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 comprising a compound for an organic optoelectronic device, the organic optoelectronic device comprising the compound or the composition, the display device comprising an organic optoelectronic device, the compound is represented by Chemical Formula 1. [Chemical Formula 1] # imgabs0 #

Description

[0001] Citation of Related Applications

[0002] This application claims the priority and benefit of Korean Patent Application No. 10-2024-0002491, filed with the Korean Intellectual Property Office on January 5, 2024, 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 (e.g., an organic optoelectronic diode) is a device capable of converting electrical energy and light energy into each other.

[0005] According to the working principle, organic optoelectronic devices can be divided into two categories. 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, and the other is a light-emitting device that generates light energy from electrical energy by applying a voltage or current to the electrodes.

[0006] Examples of organic optoelectronic devices may include organic optoelectronic devices, organic light-emitting diodes, organic solar cells, and organic photoreceptors.

[0007] Among them, due to the increasing demand for flat panel displays, organic light-emitting diodes (OLEDs) have attracted attention in recent years. An organic light-emitting diode converts electrical energy into light by applying a current to an organic light-emitting material, and the performance of the organic light-emitting diode can be affected by the organic materials disposed between the electrodes. Summary of the Invention

[0008] Embodiments can be achieved 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, L 1 is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, R 1 to R 19Each independently is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heterocyclic group, substituted or unsubstituted C1-C10 alkylsilyl, or a combination thereof, m1 is an integer from 1 to 3, and when m1 is 2 or 3, each R 5 is the same as or different from each other.

[0012] Embodiments can be achieved by providing a composition for an organic optoelectronic device, the composition comprising a first compound and a second compound, wherein the first compound is a compound for an organic optoelectronic device according to one embodiment, and the second compound is represented by Chemical Formula 2:

[0013] [Chemical Formula 2]

[0014]

[0015] In Chemical Formula 2, Z 1 to Z 6 each independently is N or C-L a -R a , provided that: at least two of Z 1 to Z 6 are N, each L a independently is a single bond, substituted or unsubstituted C6-C20 arylene, substituted or unsubstituted C2-C20 heterocyclic group, or a combination thereof, each R a independently is hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heterocyclic group, substituted or unsubstituted silyl, substituted or unsubstituted amino group, halogen, cyano, or a combination thereof, and each R a exists separately, or adjacent groups among them are connected to form a substituted or unsubstituted aliphatic monocyclic or polycyclic ring, substituted or unsubstituted aromatic monocyclic or polycyclic ring, or substituted or unsubstituted heteroaromatic monocyclic or polycyclic ring.

[0016] Embodiments can 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 at least one organic layer contains a compound for an organic optoelectronic device according to one embodiment.

[0017] Embodiments can 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 at least one organic layer contains a composition for an organic optoelectronic device according to one embodiment.

[0018] The embodiments can be implemented by providing a display device including an organic optoelectronic device according to one embodiment. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] Features will be apparent to those skilled in the art by referring to the accompanying drawings and describing exemplary embodiments in detail, where:

[0020] Figure 1 is a cross-sectional view showing an organic light-emitting diode according to some exemplary embodiments. DETAILED DESCRIPTION

[0021] 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 set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey exemplary embodiments to those skilled in the art.

[0022] In the 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 element, it can be directly on the other layer or element, or an intermediate layer may also be present. Additionally, it will be understood that when a layer is referred to as being "between" two layers, the layer may be the only layer between the two layers, or one or more intermediate layers may also be present. Like reference numerals always denote like elements. As used herein, the term "or" is not necessarily an exclusive term, e.g., "A or B" will include A, B, or A and B.

[0023] As used herein, when no additional definition is provided, "substituted" means that at least one hydrogen of a substituent or compound is replaced by the following: deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1-C30 amino, nitro, substituted or unsubstituted C1-C40 silyl, C1-C30 alkyl, C1-C10 alkylsilyl, C6-C30 arylsilyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, C1-C20 alkoxy, C1-C10 trifluoroalkyl, cyano, or a combination thereof.

[0024] In one instance, "substituted" means that at least one hydrogen of a substituent or compound is replaced by one of the following: deuterium, a C1-C30 alkyl group, a C1-C10 alkylsilyl group, a C6-C30 arylsilyl group, a C3-C30 cycloalkyl group, a C3-C30 heterocycloalkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, or a cyano group. In one specific instance, "substituted" means that at least one hydrogen of a substituent or compound is replaced by one of the following: deuterium, a C1-C20 alkyl group, a C6-C30 aryl group, or a cyano group. In one specific instance, "substituted" means that at least one hydrogen of a substituent or compound is replaced by one of the following: deuterium, a C1-C5 alkyl group, a C6-C18 aryl group, or a cyano group. In one specific instance, "substituted" means that at least one hydrogen of a substituent or compound is replaced by one of the following: deuterium, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0025] "Unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom is retained.

[0026] In this specification, "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).

[0027] As used herein, when no other definition is provided, "hetero" means containing one to three heteroatoms selected from N, O, S, P, and Si and the remaining carbon in a functional group.

[0028] As used herein, "aryl" means a group including at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have conjugated p orbitals, such as a phenyl group, a naphthyl group, etc. Two or more hydrocarbon aromatic moieties may be connected by a σ bond and may be, for example, a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as a fluorenyl group.

[0029] An aryl group may include a monocyclic, polycyclic, or fused polycyclic (i.e., rings sharing adjacent carbon atom pairs) functional group.

[0030] As used herein, "heterocyclic group" is a superordinate 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 group, a cycloalkyl group, their fused rings, or a combination thereof. When the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0031] For example, "heteroaryl" may refer to an aryl group including at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly connected by a σ bond, or when the heteroaryl group includes two or more rings, two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may include one to three heteroatoms.

[0032] More specifically, the substituted or unsubstituted C6-C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted condensed 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 chrysenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof, but is not limited thereto.

[0033] More specifically, the substituted or unsubstituted C2-C30 heterocyclic group may be a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzonaphthofuryl group, a substituted or unsubstituted benzonaphthothienyl group, a substituted or unsubstituted benzofurofluorene group, a substituted or unsubstituted benzothienofluorene group, or a combination thereof, but is not limited thereto.

[0034] As used herein, the hole property refers to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive property 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.

[0035] In addition, the electron property refers to the ability to accept electrons when an electric field is applied, and due to the conductive property 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.

