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 Related Applications

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2024-0039903, filed on March 22, 2024, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Embodiments relate to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. Background Art

[0004] An organic optoelectronic device (eg, an organic optoelectronic diode) is a device capable of converting electrical energy and light energy into each other.

[0005] Organic optoelectronic devices can be divided into two categories based on their operating principles: photovoltaic 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; and light-emitting devices that generate light energy from electrical energy by supplying voltage or current to electrodes.

[0006] Examples of the organic optoelectronic device may include an organic photoelectric device, an organic light emitting diode, an organic solar cell, or an organic photosensitive drum.

[0007] Among them, organic light emitting diodes (OLEDs) have attracted much attention in recent years due to the increasing demand for flat panel display devices. Organic light emitting diodes are devices that convert electrical energy into light, and the performance of organic light emitting diodes can be affected by the organic material between electrodes. Summary of the Invention

[0008] The embodiment may be implemented by providing a compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1:

[0009] [Chemical Formula 1]

[0010]

[0011] In Chemical Formula 1, X 1 and X 2 Each independently is O, S, CR a R b 、SiR c R d or S(O)2, Z 1 to Z 10 Each independently is N or CR e , Z 1 to Z 5 At least two of them are N, Z 6 to Z10 At least two of them are N, R a 、R b 、R c 、R d 、R e and R 1 to R 4 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, L 1 To L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m1 to m4 are each independently an integer from 1 to 3, and when m1 to m4 are 2 or greater, R 1 to R 4 are the same or different, and R 1 to R 4 Each of the groups exists separately or adjacent groups are connected to each other to form a substituted or unsubstituted aromatic monocyclic ring, a substituted or unsubstituted aromatic polycyclic ring, a substituted or unsubstituted heteroaromatic monocyclic ring or a substituted or unsubstituted heteroaromatic polycyclic ring, and each R e are the same or different, and each R e The groups may exist separately or may be linked to form a substituted or unsubstituted aromatic monocyclic ring, a substituted or unsubstituted aromatic polycyclic ring, a substituted or unsubstituted heteroaromatic monocyclic ring, or a substituted or unsubstituted heteroaromatic polycyclic ring.

[0012] The embodiment may be implemented by providing a composition for an organic optoelectronic device, the composition including a first compound and a second compound, wherein the first compound is the compound for an organic optoelectronic device according to one embodiment, 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 5 to R 9 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, L 4 and L 5are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, m5, m8 and m9 are each independently an integer from 1 to 4, m6 and m7 are each independently an integer from 1 to 3, when m5 is 2, 3 or 4, each R 5 The same or different from each other, when m6 is 2 or 3, each R 6 Same or different from each other, when m7 is 2 or 3, each R 7 The same or different from each other, when m8 is 2, 3 or 4, each R 8 The same or different from each other, when m9 is 2, 3 or 4, each R 9 are the same as or different from each other, and n is an integer from 0 to 2;

[0016]

[0017] In Chemical Formula 3 and Chemical Formula 4, two adjacent ones of a1* to a4* in Chemical Formula 3 are each a connecting carbon connected to * in Chemical Formula 4, and the remaining two of a1* to a4* in Chemical Formula 3 that are not connected to * in Chemical Formula 4 are independently CL a -R f , L a 、L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R f 、R 10 and R 11 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group, Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m10 and m11 are each independently an integer from 1 to 4, and when m10 is 2, 3 or 4, each R 10 are the same as or different from each other, and when m11 is 2, 3 or 4, each R 11 the same as or different from one another;

[0018] [Chemical Formula 5]

[0019]

[0020] In Chemical Formula 5, L 8 is a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 12 to R 15are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group, Ar 5 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m12, m14 and m15 are each independently an integer from 1 to 4, m13 is an integer from 1 to 3, and when m12 is 2, 3 or 4, each R 12 The same or different from each other, when m13 is 2 or 3, each R 13 The same or different from each other, when m14 is 2, 3 or 4, each R 14 are the same as or different from each other, and when m15 is 2, 3 or 4, each R 15 the same as or different from each other.

[0021] The embodiment may be implemented by providing an organic optoelectronic device including 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 includes the compound for an organic optoelectronic device according to one embodiment.

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

[0023] The embodiment may be implemented by providing a display device including the organic optoelectronic device according to one embodiment. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Features will become apparent to those skilled in the art by describing in detail exemplary embodiments with reference to the accompanying drawings, in which:

[0025] Figure 1 is a cross-sectional view illustrating an organic light emitting diode according to some embodiments. DETAILED DESCRIPTION

[0026] Exemplary embodiments will now be described more fully hereinafter with reference to the accompanying drawings; however, they may be embodied in different forms and should not be construed as limited to the embodiments 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 exaggerated for clarity. It will also be understood that when a layer or element is referred to as being "on" another layer or substrate, it may be directly on the other layer or substrate, or there may be an intermediate layer. Further, it will be understood that when a layer is referred to as being "below" another layer, it may be directly below, or there may be one or more intermediate layers. In addition, it will be understood that when a layer is referred to as being "between" two layers, it may be the only layer between the two layers, or there may be one or more intermediate layers. As used herein, the term "or" is not necessarily an exclusive term, for example, "A or B" will include A, B, or A and B.

[0028] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, halogen, hydroxy, amino, substituted or unsubstituted C1 to C30 amine, 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 a combination thereof.

[0029] In an example of an embodiment of the present application, "substituted" means that at least one hydrogen of a substituent or compound is replaced by 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 example of an embodiment of the present application, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C20 alkyl, C1 to C5 alkylsilyl, C6 to C20 aryl, C2 to C20 heteroaryl, or cyano. In a specific example of an embodiment of the present application, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C5 alkyl, C1 to C5 alkylsilyl, C6 to C18 aryl, C2 to C18 heteroaryl, or cyano. In a specific example of an embodiment of the present application, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trimethylsilyl, phenyl, biphenyl, tert-biphenyl or naphthyl.

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

[0031] As used herein, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)." For example, any hydrogen in any compound described herein may be protium, deuterium, or tritium (e.g., based on natural or artificial substitution).

[0032] As used herein, when no definition is otherwise provided, "hetero" means containing one to three heteroatoms selected from N, O, S, P and Si and the remaining carbon in one functional group.

[0033] As used herein, "aryl" refers to a group including at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p orbitals forming conjugation, such as phenyl, naphthyl, etc., two or more hydrocarbon aromatic moieties may be linked by a σ bond and may be, for example, biphenyl, terphenyl, quaterphenyl, etc., and two or more hydrocarbon aromatic moieties may be directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl.

[0034] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0035] As used herein, "heterocyclyl" is a general concept of heteroaryl and may include at least one heteroatom selected from N, O, S, P and Si in place of carbon (C) in a cyclic compound such as an aryl, a cycloalkyl, a fused ring thereof or a combination thereof. When the heterocyclyl is a fused ring, the entire ring or each ring of the heterocyclyl may include one or more heteroatoms.

[0036] For example, "heteroaryl" may refer to an aryl group comprising at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups may be directly linked by a sigma bond, 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.

[0037] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof, but is not limited thereto.

[0038] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted furyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted oxadiazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted The present invention also includes, but is not limited to, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted isoquinolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted benzoxazinyl, a substituted or unsubstituted benzothiazinyl, a substituted or unsubstituted acridinyl, a substituted or unsubstituted phenazinyl, a substituted or unsubstituted phenothiazinyl, a substituted or unsubstituted phenoxazinyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthofuranyl, a substituted or unsubstituted benzonaphthothiophenyl, a substituted or unsubstituted benzofuranofluorenyl, a substituted or unsubstituted benzothienofluorenyl, or a combination thereof, but is not limited thereto.

[0039] As used herein, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive properties according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0040] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductive properties according to the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0041] Hereinafter, compounds for an organic optoelectronic device according to some embodiments are described.

[0042] The compound for an organic optoelectronic device according to some embodiments may be represented by Chemical Formula 1.

[0043] [Chemical Formula 1]

[0044]

[0045] In Chemical Formula 1, X 1 and X 2 Can be or include, for example, O, S, CR a R b 、SiRc R d or S(O)2.

[0046] Z 1 to Z 10 may each independently be or include, for example, N or CR e .

[0047] In one implementation, Z 1 to Z 5 At least two of them are N.

[0048] In one implementation, Z 6 to Z 10 At least two of them are N.

[0049] R a 、R b 、R c 、R d 、R e and R 1 to R 4 Each independently may be or include, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof.

[0050] L 1 To L 3 Each independently may be or include, for example, a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0051] m1 to m4 may each independently be an integer of, for example, 1 to 3.

[0052] In one implementation, m1 can be 2 to 4, and each R 1 can be the same or different from each other, and each R 1 The groups may exist separately or adjacent groups may be linked to each other to form a substituted or unsubstituted aromatic monocyclic ring, a substituted or unsubstituted aromatic polycyclic ring, a substituted or unsubstituted heteroaromatic monocyclic ring, or a substituted or unsubstituted heteroaromatic polycyclic ring.

[0053] In one implementation, m2 can be 2 to 4, and each R 2 can be the same or different from each other, and each R 2 The groups may exist separately or adjacent groups may be linked to each other to form a substituted or unsubstituted aromatic monocyclic ring, a substituted or unsubstituted aromatic polycyclic ring, a substituted or unsubstituted heteroaromatic monocyclic ring, or a substituted or unsubstituted heteroaromatic polycyclic ring.

