Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device, and display device

Abstract

A compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device, the composition for an organic optoelectronic device comprising the compound, the organic optoelectronic device comprising the compound or the composition for an organic optoelectronic device, the display device comprising an organic optoelectronic device, the compound is represented by Chemical Formula 1. [Chemical Formula 1]

Description

[0001] Citations of relevant applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0063007, filed on May 14, 2024, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The embodiments relate to compounds for organic optoelectronic devices, compositions for organic optoelectronic devices, organic optoelectronic devices, and display devices. Background Technology

[0004] Organic optoelectronic devices (e.g., organic photodiodes) are devices that can convert electrical energy and light energy into each other.

[0005] Based on their driving principle, organic optoelectronic devices can be classified as follows. One type is optoelectronic devices that generate electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes. The other type is light-emitting devices that generate light energy from electrical energy by providing voltage or current to the electrodes.

[0006] Examples of organic optoelectronic devices can include organic photoelectric devices, organic light-emitting diodes, organic solar cells, and organic photosensitive drums.

[0007] Organic light-emitting diodes (OLEDs) have garnered significant attention in recent years due to the increasing demand for flat panel display devices. OLEDs are devices that convert electrical energy into light, and their performance is greatly influenced by the organic materials used between the electrodes. Summary of the Invention

[0008] One embodiment can be achieved by providing a compound for organic optoelectronic devices, represented by chemical formula 1:

[0009] [Chemical Formula 1]

[0010]

[0011] In chemical formula 1, Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, Ar 1 and Ar 2 At least one of them is a substituted or unsubstituted C10 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group, R 1 To R 10Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C30 alkyl or substituted or unsubstituted C6 to C30 aryl, R 11 and R 12 Each is independently either hydrogen or deuterium, and R 13 To R 20 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C20 heterocyclic.

[0012] The embodiment can be implemented by providing a composition for an organic optoelectronic device, the composition comprising a first compound and a second compound, wherein the first compound is the aforementioned compound for an organic optoelectronic device, and the second compound is represented by chemical formula 2, a combination of chemical formula 3 and chemical formula 4, or chemical formula 5:

[0013] [Chemical Formula 2]

[0014]

[0015] In chemical formula 2, R 21 To R 25 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, L 1 and L 2 Each of the C6 to C20 aryl groups is independently a single bond or a substituted or unsubstituted group, m1, m4 and m5 are independently integers from 1 to 4, m2 and m3 are independently integers from 1 to 3, and n is an integer from 0 to 2.

[0016]

[0017] In chemical formulas 3 and 4, the two adjacent carbons a1* to a4* in chemical formula 3 are the connecting carbons attached to the * in chemical formula 4, and the remaining two carbons a1* to a4* in chemical formula 3 that are not attached to the * in chemical formula 4 are CL. a -R a L a L 3 and L 4 Each is independently a single bond or a substituted or unsubstituted C6 to C20 aryl group, R a R 26 and R 27Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m6 and m7 are independently integers from 1 to 4.

[0018] [Chemical Formula 5]

[0019]

[0020] In chemical formula 5, L 5 It is a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, R 28 To R 31 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, Ar 7 It is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m8, m10 and m11 are each an integer from 1 to 4 independently, and m9 is an integer from 1 to 3.

[0021] An embodiment can be implemented by providing an organic optoelectronic device comprising an anode and a cathode facing each other and at least one organic layer between the anode and the cathode, wherein the at least one organic layer contains a compound for an organic optoelectronic device according to one embodiment.

[0022] An embodiment can be implemented by providing an organic optoelectronic device comprising an anode and a cathode facing each other and at least one organic layer between the anode and the cathode, wherein the at least one organic layer comprises a composition for an organic optoelectronic device according to one embodiment.

[0023] This can be achieved by providing a display device that includes organic optoelectronic devices. Attached Figure Description

[0024] Features will become apparent to those skilled in the art from the detailed description of exemplary embodiments with reference to the accompanying drawings, wherein:

[0025] Figure 1 This is a cross-sectional view of an organic light-emitting diode according to some exemplary embodiments. Detailed Implementation

[0026] 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 described herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey exemplary implementations to those skilled in the art.

[0027] In the accompanying drawings, the dimensions of layers and regions may be enlarged 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 "below" another layer, it may be directly below that layer, or there may be one or more intermediate layers. Additionally, 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 consistently indicate the same elements.

[0028] As used herein, unless otherwise defined, “substituted” means that at least one hydrogen atom of a substituent or compound is replaced by one of the following: 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.

[0029] In one embodiment, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by one of the following: deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, or cyano. In one embodiment, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by one of the following: deuterium, C1 to C20 alkyl, C1 to C5 alkylsilyl, C6 to C20 aryl, C2 to C20 heteroaryl, or cyano. In one embodiment, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by one of the following: deuterium, C1 to C5 alkyl, C1 to C5 alkylsilyl, C6 to C18 aryl, C2 to C18 heteroaryl, or cyano. In one implementation, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by one of the following: deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trimethylsilyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0030] "Unsubstituted" means that the hydrogen atom is not replaced by another substituent and the hydrogen atom is retained.

[0031] In this specification, “hydrogen substitution (-H)” can include “deuterium substitution (-D)” or “tritium substitution (-T)”. For example, any hydrogen in any compound described herein can be protium, deuterium, or tritium (e.g., based on natural or artificial substitution).

[0032] As used herein, unless otherwise defined, “heterogeneous” means a functional group containing one to three heteroatoms selected from N, O, S, P and Si and the remaining carbon.

[0033] As used herein, “aryl” means a group comprising at least one aromatic hydrocarbon moiety, and all elements of the aromatic hydrocarbon moiety have conjugated p orbitals, such as phenyl, naphthyl, etc., two or more aromatic hydrocarbon moiety may be linked by σ bonds and may be, for example, biphenyl, terphenyl, tetraphenyl, etc., and two or more aromatic hydrocarbon moiety may be directly or indirectly fused to provide a non-aromatic fused ring, such as fluorene.

[0034] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent carbon atom pairs) functional groups.

[0035] 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 in place of carbon (C) in cyclic compounds such as aryl, cycloalkyl, their fused rings, or combinations thereof. When the heterocyclic group is fused, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0036] For 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 a heteroaryl group comprises two or more rings, the two or more rings can be fused. When a heteroaryl group is a fused ring, each ring may comprise one to three heteroatoms.

[0037] 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 meta-terphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted trefyl, a substituted or unsubstituted benzophenanthrene, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indene, or a combination thereof.

[0038] 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, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indoleyl group, or a substituted... Or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxolinyl, substituted or unsubstituted naphthidyl, 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 carbazoyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzofuran-fluorenyl, substituted or unsubstituted benzothiophene-fluorenyl or combinations thereof.

[0039] As used herein, hole characteristics refer to the ability to provide 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 light-emitting layer due to the conductivity of the highest occupied molecular orbital (HOMO) energy level.

[0040] Furthermore, electronic properties refer to the ability to accept 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.

