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

Abstract

The present invention relates to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. Specifically, the present invention relates to a compound for an organic optoelectronic device represented by Chemical Formula 1 or Chemical Formula 2, a composition for an organic optoelectronic device including the compound for an organic optoelectronic device, an organic optoelectronic device, and a display device including the organic optoelectronic device. # imgabs0 #

Description

[0001] Citation of Related Applications

[0002] This application claims priority and the benefit of Korean Patent Application No. 10-2024-0005996, filed with the Korean Intellectual Property Office on January 15, 2024, the entire content of which is incorporated herein by reference. Technical Field

[0003] Embodiments of the present invention relate to compounds for organic optoelectronic devices, compositions for organic optoelectronic devices, organic optoelectronic devices, and display devices. 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 basically divided into two categories. One category 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 category is a light-emitting device that generates light energy from electrical energy by applying a voltage or current to an electrode.

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

[0007] Among them, due to the increasing demand for flat panel displays, organic light-emitting diodes (OLEDs) have recently attracted attention. An organic light-emitting diode converts electrical energy into light by applying a current to an organic light-emitting material, and the performance of an 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 or Chemical Formula 2:

[0009] [Chemical Formula 1]

[0010]

[0011] [Chemical Formula 2]

[0012]

[0013] In Chemical Formulas 1 and 2, L 1 is a single bond or a substituted or unsubstituted C6 to C30 arylene group, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, R 1 to R19 Each independently is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, 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.

[0014] Embodiments can be achieved by providing a composition for an organic optoelectronic device, the composition including 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 3:

[0015] [Chemical Formula 3]

[0016]

[0017] In Chemical Formula 3, 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, L a each 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, 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, substituted or unsubstituted aromatic monocyclic or polycyclic, or substituted or unsubstituted heteroaromatic monocyclic or polycyclic.

[0018] 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 located between the anode and the cathode, wherein at least one organic layer includes a compound for an organic optoelectronic device according to one embodiment.

[0019] 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 located between the anode and the cathode, wherein at least one organic layer includes a composition for an organic optoelectronic device according to one embodiment.

[0020] Embodiments can be realized by providing a display device including an organic optoelectronic device according to one embodiment. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] Features will be apparent to those skilled in the art by describing exemplary embodiments in detail with reference to the drawings, wherein:

[0022] Figure 1 is a cross-sectional view showing an organic light-emitting diode according to some example embodiments. DETAILED DESCRIPTION

[0023] Example embodiments will now be described more fully hereinafter with reference to the 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 for those skilled in the art, and will fully convey the example embodiments.

[0024] In the drawings, for clarity of illustration, the dimensions of layers and regions may be exaggerated. 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 intervening layers may also be present. Additionally, it will be understood that when a layer is referred to as being “between” two layers, it can be the only layer between the two layers, or one or more intervening layers may also be present. Throughout the invention, like reference numerals refer to like elements. As used herein, the term “or” is not necessarily an exclusive term, e.g., “A or B” will include A, B, or both A and B.

[0025] As used herein, when no other definition is provided, “substituted” means that at least one hydrogen of a substituent or compound is replaced by 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.

[0026] In one instance, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by 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 a specific instance, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, a C1 - C20 alkyl group, a C6 - C30 aryl group, or a cyano group. In a specific instance, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, a C1 - C5 alkyl group, a C6 - C18 aryl group, or a cyano group. In a specific instance, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by 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.

[0027] "Unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom is retained.

[0028] In this specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)". For example, any hydrogen in any compound described herein can be protium, deuterium, or tritium (e.g., based on natural or artificial substitution).

[0029] As used herein, when no other definition is provided, "hetero" means a group containing 1 to 3 heteroatoms selected from N, O, S, P, and Si in a functional group and the remainder being carbon.

[0030] 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. For example, a phenyl group, a naphthyl group, etc., can connect two or more hydrocarbon aromatic moieties through a σ - bond and the hydrocarbon aromatic moiety can 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, for example, a fluorenyl group.

[0031] An aryl group can include a monocyclic, polycyclic, or fused - ring polycyclic (i.e., rings sharing adjacent carbon atom pairs) functional group.

[0032] As used herein, "heterocyclic group" is a superordinate concept of heteroaryl, and can include at least one heteroatom selected from N, O, S, P, and Si in a ring compound such as an aryl group, a cycloalkyl group, its fused ring, or a combination thereof to replace carbon (C). When the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group can include one or more heteroatoms.

[0033] For example, "heteroaryl" can represent 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 a heteroaryl group includes two or more rings, the two or more rings can be fused. When the heteroaryl group is a fused ring, each ring can include 1 to 3 heteroatoms.

[0034] More specifically, the substituted or unsubstituted C6-C30 aryl group can 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 quaterphenyl 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 group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof, but not limited thereto.

[0035] More specifically, the substituted or unsubstituted C2-C30 heterocyclic group can 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 benzofuranoindenyl group, a substituted or unsubstituted benzothienoindenyl group, or a combination thereof, but not limited thereto.

[0036] As used herein, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive characteristics, according to the highest occupied molecular orbital (HOMO) level, the holes formed in the anode can be easily injected into the light-emitting layer and transported therein.

[0037] In addition, electron characteristics refer to the ability to accept electrons when an electric field is applied, and due to the conductive characteristics, according to the lowest unoccupied molecular orbital (LUMO) level, the electrons formed in the cathode can be easily injected into the light-emitting layer and transported therein.

[0038] Hereinafter, compounds for organic optoelectronic devices according to some exemplary embodiments are described.