[0054] In one implementation, m3 can be 2 to 4, and each R3 can be the same or different, and each R 3 The groups may exist separately or adjacent groups may be linked to each other to form a substituted or unsubstituted aromatic monocyclic ring, a substituted or unsubstituted aromatic polycyclic ring, a substituted or unsubstituted heteroaromatic monocyclic ring, or a substituted or unsubstituted heteroaromatic polycyclic ring.

[0055] In one implementation, m4 can be 2 to 4, and each R 4 can be the same or different, and each R 4 The groups may exist separately or adjacent groups may be linked to each other to form a substituted or unsubstituted aromatic monocyclic ring, a substituted or unsubstituted aromatic polycyclic ring, a substituted or unsubstituted heteroaromatic monocyclic ring, or a substituted or unsubstituted heteroaromatic polycyclic ring.

[0056] In one implementation, each R e can be the same or different, and each R e The groups may exist separately or adjacent groups may be linked to form a substituted or unsubstituted aromatic monocyclic ring, a substituted or unsubstituted aromatic polycyclic ring, a substituted or unsubstituted heteroaromatic monocyclic ring, or a substituted or unsubstituted heteroaromatic polycyclic ring.

[0057] By including X 1 The first position of the condensed ring of is connected to triazine, and the compound for an organic optoelectronic device represented by Chemical Formula 1 according to the present disclosure may have high charge mobility.

[0058] Furthermore, by using another triazine to contain X 2 The fused ring of the device is substituted and thus by adding a triazine that can contact an anion of the device in an electromagnetic field, the energy received by one triazine can be reduced, degradation can be prevented, and the life of the device can be significantly improved.

[0059] In addition, X 1 The lone pair of electrons can easily jump (hop, transition) in the electromagnetic field like the free electrons of the metal, and in particular, if the triazine is substituted at the 1st position, the steric hindrance caused by the substituent at the 9th position can be greatly increased, and this structural distortion can be used to greatly reduce the energy barrier that the lone pair of electrons can jump. The effect of reducing the attraction between atoms for the lone pair of electrons due to steric hindrance can promote charge transfer between molecules, and can control the charge transfer between molecules by additionally connecting the X 2 The fused rings cause the electron delocalization effect to increase the hopping speed and can increase the stability of the molecule to help solve the degradation problem.

[0060] In summary, the importance of the present disclosure is to design molecules with high stability and high charge mobility without reducing charge mobility.1 or X 2 When the condensed ring of X is connected to the triazine, delocalization occurs in which electrons are shared with each other, and since X 1 and X 2 With lone pair electrons, 1 Compared with the case of lone pair electrons, the charge mobility can be significantly improved.

[0061] Furthermore, by attaching three different substituents around the triazine, the symmetry of the molecule can be disrupted, and steric hindrance can be increased, leading to lower deposition temperatures. This effect can improve the deposited film, making it possible to develop materials with longer lifetimes.

[0062] In one implementation, Chemical Formula 1 may be represented by one of Chemical Formula 1-1 to Chemical Formula 1-4.

[0063]

[0064] In Chemical Formulas 1-1 to 1-4, X 1 and X 2 , Z 1 to Z 10 、R 1 to R 4 、L 1 To L 3 and m1 to m4 may be defined the same as those of Chemical Formula 1.

[0065] In one implementation, Chemical Formula 1 may be represented by one of Chemical Formulas 1-5 to 1-7.

[0066] [Chemical Formula 1-5]

[0067]

[0068] [Chemical formula 1-6]

[0069]

[0070] [Chemical Formula 1-7]

[0071]

[0072] In Chemical Formulas 1-5 to 1-7, X 1 and X 2 、R 1 to R 4 、L 1 To L 3 and m1 to m4 may be defined as the same as those of Chemical Formula 1, and R e1 to R e4Each of them can be defined as R e same.

[0073] In one implementation, X 1 and X 2 Can be O, S or SiR c R d , where R c and R d Each independently may be or include, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0074] In one implementation, (X 1 and X 2 ) can each be (O and O), (O and S) or (O and SiR c R d , where R c and R d Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof).

[0075] In one implementation, L 1 To L 3 Each may be a single bond.

[0076] In one implementation, R a 、R b 、R c and R d Each independently may be, for example, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group.

[0077] In one implementation, R a 、R b 、R c and R d Each independently may be, for example, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0078] In one implementation, R 1 to R 4 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl.

[0079] In one implementation, R 1 to R 4Each independently may be, 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, or substituted or unsubstituted naphthyl.

[0080] In one implementation, R e and R e1 to R e4 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, or substituted or unsubstituted C6 to C20 heterocyclic group.

[0081] In one implementation, R e and R e1 to R e4 Each independently may be, 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 naphthyl, or substituted or unsubstituted carbazolyl.

[0082] In one implementation, the compound represented by Chemical Formula 1 may be, for example, a compound of Group 1.

[0083] [Group 1]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090] wherein D is deuterium and TMS is -Si(CH3)3.

[0091] According to some embodiments, the composition for an organic optoelectronic device may include a first compound and a second compound. The first compound may be the compound for an organic optoelectronic device described above, 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.

[0092] [Chemical Formula 2]

[0093]

[0094] In Chemical Formula 2, R 5 to R 9 Each independently may be or include, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group.

[0095] Ar 1 and Ar 2 Each independently may be or include, for example, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0096] L 4 and L 5 Each independently may be or include, for example, a single bond or a substituted or unsubstituted C6 to C20 arylene group.

[0097] m5, m8, and m9 may each independently be an integer of, for example, 1 to 4.

[0098] m6 and m7 may each independently be an integer of 1 to 3, for example.

[0099] In one implementation, m5 can be 2 to 4, and each R 5 They may be the same as or different from each other.

[0100] In one implementation, m6 can be 2 or 3, and each R 6 They may be the same as or different from each other.

[0101] In one implementation, m7 can be 2 or 3, and each R 7 They may be the same as or different from each other.

[0102] In one implementation, m8 can be 2 to 4, and each R 8 They may be the same as or different from each other.

[0103] In one implementation, m9 can be 2 to 4, and each R 9 They may be the same as or different from each other.

[0104] n may be an integer from 0 to 2, for example.

[0105]

[0106] In Chemical Formula 3 and Chemical Formula 4, two adjacent ones of a1* to a4* in Chemical Formula 3 are carbon atoms connected to * in Chemical Formula 4. The remaining two of a1* to a4* in Chemical Formula 3 that are not connected to * in Chemical Formula 4 can each independently be, for example, CL a -R fAs used herein, the term "linking carbon" refers to the shared carbon to which the fused ring is attached.

[0107] L a , L 6 and L 7 Each independently may be or include, for example, a single bond or a substituted or unsubstituted C6 to C20 arylene group.

[0108] R f 、R 10 and R 11 Each independently may be or include, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group.

[0109] Ar 3 and Ar 4 Each independently may be, for example, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0110] m10 and m11 can each independently be an integer of, for example, 1 to 4,

[0111] In one implementation, m10 can be 2 to 4, and each R 10 They may be the same as or different from each other.

[0112] In one implementation, m11 can be 2 to 4, and each R 11 They may be the same as or different from each other.

[0113] [Chemical Formula 5]

[0114]

[0115] In Chemical Formula 5, L 8 It may be, for example, a single bond or a substituted or unsubstituted C6 to C20 arylene group.

[0116] R 12 to R 15 Each independently may be, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic.

[0117] Ar 5 It may be, for example, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0118] m12, m14, and m15 may each independently be an integer of, for example, 1 to 4.

[0119] m13 may be an integer from 1 to 3, for example.

[0120] In one implementation, m12 can be 2 to 4, and each R 12 They may be the same as or different from each other.

[0121] In one implementation, m13 can be 2 or 3, and each R 13 They may be the same as or different from each other.

[0122] In one implementation, m14 can be 2 to 4, and each R 14 They may be the same as or different from each other.

[0123] In one implementation, m15 can be 2 to 4, and each R 15 They may be the same as or different from each other.

[0124] The second compound may be included in the light emitting layer together with the first compound to improve light emitting efficiency and lifespan characteristics by increasing charge mobility and stability.

[0125] In one implementation, in Formula 2, Ar 1 and Ar 2 Each of them can independently be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group.

[0126] In one implementation, in Chemical Formula 2, L 4 and L 5 Each independently may be, for example, a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0127] In one implementation, in Chemical Formula 2, R 5 to R 9 Each independently may be, for example, hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group.

[0128] n can be 0 or 1.

[0129] In Chemical Formula 2, “substituted” may mean that at least one hydrogen is replaced by deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0130] In one implementation, in Formula 2, Ar 1 and Ar2 Each independently may be, for example, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group.

[0131] In one implementation, Chemical Formula 2 may be represented by one of Chemical Formula 2-1 to Chemical Formula 2-15.

[0132]

[0133]

[0134] In Chemical Formulas 2-1 to 2-15, R 5 to R 9 may be independently hydrogen, deuterium or substituted or unsubstituted C6 to C12 aryl, and the portion -L 4 -Ar 1 and -L 5 -Ar 2 Can each independently be part of, for example, Group 1.

[0135] [Group I]

[0136]

[0137] In Group I, R 16 to R 20 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl.

[0138] m16 may be an integer from 1 to 5, for example.

[0139] m17 may be an integer from 1 to 4, for example.

[0140] m18 may be an integer from 1 to 3, for example.

[0141] m19 may be an integer such as 1 or 2.

[0142] m20 may be an integer from 1 to 7, for example.

[0143] * is the connection point.

[0144] In one implementation, m16 can be 2 to 5, and each R 16 They may be the same as or different from each other.

[0145] In one implementation, m17 can be 2 to 4, and each R 17 They may be the same as or different from each other.

