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

Abstract

The present invention relates to a compound for an organic optoelectronic device represented by Chemical Formula 1, and an organic optoelectronic device and a display device including the same. The details of Chemical Formula 1 are as defined in the specification.

Description

[Technical Field]

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

[0002] An organic optoelectric diode is a device that can convert electrical energy into light energy and vice versa. Organic optoelectric diodes can be broadly divided into two types based on their operating principle. One type is a photoelectric diode, in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to generate electrical energy. The other type is a light-emitting device, in which voltage or current is supplied to the electrodes to generate light energy from electrical energy.

[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 attention in recent years due to the increasing demand for flat panel display devices. Organic light-emitting devices convert electrical energy into light, and their performance is significantly affected by the organic material located between the electrodes. Summary of the Invention [Problem to be solved by the invention]

[0004] One embodiment provides a compound for an organic optoelectronic device that can realize an organic optoelectronic device with low driving, high efficiency, and long life. Another embodiment provides an organic optoelectronic device including the compound. Yet another embodiment provides a display device including the organic optoelectronic device. [Means for solving the problem]

[0005] According to one embodiment, there is provided a compound for an organic optoelectronic device represented by the following Chemical Formula 1: [Chemical formula 1]

[0006] [ka]

[0007] In chemical formula 1, R 1 ~R 4 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C30 aryl group, Ar 3 ~Ar 6 are each independently hydrogen or a substituted or unsubstituted C6 to C30 aryl group, m1 and m4 each independently represent an integer from 1 to 4; m2 and m3 are each independently an integer from 1 to 3; R 1 ~R 4 at least one of is deuterium, Ar 1 and Ar 2 are each independently one selected from the substituents listed in Group I and Group II below, Ar 1 and Ar 2 At least one of the groups is one selected from the substituents listed in Group II below.

[0008] [Group I]

[0009] [ka]

[0010] [Group II]

[0011] [ka]

[0012] In Group I and Group II, R a and R b are each independently hydrogen, deuterium, a cyano group, or a substituted or unsubstituted C1-C10 alkyl group; R c ~R e are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group; D is deuterium, m5 and m8 each independently represent an integer from 1 to 5; m6 and m9 each independently represent an integer of 1 to 4; m7 and m10 each independently represent an integer of 1 to 3.

[0013] According to another embodiment, there is provided an organic optoelectronic device including an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, the organic layer including a compound for an organic optoelectronic device. According to yet another embodiment, there is provided a display device including the organic optoelectronic device. [Effects of the Invention]

[0014] Low-driving, highly efficient and long-life organic optoelectronic devices can be realized. [Brief explanation of the drawings]

[0015] [Figure 1] 1 is a cross-sectional view illustrating an organic light-emitting device according to an embodiment. DETAILED DESCRIPTION OF THE INVENTION

[0016] DETAILED DESCRIPTION OF THE INVENTION The following detailed description of the present invention is given by way of example only, and the present invention is not limited thereto but is defined only by the scope of the claims.

[0017] 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 C1-C30 amine group, a nitro group, a substituted or unsubstituted C1-C40 silyl group, a C1-C30 alkyl group, a C1-C10 alkylsilyl group, a C6-C30 arylsilyl group, a C3-C30 cycloalkyl group, a C3-C30 heterocycloalkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, a C1-C20 alkoxy group, a C1-C10 trifluoroalkyl group, a cyano group, or a combination thereof.

[0018] In one embodiment of the present invention, "substituted" means that at least one hydrogen atom in a substituent or compound is replaced with deuterium, a C1-C30 alkyl group, a C1-C10 alkylsilyl group, a C6-C30 arylsilyl group, a C3-C30 cycloalkyl group, a C3-C30 heterocycloalkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, or a cyano group. In another specific embodiment of the present invention, "substituted" means that at least one hydrogen atom in a substituent or compound is replaced with deuterium, a C1-C20 alkyl group, a C6-C30 aryl group, or a cyano group. In another specific embodiment of the present invention, "substituted" means that at least one hydrogen atom in a substituent or compound is replaced with deuterium, a C1-C5 alkyl group, a C6-C18 aryl group, 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.

