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

Abstract

Provided are a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. Disclosed are a compound for an organic optoelectronic device represented by Chemical Formula 1, a composition for an organic optoelectronic device comprising the same, an organic optoelectronic device, and a display device. The details of the chemical formula 1 are the same as those described in the specification.

Description

[0001] Citations of Related Applications

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0088562 filed in the Korean Intellectual Property Office on July 7, 2023, 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 according to their working principles: one is a photoelectric device that generates electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes, respectively; the other is a light-emitting device that generates 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, and an organic photosensitive drum.

[0007] Among them, organic light emitting diodes (OLEDs) have attracted attention in recent years due to an increase in demand for flat panel displays. Organic light emitting diodes convert electrical energy into light, and the performance of organic light emitting diodes may be affected by an 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 Formula 1, X is O or S, L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, R 1 To R 5Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof, m1, m2 and m5 are each independently an integer from 1 to 4, and m3 and m4 are each independently an integer from 1 to 3.

[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 a combination of Chemical Formula 2, Chemical Formula 3, and Chemical Formula 4, or Chemical Formula 5:

[0013] [Chemical formula 2]

[0014]

[0015] In chemical formula 2, R 6 To R 10 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, 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, L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, m6, m9 and m10 are each independently an integer from 1 to 4, m7 and m8 are each independently an integer from 1 to 3, 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 connecting carbons connected to the * in Chemical Formula 4, and the remaining two of a1* to a4* in Chemical Formula 3 that are not connected to the * in Chemical Formula 4 are CL a -R a , L a , L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R a , R 11 and R 12are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, Ar 5 and Ar 6 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m11 and m12 are each independently an integer of 1 to 4;

[0018] [Chemical formula 5]

[0019]

[0020] In Chemical Formula 5, L 7 is a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 13 To R 16 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, Ar 7 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m13, m15 and m16 are each independently an integer of 1 to 4, and m14 is an integer of 1 to 3.

[0021] The embodiment may be achieved 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] Embodiments may be achieved 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] Embodiments may be achieved by providing a display device including the organic optoelectronic device according to one embodiment. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Characteristics 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 showing an organic light emitting diode according to some embodiments. DETAILED DESCRIPTION

[0026] Exemplary embodiments will now be described more fully below with reference to the accompanying drawings; however, they may be embodied in different forms and should not be considered limited to the embodiments shown herein. However, these embodiments are provided so that this disclosure will be thorough and complete for those skilled in the art and will fully convey exemplary implementations.

[0027] In the accompanying drawings, the sizes 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 element, it may be directly on the other layer or element, or there may also be intervening 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 also be one or more intervening layers. Throughout the invention, similar reference numerals represent similar elements. 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 a compound is replaced by deuterium, halogen, hydroxyl, 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 one example, "substituted" refers to 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 addition, in a specific example, "substituted" refers to that at least one hydrogen of a substituent or compound is replaced by: deuterium, C1 to C20 alkyl, C6 to C30 aryl or cyano. In addition, in a specific example, "substituted" refers to that at least one hydrogen of a substituent or compound is replaced by: deuterium, C1 to C5 alkyl, C6 to C18 aryl or cyano. In addition, in a specific example, "substituted" refers to that at least one hydrogen of a substituent or compound is replaced by: deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl or naphthyl.

[0030] As used herein, "unsubstituted" means that a hydrogen atom is not replaced with another substituent and that a hydrogen atom remains.

[0031] As used herein, "hydrogen (-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 a definition is not otherwise provided, "hetero" means containing one to three heteroatoms selected from N, O, S, P and Si and the remaining carbons in one functional group.

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

[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, "heterocyclic group" has 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 condensed ring thereof or a combination thereof. When the heterocyclic group is a condensed ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0036] For example, "heteroaryl" refers to an aryl group including at least one heteroatom selected from N, O, S, P and Si. Two or more heteroaryls are directly connected by a sigma bond, or when the heteroaryl includes two or more rings, the two or more rings can be fused. When the heteroaryl is a fused ring, each ring can include 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 pyrene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted para-terphenyl group, a substituted or unsubstituted meta-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 peryl 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 furanyl, 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 invention may include, but is not limited to, a substituted quinolyl, a substituted or unsubstituted isoquinolyl, 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] In this specification, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

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

[0041] Hereinafter, a compound for an organic optoelectronic device according to some embodiments is 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 may be O or S, for example.

[0046] L 1 and L 2Each independently may be or include, for example, a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0047] Ar 1 and Ar 2 Each may independently be or include, for example, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0048] R 1 To R 5 Each independently may be or include, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0049] m1, m2 and m5 may each independently be an integer of 1 to 4, for example.

[0050] m3 and m4 may each independently be an integer of 1 to 3, for example.

[0051] The compound represented by Chemical Formula 1 has a dibenzofuran (or dibenzothiophene) structure substituted with o-N-carbazole and triazine and a bipolar structure that separates HOMO / LUMO regions and expands the LUMO region to manufacture a high-efficiency organic light emitting diode.

[0052] Furthermore, by substituting carbazole in the N direction, the π bond through the CN bond can be broken, and thus the electron cloud between HOMO-LUMO can be localized to maximize the lifetime improvement effect.

[0053] In one embodiment, m1 may be 2, 3 or 4 and each R 1 May be the same as or different from each other.

[0054] In one embodiment, m2 may be 2, 3 or 4 and each R 2 May be the same as or different from each other.

[0055] In one embodiment, m3 can be 2 or 3 and each R 3 May be the same as or different from each other.

[0056] In one embodiment, m4 can be 2 or 3 and each R 4 May be the same as or different from each other.

[0057] In one embodiment, m5 can be 2, 3 or 4 and each R 5 May be the same as or different from each other.

[0058] In one embodiment, the compound for an organic optoelectronic device may be represented by one of Chemical Formula 1-1 to Chemical Formula 1-4.

[0059]

[0060] In Chemical Formulae 1-1 to 1-4, X, L 1 and L 2 ,Ar 1 and Ar 2 , R 1 To R 5 And m1 to m5 may be defined the same as those described above.

[0061] In one embodiment, R 1 To R 4 Each of them may independently be, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, substituted or unsubstituted C2 to C18 heterocyclic group, or a combination thereof.

[0062] R 5 It may be, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, or a combination thereof.

[0063] In one embodiment, the HOMO energy level of the compound for an organic optoelectronic device may be, for example, about −5.5 to about −4.9 eV.

[0064] In one embodiment, the LUMO energy level of the compound for an organic optoelectronic device may be, for example, about −1.7 to about −2.1 eV.