[0146] In one implementation, m18 can be 2 or 3, and each R 18 They may be the same as or different from each other.

[0147] In one implementation, m19 may be 2, and each R 19 They may be the same as or different from each other.

[0148] In one implementation, m20 can be 2 to 7, and each R 20 They may be the same as or different from each other.

[0149] The combination of Chemical Formula 3 and Chemical Formula 4 can be represented by, for example, Chemical Formula 3A, Chemical Formula 3B, Chemical Formula

[0150] One of Formula 3C, Chemical Formula 3D and Chemical Formula 3E is represented.

[0151]

[0152] In Chemical Formulae 3A to 3E, L 6 , L 7 、Ar 3 、Ar 4 、R 10 、R 11 , m10, and m11 can be defined the same as above.

[0153] L a1 To L a4 It can be defined as the same as the above L 6 and L 7 same.

[0154] R f1 to R f4 It can be defined as the same as the above R 10 and R 11 same.

[0155] In one implementation, in Formula 3 and Formula 4, Ar 3 and Ar 4 Each of them can independently be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group.

[0156] R f1 to R f4 、R 10 and R 11Each independently may be, 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 dibenzothiophenyl.

[0157] In one implementation, in Formulas 3 and 4, the moiety -L 6 -Ar 3 and -L 7 -Ar 4 Can each independently be part of Group I.

[0158] In one implementation, R f1 to R f4 、R 10 and R 11 Each independently may be, 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 dibenzothiophenyl.

[0159] In one implementation, R f1 to R f4 、R 10 and R 11 Each independently may be, for example, hydrogen, deuterium, cyano, or substituted or unsubstituted phenyl.

[0160] In one implementation, R f1 to R f4 、R 10 and R 11 Each independently may be, for example, hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0161] In one implementation, the second compound may be represented by Chemical Formula 2-8, and in Chemical Formula 2-8, Ar 1 and Ar 2 L may be each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group, 4 and L 5 may each independently be, for example, a single bond or a substituted or unsubstituted C6 to C20 arylene group, and R 5 to R 8 Each independently may be, 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 dibenzothiophenyl.

[0162] In one implementation, in Chemical Formula 2-8, R 5 to R 8 may be independently hydrogen, deuterium or substituted or unsubstituted C6 to C12 aryl, and the portion -L 4 -Ar 1 and -L 5 -Ar 2 Can each independently be part of, for example, Group 1.

[0163] In one implementation, the second compound can be represented by, for example, Chemical Formula 3C, and in Chemical Formula 3C, L a3 and L a4 Each may be, for example, a single bond, L 6 and L 7 R 10 、R 11 、R f3 and R f4 can each be, for example, hydrogen, deuterium or phenyl, and Ar 3 and Ar 4 Each independently may be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0164] In one implementation, in Formula 3C, L a3 and L a4 It can be, for example, a single bond, R 10 、R 11 、R f3 and R f4 can each independently be, for example, hydrogen, deuterium or C6 to C12 aryl, and the portion -L 6 -Ar 3 and -L 7 -Ar 4 Can each independently be part of, for example, Group 1.

[0165] Chemical Formula 5 may be represented by, for example, one of Chemical Formula 5-1 to Chemical Formula 5-4.

[0166]

[0167] In Chemical Formula 5-1 to Chemical Formula 5-4, L 8 、Ar 5 、R 12 to R 15 And m12 to m15 can be defined the same as above.

[0168] In one implementation, in Chemical Formula 5, Ar 5 It may be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group.

[0169] R 12 to R 15 Each independently may be, 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 dibenzothiophenyl.

[0170] In one embodiment, in Chemical Formula 5, the moiety -L 8 -Ar 5 Can be part of Group I.

[0171] In one implementation, R 12 to R 15 Each independently may be, for example, hydrogen, deuterium, cyano, or substituted or unsubstituted phenyl.

[0172] In one implementation, the second compound for an organic optoelectronic device may be, for example, a compound of Group 2.

[0173] [Group 2]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181] In one implementation, examples are given below in which at least one hydrogen in Compounds B-1 to B-150 listed in Group 2 is replaced by deuterium.

[0182]

[0183]

[0184]

[0185] (Dn refers to the number of deuterium substitution and represents the structure substituted with one or more deuterium atoms).

[0186] The most specific structures of Compound B-151 to Compound B-195 of Group 2 are presented below as examples according to the position and substitution ratio of deuterium substitution.

[0187] In one embodiment, deuterium can be substituted, for example, as shown in the compounds exemplified below, or the deuterium substitution positions and deuterium substitution ratios can include all variable ranges within Compound B-1 to Compound B-195 (e.g., any hydrogen in any compound can be protium or deuterium).

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195] In one implementation, examples are given below of compounds C-1 to C-57 listed in Group 2 in which at least one hydrogen is replaced by deuterium.

[0196]

[0197] (Dn refers to the number of deuterium substitution and represents the structure substituted with one or more deuterium atoms).

[0198] The most specific structures of Compound C-58 to Compound C-72 of Group 2 are presented below as examples according to the position and substitution ratio of deuterium substitution.

[0199] In one implementation, deuterium can be substituted as shown in the compounds exemplified below, and the deuterium substitution position and deuterium substitution ratio can include all variable ranges within the range of Compound C-58 to Compound C-72.

[0200] In one embodiment, deuterium can be substituted as shown in the compounds exemplified below, or the deuterium substitution positions and deuterium substitution ratios can include any and all variable ranges within the range of Compound C-1 to Compound C-72 (e.g., any hydrogen in any compound can be protium or deuterium).

[0201]

[0202]

[0203]

[0204]

[0205] In one implementation, examples are given below of compounds D-1 to D-60 listed in Group 2 in which at least one hydrogen is replaced by deuterium.

[0206]

[0207]

[0208]

[0209]

[0210] (Dn refers to the number of deuterium substitution and represents the structure substituted with one or more deuterium atoms).

[0211] In one implementation, the second compound may be represented by one of Chemical Formula 2-8, Chemical Formula 3C, and Chemical Formula 5-3.

[0212] The first compound and the second compound can be included (e.g., mixed) in a weight ratio of, for example, about 1:99 to about 99:1. By being included in the above range, utilizing the electron transport ability of the first compound and the hole transport ability of the second compound, by adjusting the appropriate weight ratio, efficiency and lifespan can be improved by realizing bipolar characteristics. Within the above range, they can be included in a weight ratio of, for example, about 10:90 to about 90:10, about 20:80 to about 80:20 (e.g., about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40). In one implementation, they can be included in a weight ratio of about 40:60, about 50:50, or about 60:40.

[0213] Hereinafter, an organic optoelectronic device including the above-mentioned compound for an organic optoelectronic device or the composition for an organic optoelectronic device will be described.

[0214] The organic optoelectronic device may be a suitable device for converting electrical energy into light energy and vice versa, for example, an organic photovoltaic device, an organic light emitting diode, an organic solar cell, or an organic photosensitive drum.

[0215] Herein, an organic light emitting diode as one example of an organic optoelectronic device is described with reference to the accompanying drawings.

[0216] Figure 1 is a cross-sectional view illustrating an organic light emitting diode according to some embodiments.

[0217] Reference Figure 1 , the organic light emitting diode 100 according to some 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 .

[0218] The anode 120 may be made of a conductor having a large work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; or a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, or polyaniline.

[0219] 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, 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 an alloy thereof; or a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, or BaF2 / Ca.

[0220] The organic layer 105 may include the above-described compound for an organic optoelectronic device or composition for an organic optoelectronic device.

[0221] 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 above-mentioned compound for an organic optoelectronic device or a composition for an organic optoelectronic device, and the dopant may be, for example, a phosphorescent dopant, such as a red, green or blue phosphorescent dopant, such as a red or green phosphorescent dopant.

[0222] The dopant may be a material that is mixed in a small amount with a compound or composition used in an organic optoelectronic device to induce light emission, and may generally be a material such as a metal complex that emits light by multiple excitations to a triplet state or more. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof may be used.

[0223] Examples of the dopant may include a phosphorescent dopant, and examples of the phosphorescent dopant may include an organometallic compound containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the chemical formula Z.

[0224] [Chemical formula Z]

[0225] L 9 MX 3

[0226] In the chemical formula Z, M may be a metal, and L 9 and X 3 can be the same or different and can each independently be a ligand that forms a complex with M.

[0227] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L 9 and X 3 This can be, for example, a bidentate ligand.

[0228] By L 9 and X 3 Examples of the ligands represented may include group A ligands.

[0229] [Group A]

[0230]

[0231] In Group A, R 300 to R 302 Each may independently be hydrogen, deuterium, a C1 to C30 alkyl group which may be substituted or not substituted by a halogen, a C6 to C30 aryl group which may be substituted or not substituted by a C1 to C30 alkyl group, or a halogen.

[0232] R 303 to R 324Each may independently be 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, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

[0233] n1 may be an integer of 1 to 5, for example.

[0234] n2 may be an integer from 1 to 4, for example.

[0235] n3 may be an integer from 1 to 3, for example.

[0236] n4 may be an integer such as 1 or 2.

[0237] n5 may be an integer of 1 to 6, for example.

[0238] The dopant according to some embodiments may be an iridium complex, and may be represented by, for example, Chemical Formula 6-1 or Chemical Formula 6-2.

[0239] [Chemical Formula 6-1]

[0240]

[0241] In Chemical Formula 6-1, R 101 to R 116 can each independently be hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 .

[0242] R 132 to R 134 Each independently may be a substituted or unsubstituted C1 to C6 alkyl group.

[0243] R 101 to R 116 At least one of may be a functional group represented by Chemical Formula V-1.