[0039] Compounds for organic optoelectronic devices according to some exemplary embodiments may be represented by, for example, Chemical Formula 1 or Chemical Formula 2.

[0040] [Chemical Formula 1]

[0041]

[0042] [Chemical Formula 2]

[0043]

[0044] In Chemical Formulas 1 and 2, L 1 may be or may include, for example, a single bond or a substituted or unsubstituted C6 to C30 arylene group.

[0045] Ar 1 and Ar 2 may each independently be or include, for example, a substituted or unsubstituted C6 to C30 aryl group.

[0046] R 1 to R 19 may each independently be or include, for example, hydrogen, deuterium, cyano group, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof.

[0047] m1 may be, for example, an integer from 1 to 3. In one embodiment, m1 may be 2 or 3, and each R 5 may be the same as or different from each other.

[0048] The compound according to one embodiment may have the following structure: wherein the indolocarbazole mother nucleus having a flat structure is further substituted with a carbazole in the N-direction of indolocarbazole (e.g., through a linking group).

[0049] In one embodiment, the compound represented by Chemical Formula 1 may be additionally substituted with a carbazole in the N-direction of indolocarbazole, and it may have a shallow HOMO and thus improve the driving voltage due to fast hole transport characteristics. These characteristics may be caused by the hole characteristics of the additionally substituted carbazole, and thus these characteristics may not be expected from a structure that does not include an additionally substituted carbazole group.

[0050] In one embodiment, N-carbazole may be substituted with indolocarbazole through an o-phenylene linking group or substituted on indolocarbazole, thereby increasing steric hindrance and improving the efficiency of an organic light-emitting diode using the same.

[0051] In one embodiment, the structural rigidity may be increased through o-phenylene, and since the structural changes that occur when holes pass through are minimized, the recombination energy may be reduced and fast driving voltage characteristics may be exhibited.

[0052] In one embodiment, m1 may be 2 or greater, and each R 5 may be the same as or different from each other.

[0053] In one embodiment, Chemical Formula 1 may be represented by one of Chemical Formulas 1-1 to 1-4, for example.

[0054]

[0055] In Chemical Formulas 1-1 to 1-4, L 1 , Ar 1 and Ar 2 , R 1 to R 19 and m1 may be defined in the same manner as those in Chemical Formula 1.

[0056] In one embodiment, Chemical Formula 2 may be represented by one of Chemical Formulas 2-1 to 2-4, for example.

[0057]

[0058] In Chemical Formulas 2-1 to 2-4, L 1 , Ar 1 and Ar 2 , R 1 to R 19 and m1 may be defined in the same manner as those in Chemical Formula 2.

[0059] In one embodiment, Ar 1 and Ar 2Each may independently be (for example), a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted terphenyl.

[0060] In one embodiment, *-L 1 -Ar 1 and *-Ar 2 moieties may each independently be (for example) moieties of Group I.

[0061] [Group I]

[0062]

[0063] In Group I, R 20 to R 22 may each independently be (for example) hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C10 alkyl, or a substituted or unsubstituted C6-C12 aryl.

[0064] m2 may be (for example) an integer from 1 to 5.

[0065] m3 may be (for example) an integer from 1 to 4.

[0066] m4 may be (for example) an integer from 1 to 3.

[0067] * is a point of attachment.

[0068] In one embodiment, m2 may be 2 to 5, and each R 20 may be the same or different from each other.

[0069] In one embodiment, m3 may be 2 to 4, and each R 21 may be the same or different from each other.

[0070] In one embodiment, m4 may be 2 or 3, and each R 22 may be the same or different from each other.

[0071] In one embodiment, R 1 to R 19 may each independently be (for example) hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C6-C12 aryl, or a combination thereof.

[0072] In one embodiment, R 1 to R 19 may each independently be (for example) hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C5 alkyl, or a substituted or unsubstituted phenyl.

[0073] In one embodiment, the compound for an organic optoelectronic device represented by Chemical Formula 1 or Chemical Formula 2 may be, for example, a compound of Group 1.

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081] The composition for an organic optoelectronic device according to some example embodiments may include a first compound and a second compound. In one embodiment, the first compound may be the above-described compound for an organic optoelectronic device (e.g., the compound for an organic optoelectronic device represented by Chemical Formula 1 or Chemical Formula 2), and the second compound may be represented by Chemical Formula 3.

[0082] [Chemical Formula 3]

[0083]

[0084] In Chemical Formula 3, 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 may be N.

[0085] Each L a may independently be or include, for example, a single bond, a substituted or unsubstituted C6 to C20 arylene, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

[0086] Each R a may independently be or include, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C6 to C30 aryl, 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.

[0087] Each R aThey may exist separately or adjacent groups among them may be linked to form, for example, a substituted or unsubstituted aliphatic monocyclic or polycyclic, substituted or unsubstituted aromatic monocyclic or polycyclic, or substituted or unsubstituted heteroaromatic monocyclic or polycyclic.

[0088] The second compound may help effectively widen the LUMO energy band by including a nitrogen-containing hexagonal or six-membered ring moiety, and thus it may be included together with the first compound described above to help improve the balance of holes and electrons, thereby significantly improving the lifetime characteristics of the device to which it is applied.

[0089] In one embodiment, two of Z 1 to Z 6 may be nitrogen (N) and the remainder may be C-L a -R a .

[0090] In one embodiment, Z 1 and Z 3 may be nitrogen, Z 2 may be N or C-L a -R a , Z 4 may be N or C-L a -R a , Z 5 may be N or C-L a -R a , and Z 6 may be N or C-L a -R a .

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

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

[0093] In one embodiment, based on R aFor specific substituents, the second compound can be represented by, for example, one of Chemical Formulas 3A to 3C.

