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 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 are each independently an integer from 1 to 4; m2 and m3 are each independently an integer from 1 to 3; Chemical formula 1 simultaneously satisfies the following (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; and (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 of Chemical Formula 2 * ~a4 * The two adjacent ones in the middle are of formula 3 * and the carbon atom connected to each other. Chemical Formula 3 * a1 of Chemical Formula 2 that is not linked to * ~a4 * The remaining two are CR 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 , R 5 and R 6 each independently represents 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; Ar 10 and Ar 11 are each independently hydrogen or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, n1 and n2 each independently represent an integer from 1 to 4; Chemical Formula 2 and Chemical Formula 3 satisfy at least one of the following conditions (iii) and (iv). (iii) Ar 3 ~Ar 5 At least one of the groups is an aryl group having 6 to 20 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. (iv)R a , R 5 and R 6 At least one of these is deuterium.

[0011] According to another embodiment, there is provided an organic optoelectronic device comprising a positive electrode and a negative electrode facing each other, and at least one organic layer positioned between the positive electrode and the negative electrode, wherein the organic layer comprises a composition for an organic optoelectronic device.

[0012] According to yet another embodiment, there is provided a display device including the organic optoelectronic device described above. [Effects of the Invention]

[0013] It is possible to realize an organic optoelectronic device that has the effects of low driving, high efficiency and long life. [Brief explanation of the drawings]

[0014] [Figure 1] 1 is a cross-sectional view illustrating an organic light-emitting device according to an embodiment. DETAILED DESCRIPTION OF THE INVENTION

[0015] 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.

[0016] Unless otherwise defined, the term "substituted" used herein means that at least one hydrogen atom in a substituent or compound has been replaced with deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted amine group having 1 to 30 carbon atoms, a nitro group, a substituted or unsubstituted silyl group having 1 to 40 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a trifluoroalkyl group having 1 to 10 carbon atoms, a cyano group, or a combination thereof.

[0017] 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.

[0018] As used herein, "unsubstituted" means that the hydrogen atom is not replaced with another substituent and remains as a hydrogen atom.

[0019] As used herein, "deuterium substitution (-D)" can include "tritium substitution (-T)."

[0020] 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.

[0021] 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.

[0022] 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.

[0023] 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.

[0024] 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.

[0025] 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. A composition for an organic optoelectronic device according to one embodiment will be described below.

[0026] 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 the following chemical formula 1. [Chemical formula 1]

[0027] [ka]

[0028] 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; 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 of 1 to 4, and 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 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; and (ii)R 1 ~R 4 At least one of them must be deuterium.

[0029] 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. By substituting the benzene moiety forming the carbazole and the 9th (N-directed) substituent of the carbazole with deuterium, the zero-point energy and vibrational energy of the compound can be further lowered. This further lowers the ground state energy, weakening the intermolecular interactions and resulting in 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 driving, high efficiency, and particularly long lifetime.

[0030] 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.

[0031] [Chemical formula 1-1]

[0032] [ka]

[0033] [Chemical formula 1-2]

[0034] [ka]

[0035] [Chemical formula 1-3]

[0036] [ka]

[0037] [Chemical formula 1-4]

[0038]

change

[0039] [Chemical Formula 1-5]

[0040]

change

[0041] [Chemical formula 1-6]

[0042]

change

[0043] [Chemical Formula 1-7]

[0044]

change

[0045] [Chemical Formula 1-8]

[0046]

change

[0047] [Chemical Formula 1-9]

[0048]

change

[0049] [Chemical formula 1-10]

[0050]

change

[0051] 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 1 and 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 R4 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.

[0052] 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.

[0053] [Chemical formula 1a]

[0054] [ka]

[0055] [Formula 1b]

[0056] [ka]

[0057] [Chemical formula 1c]

[0058] [ka]

[0059] [Chemical formula 1d]

[0060] [ka]

[0061] [Chemical formula 1e]

[0062] [ka]

[0063] In chemical formulas 1a to 1e, L 1 , L 2 , Ar 1 , Ar 2 and Ar 6 ~Ar 9 The definition of is as mentioned above, and Ar 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 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 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 a hydrogen atom or an unsubstituted or substituted aryl group having 6 to 20 carbon atoms, substituted with at least one deuterium atom. For example, Ar 6 ~Ar 9are 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.

[0064] 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.