[0041] The following describes compounds for organic optoelectronic devices according to some exemplary embodiments.

[0042] Compounds for organic optoelectronic devices according to some exemplary embodiments are represented by chemical formula 1.

[0043] [Chemical Formula 1]

[0044]

[0045] In chemical formula 1, Ar 1 and Ar 2Each can be, for example, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0046] In one implementation, Ar 1 and Ar 2 At least one of them may be, for example, a substituted or unsubstituted C10 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group.

[0047] R 1 To R 10 Each can be independently, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C30 alkyl or substituted or unsubstituted C6 to C30 aryl.

[0048] R 11 and R 12 They can be, for example, hydrogen or deuterium, each independently.

[0049] R 13 To R 20 Each can be independently, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C20 heterocyclic.

[0050] In the compound represented by Formula 1, N-carbazole is substituted at the ortho position relative to the phenylene linked to the triazine, and substituted or unsubstituted phenyl groups are substituted at the two meta positions of the phenylene linked to the triazine.

[0051] The compound represented by Formula 1 has a structure containing o-carbazole relative to triazine and exhibits particularly excellent energy transfer efficiency to phosphorescent dopants, thus making it a favorable material for use as a phosphorescent host. Due to the two meta-phenyl structures substituted on the triazine-linked phenylene in Formula 1, the LUMO level is shallow, ensuring an exciplex bandgap.

[0052] Furthermore, by substituting the carbazole at the ortho position of the triazine, the dihedral angle increases due to the steric hindrance between the triazine and carbazole, and the triazine and carbazole portions are twisted together, further increasing the dihedral angle. This results in the electron clouds of the HOMO and LUMO levels being largely separated and non-overlapping, and it has a small ΔEst, enabling rapid energy transfer and exhibiting high efficiency, especially when used as a phosphorescent host. Additionally, the reduced side reaction pathways of the excited state further increase the lifetime.

[0053] In one implementation, Ar 1 and Ar 2At least one of them may be, for example, a substituted or unsubstituted C6 to C30 unfused aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group.

[0054] In one implementation, Ar 1 and Ar 2 At least one of them may be, for example, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl.

[0055] In one implementation, Ar 1 and Ar 2 At least one of them may be, for example, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl.

[0056] In one implementation, R 1 To R 10 Each can be independently, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl.

[0057] In one implementation, R 1 To R 10 Each can be independently, for example, hydrogen, deuterium, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted phenyl, or substituted or unsubstituted biphenyl.

[0058] In one implementation, R 1 To R 10 Each can be independently, for example, hydrogen, deuterium, cyano, substituted or unsubstituted tert-butyl, or substituted or unsubstituted phenyl.

[0059] In one implementation, R 13 To R 20 Each can be independently, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, or substituted or unsubstituted C2 to C12 heterocyclic.

[0060] In one implementation, R 13 To R 20Each of these can be, independently, for example, hydrogen, deuterium, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted dibenzothiophene.

[0061] In one implementation, R 13 To R 20 Each can be independently, for example, hydrogen, deuterium, cyano, substituted or unsubstituted tert-butyl, or substituted or unsubstituted phenyl.

[0062] In one implementation, the compound represented by chemical formula 1 can be a compound of group 1.

[0063] [Group 1]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070] (Dn refers to the number of deuterium substitutions and indicates a structure with one or more deuterium atoms as substitutions).

[0071] A composition for an organic optoelectronic device according to some exemplary embodiments may comprise a first compound and a second compound, wherein the first compound may be the compound described above for an organic optoelectronic device, and the second compound may be represented by chemical formula 2, a combination of chemical formula 3 and chemical formula 4, or chemical formula 5.

[0072] [Chemical Formula 2]

[0073]

[0074] In chemical formula 2, R 21 To R 25 Each can be independently, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group.

[0075] Ar 3 and Ar 4Each can be, for example, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, independently.

[0076] L 1 and L 2 They can be, for example, single bonds or substituted or unsubstituted C6 to C20 aryl groups.

[0077] m1, m4, and m5 can each be an integer from 1 to 4 independently.

[0078] m2 and m3 can each be an integer, for example, from 1 to 3, independently.

[0079] n is an integer between 0 and 2.

[0080]

[0081] In chemical formulas 3 and 4, the two adjacent carbons a1* to a4* in chemical formula 3 can be the connecting carbons *attached to chemical formula 4, and the other two carbons a1* to a4* in chemical formula 3 that are not *attached to chemical formula 4 can be CL. a -R a As used herein, the term "connecting carbon" refers to the shared carbon on which a fused ring is attached.

[0082] L a L 3 and L 4 They can be, for example, single bonds or substituted or unsubstituted C6 to C20 aryl groups.

[0083] R a R 26 and R 27 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group.

[0084] Ar 5 and Ar 6 Each can be, for example, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, independently.

[0085] m6 and m7 can each be an integer from 1 to 4, for example, independently.

[0086] [Chemical Formula 5]

[0087]

[0088] In chemical formula 5, L 5It can be, for example, a single bond or a substituted or unsubstituted C6 to C20 aryl group.

[0089] R 28 To R 31 Each can be independently, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group.

[0090] Ar 7 It can be, for example, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0091] m8, m10, and m11 can each be an integer, for example, from 1 to 4.

[0092] m9 can be an integer from 1 to 3.

[0093] The second compound can be used together with the first compound in the luminescent layer to improve luminous efficiency and lifetime characteristics by increasing charge mobility and stability.

[0094] In one implementation, in chemical formula 2, m1 can be 2, 3, or 4, and each R 21 They can be the same as or different from each other.

[0095] In one implementation, in chemical formula 2, m2 can be 2 or 3, and each R 22 They can be the same as or different from each other.

[0096] In one implementation, in chemical formula 2, m3 can be 2 or 3, and each R 23 They can be the same as or different from each other.

[0097] In one implementation, in chemical formula 2, m4 can be 2, 3, or 4, and each R 24 They can be the same as or different from each other.

[0098] In one implementation, in chemical formula 2, m5 can be 2, 3, or 4, and each R 25 They can be the same as or different from each other.

[0099] In one implementation, in chemical formulas 3 and 4, m6 can be 2, 3, or 4, and each R 26 They can be the same as or different from each other.

[0100] In one implementation, in chemical formulas 3 and 4, m7 can be 2, 3, or 4, and each R 27 They can be the same as or different from each other.

[0101] In one implementation, two Rs can exist in chemical formulas 3 and 4. a Groups, and each R a They can be the same as or different from each other.

[0102] In one implementation, in chemical formula 5, m8 can be 2, 3, or 4, and each R 28 They can be the same as or different from each other.

[0103] In one implementation, in chemical formula 5, m9 can be 2 or 3, and each R 29 They can be the same as or different from each other.

[0104] In one implementation, in chemical formula 5, m10 can be 2, 3, or 4, and each R 30 They can be the same as or different from each other.

[0105] In one implementation, in chemical formula 5, m11 can be 2, 3, or 4, and each R 31 They can be the same as or different from each other.

