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

Abstract

The present invention provides a compound for an organic optoelectronic device that can realize a highly efficient and low-driving organic optoelectronic device, a composition for an organic optoelectronic device that includes the same, an organic optoelectronic device, and a display device. According to one embodiment, there is provided a compound for an organic optoelectronic device represented by Chemical Formula 1: 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 optoelectronic 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 principle: 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 recently been attracting attention due to the increasing demand for flat panel display devices. OLEDs are devices that convert electrical energy into light, and their performance is greatly affected by the organic materials located between the electrodes. Summary of the Invention [Problem to be solved by the invention]

[0006] One embodiment provides a compound for an organic optoelectronic device that can realize a highly efficient and low driving organic optoelectronic device.

[0007] Another embodiment provides an organic optoelectronic composition comprising an organic optoelectronic compound.

[0008] Yet another embodiment provides an organic optoelectronic device comprising the compound for an organic optoelectronic device or the composition for an organic optoelectronic device.

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

[0010] According to one embodiment, there is provided a compound represented by the following Chemical Formula 1:

[0011] [Chemical formula 1] [ka] In the above chemical formula 1, R 1 is 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 6 to 20 carbon atoms, Z 1 ~Z 3 are each independently N or CR a and Z 1 ~Z 3 at least two of are N, Z 4 ~Z 6 are each independently N or CR b and Z 4 ~Z 6 at least two of are N, R a , R b , R 2 , and R 3 each independently represents hydrogen, deuterium, a cyano group, a halogen 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, L 1 ~L 4 each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, Ar 1 ~Ar 4 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, m1 and m2 each independently represent an integer from 1 to 4; m3 is an integer between 1 and 3.

[0012] According to another embodiment, there is provided a composition for an organic optoelectronic device comprising a first compound and a second compound.

[0013] The first compound is the compound for an organic optoelectronic device described above, and the second compound can be 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.

[0014] [Chemical formula 2] [ka] In the above chemical formula 2, R 4 ~R 8 and Ar 7 ~Ar 10 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 5 and Ar 6 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 5 and L 6each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, m4, m7, and m8 each independently represent an integer from 1 to 4; m5 and m6 each independently represent an integer of 1 to 3; n is an integer from 0 to 2.

[0015] [Chemical formula 3] [Chemical formula 4] [ka] In the above chemical formula 3 and chemical formula 4, a1 in Chemical Formula 3 * ~a4 * are each independently a bond carbon (C) or CL a -R c and a1 in Chemical Formula 3 * ~a4 * two adjacent ones of are bonded to * in chemical formula 4, L a , L 7 , and L 8 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R c , Ar 13 , Ar 14 , R 9 , and R 10 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 11 and Ar 12 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, m9 and m10 each independently represent an integer of 1 to 4.

[0016] [Chemical formula 5] [ka] In the above chemical formula 5, L 10 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R 16 ~R 28 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 13 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, m16 is an integer between 1 and 3.

[0017] According to another embodiment, there is provided an organic optoelectronic device including 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 includes a compound for an organic optoelectronic device or a composition for an organic optoelectronic device.

[0018] According to another embodiment, there is provided a display device including an organic optoelectronic device. [Effects of the Invention]

[0019] It is possible to realize a low-driving, highly efficient organic optoelectronic device. [Brief explanation of the drawings]

[0020] [Figure 1] 1 is a cross-sectional view illustrating an organic light-emitting device according to an embodiment. DETAILED DESCRIPTION OF THE INVENTION

[0021] DETAILED DESCRIPTION OF THE INVENTION The following detailed description of the present invention is provided by way of example only and is not intended to limit the scope of the present invention, which is defined solely by the scope of the claims that follow.

[0022] Unless otherwise defined, the term "substituted" used herein means that at least one hydrogen atom in a substituent or compound is 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.

[0023] 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 in a substituent or compound is replaced 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.

[0024] As used herein, "unsubstituted" means that the hydrogen atom is not replaced with another substituent and remains as a hydrogen atom.

[0025] As used herein, "hydrogen substitution (-H)" can include "deuterium substitution (-D)" or "tritium substitution (-T)."

[0026] 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.

[0027] 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 moieties have p-orbitals and these p-orbitals form conjugation, such as a phenyl group or naphthyl group; a form in which two or more hydrocarbon aromatic moieties are bonded 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.

[0028] Aryl groups include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings sharing adjacent pairs of carbon atoms) functional groups.

[0029] As used herein, the term "heterocyclic group" is a generic term that includes heteroaryl groups and refers to a group containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si in place of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. When a heterocyclic group is a fused ring, the entire heterocyclic group or each ring may contain one or more heteroatoms.

[0030] 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 can be directly bonded through a sigma bond, or, if the heteroaryl group contains two or more rings, the two or more rings can be fused together. If the heteroaryl group is a fused ring, each ring can contain 1 to 3 heteroatoms.

[0031] 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 ferrylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0032] More specifically, the substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms includes 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 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 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 thereto.

[0033] 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 along the HOMO level, facilitating the injection of holes formed in the cathode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the cathode, and the movement of holes in the light-emitting layer.

[0034] In addition, the electronic properties refer to the property of being able to receive electrons when an electric field is applied, and refer to the property of having conduction properties along the LUMO level, facilitating the injection of electrons formed in the anode into the light-emitting layer, the movement of electrons formed in the light-emitting layer to the anode, and the movement of electrons in the light-emitting layer.

[0035] Hereinafter, a compound for an organic optoelectronic device according to one embodiment will be described.

[0036] The compound for an organic optoelectronic device according to one embodiment is represented by the following Chemical Formula 1.

[0037] [Chemical formula 1] [ka] In the above chemical formula 1, R 1 is 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 6 to 20 carbon atoms, Z 1 ~Z 3 are each independently N or CR a and Z 1 ~Z 3 at least two of are N, Z 4 ~Z 6 are each independently N or CR b and Z 4 ~Z 6 at least two of are N, R a , R b , R 2 , and R 3 each independently represents hydrogen, deuterium, a cyano group, a halogen 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, L 1 ~L 4each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, Ar 1 ~Ar 4 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, m1 and m2 each independently represent an integer from 1 to 4; m3 is an integer between 1 and 3.

