Composition for organic optoelectronic element, organic optoelectronic element, and display

Abstract

To provide a composition for an organic optoelectronic element capable of achieving low drive, high performance, and long life.SOLUTION: The present invention relates to a first compound represented by the following formula, a composition for an organic optoelectronic element containing a specific second compound, an organic optoelectronic element containing the same, and a display.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. [Background technology]

[0002] An organic optoelectronic diode is a device that can convert electrical energy and light energy into each other. Organic optoelectronic diodes 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 separate electrodes to generate electrical energy. The other is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to the electrodes.

[0003] Examples of organic optoelectronic devices include organic photoelectric devices, organic light emitting devices, organic solar cells, and organic photoconductor drums. Among these, organic light emitting diodes (OLEDs) have been attracting much attention in recent years due to the increasing demand for flat panel display devices. Summary of the Invention [Problem to be solved by the invention]

[0004] 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. [Means for solving the problem]

[0005] One embodiment provides a composition for an organic optoelectronic device that can realize a low-driving, highly efficient, and long-life organic optoelectronic device. Another embodiment provides an organic optoelectronic device comprising the composition. Yet another embodiment provides a display device comprising the organic optoelectronic device.

[0006] According to one embodiment, there is provided a composition for an organic optoelectronic device, comprising a first compound represented by the following Chemical Formula 1, and a second compound represented by a combination of the following Chemical Formulas 2 and 3: [Chemical formula 1]

[0007] [ka]

[0008] In chemical formula 1, L 1 and L 2 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, 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, R 1 ~R 4 are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Ar 6 ~Ar 9 are each independently hydrogen or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, m1 and m4 each independently represent an integer from 1 to 4; m2 and m3 are each independently an integer of 1 to 3. Chemical formula 1 simultaneously satisfies the following conditions (i) and (ii): (i)Ar 1 and Ar 2At least one of the groups is an aryl group having 6 to 30 carbon atoms and substituted with at least one deuterium atom, or a heterocyclic group having 2 to 30 carbon atoms and substituted with at least one deuterium atom. (ii)R 1 ~R 4 At least one of these is deuterium. [Chemical formula 2] [Chemical formula 3]

[0009] [ka]

[0010] In Chemical Formula 2 and Chemical Formula 3, Ar 3 ~Ar 5 each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, a1 * ~a4 * are each independently a linking carbon (C) or CL a -R a and a1 of Chemical Formula 2 * ~a4 * The two adjacent ones in the middle are of formula 3 * and L a and L 3 ~L 6 each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, R a and R 5 ~R 12 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amino 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.

[0011] According to another embodiment, an organic optoelectronic device is provided, which includes a positive electrode and a negative electrode facing each other and at least one organic layer positioned between the positive electrode and the negative electrode, the organic layer including a composition for an organic optoelectronic device. According to yet another embodiment, a display device is provided, which includes the organic optoelectronic device. An organic optoelectronic device having the effects of low driving, high efficiency, and long life can be realized. [Brief explanation of the drawings]

[0012] [Figure 1] 1 is a cross-sectional view illustrating an organic light-emitting device according to an embodiment. DETAILED DESCRIPTION OF THE INVENTION

[0013] Hereinafter, embodiments of the present invention will be described in detail, but these are presented as examples and are not intended to limit the present invention, which is defined only by the scope of the claims set forth below.

[0014] Unless otherwise defined, the term "substituted" used herein means that at least one hydrogen atom in a substituent or 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.

[0015] In one example of the present invention, "substituted" means that at least one hydrogen atom in a substituent or compound is substituted with deuterium, an alkyl group having 1 to 30 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, or a cyano group. In another specific example of the present invention, "substituted" means that at least one hydrogen atom in a substituent or compound is substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a cyano group. In another specific example of the present invention, "substituted" means that at least one hydrogen atom in a substituent or compound is substituted with deuterium, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a cyano group. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen atom of a substituent or compound is substituted with deuterium, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0016] As used herein, "unsubstituted" means that the hydrogen atom is not replaced with another substituent and remains as a hydrogen atom.

[0017] As used herein, "deuterium substitution (-D)" can include "tritium substitution (-T)."

[0018] As used herein, unless otherwise defined, the term "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 is carbon.

[0019] As used herein, the term "aryl group" refers to a general group having one or more hydrocarbon aromatic moieties, and includes a group in which all elements of the hydrocarbon aromatic moieties have p-orbitals and these p-orbitals form conjugation, such as a phenyl group or naphthyl group, a group in which two or more hydrocarbon aromatic moieties are linked through a sigma bond, such as a biphenyl group, a terphenyl group, or a quaterphenyl group, and a non-aromatic fused ring in which two or more hydrocarbon aromatic moieties are directly or indirectly fused, such as a fluorenyl group. The aryl group includes monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings sharing adjacent pairs of carbon atoms) functional groups.

[0020] As used herein, the term "heterocyclic group" is a broader term that includes a heteroaryl group and refers to a group containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si in place of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. When a heterocyclic group is a fused ring, the heterocyclic group as a whole or each ring may contain one or more heteroatoms. For example, a "heteroaryl group" refers to an aryl group containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si. Two or more heteroaryl groups may be directly linked via a sigma bond, or when a heteroaryl group contains two or more rings, the two or more rings may be fused to each other. When a heteroaryl group is a fused ring, each ring may contain 1 to 3 heteroatoms.

[0021] 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, a substituted or unsubstituted furanyl group, or a combination thereof.

[0022] More specifically, the substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms is 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, or 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.