[0244] L 100 The bidentate ligand may be a monovalent anion and may be a ligand coordinated to iridium via a lone pair of electrons of carbon or a heteroatom.

[0245] m21 and m22 may each independently be an integer from 0 to 3, and m21+m22 may be an integer from 1 to 3,

[0246] [Chemical Formula V-1]

[0247]

[0248] In chemical formula V-1, R 135 to R 139 can each independently be hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 , and * refers to a moiety attached to a carbon atom.

[0249] [Chemical Formula 6-2]

[0250]

[0251] In Chemical Formula 6-2, R 101 to R 117 can each independently be hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 133 R 134 R 135 .

[0252] R 133 to R 135 Each independently may be a substituted or unsubstituted C1 to C6 alkyl group.

[0253] L 100 The bidentate ligand may be a monovalent anion and may be a ligand coordinated to iridium via a lone pair of electrons of carbon or a heteroatom.

[0254] n1 and n2 may each independently be an integer from 0 to 3, and n1+n2 may be an integer from 1 to 3.

[0255] The dopant according to some embodiments may be a platinum complex, and may be represented by, for example, Chemical Formula Z-1.

[0256] [Chemical Formula Z-1]

[0257]

[0258] In Chemical Formula Z-1, Rings A, B, C, and D may each independently be a 5-membered or 6-membered carbocyclic ring or heterocyclic ring.

[0259] R A 、R B 、R C and RD may each independently be, for example, mono-, di-, tri- or tetra-substituted or unsubstituted;

[0260] L B , L C and L D Each can independently be a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, or a combination thereof.

[0261] In one implementation, nA may be 1, and L E It can be 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 Does not exist.

[0262] R A 、R B 、R C 、R D R and R' can each independently be hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, or a combination thereof; any adjacent R A 、R B 、R C 、R D , R and R' may be optionally linked to each other to provide a ring; X B 、X C 、X D and X E can each independently be carbon or nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 can each independently be oxygen or a direct bond.

[0263] The platinum complex can be represented by, for example, Chemical Formula 7-1 or Chemical Formula 7-2.

[0264] [Chemical Formula 7-1]

[0265]

[0266] [Chemical Formula 7-2]

[0267]

[0268] In Chemical Formula 7-1 and Chemical Formula 7-2, X100 Can be selected from O, S or NR 132 .

[0269] R 118 to R 132 can each independently be hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 133 R 134 R 135 .

[0270] R 133 to R 135 Each independently may be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0271] In one implementation, R 118 to R 132 At least one of them may be -SiR 133 R 134 R 135 or tert-butyl.

[0272] R 133 to R 135 Each independently may be a substituted or unsubstituted C1 to C6 alkyl group.

[0273] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0274] The charge transport region may be, for example, a hole transport region 140 .

[0275] The hole transport region 140 may help to further increase hole injection or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.

[0276] 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 a compound of group B may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0277] [Group B]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284] (Dn refers to the number of deuterium substitution and represents the structure substituted with one or more deuterium atoms).

[0285] In the hole transport region 140 , in addition to the above-mentioned compounds, other suitable compounds having a similar structure may be used.

[0286] In one implementation, the charge transport region may be, for example, the electron transport region 150 .

[0287] The electron transport region 150 may help to further increase electron injection or electron mobility between the cathode 110 and the light emitting layer 130 and block holes.

[0288] 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 a compound of group C may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0289] [Group C]

[0290]

[0291]

[0292]

[0293] Some embodiments may provide an organic light emitting diode including a light emitting layer as an organic layer.

[0294] Some embodiments may provide an organic light emitting diode including a light emitting layer and a hole transport region as organic layers.

[0295] Some embodiments may provide an organic light emitting diode including a light emitting layer and an electron transport region as organic layers.

[0296] like Figure 1 As shown, the organic light emitting diode according to some embodiments further includes a hole transport region 140 and an electron transport region 150 as the organic layer 105 in addition to the light emitting layer 130 .

[0297] In one implementation, in addition to the light-emitting layer, the organic light-emitting diode may further include an electron injection layer, a hole injection layer, etc. as organic layers.

[0298] The organic light emitting diode 100 may be manufactured by forming an anode or a cathode on a substrate, then forming an organic layer by a dry film method such as vacuum deposition, sputtering, plasma plating, and ion plating, and forming the cathode or anode thereon.

[0299] Organic light emitting diodes can be applied to organic light emitting display devices.

[0300] The following examples and comparative examples are provided to highlight the features of one or more embodiments, but it will be understood that the examples and comparative examples should not be construed as limiting the scope of the embodiments, and the comparative examples should not be construed as being outside the scope of the embodiments. Further, it will be understood that the embodiments are not limited to the specific details described in the examples and comparative examples.

[0301] Hereinafter, starting materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo chemical industry, or P&H tech, or synthesized by known methods unless otherwise specified.

[0302] (Synthesis of Compounds for Organic Optoelectronic Devices)

[0303] Synthesis Example 1: Synthesis of Intermediate I-1

[0304]

[0305] In a nitrogen environment, 2-bromo-1-chloro-3-fluorobenzene (1000 g, 4,775 mmol) purchased from Henan Tianfu Chemical (www.tianfuchem.net) was dissolved in 10 L of toluene, and then 2,6-dimethoxyphenylboronic acid (1043 g, 5,730 mmol) and tetrakis(triphenylphosphine)palladium (110 g, 95.5 mmol) purchased from Bide pharma (https: / / jlchem) were added and stirred. Then, a saturated aqueous solution of potassium carbonate (1,650 g, 11,938 mmol) was added and heated under reflux at 130 ° C for 3 days. When the reaction was complete, after adding water thereto, it was extracted with dichloromethane (DCM), the moisture was removed with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain intermediate I-1 (535 g, 42%).

[0306] HRMS (70 eV, EI+): m / z calculated for C14H12ClFO2: 266.0510, found: 266.

[0307] Elemental analysis: C, 63%; H, 5%.

[0308] Synthesis Example 2: Synthesis of Intermediate I-2

[0309]

[0310] Intermediate I-1 (500 g, 1,875 mmol) and pyridine hydrochloride (1,483 g, 18,748 mmol) were added under nitrogen and heated under reflux for 12 hours at 180 ° C. After the reaction was completed, water was added to the reaction solution, the mixture was extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain intermediate I-2 (361 g, 81%).

[0311] HRMS (70 eV, EI+): m / z calculated for C12H8ClFO2: 238.0197, found: 238.

[0312] Elemental analysis: C, 60%; H, 3%.

[0313] Synthesis Example 3: Synthesis of Intermediate I-3

[0314]

[0315] In a nitrogen environment, intermediate I-2 (350g, 1,467mmol) is dissolved in 0.3L of N-methyl-2-pyrrolidone (NMP), to which potassium carbonate (406g, 2,934mmol) is then added and heated to reflux for 3 hours. After the reaction is complete, the solvent is removed by distillation, water is added to the reaction solution, the mixture is extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained is separated and purified by flash column chromatography to obtain intermediate I-3 (103g, 32%).

[0316] HRMS (70 eV, EI+): m / z calculated for C12H7ClO2: 218.0135, found: 218.

[0317] Elemental analysis: C, 66%; H, 3%.

[0318] Synthesis Example 4: Synthesis of Intermediate I-4

[0319]

[0320] In a nitrogen environment, intermediate I-3 (100g, 457mmol) is dissolved in 1.0L of dichloromethane (DCM), and then the temperature is reduced to 0°C. Pyridine (43.4g, 549mmol) is added here and stirred for 30 minutes, then trifluoromethanesulfonic anhydride (155g, 549mmol) is slowly added thereto and stirred. After 3 hours, the temperature of the reaction solution is reduced to 0°C, water is slowly added for 30 minutes, the mixture is extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained is separated and purified by flash column chromatography to obtain intermediate I-4 (157g, 98%).

[0321] HRMS (70 eV, EI+): m / z calculated for C13H6ClF3O4S: 349.9627, measured: 350.

[0322] Elemental analysis: C, 45%; H, 2%.

[0323] Synthesis Example 5: Synthesis of Intermediate I-5

[0324]

[0325] In nitrogen environment, intermediate I-3 (100g, 457mmol) is dissolved in the acetone of 1.0L, then add iodomethane (71.4,503mmol) and potassium carbonate (69.5g, 503mmol), and reflux 6 hours.After the reaction is completed, after adding water thereto, mixture is extracted with dichloromethane (DCM), is processed with anhydrous magnesium sulfate to remove moisture, filters, and is under reduced pressure concentrated.The residue thus obtained is separated and purified by flash column chromatography, to obtain intermediate I-5 (101g, 95%).

[0326] HRMS (70 eV, EI+): m / z calculated for C13H9C1O2: 232.0291, found: 232.

[0327] Elemental analysis: C, 67%; H, 4%.

[0328] Synthesis Example 6: Synthesis of Intermediate I-6

[0329]

[0330] In a nitrogen environment, after intermediate I-5 (100g, 430mmol) is dissolved in 1.0L dimethylbenzene, bis(pinacolato)diboron (131g, 516mmol), tris(dibenzylideneacetone)dipalladium (0) (3.94g, 4.3mmol), tricyclohexylphosphine (4.82g, 17.2mmol) and potassium acetate (127g, 1,290mmol) are added thereto and heated to reflux for 8 hours. After the reaction is complete, water is added to the reaction solution, the mixture is extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained is separated and purified by flash column chromatography to obtain intermediate I-6 (121g, 87%).

[0331] HRMS (70 eV, EI+): m / z calculated for C19H21BO4: 324.1533, found: 324.