[0065] [Group I-1]

[0066] [ka]

[0067] [Group I-2]

[0068] [ka]

[0069] [ka]

[0070] [ka]

[0071] In Group I-1 and Group I-2, * is a connection point.

[0072] For example, Chemical Formula 1 is represented by Chemical Formula 1-8a or Chemical Formula 1-8e below.

[0073] [Formula 1-8a]

[0074] [ka]

[0075] [Formula 1-8e]

[0076] [ka]

[0077] 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 9 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.

[0078] 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.

[0079] [Group 1]

[0080]

change

[0081]

change

[0082]

change

[0083]

change

[0084]

change

[0085]

change

[0086]

change

[0087]

change

[0088]

change

[0089]

change

[0090]

change

[0091] [ka]

[0092] [ka]

[0093] [ka]

[0094] [ka]

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] [ka]

[0099] [ka]

[0100] 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, Ar1 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.

[0101] The second compound is represented by a combination of Chemical Formula 2 and Chemical Formula 3 below. [Chemical formula 2] [Chemical formula 3]

[0102] [ka]

[0103] 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 , 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 , R 5 and R 6 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; Ar 10 and Ar 11are each independently hydrogen or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, n1 and n2 are each independently an integer of 1 to 4, and Chemical Formula 2 and Chemical Formula 3 satisfy at least one of the following conditions (iii) and (iv): (iii) Ar 3 ~Ar 5 At least one of the groups is an aryl group having 6 to 20 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. (iv)R a , R 5 and R 6 At least one of these is deuterium.

[0104] The second compound, when used in the light-emitting layer together with the first compound, can improve the charge mobility and safety, thereby improving the luminous efficiency and life characteristics. In particular, the second compound represented by the combination of Chemical Formula 2 and Chemical Formula 3 has an indolocarbazole skeleton, and the benzene moiety constituting the indolocarbazole is substituted with at least one deuterium atom, or the N-direction substituent of the indolocarbazole, Ar, is substituted with at least one deuterium atom. 3 ~Ar 5 Indolocarbazole has a structure in which at least one of the benzene moieties is substituted with deuterium. By substituting the benzene moiety of the indolocarbazole or the N-directed substituent of the indolocarbazole with deuterium, the zero-point energy and vibrational energy of the compound can be further lowered. This further lowers the ground state energy and weakens the intermolecular interactions, allowing the thin film to be formed in an amorphous state, further improving heat resistance and effectively extending the lifetime. In other words, when applied, it is possible to realize an organic light-emitting device with low driving power, high efficiency, and particularly long lifetime.

[0105] 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]

[0106] [ka]

[0107] [Chemical formula 2C] [Chemical formula 2D]

[0108] [ka]

[0109] [Chemical formula 2E] [Chemical formula 2F]

[0110] [ka]

[0111] In chemical formulas 2A to 2F, Ar 3 ~Ar 5 , Ar 10 , Ar 11 , L 3 ~L 6 , R 1 ~R 4 , n1 and n2 are as described above, and L a1 ~L a4 is the aforementioned L 3 ~L 6 is identical to the definition of R a1 ~R a4 are the R a For example, R a1 ~R a4 , R 5 and R 6 At least one of the groups may be deuterium. For example, Ar 10 and Ar 11 may each independently be an aryl group having 6 to 20 carbon atoms, which may be substituted with hydrogen or at least one deuterium, or may be unsubstituted. For example, Ar 10 and Ar 11are each independently hydrogen or 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. For example, Ar 3 ~Ar 5 At least one of R may be an aryl group having 6 to 20 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. a1 ~R a4 , R 5 and R 6 At least one of them is deuterium, and Ar 3 ~Ar 5 At least one of the groups may be an aryl group having 6 to 20 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. For example, Ar 3 ~Ar 5 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 carbazolyl 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.

[0112] In a specific embodiment of the present invention, L in Formula 2 and Formula 3 3 -Ar 3 , L 5 -Ar 4 and L6 -Ar 5 are each independently selected from the substituents listed in Group II-1 and Group II-2 below, and L 3 -Ar 3 , L 5 -Ar 4 and L 6 -Ar 5 At least one of the following is selected from the substituents listed in Group II-2.

[0113] [Group II-1]

[0114] [ka]

[0115] [Group II-2]

[0116] [ka]

[0117] In Group II-1 and Group II-2, * is a connection point.