[0106] In one implementation, in chemical formula 2, Ar 3 and Ar 4 Each of these can be independently, for example, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted fluorenyl.

[0107] In one implementation, in chemical formula 2, L 1 and L 2 Each can be, independently, a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0108] In one implementation, in chemical formula 2, R 21 To R 25 They can be, independently, for example, hydrogen, deuterium, or substituted or unsubstituted C6 to C12 aryl groups.

[0109] n can be, for example, 0 or 1.

[0110] In one implementation, in Formula 2, “substituted” can mean that at least one hydrogen atom is replaced by one of the following: deuterium, C1 to C4 alkyl, C6 to C18 aryl or C2 to C30 heteroaryl.

[0111] In one implementation, in chemical formula 2, Ar 3and Ar 4 Each can be independently, for example, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, or a substituted or unsubstituted fluorenyl.

[0112] In one implementation, chemical formula 2 can be represented by one of chemical formulas 2-1 to 2-15.

[0113]

[0114]

[0115]

[0116] In chemical formulas 2-1 to 2-15, R 21 To R 25 Each can be independently, for example, hydrogen, deuterium, or substituted or unsubstituted C6 to C12 aryl groups, and partially -L 1 -Ar 3 and -L 2 -Ar 4 Each can be an independent part of, for example, group I.

[0117] [Group I]

[0118]

[0119] In group I, R 32 To R 36 Each can be independently, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl.

[0120] m12 can be, for example, an integer from 1 to 5.

[0121] m13 can be, for example, an integer from 1 to 4.

[0122] m14 can be, for example, an integer from 1 to 3.

[0123] m15 can be an integer such as 1 or 2.

[0124] m16 can be, for example, an integer from 1 to 7.

[0125] * indicates a connection point.

[0126] In group I, m12 can be 2 or greater, and each R 32 They can be the same as or different from each other.

[0127] In group I, m13 can be 2 or greater, and each R 33 They can be the same as or different from each other.

[0128] In group I, m14 can be 2 or greater, and each R 34 They can be the same as or different from each other.

[0129] In group I, m15 can be 2, and each R 35 They can be the same as or different from each other.

[0130] In group I, m16 can be 2 or greater, and each R 36 They can be the same as or different from each other.

[0131] Combinations of chemical formulas 3 and 4 can be, for example, derived from chemical formulas 3A, 3B, and 4.

[0132] One of the following: Formula 3C, Formula 3D, and Formula 3E.

[0133]

[0134] In chemical formulas 3A to 3E, L 3 L 4 Ar 5 Ar 6 R 26 R 27 m6 and m7 can be defined as the same as those mentioned above.

[0135] L a1 To L a4 It can be defined as the L mentioned above 3 and L 4 same.

[0136] R a1 To R a4 It can be defined as R above 26 and R 27 same.

[0137] In one implementation, Ar in chemical formulas 3 and 4 5 and Ar 6 Each of these can be independently, for example, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted fluorenyl.

[0138] R a1 To R a4 R 26 and R 27Each of these can be, independently, for example, hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0139] In one implementation, in chemical formulas 3 and 4, part of -L 3 -Ar 5 and part-L 4 -Ar 6 Each can be an independent part of, for example, group I.

[0140] In one implementation, R a1 To R a4 R 26 and R 27 Each of these can be, independently, for example, hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0141] In one implementation, R a1 To R a4 R 26 and R 27 Each can be independently, for example, hydrogen, deuterium, cyano, or substituted or unsubstituted phenyl groups.

[0142] In one implementation, R a1 To R a4 R 26 and R 27 Each can be, independently, for example, hydrogen, deuterium, or substituted or unsubstituted phenyl groups.

[0143] In one implementation, the second compound can be represented by chemical formula 2-8, and in chemical formula 2-8, Ar 3 and Ar 4 Each of these can be independently, for example, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted carbazole, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene, L 1 and L 2 Each can be independently, for example, a single bond or a substituted or unsubstituted C6 to C20 aryl group, and R 21 To R 24 Each of these can be, independently, for example, hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0144] In one implementation, in chemical formula 2-8, R 21 To R 24 Each can be independently, for example, hydrogen, deuterium, or substituted or unsubstituted C6 to C12 aryl groups, and partially -L 1 -Ar 3 and -L 2 -Ar 4 Each can be an independent part of group I.

[0145] In one implementation, the second compound can be represented by the chemical formula 3C, and in the chemical formula 3C, L a3 and L a4 It could be, for example, a single bond, L 3 and L 4 Each can be independently, for example, a single bond or a substituted or unsubstituted C6 to C12 aryl group, R 26 R 27 R a3 and R a4 Each can be, for example, hydrogen, deuterium, or a substituted or unsubstituted phenyl group, and Ar 5 and Ar 6 Each of these can be independently, for example, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene.

[0146] In one implementation, in the chemical formula 3C, L a3 and L a4 They can be independent entities, such as single bonds, R 26 R 27 R a3 and R a4 Each can be independently, for example, hydrogen, deuterium, or substituted or unsubstituted C6 to C12 aryl groups, and partially -L 3 -Ar 5 and -L 4 -Ar 6 Each can be an independent part of group I.

[0147] Chemical formula 5 can be represented, for example, by one of chemical formulas 5-1 to 5-4.

[0148]

[0149] In chemical formulas 5-1 to 5-4, L 5 Ar 7 R 28 To R 31And m8 to m11 can be defined as the same as those mentioned above.

[0150] In one implementation, in chemical formula 5, Ar 7 It can be, for example, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted fluorenyl.

[0151] R 28 To R 31 Each of these can be, independently, for example, hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0152] In one implementation, in chemical formula 5, part of -L 5 -Ar 7 It can be part of group I.

[0153] In one implementation, R 28 To R 31 Each can be independently, for example, hydrogen, deuterium, cyano, or substituted or unsubstituted phenyl groups.

[0154] In one implementation, the second compound for the organic optoelectronic device may be a compound of group 2.

[0155] [Group 2]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163] Examples are given below of compounds B-1 to B-150 listed in Group 2, in which at least one hydrogen atom is replaced by deuterium.

[0164]

[0165]

[0166]

[0167] (Dn refers to the number of deuterium substitutions and indicates a structure with one or more deuterium atoms as substitutions).

[0168] Based on the position and rate of deuterium substitution, the most specific structures of compounds B-151 to B-195 of group 2 are presented below as examples.

[0169] In one implementation, deuterium may be substituted, for example as shown in the compounds illustrated below, or the deuterium substitution position, deuterium substitution rate, etc., may include all variable ranges within the range of compounds B-1 to B-195.

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177] In one implementation, an example of at least one hydrogen atom in compounds C-1 to C-57 listed in group 2 being replaced by deuterium can be shown below.

[0178]

[0179] (Dn refers to the number of deuterium substitutions and indicates a structure with one or more deuterium atoms as substitutions).

[0180] Based on the position and substitution rate of deuterium substitution, the most specific structures of compounds C-58 to C-72 of group 2 are presented below as examples.

