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 comprising the compound for an organic optoelectronic device, an organic optoelectronic device comprising the compound or the composition, and a display device comprising the organic optoelectronic device, the compound is represented by Chemical Formula 1 or Chemical Formula 2.

Description

[0001] Citations of relevant applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0126131, filed on September 13, 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 into light energy and vice versa.

[0005] Based on their working principles, organic optoelectronic devices can be divided into two categories. One category 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 category 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 attracted considerable 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 can be influenced by the organic materials between the electrodes. Summary of the Invention

[0008] The implementation can be achieved by providing a compound for an organic optoelectronic device, the compound being represented by chemical formula 1 or chemical formula 2:

[0009] [Chemical Formula 1]

[0010]

[0011] [Chemical Formula 2]

[0012]

[0013] In chemical formulas 1 and 2, R 1 To R 6 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl, R 7It is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl, m1 to m3, m5 and m7 are each independently an integer from 1 to 4, m4 is an integer from 1 to 3, m6 is an integer from 1 to 5, and when m1 is 2, 3 or 4, each R 1 Whether they are the same or different, when m2 is 2, 3 or 4, each R 2 Whether they are the same or different, when m3 is 2, 3 or 4, each R 3 Whether they are the same or different, when m4 is 2 or 3, each R 4 Whether they are the same or different, when m5 is 2, 3 or 4, each R 5 Whether they are the same or different, when m6 is 2, 3, 4 or 5, each R 6 They are the same or different from each other, and when m7 is 2, 3 or 4, each R 7 They are the same or different from each other.

[0014] The implementation can be achieved by providing a composition for an organic optoelectronic device, the composition comprising a first compound and a second compound, wherein the first compound can be a compound for an organic optoelectronic device according to one embodiment, and the second compound can be represented by chemical formula 3, a combination of chemical formulas 4 and 5, or chemical formula 6:

[0015] [Chemical Formula 3]

[0016]

[0017] In chemical formula 3, R 8 To R 12 Each of these can be 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 1 and Ar 2 Each can be 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 following can be a single bond or a substituted or unsubstituted C6 to C20 aryl group; m8, m11, and m12 can each be an integer from 1 to 4; m9 and m10 can each be an integer from 1 to 3; when m8 is 2, 3, or 4, each R 8 They can be the same or different from each other, and when m9 is 2 or 3, each R 9 They can be the same or different from each other, and when m10 is 2 or 3, each R 10 They can be the same or different from each other. When m11 is 2, 3 or 4, each R 11They can be the same or different from each other, and when m12 is 2, 3 or 4, each R 12 They can be the same or different from each other, and n can be an integer from 0 to 2;

[0018]

[0019]

[0020] In chemical formulas 4 and 5, the two adjacent carbons a1* to a4* of chemical formula 4 can be connecting carbons attached to the * position of chemical formula 5, and the remaining two carbons a1* to a4* of chemical formula 4 that are not attached to the * position of chemical formula 5 can be CL. a -R a L a L 3 and L 4 Each can be a single bond or a substituted or unsubstituted C6 to C20 aryl group, R a R 13 and R 14 Each of these can be 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 of the following can be an independently substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group; m13 and m14 can each be an independently substituted integer from 1 to 4. When m13 is 2, 3, or 4, each R 13 They can be the same or different from each other, and when m14 is 2, 3 or 4, each R 14 They can be the same as or different from each other;

[0021] [Chemical Formula 6]

[0022]

[0023] In chemical formula 6, L 5 It can be a single bond or a substituted or unsubstituted C6 to C20 aryl group, R 15 To R 18 Each of these can be 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 It can be a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. m15, m17, and m18 can each be an integer from 1 to 4 independently, and m16 can be an integer from 1 to 3. When m15 is 2, 3, or 4, each R15 They can be the same or different from each other, and when m16 is 2 or 3, each R 16 They can be the same or different from each other, and when m17 is 2, 3 or 4, each R 17 They can be the same or different from each other, and when m18 is 2, 3 or 4, each R 18 They can be the same as or different from each other.

[0024] The implementation can be achieved 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 organic layer comprises a compound or composition for an organic optoelectronic device according to some embodiments.

[0025] The implementation can be achieved by providing a display device that includes an organic optoelectronic device according to some embodiments. Attached Figure Description

[0026] The features will become apparent to those skilled in the art from the detailed description of exemplary embodiments with reference to the accompanying drawings, wherein:

[0027] Figure 1 This is a cross-sectional view of an organic light-emitting diode according to some exemplary embodiments.

[0028] <Explanation of Figure Markers>

[0029] 100: Organic Light Emitting Diode

[0030] 105: Organic layer

[0031] 110: Cathode

[0032] 120: Anode

[0033] 130: Emissive layer

[0034] 140: Hole transport region

[0035] 150: Electron transport region Detailed Implementation

[0036] 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 limited to the embodiments described herein. Rather, these embodiments are provided to make the invention disclosure complete and exhaustive, and to fully express exemplary implementations to those skilled in the art.

[0037] In the accompanying drawings, the dimensions of layers and regions may be enlarged for clarity. It will also be understood that when a layer or element is referred to as "on" another layer or substrate, it may be located directly on the other layer or substrate, or there may be intermediate layers. Furthermore, it will be understood that when a layer is referred to as "below" another layer, it may be located directly below the other layer, and one or more intermediate layers may be present. Additionally, it will be understood that when a layer is referred to as "between" two layers, it may be the only layer between the two layers, or one or more intermediate layers may be present. Throughout the specification, the same reference numerals denote the same elements.

[0038] The embodiments are described in detail below. However, these embodiments are exemplary and this disclosure is not limited thereto.

[0039] 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.

[0040] In one instance, "substituted" means that at least one hydrogen atom of a 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 a specific instance, "substituted" means that at least one hydrogen atom of a 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 a specific instance, "substituted" means that at least one hydrogen atom of a 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 specific instances, "substituted" means that at least one hydrogen atom of a 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.

[0041] "Unsubstituted" means that the hydrogen atom is not replaced by another substituent and retains the hydrogen atom.

[0042] 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).

[0043] 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.

[0044] 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 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 directly or indirectly fused to provide a non-aromatic fused ring, such as fluorene.

[0045] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent carbon atom pairs) functional groups.

[0046] 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.

[0047] In one embodiment, "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 one to three heteroatoms.

[0048] 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.

[0049] 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.

[0050] As used herein, hole properties 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 emissive layer due to the conductivity of the highest occupied molecular orbital (HOMO) energy level.

