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 represented by Chemical Formula 1, and an organic optoelectronic device and a display device containing the same. The contents of Chemical Formula 1 are as defined in the specification.

Description

[Technical Field]

[0001] 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. [Background technology]

[0002] An organic optoelectric diode is a device that can convert electrical energy and optical energy into each other.

[0003] Organic optoelectronic devices can be broadly divided into two types based on their operating principles: one is a photoelectric device in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to generate electrical energy, and the other is a light-emitting device in which voltage or current is supplied to the electrodes to generate light energy from electrical energy.

[0004] Examples of organic optoelectronic devices include organic photoelectric devices, organic light emitting devices, organic solar cells, and organic photo conductor drums.

[0005] Among these, organic light emitting diodes (OLEDs) have been attracting much attention in recent years due to the increasing demand for flat panel display devices. OLEDs are devices that convert electrical energy into light, and their performance is heavily influenced by the organic materials located between the electrodes. Summary of the Invention [Problem to be solved by the invention]

[0006] One embodiment of the present invention provides a compound for an organic optoelectronic device that can realize an organic optoelectronic device with high efficiency and long life.

[0007] Another embodiment of the present invention provides a composition for an organic optoelectronic device, comprising the compound for an organic optoelectronic device.

[0008] Yet another embodiment of the present invention provides an organic optoelectronic device comprising the compound for an organic optoelectronic device.

[0009] Yet another embodiment of the present invention provides a display device including the organic optoelectronic device. [Means for solving the problem]

[0010] According to one embodiment of the present invention, there is provided a compound for an organic optoelectronic device represented by the following Chemical Formula 1:

[0011] [ka] [Chemical formula 1]

[0012] In the above Chemical Formula 1, X 1 is O or S, R 1 ~R 13 , R 17 and R 18 each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, R 14 ~R 16 are each independently hydrogen or deuterium, Ar 1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, m1 is an integer from 1 to 3; m2 is an integer from 1 to 4.

[0013] According to another embodiment, there is provided a composition for an organic optoelectronic device comprising a first compound and a second compound.

[0014] The first compound is the compound for an organic optoelectronic device described above, and the second compound is represented by Chemical Formula 2 below, a combination of Chemical Formula 3 and Chemical Formula 4 below, or Chemical Formula 5.

[0015] [ka] [Chemical formula 2]

[0016] In the above Chemical Formula 2, R 19 ~R 23 each independently represents hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Ar 2 and Ar 3 each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, L 1 and L 2 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, m3, m6, and m7 each independently represent an integer of 1 to 4; m4 and m5 each independently represent an integer of 1 to 3; n is an integer from 0 to 2.

[0017] [ka] [Chemical formula 3] [Chemical formula 4]

[0018] In the above Chemical Formula 3 and Chemical Formula 4, a1 in chemical formula 3 * ~a4 * are each independently a linking carbon (C) or CLa -R a and a1 in chemical formula 3 * ~a4 * The adjacent two of the groups in formula 4 are * and L a , L 4 and L 5 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R a , R 24 and R 25 each independently represents hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Ar 4 and Ar 5 each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, m8 and m9 each independently represent an integer of 1 to 4.

[0019] [ka] [Chemical formula 5]

[0020] In the above Chemical Formula 5, L 6 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R 26 ~R 29 each independently represents hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Ar 6is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, m10, m12, and m13 each independently represent an integer of 1 to 4; m11 is an integer from 1 to 3.

[0021] According to yet another embodiment, there is provided an organic optoelectronic device comprising: a positive electrode and a negative electrode facing each other; and at least one organic layer located between the positive electrode and the negative electrode, wherein the organic layer comprises the compound for an organic optoelectronic device.

[0022] According to yet another embodiment, there is provided a display device including the organic optoelectronic device. [Effects of the Invention]

[0023] The present invention can realize highly efficient, long-life organic optoelectronic devices. [Brief explanation of the drawings]

[0024] [Figure 1] 1 is a cross-sectional view illustrating an organic light emitting device according to an embodiment. DETAILED DESCRIPTION OF THE INVENTION

[0025] DETAILED DESCRIPTION OF THE INVENTION The following detailed description of the present invention is given by way of example only, and the present invention is not limited thereto, but is defined only by the scope of the claims that follow.

[0026] Unless otherwise defined, the term "substituted" as used herein means that at least one hydrogen atom in a substituent or compound has been replaced with deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted amine group having 1 to 30 carbon atoms, a nitro group, a substituted or unsubstituted silyl group having 1 to 40 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a trifluoroalkyl group having 1 to 10 carbon atoms, a cyano group, or a combination thereof.

[0027] In one embodiment of the present invention, "substituted" means that at least one hydrogen atom in a substituent or compound is substituted with deuterium, an alkyl group having 1 to 30 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or a cyano group. In another specific embodiment of the present invention, "substituted" means that at least one hydrogen atom in a substituent or compound is substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a cyano group. In another specific embodiment of the present invention, "substituted" means that at least one hydrogen atom in a substituent or compound is substituted with deuterium, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a cyano group. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen atom of a substituent or compound is substituted with 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.

[0028] As used herein, "unsubstituted" means that the hydrogen atom remains as a hydrogen atom without being replaced with another substituent.

[0029] As used herein, "hydrogen substitution (-H)" can include "deuterium substitution (-D)" or "tritium substitution (-T)."

[0030] As used herein, unless otherwise defined, "hetero" means that a functional group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, P, and Si, and the remainder is carbon.

[0031] As used herein, the term "aryl group" refers to a general concept of a group having one or more hydrocarbon aromatic moieties, and includes a form in which all elements of the hydrocarbon aromatic moiety have p-orbitals and these p-orbitals form a conjugation, such as a phenyl group or naphthyl group; a form in which two or more hydrocarbon aromatic moieties are linked through a sigma bond, such as a biphenyl group, a terphenyl group, or a quaterphenyl group; and a non-aromatic fused ring in which two or more hydrocarbon aromatic moieties are directly or indirectly fused, such as a fluorenyl group.

[0032] Aryl groups include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0033] As used herein, the term "heterocyclic group" is a generic term that includes a heteroaryl group and refers to a ring compound, such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof, that contains at least one heteroatom selected from the group consisting of N, O, S, P, and Si instead of carbon (C). When the heterocyclic group is a fused ring, the entire heterocyclic group or each ring may contain one or more heteroatoms.

[0034] For example, a "heteroaryl group" refers to an aryl group containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si. Two or more heteroaryl groups may be directly linked through a sigma bond, or, if the heteroaryl group contains two or more rings, the two or more rings may be fused together. If the heteroaryl group is a fused ring, each ring may contain 1 to 3 of the heteroatoms.