[0181] In one implementation, deuterium may be substituted, as shown in the compounds illustrated below, or the deuterium substitution position, deuterium substitution rate, etc., may include all variable ranges from compound C-58 to compound C-72.

[0182]

[0183]

[0184]

[0185]

[0186]

[0187] In one implementation, an example of at least one hydrogen atom in compounds D-1 to D-60 listed in group 2 being replaced by deuterium can be shown below.

[0188]

[0189]

[0190]

[0191]

[0192] (Dn refers to the number of deuterium substitutions and indicates a structure with one or more deuterium atoms as substitutions).

[0193] In one implementation, the first compound may be represented by chemical formula 1, and the second compound may be represented by chemical formulas 2-8.

[0194] The first and second compounds can be included (e.g., mixed) in a weight ratio of, for example, from about 1:99 to about 99:1. By including them within the above range, efficiency and lifetime can be improved by utilizing the electron transport capability of the first compound and the hole transport capability of the second compound, and by adjusting the appropriate weight ratio, through achieving bipolar characteristics. Within the above range, they can be included in weight ratios of, for example, from about 10:90 to about 90:10, from about 20:80 to about 80:20, from about 20:80 to about 70:30, from about 20:80 to about 60:40, and from about 30:70 to about 60:40. In one implementation, they can be included in weight ratios of about 40:60, about 50:50, or about 60:40.

[0195] In the following text, an organic optoelectronic device comprising the above-described compound for an organic optoelectronic device or a composition for an organic optoelectronic device will be described.

[0196] Organic optoelectronic devices can be suitable devices that convert electrical energy into light energy and vice versa, such as organic photoelectric devices, organic light-emitting diodes, organic solar cells, or organic photosensitive drums.

[0197] In this paper, an organic light-emitting diode (OLED) is described as an example of an organic optoelectronic device with reference to the accompanying drawings.

[0198] Figure 1This is a cross-sectional view of an organic light-emitting diode according to some exemplary embodiments.

[0199] Reference Figure 1 An organic light-emitting diode 100 according to some exemplary embodiments may include an anode 120 and a cathode 110 facing each other and an organic layer 105 between the anode 120 and the cathode 110.

[0200] The anode 120 may be made of a conductor with a high work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or alloys thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; a combination of metals and oxides such as ZnO and Al or SnO2 and Sb; or a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, or polyaniline.

[0201] The cathode 110 may be made of a conductor with a small work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; or a multilayer material such as LiF / Al, LiO2 / Al, LiF / Ca, or BaF2 / Ca.

[0202] The organic layer 105 may contain the compounds or compositions described above for organic optoelectronic devices.

[0203] The organic layer 105 may include a light-emitting layer 130, and the light-emitting layer 130 may include a host and a dopant. The host may include the compounds or compositions described above for organic optoelectronic devices, and the dopant may be, for example, a phosphorescent dopant. In one implementation, the phosphorescent dopant may be a red, green, or blue phosphorescent dopant, such as a red or green phosphorescent dopant.

[0204] A dopant is a material that is mixed in small amounts with a compound or composition used in organic optoelectronic devices to induce luminescence, and is typically a material such as a metal complex that emits light by being excited multiple times to a triplet or more states. Dopants can be, for example, inorganic, organic, or organic-inorganic compounds, and one or more of these types can be used.

[0205] Examples of dopants can be phosphorescent dopants, and examples of phosphorescent dopants can be organometallic compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants can be, for example, compounds represented by the chemical formula Z.

[0206] [Chemical Formula Z]

[0207] L 6 MX 1

[0208] In the chemical formula Z, M can be a metal, and L 6 and X 1 Each can be an independent ligand that forms a complex with M.

[0209] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L 6 and X 1 It could be, for example, a bidentate ligand.

[0210] By L 6 and X 1 The instances of the ligands represented can include ligands of group A.

[0211] [Group A]

[0212]

[0213] In group A, R 300 To R 302 Each can be, independently, for example, hydrogen, deuterium, halogenated or unsubstituted C1 to C30 alkyl, halogenated or unsubstituted C6 to C30 aryl, or halogen.

[0214] R 303 To R 324 Each of these can be, independently, for example, hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF5, trialkylsilyl having substituted or unsubstituted C1 to C30 alkyl, dialkylarylsilyl having substituted or unsubstituted C1 to C30 alkyl and C6 to C30 aryl, or triarylsilyl having substituted or unsubstituted C6 to C30 aryl.

[0215] n1 can be, for example, an integer from 1 to 5.

[0216] n2 can be, for example, an integer from 1 to 4.

[0217] n3 can be, for example, an integer from 1 to 3.

[0218] n4 can be an integer such as 1 or 2.

[0219] n5 can be, for example, an integer from 1 to 6.

[0220] The dopant according to some exemplary embodiments may be an iridium complex and may be represented by, for example, chemical formula 6-1 or chemical formula 6-2.

[0221] [Chemical Formula 6-1]

[0222]

[0223] In chemical formula 6-1, R 101 To R 116 Each of these can be independently, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 132 R 133 R 134 .

[0224] R 132 To R 134 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0225] In one implementation, R 101 To R 116 Each can be a functional group, for example, represented by the chemical formula V-1.

[0226] L 100 It can be, for example, a bidentate ligand of a monovalent anion, and can be, for example, a ligand coordinated with iridium via the lone pair electrons of a carbon or heteroatom.

[0227] m21 and m22 can each be an integer from 0 to 3 independently, for example, and m21+m22 can be an integer from 1 to 3, for example.

[0228] [Chemical Formula V-1]

[0229]

[0230] In chemical formula V-1, R 135 To R 139 Each of these can be independently, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 132 R133 R 134 .

[0231] * refers to the part that is attached to a carbon atom.

[0232] [Chemical Formula 6-2]

[0233]

[0234] In chemical formula 6-2, R 101 To R 117 Each of these can be independently, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 133 R 134 R 135 .

[0235] R 133 To R 135 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0236] L 100 It can be, for example, a bidentate ligand of a monovalent anion, or a ligand coordinated to iridium via the lone pair electrons of a carbon or heteroatom.

[0237] n1 and n2 can each be an integer from 0 to 3 independently, and n1+n2 can be an integer from 1 to 3.

[0238] The dopant according to some exemplary embodiments may be a platinum complex and may be represented by, for example, the chemical formula Z-1.

[0239] [Chemical Formula Z-1]

[0240]

[0241] In chemical formula Z-1, rings A, B, C, and D can each be independently a 5- or 6-membered carbon ring or a heterocyclic ring.

[0242] R A R B R C and R D Each can be independently substituted, for example, monosubstituted, disubstituted, trisubstituted, or tetrasubstituted, or unsubstituted;

[0243] L B L C and L D They can be, independently, for example, direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', or combinations thereof.

[0244] In one implementation, nA can be 1, and L E It can be, for example, a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', or a combination thereof. In one implementation, nA can be 0, and L E It does not exist.