[0036] Hereinafter, compounds for an organic optoelectronic device according to some exemplary embodiments are described.

[0037] The compounds for an organic optoelectronic device according to some exemplary embodiments can be represented by Chemical Formula 1.

[0038] [Chemical Formula 1]

[0039]

[0040] In Chemical Formula 1, L 1 may be or may include, for example, a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0041] Ar 1 and Ar 2 may each independently be or include, for example, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0042] R 1 to R 19 may each independently be or include, for example, hydrogen, deuterium, a cyano group, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted C1 to C10 alkylsilyl group, or a combination thereof.

[0043] m1 may be, for example, an integer from 1 to 3.

[0044] The compound represented by Chemical Formula 1 may have the following structure, in which the indolocarbazole mother nucleus or core is additionally substituted by carbazole in the N-direction of indolocarbazole (for example, through a linking phenylene group).

[0045] By being additionally substituted by carbazole in the N-direction of indolocarbazole, it may have a shallow HOMO, and thus the driving voltage can be improved due to the fast hole transport property. These properties may be due to the hole properties of the additionally substituted carbazole and cannot be expected from a structure that does not include the additionally substituted carbazole.

[0046] In one embodiment, the N-direction of indolocarbazole may be substituted by an ortho-phenylene group for indolocarbazole (for example, as a linking group), thereby increasing steric hindrance, significantly reducing the deposition temperature, and improving thermal stability.

[0047] In one embodiment, the o-phenylene can help ensure sufficient distance between molecules, thereby weakening TTA (triplet-triplet annihilation) and improving the efficiency of the organic light-emitting diode using the same.

[0048] In one embodiment, m1 can be 2 or 3, and each R 5 can be the same as or different from each other.

[0049] In one embodiment, Chemical Formula 1 can be represented by, for example, one of Chemical Formulas 1-1 to 1-4.

[0050]

[0051]

[0052] In Chemical Formulas 1-1 to 1-4, L 1 , Ar 1 and Ar 2 , R 1 to R 19 and m1 can be defined the same as those of Chemical Formula 1.

[0053] In one embodiment, Ar 1 and Ar 2 can each independently be, for example, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted o-terphenylenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted dibenzosilolyl.

[0054] In one embodiment, the moieties *-L 1 -Ar 2 and *-Ar 1 can each independently be, for example, moieties of Group I.

[0055] [Group I]

[0056]

[0057] In Group I, R 20 to R 22 can each independently be, for example, hydrogen, deuterium, cyano, a substituted or unsubstituted C1 to C10 alkyl, or a substituted or unsubstituted C6 to C12 aryl.

[0058] m2 can be, for example, an integer from 1 to 5.

[0059] m3 can be, for example, an integer from 1 to 4.

[0060] m4 can be, for example, an integer from 1 to 3.

[0061] * is a connection point.

[0062] In one embodiment, m2 can be from 2 to 5, and each R 20 can be the same as or different from each other.

[0063] In one embodiment, m3 can be from 2 to 4, and each R 21 can be the same as or different from each other.

[0064] In one embodiment, m4 can be 2 or 3, and each R 22 can be the same as or different from each other.

[0065] In one embodiment, R 1 to R 19 can each independently be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C2-C20 heterocyclic group, substituted or unsubstituted C1-C10 alkylsilyl, or a combination thereof.

[0066] In one embodiment, R 1 to R 19 can each independently 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 fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzosilolyl, or substituted or unsubstituted trimethylsilyl.

[0067] In one embodiment, the compound for an organic optoelectronic device represented by Chemical Formula 1 can be, for example, a compound of Group 1.

[0068] [Group 1]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082] (Dn refers to the number of deuterium substitutions and indicates a structure substituted with one or more deuterium atoms). However, as described above, based on natural or artificial substitution, any hydrogen in any compound can be protium, deuterium, or tritium.

[0083] The composition for an organic optoelectronic device according to some exemplary embodiments may include a first compound and a second compound. The first compound may be the compound for an organic optoelectronic device described above. In one embodiment, the second compound may be represented by Chemical Formula 2, for example.

[0084] [Chemical Formula 2]

[0085]

[0086] In Chemical Formula 2, Z 1 to Z 6 may each independently be, for example, N or C-L a -R a . In one embodiment, at least two of Z 1 to Z 6 are N.

[0087] Each L a may independently be or include, for example, a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof.

[0088] Each R a may independently be or include, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a halogen, a cyano group, or a combination thereof.

[0089] Each R aThey may exist separately or adjacent groups among them may be connected to form a substituted or unsubstituted aliphatic monocyclic or polycyclic, substituted or unsubstituted aromatic monocyclic or polycyclic, or substituted or unsubstituted heteroaromatic monocyclic or polycyclic.

[0090] The second compound can contribute to effectively expanding the LUMO energy band by including a nitrogen-containing hexagonal or six-membered ring moiety, and thus it can be included together with the above-mentioned first compound to increase the balance of holes and electrons, thereby significantly improving the lifetime characteristics of the device to which it is applied.

[0091] In one embodiment, two of Z 1 to Z 6 can be nitrogen (N) and the rest can be C-L a -R a .

[0092] In one embodiment, Z 1 and Z 3 can be nitrogen, Z 2 can be N or C-L a -R a , Z 4 can be N or C-L a -R a , Z 5 can be N or C-L a -R a , and Z 6 can be N or C-L a -R a .

[0093] In one embodiment, three of Z 1 to Z 6 can be nitrogen (N) and the rest can be C-L a -R a .

[0094] In one embodiment, Z 1 , Z 3 and Z 5 can be nitrogen, Z 2 can be N or C-L a -R a , Z 4 can be N or C-L a -R a , and Z 6 can be N or C-L a -R a .

[0095] In one embodiment, depending on R aFor the substituents, the second compound can be represented by, for example, one of Chemical Formulas 2A to 2C.

[0096]

[0097] In Chemical Formulas 2A to 2C, Z 1 、Z 3 and Z 5 can each independently be, for example, N or C-L a -R a 。In one embodiment, at least two of Z 1 、Z 3 and Z 5 are N.

[0098] X 1 can be, for example, O, S or NR b 。

[0099] L a and L 2 to L 4 can each independently be, for example, a single bond, a substituted or unsubstituted C6-C20 arylene, a substituted or unsubstituted C2-C20 heterocyclic group, or a combination thereof.

[0100] R a 、R b and R 23 to R 44 can each independently be, for example, hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a halogen, a cyano group, or a combination thereof.

