Heterocyclic compound and organic light-emitting device containing the same

Abstract

To provide a heterocyclic compound and an organic light-emitting device including the same.SOLUTION: Provided is a heterocyclic compound represented by Formula 1. (At least one selected from Xto Xis N, provided that all of Xto Xare not N at the same time, n1 is selected from 0, 1, and 2, n2 is selected from 1, 2, and 3, a sum of n1+n2 is 3, L, L, and Rare each independently selected from a substituted or unsubstituted C-Ccarbocyclic group and a substituted or unsubstituted C-Cheterocyclic group, a1 and a2 are each independently selected from an integer from 0 to 5, and b1 is selected from an integer from 0 to 10. The heterocyclic compound represented by Formula 1 comprises at least one -F.)SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a heterocyclic compound and an organic light-emitting device containing the same. [Background technology]

[0002] An organic light emitting device is a self-emitting device that has a wider viewing angle and better contrast than conventional devices, as well as a shorter response time, superior brightness, driving voltage, and response speed characteristics, and is capable of multiple colors.

[0003] An organic light-emitting device may have a structure in which a first electrode is disposed on a substrate, and a hole transport region, an emitting layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes injected from the first electrode travel to the emitting layer via the hole transport region, and electrons injected from the second electrode travel to the emitting layer via the electron transport region. Carriers such as holes and electrons recombine in the emitting layer region to generate excitons. Light is generated when the excitons transition from the excited state to the ground state. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Korean Patent No. 10-0691543 Summary of the Invention [Problem to be solved by the invention]

[0005] The present invention provides a heterocyclic compound and an organic light-emitting device containing the same. [Means for solving the problem]

[0006] According to one embodiment of the present invention, there is provided a heterocyclic compound represented by the following Chemical Formula 1: [ka] In Chemical Formula 1, X 11 is N or C-[(L 11 ) a11 -(R 11 ) b11 ] and X 12 is N or C-[(L 12 ) a12 -(R 12 ) b12 ] and X 13 is N or C-[(L 13 ) a13 -(R 13 ) b13 ] and X 14 is N or C-[(L 14 ) a14 -(R 14 ) b14 ] and X 15 is N or C-[(L 15 ) a15 -(R 15 ) b15 ] and X 11 ~X 15 At least one of them is N, but X 11 ~X 15 is not all N at the same time, n1 is 0, 1 or 2; n2 is 1, 2 or 3; n1+n2 is 3, L1, L2, L 11 ~L 15 , R1, and R 11 ~R 15 are, independently of each other, substituted or unsubstituted C5-C 60 Carbocyclic groups and substituted or unsubstituted C1-C 60 heterocyclic groups, a1, a2, and a11 to a15 are each independently selected from integers of 0 to 5; If a1 is 0, then *-(L1) a1 -*' is a single bond, and when a2 is 0, *-(L2) a2 -*' is a single bond, and when a11 is 0, *-(L 11 ) a11 -*' is a single bond, and when a12 is 0, *-(L 12 ) a12 -*' is a single bond, and when a13 is 0, *-(L 13 ) a13 -*' is a single bond, and when a14 is 0, *-(L 14 ) a14 -*' is a single bond, and when a15 is 0, *-(L 15 ) a15 -*' is a single bond, When a1 is 2 or more, two or more L1 may be the same or different from each other. When a2 is 2 or more, two or more L2 may be the same or different from each other. When a11 is 2 or more, two or more L 11 may be the same or different from each other, and when a12 is 2 or more, two or more L 12 may be the same or different, and when a13 is 2 or more, two or more L 13 may be the same or different from each other, and when a14 is 2 or more, two or more L 14 may be the same or different from each other, and when a15 is 2 or more, two or more L 15 may be the same or different from each other, b1 and b11 to b15 are selected from integers of 1 to 10; When b1 is 2 or more, two or more R1 may be the same or different from each other. When b11 is 2 or more, two or more R 11 may be the same or different from each other, and when b12 is 2 or more, two or more R 12 may be the same or different from each other, and when b13 is 2 or more, two or more R 13may be the same or different from each other, and when b14 is 2 or more, 14 may be the same or different from each other, and when b15 is 2 or more, two or more R 15 may be the same or different from each other, L1, L2, L 11 ~L 15 , R1, and R 11 ~R 15 Any two of these may be bonded to each other and may be substituted or unsubstituted C5-C 60 Carbocyclic groups or substituted or unsubstituted C1-C 60 may form a heterocyclic group, The heterocyclic compound represented by Chemical Formula 1 contains at least one -F, Substituted C5-C 60 Carbocyclic groups and substituted C1-C 60 At least one of the substituents of the heterocyclic group is Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 alkoxy groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 alkoxy groups; C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups, and terphenyl groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group, terphenyl group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ) and -P(=O)(Q21)(Q 22 ) C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heteropolycyclic groups, biphenyl groups, and terphenyl groups; and -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ); Q1~Q3, Q 11 ~Q 13 , Q 21 ~Q 23 , and Q 31 ~Q 33are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C1-C 60 C6-C substituted with alkyl groups 60 Aryl groups, C1-C 60 selected from the group consisting of heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heteropolycyclic groups, biphenyl groups, and terphenyl groups; * indicates the bond position to the adjacent atom.

[0007] According to another embodiment of the present invention, there is provided an organic light-emitting device comprising a first electrode, a second electrode facing the first electrode, and an organic layer disposed between the first electrode and the second electrode and including a light-emitting layer, wherein the organic layer comprises one or more of the heterocyclic compounds described above. [Effects of the Invention]

[0008] The organic light-emitting device containing the heterocyclic compound of the present invention can achieve low driving voltage, high efficiency, long life, and high maximum quantum efficiency. [Brief explanation of the drawings]

[0009] [Figure 1] 1 is a diagram schematically illustrating a structure of an organic light emitting device according to an embodiment. [Figure 2] 1 is a diagram schematically illustrating a structure of an organic light emitting device according to another embodiment. [Figure 3] 1 is a diagram schematically illustrating a structure of an organic light emitting device according to another embodiment. [Figure 4]1 is a diagram schematically illustrating a structure of an organic light emitting device according to another embodiment. DETAILED DESCRIPTION OF THE INVENTION

[0010] Although the present invention can be modified in various ways and can have various aspects, specific embodiments are illustrated in the drawings and will be described in detail. The advantages, features, and methods of achieving the present invention will become clear by referring to the embodiments described in detail together with the drawings. However, the present invention is not limited to the embodiments disclosed below, and can be realized in various forms.

[0011] Hereinafter, an embodiment of the present invention will be described in detail with reference to the accompanying drawings. When describing with reference to the drawings, the same or similar components will be denoted by the same reference numerals, and duplicate descriptions thereof will be omitted.

[0012] In the following description, singular expressions include plural expressions unless the context clearly indicates otherwise.

[0013] In the following description, the terms "comprise" or "have" mean the presence of the features or components described in the specification, without excluding in advance the possibility that one or more other features or components may also be added.

[0014] In the following description, when a part such as a film, region, or component is said to be on or above another part, this does not only mean that it is directly on top of the other part, but also means that there is another film, region, component, etc. interposed between them.

[0015] In the drawings, the size of components may be exaggerated or reduced for the sake of convenience. For example, the size and thickness of each component shown in the drawings are arbitrarily shown for the sake of convenience, and the present invention is not necessarily limited to what is shown in the drawings.

[0016] [General definition of substituents] As used herein, C1-C 60 The alkyl group refers to a monovalent group of a linear or branched aliphatic hydrocarbon having 1 to 60 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. 60 The alkylene group is C1-C 60 It means a divalent group having the same structure as an alkyl group.

[0017] As used herein, C2-C 60 Alkenyl groups are C2-C 60 It means a hydrocarbon group containing one or more carbon-carbon double bonds in the middle or at the end of the alkyl group, and specific examples thereof include ethenyl, propenyl, and butenyl groups. 60 The alkenylene group is C2-C 60 It means a divalent group having the same structure as an alkenyl group.

[0018] As used herein, C2-C 60 Alkynyl groups are C2-C 60 It means a hydrocarbon group containing one or more carbon-carbon triple bonds in the middle or at the end of the alkyl group, and specific examples thereof include an ethynyl group and a propynyl group. 60 The alkynylene group is C2-C 60 It means a divalent group having the same structure as an alkynyl group.

[0019] As used herein, C1-C 60 The alkoxy group is -OA. 101 (where A 101 is C1-C 60 Specific examples of the alkoxy group include a methoxy group, an ethoxy group, and an isopropyloxy group.

[0020] As used herein, C3-C10 The cycloalkyl group refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. 10 The cycloalkylene group is C3-C 10 It means a divalent group having the same structure as a cycloalkyl group.

[0021] As used herein, C1-C 10 The heterocycloalkyl group means a monovalent monocyclic group having 1 to 10 carbon atoms and containing at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and specific examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. 10 The heterocycloalkylene group is C1-C 10 It means a divalent group having the same structure as a heterocycloalkyl group.

[0022] As used herein, C3-C 10 The cycloalkenyl group refers to a monovalent monocyclic group having 3 to 10 carbon atoms, having at least one double bond in the ring, and not having aromaticity, and specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. 10 The cycloalkenylene group is C3-C 10 It means a divalent group having the same structure as a cycloalkenyl group.

[0023] As used herein, C1-C 10 A heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms and containing at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and having at least one double bond in the ring. 10Specific examples of heterocycloalkenyl groups include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. 10 The heterocycloalkenylene group is a C1-C 10 It means a divalent group having the same structure as a heterocycloalkenyl group.

[0024] As used herein, C6-C 60 An aryl group means a monovalent carbocyclic aromatic group having 6 to 60 carbon atoms, C6-C 60 An arylene group refers to a carbocyclic aromatic divalent group having 6 to 60 carbon atoms. 60 Specific examples of the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. 60 Aryl groups and C6-C 60 When the arylene group contains more than one ring, the two or more rings can be fused together.

[0025] As used herein, C1-C 60 The heteroaryl group means a monovalent heterocyclic aromatic group containing at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom and having 1 to 60 carbon atoms, and is C1-C 60 The heteroarylene group refers to a heterocyclic aromatic divalent group having 1 to 60 carbon atoms and containing at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom. 60 Specific examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl groups. 60 Heteroaryl groups and C1-C 60 When a heteroarylene group contains more than one ring, the two or more rings can be fused together.

[0026] As used herein, C6-C 60 The aryloxy group is -OA.102 (where A 102 is C6-C 60 aryl group), and C6-C 60 The arylthio group is -SA 103 (where A 103 is C6-C 60 aryl group).

[0027] As used herein, a monovalent non-aromatic fused polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are fused together and which contains only carbon as ring-forming atoms, and the entire molecule is non-aromatic. Specific examples of monovalent non-aromatic fused polycyclic groups include a decahydronaphthalenyl group. As used herein, a divalent non-aromatic fused polycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic fused polycyclic group.

[0028] As used herein, a monovalent non-aromatic fused heteropolycyclic group refers to a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are fused together and which contains, in addition to carbon, at least one heteroatom selected from N, O, Si, P, and S as ring-forming atoms, and in which the entire molecule is non-aromatic. Specific examples of monovalent non-aromatic fused heteropolycyclic groups include a 9,10-dihydroacridinyl group. As used herein, a divalent non-aromatic fused heteropolycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic fused heteropolycyclic group.