[0051] 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.

[0052] The following describes compounds for organic optoelectronic devices according to some exemplary embodiments.

[0053] Compounds for organic optoelectronic devices according to some exemplary embodiments are represented by chemical formula 1 or chemical formula 2.

[0054] [Chemical Formula 1]

[0055]

[0056] [Chemical Formula 2]

[0057]

[0058] In chemical formulas 1 and 2, R1 To R 6 Each of these components may be, independently, or include, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl groups or substituted or unsubstituted C6 to C12 aryl groups.

[0059] R 7 It may be or include, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl.

[0060] m1 to m3, m5 and m7 can each be an integer, for example, 1 to 4, independently.

[0061] m4 can be, for example, an integer from 1 to 3.

[0062] m6 can be, for example, an integer from 1 to 5.

[0063] The compounds represented by Formula 1 or Formula 2 have structures in which the o-phenylene group attached to the triazine is replaced by carbazole, the p-phenylene or meta-phenylene group attached to the triazine is replaced by dibenzothiophene, and the triazine is replaced by a phenyl group. By replacing the o-phenylene group with carbazole, the stability of the portion with electron-hole characteristics is improved, thus organic light-emitting diodes including this compound can help achieve significantly improved lifetime characteristics while maintaining high efficiency. Furthermore, by replacing the p-phenylene or meta-phenylene group with dibenzothiophene, high efficiency characteristics can be achieved due to the heavy atom effect of sulfur. And by replacing with a phenyl group, a shallow LUMO can be maintained compared to the dibenzofuran group, thereby achieving high efficiency characteristics.

[0064] In one implementation, m1 can be 2, 3, or 4, and each R 1 They can be the same or different from each other.

[0065] In one implementation, m2 can be 2, 3, or 4, and each R 2 They can be the same or different from each other.

[0066] In one implementation, m3 can be 2, 3, or 4, and each R 3 They can be the same as or different from each other, and

[0067] In one implementation, m4 can be 2 or 3, and each R 4 They can be the same as or different from each other.

[0068] In one implementation, m5 can be 2, 3, or 4, and each R 5 They can be the same as or different from each other.

[0069] In one implementation, m6 can be 2, 3, 4, or 5, and each R 6 They can be the same as or different from each other.

[0070] In one implementation, m7 can be 2, 3, or 4, and each R 7 They can be the same as or different from each other.

[0071] In one embodiment, chemical formula 1 may be represented, for example, by one of chemical formulas 1-1 to 1-4.

[0072] [Chemical Formula 1-1]

[0073]

[0074] [Chemical Formula 1-2]

[0075]

[0076] [Chemical Formulas 1-3]

[0077]

[0078] [Chemical Formulas 1-4]

[0079]

[0080] In chemical formulas 1-1 to 1-4, R 1 To R 7 m1 to m7 can be the same as those defined above.

[0081] In one embodiment, chemical formula 2 may be represented, for example, by one of chemical formulas 2-1 to 2-4.

[0082] [Chemical Formula 2-1]

[0083]

[0084] [Chemical Formula 2-2]

[0085]

[0086] [Chemical Formula 2-3]

[0087]

[0088] [Chemical Formula 2-4]

[0089]

[0090] In chemical formulas 2-1 to 2-4, R 1 To R 7 m1 to m7 can be the same as those defined above.

[0091] In one implementation, R1 To R 6 Each of these can be, independently, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C6 alkyl, or substituted or unsubstituted phenyl.

[0092] In one implementation, R 7 It can be, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C6 alkyl or substituted or unsubstituted phenyl.

[0093] In one implementation, R 1 To R 6 Each can be, independently, for example, hydrogen, deuterium, cyano, tert-butyl, or substituted or unsubstituted phenyl.

[0094] In one implementation, R 7 It can be, for example, hydrogen, deuterium, tert-butyl, or substituted or unsubstituted phenyl.

[0095] In one embodiment, the compound represented by chemical formula 1 or chemical formula 2 may be a compound of group 1.

[0096] [Group 1]

[0097]

[0098]

[0099] According to some exemplary embodiments, the composition for an organic optoelectronic device comprises a first compound and a second compound, wherein the first compound is the compound described above for an organic optoelectronic device, and the second compound may be represented by chemical formula 3, a combination of chemical formula 4 and chemical formula 5, or chemical formula 6.

[0100] [Chemical Formula 3]

[0101]

[0102] In chemical formula 3, R 8 To R 12 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.

[0103] Ar 1 and Ar 2 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.

[0104] L 1 and L 2They can be, for example, single bonds or substituted or unsubstituted C6 to C20 aryl groups.

[0105] m8, m11, and m12 can each be an integer from 1 to 4, for example, independently.

[0106] m9 and m10 can each be an integer, for example, from 1 to 3, independently.

[0107] n can be an integer, for example, from 0 to 2.

[0108]

[0109] In chemical formulas 4 and 5, two adjacent a1* to a4* of chemical formula 4 can each be a connecting carbon affixed to * in chemical formula 5.

[0110] The two remaining parts of a1* to a4* in chemical formula 4 that are not connected to the * in chemical formula 5 can be, for example, CL. a -R a .

[0111] L a L 3 and L 4 They can be, for example, single bonds or substituted or unsubstituted C6 to C20 aryl groups.

[0112] R a R 13 and R 14 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.

[0113] Ar 3 and Ar 4 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.

[0114] m13 and m14 can each be an integer, for example, from 1 to 4, independently.

[0115] [Chemical Formula 6]

[0116]

[0117] In chemical formula 6, L 5 It can be, for example, a single bond or a substituted or unsubstituted C6 to C20 aryl group.

[0118] R 15 To R 18Each 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.

[0119] Ar 5 It can be, for example, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0120] m15, m17, and m18 can each be an integer from 1 to 4, for example, independently.

[0121] m16 can be, for example, an integer from 1 to 3.

[0122] 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.

[0123] In one implementation, m8 can be 2, 3, or 4, and each R 8 They can be the same as or different from each other.

[0124] In one implementation, m9 can be 2 or 3, and each R 9 They can be the same as or different from each other.

[0125] In one implementation, m10 can be 2 or 3, and each R 10 They can be the same as or different from each other.

[0126] In one implementation, m11 can be 2, 3, or 4, and each R 11 They can be the same as or different from each other.

[0127] In one implementation, m12 can be 2, 3, or 4, and each R 12 They can be the same as or different from each other.

