Composition for organic optoelectronic device, organic optoelectronic device, and display device

Abstract

The present invention relates to a composition for an organic optoelectronic device, comprising a first compound represented by Chemical Formula 1 and a second compound represented by a combination of Chemical Formula 2 and Chemical Formula 3, and an organic optoelectronic device and a display device comprising the same. The details of Chemical Formulas 1 to 3 are as defined in the specification.

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 Art

[0002] An organic optoelectronic diode is a device capable of mutually converting electrical energy and light energy. Organic optoelectronic devices are roughly 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 generate electrical energy while being transmitted to other electrodes, and the other is a light-emitting device that supplies a voltage or current to an electrode to generate light energy from electrical energy.

[0003] Examples of organic optoelectronic devices include organic optoelectronic devices, organic light-emitting devices, organic solar cells, and organic photo conductor drums. Among these, organic light-emitting diodes (OLEDs) have attracted much attention in recent years with the increasing demand for flat panel display devices.

Summary of the Invention

Problems 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 Problems

[0005] One embodiment provides a composition for an organic optoelectronic device that can realize a low-drive, high-efficiency, and long-life organic optoelectronic device. Another embodiment provides an organic optoelectronic device including the above composition. Still another embodiment provides a display device including the above organic optoelectronic device.

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

[0007] [Chemical Structure]

[0008] 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, 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, 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 one of the integers from 1 to 4, m2 and m3 are each independently one of the integers from 1 to 3. Chemical Formula 1 simultaneously satisfies the following conditions (i) and (ii), (i) Ar 1 and Ar 2At least one of them is an aryl group having 6 to 30 carbon atoms substituted with at least one deuterium or a heterocyclic group having 2 to 30 carbon atoms substituted with at least one deuterium. (ii)R 1 ~R 4 At least one of them is deuterium. [Chemical formula 2] [Chemical formula 3]

[0009]

Chemical

[0010] 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, a1 * ~a4 * are each independently a linking carbon (C) or C-L a -R a and a1 * ~a4 * in Chemical formula 2, two adjacent ones of them are each linked to * in Chemical formula 3, L a and L 3 ~L 6 are 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.

[0011] According to another embodiment, there is provided an organic optoelectronic device including a positive electrode and a negative electrode facing each other, and at least one organic layer located between the positive electrode and the negative electrode, wherein the organic layer contains a composition for an organic optoelectronic device. According to still another embodiment, there is provided a display device including the above organic optoelectronic device. An organic optoelectronic device having the effects of low driving, high efficiency, and long life can be realized.

Brief Description of the Drawings

[0012]

Figure 1

Modes for Carrying Out the Invention

[0013] Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example and does not limit the present invention, which is only defined by the scope of the claims described below.

[0014] As used herein, “substituted” means that, unless otherwise defined, at least one hydrogen 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 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. Also, 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. Additionally, 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.

[0016] As used herein, "unsubstituted" means that a hydrogen atom is not substituted 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, "hetero", unless otherwise defined, means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, P, and Si in one functional group, and the remainder being carbon.

[0019] As used herein, the term "aryl group" is a concept that encompasses groups having one or more hydrocarbon aromatic moieties. All elements of the hydrocarbon aromatic moiety have p-orbitals, and these p-orbitals form a conjugation, including, for example, a phenyl group, a naphthyl group, etc. It also includes forms in which two or more hydrocarbon aromatic moieties are linked through a sigma bond, such as a biphenyl group, a terphenyl group, a quarterphenyl group, etc. It can also include non-aromatic fused rings in which two or more hydrocarbon aromatic moieties are directly or indirectly fused, such as a fluorenyl group, etc. An aryl group includes monocyclic, polycyclic or fused-ring polycyclic (i.e., rings that share an adjacent pair of carbon atoms) functional groups.

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

[0021] More specifically, the 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, a substituted or unsubstituted furanyl group, or a combination thereof, but is not limited thereto.

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

[0023] 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 conduction properties 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. The electron property refers to the property of being able to receive electrons when an electric field is applied, having conduction properties 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.

[0024] Hereinafter, a composition for an organic optoelectronic device according to an embodiment will be described.

[0025] The composition for an organic optoelectronic device according to an 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 the following Chemical Formula 1. [Chemical Formula 1]

[0026] [Chemical Structure]

[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, 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, 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 one of the integers from 1 to 4, m2 and m3 are each independently one of the integers from 1 to 3, and Ar 6 ~Ar 9Each is 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 them is an aryl group having 6 to 30 carbon atoms substituted with at least one deuterium or a heterocyclic group having 2 to 30 carbon atoms substituted with at least one deuterium. (ii) At least one of R 1 ~R 4 is deuterium.