[0019] As used herein, "unsubstituted" means that the hydrogen atoms remain as hydrogen atoms without being replaced with other substituents.

[0020] As used herein, "hydrogen substitution (-H)" can include "deuterium substitution (-D)" or "tritium substitution (-T)."

[0021] As used herein, unless otherwise defined, the term "hetero" means that a functional group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, P, and Si, and the remainder is carbon.

[0022] As used herein, the term "aryl group" refers to a general group having one or more hydrocarbon aromatic moieties, and includes groups 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; groups 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 groups in which two or more hydrocarbon aromatic moieties are directly or indirectly fused to a non-aromatic fused ring, such as a fluorenyl group. Aryl groups include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings sharing adjacent pairs of carbon atoms) functional groups.

[0023] As used herein, the term "heterocyclic group" is a broader term that includes heteroaryl groups and refers to a ring compound, such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof, that contains at least one heteroatom selected from the group consisting of N, O, S, P, and Si in place of carbon (C). When a heterocyclic group is a fused ring, the entire heterocyclic group or each ring may contain one or more heteroatoms.

[0024] 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 through a sigma bond, or, if the heteroaryl group contains two or more rings, the two or more rings may be fused together. If the heteroaryl group is a fused ring, each ring may contain 1 to 3 heteroatoms.

[0025] More specifically, the substituted or unsubstituted C6 to C30 aryl group 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.

[0026] More specifically, the substituted or unsubstituted C2-C30 heterocyclic group 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, a substituted or unsubstituted benzimidazolyl group, The alkyl group may be, but is not limited to, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof.

[0027] 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 anode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the anode, and the movement of holes formed in the light-emitting layer within the light-emitting layer. The term "electron characteristic" refers to the ability to accept 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 cathode into the light-emitting layer, the movement of electrons formed in the light-emitting layer to the cathode, and the movement of electrons formed in the light-emitting layer within the light-emitting layer.

[0028] Hereinafter, a compound for an organic optoelectronic device according to one embodiment will be described.

[0029] The compound for an organic optoelectronic device according to one embodiment is represented by the following Chemical Formula 1. [Chemical formula 1]

[0030] [ka]

[0031] In formula 1, R 1 ~R 4 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C30 aryl group, and Ar 3 ~Ar 6 are each independently hydrogen or a substituted or unsubstituted C6 to C30 aryl group; m1 and m4 are each independently an integer of 1 to 4; m2 and m3 are each independently an integer of 1 to 3; R 1 ~R 4 At least one of the Ar 1 and Ar 2 are each independently one selected from the substituents listed in Group I and Group II below, and Ar 1 and Ar 2 At least one of the groups is one selected from the substituents listed in Group II below.

[0032] [Group I]

[0033] [ka]

[0034] [Group II]

[0035] [ka]

[0036] In Group I and Group II, R a and R b are each independently hydrogen, deuterium, a cyano group, or a substituted or unsubstituted C1-C10 alkyl group; R c ~R e are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C20 aryl group; D is deuterium; m5 and m8 are each independently an integer of 1 to 5; m6 and m9 are each independently an integer of 1 to 4; and m7 and m10 are each independently an integer of 1 to 3.

[0037] The compound represented by chemical formula 1 has a basic skeleton of biscarbazole, in which the benzene moiety constituting the carbazole is substituted with at least one deuterium, and at the same time, 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 constituting the carbazole and the 9th (N-directed) substituent of the carbazole are substituted with deuterium. By simultaneously substituting the benzene moiety constituting 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 lowered. This lowers the ground state energy and weakens the intermolecular interactions, allowing the creation of an amorphous thin film, which further improves heat resistance and is effective in extending the lifetime. In other words, when this is applied, it is possible to realize organic light-emitting devices with low drive, high efficiency, and particularly long lifetime.

[0038] Chemical formula 1 can be represented by, for example, any one of the following chemical formulas 1-1 to 1-10 depending on the linking position of carbazole.