[0128] In one implementation, m13 can be 2, 3, or 4, and each R 13 They can be the same as or different from each other.

[0129] In one implementation, m14 can be 2, 3, or 4, and each R 14 They can be the same as or different from each other.

[0130] In one implementation, m15 can be 2, 3, or 4, and each R 15 They can be the same as or different from each other.

[0131] In one implementation, m16 can be 2 or 3, and each R 16 They can be the same as or different from each other.

[0132] In one implementation, m17 can be 2, 3, or 4, and each R 17 They can be the same as or different from each other.

[0133] In one implementation, m18 can be 2, 3, or 4, and each R 18 They can be the same as or different from each other.

[0134] In one embodiment, in chemical formula 3, Ar 1 and Ar 2 Each 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 triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted fluorenyl.

[0135] In one embodiment, in chemical formula 3, L 1 and L 2 Each can be a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0136] In one embodiment, in chemical formula 3, R 8 To R 12 They can be hydrogen, deuterium, or substituted or unsubstituted C6 to C12 aryl groups, each independently.

[0137] In one implementation, n in chemical formula 3 can be 0 or 1.

[0138] In one embodiment, in Formula 3, "substituted" can mean that at least one hydrogen atom is replaced by a deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0139] In one embodiment, in chemical formula 3, Ar 1 and Ar 2 Each can be independently a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, or a substituted or unsubstituted fluorenyl.

[0140] In one embodiment, chemical formula 3 may be represented by one of chemical formulas 3-1 to 3-15.

[0141]

[0142]

[0143] In chemical formulas 3-1 to 3-15, R 8 To R 12 Each can be independently, for example, hydrogen, deuterium, or substituted or unsubstituted C6 to C12 aryl groups, and *-L 1 -Ar 1 and *-L 2 -Ar 2 Each part can be an independent part of group I.

[0144] [Group I]

[0145]

[0146] In group I, R 19 To R 23 Each can be independently, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl.

[0147] m19 can be, for example, an integer from 1 to 5.

[0148] m20 can be, for example, an integer from 1 to 4.

[0149] m21 can be, for example, an integer from 1 to 3.

[0150] m22 can be an integer, for example, 1 or 2.

[0151] m23 can be, for example, an integer from 1 to 7.

[0152] * indicates a connection point.

[0153] In one implementation, m19 can be 2, 3, 4, or 5, and each R 19 They can be the same as or different from each other.

[0154] In one implementation, m20 can be 2, 3, or 4, and each R 20 They can be the same as or different from each other.

[0155] In one implementation, m21 can be 2 or 3, and each R 21 They can be the same as or different from each other.

[0156] In one implementation, m22 can be 2, and each R 22 They can be the same as or different from each other.

[0157] In one implementation, m23 can be 2, 3, 4, 5, 6, or 7, and each R 23 They can be the same as or different from each other.

[0158] Combinations of chemical formulas 4 and 5 can be, for example, derived from chemical formulas 4A, 4B, and 5.

[0159] It can be represented by one of the following: Formula 4C, Formula 4D, or Formula 4E.

[0160]

[0161] In chemical formulas 4A to 4E, L 3 L 4 Ar 3 Ar 4 R 13 R 14 m13 and m14 can be the same as those defined above.

[0162] L a1 To L a4 Can be combined with the above L 3 and L 4 The definitions are the same.

[0163] R a1 To R a4 It can be used with the above R 13 and R 14 The definitions are the same.

[0164] In one implementation, in chemical formulas 4 and 5, Ar 3 and Ar 4 Each 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 triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted fluorenyl.

[0165] In one implementation, R a1 To R a4 R 13 and R 14 Each of these can be 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.

[0166] In one embodiment, in chemical formulas 4 and 5, *-L 3 -Ar 3 and *-L 4 -Ar 4 Each part can be an independent part of group I.

[0167] In some exemplary embodiments, R a1 To R a4 R 13 and R 14 Each of these can be 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.

[0168] In one implementation, R a1 To R a4 R 13 and R 14 Each can be an independent group of hydrogen, deuterium, cyano, or substituted or unsubstituted phenyl groups.

[0169] In one implementation, R a1 To R a4 R 13 and R 14 Each can be hydrogen, deuterium, or a substituted or unsubstituted phenyl group, independently.

[0170] Chemical formula 6 can be represented, for example, by one of chemical formulas 6-1 to 6-4.

[0171]

[0172]

[0173] In chemical formulas 6-1 to 6-4, L 5 Ar 5 R 15 To R 18 And m15 to m18 can be the same as those defined above.

[0174] In one implementation, in chemical formula 6, Ar 5 It can be 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 triphenylene, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted fluorenyl.

[0175] In one implementation, R 15 To R 18 Each of these can be 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.

[0176] In one embodiment, in chemical formula 6, *-L 5 -Ar 5 A part can be a part of group I.

[0177] In one implementation, R 15 To R 18 Each can be an independent group of hydrogen, deuterium, cyano, or substituted or unsubstituted phenyl groups.

[0178] In one embodiment, chemical formula 3 can be represented by chemical formula 3-8, in which Ar 1 and Ar 2 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 an independent, for example, a single bond or a substituted or unsubstituted C6 to C20 aryl group, R 8 To R 11 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.

[0179] In one embodiment, in chemical formulas 3-8, R 8 To R 11 Each can be independently, for example, hydrogen, deuterium, or substituted or unsubstituted C6 to C12 aryl groups, and *-L 1 -Ar 1 and *-L 2 -Ar 2 Each part can be, for example, a part of group I, and can be independent of each other.

[0180] In one embodiment, the second compound may be represented by the chemical formula 4C, and in the chemical formula 4C, L a3 and L a4 Each can be a single key, 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 13 R 14 R a3 and R a4 Each can be independently, for example, hydrogen, deuterium, or phenyl, and Ar 3 and Ar 4Each 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.

[0181] In one embodiment, in chemical formula 4C, L a3 and L a4 Each can be a single key, R 13 R 14 R a3 and R a4 Each can be independently, for example, hydrogen, deuterium, or C6 to C12 aryl, and *-L 3 -Ar 3 and *-L 4 -Ar 4 Each part can be, for example, a part of group I, and can be independent of each other.

[0182] In one embodiment, the second compound for the organic optoelectronic device may be a compound of group 2.

[0183] [Group 2]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192] In addition, examples are given below of at least one hydrogen atom in compounds B-1 to B-150 listed in Group 2 being replaced by deuterium.

[0193] In one embodiment, for example, deuterium may be substituted as shown in compounds B-151 to B-195, which are illustrated below.