[0065] In one embodiment, Ar 1 and Ar 2 Each of them independently 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 phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0066] In one embodiment, Ar 1 and Ar 2 At least one of the groups may be, for example, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0067] In one embodiment, the moiety -L1 -Ar 1 and -L 2 -Ar 2 Can each independently be part of group I, for example.

[0068] [Group I]

[0069]

[0070] In Group I, R 23 To R 25 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl.

[0071] m23 may be an integer from 1 to 5, for example.

[0072] m24 may be an integer from 1 to 4, for example.

[0073] m25 may be an integer from 1 to 3, for example.

[0074] * is the connection point.

[0075] In group I, m23 can be 2, 3, 4 or 5 and each R 23 May be the same as or different from each other.

[0076] In group I, m24 can be 2, 3 or 4 and each R 24 May be the same as or different from each other.

[0077] In Group I, m25 can be 2 or 3 and each R 25 May be the same as or different from each other.

[0078] In one embodiment, the compound represented by Chemical Formula 1 may be, for example, a compound of Group 1.

[0079] [Group 1]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088] (D n refers to the number of deuterium substitution and represents a structure substituted with one or more deuteriums.) Examples of A-153 to A-156 (for example, as deuterium-containing compounds) can be shown below.

[0089]

[0090] 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, for example, the compound for an organic optoelectronic device described above. In one embodiment, the second compound may be represented by a combination of Chemical Formula 2, Chemical Formula 3, and Chemical Formula 4, or Chemical Formula 5.

[0091] [Chemical formula 2]

[0092]

[0093] In chemical formula 2, R 6 To R 10 Each independently may be or include, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group.

[0094] Ar 3 and Ar 4 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.

[0095] L 3 and L 4 Each independently may be or include, for example, a single bond or a substituted or unsubstituted C6 to C20 arylene group.

[0096] m6, m9 and m10 may each independently be an integer of 1 to 4, for example.

[0097] m7 and m8 may each independently be an integer of 1 to 3, for example.

[0098] n may be an integer from 0 to 2, for example.

[0099]

[0100] In Chemical Formula 3 and Chemical Formula 4, two adjacent ones of a1* to a4* in Chemical Formula 3 are connecting carbons connected to the * in Chemical Formula 4, and the remaining two of a1* to a4* in Chemical Formula 3 that are not connected to the * in Chemical Formula 4 are CLa -R a As used herein, the term "linking carbon" refers to the shared carbon at which a fused ring is joined.

[0101] L a , L 5 and L 6 Each independently may be or include, for example, a single bond or a substituted or unsubstituted C6 to C20 arylene group.

[0102] R a , R 11 and R 12 Each independently may be or include, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group.

[0103] Ar 5 and Ar 6 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.

[0104] m11 and m12 may each independently be an integer of 1 to 4, for example.

[0105] [Chemical formula 5]

[0106]

[0107] In Chemical Formula 5, L 7 It may be or may include, for example, a single bond or a substituted or unsubstituted C6 to C20 arylene group.

[0108] R 13 To R 16 Each independently may be or include, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, 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 7 It may be or may include, for example, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0110] m13, m15 and m16 may each independently be an integer of 1 to 4, for example.

[0111] m14 may be an integer from 1 to 3, for example.

[0112] In one embodiment, m6 can be 2, 3 or 4 and each R 6May be the same as or different from each other.

[0113] In one embodiment, m7 can be 2 or 3 and each R 7 May be the same as or different from each other.

[0114] In one embodiment, m8 can be 2 or 3 and each R 8 May be the same as or different from each other.

[0115] In one embodiment, m9 can be 2, 3 or 4 and each R 9 May be the same as or different from each other.

[0116] In one embodiment, m10 may be 2, 3 or 4 and each R 10 May be the same as or different from each other.

[0117] In one embodiment, m11 may be 2, 3 or 4 and each R 11 May be the same as or different from each other.

[0118] In one embodiment, m12 can be 2, 3 or 4 and each R 12 May be the same as or different from each other.

[0119] In one embodiment, m13 may be 2, 3 or 4 and each R 13 May be the same as or different from each other.

[0120] In one embodiment, m14 can be 2 or 3 and each R 14 May be the same as or different from each other.

[0121] In one embodiment, m15 can be 2, 3 or 4 and each R 15 May be the same as or different from each other.

[0122] In one embodiment, m16 can be 2, 3 or 4 and each R 16 May be the same as or different from each other.

[0123] The second compound may be used together with the first compound in the light emitting layer to increase charge mobility and stability, thereby improving light emitting efficiency and lifespan characteristics.

[0124] In one embodiment, Ar in Chemical Formula 2 3 and Ar 4Each of them may independently be 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.

[0125] In one embodiment, L in Chemical Formula 2 3 and L 4 Each may independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0126] In one embodiment, R in Chemical Formula 2 6 To R 10 Each may independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group.

[0127] In one embodiment, n may be 0 or 1.

[0128] In one embodiment, “substituted” in Chemical Formula 2 means 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.

[0129] In one embodiment, Chemical Formula 2 may be represented by one of Chemical Formula 2-1 to Chemical Formula 2-15.

[0130]

[0131]

[0132] In Chemical Formulae 2-1 to 2-15, R 6 To R 10 may each independently be, for example, hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and R 6 To R 10 Each may independently be, for example, a group of Group II.

[0133] [Group II]

[0134]

[0135] In Group II, R 18 To R 22 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl.

[0136] m18 may be an integer from 1 to 5, for example.

[0137] m19 may be an integer from 1 to 4, for example.

[0138] m20 may be an integer of 1 to 3, for example.

[0139] m21 may be an integer of 1 to 2, for example.

[0140] m22 may be an integer from 1 to 7, for example.

[0141] * is the connection point.

[0142] In Group II, m18 may be greater than or equal to 2 and each R 18 Can be the same or different.

[0143] In Group II, m19 may be greater than or equal to 2 and each R 19 Can be the same or different.

[0144] In Group II, m20 may be greater than or equal to 2 and each R 20 Can be the same or different.

[0145] In Group II, m21 may be greater than or equal to 2 and each R 21 Can be the same or different.

[0146] In Group II, m22 may be greater than or equal to 2 and each R 22 Can be the same or different.

[0147] In one embodiment, Chemical Formula 2 may be represented by Chemical Formula 2-8.

[0148] In one embodiment, the moiety -L in Chemical Formula 2-8 3 -Ar 3 and -L 4 -Ar 4 can each independently be part of Group II.

[0149] In one embodiment, the second compound represented by the combination of Chemical Formula 3 and Chemical Formula 4 may be represented by one of Chemical Formula 3A, Chemical Formula 3B, Chemical Formula 3C, Chemical Formula 3D, and Chemical Formula 3E.

