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, a composition for an organic optoelectronic device containing the same, an organic optoelectronic device, and a display device. The details of 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 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 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 them, organic light emitting diodes (OLEDs) have been attracting much attention in recent years due to the increasing demand for flat panel display devices. Organic light emitting diodes are devices that convert electrical energy into light, and the performance of organic light emitting diodes is greatly influenced by the organic material located between electrodes. Summary of the Invention [Problem to be solved by the invention]

[0006] An embodiment of the present invention provides a compound for an organic optoelectronic device, which can realize an organic optoelectronic device with low driving, high efficiency and long life.

[0007] Another embodiment of the present invention provides a composition for an organic optoelectronic device that can realize an organic optoelectronic device with high efficiency and long life.

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

[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] In the above Chemical Formula 1, Ar 1 and Ar 2 each independently represents 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 and L 2 each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, R 1 and R 2 each independently represents hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; R 3 and R 4 are each independently hydrogen or deuterium; n1, n2, and n4 each independently represent an integer from 1 to 4; n3 is an integer from 1 to 3.

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

[0013] The first compound is as described above, and the second compound may be a compound for an organic optoelectronic device represented by the following Chemical Formula 2, or a compound for an organic optoelectronic device represented by a combination of the following Chemical Formulas 3 and 4.

[0014] [ka] In the above Chemical Formula 2, Ar 3 and 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, L 3 and L 4 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R 5 ~R 15 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, m is an integer from 0 to 2; [ka] [ka] In the above Chemical Formula 3 and Chemical Formula 4, 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, a in Chemical Formula 3 1* ~a4* two adjacent ones of the above are linking carbons (C) linked to * in Chemical Formula 4, a in Chemical Formula 3 1* ~a 4* The remaining two of the formulas not linked to * in formula 4 are each independently represented by CL a -R a and L a , L 5 and L 6 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R a and R 16 ~R 23 are each independently 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.

[0015] 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, the organic layer comprising the compound for organic optoelectronic devices or the composition for organic optoelectronic devices.

[0016] According to yet another embodiment, there is provided a display device including the organic optoelectronic device. Effect of the Invention

[0017] The present invention can realize an organic optoelectronic device with low driving, high efficiency and long life. [Brief description of the drawings]

[0018] [Figure 1] 1 is a cross-sectional view illustrating an organic light-emitting device according to an embodiment. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0019] DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will now be described in detail with reference to the accompanying drawings, which are given by way of example only and are not intended to be limiting of the present invention, as defined only by the scope of the claims that follow.

[0020] In this specification, unless otherwise defined, "substituted" means that at least one hydrogen of 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.

[0021] In one embodiment of the present invention, "substitution" 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 one specific embodiment of the present invention, "substitution" 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 one specific embodiment of the present invention, "substitution" 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 replaced with a deuterium atom, 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.

[0022] As used herein, "unsubstituted" means that the hydrogen atom remains as a hydrogen atom without being replaced with another substituent.

[0023] As used herein, "hydrogen substitution (-H)" can include "deuterium substitution (-D)" or "tritium substitution (-T)."

[0024] As used herein, unless otherwise defined, "hetero" means that one functional group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si, and the remainder are carbon.

[0025] In the present specification, the term "aryl group" refers to a general concept of a group having one or more aromatic hydrocarbon partial structures, and includes a form in which all elements of the aromatic hydrocarbon partial structure have p-orbitals and these p-orbitals form a conjugation, such as a phenyl group, naphthyl group, etc., a form in which two or more aromatic hydrocarbon partial structures are linked through a sigma bond, such as a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and a non-aromatic fused ring in which two or more aromatic hydrocarbon partial structures are directly or indirectly fused, such as a fluorenyl group, etc.

[0026] Aryl groups include monocyclic, polycyclic or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0027] As used herein, the term "heterocyclic group" is a generic concept that includes a heteroaryl group, and refers to a ring compound, such as an aryl group, a cycloalkyl group, a condensed ring thereof, or a combination thereof, that contains at least one heteroatom selected from the group consisting of N, O, S, P, and Si in place of carbon (C). When the heterocyclic group is a condensed ring, the entire heterocyclic group or each ring may contain one or more heteroatoms.

[0028] As an 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.