[0038] The compound for organic optoelectronic devices represented by Chemical Formula 1 has a structure in which nitrogen-containing six-membered rings are simultaneously substituted in the N-direction (direction 9) of carbazole and in the phenyl direction (directions 1 to 8) of carbazole with carbazole at the center.

[0039] The N-direction (9-direction) substituent of carbazole is bonded through ortho-phenylene, which adjusts the LUMO energy level to shallow, thereby improving the luminous efficiency of the device to which it is applied.

[0040] In addition, the electron mobility increases as a result of the nitrogen-containing six-membered ring being additionally substituted in the phenyl direction (1st to 8th directions) of the carbazole, thereby enabling the driving voltage of the device to which this is applied to be reduced.

[0041] That is, a device using the compound for an organic optoelectronic device represented by Chemical Formula 1 can simultaneously achieve low driving and high efficiency characteristics.

[0042] As an example, R 1 may be a substituent other than an electron withdrawing group, for example, R 1 may be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0043] The electron-withdrawing group may be, for example, a halogen atom such as F, Cl, I, or Br, a halogenated alkyl compound formed from these, or a cyano group.

[0044] R 1 When is an electron withdrawing group, the LUMO energy level cannot be adjusted to a shallow level, and in this case, the desired effect cannot be achieved.

[0045] In a specific embodiment, R 1 may be hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms.

[0046] As an example, R 2 and R 3 may each independently be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0047] As a specific example, R 2 and R 3 may each independently be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0048] For example, R 2 and R 3 may each independently be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0049] As an example, L 1 ~L 4 may each independently be a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0050] As a specific example, L 1 ~L 4 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0051] As an example, Ar 1 ~Ar 4 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.

[0052] As a specific example, Ar 1 ~Ar 4 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0053] For example, Chemical Formula 1 can be represented by any one of the following Chemical Formulas 1A to 1D depending on the specific substitution position of the nitrogen-containing 6-membered ring substituted toward the phenyl side of carbazole.

[0054] [Chemical formula 1A] [Chemical formula 1B] [ka] [Chemical formula 1C] [Chemical formula 1D] [ka] In the above Chemical Formula 1A to Chemical Formula 1D, Z1 ~Z 6 , R 1 ~R 3 , L 1 ~L 4 , Ar 1 ~Ar 4 , and m1 to m3 are as described above.

[0055] As a specific example, Chemical Formula 1 can be represented by Chemical Formula 1B or Chemical Formula 1D.

[0056] For example, Chemical Formula 1 can be represented by any one of Chemical Formulas 1-1 to 1-9 below.

[0057] [Chemical formula 1-1] [Chemical formula 1-2] [ka] [Chemical formula 1-3] [Chemical formula 1-4] [ka] [Chemical formula 1-5] [Chemical formula 1-6] [ka] [Chemical formula 1-7] [Chemical formula 1-8] [ka] [Chemical formula 1-9] [ka] In the above chemical formulas 1-1 to 1-9, R 1 ~R 3 , L 1 ~L 4 , Ar 1 ~Ar 4, and m1 to m3 are as described above.

[0058] As a specific example, Chemical Formula 1 can be represented by Chemical Formula 1-1.

[0059] As a more specific example, Chemical Formula 1 can be represented by the following Chemical Formula 1-B-1 or Chemical Formula 1-D-1.

[0060] [Chemical formula 1-B-1] [Chemical formula 1-D-1] [ka] In the above chemical formula 1-B-1 and chemical formula 1-D-1, R 1 ~R 3 , L 1 ~L 4 , Ar 1 ~Ar 4 , and m1 to m3 are as described above.

[0061] For example, the compound for an organic optoelectronic device represented by Chemical Formula 1 may be one selected from the compounds listed in Group 1 below, but is not limited thereto.

[0062] [Group 1] [A-1] [A-2] [A-3] [A-4] [A-5] [ka] [A-6] [A-7] [A-8] [A-9] [A-10] [ka] [A-11] [A-12] [A-13] [A-14] [ka] [A-15] [A-16] [A-17] [A-18] [ka] [A-19] [A-20] [A-21] [A-22] [ka] [A-23] [A-24] [A-25] [A-26] [ka] [A-27] [A-28] [A-29] [A-30] [ka] A composition for organic optoelectronic devices according to another embodiment includes a first compound and a second compound, wherein the first compound is the compound for organic optoelectronic devices described above, and the second compound can be represented by a combination of Chemical Formula 2, Chemical Formula 3, and Chemical Formula 4, or Chemical Formula 5 below.

[0063] [Chemical formula 2] [ka] In the above chemical formula 2, R 4 ~R 8 and Ar 7 ~Ar 10 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 5 and Ar 6each 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 5 and L 6 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, m4, m7, and m8 each independently represent an integer from 1 to 4; m5 and m6 each independently represent an integer of 1 to 3; n is an integer from 0 to 2.

[0064] [Chemical formula 3] [Chemical formula 4] [ka] In the above chemical formula 3 and chemical formula 4, a1 in Chemical Formula 3 * ~a4 * are each independently a bond carbon (C) or CL a -R c and a1 in Chemical Formula 3 * ~a4 * two adjacent ones of are bonded to * in chemical formula 4, L a , L 7 , and L 8 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R c , Ar 13 , Ar 14 , R 9 , and R 10 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 11 and Ar 12each 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, m9 and m10 each independently represent an integer of 1 to 4.

[0065] [Chemical formula 5] [ka] In the above chemical formula 5, L 10 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R 16 ~R 28 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 13 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, m16 is an integer between 1 and 3.

[0066] 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 the charge mobility and stability.

[0067] As an example, Ar in formula 2 5 and Ar 6 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 Chemical Formula 25 and L 6 each independently represents a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, R in Chemical Formula 2 4 ~R 8 and Ar 7 ~Ar 10 are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; n may be 0 or 1.

[0068] For example, "substituted" in Chemical Formula 2 means that at least one hydrogen atom is replaced 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.