[0029] As used herein, C5-C 60 A carbocyclic group refers to a monocyclic or polycyclic group containing only carbon atoms as ring atoms and having 5 to 60 carbon atoms. 60 A carbocyclic group is an aromatic or non-aromatic carbocyclic group. 60 A carbocyclic group is a ring such as benzene, a monovalent group such as phenyl, or a divalent group such as phenylene. 60 Depending on the number of substituents attached to the carbocyclic group, C5-C 60 The carbocyclic group may be a trivalent or tetravalent group, and various variations are possible.

[0030] As used herein, C1-C 60 Heterocyclic groups are C5-C 60 It means a group that has the same structure as a carbocyclic group, but contains at least one heteroatom selected from N, O, Si, P, and S in addition to carbon (having 1 to 60 carbon atoms) as ring-forming atoms.

[0031] In this specification, the term "fluorine-containing C5-C 60 A carbocyclic group is a C5-C 60 At least one of the substituents of the carbocyclic group is -F. 60 Carbocyclic groups are fluorine-containing C5-C 60 It means that the carbocyclic group is further substituted with at least one substituent defined herein. 60 Carbocyclic groups are fluorine-containing C5-C 60 It means that all remaining substituents of the carbocyclic group that are not -F are hydrogen.

[0032] In this specification, fluorine-containing C1-C 60 Heterocyclic groups are C1-C 60 At least one of the substituents of the heterocyclic group is -F. 60 Heterocyclic groups are fluorine-containing C1-C 60 means that the heterocyclic group is further substituted with at least one substituent defined herein; and 60 Heterocyclic groups are fluorine-containing C1-C 60 It means that the remaining substituents of the heterocyclic group other than -F are all hydrogen.

[0033] As used herein, substituted C5-C 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C3-C 10 Cycloalkylene groups, substituted C1-C 10Heterocycloalkylene groups, substituted C3-C 10 Cycloalkenylene groups, substituted C1-C 10 Heterocycloalkenylene groups, substituted C6-C 60 Arylene groups, substituted C1-C 60 Heteroarylene group, substituted divalent non-aromatic fused polycyclic group, substituted divalent non-aromatic fused polycyclic heterocyclic group, substituted C1-C 60 Alkyl groups, substituted C2-C 60 Alkenyl groups, substituted C2-C 60 Alkynyl groups, substituted C1-C 60 Alkoxy groups, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocycloalkyl groups, substituted C3-C 10 Cycloalkenyl groups, substituted C1-C 10 Heterocycloalkenyl groups, substituted C6-C 60 Aryl groups, substituted C6-C 60 Aryloxy groups, substituted C6-C 60 Arylthio groups, substituted C1-C 60 At least one of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituent of the substituted monovalent non-aromatic fused polycyclic heterocyclic group is Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 alkoxy groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 alkoxy groups; C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C60 Arylthio groups, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ) C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; and -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ); Q 11 ~Q 13 , Q 21 ~Q 23 , and Q 31 ~Q 33 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 60 Alkyl groups, C2-C 60Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C1-C 60 It may be selected from heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic hetero-fused polycyclic groups, biphenyl groups, and terphenyl groups.

[0034] As used herein, "Ph" means a phenyl group, "Me" means a methyl group, "Et" means an ethyl group, "ter-Bu" or "But" means a tert-butyl group, and "OMe" means a methoxy group.

[0035] In this specification, the term "biphenyl group" may also mean a "phenyl group substituted with a phenyl group." A "biphenyl group" is a group in which the substituent is "C6-C 60 It may also belong to the "substituted phenyl group" which is an "aryl group."

[0036] In this specification, the term "terphenyl group" may also mean a "phenyl group substituted with a biphenyl group." A "terphenyl group" is a group in which the substituent is "C6-C 60 C6-C substituted with aryl groups 60 It may also belong to the "substituted phenyl group" which is an "aryl group."

[0037] In this specification, unless otherwise defined, * and *' indicate the bond positions to adjacent atoms in the corresponding chemical formula.

[0038] [Heterocyclic compounds] The heterocyclic compound of the present invention is represented by the following chemical formula 1. [ka]

[0039] In Chemical Formula 1, X 11 is N or C-[(L 11 ) a11 -(R 11 ) b11 ] and X 12 is N or C-[(L 12 ) a12 -(R 12 ) b12 ] and X 13 is N or C-[(L 13 ) a13 -(R 13 )b 13 ] and X 14 is N or C-[(L 14 ) a14 -(R 14 ) b14 ] and X 15 is N or C-[(L 15 ) a15 -(R 15 ) b15 ]. X 11 ~X 15 At least one of them is N, but X 11 ~X 15 are not all N at the same time.

[0040] As an example, X 11 , X 12 , X 13 , X 14 or X 15 is N or X 11 and X 13 is N or X 12 and X 14 is N or X 11 and X 15 is N or X 11 , X 13 and X 15 may be N, but is not limited to these.

[0041] Another example is X 11 , X 13 and X 15 is N and X 12 is C-[(L12 ) a12 -(R 12 ) b12 ] and X 14 is C-[(L 14 ) a14 -(R 14 ) b14 ], but is not limited to these.

[0042] In Chemical Formula 1, n1 is 0, 1, or 2, and n2 is 1, 2, or 3. Here, the sum of n1 and n2 is 3.

[0043] For example, n1 may be 0 and n2 may be 3, or n1 may be 1 and n2 may be 2, or n1 may be 2 and n2 may be 1.

[0044] As an example, n1 may be 2 and n2 may be 1, but is not limited to this.

[0045] n1 is *-[(L1) a1 -(R1) b1 When n1 is 2 or more, it indicates the number of substituents represented by *-[(L1) a1 -(R1) b1 The substituents represented by the symbols

[0047] may be the same or different. The explanation for n2 is the same as that for n1, and will be understood with reference to the explanation for n1.

[0046] TIFF0007813089000003.tif56170

[0047] For example, in Chemical Formula 1, when n1 is 2 and n2 is 1, the heterocyclic compound represented by Chemical Formula 1 has the following structure (A). [ka] Furthermore, in Chemical Formula 1, when n1 is 1 and n2 is 2, the heterocyclic compound represented by Chemical Formula 1 has the following structure (B). [ka] Furthermore, in Chemical Formula 1, when n1 is 0 and n2 is 3, the heterocyclic compound represented by Chemical Formula 1 has the following structure (C). [ka]

[0048] In Chemical Formula 1, L1, L2, L 11 ~L 15 , R1, and R 11 ~R 15 are, independently of each other, substituted or unsubstituted C5-C 60 Carbocyclic groups and substituted or unsubstituted C1-C 60 The heterocyclic group is selected from the group consisting of:

[0049] As an example, L1, L2, L 11 ~L 15 , R1, and R 11 ~R 15 are independent of each other, Benzene, pentalene, indene, naphthalene, azulene, heptalene, indacene, acenaphthylene, fluorene, spirofluorene, benzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, hexacene, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, isoindole, indole, indazole, purine, quinoline, isoquinoline, benzoquinoline, fluorene Monovalent or divalent radicals of thalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, carbazole, phenanthridine, acridine, phenanthroline, phenazine, benzoxazole, benzimidazole, furan, benzofuran, thiophene, benzothiophene, thiazole, isothiazole, benzothiazole, isoxazole, oxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran, dibenzothiophene, benzocarbazole, and dibenzocarbazole; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, C6-C 20 Aryl groups, C2-C 20 Heteroaryl groups and -Si(Q 31 )(Q 32 )(Q 33benzene, pentalene, indene, naphthalene, azulene, heptalene, indacene, acenaphthylene, fluorene, spirofluorene, benzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, hexacene, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, isoindole, indole, indazole, purine, quinoline, isoquinoline, benzoquinoline, fluorene, Monovalent or divalent radicals of thalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, carbazole, phenanthridine, acridine, phenanthroline, phenazine, benzoxazole, benzimidazole, furan, benzofuran, thiophene, benzothiophene, thiazole, isothiazole, benzothiazole, isoxazole, oxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran, dibenzothiophene, benzocarbazole, and dibenzocarbazole;

[0050] In another example, L1, L2, and L 11 ~L 15 are each independently selected from the group represented by the following Chemical Formula 3-1 to Chemical Formula 3-47, but are not limited thereto. [ka] JPEG0007813089000008.jpg223154JPEG0007813089000009.jpg169139JPEG0007813089000010.jpg204153

[0051] In Chemical Formula 3-1 to Chemical Formula 3-47, Y1 is O, S, C(Z3)(Z4), N(Z5) or Si(Z6)(Z7); Z1 to Z7 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, or a C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclopentenyl groups, cyclohexenyl groups, phenyl groups, biphenyl groups, naphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyridinyl groups, pyrazinyl groups, pyrimidinyl groups, quinolinyl groups, isoquinolinyl groups, benzoquinolinyl groups, naphthyridinyl groups, quinoxalinyl groups, quinazolinyl groups, carbazolyl groups, phenanthridinyl groups, acridinyl groups, phenanthrolinyl groups, phenazinyl groups, triazinyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, and -Si(Q 31 )(Q 32 )(Q 33 ), d2 is selected from integers of 0 to 2, and when d2 is 2 or more, two or more Z1 may be the same or different from each other; d3 is selected from integers of 0 to 3, and when d3 is 2 or more, two or more Z1 and Z2 may be the same or different from each other; d4 is selected from integers of 0 to 4, and when d4 is 2 or more, two or more Z1 and Z2 may be the same or different from each other; d5 is selected from integers of 0 to 5, and when d5 is 2 or more, two or more Z1 and Z2 may be the same or different from each other; d6 is selected from integers of 0 to 6, and when d6 is 2 or more, two or more Z1 may be the same or different from each other; d8 is selected from integers of 0 to 8, and when d8 is 2 or more, two or more Z1 may be the same or different from each other; * and *' indicate the bond position to the adjacent atom.

[0052] In yet another example, L1, L2, and L 11 ~L 15 are each independently selected from the group represented by the following chemical formulas 4-1 to 4-24, but are not limited thereto. [ka] JPEG0007813089000012.jpg188135

[0053] In Chemical Formula 4-1 to Chemical Formula 4-24, Y 21 is O, S, C(Z 23 )(Z 24 ), N(Z 25 ) or Si(Z 26 )(Z 27 ) and Z 21 ~Z 27 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C1-C 20 Alkyl groups, C1-C 20 selected from the group consisting of alkoxy, phenyl and naphthyl; d2 is selected from integers of 0 to 2, and when d2 is 2 or more, 2 or more Z 21 may be the same or different from each other, d3 is selected from integers of 0 to 3, and when d3 is 2 or more, 2 or more Z 21 and Z 22 may be the same or different from each other, d4 is selected from integers of 0 to 4, and when d4 is 2 or more, 2 or more Z 21 and Z 22 may be the same or different from each other, d6 is selected from integers of 0 to 6, and when d6 is 2 or more, 2 or more Z 21 may be the same or different from each other, d8 is selected from integers of 0 to 8, and when d8 is 2 or more, 2 or more Z 21may be the same or different from each other, * and *' indicate the bond position to the adjacent atom.

[0054] In Chemical Formula 1, a1, a2, and a11 to a15 may be independently selected from integers of 0 to 5, but are not limited thereto.

[0055] a1 indicates the number of L1, and when a1 is 2 or more, the two or more L1 may be the same or different. The explanation for a2 and a11 to a15 is the same as for a1, and will be understood with reference to the explanation for a1.

[0056] If a1 is 0, then *-(L1) a1 -*' is a single bond, and when a2 is 0, *-(L2) a2 -*' is a single bond, and when a11 is 0, *-(L 11 ) a11 -*' is a single bond, and when a12 is 0, *-(L 12 ) a12 -*' is a single bond, and when a13 is 0, *-(L 13 ) a13 -*' is a single bond, and when a14 is 0, *-(L 14 ) a14 -*' is a single bond, and when a15 is 0, *-(L 15 ) a15 -*' is a single bond.