[0023] In this specification, the term "hole characteristic" refers to the ability to donate electrons to form holes when an electric field is applied, and refers to the ability to have conduction characteristics depending on the HOMO level, 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 of holes in the light-emitting layer. The term "electron characteristic" refers to the ability to receive electrons when an electric field is applied, and refers to the ability to have conduction characteristics depending on the LUMO level, 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 of electrons in the light-emitting layer.

[0024] A composition for an organic optoelectronic device according to one embodiment will be described below.

[0025] A composition for an organic optoelectronic device according to one embodiment includes a first compound represented by Chemical Formula 1 and a second compound represented by a combination of Chemical Formula 2 and Chemical Formula 3. The first compound is represented by Chemical Formula 1 below. [Chemical formula 1]

[0026] [ka]

[0027] In chemical formula 1, L 1 and L 2 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and 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, and R 1 ~R 4 are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; m1 and m4 are each independently an integer of 1 to 4; m2 and m3 are each independently an integer of 1 to 3; Ar 6 ~Ar 9are each independently hydrogen or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Chemical formula 1 simultaneously satisfies the following conditions (i) and (ii): (i)Ar 1 and Ar 2 At least one of the groups is an aryl group having 6 to 30 carbon atoms and substituted with at least one deuterium atom, or a heterocyclic group having 2 to 30 carbon atoms and substituted with at least one deuterium atom. (ii)R 1 ~R 4 At least one of these is deuterium.

[0028] The first compound represented by chemical formula 1 has a biscarbazole skeleton, in which the benzene moiety forming the carbazole is substituted with at least one deuterium atom, and the 9th (N-direction) substituent of the carbazole is Ar. 1 and Ar 2 The compound has a structure in which at least one of the benzene moieties forming the carbazole and the 9th (N-directed) substituent of the carbazole are substituted with deuterium. The simultaneous substitution of deuterium with deuterium can further lower the zero-point energy and vibrational energy of the compound. This further lowers the ground state energy, weakening the intermolecular interactions and allowing the formation of an amorphous thin film, which further improves heat resistance and is effective in extending the lifetime. In other words, when this is applied, it is possible to realize organic light-emitting devices with low drive, high efficiency, and particularly long lifetime.

[0029] Chemical formula 1 can be expressed, for example, as any one of the following chemical formulas 1-1 to 1-10, depending on the linking position of carbazole. [Chemical formula 1-1]

[0030] [ka]

[0031] [Chemical formula 1-2]

[0032] [ka]

[0033] [Chemical formula 1-3]

[0034]

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[0035] [Chemical formula 1-4]

[0036]

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[0037] [Chemical Formula 1-5]

[0038]

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[0039] [Chemical formula 1-6]

[0040]

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[0041] [Chemical Formula 1-7]

[0042]

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[0043] [Chemical Formula 1-8]

[0044]

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[0045] [Chemical Formula 1-9]

[0046]

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[0047] [Chemical formula 1-10]

[0048] [ka]

[0049] In chemical formulas 1-1 to 1-10, L 1 , L 2 , Ar 1 , Ar 2 , Ar 6 ~Ar 9 , R 1 ~R 4 The definitions of m1 to m4 are as described above. 1 If is 2 or more, each R 1 may be the same or different from each other. 2 If is 2 or more, each R 2 may be the same or different from each other. 3 If is 2 or more, each R 3 may be the same or different from each other. 4 If is 2 or more, each R 4 may be the same or different from each other. 6 If is 2 or more, each Ar 6 may be the same or different from each other. 7 If is 2 or more, each Ar 7 may be the same or different from each other. 8 If is 2 or more, each Ar 8 may be the same or different from each other. 9 If is 2 or more, each Ar 9 may be the same or different from each other. For example, R 1 ~R 4 At least two of the may be deuterium. For example, R 1 ~R 4 are each deuterium, m1 and m4 are each an integer of 4, and m2 and m3 are each an integer of 3. For example, R 1and R 2 are each deuterium, m1 is an integer from 1 to 4, m2 is an integer from 1 to 3, and R 3 and R 4 may each be hydrogen. For example, R 3 and R 4 are deuterium, m3 is an integer from 1 to 3, m4 is an integer from 1 to 4, and R 1 and R 2 may each be hydrogen. For example, R 1 and R 4 are each deuterium, m1 and m4 are each an integer from 1 to 4, and R 2 and R 3 may each be hydrogen. For example, R 1 ~R 3 are each deuterium, m2 and m3 are each an integer of 1 to 3, m1 is an integer of 1 to 4, and R 4 may be deuterium or an aryl group having 6 to 30 carbon atoms which may be substituted or unsubstituted with deuterium.

[0050] For example, R 1 ~R 4 Depending on the substitution position of the deuterium substituted in, Chemical Formula 1 can be represented by any one of Chemical Formulas 1a to 1e below. [Chemical formula 1a]

[0051] [ka]

[0052] [Formula 1b]

[0053] [ka]

[0054] [Chemical formula 1c]

[0055] [ka]

[0056] [Chemical formula 1d]

[0057] [ka]

[0058] [Chemical formula 1e]

[0059] [ka]