[0028] The first compound represented by chemical formula 1 has a basic skeleton of biscarbazole, and the benzene moiety forming carbazole is substituted with at least one deuterium, and at the same time, Ar which is the 9-position (N-direction) substituent of carbazole 1 and Ar 2 At least one of them has a structure substituted with deuterium. By simultaneously substituting the benzene moiety forming carbazole and the 9-position (N-direction) substituent of carbazole with deuterium, the zero-point energy and vibrational energy of the compound may be further lowered. As a result, the energy of the ground state is further lowered, and the intermolecular interaction becomes weak, so that a thin film in an amorphous state can be formed, and thus the heat resistance is further improved and effective in improving the lifetime. That is, when this is applied, an organic light-emitting device with low drive, high efficiency, and particularly long lifetime can be realized.

[0029] Chemical formula 1 can be represented by, for example, any one of the following chemical formulas 1-1 to 1-10 according to the linking position of carbazole. [Chemical formula 1-1]

[0030]

Chemical formula

[0031] [Chemical formula 1-2]

[0032]

Chemical formula

[0033] [Chemical Formula 1-3]

[0034] [Chemistry]

[0035] [Chemical Formula 1-4]

[0036] [Chemistry]

[0037] [Chemical Formula 1-5]

[0038] [Chemistry]

[0039] [Chemical Formula 1-6]

[0040] [Chemistry]

[0041] [Chemical Formula 1-7]

[0042] [Chemistry]

[0043] [Chemical Formula 1-8]

[0044] [Chemistry]

[0045] [Chemical Formula 1-9]

[0046] [Chemistry]

[0047] [Chemical Formula 1-10]

[0048] [Chem.]

[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 and the definitions of m1 to m4 are as described above. When R 1 is 2 or more, each R 1 may be the same or different from each other. When R 2 is 2 or more, each R 2 may be the same or different from each other. When R 3 is 2 or more, each R 3 may be the same or different from each other. When R 4 is 2 or more, each R 4 may be the same or different from each other. When Ar 6 is 2 or more, each Ar 6 may be the same or different from each other. When Ar 7 is 2 or more, each Ar 7 may be the same or different from each other. When Ar 8 is 2 or more, each Ar 8 may be the same or different from each other. When Ar 9 is 2 or more, each Ar 9 may be the same or different from each other. For example, at least two of R 1 ~R 4 may be deuterium. For example, R 1 ~R 4 may each be deuterium, m1 and m4 may each be an integer of 4, and m2 and m3 may each be an integer of 3. For example, R 1and R 2 are each deuterium, m1 is one of the integers from 1 to 4, m2 is one of the integers from 1 to 3, R 3 and R 4 may each be hydrogen. For example, R 3 and R 4 are each deuterium, m3 is one of the integers from 1 to 3, m4 is one of the integers from 1 to 4, R 1 and R 2 may each be hydrogen. For example, R 1 and R 4 are each deuterium, m1 and m4 are each one of the integers from 1 to 4, R 2 and R 3 may each be hydrogen. For example, R 1 ~R 3 are each deuterium, m2 and m3 are each one of the integers from 1 to 3, m1 is one of the integers from 1 to 4, R 4 may be deuterium or an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium.

[0050] For example, depending on the substitution positions of deuterium substituted in R 1 ~R 4 Chemical formula 1 is represented by any one of the following chemical formula 1a to chemical formula 1e. [Chemical formula 1a]

[0051] [Chemical formula]

[0052] [Chemical formula 1b]

[0053] [Chemical formula]

[0054] [Chemical formula 1c]

[0055] [Chemical formula]

[0056] [Chemical formula 1d]

[0057] [Chem.]

[0058] [Chemical formula 1e]

[0059] [Chem.]