[0150]

[0151] In Chemical Formulae 3A to 3E, Ar 5 ,Ar 6 , L 5 , L 6 , R 11 and R 12 The definitions may be the same as those described above.

[0152] La1 To L a4 Can be used with L 5 and L 6 The definition is the same.

[0153] R a1 To R a4 Can be used with Ar 5 ,Ar 6 , R 11 and R 12 The definition is the same.

[0154] In one embodiment, Ar in Chemical Formulas 3 and 4 5 and Ar 6 Each of them may independently be 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.

[0155] In one embodiment, R a1 To R a4 ,Ar 5 ,Ar 6 , R 11 and R 12 Each of them may independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl.

[0156] In one embodiment, Ar in Chemical Formula 3 and Chemical Formula 4 5 and Ar 6 may each independently be a group of Group II.

[0157] In one embodiment, R a1 To R a4 , R 11 and R 12 Each of them may independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl.

[0158] In one embodiment, R a1 To R a4 , R 11 and R 12 They may each independently be hydrogen, deuterium, cyano or substituted or unsubstituted phenyl.

[0159] In one embodiment, R a1 To Ra4 , R 11 and R 12 and may each independently be hydrogen, deuterium, or substituted or unsubstituted phenyl.

[0160] In one embodiment, the second compound may be represented by Chemical Formula 2-8, and Ar of Chemical Formula 2-8 5 and Ar 6 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, L 5 and L 6 may each independently be a single bond or a substituted or unsubstituted C6 to C20 arylene group, and R 11 and R 12 Each of them may independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl.

[0161] In one embodiment, the second compound may be represented by Chemical Formula 3C, and L in Chemical Formula 3C a3 and L a4 Can be a single bond, L 5 and L 6 may be each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, R 11 , R 12 , R a3 and R a4 may each independently be hydrogen, deuterium or phenyl, and Ar 5 and Ar 6 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0162] Chemical Formula 5 may be represented, for example, by one of Chemical Formula 5-1 to Chemical Formula 5-4.

[0163]

[0164] In Chemical Formula 5-1 to Chemical Formula 5-4, L 7 ,Ar 7 and R 13 To R 16 The definitions may be the same as those described above.

[0165] In one embodiment, Ar in Chemical Formula 5 7It may be 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.

[0166] In one embodiment, R 13 To R 16 Each of them may independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl.

[0167] In one embodiment, the moiety -L in Chemical Formula 5 7 -Ar 7 Can be part of Group II.

[0168] In one embodiment, R 13 To R 16 They may each independently be hydrogen, deuterium, cyano or substituted or unsubstituted phenyl.

[0169] In one embodiment, the second organic optoelectronic device compound may be a compound of Group 2.

[0170] [Group 2]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178] [B-150]

[0179]

[0180] In one embodiment, an example in which at least one hydrogen in Compounds B-1 to B-150 listed in Group 2 is substituted with deuterium is shown.

[0181]

[0182]

[0183]

[0184] (D n refers to the number of deuterium substitutions and represents structures substituted with one or more deuteriums).

[0185] For Compound B-151 to Compound B-195 of Group 2, the most specific structures according to the deuterium substitution position and substitution ratio are exemplarily shown below.

[0186] In one embodiment, for example, it can be substituted with deuterium as shown in the following exemplary compounds, or the deuterium substitution position and deuterium substitution ratio can include all variable ranges within the range of Compound B-1 to Compound B-195 (for example, any hydrogen in any compound can be protium or deuterium).

[0187]

[0188]

[0189]

[0190]

[0191] [B-234]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197] [C-57]

[0198]

[0199] In one embodiment, examples in which at least one hydrogen in compounds C-1 to C-57 listed in Group 2 is substituted with deuterium may be as shown.

[0200]

[0201]

[0202] (D nrefers to the number of deuterium substitutions and represents structures substituted with one or more deuteriums).

[0203] For compounds C-58 to C-72 of Group 2, the most specific structures according to deuterium substitution positions and substitution ratios are exemplarily shown below.

[0204] In one embodiment, it can be substituted with deuterium as shown in the following exemplary compounds, or the deuterium substitution position and deuterium substitution ratio can include any and all variable ranges within the range of Compound C-1 to Compound C-72 (for example, any hydrogen in any compound can be protium or deuterium).

[0205]

[0206]

[0207]

[0208]

[0209]

[0210] In one embodiment, examples in which at least one hydrogen in compounds D-1 to D-60 listed in Group 2 is substituted with deuterium may be as shown.

[0211]

[0212]

[0213]

[0214] (D n refers to the number of deuterium substitutions and represents structures substituted with one or more deuteriums).

[0215] The first compound and the second compound may be included (e.g., mixed) in a weight ratio of, for example, about 1:99 to about 99:1. Within this range, the desired weight ratio can be adjusted using the electron transport capability of the first compound and the hole transport capability of the second compound to achieve bipolar characteristics, thereby improving efficiency and lifespan. Within this range, for example, they may be included in a weight ratio of about 10:90 to about 90:10, about 20:80 to about 80:20, about 20:80 to about 70:30, about 20:80 to about 60:40, or about 30:70 to about 60:40. In one embodiment, they may be included in a weight ratio of about 40:60, about 50:50, or about 60:40.

[0216] Hereinafter, an organic optoelectronic device including the above-mentioned compound for an organic optoelectronic device or the composition for an organic optoelectronic device is described.

[0217] The organic optoelectronic device may be a suitable device that converts electrical energy into light energy, or vice versa, and may be, for example, an organic photovoltaic device, an organic light emitting diode, an organic solar cell, or an organic photosensitive drum.

[0218] Herein, an organic light emitting diode as one example of an organic optoelectronic device is described with reference to the accompanying drawings.

[0219] Figure 1 is a cross-sectional view showing an organic light emitting diode according to some embodiments.

[0220] 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 .

[0221] 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, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or the like; 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.

[0222] The cathode 110 may be made of a conductor having a small work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc., or an alloy thereof; or a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, or BaF2 / Ca.

[0223] The organic layer 105 may include the above-described compound for an organic optoelectronic device or the composition for an organic optoelectronic device.

[0224] The organic layer 105 may include a light emitting layer 130 , which may include a host and a dopant, the host may include the above-described compound for an organic optoelectronic device or a composition for an organic optoelectronic device, and the dopant may include, for example, a platinum complex.

[0225] The composition for an organic optoelectronic device further including a dopant may be, for example, a green light emitting composition.

[0226] The dopant is a material mixed in a small amount with a compound for an organic optoelectronic device or a composition for an organic optoelectronic device to cause light emission, and generally may 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.

[0227] Examples of the dopant may include a phosphorescent dopant, and examples of the phosphorescent dopant may include an organic metal 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.