[0101] R 23 to R 30 can exist separately or adjacent groups among them can be joined to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring.

[0102] R 31 to R 35 can exist separately or adjacent groups among them are joined to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring.

[0103] Ar 3 and Ar 4 can each independently be, for example, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof.

[0104] R a 、Ar 3 and Ar 4may exist separately, or R a , Ar 3 and Ar 4 The adjacent groups in may be joined to form a substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic ring.

[0105] m5 and m6 can each independently be, for example, an integer from 1 to 3.

[0106] In Chemical Formula 2B, m5 can be 2 or greater, and each R 31 can be the same or different.

[0107] In Chemical Formula 2C, m6 can be 2 or greater, and each R 36 can be the same or different.

[0108] In this specification, "the adjacent groups may be joined to form a substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic ring" means that any two adjacent substituents are joined to form a ring. In one embodiment, in Chemical Formula 2A, R 23 to R 30 The adjacent groups in can be joined to each other to form a substituted or unsubstituted aromatic monocyclic ring. The formed aromatic monocyclic ring can include, for example, a substituted or unsubstituted phenyl group.

[0109] In one embodiment, Chemical Formula 2A can be represented by, for example, one of Chemical Formulas 2A-I to 2A-XVIII.

[0110]

[0111]

[0112]

[0113]

[0114] In Chemical Formulas 2A-I to 2A-XVIII, L 2 to L 4 , Ar 3 and Ar 4 , R 23 to R 30 can be the same as those described above.

[0115] Ar 6 can be, for example, a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group.

[0116] L 9 can be, for example, a single bond, a substituted or unsubstituted C6-C20 arylene group or a substituted or unsubstituted C2-C20 heterocyclic group.

[0117] R 45 to R 64 may each independently be, for example, hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, a substituted or unsubstituted C1-C10 alkylsilyl group, a substituted or unsubstituted amino group, a halogen, a cyano group, or a combination thereof.

[0118] In one embodiment, L 2 to L 4 may each independently be, for example, a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group.

[0119] In one embodiment, Ar 3 , Ar 4 and Ar 6 may each 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 quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0120] In one embodiment, R 23 to R 30 and R 45 to R 64 may each independently be, for example, hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 alkylsilyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0121] In one embodiment, Chemical Formula 2B may be represented by, for example, one of Chemical Formulas 2B-I to 2B-IV.

[0122]

[0123]

[0124] In Chemical Formulas 2B-I to 2B-IV, L 2 to L 4 , Ar 3 and Ar 4 , R 31 to R 35 and m5 may be defined as the same as above.

[0125] In one embodiment, Chemical Formula 2C can be represented by Chemical Formula 2C-I or Chemical Formula 2C-II.

[0126]

[0127] In Chemical Formula 2C-I and Chemical Formula 2C-II, L 2 to L 4 , Ar 3 and Ar 4 , R 36 to R 44 and m6 can be defined as the same as above.

[0128] In one embodiment, Chemical Formula 2 can be represented by, for example, one of Chemical Formula 2A-XIV or Chemical Formula 2C-I.

[0129] In one embodiment, in Chemical Formula 2A-XIV, L 2 to L 4 and L 9 can each independently be, for example, a single bond or a substituted or unsubstituted C6-C12 aryl group, Ar 3 , Ar 4 and Ar 6 can each 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 terphenylene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted carbazolyl group, and R 23 to R 28 and R 61 to R 64 can each independently be, for example, hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C12 aryl group.

[0130] In one embodiment, in Chemical Formula 2C-I, L 2 to L 4 can each independently be a single bond or a substituted or unsubstituted C6-C12 aryl group, Ar 3 and Ar 4 can each 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 terphenylene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted carbazolyl group, and R 36 to R 44They can each independently be, for example, hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C12 aryl group.

[0131] In one embodiment, the second compound can be, for example, a compound of Group 2.

[0132] [Group 2]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160] The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. Within the above range, by utilizing the hole transport ability of the first compound and the electron transport ability of the second compound, and by adjusting an appropriate weight ratio, the efficiency and lifetime can be improved by achieving bipolar characteristics. In one embodiment, they may be included in a weight ratio of, for example, about 10:90 to 90:10, about 20:80 to 80:20 (e.g., 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 40:60, 50:50, or 60:40.

[0161] Hereinafter, an organic optoelectronic device including the above compound for an organic optoelectronic device or a composition for an organic optoelectronic device will be described.

[0162] The organic optoelectronic device may be a suitable device that converts electrical energy into light energy and vice versa, for example, an organic optoelectronic device, an organic light emitting diode, an organic solar cell, or an organic photosensitive drum.

[0163] Herein, an organic light emitting diode as an example of an organic optoelectronic device is described with reference to the accompanying drawings.

[0164] Figure 1 is a cross-sectional view showing an organic light emitting diode according to some exemplary embodiments.

[0165] Referring to Figure 1 , an organic light emitting diode 100 according to some exemplary embodiments may include an anode 120 and a cathode 110 facing each other and an organic layer 105 between the anode 120 and the cathode 110.

[0166] The anode 120 can be made of a conductor with a high work function to assist hole injection, and can be, for example, a metal, a metal oxide, or a conductive polymer. The anode 120 can be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, etc. or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; 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-(ethylenedioxy)thiophene) (PEDOT), polypyrrole, or polyaniline.

[0167] The cathode 110 can be made of a conductor with a low work function to assist electron injection, and can be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 can be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc. or an alloy thereof; or a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, or BaF2 / Ca.

[0168] The organic layer 105 can contain the compounds or compositions for organic optoelectronic devices described above.

[0169] The organic layer 105 can include a light-emitting layer 130. The light-emitting layer 130 can contain a host and a dopant. The host can include the compounds or compositions for organic optoelectronic devices described above, and the dopant can be, for example, a phosphorescent dopant such as a red, green, or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0170] The dopant can be a material that is mixed in a small amount with the compounds or compositions for organic optoelectronic devices to cause luminescence, and can be a material such as a metal complex that emits light by being excited to a triplet state or more states multiple times. The dopant can be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof can be used.

[0171] Examples of the dopant can include phosphorescent dopants, and examples of the phosphorescent dopants can be organometallic compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. In one embodiment, the phosphorescent dopant can be, for example, a compound represented by Chemical Formula Z.