[0069] For example, Ar in formula 2 5 and Ar 6 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.

[0070] In a specific embodiment of the present invention, Chemical Formula 2 can be represented by one of the following Chemical Formulas 2-1 to 2-15.

[0071] [Chemical formula 2-1] [Chemical formula 2-2] [Chemical formula 2-3] [ka] [Chemical formula 2-4] [Chemical formula 2-5] [Chemical formula 2-6] [ka] [Formula 2-7] [Formula 2-8] [Formula 2-9] [ka] [Formula 2-10] [Formula 2-11] [Formula 2-12] [ka] [Formula 2-13] [Formula 2-14] [Formula 2-15] [ka] In the above chemical formulas 2-1 to 2-15, R 4 ~R 8 and Ar 7 ~Ar 10 are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; 5 -Ar 5 and *-L 6 -Ar 6 may each independently be one of the substituents listed in Group I below.

[0072] [Group I] [ka] In Group I above, R 11 ~R 15 are each independently hydrogen, deuterium, a cyano group, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms, m11 is an integer from 1 to 5, m12 is an integer between 1 and 4, m13 is an integer between 1 and 3, m14 is an integer of 1 or 2, m15 is an integer between 1 and 7, * indicates the binding site.

[0073] In a specific embodiment of the present invention, the combination of Chemical Formula 3 and Chemical Formula 4 can be represented by any one of the following Chemical Formulas 3A, 3B, 3C, 3D, and 3E.

[0074] [Formula 3A] [Formula 3B] [Formula 3C] [ka] [Chemical formula 3D] [Chemical formula 3E] [ka] In the above chemical formulas 3A to 3E, Ar 11 , Ar 12 , L 7 , L 8 , Ar 13 , Ar 14 , R 9 , and R 10 is as mentioned above, L a1 ~L a4 is the aforementioned L 7 and L 8 As defined in R c1 ~R c4 is the aforementioned Ar 13 , Ar 14 , R 9 , and R 10 This is as defined above.

[0075] For example, Ar in formulas 3 and 4 11 and Ar 12 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; Rc1 ~R c4 , Ar 13 , Ar 14 , R 9 , and R 10 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.

[0076] In a specific embodiment of the present invention, *-L in Formulas 3 and 4 7 -Ar 11 and *-L 8 -Ar 12 can each independently be selected from the substituents listed in Group I.

[0077] In one embodiment, R c1 ~R c4 , Ar 13 , Ar 14 , R 9 , and R 10 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.

[0078] For example, R c1 ~R c4 , Ar 13 , Ar 14 , R 9 , and R 10 each independently may be hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group; In a specific embodiment, R c1 ~R c4 , Ar 13 , Ar 14 , R 9 , and R 10may each independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0079] In a specific embodiment of the present invention, Chemical Formula 5 can be represented by any one of the following Chemical Formulas 5-1 to 5-4.

[0080] [Chemical formula 5-1] [Chemical formula 5-2] [ka] [Chemical formula 5-3] [Chemical formula 5-4] [ka] In the above chemical formulas 5-1 to 5-4, L 10 , R 16 ~R 28 , Ar 13 , and m16 are as described above.

[0081] For example, Ar in Formula 5 13 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 16 ~R 28 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.

[0082] In a specific embodiment of the present invention, the second compound can be represented by Formula 2-8, and Ar in Formula 2-8 5 and Ar 6 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 5 and L 6 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and Ar 7 ~Ar 10 and R 4 ~R 7 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.

[0083] For example, Ar in formula 2-8 7 ~Ar 10 and R 4 ~R 7 are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; 5 -Ar 5 and *-L 6 -Ar 6 may each independently be one of the substituents listed in Group I.

[0084] In another specific embodiment of the present invention, the second compound can be represented by Formula 3C, and L of Formula 3C a3 and L a4 is a single bond, and L 7 and L 8 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, and Ar 13 , Ar 14 , R 9 , R10 , R c3 , and R c4 are hydrogen, deuterium, or a phenyl group, and Ar 11 and Ar 12 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.

[0085] For example, L in formula 3C c3 and L c4 is a single bond, and Ar 13 , Ar 14 , R 9 , R 10 , R c3 , and R c4 are each independently hydrogen, deuterium, or an aryl group having 6 to 12 carbon atoms, and *-L 7 -Ar 11 and *-L 8 -Ar 12 may each independently be one of the substituents listed in Group I.

[0086] In another specific embodiment of the present invention, the second compound can be represented by Formula 5-2 or Formula 5-3, and L 10 -Ar 13 can be selected from the substituents listed in Group I.

[0087] For example, R 16 ~R 28 may each independently be hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group.

[0088] 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.

[0089] [Group 2] [B-1] [B-2] [B-3] [B-4] [B-5]

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[0090] [B-153][B-154][B-155][B-156][B-157] [ka] [B-158][B-159][B-160][B-161][B-162] [ka] [B-163][B-164][B-165][B-166][B-167] [ka] [B-168][B-169][B-170][B-171][B-172] [ka] [B-173][B-174][B-175][B-176][B-177] [ka] [B-178][B-179][B-180][B-181][B-182] [ka] [B-183][B-184][B-185][B-186][B-187] [ka] [B-188][B-189][B-190][B-191][B-192] [ka] [B-193][B-194][B-195][B-196][B-197] [ka] (Dn means the number of deuterium atoms substituted, and indicates a structure in which one or more deuterium atoms have been substituted.) The most specific structures of Compounds B-153 to B-197 in Group 2 according to the deuterium substitution position and substitution rate are presented below as examples only, and are not intended to limit the scope of rights to compounds not presented below.

[0091] The scope of the present invention is determined by the claims. When deuterium is substituted, the compounds are not limited to those exemplified below, and the deuterium substitution position and deuterium substitution rate may include all variable ranges within the scope of Compounds B-1 to B-197.

