Compound, organic light-emitting device including same, and display apparatus

Abstract

The invention provides a compound, an organic light-emitting device including the compound, and a display apparatus including the organic light-emitting device. An organic light emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including a light emitting layer, in which the organic layer includes a compound of Formula 1: Formula 1 # imgabs0 # according to one or more embodiments of the present disclosure, characteristics of the organic light emitting device may be improved by including the compound of Formula 1.

Description

[0001] This application is a divisional application of an invention patent application with an application date of August 23, 2016, application number 201610710972.9, and invention name “Compounds, organic light-emitting devices including the same, and display devices”.

[0002] CROSS-REFERENCE TO RELATED APPLICATIONS

[0003] This application claims priority to and the benefit of Korean Patent Application No. 10-2015-0147537 filed on October 22, 2015, in the Korean Intellectual Property Office, the disclosure of which is incorporated herein in its entirety by reference. Technical Field

[0004] One or more aspects of embodiments of the present disclosure are directed to a compound, an organic light-emitting device including the same, and a display apparatus. Background Art

[0005] Organic light-emitting devices are self-luminous devices that have wide viewing angles, high contrast, short response times, and excellent brightness, driving voltage, and / or response speed characteristics, and can produce full-color images.

[0006] The organic light-emitting device may include a first electrode arranged (e.g., placed) on a substrate, and a hole transport region, a light-emitting layer, an electron transport region, and a second electrode sequentially arranged on the first electrode. Holes provided by the first electrode, for example, may move through the hole transport region to the light-emitting layer, and electrons provided by the second electrode, for example, may move through the electron transport region to the light-emitting layer. Carriers such as holes and electrons may then recombine in the light-emitting layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light. Summary of the invention

[0007] One or more aspects of embodiments of the present disclosure are directed to a material for forming a hole transport region and an organic light-emitting device having improved characteristics due to inclusion of the material.

[0008] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the embodiments.

[0009] According to one or more embodiments, there is provided a compound represented by Formula 1:

[0010] Formula 1

[0011]

[0012] In formula 1,

[0013] R 1 To R 17may be independently selected from hydrogen, deuterium, halogen, amino, nitro, nitrile, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;

[0014] R 1 To R 17 At least one of them includes a group represented by Formula 1-1:

[0015] Formula 1-1

[0016]

[0017] Where Ar in Formula 1-1 1 and Ar 2 Can be selected from substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups, provided that Ar 1 and Ar 2 each of which is not a substituted or unsubstituted dibenzazepine or a substituted or unsubstituted tribenzazepine;

[0018] X can be selected from substituted or unsubstituted C 6 -C60 Arylene, substituted or unsubstituted C 1 -C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;

[0019] m may be an integer selected from 0 to 5;

[0020] When m is 2 or greater, 2 or more X may be the same as or different from each other; and

[0021] The substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 2 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted monovalent non-aromatic fused polycyclic group, substituted monovalent non-aromatic fused heteropolycyclic group, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 At least one substituent of the heteroarylene group, the substituted divalent non-aromatic fused polycyclic group, and the substituted divalent non-aromatic fused heteropolycyclic group may be selected from the group consisting of:

[0022] deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C60 Alkoxy,

[0023] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 ) and -B(Q 16 )(Q 17 ),

[0024] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups,

[0025] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 ) and -B(Q 26 )(Q 27 ),as well as

[0026] Si(Q 13 )(Q 14 )(Q 15 ),

[0027] Where Q 11 To Q 17 and Q 21 To Q 27 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group.

[0028] Another embodiment of the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including a light-emitting layer, wherein the organic layer includes the compound of Formula 1.

[0029] Another embodiment of the present disclosure provides a display apparatus including an organic light emitting device, wherein a first electrode of the organic light emitting device is electrically coupled to a source electrode or a drain electrode of a thin film transistor. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] These and / or other aspects will become apparent and more easily understood from the following description of the embodiments in conjunction with the accompanying drawings, which are schematic diagrams of organic light-emitting devices according to embodiments of the present disclosure. DETAILED DESCRIPTION

[0031] Now will be referred to in detail embodiment, its example is described in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this regard, the present embodiment can have different forms and should not be construed as being limited to the description listed herein. Therefore, by referring to the accompanying drawings, only the embodiment is described below to explain the various aspects of this description. The term "and / or" used herein includes any and all combinations of one or more listed related items. Statements such as "at least one of", "one of" and "selected from", when before / after a column of elements, modify the entire column of elements, rather than modifying the individual elements in the column. In addition, the use of "may" refers to "one or more embodiments of the present invention" when describing embodiments of the present invention.

[0032] The compound according to the embodiment may be represented by the following Formula 1:

[0033] Formula 1

[0034]

[0035] In formula 1,

[0036] R 1 To R 17 may be independently selected from hydrogen, deuterium, halogen, amino, nitro, nitrile, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;

[0037] Where R 1 To R 17 At least one of them includes a group represented by Formula 1-1:

[0038] Formula 1-1

[0039]

[0040] Where Ar in formula 1-1 1 and Ar 2 Can be selected from substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups, provided that Ar 1 and Ar 2 each of which is not a substituted or unsubstituted dibenzazepine or a substituted or unsubstituted tribenzazepine;

[0041] X can be selected from substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;

[0042] m may be an integer selected from 0 to 5;

[0043] When m is 2 or more, a plurality of Xs may be the same as or different from each other; and

[0044] The substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 2 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted monovalent non-aromatic fused polycyclic group, substituted monovalent non-aromatic fused heteropolycyclic group, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 At least one substituent of the heteroarylene group, the substituted divalent non-aromatic fused polycyclic group, and the substituted divalent non-aromatic fused heteropolycyclic group may be selected from the group consisting of:

[0045] deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;

[0046] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q12 )、-Si(Q 13 )(Q 14 )(Q 15 ) and -B(Q 16 )(Q 17 );

[0047] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;

[0048] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 ) and -B(Q 26 )(Q 27 );as well as

[0049] Si(Q 13 )(Q 14 )(Q 15 ),

[0050] Where Q 11 To Q 17 and Q 21 To Q 27 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group.

[0051] A compound including an azapine moiety, which is a nitrogen-containing 7-membered ring compound, can be used as a charge transport material for electrophotography or an organic light-emitting device. Among such compounds, an ethylene-based compound including an azapine moiety, a hydrazone compound having a benzazepine skeleton, and / or a compound having two or more benzazepine moieties can be used in a hole transport layer of an organic device.

[0052] Various compounds including an azapine moiety can be used as phosphorescent hosts, fluorescent hosts, dopants and / or materials for electron transport layers, and can also be included in hole transport layers. For example, azapine-containing arylamine compounds have been used as materials for hole transport layers.

[0053] However, monoamine or diamine derivatives with two or more azepine groups can have low efficiency and relatively short life when they are used as hole transport materials. Due to these characteristics, such monoamine or diamine derivatives are not commercially available. Therefore, efforts have been made to use other arylamine derivatives to develop hole injection materials with low voltage, high efficiency and long life.

[0054] Recently, in order to improve the efficiency of an organic light-emitting device and to increase the efficiency of singlet exciton generation due to triplet-triplet coupling (TTF), which effectively uses excitons generated in a light-emitting layer, a first hole transport layer having a conventional triplet energy level and a second hole transport layer having a triplet energy level higher than the conventional triplet energy level have been described. For example, various compounds can be used for such a second hole transport layer.

[0055] In an embodiment of the present disclosure, a monoamine compound (eg, a compound including one azapine moiety) is used as a hole transport material to improve characteristics of an organic light-emitting device.

[0056] The substituents of Formula 1 will now be described in more detail.

[0057] In various embodiments, R selected from Formula 1 13 To R 17 Two or more adjacent substituents of may be connected to each other to form a ring. Non-limiting examples of compounds of Formula 1 (wherein R 13 To R 17 Two or more adjacent substituents of are connected to each other to form a ring) include compounds 32, 36, 40-45 and 47.

[0058] In various embodiments, Ar in Formula 1-1 1 and Ar 2 The compound of Formula 1 (wherein Ar in Formula 1-1 1 and Ar 2 Non-limiting examples of the compounds (which are connected to each other to form a ring) include compounds 58-60.

[0059] In various embodiments, m in Formula 1-1 may be an integer selected from 0 to 3.

[0060] In various embodiments, R in Formula 1 3 and R 10 Each independently may be a substituted or unsubstituted phenyl group.

[0061] In various embodiments, R in Formula 1 and Formula 4 (shown below) 1 , R 4 To R 9 , R 12 , R 13 and R 17 can each independently be hydrogen or deuterium.

[0062] In various embodiments, X in Formula 1-1 may be a group represented by any one selected from Formulae 2a to 2f:

[0063]

[0064] In Formulas 2a to 2f, H 1 Can be selected from O, S, NR 21 and CR 22 R 23 ,

[0065] R 21 To R 23 may each be independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C1-C20 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group; and * represents a binding site to an adjacent atom.

[0066] In various embodiments, Ar in Formula 1-1 1 and Ar 2 may each independently be a group represented by one selected from Formulae 3a to 3g:

[0067]

[0068] In Formulas 3a to 3g, H 1 Can be selected from O, S, NR 21 and CR 22 R 23 ,

[0069] R 21 To R 23 and Z 1The substituted or unsubstituted C1-C20 alkyl groups may be independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C6-C20 aryl groups, substituted or unsubstituted C1-C20 heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups, and Si(Q) 13 )(Q 14 )(Q 15 ), where Q 13 To Q 15 As defined herein;

[0070] p in Formula 3a may be an integer selected from 1 to 5, p in Formulas 3b and 3c may be an integer selected from 1 to 7, p in Formula 3d may be an integer selected from 1 to 4, and p in Formulas 3e to 3g may be an integer selected from 1 to 9,

[0071] When p is 2 or greater, 2 or more Z 1 may be the same as or different from each other; and

[0072] *Indicates the binding site with the adjacent atom.

[0073] In some embodiments, when H in Formula 3c 1 CR 22 R 23 When R 22 and R 23 Can be connected to each other to form a ring.