[0035] More specifically, the substituted or unsubstituted aryl group having 6 to 30 carbon atoms may be, but is not limited to, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthacenyl 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 benzophenanthrenyl 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.

[0036] More specifically, the substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms is a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl 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 benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzophenone ... or an 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 benzthiazinyl 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 dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted benzofuranofluorenyl group, a substituted or unsubstituted benzothiophenefluorenyl group, or a combination thereof, but is not limited to these.

[0037] In this specification, the term "hole characteristic" refers to the ability to donate electrons to form holes when an electric field is applied, and refers to the ability to have conduction characteristics depending on the HOMO level, and to facilitate the injection of holes formed in the positive electrode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the positive electrode, and the movement of holes in the light-emitting layer.

[0038] The electronic properties refer to the ability to receive electrons when an electric field is applied, and refer to the properties of having conduction properties according to the LUMO level, facilitating the injection of electrons formed in the negative electrode into the light-emitting layer, and the movement of electrons formed in the light-emitting layer to the negative electrode and within the light-emitting layer.

[0039] Hereinafter, a compound for an organic optoelectronic device according to an embodiment will be described.

[0040] The compound for an organic optoelectronic device according to one embodiment is represented by the following Chemical Formula 1:

[0041] [ka] [Chemical formula 1]

[0042] In the above Chemical Formula 1, X 1 is O or S, R 1 ~R 13 , R 17 and R 18 each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, R 14 ~R 16 are each independently hydrogen or deuterium, Ar 1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, m1 is an integer from 1 to 3; m2 is an integer from 1 to 4.

[0043] The compound represented by Chemical Formula 1 is substituted with N-carbazole at the ortho position of the phenylene linked to the triazine, and with a substituted or unsubstituted phenyl group at the other ortho position, and the triazine is substituted with at least one dibenzofuran (or dibenzothiophene).

[0044] The compound represented by Formula 1 has a structure containing ortho-carbazole in triazine, and exhibits particularly excellent energy transfer efficiency to phosphorescent dopants, making it an advantageous material for use as a phosphorescent host. The ortho-biphenyl structure in Formula 1, along with the carbazole substituted at the ortho position of the triazine, significantly increases steric hindrance. As a result, the triazine moiety, the carbazole moiety, and the ortho-phenyl moiety are twisted relative to each other as the dihedral angle increases. This also results in the electron clouds of the HOMO and LUMO levels being largely separated with no overlap, resulting in a small ΔEst and enabling fast energy transfer, demonstrating high efficiency, particularly when used as a phosphorescent host.

[0045] In addition, by substituting at least one dibenzofuran (or dibenzothiophene) in the triazine, the electron mobility is increased compared to mono-phenyl or bi-phenyl triazine, and the stability is increased, resulting in improved driving performance.

[0046] In the above Chemical Formula 1, when m1 is 2 or more, each R 17 may be the same or different from each other.

[0047] In the above Chemical Formula 1, when m2 is 2 or more, each R 18 may be the same or different from each other.

[0048] As an example, Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-4 below.

[0049] [ka] [Chemical formula 1-1] [Chemical formula 1-2]

[0050] [ka] [Chemical formula 1-3] [Chemical formula 1-4]

[0051] In the above Chemical Formulas 1-1 to 1-4, R 1 ~R 18 , Ar 1 , m1 and m2 are defined as above.

[0052] As a specific example, the formula 1 is represented by the formula 1-3 or 1-4.

[0053] As an example, the Ar 1 can be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0054] As an example, the above-mentioned R 1 ~R 13 , R 17 and R 18 may each independently be hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0055] As a specific example, the R 17 and R 18 can each independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0056] In a most specific embodiment, the compound represented by Chemical Formula 1 may be one selected from the compounds listed in Group 1 below, but is not limited thereto.

[0057] [Group 1] [ka]

[0058] [ka]

[0059]

change

[0060]

change

[0061]

change

[0062]

change

[0063]

change

[0064]

change

[0065]

change

[0066]

change

[0067]

change

[0068]

change

[0069] [ka]

[0070] [ka]

[0071] A composition for an organic optoelectronic device according to one embodiment includes a first compound and a second compound, wherein the first compound is the compound for an organic optoelectronic device described above, and the second compound is represented by the following Chemical Formula 2, a combination of Chemical Formula 3 and Chemical Formula 4, or Chemical Formula 5:

[0072] [ka] [Chemical formula 2]

[0073] In the above Chemical Formula 2, R 19 ~R 23 each independently represents hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Ar 2 and Ar 3 each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, L 1 and L 2 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, m3, m6, and m7 each independently represent an integer of 1 to 4; m4 and m5 each independently represent an integer of 1 to 3; n is an integer from 0 to 2.

[0074] [ka] [Chemical formula 3] [Chemical formula 4]

[0075] In the above Chemical Formula 3 and Chemical Formula 4, a1 in chemical formula 3 * ~a4 * are each independently a linking carbon (C) or CL a -R a and a1 in chemical formula 3 * ~a4 * The adjacent two of the groups in formula 4 are * and L a , L 4 and L 5 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R a , R 24 and R 25 each independently represents hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Ar 4 and Ar 5 each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, m8 and m9 each independently represent an integer of 1 to 4.

[0076] [ka] [Chemical formula 5]

[0077] In the above Chemical Formula 5, L 6 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R26 ~R 29 each independently represents hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Ar 6 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, m10, m12, and m13 each independently represent an integer of 1 to 4; m11 is an integer from 1 to 3.

[0078] The second compound, when used in the light-emitting layer together with the first compound, can improve the luminous efficiency and life characteristics by increasing charge mobility and stability.

[0079] In the above Chemical Formula 2, when m3 is 2 or more, each R 19 may be the same or different.

[0080] In the above Chemical Formula 2, when m4 is 2 or more, each R 20 may be the same or different.

[0081] In the above Chemical Formula 2, when m5 is 2 or more, each R 21 may be the same or different.

[0082] In the above Chemical Formula 2, when m6 is 2 or more, each R 22 may be the same or different.

[0083] In the above Chemical Formula 2, when m7 is 2 or more, each R 23 may be the same or different.

[0084] In the above Chemical Formula 3 and Chemical Formula 4, when m8 is 2 or more, each R 24 may be the same or different.

[0085] In the above Chemical Formula 3 and Chemical Formula 4, when m9 is 2 or more, each R 25 may be the same or different.

[0086] In the above Chemical Formula 3 and Chemical Formula 4, R a When two or more R are substituted, each R a may be the same or different.

[0087] In the above Chemical Formula 5, when m10 is 2 or more, each R 26 may be the same or different.

[0088] In the above Chemical Formula 5, when m11 is 2 or more, each R 27 may be the same or different.

[0089] In the above Chemical Formula 5, when m12 is 2 or more, each R 28 may be the same or different.