[0060] In Chemical formulas 1a to 1e, L 1 , L 2 , Ar 1 , Ar 2 and Ar 6 ~Ar 9 are defined as described above. Ar 6 ~Ar 9 are each independently an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with hydrogen or deuterium, and D 3 means that three deuteriums are substituted. For example, at least one of Ar 1 and Ar 2 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. As specific examples, Ar 1 and Ar 2At least one of them 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. As specific examples, Ar 6 ~Ar 9 may each independently be an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with hydrogen or deuterium. For example, Ar 6 ~Ar 9 may each independently be a phenyl group which is hydrogen or substituted or unsubstituted with deuterium, a biphenyl group which is substituted or unsubstituted with deuterium, a biphenyl group which is substituted or unsubstituted with deuterium, a naphthyl group which is substituted or unsubstituted with deuterium, a phenanthrenyl group which is substituted or unsubstituted with deuterium, an anthracenyl group which is substituted or unsubstituted with deuterium, a triphenylene group which is substituted or unsubstituted with deuterium, or a fluorenyl group which is substituted or unsubstituted with deuterium.

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

[0062] [Group I-1]

[0063] [Chemical formula]

[0064] [Group I-2]

[0065] [Chemistry]

[0066] [Chemistry]

[0067] [Chemistry]

[0068] In Group I-1 and Group I-2, * are the connection points.

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

[0070] [Chemistry]

[0071] [Chemical Formula 1-8e]

[0072] [Chemistry]

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

[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] [Chemical formula]

[0076] [Chemical formula]

[0077] [Chemical formula]

[0078] [Chemical formula]

[0079] [Chemical formula]

[0080] [Chemical formula]

[0081] [Chemical formula]

[0082]

Chem.

[0083]

Chem.

[0084]

Chem.

[0085]

Chem.

[0086]

Chem.

[0087]

Chem.

[0088]

Chem.

[0089]

Chem.

[0090]

Chem.

[0091]

Chem.

[0092]

Chem.

[0093] [Chemical formula]

[0094] [Chemical formula]

[0095] [Chemical formula]

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

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

[0098] [Chemical formula]

[0099] In Chemical Formula 2 and Chemical Formula 3, Ar 3 to 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 * to a4 * in Chemical Formula 2 are each independently a linking carbon (C) or C-L a -R a and a1 *~a4 * Two adjacent ones are the connecting carbons that are each connected to * and L is a connecting carbon, a L, 3 ~L 6 are 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, and 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, and can improve the light-emitting efficiency and lifetime characteristics by enhancing the charge mobility and safety.

[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]

Chemical Structure

[0102] [Chemical Formula 2C] [Chemical Formula 2D]

[0103]

Chemical Structure

[0104] [Chemical Formula 2E] [Chemical Formula 2F]

[0105]

Chemical Structure

[0106] In Chemical Formulas 2A to 2F, Ar 3 ~Ar5 , L 3 ~L 6 , and R 5 ~R 12 are as described above, and L a1 ~L a4 is the same as the aforementioned L 3 ~L 6 and R a1 ~R a4 is the same as the aforementioned R 5 ~R 12 and the definition 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. R a1 ~R a4 and R 5 ~R 12 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.

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

[0108] [Group II]

[0109] [Chemical Formula]

[0110] In Group II, *is a connection point. In one embodiment, R 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. In a more specific embodiment, R 5 ~R 12 may each independently be hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group. In a more specific embodiment, R 5 ~R 12 may each independently be hydrogen, deuterium, or a cyano group. 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, and 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 are single bonds, L 3 ~L 6 are each independently 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 or a substituted or unsubstituted phenyl group, and Ar 3 ~Ar 5Each may 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] [Chemical formula]

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

[0116] [Chemical formula]

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

[0118] [Chemical formula]

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

[0120] [Chemical formula]

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

[0122] [Chemical formula]

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

[0124]

Chem.

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

[0126]

Chem.

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

[0128]

Chem.

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

[0130]

Chem.

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

[0132]

Chem.

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

[0134]

Chem.

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

[0136] [Chemical]

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

[0138] [Chemical]

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

[0140] [Chemical]

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

[0142] [Chemical]

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

[0144] [Chemical]

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

[0146] [Chemical]

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

[0148]

Chem.

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

[0150]

Chem.

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

[0152]

Chem.

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

[0154]

Chem.

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

[0156]

Chem.

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

[0158]

Chem.

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

[0160] [Chemical]

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

[0162] [Chemical]

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

[0164] [Chemical]

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

[0166] [Chemical]

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

[0168] [Chemical]

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

[0170] [Chemical]

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

[0172] [Chemical]

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

[0174] [Chemical]

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

[0176] [Chemical]

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

[0178] [Chemical]

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

[0180] [Chemical]

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

[0182] [Chemical]

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

[0184] [Chemical]

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

[0186] [Chemical]

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

[0188] [Chemical]

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

[0190] [Chemical]

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

[0192] [Chemical]

[0193] [E-26] [E-27] [E-28] [E-29] [E-30] [Chemical]

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

[0195]

Chem.