[0245] R A R B R C R D R and R' can each independently be, for example, hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, or combinations thereof. In one implementation, any adjacent R A R B R C R D R and R' can be separate or connected to each other to provide a ring; X B X C X D and X E Each can be either carbon or nitrogen independently; and Q 1 Q 2 Q 3 and Q 4 Each can be an oxygen atom or a direct bond.

[0246] Platinum complexes can be represented, for example, by chemical formula 7-1 or chemical formula 7-2.

[0247] [Chemical Formula 7-1]

[0248]

[0249] [Chemical Formula 7-2]

[0250]

[0251] In chemical formulas 7-1 and 7-2, X 100 These can be, for example, O, S, and NR. 132 .

[0252] R 118 To R 132 Each of these can be independently, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 133 R 134 R 135 .

[0253] R 133 To R 135 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0254] In one implementation, R 118 To R 132 At least one of them can be, for example, -SiR 133 R 134 R 135 Or tert-butyl.

[0255] R 133 To R 135 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0256] In addition to the light-emitting layer, the organic layer may also include charge transport regions.

[0257] The charge transport region can be, for example, the hole transport region 140.

[0258] The hole transport region 140 can further increase hole injection and / or hole mobility between the anode 120 and the light-emitting layer 130, and block electrons.

[0259] In one implementation, the hole transport region 140 may include a hole transport layer between the anode 120 and the light-emitting layer 130 and a hole transport auxiliary layer between the light-emitting layer 130 and the hole transport layer, and at least one of the hole transport layer and the hole transport auxiliary layer may include a compound of group B.

[0260] [Group B]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267] (Dn refers to the number of deuterium substitutions and indicates a structure with one or more deuterium atoms as substitutions).

[0268] In the hole transport region 140, in addition to the compounds mentioned above, other suitable compounds with similar structures may be used.

[0269] In addition, the charge transport region can be, for example, the electron transport region 150.

[0270] The electron transport region 150 can further increase electron injection and / or electron mobility between the cathode 110 and the light-emitting layer 130 and block holes.

[0271] In one implementation, the electron transport region 150 may include an electron transport layer between the cathode 110 and the light-emitting layer 130 and an electron transport auxiliary layer between the light-emitting layer 130 and the electron transport layer, and at least one of the electron transport layer and the electron transport auxiliary layer may include a compound of group C.

[0272] [Group C]

[0273]

[0274]

[0275]

[0276] Some exemplary implementations may be organic light-emitting diodes that include an organic light-emitting layer as an organic layer.

[0277] Some exemplary implementations may be organic light-emitting diodes that include an emitting layer and a hole transport region as organic layers.

[0278] Some exemplary implementations may be organic light-emitting diodes that include an emitting layer and an electron transport region as organic layers.

[0279] like Figure 1 As shown, in addition to the light-emitting layer 130, an organic light-emitting diode according to some exemplary embodiments may also include a hole transport region 140 and an electron transport region 150 as an organic layer 105.

[0280] In some exemplary embodiments, in addition to the light-emitting layer, the organic light-emitting diode may also include an electron injection layer, a hole injection layer, etc., as an organic layer.

[0281] An organic light-emitting diode 100 can be manufactured by forming an anode or cathode on a substrate, then forming an organic layer by a dry film method (such as vacuum deposition, sputtering, plasma electroplating and ion electroplating), and forming a cathode or anode thereon.

[0282] Organic light-emitting diodes (OLEDs) can be used in organic light-emitting display devices.

[0283] The following embodiments and comparative examples are provided to highlight features of one or more implementations; however, it will be understood that the embodiments and comparative examples should not be construed as limiting the scope of the implementations, nor should the comparative examples be construed as being outside the scope of the implementations. Furthermore, it will be understood that the implementations are not limited to the specific details described in the embodiments and comparative examples.

[0284] In the following examples and synthesis examples, the starting materials and reactants used were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry, or P&H Tech, or synthesized by suitable methods, unless otherwise specified.

[0285] (Synthesis of compounds for organic optoelectronic devices)

[0286] Synthesis Example 1: Synthesis of Compound 13

[0287] [Reaction Formula 1]

[0288]

[0289] Step 1: Synthesis of intermediate I-1

[0290] 4-Bromo-2-chloro-1-fluorobenzene (45.0 g, 214.9 mmol), [1,1'-biphenyl]-3-ylboronic acid (42.5 g, 214.9 mmol), K₂CO₃ (59.4 g, 429.7 mmol), and Pd(PPh₃)₄ (12.4 g, 10.7 mmol) were placed in a round-bottom flask, dissolved in tetrahydrofuran (THF) (850 ml) and distilled water (210 ml), and stirred under reflux at 70 °C for 12 hours. When the reaction was complete, the organic solvent was also removed from the mixture after separation and removal of the aqueous layer under reduced pressure. 45.6 g (75%) of intermediate I-1 was obtained by column chromatography (hexane:DCM (10% to 25%).

[0291] Step 2: Synthesis of intermediate I-2

[0292] Intermediate I-1 (45.6 g, 161.3 mmol), phenylboronic acid (35.4 g, 290.3 mmol), Cs₂CO₃ (78.8 g, 241.9 mmol), tri-tert-butylphosphine (13.1 g, 32.3 mmol), and Pd₂(dba)₃ (4.4 g, 4.8 mmol) were placed in a round-bottom flask, dissolved in 1,4-dioxane (800 mL), and stirred under reflux at 120 °C for 8 hours. After the reaction was complete, the organic solvent was removed under reduced pressure. 30.9 g (59%) of intermediate I-2 was obtained by column chromatography (hexane:DCM (10% to 30%)).

[0293] Step 3: Synthesis of intermediate I-3

[0294] Intermediate I-2 (30.9 g, 95.3 mmol) was dissolved in THF (350 ml) and stirred at -78 °C for 30 min. Lithium 2,2,6,6-tetramethylpiperidine (18.2 g, 123.8 mmol) was separately dissolved in THF (100 ml) and then slowly added to the mixture while stirring for 1 h. Triisopropylboronic acid ester (29 ml, 123.8 mmol) was then added and the mixture was stirred for 8 h while slowly increasing the temperature to ambient temperature. A 1 N HCl aqueous solution was added to adjust the pH to approximately 4-5 and the mixture was stirred for 2 h. After extraction with excess ethyl acetate, the organic layer was removed under reduced pressure. Excess hexane was added to precipitate it as a solid and then filtered. After drying at high temperature, 28.4 g (81%) of intermediate I-3 was obtained.

[0295] Step 4: Synthesis of intermediate I-4

[0296] Intermediate I-3 (28.4 g, 77.1 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (26.5 g, 77.1 mmol), K₂CO₃ (21.3 g, 154.3 mmol), and Pd(PPh₃)₄ (4.5 g, 3.9 mmol) were placed in a round-bottom flask, dissolved in THF (400 ml) and distilled water (80 ml), and stirred under reflux at 70 °C for 12 hours. After the reaction was complete, the product was cooled to ambient temperature, and the reactants were poured into excess methanol to precipitate a solid, which was then filtered. Recrystallization with monochlorobenzene (hereinafter referred to as MCB) yielded 40.4 g (83%) of intermediate I-4.