[0060] In chemical formulas 1a to 1e, L 1 , L 2 , Ar 1 , Ar 2 and Ar 6 ~Ar 9 The definition of Ar is as described above. 6 ~Ar 9 are each independently an aryl group having 6 to 30 carbon atoms, which may be substituted with hydrogen or deuterium, or may not be substituted, and D3 means that three deuterium atoms are substituted. For example, Ar 1 and Ar 2 At least one of the groups may be a phenyl group substituted with at least one deuterium, a biphenyl group substituted with at least one deuterium, a terphenyl group substituted with at least one deuterium, a naphthyl group substituted with at least one deuterium, an anthracenyl group substituted with at least one deuterium, a phenanthrenyl group substituted with at least one deuterium, a triphenylene group substituted with at least one deuterium, a fluorenyl group substituted with at least one deuterium, a dibenzofuranyl group substituted with at least one deuterium, or a dibenzothiophenyl group substituted with at least one deuterium. 1 and Ar 2At least one of the groups may be a phenyl group substituted with at least one deuterium, a biphenyl group substituted with at least one deuterium, a terphenyl group substituted with at least one deuterium, a triphenylene group substituted with at least one deuterium, a dibenzofuranyl group substituted with at least one deuterium, or a dibenzothiophenyl group substituted with at least one deuterium. 6 ~Ar 9 may each independently be an aryl group having 6 to 20 carbon atoms, which may be substituted or unsubstituted with hydrogen or deuterium. For example, Ar 6 ~Ar 9 are each independently hydrogen or may be a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a deuterium-substituted or unsubstituted naphthyl group, a deuterium-substituted or unsubstituted phenanthrenyl group, a deuterium-substituted or unsubstituted anthracenyl group, a deuterium-substituted or unsubstituted triphenylene group, or a deuterium-substituted or unsubstituted fluorenyl group.

[0061] For example, L in Formula 1 1 -Ar 1 and L 2 -Ar 2 are each independently selected from the substituents listed in Group I-1 and Group I-2 below, and L 1 -Ar 1 and L 2 -Ar 2 At least one of the following is selected from the substituents listed in Group I-2 below.

[0062] [Group I-1]

[0063] [ka]

[0064] [Group I-2]

[0065] [ka] JPEG2025134728000022.jpg84142

[0066] [ka] JPEG2025134728000024.jpg90153

[0067] [ka]

[0068] In Group I-1 and Group I-2, * is a connection point.

[0069] For example, Chemical Formula 1 is represented by Chemical Formula 1-8a or Chemical Formula 1-8e below. [Formula 1-8a]

[0070] [ka]

[0071] [Formula 1-8e]

[0072] [ka]

[0073] In Chemical Formula 1-8a and Chemical Formula 1-8e, L 1 , L 2 , Ar 1 and Ar 2 is as mentioned above, and Ar 9 is a deuterium-substituted or unsubstituted aryl group having 6 to 30 carbon atoms. For example, Ar 9may be a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a deuterium-substituted or unsubstituted naphthyl group, a deuterium-substituted or unsubstituted phenanthrenyl group, a deuterium-substituted or unsubstituted anthracenyl group, a deuterium-substituted or unsubstituted triphenylene group, or a deuterium-substituted or unsubstituted fluorenyl group.

[0074] For example, the compound for an organic optoelectronic device represented by Chemical Formula 1 may be one selected from the compounds listed in Group 1 below, but is not limited thereto. [Group 1]

[0075] [ka] JPEG2025134728000029.jpg43136

[0076] [ka] JPEG2025134728000031.jpg47136 JPEG2025134728000032.jpg48134 JPEG2025134728000033.jpg45132

[0077] [ka] JPEG2025134728000035.jpg57134 JPEG2025134728000036.jpg64151

[0078] [ka] JPEG2025134728000038.jpg59153 JPEG2025134728000039.jpg57148

[0079]

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[0080]

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[0081]

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[0082]

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[0083]

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[0084]

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[0085]

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[0086]

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[0087]

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[0088]

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[0089]

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[0090]

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[0091]

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[0092]

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[0093]

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[0094]

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[0095] [ka]

[0096] As a more specific example, the compound for an organic optoelectronic device according to the present invention is represented by Chemical Formula 1-8a, 1 and L 2 is a single bond or a substituted or unsubstituted phenylene group, and Ar 1 and Ar 2 may be a deuterium-substituted phenyl group, a deuterium-substituted biphenyl group, a deuterium-substituted biphenyl group, or a deuterium-substituted triphenylene group, respectively.

[0097] The second compound is represented by a combination of Chemical Formula 2 and Chemical Formula 3 below. [Chemical formula 2] [Chemical formula 3]

[0098] [ka]

[0099] In Chemical Formula 2 and Chemical Formula 3, Ar 3 ~Ar 5 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, and a1 in Chemical Formula 2 * ~a4 * are each independently a linking carbon (C) or CL a -R a and a1 in Chemical Formula 2 * ~a4 * The two adjacent ones in the middle are of formula 3 * and L a , L 3 ~L 6are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms; R a and R 5 ~R 12 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amino 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. The second compound is used in the light-emitting layer together with the first compound to increase charge mobility and safety, thereby improving luminous efficiency and life characteristics.

[0100] For example, the second compound is represented by any one of the following Chemical Formula 2A, Chemical Formula 2B, Chemical Formula 2C, Chemical Formula 2D, Chemical Formula 2E, and Chemical Formula 2F. [Chemical formula 2A] [Chemical formula 2B]

[0101] [ka]

[0102] [Chemical formula 2C] [Chemical formula 2D]

[0103] [ka]

[0104] [Chemical formula 2E] [Chemical formula 2F]

[0105] [ka]

[0106] In chemical formulas 2A to 2F, Ar 3 ~Ar 5 , L 3 ~L 6 , and R 5 ~R 12 is as mentioned above, and L a1 ~La4 is the aforementioned L 3 ~L 6 is identical to the definition of R a1 ~R a4 is the aforementioned R 5 ~R 12 For example, the definition of Ar in formulas 2 and 3 is the same as that of 3 ~Ar 5 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl 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. a1 ~R a4 and R 5 ~R 12 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.

[0107] In a specific embodiment of the present invention, Ar of Formula 2 and Formula 3 3 ~Ar 5 are each independently selected from the substituents listed in Group II below.