[0092] [B-198][B-199][B-200] [ka] [B-201] [B-202] [B-203] [B-204] [ka] [B-205] [B-206] [B-207] [B-208] [ka] [B-209][B-210] [B-211] [B-212]

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[0093] [C-58] [C-59] [C-60] [C-61] [C-62] [ka] [C-63] [C-64] [C-65] [C-66] [C-67] [ka] [C-68] [C-69] [C-70] [C-71] [C-72] [ka] (Dn means the number of deuterium atoms substituted, and indicates a structure in which one or more deuterium atoms have been substituted.) [D-1] [D-2] [D-3] [D-4] [D-5] [ka] [D-6] [D-7] [D-8] [D-9] [D-10] [ka] [D-11] [D-12] [D-13] [D-14] [D-15] [ka] [D-16] [D-17] [D-18] [D-19] [D-20] [ka] [D-21] [D-22] [D-23] [D-24] [D-25] [ka] [D-26] [D-27] [D-28] [D-29] [D-30] [ka] [D-31] [D-32] [D-33] [D-34] [D-35] [ka] [D-36] [D-37] [D-38] [D-39] [D-40] [ka] [D-41] [D-42] [D-43] [D-44] [D-45] [ka] [D-46] [D-47] [D-48] [D-49] [D-50] [ka] [D-51] [D-52] [D-53] [D-54] [D-55] [ka] [D-56] [D-57] [D-58] [D-59] [D-60] [ka] Additionally, examples of compounds D-1 to D-60 listed in Group 2 in which at least one hydrogen atom is replaced with deuterium are given below, but the present invention is not limited thereto.

[0094] [D-61] [D-62] [D-63] [D-64] [D-65] [ka] [D-66] [D-67] [D-68] [D-69] [D-70] [Chemistry] [D-71] [D-72] [D-73] [D-74] [D-75] [Chemistry] [D-76] [D-77] [D-78] [D-79] [D-80] [Chemistry] [D-81] [D-82] [D-83] [D-84] [D-85] [Chemistry] [D-86] [D-87] [D-88] [D-89] [D-90] [Chemistry] <所 [D-91] [D-92] [D-93] [D-94] [D-95] [Chemistry] [D-96] [D-97] [D-98] [D-99] [D-100] [Chemistry] [D-101][D-102] [D- 103] [D-104] [D-105] [Chemistry] 注意:原内容中“所0001515”疑似有误,我按原样翻译,你可根据实际情况修正。[D-106][D-107] [D-108] [D-109] [D-110] [ka] [D-111][D-112] [D-113] [D-114] [D-115] [ka] [D-116][D-117] [D-118] [D-119] [D-120] [ka] (Dn means the number of deuterium atoms substituted, and indicates a structure in which one or more deuterium atoms have been substituted.)

[0095] The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. By including them in this range, the electron transport capability of the first compound and the hole transport capability of the second compound can be combined to achieve bipolar characteristics and improve efficiency and lifetime. Within this range, the first compound and the second compound may 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.

[0096] In addition to the first and second compounds described above, one or more compounds may be further included.

[0097] 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.

[0098] The dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, such as a red or green phosphorescent dopant.

[0099] A 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 excites the compound to a triplet state or higher. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may contain one or more types.

[0100] 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 may be, for example, a compound represented by the following chemical formula Z, but is not limited thereto.

[0101] [Chemical formula Z] L 9 MX In the above chemical formula Z, M is a metal, and L 9 and X are the same or different and are ligands that form a complex with M.

[0102] M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof; L 9 and X may be, for example, a bidentate ligand.

[0103] L 9 Examples of the ligand represented by X can be selected from the chemical formulae listed in Group A below, but are not limited thereto.

[0104] [Group A] [ka] In Group A above, R 300 ~R 302 each independently represents hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms which may or may not be substituted with a halogen, an aryl group having 6 to 30 carbon atoms which may or may not be substituted with an alkyl group having 1 to 30 carbon atoms, or a halogen; R 303 ~R 324 are 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.

[0105] The dopant according to an embodiment may be an iridium complex, which may be represented by, for example, the following formula 6-1 or 6-2.

[0106] [Chemical formula 6-1] [ka] In the above chemical formula 6-1, 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 an 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 100 is a monovalent anionic bidentate ligand that coordinates to iridium through a lone pair of carbon or heteroatoms, m19 and m20 are each independently an integer of 0 to 3, and m19 + m20 is an integer of 1 to 3; [Chemical formula V-1] [ka] 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 * denotes a moiety bonded to a carbon atom.

[0107] [Chemical formula 6-2] [ka] In the above chemical formula 6-2, 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 100 is a monovalent anionic bidentate ligand that coordinates to iridium through a lone pair of carbon or heteroatoms, n1 and n2 are each independently an integer of 0 to 3, and n1+n2 is an integer of 1 to 3.

[0108] For example, a dopant represented by the following chemical formula Z-1 may be included.

[0109] [Chemical formula Z-1] [ka] In the above 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, SO2, 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 group, cycloalkyl group, heteroalkyl group, arylalkyl group, alkoxy group, aryloxy group, amino group, silyl group, alkenyl group, cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, and any adjacent R A , R B , R C , R D , R, and R' are optionally bonded to form a ring, and X B , X C , X D , and X E are each independently selected from the group consisting of carbon and nitrogen, and Q 1 , Q 2 , Q 3 , and Q 4 indicates an oxygen or a direct bond, respectively.

[0110] The platinum complex can be represented by, for example, the following chemical formula 7-1 or 7-2.

[0111] [Chemical formula 7-1] [ka] [Chemical formula 7-2] [ka] In the above chemical formula 7-1 and chemical formula 7-2, X 100 are O, S, and NR 132 is selected from R 118 ~R 132 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 R134 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 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.

[0112] 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.

[0113] The organic optoelectronic device is not particularly limited as long as it is a device capable of converting electrical energy and light energy into each other, and examples thereof include organic photoelectric devices, organic light-emitting devices, organic solar cells, and organic photoreceptor drums.

[0114] Here, an organic light-emitting element, which is an example of an organic optoelectronic element, will be described with reference to the drawings.

[0115] FIG. 1 is a cross-sectional view showing an organic light-emitting device according to one embodiment.