[0057] In one example, a1 may be 0, but is not limited to this.

[0058] In one example, a2 may be 0, 1, 2, 3 or 4, but is not limited to these.

[0059] In one example, a11 to a15 may be, independently of one another, 0, 1 or 2, but are not limited thereto.

[0060] In another example, a1 is 0, a2 is 0, 1, 2, 3 or 4, and a11 to a15 may be independently 0, 1 or 2, but are not limited to these.

[0061] In one example, R and R 11 ~R 15 may be independently selected from the group represented by the following Chemical Formula 5-1 to Chemical Formula 5-79, but are not limited thereto. [ka] JPEG0007813089000014.jpg215140JPEG0007813089000015.jpg211147JPEG0007813089000016.jpg21815 3JPEG0007813089000017.jpg215154JPEG0007813089000018.jpg208153JPEG0007813089000019.jpg40132

[0062] In Chemical Formula 5-1 to Chemical Formula 5-79, Y 31 is O, S, C(Z 33 )(Z34), N(Z 35 ) or Si(Z 36 )(Z 37 ) and Z 31 ~Z 37 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20Alkoxy groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclopentenyl groups, cyclohexenyl groups, phenyl groups, biphenyl groups, naphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, spiro-fluorene-benzofluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyridinyl groups, pyrazinyl groups, pyrimidinyl groups, quinolinyl groups, isoquinolinyl groups, benzoquinolinyl groups, naphthyridinyl groups, quinoxalinyl groups, quinazolinyl groups, carbazolyl groups, phenanthridinyl groups, acridinyl groups, phenanthrolinyl groups, phenazinyl groups, triazinyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, and -Si(Q 31 )(Q 32 )(Q 33 ), e2 is selected from integers of 0 to 2, and when e2 is 2 or more, Z 32 may be the same or different from each other, e3 is selected from integers of 0 to 3, and when e3 is 2 or more, it is 2 or more Z 31 and Z 32 may be the same or different from each other, e4 is selected from integers of 0 to 4, and when e4 is 2 or more, 2 or more Z 31 and Z 32 may be the same or different from each other, e5 is selected from integers from 0 to 5, and when e5 is 2 or more, it is 2 or more Z 31 and Z 32 may be the same or different from each other, e6 is selected from integers from 0 to 6, and when e6 is 2 or more, it is 2 or more Z 31 and Z 32 may be the same or different from each other, e7 is selected from integers from 0 to 7, and when e7 is 2 or more, it is 2 or more Z 31 may be the same or different from each other, e9 is selected from integers from 0 to 9, and when e9 is 2 or more, 2 or more Z 31 may be the same or different from each other, * indicates the bond position to the adjacent atom.

[0063] In another example, R1 is a phenyl group and a naphthyl group; and -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 The alkyl group may be selected from, but is not limited to, an alkoxy group, a phenyl group, and a naphthyl group substituted with at least one selected from the group consisting of a phenyl group and a naphthyl group.

[0064] b1 and b11 to b15 may be selected from integers of 1 to 10, each independently.

[0065] b1 indicates the number of R1, and when b1 is 2 or more, the two or more R1 may be the same or different. The explanation for b11 to b15 is the same as that for b1, and will be understood with reference to the explanation for b1.

[0066] In Chemical Formula 1, L1, L2, L 11 ~L 15 , R1, and R 11 ~R 15 Any two of these may be bonded to each other and may be substituted or unsubstituted C5-C 60 Carbocyclic groups or substituted or unsubstituted C1-C 60 A heterocyclic group may be formed.

[0067] In one example, the heterocyclic compound represented by Chemical Formula 1 is represented by the following Chemical Formula 1-2 or 1-3. [ka] JPEG0007813089000021.jpg50147

[0068] In Chemical Formula 1-2 and Chemical Formula 1-3, A1 and A2 are independently C5-C 60 Carbocyclic groups and C1-C 60 heterocyclic groups, X 21 is a single bond, C(R 21 )(R 22 ), N(R 21 ), O, S or Si(R 21 )(R 22 ) and The explanation regarding L3 is the same as that regarding L1 in the explanation regarding Chemical Formula 1, The explanation for a3 is the same as that for a1 in the explanation for Chemical Formula 1, R 21 , R 22 , Z1, Z 31 and Z 32 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C2-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C2-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 31 )(Q 32 )(Q33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ), e51, e52, and d51 are each independently selected from integers of 1 to 10; X 11 ~X 15 , L1, L2, a1, a2, R1 and b1 are the same as those described in the explanation of Chemical Formula 1.

[0069] The heterocyclic compound represented by Chemical Formula 1 contains at least one -F.

[0070] The heterocyclic compound represented by Chemical Formula 1 contains at least one -F, which means that L1, L2, L 11 ~L 15 , R1, and R 11 ~R 15 At least one of the above is a substituted or unsubstituted fluorine-containing C5-C 60 Carbocyclic groups and substituted or unsubstituted fluorine-containing C1-C 60 It means that the ring is selected from heterocyclic groups.

[0071] The heterocyclic compound represented by Chemical Formula 1 may contain an integer number of -F selected from the integers of 1 to 20, but is not limited thereto.

[0072] For example, but not limited to, the heterocyclic compound may contain 1, 2, 3, 4, or 6 -F.

[0073] In one example, R 11 ~R 15 At least one of the above is a substituted or unsubstituted fluorine-containing C5-C 60 Carbocyclic groups and substituted or unsubstituted fluorine-containing C1-C60 The heterocyclic group may be selected from the group consisting of aryl, ...

[0074] In another example, R 11 ~R 15 At least one of the above is a substituted or unsubstituted fluorine-containing C5-C 60 It may also be a carbocyclic group.

[0075] In yet another example, R 11 ~R 15 are independent of each other, Benzene, pentalene, indene, naphthalene, azulene, heptalene, indacene, acenaphthylene, fluorene, spirofluorene, benzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, tetracene, picene, perylene, pentaphene, hexacene, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, isoindole, indole, indazole, purine, quinoline, isoquinoline, benzoquinoline , phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, carbazole, phenanthridine, acridine, phenanthroline, phenazine, benzoxazole, benzimidazole, furan, benzofuran, thiophene, benzothiophene, thiazole group, isothiazole, benzothiazole, isoxazole, oxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran, dibenzothiophene, benzocarbazole, and dibenzocarbazole monovalent radicals; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, C6-C 20 Aryl groups, C2-C 20 Heteroaryl groups and -Si(Q 31 )(Q 32 )(Q 33benzene, pentalene, indene, naphthalene, azulene, heptalene, indacene, acenaphthylene, fluorene, spirofluorene, benzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, tetracene, picene, perylene, pentaphene, hexacene, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, isoindole, indole, indazole, purine, quinoline, isoquinoline, , benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, carbazole, phenanthridine, acridine, phenanthroline, phenazine, benzoxazole, benzimidazole, furan, benzofuran, thiophene, benzothiophene, thiazole group, isothiazole, benzothiazole, isoxazole, oxazole, triazole group, tetrazole, oxadiazole, triazine, dibenzofuran, dibenzothiophene, benzocarbazole and dibenzocarbazole group, R 11 Or R 15 At least one of may be substituted with at least one -F, but is not limited thereto.

[0076] In yet another example, R 11 ~R 15 At least one of may be selected from the group represented by the following Chemical Formula 7-1 to Chemical Formula 7-77, but is not limited thereto. [ka] JPEG0007813089000023.jpg202155JPEG0007813089000024.jpg212155JPEG00078130890 00025.jpg199154JPEG0007813089000026.jpg223155JPEG0007813089000027.jpg180156

[0077] In Chemical Formula 7-1 to Chemical Formula 7-77, Z 41 represents hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclopentenyl groups, cyclohexenyl groups, phenyl groups, biphenyl groups, naphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, spiro-fluorene-benzofluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyridinyl groups, pyrazinyl groups, pyrimidinyl groups, quinolinyl groups, isoquinolinyl groups, benzoquinolinyl groups, naphthyridinyl groups, quinoxalinyl groups, quinazolinyl groups, carbazolyl groups, phenanthridinyl groups, acridinyl groups, phenanthrolinyl groups, phenazinyl groups, triazinyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, and -Si(Q 31 )(Q 32 )(Q 33 ), f2 is selected from integers of 1 to 2, and when f2 is 2 or more, 2 or more Z 41 may be the same or different from each other, f3 is selected from integers of 1 to 3, and when f3 is 2 or more, 2 or more Z 41 may be the same or different from each other, f4 is selected from integers of 1 to 4, and when f4 is 2 or more, 2 or more Z 41 may be the same or different from each other, f5 is selected from integers of 1 to 5, and when f5 is 2 or more, 2 or more Z 41 may be the same or different from each other, f6 is selected from integers from 1 to 6, and when f6 is 2 or more, 2 or more Z 41 may be the same or different from each other, * indicates the bond position to the adjacent atom.

[0078] In one example, R1 is a phenyl group and a naphthyl group; and -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 phenyl and naphthyl groups substituted with at least one selected from alkoxy groups, phenyl groups, and naphthyl groups; R 11 ~R 15 At least one of may be selected from the group represented by Chemical Formula 7-1 to Chemical Formula 7-77, but is not limited thereto.

[0079] In one example, X 11 , X 13 and X 15 is N and X 12 is C-[(L 12 ) a12 -(R 12 ) b12 ] and X 14 is C-[(L 14 ) a14 -(R 14 ) b14 ] and R 12 and R 14 At least one of the above is a substituted or unsubstituted fluorine-containing C5-C 60 Carbocyclic groups and substituted or unsubstituted fluorine-containing C1-C 60 The heterocyclic group may be selected from, but is not limited to, heterocyclic groups.

[0080] In another example, X 11 , X 13 and X 15 is N and X 12 is C-[(L 12 ) a12 -(R 12 ) b12 ] and X 14 is C-[(L 14 )a14 -(R 14 ) b14 ] and R 12 and R 14 At least one of may be selected from the group represented by Chemical Formula 7-1 to Chemical Formula 7-77, but is not limited thereto.

[0081] In one example, the heterocyclic compound represented by Chemical Formula 1 may be any one of Compounds 1 to 132 below, but is not limited thereto. [ka] JPEG0007813089000029.jpg226126JPEG0007813089000030.jpg218153JPEG0007813089000031.j pg216153JPEG0007813089000032.jpg219150JPEG0007813089000033.jpg226153JPEG00078130890 00034.jpg193117JPEG0007813089000035.jpg206139JPEG0007813089000036.jpg213139JPEG000 7813089000037.jpg215155JPEG0007813089000038.jpg223147JPEG0007813089000039.jpg195142

[0082] The heterocyclic compound represented by Chemical Formula 1 contains at least one fluorine substituent in the molecule. Fluorine has a large electronegativity and electron affinity, which increases the dipole moment of the molecule and improves the electron injection and electron transport capabilities of the compound. Therefore, the heterocyclic compound represented by Chemical Formula 1 contains at least one F, and therefore can have high electron injection and electron transport capabilities.

[0083] The heterocyclic compound represented by Chemical Formula 1 also contains a phosphine oxide structure. Phosphine oxide compounds have a tetrahedral structure and can form amorphous films due to their steric molecular structure. Furthermore, they are capable of negative hyperconjugation (back donation) and hydrogen bonding, and have a large electronegativity, which can stabilize the molecule and form a dipole within the molecule, thereby enhancing electron transport ability.

[0084] Furthermore, electronic devices containing heterocyclic compounds, such as organic light-emitting devices, can achieve low driving voltage, high current density, and high efficiency.