[0332] Elemental analysis: C, 70%; H, 7%.

[0333] Synthesis Example 7: Synthesis of Intermediate I-7

[0334]

[0335] In a nitrogen environment, after intermediate I-6 (120g, 370mmol) is dissolved in the dioxane of 1.2L, intermediate I-4 (130g, 370mmol) and tetrakis (triphenylphosphine) palladium (8.55g, 7.4mmol) are added thereto and stirred. Then, potassium carbonate (128g, 925mmol) saturated aqueous solution is added, and heated to reflux for 8 hours at 100°C. After the reaction is complete, after water is added thereto, the mixture is extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, and concentrated under reduced pressure. The residue thus obtained is separated and purified by flash column chromatography to obtain intermediate I-7 (145g, 98%).

[0336] HRMS (70 eV, EI+): m / z calculated for C25H15C1O3: 398.0710, found: 398.

[0337] Elemental analysis: C, 75%; H, 4%.

[0338] Synthesis Example 8: Synthesis of Intermediate I-8

[0339]

[0340] In the same manner as in Synthesis Example 6, Intermediate I-7 (140 g, 351 mmol) was used to obtain Intermediate I-8 (86.1 g, 50%).

[0341] HRMS (70 eV, EI+): m / z calculated for C31H27BO5: 490.1952, found: 490.

[0342] Elemental analysis: C, 76%; H, 6%.

[0343] Synthesis Example 9: Synthesis of Intermediate I-9

[0344]

[0345] In the same manner as in Synthesis Example 7, Intermediate I-9 (89.7 g, 87%) was obtained by using Intermediate I-8 (85 g, 173 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (55.7 g, 208 mmol) purchased from Tokyo Chemical Industries (http: / / www.tcichemicals.com / ).

[0346] HRMS (70 eV, EI+): m / z calculated for C40H25N3O3: 595.1896, found: 595.

[0347] Elemental analysis: C, 81%; H, 4%.

[0348] Synthesis Example 10: Synthesis of Intermediate I-10

[0349]

[0350] In the same manner as in Synthesis Example 2, Intermediate I-9 (88 g, 148 mmol) was used to obtain Intermediate I-10 (85.2 g, 99%).

[0351] HRMS (70 eV, EI+): m / z calculated for C39H23N3O3: 581.1739, measured: 581.

[0352] Elemental analysis: C, 81%; H, 4%.

[0353] Synthesis Example 11: Synthesis of Intermediate I-11

[0354]

[0355] In the same manner as in Synthesis Example 4, Intermediate I-10 (84 g, 144 mmol) was used to obtain Intermediate I-11 (93.8 g, 91%).

[0356] HRMS (70 eV, EI+): m / z calculated for C40H22F3N3O5S: 713.1232, found: 713.

[0357] Elemental analysis: C, 67%; H, 3%.

[0358] Synthesis Example 12: Synthesis of Intermediate I-12

[0359]

[0360] In a nitrogen environment, after intermediate I-11 (92g, 129mmol) is dissolved in 1.0L dioxane, bis(pinacolato)diboron (49.1g, 193mmol) and 1,1-bis(diphenylphosphino)ferrocenedichloropalladium (3.16g, 3.87mmol) are added thereto, and triethylamine (39.2g, 387mmol) is added and heated to reflux for 15 hours. After the reaction is complete, water is added to the reaction solution, the mixture is extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained is separated and purified by flash column chromatography to obtain intermediate I-12 (43.7g, 49%).

[0361] HRMS (70 eV, EI+): m / z calculated for C45H34BN3O4: 691.2642, measured: 691.

[0362] Elemental analysis: C, 78%; H, 5%.

[0363] Synthesis Example 13: Synthesis of Compound 1

[0364]

[0365] In the same manner as in Synthesis Example 7, Compound 1 (18.4 g, 80%) was obtained by using Intermediate I-12 (20 g, 28.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.29 g, 34.7 mmol) purchased from Tokyo Chemical Industries.

[0366] HRMS (70 eV, EI+): m / z calculated for C54H32N6O2: 796.2587, measured: 796.

[0367] Elemental analysis: C, 81%; H, 4%.

[0368] Synthesis Example 14: Synthesis of Compound 2

[0369]

[0370] In the same manner as in Synthesis Example 7, Compound 2 (20.9 g, 83%) was obtained by using Intermediate I-12 (20 g, 28.9 mmol) and 2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (11.9 g, 34.7 mmol) purchased from Tokyo Chemical Industries.

[0371] HRMS (70 eV, EI+): m / z calculated for C60H36N6O2: 872.2900, measured: 872.

[0372] Elemental analysis: C, 83%; H, 4%.

[0373] Synthesis Example 15: Synthesis of Intermediate I-13

[0374]

[0375] In the same manner as in Synthesis Example 7, Intermediate I-13 (117 g, 95%) was obtained by using Intermediate I-6 (100 g, 308 mmol) and 8-bromo-1-chlorodibenzofuran (86.8 g, 308 mmol) purchased from P&H tech (http: / / www.phtech.co.kr / ).

[0376] HRMS (70 eV, EI+): m / z calculated for C25H15C1O3: 398.0710, found: 398.

[0377] Elemental analysis: C, 75%; H, 4%.

[0378] Synthesis Example 16: Synthesis of Intermediate I-14

[0379]

[0380] In the same manner as in Synthesis Example 6, Intermediate I-14 (101 g, 75%) was obtained using Intermediate I-13 (110 g, 276 mmol).

[0381] HRMS (70 eV, EI+): m / z calculated for C31H27BO5: 490.1952, found: 490.

[0382] Elemental analysis: C, 76%; H, 6%.

[0383] Synthesis Example 17: Synthesis of Intermediate I-15

[0384]

[0385] In the same manner as in Synthesis Example 7, Intermediate I-15 (109 g, 90%) was obtained by using Intermediate I-14 (100 g, 204 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (54.6 g, 204 mmol) purchased from Tokyo Chemical Industries.

[0386] HRMS (70 eV, EI+): m / z calculated for C40H25N3O3: 595.1896, found: 595.

[0387] Elemental analysis: C, 81%; H, 4%.

[0388] Synthesis Example 18: Synthesis of Intermediate I-16

[0389]

[0390] In the same manner as in Synthesis Example 2, Intermediate I-16 (98.3 g, 96%) was obtained using Intermediate I-15 (105 g, 176 mmol).

[0391] HRMS (70 eV, EI+): m / z calculated for C39H23N3O3: 581.1739, measured: 581.

[0392] Elemental analysis: C, 81%; H, 4%.

[0393] Synthesis Example 19: Synthesis of Intermediate I-17

[0394]

[0395] In the same manner as in Synthesis Example 4, Intermediate I-17 (111 g, 95%) was obtained using Intermediate I-16 (95 g, 163 mmol).

[0396] HRMS (70 eV, EI+): m / z calculated for C40H22F3N3O5S: 713.1232, found: 713.

[0397] Elemental analysis: C, 67%; H, 3%.

[0398] Synthesis Example 20: Synthesis of Intermediate I-18

[0399]

[0400] In the same manner as in Synthesis Example 12, Intermediate I-18 (54.3 g, 51%) was obtained using Intermediate I-17 (110 g, 154 mmol).

[0401] HRMS (70 eV, EI+): m / z calculated for C45H34BN3O4: 691.2642, measured: 691.

[0402] Elemental analysis: C, 78%; H, 5%.

[0403] Synthesis Example 21: Synthesis of Compound 9

[0404]

[0405] In the same manner as in Synthesis Example 7, Compound 9 (17.5 g, 76%) was obtained by using Intermediate I-18 (20 g, 28.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.28 g, 34.7 mmol) purchased from Tokyo Chemical Industries.

[0406] HRMS (70 eV, EI+): m / z calculated for C54H32N6O2: 796.2587, measured: 796.

[0407] Elemental analysis: C, 81%; H, 4%.

[0408] Synthesis Example 22: Synthesis of Intermediate I-19

[0409]

[0410] In the same manner as in Synthesis Example 7, Intermediate I-19 (112 g, 91%) was obtained by using Intermediate I-6 (100 g, 308 mmol) and 7-bromo-1-chlorodibenzofuran (86.8 g, 308 mmol) purchased from P&H tech.

[0411] HRMS (70 eV, EI+): m / z calculated for C25H15C1O3: 398.0710, found: 398.

[0412] Elemental analysis: C, 75%; H, 4%.

[0413] Synthesis Example 23: Synthesis of Intermediate I-20

[0414]

[0415] In the same manner as in Synthesis Example 6, Intermediate I-19 (110 g, 276 mmol) was used to obtain Intermediate I-20 (89.3 g, 66%).

[0416] HRMS (70 eV, EI+): m / z calculated for C31H27BO5: 490.1952, found: 490.

[0417] Elemental analysis: C, 76%; H, 6%.

[0418] Synthesis Example 24: Synthesis of Intermediate I-21

[0419]

[0420] In the same manner as in Synthesis Example 7, Intermediate I-21 (94.8 g, 92%) was obtained by using Intermediate I-20 (85 g, 173 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (51.0 g, 191 mmol) purchased from Tokyo Chemical Industries.

[0421] HRMS (70 eV, EI+): m / z calculated for C40H25N3O3: 595.1896, found: 595.

[0422] Elemental analysis: C, 81%; H, 4%.

[0423] Synthesis Example 25: Synthesis of Intermediate I-22

[0424]

[0425] In the same manner as in Synthesis Example 2, Intermediate I-22 (80.8 g, 90%) was obtained using Intermediate I-21 (92 g, 154 mmol).