[0108] [Group II]

[0109] [ka] JPEG2025134728000097.jpg66117

[0110] In Group II, * is a connection point. In one embodiment, R a1 ~R a4 and R 5 ~R12 may each independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. 5 ~R 12 may each independently be hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group. 5 ~R 12 Each of L may independently be hydrogen, deuterium, or a cyano group. 3 ~L 6 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted pyridinylene group; Ar 3 ~Ar 5 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0111] In a specific embodiment of the present invention, the second compound can be represented by Chemical Formula 2B, and L a1 and L a2 is a single bond, and L 3 ~L 6 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, and R 5 ~R 12 , R a1 and R a2 are each independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group; Ar 3 ~Ar 5 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0112] For example, the second compound may be one selected from the compounds listed in Group 2 below, but is not limited thereto.

[0113] [Group 2] [A-1] [A-2] [A-3] [A-4] [A-5]

[0114] [ka]

[0115] [A-6] [A-7] [A-8] [A-9] [A-10]

[0116] [ka]

[0117] [A-11] [A-12] [A-13] [A-14] [A-15]

[0118] [ka]

[0119] [A-16] [A-17] [A-18] [A-19] [A-20]

[0120] [ka]

[0121] [A-21] [A-22] [A-23] [A-24] [A-25]

[0122] [ka]

[0123] [A-26] [A-27] [A-28] [A-29] [A-30]

[0124]

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[0125] [B-1] [B-2] [B-3] [B-4] [B-5]

[0126]

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[0127] [B-6] [B-7] [B-8] [B-9] [B-10]

[0128]

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[0129] [B-11] [B-12] [B-13] [B-14] [B-15]

[0130]

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

[0132]

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[0133] [B-21] [B-22] [B-23] [B-24] [B-25]

[0134]

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[0135] [B-26] [B-27] [B-28] [B-29] [B-30]

[0136]

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[0137] [B-31] [B-32] [B-33] [B-34] [B-35]

[0138]

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[0139] [B-36] [B-37] [B-38] [B-39] [B-40]

[0140]

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[0141] [B-41] [B-42] [B-43] [B-44] [B-45]

[0142]

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[0143] [B-46] [B-47] [B-48] [B-49] [B-50]

[0144]

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[0145] [B-51] [B-52] [B-53] [B-54] [B-55]

[0146]

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[0147] [B-56] [B-57] [B-58] [B-59] [B-60]

[0148]

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[0149] [B-61] [B-62] [B-63] [B-64]

[0150]

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[0151] [B-65] [B-66] [B-67] [B-68] [B-69]

[0152]

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[0153] [B-70] [B-71] [B-72] [B-73] [B-74]

[0154]

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[0155] [B-75] [B-76] [B-77] [B-78]

[0156]

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[0157] [B-79] [B-80] [B-81] [B-82]

[0158]

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[0159] [C-1] [C-2] [C-3] [C-4] [C-5]

[0160]

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[0161] [C-6] [C-7] [C-8] [C-9] [C-10]

[0162]

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[0163] [C-11] [C-12] [C-13] [C-14] [C-15]

[0164]

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[0165] [C-16] [C-17] [C-18] [C-19] [C-20]

[0166]

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[0167] [C-21] [C-22] [C-23] [C-24] [C-25]

[0168]

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[0169] [C-26] [C-27] [C-28] [C-29] [C-30]

[0170]

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[0171] [D-1] [D-2] [D-3] [D-4] [D-5]

[0172]

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[0173] [D-6] [D-7] [D-8] [D-9] [D-10]

[0174] [Chemical formula]

[0175] [D-11] [D-12] [D-13] [D-14] [D-15]

[0176] [Chemical formula]

[0177] [D-16] [D-17] [D-18] [D-19] [D-20]

[0178] [Chemical formula]

[0179] [D-21] [D-22] [D-23] [D-24] [D-25]

[0180] [Chemical formula]

[0181] [D-26] [D-27] [D-28] [D-29] [D-30]

[0182] [Chemical formula]

[0183] [E-1] [E-2] [E-3] [E-4] [E-5]

[0184] [Chemical formula]

[0185] [E-6] [E-7] [E-8] [E-9] [E-10]

[0186] [Chemistry]

[0187] [E-11] [E-12] [E-13] [E-14] [E-15]

[0188] [Chemistry]

[0189] [E-16] [E-17] [E-18] [E-19] [E-20]

[0190] [Chemistry]

[0191] [E-21] [E-22] [E-23] [E-24] [E-25]

[0192] [Chemistry]

[0193] [E-26] [E-27] [E-28] [E-29] [E-30] [Chemistry] <s

[0194] [F-1] [F-2] [F-3] [F-4] [F-5]

[0195] [Chemistry]

[0196] [F-6] [F-7] [F-8] [F-9] [F-10]

[0197] [ka]

[0198] [F-11] [F-12] [F-13] [F-14] [F-15]

[0199] [ka]

[0200] [F-16] [F-17] [F-18] [F-19] [F-20]

[0201] [ka]

[0202] [F-21] [F-22] [F-23] [F-24] [F-25]

[0203] [ka]

[0204] [F-26] [F-27] [F-28] [F-29] [F-30]

[0205] [ka]

[0206] In a more specific embodiment of the present invention, the first compound is represented by Chemical Formula 1-8a, and the second compound is represented by Chemical Formula 2B.

[0207] The first compound and the second compound are included in a weight ratio of, for example, 1:99 to 99:1. By including them in this range, bipolar characteristics can be achieved by utilizing the electron transport ability of the first compound and the hole transport ability of the second compound, resulting in improved efficiency and lifetime. Within this range, the weight ratios are, for example, about 10:90 to 90:10, about 20:80 to 80:20, and, for example, about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40. Specific examples include a weight ratio of 40:60, 50:50, or 60:40.