[0085] The heterocyclic compound represented by Chemical Formula 1 can be synthesized using known organic synthesis methods. Those skilled in the art will recognize the synthesis method of the heterocyclic compound by referring to the examples described below.

[0086] At least one heterocyclic compound represented by Chemical Formula 1 is used between a pair of electrodes of an organic light-emitting device. For example, the heterocyclic compound may be included in at least one of a hole transport region, an electron transport region, and an emitting layer. Alternatively, the heterocyclic compound represented by Chemical Formula 1 may be used as a capping layer material located outside the pair of electrodes of an organic light-emitting device.

[0087] Therefore, there is provided an organic light-emitting device comprising a first electrode, a second electrode facing the first electrode, and an organic layer disposed between the first electrode and the second electrode and including a light-emitting layer, wherein the organic layer comprises one or more heterocyclic compounds represented by Chemical Formula 1.

[0088] In this specification, the phrase "(the organic layer) contains one or more heterocyclic compounds" is interpreted as "(the organic layer) may contain one heterocyclic compound belonging to the category of Chemical Formula 1, or two or more different heterocyclic compounds belonging to the category of Chemical Formula 1."

[0089] For example, the organic layer may contain only the above-described compound 1 as a heterocyclic compound. In this case, compound 1 may be used in the light-emitting layer of an organic light-emitting device. Alternatively, the organic layer may contain compound 1 and compound 2 as heterocyclic compounds. In this case, compound 1 and compound 2 may be present in the same layer (e.g., compound 1 and compound 2 may both be used in the light-emitting layer) or may be present in different layers (e.g., compound 1 may be used in the light-emitting layer and compound 2 may be used in the electron-transporting layer).

[0090] In this specification, the term "organic layer" refers to any single and / or multiple layers interposed between a first electrode and a second electrode in an organic light-emitting device. The materials contained in the "organic layer" are not limited to organic materials.

[0091] According to one example, the first electrode is an anode, the second electrode is a cathode, and the organic layer includes an emitting layer disposed between the first electrode and the second electrode, a hole transport region disposed between the first electrode and the emitting layer, and an electron transport region disposed between the emitting layer and the second electrode, wherein the hole transport region may include a hole injection layer, a hole transport layer, an emitting auxiliary layer, an electron blocking layer, or any combination thereof, and the electron transport region may include a buffer layer, a hole blocking layer, an electron modulating layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0092] In one example, the electron transport region may include, but is not limited to, a heterocyclic compound.

[0093] In another example, the electron transport region may include an electron transport layer, and the electron transport layer may include, but is not limited to, a heterocyclic compound represented by Chemical Formula 1.

[0094] In one example, the light-emitting layer may include, but is not limited to, a heterocyclic compound.

[0095] In one example, the hole transport region includes a p-dopant, and the LUMO (lowest unoccupied molecular orbital) of the p-dopant may be less than or equal to −3.5 eV.

[0096] The p-dopant may include at least one selected from the group consisting of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, the p-dopant may include, but is not limited to, a cyano group-containing compound.

[0097] The light-emitting layer includes a first light-emitting layer that emits a first color light. Furthermore, between the first electrode and the second electrode, i) at least one second light-emitting layer that emits a second color light may be additionally included, or ii) at least one second light-emitting layer that emits the second color light and at least one third light-emitting layer that emits a third color light may be additionally included. The maximum emission wavelengths of the first color light, the second color light, and the third color light may be the same or different from one another, and mixed color light obtained by mixing the first color light and the second color light, or mixed color light obtained by mixing the first color light, the second color light, and the third color light, may be emitted.

[0098] [Organic light-emitting element 10] 1 is a schematic cross-sectional view of an organic light emitting device 10 according to one 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.

[0099] Hereinafter, the structure and manufacturing method of an organic light emitting device 10 according to an embodiment of the present invention will be described with reference to FIG.

[0100] [First electrode 110] 1, a substrate (not shown) may be additionally disposed below the first electrode 110 or above the second electrode 190. As the substrate, a glass substrate or a plastic substrate, which has excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness, may be used.

[0101] The first electrode 110 is formed by depositing a first electrode material on the substrate using, for example, evaporation or sputtering. When the first electrode 110 is an anode, the first electrode material may be selected from materials having a high work function to facilitate hole injection.

[0102] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. To form the first electrode 110 as a transmissive electrode, the first electrode material may be selected from, but is not limited to, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof. To form the first electrode 110 as a semi-transmissive electrode or a reflective electrode, the first electrode material may be selected from, but is not limited to, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof.

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

[0104] [Organic layer 150] The organic layer 150 is disposed on the first electrode 110. The organic layer 150 includes a light-emitting layer.

[0105] The organic layer 150 may further include a hole transport region disposed between the first electrode 110 and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode 190.

[0106] [Hole transport region in organic layer 150] The hole transport region can have i) a single layer structure consisting of a single layer made of a single material, ii) a single layer structure consisting of single layers made of multiple different materials, or iii) a multilayer structure having multiple layers made of multiple different materials.

[0107] The hole transport region may include at least one layer selected from a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting auxiliary layer, and an electron blocking layer (EBL).

[0108] For example, the hole transport region may have a single layer structure consisting of a plurality of single layers made of different materials, or a multilayer structure consisting of a hole injection layer / hole transport layer, a hole injection layer / hole transport layer / light emitting auxiliary layer, a hole injection layer / light emitting auxiliary layer, a hole transport layer / light emitting auxiliary layer, or a hole injection layer / hole transport layer / electron blocking layer, which are stacked in this order from the first electrode 110, but is not limited to these.

[0109] The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by the following chemical formula 201, and a compound represented by the following chemical formula 202.

[0110] [ka] JPEG0007813089000041.jpg155141 JPEG0007813089000042.jpg77142

[0111] In Chemical Formula 201 and Chemical Formula 202, L 201 ~L 204 are, independently of each other, substituted or unsubstituted C3-C 10 Cycloalkylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkylene groups, substituted or unsubstituted C3-C 10 Cycloalkenylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkenylene group, substituted or unsubstituted C6-C 60 Arylene groups, substituted or unsubstituted C1-C 60 selected from the group consisting of heteroarylene groups, substituted or unsubstituted divalent non-aromatic fused polycyclic groups, and substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic groups; L 205 *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C1-C 20 Alkylene group, substituted or unsubstituted C2-C 20 Alkenylene group, substituted or unsubstituted C3-C 10 Cycloalkylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkylene groups, substituted or unsubstituted C3-C 10 Cycloalkenylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkenylene group, substituted or unsubstituted C6-C 60 Arylene groups, substituted or unsubstituted C1-C 60 selected from the group consisting of heteroarylene groups, substituted or unsubstituted divalent non-aromatic fused polycyclic groups, and substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic groups; xa1 to xa4 are each independently selected from integers of 0 to 3; xa5 is selected from integers from 1 to 10; R 201 ~R 204 , and Q 201 are, independently of each other, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 It may be selected from a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused polycyclic hetero group.

[0112] For example, in formula 202, R 201 and R 202 may optionally be bonded to each other via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group, and R 203 and R 204 may alternatively be bonded to each other via a single bond, a dimethyl-methylene group or a diphenyl-methylene group.

[0113] As an example, in chemical formula 201 and chemical formula 202, L 201~ L 205 are independent of each other, a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, perylenylene groups, pentaphenylene groups, hexacenylene groups, pentacenylene groups, rubicenylene groups, coronenylene groups, ovalenylene groups, thiophenylene groups, furanylene groups, carbazolylene groups, indolylene groups, isoindolylene groups, benzofuranylene groups, benzothiophenylene groups, dibenzofuranylene groups, dibenzothiophenylene groups, benzocarbazolylene groups, dibenzocarbazolylene groups, dibenzosilolylene groups, and pyridinylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 Phenyl groups substituted with alkyl groups, phenyl groups substituted with -F, pentalenyl groups, indenyl groups, naphthyl groups, azulenyl groups, heptalenyl groups, indacenyl groups, acenaphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, chrysenyl groups, naphthyl groups, Tacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, -Si(Q 31 )(Q 32)(Q 33 ), and -N(Q 31 )(Q 32 a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, or a naphthacenylene group, each of which is substituted with at least one selected from the group consisting of groups, picenylene groups, perylenylene groups, pentaphenylene groups, hexacenylene groups, pentacenylene groups, rubicenylene groups, coronenylene groups, ovalenylene groups, thiophenylene groups, furanylene groups, carbazolylene groups, indolylene groups, isoindolylene groups, benzofuranylene groups, benzothiophenylene groups, dibenzofuranylene groups, dibenzothiophenylene groups, benzocarbazolylene groups, dibenzocarbazolylene groups, dibenzosilolylene groups, and pyridinylene groups; Q 31 ~Q 33 are independent of each other, C1-C 10 Alkyl groups, C1-C 10 It may be selected from alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups and naphthyl groups.

[0114] According to another example, xa1 to xa4 may be 0, 1 or 2, independently of one another.

[0115] In yet another example, xa5 may be 1, 2, 3 or 4.

[0116] According to yet another example, R 201 ~R 204 , and Q 201are each independently a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthyl group, tacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, and pyridinyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 Phenyl groups substituted with alkyl groups, phenyl groups substituted with -F, pentalenyl groups, indenyl groups, naphthyl groups, azulenyl groups, heptalenyl groups, indacenyl groups, acenaphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, chrysenyl groups, naphthyl groups, Tacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, -Si(Q 31 )(Q 32 )(Q 33), and -N(Q 31 )(Q 32 a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group; Q 31 ~Q 33 For the relevant explanation, please refer to the description in this specification.

[0117] According to yet another example, in formula 201, R 201 ~R 203 At least one of the fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10The phenyl group may be selected from, but is not limited to, a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from the group consisting of a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

[0118] According to yet another example, in Formula 202, i) R 201 and R 202 may be bonded to each other via a single bond, and / or ii) R 203 and R 204 may be bonded to each other via a single bond.

[0119] According to yet another example, in formula 202, R 201 ~R 204 At least one of the a carbazolyl group; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 The phenyl group may be selected from, but is not limited to, a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a carbazolyl group substituted with at least one selected from a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

[0120] The compound represented by chemical formula 201 may also be represented by chemical formula 201A below. [ka] ...Chemical formula 201A

[0121] For example, the compound represented by chemical formula 201 may be represented by the following chemical formula 201A(1), but is not limited thereto. [ka] ...Chemical formula 201A(1)

[0122] As yet another example, the compound represented by Chemical Formula 201 may be represented by Chemical Formula 201A-1 below, but is not limited thereto. [ka] ...Chemical formula 201A-1

[0123] Alternatively, the compound represented by formula 202 may be represented by formula 202A. [ka] ...Chemical formula 202A

[0124] According to yet another example, the compound represented by formula 202 may be represented by the following formula 202A-1: [ka] ...Chemical formula 202A-1

[0125] In chemical formulas 201A, 201A(1), 201A-1, 202A and 202A-1, L 201 ~L 203 , xa1 to xa3, xa5, and R 202 ~R 204 For a description of the above, please refer to the description in this specification. R 211 and R 212 The explanation regarding R 203 Please refer to the explanation regarding R 213 ~R217 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 10 Phenyl groups substituted with alkyl groups, phenyl groups substituted with -F, pentalenyl groups, indenyl groups, naphthyl groups, azulenyl groups, heptalenyl groups, indacenyl groups, acenaphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, chrysenyl groups, and naphthacenyl groups , picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, and pyridinyl group.