[0094]

[0095] [Chemical Formula 3C]

[0096]

[0097] In Chemical Formulas 3A to 3C, 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 to C20 arylene, a substituted or unsubstituted C2 to 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 to C30 alkyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl, a substituted or unsubstituted amino group, a halogen, a cyano group, or a combination thereof.

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

[0102] R 31 to R 35 each independently exist or adjacent groups among them are linked to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring,

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

[0104] R a 、Ar 3 and Ar 4 may each be present separately or R a 、Ar 3 and Ar 4 adjacent groups of may be joined to form a substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic ring.

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

[0106] In Chemical Formula 3B, m5 may be 2 or 3, and each R 31 may be the same or different.

[0107] In Chemical Formula 3C, m6 may be 2 or 3, and each R 36 may be the same or different.

[0108] In this specification, the representation that 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 3A, adjacent groups among R 23 to R 30 may be joined to each other to form a substituted or unsubstituted aromatic monocyclic ring. The formed aromatic monocyclic ring may include, for example, a substituted or unsubstituted phenyl group.

[0109] In one embodiment, Chemical Formula 3A may be represented by, for example, one of Chemical Formulas 3A-I to 3A-VIII.

[0110]

[0111]

[0112]

[0113]

[0114] In Chemical Formulas 3A-I to 3A-VIII, L 2 to L 4 、Ar 3 and Ar 4 、R 23 to R 30 may have the same definitions as those described above.

[0115] Ar 5 may be, for example, a substituted or unsubstituted C6-C30 aryl or a substituted or unsubstituted C2-C30 heterocyclic group.

[0116] L 5 may be, for example, a single bond, a substituted or unsubstituted C6-C20 arylene 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, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl.

[0119] In one embodiment, Ar 3 to Ar 5 may each independently be, for example, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted quaterphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted terphenylene, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl.

[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, a substituted or unsubstituted biphenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl.

[0121] In one embodiment, Chemical Formula 3B may be represented by, for example, one of Chemical Formulas 3B-I to 3B-IV.

[0122]

[0123]

[0124] In Chemical Formulas 3B-I to 3B-IV, L 2 to L 4 , Z 1 , Z 3 and Z 5 , X 1 , Ar 3 and Ar 4 , R 31 to R 35 and m5 can have the same definitions as those described above.

[0125] In one embodiment, Chemical Formula 3C can be represented by, for example, Chemical Formula 3C-I or Chemical Formula 3C-II.

[0126]

[0127] In Chemical Formulas 3C-I and 3C-II, L 2 to L 4 , Z 1 , Z 3 and Z 5 , m6, Ar 3 and Ar 4 , R 36 to R 44 can have the same definitions as those described above.

[0128] In one embodiment, Chemical Formula 3 can be represented by, for example, Chemical Formula 3A-I, Chemical Formula 3B-I, Chemical Formula 3B-II, or Chemical Formula 3C-I.

[0129] In one embodiment, in Chemical Formula 3A-I, L 2 to L 4 can each independently be, for example, a single bond or a substituted or unsubstituted C6 to 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 23 to R 30 can each independently be, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0130] In one embodiment, in Formula 3B-I and Formula 3B-II, L 2 to L 4 can each independently be, for example, 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 31 to R 35 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, in Formula 3C-I, L 2 to L 4 can each independently be, for example, 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 44 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.

[0132] In one embodiment, the second compound can be, for example, a compound of Group 2.

[0133] Group 2

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155] The first and second compounds may be included (e.g., mixed) at a weight ratio of, for example, 1:99 to 99:1. By including within the above range, bipolar characteristics can be achieved by adjusting the appropriate weight ratio and utilizing the hole-transporting ability of the first compound and the electron-transporting ability of the second compound, thereby improving efficiency and lifespan. In one embodiment, they may be included at a weight ratio of, for example, about 10:90 to 90:10, about 20:80 to 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 at a weight ratio of 40:60, 50:50, or 60:40.

[0156] Hereinafter, an organic optoelectronic device including the above-described compound for an organic optoelectronic device or a composition for an organic optoelectronic device will be described.

[0157] The organic optoelectronic device may be a suitable device that converts electrical energy into light energy (and vice versa), such as, for example, an organic optoelectronic device, an organic light-emitting diode, an organic solar cell, or an organic photoconductive drum.

[0158] In this document, with reference to the accompanying drawings, an organic light-emitting diode, which is an example of an organic optoelectronic device, is described.

[0159] Figure 1 is a cross-sectional view showing an organic light-emitting diode according to some example embodiments.

[0160] With reference to the accompanying drawings, an organic light-emitting diode 100 according to some example embodiments may include an anode 120 and a cathode 110 that face each other, and an organic layer 105 disposed between the anode 120 and the cathode 110.

[0161] The anode 120 may be made of a conductor having a large work function to facilitate hole injection, and may be (for example) a metal, a metal oxide, or a conductive polymer. The anode 120 may be (for example) a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, 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, and polyaniline.

[0162] 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, 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.

[0163] The organic layer 105 may include the compounds or compositions for the organic optoelectronic device described above.

[0164] The organic layer 105 may include a light-emitting layer 130, the light-emitting layer 130 may include a host and a dopant, the host may include the compounds or compositions for the organic optoelectronic device described above, and the dopant may be (for example) a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0165] The dopant may be a material that is mixed in a small amount with the compounds or compositions for the organic optoelectronic device to cause luminescence, and may 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 may be (for example) an inorganic, organic, or organic-inorganic compound, and one or more types thereof may be used.