[0039] [Chemical formula 1-1]

[0040] [ka]

[0041] [Chemical formula 1-2]

[0042]

change

[0043] [Chemical formula 1-3]

[0044]

change

[0045] [Chemical formula 1-4]

[0046]

change

[0047] [Chemical Formula 1-5]

[0048]

change

[0049] [Chemical formula 1-6]

[0050]

change

[0051] [Chemical Formula 1-7]

[0052]

change

[0053] [Chemical Formula 1-8]

[0054]

change

[0055] [Chemical formula 1-9]

[0056] [ka]

[0057] [Chemical formula 1-10]

[0058] [ka]

[0059] In chemical formulas 1-1 to 1-10, Ar 1 ~Ar 6 , 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. 2 If is 2 or more, each R 2 may be the same or different. 3 If is 2 or more, each R 3 may be the same or different. 4 If is 2 or more, each R 4 may be the same or different. 3 If is 2 or more, each Ar 3 may be the same or different. 4 If is 2 or more, each Ar 4 may be the same or different. 5 If is 2 or more, each Ar 5 may be the same or different. 6 If is 2 or more, each Ar 6 may be the same or different from each other.

[0060] As an example, R 1 ~R 4 At least two of the R1 ~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 of 1 to 4, m2 is an integer of 1 to 3, and R 3 and R 4 may each be hydrogen. For example, R 3 and R 4 are each deuterium, m3 is an integer from 1 to 3, m4 is an integer from 1 to 4, and R 1 and R 2 may each be hydrogen. For example, R 1 and R 4 are each deuterium, m1 and m4 are each an integer of 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 a C6-C30 aryl group that is unsubstituted or substituted with deuterium.

[0061] As an 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.

[0062] [Chemical formula 1a]

[0063] [ka]

[0064] [Formula 1b]

[0065] [ka]

[0066] [Chemical formula 1c]

[0067] [ka]

[0068] [Chemical formula 1d]

[0069] [ka]

[0070] [Chemical formula 1e]

[0071] [ka]

[0072] In chemical formula 1a to chemical formula 1e, Ar 1 ~Ar 6 The definition of Ar is as described above. 3 ~Ar 6 are each independently a C6 to C30 aryl group substituted or unsubstituted with hydrogen or deuterium, and D3 means that three deuterium atoms are substituted. 3 ~Ar 6 may each independently be a C6-C20 aryl group substituted or unsubstituted with hydrogen or at least one deuterium. For example, Ar 3 ~Ar 6 are each independently hydrogen or a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a deuterium-substituted or unsubstituted terphenyl 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 in Formula 1 1and Ar 2 are each independently one selected from the substituents listed in Group I-1 and Group II-1 below, and Ar 1 and Ar 2 At least one of the groups may be one selected from the substituents listed in Group II-1 below.

[0073] [Group I-1]

[0074] [ka]

[0075] [Group II-1]

[0076] [ka]

[0077] [ka]

[0078] [ka]

[0079] In Group I-1 and Group II-1, * is the point of attachment.

[0080] As an example, Chemical Formula 1 can be represented by the following Chemical Formula 1-8a or Chemical Formula 1-8e.

[0081] [Formula 1-8a]

[0082] [ka]

[0083] [Formula 1-8e]

[0084] [ka]

[0085] In formula 1-8a and formula 1-8e, Ar 1 and Ar 2 is as mentioned above, and Ar 6 is a C6-C30 aryl group substituted or unsubstituted with deuterium. For example, Ar 6 may be a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a deuterium-substituted or unsubstituted terphenyl 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, 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.

[0086] [Group 1]

[0087] [ka]

[0088] [ka]

[0089] [ka]

[0090] [ka]

[0091] [ka]

[0092]

change

[0093]

change

[0094]

change

[0095]

change

[0096]

change

[0097]

change

[0098]

change

[0099]

change

[0100]

change

[0101]

change

[0102] [ka]

[0103] [ka]

[0104] [ka]

[0105] [ka]

[0106] [ka]

[0107] 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 Ar 2 may each be a phenyl group substituted with at least one deuterium, a biphenyl 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.