[0118] In a more specific embodiment of the present invention, the second compound is represented by the following chemical formula 2B-a:

[0119] [Chemical formula 2B-a]

[0120] [ka]

[0121] In chemical formula 2B-a, Ar 3 ~Ar 5 , Ar 10 , Ar 11 and L 3 ~L 6is as described above, n1 and n2 are each independently an integer of 1 to 4, and n3 is an integer of 1 or 2. For example, Ar 3 ~Ar 5 Each of L may independently be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group. 3 ~L 6 may each independently be a single bond or a substituted or unsubstituted phenylene group. For example, the second compound may be one selected from the compounds listed in Group 2 below, but is not limited thereto.

[0122] [Group 2] [2-A-1] [2-A-2] [2-A-3]

[0123] [ka]

[0124] [2-A-4] [2-A-5] [2-A-6]

[0125] [ka]

[0126] [2-A-7] [2-A-8] [2-A-9]

[0127] [ka]

[0128] [2-A-10] [2-A-11] [2-A-12]

[0129] [ka]

[0130] [2-A-13] [2-A-14]

[0131] [ka]

[0132] [2-A-15] [2-A-16] [2-A-17]

[0133] [ka]

[0134] [2-A-18] [2-A-19]

[0135] [ka]

[0136] [2-A-20] [2-A-21]

[0137] [ka]

[0138] [2-A-22] [2-A-23]

[0139] [ka]

[0140] [2-A-24] [2-A-25]

[0141] [ka]

[0142] [2-A-26] [2-A-27]

[0143] [ka]

[0144] [2-A-28]

[0145] [ka]

[0146] [2-A-29] [2-A-30] [2-A-31]

[0147] [ka]

[0148] [2-A-32] [2-A-33]

[0149] [ka]

[0150] [2-A-34] [2-A-35]

[0151] [ka]

[0152] [2-A-36] [2-A-37] [2-A-38]

[0153] [ka]

[0154] [2-A-39] [2-A-40]

[0155] [ka]

[0156] [2-A-41] [2-A-42]

[0157] [ka]

[0158] [2-A-43] [2-A-44] [2-A-45]

[0159] [ka]

[0160] [2-A-46] [2-A-47]

[0161] [ka]

[0162] [2-A-48] [2-A-49]

[0163] [ka]

[0164] [2-A-50] [2-A-51] [2-A-52]

[0165] [ka]

[0166] [2-A-53] [2-A-54]

[0167] [ka]

[0168] [2-A-55] [2-A-56]

[0169] [ka]

[0170] [2-A-57] [2-A-58] [2-A-59]

[0171] [ka]

[0172] [2-A-60] [2-A-61]

[0173] [ka]

[0174] [2-A-62] [2-A-63]

[0175] [ka]

[0176] [2-A-64] [2-A-65] [2-A-66]

[0177] [ka]

[0178] [2-A-67] [2-A-68]

[0179] [ka]

[0180] [2-A-69] [2-A-70]

[0181] [ka]

[0182] [2-A-71] [2-A-72] [2-A-73]

[0183] [ka]

[0184] [2-A-74] [2-A-75]

[0185] [ka]

[0186] [2-A-76] [2-A-77]

[0187] [ka]

[0188] [2-A-78] [2-A-79] [2-A-80]

[0189] [ka]

[0190] [2-A-81] [2-A-82]

[0191] [ka]

[0192] [2-A-83] [2-A-84]

[0193] [ka]

[0194] [2-B-1] [2-B-2] [2-B-3]

[0195] [ka]

[0196] [2-B-4] [2-B-5]

[0197]

change

[0198] [2-B-6] [2-B-7]

[0199]

change

[0200] [2-B-8] [2-B-9] [2-B-10]

[0201]

change

[0202]

change

[0203] [2-B-13] [2-B-14]

[0204]

change

[0205] [2-B-15] [2-B-16] [2-B-17]

[0206]

change

[0207] [2-B-18] [2-B-19]

[0208]

change

[0209] [2-B-20] [2-B-21]

[0210]

change

[0211] [2-B-22]

[0212]

change

[0213] [2-B-23] [2-B-24]

[0214]

change

[0215] [2-B-25] [2-B-26]

[0216]

change

[0217] [2-B-27] [2-B-28]

[0218]

change

[0219] [2-B-29] [2-B-30]

[0220]

change

[0221] [2-B-31] [2-B-32] [2-B-33]

[0222]

change

[0223] [2-B-34] [2-B-35]

[0224]

change

[0225] [2-B-36] [2-B-37]