[0090] In the above Chemical Formula 5, when m13 is 2 or more, each R 29 may be the same or different.

[0091] As an example, Ar in the above Chemical Formula 2 2 and Ar 3 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group; L in the above Chemical Formula 2 2 and L 3 each independently represents a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group; R in the above Chemical Formula 2 19 ~R 23 are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; n can be 0 or 1.

[0092] For example, the term "substituted" in Chemical Formula 2 means that at least one hydrogen atom is substituted with deuterium, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms.

[0093] For example, Ar in Chemical Formula 2 2 and Ar 3 may each independently be a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group.

[0094] In a specific embodiment of the present invention, the formula 2 is represented by one of the following formulas 2-1 to 2-15.

[0095] [ka] [Chemical formula 2-1] [Chemical formula 2-2] [Chemical formula 2-3]

[0096] [ka] [Chemical formula 2-4] [Chemical formula 2-5] [Chemical formula 2-6]

[0097] [ka] [Formula 2-7] [Formula 2-8] [Formula 2-9]

[0098] [ka] [Formula 2-10] [Formula 2-11] [Formula 2-12]

[0099] [ka] [Formula 2-13] [Formula 2-14] [Formula 2-15]

[0100] In the above Chemical Formulas 2-1 to 2-15, R 19 ~R 23 are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; L 2 -Ar 2 and L 3 -Ar 3 may each independently be one of the substituents listed in Group I below.

[0101] [Group I] [ka]

[0102] In Group I, R 30 ~R 34 each independently represents hydrogen, deuterium, a cyano group, an arylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; m14 is an integer between 1 and 5; m15 is an integer between 1 and 4, m16 is an integer between 1 and 3, m17 is an integer of 1 or 2, m18 is an integer between 1 and 7, * is the connection point.

[0103] In Group I, when m14 is 2 or more, each R 30 may be the same or different.

[0104] In Group I, when m15 is 2 or more, each R 31 may be the same or different.

[0105] In Group I, when m16 is 2 or more, each R 32 may be the same or different.

[0106] In Group I, when m17 is 2 or more, each R 33 may be the same or different.

[0107] In Group I, when m18 is 2 or more, each R 34 may be the same or different.

[0108] The combination of Chemical Formula 3 and Chemical Formula 4 is represented by, for example, any one of Chemical Formula 3A, Chemical Formula 3B, Chemical Formula 3C, Chemical Formula 3D, and Chemical Formula 3E below.

[0109] [ka] [Formula 3A] [Formula 3B] [Formula 3C]

[0110] [ka] [Chemical formula 3D] [Chemical formula 3E]

[0111] In the chemical formulas 3A to 3E, L 4 , L 5 , Ar 4 , Ar 5 , R 24 , and R 25 is as described above, L a1 ~L a4 is the above-mentioned L 4 and L 5 As defined in Ra1 ~R a4 is the above-mentioned R 24 , and R 25 As defined in

[0112] For example, Ar in the above chemical formulas 3 and 4 4 and Ar 5 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group; R a1 ~R a4 , R 24 , and R 25 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0113] In a specific embodiment of the present invention, L in Formulas 3 and 4 4 -Ar 4 and L 5 -Ar 5 can each independently be selected from the substituents listed in Group I above.

[0114] In one embodiment, the R a1 ~R a4 , R 24 and R 25 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0115] For example, the R a1 ~R a4 , R 24 and R 25 are each independently hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group; In a specific embodiment, the R a1 ~R a4 , R 24 and R 25 can each independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0116] In a specific embodiment of the present invention, the second compound is represented by Formula 2-8, and Ar 2 and Ar 3 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group; L 2 and L 3 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and R 19 ~R 22 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0117] For example, R in Chemical Formula 2-8 19 ~R 22 are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; L 2 -Ar 2 and L 3 -Ar 3 may each independently be one of the substituents listed in Group I above.

[0118] In another specific embodiment of the present invention, the second compound is represented by Formula 3C, and L in Formula 3C a3 and L a4 is a single bond, and L 4 and L 5 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms; R 24 , R 25 , R a3 and R a4 are hydrogen, deuterium, or a phenyl group, and Ar 2 and Ar 3 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0119] For example, L in Chemical Formula 3C a3 and L a4 is a single bond, and R 24 , R 25 , R a3 and R a4 are each independently hydrogen, deuterium, or an aryl group having 6 to 12 carbon atoms; L 4 -Ar 4 and L 5 -Ar 5 may each independently be one of the substituents listed in Group I above.

[0120] The chemical formula 5 is represented by, for example, any one of the following chemical formulas 5-1 to 5-4.

[0121] [ka] [Chemical formula 5-1] [Chemical formula 5-2]

[0122] [ka] [Chemical formula 5-3] [Chemical formula 5-4]

[0123] In the above Chemical Formulas 5-1 to 5-4, L 6 , Ar 6 , and R 26 ~R 29 is as described above.

[0124] For example, Ar in Chemical Formula 5 6 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group; R 26 ~R 29 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0125] In a specific embodiment of the present invention, L in Formula 5 6 -Ar 6 can be selected from the substituents listed in Group I above.

[0126] For example, the R 26 ~R 29 can each independently be hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group.

[0127] For example, the second compound for an organic optoelectronic device may be one selected from the compounds listed in Group 2 below, but is not limited thereto.

[0128] [Group 2] [ka] [B-1][B-2][B-3][B-4][B-5]

[0129] [ka] [B-6][B-7][B-8][B-9][B-10]

[0130] [ka] [B-11][B-12][B-13][B-14][B-15]

[0131] [ka] [B-16][B-17][B-18][B-19][B-20]

[0132] [ka] [B-21][B-22][B-23][B-24][B-25]

[0133] [ka] [B-26][B-27][B-28][B-29][B-30]

[0134] [ka] [B-31][B-32][B-33][B-34][B-35]

[0135]

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[0136]

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[0137]

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[0138]

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[0139]

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[0140]

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[0141]

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[0142]

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[0143]

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[0144]

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[0145]

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[0146]

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[0147]

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[0148]

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[0149]

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[0150]

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[0151]

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[0152]

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[0153]

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[0154]

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[0155]

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[0156]

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[0157] [ka] [B-143][B-144][B-145]

[0158] [ka] [B-146][B-147][B-148][B-149]

[0159] [ka] [B-150]

[0160] Furthermore, examples of compounds in which at least one hydrogen atom in Compounds B-1 to B-150 listed in Group 2 is substituted with deuterium are shown below, but the present invention is not limited to these.