[0074] In various embodiments, the compound of Formula 1 may be represented by Formula 2:

[0075] Formula 2

[0076]

[0077] In various embodiments, the compound of Formula 1 may be represented by Formula 3:

[0078] Formula 3

[0079]

[0080] In various embodiments, the compound of Formula 1 may be represented by Formula 4:

[0081] Formula 4

[0082]

[0083] In various embodiments, the compound of Formula 1 may be represented by Formula 5:

[0084] Formula 5

[0085]

[0086] In various embodiments, the compound of Formula 1 may be represented by Formula 6:

[0087] Formula 6

[0088]

[0089] In various embodiments, the compound of Formula 1 may be one of the following compounds 1 to 117:

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098] The term "organic layer" used herein may refer to a single layer and / or a plurality of layers arranged (eg, placed) between a first electrode and a second electrode of an organic light-emitting device. Materials included in the "organic layer" are not limited to organic materials.

[0099] The accompanying drawings are schematic diagrams of an organic light-emitting device 10 according to an embodiment of the present invention. The organic light-emitting device 10 includes a first electrode 110 , an organic layer 150 , and a second electrode 190 .

[0100] Hereinafter, a structure of an organic light-emitting device according to an embodiment and a method of manufacturing the organic light-emitting device according to an embodiment will be described with reference to the accompanying drawings.

[0101] In the drawings, the substrate may be additionally disposed under the first electrode 110 or on the second electrode 190. The substrate may be a glass substrate and / or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and / or waterproofness.

[0102] The first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be selected from materials having a high work function to facilitate hole injection. The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 110 may be a transparent and highly conductive material, and non-limiting examples of such materials include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ) and zinc oxide (ZnO). When the first electrode 110 is a semi-transmissive electrode or a reflective electrode, at least one of magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) may be used as a material for forming the first electrode 110.

[0103] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited thereto.

[0104] The organic layer 150 may be disposed on the first electrode 110 , and the second electrode 190 may be disposed on the organic layer 150 .

[0105] The organic layer 150 may include a light emitting layer and may further include a hole transport region disposed between the first electrode and the light emitting layer, and an electron transport region disposed between the light emitting layer and the second electrode.

[0106] In various embodiments, the hole transport region may include at least one selected from a hole transport layer (HTL), a hole injection layer (HIL), and an electron blocking layer; and the electron transport region may include at least one selected from a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL). However, it is understood that the embodiments of the present disclosure are not limited thereto.

[0107] The hole transport region may have a single-layer structure formed of a single material, a single-layer structure formed of a plurality of different materials, or a multi-layer structure having a plurality of layers formed of a plurality of different materials.

[0108] The hole transport layer may include a first hole transport layer and a second hole transport layer.

[0109] In some embodiments, the first hole transport layer may include the compound of Formula 1 according to an embodiment of the present disclosure.

[0110] For example, the hole transport region may have a single-layer structure formed of a plurality of different materials, or a structure of hole injection layer / hole transport layer, a structure of hole injection layer / first hole transport layer / second hole transport layer, a structure of hole injection layer / first hole transport layer / second hole transport layer / electron blocking layer, or a structure of hole injection layer / hole transport layer / electron blocking layer, wherein the layers of each structure are stacked sequentially starting from the first electrode 110 in the order described above, but the structure of the hole transport region is not limited thereto.

[0111] When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 110 by using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Brokett (LB) method, inkjet printing, laser printing and / or laser induced thermal imaging.

[0112] When the hole injection layer is formed by vacuum deposition, for example, the vacuum deposition may be performed at a deposition temperature of about 100° C. to about 500° C., at a ... -8 to about 10 -3 Torr vacuum and about / second to about The deposition rate was carried out at / s.

[0113] When the hole injection layer is formed by spin coating, for example, the spin coating may be performed at a coating rate of about 2000 rpm to about 5000 rpm and at a temperature of about 80° C. to 200° C., considering the compound for forming the hole injection layer to be deposited and the structure of the hole injection layer to be formed.

[0114] When the hole transport region includes a hole transport layer, the hole transport layer may be formed on the first electrode 110 or the hole injection layer by using one or more suitable methods such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing and / or laser induced thermal imaging. When the hole transport layer is formed by vacuum deposition and / or spin coating, the deposition and coating conditions for the hole transport layer may be the same (or substantially similar) to the deposition and coating conditions for the hole injection layer.

[0115] In various embodiments, the first hole transport layer may include a compound represented by Formula 201A:

[0116] Formula 201A

[0117]

[0118] In formula 201A,

[0119] L 201 To L 203Can be independently selected from the group consisting of:

[0120] phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene, chrysene, pyridylene, pyrazinylene, pyrimidinylene, pyridazinylene, quinolylene, isoquinolylene, quinoxalylene, quinazolinylene, carbazolylene and triazinylene, and

[0121] each of which is selected from at least one substituted phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene, chrysene, pyridylene, pyrazinylene, pyrimidylene, pyridazinylene, quinolylene, isoquinolylene, quinoxalylene, quinazolinylene, carbazolylene and triazinylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl;

[0122] xa1 to xa3 can each independently be 0 or 1;

[0123] R 203 and R 211 Can be independently selected from the group consisting of:

[0124] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, and

[0125] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, each of which is substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl;

[0126] R 213 and R 214 Can be independently selected from the group consisting of:

[0127] C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy,

[0128] Each of the following C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl,

[0129] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, and

[0130] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, each of which is substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, and triazinyl; and R 215 and R 216Can be independently selected from the group consisting of:

[0131] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy,

[0132] Each of the following C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl,

[0133] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, and

[0134] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, each of which is substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl.

[0135] In various embodiments, R in Formula 201A 211 It may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyridyl group.

[0136] In various embodiments, R in Formula 201A 213 and R 214 Each may independently be a methyl group or a phenyl group.

[0137] In various embodiments, the compound of formula 201A may be one of the following compounds HT1 to HT33:

[0138]

[0139]

[0140]

[0141] In various embodiments, the second hole transport region may include the compound of Formula 1 according to an embodiment of the present disclosure.

[0142] The thickness of the hole transport region may be about to about For example, about to about When the hole transport region includes a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about to less than about For example, about to about and the thickness of the hole transport layer (i.e., the sum of the thickness of the first hole transport layer and the second hole transport layer) may be in the range of about to about For example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, satisfactory (or suitable) hole transport characteristics may be obtained without a significant increase in driving voltage.

[0143] In addition to the materials described above, the hole transport region may further include a charge generating material for improving conductivity. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.

[0144] The charge generating material may be, for example, a p-type dopant. The p-type dopant may be one selected from a quinone derivative, a metal oxide, and a cyano compound, but the embodiment is not limited thereto. Non-limiting examples of p-type dopants include quinone derivatives (e.g., tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ)); metal oxides (e.g., tungsten oxide and / or molybdenum oxide); and compound HT-D1 described below.

[0145]

[0146]

[0147] In addition to the hole injection layer and / or the hole transport layer, the hole transport region may further include a buffer layer and / or an electron blocking layer. The buffer layer may compensate for the optical resonance distance according to the wavelength of light emitted by the light emitting layer, and thus may improve the luminous efficiency of the formed organic light emitting device. As the material included in the buffer layer, any material included in the hole transport region may be used. The electron blocking layer may be used to prevent or reduce the injection of electrons from the electron transport region.

[0148] The light emitting layer may be formed on the first electrode 110 or the hole transport region by using one or more suitable methods such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing and / or laser induced thermal imaging. When the light emitting layer is formed by vacuum deposition and / or spin coating, the deposition and coating conditions for the light emitting layer may be the same (or substantially similar) to those for the hole injection layer.

[0149] When the organic light-emitting device 10 is a full-color organic light-emitting device, the light-emitting layer may be patterned into a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer according to sub-pixels. In various embodiments, the light-emitting layer may have a stacked structure of a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer, or may include a red light-emitting material, a green light-emitting material, and a blue light-emitting material mixed with each other in a single layer to emit white light.

[0150] The light emitting layer may include a host and a dopant.

[0151] For example, the subject may include at least one selected from TPBi, TBADN, ADN (also referred to herein as "DNA"), CBP, CDBP, and TCP:

[0152]

[0153] In various embodiments, the host may include a compound represented by Formula 301 below.

[0154] Formula 301

[0155] Ar 301 -[(L 301 ) xb1 -R 301 ] xb2 .

[0156] In formula 301,

[0157] Ar 301 Can be selected from the group consisting of:

[0158] naphthyl, heptalenyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl and indenoanthryl, and

[0159] each of which is selected from at least one substituted naphthyl, heptalenyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, naphthacene, pyrenyl, peryl, pentaphenyl and indenoanthryl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group and -Si(Q 301 )(Q 302 )(Q 303 )(where Q 301 To Q 303 can be independently selected from hydrogen, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 6 -C 60 Aryl and C 1 -C 60 heteroaryl);

[0160] L 301 Can be selected from the group consisting of:

[0161] phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene, chrysene, pyridylene, pyrazinylene, pyrimidinylene, pyridazinylene, quinolylene, isoquinolylene, quinoxalylene, quinazolinylene, carbazolylene and triazinylene, and

[0162] each of which is selected from at least one substituted phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene, chrysene, pyridylene, pyrazinylene, pyrimidylene, pyridazinylene, quinolylene, isoquinolylene, quinoxalylene, quinazolinylene, carbazolylene and triazinylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl;

[0163] R 301 Can be selected from the group consisting of:

[0164] C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy,

[0165] Each of the following C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl,

[0166] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, and

[0167] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, each of which is substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl;

[0168] xb1 can be selected from 0, 1, 2, and 3; and

[0169] xb2 can be selected from 1, 2, 3 and 4.

[0170] For example, in Equation 301,

[0171] L 301 may be selected from the group consisting of phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene and chrysene, and

[0172] each of which is selected from at least one substituted phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene and chrysene group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl and chrysene;

[0173] R 301 Can be selected from the group consisting of:

[0174] C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy,

[0175] Each of the following C 1 -C20 Alkyl and C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl and chrysene,

[0176] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl and chrysene, and

[0177] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl and chrysene, each of which is substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, and chrysene, but the embodiments of the present disclosure are not limited thereto.

[0178] For example, the host may include a compound represented by Formula 301A below:

[0179] Formula 301A

[0180]

[0181] The description of the substituents of Formula 301A can be understood by reference to the descriptions thereof provided herein.