[0116] Referring to FIG. 1, an organic light emitting device 100 according to an embodiment includes an anode 120 and an anode 110 facing each other, and an organic layer 105 disposed between the anode 120 and the anode 110 .

[0117] The positive electrode 120 can be 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.

[0118] The negative electrode 110 can be made of a conductor with a low work function to facilitate electron injection, such as a metal, a metal oxide, and / or a conductive polymer. 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, LiF / Al, and BaF / Ca.

[0119] The organic layer 105 can include the organic optoelectronic compound or composition described above.

[0120] The organic layer 105 includes a light-emitting layer 130, which may include the organic optoelectronic compound or composition described above.

[0121] The organic optoelectronic composition further comprising a dopant may be, for example, a green-emitting composition.

[0122] The light-emitting layer 130 may include, for example, the aforementioned organic optoelectronic device compound or composition as a phosphorescent host.

[0123] The organic layer may further include a charge transport region in addition to the light-emitting layer.

[0124] The charge transport region may be, for example, a hole transport region 140 .

[0125] The hole transport region 140 can further enhance hole injection and / or hole mobility between the positive electrode 120 and the light-emitting layer 130 and block electrons.

[0126] Specifically, the hole transport region 140 may include a hole transport layer between the anode 120 and the light-emitting layer 130, and a hole transport auxiliary layer between the light-emitting layer 130 and the hole transport layer, and 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.

[0127] [Group B] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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[0128] The charge transport region may also be, for example, an electron transport region 150 .

[0129] The electron transport region 150 can further enhance electron injection and / or electron mobility between the negative electrode 110 and the light-emitting layer 130 and block holes.

[0130] Specifically, the electron transport region 150 may include an electron transport layer between the anode 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.

[0131] [Group C] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] One embodiment may be an organic light-emitting device including a light-emitting layer as the organic layer.

[0132] Another embodiment may be an organic light emitting device including an emissive layer and a hole transport region as organic layers.

[0133] Another embodiment may be an organic light-emitting device including an emitting layer and an electron transport region as organic layers.

[0134] 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 as shown in FIG.

[0135] Meanwhile, the organic light emitting device may further include an electron injection layer (not shown) and a hole injection layer (not shown) in addition to the light emitting layer as the organic layer.

[0136] 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 deposition method such as vacuum evaporation, sputtering, plasma plating, or ion plating, and then forming an anode or cathode thereon.

[0137] The organic light emitting device described above can be applied to an organic light emitting display device.

[0138] The above-described embodiments will be described in more detail with reference to the following examples, which are for illustrative purposes only and are not intended to limit the scope of the invention. [Example]

[0139] 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.

[0140] (Manufacturing compounds for organic photoelectron devices) <Synthesis Example 1: Synthesis of Compound A-1> [Reaction Scheme 1] [ka] Step 1: Synthesis of Compound A-1-3 23.4 g (87.3 mmol, A-1-1) of 2-chloro-4,6-diphenyl-1,3,5-triazine (1 equivalent) was added to 200 mL of toluene and 100 mL of distilled water. The mixture was stirred at 80 °C for 6 hours under a nitrogen atmosphere with 1 equivalent of 9H-carbazole-4-pinacol boron ester (A-1-2, cass: 1255309-13-7), 0.03 equivalents of Pd(PPh3), and 2 equivalents of K2CO3. The aqueous layer was removed, and the organic layer was dried under reduced pressure. The resulting solid was washed with water and hexane and then recrystallized from 300 mL of toluene to give compound A-1-3 in 60% yield.

[0141] Step 2: Synthesis of Compound A-1 12 g (30.1 mmol) of compound A-1-3 (1 equivalent) was added to 100 mL of DMF, and 1 equivalent of intermediate A-1-4 (cas: 1818371-42-4) and 3 equivalents of KPO were added and stirred at 140 °C for 6 hours under a nitrogen atmosphere. The organic layer was dried under reduced pressure, and the resulting solid was washed with water and hexane. The solid was then recrystallized from 150 mL of toluene to obtain white solid compound A-1 in 70% yield. (LC / MS: theoretical value 705.26 g / mol, measured value: 706.37 g / mol)

[0142] <Synthesis Example 2: Synthesis of Compound A-15> [Reaction Scheme 2] [ka] Step 1: Synthesis of compound A-15-2 23.4 g (87.3 mmol, A-1-1) of 2-chloro-4,6-diphenyl-1,3,5-triazine (1 equivalent) was added to 200 mL of toluene and 100 mL of distilled water. The mixture was stirred at 80 °C for 6 hours under a nitrogen atmosphere with 1 equivalent of 9H-carbazole-2-pinacol boron ester (A-15-1, cass: 1242412-60-7), 0.03 equivalents of Pd(PPh3), and 2 equivalents of K2CO3. The aqueous layer was removed, and the organic layer was dried under reduced pressure. The resulting solid was washed with water and hexane and then recrystallized from 300 mL of toluene to give intermediate A-15-2 in 60% yield.

[0143] Step 2: Synthesis of compound A-15 Compound A-15 was synthesized in 75% yield using 1 equivalent of compound A-15-2 and 1 equivalent of compound A-1-4 in the same manner as in the two steps of Synthesis Example 1. (LC / MS: theoretical value 705.26 g / mol, measured value: 706.35 g / mol)

[0144] <Synthesis Example 3: Synthesis of Compound A-27> [Reaction Scheme 3] [ka] Step 1: Synthesis of compound A-27-1 Under nitrogen, 4-Bromo-9H-carbazole (16.4 g, 66.5 mmol), Trifilc acid (29.9 g, 199.5 mmol), and Benzene-D6 (78.4 g, 931.0 mmol) were placed in a round-bottom flask and refluxed at 50°C for 20 hours. After the reaction was complete, DO (10 ml) was slowly added to quench the reaction and the mixture was thoroughly stirred. The mixture was neutralized by titration with saturated KPO(aq) solution. After the reaction was complete, the aqueous layer was removed using a separatory funnel, and the organic solvent was removed under reduced pressure to obtain a solid. The resulting solid was dissolved in Toluene, and the water was removed using MgSO. After that, the organic solvent was filtered using a silica gel pad, and the filtrate was dried under vacuum to obtain 14.2 g (84%) of compound A-27-1.