[0226]

change

[0227] [2-B-38] [2-B-39] [2-B-40]

[0228]

change

[0229] [2-B-41] [2-B-42]

[0230]

change

[0231] [2-B-43] [2-B-44]

[0232]

change

[0233] [2-B-45] [2-B-46] [2-B-47]

[0234]

change

[0235] [2-B-48] [2-B-49]

[0236]

change

[0237] [2-B-50] [2-B-51]

[0238]

change

[0239] [2-B-52] [2-B-53] [2-B-54]

[0240]

change

[0241] [2-B-55] [2-B-56]

[0242]

change

[0243] [2-B-57] [2-B-58]

[0244]

change

[0245] [2-B-59] [2-B-60] [2-B-61]

[0246]

change

[0247] [2-B-62] [2-B-63]

[0248]

change

[0249] [2-B-64] [2-B-65]

[0250]

change

[0251] [2-B-66] [2-B-67] [2-B-68]

[0252]

change

[0253] [2-B-69] [2-B-70]

[0254]

change

[0255] [2-B-71] [2-B-72]

[0256]

change

[0257] [2-B-73] [2-B-74] [2-B-75]

[0258]

change

[0259] [2-B-76] [2-B-77]

[0260]

change

[0261] [2-B-78] [2-B-79]

[0262]

change

[0263] [2-B-80] [2-B-81] [2-B-82]

[0264]

change

[0265] [2-B-83] [2-B-84]

[0266]

change

[0267] [2-B-85] [2-B-86]

[0268]

change

[0269] [2-B-87] [2-B-88]

[0270]

change

[0271] [2-B-89] [2-B-90]

[0272]

change

[0273] [2-B-91] [2-B-92]

[0274]

change

[0275] [2-B-93] [2-B-94]

[0276]

change

[0277] [2-B-95] [2-B-96]

[0278]

change

[0279] [2-B-97] [2-B-98]

[0280]

change

[0281] [2-B-99] [2-B-100]

[0282]

change

[0283] [2-C-1] [2-C-2] [2-C-3]

[0284]

change

[0285] [2-C-4] [2-C-5]

[0286]

change

[0287] [2-C-6] [2-C-7]

[0288]

change

[0289] [2-C-8] ​​[2-C-9] [2-C-10]

[0290]

change

[0291] [2-C-11] [2-C-12]

[0292]

change

[0293] [2-C-13] [2-C-14]

[0294]

change

[0295] [2-C-15] [2-C-16] [2-C-17]

[0296]

change

[0297] [2-C-18] [2-C-19]

[0298]

change

[0299] [2-C-20] [2-C-21]

[0300]

change

[0301] [2-C-22] [2-C-23] [2-C-24]

[0302]

change

[0303] [2-C-25] [2-C-26]

[0304]

change

[0305] [2-C-27] [2-C-28]

[0306]

change

[0307] [2-C-29] [2-C-30] [2-C-31]

[0308]

change

[0309] [2-C-32] [2-C-33] [2-C-34]

[0310]

change

[0311] [2-D-1] [2-D-2] [2-D-3]

[0312]

change

[0313] [2-D-4] [2-D-5] [2-D-6]

[0314] [ka]

[0315] [2-D-7] [2-E-1] [2-E-2]

[0316] [ka]

[0317] [2-E-3] [2-E-4] [2-E-5]

[0318] [ka]

[0319] [2-E-6] [2-E-7]

[0320] [ka]

[0321] [2-E-8] [2-E-9] [2-E-10]

[0322] [ka]

[0323] [2-E-11] [2-E-12]

[0324] [ka]

[0325] [2-E-13] [2-E-14]

[0326] [ka]

[0327] [2-E-15] [2-E-16] [2-E-17]

[0328] [ka]

[0329] [2-E-18] [2-E-19]

[0330] [ka]

[0331] [2-E-20] [2-E-21]

[0332] [ka]

[0333] [2-E-22] [2-E-23] [2-E-24]

[0334] [ka]

[0335] [2-E-25] [2-E-26]

[0336] [ka]

[0337] [2-E-27] [2-E-28]

[0338] [ka]

[0339] [2-E-29] [2-E-30]

[0340]

change

[0341] [2-E-31] [2-E-32]

[0342]

change

[0343] [2-E-33] [2-E-34]

[0344]

change

[0345] [2-F-1] [2-F-2] [2-F-3]