[0161] [ka] [B-151][B-152][B-153][B-154][B-155]

[0162] [ka] [B-156][B-157][B-158][B-159][B-160]

[0163] [ka] [B-161][B-162][B-163][B-164][B-165]

[0164] [ka] [B-166][B-167][B-168][B-169][B-170]

[0165] [ka] [B-171][B-172][B-173][B-174][B-175]

[0166] [ka] [B-176][B-177][B-178][B-179][B-180]

[0167] [ka] [B-181][B-182][B-183][B-184][B-185]

[0168] [ka] [B-186][B-187][B-188][B-189][B-190]

[0169] [ka] [B-191][B-192][B-193][B-194][B-195] (Dn means the number of deuterium atoms substituted, and indicates a structure with one or more deuterium atoms substituted.)

[0170] The most specific structures of Compounds B-151 to B-195 in Group 2 according to the deuterium substitution position and substitution rate are presented below as examples, and are not intended to limit the scope of rights to compounds not presented below.

[0171] The scope of the present invention is determined by the claims. When deuterium is substituted, the compounds are not limited to those shown below, and the deuterium substitution position, deuterium substitution rate, etc. may include all variable ranges within the scope of Compounds B-1 to B-195.

[0172] [ka] [B-196][B-197][B-198]

[0173] [ka] [B-199][B-200][B-201][B-202]

[0174] [ka] [B-203][B-204][B-205][B-206]

[0175] [ka] [B-207][B-208][B-209][B-210]

[0176] [ka] [B-211][B-212][B-213][B-214]

[0177] [ka] [B-215][B-216][B-217]

[0178] [ka] [B-218][B-219][B-220][B-221]

[0179]

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[0180]

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[0181]

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[0182]

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[0183]

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[0184]

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[0185]

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[0186]

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[0188]

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[0190]

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[0191]

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[0192]

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[0193]

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[0194] [ka] [C-45][C-46][C-47][C-48]

[0195] [ka] [C-49][C-50][C-51][C-52]

[0196] [ka] [C-53][C-54][C-55][C-56]

[0197] [ka] [C-57]

[0198] Furthermore, examples of compounds in which at least one hydrogen atom in Compounds C-1 to C-57 listed in Group 2 is replaced with deuterium are shown below, but the present invention is not limited thereto.

[0199] [ka] [C-58][C-59][C-60][C-61][C-62]

[0200] [ka] [C-63][C-64][C-65][C-66][C-67]

[0201] [ka] [C-68][C-69][C-70][C-71][C-72] (Dn means the number of deuterium atoms substituted, and indicates a structure with one or more deuterium atoms substituted.)

[0202] The most specific structures of Compounds C-58 to C-72 in Group 2 according to the deuterium substitution position and substitution rate are presented below as examples, and are not intended to limit the scope of rights to compounds not presented below.

[0203] The scope of the present invention is determined by the claims. When deuterium is substituted, the compounds are not limited to those shown below, and the deuterium substitution position, deuterium substitution rate, etc. may include all variable ranges within the scope of Compounds C-1 to C-72.

[0204] [ka] [C-73][C-74]

[0205] [ka] [C-75][C-76][C-77][C-78]

[0206] [ka] [C-79][C-80][C-81][C-82]

[0207] [ka] [C-83][C-84][C-85][C-86]

[0208] [ka] [C-87][C-88][C-89][C-90]

[0209]

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[0213]

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[0214]

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[0215]

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[0216]

Chem.

[0217]

Chem.

[0218]

Chem.

[0219]

Chem.

[0220]

Chem.

[0221]

Chem.

[0222]

Chem.

[0223] It should be noted that the content seems to be some kind of chemical or technical notations. The translation attempts to convert the Chinese "

化

Chem.

[0224] Furthermore, examples of compounds in which at least one hydrogen atom in Compounds D-1 to D-60 listed in Group 2 is substituted with deuterium are presented below, but the present invention is not limited thereto.

[0225] [ka] [D-61][D-62][D-63][D-64][D-65]

[0226] [ka] [D-66][D-67][D-68][D-69][D-70]

[0227] [ka] [D-71][D-72][D-73][D-74][D-75]

[0228] [ka] [D-76][D-77][D-78][D-79][D-80]

[0229] [ka] [D-81][D-82][D-83][D-84][D-85]

[0230] [ka] [D-86][D-87][D-88][D-89][D-90]

[0231] [ka] [D-91][D-92][D-93][D-94][D-95]

[0232] [ka] [D-96][D-97][D-98][D-99][D-100]

[0233] [ka] [D-101][D-102][D-103][D-104][D-105]

[0234] [ka] [D-106][D-107][D-108][D-109][D-110]

[0235] [ka] [D-111][D-112][D-113][D-114][D-115]

[0236] [ka] [D-116][D-117][D-118][D-119][D-120] (Dn means the number of deuterium atoms substituted, and indicates a structure with one or more deuterium atoms substituted.)

[0237] In a most specific embodiment, the first compound is represented by Formula 1-3 or Formula 1-4, and the second compound is represented by Formula 2-8.

[0238] The first compound and the second compound are included in a weight ratio of, for example, 1:99 to 99:1. By including them in this range, the electron transport ability of the first compound and the hole transport ability of the second compound can be utilized to achieve bipolar characteristics by combining an appropriate weight ratio, thereby improving efficiency and lifetime. Within this range, the first compound and the second compound can be included in a weight ratio of, for example, about 10:90 to 90:10, about 20:80 to 80:20, or about 20:80 to 70:30, about 20:80 to 60:40, or about 30:70 to 60:40. Specific examples include a weight ratio of 40:60, 50:50, or 60:40.

[0239] In addition to the first and second compounds described above, one or more further compounds may be included.

[0240] The compound for an organic optoelectronic device or the composition for an organic optoelectronic device described above may be a composition further comprising a dopant.

[0241] The dopant can be, for example, a phosphorescent dopant, for example, a red, green or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0242] The dopant is a material that emits light when mixed in a small amount into a compound or composition for an organic optoelectronic device, and typically includes a material such as a metal complex that emits light by multiple excitation, which is excited to a triplet state or higher. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one or more types.

[0243] An example of the dopant is a phosphorescent dopant, and examples of the phosphorescent dopant include organometallic compounds containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant can be, for example, a compound represented by the following chemical formula Z, but is not limited thereto.

[0244] [Chemical formula Z] L 6 MX 2 In the chemical formula Z, M is a metal, and L 6 and X 2 are the same or different and are ligands that form a complex with M.

[0245] The M is, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and the L 6 and X 2 can be, for example, a bidentate ligand.

[0246] L 6 and X 2 Examples of the ligand represented by the formula (I) can be selected from the chemical formulae listed in Group A below, but are not limited thereto.

