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

The compound with a para-biphenyl structure and ortho-carbazole substitution on triazine, used as a phosphorescent host, addresses the challenges of low driving voltage, high efficiency, and long life in organic optoelectronic devices, achieving superior performance and stability.

JP7699723B2Active Publication Date: 2025-06-27SAMSUNG SDI CO LTD
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Patent Information

Application Number
JP2024539045
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Priority Date
2021-12-30
Filing Date
2022-12-26
Publication Date
2025-06-27
Estimated Expiration
2042-12-26

AI Technical Summary

Technical Problem

Existing organic optoelectronic devices face challenges in achieving low driving voltage, high efficiency, and long life.

Method used

A compound represented by Chemical Formula 1, which includes a para-biphenyl structure substituted with ortho-carbazole on triazine, is used as a phosphorescent host to enhance energy transfer efficiency and stability in organic optoelectronic devices.

Benefits of technology

The use of this compound results in organic optoelectronic devices with improved efficiency, extended lifespan, and reduced side reactions, leading to enhanced performance and reliability.

✦ Generated by Eureka AI based on patent content.

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Patent Text Reader

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.
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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 Art

[0002] An organic optoelectric diode is a device capable of converting electrical energy and light energy into each other.

[0003] Organic optoelectronic devices can be broadly classified into two types according to their operating principles. One is a photoelectric device in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transmitted to different electrodes to generate electrical energy. The other is a light-emitting device that supplies a voltage or current to an electrode to generate light energy from electrical energy.

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

[0005] Among these, organic light-emitting diodes (OLEDs) have attracted much attention in recent years with the increasing demand for flat panel display devices. An organic light-emitting device is a device that converts electrical energy into light, and the performance of the organic light-emitting device is greatly affected by the organic material located between the electrodes.

Summary of the Invention

Problems to be Solved by the Invention

[0006] One embodiment of the present invention provides a compound for an organic optoelectronic device capable of realizing an organic optoelectronic device with low drive, high efficiency, and long life.

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

[0008] Still another embodiment of the present invention provides an organic optoelectronic device containing the above compound.

[0009] Still another embodiment of the present invention provides a display device containing the above organic optoelectronic device.

Means for Solving the Problems

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

[0011]

Chem.

[0012] According to another embodiment of the present invention, there is provided a composition for an organic optoelectronic device including 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 Formula 3 and Chemical Formula 4.

[0014]

Chemical Formula

Chemical Formula

Chemical Formula

[0015] According to still 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 contains the compound for an organic optoelectronic device or the composition for an organic optoelectronic device.

[0016] According to still another embodiment, there is provided a display device including the organic optoelectronic device.

Advantages 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

Modes for Carrying Out the Invention

[0019] Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, and the present invention is not limited thereby, and is defined only by the scope of the claims described below.

[0020] In this specification, "substituted" means that, unless otherwise defined, at least one hydrogen in a substituent or a compound is substituted 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 an example of the present invention, "substituted" means that at least one hydrogen in a substituent or a 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. Further, in a specific example of the present invention, "substituted" means that at least one hydrogen in a substituent or a 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. Further, in a specific example of the present invention, "substituted" means that at least one hydrogen in a substituent or a 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. Further, in a specific example of the present invention, "substituted" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

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

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

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

[0025] As used herein, the term "aryl group" is a general concept encompassing groups having one or more hydrocarbon aromatic substructures. All elements of the hydrocarbon aromatic substructure have p-orbitals, and these p-orbitals form a conjugation, such as a phenyl group, a naphthyl group, etc. It also includes forms where two or more hydrocarbon aromatic substructures are linked through a sigma bond, such as a biphenyl group, a terphenyl group, a quarterphenyl group, etc. Additionally, it can include non-aromatic condensed rings where two or more hydrocarbon aromatic substructures are directly or indirectly condensed, such as a fluorenyl group, etc.

[0026] An aryl group includes monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings sharing adjacent pairs of carbon atoms) functional groups.

[0027] As used herein, the term "heterocyclic group" is a superordinate concept that includes heteroaryl groups and means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si in place of carbon in a ring compound such as an aryl group, a cycloalkyl group, their fused rings, or combinations thereof. When the heterocyclic group is a fused ring, the entire heterocyclic group or each ring thereof can contain one or more heteroatoms.