[0029] 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 triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0030] 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 benzyl group, a substituted or unsubstituted phenyl ... The alkyl group may be, but is not limited to, an aryl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted 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, or a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof.

[0031] In this specification, the hole characteristic refers to a characteristic in which an electron can be donated to form a hole when an electric field is applied, and refers to a characteristic that has a conductive characteristic according to the HOMO level and facilitates the injection of a hole formed in the positive electrode into the light-emitting layer, the movement of a hole formed in the light-emitting layer to the positive electrode, and the movement within the light-emitting layer.

[0032] 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 conductive properties according to the LUMO level and facilitating the injection of electrons formed in the negative electrode into the light-emitting layer, the movement of electrons formed in the light-emitting layer to the negative electrode, and the movement within the light-emitting layer.

[0033] Hereinafter, a compound for an organic optoelectronic device according to an embodiment will be described.

[0034] The compound for an organic optoelectronic device according to an embodiment is represented by the following Chemical Formula 1.

[0035] [ka] In the above Chemical Formula 1, Ar 1 and Ar 2 each independently represents 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 and L 2 each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, R 1 and R 2 each independently represents hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; R 3 and R 4 are each independently hydrogen or deuterium; n1, n2, and n4 each independently represent an integer from 1 to 4; n3 is an integer from 1 to 3.

[0036] The compound represented by Chemical Formula 1 has a structure containing a para-biphenyl substituted with an ortho-carbazole in a triazine, and has particularly excellent energy transfer efficiency to a phosphorescent dopant, and is used as an advantageous material as a phosphorescent host.

[0037] The para-biphenyl structure contained in Formula 1 can increase the electron mobility and improve the electron stability due to the resonance effect compared to mono-phenyl, and can improve the lifetime, especially when applied to a phosphorescent host.

[0038] In addition, triazine and carbazole are substituted at the ortho position of the para-biphenyl, and the dihedral angle is increased due to the steric hindrance of triazine and carbazole, and the triazine moiety and the carbazole moiety are twisted with each other.

[0039] This allows the HOMO and LUMO energy levels to be separated with almost no overlap, enabling fast energy transfer with a small ΔEst, and therefore exhibits high efficiency characteristics, especially when applied to a phosphorescent host.

[0040] Moreover, side reaction pathways in the excited state are reduced, which increases lifetime, especially when applied to phosphorescent hosts.

[0041] On the other hand, ortho-substitution of triazine and carbazole can minimize degradation and decomposition with a deposition temperature reduction of about 10% compared to para-substitution and meta-substitution.

[0042] When n1 is 2 or more, each R 1 may be the same or different from each other.

[0043] When n2 is 2 or more, each R 2 may be the same or different from each other.

[0044] When n3 is 2 or more, each R 3 may be the same or different from each other.

[0045] If n4 is 2 or more, each R 4 may be the same or different from each other.

[0046] The above-mentioned Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.

[0047] [ka] In the above Chemical Formula 1-1 to Chemical Formula 1-4, Ar 1 ~Ar 3 , R 1 ~R 4 , n1~n4, L 1 and L 2 The definition is as described above.

[0048] As an example, the formula 1 is represented by the formula 1-2.

[0049] As an example, the above-mentioned R 1 and R 2 may each independently be hydrogen, deuterium, 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, or a substituted or unsubstituted triphenylene group.

[0050] As a specific example, R 1 and R 2 may each independently be hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0051] For example, the above R 1 and R 2 may each independently be hydrogen, deuterium, or an unsubstituted phenyl group.

[0052] As an example, the Ar 1 and Ar 2may 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 carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0053] As a specific example, for example, the above-mentioned *-L 1 -Ar 1 and *-L 2 -Ar 2 are each independently selected from the substituents listed in Group I below.

[0054] [ka] In Group I, * denotes a connection point.

[0055] For example, the Ar 1 and Ar 2 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0056] In a most specific embodiment, 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.