[0297] Step 5: Synthesis of Compound 13

[0298] Intermediate I-4 (21.0 g, 33.2 mmol), 2-phenyl-9H-carbazole (14.6 g, 59.8 mmol), and K3PO4 (14.1 g, 66.5 mmol) were placed in a round-bottom flask and dissolved in DMF (250 ml) at 150 °C. The mixture was then stirred and refluxed at 150 °C for 8 hours. After the reaction was complete, the reactants were slowly poured into excess water and stirred for 30 minutes. The precipitated solid was filtered, placed in MCB, heated until dissolved, and then filtered through a silica pad. The filtrate was distilled under reduced pressure, and the precipitated solid was filtered to obtain 25.0 g (88%) of compound 13.

[0299] Synthesis Example 2: Synthesis of Compound 24

[0300] [Reaction 2]

[0301]

[0302] Step 1: Synthesis of intermediate I-5

[0303] 22.1 g (62%) of intermediate I-5 was obtained by synthesizing 4-bromo-2-chloro-1-fluorobenzene (30.0 g, 143.2 mmol), phenylboronic acid (43.7 g, 358.1 mmol), K2CO3 (43.6 g, 315.1 mmol) and Pd(PPh3)4 (8.3 g, 7.2 mmol) in the same manner as in step 1 of Synthetic Example 1.

[0304] Step 2: Synthesis of intermediate I-6

[0305] Intermediate I-5 (22.1 g, 89.0 mmol) was synthesized in the same manner as in step 3 of Synthesis Example 1 to obtain 17.9 g (69%) of intermediate I-6.

[0306] Step 3: Synthesis of intermediate I-7

[0307] Intermediate I-6 (17.9 g, 61.3 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (21.9 g, 61.3 mmol), K2CO3 (16.9 g, 122.6 mmol) and Pd(PPh3)4 (3.5 g, 3.1 mmol) were synthesized in the same manner as in step 4 of Synthetic Example 1 to obtain 25.1 g (72%) of intermediate I-7.

[0308] Step 4: Synthesis of Compound 24

[0309] Using intermediate I-7 (21.0 g, 33.2 mmol), 9H-carbazole (11.1 g, 66.4 mmol), and K3PO4 (15.7 g, 73.7 mmol), 21.1 g (80%) of compound 24 was synthesized in the same manner as in step 5 of Synthetic Example 1.

[0310] Synthesis Example 3: Synthesis of Compound 46

[0311] [Reaction 3]

[0312]

[0313] Step 1: Synthesis of intermediate I-8

[0314] 2,4-Dichloro-6-phenyl-1,3,5-triazine (25.0 g, 110.6 mmol), 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-2-yl)-1,3,2-dioxane (34.8 g, 94.0 mmol), K₂CO₃ (30.6 g, 221.2 mmol), and Pd(dppf)Cl₂ (4.0 g, 5.5 mmol) were added to a round-bottom flask, dissolved in toluene (400 ml) and distilled water (120 ml), and then stirred under reflux at 60 °C for 8 hours. After the reaction was complete, the product was cooled to ambient temperature, and the precipitated solid was filtered off. The solid was added to MCB and dissolved by heating, and then filtered through a silica pad. The filtrate obtained was distilled under reduced pressure to precipitate a solid, which was then filtered to obtain 20.8 g (51%) of intermediate I-8.

[0315] Step 2: Synthesis of intermediate I-9

[0316] Using intermediate I-8 (20.8 g, 47.9 mmol), intermediate I-6 (14.0 g, 47.9 mmol), K2CO3 (13.3 g, 95.9 mmol), and Pd(PPh3)4 (2.8 g, 2.4 mmol), 26.3 g (85%) of intermediate I-9 was obtained in the same manner as in step 4 of Synthesis Example 1.

[0317] Step 3: Synthesis of Compound 46

[0318] Using intermediate I-9 (26.3 g, 40.7 mmol), 9H-carbazole (12.3 g, 73.3 mmol) and K3PO4 (17.3 g, 81.5 mmol), 27.1 g (84%) of compound 46 was synthesized in the same manner as in step 5 of Synthetic Example 1.

[0319] Synthesis Example 4: Synthesis of Compound C-4

[0320] [Reaction 4]

[0321]

[0322] 10.0 g (24.5 mmol) of intermediate 9-1, 6.3 g (26.9 mmol) of intermediate 9-2, 1.1 g (1.2 mmol) of Pd2(dba)3, 3.5 g (36.7 mmol) of NaOtBu and 0.7 g (3.7 mmol) of P(t-Bu)3 were added to a round-bottom flask and dissolved in 122 mL of xylene. The mixture was then stirred and refluxed at 140 °C for 12 hours. When the reaction was complete, distilled water was added, the mixture was stirred and the aqueous layer was removed. The resulting organic layer was filtered through silica gel and recrystallized to obtain 10.3 g (75%) of compound C-4.

[0323] (LC / MS theoretical value: 560.23 g / mol, measured value: M+ = 561.54 g / mol).

[0324] Synthesis Example 5: Synthesis of Compound C-5

[0325] [Reaction 5]

[0326]

[0327] 10.0 g (24.5 mmol) of intermediate 10⁻¹, 6.3 g (26.9 mmol) of intermediate 10⁻², 1.1 g (1.2 mmol) of Pd²(dba)³, 3.5 g (36.7 mmol) of NaOtBu, and 0.7 g (3.7 mmol) of P(t-Bu)³ were added to a round-bottom flask and dissolved in 122 mL of xylene. The mixture was then stirred and refluxed at 140 °C for 12 hours. When the reaction was complete, the result was added to distilled water, the mixture was stirred, and the aqueous layer was removed. The resulting organic layer was filtered through silica gel and recrystallized to obtain 9.7 g (71%) of compound C-5.

[0328] (LC / MS theoretical value: 560.23 g / mol, measured value: M+ = 561.57 g / mol).

[0329] Comparative Synthesis Example 1: Synthesis of Compound R-1

[0330] [Reaction Formula 6]

[0331]

[0332] Step 1: Synthesis of intermediate I-11

[0333] Intermediate I-11 was synthesized in the same manner as step 4 of Synthesis Example 1 by using 2-chloro-4,6-diphenyl-1,3,5-triazine and intermediate I-10.

[0334] Step 2: Synthesis of compound R-1

[0335] Compound R-1 was synthesized in the same manner as step 5 of Synthesis Example 1 by using intermediate I-11 and 9H-carbazole.

[0336] Comparative Synthesis Example 2: Synthesis of Compound R-2

[0337] [Reaction Formula 7]

[0338]

[0339] Step 1: Synthesis of intermediate I-12

[0340] Intermediate I-12 was synthesized using 2-chloro-4,6-diphenyl-1,3,5-triazine and 5-chloro-2-fluorophenylboronic acid in the same manner as step 4 of Synthetic Example 1.