[0172] [Chemical Formula Z]

[0173] L 5 MX 3

[0174] In Chemical Formula Z, M can be a metal, and L5 and X 3 may each independently be, for example, a ligand to form a complex with M.

[0175] M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L 5 and X 3 may each independently be, for example, a bidentate ligand.

[0176] Examples of the ligand represented by L 5 and X 3 may include the ligands of Group A.

[0177] [Group A]

[0178]

[0179] In Group A, R 300 to R 302 may each independently be, for example, hydrogen, deuterium, a halogen-substituted or unsubstituted C1-C30 alkyl group, a C1-C30 alkyl group-substituted or unsubstituted C6-C30 aryl group, or a halogen.

[0180] R 303 to R 324 may each independently be, for example, hydrogen, deuterium, a halogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C1-C30 heteroaryl group, a substituted or unsubstituted C1-C30 amino group, a substituted or unsubstituted C6-C30 arylamino group, SF5, a trialkylsilyl group having a substituted or unsubstituted C1-C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1-C30 alkyl group and a C6-C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6-C30 aryl group.

[0181] n1 may be an integer from 1 to 5.

[0182] n2 may be an integer from 1 to 4.

[0183] n3 may be an integer from 1 to 3.

[0184] n4 may be an integer of 1 or 2.

[0185] n5 may be an integer from 1 to 6.

[0186] The dopant according to some exemplary embodiments may be an iridium complex and may include, for example, a dopant represented by Chemical Formula 4-1 or Chemical Formula 4-2.

[0187] [Chemical Formula 4-1]

[0188]

[0189] In Chemical Formula 4-1, R 101 to R 116 may each independently be, for example, hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 132 R 133 R 134 .

[0190] R 132 to R 134 may each independently be, for example, a substituted or unsubstituted C1-C6 alkyl group.

[0191] In one embodiment, at least one of R 101 to R 116 may be a functional group represented by Chemical Formula V-1.

[0192] L 100 may be, for example, a bidentate ligand of a monovalent anion and is a ligand coordinated to iridium through a lone pair of electrons of a carbon or heteroatom.

[0193] m21 and m22 may each independently be, for example, an integer from 0 to 3, and m21 + m22 may be an integer from 1 to 3.

[0194] [Chemical Formula V-1]

[0195]

[0196] In Chemical Formula V-1, R 135 to R 139 may each independently be, for example, hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 132 R 133 R 134 .

[0197] * refers to the moiety connected to the carbon atom.

[0198] [Chemical Formula 4-2]

[0199]

[0200] In Chemical Formula 4-2, R 101 to R 117can each independently be, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 133 R 134 R 135 .

[0201] R 133 To R 135 Each independently may be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0202] L 100 The ligand may be, for example, a bidentate ligand of a monovalent anion and is a ligand coordinated to iridium via a lone electron pair of carbon or a heteroatom.

[0203] n1 and n2 may each independently be an integer of, for example, 0 to 3, and n1+n2 may be an integer of 1 to 3.

[0204] The dopant according to some exemplary embodiments may be a platinum complex, and may be represented by, for example, Chemical Formula Z-1.

[0205] [Chemical formula Z-1]

[0206]

[0207] In the chemical formula Z-1, the rings A, B, C and D may each independently be, for example, a 5-membered or 6-membered carbocyclic ring or a heterocyclic ring.

[0208] R A , R B , R C and R D may each independently be, for example, mono-, di-, tri- or tetra-substituted or unsubstituted;

[0209] L B , L C and L D Each may independently be, for example, a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, GeRR′, or a combination thereof.

[0210] 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' or a combination thereof. In one embodiment, nA can be 0, and L E Does not exist.

[0211] R A , R B , R C , RD , R and R' can each independently be, for example, hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxyl, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphino or a combination thereof; any adjacent R A , R B , R C , R D , R and R' are optionally connected to each other to provide a ring; X B , X C , X D and X E are each independently selected from carbon and nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 each represents oxygen or a direct bond.

[0212] The platinum complex can be represented, for example, by Chemical Formula 5-1 or Chemical Formula 5-2.

[0213] [Chemical Formula 5-1]

[0214]

[0215] [Chemical Formula 5-2]

[0216]

[0217] In Chemical Formula 5-1 and Chemical Formula 5-2, X 100 can be, for example, O, S or NR 132 .

[0218] R 118 to R 132 can each independently be, for example, hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C20 aryl or -SiR 133 R 134 R 135 .

[0219] R 133 to R 135 can each independently be, for example, substituted or unsubstituted C1-C6 alkyl.

[0220] In one embodiment, at least one of R 118 to R 132 can be -SiR 133 R 134 R 135 or tert-butyl.

[0221] R 133 to R 135 may each independently be, for example, a substituted or unsubstituted C1-C6 alkyl group.

[0222] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0223] The charge transport region may be, for example, the hole transport region 140.

[0224] The hole transport region 140 may help to further increase the hole injection and / or hole mobility between the anode 120 and the light-emitting layer 130, and block electrons.

[0225] 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 assisting layer between the light-emitting layer 130 and the hole transport layer, and the compound of Group B may be contained in at least one of the hole transport layer and the hole transport assisting layer.

[0226] [Group B]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233] (Dn refers to the number of deuterium substitutions and represents a structure substituted with one or more deuterium atoms). However, as described above, any hydrogen in any compound may be protium, deuterium or tritium based on natural or artificial substitution.

[0234] In the hole transport region, in addition to the above compounds, other suitable compounds and compounds with similar structures may also be used.

[0235] In one embodiment, the charge transport region may be, for example, the electron transport region 150.

[0236] The electron transport region 150 may help to further increase the electron injection and / or electron mobility between the cathode 110 and the light-emitting layer 130 and block holes.

[0237] 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 assisting layer between the light-emitting layer 130 and the electron transport layer, and the compound of Group C may be included in at least one of the electron transport layer and the electron transport assisting layer.

[0238] [Group C]

[0239]

[0240]

[0241]

[0242] Some exemplary embodiments may provide an organic light-emitting diode including a light-emitting layer as an organic layer.

[0243] Some exemplary embodiments may provide an organic light-emitting diode including a light-emitting layer and a hole transport region as organic layers.

[0244] Some exemplary embodiments may provide an organic light-emitting diode including a light-emitting layer and an electron transport region as organic layers.

[0245] As Figure 1 shown, in addition to the light-emitting layer 130, some exemplary embodiments may also provide an organic light-emitting diode including a hole transport region 140 and an electron transport region 150 as an organic layer 105.