[0194]

[0195]

[0196] (Dn refers to the number of deuterium substitutions and indicates the structure substituted by one or more deuterium atoms)

[0197] The deuterium substitution position and deuterium substitution rate can include all variable ranges from compound B-1 to compound B-195 (e.g., any hydrogen in any compound can be protium or deuterium).

[0198] The most specific structures of compounds B-151 to B-195 of Group 2 are presented below as examples based on the position and rate of deuterium substitution.

[0199] In one embodiment, for example, deuterium may be substituted as shown in compounds B-196 to B-234.

[0200]

[0201]

[0202]

[0203]

[0204] In one embodiment, the second compound for the organic optoelectronic device may be, for example, a compound from group 3.

[0205] [Group 3]

[0206]

[0207]

[0208]

[0209]

[0210] In one embodiment, examples are given below of at least one hydrogen atom in compounds C-1 to C-57 listed in Group 3 being replaced by deuterium. In one embodiment, for example, deuterium may be substituted as illustrated below by compounds C-58 to C-72.

[0211]

[0212]

[0213] (Dn refers to the number of deuterium substitutions and indicates the structure substituted by one or more deuterium atoms)

[0214] The deuterium substitution position and deuterium substitution rate can include all variable ranges from compound C-1 to compound C-72 (e.g., any hydrogen in any compound can be protium or deuterium).

[0215] The most specific structures of compounds C-58 to C-72 of Group 3 are presented below as examples based on the position and rate of deuterium substitution.

[0216] In one embodiment, deuterium may be substituted as shown in compounds C-73 to C-102.

[0217]

[0218]

[0219]

[0220] In one embodiment, the second compound for the organic optoelectronic device may be, for example, a compound from group 4.

[0221] [Group 4]

[0222]

[0223]

[0224]

[0225] In addition, examples are given below of at least one hydrogen atom in compounds D-1 to D-60 listed in group 4 being replaced by deuterium.

[0226] In one embodiment, for example, deuterium may be substituted as shown by compounds D-61 to D-120, which are illustrated below.

[0227]

[0228]

[0229]

[0230]

[0231] (Dn refers to the number of deuterium substitutions and indicates the structure substituted by one or more deuterium atoms)

[0232] The first and second compounds can be included in a weight ratio of, for example, from about 1:99 to about 99:1. By including them within the above range, bipolar characteristics can be achieved by adjusting the appropriate weight ratio using the electron transport capability of the first compound and the hole transport capability of the second compound, thereby improving efficiency and lifetime. 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, for example, 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 embodiment, they can be included in a weight ratio of about 40:60, about 50:50, or about 60:40.

[0233] In the following text, organic optoelectronic devices comprising the compounds or compositions described above for use in organic optoelectronic devices will be described.

[0234] 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.

[0235] 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.

[0236] Figure 1 This is a cross-sectional view of an organic light-emitting diode according to some exemplary embodiments.

[0237] refer to 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.

[0238] The anode 120 can be made of a conductor with a high work function to facilitate hole injection, and can be, for example, a metal, a metal oxide, or a conductive polymer. The anode 120 can 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.

[0239] The cathode 110 can be made of a conductor with a small work function to aid electron injection, and can be, for example, a metal, a metal oxide, or a conductive polymer. The cathode 110 can 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, and BaF2 / Ca.

[0240] The organic layer 105 may include the compounds or compositions described above for organic optoelectronic devices.

[0241] 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, such as a red, green or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0242] The dopant can be a material mixed in small amounts with a compound or composition for 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. The dopant can be, for example, an inorganic, organic, or organic-inorganic compound, and one or more of these types can be used.

[0243] Examples of dopants may be or include phosphorescent dopants, and examples of phosphorescent dopants may be or include organometallic compounds comprising Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants may be, for example, compounds represented by the chemical formula Z.

[0244] [Chemical Formula Z]

[0245] L 6 MX 1

[0246] In the chemical formula Z, M can be, for example, a metal, and L 6 and X 1 They can be the same or different and can be, for example, ligands that form complexes with M.

[0247] 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.

[0248] By L 6 and X 1The ligand represented can be, for example, one of the chemical formulas Z-1 to Z-8.

[0249] [Chemical Formula Z-1][Chemical Formula Z-2][Chemical Formula Z-3]

[0250]

[0251] [Chemical Formula Z-8]

[0252]

[0253] In chemical formulas Z-1 to Z-8, X 14 It can be, for example, carbon or nitrogen.

[0254] Y 100 It can be, for example, O or S.

[0255] R 101 To R 122 Each of these can be independently, for example, hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, -SiR 133 R 134 R 135 Or -GeR 133 R 134 R 135 Alternatively, it can be attached to an adjacent substituent to form a substituted or unsubstituted ring, and for example, together with pyridine, it can form a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuranopyridine, a substituted or unsubstituted benzothiophenopyridine, a substituted or unsubstituted indenepyridine, a substituted or unsubstituted benzofuranoquinoline, a substituted or unsubstituted benzothiophenoquinoline, or a substituted or unsubstituted indenequinoline.

[0256] R 133 To R 135 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0257] m111 can be an integer such as 1 or 2.

[0258] m18 can be, for example, an integer from 1 to 4.

[0259] m19 can be, for example, an integer from 1 to 5.

[0260] By L 6 and X 1 Examples of ligands can be, for example, chemical formulas of group A.

[0261] [Group A]

[0262]

[0263]

[0264] In group A, R 300 To R 302 Each of these can be, independently, for example, hydrogen, deuterium, halogen-substituted or unsubstituted C1 to C30 alkyl groups, halogen-substituted or unsubstituted C6 to C30 aryl groups, or halogens.

[0265] R 303 To R 308 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.

[0266] m25 can be, for example, an integer from 1 to 5.

[0267] m26 can be, for example, an integer from 1 to 4.

[0268] m27 can be, for example, an integer from 1 to 3.

[0269] m28 can be an integer, for example, 1 or 2.

[0270] m29 can be, for example, an integer from 1 to 6.

[0271] In one implementation, any one of m25 to m27 and m29 can be an integer of 2 or greater, m28 can be 2, and R 303 To R 307 Each can be the same as or different from the other.

[0272] The dopant according to some exemplary embodiments may be an iridium complex and may be represented, for example, by one of chemical formulas 7 to 9.