[0182] The compound represented by Formula 301 may include one of Compounds H1 to H42, but is not limited thereto:

[0183]

[0184]

[0185]

[0186]

[0187] In various embodiments, the host may include one of the following compounds H43 to H49, but is not limited thereto:

[0188]

[0189]

[0190] The dopant may be at least one selected from a suitable fluorescent dopant and a suitable phosphorescent dopant.

[0191] The phosphorescent dopant may include an organic metal complex represented by the following Formula 401:

[0192] Formula 401

[0193]

[0194] In formula 401,

[0195] M may be selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm);

[0196] X 401 To X 404 may each independently be nitrogen or carbon;

[0197] A 401 and A 402 The rings may each be independently selected from substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted spiro-fluorene, substituted or unsubstituted indene, substituted or unsubstituted pyrrole, substituted or unsubstituted thiophene, substituted or unsubstituted furan, substituted or unsubstituted imidazole, substituted or unsubstituted pyrazole, substituted or unsubstituted thiazole, substituted or unsubstituted isothiazole, substituted or unsubstituted oxazole, substituted or unsubstituted isoxazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridazine, substituted or unsubstituted substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzoquinoline, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazoline, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzimidazole, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene, substituted or unsubstituted isobenzothiophene, substituted or unsubstituted benzoxazole, substituted or unsubstituted isobenzoxazolyl, substituted or unsubstituted triazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuran and substituted or unsubstituted dibenzothiophene; and

[0198] At least one substituent of the substituted benzene, substituted naphthalene, substituted fluorene, substituted spiro-fluorene, substituted indene, substituted pyrrole, substituted thiophene, substituted furan, substituted imidazole, substituted pyrazole, substituted thiazole, substituted isothiazole, substituted oxazole, substituted isoxazole, substituted pyridine, substituted pyrazine, substituted pyrimidine, substituted pyridazine, substituted quinoline, substituted isoquinoline, substituted benzoquinoline, substituted quinoxaline, substituted quinazoline, substituted carbazole, substituted benzimidazole, substituted benzofuran, substituted benzothiophene, substituted isobenzothiophene, substituted benzoxazole, substituted isobenzoxazolyl, substituted triazole, substituted oxadiazole, substituted triazine, substituted dibenzofuran and substituted dibenzothiophene may be selected from the group consisting of:

[0199] deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy,

[0200] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q401 )(Q 402 )、-Si(Q 403 )(Q 404 )(Q 405 ) and -B(Q 406 )(Q 407 ),

[0201] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups,

[0202] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 411 )(Q 412 )、-Si(Q 413 )(Q 414 )(Q 415 ) and -B(Q 416 )(Q 417 ),as well as

[0203] -N(Q 421 )(Q 422 )、-Si(Q 423 )(Q 424 )(Q 425 ) and -B(Q 426 )(Q 427 ),

[0204] Where Q 401 To Q 407 , Q 411 To Q 417 and Q 421 To Q 427 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;

[0205] L 401 It can be an organic ligand;

[0206] xc1 can be 1, 2, or 3; and

[0207] xc2 can be 0, 1, 2, or 3.

[0208] For example, in equation 401, L 401 It can be a monovalent, divalent or trivalent organic ligand. For example, L 401 The ligands may be selected from halogen ligands (e.g., Cl and / or F), diketone ligands (e.g., acetylacetonate, 1,3-diphenyl-1,3-propandionate, 2,2,6,6-tetramethyl-3,5-heptanedione (heptanedionate) and / or hexafluoropyruvate), carboxylic acid ligands (e.g., picolinate, dimethyl-3-pyrazolecarboxylate and / or benzoate), carbon monoxide ligands, isonitrile ligands, cyano ligands and phosphorus ligands (e.g., phosphine and / or phosphite), but are not limited thereto.

[0209] When A in formula 401 401 When there are two or more substituents, A 401 Two or more substituents of may be linked to form a saturated or unsaturated ring.

[0210] When A in formula 401 402 When there are two or more substituents, A 402 Two or more substituents of may be linked to form a saturated or unsaturated ring.

[0211] When xc1 in Formula 401 is 2 or greater, the multiple ligands in Formula 401 When xc1 in Formula 401 is 2 or greater, A of a ligand 401 and A 402 Each may be independently linked directly (e.g., via a bond such as a single bond) or via a linker (e.g., C 1 -C 5 Alkylene group, -N(R')-(wherein R' is C 1 -C 10 Alkyl or C 6 -C 20 aryl), and / or -C(=O)-) are respectively connected to the A of another adjacent ligand 401 and A 402connect.

[0212] The phosphorescent dopant may include one of the following compounds PD1 to PD74, but is not limited thereto:

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219] In various embodiments, the phosphorescent dopant may include PtOEP:

[0220]

[0221] In some embodiments, the fluorescent dopant may include one selected from DPVBi, DPAVBi, TBPe, DCM, DCJTB, coumarin 6, and C545T.

[0222]

[0223] In various embodiments, the fluorescent dopant may include a compound represented by the following Formula 501:

[0224] Formula 501

[0225]

[0226] In formula 501,

[0227] Ar 501 Can be selected from the group consisting of:

[0228] naphthyl, heptalenyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl and indenoanthryl, and

[0229] each of which is selected from at least one substituted naphthyl, heptalenyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, naphthacene, pyrenyl, peryl, pentaphenyl and indenoanthryl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group and -Si(Q 501 )(Q 502 )(Q 503 )(where Q 501 To Q 503 can be independently selected from hydrogen, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 6 -C 60 Aryl and C 1 -C 60 heteroaryl).

[0230] L 501 To L 503 The description can be compared with the one provided in this article and L 301 The relevant descriptions are the same;

[0231] R 501 and R 502 Can be independently selected from the group consisting of:

[0232] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl and dibenzothiophenyl, and

[0233] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl and dibenzothiophenyl groups, each of which is substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl and dibenzothiophenyl;

[0234] xd1 to xd3 may each independently be selected from 0, 1, 2 and 3; and

[0235] xd4 can be chosen from 1, 2, 3 and 4.

[0236] The fluorescent dopant may include one of compounds FD1 to FD8:

[0237]

[0238] The amount of the dopant in the light emitting layer may be, for example, in the range of about 0.01 to about 15 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

[0239] The thickness of the light-emitting layer can be about to about For example, about to about When the thickness of the light-emitting layer is within any one of these ranges, excellent (or suitable) light-emitting characteristics may be obtained without a significant increase in driving voltage.

[0240] The electron transport region may be arranged (eg, placed) on the light emitting layer.

[0241] The electron transport region may include at least one selected from a hole blocking layer, an electron transport layer (ETL), and an electron injection layer, but is not limited thereto.

[0242] When the electron transport region includes a hole blocking layer, the hole blocking layer can be formed on the light emitting layer by using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Brockett (LB) method, inkjet printing, laser printing and / or laser induced thermal imaging. When the hole blocking layer is formed by vacuum deposition and / or spin coating, the deposition and coating conditions for the hole blocking layer can be determined by referring to the deposition and coating conditions for the hole injection layer.

[0243] The hole blocking layer may include, for example, at least one selected from BCP and Bphen, but is not limited thereto.

[0244]

[0245] The thickness of the hole blocking layer can be about to about For example, about to about When the thickness of the hole blocking layer is within any one of these ranges, the hole blocking layer may have excellent (or suitable) hole blocking characteristics without a significant increase in driving voltage.

[0246] For example, the electron transport region may have a structure of electron transport layer / electron injection layer or a structure of hole blocking layer / electron transport layer / electron injection layer, wherein the layers of each structure are sequentially stacked in the order described starting from the light-emitting layer, but the structure of the electron transport region is not limited thereto.

[0247] According to an embodiment of the present disclosure, the organic layer 150 of the organic light-emitting device includes an electron transport region disposed between the light-emitting layer and the second electrode 190, and the electron transport region may include an electron transport layer. The electron transport layer may include a plurality of layers. For example, the electron transport layer may include a first electron transport layer and a second electron transport layer.

[0248] The electron transport layer may also include BCP, Bphen, Alq 3 , BAlq, TAZ and NTAZ.

[0249]

[0250] In various embodiments, the electron transport layer may include at least one compound selected from the group consisting of a compound represented by Formula 601 and a compound represented by Formula 602 shown below:

[0251] Formula 601

[0252] Ar 601 -[(L 601 ) xe1 -E 601 ] xe2.

[0253] In formula 601,

[0254] Ar 601 Can be selected from the group consisting of:

[0255] naphthyl, heptalenyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl and indenoanthryl, and

[0256] each of which is selected from at least one substituted naphthyl, heptalenyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, naphthacene, pyrenyl, peryl, pentaphenyl and indenoanthryl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 3 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group and -Si(Q 301 )(Q 302 )(Q 303 )(where Q 301 To Q 303 can be independently selected from hydrogen, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 6 -C 60 Aryl and C 1 -C 60heteroaryl);

[0257] L 601 A description may be obtained by referring to the provided 301 Related descriptions to understand;

[0258] E 601 Can be selected from the group consisting of:

[0259] pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and

[0260] pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzo furanyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridyl, imidazopyrimidyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl and imidazopyrimidinyl;

[0261] xe1 can be selected from 0, 1, 2, and 3; and

[0262] xe2 can be selected from 1, 2, 3 and 4.

[0263] Formula 602

[0264]

[0265] In equation 602,

[0266] X 611 Can be N or C-(L 611 ) xe611 -R 611 , X 612 Can be N or C-(L 612 ) xe612 -R 612 , X 613 Can be N or C-(L 613 ) xe613 -R 613 , and selected from X 611 To X 613 At least one of may be N;

[0267] By referring to the L 301 The relevant descriptions are used to understand L independently 611 To L 616 Description of

[0268] R 611 To R 616 Can be independently selected from the group consisting of:

[0269] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, and

[0270] phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, each of which is substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, and triazinyl; and

[0271] xe611 to xe616 can each be independently selected from 0, 1, 2 and 3.

[0272] The compound represented by Formula 601 and the compound represented by Formula 602 may each independently be selected from compounds ET1 to ET15 shown below.

[0273]

[0274]

[0275] The thickness of the electron transport layer can be about to about For example, about to about When the thickness of the electron transport layer is within any one of the ranges described above, the electron transport layer may have satisfactory (or suitable) electron transport characteristics without a significant increase in driving voltage.