[0426] HRMS (70 eV, EI+): m / z calculated for C39H23N3O3: 581.1739, measured: 581.

[0427] Elemental analysis: C, 81%; H, 4%.

[0428] Synthesis Example 26: Synthesis of Intermediate I-23

[0429]

[0430] In the same manner as in Synthesis Example 4, Intermediate I-22 (79 g, 136 mmol) was used to obtain Intermediate I-23 (86.4 g, 89%).

[0431] HRMS (70 eV, EI+): m / z calculated for C40H22F3N3O5S: 713.1232, found: 713.

[0432] Elemental analysis: C, 67%; H, 3%.

[0433] Synthesis Example 27: Synthesis of Intermediate I-24

[0434]

[0435] Intermediate I-24 (26.4 g, 32%) was obtained using Intermediate I-23 (85 g, 119 mmol) in the same manner as in Synthesis Example 12.

[0436] HRMS (70 eV, EI+): m / z calculated for C45H34BN3O4: 691.2642, measured: 691.

[0437] Elemental analysis: C, 78%; H, 5%.

[0438] Synthesis Example 28: Synthesis of Compound 10

[0439]

[0440] In the same manner as in Synthesis Example 7, by using Intermediate I-24 (20 g, 28.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.28 g, 34.7 mmol) purchased from Tokyo Chemical Industries, Compound 10 (11.5 g, 50%) was obtained.

[0441] HRMS (70 eV, EI+): m / z calculated for C54H32N6O2: 796.2587, measured: 796.

[0442] Elemental analysis: C, 81%; H, 4%.

[0443] Synthesis Example 29: Synthesis of Intermediate I-25

[0444]

[0445] In the same manner as in Synthesis Example 7, by using Intermediate I-6 (100 g, 308 mmol) and 6-bromo-1-chlorodibenzofuran (86.8 g, 308 mmol) purchased from P&H tech, Intermediate I-25 (117 g, 95%) was obtained.

[0446] HRMS (70 eV, EI+): m / z calculated for C25H15C1O3: 398.0710, found: 398.

[0447] Elemental analysis: C, 75%; H, 4%.

[0448] Synthesis Example 30: Synthesis of Intermediate I-26

[0449]

[0450] In the same manner as in Synthesis Example 6, Intermediate I-25 (115 g, 288 mmol) was used to obtain Intermediate I-26 (113 g, 80%).

[0451] HRMS (70 eV, EI+): m / z calculated for C31H27BO5: 490.1952, found: 490.

[0452] Elemental analysis: C, 76%; H, 6%.

[0453] Synthesis Example 31: Synthesis of Intermediate I-27

[0454]

[0455] In the same manner as in Synthesis Example 7, Intermediate I-27 (123 g, 92%) was obtained by using Intermediate I-26 (110 g, 224 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (66.1 g, 247 mmol) purchased from Tokyo Chemical Industries.

[0456] HRMS (70 eV, EI+): m / z calculated for C40H25N3O3: 595.1896, found: 595.

[0457] Elemental analysis: C, 81%; H, 4%.

[0458] Synthesis Example 32: Synthesis of Intermediate I-28

[0459]

[0460] In the same manner as in Synthesis Example 2, Intermediate I-28 (115 g, 98%) was obtained using Intermediate I-27 (120 g, 201 mmol).

[0461] HRMS (70 eV, EI+): m / z calculated for C39H23N3O3: 581.1739, measured: 581.

[0462] Elemental analysis: C, 81%; H, 4%.

[0463] Synthesis Example 33: Synthesis of Intermediate I-29

[0464]

[0465] In the same manner as in Synthesis Example 4, Intermediate I-28 (113 g, 194 mmol) was used to obtain Intermediate I-29 (126 g, 91%).

[0466] HRMS (70 eV, EI+): m / z calculated for C40H22F3N3O5S: 713.1232, found: 713.

[0467] Elemental analysis: C, 67%; H, 3%.

[0468] Synthesis Example 34: Synthesis of Intermediate I-30

[0469]

[0470] In the same manner as in Synthesis Example 12, Intermediate I-29 (125 g, 174 mmol) was used to obtain Intermediate I-30 (48.2 g, 40%).

[0471] HRMS (70 eV, EI+): m / z calculated for C45H34BN3O4: 691.2642, measured: 691.

[0472] Elemental analysis: C, 78%; H, 5%.

[0473] Synthesis Example 35: Synthesis of Compound 11

[0474]

[0475] In the same manner as in Synthesis Example 7, Compound 11 (20.0 g, 87%) was obtained by using Intermediate I-30 (20 g, 28.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.28 g, 34.7 mmol) purchased from Tokyo Chemical Industries.

[0476] HRMS (70 eV, EI+): m / z calculated for C54H32N6O2: 796.2587, measured: 796.

[0477] Elemental analysis: C, 81%; H, 4%.

[0478] Synthesis Example 36: Synthesis of Intermediate I-31

[0479]

[0480] In the same manner as in Synthesis Example 6, 7-bromo-1-chlorodibenzofuran (100 g, 355 mmol) was used to obtain Intermediate I-31 (91.0 g, 78%).

[0481] HRMS (70 eV, EI+): m / z calculated for C18H18BC1O3: 328.1038, found: 328.

[0482] Elemental analysis: C, 66%; H, 6%.

[0483] Synthesis Example 37: Synthesis of Intermediate I-32

[0484]

[0485] In the same manner as in Synthesis Example 7, Intermediate I-32 (117 g, 98%) was obtained by using Intermediate I-31 (90 g, 274 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (80.7 g, 301 mmol) purchased from Tokyo Chemical Industries.

[0486] HRMS (70 eV, EI+): m / z calculated for C27H16ClN3O: 433.0982, found: 433.

[0487] Elemental analysis: C, 74%; H, 4%.

[0488] Synthesis Example 38: Synthesis of Intermediate I-33

[0489]

[0490] In the same manner as in Synthesis Example 6, Intermediate I-32 (115 g, 265 mmol) was used to obtain Intermediate I-33 (90.5 g, 65%).

[0491] HRMS (70 eV, EI+): m / z calculated for C33H28BN3O3: 525.2224, found: 525.

[0492] Elemental analysis: C, 75%; H, 5%.

[0493] Synthesis Example 39: Synthesis of Intermediate I-34

[0494]

[0495] In the same manner as in Synthesis Example 7, Intermediate I-33 (89 g, 169 mmol) and 8-bromo-1-chlorodibenzofuran (47.7 g, 169 mmol) were used to obtain Intermediate I-34 (92.3 g, 91%).

[0496] HRMS (70 eV, EI+): m / z calculated for C39H22ClN3O2: 599.1401, found: 599.

[0497] Elemental analysis: C, 78%; H, 4%.

[0498] Synthesis Example 40: Synthesis of Intermediate I-35

[0499]

[0500] In the same manner as in Synthesis Example 6, Intermediate I-34 (91 g, 152 mmol) was used to obtain Intermediate I-35 (57.7 g, 55%).

[0501] HRMS (70 eV, EI+): m / z calculated for C45H34BN3O4: 691.2642, measured: 691.

[0502] Elemental analysis: C, 78%; H, 5%.

[0503] Synthesis Example 41: Synthesis of Compound 17

[0504]

[0505] In the same manner as in Synthesis Example 7, Compound 17 (18.4 g, 80%) was obtained by using Intermediate I-35 (20 g, 28.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.28 g, 34.7 mmol) purchased from Tokyo Chemical Industries.

[0506] HRMS (70 eV, EI+): m / z calculated for C54H32N6O2: 796.2587, measured: 796.

[0507] Elemental analysis: C, 81%; H, 4%.

[0508] Synthesis Example 42: Synthesis of Intermediate I-36

[0509]

[0510] In the same manner as in Synthesis Example 6, 8-bromo-1-chlorodibenzofuran (100 g, 355 mmol) was used to obtain Intermediate I-36 (103 g, 88%).

[0511] HRMS (70 eV, EI+): m / z calculated for C18H18BC1O3: 328.1038, found: 328.

[0512] Elemental analysis: C, 66%; H, 6%.

[0513] Synthesis Example 43: Synthesis of Intermediate I-37

[0514]

[0515] In the same manner as in Synthesis Example 7, Intermediate I-37 (125 g, 95%) was obtained by using Intermediate I-36 (100 g, 304 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (89.6 g, 335 mmol) purchased from Tokyo Chemical Industries.

[0516] HRMS (70 eV, EI+): m / z calculated for C27H16ClN3O: 433.0982, found: 433.

[0517] Elemental analysis: C, 74%; H, 4%.

[0518] Synthesis Example 44: Synthesis of Intermediate I-38

[0519]

[0520] In the same manner as in Synthesis Example 6, Intermediate I-38 (76.7 g, 72%) was obtained using Intermediate I-37 (88 g, 203 mmol).

[0521] HRMS (70 eV, EI+): m / z calculated for C33H28BN3O3: 525.2224, found: 525.

[0522] Elemental analysis: C, 75%; H, 5%.

[0523] Synthesis Example 45: Synthesis of Intermediate I-39

[0524]

[0525] In the same manner as in Synthesis Example 7, Intermediate I-38 (75 g, 143 mmol) and 7-bromo-1-chlorodibenzofuran (40.2 g, 143 mmol) were used to obtain Intermediate I-39 (65.2 g, 76%).

[0526] HRMS (70 eV, EI+): m / z calculated for C39H22ClN3O2: 599.1401, found: 599.

[0527] Elemental analysis: C, 78%; H, 4%.