[0341] Step 2: Synthesis of intermediate I-13

[0342] Intermediate I-13 was synthesized using intermediate I-12 and phenylboronic acid in the same manner as step 4 of Synthesis Example 1.

[0343] Step 3: Synthesis of compound R-2

[0344] Compound R-2 was synthesized using intermediate I-13 and 9H-carbazole in the same manner as step 5 of Synthesis Example 1.

[0345] Comparative Synthesis Example 3: Synthesis of Compound R-3

[0346]

[0347] Compound R-3 was synthesized by referring to the synthesis method described in Chinese patent CN114685462.

[0348] Comparative Synthesis Example 4: Synthesis of Compound R-4

[0349] [Reaction Equation 8]

[0350]

[0351] Step 1: Synthesis of intermediate I-14

[0352] Intermediate I-14 was synthesized using 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine and 4-chloro-2-fluorophenylboronic acid in the same manner as step 4 of Synthetic Example 1.

[0353] Step 2: Synthesis of intermediate I-15

[0354] Intermediate I-15 was synthesized using intermediate I-14 and phenylboronic acid in the same manner as step 4 of Synthesis Example 1.

[0355] Step 3: Synthesis of compound R-4

[0356] Compound R-4 was synthesized using intermediate I-15 and 9H-carbazole in the same manner as step 5 of Synthesis Example 1.

[0357] Example 1: Fabrication of a Green Organic Light Emitting Diode (Single Component)

[0358] 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 isopropanol, acetone, or methanol, dried, and then moved to a plasma cleaner for cleaning with oxygen plasma for 10 minutes, followed by a vacuum deposition process. Using this prepared ITO transparent electrode as the anode, compound A doped with 3% NDP-9 (Novaled GmbH) 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. Compound B is deposited on the hole transport layer to... The thickness was adjusted to form a hole transport auxiliary layer. Compound 13 was used as the host and PhGD was doped at 7 wt% as a dopant on the hole transport auxiliary layer by vacuum deposition. A thick luminescent layer. Then, compound C is deposited on the luminescent layer until... The thickness is sufficient to form an electron transport auxiliary layer, and compounds D and LiQ are simultaneously vacuum-deposited at a 1:1 weight ratio 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.

[0359] ITO / Compound A (3% NDP-9 doped) Compound A / Compound B / EML[Body (Compound 13): PhGD = 93 wt% : 7 wt%] / Compound C / Compound D:LiQ / LiQ / Al

[0360] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0361] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluorene-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0362] Compound C: 2,4-Diphenyl-6-(4',5',6'-triphenyl[1,1':2',1”:3”,1”':3”',1””-pentaphenyl]-3””-yl)-1,3,5-triazine

[0363] Compound D: 2-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluorene-4-yl)-6-phenyl-1,3,5-triazine

[0364] [PhGD]

[0365]

[0366] Examples 2 to 3 and Comparative Examples 1 to 4

[0367] Each organic light-emitting diode was manufactured in the same manner as in Example 1, except that the composition was changed to those shown in Table 1.

[0368] Example 4: Manufacturing of a Green Organic Light Emitting Diode (Hybrid Body)

[0369] A 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 isopropanol, acetone, or methanol, dried, and then moved to a plasma cleaner for cleaning with oxygen plasma for 10 minutes, followed by a vacuum deposition process. Using this prepared ITO transparent electrode as the anode, compound E doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited onto the ITO substrate to form... A thick hole injection layer, and compound E is deposited on the hole injection layer to... The thickness is increased to form a hole transport layer. Compound F is deposited on the hole transport layer to... The thickness was adjusted to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compound 13 and compound C-4 were used simultaneously in a 4:6 weight ratio as the host material, and 10 wt% PhGD was used as the dopant, by vacuum deposition to form... A thick luminescent layer. Subsequently, compound G is deposited on the luminescent layer until... The thickness is such that an electron transport auxiliary layer is formed, and compounds H and LiQ are simultaneously vacuum-deposited at a weight ratio of approximately 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.

[0370] ITO / compound E (3% NDP-9 doped) ) / Compound E / compound F / EML[Body (Compound 13: Compound C-4 = 4: 6 wt% / wt%): PhGD = 90 wt%: 10 wt%] / Compound G / Compound H:LiQ / LiQ / Al

[0371] Compound E: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine

[0372] Compound F: 9,9-Dimethyl-N-[3-(9-phenyl-9H-fluorene-9-yl)phenyl]-4-(4-phenylphenyl)-9H-fluorene-2-amine

[0373] Compound G: 4-{4-[4-(9,9-dimethyl-9H-fluoren-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[0374] Compound H: 2-(4-{1-[4-(diphenyl-1,3,5-triazin-2-yl)phenyl]naphthyl-2-yl}-4,6-diphenyl-1,3,5-triazine)

[0375] Examples 5 to 6 and Comparative Examples 5 to 8

[0376] Each organic light-emitting diode was manufactured in the same manner as in Example 4, except that the composition was changed to those shown in Table 2.

[0377] evaluate

[0378] The driving voltage, luminous efficiency, and lifetime characteristics of the organic light-emitting diodes according to Examples 1 to 6 and Comparative Examples 1 to 8 were evaluated.

[0379] The specific measurement methods are as follows, and the results are shown in Tables 1 and 2.

[0380] (1) Measure the change in current density based on voltage change.

[0381] While increasing the voltage from 0V to 10V, the current flowing through the unit device in the obtained organic light-emitting diode is measured using an ammeter-voltmeter (Keithley 2400), and the measured current value is divided by the area to provide the result.

[0382] (2) Measure the brightness change based on voltage changes

[0383] While increasing the voltage of the organic light-emitting diode from 0V to 10V, the brightness was measured using a luminance meter (MinoltaCs-1000A).

[0384] (3) Measure luminous efficiency

[0385] Using the brightness and current density from (1) and (2) above, and the voltage, calculations were performed at the same current density (10 mA / cm²). 2 Luminous efficiency (cd / A) at ).

[0386] Based on Comparative Example 1, the luminous efficiency values ​​of Examples 1 to 3 and Comparative Examples 1 to 4 were calculated as relative values ​​and are shown in Table 1.

[0387] Based on Comparative Example 5, the luminous efficiency values ​​of Examples 4 to 6 and Comparative Examples 5 to 8 were calculated as relative values ​​and are shown in Table 2.

[0388] (4) Measurement of lifespan

[0389] In terms of brightness (cd / m 2 Maintained at 24,000 cd / m 2 The lifetime is the time it takes for each luminous efficiency (cd / A) to decrease to 97%.

[0390] Based on Comparative Example 1, the lifetime values ​​of Examples 1 to 3 and Comparative Examples 1 to 4 were calculated as relative values ​​and are shown in Table 1.

[0391] Based on Comparative Example 5, the lifetime values ​​of Examples 4 to 6 and Comparative Examples 5 to 8 were calculated as relative values ​​and are shown in Table 2.