[0276] In some embodiments, the electron transport layer may further include a metal-containing material in addition to the materials described above.

[0277] The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (8-hydroxyquinoline lithium, LiQ) and / or compound ET-D2.

[0278]

[0279] The electron transport region may include an electron injection layer that may be used to facilitate injection of electrons from the second electrode 190 .

[0280] The electron injection layer can be formed on the electron transport layer by using one or more suitable methods such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing and / or laser induced thermal imaging. When the electron injection layer is formed by vacuum deposition and / or spin coating, the deposition and coating conditions for the electron injection layer can be the same (or substantially similar) as those for the hole injection layer.

[0281] The electron injection layer may include a material selected from LiF, NaCl, CsF, Li 2 At least one of O, BaO and LiQ.

[0282] The thickness of the electron injection layer can be about to about For example, about to about When the thickness of the electron injection layer is within any one of the ranges described above, the electron injection layer may have satisfactory (or suitable) electron injection characteristics without a significant increase in driving voltage.

[0283] The second electrode 190 may be arranged on the organic layer 150 having a structure according to an embodiment of the present disclosure. The second electrode 190 may be a cathode, which is an electron injection electrode, and in this regard, the material for forming the second electrode 190 may be selected from metals, alloys, conductive compounds, and mixtures thereof having a lower work function. Non-limiting examples of materials for forming the second electrode 190 include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). In various embodiments, the material for forming the second electrode 190 may be ITO and / or IZO. The second electrode 190 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode.

[0284] The organic layer according to the embodiment may be formed by depositing the compound according to the embodiment of the present disclosure, or may be formed by using a wet method in which the compound according to the embodiment of the present disclosure is prepared in the form of a solution and then the solution of the compound is used for coating.

[0285] The organic light-emitting device according to the embodiment can be used in various display devices such as a passive matrix organic light-emitting display device and / or an active matrix organic light-emitting display device. For example, when the organic light-emitting device is included in an active matrix organic light-emitting display device, the first electrode arranged on the substrate can be used as a pixel electrode and can be electrically connected (e.g., coupled) to a source electrode or a drain electrode of a thin film transistor. In addition, the organic light-emitting device can be included in a display device that emits light in opposite directions (e.g., it can emit light from both sides of a display panel).

[0286] Hereinabove, the organic light emitting device has been described with reference to the accompanying drawings, but embodiments of the present disclosure are not limited thereto.

[0287] In the following, the definitions of the substituents of the compounds used herein may be presented. However, the number of carbon atoms used to limit the substituents is not limited, and the nature of the substituents is not limited. Unless otherwise defined, the definitions of substituents are consistent with their general definitions.

[0288] The C used in this paper 1 -C 60 The alkyl group may refer to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof are methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. 1 -C 60 Alkylene may refer to a group having 1 -C 60 Alkyl is a divalent group of the same structure.

[0289] The C used in this paper 1 -C 60 Alkoxy may refer to 101 (A 101 C 1 -C 60 The term "alkyl" refers to a monovalent group represented by an alkyl group, and non-limiting examples thereof are methoxy, ethoxy and isopropoxy.

[0290] The C used in this paper 2 -C 60 Alkenyl may refer to 2 -C 60 At one or more positions of the hydrocarbon chain of the alkyl group (e.g., at C 2 -C 60 The C used herein is a hydrocarbon group having at least one carbon double bond (in the middle or at either end of the alkyl group), and its limiting examples are ethenyl, propenyl and butenyl. 2 -C 60 Alkenylene may refer to a 2 -C 60Alkenyl is a divalent group of the same structure.

[0291] The C used in this paper 2 -C 60 Alkynyl refers to 2 -C 60 At one or more positions of the hydrocarbon chain of the alkyl group (e.g., at C 2 -C 60 The term C as used herein refers to a hydrocarbon group having at least one carbon triple bond (in the middle or at either end of an alkyl group), and non-limiting examples thereof are ethynyl and propynyl. 2 -C 60 Alkyne may refer to a 2 -C 60 Alkynyl is a divalent group of the same structure.

[0292] The C used in this paper 3 -C 10 The cycloalkyl group may refer to a monovalent hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. 3 -C 10 Cycloalkylene may refer to a cycloalkylene having 3 -C 10 Cycloalkyl is a divalent group of the same structure.

[0293] The C used in this paper 1 -C 10 The heterocycloalkyl group may refer to a monovalent monocyclic group having at least one heteroatom selected from N, O, P and S as a ring-forming atom and 1 to 10 carbon atoms, and non-limiting examples thereof are tetrahydrofuranyl and tetrahydrothienyl. 1 -C 10 Heterocycloalkylene may refer to a 1 -C 10 Heterocycloalkyl is a divalent group of the same structure.

[0294] The C used in this paper 3 -C 10 The cycloalkenyl group may refer to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one double bond in its ring and not having aromaticity, and non-limiting examples thereof are cyclopentenyl, cyclohexenyl, and cycloheptenyl. 3 -C 10 Cycloalkenylene may refer to a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.

[0295] The C used in this paper 2 -C 10The heterocycloalkenyl group may refer to a monovalent monocyclic group having at least one heteroatom selected from N, O, P and S as a ring-forming atom, 2 to 10 carbon atoms and at least one double bond in its ring. 2 -C 10 Non-limiting examples of heterocycloalkenyl are 2,3-dihydrofuranyl and 2,3-dihydrothienyl. 2 -C 10 Heterocycloalkenylene may refer to a 2 -C 10 Heterocycloalkenyl is a divalent group of the same structure.

[0296] The C used in this paper 6 -C 60 Aryl may refer to a monovalent group having a carbocyclic aromatic system (having 6 to 60 carbon atoms), and the C 6 -C 60 The arylene group may refer to a divalent group having a carbocyclic aromatic system (having 6 to 60 carbon atoms). 6 -C 60 Non-limiting examples of aryl groups are phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and chrysene. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each independently include two or more rings, the respective rings may be fused to each other.

[0297] The C used in this paper 1 -C 60 The heteroaryl group may refer to a monovalent group having a carbocyclic aromatic system having at least one heteroatom selected from N, O, P and S as a ring-forming atom and 1 to 60 carbon atoms. 1 -C 60 The heteroarylene group may refer to a divalent group having a carbocyclic aromatic system having at least one heteroatom selected from N, O, P and S as a ring-forming atom and 1 to 60 carbon atoms. 1 -C 60 Non-limiting examples of heteroaryl are pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl and isoquinolinyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each independently include two or more rings, the respective rings may be fused to each other.

[0298] The C used in this paper 6 -C 60 Aryloxy can refer to 102 The monovalent group represented by102 C 6 -C 60 aryl), and C 6 -C 60 Arylthio can refer to –SA 103 The monovalent group represented by 103 C 6 -C 60 aryl).

[0299] The monovalent non-aromatic fused polycyclic group used herein may refer to a monovalent group having two or more rings fused to each other (e.g., fused), having only carbon atoms as ring atoms (e.g., having 8 to 60 carbon atoms) and having non-aromaticity (e.g., not having overall aromaticity) in the entire molecular structure. A non-limiting example of a monovalent non-aromatic fused polycyclic group is a fluorenyl group. The divalent non-aromatic fused polycyclic group used herein may refer to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.

[0300] The monovalent non-aromatic fused heteropolycyclic group used herein may refer to a monovalent group having two or more rings fused (e.g., fused) to each other, having at least one heteroatom selected from N, O, P, and S as a ring-forming atom in addition to carbon atoms (e.g., 2 to 60 carbon atoms) and having non-aromaticity (e.g., not having overall aromaticity) in the entire molecular structure. The divalent non-aromatic fused heteropolycyclic group used herein may refer to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group.

[0301] As used herein, the substituted C 3 -C 10 Cycloalkylene, substituted C 1 -C 10 Heterocycloalkylene, substituted C 3 -C 10 Cycloalkenylene, substituted C 2 -C 10 Heterocycloalkenylene, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 2 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from the group consisting of:

[0302] deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy,

[0303] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 ) and -B(Q 16 )(Q 17 ),

[0304] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups,

[0305] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 ) and -B(Q 26 )(Q 27 ),as well as

[0306] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 ) and -B(Q 36 )(Q 37 ),

[0307] Where Q 11 To Q 17 , Q 21 To Q 27 and Q 31 To Q 37 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group.

[0308] For example, the substituted C 3 -C 10 Cycloalkylene, substituted C 1 -C 10 Heterocycloalkylene, substituted C 3 -C 10 Cycloalkenylene, substituted C 2 -C 10 Heterocycloalkenylene, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 2 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from the group consisting of:

[0309] deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy,

[0310] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphate or its salt, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl , thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 ) and -B(Q 16 )(Q 17 ),

[0311] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidine , pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl and imidazopyrimidinyl,

[0312] each selected from at least one substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetraphenyl, phenanthrenyl, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, rubenyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl , quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl and imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidine yl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 ) and -B(Q 26 )(Q 27 ),as well as

[0313] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 ) and -B(Q 36 )(Q 37 ),

[0314] Where Q 11 To Q 17 , Q 21 To Q 27 and Q 31 To Q 37 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl and imidazopyrimidinyl.

[0315] The expression "Ph" as used herein may refer to a phenyl group, the expression "Me" as used herein may refer to a methyl group, the expression "Et" as used herein may refer to an ethyl group, the expression "ter-Bu" or "Bu" as used herein may refer to a phenyl group. t ” may refer to tert-butyl, and “D” may refer to deuterium.

[0316] Hereinafter, an organic light-emitting device according to one or more embodiments of the present disclosure will be described in more detail with reference to Synthesis Examples and Examples.

[0317] Synthesis example

[0318] [Synthesis Example: Synthesis Intermediate]

[0319]

[0320] Synthetic intermediate I-1

[0321] 3.44 g (20 mmol) of 2-bromoaniline, 7.0 g (30.0 mmol) of 2-bromobiphenyl, 0.92 g (1.0 mmol) of Pd 2 (dba) 3 、0.2g(1.0mmol)P(tBu) 3 2.88g (30.0mol) of NaOtBu was dissolved in 60mL of toluene, and the resulting mixture was stirred at a temperature of about 80°C for 5 hours. The reaction solution obtained was returned to room temperature. Then, three extraction processes were performed by using 40mL of water and 40mL of ether respectively. The organic layer obtained was purified by using magnesium sulfate (MgSO 4) was dried. Next, the solvent was removed therefrom by evaporation. The obtained residue was separated and purified by silica gel column chromatography to obtain 5.12 g of Intermediate I-1 (yield: 79%). The obtained compound was identified by liquid chromatography-mass spectrometry (LC-MS).