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

[0197]

Chem.

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

[0199]

Chem.

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

[0201]

Chem.

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

[0203]

Chem.

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

[0205]

Chem.

[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, for example, in a weight ratio of 1:99 to 99:1. By being included within the above range, an appropriate weight ratio can be adjusted by utilizing the electron transport ability of the first compound and the hole transport ability of the second compound to realize bipolar characteristics, and the efficiency and lifespan can be improved. Within the above range, for example, they are included in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20, for example, in a weight ratio of about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40. As specific examples, they are included in a weight ratio of 40:60, 50:50, or 60:40.

[0208] In addition to the first compound and the second compound, one or more additional compounds can be further included. For example, the composition for an organic optoelectronic device can further include a dopant. 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 phosphorescent dopant. A dopant is a substance that is mixed in trace amounts in the composition for an organic optoelectronic device to cause luminescence, and generally, a substance such as a metal complex that emits light by multiple excitation that excites to a triplet state or higher is used. The dopant can be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types are included.

[0209] As an example of the dopant, a phosphorescent dopant is mentioned, and examples of the phosphorescent dopant include organometallic compounds containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. As the phosphorescent dopant, for example, a compound represented by the following Chemical Formula Z can be used, but it is not limited thereto. [Chemical Formula Z] L 7 MX In the above 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. 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, bidentate ligands. The examples of the ligands represented by L 7 and X are selected from the chemical formulas arranged in the following Group A, but are not limited thereto.

[0210] [Group A]

[0211] [Chemical formula]

[0212] In 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 by a halogen, an aryl group having 6 to 30 carbon atoms which may or may not be substituted by an alkyl group having 1 to 30 carbon atoms, or a halogen, and R 303 ~R 324 are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, a substituted or unsubstituted amino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, SF 5 , 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 can contain a dopant represented by the following chemical formula V. [Chemical formula V]

[0214]

Chem.

[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 at least one of R 101 ~R 116 is a functional group represented by the following chemical formula V-1, L 100 is a bidentate ligand of a monovalent anion, a ligand that coordinates to iridium through a lone pair of electrons of a carbon or heteroatom, m15 and m16 are each independently any one of the integers from 0 to 3, and m15 + m16 is any one of the integers from 1 to 3.

[0216] [Chemical formula V-1]

[0217]

Chem.

[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 the part connected to the carbon atom.

[0219] For example, it can also contain a dopant represented by the following chemical formula Z-1. [Chemical formula Z-1]

[0220]

Chem.

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

[0222] A dopant according to one embodiment is a platinum complex, for example, represented by the following Chemical Formula VI. [Chemical Formula VI]

[0223]

Chem.

[0224] In Chemical Formula VI, X 100 is selected from O, S, and NR 131 , R 117 to 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 to R 134 are each independently an alkyl group having 1 to 6 carbon atoms, and at least one of R 117 to R 131 is -SiR 132 R 133 R 134 or a tert-butyl group.

[0225] Hereinafter, an organic optoelectronic device to which the above-described compound for an organic optoelectronic device is applied will be described. The organic optoelectronic device is not particularly limited as long as it can mutually convert electrical energy and optical energy, and examples thereof include an organic optoelectronic device, an organic light-emitting device, an organic solar cell, and an organic photoreceptor drum. Here, an organic light-emitting device, which is an example of an organic optoelectronic device, will be described with reference to the drawings.

[0226] FIG. 1 is a cross-sectional view showing 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 positioned between the positive electrode 120 and the negative electrode 110.

[0227] The positive electrode 120 is formed of a conductor having a high work function so that, for example, hole injection is smoothly performed, and is formed of, for example, a metal, a metal oxide, and / or a conductive polymer. Examples of the positive electrode 120 include metals such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or alloys thereof, metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), combinations of metals and oxides such as ZnO and Al or SnO2, conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0228] The negative electrode 110 is formed of a conductor having a low work function so that, for example, electron injection is smoothly performed, and is formed of, for example, a metal, a metal oxide, and / or a conductive polymer. Examples of the negative electrode 110 include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof, and multilayer structured materials such as LiF / Al, LiO 2 / Al, LiF / Ca, and BaF 2 / Ca, but are not limited thereto.