[0228] [Chemical formula Z]

[0229] L 8 MX 1

[0230] In the chemical formula Z, M may be a metal, and L 8 and X 1 Each may independently be a ligand that forms a complex with M.

[0231] 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 2 and X 2 This may be, for example, a bidentate ligand.

[0232] By L 8 and X 1 Examples of the ligands represented may include group A ligands.

[0233] [Group A]

[0234]

[0235]

[0236] In group A, R 300 To R 302 Each may independently be hydrogen, deuterium, a C1 to C30 alkyl group which may or may not be substituted with a halogen, a C6 to C30 aryl group which may or may not be substituted with a C1 to C30 alkyl group, or a halogen.

[0237] R303 To R 324 Each 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.

[0238] The dopant according to some embodiments may be an iridium complex, and may be mixed with the above-mentioned compound for an organic optoelectronic device in a trace amount.

[0239] In one embodiment, the iridium complex may be represented by Chemical Formula 6.

[0240] [Chemical formula 6]

[0241]

[0242] In Chemical Formula 6, R 101 To R 117 may be each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 133 R 134 R 135 .

[0243] R 133 To R 135 Each may independently be a substituted or unsubstituted C1 to C6 alkyl group.

[0244] L 100 It can be a bidentate ligand of a monovalent anion and is a ligand coordinated to iridium via a lone electron pair of carbon or a heteroatom.

[0245] n1 and n2 may each independently be an integer of 0 to 3 and n1+n2 is any one of an integer of 1 to 3.

[0246] In one embodiment, a dopant represented by Chemical Formula Z-1 may be included.

[0247] [Chemical formula Z-1]

[0248]

[0249] In the chemical formula Z-1, the rings A, B, C and D may each independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring.

[0250] R A , R B , R C and R D Each independently may represent mono-, di-, tri- or tetra-substituted or unsubstituted.

[0251] L B , L C and L D Each may independently be a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′ or a combination thereof.

[0252] In one embodiment, 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' and combinations thereof. In one embodiment, nA can be 0, and L E Does not exist.

[0253] R A , R B , R C , R D R and R' can each independently be hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxyl, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino or a combination thereof. In one embodiment, any adjacent R A , R B , R C , R D , R and R' may be separate or may be linked to each other to provide a ring; X B , X C , X D and X E may 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.

[0254] The dopant according to some embodiments may be a platinum complex, and may be mixed with the composition for an organic optoelectronic device in a trace amount.

[0255] The platinum complex may be represented by Chemical Formula 7, for example.

[0256] [Chemical formula 7]

[0257]

[0258] In chemical formula 7, X 100 Can be O, S or NR 132 .

[0259] R 118 To R 132 may be each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 133 R 134 R 135 .

[0260] R 133 To R 135 Can be each independently substituted or unsubstituted C1 to C6 alkyl. In one embodiment, R 118 To R 132 At least one of them may be -SiR 133 R 134 R 135 or tert-butyl.

[0261] R 133 To R 135 Each may independently be a substituted or unsubstituted C1 to C6 alkyl group.

[0262] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0263] The charge transport region may be, for example, a hole transport region 140 .

[0264] The hole transport region 140 may help to further increase hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.

[0265] In one embodiment, 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.

[0266] [Group B]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273] (D n refers to the number of deuterium substitutions and represents structures substituted with one or more deuteriums).

[0274] In the hole transport region 140 , in addition to the above-mentioned compounds, other suitable compounds may be included.

[0275] In one embodiment, the charge transport region may be, for example, the electron transport region 150 .

[0276] 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.

[0277] In one embodiment, the electron transport region 150 may include an electron transport layer between the cathode 110 and the light emitting layer 130 and an electron transport auxiliary layer between the light emitting layer 130 and the electron transport layer, and a compound of group C may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0278] [Group C]

[0279]

[0280]

[0281]

[0282] Some embodiments may provide an organic light emitting diode including a light emitting layer as an organic layer.

[0283] Some embodiments may provide an organic light emitting diode including a light emitting layer and a hole transport region as an organic layer.

[0284] Some embodiments may provide an organic light emitting diode including a light emitting layer and an electron transport region as an organic layer.

[0285] like Figure 1 As shown, the organic light emitting diode according to the embodiment may further include a hole transport region 140 and an electron transport region 150 as the organic layer 105 in addition to the light emitting layer 130 .

[0286] In one embodiment, 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 the organic layer.

[0287] The organic light emitting diode 100 may be produced by forming an anode or a cathode on a substrate, forming an organic layer using a dry film forming method such as vacuum deposition (evaporation), sputtering, plasma plating, and ion plating, and forming a cathode or an anode thereon.

[0288] The organic light emitting diode may be applied to an organic light emitting display device.

[0289] The following examples and comparative examples are provided to highlight the characteristics of one or more embodiments, but it will be understood that the examples and comparative examples should not be considered as limiting the scope of the embodiments, and the comparative examples should not be considered as being outside the scope of the embodiments. In addition, it will be understood that the embodiments are not limited to the specific details described in the examples and comparative examples.

[0290] 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 appropriate methods unless otherwise specified.

[0291] Synthesis Example 1: Synthesis of Compound A-3

[0292] [Reaction 1]

[0293]

[0294] Step 1: Synthesis of intermediate Int-1

[0295] Under nitrogen flow, 20 g (71 mmol) of 1-bromo-7-chlorodibenzo [b, d] furan, 20.40 g (71 mmol) of (2- (9H-carbazole-9-yl) phenyl) boronic acid, 29.46 g (213 mmol) of K2CO3 and 4.10 g (4 mmol) of Pd (PPh3)4 were suspended in 236 ml of tetrahydrofuran (THF) and 106 ml of distilled water, and then stirred and refluxed for 12 hours. After the reaction was completed, the resultant was extracted and then recrystallized from toluene to obtain 25 g (79.3%) of intermediate Int-1.

[0296] Step 2: Synthesis of intermediate Int-2

[0297] In a round-bottom flask, 22g (50mmol) of intermediate Int-1, 16.36g (64mmol) of biboric acid pinacol ester, 2.43g (3mmol) of Pd (dppf) Cl2, 3.34g (12mmol) of tricyclohexylphosphine and 14.59g (149mmol) of potassium acetate were dissolved in 165ml of DMF. The mixture was stirred and refluxed at 120°C for 10 hours. When the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered and then dissolved in dichloromethane (DCM). After removing moisture with MgSO4, the organic solvent was filtered using a silica gel pad and then removed under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to obtain 25g (94.2%) of intermediate Int-2.