[0028] As an example, a "heteroaryl group" means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si within an aryl group. Two or more heteroaryl groups may be directly linked through a sigma bond, or when the heteroaryl group contains two or more rings, the two or more rings may be fused to each other. When the heteroaryl group is a fused ring, each ring can contain 1 to 3 of the heteroatoms.

[0029] More specifically, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms may be 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, but is not limited thereto.

[0030] More specifically, the substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms may be 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 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, or a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof, but is not limited thereto.

[0031] In this specification, the hole property refers to the property of being able to donate electrons to form holes when an electric field is applied, having a conduction property according to the HOMO level, and meaning the property of facilitating the injection of holes formed at the positive electrode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the positive electrode, and the movement in the light-emitting layer.

[0032] Also, the electron property refers to the property of being able to receive electrons when an electric field is applied, having a conduction property according to the LUMO level, and meaning the property of facilitating the injection of electrons formed at 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 in 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] [Chemical formula] In the Chemical Formula 1, Ar 1 and Ar 2 are each independently 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 are each independently 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 are each independently 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 are each independently one of the integers from 1 to 4, n3 is one of the integers from 1 to 3.

[0036] The compound represented by Chemical Formula 1 has a structure containing para-biphenyl substituted with ortho-carbazole on 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 the Chemical Formula 1 has a faster electron mobility than mono-phenyl, improves the stability of electrons by a resonance effect, and can improve the lifetime particularly when applied to a phosphorescent host.

[0038] In addition, a triazine and a carbazole are substituted at the ortho positions of the para-biphenyl, so that the dihedral angle increases due to the steric hindrance of the triazine and the carbazole, and the triazine partial structure and the carbazole partial structure are twisted with respect to each other.

[0039] This is almost separated with little overlap of the HOMO energy level and the LUMO energy level, and fast energy transfer is enabled using a small ΔEst. Therefore, particularly when applied to a phosphorescent host, it exhibits high-efficiency characteristics.

[0040] Moreover, the side reaction path in the excited state is reduced, and particularly when applied to a phosphorescent host, the lifetime is increased.

[0041] On the other hand, the ortho substitution of triazine and carbazole can minimize degradation by reducing the deposition temperature by about 10% compared to para substitution and meta substitution.

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

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

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

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

[0046] The chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4.

[0047]

Chemical formula

[0048] As an example, the above Chemical Formula 1 is represented by the above Chemical Formula 1-2.

[0049] As an example, the above 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 above Ar 1 and Ar 2Each may 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 instance, the aforesaid *-L 1 -Ar 1 and *-L 2 -Ar 2 are each independently selected from among the substituents listed in Group I below.

[0054]

Chemical formula

[0055] For instance, the aforesaid 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 the 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]

Chemical formula

Chemical formula

[0058] The composition for an organic optoelectronic device according to another embodiment includes a first compound and a second compound. The first compound is the compound for an organic optoelectronic device 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 Formula 3 and Chemical Formula 4.

[0059] [Chemistry] In the above Chemical Formula 2, Ar 3 and Ar 4 are each independently 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 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms. R 5 ~R 15 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. m is one of the integers from 0 to 2. [Chemistry] [Chemistry] In the above Chemical Formula 3 and Chemical Formula 4, Ar 5and Ar 6 is each independently 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* Of the two adjacent ones, each is a linking carbon (C) linked to * in Chemical Formula 4, a in Chemical Formula 3 1* ~a 4* The remaining two that are not linked to * in Chemical Formula 4 among a in Chemical Formula 3 are each independently C-L a -R a and are, L a L 5 and L 6 are each independently 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, and can improve the light-emitting efficiency and lifetime characteristics by enhancing the charge mobility and safety.

[0061] As an example, Ar 3 and Ar 4 in Chemical Formula 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 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 3and L 4 is each independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, R in the chemical formula 2 5 ~R 15 is each independently 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 the chemical formula 2 means that at least one hydrogen is substituted with deuterium, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms.

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

[0064]

Chemical formula

Chemical formula

[0065]

Chemical formula

[0066] In one embodiment, the chemical formula 2 is represented by the chemical formula 2-8.

[0067] Also, *-L in Chemical Formula 2-8 3 -Ar 3 and *-L 4 -Ar 4 are each independently selected from Group II above 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 the following Chemical Formula 3A, Chemical Formula 3B, Chemical Formula 3C, Chemical Formula 3D, and Chemical Formula 3E.