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

[0230] Specifically, the hole transport region 140 can 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 arranged in the following Group B is included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0231] [Group B]

[0232] [Chemical formula]

[0233] [Chemical formula]

[0234] [Chemical formula]

[0235] [Chemical formula]

[0236] [Chemical formula]

[0237] In the positive hole transport region 140, 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.

[0238] Also, the charge transport region may be, for example, the electron transport region 150. 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. 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 arranged in the following Group C is included in at least one of the electron transport layer and the transport auxiliary layer.

[0239] [Group C]

[0240] [Chemical formula]

[0241] [Chemical formula]

[0242] [Chemical formula]

[0243] [Chemical formula]

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

[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 in addition to a light-emitting layer 130 as an organic layer 105. 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. 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. The above-described organic light-emitting device is applied to an organic light-emitting display device.

Examples

[0246] Hereinafter, the above-described embodiments will be described in more detail with reference to examples. However, the following examples are for illustrative purposes only and do not limit the scope of the rights.

[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&Htech, or synthesized by known methods.

[0248] (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. (Synthesis of the First Compound) The compounds presented as more specific examples of the compounds of the present invention were synthesized by the following steps.

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

[0250] [Chem.]

[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 Compound 1-38 30 g (0.0535 mol) of Compound Int1, 40 g (0.267 mol) of Trifluoromethanesulfonic acid, and D 6 -benzene 282 g (3.35 mol) were mixed and stirred at 10 °C for 24 hours. Purified water was added and neutralized with a saturated K 3 PO 4 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 N 2 ).

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

[0254] [Chem.]

[0255] (phenyl-4-boronic acid)-9H-carbazole 35 g (0.095 mol), bromobenzene-D 5 17 g (0.105 mol), Pd(PPh 3 ) 4 3.3 g (0.0028 mol), K 2 CO 332.7 g (0.237 mol), 120 ml of purified water, and 320 ml of THF were mixed and refluxed with stirring. After the reaction was completed, it was cooled, purified water was added, the organic layer was separated, and concentrated. The concentrate was purified by column chromatography to obtain 25 g 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. Stirring was carried out at room temperature to terminate the reaction, and purified water was added to form a solid. The solid was purified by column chromatography 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, Pd(PPh 3 ) 4 1.72 g (0.0015 mol), K 2 CO 3 13.7 g (0.099 mol), 50 ml of purified water, and 165 ml of THF were mixed and refluxed with stirring. After the reaction was completed, it was cooled, purified water was added, the organic layer was separated and concentrated. The concentrate was purified by column chromatography to obtain 11.5 g of compound Y1 (molecular weight 565.72).

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

[0259]

Chemical Formula

[0260] 47 g (0.281 mol) of Carbazole, 50 g (0.310 mol) of bromobenzene-D 5 50 g (0.310 mol), 53 g (0.028 mol) of CuI, K 2 CO 358 g (0.42 mol), 1,10-phenanthroline 5 g (0.028 mol), and 560 ml of DMF were mixed and refluxed with stirring. After the reaction was completed, it was cooled to room temperature, and purified water was added to form a solid. The solid was purified by column chromatography to obtain 62 g 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 mixture was stirred at room temperature to terminate the reaction. Purified water was added to the reaction solution to form crystals, and the solid was purified by column chromatography to obtain 80 g of Int5 (molecular weight 327.23).

[0262] 80 g (0.245 mol) of Int5, 120 g (0.27 mol) of 4-biphenyl-carbazole-3-boronic ester, K 2 CO 3 68 g (0.49 mol), Pd(PPh 3 ) 4 14 g (0.0122 mol), 320 ml of purified water, and 490 ml of THF were mixed and refluxed with stirring. After the reaction was completed, purified water was added for extraction, and the organic layer was concentrated. The mixture was purified by column chromatography to obtain 90 g of compound Y2 (molecular weight 565.72).

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

[0264]

Chemical formula

[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 Pd 2(dba) 3 (7g, 7.64 mmol) was suspended in 1,400 ml of toluene, and then P(t-Bu) 3 (3.64 ml, 15.28 mmol) was added, and the mixture was refluxed and stirred for 12 hours. Distilled water was added to the reaction solution to separate the mixture. The product thus obtained was purified by 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 a mixed solution of tetrahydrofuran (THF) and distilled water (3:1), 0.7 L. Then, sodium tert-butoxide (68.32 g, 494.34 mmol) was added, and the mixture was refluxed and stirred for 12 hours. The reaction solution was cooled, and after layer separation, the organic layer was collected and concentrated. The concentrated residue was purified by a silica gel column to obtain intermediate M-3 (75.9 g, 67%).