[0166] Examples of dopants can include phosphorescent dopants, and examples of phosphorescent dopants can be organometallic compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. The phosphorescent dopant can be, for example, a compound represented by Chemical Formula Z.

[0167] [Chemical Formula Z]

[0168] L 6 MX 3

[0169] In Chemical Formula Z, M can be a metal, and L 6 and X 3 can each independently be a ligand that forms a complex with M.

[0170] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L 3 and X 2 can be, for example, bidentate ligands.

[0171] Examples of the ligands represented by L 6 and X 3 can include ligands of Group A.

[0172] [Group A]

[0173]

[0174] In Group A, R 300 to R 302 can each independently be, for example, hydrogen, deuterium, halogen-substituted or unsubstituted C1 to C30 alkyl, C6 to C30 aryl substituted or unsubstituted with C1 to C30 alkyl, or halogen.

[0175] R 303 to R 324 can each independently be, for example, hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF5, trialkylsilyl having substituted or unsubstituted C1 to C30 alkyl, dialkylarylsilyl having substituted or unsubstituted C1 to C30 alkyl and C6 to C30 aryl, or triarylsilyl having substituted or unsubstituted C6 to C30 aryl.

[0176] According to some example embodiments, the dopant may be an iridium complex and may include, for example, a dopant represented by Chemical Formula 4-1 or Chemical Formula 4-2.

[0177] [Chemical Formula 4-1]

[0178]

[0179] 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 .

[0180] R 132 to R 134 may each independently be, for example, a substituted or unsubstituted C1-C6 alkyl group.

[0181] In one embodiment, at least one of R 101 to R 116 may be a functional group represented by Chemical Formula V-1.

[0182] L 100 may be 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.

[0183] 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.

[0184] [Chemical Formula V-1]

[0185]

[0186] 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 .

[0187] * represents a moiety attached to a carbon atom.

[0188] [Chemical Formula 4-2]

[0189]

[0190] In Chemical Formula 4-2, R 101 to R 117 can 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 133 R 134 R 135 .

[0191] R 133 to R 135 can each independently be (for example) a substituted or unsubstituted C1-C6 alkyl group.

[0192] L 100 can 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] n1 and n2 can each independently be (for example) an integer from 0 to 3, and n1 + n2 can be an integer from 1 to 3.

[0194] The dopant according to some exemplary embodiments can be a platinum complex and can be (for example) represented by Chemical Formula Z-1.

[0195] [Chemical Formula Z-1]

[0196]

[0197] In Chemical Formula Z-1, rings A, B, C, and D can each independently be (for example) a 5-membered or 6-membered carbocyclic or heterocyclic ring.

[0198] R A 、R B 、R C and R D can each independently be (for example) monosubstituted, disubstituted, trisubstituted, tetrasubstituted, or unsubstituted.

[0199] L B 、L C and L D can each independently be (for example) a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', or a combination thereof.

[0200] In one embodiment, nA can be 1, and L E 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 is absent;

[0201] R A 、R B 、R C 、R D 、R and R' can each independently be, for example, hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxyl, ester, cyano, isocyano, thioalkyl, sulfinyl, sulfonyl, phosphino or combinations thereof; any adjacent R A 、R B 、R C 、R D 、R and R' are optionally joined to each other to provide a ring; X B 、X C 、X D and X E each independently selected from carbon and nitrogen; and Q 1 、Q 2 、Q 3 and Q 4 respectively represent oxygen or a direct bond.

[0202] The platinum complex can be represented, for example, by Chemical Formula 5-1 or Chemical Formula 5-2.

[0203] [Chemical Formula 5-1]

[0204]

[0205] [Chemical Formula 5-2]

[0206]

[0207] In Chemical Formula 5-1 and Chemical Formula 5-2, X 100 can be, for example, O, S or NR 132 .

[0208] 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 .

[0209] R 133 to R 135 can each independently be, for example, substituted or unsubstituted C1-C6 alkyl.

[0210] In one embodiment, R 118 to R 132At least one of them can be -SiR 133 R 134 R 135 or tert-butyl.

[0211] R 133 to R 135 can each independently be (for example) a substituted or unsubstituted C1 to C6 alkyl group.

[0212] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0213] The charge transport region can be (for example) the hole transport region 140.

[0214] The hole transport region 140 can help further improve the hole injection and / or hole mobility between the anode 120 and the light-emitting layer 130 and block electrons.

[0215] In one embodiment, the hole transport region 140 may include a hole transport layer located between the anode 120 and the light-emitting layer 130, and a hole transport auxiliary layer located 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.

[0216] [Group B]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222] (Dn refers to the number of deuterium substitutions and represents 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.

[0223] In the hole transport region, in addition to the compounds described above, other suitable compounds can also be used.

[0224] In one embodiment, the charge transport region can be (for example) the electron transport region 150.

[0225] The electron transport region 150 can help further improve the electron injection and / or electron mobility between the cathode 110 and the light-emitting layer 130 and block holes.

[0226] 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.

[0227] [Group C]

[0228]

[0229]

[0230]

[0231] Some example embodiments may provide an organic light-emitting diode including a light-emitting layer as an organic layer.

[0232] Some example embodiments may provide an organic light-emitting diode including a light-emitting layer and a hole transport region as organic layers.

[0233] Some example embodiments may provide an organic light-emitting diode including a light-emitting layer and an electron transport region as organic layers.

[0234] Some example embodiments may provide an organic light-emitting diode including, in addition to the light-emitting layer 130, a hole transport region 140 and an electron transport region 150 as organic layers 105, as shown.

[0235] 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.