[0346]

change

[0347] [2-F-4] [2-F-5]

[0348]

change

[0349] [2-F-6] [2-F-7]

[0350]

change

[0351] [2-F-8] [2-F-9] [2-F-10]

[0352]

change

[0353] [2-F-11] [2-F-12]

[0354]

change

[0355] [2-F-13] [2-F-14]

[0356]

change

[0357] [2-F-15] [2-F-16] [2-F-17]

[0358]

change

[0359] [2-F-18] [2-F-19]

[0360]

change

[0361] [2-F-20] [2-F-21]

[0362]

change

[0363] [2-F-22] [2-F-23] [2-F-24]

[0364]

change

[0365] [2-F-25] [2-F-26]

[0366]

change

[0367] [2-F-27] [2-F-28]

[0368] [ka]

[0369] [2-F-29] [2-F-30]

[0370] [ka]

[0371] [2-F-31] [2-F-32]

[0372] [ka]

[0373] [2-F-33] [2-F-34]

[0374] [ka]

[0375] 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-a-1 below.

[0376] [Chemical formula 2B-a-1]

[0377] [ka]

[0378] In chemical formula 2B-a-1, Ar 3 ~Ar 5are each independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group; L 3 ~L 6 are each independently a single bond or a substituted or unsubstituted phenylene group.

[0379] 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, the electron transport ability of the first compound and the hole transport ability of the second compound can be utilized to achieve bipolar characteristics by combining an appropriate weight ratio, thereby improving efficiency and lifetime. Within this range, the first compound and the second compound are included in a weight ratio of, 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.

[0380] In addition to the first compound and the second compound, the composition may further include one or more compounds. For example, the composition for an organic optoelectronic device may further include a dopant. The dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, or 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. Typically, a substance such as a metal complex that emits light by multiple excitation to a triplet state or higher is used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and one or more dopants may be included. Examples of dopants include phosphorescent dopants, such as organometallic compounds containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. The phosphorescent dopant may be, for example, a compound represented by the following chemical formula Z, but is not limited thereto.

[0381] [Chemical formula Z] L7 MX In the chemical formula Z, M is a metal and L 7 and X are the same or different and are ligands that form a complex with M. 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.

[0382] [Group A]

[0383] [ka]

[0384] 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.

[0385] For example, it may contain a dopant represented by the following chemical formula V. [Chemical formula V]

[0386] [ka]

[0387] 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.

[0388] [Chemical formula V-1]

[0389] [ka]

[0390] 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.

[0391] For example, a dopant represented by the following chemical formula Z-1 may be included. [Chemical formula Z-1]

[0392] [ka]

[0393] In chemical formula Z-1, rings A, B, C, and D each independently represent a 5- or 6-membered carbocyclic or heterocyclic ring. RA, RB, RC, and RD each independently represent mono-, di-, tri-, or tetra-substituted, or unsubstituted. LB, LC, and LD 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, LE 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, LE is absent. R, R, R, R, R, 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. Any adjacent R, R, R, R, R, R, R, R, and R' may be optionally joined to form a ring. X, X, X, X, and X are each independently selected from the group consisting of carbon and nitrogen. Q, Q, Q, and Q each represent oxygen or a direct bond.

[0394] The dopant according to one embodiment is a platinum complex, for example, represented by the following formula VI: [Chemical formula VI]

[0395] [ka]

[0396] 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.

[0397] 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.

[0398] 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.

[0399] The positive electrode 120 is made of a conductor with a high work function to facilitate hole injection, such as a metal, metal oxide, and / or conductive polymer. Examples of the positive electrode 120 include, but are not limited to, metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO and Al or SnO and Sb; and conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyethylenedioxythiophene: PEDOT), polypyrrole, and polyaniline.

[0400] The negative electrode 110 is formed of a conductor with a low work function, for example, a metal, a metal oxide, and / or a conductive polymer, to facilitate electron injection. 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, alloys thereof, and multilayer structures such as LiF / Al, LiO / Al, LiF / Ca, and BaF / Ca.

[0401] The organic layer 105 may include the composition for an organic optoelectronic device described above. The organic layer 105 may include an emitting layer 130, which may include the composition for an organic optoelectronic device described above. The composition for an organic optoelectronic device further including a dopant may be, for example, a red-emitting composition. The emitting layer 130 may include, for example, the composition for an organic optoelectronic device described above as a phosphorescent host.