[0126] The hole transport region may contain at least one compound selected from the following compounds HT1 to HT39, but is not limited thereto. [ka] JPEG0007813089000049.jpg82138 JPEG0007813089000050.jpg79133 JPEG0007813089000051.jpg87137 JPEG0007813089000052.jpg81139 JPEG0007813089000053.jpg79137 JPEG0007813089000054.jpg38139

[0127] The thickness of the hole transport region may be about 10 nm to about 1,000 nm, for example, about 10 nm to about 100 nm. When the hole transport region includes at least one layer selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about 10 nm to about 900 nm, for example, about 10 nm to about 100 nm, and the thickness of the hole transport layer may be about 5 nm to about 200 nm, for example, about 10 nm to about 150 nm. When the thicknesses of the hole transport region, hole injection layer, and hole transport layer satisfy the above-mentioned ranges, satisfactory hole transport properties can be obtained without a substantial increase in driving voltage.

[0128] The light-emitting auxiliary layer compensates for the optical resonance distance depending on the wavelength of light emitted from the light-emitting layer, thereby increasing light emission efficiency. The electron-blocking layer prevents electron injection from the electron-transporting region. The light-emitting auxiliary layer and the electron-blocking layer may contain the materials described above.

[0129] [p-dopant] In addition to the materials described above, the hole transport region may further include a charge generating material to improve conductivity. The charge generating material may be uniformly or non-uniformly dispersed within the hole transport region.

[0130] The charge generating material can be, for example, a p-dopant. In one example, the LUMO of the p-dopant can be −3.5 eV or less.

[0131] The p-dopant may include at least one selected from the group consisting of quinone derivatives, metal oxides, and cyano group-containing compounds, but is not limited thereto. For example, the p-dopant may be quinone derivatives such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxide and molybdenum oxide; 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and The compound may include at least one selected from the following compounds represented by the following chemical formula 221; but is not limited to these: [ka]

[0132] In chemical formula 221, R 221 ~R 223 are, independently of each other, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C1-C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused polycyclic heterocyclic group, wherein R 221 ~R 223 At least one of the C1-C substituted with cyano group, -F, -Cl, -Br, -I, -F 20 Alkyl groups, C1-C substituted with -Cl 20 Alkyl groups, C1-C substituted with -Br 20 C1-C substituted with alkyl groups and -I 20 It has at least one substituent selected from alkyl groups.

[0133] [Light-emitting layer in organic layer 150] 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 a blue light emitting layer for each subpixel, or may have a structure in which two or more layers selected from the red light emitting layer, the green light emitting layer, and the blue light emitting layer are stacked in contact with or spaced apart from each other, or a structure in which two or more materials selected from the red light emitting material, the green light emitting material, and the blue light emitting material are mixed without layer division, thereby emitting white light.

[0134] The light-emitting layer may include a host and a dopant. The dopant may include at least one of a phosphorescent dopant and a fluorescent dopant.

[0135] In the light-emitting layer, the content of the dopant is generally selected in the range of about 0.01 to about 15 parts by weight per about 100 parts by weight of the host, but is not limited thereto.

[0136] The thickness of the light-emitting layer is about 10 nm to about 100 nm, for example, about 20 nm to about 60 nm. When the thickness of the light-emitting layer satisfies the above range, excellent light-emitting characteristics can be exhibited without a substantial increase in driving voltage.

[0137] [Host in the light-emitting layer] The host may include a compound represented by formula 301. [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ...Chemical formula 301

[0138] In chemical formula 301, Ar 301 is a substituted or unsubstituted C5-C 60 Carbocyclic groups or substituted or unsubstituted C1-C 60 is a heterocyclic group, xb11 is 1, 2, or 3, L 301 is a substituted or unsubstituted C3-C 10Cycloalkylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkylene groups, substituted or unsubstituted C3-C 10 Cycloalkenylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkenylene group, substituted or unsubstituted C6-C 60 Arylene groups, substituted or unsubstituted C1-C 60 selected from the group consisting of heteroarylene groups, substituted or unsubstituted divalent non-aromatic fused polycyclic groups, and substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic groups; xb1 is selected from integers from 0 to 5; R 301 is deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 Alkenyl groups, substituted or unsubstituted C2-C 60 Alkynyl groups, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 301 )(Q 302 )(Q 303 ), -N(Q 301 )(Q 302 ), -B(Q 301 )(Q 302 ), -C(=O)(Q 301), -S(=O)2(Q 301 ), and -P(=O)(Q 301 )(Q 302 ), xb21 is selected from integers from 1 to 5; Q 301 ~Q 303 are independent of each other, C1-C 10 Alkyl groups, C1-C 10 It is selected from, but not limited to, an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

[0139] According to one example, in formula 301, Ar 301 teeth, The ring structures of naphthalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, indenoanthracene, dibenzofuran, and dibenzothiophene; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32naphthalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, indenoanthracene, dibenzofuran, and dibenzothiophene ring structures substituted with at least one selected from the group consisting of Q 31 ~Q 33 are independent of each other, C1-C 10 Alkyl groups, C1-C 10 It may also be selected from, but is not limited to, an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

[0140] In chemical formula 301, when xb11 is 2 or more, 2 or more Ar 301 may be bonded to each other via a single bond.

[0141] In another example, the compound represented by formula 301 is represented by the following formula 301-1 or 301-2: [ka] ...Chemical formula 301-1 JPEG0007813089000057.jpg43141...Chemical formula 301-2

[0142] Chemical formulas 301-1 to 301-2: A 301 ~A 304have, independently from one another, a ring structure selected from benzene, naphthalene, phenanthrene, fluoranthene, triphenylene, pyrene, chrysene, pyridine, pyrimidine, indene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, indole, carbazole, benzocarbazole, dibenzocarbazole, furan, benzofuran, dibenzofuran, naphthofuran, benzonaphthofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthothiophene, benzonaphthothiophene and dinaphthothiophene; X 301 is O, S or N-[(L 304 ) xb4 -R 304 ] and R 311 ~R 314 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q31)(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q31), -S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ), xb22 and xb23 are independently 0, 1 or 2; L 301 , xb1, R 301 , and Q 31 ~Q 33 For a description of the above, please refer to the description in this specification. L 302 ~L 304 The explanations for L 301 Please refer to the explanation regarding The explanations for xb2 to xb4 are independent of each other and refer to the explanation for xb1. R 302 ~R 304 The explanations for R 301 Please refer to the explanation related to this.

[0143] For example, in Chemical Formula 301, Chemical Formula 301-1, and Chemical Formula 301-2, L 301 ~L 304 are independent of each other, Phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imidazolylene group, pyrazolylene group, thiazolylene group , isothiazolylene groups, oxazolylene groups, isoxazolylene groups, thiadiazolylene groups, oxadiazolylene groups, pyrazinylene groups, pyrimidinylene groups, pyridazinylene groups, triazinylene groups, quinolinylene groups, isoquinolinylene groups, benzoquinolinylene groups, phthalazinylene groups, naphthyridinylene groups, quinoxalinylene groups, quinazolinylene groups, cinnolinylene groups, phenanthridinylene groups, acridinylene groups, phenanthrolinylene groups, phenazinylene groups, benzimidazolylene groups, isobenzothiazolylene groups, benzoxazolylene groups, isobenzoxazolylene groups, triazolylene groups, tetrazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups, and azacarbazolylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazo a aryl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, or a pyrazolylene group; a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group; Q 31 ~Q 33 For the explanation of this, please refer to the description in this specification.

[0144] As another example, in Formula 301, Formula 301-1, and Formula 301-2, R 301 ~R 304 are independent of each other, Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group , thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazo a aryl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; Q 31 ~Q 33 For the explanation of this, please refer to the description in this specification.

[0145] As yet another example, the host may include an alkaline earth metal complex, for example, the host may be selected from the group consisting of a Be complex (e.g., see compound H55 below), a Mg complex, and a Zn complex.

[0146] The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and Compounds H1 to H55 below, but is not limited thereto. [ka] JPEG0007813089000059.jpg63138 JPEG0007813089000060.jpg85138 JPEG0007813089000061.jpg56137 JPEG0007813089000062.jpg87140 JPEG0007813089000063.jpg65139 JPEG0007813089000064.jpg59137

[0147] [Phosphorescent dopant included in the light-emitting layer of organic layer 150] The phosphorescent dopant may include organometallic complexes represented by Formula 401 and Formula 402 below. M(L 401 ) xc1 (L 402 ) xc2 ...Chemical formula 401 [ka] ...Chemical formula 402

[0148] In Chemical Formula 401 and Chemical Formula 402, M is selected from the group consisting of iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), and thulium (Tm); L 401 is selected from the ligands represented by formula 402, xc1 is 1, 2 or 3, and when xc1 is 2 or more, two or more L 401 may be the same or different from each other, L 402 is an organic ligand, xc2 is selected from integers of 0 to 4, and when xc2 is 2 or more, L 402 may be the same or different from each other, X 401 ~X 404 are, independently of each other, nitrogen or carbon, X 401 and X 403 are bonded via a single or double bond, and X 402 and X 404 is attached via a single or double bond, A 401 and A 402 are independent of each other, C5-C 60 Carbocyclic group or C1-C 60 is a heterocyclic group, X 405 is a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*', *-C(Q 411 )(Q 412 )-*', *-C(Q 411 )=C(Q 412 )-*', *-C(Q 411 )=*' or *=C=*' and Q 411 and Q 412 are hydrogen, deuterium, C1-C 20 Alkyl groups, C1-C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; X 406is a single bond, O or S, R 401 and R 402 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C1-C 20 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 401 )(Q 402 )(Q 403 ), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O)2(Q 401 ), and -P(=O)(Q 401 )(Q 402 ), and Q 401 ~Q 403 are independent of each other, C1-C 10 Alkyl groups, C1-C 10 Alkoxy groups, C6-C 20 Aryl groups and C1-C 20 heteroaryl groups, xc11 and xc12 are each independently selected from integers of 0 to 10; In the chemical formula 402, * and *' represent the chemical formula 401The bond position with M is shown.

[0149] According to one example, in formula 402, A 401 and A 402 are independent of each other, The ring structure may be selected from benzene, naphthalene, fluorene, spiro-bifluorene, indene, pyrrole, thiophene, furan, imidazole, pyrazole, thiazole, isothiazole, oxazole, oxazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline, isoquinoline, benzoquinoline, quinoxaline, quinazoline, carbazole, benzimidazole, benzofuran, benzothiophene, isobenzothiophene, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran, and dibenzothiophene.

[0150] According to another example, in formula 402, i) X 401 is nitrogen and X 402 may be carbon, or ii) X 401 and X 402 and may both be nitrogen.

[0151] According to yet another example, in formula 402, R 401 and R 402 are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups and C1-C 20 alkoxy groups; C1-C substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a phenyl group, a naphthyl group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, and a norbornenyl group; 20 Alkyl groups and C1-C 20 alkoxy groups; cyclopentyl group, cyclohexyl group, adamantanyl group, norbornanyl group, norbornenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 selected from the group consisting of an alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group cyclopentyl, cyclohexyl, adamantanyl, norbornanyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl groups, each substituted with at least one of the following: -Si(Q 401 )(Q 402 )(Q 403 ), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O)2(Q 401 ) and -P(=O)(Q 401 )(Q 402 ); Q 401 ~Q 403 are independent of each other, C1-C 10 Alkyl groups, C1-C10 It is selected from, but not limited to, an alkoxy group, a phenyl group, a biphenyl group, and a naphthyl group.