[0247] [Group A] [ka]

[0248] In said Group A, R 300 ~R 302 each independently represents hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms and substituted or unsubstituted with a halogen, an aryl group having 6 to 30 carbon atoms and substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms, or a halogen; R 303 ~R 324are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a substituted or unsubstituted amino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, SF5, a trialkylsilyl group having a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a dialkylarylsilyl group having a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and an aryl group having 6 to 30 carbon atoms, or a triarylsilyl group having a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0249] The dopant according to one embodiment is an iridium complex, for example, represented by the following Formula 5-1 or 5-2.

[0250] [ka] [Chemical formula 5-1]

[0251] In the above chemical formula 5-1, R 101 ~R 116 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or -SiR 132 R 133 R 134 and R 132 ~R 134 are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, R 101 ~R 116 At least one of the functional groups is represented by the following chemical formula V-1: L 100is a monovalent anionic bidentate ligand that coordinates to iridium via a carbon or heteroatom lone electron pair. m19 and m20 each independently represent any one of integers of 0 to 3, and m19 and m20 each independently represent any one of integers of 1 to 3.

[0252] [ka] [Chemical formula V-1]

[0253] In the above chemical formula V-1, R 135 ~R 139 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or -SiR 132 R 133 R 134 and * means a moiety connected to a carbon atom.

[0254] [ka] [Chemical formula 5-2]

[0255] In the above chemical formula 5-2, R 101 ~R 117 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or -SiR 133 R 134 R 135 and R 133 ~R 135 are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, L 100is a monovalent anionic bidentate ligand that coordinates to iridium via a carbon or heteroatom lone electron pair. n1 and n2 are each independently any one of integers from 0 to 3, and n1+n2 is any one of integers from 1 to 3.

[0256] According to another embodiment, the dopant is a platinum complex, for example, represented by the following chemical formula Z-1:

[0257] [ka] [Chemical formula Z-1]

[0258] In the chemical formula Z-1, rings A, B, C, and D each independently represent a 5- or 6-membered carbocyclic or heterocyclic ring; R A , R B , R C , and R D each independently represents mono-, di-, tri- or tetra-substituted, or unsubstituted; L B , L C , and L D are each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO, CRR′, SiRR′, GeRR′, and combinations thereof; If nA is 1, L E is selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO, CRR′, SiRR′, GeRR′, and combinations thereof; when nA is 0, L E does not exist, R A , R B , R C , R D, R, and R' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; A , R B , R C , R D , R, and R' are optionally joined to form a ring; X B , X C , X D , and X E are each independently selected from the group consisting of carbon and nitrogen; Q 1 , Q 2 , Q 3 , and Q 4 indicates an oxygen or a direct bond, respectively.

[0259] The platinum complex is represented by, for example, the following chemical formula 6-1 or 6-1.

[0260] [ka] [Chemical formula 6-1]

[0261] [ka] [Chemical formula 6-2]

[0262] In the above Chemical Formula 6-1 and Chemical Formula 6-2, X 100 are O, S and NR 132 is selected from R 118 ~R 132are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or -SiR 133 R 134 R 135 and R 133 ~R 135 are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, R 118 ~R 132 At least one of the groups is -SiR 133 R 134 R 135 or a tert-butyl group, R 133 ~R 135 are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0263] An organic optoelectronic device to which the above-mentioned compound for an organic optoelectronic device or composition for an organic optoelectronic device is applied will be described below.

[0264] The organic optoelectronic element is not particularly limited as long as it is an element capable of converting electrical energy and light energy into each other, and examples thereof include organic photoelectric elements, organic light-emitting elements, organic solar cells, and organic photosensitive drums.

[0265] Here, an organic light-emitting element, which is an example of an organic optoelectronic element, will be described with reference to the drawings.

[0266] FIG. 1 is a cross-sectional view illustrating an organic light emitting device according to an embodiment.

[0267] Referring to FIG. 1, an organic light emitting device 100 according to one embodiment includes a positive electrode 120 and a negative electrode 110 facing each other, and an organic layer 105 located between the positive electrode 120 and the negative electrode 110 .

[0268] The positive electrode 120 is made of a conductor with a high work function to facilitate hole injection, such as a metal, metal oxide, and / or conductive polymer. Examples of the positive electrode 120 include, but are not limited to, metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO and Al or SnO and Sb; and conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyethylenedioxythiophene: PEDOT), polypyrrole, and polyaniline.

[0269] The negative electrode 110 is made of a conductor with a low work function, such as a metal, a metal oxide, and / or a conductive polymer, to facilitate electron injection. Examples of the negative electrode 110 include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, and barium, or alloys thereof; and multilayer structures such as LiF / Al, LiO / Al, LiF / Ca, and BaF / Ca.

[0270] The organic layer 105 can include the organic optoelectronic compound or composition described above.

[0271] The organic layer 105 includes a light-emitting layer 130, which may include the above-described compound or composition for an organic optoelectronic device.

[0272] The organic optoelectronic device composition further comprising a dopant can be, for example, a green-emitting composition.

[0273] The light-emitting layer 130 can include, for example, each of the above-mentioned compounds for organic optoelectronic devices as a phosphorescent host.

[0274] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0275] The charge transport region can be, for example, a hole transport region 140 .

[0276] The hole transport region 140 can further enhance hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and can block electrons.

[0277] Specifically, the hole transport region 140 may include a hole transport layer between the positive electrode 120 and the light-emitting layer 130, and a hole transport auxiliary layer between the light-emitting layer 130 and the hole transport layer, and at least one of the compounds listed in Group B below may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0278] [Group B] [ka]

[0279] [ka]

[0280] [ka]

[0281] [ka]

[0282] [ka]

[0283] [ka]

[0284]

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[0285]

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[0286]

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[0287]

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[0288]

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[0289]

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[0290]

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[0291]

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[0292]

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[0293]

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[0294]

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[0295]

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[0296]

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[0297]

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[0298]

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[0299]

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[0306] [ka]

[0307] [ka]

[0308] [ka]

[0309] [ka]

[0310] [ka] (Dn means the number of deuterium atoms substituted, and indicates a structure with one or more deuterium atoms substituted.)

[0311] In addition to the compounds described above, the hole transport region 140 may also use known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc., or compounds with similar structures.

[0312] The charge transport region can also be, for example, an electron transport region 150 .

[0313] The electron transport region 150 can further enhance electron injection and / or electron mobility between the anode 110 and the light-emitting layer 130 and block holes.

[0314] Specifically, the electron transport region 150 may include an electron transport layer between the negative electrode 110 and the light-emitting layer 130, and an electron transport auxiliary layer between the light-emitting layer 130 and the electron transport layer, and at least one of the compounds listed in Group C below may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0315] [Group C] [ka]

[0316] [ka]

[0317] [ka]

[0318] [ka]

[0319] [ka]

[0320] [ka]

[0321] [ka]

[0322] [ka]

[0323] [ka]

[0324] [ka]

[0325] [ka]

[0326] [ka]

[0327] [ka]

[0328] [ka]

[0329] [ka]

[0330] [ka]

[0331] [ka]

[0332] One embodiment may be an organic light-emitting device including a light-emitting layer as the organic layer.