[0057] [ka] [ka] [ka] [ka]

[0058] According to another embodiment, the composition for an organic optoelectronic device includes a first compound and a second compound, the first compound being the compound for an organic optoelectronic device described above, and the second compound being a compound for an organic optoelectronic device represented by the following Chemical Formula 2, or a compound for an organic optoelectronic device represented by a combination of the following Chemical Formulas 3 and 4:

[0059] [ka] In the above Chemical Formula 2, Ar 3 and 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, L 3 and L 4 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R 5 ~R 15 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, m is an integer from 0 to 2; [ka] [ka] In the above Chemical Formula 3 and Chemical Formula 4, Ar 5and 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, a in Chemical Formula 3 1* ~a 4* two adjacent ones of the above are linking carbons (C) linked to * in Chemical Formula 4, a in Chemical Formula 3 1* ~a 4* The remaining two of the formulas not linked to * in formula 4 are each independently represented by CL a -R a and L a , L 5 and L 6 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R a and R 16 ~R 23 are each independently 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.

[0060] The second compound is used in the light-emitting layer together with the first compound to increase charge mobility and safety, thereby improving the light-emitting efficiency and life characteristics.

[0061] As an example, Ar in Formula 2 3 and Ar 4 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 3and L 4 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 5 ~R 15 each independently represents hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; m may be 0 or 1.

[0062] As an 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.

[0063] In a specific embodiment of the present invention, the formula 2 is represented by one of the following formulas 2-1 to 2-15.

[0064] [ka] [ka] In the above Chemical Formula 2-1 to Chemical Formula 2-15, R 5 ~R 14 are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; 3 -Ar 3 and *-L 4 -Ar 4 may each independently be one of the substituents listed in Group II below.

[0065] [ka] In Group II, * indicates a linking point.

[0066] In one embodiment, Formula 2 is represented by Formula 2-8.

[0067] In addition, *-L in the above-mentioned chemical formula 2-8 3 -Ar 3 and *-L 4 -Ar 4 are each independently selected from Group II and may be, for example, any one of C-1, C-2, C-3, C-4, C-7, C-8, and C-9.

[0068] As an example, the second compound represented by the combination of Chemical Formula 3 and Chemical Formula 4 is represented by any one of Chemical Formula 3A, Chemical Formula 3B, Chemical Formula 3C, Chemical Formula 3D, and Chemical Formula 3E below.

[0069] [ka] In the chemical formulas 3A to 3E, Ar 5 , Ar 6 , L 3 , L 4 , and R 16 ~R 23 is as described above, L a1 ~L a4 is the above mentioned L 5 and L 6 As defined by R a1 ~R a4 is the above-mentioned R 16 ~R 23 This is as defined above.

[0070] For example, Ar in Formula 3 and Formula 4 5 and Ar 6 each independently represents 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; R a1 ~R a4 and R 16 ~R23 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.

[0071] In a specific embodiment of the present invention, Ar in Formula 3 and Formula 4 5 and Ar 6 may each independently be selected from the substituents listed in Group III above.

[0072] In one embodiment, the R a1 ~R a4 and R 16 ~R 23 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.

[0073] For example, the above R a1 ~R a4 and R 16 ~R 23 are each independently hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group; In a specific embodiment, the R a1 ~R a4 , and R 16 ~R 23 may each independently be a hydrogen atom or a phenyl group.

[0074] In a specific embodiment of the present invention, the second compound is represented by Formula 2-8, wherein Ar 3 and Ar 4are 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 3 and L 4 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; R 5 ~R 14 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.

[0075] In another specific embodiment of the present invention, the second compound is represented by Formula 3C, wherein L a3 and L a4 is a single bond, L 5 and L 6 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms; R 16 ~R 23 , R a3 and R a4 are hydrogen or a phenyl group, and Ar 5 and Ar 6 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0076] For example, the second compound may be one selected from the compounds listed in Group 2 below, but is not limited thereto.

[0077] [ka] [ka]

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[0078] The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. By being included in the above range, it is possible to realize bipolar characteristics at an appropriate weight ratio by utilizing the electron transport ability of the first compound and the hole transport ability of the second compound, thereby improving efficiency and life. Within the above range, for example, they may be included in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20, for example, about 20:80 to about 70:30, about 20:80 to about 60:40, and about 20:80 to about 50:50. As a specific example, they may be included in a weight ratio of 20:80, 30:70, or 40:60.

[0079] In addition to the first and second compounds described above, one or more further compounds may be included.

[0080] For example, the compound for an organic optoelectronic device or the composition for an organic optoelectronic device described above may further include a dopant.