[0208] In addition to the first compound and the second compound, the composition may further contain one or more compounds. For example, the composition for an organic optoelectronic device may further contain a dopant. The dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, or may be, for example, a red phosphorescent dopant. The dopant is a substance that is mixed in a small amount into the composition for an organic optoelectronic device to cause light emission, and is generally a substance such as a metal complex that emits light by multiple excitation, which is excited to a triplet state or higher. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and one or more dopants may be included.

[0209] An example of the dopant is a phosphorescent dopant, and examples of the phosphorescent dopant include Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or organometallic compounds containing a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the following chemical formula Z, but is not limited thereto. [Chemical formula Z] L 7 MX In the above chemical formula Z, M is a metal, and L 7and X are the same or different and are ligands that form a complex with M. M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L 7 and X may be, for example, a bidentate ligand. 7 Examples of the ligand represented by X are selected from the chemical formulae listed in Group A below, but are not limited thereto.

[0210] [Group A]

[0211] [ka]

[0212] Group A, R 300 ~R 302 are each independently hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms which may or may not be substituted with a halogen, an aryl group having 6 to 30 carbon atoms which may or may not be substituted with an alkyl group having 1 to 30 carbon atoms, or a halogen; R 303 ~R 324 are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a substituted or unsubstituted amino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, SF5, a trialkylsilyl group having a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a dialkylarylsilyl group having a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and an aryl group having 6 to 30 carbon atoms, or a triarylsilyl group having a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0213] For example, it may contain a dopant represented by the following chemical formula V. [Chemical formula V]

[0214] [ka]

[0215] In chemical formula V, R 101 ~R 116 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or -SiR 132 R 133 R 134 and R 132 ~R 134 are each independently an alkyl group having 1 to 6 carbon atoms, and R 101 ~R 116 At least one of the functional groups represented by the following chemical formula V-1 is 100 is a bidentate ligand of a monovalent anion that coordinates to iridium via an unshared electron pair of a carbon or heteroatom; m15 and m16 are each independently an integer of 0 to 3; and m15+m16 is an integer of 1 to 3.

[0216] [Chemical formula V-1]

[0217] [ka]

[0218] In chemical formula V-1, R 135 ~R 139 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or -SiR 132 R 133 R 134 and R 132 ~R 134 are each independently an alkyl group having 1 to 6 carbon atoms, * means a moiety connected to a carbon atom.

[0219] For example, a dopant represented by the following chemical formula Z-1 may be included. [Chemical formula Z-1]

[0220] [ka]

[0221] In the chemical formula Z-1, rings A, B, C, and D each independently represent a 5- or 6-membered carbocyclic or heterocyclic ring. A , R B , R C , and R D Each independently represents mono-, di-, tri- or tetra-substituted, or unsubstituted. 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. When nA is 1, L E is selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; when nA is 0, L E does not exist. R A , R B , R C , R D R, R, and R' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. A , R B , R C , R D , R, and R′ are optionally linked to form a ring. X B , XC , X D , and X E are each independently selected from the group consisting of carbon and nitrogen. 1 , Q 2 , Q 3 , and Q 4 indicates an oxygen or a direct bond, respectively.

[0222] The dopant according to one embodiment is a platinum complex, for example, represented by the following formula VI: [Chemical formula VI]

[0223] [ka]

[0224] In chemical formula VI, X 100 are O, S and NR 131 is selected from R 117 ~R 131 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or -SiR 132 R 133 R 134 and R 132 ~R 134 are each independently an alkyl group having 1 to 6 carbon atoms, and R 117 ~R 131 At least one of the groups is -SiR 132 R 133 R 134 Or a tert-butyl group.

[0225] Hereinafter, an organic optoelectronic device using the above-mentioned compound for an organic optoelectronic device will be described. The organic optoelectronic device is not particularly limited as long as it is a device that can convert electrical energy and light energy into each other, and examples thereof include organic photoelectric devices, organic light-emitting devices, organic solar cells, and organic photoreceptor drums. Hereinafter, an organic light-emitting device, which is one example of an organic optoelectronic device, will be described with reference to the drawings.

[0226] 1 is a cross-sectional view illustrating an organic light-emitting device according to an embodiment. Referring to FIG. 1, an organic light-emitting device 100 according to an embodiment includes a positive electrode 120 and a negative electrode 110 facing each other, and an organic layer 105 disposed between the positive electrode 120 and the negative electrode 110.

[0227] The positive electrode 120 is formed of a conductor with a high work function to facilitate hole injection, such as a metal, metal oxide, and / or conductive polymer. Examples of the positive electrode 120 include, but are not limited to, metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO and Al or SnO and Sb; and conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyethylenedioxythiophene: PEDOT), polypyrrole, and polyaniline.

[0228] The negative electrode 110 is formed of a conductor with a low work function, for example, to facilitate electron injection, such as a metal, metal oxide, and / or conductive polymer. Examples of the negative electrode 110 include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, and barium, or alloys thereof, and multilayer structures such as LiF / Al, LiO / Al, LiF / Ca, and BaF / Ca.

[0229] The organic layer 105 may include the organic optoelectronic device composition described above. The organic layer 105 may include an emitting layer 130, which may include the organic optoelectronic device composition described above. The organic optoelectronic device composition further including a dopant may be, for example, a red-emitting composition. The emitting layer 130 may include, for example, the organic optoelectronic device composition described above as a phosphorescent host. The organic layer may further include a charge transport region in addition to the emitting layer. The charge transport region may be, for example, a hole transport region 140. The hole transport region 140 may further enhance hole injection and / or hole mobility between the anode 120 and the emitting layer 130 and block electrons.

[0230] 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 is contained in at least one of the hole transport layer and the hole transport auxiliary layer.