[0298] Step 3: Synthesis of Compound A-3

[0299] Under nitrogen flow, 20g (37mmol) of intermediate Int-2, 11.00g (41mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 12.91g (93mmol) of K2CO3 and 2.16g (2mmol) of Pd (PPh3) 4 were suspended in 124ml of THF and 46ml of distilled water, and then stirred and refluxed for 12 hours. After the reaction was completed, a solid was obtained by extraction with DCM, and then recrystallized from 150ml of toluene to obtain 18g (75.2%) of compound A-3.

[0300] LC-Mass (theoretical value: 640.23 g / mol, measured value: M+=640.75 g / mol)

[0301] Synthesis Example 2: Synthesis of Compound A-21

[0302] [Reaction 2]

[0303]

[0304] Step 1: Synthesis of intermediate Int-3

[0305] Under nitrogen flow, 30 g (107 mmol) of 1-bromo-9-chlorodibenzo [b, d] furan, 30.60 g (107 mmol) of (2- (9H-carbazole-9-yl) phenyl) boronic acid, 44.18 g (320 mmol) of K2CO3 and 6.16 g (5 mmol) of Pd (PPh3)4 were suspended in 355 ml of THF and 159 ml of distilled water, and then stirred and refluxed for 12 hours. After the reaction was completed, the resultant was extracted and then recrystallized from toluene to obtain 38 g (80.3%) of intermediate Int-3.

[0306] Step 2: Synthesis of intermediate Int-4

[0307] In a round-bottom flask, 25g (56mmol) of intermediate Int-3, 18.59g (73mmol) of biboric acid pinacol ester, 2.76g (3mmol) of Pd (dppf) Cl2, 3.79g (14mmol) of tricyclohexylphosphine and 16.58g (169mmol) of potassium acetate were dissolved in 187ml of DMF. The mixture was stirred and refluxed at 120°C for 10 hours. When the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered and then dissolved in DCM. After removing moisture with MgSO4, the organic solvent was filtered using a silica gel pad and then removed under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to obtain 26g (86.2%) of intermediate Int-4.

[0308] Step 3: Synthesis of Compound A-21

[0309] Under nitrogen flow, 26g (49mmol) of intermediate Int-4, 18.36g (53mmol) of 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine, 16.78g (121mmol) of K2CO3 and 2.81g (2mmol) of Pd(PPh3)4 were suspended in 161ml of THF and 60ml of distilled water, and then stirred and refluxed for 12 hours. After the reaction was completed, a solid was obtained by extraction with DCM, and then recrystallized with 300ml of toluene to obtain 30g (86.2%) of compound A-21.

[0310] LC-Mass (theoretical value: 716.26 g / mol, measured value: M+=716.84 g / mol)

[0311] Synthesis Example 3: Synthesis of Compound A-48

[0312] [Reaction 3]

[0313]

[0314]

[0315] Step 1: Synthesis of intermediate Int-5

[0316] Under nitrogen flow, 30 g (107 mmol) of 1-bromo-6-chlorodibenzo [b, d] furan, 30.60 g (107 mmol) of (2- (9H-carbazole-9-yl) phenyl) boronic acid, 44.18 g (320 mmol) of K2CO3 and 6.16 g (5 mmol) of Pd (PPh3)4 were suspended in 355 ml of THF and 159 ml of distilled water, and then stirred and refluxed for 12 hours. After the reaction was completed, the resultant was extracted and then recrystallized from toluene to obtain 40 g (84.6%) of intermediate Int-5.

[0317] Step 2: Synthesis of intermediate Int-6

[0318] In a round-bottom flask, 30g (68mmol) of intermediate Int-5, 22.31g (88mmol) of biboric acid pinacol ester, 3.31g (4mmol) of Pd (dppf) Cl2, 4.55g (16mmol) of tricyclohexylphosphine and 19.90g (203mmol) of potassium acetate were dissolved in 225ml of DMF. The mixture was stirred and refluxed at 120°C for 10 hours. When the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered and then dissolved in DCM. After removing moisture with MgSO4, the organic solvent was filtered using a silica gel pad and then removed under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to obtain 30g (82.9%) of intermediate Int-6.

[0319] Step 3: Synthesis of Compound A-48

[0320] Under nitrogen flow, 20g (37mmol) of intermediate Int-6, 14.70g (41mmol) of 2-chloro-4-(1-dibenzofuranyl)-6-phenyl-1,3,5-triazine, 12.91g (93mmol) of K2CO3 and 2.16g (2mmol) of Pd(PPh3)4 were suspended in 124ml of THF and 46ml of distilled water, and then stirred and refluxed for 12 hours. After the reaction was completed, a solid was obtained by extraction with DCM, and then recrystallized from 300ml of toluene to obtain 25g (91.6%) of compound A-48.

[0321] LC-Mass (theoretical value: 730.24 g / mol, measured value: M+ = 730.83 g / mol)

[0322] Synthesis Example 4: Synthesis of Compound A-130

[0323] [Reaction 4]

[0324]

[0325] Step 1: Synthesis of intermediate Int-7

[0326] Under nitrogen flow, 50 g (168 mmol) of 1-bromo-8-chlorodibenzo [b, d] thiophene, 48.24 g (168 mmol) of (2- (9H-carbazole-9-yl) phenyl) boronic acid, 69.66 g (504 mmol) of K2CO3 and 9.71 g (8 mmol) of Pd (PPh3) 4 were dissolved in 560 ml of THF and 252 ml of distilled water, and then stirred and refluxed for 12 hours. After the reaction was completed, the resultant was extracted and then recrystallized from toluene to obtain 65 g (84.1%) of intermediate Int-7.

[0327] Step 2: Synthesis of intermediate Int-8

[0328] In a round-bottom flask, 60g (130mmol) of intermediate Int-7, 43.06g (170mmol) of biboric acid pinacol ester, 6.39g (8mmol) of Pd (dppf) Cl2, 8.78g (31mmol) of tricyclohexylphosphine and 38.41g (391mmol) of potassium acetate were dissolved in 434ml of DMF. The mixture was stirred and refluxed at 120°C for 10 hours. When the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered and then dissolved in DCM. After removing moisture with MgSO4, the organic solvent was filtered using a silica gel pad and then removed under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to obtain 65g (90.4%) of intermediate Int-8.

[0329] Step 3: Synthesis of Compound A-130

[0330] Under nitrogen flow, 30g (54mmol) of intermediate Int-8, 20.57g (60mmol) of 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine, 18.80g (136mmol) of K2CO3 and 3.14g (3mmol) of Pd(PPh3)4 were suspended in 181ml of THF and 68ml of distilled water, and then stirred and refluxed for 12 hours. After the reaction was completed, a solid was obtained by extraction with DCM, and then recrystallized with 400ml of toluene to obtain 35g (87.8%) of compound A-130.