[0108] In addition to the compound for an organic optoelectronic device described above, one or more additional compounds may be included. For example, the compound for an organic optoelectronic device described above may be applied in the form of a composition further including a known host material. For example, the compound for an organic optoelectronic device described above may further include a dopant. The dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, for example, a red phosphorescent dopant. The dopant is a substance that emits light when mixed in a small amount with the compound for an organic optoelectronic device. Typically, a substance such as a metal complex that emits light by multiple excitation to a triplet state or higher may be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types may be included. An example of the dopant is a phosphorescent dopant, such as an organometallic compound containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the following chemical formula Z, but is not limited thereto.

[0109] [Chemical formula Z] LMX In the chemical formula Z, M is a metal, and L and X are the same or different 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 and X may be, for example, a bidentate ligand. Examples of the ligands represented by L and X can be selected from the chemical formulas listed in Group A below, but are not limited thereto.

[0110] [Group A]

[0111] [ka]

[0112] In Group A, R 300 ~R 302 are each independently hydrogen, deuterium, a C1-C30 alkyl group substituted or unsubstituted with a halogen, a C6-C30 aryl group substituted or unsubstituted with a C1-C30 alkyl, or a halogen; R 303 ~R 324 are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

[0113] As an example, the dopant may be represented by the following chemical formula V. [Chemical formula V]

[0114] [ka]

[0115] In the chemical formula V, R 101 ~R 116 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 and R 132 ~R 134 are each independently a C1 to C6 alkyl group, and R 101 ~R 116 At least one of the functional groups represented by the following chemical formula V-1 is100 is a monovalent anionic bidentate ligand that coordinates to iridium through 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.

[0116] [Chemical formula V-1]

[0117] [ka]

[0118] In the chemical formula V-1, R 135 ~R 139 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 and R 132 ~R 134 are each independently a C1 to C6 alkyl group, and * means a moiety linked to a carbon atom.

[0119] For example, a dopant represented by the following chemical formula Z-1 may be included. [Chemical formula Z-1]

[0120] [ka]

[0121] In formula Z-1, rings A, B, C, and D each independently represent a penta- or hexa-component carbocyclic or heterocyclic ring. A , R B , R C , and R D each independently represents mono-, di-, tri-, or tetra-substituted, or unsubstituted. B , L C , and L Dare each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof. When nA is 1, L E is selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; when nA is 0, L E does not exist. R A , R B , R C , R D R, R, and R' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. A , R B , R C , R D , R, and R′ are optionally linked to form a ring. X B , X C , X D , and X E are each independently selected from the group consisting of carbon and nitrogen. 1 , Q 2 , Q 3 , and Q 4 indicates an oxygen or a direct bond, respectively.

[0122] In one embodiment, the dopant may be a platinum compound, which may be represented, for example, by Formula VI below. [Chemical formula VI]

[0123] [ka]

[0124] In formula VI, X 100 are O, S and NR 131 Selected from among R 117 ~R 131 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 R 132 ~R 134 are each independently a C1 to C6 alkyl group, and R 117 ~R 131 At least one of the groups is -SiR 132 R 133 R 134 Or a tert-butyl group.

[0125] 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 an element that can convert electrical energy and light energy into each other, and examples thereof include an organic photoelectric element, an organic light-emitting element, an organic solar cell, and an organic photoreceptor drum. Here, an organic light-emitting element, which is an example of an organic optoelectronic device, will be described with reference to the drawings.

[0126] 1 is a cross-sectional view showing an organic light-emitting device according to one embodiment. Referring to FIG. 1, an organic light-emitting device 100 according to one embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 located between the anode 120 and the cathode 110.

[0127] The anode 120 may be formed of a conductor with a high work function to facilitate hole injection, such as a metal, metal oxide, and / or conductive polymer. Examples of the anode 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.

[0128] The cathode 110 may be formed of a conductor with a low work function to facilitate electron injection, such as a metal, metal oxide, and / or conductive polymer. Examples of the cathode 110 include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, and barium, or alloys thereof, and multilayer structures such as LiF / Al, LiO / Al, LiF / Ca, and BaF / Ca.