[0231] [Group B]

[0232] [ka] JPEG2025134728000151.jpg43131

[0233] [ka] JPEG2025134728000153.jpg38134 JPEG2025134728000154.jpg42136 JPEG2025134728000155.jpg36137 JPEG2025134728000156.jpg42132

[0234] [ka] JPEG2025134728000158.jpg37129 JPEG2025134728000159.jpg38129 JPEG2025134728000160.jpg38135 JPEG2025134728000161.jpg30129

[0235] [ka] JPEG2025134728000163.jpg33129 JPEG2025134728000164.jpg38123 JPEG2025134728000165.jpg33122 JPEG2025134728000166.jpg38101

[0236] [ka] JPEG2025134728000168.jpg24134 JPEG2025134728000169.jpg29134 JPEG2025134728000170.jpg26134 JPEG2025134728000171.jpg28134 JPEG2025134728000172.jpg29134

[0237] In addition to the compounds described above, known compounds described in US Pat. No. 5,061,569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc., and compounds with similar structures can also be used in the hole transport region 140.

[0238] The charge transport region may also be, for example, the electron transport region 150. 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. Specifically, the electron transport region 150 may include an electron transport layer between the negative electrode 110 and the light-emitting layer 130 and an electron transport auxiliary layer between the light-emitting layer 130 and the electron transport layer, and at least one of the compounds listed in Group C below is contained in at least one of the electron transport layer and the transport auxiliary layer.

[0239] [Group C]

[0240] [ka] JPEG2025134728000174.jpg29135

[0241] [ka] JPEG2025134728000176.jpg31134 JPEG2025134728000177.jpg26134 JPEG2025134728000178.jpg2690 JPEG2025134728000179.jpg38115 JPEG2025134728000180.jpg2197

[0242] [ka] JPEG2025134728000182.jpg45127 JPEG2025134728000183.jpg50127 JPEG2025134728000184.jpg37139 JPEG2025134728000185.jpg3582

[0243] [ka] JPEG2025134728000187.jpg36102 JPEG2025134728000188.jpg35115 JPEG2025134728000189.jpg26106

[0244] One embodiment may be an organic light-emitting device including an emitting layer as the organic layer. Another embodiment may be an organic light-emitting device including an emitting layer and a hole transport region as the organic layer. Yet another embodiment may be an organic light-emitting device including an emitting layer and an electron transport region as the organic layer.

[0245] As shown in FIG. 1, an organic light emitting device according to an embodiment of the present invention may include a hole transport region 140 and an electron transport region 150 as the organic layer 105 in addition to the light emitting layer 130. Meanwhile, the organic light emitting device may further include an electron injection layer (not shown) and a hole injection layer (not shown) as the organic layer in addition to the light emitting layer. The organic light emitting device 100 may be manufactured by forming an anode or cathode on a substrate, forming an organic layer using a dry deposition method such as vacuum evaporation, sputtering, plasma plating, or ion plating, and then forming an anode or cathode thereon. The above-described organic light emitting device may be used in an organic light emitting display device. [Example]

[0246] The above-described embodiments will be described in more detail below with reference to examples. However, the following examples are provided for illustrative purposes only and are not intended to limit the scope of the invention.

[0247] 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.

[0248] (Manufacturing compounds for organic photoelectron devices) The compounds presented as more specific examples of the compounds of the present invention were synthesized according to the following steps. (Synthesis of the first compound) The compounds presented as more specific examples of the compounds of the present invention were synthesized according to the following steps.

[0249] Synthesis Example 1: Synthesis of Compound 1-38 [Reaction Scheme 1]

[0250] [ka]

[0251] Step 1: Synthesis of compound Int1 Compound Int1 was synthesized with reference to the method disclosed in Korean Patent Publication No. 10-2016-0049842.

[0252] Step 2: Synthesis of Compounds 1-38 30 g (0.0535 mol) of compound Int1, 40 g (0.267 mol) of trifluoromethanesulfonic acid, and 282 g (3.35 mol) of D6-benzene were mixed and stirred at 10°C for 24 hours. Purified water was added and neutralized with saturated K3PO4 solution. The organic layer was concentrated and purified by column chromatography to obtain 18 g of compound 1-38 (white solid, LC-Mass Mz 578.79, C 42 H 10 D 18 N2) was obtained.

[0253] Comparative Synthesis Example 1: Synthesis of Compound Y1 [Reaction Scheme 2]

[0254] [ka]

[0255] 35g (0.095mol) of (phenyl-4-boronic acid)-9H-carbazole, 517g (0.105mol) of bromobenzene-D, 43.3g (0.0028mol) of Pd(PPh3), 32.7g (0.237mol) of K2CO3, 120ml of purified water, and 320ml of THF were mixed and stirred under reflux. After the reaction was complete, the mixture was cooled, purified water was added, and the organic layer was separated and concentrated. The concentrate was purified using a column to obtain 25g of Int2 (molecular weight 324.43).

[0256] 20 g (0.062 mol) of Int2 was dissolved in 200 ml of DMF, and 11.5 g (0.065 mol) of NBS was slowly added at 0°C. The reaction was terminated by stirring at room temperature, and purified water was added to produce a solid. The solid was purified using a column to obtain 23 g of Int3 (molecular weight 403.33).

[0257] 20 g (0.0496 mol) of Int3, 22 g (0.06 mol) of phenyl-9H-carbazole-3-boronic ester, 1.72 g (0.0015 mol) of Pd(PPh3)4, 13.7 g (0.099 mol) of K2CO3, 50 ml of purified water, and 165 ml of THF were mixed and stirred under reflux. After the reaction was complete, the mixture was cooled, purified water was added, and the organic layer was separated and concentrated. The concentrate was purified using a column to obtain 11.5 g of compound Y1 (molecular weight 565.72).