[0081] The dopant can be, for example, a phosphorescent dopant, which can be, for example, a red, green or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0082] The dopant is a material that emits light when mixed in a small amount with a compound for an organic optoelectronic device, and generally may be a material such as a metal complex that emits light by multiple excitation 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.

[0083] An example of the dopant is a phosphorescent dopant, and an example of the phosphorescent dopant is an organometallic compound containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the following chemical formula Z, but is not limited thereto.

[0084] [Chemical formula Z] L 7 MX In the above chemical formula Z, M is a metal, and L 7 and X are the same or different and are ligands that form a complex with M.

[0085] 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 7 and X may be, for example, a bidentate ligand.

[0086] L 7 Examples of the ligand represented by X may be selected from the chemical formulae listed in Group A below, but are not limited thereto.

[0087] [ka] In said Group A, R 300 ~R 302each independently represents hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms which is substituted or unsubstituted with a halogen, an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms, or a halogen; R 303 ~R 324 are each independently hydrogen, deuterium, a 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 substituted or unsubstituted triarylsilyl group having an aryl group having 6 to 30 carbon atoms.

[0088] As an example, the dopant may be represented by the following formula V:

[0089] [ka] In the above chemical formula V, R 101 ~R 116 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 -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 monoanionic bidentate ligand that coordinates to iridium via the unshared electron pair of a carbon or heteroatom. n1 and n2 are each independently an integer of 0 to 3, and n1+n2 is an integer of 1 to 3; [ka] In the above chemical formula V-1, R 135 ~R 139 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 -SiR 132 R 133 R 134 and * denotes a moiety connected to a carbon atom.

[0090] As an example, a dopant represented by the following chemical formula Z-1 may be included.

[0091] [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, SO2, CRR', SiRR', GeRR', and combinations thereof; If nA is 1, then L Eis 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, 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, and any adjacent R 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.

[0092] According to one embodiment, the dopant may be a platinum complex, for example, represented by Formula VI:

[0093] [ka] In the above formula VI, X 100 are O, S and NR 131 is selected from among R 117 ~R 131each 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 -SiR 132 R 133 R 134 and R 132 ~R 134 are each independently an alkyl group having 1 to 6 carbon atoms, R 117 ~R 131 At least one of the groups is -SiR 132 R 133 R 134 Or a tert-butyl group.

[0094] Hereinafter, 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.

[0095] The organic optoelectronic element is not particularly limited as long as it is an element capable of converting electrical energy into light energy and vice versa, and examples thereof include an organic photoelectric element, an organic light-emitting element, an organic solar cell, and an organic photoconductor drum.

[0096] Here, an organic light-emitting element, which is an example of an organic optoelectronic element, will be described with reference to the drawings.

[0097] FIG. 1 is a cross-sectional view illustrating an organic light emitting device according to an embodiment.

[0098] Referring to FIG. 1, an organic light emitting device 100 according to one embodiment includes a positive electrode 120, a negative electrode 110, and an organic layer 105 located between the positive electrode 120 and the negative electrode 110, which face each other.

[0099] The positive electrode 120 is made of a conductor having a high work function so that hole injection can be performed smoothly, for example, a metal, a metal oxide, and / or a conductive polymer. The positive electrode 120 may be made of, but is not limited to, metals such as nickel, platinum, vanadium, chromium, copper, zinc, 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 SnO2 and Sb, or conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDOT), polypyrrole, and polyaniline.

[0100] The negative electrode 110 is made of a conductor having a low work function so that electron injection can be smoothly performed, for example, 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, barium, and alloys thereof, and multilayered materials such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca.

[0101] The organic layer 105 can include an organic optoelectronic compound or composition as described above.

[0102] The organic layer 105 includes a light-emitting layer 130, which may include an organic optoelectronic compound or composition as described above.

[0103] The organic optoelectronic composition further comprising a dopant may be, for example, a red or green light emitting composition.

[0104] Light-emitting layer 130 can include, for example, an organic optoelectronic compound or composition described above as a phosphorescent host.

[0105] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0106] The charge transport region may be, for example, a hole transport region 140 .

[0107] 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.

[0108] 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.

[0109] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0110] 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.

[0111] The charge transport region may also be, for example, an electron transport region 150 .

[0112] 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.