[0322] C 18 H 14 BrN:M+1 324.0

[0323] Synthetic intermediate I-2

[0324] 3.37 g (30.0 mmol) of tBuONa was added to 100 mL of dried dimethyl sulfoxide (DMSO) (wherein oxygen was removed). 5 minutes after the addition, 4.86 g (15.0 mmol) of intermediate I-1 was added thereto, and the resulting mixture was then subjected to reaction for about 60 minutes under a 400 W lamp (350 nm). Once the reaction was complete, the resultant was neutralized with water and a large amount of ammonium nitrate, and then extracted three times with 100 mL of dichloromethane. The organic layer obtained was purified by using MgSO 4 Drying was performed. Next, the solvent was removed therefrom by evaporation. The obtained residue was separated and purified by silica gel column chromatography to obtain 1.82 g of Intermediate I-2 (yield: 50%). The obtained compound was identified by LC-MS.

[0325] C 18 H 13 N:M+1 244.1

[0326] Synthetic intermediate I-3

[0327] 1.82 g (7.5 mmol) of intermediate I-2, 2.54 g (9.0 mmol) of 1-bromo-4-iodobenzene, 0.13 g (0.7 mmol) of CuI, 0.17 g (0.7 mmol) of 18-crown ether-6 and 2.90 g (21.0 mmol) of K 2 CO 2 Dissolved in 30 mL of dimethylformamide (DMF), the resulting mixture was then stirred at a temperature of about 140° C. for about 12 hours. The obtained reaction solution was returned to room temperature. Then, three extraction processes were performed on it by using 30 mL of water and 30 mL of ether respectively. The obtained organic layer was extracted by using MgSO 4 Drying was performed. Next, the solvent was removed therefrom by evaporation. The obtained residue was separated and purified by silica gel column chromatography to obtain 2.69 g of Intermediate I-3 (yield: 90%). The obtained compound was identified by LC-MS.

[0328] C 24 H 16BrN:M+1 398.0

[0329] Synthetic intermediate I-4

[0330] Intermediate I-4 was synthesized in the same (or substantially the same) manner as Intermediate I-3 (yield: 89%), except that 1-bromo-3-iodobenzene was used instead of 1-bromo-4-iodobenzene. The obtained compound was identified by LC-MS.

[0331] C 24 H 16 BrN:M+1 398.0

[0332]

[0333] Synthetic intermediate I-5

[0334] Intermediate I-5 was synthesized in the same (or substantially the same) manner as Intermediate I-1 (yield: 73%), except that 2-bromo-4-nitroaniline was used instead of 2-bromoaniline. The obtained compound was identified by LC-MS.

[0335] C 18 H 13 Bn 2 O 2 :M+1 369.0

[0336] Synthetic intermediate I-6

[0337] Intermediate I-6 was synthesized in the same (or substantially the same) manner as Intermediate I-2 (yield: 42%), except that Intermediate I-5 was used instead of Intermediate I-1. The obtained compound was identified by LC-MS.

[0338] C 18 H 12 N 2 O 2 :M+1 289.1

[0339] Synthetic intermediate I-7

[0340] Intermediate I-7 was synthesized in the same (or substantially the same) manner as Intermediate I-3 (yield: 92%), except that Intermediate I-6 was used instead of Intermediate I-2 and iodobenzene was used instead of 1-bromo-4-iodobenzene. The obtained compound was identified by LC-MS.

[0341] C 24 H 16 N 2 O 2 :M+1 365.1

[0342] Synthetic intermediate I-8

[0343] 3.64 g (10.0 mmol) of intermediate I-7 and 100 mg of Pd / carbon (10%) were dissolved in 40 mL of methanol, and the resulting mixture was stirred under H 2 The reaction mixture was filtered and then precipitated with MgSO 4 The mixture was dried. Then, the solvent was removed therefrom by evaporation. 20 mL of distilled water was added to the residue, and 5 mL of a 10% aqueous HCl solution was added thereto. The resultant was cooled to a temperature of 0° C., and a solution (wherein 1.0 g (14.4 mmol) of NaNO 2 2.87 g (20.0 mmol) of CuBr was added to the solution, and then the resulting solution was stirred at the same temperature for about 2 hours. Then, the resulting solution was heated to 100 ° C and stirred for about 3 hours. The obtained reaction solution was returned to room temperature. Then, it was subjected to three extraction processes using 30 mL of ether. The organic layer was obtained by using MgSO 4 Drying was performed. Next, the solvent was removed therefrom by evaporation. The obtained residue was separated and purified by silica gel column chromatography to obtain 2.98 g of Intermediate I-8 (yield: 75%). The obtained compound was identified by LC-MS.

[0344] C 24 H 16 BrN:M+1 398.0

[0345]

[0346] Synthetic intermediate I-9

[0347] Intermediate I-9 was synthesized in the same (or substantially the same) manner as Intermediate I-5 (yield: 78%), except that 2-bromo-5-nitroaniline was used instead of 2-bromo-4-nitroaniline. The obtained compound was identified by LC-MS.

[0348] C 18 H 13 Bn 2 O 2 :M+1 369.0

[0349] Synthetic intermediate I-10

[0350] Intermediate I-10 was synthesized in the same (or substantially the same) manner as Intermediate I-6 (yield: 46%), except that Intermediate I-9 was used instead of Intermediate I-5. The obtained compound was identified by LC-MS.

[0351] C 18 H 12 N 2 O 2 :M+1 289.1

[0352] Synthetic intermediate I-11

[0353] Intermediate I-11 was synthesized in the same (or substantially the same) manner as Intermediate I-7 (yield: 90%), except that Intermediate I-10 was used instead of Intermediate I-6. The obtained compound was identified by LC-MS.

[0354] C 24 H 16 N 2 O 2 :M+1 365.1

[0355] Synthetic intermediate I-12

[0356] Intermediate I-12 was synthesized in the same (or substantially the same) manner as Intermediate I-8 (yield: 73%), except that Intermediate I-11 was used instead of Intermediate I-7. The obtained compound was identified by LC-MS.

[0357] C 24 H 16 BrN:M+1 398.0

[0358]

[0359] Synthetic intermediate I-13

[0360] 4.38 g (11.0 mmol) of intermediate I-12, 2.00 g (10.0 mmol) of (4-bromophenyl)boronic acid, 0.58 g (0.5 mmol) of Pd(PPh 3 ) 4 and 4.14 g (30.0 mmol) K 2 CO 3 Dissolve in 40 mL THF and H 2 O (in a volume ratio of 1: 1) in a mixture solution, and then stirred at a temperature of 60° C. for 4 hours. The resulting reaction solution was returned to room temperature, and then 30 mL of water was added thereto. The extraction process was performed three times using 30 mL of ether. The obtained organic layer was obtained by using MgSO 4Drying was performed. Next, the solvent was removed therefrom by evaporation. The obtained residue was separated and purified by silica gel column chromatography to obtain 3.75 g of Intermediate I-13 (yield: 79%). The obtained compound was identified by LC-MS.

[0361] C 30 H 20 BrN:M+1 474.1

[0362]

[0363] Synthetic intermediate I-14

[0364] Intermediate I-14 was synthesized in the same (or substantially the same) manner as Intermediate I-7 (yield: 84%), except that 1-bromo-4-fluorobenzene was used instead of iodobenzene. The obtained compound was identified by LC-MS.

[0365] C 24 H 15 FN 2 O 2 :M+1 383.1

[0366] Synthetic intermediate I-15

[0367] Intermediate I-15 was synthesized in the same (or substantially the same) manner as Intermediate I-8 (yield: 72%), except that Intermediate I-14 was used instead of Intermediate I-7. The obtained compound was identified by LC-MS.

[0368] C 24 H 15 FN: M+1 416.0

[0369] Synthetic intermediate I-16

[0370] Intermediate I-16 was synthesized in the same (or substantially the same) manner as Intermediate I-13 (yield: 76%), except that Intermediate I-15 was used instead of Intermediate I-12. The obtained compound was identified by LC-MS.

[0371] C 30 H 19 BrFN: M+1 492.1

[0372] Synthetic intermediates I-17 to I-23

[0373] Based on the above-mentioned synthesis methods of intermediates 1-13 and 1-16 and by using appropriate intermediates, the synthesis methods of intermediates 1-17 to 1-23 should be obvious to those skilled in the art.

[0374]

[0375] Synthetic amine intermediates A-1 to A-18

[0376]

[0377] Synthetic intermediate A-1

[0378] 2.33 g (10.0 mmol) of 4-bromo-1,1'-biphenyl, 2.03 g (12.0 mmol) of 4-amino-1,1'-biphenyl, 0.46 g (0.5 mmol) of Pd 2 (dba) 3 、0.10g (0.5mmol) P (tBu) 3 1.44 g (15.0 mol) of NaOtBu was dissolved in 30 mL of toluene, and the resulting mixture was stirred at a temperature of about 80° C. for 5 hours. The obtained reaction solution was returned to room temperature. Then, three extraction processes were performed by using 30 mL of water and 30 mL of ether respectively. The obtained organic layer was extracted by using MgSO 4 Drying was performed. Next, the solvent was removed therefrom by evaporation. The obtained residue was separated and purified by silica gel column chromatography to obtain 2.76 g of Intermediate A-1 (yield: 86%). The obtained compound was identified by LC-MS.

[0379] C 24 H 19 N: M+1 322.2

[0380] Synthetic intermediate A-1'

[0381] 2.57 g (8.0 mmol) of intermediate A-1, 4.53 g (16.0 mmol) of 1-bromo-3-iodobenzene, 0.37 g (0.4 mmol) of Pd 2 (dba) 3 、0.08g (0.4mmol) P (tBu) 3 1.15 g (12.0 mol) of NaOtBu was dissolved in 30 mL of toluene, and the mixture was stirred at a temperature of about 80° C. for 5 hours. The obtained reaction solution was returned to room temperature. Then, three extraction processes were performed by using 30 mL of water and 30 mL of ether respectively. The obtained organic layer was extracted by using MgSO 4 Drying was performed. Next, the solvent was removed therefrom by evaporation. The obtained residue was separated and purified by silica gel column chromatography to obtain 2.86 g of Intermediate A-1' (yield: 75%). The obtained compound was identified by LC-MS.