[0258] Comparative Synthesis Example 2: Synthesis of Compound Y2 [Reaction Scheme 3]

[0259] [ka]

[0260] 47g (0.281mol) of carbazole, 550g (0.310mol) of bromobenzene-D, 53g (0.028mol) of CuI, 58g (0.42mol) of KCO, 5g (0.028mol) of 1,10-phenanthroline, and 560ml of DMF were mixed and stirred under reflux. After the reaction was complete, the mixture was cooled to room temperature and purified water was added to form a solid. The solid was purified using a column to obtain 62g of Int4 (molecular weight 248.33).

[0261] 62 g (0.25 mol) of Int4 was dissolved in DMF. 45 g (0.25 mol) of NBS was slowly added at 0°C, and the reaction was terminated by stirring at room temperature. Purified water was added to the reaction solution to generate crystals, and the solid was purified using a column to obtain 80 g of Int5 (molecular weight 327.23).

[0262] 80g (0.245mol) of Int5, 120g (0.27mol) of 4-biphenyl-carbazole-3-boronic ester, 68g (0.49mol) of K2CO3, 414g (0.0122mol) of Pd(PPh3), 320ml of purified water, and 490ml of THF were mixed and stirred under reflux. After the reaction was completed, purified water was added for extraction, and the organic layer was concentrated. The mixture was purified using a column to obtain 90g of compound Y2 (molecular weight 565.72).

[0263] (Synthesis of the second compound) Synthesis Example 2: Synthesis of Compound B-12 [Reaction Scheme 4]

[0264] [ka] JPEG2025134728000194.jpg26135 JPEG2025134728000195.jpg41138

[0265] Step 1: Synthesis of intermediate M-2 11,12-Dihydroindolo[2,3-a]carbazole (78.35 g, 305.69 mmol, CAS No. 60511-85-5), 3-bromobiphenyl (59.38 g, 254.74 mmol), NaOt-Bu (26.93 g, 280.22 mmol), and Pd2(dba)3 (7 g, 7.64 mmol) were suspended in 1,400 mL of toluene, and P(t-Bu)3 (3.64 mL, 15.28 mmol) was added. The mixture was refluxed and stirred for 12 hours. Distilled water was added to the reaction mixture to separate the mixture. The resulting product was purified using a silica gel column to obtain intermediate M-2 (68.7 g, 57%).

[0266] Step 2: Synthesis of intermediate M-3 2,4-dichloro-6-phenyl-1,3,5-triazine (74.50 g, 329.56 mmol) and 4-biphenylboronic acid (55.47 g, 280.12 mmol) were dissolved in 0.7 L of a 3:1 mixture of tetrahydrofuran (THF) and distilled water, followed by the addition of sodium tert-butoxide (68.32 g, 494.34 mmol) and refluxing for 12 hours. The reaction mixture was cooled and the layers were separated. The organic layer was collected and concentrated. The concentrated residue was purified using a silica gel column to obtain intermediate M-3 (75.9 g, 67%).

[0267] Step 3: Synthesis of Compound B-12 Compound B-12 was obtained using intermediates M-2 and M-3 in the same manner as in the synthesis of intermediate M-2.

[0268] (Fabrication of organic light-emitting devices) Example 1 A glass substrate coated with a thin film of ITO (indium tin oxide) was ultrasonically cleaned with distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, and then dried. The substrate was then transferred to a plasma cleaning device and cleaned using oxygen plasma for 10 minutes. It was then transferred to a vacuum deposition device. The prepared ITO transparent electrode was used as the anode. Compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum-deposited on the top of the ITO substrate to form a 100 Å thick hole injection layer. Compound A was then deposited on the hole injection layer to a thickness of 1350 Å to form a hole transport layer. Compound B was then deposited on the hole transport layer to a thickness of 350 Å to form a hole transport auxiliary layer. Compound 1-38 and compound B-12 obtained in the synthesis example were used together as hosts in a weight ratio of 4:6, and doped with 10 wt% PhGD as a dopant to form a 330 Å thick light-emitting layer by vacuum deposition on top of the hole-transporting auxiliary layer. Compound C was then vacuum-deposited on top of the light-emitting layer to a thickness of 50 Å to form an electron-transporting auxiliary layer, and compound D and LiQ were simultaneously vacuum-deposited in a weight ratio of 1:1 to form a 300 Å thick electron-transporting layer. LiQ (15 Å) and Al (1200 Å) were sequentially vacuum-deposited on top of the electron-transporting layer to form a negative electrode, completing the fabrication of an organic light-emitting device. The structure was ITO / compound A (3% NDP-9 doping, 100 Å) / compound A (1350 Å) / compound B (350 Å) / EML [90 wt% host (compounds 1-38:compound B-12 = 4:6 w / w): 10 wt% PhGD] (330 Å) / compound C (50 Å) / compound D: LiQ (300 Å) / LiQ (15 Å) / Al (1200 Å). 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,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluorene)-2-amine Compound C: 2-[3'-(9,9-Dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine Compound D: 2-(Biphenyl-4-yl)-4-(9,9-diphenyl-9H-fluoren-4-yl)-6-phenyl-1,3,5-triazine [PhGD]

[0269] [ka]

[0270] Comparative Examples 1 to 3 The devices of Comparative Examples 1 to 3 were prepared in the same manner as in Example 1, except that the host was changed as shown in Table 1 below.

[0271] 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). The measured current value was divided by the area to obtain the result.

[0272] (2) Measurement of brightness change according to voltage change The voltage of the fabricated organic light emitting device was increased from 0V to 10V, and the luminance at that time was measured using a luminance meter (Minolta Cs-1000A) to obtain the results.