[0246] 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 organic layers.

[0247] 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 a cathode or an anode thereon.

[0248] The above organic light-emitting diode may be applied to an organic light-emitting display device.

[0249] 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.

[0250] Hereinafter, starting materials and reactants used in the examples and synthesis examples are purchased from Sigma-Aldrich Co., Ltd., TCI Inc., Tokyo chemical industry, or P&H tech or synthesized by appropriate methods unless otherwise specified.

[0251] (Synthesis of Compounds for Organic Optoelectronic Devices)

[0252] Synthesis Example 1: Synthesis of Intermediate I-1

[0253] [Reaction Formula 1]

[0254]

[0255] In a nitrogen atmosphere, after dissolving 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (50 g, 135.4 mmol) in 0.5 L of dioxane purchased from Ukseung Chemical Co., Ltd. (http: / / www.ukseung.co.kr / ), 1-bromo-2-iodobenzene (57.5 g, 203 mmol) and tetrakis(triphenylphosphine)palladium (3.1 g, 2.7 mmol) purchased from Sigma Aldrich Co., Ltd. (http: / / www.sigmaaldrich.com / ) were added thereto, and then stirred. Subsequently, a saturated aqueous solution of potassium carbonate (46.8 g, 339 mmol) was added thereto, and then, the mixture was heated under reflux at 120 °C for 1 hour. After the reaction was completed, water was added to the reaction solution, and then filtered. The obtained residue was separated and purified by flash column chromatography to obtain Intermediate I-1 (37 g, 69%).

[0256] HRMS (70 eV, EI+): Calculated m / z for C24H16BrN: 397.0466, measured value: 397.

[0257] Elemental analysis: C, 72%; H, 4%.

[0258] Synthesis Example 2: Synthesis of Compound 2.

[0259] [Reaction Formula 2]

[0260]

[0261] In a nitrogen atmosphere, after dissolving 5-phenyl-5,8-dihydroindolo[2,3-c]carbazole (19 g, 57.2 mmol) in 0.2 L of dodecylbenzene purchased from Ukseung Chemical Co., Ltd. (http: / / www.ukseung.co.kr / ), intermediate I-1 (27.3 g, 68.6 mmol), copper (0.73 g, 11.4 mmol), potassium carbonate (11.8 g, 86 mmol), and 3,5-di-tert-butylsalicylic acid (2.9 g, 11.4 mmol) were added thereto, and then the mixture was heated at 260 °C for 40 hours. After completion of the reaction and after adding water to the reaction solution, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain compound 2 (31.6 g, 85%).

[0262] HRMS (70 eV, EI+): Calculated m / z for C48H31N3: 649.2518, measured: 649.

[0263] Elemental analysis: C, 89%; H, 5%.

[0264] Synthesis Example 3: Synthesis of Intermediate I-2

[0265] [Reaction Scheme 3]

[0266]

[0267] Intermediate I-2 (38.3 g, 71%) was obtained in the same manner as in Synthesis Example 1, except that 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (50 g, 135.4 mmol) purchased from Ukseung Co., Ltd. (http: / / www.ukseung.co.kr / ) and 1-bromo-2-iodobenzene (57.5 g, 203 mmol) purchased from Sigma Aldrich Co., Ltd. (http: / / www.sigmaaldrich.com / ) were used.

[0268] HRMS (70 eV, EI+): Calculated m / z for C24H16BrN: 397.0466, measured: 397.

[0269] Elemental analysis: C, 72%; H, 4%.

[0270] Synthesis Example 4: Synthesis of Compound 3.

[0271] [Reaction Scheme 4]

[0272]

[0273] Compound 3 (38.3 g, 71%) was obtained in the same manner as in Synthesis Example 2, except that 5-phenyl-5,8-dihydroindolo[2,3-c]carbazole (19 g, 57.2 mmol) purchased from Ukseung Co., Ltd. (http: / / www.ukseung.co.kr / ) and Intermediate I-2 (27.3 g, 68.6 mmol) were used.

[0274] HRMS (70 eV, EI+): Calculated m / z for C48H31N3: 649.2518, Measured: 649.

[0275] Elemental analysis: C, 89%; H, 5%.

[0276] Synthesis Example 5: Synthesis of Intermediate I-3

[0277] [Reaction Scheme 5]

[0278]

[0279] Intermediate I-3 (38.3 g, 71%) was obtained in the same manner as in Synthesis Example 1, except that 9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (50 g, 135.4 mmol) purchased from Ukseung Co., Ltd. (http: / / www.ukseung.co.kr / ) and 1-bromo-2-iodobenzene (57.5 g, 203 mmol) purchased from Sigma Aldrich Co., Ltd. (http: / / www.sigmaaldrich.com / ) were used.

[0280] HRMS (70 eV, EI+): Calculated m / z for C24H16BrN: 397.0466, Measured: 397.

[0281] Elemental analysis: C, 72%; H, 4%.

[0282] Synthesis Example 6: Synthesis of Compound 4

[0283] [Reaction Scheme 6]

[0284]

[0285] Compound 4 (38.3 g, 71%) was obtained in the same manner as in Synthesis Example 2, except that 5-phenyl-5,8-dihydroindolo[2,3-c]carbazole (19 g, 57.2 mmol) and Intermediate I-3 (27.3 g, 68.6 mmol) purchased from Ukseung Co., Ltd. (http: / / www.ukseung.co.kr / ) were used.

[0286] HRMS (70 eV, EI+): Calculated m / z for C48H31N3: 649.2518, Measured: 649.

[0287] Elemental analysis: C, 89%; H, 5%.

[0288] Synthesis Example 7: Synthesis of Compound 15

[0289] [Reaction Scheme 7]

[0290]

[0291] Compound 15 (26.5 g, 64%) was obtained in the same manner as in Synthesis Example 2, except that 5-([1,1'-biphenyl]-2-yl)-5,8-dihydroindolo[2,3-c]carbazole (23.4 g, 57.2 mmol) and Intermediate I-2 (27.3 g, 68.6 mmol) purchased from Yantai Gem Chemicals Co., Ltd. (http: / / www.ytgemchem.com) were used.

[0292] HRMS (70 eV, EI+): Calculated m / z for C54H35N3: 725.2831, Measured: 725.

[0293] Elemental analysis: C, 89%; H, 5%.