[0331] LC-Mass (theoretical value: 732.23 g / mol, measured value: M+=732.91 g / mol)

[0332] Synthesis Example 5: Synthesis of Compound B-136

[0333]

[0334] Compound B-136 was synthesized by referring to the synthesis method of European Patent EP3034581.

[0335] HRMS (70 eV, EI+): m / z calculated for C42H28N2: 560.2252, measured: 560.

[0336] Elemental analysis: C, 90%; H, 5%

[0337] Comparative Synthesis Example 1: Synthesis of Compound Main Body-1

[0338] [Reaction 5]

[0339]

[0340] Step 1: Synthesis of intermediate Int-9

[0341] Under nitrogen flow, 25 g (89 mmol) of 2-bromo-8-chlorodibenzo [b, d] furan, 25.50 g (89 mmol) of (2- (9H-carbazole-9-yl) phenyl) boronic acid, 36.82 g (266 mmol) of K2CO3 and 5.13 g (4 mmol) of Pd (PPh3)4 were suspended in 296 ml of THF and 133 ml of distilled water, and then stirred and refluxed for 12 hours. After the reaction was completed, the resultant was extracted and then recrystallized from toluene to obtain 30 g (76.1%) of intermediate Int-9.

[0342] Step 2: Synthesis of intermediate Int-10

[0343] In a round-bottom flask, 30g (68mmol) of intermediate Int-9, 22.31g (88mmol) of biboric acid pinacol ester, 3.31g (4mmol) of Pd (dppf) Cl2, 4.55g (16mmol) of tricyclohexylphosphine and 19.90g (203mmol) of potassium acetate were dissolved in 225ml of DMF. The mixture was stirred and refluxed at 120°C for 10 hours. When the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered and then dissolved in DCM. After removing moisture with MgSO4, the organic solvent was filtered using a silica gel pad and then removed under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to obtain 35g (96.7%) of intermediate Int-10.

[0344] Step 3: Synthesis of Compound Host-1

[0345] Under nitrogen flow, 35g (65mmol) of intermediate Int-10, 19.25g (72mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 22.59g (163mmol) of K2CO3 and 3.78g (3mmol) of Pd (PPh3) 4 were suspended in 217ml of THF and 81ml of distilled water, and then stirred and refluxed for 12 hours. After the reaction was completed, a solid was obtained by extraction with DCM, and then recrystallized with 300ml of toluene to obtain 35g (83.6%) of compound main body-1.

[0346] LC-Mass (theoretical value: 640.23 g / mol, measured value: M+=640.75 g / mol)

[0347] Comparative Synthesis Example 2: Synthesis of Compound Main Body-2

[0348] [Reaction formula 6]

[0349]

[0350] Step 1: Synthesis of intermediate Int-11

[0351] Under nitrogen flow, 30 g (136 mmol) of 2-chloro-9-fluorodibenzo [b, d] furan, 25.01 g (150 mmol) of carbazole and 86.59 g (408 mmol) of K3PO4 were dissolved in 453 ml of DMF, and then stirred and refluxed at 120° C. for 12 hours. After the reaction was completed, the resultant was extracted and then recrystallized from toluene to obtain 50 g (82.8%) of intermediate Int-11.

[0352] Step 2: Synthesis of intermediate Int-12

[0353] In a round-bottom flask, 50g (136mmol) of intermediate Int-11, 44.87g (177mmol) of biboric acid pinacol ester, 6.66g (8mmol) of Pd (dppf) Cl2, 9.15g (33mmol) of tricyclohexylphosphine and 40.03g (408mmol) of potassium acetate were dissolved in 453ml of DMF. The mixture was stirred and refluxed at 120°C for 10 hours. When the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered and then dissolved in DCM. After removing moisture with MgSO4, the organic solvent was filtered using a silica gel pad and then removed under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to obtain 45g (72.1%) of intermediate Int-12.

[0354] Step 3: Synthesis of Compound Host-2

[0355] 45g (98mmol) of intermediate Int-12, 28.85g (108mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 33.85g (245mmol) of K2CO3 and 5.66g (5mmol) of Pd(PPh3)4 were suspended in 326ml of THF and 122ml of distilled water, and then stirred and refluxed for 12 hours under a nitrogen stream. After the reaction was completed, a solid was obtained by extraction with DCM, and then recrystallized with 400ml of toluene to obtain 47g (85.0%) of compound main body-2.

[0356] LC-Mass (theoretical value: 564.20 g / mol, measured value: M+=564.65 g / mol)

[0357] Comparative Synthesis Example 3: Synthesis of Compound Main Body-3

[0358] [Reaction 7]

[0359]

[0360]

[0361] Step 1: Synthesis of intermediate Int-13

[0362] Under nitrogen flow, 20 g (71 mmol) of 1-bromo-8-chlorodibenzo [b, d] furan, 20.40 g (71 mmol) of (4- (9H-carbazole-9-yl) phenyl) boronic acid, 29.46 g (213 mmol) of K2CO3 and 4.10 g (5 mmol) of Pd (PPh3)4 were suspended in 236 ml of THF and 106 ml of distilled water, and then stirred and refluxed for 12 hours. After the reaction was completed, the resultant was extracted and recrystallized from toluene to obtain 28 g (88.8%) of intermediate Int-13.

[0363] Step 2: Synthesis of intermediate Int-14

[0364] In a round-bottom flask, 28g (63mmol) of intermediate Int-13, 20.82g (82mmol) of biboric acid pinacol ester, 3.09g (4mmol) of Pd (dppf) Cl2, 4.25g (15mmol) of tricyclohexylphosphine and 18.57g (189mmol) of potassium acetate were dissolved in 210ml of DMF. The mixture was stirred and refluxed at 120°C for 10 hours. When the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered and then dissolved in DCM. After removing moisture with MgSO4, the organic solvent was filtered using a silica gel pad and then removed under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to obtain 30g (88.8%) of intermediate Int-14.

[0365] Step 3: Synthesis of Compound Host-3

[0366] 30g (56mmol) of intermediate Int-14, 16.50g (62mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 19.36g (140mmol) of K2CO3 and 3.24g (3mmol) of Pd (PPh3) 4 were suspended in 186ml of THF and 70ml of distilled water, and then stirred and refluxed for 12 hours under a nitrogen stream. After the reaction was completed, the solid was extracted therefrom with DCM, and then recrystallized with 300ml of toluene to obtain 32g (89.1%) of the compound main body-3.