[0145] Step 2: Synthesis of compound A-27-2 In a 500 mL round-bottom flask, 14.2 g (56.1 mmol) of compound A-27-1 was placed in 200 mL of toluene, and 0.05 equivalents of dichlorodiphenylphosphinoferrocenepalladium, 1.2 equivalents of bis-pinacolatodiboron, and 2 equivalents of potassium acetate were added. The mixture was heated to reflux under a nitrogen atmosphere for 4 hours. 200 mL of warmed toluene (80 °C) was added to the reaction mixture, which was then filtered through silica gel and the filtrate was concentrated. The concentrated solid (A-27-2) was dried and used in the next reaction without further purification.

[0146] Step 3: Synthesis of compound A-27-3 Compound A-27-3 was synthesized in a 60% yield in the same manner as in Step 1 of Synthesis Example 1 using 1 equivalent of compound A-27-2.

[0147] Step 4: Synthesis of Compound A-27 Compound A-27 was synthesized in 70% yield using 1 equivalent of compound A-27-3 and 1 equivalent of compound A-1-4 in the same manner as in the two steps of Synthesis Example 1. (LC / MS: theoretical value 712.31 g / mol, measured value: 713.29 g / mol)

[0148] <Comparative Synthesis Example 1: Synthesis of Compound C1> [ka] Compound C1 was synthesized with reference to patent EP3315581.

[0149] <Comparative Synthesis Example 2: Synthesis of Compound C2> [Reaction Scheme 4] [ka] Compound C2 was synthesized using compound A-15-2 and compound C2-1 (see EP3315581) according to the synthesis method of EP3315581.

[0150] Comparative Synthesis Example 3: Synthesis of Compound C3 [Reaction Scheme 5] [ka] 1 equivalent of intermediate A-1-1 8g (30mmol), 1 equivalent of compound A-1-3 12.0g (30mmol), 1.5 equivalents of NaOtBu, 0.03 equivalents of Pd2(dba)3, and 0.12 equivalents of P(t-Bu)3 were added to 150mL of xylene and stirred under reflux for 12 hours under a nitrogen atmosphere. After removing the xylene, 200mL of methanol was added to the resulting mixture, and the crystallized solid was filtered. It was then dissolved in MCB and filtered through silica gel. The organic solvent was then concentrated to an appropriate amount to obtain compound C3 in a 60% yield. (LC / MS theoretical value: 629.23 g / mol, measured value: M+1 = 630.32 g / mol)

[0151] Comparative Synthesis Example 4: Synthesis of Compound C4 [Reaction Scheme 6] [ka] Compound C4 was synthesized in 80% yield in the same manner as in Comparative Synthesis Example 3 using 1 equivalent of intermediate C4-1 and 1 equivalent of compound A-1-3. (LC / MS theoretical value: 705.26 g / mol, measured value: M+1 = 706.31 g / mol)

[0152] Comparative Synthesis Example 5: Synthesis of Compound C5 [Reaction Scheme 7] [ka] C5 was synthesized in a 75% yield in the same manner as in Comparative Synthesis Example 3 using 1 equivalent of intermediate C5-1 and 1 equivalent of compound A-1-3. (LC / MS theoretical value: 705.26 g / mol, measured value: M+1 = 706.30 g / mol)

[0153] (Production of the second compound) Compound B-99 was synthesized in the same manner as disclosed in US2017-0317293A1.

[0154] <Synthesis Example 4: Synthesis of Compound B-186> [Reaction Scheme 8] [ka] Step 1: Synthesis of compound Int5 Compound Int1 was synthesized with reference to the method disclosed in Korean Patent Publication No. 2016-0049842.

[0155] Step 2: Synthesis of compound B-186 30 g (0.0535 mol) of compound Int5, 40 g (0.267 mol) of trifluoromethanesulfonic acid, and 282 g (3.35 mol) of D6-benzene were added and stirred at 10°C for 24 hours. Purified water was added and neutralized with saturated K3PO4 solution. The organic layer was concentrated and purified by column chromatography to obtain 18 g of compound B-186 (white solid, LC-Mass Mz 578.79, C 42 H 10 D 18 N2).

[0156] <Synthesis Example 5: Synthesis of Compound C-5> [Reaction Scheme 9] [ka] Step 1: Synthesis of intermediate C-5-1 In a round-bottom flask, 10.44 g (42.41 mmol) of 4-bromo-9H-carbazole, 11.88 g (42.41 mmol) of 4-iodo-1,1'-biphenyl (purchased from Aldrich), 0.388 g (0.424 mmol) of Pd2(dba)3, 0.206 g (0.848 mmol) of P(t-Bu)3, and 6.11 g (63.61 mmol) of NaO(t-Bu) were suspended in 420 mL of toluene and stirred at 60 °C for 12 hours. After the reaction was complete, distilled water was added and the mixture was stirred for 30 minutes. The organic layer was extracted and then columnated on a silica gel column (hexane / dichloromethane = 9:1 (v / v)) to obtain 14.70 g (87% yield) of intermediate C-5-1.

[0157] Step 2: Synthesis of intermediate C-5-2 In a round-bottom flask, 15.50 g (38.92 mmol) of the synthesized intermediate C-5-1, 7.15 g (42.81 mmol) of (2-nitrophenyl)-boronic acid, 16.14 g (116.75 mmol) of potassium carbonate, and 1.35 g (1.17 mmol) of tetrakis-(triphenylphosphine)palladium(0) (Pd(PPh3)4) were suspended in 150 mL of toluene and 70 mL of distilled water and refluxed for 12 hours. The mixture was then extracted with dichloromethane and distilled water, and the organic layer was filtered through silica gel. The organic solution was then removed, and the solid product was recrystallized from dichloromethane and n-hexane to obtain 13.72 g (80% yield) of intermediate C-5-2.