[0129] The organic layer 105 may include the compound for an organic optoelectronic device described above. The organic layer 105 may include an emitting layer 130, which may include the compound 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 compound for an organic optoelectronic device described above as a phosphorescent host.

[0130] 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 anode 120 and the light-emitting layer 130 and block electrons. Specifically, the hole transport region 140 may include a hole transport layer between the anode 120 and the light-emitting layer 130 and a hole transport auxiliary layer between the light-emitting layer 130 and the hole transport layer, and at least one of the compounds listed in Group B below may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0131] [Group B]

[0132] [ka]

[0133] [ka]

[0134] [ka]

[0135] [ka]

[0136] [ka]

[0137] 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.

[0138] The charge transport region may be, for example, the electron transport region 150. The electron transport region 150 can further enhance electron injection and / or electron mobility between the cathode 110 and the light-emitting layer 130 and block holes. Specifically, the electron transport region 150 may include an electron transport layer between the cathode 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 may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0139] [Group C]

[0140] [ka]

[0141] [ka]

[0142] [ka]

[0143] [ka]

[0144] One embodiment may be an organic light-emitting device including an emitting layer as an organic layer. Another embodiment may be an organic light-emitting device including an emitting layer and a hole transport region as an organic layer. Still another embodiment may be an organic light-emitting device including an emitting layer and an electron transport region as an organic layer. An organic light-emitting device according to one embodiment of the present invention may include, as shown in FIG. 1, a hole transport region 140 and an electron transport region 150 in addition to the emitting layer 130 as the organic layer 105. Meanwhile, the organic light-emitting device may further include an electron injection layer (not shown) and a hole injection layer (not shown) in addition to the emitting layer as the organic layer. The organic light-emitting device 100 may be manufactured by forming an anode or cathode on a substrate, forming an organic layer using a dry deposition method such as vacuum evaporation, sputtering, plasma plating, or ion plating, and then forming a cathode or anode thereon. The above-described organic light-emitting device may be used in an organic light-emitting display device. [Example]

[0145] The above-described embodiments will be described in more detail with reference to the following examples, which are provided for illustrative purposes only and are not intended to limit the scope of the present invention.

[0146] Unless otherwise specified, the starting materials and reactants used in the following examples and synthesis examples were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry, or P&H Tech, or synthesized by known methods.

[0147] (Manufacturing compounds for organic photoelectron devices) The compounds presented as more specific examples of the compounds of the present invention were synthesized through the following steps.

[0148] Synthesis Example 1: Synthesis of Compound 1-38 [Reaction Scheme 1]

[0149] [ka]

[0150] Step 1: Synthesis of compound Int 1 Compound Int 1 was synthesized with reference to the method disclosed in Korean Patent Publication No. 2016-0049842.

[0151] Step 2: Synthesis of Compounds 1-38 30 g (0.0535 mol) of compound Int 1, 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.

[0152] Synthesis Example 2: Synthesis of Compound 1-98 [Reaction Scheme 2]

[0153] [ka]

[0154] Compound 1-98 (19 g, white solid, LC-mass Mz 655.29, C) was synthesized in the same manner as in Synthesis Example 1, except that 30 g (0.047 mol) of Int 2 was used instead of Int 1. 48 H 14 D 18 N2) was obtained.

[0155] Synthesis Example 3: Synthesis of Compound 1-110 [Reaction Scheme 3]

[0156] [ka]

[0157] Compound 1-110 (15 g, white solid, LC-mass Mz 657.31, C) was synthesized in the same manner as in Synthesis Example 1, except that 20 g (0.036 mol) of Int 3 was used instead of Int 1. 48 H 13 D 19 N2) was obtained.

[0158] Comparative Synthesis Example 1: Synthesis of Compound Y1

[0159] [ka]

[0160] 47g (0.281mol) of carbazole, 50g (0.310mol) of bromobenzene-D5, 53g (0.028mol) of CuI, 58g (0.42mol) of KCO, 5g (0.028mol) of 1,10-phenanthroline, and 560ml of DMF were mixed and stirred under reflux. After the reaction was completed, the mixture was cooled to room temperature and purified water was added to precipitate a solid. The solid was purified using a column to obtain 62g of Int 4 (molecular weight 248.33).