[0113] Specifically, the electron transport region 150 can 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 can be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0114] [ka] [ka] [ka] [ka] [ka] [ka]

[0115] One embodiment may be an organic light emitting device including a light emitting layer as the organic layer.

[0116] Another embodiment may be an organic light emitting device that includes an emissive layer and a hole transport region as organic layers.

[0117] Yet another embodiment may be an organic light emitting device that includes an emissive layer and an electron transport region as organic layers.

[0118] As shown in FIG. 1, an organic light emitting device according to an embodiment of the present invention may include an organic layer 105 including a hole transport region 140 and an electron transport region 150 in addition to an emission layer 130 .

[0119] 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 other than the light emitting layer.

[0120] The organic light emitting device 100 may be manufactured by forming a positive electrode or a negative electrode 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 a positive electrode or a negative electrode thereon.

[0121] The above-described organic light-emitting device can be applied to an organic light-emitting display device. EXAMPLES

[0122] The above-mentioned embodiments will be described in more detail with reference to the following examples, which are merely for illustrative purposes and are not intended to limit the scope of the invention.

[0123] 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.

[0124] (Manufacture of compounds for organic optoelectronic devices) The compounds presented as more specific examples of the compounds of the present invention were synthesized according to the following steps.

[0125] Synthesis Example 1: Synthesis of Compound A-1 [ka]

[0126] Step 1: Synthesis of intermediate P-1 2-chloro-4,6-diphenyl-1,3,5-triazine (50 g / 1.0 eq.), (3-fluoro-[1,1'-biphenyl]-4-yl)boronic acid (1.1 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask with THF (500 mL) and distilled water (165 mL) and refluxed at 80 °C. After 12 h, the reaction was stopped, diluted with DCM, washed three times with brine, and dried over MgSO4. Column chromatography was used to obtain 60 g of intermediate P-1.

[0127] Step 2: Synthesis of compound A-1 Intermediate P-1 (30 g / 1.0 eq.), 9H-carbazole (1.5 eq.), and K3PO4 (3.0 eq.) were poured into a flask with DMF (500 mL) and refluxed at 150° C. After 12 h, the reaction was stopped, diluted with DCM, washed with brine three times, and dried over MgSO4. Column chromatography was used to obtain 32 g of compound A-1.

[0128] Synthesis Example 2: Synthesis of Compound A-3 [ka]

[0129] Step 1: Synthesis of intermediate P-1 Intermediate P-1 (60 g) was obtained by the same synthesis method as in step 1 of Synthesis Example 1.

[0130] Step 2: Synthesis of compound A-3 Intermediate P-1 (30 g / 1.0 eq.), 2-phenyl-9H-carbazole (1.5 eq.), and K3PO4 (3.0 eq.) were poured into a flask with DMF (500 mL) and refluxed at 150°C. After 12 h, the reaction was stopped, diluted with DCM, washed with brine three times, and dried over MgSO4. Column chromatography was used to obtain 38 g of compound A-3.

[0131] Synthesis Example 3: Synthesis of Compound A-11 [ka]

[0132] Step 1: Synthesis of intermediate P-2 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (30 g / 1.0 eq.), (3-fluoro-[1,1'-biphenyl]-4-yl)boronic acid (1.1 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask with THF (500 mL) and distilled water (165 mL) and refluxed at 80 °C. After 12 h, the reaction was stopped, diluted with DCM, washed three times with brine, and dried over MgSO4. Column chromatography was used to obtain 33 g of intermediate P-2.

[0133] Step 2: Synthesis of compound A-11 Intermediate P-2 (33 g / 1.0 eq.), 9H-carbazole (1.5 eq.), and K3PO4 (3.0 eq.) were poured into a flask with DMF (500 mL) and refluxed at 150° C. After 12 h, the reaction was stopped, diluted with DCM, washed with brine three times, and dried over MgSO4. Column chromatography was used to obtain 25 g of compound A-11.

[0134] Synthesis Example 4: Synthesis of Compound A-21 [ka]

[0135] Step 1: Synthesis of intermediate P-3 2-chloro-4-phenyl-6-(triphenylen-2-yl)-1,3,5-triazine (40 g / 1.0 eq.), (3-fluoro-[1,1'-biphenyl]-4-yl)boronic acid (1.1 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask with THF (500 mL) and distilled water (165 mL) and refluxed at 80 °C. After 12 h, the reaction was stopped, diluted with DCM, washed three times with brine, and dried over MgSO4. Column chromatography was used to obtain 42 g of intermediate P-3.