[0402] The organic layer may further include 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 may further enhance hole injection and / or hole mobility between the positive electrode 120 and the light-emitting layer 130 and block electrons. Specifically, the hole transport region 140 may include a hole transport layer between the positive electrode 120 and the light-emitting layer 130 and a hole transport auxiliary layer between the light-emitting layer 130 and the hole transport layer, and at least one of the compounds listed in Group B below may be contained in at least one of the hole transport layer and the transport auxiliary layer.

[0403] [Group B]

[0404] [ka]

[0405] [ka]

[0406] [ka]

[0407] [ka]

[0408] [ka]

[0409] 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.

[0410] 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 electron transport auxiliary layer.

[0411] [Group C]

[0412] [ka]

[0413] [ka]

[0414] [ka]

[0415] [ka]

[0416] 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.

[0417] 1, the organic light emitting device according to one embodiment of the present invention may include a hole transport region 140 and an electron transport region 150 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), a hole injection layer (not shown), etc. as the organic layer in addition to the light emitting layer.

[0418] The organic light emitting device 100 can be manufactured by forming an anode or cathode on a substrate, forming an organic layer by a dry deposition method such as vacuum evaporation, sputtering, plasma plating, or ion plating, and then forming an anode or cathode thereon. The organic light emitting device described above is applicable to an organic light emitting display device. [Example]

[0419] The above-described embodiments will be described in more detail below with reference to examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention. 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 were synthesized by known methods.

[0420] (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. Synthesis Example 1: Synthesis of Compound 1-38 [Reaction Scheme 1]

[0421] [ka]

[0422] Step 1: Synthesis of compound Int1 Compound Int1 was synthesized with reference to the method disclosed in Korean Patent Publication No. 2016-0049842.

[0423] 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.

[0424] Synthesis Example 2: Synthesis of Compound 1-110 [Reaction Scheme 2]

[0425] [ka]

[0426] Compound Int9 was synthesized by referring to the method disclosed in Korean Patent Publication KR10-2018-0035076. Compound 1-110 was synthesized in the same manner as in Synthesis Example 1, except that compound Int9 was used instead of Int1 in step 2.

[0427] (Synthesis of the second compound) Synthesis Example 3: Synthesis of Compound 2-B-30 [Reaction Scheme 3]

[0428] [ka]

[0429] 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%).

[0430] 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%).

[0431] Step 3: Synthesis of compound Int3 Compound Int3 was obtained using intermediates M-2 and M-3 in the same manner as in the synthesis of intermediate M-2.

[0432] Step 4: Synthesis of Compound 2-B-30 20 g (0.0279 mol) of compound Int3, 12.33 ml (0.1397 mol) of trifluoromethanesulfonic acid, and 335.49 ml (3.4924 mol) of D6-benzene were mixed and stirred at 10° C. for 24 hours. Purified water was added and neutralized with saturated KPO solution. The organic layer was concentrated and purified using a column to obtain compound 2-B-30 (14 g, 70%).

[0433] Synthesis Example 4: Synthesis of Compound 2-B-22 Compound Int4 and compound 2-B-22 were synthesized in the same manner as in steps 1 to 4 of Synthesis Example 3, except that 3-biphenylboronic acid was used instead of 4-biphenylboronic acid in step 2 of Synthesis Example 3. [Reaction Scheme 4]

[0434] [ka]

[0435] Synthesis Example 5: Synthesis of Compound 2-B-80 [Reaction Scheme 5]

[0436] [ka] Compound Int5 and compound 2-B-80 were synthesized in the same manner as in steps 1 to 4 of Synthesis Example 3, except that 2-Bromo-1,1':4',1''-terphenyl (CAS No. 3282-24-4) was used instead of 3-bromobiphenyl in step 1 of Synthesis Example 3.

[0437] Synthesis Example 6: Synthesis of Compound 2-B-82 [Reaction Scheme 6]

[0438] [ka] Compound Int6 and compound 2-B-82 were synthesized in the same manner as in steps 1 to 4 of Synthesis Example 3, except that 4'-Bromo-1,1':3',1''-terphenyl (CAS No. 60631-83-6) was used instead of 3-bromobiphenyl in step 1 of Synthesis Example 3, and 3-biphenylboronic acid was used instead of 4-biphenylboronic acid in step 2.