[0236] The organic light-emitting diode 100 can be produced by forming an anode or a cathode on a substrate, and then forming the organic layers by dry film formation such as vacuum deposition, sputtering, plasma plating, and ion plating, and forming a cathode or an anode thereon.

[0237] The above organic light-emitting diode can be applied to an organic light-emitting diode display device.

[0238] 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 regarded as limiting the scope of the embodiments, nor should the comparative examples be regarded as 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.

[0239] Hereinafter, unless otherwise specified, starting materials and reactants used in the examples and synthetic examples were purchased from Sigma-Aldrich Co., Ltd., TCI Inc., Tokyo Chemical Industry, or P&H tech, or were synthesized by known methods.

[0240] (Synthesis of Compounds for Organic Optoelectronic Devices)

[0241] Synthetic Example 1: Synthesis of Compound A-1

[0242] [Reaction Scheme 1]

[0243]

[0244] a) Synthesis of Intermediate A-1-1

[0245] 1-Bromo-9H-carbazole (50 g, 203.2 mmol), iodobenzene (62.2 g, 304.7 mmol), copper(I) iodide (7.7 g, 40.6 mmol), potassium carbonate (42.1 g, 304.7 mmol), and 1,10-phenanthroline (4.4 g, 24.4 mmol) were dissolved in 1 L of N,N-dimethylformamide, and then refluxed and stirred at 180 °C for 12 hours. After the reaction was completed, the resulting product was purified by column chromatography using a mixed solvent of dichloromethane and n-hexane to obtain 53.8 g (yield: 82.2%) of Intermediate A-1-1.

[0246] b) Synthesis of Intermediate A-1-2

[0247] Intermediate A-1-1 (53.8 g, 167.0 mmol) was dissolved in 300 mL of anhydrous tetrahydrofuran and then maintained at -78 °C. Subsequently, a 2.5 M n-butyllithium solution (200.4 mmol) was slowly added dropwise thereto. After about 30 minutes, triisopropyl borate (37.7 g, 200.4 mmol) was slowly added dropwise thereto. After stirring for 12 hours and after the reaction was completed, a small amount of hydrochloric acid was added thereto, and then stirred for 30 minutes. After removing the solvent therefrom, the residue was extracted again with ethyl acetate and distilled water. Thus, 45.2 g (yield: 94.3%) of Intermediate A-1-2 was obtained without further purification.

[0248] c) Synthesis of Intermediate A-1-3

[0249] Intermediate A-1-2 (45.2 g, 157.4 mmol), 1-bromo-2-nitrobenzene (33.4 g, 165.3 mmol), Pd(PPh3)4 (9.1 g, 7.9 mmol) and potassium carbonate (65.3 g, 472.3 mmol) were added to a mixed solution of 800 mL of tetrahydrofuran: deionized water, and then refluxed and stirred for 12 hours. After the reaction was completed, the obtained product was purified by column chromatography using a mixed solvent of dichloromethane and n-hexane to obtain 38.8 g (yield: 67.7%) of Intermediate A-1-3.

[0250] d) Synthesis of Intermediate A-1-4

[0251] Intermediate A-1-3 (38.8 g, 106.5 mmol) and triphenylphosphine (83.8 g, 19.4 mmol) were added to 500 mL of 1,2-dichlorobenzene, and then refluxed and stirred for 16 hours. After the reaction was completed, the obtained product was purified by column chromatography using a mixed solvent of dichloromethane and n-hexane to obtain 20.4 g (yield: 59.5%) of Intermediate A-1-4.

[0252] e) Synthesis of Compound A-1

[0253] Intermediate A-1-4 (3.0 g, 9.3 mmol), 2-(2-fluorophenyl)-9-phenyl-9H-carbazole (3.5 g, 102.mmol) and potassium carbonate (3.9 g, 27.9 mmol) were added to 50 mL of N-methylpyrrolidone, and then refluxed and stirred for 12 hours. After the reaction was completed, the obtained product was purified by column chromatography using a mixed solvent of dichloromethane and n-hexane to obtain 4.6 g (yield: 76.5%) of Compound A-1.

[0254] Synthesis Examples 2 to 7

[0255] Each compound was synthesized using Reactant 1 and Reactant 2 as starting materials through the final reaction (nucleophilic aromatic substitution) of Synthesis Example 1.

[0256] (Table 1)

[0257]

[0258]

[0259] Synthesis Example 8: Synthesis of Compound B-8

[0260] [Reaction Formula 2]

[0261]

[0262] a) Synthesis of Intermediate B-8-1

[0263] Using 4-bromo-9H-carbazole and 4-biphenylboronic acid as starting materials in the same manner as in Intermediate A-1-3 of Synthesis Example 1. After completion of the reaction, the resulting product was recrystallized and purified with a mixed solvent of dichloromethane and n-hexane to obtain 26.0 g (yield: 66.8%) of Intermediate B-8-1.

[0264] b) Synthesis of Compound B-8

[0265] Using Intermediate B-8-1 and 2-([1,1'-biphenyl]-4-yl)-4-(2-fluorophenyl)-6-phenyl-1,3,5-triazine as starting materials, the synthesis was carried out in the same manner as in Compound A-1 of Synthesis Example 1. After completion of the reaction, the resulting product was recrystallized and purified with toluene to obtain 8.5 g (yield: 77.1%) of Compound B-8.

[0266] Synthesis Example 9: Synthesis of Compound B-15

[0267] [Reaction Scheme 3]

[0268]

[0269] a) Synthesis of Intermediate B-15-1

[0270] Using 1-bromo-2-fluoro-4-iodobenzene and phenylboronic acid as starting materials, the synthesis was carried out in the same manner as in A-1-3 of Synthesis Example 1. After completion of the reaction, the resulting product was recrystallized and purified with a mixed solvent of dichloromethane and n-hexane to obtain 35.3 g (yield: 71.2%) of Intermediate B-15-1.