[0382] C30 H 22 BrN:M+1 476.1

[0383] Synthetic intermediate A-17

[0384] 2.86g (6.0mmol) of intermediate A-1' was dissolved in 20mL THF. Then, 2.4mL n-BuLi (2.5 moles (M) in hexane) was slowly added thereto at a temperature of -78°C, and the resulting mixture was stirred at the same temperature for about 1 hour. 1mL (9.0mmol) of trimethyl borate was added dropwise to the solution obtained at the same temperature, and the solution was then returned to room temperature and stirred for about 3 hours. 20mL of water and 10mL of saturated aqueous ammonium chloride solution were sequentially added to the reaction solution obtained, and then stirred for about 1 hour. Three extraction processes were carried out using 30mL of ether. The organic layer obtained was obtained by using MgSO 4 Drying was performed. Next, the solvent was removed therefrom by evaporation. The obtained residue was separated and purified by silica gel column chromatography to obtain 2.28 g of Intermediate A-17 (yield: 89%). The obtained compound was identified by LC-MS.

[0385] C 30 H 24 BNO 2 :M+1 442.2

[0386] Based on the above synthesis methods of intermediates A-1 and A-17 and by using appropriate intermediates, the synthesis methods of intermediates A-2 to A-18 should be obvious to those of ordinary skill in the art.

[0387]

[0388] Synthesis Example: Synthesis of Compounds According to One or More Embodiments

[0389]

[0390] Synthesis of compound 3

[0391] 4.74 g (10.0 mmol) of intermediate I-13, 3.21 g (10.0 mmol) of intermediate A-1, 0.46 g (0.5 mmol) of Pd 2 (dba) 3 、0.10g (0.5mmol) P (tBu) 31.44 g (15.0 mol) of NaOtBu was dissolved in 30 mL of toluene, and the resulting mixture was stirred at a temperature of about 80° C. for 5 hours. The obtained reaction solution was returned to room temperature. Then, three extraction processes were performed by using 30 mL of water and 30 mL of ether respectively. The obtained organic layer was extracted by using MgSO 4 The obtained compound was purified by LC-MS and 1 H-nuclear magnetic resonance (NMR) was used for identification.

[0392] C 54 H 38 N 2 :M+1 715.3

[0393] 1 H NMR (CDCl 3 ,300MHz)δ7.65-7.58(m,8H),7.54-7.37(m,15H),7.29(dd,1H),7.18(dd,1H ),7.10-6.99(m,4H),6.95-6.90(m,4H),6.87-6.83(m,3H),6.79-6.72(m,2H)

[0394] Synthesis of compound 5

[0395] Compound 5 (yield: 91%) was obtained by the same (or substantially the same) method as that for synthesizing compound 3, except that intermediate I-13 was reacted with intermediate A-2 instead of intermediate A-1. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0396] C 58 H 40 N 2 :M+1 765.3

[0397] 1 H NMR (CDCl 3 ,300MHz)δ7.83-7.80(m,2H),7.66-7.58(m,7H),7.53-7.36(m,14H),7.31(d,1H),7.23(dt,1 H),7.18(dd,1H),7.13-7.02(m,7H),6.99-6.94(m,2H),6.89-6.83(m,3H),6.78-6.72(m,2H)

[0398] Synthesis of compound 7

[0399] Compound 7 (yield: 92%) was obtained by the same (or substantially the same) method as that for synthesizing compound 3, except that intermediate I-13 was reacted with intermediate A-3 instead of intermediate A-1. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0400] C 57 H 42 N 2 :M+1 755.3

[0401] 1 H NMR (CDCl 3 ,300MHz)δ7.78(d,1H),7.71-7.32(m,19H),7.24-7.07(m,7H),6.99-6.89(m,6H),6.84(d,1H),6.81-6.76(m,2H),1.63(s,6H)

[0402] Synthesis of compound 8

[0403] Compound 8 (yield: 90%) was obtained by the same (or substantially the same) method as that for synthesizing compound 3, except that intermediate I-13 was reacted with intermediate A-4 instead of intermediate A-1. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0404] C 54 H 36 N 2 O: M+1 729.3

[0405] 1 H NMR (CDCl 3 ,300MHz)δ7.78-7.72(m,2H),7.69-7.59(m,7H),7.55-7.36(m,12H),7.32(d,1H),7 .23(dd,1H),2.18-7.06(m,6H),6.98-6.90(m,4H),6.86(dt,1H),6.83-6.78(m,2H)

[0406] Synthesis of compound 10

[0407] Compound 10 (yield: 92%) was obtained by the same (or substantially the same) method as for the synthesis of compound 3, except that intermediate I-13 was reacted with intermediate A-5 instead of intermediate A-1. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0408] C 60 H 40 N 2 O: M+1 805.3

[0409] 1 H NMR (CDCl 3 ,300MHz)δ7.95-7.90(m,2H),7.81(d,1H),7.73-7.62(m,7H),7.58-7.34(m,16H),7.21(d,1H) ,7.15-7.04(m,4H),7.01-6.96(m,2H),6.92-6.87(m,2H),6.82-6.77(m,3H),6.72-6.69(m,2H)

[0410] Synthesis of compound 13

[0411] Compound 13 (yield: 83%) was obtained by the same (or substantially the same) method as that for synthesizing compound 3, except that intermediate I-13 was reacted with intermediate A-6 instead of intermediate A-1. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0412] C 53 H 37 N 3 :M+1 716.3

[0413] 1 H NMR (CDCl 3 ,300MHz)δ8.83(s,1H),8.60(d,1H),7.94-7.91(m,1H),7.81-7.65(m,6H),7.60-7.41(m,11H),7.35- 7.29(m,3H),7.21(d,1H),7.17-7.08(m,4H),7.03-6.99(m,2H),6.93-6.86(m,5H),6.82-6.78(m,2H)

[0414] Synthesis of compound 15

[0415] Compound 15 (yield: 79%) was obtained by the same (or substantially the same) method as for the synthesis of compound 3, except that intermediate I-17 was reacted with intermediate A-1 instead of intermediate I-13. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0416] C 53 H 37 N 3:M+1 716.3

[0417] 1 H NMR (CDCl 3 ,300MHz)δ8.42(s,1),7.71-7.52(m,18H),7.46-7.39(m,3H),7.34-7.25(m,3H),7.18-7.10(m,4H),7.04-6.96(m,6H),6.84-6.79(m,2H)

[0418] Synthesis of compound 22

[0419] Compound 22 (yield: 89%) was obtained by the same (or substantially the same) method as for the synthesis of compound 3, except that intermediate I-13 was reacted with intermediate A-7 instead of intermediate A-1. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0420] C 60 H 41 N 3 :M+1 804.3

[0421] 1 H NMR (CDCl 3 ,300MHz)δ8.23(d,1H),7.69-7.31(m,27H),7.21-7.06(m,5H),6.99-6.90(m,6H),6.84-6.79(m,2H)

[0422] Synthesis of compound 28

[0423] Compound 28 (yield: 90%) was obtained by the same (or substantially the same) method as for the synthesis of compound 3, except that intermediate I-13 was reacted with intermediate A-8 instead of intermediate A-1. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0424] C 49 H 33 N 3 :M+1 664.3

[0425] 1 H NMR (CDCl 3,300MHz)δ7.71-7.62(m,6H),7.58-7..40(m,12H),7.36(d,1H),7.25-7.10(m,5H),7.03-6.97(m,4H),6.91-6.86(m,3H),6.82-6.76(m,2H)

[0426] Synthesis of compound 30

[0427] Compound 30 (yield: 92%) was obtained by the same (or substantially the same) method as that for synthesizing compound 3, except that intermediate I-16 was reacted with intermediate A-1 instead of intermediate I-13. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0428] C 54 H 37 FN 2 :M+1 733.3

[0429] 1H NMR(CDCl3,300MHz)δ7.69-7.59(m,8H),7.56-7.39(m,15H),7.35(d,1H),7.22-7.02(m,9H),6.94-6.89(m,2H),6.82-6.76(m,2H)

[0430] Synthesis of compound 31

[0431] Compound 31 (yield: 88%) was obtained by the same (or substantially the same) method as for the synthesis of compound 3, except that intermediate I-21 was reacted with intermediate A-1 instead of intermediate I-13. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0432] C 54 H 33 D 5 N 2 :M+1 720.3

[0433] 1 H NMR (CDCl 3 ,300MHz)δ7.65-7.58(m,8H),7.54-7.37(m,15H),7.31(d,1H),7.21(d,1H),7.13-7.05(m,2H),6.97-6.92(m,4H),6.84-6.79(m,2H)

[0434] Synthesis of compound 38

[0435] Compound 38 (yield: 93%) was obtained by the same (or substantially the same) method as that for synthesizing compound 3, except that intermediate I-13 was reacted with intermediate A-9 instead of intermediate A-1. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0436] C 67 H 46 N 2 :M+1 879.4

[0437] 1 H NMR (CDCl 3 ,300MHz)δ7.86(d,1H),7.73-7.42(m,18H),7.34(d,1H),7.27-7.03(m,16H) ,6.97(d,1H),6.93(d,1H),6.89-6.80(m,5H),6.77(s,1H),6.74-6.69(m,2H)

[0438] Synthesis of compound 43

[0439] Compound 43 (yield: 91%) was obtained by the same (or substantially the same) method as for the synthesis of compound 3, except that intermediate I-22 was reacted with intermediate A-1 instead of intermediate I-13. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0440] C 60 H 40 N 2 O: M+1 805.3

[0441] 1 H NMR (CDCl 3 ,300MHz)δ7.74(d,2H),7.69-7.60(9H),7.55-7.39(m,17H),7.31(d,1H),7.21-7.02(m,5H),6.97-6.92(m,4H),6.83-6.78(m,2H)

[0442] Synthesis of compound 58

[0443]

[0444] 2.37 g (5.0 mmol) of intermediate I-13, 0.92 g (5.0 mmol) of carbazole, 0.1 g (0.5 mmol) of CuI, 0.13 g (0.5 mmol) of 18-crown ether-6 and 2.07 g (15.0 mmol) of K 2CO 3 Dissolve in 20 mL of DMF and then stir at a temperature of about 140° C. for about 12 hours. Allow the resulting reaction solution to return to room temperature. Then, extract it three times using 20 mL of water and 20 mL of ether each. The obtained organic layer is extracted by using MgSO 4 The obtained compound was purified by LC-MS and 1 Identified by H-NMR.