[0069]

Chemical Structure

[0070] For example, Ar 5 and Ar 6 in Chemical Formulas 3 and 4 above 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, 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 the chemical formula 3 and the chemical 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 R a1 ~R a4 and R 16 ~R 23 may each independently be hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group, In a specific embodiment, the R a1 ~R a4 and the R 16 ~R 23 may each independently be hydrogen or a phenyl group.

[0074] In a specific embodiment of the present invention, the second compound is represented by the chemical formula 2-8, and Ar in the chemical formula 2-8 3 and Ar 4is 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, and L 3 and L 4 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and R 5 ~R 14 are each independently 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 the chemical formula 3C, and L a3 and L a4 are single bonds, and L 5 and L 6 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, and R 16 ~R 23 , R a3 and R a4 are each hydrogen or a phenyl group, and Ar 5 and Ar 6 are each independently 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]

Chemical formula

Chemical formula

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

[0078] The first compound and the second compound can be included, for example, in a weight ratio of 1:99 to 99:1. By being included within the above range, the bipolar characteristics can be realized 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 the efficiency and lifespan. Within the above range, for example, they can be included in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20, and for example, in a weight ratio of 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 can be included in a weight ratio of 20:80, 30:70, or 40:60.

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

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

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

[0082] A dopant is a substance that is mixed in trace amounts with a compound for an organic optoelectronic device to cause luminescence, and generally substances such as metal complexes that emit light by multiple excitation that excites to a triplet state or higher can be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and one or more kinds can be included.

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

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

[0085] The M is, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and the L 7 and X may be, for example, bidentate ligands.

[0086] L 7 Examples of the ligands represented by L and X can be selected from the chemical formulas listed in the following Group A, but are not limited thereto.

[0087]

Chemical formula

[0088] As an example, it can contain a dopant represented by the following chemical formula V.

[0089]

Chemical formula

Chemical formula

[0090] As an example, it can also contain a dopant represented by the following chemical formula Z-1.

[0091]

Chemical formula

[0092] The dopant according to one embodiment may be a platinum complex, for example, represented by the following Chemical Formula VI.

[0093]

Chemical formula

[0094] Hereinafter, an organic optoelectronic device to which the above-described compound for an organic optoelectronic device or a composition for an organic optoelectronic device is applied will be described.

[0095] The organic optoelectronic device is not particularly limited as long as it can convert electrical energy and light energy into each other, and examples thereof include an organic optoelectronic device, an organic light-emitting device, an organic solar cell, and an organic photoreceptor drum.

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

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

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

[0099] The positive electrode 120 is made of, for example, a conductor with a high work function so that hole injection can be smoothly performed, and is made of, for example, a metal, a metal oxide, and / or a conductive polymer. The positive electrode 120 is, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold or an alloy thereof, a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb, or a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene:PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0100] The negative electrode 110 is made of, for example, a conductor with a low work function so that electron injection can be smoothly performed, and is made of, for example, a metal, a metal oxide, and / or a conductive polymer. The negative electrode 110 is, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium or an alloy thereof, or a multilayer structured material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0101] The organic layer 105 can contain the above-described compound for an organic optoelectronic device or the composition for an organic optoelectronic device.

[0102] The organic layer 105 includes a light-emitting layer 130, and the light-emitting layer 130 can contain the above-described compound for an organic optoelectronic device or the composition for an organic optoelectronic device.

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

[0104] The light-emitting layer 130 can contain, for example, the above-described compound for an organic optoelectronic device or the composition for an organic optoelectronic device as a phosphorescent host.

[0105] In addition to the light-emitting layer, the organic layer can 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 enhance the hole injection and / or hole mobility between the anode 120 and the light-emitting layer 130 and block electrons.

[0108] Specifically, the hole transport region 140 can 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 can be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0109] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula]

[0110] In addition to the compounds described above, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds having a structure similar thereto can also be used in the positive hole transport region 140.

[0111] Further, the charge transport region may be, for example, the electron transport region 150.

[0112] The electron transport region 150 can further enhance the 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]

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

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

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

[0117] Still another embodiment may be an organic light-emitting device including a light-emitting layer and an electron transport region as organic layers.

[0118] As shown in FIG. 1, the organic light-emitting device according to one 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.

[0119] On the other hand, the organic light-emitting device may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. in addition to the light-emitting layer as the above-described organic layer.

[0120] The organic light-emitting device 100 can be manufactured by forming a positive electrode or a negative electrode on a substrate, then forming an organic layer by a dry film-forming method such as evaporation, sputtering, plasma plating, and ion plating, and then forming a negative electrode or a positive electrode thereon.