[0152] According to yet another example, in chemical formula 401, when xc1 is 2 or more, two or more L 401 In this case, two A 401 optionally, a linking group, X 407 or two A 402 optionally, a linking group, X 408 (See Compounds PD1 to PD4 and Compound PD7 below.) 407 and X 408 are, independently of each other, a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 413 )-*', *-C(Q 413 )(Q 414 )-*' or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q 414 are, independently of each other, hydrogen, deuterium, C1-C 20 Alkyl groups, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl), but are not limited to these.

[0153] In chemical formula 401, L 402 is any monovalent, divalent, or trivalent organic ligand. For example, L 402 is selected from, but is not limited to, halogens, diketones (e.g., acetylacetonate), carboxylic acids (e.g., picolinate), —C(═O), isonitrile, —CN, and phosphorus-containing groups (e.g., phosphine, phosphite).

[0154] Alternatively, the phosphorescent dopant may be selected from, for example, compounds PD1 to PD25 below, but is not limited thereto. [ka] JPEG0007813089000067.jpg58139 JPEG0007813089000068.jpg33139

[0155] [Fluorescent dopants in the light-emitting layer] The fluorescent dopant may include an arylamine compound or a styrylamine compound. The fluorescent dopant may include a compound represented by the following chemical formula 501: [ka]

[0156] In chemical formula 501, Ar 501 is a substituted or unsubstituted C5-C 60 Carbocyclic groups or substituted or unsubstituted C1-C 60 is a heterocyclic group, L 501 ~L 503 are, independently of each other, substituted or unsubstituted C3-C 10 Cycloalkylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkylene groups, substituted or unsubstituted C3-C 10 Cycloalkenylene group, substituted or unsubstituted C1-C 10 Heterocycloalkenylene group, substituted or unsubstituted C6-C 60 Arylene groups, substituted or unsubstituted C1-C 60 selected from the group consisting of heteroarylene groups, substituted or unsubstituted divalent non-aromatic fused polycyclic groups, and substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic groups; xd1 to xd3 are independently selected from integers of 0 to 3; R 501 and R 502 are, independently of each other, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 is selected from the group consisting of a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused polycyclic heterocyclic group; xd4 may be selected from integers from 1 to 6.

[0157] According to one example, in formula 501, Ar 501 teeth, naphthalene, heptalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, tetracene, picene, perylene, pentaphene, indenoanthracene and indenophenanthrene; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 The ring structure may be selected from the group consisting of naphthalene, heptalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, tetracene, picene, perylene, pentaphene, indenoanthracene, and indenophenanthrene, substituted with at least one selected from the group consisting of an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

[0158] According to another example, in formula 501, L 501 ~L 503 are independent of each other, Phenylene groups, naphthylene groups, fluorenylene groups, spiro-bifluorenylene groups, benzofluorenylene groups, dibenzofluorenylene groups, phenanthrenylene groups, anthracenylene groups, fluoranthenylene groups, triphenylenylene groups, pyrenylene groups, chrysenylene groups, perylenylene groups, pentaphenylene groups, hexacenylene groups, pentacenylene groups, thiophenylene groups, furanylene groups, carbazolylene groups, indolylene groups, isoindolylene groups, benzofuranylene groups, benzothiophenylene groups, dibenzofuranylene groups, dibenzothiophenylene groups, benzocarbazolylene groups, dibenzocarbazolylene groups, dibenzosilolylene groups, pyridinylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20and substituted with at least one selected from the group consisting of an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group. It may also be selected from the group consisting of a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, and a pyridinylene group.

[0159] According to yet another example, in formula 501, R 501 and R 502 are independent of each other, Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, and pyridinyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, chrysenyl groups, perylenyl groups, pentaphenyl groups, hexacenyl groups, pentacenyl groups, thiophenyl groups, furanyl groups, carbazolyl groups, indolyl groups, isoindolyl groups, benzofuranyl groups, benzothiophenyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, benzocarbazolyl groups, dibenzocarbazolyl groups, dibenzosilolyl groups, pyridinyl groups, and -Si(Q 31 )(Q 32 )(Q 33a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group, Q 31 ~Q 33 is C1-C 10 Alkyl groups, C1-C 10 It may be selected from the group consisting of alkoxy, phenyl, biphenyl, terphenyl and naphthyl groups.

[0160] According to yet another example, in chemical formula 501, xd4 may be 2, but is not limited to this.

[0161] For example, the fluorescent dopant may be selected from the following compounds FD1 to FD22. [ka] JPEG0007813089000071.jpg71134 JPEG0007813089000072.jpg50134 JPEG0007813089000073.jpg38134 JPEG0007813089000074.jpg42130 JPEG0007813089000075.jpg39132 JPEG0007813089000076.jpg63133 JPEG0007813089000077.jpg43136 JPEG0007813089000078.jpg4568

[0162] The fluorescent dopant may be selected from the following compounds, but is not limited thereto: [ka] JPEG0007813089000080.jpg46138

[0163] [Electron transport region in organic layer 150] The electron transport region can have i) a single layer structure consisting of a single layer of a single material, ii) a single layer structure consisting of multiple single layers of different materials, or iii) a multilayer structure having multiple layers consisting of multiple different materials.

[0164] The electron transport region may include, but is not limited to, at least one layer selected from a buffer layer, a hole blocking layer, an electron modulating layer, an electron transport layer (ETL), and an electron injection layer.

[0165] For example, the electron transport region may have a structure such as, but not limited to, an electron transport layer / electron injection layer, a hole blocking layer / electron transport layer / electron injection layer, an electron modulation layer / electron transport layer / electron injection layer, or a buffer layer / electron transport layer / electron injection layer, which are stacked in this order from the light emitting layer.

[0166] The electron transport region may include a heterocyclic compound represented by Chemical Formula 1.

[0167] In addition, the electron transport region (e.g., a buffer layer, a hole blocking layer, an electron modulating layer, or an electron transport layer in the electron transport region) may contain a non-metal-containing compound containing at least one π-electron-deficient nitrogen-containing ring in addition to the heterocyclic compound represented by Chemical Formula 1.

[0168] A "π-electron deficient nitrogen-containing ring" is a ring-forming moiety having at least one C1-C '-N=' structure. 60 For example, the "π-electron-deficient nitrogen-containing ring" refers to i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' structure, ii) a heteropolycyclic group in which two or more of the 5- to 7-membered heteromonocyclic groups having at least one *-N=*' structure are condensed with each other, or iii) a heteropolycyclic group in which at least one of the 5- to 7-membered heteromonocyclic groups having at least one *-N=*' structure and at least one C5-C 60 A heteropolycyclic group is a group in which carbocyclic groups and heterocyclic groups are fused together.

[0169] Specific examples of the π-electron deficient nitrogen-containing ring include, but are not limited to, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole.

[0170] For example, the electron transport region may include a compound represented by formula 601 below. [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 ...Chemical formula 601

[0171] In chemical formula 601, Ar 601 is a substituted or unsubstituted C5-C 60 Carbocyclic groups or substituted or unsubstituted C1-C 60is a heterocyclic group, xe11 is 1, 2 or 3, L 601 is a substituted or unsubstituted C3-C 10 Cycloalkylene groups, substituted or unsubstituted C1-C 10 Heterocycloalkylene groups, substituted or unsubstituted C3-C 10 Cycloalkenylene group, substituted or unsubstituted C1-C 10 Heterocycloalkenylene group, substituted or unsubstituted C6-C 60 Arylene groups, substituted or unsubstituted C1-C 60 selected from the group consisting of heteroarylene groups, substituted or unsubstituted divalent non-aromatic fused polycyclic groups, and substituted or unsubstituted divalent non-aromatic fused polycyclic heterocyclic groups; xe1 is selected from integers 0 to 5, R 601 is a substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601 ), -S(=O)2(Q 601 ), and -P(=O)(Q 601 )(Q 602 ), Q 601 ~Q 603 are independent of each other, C1-C 10 Alkyl groups, C1-C 10an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; xe21 is selected from integers from 1 to 5.

[0172] According to one example, xe11 Ar 601 , and xe21 R 601 At least one of the above may contain the above-mentioned π-electron deficient nitrogen-containing ring.

[0173] According to one example, Ar having a ring structure in formula 601 601 teeth, Benzene, naphthalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, tetracene, picene, perylene, pentaphene, indenoanthracene, dibenzofuran, dibenzothiophene, carbazole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, isopropyl a ring structure selected from among thiamidazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32benzene, naphthalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, tetracene, picene, perylene, pentaphene, indenoanthracene, dibenzofuran, dibenzothiophene, carbazole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, picene, a ring structure selected from the group consisting of imidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole; Q 31 ~Q 33 are independent of each other, C1-C 10 Alkyl groups, C1-C 10 It may be selected from the group consisting of alkoxy, phenyl, biphenyl, terphenyl and naphthyl groups.

[0174] In chemical formula 601, when xe11 is 2 or more, 2 or more Ar 601 may be bonded to each other via a single bond.

[0175] According to another example, in formula 601, Ar 601 may have an anthracene structure.

[0176] According to yet another example, the compound represented by chemical formula 601 may be represented by the following chemical formula 601-1: [ka] ...Chemical formula 601-1

[0177] In chemical formula 601-1, X 614 is N or C(R 614 ) and X 615 is N or C(R 615 ) and X 616 is N or C(R 616 ) and X 614 ~X 616 At least one of is N, L 611 ~L 613 are, independently of each other, L 601 Please refer to the explanation regarding xe611 to xe613 are independent of each other and refer to the explanation related to xe1. R 611 ~R 613 are, independently of each other, R 601 Please refer to the explanation regarding R 614 ~R 616 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20 It may be selected from the group consisting of alkoxy, phenyl, biphenyl, terphenyl and naphthyl groups.

[0178] According to one example, in formula 601 and formula 601-1, L 601 , and L 611 ~L 613 are independent of each other, Phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imidazolylene group, pyrazolylene group, thiazolylene group , isothiazolylene groups, oxazolylene groups, isoxazolylene groups, thiadiazolylene groups, oxadiazolylene groups, pyrazinylene groups, pyrimidinylene groups, pyridazinylene groups, triazinylene groups, quinolinylene groups, isoquinolinylene groups, benzoquinolinylene groups, phthalazinylene groups, naphthyridinylene groups, quinoxalinylene groups, quinazolinylene groups, cinnolinylene groups, phenanthridinylene groups, acridinylene groups, phenanthrolinylene groups, phenazinylene groups, benzimidazolylene groups, isobenzothiazolylene groups, benzoxazolylene groups, isobenzoxazolylene groups, triazolylene groups, tetrazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups, and azacarbazolylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazo a phenyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl ...benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolin a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexaphenylene group, or a phenylene group, each of which is substituted with at least one selected from the group consisting of an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; a cenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group,The alkyl group may be selected from, but is not limited to, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group.

[0179] According to another example, in chemical formula 601 and chemical formula 601-1, xe1 and xe611 to xe613 are 0, 1, or 2, independently of one another.

[0180] According to yet another example, in chemical formula 601 and chemical formula 601-1, R 601 , and R 611 ~R 613 are independent of each other, Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 Alkyl groups, C1-C 20Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarba a zolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptyl group, a phenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptyl ... an oxacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group,benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl groups; and -S(=O)2(Q 601 ) and -P(=O)(Q 601 )(Q 602 ); Q 601 and Q 602 For the relevant explanation, please refer to the description in this specification.