[0273] (3) Luminous efficiency measurement Using the luminance and current density measured in 1 and 2, the same current density (10 mA / cm 2 The luminous efficiency (cd / A) of the

[0274] (4) Lifespan measurement Luminance (cd / m 2 ) to 24000cd / m 2The time it took for the luminous efficiency (cd / A) to decrease to 95% was measured while maintaining the lamp at this temperature. The values ​​shown in Table 1 are relative values ​​based on the values ​​of Comparative Example 2.

[0275] [Table 1]

[0276] Referring to Table 1, it can be seen that the organic light emitting device according to the embodiment of the present invention has a significantly improved lifespan characteristic compared to the organic light emitting device according to the comparative example.

[0277] Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic concept of the present invention defined in the following claims also fall within the scope of the present invention. [Explanation of symbols]

[0278] 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 first compound represented by the following chemical formula 1, and The compound includes a second compound represented by a combination of the following chemical formula 2 and chemical formula 3: [Chemical formula 1] 【Chemical 1】 In the above Chemical Formula 1, L １ and L ２ each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, Ar １ and Ar ２ each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, R １ ~R ４ are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Ar ６ ~Ar ９ are each independently hydrogen or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, m1 and m4 are each independently an integer from 1 to 4; m2 and m3 are each independently an integer from 1 to 3; The chemical formula 1 satisfies the following conditions (i) and (ii) simultaneously: (i) Ar １ and Ar ２ at least one of is a dibenzofuranyl group substituted with at least one deuterium or a dibenzothiophenyl group substituted with at least one deuterium; and (ii) R １ ~R ４ at least one of which is deuterium; [Chemical formula 2] [Chemical formula 3] 【Chemistry 2】 In Chemical Formula 2 and Chemical Formula 3, Ar ３ ~Ar ５ each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, a1* to a4* each independently represent a linking carbon (C) or C-La-Ra; two adjacent ones of a1* to a4* in Chemical Formula 2 are linked to * in Chemical Formula 3, L ａ , L ３ ~L ６ each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, R ａ and R ５ ~R １２ are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amino 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.

2. The first compound is represented by the following chemical formula 1-8: [Chemical formula 1-8] 【Chemistry 3】 In the above chemical formula 1-8, L １ , L ２ , Ar １ , Ar ２ , Ar ６ ~Ar ９ , R １ ~R ４ 2. The composition for organic optoelectronic devices according to claim 1, wherein the definitions of m1 to m4 are as defined in claim 1.

3. L of Formula 1 １ -Ar １ and L ２ -Ar ２ are each independently one selected from the substituents listed in Group I-1 below, L １ -Ar １ and L ２ -Ar ２ At least one of the groups is one selected from the substituents listed in Group I-2 below, [Group I-1] 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 [Group I-2] 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 2. The composition for organic optoelectronic devices according to claim 1, wherein * in Group I-1 and Group I-2 represents a connecting point.

4. The first compound is represented by the following chemical formula 1-8a: [Chemical formula 1-8a] 【Chemistry 14】 In the above chemical formula 1-8a, L １ , L ２ , Ar １ and Ar ２ The composition for organic optoelectronic devices according to claim 1, wherein is as defined in claim 1.

5. The composition for organic optoelectronic devices according to claim 1 , wherein the first compound is one selected from the compounds listed in Group 1 below: [Group 1] 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemical 21】 【Chemical 22】 【Chemical 23】 【Chemistry 24】 【Chemistry 25】 【Chemical 26】 【Chemical 27】 【Chemical 28】 【Chemical 29】 【Chemistry 30】 【Chemical 31】 【Chemical 32】 【Chemical 33】 【Chemical 34】 【Chemistry 35】 【Chemical 36】 【Chemical 37】 【Chemical 38】 【Chemical 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemical 44】

6. The second compound is represented by any one of the following Chemical Formulas 2A to 2F: [Chemical formula 2A] [Chemical formula 2B] 【Chemistry 45】 [Chemical formula 2C] [Chemical formula 2D] 【Chemistry 46】 [Chemical formula 2E] [Chemical formula 2F] 【Chemistry 47】 In the chemical formulas 2A to 2F, Ar ３ ~Ar ５ , L ３ ~L ６ , and R ５ ~R １２ is as defined in claim 1, L ａ１ ~La ４ is the L ａ is the same as the definition of R ａ１ ~R ａ４ is the aforementioned R ａ The composition for organic optoelectronic devices according to claim 1 , wherein the definition is the same as that of

7. R of Formulas 2 and 3 ５ ~R １２ are each independently hydrogen, deuterium, or a cyano group; Said L ３ ~L ６ is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted pyridinylene group, The Ar ３ ~Ar ５ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

8. The first compound is represented by the following chemical formula 1-8a: The second compound is represented by the following formula 2B: [Chemical formula 1-8a] 【Chemistry 48】 In the above chemical formula 1-8a, L １ and L ２ is a single bond or a substituted or unsubstituted phenylene group, Ar １ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted triphenylene group, Ar ２ is a deuterium-substituted dibenzofuranyl group or a deuterium-substituted dibenzothiophenyl group, [Chemical formula 2B] 【Chemistry 49】 In the above Chemical Formula 2B, L ａ１ and L ａ２ is a single bond, L ３ ~L ６ each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, R ５ ~R １２ , R ａ１ and R ａ２ are each independently hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group; Ar ３ ~Ar ５ 2. The composition for organic optoelectronic devices according to claim 1, wherein each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted triphenylene group.

9. The positive and negative electrodes face each other, at least one organic layer located between the positive electrode and the negative electrode; The organic layer comprises the composition for organic optoelectronic devices according to any one of claims 1 to 8.

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

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

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