[0273] [Chemical Formula 7]

[0274]

[0275] In chemical formula 7, ring A can be, for example, a monocyclic or polycyclic fused ring, wherein each ring in the monocyclic or polycyclic fused ring can be, for example, a 5- or 6-membered carbon ring or a heterocyclic ring.

[0276] R 100 It can represent, for example, one to a maximum number of monovalent substituents.

[0277] In one implementation, there may be two or more Rs. 100 Groups, and each R 100 They can be the same as or different from each other.

[0278] R 101 To R 104 Each of these can be independently, for example, hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 114 R 115 R 116 -GeR 114 R 115 R 116 Or a combination thereof.

[0279] R 114 To R 116 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0280] X 10 and X 11 They can be, for example, carbon or nitrogen, each independently.

[0281] L 100 It can be, for example, a monovalent anion ligand or a bidentate ligand that coordinates to iridium via a non-shared electron pair of a carbon or heteroatom.

[0282] m21 can be, for example, an integer from 0 to 3.

[0283] [Chemical Formula 8]

[0284]

[0285] In Formula 8, ring B can be, for example, a monocyclic or polycyclic fused ring, wherein each ring in the monocyclic or polycyclic fused ring can be, for example, a 5- or 6-membered carbon ring or a heterocyclic ring.

[0286] Y 100 It can be, for example, O or S.

[0287] R 201 It can represent, for example, one to a maximum number of monovalent substituents.

[0288] In one implementation, there may be two or more Rs. 201 Groups, and each R 201 They can be the same as or different from each other.

[0289] R206 To R 213 Each of these can be independently, for example, hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 114 R 115 R 116 -GeR 114 R 115 R 116 Or a combination thereof.

[0290] R 114 To R 116 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0291] X 12 and X 13 They can be, for example, carbon or nitrogen, each independently.

[0292] L 100 It can be, for example, a monovalent anion ligand or a bidentate ligand that coordinates to iridium via a non-shared electron pair of a carbon or heteroatom.

[0293] m21 can be, for example, an integer from 0 to 3.

[0294] m100 can be, for example, an integer from 1 to 3.

[0295] m101 can be an integer such as 1 or 2.

[0296] n100 can be an integer, for example, 0 or 1.

[0297] [Chemical Formula 9]

[0298]

[0299] In chemical formula 9, Y 100 It can be, for example, O or S.

[0300] R 101 To R 111 Each of these can be independently, for example, hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 114 R 115 R 116 -GeR 114 R 115 R 116 Or a combination thereof.

[0301] R 114 To R 116 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0302] L 100 It can be, for example, a monovalent anion ligand or a bidentate ligand that coordinates to iridium via a non-shared electron pair of a carbon or heteroatom.

[0303] m21 can be, for example, an integer from 0 to 3.

[0304] In one embodiment, the iridium complex may be represented by, for example, one of chemical formulas 7-1 to 7-6.

[0305] [Chemical Formula 7-1]

[0306]

[0307] In chemical formula 7-1, R 101 To R 116 Each of these can be independently, for example, hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 132 R 133 R 134 Or -GeR 132 R 133 R 134 .

[0308] R 132 To R 134 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0309] R 101 To R 116 At least one of them can be a functional group, for example, represented by the chemical formula V-1.

[0310] L 100 It can be, for example, a bidentate ligand of a monovalent anion, and can be, for example, a ligand coordinated to iridium via a lone pair of electrons of a carbon or heteroatom.

[0311] m21 and m22 can each be an integer from 0 to 3 independently, and m21+m22 can be an integer from 1 to 3.

[0312] [Chemical Formula V-1]

[0313]

[0314] 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 R 133 R 134 .

[0315] * refers to the part that is attached to a carbon atom.

[0316] [Chemical Formula 7-2]

[0317]

[0318] [Chemical Formula 7-3]

[0319]

[0320] [Chemical Formula 7-4]

[0321]

[0322] [Chemical Formula 7-5]

[0323]

[0324] [Chemical Formula 7-6]

[0325]

[0326] In chemical formulas 7-2 to 7-6, X 14 It can be, for example, carbon or nitrogen.

[0327] Y 100 It can be, for example, O or S.

[0328] R 101 To R 122 Each of these can be independently, for example, hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 133 R 134 R 135 Or -GeR 133 R 134 R 135 .

[0329] R 133 To R 135 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0330] L 100 It can be, for example, a bidentate ligand of a monovalent anion, and can be, for example, a ligand coordinated to iridium via a lone pair of electrons of a carbon or heteroatom.

[0331] m111 can be, for example, an integer from 1 to 2.

[0332] n1 and n2 can each be an integer from 0 to 3 independently, and n1+n2 can be an integer from 1 to 3.

[0333] According to one embodiment, the dopant may be, for example, a platinum complex, and may be represented by, for example, the chemical formula Z-1.

[0334] [Chemical Formula Z-1]

[0335]

[0336] In chemical formula Z-1, rings A, B, C, and D can each be, for example, a 5- or 6-membered carbon ring or a heterocycle.

[0337] R A R B R C and R D They can be individually, for example, mono-, di-, tri-, or tetra-substituted or unsubstituted.

[0338] nA can be an integer, for example, 0 or 1.

[0339] 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.

[0340] 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.

[0341] In one implementation, nA can be 0, and L E It can be non-existent.

[0342] 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; any adjacent R A R B R C R D R and R' can be optionally connected to each other to provide a ring; X B X C X D and X EEach can be, for example, carbon or nitrogen; and Q 1 Q 2 Q 3 and Q 4 Each can be an oxygen bond or a direct bond, for example, independently.

[0343] Platinum complexes can be represented, for example, by chemical formula 8-1 or chemical formula 8-2.

[0344] [Chemical Formula 8-1]

[0345]

[0346] [Chemical Formula 8-2]

[0347]

[0348] In chemical formulas 8-1 and 8-2, X 100 It can be, for example, O, S, or NR. 132 .

[0349] 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 .

[0350] R 133 To R 135 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0351] 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.

[0352] R 133 To R 135 Each can be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0353] In addition to the light-emitting layer, the organic layer may also include charge transport regions.

[0354] The charge transport region can be, for example, the hole transport region 140.

[0355] Hole transport region 140 can help to further increase hole injection or hole mobility between anode 120 and light-emitting layer 130 and block electrons.

[0356] In one embodiment, the hole transport region 140 may include, for example, 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 contain a compound of group B.

[0357] [Group B]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364] (Dn refers to the number of deuterium substitutions and indicates the structure substituted by one or more deuterium atoms)

[0365] In the hole transport region 140, in addition to the compounds mentioned above, other suitable compounds with similar structures may be used.