[0271] b) Synthesis of Intermediate B-15-2

[0272] Using Intermediate B-15-1 and carbazole as starting materials, the synthesis was carried out in the same manner as in Compound A-1 of Synthesis Example 1. After completion of the reaction, the resulting product was recrystallized and purified with a mixed solvent of dichloromethane and n-hexane to obtain 25.5 g (yield: 69.9%) of Intermediate B-15-2.

[0273] c) Synthesis of Intermediate B-15-3

[0274] Using Intermediate B-15-2 as a starting material in the same manner as in Intermediate A-1-2 of Synthesis Example 1. After completion of the reaction, the slurry was purified with n-hexane to obtain 16.5 g (yield: 92.5%) of Intermediate B-15-3.

[0275] d) Synthesis of Compound B-15

[0276] Synthesis was carried out in the same manner as Intermediate A-1-3 of Synthesis Example 1 using Intermediate B-15-3 and 9-(4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazin-2-yl)-9H-carbazole as starting materials. After completion of the reaction, the slurry was recrystallized and purified with toluene to obtain 10.0 g (yield: 68.5%) of Intermediate B-15.

[0277] Synthesis Example 10: Synthesis of Compound B-69

[0278] [Reaction Scheme 4]

[0279]

[0280] Synthesis was carried out in the same manner as Compound A-1 of Synthesis Example 1 using 2-([1,1'-biphenyl]-4-yl-d9)-4-(2-fluorophenyl-3,4,5,6-d4)-6-(phenyl-d5)-1,3,5-triazine and 4-([1,1'-biphenyl]-3-yl-d9)-9H-carbazole-1,2,3,5,6,7,8-d7. After completion of the reaction, the slurry was recrystallized and purified with toluene to obtain 7.2 g (yield: 85.1%) of Compound B-69.

[0281] Synthesis Example 11: Synthesis of Compound B-108

[0282] [Reaction Scheme 5]

[0283]

[0284] Synthesis was carried out in the same manner as Intermediate A-1-3 of Synthesis Example 1 using 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-(9-phenyldibenz[b,d]furan-3-yl)-1,3,5-triazine and 4,4,5,5-tetramethyl-2-(9-phenyldibenz[b,d]furan-4-yl)-1,3,2-dioxaborolane. After completion of the reaction, the slurry was recrystallized and purified with toluene to obtain 10.2 g (yield: 85.2%) of Compound B-108.

[0285] Synthesis Example 12: Synthesis of Compound B-217

[0286] [Reaction Scheme 6]

[0287]

[0288] Synthesis was carried out in the same manner as A-1-3 of Synthesis Example 1 using 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-(triphenylene-2-yl)-1,3,5-triazine and ([1,1'-biphenyl]-4-yl-d9)boronic acid. After completion of the reaction, the slurry was recrystallized and purified with monochlorobenzene to obtain 10.0 g (yield: 83.2%) of Compound B-217.

[0289] Comparative Synthesis Example 1: Synthesis of Compound C-1

[0290] [Reaction Formula 7]

[0291]

[0292] Synthesis was carried out in the same manner as Compound A-1 of Synthesis Example 1 using Intermediate A-1-4 and 3-(2-fluorophenyl)dibenzofuran as starting materials to obtain 3.6 g (yield: 60.2%) of Compound C-1.

[0293] Comparative Synthesis Example 2: Synthesis of Compound C-2

[0294] [Reaction Formula 8]

[0295]

[0296] Synthesis was carried out in the same manner as Compound A-1 of Synthesis Example 1 using Intermediate A-1-4 and 1-(2-fluorophenyl)dibenzothiophene as starting materials to obtain 2.2 g (yield: 42.6%) of Compound C-2.

[0297] Comparative Synthesis Example 3: Synthesis of Compound C-3

[0298] [Reaction Formula 9]

[0299]

[0300] Intermediate A-1-4 (3.0 g, 9.3 mmol), 3-(4-chlorophenyl)-9-phenyl-9H-carbazole (3.6 g, 10.2 mmol), Pd2(dba)3 (0.4 g, 0.5 mmol), sodium tert-butoxide (1.3 g, 14.0 mmol) and tris(tert-butyl)phosphine (0.3 g, 1.4 mmol) were added to 50 mL of xylene, and then refluxed and stirred for 12 hours. After completion of the reaction, 3.2 g (yield: 52.1%) of Compound C-3 was obtained by column chromatography using a mixed solvent of dichloromethane and n-hexane.

[0301] Comparative Synthesis Example 4: Synthesis of Compound C-4

[0302] [Reaction Formula 10]

[0303]

[0304] Synthesis was carried out in the same manner as in the case of Compound C-3 of Comparative Synthesis Example 3 using Intermediate A-1-4 and 4-(3-chlorophenyl)-9-phenyl-9H-carbazole as starting materials, thereby obtaining 3.0 g (yield: 51.0%) of Compound C-4.

[0305] Comparative Synthesis Example 5: Synthesis of Compound C-5

[0306] [Reaction Scheme 11]

[0307]

[0308] Synthesis was carried out in the same manner as in the case of Compound C-3 of Comparative Synthesis Example 3 using Intermediate 5-phenyl-5,12-dihydroindolo[3,2-a]carbazole and 2-(4-chlorophenyl)-9-phenyl-9H-carbazole as starting materials, thereby obtaining 2.9 g (yield: 50.0%) of Compound C-5.