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

Examples

[0122] Hereinafter, the above-described embodiments will be described in more detail through examples. However, the following examples are for illustrative purposes only and do not limit the scope of the rights.

[0123] Hereinafter, starting materials and reactants used in the examples and synthesis examples were purchased from Sigma-Aldrich, TCI, tokyo chemical industry, or P&H tech or synthesized by known methods unless otherwise specified.

[0124] (Production of Compounds for Organic Optoelectronic Devices) The compounds presented as more specific examples of the compounds of the present invention were synthesized by the following steps.

[0125] Synthesis Example 1: Synthesis of Compound A-1 [Chemical Formula]

[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 injected into a flask together with THF (500 mL) and distilled water (165 mL) and refluxed at 80 °C. After 12 hours, the reaction was terminated, diluted with DCM, washed three times with brine, and dried over MgSO4. 60 g of intermediate P-1 was obtained using column chromatography.

[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 injected into a flask together with DMF (500 mL) and refluxed at 150 °C. After 12 hours, the reaction was terminated, diluted with DCM, washed three times with brine, and dried over MgSO4. 32 g of Compound A-1 was obtained using column chromatography.

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

[0129] Step 1: Synthesis of Intermediate P-1 Synthesis was carried out in the same manner as in the first step of Synthesis Example 1 to obtain 60 g of Intermediate P-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 charged into a flask together with DMF (500 mL) and refluxed at 150 °C. After 12 hours, the reaction was terminated, diluted with DCM, washed three times with brine, and dried over MgSO4. Using column chromatography, 38 g of Compound A-3 was obtained.

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

[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 charged into a flask together with THF (500 mL) and distilled water (165 mL) and refluxed at 80 °C. After 12 hours, the reaction was terminated, diluted with DCM, washed three times with brine, and dried over MgSO4. Using column chromatography, 33 g of Intermediate P-2 was obtained.

[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 injected into a flask together with DMF (500 mL) and refluxed at 150 °C. After 12 hours, the reaction was terminated, diluted with DCM, washed three times with brine, and dried over MgSO4. Using column chromatography, 25 g of Compound A-11 was obtained.

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

Chem.

[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 injected into a flask together with THF (500 mL) and distilled water (165 mL) and refluxed at 80 °C. After 12 hours, the reaction was terminated, diluted with DCM, washed three times with brine, and dried over MgSO4. Using column chromatography, 42 g of Intermediate P-3 was obtained.

[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 injected into a flask together with DMF (500 mL) and refluxed at 150 °C. After 12 hours, the reaction was terminated, diluted with DCM, washed three times with brine, and dried over MgSO4. Using column chromatography, 32 g of Compound A-21 was obtained.

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

Chem.

[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

Chemical formula

[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 injected into a flask together with THF (500 mL) and distilled water (165 mL), and refluxed at 80 °C. After 12 hours, the reaction was terminated, diluted with DCM, washed three times with brine, and dried over MgSO4. 26 g of intermediate P-4 was obtained using column chromatography.

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

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

Chemical formula

[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 charged into a flask together with THF (500 mL) and distilled water (165 mL), and refluxed at 80 °C. After 12 hours, the reaction was terminated, diluted with DCM, washed three times with brine, and dried over MgSO4. 26 g of intermediate P-5 was obtained using column chromatography.

[0144] Step 2: Synthesis of Compound R-2 Intermediate P-5 (26 g / 1.0 eq.), 9H-carbazole (1.5 eq.), and K3PO4 (3.0 eq.) were charged into a flask together with DMF (500 mL) and refluxed at 150 °C. After 12 hours, the reaction was terminated, diluted with DCM, washed three times with brine, and dried over MgSO4. 15 g of compound R-2 was obtained using column chromatography.

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

Chemical formula

[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 charged into a flask together with THF (500 mL) and distilled water (165 mL), and refluxed at 80 °C. After 12 hours, the reaction was terminated, diluted with DCM, washed three times with brine, and dried over MgSO4. 30 g of intermediate P-6 was obtained using column chromatography.

[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 injected into a flask together with DMF (500 mL) and refluxed at 150 °C. After 12 hours, the reaction was terminated, diluted with DCM, washed three times with brine, and dried over MgSO4. 8 g of compound R-3 was obtained using column chromatography.