[0136] Step 2: Synthesis of compound A-21 Intermediate P-3 (42 g / 1.0 eq.), 9H-carbazole (1.5 eq.), and K3PO4 (3.0 eq.) were poured into a flask with DMF (500 mL) and refluxed at 150° C. After 12 h, the reaction was stopped, diluted with DCM, washed with brine three times, and dried over MgSO4. Column chromatography was used to obtain 32 g of compound A-21.

[0137] Synthesis Example 5: Synthesis of Compound B-136 [ka]

[0138] Compound B-136 was synthesized with reference to the synthesis method disclosed in US 10476008 B2.

[0139] Comparative Synthesis Example 1: Synthesis of Compound R-1 [ka]

[0140] Step 1: Synthesis of intermediate P-4 2-Chloro-4,6-diphenyl-1,3,5-triazine (30 g / 1.0 eq.), (2-fluoro-[1,1'-biphenyl]-3-yl)boronic acid (1.1 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask with THF (500 mL) and distilled water (165 mL) and refluxed at 80 °C. After 12 h, the reaction was stopped, diluted with DCM, washed three times with brine, and dried over MgSO4. Column chromatography was used to obtain 26 g of intermediate P-4.

[0141] Step 2: Synthesis of compound R-1 Intermediate P-4 (26 g / 1.0 eq.), 9H-carbazole (1.5 eq.), K3PO4 (3.0 eq.) were poured into a flask with DMF (500 mL) and refluxed at 150°C. After 12 h, the reaction was stopped, diluted with DCM, washed with brine three times, and dried over MgSO4. Column chromatography was used to obtain 20 g of compound R-1.

[0142] Comparative Synthesis Example 2: Synthesis of Compound R-2 [ka]

[0143] Step 1: Synthesis of intermediate P-5 2-Chloro-4,6-diphenyl-1,3,5-triazine (30 g / 1.0 eq.), (6-fluoro-[1,1'-biphenyl]-3-yl)boronic acid (1.1 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask with THF (500 mL) and distilled water (165 mL) and refluxed at 80 °C. After 12 h, the reaction was stopped, diluted with DCM, washed three times with brine, and dried over MgSO4. Column chromatography was used to obtain 26 g of intermediate P-5.

[0144] Step 2: Synthesis of compound R-2 Intermediate P-5 (26 g / 1.0 eq.), 9H-carbazole (1.5 eq.), K3PO4 (3.0 eq.) were poured into a flask with DMF (500 mL) and refluxed at 150°C. After 12 h, the reaction was stopped, diluted with DCM, washed with brine three times, and dried over MgSO4. Column chromatography was used to obtain 15 g of compound R-2.

[0145] Comparative Synthesis Example 3: Synthesis of Compound R-3 [ka]

[0146] Step 1: Synthesis of intermediate P-6 2-Chloro-4,6-diphenyl-1,3,5-triazine (30 g / 1.0 eq.), (3,3'-difluoro-[1,1'-biphenyl]-4-yl)boronic acid (1.1 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask with THF (500 mL) and distilled water (165 mL) and refluxed at 80 °C. After 12 h, the reaction was stopped, diluted with DCM, washed three times with brine, and dried over MgSO4. Column chromatography was used to obtain 30 g of intermediate P-6.

[0147] Step 2: Synthesis of compound R-3 Intermediate P-6 (30 g / 1.0 eq.), 9H-carbazole (1.2 eq.), and K3PO4 (2.5 eq.) were poured into a flask with DMF (500 mL) and refluxed at 150° C. After 12 h, the reaction was stopped, diluted with DCM, washed with brine three times, and dried over MgSO4. Column chromatography was used to obtain 8 g of compound R-3.

[0148] Comparative Synthesis Example 4: Synthesis of Compound R-4 [ka]

[0149] Step 1: Synthesis of intermediate P-7 2-Chloro-4,6-diphenyl-1,3,5-triazine (30 g / 1.0 eq.), (2-fluorophenyl)boronic acid (1.1 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask along with THF (500 mL) and distilled water (165 mL) and refluxed at 80 °C. After 12 h, the reaction was stopped, diluted with DCM, washed three times with brine, and dried over MgSO4. Column chromatography was used to obtain 25 g of intermediate P-7.