[0158] Step 3: Synthesis of intermediate C-5-3 A round-bottom flask was charged with 22.46 g (51.00 mmol) of the synthesized intermediate C-5-2 and 52.8 ml of triethyl phosphite, and the mixture was stirred at 160 °C for 12 hours after nitrogen substitution. After the reaction was completed, 3 L of MeOH was added and stirred, then filtered and the filtrate was evaporated. Purification by column chromatography (hexane) yielded 10.42 g of intermediate C-5-3 (50% yield).

[0159] Step 4: Synthesis of Compound C-5 Using the synthesized intermediate C-5-3 and 1-iodo-3-phenylbenzene, compound C-5 was synthesized in the same manner as in Step 1 of Synthesis Example 5 (yield: 60%). (LC / MS: theoretical value 560.23 g / mol, measured value: 561.57 g / mol)

[0160] (Fabrication of organic light-emitting devices) 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, it was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned using oxygen plasma for 10 minutes and then transferred to a vacuum deposition machine. Using the prepared ITO transparent electrode as the anode, Compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum-deposited on the top of the ITO substrate to form a 100 Å-thick hole injection layer. Compound A was vacuum-deposited on top of the hole injection layer to a thickness of 1350 Å to form a hole transport layer. Compound B was vacuum-deposited on top of the hole transport layer to a thickness of 350 Å to form a hole transport auxiliary layer. Compound A-1 obtained in Synthesis Example 1 was used as the host, and 7 wt% PhGD was doped as the dopant to form a 400 Å-thick emissive layer on top of the hole transport auxiliary layer via vacuum deposition. 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.

[0161] The structure was ITO / compound A (3% NDP-9 doping, 100 Å) / compound A (1350 Å) / compound B (350 Å) / EML [93 wt% host (compound A-1): 7 wt% PhGD] (400 Å) / compound C (50 Å) / compound D: LiQ (300 Å) / LiQ (15 Å) / Al (1200 Å).

[0162] 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-(1,1'-Biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine [PhGD] [ka]

[0163] <Example 2> A glass substrate coated with a thin film of ITO (indium tin oxide) was ultrasonically cleaned with distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned using oxygen plasma for 10 minutes and then transferred to a vacuum deposition machine. Using the prepared ITO transparent electrode as the anode, Compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum-deposited on top of the ITO substrate to form a 100 Å thick hole injection layer. Compound A was then deposited on top of the hole injection layer to a thickness of 1350 Å to form a hole transport layer. Compound E was then deposited on top of the hole transport layer to a thickness of 350 Å to form a hole transport auxiliary layer. Compound A-1 obtained in Synthesis Example 1 and compound B-186 obtained in Synthesis Example 4 were simultaneously used as hosts on the hole transport assisting layer, and doped with 10 wt% PhGD as a dopant by vacuum deposition to form a 330 Å thick light-emitting layer. 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 1:1 weight ratio 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.

[0164] The structure was ITO / Compound A (3% NDP-9 doping, 100 Å) / Compound A (1350 Å) / Compound E (350 Å) / EML [90 wt% host (Compound A-1:Compound B-186 = 4:6 w / w):10 wt% PhGD] (330 Å) / Compound F (50 Å) / Compound G: LiQ (300 Å) / LiQ (15 Å) / Al (1200 Å).

[0165] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine 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

[0166] <Examples 3 to 8 and Comparative Examples 1 to 11> The devices of Examples 3 to 8 and Comparative Examples 1 to 11 were fabricated in the same manner as in Example 1 or Example 2, except that the host and composition were changed as shown in Tables 1 and 2 below.

[0167] <Evaluation> (1) Measurement of changes in current density due 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.

[0168] (2) Measurement of brightness change due to voltage change The voltage of the fabricated organic light emitting device was increased from 0V to 10V, and the luminance at that time was measured using a luminance meter (Minolta Cs-1000A) to obtain the results.

[0169] (3) Luminous efficiency measurement Using the luminance and current density measured from (1) and (2), the same current density (10 mA / cm 2 The luminous efficiency (cd / A) of the

[0170] The relative values ​​based on the luminous efficiency of Comparative Example 1 are shown in Table 1 below.

[0171] The relative values ​​based on the luminous efficiency of Comparative Example 6 are shown in Table 2 below.

[0172] (4) Lifespan measurement The initial luminance (cd / m) of the fabricated organic light-emitting device was measured using a Polaronics lifetime measurement system. 2 ) to 24,000 cd / m 2 The decrease in brightness over time was measured, and the time when the brightness decreased to 95% of the initial brightness was measured as the T95 life.

[0173] The relative values ​​based on the T95 life of Comparative Example 1 are shown in Table 1 below.

[0174] The relative values ​​based on the T95 life of Comparative Example 6 are shown in Table 2 below.

[0175] [Table 1]

[0176] [Table 2]

[0177] Referring to Table 1, it can be seen that the organic light emitting device to which the compound according to the embodiment of the present invention is applied has significantly improved efficiency and lifespan characteristics compared to the organic light emitting device according to the comparative example. In particular, referring to Table 2, it can be seen that the efficiency and lifespan characteristics of the organic light emitting device to which the composition containing the compound according to the embodiment of the present invention is applied are also improved.

[0178] Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic concept of the present invention defined in the following claims also fall within the scope of the present invention. [Explanation of symbols]

[0179] 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: [Chemical formula 1] 【Chemical 1】 In the above chemical formula 1, R １ is 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 6 to 20 carbon atoms, Z １ ~Z ３ are each independently N or CR ａ and Z １ ~Z ３ at least two of are N; Z ４ ~Z ６ are each independently N or CR ｂ and Z ４ ~Z ６ at least two of are N; R ａ , R ｂ , R ２ , and R ３ each independently represents hydrogen, deuterium, a cyano group, a halogen 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, L １ ~L ４ each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, Ar １ ~Ar ４ 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, m1 and m2 each independently represent an integer from 1 to 4; m3 is an integer from 1 to 3.