[0439] Synthesis Example 7: Synthesis of Compound 2-B-36 [Reaction Scheme 7]

[0440] [ka]

[0441] Compound Int7 and compound 2-B-36 were synthesized in the same manner as in steps 1 to 4 of Synthesis Example 3, except that 2'-Bromo-1,1':4',1''-terphenyl (CAS No. 3282-25-5) was used instead of 3-bromobiphenyl in step 1 of Synthesis Example 3.

[0442] Synthesis Example 8: Synthesis of Compound 2-B-2 [Reaction Scheme 8]

[0443] [ka]

[0444] Compound Int8 and compound 2-B-2 were synthesized in the same manner as in steps 1 to 4 of Synthesis Example 3, except that 11,12-Dihydro-11-phenylindolo[2,3-a]carbazole (CAS No. 1024598-06-8) was used instead of intermediate M-2 in step 3 of Synthesis Example 3, and 9-Phenylcarbazole-2-boronic acid (CAS No. 1001911-63-2) was used instead of 4-biphenylboronic acid in step 2.

[0445] (Fabrication of organic light-emitting devices) Example 1 An ITO (indium tin oxide)-coated glass substrate was ultrasonically cleaned in distilled water. After the distilled water cleaning, the substrate was washed with solvents such as isopropyl alcohol, acetone, and methanol and dried. The substrate was then transferred to a plasma cleaning device and cleaned using oxygen plasma for 10 minutes. The substrate was then transferred to a vacuum deposition device. Using the prepared ITO transparent electrode as the anode, Compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum-deposited on top of the ITO substrate to form a 100 Å-thick hole injection layer. Compound A was then deposited on top of the hole injection layer to a thickness of 1350 Å to form a hole transport layer. Compound B was then deposited on top of the hole transport layer to a thickness of 350 Å to form a hole transport auxiliary layer. Compound 1-38 obtained in Synthesis Example 1 and compound 2-B-30 obtained in Synthesis Example 3 were simultaneously used as hosts on top of the hole transport assisting layer, and the dopant PhGD was doped at 7 wt% by vacuum deposition to form a 330 Å thick light-emitting layer. Subsequently, compound C was deposited on top of the light-emitting layer to a thickness of 50 Å to form an electron transport assisting layer, and compound D and LiQ were simultaneously vacuum-deposited in a 1:1 weight ratio 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, thereby fabricating 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 [93 wt% host (compounds 1-38:compounds 2-B-30 = 4:6 w / w): 7 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-[4-[4-(4'-Cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine [PhGD]

[0446] [ka]

[0447] Examples 2 to 6 and Comparative Examples 1 to 18 The devices of Examples 2 to 6 and Comparative Examples 1 to 18 were prepared in the same manner as in Example 1, except that the host was changed as shown in Tables 1 to 6 below.

[0448] 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.

[0449] (2) Measurement of luminance 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.

[0450] (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

[0451] (4) Lifespan measurement Luminance (cd / m 2) to 6,000 cd / m 2 The time it took for the luminous efficiency (cd / A) to decrease to 90% was measured.

[0452] The values ​​shown in Tables 1 to 6 are those of Comparative Example 1, Comparative Example 4, Comparative Example 7, Comparative Example 10, Comparative Example 13, and Comparative Example 14, respectively. of 6 It is a relative value based on the value.

[0453] [Table 1]

[0454] [Table 2]

[0455] [Table 3]

[0456] [Table 4]

[0457] [Table 5]

[0458] [Table 6]

[0459] Referring to Tables 1 to 6, it can be seen that the organic light emitting devices according to the examples of the present invention have significantly improved life characteristics compared to the organic light emitting devices according to the comparative examples.

[0460] 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]

[0461] 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 It includes a second compound represented by the following chemical formula 2B: [Chemical formula 1] 【Chemical 1】 In the above Chemical Formula 1, L １ and L ２ is a single bond, 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, 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 the groups is a C6-C30 aryl group partially substituted with deuterium or a C2-C30 heterocyclic group substituted with at least one deuterium; and (ii) R １ ~R ４ are all deuterium, [Chemical formula 2B] 【Chemistry 2】 In the above Chemical Formula 2B, 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, L ３ ~L ６ is a single bond, Ar １０ and Ar １１ are each independently hydrogen or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; n1 and n2 are each independently an integer from 1 to 4; The formula 2B satisfies at least one of the following conditions (iii) and (iv): (iii) Ar ３ The aryl group or the heterocyclic group is substituted with deuterium, and Ar ４ and Ar ５ The aryl group or the heterocyclic group is bonded to hydrogen or partially bonded to hydrogen and partially substituted with deuterium, (iv) R ａ , R ５ , and R ６ and are both deuterium.