[0333] Another embodiment can be an organic light emitting device that includes an emissive layer and a hole transport region as organic layers.

[0334] Yet another embodiment can be an organic light-emitting device that includes, as organic layers, an emissive layer and an electron transport region.

[0335] As shown in FIG. 1, the organic light emitting device according to an embodiment of the present invention may include a hole transport region 140 and an electron transport region 150 in addition to the light emitting layer 130 as the organic layer 105 .

[0336] Meanwhile, the organic light emitting device may further include an electron injection layer (not shown) and a hole injection layer (not shown) as the organic layer in addition to the light emitting layer.

[0337] The organic light emitting device 100 can be manufactured by forming an anode or cathode on a substrate, forming an organic layer using a dry film formation method such as vacuum evaporation, sputtering, plasma plating, or ion plating, and then forming an anode or cathode thereon.

[0338] The above-described organic light emitting device can be applied to an organic light emitting display device.

[0339] The above-described embodiments will be described in more detail with reference to the following examples, which are provided for illustrative purposes only and are not intended to limit the scope of the invention.

[0340] Unless otherwise specified, the starting materials and reactants used in the following examples and synthesis examples were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry, or P&H Tech, or synthesized by known methods. [Example]

[0341] (Manufacturing compounds for organic photoelectron devices) Synthesis Example 1: Synthesis of Compound 9

[0342] [Reaction Scheme 1] [ka]

[0343] Step 1: Synthesis of intermediate int-01 2-Bromo-1-fluoro-3-iodobenzene (50.0 g, 166.2 mmol), phenylboronic acid (22.3 g, 182.8 mmol), K2CO3 (45.9 g, 332.4 mmol), and Pd(PPh3)4 (9.6 g, 8.3 mmol) were placed in a round-bottom flask and dissolved in THF (350 mL) and distilled water (160 mL). The mixture was then refluxed at 70 °C for 6 hours. After the reaction was complete, the aqueous layer was removed and the mixture was purified by column chromatography (Hexane:DCM (30%)) to obtain intermediate int-01 (28.9 g, 69%).

[0344] Step 2: Synthesis of intermediate int-02 Intermediate int-01 (21.7 g, 105.0 mmol), Bis(pinacolato)diboron (35.1 g, 138.1 mmol), potassium acetate (22.6 g, 230.2 mmol), and Pd(dppf)Cl2 (4.7 g, 5.8 mmol) were placed in a round-bottom flask and dissolved in 380 mL of xylene. The mixture was refluxed and stirred at 140 °C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered to remove salts, and extracted with excess DCM and distilled water. Column chromatography (Hexane:DCM (30% to 50%)) yielded 20.6 g (60%) of intermediate int-02.

[0345] Step 3: Synthesis of intermediate int-04 Intermediate int-02 (20.6 g, 69.1 mmol), intermediate int-03 (20.6 g, 57.6 mmol), K2CO3 (15.9 g, 115.2 mmol), and Pd(PPh3)4 (3.33 g, 2.88 mmol) were placed in a round-bottom flask and dissolved in THF (300 mL) and distilled water (60 mL). The mixture was then refluxed at 70 °C for 6 hours. After the reaction was completed, the aqueous layer was removed and the mixture was purified by column chromatography (Hexane:DCM (30%)) to obtain intermediate int-04 (19.9 g, 70%).

[0346] Step 4: Synthesis of Compound 9 Intermediate int-04 (19.9 g, 40.3 mmol), 2-Phenyl-9H-carbazole (19.6 g, 80.6 mmol), and KPO (17.1 g, 80.6 mmol) were placed in a round-bottom flask and dissolved in DMF (130 ml). The mixture was then refluxed and stirred at 150 °C for 4 hours. After the reaction was complete, the reactant was slowly added dropwise to excess water to precipitate a solid. The solid was then filtered and separated by column chromatography (Hexane:DCM (30%)) to obtain 17.9 g (62%) of compound 9.

[0347] Synthesis Example 2: Synthesis of Compound 30 [Reaction Scheme 2] [ka]

[0348] Step 1: Synthesis of intermediate int-05 2-(4-Biphenylyl)-4,6-dichloro-1,3,5-triazine (35.0 g, 115.8 mmol), dibenzothiophene-4-boronic acid (25.1 g, 110.0 mmol), K2CO3 (32.0 g, 231.7 mmol), and Pd(dppf)Cl2 (4.73 g, 5.79 mmol) were dissolved in toluene (400 mL) and distilled water (120 mL) in a round-bottom flask and stirred at 60 °C for 6 h. After the reaction was complete, the aqueous layer was separated using a separatory funnel and purified by column chromatography (Hexane:DCM (35%)) to obtain intermediate int-05 (27.7 g, 56%).

[0349] Step 2: Synthesis of intermediate int-06 Intermediate int-06 (27.7 g, 61.6 mmol), intermediate int-02 (19.3 g, 64.6 mmol), K2CO3 (17.0 g, 123.1 mmol), and Pd(PPh3)4 (3.56 g, 3.08 mmol) were placed in a round-bottom flask and dissolved in THF (200 mL) and distilled water (60 mL). The mixture was then refluxed at 70 °C for 6 hours. After the reaction was complete, the aqueous layer was removed and the mixture was purified by column chromatography (Hexane:DCM (30%)) to obtain 26.5 g (70%) of intermediate int-06.

[0350] Step 3: Synthesis of compound 30 Intermediate int-06 (14.6 g, 24.9 mmol), 9H-carbazole (5.0 g, 29.9 mmol), and KPO (10.6 g, 49.9 mmol) were placed in a round-bottom flask and dissolved in DMF (100 mL). The mixture was refluxed at 150 °C for 4 hours with stirring. After the reaction was complete, the reactant was slowly added dropwise to excess water to precipitate a solid. The solid was filtered and recrystallized in Toluene to give compound 30 (16.1 g, 88%).

[0351] Synthesis Example 3: Synthesis of Compound B-136

[0352] [ka]

[0353] Compound B-136 was synthesized with reference to the synthesis method of patent EP3034581.

[0354] Comparative Synthesis Example 1: Synthesis of Compound Host 1 [Reaction Scheme 3]

[0355] [ka]

[0356] Step 1: Synthesis of intermediate int-09 Intermediate int-09 (24.4 g, 65%) was obtained by synthesis in the same manner as in step 1 of Synthesis Example 1 using 2,4-Dichloro-6-phenyl-1,3,5-triazine (25.0 g, 110.6 mmol), 2-dibenzofuranylboronic acid (22.3 g, 105.1 mmol), K2CO3 (30.6 g, 221.2 mmol), and Pd(dppf)Cl2 (4.52 g, 5.53 mmol).