[0161] 62 g (0.25 mol) of Int 4 was added to DMF and dissolved. 45 g (0.25 mol) of NBS was gradually added at 0°C, and the reaction was terminated by stirring at room temperature. Purified water was added to the reaction solution to generate crystals, and the solid was purified using a column to obtain 80 g of Int 5 (molecular weight 327.23).

[0162] 80 g (0.245 mol) of Int 5, 120 g (0.27 mol) of 4-biphenyl-carbazole-3-boronicester, 68 g (0.49 mol) of K2CO3, 414 g (0.0122 mol) of Pd(PPh3), 320 ml of purified water, and 490 ml of THF were mixed and stirred under reflux. After the reaction was completed, purified water was added for extraction, and the organic layer was concentrated. The mixture was purified using a column to obtain 90 g of compound Y1 (molecular weight 565.72).

[0163] Comparative Synthesis Example 2: Synthesis of Compound Y2

[0164] [ka]

[0165] 35g (0.095mol) of (phenyl-4-boronic acid)-9H-carbazole, 17g (0.105mol) of bromobenzene-D5, 43.3g (0.0028mol) of Pd(PPh3), 32.7g (0.237mol) of K2CO3, 120ml of purified water, and 320ml of THF were mixed and stirred under reflux. After the reaction was completed, the mixture was cooled, purified water was added, and the organic layer was separated and concentrated. The concentrate was purified using a column to obtain 25g of Int 6 (molecular weight 324.43).

[0166] 20 g (0.062 mol) of Int 6 was dissolved in 200 ml of DMF, and 11.5 g (0.065 mol) of NBS was slowly added at 0°C. The reaction was terminated by stirring at room temperature, and purified water was added to produce a solid. The solid was purified using a column to obtain 23 g of Int 7 (molecular weight 403.33).

[0167] 20 g (0.0496 mol) of Int 7, 22 g (0.06 mol) of phenyl-9H-carbazole-3-boronic ester, 1.72 g (0.0015 mol) of Pd(PPh3), 13.7 g (0.099 mol) of K2CO3, 50 ml of purified water, and 165 ml of THF were mixed and stirred under reflux. After the reaction was completed, the mixture was cooled, purified water was added, and the organic layer was separated and concentrated. The concentrate was purified using a column to obtain 11.5 g of compound Y2 (molecular weight 565.72).

[0168] Comparative Synthesis Example 3: Synthesis of Compound Y3

[0169] [ka]

[0170] Compound Y3 (5 g, white solid, LC-mass Mz 659.78, C) was synthesized in the same manner as in Synthesis Example 1, except that 20 g (0.036 mol) of Int 8 was used instead of Int 1. 48 H 10 D 22 N2) was obtained.

[0171] (Fabrication of organic light-emitting devices) Example 1 A glass substrate coated with a thin film of ITO (indium tin oxide) was ultrasonically cleaned with distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, and then dried. The substrate was then transferred to a plasma cleaner and cleaned using oxygen plasma for 10 minutes, after which it was transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as an anode, Compound A doped with 1% NDP-9 (commercially available from Novaled) was vacuum-deposited on the ITO substrate to form a 100 Å thick hole injection layer. Compound A was vacuum-deposited on the hole injection layer to a thickness of 1350 Å to form a hole transport layer. Compound B was vacuum-deposited on 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 was used as a host, doped with 7 wt% PhGD as a dopant, and a 400 Å thick emissive layer was vacuum-deposited on the hole transport auxiliary layer. Next, compound C was deposited on the light-emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compound D and LiQ were simultaneously vacuum-deposited in a 1:1 weight ratio to form an electron transport layer to a thickness of 300 Å. LiQ and Al were sequentially vacuum-deposited to a thickness of 15 Å and 1200 Å on the electron transport layer to form a cathode, thereby fabricating an organic light-emitting device.