[0150] Step 2: Synthesis of compound R-4 Intermediate P-7 (25 g / 1.0 eq.), 2-phenyl-9H-carbazole (1.5 eq.), K3PO4 (3.0 eq.) were poured into a flask with DMF (500 mL) and refluxed at 150°C. After 12 hours, the reaction was stopped, diluted with DCM, washed with brine three times, and dried over MgSO4. Column chromatography was used to obtain 20 g of compound R-4.

[0151] (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, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, and dried. After that, the substrate was transferred to a plasma cleaning device, and then cleaned with oxygen plasma for 10 minutes, and then transferred to a vacuum deposition device. Using the ITO transparent electrode prepared in this way as a positive electrode, compound A doped with 3% NDP-9 (manufactured by Novaled) was vacuum-deposited on the top of the ITO substrate to form a hole injection layer with a thickness of 100 Å, and compound A was vacuum-deposited on the top of the hole injection layer to a thickness of 1350 Å to form a hole transport layer. Compound B was vacuum-deposited on the 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 a host on the top of the hole transport auxiliary layer, and 7 wt% PhGD was doped as a dopant to form a luminescent layer with a thickness of 400 Å by 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 weight ratio of 1:1 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 a negative electrode, thereby fabricating an organic light-emitting device.

[0152] The structure was ITO / compound A (1% 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).

[0153] 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]

[0154] Examples 2 to 4 and Comparative Examples 1 to 4 The devices of Examples 2 to 4 and Comparative Examples 1 to 4 were produced in the same manner as in Example 1, except that the host was changed as shown in Table 1 below.

[0155] Example 5 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. After that, the substrate was transferred to a plasma cleaning device, and then cleaned for 10 minutes using oxygen plasma, and then transferred to a vacuum deposition device. Using the ITO transparent electrode prepared in this way as a positive electrode, compound A doped with 3% NDP-9 (Novaled) was vacuum-deposited on the top of the ITO substrate to form a hole injection layer with a thickness of 100 Å, and compound A was deposited on the top of the hole injection layer with a thickness of 1350 Å to form a hole transport layer. Compound E was deposited on the top of the hole transport layer with a thickness of 350 Å to form a hole transport auxiliary layer. Compound A-1 obtained in Synthesis Example 1 and compound B-136 obtained in Synthesis Example 5 were used as hosts on the top of the hole transport auxiliary layer, and 10 wt% PhGD was doped as a dopant to form a 400 Å thick light emitting layer by vacuum deposition. Compound A-1 and compound B-136 were used in a weight ratio of 3:7. Compound F was then deposited on the top of the light emitting layer to a thickness of 50 Å to form an electron transport auxiliary 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 top of the electron transport layer to form a negative electrode, thereby fabricating an organic light emitting device.

[0156] The structure was ITO / compound A (3% NDP-9 doping, 100 Å) / compound A (1350 Å) / compound E (350 Å) / EML [host (compound A-1:compound B-136=3:7):PhGD=90wt%:10wt%] (400 Å) / compound F (50 Å) / compound G: LiQ (300 Å) / LiQ (15 Å) / Al (1200 Å).

[0157] 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

[0158] Examples 6 to 8 and Comparative Examples 5 to 8 The devices of Examples 6 to 8 and Comparative Examples 5 to 8 were produced in the same manner as in Example 5, except that the host was changed as shown in Table 2 below.

[0159] evaluation (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), and the measured current was divided by the area to obtain the result.

[0160] (2) Measurement of luminance change according to voltage change The voltage of the manufactured 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.

[0161] (3) Luminous efficiency measurement Using the luminance and current density measured in (1) and (2), the same current density (10 mA / cm 2 ) and the luminous efficiency (cd / A) were calculated.

[0162] The relative values ​​based on the luminous efficiency of Comparative Example 1 are shown in Table 1 below.

[0163] The relative values ​​based on the luminous efficiency of Comparative Example 5 are shown in Table 2 below.