[0357] Step 2: Synthesis of intermediate int-10 Intermediate int-9 (24.4 g, 68.2 mmol), 2-Fluorophenylboronic acid (11.5 g, 81.8 mmol), K2CO3 (18.9 g, 136.4 mmol), and Pd(PPh3)4 (3.94 g, 3.41 mmol) were placed in a round-bottom flask and dissolved in THF (270 mL) and distilled water (70 mL). The mixture was then refluxed at 70 °C for 6 hours. After the reaction was complete, the aqueous layer was removed and the mixture was purified by column chromatography (Hexane:DCM (30%)) to afford intermediate int-10 (17.1 g, 60%).

[0358] Step 3: Synthesis of Compound Host 1 Intermediate int-10 (17.1 g, 41.0 mmol), 9H-Carbazole (13.7 g, 81.9 mmol), and KPO (17.4 g, 81.9 mmol) were placed in a round-bottom flask and dissolved in DMF (150 ml). The mixture was then refluxed and stirred at 150 °C for 4 hours. After the reaction was complete, the reactants were slowly added dropwise to excess water to precipitate a solid. The solid obtained after filtration was recrystallized with monochlorobenzene to obtain 18.5 g (80%) of compound Host 1.

[0359] Comparative Synthesis Example 2: Synthesis of Compound Host 2

[0360] [ka]

[0361] Compound Host 2 was synthesized according to the synthesis method of patent KR2017-0131398.

[0362] Comparative Synthesis Example 3: Synthesis of Compound Host 3

[0363] [ka]

[0364] Compound Host 3 was synthesized by referring to the synthesis method of patent WO2019-053049.

[0365] Example 1 A glass substrate coated with a thin film of ITO (indium tin oxide) was ultrasonically cleaned with distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, and then dried. The substrate was then transferred to a plasma cleaning device and cleaned using oxygen plasma for 10 minutes. The substrate was then transferred to a vacuum deposition device. Using the prepared ITO transparent electrode as the anode, Compound A doped with 3% NDP-9 (Novaled) was vacuum-deposited on the top of the ITO substrate to form a 100 Å thick hole injection layer. Compound A was then vacuum-deposited on the top of the hole injection layer to form a 1350 Å thick hole transport layer. Compound B was then vacuum-deposited on the top of the hole transport layer to form a 350 Å thick hole transport auxiliary layer. A 350 Å thick emissive layer was then vacuum-deposited on the top of the hole transport auxiliary layer using Compound 9 (synthesized in Synthesis Example 1) as the host and doped with 9 wt% PhGD as the dopant. The ratios are listed separately in the following examples and comparative examples. Next, compound C was deposited on the light-emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compound D and Liq were simultaneously vacuum-deposited in a 1:1 weight ratio to form an electron transport layer to a thickness of 300 Å. LiQ 15 Å and Al 1200 Å were sequentially vacuum-deposited on the electron transport layer to form an anode, thereby fabricating an organic light-emitting device.

[0366] The structure was ITO / compound A (3% NDP-9 doping, 100 Å) / compound A (1350 Å) / compound B (350 Å) / EML [compound 9 (91 wt%): PhGD (9 wt%)] (350 Å) / compound C (50 Å) / compound D: LiQ (300 Å) / LiQ (15 Å) / Al (1200 Å).

[0367] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine Compound B: N-[4-(4-Dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine Compound C:2,4-Diphenyl-6-(4',5',6'-triphenyl[1,1':2',1'':3'',1''':3''',1''''-quinquephenyl]-3''''-yl)-1,3,5-triazine Compound D: 2-[4-[4-(4'-Cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0368] [ka] [PhGD]

[0369] Example 2 and Comparative Examples 1 to 3 An organic light emitting device was fabricated in the same manner as in Example 1, except that the composition was changed as shown in Table 1 below.

[0370] Example 3 A glass substrate coated with a thin film of ITO (indium tin oxide) was ultrasonically cleaned with distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, and then dried. The substrate was then transferred to a plasma cleaning device and cleaned using oxygen plasma for 10 minutes. The substrate was then transferred to a vacuum deposition device. Using the prepared ITO transparent electrode as the anode, Compound A doped with 3% NDP-9 (Novaled) was vacuum-deposited on the top of the ITO substrate to form a 100 Å thick hole injection layer. Compound A was then deposited on the hole injection layer to a thickness of 1350 Å to form a hole transport layer. Compound E was then deposited on the hole transport layer to a thickness of 350 Å to form a hole transport auxiliary layer. Compound 9 (synthesized in Synthesis Example 1) and compound B-136 (synthesized in Synthesis Example 3) were simultaneously used as hosts on the hole transport assisting layer, and doped with 9 wt% PhGD as a dopant by vacuum deposition to form a 380 Å thick light-emitting layer. Compound 1 and compound B-136 were used in a weight ratio of 3:7. Next, compound F was deposited on the light-emitting layer to a thickness of 50 Å to form an electron transport assisting layer, and compound G and LiQ were simultaneously vacuum-deposited in a weight ratio of 1:1 to form a 300 Å thick electron transport layer. LiQ (15 Å) and Al (1200 Å) were sequentially vacuum-deposited on the electron transporting layer to form a cathode, thereby fabricating an organic light-emitting device.

[0371] The structure was ITO / Compound A (3% NDP-9 doping, 100 Å) / Compound A (1350 Å) / Compound E (350 Å) / EML [host (Compound 9:Compound B-136):dopant (PhGD) = 91 wt%:9 wt%] (380 Å) / Compound F (50 Å) / Compound G:LiQ (300 Å) / LiQ (15 Å) / Al (1200 Å).

[0372] Compound E: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluorene)-2-amine Compound F:2-[3'-(9,9-Dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine Compound G: 2-[4-[4-(4'-Cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0373] Example 4 and Comparative Examples 4 to 6 An organic light emitting device was fabricated in the same manner as in Example 3, except that the composition was changed as shown in Table 2 below.

[0374] evaluation The driving voltage and luminous efficiency of the organic light-emitting devices according to Examples 1 to 4 and Comparative Examples 1 to 6 were evaluated.

[0375] The specific measurement method is as follows, and the results are shown in Tables 1 and 2.

[0376] (1) Measurement of changes in current density in response to voltage changes The voltage of the fabricated organic light emitting device was increased from 0 V to 10 V, and the current flowing through the unit element was measured using a current-voltage meter (Keithley 2400). The measured current was divided by the area to obtain the results.