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

[0268] (Fabrication of Organic Light-Emitting Device) Example 1 A glass substrate coated with ITO (Indium tin oxide) was washed with distilled water using ultrasonic waves. After the washing with distilled water was completed, it was ultrasonically washed with solvents such as isopropyl alcohol, acetone, and methanol and then dried. After that, it was transferred to a plasma cleaning device, and the substrate was washed 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 (commercially available from Novaled) was vacuum-evaporated on the ITO substrate to form a hole injection layer with a thickness of 100 Å, and compound A was evaporated on the hole injection layer with a thickness of 1350 Å to form a hole transport layer. Compound B was evaporated on the hole transport layer with a thickness of 350 Å to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compound 1-38 obtained in the synthesis example and compound B-12 were used simultaneously as hosts at a weight ratio of 4:6, and PhGD was doped at 10 wt% with a dopant, and a light-emitting layer with a thickness of 330 Å was formed by vacuum evaporation. Subsequently, compound C was evaporated on the light-emitting layer with a thickness of 50 Å 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. By sequentially vacuum-evaporating LiQ 15 Å and Al 1200 Å on the electron transport layer to form a negative electrode, an organic light-emitting device was fabricated. It was fabricated with the structure of ITO / compound A (3% NDP-9 doping, 100 Å) / compound A (1350 Å) / compound B (350 Å) / EML [90 wt% host (compound 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]

Chem.

[0270] Comparative Examples 1 to 3 Except for changing the host as described in Table 1 below, the elements of Comparative Examples 1 to 3 were fabricated in the same manner as in Example 1.

[0271] Evaluation (1) Measurement of the change in current density in response to a 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 result was obtained by dividing the measured current value by the area.

[0272] (2) Measurement of the change in luminance in response to a 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.

[0273] (3) Measurement of luminous efficiency Using the luminance and current density measured in 1 and 2, the luminous efficiency (cd / A) at the same current density (10 mA / cm 2 ) was calculated.

[0274] (4) Measurement of lifetime Luminance (cd / m 2 ) was 24000 cd / m 2It was maintained and the time when the luminous efficiency (cd / A) decreased to 95% was measured to obtain the results. The values shown in Table 1 are relative values based on the values of Comparative Example 2 respectively.

[0275]

Table 1

[0276] Referring to Table 1, it can be confirmed that the organic light-emitting device according to the example of the present invention has significantly improved lifetime characteristics compared to the organic light-emitting device according to the comparative example.

[0277] Although the examples have been described in detail, the scope of the rights 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 belong to the scope of the rights of the present invention.

Explanation of symbols

[0278] 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 first compound represented by the following chemical formula 1a, and a second compound represented by the following chemical formula 2B, [Chemical formula 1a] 【Chemical 1】 In the chemical formula 1a, D3 represents that three deuteriums are bonded, L １ and L ２ is a single bond, Ar １ is a phenyl group having one, two, or three deuteriums, Ar2 is a biphenyl group having one deuterium, [Chemical formula 2B] 【Chemical 2】 In the chemical formula 2B, Ar ３ ~Ar ５ are each independently an unsubstituted aryl group having 6 to 20 carbon atoms, La1, La2, L ３ ~L ６ are single bonds, Ra1, Ra2, and R ５ ~R １２ is a composition for an organic optoelectronic device that is hydrogen.

2. L of the chemical formula 1a １ -Ar1 is one selected from the following groups, [Chemical Formula 3] The L of the chemical formula 1a ２ -Ar2 is one selected from the following groups, 【Chemical Formula 4】 The composition for an organic optoelectronic device according to claim 1, wherein * is a connection point.

3. The first compound is represented by the following chemical formula 1-8a, [Chemical formula 1-8a] 【Chemical Formula 5】 In the above Chemical Formula 1-8a, L １ , L ２ , Ar １ and Ar ２ are as defined in Claim 1. The composition for an organic optoelectronic device according to claim 1.

4. The composition for an organic optoelectronic device according to claim 1, wherein the first compound is one selected from the following compounds. 【Chemical Formula 6】

5. 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, The organic optoelectronic device, wherein the organic layer contains the composition for an organic optoelectronic device according to any one of claims 1 to 4.

6. The organic layer includes a light-emitting layer, The organic optoelectronic device according to claim 5, wherein the light-emitting layer contains the composition for an organic optoelectronic device.

7. A display device including the organic optoelectronic device according to claim 5.

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