[0366] In one embodiment, the charge transport region may be, for example, the electron transport region 150.

[0367] The electron transport region 150 can help to further increase the electron injection or electron mobility between the cathode 110 and the light-emitting layer 130 and help to block holes.

[0368] In one embodiment, 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 contain a compound of group C.

[0369] [Group C]

[0370]

[0371]

[0372]

[0373] Some exemplary implementations may be organic light-emitting diodes that include an organic light-emitting layer as an organic layer.

[0374] Some exemplary implementations may be organic light-emitting diodes that include an emitting layer and a hole transport region as organic layers.

[0375] Some exemplary implementations may be organic light-emitting diodes that include an emitting layer and an electron transport region as organic layers.

[0376] In addition to the light-emitting layer 130 serving as the organic layer 105, an organic light-emitting diode according to one embodiment may further include a hole transport region 140 and an electron transport region 150, such as... Figure 1 As shown.

[0377] In one embodiment, 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 organic layers.

[0378] 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 (e.g., vacuum deposition, sputtering, plasma electroplating, or ion electroplating), and forming a cathode or anode thereon.

[0379] Organic light-emitting diodes (OLEDs) can be used in organic light-emitting display devices.

[0380] 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 considered as limiting the scope of the implementations, nor should the comparative examples be considered as 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.

[0381] 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 appropriate methods, unless otherwise specified.

[0382] (Synthesis of compounds for organic optoelectronic devices)

[0383] Synthesis Example 1: Synthesis of Compound A-1

[0384] [Reaction Formula 1]

[0385]

[0386] Step 1: Synthesis of intermediate P-1

[0387] 2-Chloro-4-(4-(dibenzo[b,d]thiophene-4-yl)phenyl)-6-phenyl-1,3,5-triazine (100 g / 1.0 eq.), (2-fluorophenyl)boronic acid (1.1 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask along with THF (tetrahydrofuran) (750 mL) and distilled water (250 mL), and then refluxed at 80 °C. After 12 hours, the reaction was terminated, and the product was diluted with DCM (dichloromethane), washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 85 g of intermediate P-1.

[0388] Step 2: Synthesis of compound A-1

[0389] Intermediate P-1 (20 g / 1.0 eq.), 9H-carbazole (1.5 eq.), and K3PO4 (3.0 eq.) were added together with DMF (dimethylformamide) (400 mL) into a flask, and then refluxed at 150 °C. After 12 hours, the reaction was terminated, and the product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 15 g of compound A-1.

[0390] Synthesis Example 2: Synthesis of Compound A-19

[0391] [Reaction 2]

[0392]

[0393] Intermediate P-1 (20 g / 1.0 eq.), 4-phenyl-9H-carbazole (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask along with DMF (400 mL), and the mixture was refluxed at 150 °C. After 12 hours, the reaction was terminated, and the product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 17 g of compound A-19.

[0394] Synthesis Example 3: Synthesis of Compound A-32

[0395] [Reaction 3]

[0396]

[0397] Intermediate P-1 (20 g / 1.0 eq.), 9H-carbazole-4-onitrile (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask along with DMF (400 mL), and the mixture was refluxed at 150 °C. After 12 hours, the reaction was terminated, and the product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 11 g of compound A-32.

[0398] Synthesis Example 4: Synthesis of Compound A-34

[0399] [Reaction 4]

[0400]

[0401] Intermediate P-1 (20 g / 1.0 eq.), 9H-carbazole-d8 (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask along with DMF (400 mL), and the mixture was refluxed at 150 °C. After 12 hours, the reaction was terminated, and the product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 18 g of compound A-34.

[0402] Synthesis Example 5: Synthesis of Compound C-4

[0403] [Reaction 5]

[0404]

[0405] 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 xylene (122 mL). The mixture was then stirred and refluxed at 140 °C for 8 hours. When the reaction was complete, distilled water was added, and the mixture was stirred. After removing the aqueous layer, the resulting organic layer was filtered through silica gel to obtain 10.3 g (75%) of compound C-4.

[0406] (LC / MS theoretical value: 560.23 g / mol, measured value: M+ = 561.54 g / mol)

[0407] Synthesis Example 6: Synthesis of Compound B-136

[0408]

[0409] Compound B-136 was obtained by purchasing it from Gemchem.

[0410] HRMS (70eV, EI+): Theoretical m / z value of C42H28N2: 560.2252, experimental value: 560.

[0411] Elemental analysis: C, 90%; H, 5%

[0412] Synthesis Example 7: Synthesis of Compound R-1

[0413] [Reaction Formula 6]

[0414]

[0415] Step 1: Synthesis of intermediate P-2

[0416] 2-Chloro-4-(dibenzo[b,d]thiophene-4-yl)-6-phenyl-1,3,5-triazine (20 g / 1.0 eq.), (2-fluorophenyl)boronic acid (1.1 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask along with THF (750 mL) and distilled water (250 mL), and then refluxed at 80 °C. After 12 hours, the reaction was terminated, and the product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 15 g of intermediate P-2.

[0417] Step 2: Synthesis of compound R-1

[0418] Intermediate P-2 (15 g / 1.0 eq.), 9H-carbazole (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask with DMF (400 mL), and the mixture was refluxed at 150 °C. After 12 hours, the reaction was terminated, and the product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 10 g of compound R-1.

[0419] Synthesis Example 8: Synthesis of Compound R-2

[0420] [Reaction Formula 7]

[0421]

[0422] Step 1: Synthesis of intermediate P-4

[0423] 2,4-Dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (40 g / 1.0 eq.), (4-(dibenzo[b,d]thiophene-4-yl)phenyl)boronic acid (0.9 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask along with THF (750 mL) and distilled water (250 mL), and then refluxed at 80 °C. After 12 hours, the reaction was terminated, and the product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 30 g of intermediate P-4.

[0424] Step 2: Synthesis of intermediate P-3

[0425] Intermediate P-4 (30 g / 1.0 eq.), (2-fluorophenyl)boronic acid (1.1 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask along with THF (750 mL) and distilled water (250 mL), and then refluxed at 80 °C. After 12 hours, the reaction was terminated, and the product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 25 g of intermediate P-3.

[0426] Step 3: Synthesis of compound R-2

[0427] Intermediate P-3 (25 g / 1.0 eq.), 9H-carbazole-d8 (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask along with DMF (400 mL), and the mixture was refluxed at 150 °C. After 12 hours, the reaction was terminated, and the product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 18 g of compound R-2.