[0377] (2) Measurement of luminance change according to voltage change The voltage of the fabricated organic light emitting device was increased from 0V to 10V, and the luminance was measured using a luminance meter (Minolta Cs-1000A) to obtain the results.

[0378] (3) Luminous efficiency measurement Using the luminance, current density, and voltage measured from (1) and (2) above, the same current density (10 mA / cm 2 The current efficiency (cd / A) of the

[0379] The luminous efficiency values ​​of Examples 1 and 2 and Comparative Examples 1 to 3 were calculated as relative values ​​based on Comparative Example 1, and are shown in Table 1 below.

[0380] The luminous efficiency values ​​of Examples 3 and 4 and Comparative Examples 4 to 6 were calculated as relative values ​​based on Comparative Example 4, and are shown in Table 2 below.

[0381] (4) Drive voltage measurement 15 mA / cm using a current-voltage meter (Keithley 2400) 2 The driving voltage of each element was measured and the results were obtained.

[0382] The driving voltages of Examples 1 and 2 and Comparative Examples 1 to 3 were calculated as relative values ​​based on Comparative Example 1, and are shown in Table 1 below.

[0383] The driving voltages of Examples 3 and 4 and Comparative Examples 4 to 6 were calculated as relative values ​​based on Comparative Example 4, and are shown in Table 2 below.

[0384] [Table 1]

[0385] [Table 2]

[0386] Referring to Tables 1 and 2, it can be seen that the organic light emitting devices according to Examples 1 to 4 have significantly improved driving voltage and luminous efficiency compared to the organic light emitting devices according to Comparative Examples 1 to 6. [Explanation of symbols]

[0387] 100 Organic light-emitting element 105 Organic layer 110 Negative electrode 120 positive electrode 130 Light-emitting layer 140 Hole transport region 150 Electron transport area

Claims

1. A compound for an organic optoelectronic device represented by the following chemical formula 1: 【Chemistry 1】 [Chemical formula 1] In the above Chemical Formula 1, X １ is O or S, R １ ~R １３ , R １７ and R １８ each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms; R １４ ~R １６ are each independently hydrogen or deuterium, Ar １ is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, m1 is one of the integers 1 to 3; m2 is one of the integers from 1 to 4.

2. The compound for an organic optoelectronic device according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4: 【Chemistry 2】 [Chemical formula 1-1] [Chemical formula 1-2] 【Transformation 3】 [Chemical formula 1-3] [Chemical formula 1-4] In the chemical formulas 1-1 to 1-4, R １ ~R １８ , Ar １ , m1 and m2 are as defined in claim 1.

3. The Ar １ 2. The compound for an organic optoelectronic device according to claim 1, wherein is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

4. The R １ ~R １３ , R １７ and R １８ 2. The compound for an organic optoelectronic device according to claim 1, wherein each of the is independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

5. The compound for organic optoelectronic devices according to claim 1, which is one selected from the compounds listed in Group 1 below: [Group 1] 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 。

6. comprising a first compound and a second compound; The first compound is the compound for an organic optoelectronic device according to claim 1 , The second compound is a composition for an organic optoelectronic device represented by the following Chemical Formula 2; a combination of the following Chemical Formula 3 and Chemical Formula 4; or the following Chemical Formula 5: [Chemistry 18] [Chemical formula 2] In the above Chemical Formula 2, R １９ ~R ２３ each independently represents hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Ar ２ and Ar ３ each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, L １ and L ２ each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, m3, m6, and m7 each independently represent an integer from 1 to 4; m4 and m5 each independently represent an integer from 1 to 3; n is an integer from 0 to 2; 【Chemistry 19】 [Chemical formula 3] [Chemical formula 4] In Chemical Formula 3 and Chemical Formula 4, a in Chemical Formula 3 １ ＊ ~a ４ ＊ are each independently a linking carbon (C) or C-L ａ -R ａ and a in Chemical Formula 3 １ ＊ ~a ４ ＊ The adjacent two of the groups in formula 4 are ＊ and L ａ , L ４ and L ５ each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R ａ , R ２４ and R ２５ each independently represents hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Ar ４ and Ar ５ each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, m8 and m9 each independently represent an integer from 1 to 4; 【Chemistry 20】 [Chemical formula 5] In the above Chemical Formula 5, L ６ each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R ２６ ~R ２９ each independently represents hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Ar ６ is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, m10, m12, and m13 each independently represent an integer from 1 to 4; m11 is one of integers from 1 to 3.

7. The composition for organic optoelectronic devices according to claim 6, wherein the chemical formula 2 is represented by the following chemical formula 2-8: 【Chemistry 21】 [Chemical formula 2-8] In the above chemical formula 2-8, R １９ ~R ２２ are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; m3 and m6 each independently represent an integer from 1 to 4; m4 and m5 each independently represent an integer from 1 to 3; L １ -Ar ２ and L ２ -Ar ３ are each independently one of the substituents listed in Group I below, [Group I] 【Chemistry 22】 In Group I, R ３０ ~R ３４ each independently represents hydrogen, deuterium, a cyano group, an arylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms, m14 is one of integers from 1 to 5; m15 is an integer from 1 to 4; m16 is an integer from 1 to 3; m17 is an integer of 1 or 2, m18 is one of the integers from 1 to 7; ＊ is the connection point.

8. The composition for organic optoelectronic devices according to claim 6, wherein the combination of Chemical Formula 3 and Chemical Formula 4 is represented by the following Chemical Formula 3C: 【Chemistry 23】 [Chemical formula 3C] In the above Chemical Formula 3C, L ａ３ and L ａ４ is a single bond, R ２４ , R ２５ , R ａ３ and R ａ４ are each independently hydrogen, deuterium, or an aryl group having 6 to 12 carbon atoms; m8 and m9 each independently represent an integer from 1 to 4; L ４ -Ar ４ and L ５ -Ar ５ are each independently one of the substituents listed in Group I below, [Group I] 【Chemistry 24】 In Group I, R ３０ ~R ３４ each independently represents hydrogen, deuterium, a cyano group, an arylsilyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms, m14 is one of integers from 1 to 5; m15 is an integer from 1 to 4; m16 is an integer from 1 to 3; m17 is an integer of 1 or 2, m18 is one of the integers from 1 to 7; ＊ is the connection point.

9. A positive electrode and a negative electrode facing each other, at least one organic layer located between the positive electrode and the negative electrode; The organic layer comprises the compound for an organic optoelectronic device according to any one of claims 1 to 5, or An organic optoelectronic device comprising the composition for organic optoelectronic devices according to any one of claims 6 to 8.

10. the organic layer includes an emitting layer, The organic optoelectronic device according to claim 9 , wherein the light-emitting layer comprises the compound for an organic optoelectronic device or the composition for an organic optoelectronic device.

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

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