[0367] LC-Mass (theoretical value: 640.23 g / mol, measured value: M+=640.75 g / mol)

[0368] (Table 1)

[0369] Compound HOMO level (eV) LUMO level (eV) A-3 -5.37 -1.99 A-21 -5.17 -1.98 A-48 -5.37 -1.93 A-130 -5.47 -1.90 Main Body-1 -5.43 -1.91 Main Body-2 -5.32 -1.91 Main body-3 -5.33 -1.90

[0370] Example 1: Fabrication of a green organic light emitting diode (single body)

[0371] 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 moved to a plasma cleaner, cleaned for 10 minutes by using oxygen plasma, and moved to a vacuum depositor. The obtained ITO transparent electrode was used as an anode, and Compound A doped with 3% NDP-9 (available from Novaled) was vacuum deposited on the ITO substrate to form A thick hole injection layer is formed, and compound A is deposited on the hole injection layer to form On the hole transport layer, a compound B is deposited to form On the hole transport auxiliary layer, a composite A-3 as a host (doped with 7 wt % of PhGD as a dopant) was formed by vacuum deposition. Subsequently, compound C is deposited on the light-emitting layer to form The electron transport auxiliary layer is formed by vacuum depositing compound D and Liq at a weight ratio of 1:1 simultaneously. Thick electron transport layer. and Al The cathode is formed by vacuum deposition on the electron transport layer in sequence, thereby manufacturing an organic light emitting diode.

[0372] ITO / Compound A (3% NDP-9 doping, ) / Compound A / Compound B / EML[host (compound A-3):PhGD=93wt%:7wt%] / Compound C / Compound D:LiQ / LiQ / Al

[0373] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0374] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0375] 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

[0376] Compound D: 2-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0377] [PhGD]

[0378]

[0379] Examples 2 to 4 and Comparative Example 1

[0380] Each organic light emitting diode was manufactured in the same manner as in Example 1, except that the composition was changed to those shown in Table 2.

[0381] Example 5: Fabrication of Green Organic Light Emitting Diode (Host Hybrid)

[0382] 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 moved to a plasma cleaner, cleaned for 10 minutes by using oxygen plasma, and moved to a vacuum depositor. The obtained ITO transparent electrode was used as an anode, and Compound A doped with 3% NDP-9 (available from Novaled) was vacuum deposited on the ITO substrate to form A thick hole injection layer is formed, and compound A is deposited on the hole injection layer to form On the hole transport layer, a compound E is deposited to form On the hole transport auxiliary layer, a thick hole transport auxiliary layer was formed by simultaneously vacuum depositing compound A-3 as a host and compound B-136 (and doping 15 wt % of PtGD as a dopant) in a weight ratio of 3:7. Subsequently, compound F is deposited on the light-emitting layer to form The thick electron transport auxiliary layer is formed by vacuum depositing compound G and Liq at a ratio of 1:1 simultaneously. Thick electron transport layer. and Al Vacuum deposition is sequentially performed on the electron transport layer to form a cathode, thereby manufacturing an organic light emitting diode.

[0383] ITO / Compound A (3% NDP-9 doping, ) / Compound A / Compound E / EML[host (Compound A-3:Compound B-136=3:7w / w):PtGD=85wt%:15wt%] / Compound F / Compound G:LiQ / LiQ / Al

[0384] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine

[0385] Compound E: 9,9-dimethyl-N-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-4-(4-phenylphenyl)-9H-fluoren-2-amine

[0386] Compound F: 4-{4-[4-(9,9-dimethyl-9H-fluoren-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[0387] Compound G: 2-(4-{1-[4-(diphenyl-1,3,5-triazine-2-yl)phenyl]naphthalen-2-yl}-4,6-diphenyl-1,3,5-triazine

[0388] [PtGD]

[0389]

[0390] Examples 6 to 8 and Comparative Examples 2 to 4

[0391] Each organic light emitting diode was manufactured in the same manner as in Example 5, except that the composition was changed to those shown in Tables 3 to 5.

[0392] evaluate

[0393] The driving voltage, luminous efficiency, and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 8 and Comparative Examples 1 to 4 were evaluated.

[0394] The specific measurement method is as follows, and the results are shown in Tables 2 to 5.

[0395] (1) Measuring the change in current density due to voltage change

[0396] 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.

[0397] (2) Measuring the change in brightness due to voltage changes

[0398] While increasing the voltage of the organic light emitting diode from 0 V to 10 V, the luminance was measured using a luminance meter (Minolta Cs-1000A).

[0399] (3) Measurement of luminous efficiency

[0400] Using the luminance and current density measured according to the above items (1) and (2), calculate the same current density (10 mA / cm 2 ) under luminous efficiency (cd / A).

[0401] Based on Comparative Example 1, the luminous efficiency values ​​of Examples 1 to 4 and Comparative Example 1 were calculated as relative values ​​and are listed in Table 2.

[0402] Based on Comparative Example 2, the luminous efficiency values ​​of Examples 5 to 8 and Comparative Example 2 were calculated as relative values ​​and are listed in Table 3.

[0403] Based on Comparative Example 3, the luminous efficiency values ​​of Examples 5 to 8 and Comparative Example 3 were calculated as relative values ​​and are listed in Table 4.

[0404] Based on Comparative Example 4, the luminous efficiency values ​​of Examples 5 to 8 and Comparative Example 1 were calculated as relative values ​​and are listed in Table 5.

[0405] (4) Measurement life

[0406] By converting the brightness (cd / m 2 ) maintained at 24000cd / m 2 The time required for the luminous efficiency (cd / A) to decrease to 97% was measured to obtain the result.

[0407] Based on Comparative Example 1, the life measurement values ​​of Examples 1 to 4 and Comparative Example 1 were calculated as relative values ​​and are listed in Table 2.

[0408] Based on Comparative Example 2, the life measurement values ​​of Examples 5 to 8 and Comparative Example 2 were calculated as relative values ​​and are listed in Table 3.

[0409] Based on Comparative Example 3, the life measurement values ​​of Examples 5 to 8 and Comparative Example 3 were calculated as relative values ​​and are listed in Table 4.

[0410] Based on Comparative Example 4, the life measurement values ​​of Examples 5 to 8 and Comparative Example 4 were calculated as relative values ​​and are listed in Table 5.

[0411] (5) Measure the driving voltage

[0412] An amperovoltmeter (Keithley 2400) was used at 15 mA / cm 2 The driving voltage of each diode is measured.

[0413] Based on Comparative Example 1, the driving voltages of Examples 1 to 4 and Comparative Example 1 were calculated as relative values ​​and are shown in Table 2.

[0414] Based on Comparative Example 2, the driving voltages of Examples 5 to 8 and Comparative Example 2 were calculated as relative values ​​and are shown in Table 3.

[0415] Based on Comparative Example 3, the driving voltages of Examples 5 to 8 and Comparative Example 3 were calculated as relative values ​​and are shown in Table 4.