2. The first compound is represented by any one of the following formulas 1-1 to 1-10: [Chemical formula 1-1] 【Chemistry 3】 [Chemical formula 1-2] 【Chemistry 4】 [Chemical formula 1-3] 【Chemistry 5】 [Chemical formula 1-4] 【Chemistry 6】 [Chemical formula 1-5] 【Chemistry 7】 [Chemical formula 1-6] 【Chemistry 8】 [Chemical formula 1-7] 【Chemistry 9】 [Chemical formula 1-8] 【Chemistry 10】 [Chemical formula 1-9] 【Chemistry 11】 [Chemical formula 1-10] 【Chemistry 12】 In the above Chemical Formulas 1-1 to 1-10, L １ , L ２ , Ar １ , Ar ２ , Ar ６ ~Ar ９ , R １ ~R ４ and m1 to m4 are defined as defined in claim 1. The composition for organic optoelectronic devices according to claim 1.

3. Ar in Formula 1 １ and Ar ２ 2. The composition for organic optoelectronic devices according to claim 1, wherein at least one of the groups is at least one partially deuterium-substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, triphenylene group, fluorenyl group, dibenzofuranyl group, or dibenzothiophenyl group.

4. L of Formula 1 １ -Ar １ and L ２ -Ar ２ At least one of the substituents is one selected from the substituents listed in Group I-2 below, [Group I-2] 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 In Group I-2, ＊ The composition for organic optoelectronic devices according to claim 1 , wherein is a connecting point.

5. The formula 1 is represented by the following formula 1-8a or 1-8e: [Chemical formula 1-8a] 【Chemistry 18】 [Chemical formula 1-8e] 【Chemistry 19】 In the above Chemical Formula 1-8a and Chemical Formula 1-8e, L １ , L ２ , Ar １ , Ar ２ and Ar ９ The composition for organic optoelectronic devices according to claim 1, wherein is as defined in claim 1.

6. 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 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】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 【Chemistry 50】 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemical Formula 54】

7. The second compound is represented by the following chemical formula 2B-a: [Chemical formula 2B-a] 【Chemistry 55】 In Chemical Formula 2B-a, Ar ３ ~Ar ５ , Ar １０ , Ar １１ and L ３ ~L ６ is as defined in claim 1, n1 and n2 are each independently an integer from 1 to 4; 2. The composition for organic optoelectronic devices of claim 1, wherein n3 is one of the integers 1 or 2.

8. The Ar ３ ~Ar ５ 2. The composition for organic optoelectronic devices according to claim 1, wherein at least one of the groups selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylene group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

9. Said L ３ -Ar ３ is one selected from the substituents listed in Group II-1 below, L ５ -Ar ４ and L ６ -Ar ５ At least one of the substituents is one selected from the substituents listed in Group II-2 below, [Group II-1] 【Chemical 56】 [Group II-2] 【Chemical Formula 57】 In Group II-1 and Group II-2, ＊ The composition for organic optoelectronic devices according to claim 1 , wherein is a connecting point.

10. The composition for organic optoelectronic devices according to claim 1 , wherein the second compound is one selected from the compounds listed in Group 2 below. [Group 2] 【Chemistry 58】 【Chemical 59】 【Chemistry 60】 【Hua 61】 【Hua 62】 【Chemistry 63】 【Hua 64】 【Chemistry 65】 【Hua 66】 【Hua 67】 【Chemistry 68】 【Chemical Formula 69】 【Chemistry 70】 【Chemical Formula 71】 【Chemical 72】 【Chemical 73】 【Chemical 74】 【Chemistry 75】

11. The first compound is represented by the following chemical formula 1-8a: The second compound is represented by the following chemical formula 2B-a-1: [Chemical formula 1-8a] 【Chemical 76】 In the above chemical formula 1-8a, Ar １ and Ar ２ is a phenyl group, a biphenyl group, a biphenyl group, or a triphenylene group, [Chemical formula 2B-a-1] 【Chemical 77】 In the above chemical formula 2B-a-1, Ar ３ ~Ar ５ The composition for organic optoelectronic devices according to claim 1 , wherein each independently represents a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

12. 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 11.

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

14. A display device comprising the organic optoelectronic device of claim 12.

Images