[0294] Synthesis Example 8: Synthesis of Intermediate I-4

[0295] [Reaction Scheme 8]

[0296]

[0297] In a nitrogen atmosphere, after dissolving 5,8-dihydroindolo[2,3-c]carbazole (50 g, 195 mmol) purchased from P&H Tech Co., Ltd. (http: / / www.phtech.co.kr / ) and 1-fluoroterphenyl (48 g, 195 mmol) purchased from Yantai Gem Chemicals Co., Ltd. (http: / / www.ytgemchem.com) in 0.5 L of dimethylformamide (DMF), potassium phosphate tribasic (41.4 g, 195 mmol) was added thereto, and then the mixture was heated under reflux for 18 hours.

[0298] After the reaction was completed, and after removing the solvent by distillation and adding water to the reaction solution, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain Intermediate I-4 (37.6 g, 40%).

[0299] HRMS (70 eV, EI+): Calculated m / z for C36H22N2: 482.1783, Measured: 482.

[0300] Elemental analysis: C, 90%; H, 5%.

[0301] Synthesis Example 9: Synthesis of Compound 190

[0302] [Reaction Scheme 9]

[0303]

[0304] Compound 190 (26.5 g, 61%) was obtained in the same manner as in Synthesis Example 2, except that Intermediate I-4 (20 g, 41.4 mmol) and Intermediate I-2 (20.2 g, 49.7 mmol) were used.

[0305] HRMS (70 eV, EI+): Calculated m / z for C90H37N3: 799.2987, Measured: 799.

[0306] Elemental analysis: C, 90%; H, 5%.

[0307] Synthesis Example 10: Synthesis of Intermediate I-5

[0308] [Reaction Scheme 10]

[0309]

[0310] Intermediate I-5 (125 g, 91%) was obtained in the same manner as in Synthesis Example 1, except that 2,6-dimethoxyphenylboronic acid (100 g, 550 mmol) and 2-bromo-1,3-difluorobenzene (106 g, 550 mmol) were used.

[0311] HRMS (70 eV, EI+): Calculated m / z for C14H12F2O2: 250.0805, measured: 250.

[0312] Elemental analysis: C, 67%; H, 5%.

[0313] Synthesis Example 11: Synthesis of Intermediate I-6

[0314] [Reaction Scheme 11]

[0315]

[0316] In a nitrogen atmosphere, Intermediate I-5 (121 g, 486 mmol) and pyridine hydrochloride (562 g, 4,861 mmol) were added, and then the mixture was heated under reflux at 180 °C for 1 hour. After the reaction was completed and 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 obtained residue was separated and purified by flash column chromatography to obtain Intermediate I-6 (102 g, 95%).

[0317] HRMS (70 eV, EI+): Calculated m / z for C12H8F2O2: 222.0492, measured: 222.

[0318] Elemental analysis: C, 65%; H, 4%.

[0319] Synthesis Example 12: Synthesis of Intermediate I-7

[0320] [Reaction Scheme 12]

[0321]

[0322] Intermediate I-7 (72.5 g, 80%) was obtained in the same manner as in Synthesis Example 8, except that Intermediate I-6 (99.5 g, 448 mmol) was used.

[0323] HRMS (70 eV, EI+): Calculated m / z for C12H7FO2: 202.0430, measured: 202.

[0324] Elemental analysis: C, 71%; H, 3%.

[0325] Synthesis Example 13: Synthesis of Intermediate I-8

[0326] [Reaction Formula 13]

[0327]

[0328] In a nitrogen atmosphere, intermediate I-7 (72 g, 356 mmol) was dissolved in 0.1 L of dichloromethane (DCM), and then cooled to 0 °C. Subsequently, pyridine (120 g, 427 mmol) was added thereto and then stirred for 30 minutes, and trifluoromethanesulfonic anhydride (33.8 g, 427 mmol) was slowly added thereto and then stirred. After 3 hours, the reaction solution was cooled to 0 °C, and water was slowly added thereto within 30 minutes. The mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain intermediate I-8 (116 g, 98%).

[0329] HRMS (70 eV, EI+): Calculated m / z for C13H6F4O4S: 333.9923, measured: 333.

[0330] Elemental analysis: C, 47%; H, 2%.

[0331] Synthesis Example 14: Synthesis of Intermediate I-9

[0332] [Reaction Formula 14]

[0333]

[0334] Intermediate I-9 (69.4 g, 78%) was obtained in the same manner as in Synthesis Example 1, except that intermediate I-8 (113 g, 339 mmol) and phenylboronic acid (45.5 g, 373 mmol) purchased from Tokyo Chemical Industry Co., Ltd. were used.

[0335] HRMS (70 eV, EI+): Calculated m / z for C18H11FO: 262.0794, measured: 262.

[0336] Elemental analysis: C, 82%; H, 4%.

[0337] Synthesis Example 15: Synthesis of Intermediate I-10

[0338] [Reaction Formula 15]

[0339]

[0340] Intermediate I-10 (43.8 g, 45%) was obtained in the same manner as in Synthesis Example 8, except that 5,8-dihydroindolo[2,3-c]carbazole (50 g, 195 mmol) and Intermediate I-9 (51 g, 195 mmol) purchased from P&H Tech Co., Ltd. (http: / / www.phtech.co.kr / ) were used.

[0341] HRMS (70 eV, EI+): Calculated m / z for C36H22N2O: 498.1732, Measured: 498.

[0342] Elemental analysis: C, 87%; H, 4%.

[0343] Synthesis Example 16: Synthesis of Compound 240

[0344] [Reaction Scheme 16]

[0345]

[0346] Compound 240 (19 g, 58%) was obtained in the same manner as in Synthesis Example 2, except that Intermediate I-10 (20 g, 40.1 mmol) and Intermediate I-2 (19.1 g, 48.1 mmol) were used.

[0347] HRMS (70 eV, EI+): Calculated m / z for C60H37N3O: 815.2937, Measured: 815.

[0348] Elemental analysis: C, 88%; H, 5%.

[0349] Synthesis Example 17: Synthesis of Compound R-1

[0350]

[0351] Compound R-1 was synthesized by referring to the synthesis method of Chinese Patent No. CN 110776513.

[0352] HRMS (70 eV, EI+): Calculated m / z for C58H36N4S: 820.2661, Measured: 820.

[0353] Elemental analysis: C, 85%; H, 4%.