[0428] Synthesis Example 9: Synthesis of Compound R-3

[0429] [Reaction Equation 8]

[0430]

[0431] Step 1: Synthesis of intermediate P-5

[0432] 2-Chloro-4-(4-(dibenzo[b,d]furan-4-yl)phenyl)-6-phenyl-1,3,5-triazine (30 g / 1.0 eq.), (2-fluorophenyl)boronic acid (1.1 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask along with THF (750 mL) and distilled water (250 mL), and then refluxed at 80 °C. After 12 hours, the reaction was terminated, and the product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 20 g of intermediate P-5.

[0433] Step 2: Synthesis of compound R-3

[0434] Intermediate P-5 (20 g / 1.0 eq.), 9H-carbazole (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask with DMF (400 mL), and the mixture was refluxed at 150 °C. After 12 hours, the reaction was terminated, and the product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 12 g of compound R-3.

[0435] Example 1: Fabrication of a Green Organic Light Emitting Diode (Single Entity)

[0436] 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 and dried. It was then transferred to a plasma cleaner for 10 minutes using oxygen plasma and then moved to a vacuum depositor. 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. On the hole transport auxiliary layer, compound A-1 was used as the host and doped with 7 wt% PhGD as a dopant, to form the layer by vacuum deposition. A thick luminescent layer. Then, compound C is deposited on the luminescent layer until... The thickness is such that an electron transport auxiliary layer is formed, and compounds D 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, thereby manufacturing an organic light-emitting diode.

[0437] The manufactured organic light-emitting diode has the following structure: ITO / compound A (3% NDP-9 doped). Compound A / Compound B / EML[Body (Compound A-1): PhGD = 93wt% : 7wt%] / Compound C / Compound D:LiQ / LiQ / Al

[0438] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0439] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluorene-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0440] 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

[0441] Compound D: 2-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluorene-4-yl)-6-phenyl-1,3,5-triazine

[0442] [PhGD]

[0443]

[0444] Examples 2 to 4 and Comparative Examples 1 to 3

[0445] 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.

[0446] Example 5: Fabrication of a Green Organic Light Emitting Diode (Hybrid Body)

[0447] 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 and dried. It was then transferred to a plasma cleaner for 10 minutes using oxygen plasma and then moved to a vacuum depositor. 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, compounds A-1 and C-4 in a 4:6 weight ratio were used simultaneously as the host and doped with 10 wt% PhGD as a dopant, to form the layer by vacuum deposition. 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 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, thereby manufacturing an organic light-emitting diode.

[0448] The manufactured organic light-emitting diode has the following structure: ITO / compound E (3% NDP-9 doped). ) / Compound E / compound F / EML[body(compound A-1:compound C-4 = 4: 6wt% / wt%):PhGD = 90wt%:10wt%] / Compound G / Compound H:LiQ / LiQ / Al

[0449] Compound E: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine

[0450] Compound F: 9,9-Dimethyl-N-[3-(9-phenyl-9H-fluorene-9-yl)phenyl]-4-(4-phenylphenyl)-9H-fluorene-2-amine

[0451] Compound G: 4-{4-[4-(9,9-dimethyl-9H-fluoren-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[0452] Compound H: 2-(4-{1-[4-(diphenyl-1,3,5-triazin-2-yl)phenyl]naphthyl-2-yl}-4,6-diphenyl-1,3,5-triazine)

[0453] Examples 6 to 8 and Comparative Examples 4 to 6

[0454] Each organic light-emitting diode was manufactured in the same manner as in Example 5, except that the composition was changed to those shown in Table 2.

[0455] evaluate

[0456] The driving voltage, luminous efficiency, and lifetime characteristics of the organic light-emitting diodes according to Examples 1 to 8 and Comparative Examples 1 to 6 were evaluated.

[0457] The specific measurement methods are shown below, and the results are shown in Tables 1 and 2.

[0458] (1) Measure the change in current density based on voltage change.

[0459] 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.

[0460] (2) Measure the brightness change based on voltage changes

[0461] 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).

[0462] (3) Measure luminous efficiency

[0463] Using the brightness and current density from (1) and (2) above, the same current density (10 mA / cm²) was calculated. 2 Luminous efficiency (cd / A) at )

[0464] The luminous efficiency values ​​of Examples 1 to 4 and Comparative Examples 1 to 3 were calculated based on the relative values ​​of Comparative Example 1 and are shown in Table 1.

[0465] The luminous efficiency values ​​of Examples 5 to 8 and Comparative Examples 4 to 6 were calculated based on the relative values ​​of Comparative Example 4 and are shown in Table 2.

[0466] (4) Measuring lifespan

[0467] In terms of brightness (cd / m 2 Maintained at 24,000 cd / m 2 At the same time, the time it takes for the current efficiency (cd / A) to drop to 97% is measured as the lifetime.

[0468] The lifetime measurements of Examples 1 to 4 and Comparative Examples 1 to 3 were calculated as relative values ​​based on Comparative Example 1 and are listed in Table 1.

[0469] The lifetime measurements of Examples 5 to 8 and Comparative Examples 4 to 6 were calculated based on the relative values ​​of Comparative Example 4 and are listed in Table 2.

[0470] (Table 1)

[0471] serial number main body Luminous efficiency (%) life(%) Example 1 A-1 107 110 Example 2 A-19 108 140 Example 3 A-32 108 150 Example 4 A-34 108 150 Comparative Example 1 R-1 100 100 Comparative Example 2 R-2 102 110 Comparative Example 3 R-3 104 80

[0472] (Table 2)

[0473] serial number main body Luminous efficiency (%) life(%) Example 5 A-1 / C-4 110 120 Example 6 A-19 / C-4 110 150 Example 7 A-32 / C-4 109 150 Example 8 A-34 / C-4 110 160 Comparative Example 4 R-1 / C-4 100 100 Comparative Example 5 R-2 / C-4 102 120 Comparative Example 6 R-3 / C-4 104 70

[0474] Referring to Tables 1 and 2, compared with the organic light-emitting diodes according to Comparative Examples 1 to 6, the organic light-emitting diodes according to Examples 1 to 8 show improved luminous efficiency, and in particular, significantly improved lifetime characteristics.

[0475] By summarizing and reviewing, some exemplary embodiments can provide compounds for organic optoelectronic devices that can reduce driving voltage and achieve organic optoelectronic devices with high efficiency and long lifetime.