[0164] (4) Lifespan measurement The initial luminance (cd / m2) of the fabricated organic light-emitting device was measured using a Polaronics lifetime measurement system. 2 ) at 24,000cd / m 2 The decrease in luminance over time was measured, and the time when the luminance decreased to 95% of the initial luminance was measured as the T95 life.

[0165] The relative values ​​based on the T95 life of Comparative Example 1 are shown in Table 1 below.

[0166] The relative values ​​based on the T95 life of Comparative Example 5 are shown in Table 2 below.

[0167] (5) Driving voltage measurement 15mA / cm using a current-voltage meter (Keithley 2400) 2 The driving voltage of each element was measured and the results were obtained.

[0168] The relative values ​​based on the driving voltage of Comparative Example 1 are shown in Table 1 below.

[0169] [Table 1]

[0170] [Table 2]

[0171] 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 driving, efficiency, and life characteristics compared to the organic light emitting device according to the comparative example.

[0172] In particular, referring to Table 2, it can be seen that the efficiency and life characteristics of the organic light emitting device to which the composition including the compound according to the embodiment of the present invention is applied are also improved.

[0173] 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 claims also fall within the scope of the present invention. [Explanation of symbols]

[0174] 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】 In the above Chemical Formula 1, Ar １ and Ar ２ each independently represents 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 and L ２ each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, R １ and R ２ each independently represents hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; R ３ and R ４ are each independently hydrogen or deuterium; n1, n2, and n4 each independently represent an integer from 1 to 4; n3 is an integer from 1 to 3.

2. The compound for organic optoelectronic devices according to claim 1, which is represented by any one of the following chemical formulas 1-1 to 1-4: 【Chemistry 2】 In the above Chemical Formula 1-1 to Chemical Formula 1-4, Ar １ ~Ar ３ , R １ , R ２ , n1, n3, n4, L １ and L ２ is as defined in claim 1.

3. The R １ and R ２ are each independently hydrogen, deuterium, 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, or a substituted or unsubstituted triphenylene group.

4. The Ar １ and Ar ２ 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 phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

5. Said *-L １ -Ar １ and *-L ２ -Ar ２ is independently one selected from the substituents listed in Group I below: 【Chemistry 3】 In Group I, * denotes a connection point.

6. The compound for organic optoelectronic devices according to claim 1, which is one selected from the compounds listed in Group 1 below: 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 。

7. 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 compound for an organic optoelectronic device represented by the following Chemical Formula 2, or a compound for an organic optoelectronic device represented by a combination of the following Chemical Formula 3 and Chemical Formula 4: 【Chemistry 8】 In the above Chemical Formula 2, Ar ３ and 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, L ３ and L ４ each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R ５ ~R １５ 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; m is an integer from 0 to 2; 【Chemistry 9】 【Chemistry 10】 In the above Chemical Formula 3 and Chemical Formula 4, 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, a in Chemical Formula 3 １＊ ~a ４＊ two adjacent ones of are linking carbons (C) linked to * in Chemical Formula 4, a in Chemical Formula 3 １＊ ~a ４＊ The remaining two of the groups not linked to * in Chemical Formula 4 are each independently C-L ａ -R ａ and L ａ , L ５ and L ６ each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R ａ and R １６ ~R ２３ are each independently 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.

8. The composition for organic optoelectronic devices according to claim 7, wherein the chemical formula 2 is represented by the following chemical formula 2-8: 【Chemistry 11】 In the above Chemical Formula 2-8, R ５ ~R １４ each independently represents hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; *-L ３ -Ar ３ and *-L ４ -Ar ４ are each independently one of the substituents listed in Group II below, 【Chemistry 12】 In the above Group II, * indicates a linking point.

9. The composition for organic optoelectronic devices according to claim 7, wherein the combination of Chemical Formula 3 and Chemical Formula 4 is represented by the following Chemical Formula 3C: 【Chemistry 13】 In the above Chemical Formula 3C, L ａ３ and L ａ４ is a single bond, L ５ and L ６ each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, R １６ ~R ２３ , R ａ３ and R ａ４ each independently represents a hydrogen atom or an aryl group having 6 to 12 carbon atoms; Ar ５ and Ar ６ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group.

10. 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 a compound for organic optoelectronic devices according to any one of claims 1 to 6, or a composition for organic optoelectronic devices according to any one of claims 7 to 9.

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

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

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