[0354] Synthesis Example 18: Synthesis of Compound R-2

[0355]

[0356] Compound R-2 was synthesized by referring to the synthesis method of Korean Patent No. KR 2017-0048094.

[0357] HRMS (70eV, EI+): Calculated m / z for C48H31N3: 649.2518, Measured: 649.

[0358] Elemental analysis: C, 89%; H, 5%.

[0359] Synthesis Example 19: Synthesis of Compound R-3

[0360]

[0361] Compound R-3 was synthesized by referring to the synthesis method of Korean Patent No. KR 2017-0048094.

[0362] HRMS (70eV, EI+): Calculated m / z for C48H31N3: 649.2518, Measured: 649.

[0363] Elemental analysis: C, 89%; H, 5%.

[0364] Synthesis Example 20: Synthesis of Compound R-4

[0365]

[0366] Compound R-4 was synthesized by referring to the synthesis method of Korean Patent No. KR 2017-0048094.

[0367] HRMS (70eV, EI+): Calculated m / z for C48H31N3: 649.2518, Measured: 649.

[0368] Elemental analysis: C, 89%; H, 5%.

[0369] Synthesis Example 21: Synthesis of Compound R-5

[0370]

[0371] Compound R-5 was synthesized by referring to the synthesis method of Korean Patent No. KR 2017-0048094.

[0372] HRMS (70eV, EI+): Calculated m / z for C48H31N3: 649.2518, Measured: 649.

[0373] Elemental analysis: C, 89%; H, 5%.

[0374] Synthesis Example 22: Synthesis of Compound E-86

[0375]

[0376] Compound E-86 was synthesized by referring to the synthesis method described in Korean Published Patent No. KR 10-2022-0095942A.

[0377] Synthesis Example 23: Synthesis of Compound D-33

[0378]

[0379] Compound D-33 was synthesized by referring to the synthesis method described in Korean Registered Published Patent No. KR 10-1618683B1.

[0380] Example 1: Fabrication of a green organic light-emitting diode (single host)

[0381] A glass substrate coated with an ITO (indium tin oxide) film was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically washed with isopropyl alcohol, acetone, or methanol and dried, then moved to a plasma cleaner and cleaned with oxygen plasma for 10 minutes, and then moved to a vacuum depositor. This prepared ITO transparent electrode was used as the anode, and compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO substrate to form a thick hole injection layer, and compound A was deposited on the hole injection layer to a thickness to form a hole transport layer. On the hole transport layer, compound B was deposited to a thickness to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compound 2 (synthesized in Synthesis Example 2) was used as the host and 10 wt% of PhGD was doped as a dopant to form a thick light-emitting layer by vacuum deposition. Subsequently, on the light-emitting layer, compound C was deposited to form a thick electron transport auxiliary layer, and at the same time, compound D and LiQ with a weight ratio of 1:1 were vacuum deposited to form a thick electron transport layer. On the electron transport layer, a cathode was formed by sequentially vacuum depositing LiQ and Al to fabricate an organic light-emitting diode.

[0382] An organic light-emitting diode was fabricated to have ITO / compound A (doped with 3% NDP-9, ) / compound A / compound B / EML [host (compound 2):PhGD = 90 wt%:10 wt%] / compound C / compound D:LiQ / LiQ / Al Structure

[0383] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0384] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0385] Compound C: 2,4-diphenyl-6-(4',5',6'-triphenyl[1,1':2',1”:3”,1”':3”',1””-quaterphenyl]-3””-yl)-1,3,5-triazine

[0386] Compound D: 2-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0387] [PhGD]

[0388]

[0389] Examples 2 to 6 and Comparative Examples 1 to 5

[0390] Organic light-emitting diodes were fabricated in the same manner as in Example 1, except that the composition was changed to those shown in Table 1

[0391] Example 7: Fabrication of a green organic light-emitting diode (mixed host)

[0392] A glass substrate coated with an ITO (indium tin oxide) film was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically washed with isopropyl alcohol, acetone or methanol and dried, and then moved to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and moved to a vacuum evaporator. The prepared ITO transparent electrode was used as the anode, and Compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO substrate to form a thick hole injection layer, and Compound A was deposited on the hole injection layer to a thickness to form a hole transport layer. On the hole transport layer, Compound E was deposited to a thickness to form a hole transport auxiliary layer. On the hole transport auxiliary layer, Compound 2 (synthesized in Synthesis Example 2) and Compound E-86 (synthesized in Synthesis Example 22) were used as hosts at a weight ratio of 7:3, and 15 wt% of PtGD was doped as a dopant to form a A thick light-emitting layer. Subsequently, on the light-emitting layer, Compound F was deposited to a thickness to form an electron transport assisting layer, and Compound G and LiQ were co-evaporated at a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 . On the electron transport layer, by successively co-evaporating of LiQ and of Al, a cathode was formed, thereby fabricating an organic light-emitting diode.

[0393] The organic light-emitting diode was fabricated to have the structure of ITO / Compound A (3% NDP-9 doped, ) / Compound A / Compound E / / EML[host (Compound 2:Compound E-86 = 7:3 wt% / wt%):PtGD = 85 wt%:15 wt%] / Compound F / Compound G:LiQ / LiQ / Al .

[0394] Compound E: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluorene)-2-amine

[0395] Compound F: 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0396] Compound G: 2-[4-[4-(4'-cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0397] [PtGD]

[0398]

[0399] Example 8 and Example 10

[0400] Each organic light-emitting diode was fabricated in the same manner as in Example 7, except that the host mixing ratio was changed to a weight ratio of 6:4.

[0401] Example 9 and Examples 11 to 15 and Comparative Examples 6 to 10

[0402] Each organic light-emitting diode was fabricated in the same manner as in Example 7, except that the composition was changed to those shown in Table 2.

[0403] Evaluation

[0404] The luminous efficiency and lifetime characteristics of the organic light-emitting diodes according to Examples 1 to 15 and Comparative Examples 1 to 10 were evaluated.

[0405] The measurement methods are as follows, and the results are shown in Tables 1 and 2.

[0406] (1) Measuring the change in current density according to voltage change

[0407] 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 the result.

[0408] (2) Measuring the change in luminance according to voltage change

[0409] 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).

[0410] (3) Measuring the luminous efficiency

[0411] The luminous efficiency (cd / A) at the same current density (10 mA / cm 2 ) was calculated by using the luminance, current density, and voltage from (1) and (2) above.