[0392] (5) Drive voltage measurement

[0393] The current-voltmeter (Keithley 2400) was used to measure at 15 mA / cm.2 The result is obtained by applying the driving voltage to each diode.

[0394] Based on Comparative Example 1, the driving voltages of Examples 1 to 3 and Comparative Examples 1 to 4 were calculated as relative values ​​and are listed in Table 1.

[0395] (Table 1)

[0396] serial number compound Drive voltage (%) Luminous efficiency (%) life(%) Example 1 13 93 108 120 Example 2 24 92 108 125 Example 3 46 95 110 115 Comparative Example 1 R-1 100 100 100 Comparative Example 2 R-2 104 101 100 Comparative Example 3 R-3 108 98 55 Comparative Example 4 R-4 103 102 90

[0397] (Table 2)

[0398] serial number First compound Second compound Luminous efficiency (%) life(%) Example 4 13 C-4 106 118 Example 5 24 C-4 107 120 Example 6 46 C-5 110 111 Comparative Example 5 R-1 C-4 100 100 Comparative Example 6 R-2 C-4 101 79 Comparative Example 7 R-3 C-5 100 42 Comparative Example 8 R-4 C-5 102 70

[0399] Referring to Tables 1 and 2, the driving voltage, luminous efficiency, and lifetime characteristics of the organic light-emitting diodes according to Examples 1 to 6 are significantly improved compared with those according to Comparative Examples 1 to 8.

[0400] One or more embodiments may provide compounds for organic optoelectronic devices that can reduce driving voltage and enable high-efficiency and long-life organic optoelectronic devices.

[0401] One or more embodiments may provide a composition for an organic optoelectronic device comprising a compound for an organic optoelectronic device.

[0402] It can realize high-efficiency, long-life organic optoelectronic devices while reducing driving voltage.

[0403] Exemplary embodiments have been disclosed herein, and although specific terminology has been used, it is used and interpreted in a superlative and descriptive sense only and not for limiting purposes. In some instances, as of the time of filing of this application, it will be apparent to those skilled in the art that 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 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 for use in organic optoelectronic devices, said compound being represented by chemical formula 1: [Chemical Formula 1] In chemical formula 1, Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. Ar 1 and Ar 2 At least one of them is a substituted or unsubstituted C10 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group. R 1 To R 10 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C30 alkyl or substituted or unsubstituted C6 to C30 aryl. R 11 and R 12 Each is independently either hydrogen or deuterium, and R 13 To R 20 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C20 heterocyclic.

2. The compound for organic optoelectronic devices according to claim 1, wherein, Ar 1 and Ar 2 At least one of them is a substituted or unsubstituted C6 to C30 unfused aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group.

3. The compound for organic optoelectronic devices according to claim 1, wherein, Ar 1 and Ar 2 At least one of them is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene.

4. The compound for organic optoelectronic devices according to claim 1, wherein, R 1 To R 10 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl.

5. The compound for organic optoelectronic devices according to claim 1, wherein, R 1 To R 10 Each of them independently is hydrogen, deuterium, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted phenyl, or substituted or unsubstituted biphenyl.

6. The compound for organic optoelectronic devices according to claim 1, wherein, R 13 To R 20 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, or substituted or unsubstituted C2 to C12 heterocyclic.

7. The compound for organic optoelectronic devices according to claim 1, wherein, R 13 To R 20 Each of these elements is independently hydrogen, deuterium, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted dibenzothiopheneyl.

8. The compound for organic optoelectronic devices according to claim 1, wherein, The compound is a compound from group 1: [Group 1] Dn refers to the number of deuterium substitutions and indicates a structure with one or more deuterium atoms as substitutions.

9. A composition for use in an organic optoelectronic device, comprising: The first compound; and The second compound, in: The first compound is the compound for organic optoelectronic devices according to any one of claims 1 to 8, and The second compound is represented by the following: Chemical formula 2, The combination of chemical formula 3 and chemical formula 4, Or chemical formula 5: [Chemical Formula 2] In chemical formula 2, R 21 To R 25 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. L 1 and L 2 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. m1, m4, and m5 are each an independent integer from 1 to 4. m2 and m3 are each an independent integer from 1 to 3, and n is an integer from 0 to 2; [Chemical Formula 3][Chemical Formula 4] In chemical formulas 3 and 4 In chemical formula 3, the two adjacent a1* to a4* are the connecting carbons attached to the * of chemical formula 4, and the remaining two a1* to a4* in chemical formula 3 that are not attached to the * of chemical formula 4 are CL. a -R a , L a L 3 and L 4 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. R a R 26 and R 27 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. m6 and m7 are each an independent integer from 1 to 4; [Chemical Formula 5] In chemical formula 5, L 5 It is a single-bonded or substituted or unsubstituted C6 to C20 arylene group. R 28 To R 31 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 7 It is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. m8, m10, and m11 are each an independent integer from 1 to 4, and m9 is an integer from 1 to 3.

10. The composition for an organic optoelectronic device according to claim 9, wherein: The second compound is represented by chemical formula 2. Chemical formula 2 is represented by chemical formula 2-8: [Chemical Formula 2-8] In chemical formula 2-8, R 21 To R 24 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group. m1 and m4 are each an independent integer from 1 to 4. m2 and m3 are each an independent integer from 1 to 3, and Partial -L 1 -Ar 3 and -L 2 -Ar 4 Each is an independent part of group I. [Group I] In group I, R 32 To R 36 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m12 is an integer from 1 to 5. m13 is an integer from 1 to 4. m14 is an integer from 1 to 3. m15 is 1 or 2. m16 is an integer from 1 to 7, and * indicates a connection point.

11. The composition for an organic optoelectronic device according to claim 9, wherein: The second compound is represented by a combination of chemical formulas 3 and 4. The combination of chemical formulas 3 and 4 is represented by chemical formula 3C: [Chemical formula 3C] In the chemical formula 3C, L a3 and L a4 Each is a single key. R 26 R 27 R a3 and R a4 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group. m6 and m7 are each an independent integer from 1 to 4. Partial -L 3 -Ar 5 and -L 4 -Ar 6 Each is an independent part of group I. [Group I] In group I, R 32 To R 36 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m12 is an integer from 1 to 5. m13 is an integer from 1 to 4. m14 is an integer from 1 to 3. m15 is 1 or 2. m16 is an integer from 1 to 7, and * indicates a connection point.

12. An organic optoelectronic device, comprising: The anode and cathode facing each other, and At least one organic layer between the anode and the cathode, Wherein, the at least one organic layer comprises a compound for an organic optoelectronic device as described in any one of claims 1 to 8; or The composition for an organic optoelectronic device according to any one of claims 9 to 11.

13. The organic optoelectronic device according to claim 12, wherein: The at least one organic layer includes a light-emitting layer, and The light-emitting layer comprises the compound for organic optoelectronic devices or the composition for organic optoelectronic devices.

14. A display device comprising the organic optoelectronic device of claim 12 or 13.

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