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

Chemical Structure

[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 injected into a flask together with THF (500 mL) and distilled water (165 mL) and refluxed at 80 °C. After 12 hours, the reaction was terminated, diluted with DCM, washed three times with brine, and dried over MgSO4. 25 g of intermediate P-7 was obtained using column chromatography.

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

[0151] (Fabrication of Organic Light-Emitting Devices) Example 1 A glass substrate thin-film coated with ITO (Indium tin oxide) was ultrasonically cleaned with distilled water. After the distilled water cleaning was completed, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, and then it was dried. Then, after transferring it to a plasma cleaning device, the substrate was cleaned with oxygen plasma for 10 minutes, and then the substrate was transferred to a vacuum evaporation device. Using the thus-prepared ITO transparent electrode as the positive electrode, compound A doped with 3% NDP-9 (manufactured by Novaled) was vacuum-evaporated on the top of the ITO substrate to form a hole injection layer with a thickness of 100 Å, and compound A was evaporated to a thickness of 1350 Å on the top of the hole injection layer to form a hole transport layer. Compound B was evaporated to a thickness of 350 Å on the top of the hole transport layer to form a hole transport auxiliary layer. Using compound A-1 obtained in Synthesis Example 1 as a host and doping 7 wt% of PhGD as a dopant, a light-emitting layer with a thickness of 400 Å was formed by vacuum evaporation. Next, compound C was evaporated to a thickness of 50 Å on the top of the light-emitting layer to form an electron transport auxiliary layer, and compound D and Liq were simultaneously vacuum-evaporated at a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å. An organic light-emitting device was fabricated by sequentially vacuum-evaporating 15 Å of LiQ and 1200 Å of Al on the top of the electron transport layer to form a negative electrode.

[0152] It was fabricated with the structure of 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 [Chemical Structure]

[0154] Examples 2 to 4 and Comparative Examples 1 to 4 Devices of Examples 2 to 4 and Comparative Examples 1 to 4 were fabricated in the same manner as in Example 1, except that the host was changed as described in Table 1 below.

[0155] Example 5 A glass substrate thin-film coated with ITO (Indium tin oxide) was ultrasonically cleaned with distilled water. After the distilled water cleaning was completed, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, and then dried. Thereafter, after transferring to a plasma cleaning apparatus, the substrate was cleaned with oxygen plasma for 10 minutes, and then the substrate was transferred to a vacuum evaporation apparatus. Using the thus-prepared ITO transparent electrode as the positive electrode, compound A doped with 3% of NDP-9 (manufactured by Novaled) was vacuum-evaporated on the upper part of the ITO substrate to form a hole injection layer with a thickness of 100 Å, and compound A was evaporated to a thickness of 1350 Å on the upper part of the hole injection layer to form a hole transport layer. Compound E was evaporated to a thickness of 350 Å on the upper part of the hole transport layer to form a hole transport auxiliary layer. On the upper part of the hole transport auxiliary layer, compound A-1 obtained in Synthesis Example 1 and compound B-136 obtained in Synthesis Example 5 were simultaneously used as hosts, and PhGD was doped at 10 wt% as a dopant, and a light-emitting layer with a thickness of 400 Å was formed by vacuum evaporation. Here, compound A-1 and compound B-136 were used at a weight ratio of 3:7. Next, compound F was evaporated to a thickness of 50 Å on the upper part of the light-emitting layer to form an electron transport auxiliary layer, and compound G and Liq were simultaneously vacuum-evaporated at a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å. An organic light-emitting device was fabricated by sequentially vacuum-evaporating 15 Å of LiQ and 1200 Å of Al on the upper part of the electron transport layer to form a negative electrode.

[0156] It was fabricated with the structure of 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 = 90 wt%:10 wt%] (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-fluorene-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 Devices of Examples 6 to 8 and Comparative Examples 5 to 8 were fabricated in the same manner as in Example 5, except that the host was changed as described in Table 2 below.

[0159] Evaluation (1) Measurement of change in current density according to voltage change For the fabricated organic light-emitting device, while increasing the voltage from 0 V to 10 V, the current value flowing through the unit device was measured using a current-voltage meter (Keithley 2400), and the measured current value was divided by the area to obtain the result.

[0160] (2) Measurement of change in luminance according to voltage change For the fabricated organic light-emitting device, while increasing the voltage from 0 V to 10 V, the luminance at that time was measured using a luminance meter (Minolta Cs-1000A) to obtain the result.