[0445] C 42 H 28 N 2 :M+1 561.2

[0446] 1 H NMR (CDCl 3 ,300MHz)δ8.12(d,2H),7.74-7.63(m,4H),7.52-7.25(m,14H),7.19(d,1H),7.09-7.01(m,4H),6.96-6.91(m,1H),6.84-6.79(m,2H)

[0447] Synthesis of compound 61

[0448] Compound 61 (yield: 90%) was obtained by the same (or substantially the same) method as for the synthesis of compound 3, except that intermediate I-18 was reacted with intermediate A-1 instead of intermediate I-13. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0449] C 54 H 38 N 2 :M+1 715.3

[0450] 1 H NMR (CDCl 3 ,300MHz)δ7.69-7.61(m,7H),7.56-7.27(m,16H),7.21-7.14(m,2H),7.09-7.01(m,5H),6.94-6.86(m,5H),6.82-6.76(m,3H)

[0451] Synthesis of compound 66

[0452] Compound 66 (yield: 91%) was obtained by the same (or substantially the same) method as that for synthesizing compound 3, except that intermediate I-20 was used instead of intermediate I-13, and intermediate A-3 was used instead of intermediate A-1. The obtained compound was identified by LC-MS and 1 Identified by H-NMR.

[0453] C 57 H 42 N 2 :M+1 755.3

[0454] 1 H NMR (CDCl 3 ,300MHz)δ7.78(d,1H),7.71-7.29(m,19H),7.21(s,1H),7.17-7.02(m,6H),6.97-6.91(m,6H),6.86(s,1H),6.82-6.76(m,2H),1.61(s,6H)

[0455] Synthesis of compound 68

[0456]

[0457] 2.37 g (5.0 mmol) of intermediate I-18, 2.21 g (5.0 mmol) of intermediate A-17, 0.29 g (0.25 mmol) of Pd(PPh 3 ) 4 and 2.07 g (15.0 mmol) K 2 CO 3 Dissolve in 20 mL of THF and H 2 O (in a volume ratio of 1: 1) and stirred at 60 ° C for 4 hours. The resulting reaction solution was returned to room temperature and then 20 mL of water was added thereto. Then, 20 mL of ether was used to perform three extraction processes. The obtained organic layer was obtained by using MgSO 4 The obtained compound was purified by LC-MS and 1 Identified by H-NMR.

[0458] C 60 H 42 N 2 :M+1 791.3

[0459] 1 H NMR (CDCl 3,300MHz)δ7.81(s,1H),7.68-7.39(m,23H),7.32-7.23(m,3H),7.18-7.02(m,7H),6.95-6.90(m,5H),6.84-6.79(m,3H)

[0460] Synthesis of compound 70

[0461] Compound 70 (yield: 87%) was obtained by the same (or substantially the same) method as for the synthesis of compound 3, except that intermediate I-19 was used instead of intermediate I-13, and N-phenylnaphthalene-1-amine was used instead of intermediate A-1. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0462] C 55 H 40 N 2 :M+1 729.3

[0463] 1 H NMR (CDCl 3 ,300MHz)δ8.13(d,1H),7.87(d,1H),7.73-7.28(m,16H),7.15-7.03(m,7 H),6.97-6.91(m,4H),6.86-6.82(m,3H),6.79-6.72(m,2H),1.64(s,6H)

[0464] Synthesis of compound 81

[0465] Compound 81 (yield: 81%) was obtained by the same (or substantially the same) method as that for synthesizing compound 3, except that intermediate I-8 was used instead of intermediate I-13, and intermediate A-10 was used instead of intermediate A-1. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0466] C 54 H 42 N 2 :M+1 719.3

[0467] 1 H NMR (CDCl 3 ,300MHz)δ7.76(d,2H),7.71-7.60(m,4H),7.49-7.32(m,7H),7.24-7.07(m ,8H),7.01-6.94(m,4H),6.89-6.82(m,3H),6.77-6.71(m,2H),1.63(s,12H)

[0468] Synthesis of compound 85

[0469] Compound 85 (yield: 83%) was obtained by the same (or substantially the same) method as for the synthesis of compound 3, except that intermediate I-8 was used instead of intermediate I-13, and intermediate A-11 was used instead of intermediate A-1. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0470] C 48 H 34 N 2 :M+1 639.3

[0471] 1 H NMR (CDCl 3 ,300MHz)δ7.69-7.58(m,6H),7.48-7.33(m,12H),7.22-7.02(m,10H),6.96-6.88(m,2H),6.84-6.80(m,2H),6.76-6.71(m,2H)

[0472] Synthesis of compound 88

[0473] Compound 88 (yield: 85%) was obtained by the same (or substantially the same) method as for the synthesis of compound 3, except that intermediate I-8 was used instead of intermediate I-13, and intermediate A-12 was used instead of intermediate A-1. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0474] C 54 H 38 N 2 :M+1 715.3

[0475] 1 H NMR (CDCl 3 ,300MHz)δ7.71-7.29(m,24H),7.17(s,1H),7.12-7.02(m,4H),6.97(d,1H),6.93-6.84(m,6H),6.78-6.72(m,2H)

[0476] Synthesis of compound 92

[0477] Compound 92 (yield: 87%) was obtained by the same (or substantially the same) method as for the synthesis of compound 3, except that intermediate I-3 was used instead of intermediate I-13, and intermediate A-13 was used instead of intermediate A-1. The obtained compound was analyzed by LC-MS and1 Identified by H-NMR.

[0478] C 42 H 29 FN 2 :M+1 581.2

[0479] 1 H NMR (CDCl 3 ,300MHz)δ7.69-7.59(m,4H),7.56-7.35(m,9H),7.18-7.07(m,6H),7.02-6.92(m,4H),6.84-6.72(m,6H)

[0480] Synthesis of compound 95

[0481] Compound 95 (yield: 79%) was obtained by the same (or substantially the same) method as for the synthesis of compound 3, except that intermediate I-3 was used instead of intermediate I-13, and intermediate A-14 was used instead of intermediate A-1. The obtained compound was identified by LC-MS and 1 Identified by H-NMR.

[0482] C 54 H 38 N 2 :M+1 715.3

[0483] 1 H NMR (CDCl 3 ,300MHz)δ7.69-7.57(m,8H),7.51-7.38(m,16H),7.13-7.07(m,6H),6.97(d,2H),6.86-6.70(m,6H)

[0484] Synthesis of compound 99

[0485] Compound 99 (yield: 81%) was obtained by the same (or substantially the same) method as that for synthesizing compound 3, except that intermediate I-3 was used instead of intermediate I-13, and intermediate A-15 was used instead of intermediate A-1. The obtained compound was identified by LC-MS and 1 Identified by H-NMR.

[0486] C 54 H 36 N 2 O: M+1 729.3

[0487] 1 H NMR (CDCl 3,300MHz)δ7.90(dd,1H),7.78(d,1H),7.72-7.57(m,7H),7.54-7.33(m,12H),7. 24(t,1H),7.16-7.09(m,7H),7.03(t,1H),6.93-6.89(m,2H),6.82-6.74(m,4H)

[0488] Synthesis of compound 105

[0489] Compound 105 (yield: 86%) was obtained by the same (or substantially the same) method as that for synthesizing compound 58, except that intermediate I-23 was used instead of intermediate I-13, and 3,6-diphenyl-9H-carbazole was used instead of carbazole. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0490] C 54 H 36 N 2 :M+1 713.3

[0491] 1 H NMR (CDCl 3 ,300MHz)δ8.16(s,2H),7.75-7.69(m,6H),7.63-7.37(m,20H),7.15-7.07(m,6H),6.86-6.80(m,2H)

[0492] Synthesis of compound 106

[0493] Compound 106 (yield: 88%) was obtained by the same (or substantially the same) method as for the synthesis of compound 3, except that intermediate I-23 was reacted with intermediate A-1 instead of intermediate I-13. The obtained compound was analyzed by LC-MS and 1 Identified by H-NMR.

[0494] C 54 H 38 N 2 :M+1 715.3

[0495] 1 H NMR (CDCl 3 ,300MHz)δ7.65-7.57(m,6H),7.52-7.33(m,18H),7.13-7.05(m,6H),6.95-6.88(m,6H),6.79-6.72(m,2H)

[0496] Synthesis of compound 107

[0497] Compound 107 (yield: 81%) was obtained by the same (or substantially the same) method as for the synthesis of compound 68, except that intermediate I-4 was used instead of intermediate I-18, and intermediate A-16 was used instead of intermediate A-17. The obtained compound was identified by LC-MS and 1 Identified by H-NMR.

[0498] C 52 H 36 N 2 :M+1 689.3

[0499] 1 H NMR (CDCl 3 ,300MHz)δ8.13(d,1H),7.87(d,1H),7.68-7.38(m,16H),7.29-7.18(m,5H),7.09-6.98(m,6H),6.93-6.81(m,5H),6.74-6.70(m,2H)

[0500] Synthesis of compound 112

[0501] Compound 112 (yield: 80%) was obtained by the same (or substantially the same) method as for the synthesis of compound 68, except that intermediate I-3 was used instead of intermediate I-18, and intermediate A-18 was used instead of intermediate A-17. The obtained compound was identified by LC-MS and 1 Identified by H-NMR.

[0502] C 60 H 42 N 2 :M+1 791.3

[0503] 1 H NMR (CDCl 3 ,300MHz)δ7.72-7.67(m,4H),7.65-7.56(m,6H),7.52-7.33(m,18H),7.23-7.15(m,6H),7.06-6.96(m,6H),6.83-6.78(m,2H)

[0504] Example

[0505] Example 1

[0506] The substrates (ITO, Ag and ITO) were and A glass substrate having a thickness of 0.50 mm and a thickness of 0.50 mm was cut into a size of 50 mm x 50 mm x 0.5 mm, ultrasonically treated in isopropyl alcohol and pure water for 5 minutes in each solvent, and cleaned by exposure to ultraviolet rays with ozone, thereby using the obtained glass substrate as an anode. Then, the glass substrate was installed in a vacuum deposition device.