2. The compound for an organic optoelectronic device according to claim 1, wherein the formula 1 is represented by any one of the following formulas 1A to 1D: [Chemical formula 1A] [Chemical formula 1B] 【Chemistry 2】 [Chemical formula 1C] [Chemical formula 1D] 【Chemistry 3】 In the above Chemical Formula 1A to Chemical Formula 1D, Z １ ~Z ６ , R １ ~R ３ , L １ ~L ４ , Ar １ ~Ar ４ , and m1 to m3 are as defined in claim 1.

3. 2. The compound for an organic optoelectronic device according to claim 1, wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-9. [Chemical formula 1-1] [Chemical formula 1-2] 【Chemistry 4】 [Chemical formula 1-3] [Chemical formula 1-4] 【Chemistry 5】 [Chemical formula 1-5] [Chemical formula 1-6] 【Chemistry 6】 [Chemical formula 1-7] [Chemical formula 1-8] 【Chemistry 7】 [Chemical formula 1-9] 【Chemistry 8】 In the above chemical formulas 1-1 to 1-9, R １ ~R ３ , L １ ~L ４ , Ar １ ~Ar ４ , and m1 to m3 are as defined in claim 1.

4. 2. The compound for an organic optoelectronic device according to claim 1, wherein the formula 1 is represented by the following formula 1-B-1 or 1-D-1: [Chemical formula 1-B-1] [Chemical formula 1-D-1] 【Chemistry 9】 In the above Chemical Formula 1-B-1 and Chemical Formula 1-D-1, R １ ~R ３ , L １ ~L ４ , Ar １ ~Ar ４ , and m1 to m3 are as defined in claim 1.

5. The Ar １ ~Ar ４ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

6. A compound for an organic optoelectronic device, which is one selected from the compounds listed in Group 1 below. [Group 1] [A-1] [A-2] [A-3] [A-4] [A-5] 【Chemistry 10】 [A-6] [A-7] [A-8] [A-9] [A-10] 【Chemistry 11】 [A-11] [A-12] [A-13] [A-14] 【Chemistry 12】 [A-15] [A-16] [A-17] [A-18] 【Chemistry 13】 [A-19] [A-20] [A-21] [A-22] 【Chemistry 14】 [A-23] [A-24] [A-25] [A-26] 【Chemistry 15】 [A-27] [A-28] [A-29] [A-30] 【Chemistry 16】

7. comprising a first compound and a second compound; The first compound is a 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: [Chemical formula 2] 【Chemistry 17】 In the above chemical formula 2, R ４ ~R ８ and Ar ７ ~Ar １０ 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 ５ and Ar ６ 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 ５ and L ６ each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, m4, m7, and m8 each independently represent an integer from 1 to 4; m5 and m6 each independently represent an integer of 1 to 3; n is an integer from 0 to 2; [Chemical formula 3] [Chemical formula 4] 【Chemistry 18】 In the above Chemical Formula 3 and Chemical Formula 4, a in Chemical Formula 3 １ ＊ ~a ４ ＊ are each independently a bonding carbon (C) or C-L ａ -R ｃ and a in Chemical Formula 3 １ ＊ ~a ４ ＊ two adjacent ones of are bonded to * in Chemical Formula 4, L ａ , L ７ , and L ８ each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R ｃ , Ar １３ , Ar １４ , R ９ , and R １０ 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 １１ and Ar １２ 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, m9 and m10 each independently represent an integer of 1 to 4; [Chemical formula 5] 【Chemistry 19】 In the above chemical formula 5, L １０ each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R １６ ~R ２８ 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 １３ 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, m16 is an integer from 1 to 3.

8. The composition for organic optoelectronic devices according to claim 7, wherein the formula 2 is represented by the following formula 2-8: [Chemical formula 2-8] 【Chemistry 20】 In the above chemical formula 2-8, Ar ７ ~Ar １０ and R ４ ~R ７ are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; m4 and m7 each independently represent an integer from 1 to 4; m5 and m6 each independently represent an integer of 1 to 3; *-L ５ -Ar ５ and *-L ６ -Ar ６ are each independently one of the substituents listed in Group I below, [Group I] 【Chemical 21】 In the above Group I, R １１ ~R １５ are each independently hydrogen, deuterium, a cyano group, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms, m11 is an integer from 1 to 5; m12 is an integer from 1 to 4; m13 is an integer from 1 to 3; m14 is an integer of 1 or 2, m15 is an integer from 1 to 7; * indicates the binding site.

9. The composition for an organic optoelectronic device according to claim 7 , wherein the combination of Chemical Formula 3 and Chemical Formula 4 is represented by Chemical Formula 3C: [Chemical formula 3C] 【Chemical 22】 In the above chemical formula 3C, L ａ３ and L ａ４ is a single bond, Ar １３ , Ar １４ , R ９ , R １０ , R ｃ３ , and R ｃ４ are each independently hydrogen, deuterium, or an aryl group having 6 to 12 carbon atoms; m9 and m10 each independently represent an integer of 1 to 4; *-L ７ -Ar １１ and *-L ８ -Ar １２ are each independently one of the substituents listed in Group I below, [Group I] 【Chemical 23】 In the above Group I, R １１ ~R １５ are each independently hydrogen, deuterium, a cyano group, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms, m11 is an integer from 1 to 5; m12 is an integer from 1 to 4; m13 is an integer from 1 to 3; m14 is an integer of 1 or 2, m15 is an integer from 1 to 7; * indicates the binding site.

10. The composition for organic optoelectronic devices according to claim 7, wherein the formula 5 is represented by the following formula 5-2 or 5-3: [Chemical formula 5-2] [Chemical formula 5-3] 【Chemistry 24】 In the above chemical formula 5-2 and chemical formula 5-3, L １０ , R １６ ~R ２８ , Ar １３ , and m １６ is as defined in claim 7.

11. 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 is a compound for an organic optoelectronic device according to any one of claims 1 to 6, or An organic optoelectronic device comprising the composition for an organic optoelectronic device according to any one of claims 7 to 10.

12. the organic layer includes an emitting layer; The organic optoelectronic device according to claim 11 , wherein the light-emitting layer comprises the compound for an organic optoelectronic device or the composition for an organic optoelectronic device.

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

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