[0412] Based on Comparative Example 1, the luminous efficiency values of Examples 1 to 6 and Comparative Examples 1 to 5 were calculated as relative values and shown in Table 1.

[0413] Based on Comparative Example 6, the luminous efficiency values of Examples 7 to 15 and Comparative Examples 6 to 10 were calculated as relative values and shown in Table 2.

[0414] (4) Measuring the lifetime

[0415] The result was obtained by maintaining the luminance (cd / m 2 ) at 24,000 cd / m 2 and measuring the time when the luminous efficiency (cd / A) decreased to 97%.

[0416] Based on Comparative Example 1, the lifetime measurement values of Examples 1 to 6 and Comparative Examples 1 to 5 were calculated as relative values and shown in Table 1.

[0417] Based on Comparative Example 6, the lifetime measurement values of Examples 7 to 15 and Comparative Examples 6 to 10 were calculated as relative values and shown in Table 2.

[0418] (Table 1)

[0419]

[0420]

[0421] (Table 2)

[0422]

[0423] Referring to Tables 1 and 2, compared with the organic light-emitting diodes according to Comparative Examples 1 to 10, the organic light-emitting diodes according to Examples 1 to 15 have significantly improved luminous efficiency and lifetime characteristics.

[0424] One or more embodiments can provide a compound for an organic optoelectronic device, the compound capable of reducing the driving voltage and realizing an organic optoelectronic device with high efficiency and long lifetime.

[0425] An organic optoelectronic device with high efficiency and long lifetime can be realized while reducing the driving voltage.

[0426] Exemplary embodiments have been disclosed herein, and although specific terms have been employed, they have been used and interpreted in an overarching and descriptive sense only and not for purposes of limitation. In some instances, as of the filing date of the present application, it will be apparent to those of ordinary skill in the art that features, characteristics, and / or elements described in connection with a particular embodiment may be used alone or in combination with features, characteristics, and / or elements described in connection with other embodiments, unless otherwise expressly indicated. Accordingly, those skilled in the art will understand 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, L 1 is a single bond, a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C2-C30 heteroarylene group, Ar 1 and Ar 2 each independently is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, R 1 to R 19 each independently is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heterocyclic group, substituted or unsubstituted C1-C10 alkylsilyl or a combination thereof, m1 is an integer from 1 to 3, and When m1 is 2 or 3, each R 5 is the same as or different from one another.

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, L 1 , Ar 1 and Ar 2 , R 1 to R 19 and m1 are defined to be the same as those in Chemical Formula 1.

3. The compound for an organic optoelectronic device according to claim 1, wherein Ar 1 and Ar 2 each independently is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted terphenylene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl or a substituted or unsubstituted dibenzosilolyl.

4. The compound for an organic optoelectronic device according to claim 1, wherein: Part *-L 1 -Ar 2 and *-Ar 1 are each independently a part of Group I: [Group I] In Group I, R 20 to R 22 each independently is hydrogen, deuterium, cyano, substituted or unsubstituted C1-C10 alkyl or substituted or unsubstituted C6-C12 aryl, m2 is an integer from 1 to 5, m3 is an integer from 1 to 4, m4 is an integer from 1 to 3, and * is a connection point.

5. The compound for an organic optoelectronic device according to claim 1, wherein R 1 to R 19 each independently is hydrogen, deuterium, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C2-C20 heterocyclic group, substituted or unsubstituted C1-C10 alkylsilyl or a combination thereof.

6. The compound for an organic optoelectronic device according to claim 1, wherein: The compound is a compound of Group 1: [Group 1] In Group 1, Dn refers to the number of deuterium substitutions and represents a structure substituted with one or more deuterium atoms.

7. A composition for an organic optoelectronic device, the composition comprising: a first compound; and a second compound, wherein: the first compound is the compound for an organic optoelectronic device according to any one of claims 1 to 6, and the second compound is represented by Chemical Formula 2: [Chemical Formula 2] In Chemical Formula 2, Z 1 to Z 6 each independently is N or C-L a -R a provided that: Z 1 to Z 6 at least two of which are N, Each L a independently is a single bond, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C20 heterocyclic group, or a combination thereof, Each R a is independently hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a halogen, a cyano group, or a combination thereof, and Each R a exists separately, or adjacent groups among them are connected to form a substituted or unsubstituted aliphatic monocyclic or polycyclic, substituted or unsubstituted aromatic monocyclic or polycyclic, or substituted or substituted heteroaromatic monocyclic or polycyclic.

8. The composition for an organic optoelectronic device according to claim 7, wherein: Chemical Formula 2 is represented by one of Chemical Formulas 2A to 2C: [Chemical Formula 2C] In Chemical Formulas 2A to 2C, Z 1 , Z 3 and Z 5 Each independently is N or CL a -R a , the condition is: Z 1 , Z 3 and Z 5 At least two of them are N, X 1 is O, S or NR b , L a and L 2 to L 4 each independently is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof R a 、R b and R 23 to R 44 each independently is hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a halogen, a cyano group, or a combination thereof. R 23 to R 30 each exist separately or adjacent groups among them are linked to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring, R 31 to R 35 each exist separately or adjacent groups among them are linked to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring, Ar 3 and Ar 4 each independently is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof, R a 、 Ar 3 and Ar 4 are each present separately, or R a 、 Ar 3 and Ar 4 adjacent groups in are joined to form a substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic ring, and m5 and m6 are each independently an integer from 1 to 3.

9. The composition for an organic optoelectronic device according to claim 7, wherein: Chemical Formula 2 is represented by Chemical Formula 2A-XIV or Chemical Formula 2C-I: In Chemical Formula 2A-XIV and Chemical Formula 2C-I, L 2 to L 4 and L 9 each independently is a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenyl, Ar 3 、Ar 4 and Ar 6 are each independently a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted terphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl. R 23 to R 28 、R 36 to R 44 and R 61 to R 64 each independently is hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl, and m6 is an integer from 1 to 3.

10. An organic optoelectronic device, comprising: an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, wherein the at least one organic layer contains the compound for an organic optoelectronic device according to any one of claims 1 to 6; or the composition for an organic optoelectronic device according to any one of claims 7 to 9.

11. The organic optoelectronic device according to claim 10, wherein: the at least one organic layer includes a light-emitting layer, and the light-emitting layer contains the compound for an organic optoelectronic device or the composition for an organic optoelectronic device.

12. A display device, comprising the organic optoelectronic device according to claim 10 or 11.

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