[0181] The electron transport region may contain at least one compound selected from the following compounds ET1 to ET36, but is not limited thereto. [ka] JPEG0007813089000083.jpg35131 JPEG0007813089000084.jpg52131 JPEG0007813089000085.jpg57132 JPEG0007813089000086.jpg51137 JPEG0007813089000087.jpg55132 JPEG0007813089000088.jpg58128 JPEG0007813089000089.jpg41132 JPEG0007813089000090.jpg42134 JPEG0007813089000091.jpg45131 JPEG0007813089000092.jpg43130 JPEG0007813089000093.jpg46133

[0182] The electron transport region may also include at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ. [ka]

[0183] The thickness of the buffer layer, hole blocking layer, or electron control layer is, independently of one another, about 2 nm to about 100 nm, for example, about 3 nm to about 30 nm. When the thickness of the buffer layer, hole blocking layer, or electron control layer satisfies the above-mentioned range, excellent hole blocking properties or electron control properties can be obtained without a substantial increase in driving voltage.

[0184] The thickness of the electron transport layer is about 10 nm to about 100 nm, for example, about 15 nm to about 50 nm. When the thickness of the electron transport layer satisfies the above range, satisfactory electron transport properties can be obtained without a substantial increase in driving voltage.

[0185] The electron transport region (for example, the electron transport layer in the electron transport region) may further include a metal-containing material in addition to the materials described above.

[0186] The metal-containing substance may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The metal ion of the alkali metal complex may be selected from Li ion, Na ion, K ion, Rb ion, and Cs ion, and the metal ion of the alkaline earth metal complex may be selected from Be ion, Mg ion, Ca ion, Sr ion, and Ba ion. The ligands coordinated to the metal ions of the alkali metal complex and the alkaline earth metal complex are independently selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but are not limited thereto.

[0187] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, the following compound ET-D1 (lithium quinolate (LiQ)) or the following compound ET-D2. [ka]

[0188] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.

[0189] The electron injection layer may have i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a plurality of single layers made of different materials, or iii) a multilayer structure having multiple layers made of a plurality of different materials.

[0190] The electron injection layer may comprise an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0191] The alkali metal may be selected from the group consisting of Li, Na, K, Rb, and Cs. According to one example, the alkali metal may be Li, Na, or Cs. According to another example, the alkali metal may be Li or Cs, but is not limited thereto.

[0192] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

[0193] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb and Gd.

[0194] The alkali metal compounds, alkaline earth metal compounds and rare earth metal compounds may be selected from oxides and halides (e.g., fluorides, chlorides, bromides, iodides, etc.) of alkali metals, alkaline earth metals and rare earth metals.

[0195] The alkali metal compound may be selected from alkali metal oxides such as LiO, CsO, and KO, and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and KI. According to an example, the alkali metal compound may be selected from, but is not limited to, LiF, LiO, NaF, LiI, NaI, CsI, and KI.

[0196] Alkaline earth metal compounds include BaO, SrO, CaO, and Ba x Sr 1-x O(0 <x<1)、Ba x Ca 1-xIt may be selected from alkaline earth metal compounds such as O(0 < x < 1). According to one example, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but is not limited thereto.

[0197] The rare earth metal compound may be selected from YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3, and TbF3. According to one example, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but is not limited thereto.

[0198] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex contain the ions of the aforementioned alkali metal, alkaline earth metal, and rare earth metal, and the ligands coordinated to the metal ions of the alkali metal complex, alkaline earth metal complex, and rare earth metal complex may be independently selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but are not limited thereto.

[0199] The electron injection layer may consist solely of the aforementioned alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof, or may further contain the organic substance. When the electron injection layer further contains an organic substance, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix composed of the organic substance.

[0200] The thickness of the electron injection layer is about 0.1 nm to about 10 nm, or about 0.3 nm to about 9 nm. When the thickness of the electron injection layer satisfies the above range, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0201] [Second electrode 190] The second electrode 190 is disposed on the organic layer 150. The second electrode 190 is a cathode, which is an electron injection electrode. In this case, the material for the second electrode 190 may be a metal, alloy, electrically conductive compound, or a combination thereof, each having a low work function.

[0202] The second electrode 190 may include at least one selected from the group consisting of lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), indium tin oxide (ITO), and indium zinc oxide (IZO), but is not limited thereto. The second electrode 190 is a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0203] The second electrode 190 may have a single-layer structure, which is a single layer, or a multi-layer structure, which has multiple layers.

[0204] [Organic Light-Emitting Devices 20 to 40] Meanwhile, the organic light emitting device 20 of FIG. 2 has a structure in which a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190 are stacked in this order, the organic light emitting device 30 of FIG. 3 has a structure in which a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 are stacked in this order, and the organic light emitting device 40 of FIG. 4 has a structure in which a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 are stacked in this order.

[0205] For the explanation of the first electrode 110, the organic layer 150, and the second electrode 190 in FIGS. 2 to 4, refer to the explanation of FIG.

[0206] Light generated in the light-emitting layer of the organic layer 150 of the organic light-emitting device 20, 40 is extracted to the outside through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer 210. Light generated in the light-emitting layer of the organic layer 150 of the organic light-emitting device 30, 40 is extracted to the outside through the second electrode 190, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer 220.

[0207] The first capping layer 210 and the second capping layer 220 serve to improve external luminous efficiency by the principle of constructive interference. The first capping layer 210 and the second capping layer 220 may be, independently of each other, an organic capping layer made of an organic material, an inorganic capping layer made of an inorganic material, or a composite capping layer containing an organic material and an inorganic material.

[0208] At least one of the first capping layer 210 and the second capping layer 220 may independently include at least one material selected from the group consisting of carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphine derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine-based compounds may optionally be substituted with a substituent containing at least one element selected from the group consisting of O, N, S, Se, Si, F, Cl, Br, and I. According to one example, at least one of the first capping layer 210 and the second capping layer 220 may independently include an amine-based compound.

[0209] According to another example, at least one of the first capping layer 210 and the second capping layer 220 may independently include a compound represented by formula 201 or a compound represented by formula 202.

[0210] According to yet another example, at least one of the first capping layer 210 and the second capping layer 220 may contain, independently of each other, a compound selected from compounds HT28 to HT33, and compounds CP1 to CP5 listed below, but is not limited to these. [ka]

[0211] The organic light-emitting devices 10 to 40 have been described above with reference to FIGS. 1 to 4, but the organic light-emitting devices according to the present invention are not limited to these.

[0212] Each layer included in the hole transport region, the light emitting layer, and the electron transport region can be formed in a predetermined region using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, ink jet printing, laser printing, and laser induced thermal imaging (LITI).

[0213] When each layer included in the hole transport region, the light emitting layer, and each layer included in the electron transport region are formed by vacuum deposition, the deposition conditions are, for example, a deposition temperature of about 100° C. to about 500° C., a deposition temperature of about 10 -8 torr ~ approx. 10 -3 The vacuum level may be selected within the range of torr and the deposition rate of about 0.001 nm / sec to about 10 nm / sec, taking into consideration the material contained in the layer to be formed and the structure of the layer to be formed.

[0214] When each layer included in the hole transport region, the light-emitting layer, and each layer included in the electron transport region are formed by spin coating, the coating conditions may be selected, for example, within the range of a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to 200°C, taking into consideration the materials included in the layer to be formed and the structure of the layer to be formed. [Example]

[0215] The compound and organic light-emitting device according to one embodiment of the present invention will be described in more detail below with reference to synthesis examples and examples. In the synthesis examples below, when the expression "B was used instead of A" is used, the molar equivalents of A and B are the same.

[0216] [Synthesis example] Synthesis Example 1: Synthesis of Compound 2 [ka]

[0217] Synthesis of intermediate I-1 1.84 g (10 mmol) of cyanuric chloride, 1.22 g (10 mmol) of phenylboronic acid, 1.15 g (1 mmol) of Pd(PPh3), and 4.14 g (30 mmol) of potassium carbonate were dissolved in 100 mL of tetrahydrofuran (THF):HO (2:1) and stirred at 80 °C for 24 h. Distilled water was added to the resulting product, which was then extracted three times with 60 mL of ethyl acetate. The resulting organic layer was dried over MgSO4, and the solvent was evaporated. The residue was purified by silica gel column chromatography to obtain 1.92 g (85% yield) of intermediate I-1. The product was characterized by LC-MS (liquid chromatography-mass spectrometry). C9H5Cl2N3:M + 225.03

[0218] Synthesis of intermediate I-2 2.26 g (10 mmol) of intermediate I-1 was dissolved in 100 mL of THF, and then 10 mL (10 mmol) of 4-fluorophenylmagnesium bromide was added dropwise at 0 °C. The mixture was stirred for 12 hours, starting from 0 °C and then increasing to room temperature. Distilled water was added to the resulting product, which was then extracted three times with 60 mL of ethyl acetate. The resulting organic layer was dried over MgSO4, and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography to obtain 2.14 g (75% yield) of intermediate I-2. The compound produced was identified by LC-MS. C 15 H9ClFN3:M + 285.13

[0219] Synthesis of compound 2 2.85 g (10 mmol) of intermediate I-2, 4.44 g (11 mmol) of diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide, 1.14 g (10 mol%) of Pd(PPh3), and 4.15 g (30 mmol) of K2CO3 were dissolved in 100 mL of THF:HO (2:1) and stirred at 80 °C for 24 hours. The resulting product was cooled to room temperature and extracted three times with 60 mL of ethyl acetate. The resulting organic layer was dried over MgSO4, and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography to obtain 4.06 g (77% yield) of compound 2. The resulting compound was characterized by mass spectrometry (MS) / fast atom bombardment (FAB) and NMR. 1 Confirmed by 1 H NMR. C 33 H 23 FN3OP:M + 527.17

[0220] Synthesis Example 2: Synthesis of Compound 3 In the synthesis of the intermediate I-2, 1.84 g (10 mmol) of cyanuric chloride was used as the starting material, and 20 mL (20 mmol) of 4-fluorophenylmagnesium bromide was added dropwise. The same method as in the synthesis of the compound 2 was used to obtain 3.97 g (73% yield). The compound thus obtained was analyzed by MS / FAB. 1 Confirmed by 1 H NMR. C 33 H 22 F2N3O P :M + 545.14

[0221] Synthesis Example 3: Synthesis of Compound 6 In the synthesis of compound 3, except that 4-bromo-1,2-difluorobenzene (10 mmol) was used instead of 4-fluorophenylmagnesium bromide, 3.60 g (62% yield) of compound 6 was obtained in the same manner as in the synthesis of compound 3. The compound thus obtained was analyzed by MS / FAB. 1 Confirmed by 1 H NMR. C33 H 20 F4N3OP:M + 581.15

[0222] Synthesis Example 4: Synthesis of Compound 17 In the synthesis of the compound 2, 4.71 g (75% yield) of compound 17 was obtained in the same manner as in the synthesis of the compound 2, except that (4-cyanophenyl)boronic acid was used instead of phenylboronic acid, and diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide was used instead of diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide. The compound 17 was analyzed by MS / FAB and NMR. 1 Confirmed by 1 H NMR. C 40 H 26 FN4OP:M + 628.17

[0223] Synthesis Example 5: Synthesis of Compound 30 In the synthesis of the compound 3, except that diphenyl(4-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide was used instead of diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide, 4.78 g of compound 30 was obtained (yield 64%) in the same manner as in the synthesis of the compound 3. The compound produced was analyzed by MS / FAB and 1 Confirmed by 1 H NMR. C 49 H 32 F2N3OP:M + 747.25

[0224] Synthesis Example 6: Synthesis of Compound 78 In the synthesis of the compound 3, except that diphenyl(3-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide was used instead of diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide, 4.49 g (yield 60%) of compound 78 was obtained in the same manner as in the synthesis of the compound 3. The compound produced was analyzed by MS / FAB and 1 Confirmed by 1 H NMR. C 49 H 32 F2N3OP:M + 747.24

[0225] Synthesis Example 7: Synthesis of Compound 98 In the synthesis of the compound 3, except that diphenyl(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)phenyl)phosphine oxide was used instead of diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide, 4.13 g (yield 58%) of compound 98 was obtained in the same manner as in the synthesis of the compound 3. The compound thus produced was analyzed by MS / FAB and 1 Confirmed by 1 H NMR. C 45 H 28 F2N3O2P:M + 711.20

[0226] Synthesis Example 8: Synthesis of Compound 116 In the synthesis of the compound 3, except that 5-phenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[b]phosphindole-5-oxide was used instead of diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide, 3.40 g (yield 55%) of compound 116 was obtained in the same manner as in the synthesis of the compound 3. The compound produced was analyzed by MS / FAB and 1Confirmed by 1 H NMR. C 39 H 24 F2N3OP:M + 619.18

[0227] [Table 1]

[0228] Example 1 Corning 15 Ω / cm substrate and anode 2 A (120 nm) ITO glass substrate was cut to a size of 50 mm × 50 mm × 0.7 mm, ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, then irradiated with ultraviolet light for 30 minutes and exposed to ozone for cleaning, and the glass substrate was then placed in a vacuum deposition apparatus.