[0528] Synthesis Example 46: Synthesis of Intermediate I-40

[0529]

[0530] In the same manner as in Synthesis Example 6, Intermediate I-39 (63 g, 105 mmol) was used to obtain Intermediate I-40 (43.6 g, 60%).

[0531] HRMS (70 eV, EI+): m / z calculated for C45H34BN3O4: 691.2642, measured: 691.

[0532] Elemental analysis: C, 78%; H, 5%.

[0533] Synthesis Example 41: Synthesis of Compound 18

[0534]

[0535] In the same manner as in Synthesis Example 7, Compound 18 (17.7 g, 77%) was obtained by using Intermediate I-40 (20 g, 28.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.28 g, 34.7 mmol) purchased from Tokyo Chemical Industries.

[0536] HRMS (70 eV, EI+): m / z calculated for C54H32N6O2: 796.2587, measured: 796.

[0537] Elemental analysis: C, 81%; H, 4%.

[0538] Synthesis Example 42: Synthesis of Intermediate I-41

[0539]

[0540] In the same manner as Synthesis Example 7, 2,4-dichloro-6-phenyl-1,3,5-triazine (100 g, 442 mmol) and (4-cyanophenyl)boronic acid (32.5 g, 221 mmol) were used to obtain Intermediate I-41 (33.6 g, 52%).

[0541] HRMS (70 eV, EI+): m / z calculated for C16H9ClN4: 292.0516, measured: 292.

[0542] Elemental analysis: C, 66%; H, 3%.

[0543] Synthesis Example 43: Synthesis of Compound 61

[0544]

[0545] In the same manner as in Synthesis Example 7, Intermediate I-12 (20 g, 28.9 mmol) and Intermediate I-41 (10.2 g, 34.7 mmol) were used to obtain Compound 61 (15.7 g, 66%).

[0546] HRMS (70 eV, EI+): m / z calculated for C55H31N7O2: 821.2539, measured: 821.

[0547] Elemental analysis: C, 80%; H, 4%.

[0548] Synthesis Example 44: Synthesis of Intermediate I-42

[0549]

[0550] In a nitrogen atmosphere, 9H-carbazole (100 g, 598 mmol) and 2,4-dichloro-6-phenyl-1,3,5-triazine (203 g, 897 mmol) purchased from Tokyo Chemical Industries were dissolved in 1 L of tetrahydrofuran (THF), and sodium tert-butoxide (63.2 g, 658 mmol) was slowly added at 0°C and stirred. After 12 hours, water was added to the reaction solution and the mixture was filtered. The residue thus obtained was separated and purified by flash column chromatography to obtain intermediate I-42 (194 g, 91%).

[0551] HRMS (70 eV, EI+): m / z calculated for C21H13ClN4: 356.0829, found: 356.

[0552] Elemental analysis: C, 71%; H, 4%.

[0553] Synthesis Example 45: Synthesis of Compound 101

[0554]

[0555] In the same manner as in Synthesis Example 7, Intermediate I-12 (20 g, 28.9 mmol) and Intermediate I-41 (12.4 g, 34.7 mmol) were used to obtain Compound 101 (12.8 g, 50%).

[0556] HRMS (70 eV, EI+): m / z calculated for C60H35N7O2: 885.2852, measured: 885.

[0557] Elemental analysis: C, 81%; H, 4%.

[0558] Synthesis Example 46: Synthesis of Compound R-1

[0559]

[0560] Compound R-1 was synthesized with reference to Korean patent KR2022-0013909.

[0561] HRMS (70 eV, EI+): m / z calculated for C51H30N4O2: 730.2369, measured: 730.

[0562] Elemental analysis: C, 84%; H, 4%.

[0563] Synthesis Example 47: Synthesis of Compound R-2

[0564]

[0565] The comparative compound R-2 was synthesized with reference to Korean patent KR2022-0013909.

[0566] HRMS (70 eV, EI+): m / z calculated for C51H30N4O2: 730.2369, measured: 730.

[0567] Elemental analysis: C, 84%; H, 4%.

[0568] Synthesis Example 48: Synthesis of Compound R-3

[0569]

[0570] Compound R-3 was synthesized with reference to Korean patent KR2018-0068869.

[0571] HRMS (70 eV, EI+): m / z calculated for C45H27N3O2: 641.2103, measured: 641.

[0572] Elemental analysis: C, 84%; H, 4%.

[0573] Synthesis Example 49: Synthesis of Compound B-40

[0574]

[0575] Compound B-40 was purchased from Gemchem (http: / / www.ytgemchem.com).

[0576] HRMS (70 eV, EI+): m / z calculated for C48H31N3: 649.2518, found: 649.

[0577] Elemental analysis: C, 89%; H, 5%.

[0578] Synthesis Example 50: Synthesis of Compound B-136

[0579]

[0580] Compound B-136 was purchased from Gemchem.

[0581] HRMS (70 eV, EI+): m / z calculated for C42H28N2: 560.2252, found: 560.

[0582] Elemental analysis: C, 90%; H, 5%.

[0583] Synthesis Example 51: Synthesis of Compound C-4

[0584]

[0585] Compound C-4 was purchased from Gemchem.

[0586] HRMS (70 eV, EI+): m / z calculated for C42H28N2: 560.2252, found: 560.

[0587] Elemental analysis: C, 90%; H, 5%.

[0588] Example 1

[0589] A glass substrate coated with an ITO (indium tin oxide) thin film was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with isopropyl alcohol, acetone, or methanol and dried. Then, the glass substrate was moved to a plasma cleaner, cleaned for 10 minutes using oxygen plasma, and moved to a vacuum depositor. The ITO transparent electrode thus prepared was used as an anode, and Compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO substrate to form a A hole injection layer is formed, and compound A is deposited on the hole injection layer to Compound B is deposited on the hole transport layer to a thickness of To form a hole transport auxiliary layer, and on the hole transport auxiliary layer, Compound 1 (synthesized in Synthesis Example 13) was used as a host and doped with 7 wt % of PhGD as a dopant to form a hole transport auxiliary layer by vacuum deposition. The ratios are described in the following examples and comparative examples. Subsequently, compound C is deposited on the luminescent layer to The thickness of the electron transport auxiliary layer is formed, and the compound D and LiQ are simultaneously vacuum deposited at a weight ratio of 1:1 to form The thick electron transport layer is formed by vacuum deposition on the electron transport layer. LiQ and Al is used to form the cathode to manufacture organic light-emitting diodes.

[0590] ITO / Compound A (3% NDP-9 doping, ) / Compound A / Compound B / EML[Compound 1 (93 wt%):PhGD (7 wt%)] Compound C / Compound D:LiQ / LiQ / Al

[0591] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0592] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0593] 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

[0594] Compound D: 2-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0595] [PhGD]

[0596]

[0597] Examples 2 to 9 and Comparative Examples 1 to 3

[0598] An organic light emitting diode was manufactured in the same manner as in Example 1, except that the composition was changed to the composition shown in Table 1.

[0599] Example 10

[0600] A glass substrate coated with an ITO (indium tin oxide) thin film was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with isopropyl alcohol, acetone, or methanol and dried. Then, the glass substrate was moved to a plasma cleaner, cleaned for 10 minutes using oxygen plasma, and moved to a vacuum depositor. The ITO transparent electrode thus prepared was used as an anode, and Compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO substrate to form a A hole injection layer is formed, and compound A is deposited on the hole injection layer to Compound E is deposited on the hole transport layer to a thickness of On the hole transport auxiliary layer, the compound 1 synthesized in Synthesis Example 13 and the compound B-136 synthesized in Synthesis Example 50 were used as hosts at the same time, and PhGD was doped at 10 wt % as a dopant to form a hole transport auxiliary layer by vacuum deposition. Thick emitting layer. Here, compound 1 and compound B-136 were used in a weight ratio of 3:7. Then, compound F was deposited on the emitting layer to The thickness of the electron transport auxiliary layer is formed, and the compound G and LiQ are vacuum deposited at a weight ratio of 1:1 to form By sequentially vacuum depositing LiQ and Al is used to form the cathode to manufacture organic light-emitting diodes.

[0601] ITO / Compound A (3% NDP-9 doping, ) / Compound A / Compound E / EML[Compound 1:Compound B-136:PhGD=27:63:10 wt%)] / Compound F / Compound G:LiQ / LiQ / Al

[0602] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0603] Compound E: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluoren)-2-amine

[0604] Compound F: 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0605] Compound G: 2-[4-[4-(4'-cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0606] Examples 11 to 22 and Comparative Examples 4 to 6

[0607] An organic light emitting diode was prepared in the same manner as in Example 10, except that the composition was changed to that shown in Table 2.

[0608] evaluate

[0609] The driving voltage, luminous efficiency, and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 22 and Comparative Examples 1 to 6 were evaluated.

[0610] The measurement method is as follows, and the results are shown in Tables 1 and 2.

[0611] (1) Measuring the change in current density according to voltage change

[0612] While increasing the voltage from 0 V to 10 V, the current value flowing through the unit device in the obtained organic light emitting diode was measured using a current-voltage meter (Keithley 2400), and the measured current value was divided by the area to provide a result.

[0613] (2) Measuring the brightness change according to the voltage change

[0614] While increasing the voltage of the organic light emitting diode from 0 V to 10 V, the luminance was measured by using a luminance meter (Minolta Cs-1000A).

[0615] (3) Measure luminous efficiency

[0616] By using the luminance and current density and voltage from (1) and (2) above, the luminance at the same current density (10 mA / cm 2 ) under the current efficiency (cd / A).