[0476] Some exemplary embodiments may provide compositions for organic optoelectronic devices that contain compounds for organic optoelectronic devices.

[0477] Some exemplary embodiments may provide organic optoelectronic devices comprising compounds for organic optoelectronic devices or compositions for organic optoelectronic devices.

[0478] Some exemplary embodiments may provide a display device including an organic optoelectronic device.

[0479] It is possible to achieve high efficiency and long lifespan organic optoelectronic devices while reducing operating voltage.

[0480] Exemplary embodiments have been disclosed herein, and although specific terminology has been used, it is used and understood in a general and descriptive sense only and not for limiting purposes. In some instances, as will be apparent to those skilled in the art up to the time of filing this application, features, characteristics, and / or elements described in connection with particular embodiments may be used alone or in combination with features, characteristics, and / or elements described in connection with other embodiments, unless otherwise specifically indicated. Therefore, it will be understood that various changes in form and detail may be made by those skilled in the art 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 or chemical formula 2: [Chemical Formula 1] [Chemical Formula 2] In chemical formula 1 and chemical formula 2, R 1 To R 6 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. R 7 It is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m1 to m3, m5 and m7 are each an independent integer from 1 to 4. m4 is an integer from 1 to 3. m6 is an integer from 1 to 5. When m1 is 2, 3, or 4, each R 1 Whether they are the same or different, When m2 is 2, 3, or 4, each R 2 Whether they are the same or different, When m3 is 2, 3, or 4, each R 3 Whether they are the same or different, When m4 is 2 or 3, each R 4 Whether they are the same or different, When m5 is 2, 3, or 4, each R 5 Whether they are the same or different, When m6 is 2, 3, 4, or 5, each R 6 They are the same or different from each other, and when m7 is 2, 3 or 4, each R 7 They are the same or different from each other.

2. The compound for organic optoelectronic devices according to claim 1, wherein, Chemical formula 1 is represented by one of chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] [Chemical Formulas 1-4] In chemical formulas 1-1 to 1-4, R 1 To R 7 The definitions of m1 to m7 are the same as those of chemical formula 1.

3. The compound for organic optoelectronic devices according to claim 1, wherein, Chemical formula 2 is represented by one of chemical formulas 2-1 to 2-4: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] In chemical formulas 2-1 to 2-4, R 1 To R 7 The definitions of m1 to m7 are the same as those of chemical formula 2.

4. The compound for organic optoelectronic devices according to claim 1, wherein, R 1 To R 6 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C6 alkyl, or substituted or unsubstituted phenyl, and R 7 It is hydrogen, deuterium, substituted or unsubstituted C1 to C6 alkyl or substituted or unsubstituted phenyl.

5. The compound for an organic optoelectronic device according to claim 1, wherein the compound is a compound of group 1: [Group 1] 6. A composition for use in an organic optoelectronic device, the composition comprising: First compound and second compound, in, The first compound is the compound for organic optoelectronic devices as described in claim 1, and The second compound is represented by chemical formula 3, a combination of chemical formulas 4 and 5, or chemical formula 6: [Chemical Formula 3] In chemical formula 3, R 8 To R 12 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 1 and Ar 2 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. m8, m11, and m12 are each an independent integer from 1 to 4. m9 and m10 are each an independent integer from 1 to 3. When m8 is 2, 3, or 4, each R 8 Whether they are the same or different, When m9 is 2 or 3, each R 9 Whether they are the same or different, When m10 is 2 or 3, each R 10 Whether they are the same or different, When m11 is 2, 3, or 4, each R 11 Whether they are the same or different, When m12 is 2, 3, or 4, each R 12 They are either the same or different from each other, and n is an integer from 0 to 2; In chemical formulas 4 and 5, In chemical formula 4, two adjacent a1* to a4* are bonding carbons attached to the * position in chemical formula 5. Of chemical formula 4, the two that are not connected to the * in chemical formula 5 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 13 and R 14 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. m13 and m14 are each an independent integer from 1 to 4. When m13 is 2, 3, or 4, each R 13 They are the same or different from each other, and when m14 is 2, 3 or 4, each R 14 They are the same or different from each other; [Chemical Formula 6] In chemical formula 6, L 5 It is a single-bonded or substituted or unsubstituted C6 to C20 arylene group. R 15 To R 18 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 It is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. m15, m17, and m18 are each an independent integer from 1 to 4. m16 is an integer from 1 to 3. When m15 is 2, 3, or 4, each R 15 Whether they are the same or different, When m16 is 2 or 3, each R 16 Whether they are the same or different, When m17 is 2, 3, or 4, each R 17 They are the same or different from each other, and when m18 is 2, 3 or 4, each R 18 They are the same or different from each other.

7. The composition for an organic optoelectronic device according to claim 6, wherein, The second compound is represented by chemical formula 3. Chemical formula 3 is represented by chemical formula 3-8: [Chemical Formula 3-8] In chemical formula 3-8, R 8 To R 11 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group. m8 and m11 are each an independent integer from 1 to 4. m9 and m10 are each an independent integer from 1 to 3, and *-L 1 -Ar 1 and *-L 2 -Ar 2 Each part is an independent part of group I. [Group I] In group I, R 19 To R 23 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m19 is an integer from 1 to 5. m20 is an integer from 1 to 4. m21 is an integer from 1 to 3. m22 is an integer of 1 or 2. m23 is an integer from 1 to 7, and * indicates a connection point.

8. The composition for an organic optoelectronic device according to claim 6, wherein, The second compound is represented by a combination of chemical formulas 4 and 5, which is represented by chemical formula 4C: [Chemical formula 4C] In the chemical formula 4C, L a3 and L a4 Each is a single key. R 13 R 14 R a3 and R a4 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group. m13 and m14 are each an independent integer from 1 to 4. *-L 3 -Ar 3 and *-L 4 -Ar 4 Each part is an independent part of group I. [Group I] In group I, R 19 To R 23 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m19 is an integer from 1 to 5. m20 is an integer from 1 to 4. m21 is an integer from 1 to 3. m22 is an integer of 1 or 2. m23 is an integer from 1 to 7, and * indicates a connection point.

9. An organic optoelectronic device, comprising: The anode and cathode facing each other, and At least one organic layer between the anode and the cathode, The organic layer comprises: The compound for an organic optoelectronic device according to any one of claims 1 to 5; or The composition for an organic optoelectronic device according to any one of claims 6 to 8.

10. The organic optoelectronic device according to claim 9, 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.

11. A display device comprising the organic optoelectronic device of claim 9 or claim 10.

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