[0229] A hole injection layer with a thickness of 60 nm was formed on top of the ITO anode formed on a glass substrate by vacuum deposition of 2-TNATA. Next, a hole transport layer with a thickness of 30 nm was formed on top of the hole injection layer by vacuum deposition of 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB).

[0230] A 30-nm-thick light-emitting layer was formed on top of the hole-transporting layer by co-evaporating the host 9,10-di(2-naphthyl)anthracene (ADN) and the dopant 4,4′-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi) in a weight ratio of 98:2.

[0231] Compound 2 was deposited on the light-emitting layer to a thickness of 30 nm to form an electron transport layer, and then LiF was deposited on the electron transport layer to a thickness of 1 nm to form an electron injection layer. Al was then vacuum-deposited on the electron injection layer to a thickness of 300 nm (negative electrode) to form a LiF / Al electrode, thereby producing an organic light-emitting device. [ka]

[0232] Examples 2 to 8 and Comparative Examples 1 to 3 In Examples 2 to 8, organic light-emitting devices were fabricated using the same method as in Example 1, except that the compounds shown in Table 1 were used instead of Compound 2 when forming the electron transport layer. In Comparative Examples 1 to 3, organic light-emitting devices were fabricated using the same method as in Example 1, except that the following Compound 200, Compound A, and Compound B were used instead of Compound 2 when forming the electron transport layer. [ka] JPEG0007813089000101.jpg4484 JPEG0007813089000102.jpg28108

[0233] For the organic light-emitting devices fabricated in Examples 1 to 8 and Comparative Examples 1 to 3, a current density of 50 mA / cm 2 Device performance (driving voltage, luminance, efficiency) at a current density of 100mA / cm 2 The half-life at room temperature was measured using the following method, and the results are shown in Table 1.

[0234] Efficiency and luminance: Power was supplied by a current-voltage meter (Kethley SMU 236) and measured using a luminance meter PR650. [Table 2]

[0235] As can be seen from Table 1, the organic light-emitting devices of Examples 1 to 8 exhibit excellent IVL characteristics with improved driving voltage and improved efficiency compared to the organic light-emitting devices of Comparative Examples 1 to 3, and in particular, have an outstanding effect in improving lifetime.

[0236] That is, when the compound of the present invention is used as an electron transport material of a device, it exhibits excellent effects in terms of driving voltage, luminance, efficiency and lifespan.

[0237] Although the present invention has been described with reference to synthesis examples and examples, these are merely illustrative, and a person skilled in the art to which the present invention pertains would understand that various modifications and equivalent embodiments are possible. Therefore, the true technical scope of protection of the present invention is determined by the technical spirit of the claims. [Industrial Applicability]

[0238] The heterocyclic compound and the organic light emitting device including the heterocyclic compound of the present invention can be effectively applied to, for example, light emitting related technical fields. [Explanation of symbols]

[0239] 10,20,30,40 Organic light-emitting devices 110 1st electrode 150 Organic layer 190 2nd electrode 210 First capping layer 220 Second Capping Layer

Claims

1. A heterocyclic compound represented by the following chemical formula 1: 【Chemistry 1】 (In the above Chemical Formula 1, X １１ is N, X １２ is C-[(L １２ ) ａ１２ - (R １２ ) ｂ１２ ], X １３ is N, X １４ is C-[(L １４ ) ａ１４ - (R １４ ) ｂ１４ ], X １５ is N, The R １２ and R １４ At least one of the above is a substituted or unsubstituted fluorine-containing C ６ -C １０ carbocyclic groups, n1 is 2, n2 is 1, The sum of n1 and n2 is 3, L １ and L ２ is a substituted or unsubstituted C ６ -C １４ Carbocyclic groups and unsubstituted C ３ -C １２ heterocyclic groups, L １２ and L １４ are each independently a substituted or unsubstituted C ６ -C １０ carbocyclic groups, R １ is a substituted or unsubstituted C ６ -C １０ carbocyclic groups, R １２ , and R １４ are each independently a substituted or unsubstituted C ６ -C １０ Carbocyclic groups and unsubstituted C 3 -C １２ heterocyclic groups, a1 is 0, a2 is selected from the group consisting of integers from 0 to 4; a12 and a14 are each independently selected from integers of 0 to 1; When a1 is 0, *-(L １ ) ａ１ -*' is a single bond, and when a2 is 0, *-(L ２ ) ａ２ -*' is a single bond, and when a12 is 0, *-(L １２ ) ａ１２ -*' is a single bond, and when a14 is 0, *-(L １４ ) ａ１４ -*' is a single bond, When a2 is 2 or more, L is 2 or more ２ are the same or different from each other, and when a12 is 2 or more, two or more L １２ are the same or different from each other, and when a14 is 2 or more, １４ are the same or different from each other, b1 is 1, and b12 and b14 are 1 or 2; When b12 is 2 or more, R is 2 or more １２ are the same as each other, and when b14 is 2 or more, two or more R １４ are identical to each other, The substituted C ６ -C １４ Carbocyclic groups and C ６ -C １０ At least one of the carbocyclic groups is -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C １ -C ６ alkyl groups, * indicates the bond position with the adjacent atom.)

2. L ２ is selected from the monovalent or divalent radicals of benzene, naphthalene, anthracene, fluorene, furan, benzofuran, and dibenzofuran; L １２ , L １４ , R １ , R １２ and R １４ 2. The heterocyclic compound according to claim 1, wherein each of the groups is independently selected from the monovalent or divalent radicals of benzene, naphthalene, phenanthroline, furan, benzofuran, and dibenzofuran.

3. Said L ２ is selected from the group represented by the following formulas 3-3, 3-4, and 3-47: 【Chemistry 2】 【change】 (L above) ２ is selected from the group represented by Chemical Formula 3-3, Chemical Formula 3-4, and Chemical Formula 3-47, Y １ is O or C(Z ３ ) (Z ４ ) and In the chemical formula 3-3, chemical formula 3-4, and chemical formula 3-47, Z １ ~Z ４ are each independently hydrogen, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, C １ -C ６ alkyl groups, d2 is selected from integers of 0 to 2, and when d2 is 2 or more, 2 or more Z １ are identical or different from each other, d3 is selected from integers of 0 to 3, and when d3 is 2 or more, 2 or more Z １ and Z ２ are identical or different from each other, d4 is selected from integers of 0 to 4, and when d4 is 2 or more, 2 or more Z １ and Z ２ are identical or different from each other, * and *' indicate the bond positions to adjacent atoms.)

4. The R １２ and R １４ are each independently selected from the group represented by the following Chemical Formula 5-1 to Chemical Formula 5-3, Chemical Formula 5-14 to Chemical Formula 5-16, Chemical Formula 5-24 to Chemical Formula 5-28, and Chemical Formula 5-76 to Chemical Formula 5-79. The heterocyclic compound according to claim 1, 【Transformation 3】 【change】 【change】 【change】 【change】 (In the above Chemical Formulas 5-1 to 5-3, 5-14 to 5-16, 5-24 to 5-28, and 5-76 to 5-79, Y ３１ is O, Z ３１ ~Z ３２ are each independently hydrogen, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, C １ -C ６ selected from alkyl groups and phenyl groups; e2 is selected from integers of 0 to 2, and when e2 is 2 or more, two or more Z ３２ are identical to each other, e3 is selected from integers of 0 to 3, and when e3 is 2 or more, two or more Z ３１ and Z ３２ are identical to each other, e4 is selected from integers of 0 to 4, and when e4 is 2 or more, two or more Z ３１ and Z ３２ are identical to each other, e5 is selected from integers of 0 to 5, and when e5 is 2 or more, two or more Z ３１ and Z ３２ are identical to each other, e6 is selected from integers of 0 to 6, and when e6 is 2 or more, two or more Z ３１ and Z ３２ are identical to each other, e7 is selected from integers of 0 to 7, and when e7 is 2 or more, two or more Z ３１ are identical to each other, * indicates the bond position with the adjacent atom.)

5. The R １２ and R １４ At least one of the a monovalent radical selected from benzene, naphthalene, phenanthroline, furan, benzofuran, and dibenzofuran; The R １２ and R １４ The heterocyclic compound according to claim 1, wherein at least one of the groups is substituted with at least one -F.

6. The R １２ and R １４ The heterocyclic compound according to claim 1, wherein at least one of the following is selected from the group represented by the following chemical formulas 7-1 to 7-19: 【Chemistry 4】 【change】 (In the above Chemical Formula 7-1 to Chemical Formula 7-19, Z ４１ is hydrogen, f2 is selected from the integers 1 to 2; f3 is selected from the group consisting of integers 1 to 3; f4 is selected from the group consisting of integers 1 to 4; * indicates the bond position with the adjacent atom.)

7. A heterocyclic compound selected from the following compounds 1 to 132. 【Transformation 6】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

8. A first electrode; a second electrode facing the first electrode; an organic layer disposed between the first electrode and the second electrode and including a light-emitting layer; The organic light-emitting device, wherein the organic layer comprises one or more heterocyclic compounds according to claim 1 .

9. the first electrode is an anode; the second electrode is a cathode; the organic layer includes 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 a second electrode; the hole transport region includes a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer, or any combination thereof; The organic light emitting device of claim 8 , wherein the electron transport region comprises a buffer layer, a hole blocking layer, an electron modulating layer, an electron transport layer, an electron injection layer, or any combination thereof.

10. The organic light-emitting device according to claim 9 , wherein the electron transport region comprises the heterocyclic compound.

11. The organic light-emitting device according to claim 9 , wherein the electron transport region includes an electron transport layer, and the electron transport layer includes the heterocyclic compound.

12. The organic light-emitting device according to claim 8 , wherein the light-emitting layer contains the heterocyclic compound.

13. the hole transport region comprises a p-dopant; The organic light emitting device according to claim 9, wherein the LUMO of the p-dopant is −3.5 eV or less.

14. The organic light emitting device according to claim 13, wherein the p-dopant comprises a cyano group-containing compound.

15. the light-emitting layer is a first color light-emitting—first light-emitting layer; i) at least one second light-emitting layer emitting a second color light is further included between the first electrode and the second electrode, or ii) at least one second light-emitting layer emitting a second color light and at least one third light-emitting layer emitting a third color light are further included; a maximum emission wavelength of the first color light, a maximum emission wavelength of the second color light, and a maximum emission wavelength of the third color light are the same or different from each other; The organic light emitting device of claim 8, wherein mixed color light obtained by mixing the first color light and the second color light or mixed color light obtained by mixing the first color light, the second color light, and the third color light is emitted.

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