[0309] Example 1: Production of a green organic light-emitting diode (single host)

[0310] A glass substrate coated with an ITO (indium tin oxide) film was ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrate was ultrasonically cleaned with isopropyl alcohol, acetone or methanol and dried, then transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and transferred 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 of to form a hole transport layer. Compound B was deposited on the hole transport layer to a thickness of to form a hole transport auxiliary layer. On the hole transport auxiliary layer, Compound A-1 was used as the host and doped with 7 wt% of PhGD 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 Compound D and Liq were co-vacuum deposited at a weight ratio of 1:1 to form a -thick electron transport layer. On the electron transport layer, a cathode was formed by sequentially vacuum depositing LiQ and Al, thereby producing an organic light-emitting diode.

[0311] An organic light-emitting diode is produced to have the following structure: ITO / Compound A (doped with 3% NDP-9, ) / Compound A / Compound B / EML [Host (Compound A-1): PhGD = 93 wt%: 7 wt%] / Compound C / Compound D: LiQ / LiQ / Al

[0312] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0313] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0314] 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

[0315] Compound D: 2-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0316] [PhGD]

[0317]

[0318] Examples 2 to 7 and Comparative Examples 1 to 5

[0319] Except that the composition is changed to those shown in Table 2, an organic light-emitting diode is produced in the same manner as in Example 1.

[0320] Example 8: Production of a green organic light-emitting diode (mixed host)

[0321] A glass substrate coated with an ITO (indium tin oxide) film is ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrate is ultrasonically cleaned with isopropyl alcohol, acetone, or methanol and dried, then transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and transferred to a vacuum depositor. This prepared ITO transparent electrode is used as the anode, and Compound E doped with 3% NDP-9 (Novaled GmbH) is vacuum deposited on the ITO substrate to form - A thick hole injection layer, and deposit compound E on the hole injection layer to of a thickness to form a hole transport layer. Deposit compound F on the hole transport layer to of a thickness to form a hole transport auxiliary layer. On the hole transport auxiliary layer, use compound A-1 and compound B-8 as hosts simultaneously at a weight ratio of 3:7, and dope PtGD at 15 wt% as a dopant to form - thick light-emitting layer by vacuum deposition. Subsequently, on the light-emitting layer, deposit compound G to of a thickness to form an electron transport auxiliary layer, and co-vacuum deposit compound H and Liq at a weight ratio of 1:1 to form a thickness of of the electron transport layer. On the electron transport layer, form the cathode by sequentially vacuum depositing LiQ and Al, thereby producing an organic light-emitting diode.

[0322] Produce an organic light-emitting diode to have the following structure: ITO / Compound E (doped with 3% NDP-9, ) / Compound E / Compound F / EML [Host (Compound A-1:Compound B-8 = 3:7 w / w):PtGD = 85 wt%:15 wt%] / Compound / Compound H:LiQ / LiQ / Al

[0323] Compound E: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine

[0324] Compound F: 9,9-dimethyl-N-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-4-(4-phenylphenyl)-9H-fluoren-2-amine

[0325] Compound G: 4-{4-[4-(9,9-dimethyl-9H-fluoren-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[0326] Compound H: 2-(4-{1-[4-(diphenyl-1,3,5-triazin-2-yl)phenyl]naphthalen-2-yl}-4,6-diphenyl-1,3,5-triazine

[0327] [PtGD]

[0328]

[0329] Examples 9 to 18 and Comparative Examples 6 to 10

[0330] Each organic light emitting diode was produced in the same manner as in Example 8, except that the composition was changed to those shown in Table 3.

[0331] Evaluation

[0332] The driving voltage, luminous efficiency, and lifetime characteristics of the organic light emitting diodes according to Examples 1 to 18 and Comparative Examples 1 to 10 were evaluated.

[0333] The measurement methods are as shown below, and the results are shown in Tables 2 and 3.

[0334] (1) Measuring the change in current density according to voltage change

[0335] While increasing the voltage from 0 V to 10 V using a voltmeter (Keithley 2400), the measured organic light emitting diode was measured for the current value flowing into the unit device, and the measured current value was divided by the area to provide the result.

[0336] (2) Measuring the change in luminance according to voltage change

[0337] While increasing the voltage of the organic light emitting diode from 0 V to 10 V, the luminance was measured using a photometer (Minolta Cs-1000A).

[0338] (3) Measurement of luminous efficiency

[0339] Using the luminance, current density, and voltage from (1) and (2) above, the luminous efficiency (cd / A) at the same current density (10 mA / cm 2 ) was calculated.

[0340] The luminous efficiency values of Examples 1 to 7 and Comparative Examples 1 to 5 were calculated as relative values based on Example 1 (e.g., as a reference value) and are shown in Table 2.

[0341] The luminous efficiency values of Examples 8 to 18 and Comparative Examples 6 to 10 were calculated as relative values based on Example 8 (e.g., as a reference value) and are shown in Table 3.

[0342] (4) Measurement of lifetime

[0343] By maintaining the luminance (cd / m 2 ) at 24,000 cd / m 2 and measuring the time when the current efficiency (cd / A) decreases to 97%, the result was obtained.

[0344] The lifetime measurements of Examples 1 to 7 and Comparative Examples 1 to 5 were calculated as relative values based on Example 1 and are shown in Table 2.

[0345] The lifetime measurements of Examples 8 to 18 and Comparative Examples 6 to 10 were calculated based on Example 8 as a relative value and are shown in Table 3.

[0346] (5) Measurement of driving voltage

[0347] Using a current-voltage meter (Keithley 2400) at 15 mA / cm 2 The driving voltage of each diode was measured to obtain the results.