[0161] (3) Measurement of luminous efficiency (1) and (2) Using the measured luminance and current density, the luminous efficiency (cd / A) at the same current density (10 mA / cm 2 ) was 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) Lifetime measurement For the manufactured organic light-emitting device, using a Polarox lifetime measurement system, the initial luminance (cd / m 2 ) was made to emit light at 24,000 cd / m 2 , the decrease in luminance over time was measured, and the time point when the luminance decreased to 95% of the initial luminance was measured as the T95 lifetime.

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

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

[0167] (5) Measurement of driving voltage Using a current-voltage meter (Keithley 2400), the driving voltage of each device was measured at 15 mA / cm 2 to obtain the results.

[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 confirmed that the organic light-emitting device to which the compound according to the embodiment of the present invention is applied has very improved driving, efficiency, and lifetime characteristics compared to the organic light-emitting device according to the comparative example.

[0172] In particular, referring to Table 2, it can be confirmed that the efficiency and lifetime 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.

[0173] Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements by those skilled in the art using the basic concept of the present invention defined in the claims also belong to the scope of the present invention.

Description of Reference Numerals

[0174] 100 Organic light-emitting device 105 Organic layer 110 Negative electrode 120 Positive electrode 130 Light-emitting layer 140 Hole transport region 150 Electron transport region

Claims

1. A compound for an organic optoelectronic device represented by the following Chemical Formula 1: 【Chemical Formula 1】 In the 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 are each independently 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 are each independently one of the integers from 1 to 4, n3 is one of the integers from 1 to 3.

2. The compound for an organic optoelectronic device according to Claim 1, represented by any one of the following Chemical Formulas 1-1 to 1-4: [Chemical 2] In the Chemical Formulas 1-1 to 1-4, Ar 1 ~Ar 3 、R 1 、R 2 、n1, n3, n4, L 1 and L 2 are as defined in claim 1.

3. Said 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, and the compound for an organic optoelectronic device according to claim 1.

4. The above-mentioned 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, and the compound for an organic optoelectronic device according to Claim 1.

5. Said *-L 1 -Ar 1 and *-L 2 -Ar 2 each independently represents one selected from the substituents listed in Group I below: The compound for an organic optoelectronic device according to Claim 1 [Chemical Formula 3] In the Group I, * is the connection point.

6. The compound for an organic optoelectronic device according to Claim 1, which is one selected from the compounds listed in the following Group 1: 【Chemical Formula 4】 【Chemical Formula 5】 ​ 【Chemical Formula 7】 。

7. An organic optoelectronic device composition comprising a first compound and a second compound, wherein the first compound is the compound for an organic optoelectronic device according to Claim 1, and the second compound is 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: 【Chemical 8】 In the Chemical Formula 2, Ar 3 and Ar 4 are each independently 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 to 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 one of the integers from 0 to 2, 【Chemical Formula 9】 【Chemical Formula 10】 In the Chemical Formulas 3 and 4, Ar 5 and Ar 6 are each independently 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* Of the two adjacent ones among them, each is a linking carbon (C) linked to * in Chemical Formula 4, a in Chemical Formula 3 1* ~a 4* Of these, the remaining two that are not linked to * in Chemical Formula 4 are each independently C-L a -R a and are L a 、 L 5 and L 6 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, R a and R 16 to 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 organic optoelectronic device composition according to Claim 7, wherein the Chemical Formula 2 is represented by the following Chemical Formula 2-8: 【Chemical 11】 In the Chemical Formula 2-8, R 5 to 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 each is independently one of the substituents listed in Group II below, 【Chemical Formula 12】 In the Group II, * is the connection point.

9. The organic optoelectronic device composition according to Claim 7, wherein the combination of the Chemical Formulas 3 and 4 is represented by the following Chemical Formula 3C: 【Chemical 13】 In the 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 およびR a4 are each independently hydrogen 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, including at least one organic layer located between the positive electrode and the negative electrode, wherein the organic layer contains the compound for an organic optoelectronic device according to any one of Claims 1 to 6, or the organic optoelectronic device composition according to any one of Claims 7 to 9, an organic optoelectronic device.

11. The organic layer includes a light-emitting layer, and the light-emitting layer contains the compound for an organic optoelectronic device or the organic optoelectronic device composition, the organic optoelectronic device according to Claim 10.

12. A display device including the organic optoelectronic device according to Claim 10.

Citation Information

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