[0172] The structure was ITO / compound A (1% NDP-9 doping, 100 Å) / compound A (1350 Å) / compound B (350 Å) / EML [93 wt% host (compounds 1-38): 7 wt% PhGD] (400 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]

[0173] [ka]

[0174] Comparative Examples 1 to 3 The devices of Comparative Examples 1 to 3 were fabricated in the same manner as in Example 1, except that the host was changed as shown in Tables 1 and 2 below.

[0175] 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.

[0176] (2) Measurement of changes in brightness in response to voltage changes 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.

[0177] (3) Luminous efficiency measurement Using the luminance and current density measured from (1) and (2) above, the same current density (10 mA / cm 2 The luminous efficiency (cd / A) of each sample was calculated. The relative values ​​based on the luminous efficiency of Comparative Example 3 are shown in Table 2 below.

[0178] (4) Lifespan measurement Luminance (cd / m 2 ) to 6,000 cd / m 2 The time until the luminous efficiency (cd / A) decreased to 97% was measured. The relative values ​​based on the life of Comparative Example 1 are shown in Table 1 below.

[0179] (5) Drive voltage measurement 15mA / cm using a current-voltage meter (Keithley 2400) 2 The driving voltage of each element was measured and the results were obtained. The relative values ​​based on the driving voltage of Comparative Example 3 are shown in Table 2 below.

[0180] [Table 1]

[0181] [Table 2]

[0182] Referring to Tables 1 and 2, it can be seen that the organic light emitting devices according to the embodiments of the present invention have significantly improved driving voltage, efficiency, and lifespan characteristics compared to the organic light emitting device according to the comparative example.

[0183] Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic concept of the present invention defined in the claims also fall within the scope of the present invention. [Explanation of symbols]

[0184] 100: Organic light-emitting element 105:Organic layer 110: Cathode 120:Anode 130: Light-emitting layer 140: Hole transport region 150: Electron transport area

Claims

1. Represented by the following chemical formula 1a: [Chemical formula 1a] 【Chemical 1】 In the above formula 1a, D ３ indicates that three deuterium atoms are bonded, Ar １ and Ar ２ are different from each other and are one selected from the substituents listed in Group II below, [Group II] 【Chemistry 2】 In said Group II, R ａ and R ｂ is deuterium, m5 is 1, 2, or 3; m6 is 0 or 1,

2. The chemical formula 1a is represented by any one of the following chemical 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 chemical formulas 1-1 to 1-10, R １ , R ２ , R ３ , R ４ are both deuterium, 2. The compound for organic optoelectronic devices according to claim 1, wherein m1 and m4 are 4, and m2 and m3 are 3.

3. Ar in Formula 1a １ and Ar ２ are each independently one selected from the substituents listed in Group II-1 below, [Group II-1] 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 The compound for an organic optoelectronic device according to claim 1, wherein in Group II-1, * represents a linking point.

4. The compound for an organic optoelectronic device according to claim 1, wherein the formula 1a is represented by the following formula 1-8a: [Chemical formula 1-8a] 【Chemistry 19】 In the above formula 1-8a, Ar １ and Ar ２ are different from each other and are one selected from the substituents listed in Group II below, [Group II] 【Chemistry 20】 In said Group II, R ａ and R ｂ is deuterium, m5 is 1, 2, or 3; m6 is 0 or 1,

5. The compound for an organic optoelectronic device according to claim 1 , which is one selected from the compounds listed in Group 1 below. [Group 1] 【Chemical 21】 【Chemical 22】 【Chemical 23】 【Chemistry 24】 【Chemistry 25】 【Chemical 26】 【Chemical 27】 【Chemical Formula 28】 【Chemical 29】 【Chemistry 30】

6. an anode and a cathode facing each other, and at least one organic layer located between the anode and the cathode; The organic layer comprises the compound for organic optoelectronic devices according to any one of claims 1 to 5.

7. the organic layer includes an emitting layer, The organic optoelectronic device according to claim 6 , wherein the light-emitting layer comprises the compound for an organic optoelectronic device.

8. A display device comprising the organic optoelectronic device of claim 6.

Images