thickness is such that an electron transport auxiliary layer is formed, and compounds B and Liq are simultaneously vacuum-deposited at a weight ratio of 1:1 to form... A thick electron transport layer. This is achieved by sequential vacuum deposition on the electron transport layer. LiQ and Al is used to form the cathode to manufacture organic light-emitting diodes.

[0278] ITO / Compound A (3% NDP-9 doped) Compound A / mCP / EML[Body (Compound H-9: Compound E-284): P31: D3 = 85.5wt%: 13wt%: 1.5wt%] / BCP / Compound B: LiQ / LiQ / Al

[0279]

[0280] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine

[0281] Compound B: 8-{4-[bis(naphthyl-2-yl)-1,3,5-triazin-2-yl]phenyl}quinoline

[0282]

[0283] Example 4

[0284] Organic light-emitting diodes were manufactured in the same manner as in Example 3, except that compounds H-33 of Synthesis Example 2 and E-284 of Synthesis Example 3 were used instead of compounds H-9 of Synthesis Example 1 and E-284 of Synthesis Example 3 as the main body of the light-emitting layer.

[0285] Comparative Example 3

[0286] Organic light-emitting diodes were manufactured in the same manner as in Example 3, except that compounds F-1 of Comparative Synthesis Example 1 and E-284 of Synthesis Example 3 were used instead of compounds H-9 of Synthesis Example 1 and E-284 of Synthesis Example 3 as the main body of the light-emitting layer.

[0287] Comparative Example 4

[0288] Organic light-emitting diodes were manufactured in the same manner as in Example 3, except that compounds F-2 from comparative synthesis example 2 and E-284 from synthesis example 3 were used instead of compounds H-9 from synthesis example 1 and E-284 from synthesis example 3 as the main body of the light-emitting layer.

[0289] Assessment II

[0290] The luminous efficiency and lifetime characteristics of the organic light-emitting diodes according to the embodiments and comparative examples were evaluated.

[0291] The results are shown in Table 2.

[0292] [Table 2]

[0293]

[0294]

[0295] Referring to Table 2, compared with the organic light-emitting diode according to Comparative Example 3, it is confirmed that the organic light-emitting diode according to the embodiment exhibits improved driving voltage and lifetime characteristics, and compared with the organic light-emitting diode according to Comparative Example 4, it exhibits improved lifetime characteristics.

[0296] By summarizing and reviewing, some exemplary embodiments provide compounds for organic optoelectronic devices that can achieve high efficiency and long lifespan characteristics. Some exemplary embodiments provide compositions for organic optoelectronic devices comprising compounds for organic optoelectronic devices. Some exemplary embodiments provide organic optoelectronic devices comprising compounds or compositions. Some exemplary embodiments provide display devices including organic optoelectronic devices.

[0297] Exemplary embodiments have been disclosed herein, and although specific terminology has been used, it is used and interpreted in a general and descriptive sense only and not for limiting purposes. In some instances, it will be apparent to those skilled in the art that features, characteristics, and / or elements described in connection with specific embodiments may be used alone or in combination with features, characteristics, and / or elements described in connection with other embodiments, as of the date of filing of this application, unless expressly indicated otherwise. Therefore, those skilled in the art will understand that various changes in form and detail may be made without departing from the spirit and scope of the invention as set forth in the appended claims.

Claims

1. A compound represented by chemical formula 1: [Chemical Formula 1] In chemical formula 1, X 1 and X 2 Each is an independent NR a ,O,S,Se or Te, R 1 To R 10 Each of them is a group represented by the chemical formula A. R 1 To R 10 The remaining ones and R a Each of these elements is independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted silyl, cyano, or halogen. R 1 To R 10 and R a Each exists independently, or R 1 To R 10 and R a Two adjacent connections in the middle form a loop. [Chemical Formula A] In chemical formula A, R 11 To R 18 Each of these elements is independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted silyl, cyano, or halogen. The condition is that R 11 To R 18 One of them is a substituted or unsubstituted carbazole group. R 11 To R 18 Each exists independently, or R 11 To R 18 Two adjacent connections in the middle form a loop, and * indicates the connection point with chemical formula 1.