[0348] The driving voltages of Examples 1 to 7 and Comparative Examples 1 to 5 were calculated based on Example 1 as a relative value and are shown in Table 2.

[0349] The driving voltages of Examples 8 to 18 and Comparative Examples 6 to 10 were calculated based on Example 8 as a relative value and are shown in Table 3.

[0350] (Table 2)

[0351] Number Main body Driving voltage (%) Luminous efficiency (%) Lifetime (%) Example 1 A-1 100 100 100 Example 2 A-4 98 103 85 Example 3 A-14 98 101 95 Example 4 A-38 97 103 110 Example 5 A-51 97 101 90 Example 6 A-82 98 100 90 Example 7 A-83 98 102 80 Comparative example 1 C-1 110 95 60 Comparative example 2 C-2 110 97 1 Comparative example 3 C-3 100 90 50 Comparative example 4 C-4 103 92 30 Comparative example 5 C-5 104 93 50

[0352] (Table 3)

[0353]

[0354]

[0355] Referring to Tables 2 and 3, compared with the organic light-emitting diodes according to Comparative Examples 1 to 10, the organic light-emitting diodes according to Examples 1 to 18 have improved driving voltage and luminous efficiency, and at the same time, Examples 1 to 18 have significantly improved lifetime characteristics.

[0356] One or more embodiments can provide a compound for an organic optoelectronic device that can reduce the driving voltage and achieve an organic optoelectronic device with high efficiency and long lifetime.

[0357] It is possible to achieve an organic optoelectronic device with high efficiency and long lifetime while reducing the driving voltage.

[0358] Example embodiments have been disclosed herein, and although specific terms have been used, these terms will be used and understood only in a general and descriptive sense and not for purposes of limitation. In some cases, since the filing of this application, it will be apparent to those skilled in the art that, unless otherwise specifically specified, the features, characteristics, and / or elements described in connection with a specific embodiment may be used alone or in combination with the features, characteristics, and / or elements described in connection with other embodiments. Accordingly, those skilled in the art will understand that various changes can be made in form and detail without departing from the spirit and scope of the invention as described in the appended claims.

Claims

1. A compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1 or Chemical Formula 2: [Chemical Formula 1] [Chemical Formula 2] In Chemical Formula 1 and Chemical Formula 2, L 1 is a single bond or a substituted or unsubstituted C6-C30 arylene group, Ar 1 and Ar 2 each independently is a substituted or unsubstituted C6-C30 aryl 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, 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: The compound is represented by Chemical Formula 1, Chemical Formula 1 is represented by one of Chemical Formula 1-1 to Chemical Formula 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 the same as defined in Chemical Formula 1.

3. The compound for an organic optoelectronic device according to claim 1, wherein: The compound is represented by Chemical Formula 2, Chemical Formula 2 is represented by one of Chemical Formula 2-1 to Chemical Formula 2-4: In Chemical Formulas 2-1 to 2-4, L 1 , Ar 1 and Ar 2 , R 1 to R 19 and m1 are the same as defined in Chemical Formula 2.

4. The compound for an organic optoelectronic device according to claim 1, wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

5. The compound for an organic optoelectronic device according to claim 1, wherein: *-L 1 -Ar 1 and *-Ar 2 The *-L, -Ar, and *-Ar moieties are each independently a moiety 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, When m2 is 2, 3, 4 or 5, each R 20 is the same as or different from each other, When m3 is 2, 3 or 4, each R 21 is the same as or different from one another, When m4 is 2 or 3, each R 22 is the same as or different from each other, and * is a connection point.

6. The compound for an organic optoelectronic device according to claim 1, wherein R 1 to R 19 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C12 aryl, or a combination thereof.

7. The compound for an organic optoelectronic device according to claim 1, wherein the compound is a compound of Group 1: Group 1 8. 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 claim 1, and The second compound is represented by Chemical Formula 3: [Chemical Formula 3] In Chemical Formula 3, Z 1 from Z to Z 6 each independently is N or C-L a -R a provided that Z 1 from Z to Z 6 at least two of them are N, L a each 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 are present separately or adjacent groups among them are linked 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 ring.

9. The composition for an organic optoelectronic device according to claim 8, wherein: Chemical Formula 3 is represented by one of Chemical Formula 3A to Chemical Formula 3C: [Chemical Formula 3C] In Chemical Formula 3A to 3C, Z 1 , Z 3 and Z 5 Each independently is N or CL a -R a , the condition is that 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 represents 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.

10. The composition for an organic optoelectronic device according to claim 8, wherein: The second compound is represented by Chemical Formula 3A-I, Chemical Formula 3B-I, Chemical Formula 3B-II or Chemical Formula 3C-I: In Chemical Formula 3A-I, Chemical Formula 3B-I, Chemical Formula 3B-II, and Chemical Formula 3C-I, L 2 to L 4 are each independently a single bond or a substituted or unsubstituted C6 to C12 aryl group, Ar 3 and Ar 4 each independently is a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl or substituted or unsubstituted carbazolyl, R 23 to R 44 each independently is hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl or substituted or unsubstituted C6-C12 aryl, m5 and m6 are each independently an integer from 1 to 3, When m5 is 2 or greater, each R 31 is the same as or different from each other, and When m6 is 2 or greater, each R 36 is the same as or different from one another.

11. An organic optoelectronic device, comprising: An anode and a cathode facing each other, and At least one organic layer located 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 7; or The composition for an organic optoelectronic device according to any one of claims 8 to 10.

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

13. A display device, comprising the organic optoelectronic device according to claim 11.

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