[0416] Based on Comparative Example 4, the driving voltages of Examples 5 to 8 and Comparative Example 4 were calculated as relative values ​​and are shown in Table 5.

[0417] (Table 2)

[0418]

[0419] (Table 3)

[0420]

[0421]

[0422] (Table 4)

[0423]

[0424] (Table 5)

[0425]

[0426] Referring to Tables 2 to 5, the organic light emitting diodes according to Examples 1 to 8 have improved driving voltage and light emitting efficiency, and at the same time, significantly improved lifespan characteristics, compared to the organic light emitting diodes according to Comparative Examples 1 to 4.

[0427] 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 having high efficiency and a long lifespan.

[0428] While reducing the driving voltage, high-efficiency and long-life organic optoelectronic devices can be achieved.

[0429] Exemplary embodiments have been disclosed herein, and although specific terms are used, these terms are used and understood only in a general and descriptive sense and not for limiting purposes. In some cases, as will be apparent to those skilled in the art upon filing this application, unless otherwise specifically indicated, the characteristics, features, and / or elements described in conjunction with a specific embodiment may be used alone or in combination with the characteristics, features, and / or elements described in conjunction with other embodiments. Therefore, those skilled in the art will appreciate that changes in various forms and details may be made without departing from the spirit and scope of the invention as set forth in the appended claims.

Claims

1. A compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1: [Chemical formula 1] In Chemical Formula 1, X is O or S, L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, R 1 To R 5 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, m1, m2 and m5 are each independently an integer from 1 to 4, and m3 and m4 are each independently an integer of 1 to 3.

2. The compound for an organic optoelectronic device according to claim 1, wherein The compound is represented by one of Compound 1-1 to Compound 1-4: In Chemical Formulae 1-1 to 1-4, X, L 1 and L 2 ,Ar 1 and Ar 2 , R 1 To R 5 And m1 to m5 are the same as those defined in Chemical Formula 1.

3. The compound for an organic optoelectronic device according to claim 1, wherein R 1 To R 4 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, substituted or unsubstituted C2 to C18 heterocyclic group, or a combination thereof, and R 5 is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, or a combination thereof. 4 . The compound for an organic optoelectronic device according to claim 1 , wherein the compound has a HOMO level of −5.5 eV to −4.9 eV. 5 . The compound for an organic optoelectronic device according to claim 1 , wherein the compound has a LUMO energy level of −2.1 eV to −1.7 eV.

6. The compound for an organic optoelectronic device according to claim 1, wherein Ar 1 and Ar 2 Each is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenyl group.

7. The compound for an organic optoelectronic device according to claim 6, wherein Ar 1 and Ar 2 At least one of the following is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group.

8. The compound for an organic optoelectronic device according to claim 1, wherein Part-L 1 -Ar 1 and -L 2 -Ar 2 Each independently is part of Group I: [Group I] In Group I, R 23 To R 25 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, m23 is an integer from 1 to 5, m24 is an integer from 1 to 4, m25 is an integer from 1 to 3, and * is the connection point.

9. A compound for an organic optoelectronic device, the compound being a compound of Group 1: [Group 1] 10. A composition for an organic optoelectronic device, comprising: a first compound, and a second compound; in, The first compound is the compound for an organic optoelectronic device according to claim 1, 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 6 To R 10 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, 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, L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, m6, m9 and m10 are each independently an integer from 1 to 4, m7 and m8 are each independently an integer from 1 to 3, and n is an integer from 0 to 2; In Chemical Formula 3 and Chemical Formula 4, Two adjacent ones of a1* to a4* in Chemical Formula 3 are connecting carbons connected to the * in Chemical Formula 4, and the remaining two of a1* to a4* in Chemical Formula 3 not connected to the * in Chemical Formula 4 are CL a -R a , L a , L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R a , R 11 and R 12 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, Ar 5 and Ar 6 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m11 and m12 are each independently an integer from 1 to 4; [Chemical formula 5] In Chemical Formula 5, L 7 is a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 13 To R 16 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, Ar 7 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m13, m15 and m16 are each independently an integer from 1 to 4, and m14 is an integer from 1 to 3.

11. The composition for an organic optoelectronic device according to claim 10, wherein: The second compound is represented by Chemical Formula 2, Chemical formula 2 is represented by Chemical formula 2-8: [Chemical formula 2-8] In Chemical Formula 2-8, R 6 To R 9 are each independently hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, m6 and m9 are each independently an integer from 1 to 4, m7 and m8 are each independently an integer from 1 to 3, Part-L 3 -Ar 3 and -L 4 -Ar 4 each independently being part of Group II, [Group II] In Group II, R 18 To R 22 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, m18 is an integer from 1 to 5, m19 is an integer from 1 to 4, m20 is an integer from 1 to 3, m21 is an integer from 1 to 2, m22 is an integer from 1 to 7, and * is the connection point.

12. The composition for an organic optoelectronic device according to claim 10, wherein The second compound is represented by a combination of Chemical Formula 3 and Chemical Formula 4, 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, L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, R 11 , R 12 , R a3 and R a4 are each independently hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, Ar 5 and Ar 6 are each independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted biphenyl, and m11 and m12 are each independently an integer of 1 to 4.

13. 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, The at least one organic layer comprises the compound for an organic optoelectronic device according to any one of claims 1 to 9 or the composition for an organic optoelectronic device according to any one of claims 10 to 12.

14. The organic optoelectronic device according to claim 13, wherein: The at least one organic layer comprises a light emitting layer, The light-emitting layer comprises a host and a dopant, The host comprises the compound, and The dopant includes an iridium complex.

15. The organic optoelectronic device according to claim 14, wherein: The iridium complex is represented by Chemical Formula 6: [Chemical formula 6] In Chemical Formula 6, R 101 To R 117 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 133 R 134 R 135 , R 133 To R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group, L 100 is a bidentate ligand for a monovalent anion and is coordinated to iridium via a lone electron pair of a carbon or heteroatom, and n1 and n2 are each independently an integer from 0 to 3 and n1+n2 is an integer from 1 to 3.

16. The organic optoelectronic device according to claim 13, wherein: The at least one organic layer comprises a light emitting layer, The light-emitting layer comprises a host and a dopant, The body comprises the composition, and The dopant includes a platinum complex.

17. The organic optoelectronic device according to claim 16, wherein: The platinum complex is represented by Chemical Formula 7: [Chemical formula 7] In Chemical Formula 7, X 100 O, S or NR 132 , R 118 To R 132 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 133 R 134 R 135 , R 133 To R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group, R 118 To R 132 At least one of them is -SiR 133 R 134 R 135 or tert-butyl, and R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. 18 . A display device comprising the organic optoelectronic device according to claim 13 .

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