2. The compound according to claim 1, wherein the R of chemical formula A 11 To R 18 Any one of them is represented by the chemical formula Aa: [Chemical formula Aa] In the chemical formula Aa, R 19 To R 26 Each of these elements is independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted silyl, cyano, or halogen. R 19 To R 26 Each exists independently, or R 11 To R 18 Two adjacent connections in the middle form a loop, and * indicates the connection point with chemical formula A.

3. The compound according to claim 2, wherein the R of chemical formula Aa 19 To R 26 At least one of them is deuterium.

4. The compound according to claim 1, wherein chemical formula A is represented by chemical formula A-1: [Chemical Formula A-1] In chemical formula A-1, R 11 To R 15 and R 17 To R 26 Each of these elements is independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted silyl, cyano, or halogen. R 11 To R 15 and R 17 To R 26 Each exists independently, or R 11 To R 15 and R 17 To R 26 Two adjacent connections in the middle form a loop, and * indicates the connection point with chemical formula 1.

5. The compound according to claim 1, wherein R of chemical formula 1 1 To R 4 and R 7 To R 10 Each of them is a group represented by the chemical formula A.

6. The compound according to claim 1, wherein: X 1 and X 2 At least one of them is NR a ,and R a Each of these elements independently is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted benzothiophenyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzothiophenyl, or a substituted or unsubstituted dibenzothiophenyl.

7. The compound according to claim 1, wherein R 1 To R 18 At least one of them is deuterium.

8. A composition for use in an organic optoelectronic device, comprising: First compound and second compound, in, The first compound is the compound according to any one of claims 1 to 7, and The second compound is represented by chemical formula 2: [Chemical Formula 2] In chemical formula 2, Z 1 To Z 6 Each is independently N or CL a -R e , Z 1 To Z 6 At least two of them are N. L a Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted divalent C2 to C20 heterocyclic group, or a combination thereof. R e Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof, and R e They exist independently, or two adjacent R. e The linkages form substituted or unsubstituted aliphatic, aromatic, or heteroaromatic monocyclic or polycyclic rings.

9. The composition according to claim 8, wherein, The second compound represented by chemical formula 2 is represented by any one of chemical formulas 2A to 2C: In chemical formulas 2A to 2C Z 1 Z 3 and Z 5 Each is independently N or CL a -R e , Z 1 Z 3 and Z 5 At least two of them are N. X 2 Is it O, S, or NR? f , L a and L 3 To L 5 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof. R e R f and R 23 To R 44 Each of these elements independently comprises hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof. R 23 To R 30 Each exists independently, or R 23 To R 30 Two adjacent links in the middle form substituted or unsubstituted aromatic monocyclic or polycyclic rings. R 31 To R 35 Each exists independently, or R 31 To R 35 Two adjacent links in the middle form substituted or unsubstituted aromatic monocyclic or polycyclic rings. Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof. R a Ar 3 and Ar 4 Each exists independently, or R a Ar 3 and Ar 4 Two adjacent connections in the middle form substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic rings, and m5 and m6 are each independently an integer from 1 to 3.

10. An organic optoelectronic device, comprising: The anode and cathode facing each other, and A light-emitting layer between the anode and the cathode, the light-emitting layer comprising any one of claims 1 to 7.

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

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

13. A display device comprising the organic optoelectronic device according to any one of claims 10 to 12.

14. An organic optoelectronic device, comprising: The anode and cathode facing each other, and A light-emitting layer between the anode and the cathode, the light-emitting layer comprising the composition of claim 8 or 9.

15. The organic optoelectronic device of claim 14, wherein the light-emitting layer further comprises a fluorescent dopant, a phosphorescent photosensitizer, or a combination thereof.

16. The organic optoelectronic device according to claim 15, wherein: The phosphorus photosensitizer is an organometallic compound, and The fluorescent dopant is a condensed polycyclic compound comprising boron, nitrogen, or a combination thereof.

17. A display device comprising an organic optoelectronic device according to any one of claims 14 to 16.

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