[0507] N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine (HT1) and F4-TCNQ were co-vacuum deposited on an ITO substrate at a weight ratio of about 98:2 to form a 30-nm 2-thick film having a thickness of about 100 nm. Compound HT1 was vacuum-deposited on the hole injection layer to form a hole injection layer having a thickness of about Compound 3 was vacuum-deposited on the first hole transport layer to form a first hole transport layer having a thickness of about Then, 9,10-di-naphthalene-2-yl-anthracene (ADN) (as a blue fluorescent host) and N,N,N',N'-tetraphenyl-pyrene-1,6-diamine (TPD) (as a blue fluorescent dopant) were co-deposited on the second hole transport layer at a weight ratio of about 98:2 to form a second hole transport layer having a thickness of about 100 nm. Then, 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (L201) was deposited on the light-emitting layer to form a light-emitting layer having a thickness of about LiF (which is an alkali metal halide) is deposited on the electron transport layer to form a layer having a thickness of about The electron injection layer is formed by vacuum-depositing Mg:Ag at a weight ratio of about 90:10 on the electron injection layer to form a layer having a thickness of about A cathode with a thickness of 100 nm is formed, thereby completing the manufacture of the organic light-emitting device.

[0508]

[0509] Examples 2 to 28

[0510] An organic light-emitting device was manufactured in the same (or substantially the same) manner as Example 1, except that Compounds 5 to 112 (as shown in Table 1) were used instead of Compound 3 to form the second hole transport layer.

[0511] Examples 29 to 38

[0512] An organic light-emitting device was manufactured in the same (or substantially the same) manner as Example 1, except that Compounds 7 to 105 (as shown in Table 1) were used instead of Compound HT1 to form the first hole transport layer.

[0513] Comparative Examples 1 to 4

[0514] An organic light-emitting device is manufactured in the same (or substantially the same) manner as in Example 1, except that Compound A, D, F and G are used instead of Compound 3 to form the second hole transport layer.

[0515]

[0516] At about 10 mA / cm 2 The device performance, namely, driving voltage, luminance, efficiency, and color coordinates of the organic light-emitting devices manufactured in Examples 1 to 38 and Comparative Examples 1 to 4 were measured at a current density of about 50 mA / cm 2 The time for the initial brightness to be reduced to half was measured at a current density of . The results are shown in Table 1.

[0517] Referring to the results shown in Table 1, when the compound according to one or more embodiments of the present disclosure is used in the first hole transport layer and / or the second hole transport layer, the organic light-emitting device can exhibit improved or the same driving voltage and improved efficiency, and its brightness half-life can also be improved compared to the organic light-emitting device of the comparative example.

[0518] Table 1

[0519]

[0520]

[0521]

[0522] According to one or more embodiments of the present disclosure, characteristics of an organic light-emitting device may be improved due to inclusion of the compound of Formula 1 according to the embodiments.

[0523] As used herein, the terms "use," "using," and "used" may be considered synonymous with the terms "utilize," "utilizing," and "utilized," respectively.

[0524] Furthermore, the terms "substantially," "about," and similar terms as used herein are used as terms of approximation rather than terms of degree, and are intended to account for the inherent variations in measurements or calculations that are recognized by those of ordinary skill in the art.

[0525] Likewise, any numerical range listed herein is intended to include all sub-ranges of the same numerical precision included in the listed range. For example, the range of "1.0 to 10.0" is intended to include between the listed minimum value 1.0 and the listed maximum value 10.0 (and including the end value), that is, all sub-ranges with a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limit listed herein is intended to include all lower numerical limits included therein and any minimum numerical limit listed in this specification is intended to include all higher numerical limits included therein. Therefore, the applicant reserves the right to modify this specification (including claims) to explicitly list any sub-ranges included in the scope explicitly listed herein.

[0526] It should be understood that the exemplary embodiments described herein should be considered in a descriptive sense rather than for purposes of limitation. Descriptions of features or aspects within each embodiment should generally be considered as available for other similar features or aspects in other embodiments.

[0527] While one or more embodiments of the present invention have been described with reference to the drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the following claims and their equivalents.

Claims

1. An organic light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; as well as an organic layer between the first electrode and the second electrode, the organic layer comprising a light-emitting layer, in The first electrode is an anode, The second electrode is a cathode, and The organic layer further comprises: i) a hole transport region between the first electrode and the light emitting layer, the hole transport region comprising a hole transport layer and at least one layer selected from a hole injection layer and an electron blocking layer, and ii) an electron transport region between the light emitting layer and the second electrode, the electron transport region comprising at least one layer selected from an electron transport layer, a hole blocking layer and an electron injection layer, in The hole transport layer comprises: A compound represented by Formula 1, wherein the compound comprises only one azepine moiety; or A compound represented by one of compounds 43 to 45: Among them, in formula 1, R1 to R 17 each independently selected from hydrogen, deuterium, halogen, amino, nitro, nitrile, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, methoxy, ethoxy and isopropoxy; Among them, only R2, R3, R 10 , R 11 , R 14 To R 16 One of the compounds comprises a group represented by Formula 1-1: Formula 1-1 Wherein, in Formula 1-1, Ar1 and Ar2 in Formula 1-1 are each independently a group represented by one of Formulas 3a to 3c and 3e to 3g: Wherein, in Formula 3c, H1 is selected from O, S and CR 22 R 23 ; In formula 3g, H1 is selected from O, S, NR 21 and CR 22 R 23 ; R 21 To R 23 and Z1 are each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C6-C 20 Aryl, substituted or unsubstituted C1-C 20 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group and Si(Q 13 )(Q 14 )(Q 15 ); p in Formula 3a is an integer selected from 1 to 5, p in Formulas 3b and 3c is an integer selected from 1 to 7, and p in Formulas 3e to 3g is an integer selected from 1 to 9, wherein when p is 2 or greater, 2 or more Z1 are the same as or different from each other; and * indicates the binding site with the adjacent atom, Provided that each of Ar1 and Ar2 is not a substituted or unsubstituted dibenzazepine or a substituted or unsubstituted tribenzazepine; X is a group represented by one of formulae 2a, 2c to 2f: Wherein, in formula 2d, H1 is selected from O, S, NR 21 and CR 22 R 23 ; R 21 To R 23 are each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C6-C 20 Aryl, substituted or unsubstituted C1-C 20 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group; and * indicates the binding site with the adjacent atom; and m is an integer selected from 0 to 5, and when m is 2 or more, 2 or more X are the same as or different from each other; wherein the substituted C1-C 20 Alkyl, substituted C6-C 20 Aryl, substituted C1-C 20 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is selected from the group consisting of: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphate or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy, Each of the following C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 ) and -B(Q 16 )(Q 17 ), C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups, Each of the C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 ) and -B(Q 26 )(Q 27 ),as well as If(Q 13 )(Q 14 )(Q 15 ), Where Q 11 To Q 17 and Q 21 To Q 27 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphate or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group.

2. The organic light-emitting device according to claim 1, wherein the hole transport layer comprises a first hole transport layer and a second hole transport layer, and The first hole transport layer is different from the second hole transport layer. The organic light-emitting device as claimed in claim 1 , wherein the second hole transport layer comprises the compound.

4. The organic light-emitting device of claim 1, wherein the first hole transport layer comprises another compound represented by Formula 201A: Formula 201A in, In formula 201A, L 201 To L 203 Each is independently selected from the group consisting of: phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene, chrysene, pyridylene, pyrazinylene, pyrimidinylene, pyridazinylene, quinolylene, isoquinolylene, quinoxalylene, quinazolinylene, carbazolylene and triazinylene, and each of which is selected from at least one substituted phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene, chrysene, pyridylene, pyrazinylene, pyrimidinylene, pyridazinylene, quinolylene, isoquinolylene, quinoxalylene, quinazolinylene, carbazolylene and triazinylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl; xa1 to xa3 are each independently 0 or 1; R 203 and R 211 Each is independently selected from the group consisting of: Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, and phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, each of which is substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl; R 213 and R 214 Each is independently selected from the group consisting of: C1-C 20 Alkyl and C1-C 20 Alkoxy, Each of the following C1-C 20 Alkyl and C1-C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, and phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, each of which is substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl; R 215 and R 216 Each is independently selected from the group consisting of: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 20 Alkyl and C1-C 20 Alkoxy, Each of the following C1-C 20 Alkyl and C1-C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, and phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl, each of which is substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl.

5. The organic light-emitting device of claim 4, wherein the compound represented by Formula 201A is represented by one of compounds HT1 to HT33: 6 . The organic light-emitting device of claim 1 , wherein Ar1 and Ar2 in Formula 1-1 are connected to each other to form a ring. 7 . The organic light-emitting device as claimed in claim 1 , wherein m in Formula 1-1 is an integer selected from 0 to 3.

8. The organic light-emitting device according to claim 1, wherein R1, R4 to R9, R 12 , R 13 and R 17 are each independently hydrogen or deuterium.

9. The organic light-emitting device as claimed in claim 1, wherein when H1 in Formula 3c is CR 22 R 23 When R 22 and R 23 Connect to form a ring.

10. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 2: Formula 2 Where R1, R2, R4 to R 17 , Ar1, Ar2, X and m are the same as those defined in claim 1.

11. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 3: Formula 3 Where R1, R3 to R 17 , Ar1, Ar2, X and m are the same as those defined in claim 1.

12. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 4: Formula 4 Where R1 to R 14 , R 16 , R 17 , Ar1, Ar2, X and m are the same as those defined in claim 1.

13. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 5: Formula 5 Where R1 to R 15 , R 17 , Ar1, Ar2, X and m are the same as those defined in claim 1.

14. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 6: Formula 6 Where R1 to R 16 , Ar1, Ar2, X and m are the same as those defined in claim 1.

15. The organic light-emitting device of claim 1, wherein the compound represented by Formula 1 is represented by one of Compounds 1 to 11, 16 to 21, 23 to 31, 35, 37, 38, 46, 48 to 51, 54 to 83, 85 to 95, and 97 to 117: 16 . A display device comprising the organic light-emitting device according to claim 1 , wherein a first electrode of the organic light-emitting device is electrically coupled to a source electrode or a drain electrode of a thin film transistor.

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