[0617] Based on Comparative Example 1, the luminous efficiency values ​​of Examples 1 to 9 and Comparative Examples 1 to 3 were calculated as relative values ​​and shown in Table 1.

[0618] Based on Comparative Example 4, the luminous efficiency values ​​of Examples 10 to 22 and Comparative Examples 4 to 6 were calculated as relative values ​​and shown in Table 2.

[0619] (4) Measurement life

[0620] In the case of brightness (cd / m 2 ) maintained at 24,000cd / m 2 The time required for each current efficiency (cd / A) to drop to 97% was measured as the lifetime.

[0621] Based on Comparative Example 1, the lifespan values ​​of Examples 1 to 9 and Comparative Examples 1 to 3 were calculated as relative values ​​and shown in Table 1.

[0622] Based on Comparative Example 4, the lifespan values ​​of Examples 10 to 22 and Comparative Examples 4 to 6 were calculated as relative values ​​and shown in Table 2.

[0623] (5) Measure the driving voltage

[0624] The current-voltage of each device was measured at 15 mA / cm using an ampere-voltmeter (Keithley 2400). 2 The driving voltage is as follows.

[0625] Based on Comparative Example 1, the driving voltages of Examples 1 to 9 and Comparative Examples 1 to 3 were calculated as relative values ​​and shown in Table 1.

[0626] Based on Comparative Example 4, the driving voltages of Examples 10 to 22 and Comparative Examples 4 to 6 were calculated as relative values ​​and shown in Table 2.

[0627] (Table 1)

[0628] serial number Compound (wt%) Driving voltage (%) Color (EL color) efficiency(%) life(%) Example 1 1(93) 86 green 145 193 Example 2 2(93) 85 green 149 233 Example 3 9(93) 88 green 133 260 Example 4 10(93) 88 green 130 233 Example 5 11(93) 89 green 122 267 Example 6 17(93) 90 green 112 200 Example 7 18(93) 88 green 109 273 Example 8 61(93) 92 green 102 320 Example 9 101(93) 89 green 118 367 Comparative Example 1 R-1(93) 100 green 100 100 Comparative Example 2 R-2(93) 102 green 89 133 Comparative Example 3 R-3(93) 95 green 84 167

[0629] (Table 2)

[0630]

[0631]

[0632] Referring to Table 1 and Table 2, the organic light emitting diodes according to Examples 1 to 22 have significantly improved light emitting efficiency and lifespan characteristics compared to the organic light emitting diodes according to Comparative Examples 1 to 6.

[0633] One or more embodiments may provide a compound for an organic optoelectronic device capable of reducing a driving voltage and realizing an organic optoelectronic device with high efficiency and a long lifespan.

[0634] While reducing the driving voltage, high-efficiency and long-life organic optoelectronic devices can be achieved.

[0635] Exemplary embodiments have been disclosed herein, and although specific terms are employed, they are used and interpreted in their supra- and descriptive sense only, and not for purposes of limitation. In some cases, as of the time of filing this application, it will be apparent to one of ordinary skill in the art that features, characteristics, and / or elements described in association with a particular embodiment may be used alone, or they may be used in combination with features, characteristics, and / or elements described in association with other embodiments, unless otherwise expressly indicated. Therefore, it will be understood by those skilled in the art that various changes may be made in form and detail without departing from the spirit and scope of the invention as set forth in the appended claims.

Claims

1. A compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, X 1 and X 2 Each independently is O, S, CR a R b 、SiR c R d or S(O)2, Z 1 to Z 10 Each independently is N or CR e , Z 1 to Z 5 At least two of them are N, Z 6 to Z 10 At least two of them are N, R a 、R b 、R c 、R d 、R e and R 1 to R 4 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, L 1 To L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m1 to m4 are each independently an integer from 1 to 3, When m1 to m4 are 2 or more, R 1 to R 4 are the same or different, and R 1 to R 4 Each exists separately or adjacent groups are linked to each other to form a substituted or unsubstituted aromatic monocyclic ring, a substituted or unsubstituted aromatic polycyclic ring, a substituted or unsubstituted heteroaromatic monocyclic ring or a substituted or unsubstituted heteroaromatic polycyclic ring, and Each R e are the same or different, and each R e The groups may exist separately or may be linked to form a substituted or unsubstituted aromatic monocyclic ring, a substituted or unsubstituted aromatic polycyclic ring, a substituted or unsubstituted heteroaromatic monocyclic ring, or a substituted or unsubstituted heteroaromatic polycyclic ring.

2. The compound for an organic optoelectronic device according to claim 1, wherein: Chemical Formula 1 is represented by one of Chemical Formulas 1-1 to 1-4: In Chemical Formulas 1-1 to 1-4, X 1 and X 2 , Z 1 to Z 10 、R 1 to R 4 、L 1 To L 3 And m1 to m4 are defined the same as those of Chemical Formula 1.

3. The compound for an organic optoelectronic device according to claim 1, wherein: Chemical Formula 1 is represented by one of Chemical Formulas 1-5 to 1-7: [Chemical Formula 1-5] [Chemical formula 1-6] [Chemical Formula 1-7] In Chemical Formulas 1-5 to 1-7, X 1 and X 2 、R 1 to R 4 、L 1 To L 3 and m1 to m4 are defined as the same as those of Chemical Formula 1, and R e1 to R e4 Defined as R in formula 1 e same.

4. The compound for an organic optoelectronic device according to claim 1, wherein: X 1 and X 2 Each independently is O, S or SiR c R d ,and R c and R d Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

5. The compound for an organic optoelectronic device according to claim 1, wherein L 1 To L 3 Each is a single bond.

6. The compound for an organic optoelectronic device according to claim 1, which is a compound of Group 1: [Group 1] in, TMS is -Si(CH3)3.

7. The compound for an organic optoelectronic device according to claim 6, which is a compound of Group 1-1: [Group 1-1] 8. A composition for an organic optoelectronic device, comprising: a first compound; and The second compound, in: The first compound is the compound for an organic optoelectronic device according to any one of claims 1 to 7, and The second compound is represented by: Chemical formula 2, A combination of Chemical Formula 3 and Chemical Formula 4, or Chemical formula 5: [Chemical Formula 2] In Chemical Formula 2, R 5 to R 9 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, m5, m8 and m9 are each independently an integer from 1 to 4, m6 and m7 are each independently an integer from 1 to 3, When m5 is 2, 3, or 4, each R 5 Same or different from each other, When m6 is 2 or 3, each R 6 Same or different from each other, When m7 is 2 or 3, each R 7 Same or different from each other, When m8 is 2, 3, or 4, each R 8 Same or different from each other, When m9 is 2, 3, or 4, each R 9 are the same as or different from each other, and n is an integer from 0 to 2; In Chemical Formula 3 and Chemical Formula 4, Each of adjacent two of a1* to a4* in Chemical Formula 3 is a connecting carbon connected to * in Chemical Formula 4, The remaining two of a1* to a4* in Chemical Formula 3 that are not connected to * in Chemical Formula 4 are independently CL a -R f , L a 、L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R f 、R 10 and R 11 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group, Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m10 and m11 are each independently an integer from 1 to 4, When m10 is 2, 3, or 4, each R 10 are the same as or different from each other, and When m11 is 2, 3, or 4, each R 11 the same as or different from one another; [Chemical Formula 5] In Chemical Formula 5, L 8 is a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 12 to R 15 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group, Ar 5 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m12, m14 and m15 are each independently an integer from 1 to 4, m13 is an integer from 1 to 3, When m12 is 2, 3, or 4, each R 12 Same or different from each other, When m13 is 2 or 3, each R 13 Same or different from each other, When m14 is 2, 3, or 4, each R 14 are the same as or different from each other, and When m15 is 2, 3, or 4, each R 15 the same as or different from each other.

9. The composition for an organic optoelectronic device according to claim 8, wherein: The second compound is represented by Chemical Formula 2, and Chemical formula 2 is represented by Chemical formula 2-8: [Chemical Formula 2-8] In Chemical Formula 2-8, R 5 to R 8 are each independently hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, m5 and m8 are each independently an integer from 1 to 4, m6 and m7 are each independently an integer from 1 to 3, Part-L 4 -Ar 1 and -L 5 -Ar 2 each independently being part of Group I, [Group I] In Group I, R 16 to R 20 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, m16 is an integer from 1 to 5, m17 is an integer from 1 to 4, m18 is an integer from 1 to 3, m19 is an integer of 1 or 2, m20 is an integer from 1 to 7, and * is the connection point.

10. The composition for an organic optoelectronic device according to claim 8, wherein: The second compound is represented by a combination of Chemical Formula 3 and Chemical Formula 4, and The combination of Chemical Formula 3 and Chemical Formula 4 is represented by Chemical Formula 3C: [Chemical formula 3C] In Chemical Formula 3C, L a3 and L a4 Each is a single bond, R 10 、R 11 、R f3 and R f4 are each independently hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, m10 and m11 are each independently an integer from 1 to 4, and Part-L 6 -Ar 3 and -L 7 -Ar 4 each independently being part of Group I, [Group I] In Group I, R 16 to R 20 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, m16 is an integer from 1 to 5, m17 is an integer from 1 to 4, m18 is an integer from 1 to 3, m19 is an integer of 1 or 2, m20 is an integer from 1 to 7, and * is the connection point.

11. 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 the compound for an organic optoelectronic device according to any one of claims 1 to 7; or The composition for an organic optoelectronic device according to any one of claims 8 to 10.

12. The organic optoelectronic device according to claim 11, wherein: The at least one organic layer includes a light emitting layer, and The light-emitting layer includes the compound or the composition. 13 . A display device comprising the organic optoelectronic device according to claim 11 .

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