Organic compound and organic light-emitting display device using the same

Abstract

The present disclosure relates to an organic compound and an organic light-emitting display device using the same, and more particularly to an organic compound represented by Chemical Formula 1 and a display device using the organic compound. The organic compound represented by the following Chemical Formula 1 according to the present disclosure has excellent electron transport properties and durability, and is used in the electron transport layer of an organic light-emitting element, thereby reducing the driving voltage and improving the luminous efficiency and lifespan. In the following Chemical Formula 1, at least two of X1, X2 and X3 are N, Y1 and Y2 are each independently a substituted or unsubstituted phenylene group or a single bond, and at least one of Ar1 and Ar2 is selected from a substituted or unsubstituted triazine group, a functional group represented by Chemical Formula 2 and a functional group represented by Chemical Formula 3. [Chemical Formula 1]#imgabs0#

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the priority of Korean Patent Application No. 10-2019-0179779 filed in the Korean Intellectual Property Office on December 31, 2019, the disclosure of which is incorporated herein by reference. Technical Field

[0003] The present disclosure relates to an organic compound and an organic light-emitting display device using the same. More particularly, the present disclosure relates to a novel organic compound having excellent electron transport characteristics and durability, and an organic light-emitting display device having high efficiency and long life by applying the organic compound to an organic layer. Background Art

[0004] An organic light emitting display device (OLED) uses an organic light emitting element as a self-luminous element. Therefore, the organic light emitting display device has a simple structure and is easy to manufacture. In addition, since the organic light emitting display device is driven at a low voltage, it is advantageous in terms of power consumption. In addition, the organic light emitting display device has excellent color expression capability, high brightness, wide viewing angle, high response speed, and high contrast. Therefore, the organic light emitting display device is being actively developed as a next-generation display device.

[0005] When voltage is applied to the organic light emitting element, holes injected from the anode and electrons injected from the cathode recombine in the light emitting layer to form excitons. When the excitons transition from an unstable excited state to a stable ground state, the organic light emitting element emits light through an organic light emitting phenomenon.

[0006] Generally, in addition to an anode for supplying holes, a cathode for supplying electrons, and an organic light-emitting layer (EML), an organic light-emitting element also includes various layers for improving light-emitting efficiency and stability. For example, an organic light-emitting element has a structure in which an anode, a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer, an electron transport layer (ETL), and an electron injection layer (EIL) are laminated.

[0007] In recent years, displays using organic light-emitting elements have been enlarged and thinned. According to this trend, displays are required to be driven at low power while having a lifespan and luminous efficiency equal to or greater than that of conventional displays. However, organic compounds used in conventional organic light-emitting elements cannot fully meet the currently required characteristics, such as low-power driving, high luminous efficiency, and long lifespan. Summary of the invention

[0008] In order to achieve high efficiency and long life, the light-emitting layer of the organic light-emitting element needs to be designed so that holes and electrons can be smoothly transferred and the charges injected into the light-emitting layer do not leak to adjacent layers.

[0009] One object of the present disclosure is to provide a specific electron transport material that can be applied to an organic light-emitting display device to improve the luminous efficiency and lifespan and reduce the driving voltage. In addition, another object of the present disclosure is to provide an organic light-emitting display device that uses these materials and thus has high efficiency and long lifespan.

[0010] The objects of the present disclosure are not limited to the above objects, and other objects not mentioned above can be clearly understood by those skilled in the art from the following description.

[0011] According to one aspect of the present disclosure, the organic compound is represented by the following Chemical Formula 1:

[0012] [Chemical formula 1]

[0013]

[0014] Wherein in the above chemical formula 1,

[0015] R1 is selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0016] o is an integer from 0 to 4,

[0017] X1, X2 and X3 are each independently N or C, and at least two of X1, X2 and X3 are N,

[0018] Y1 and Y2 are each independently a substituted or unsubstituted phenylene group or a single bond,

[0019] Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0020] At least one of Ar1 and Ar2 is selected from a substituted or unsubstituted triazine group, a functional group represented by the following Chemical Formula 2, and a functional group represented by the following Chemical Formula 3,

[0021] [Chemical formula 2]

[0022]

[0023] [Chemical formula 3]

[0024] as well as

[0025] In the above chemical formulas 2 and 3,

[0026] Z1 and Z2 are each independently O or S,

[0027] R2, R3 and R4 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0028] p is an integer from 0 to 4,

[0029] q is an integer from 0 to 3, and

[0030] Asterisks represent bonding sites.

[0031] According to another aspect of the present disclosure, an organic light-emitting display device includes a plurality of sub-pixels. At least one of the plurality of sub-pixels includes an organic light-emitting element. The organic light-emitting element includes: an anode; an organic layer disposed on the anode and containing an organic compound represented by Chemical Formula 1; and a cathode disposed on the organic layer.

[0032] In the organic light-emitting display device according to the present disclosure, the organic layer includes the organic compound represented by Chemical Formula 1, so electrons injected from the cathode can be smoothly transferred to the organic light-emitting layer. Therefore, the light emission efficiency and lifespan of the organic light-emitting display device can be improved.

[0033] Additional details of exemplary embodiments are included in the detailed description and accompanying drawings.

[0034] According to the present disclosure, an electron transport organic compound having a specific structure can be provided. The organic compound disclosed in the present disclosure has excellent electron transport properties and high durability. In addition, the organic compound is used for the organic layer of an organic light-emitting display device, specifically the electron transport layer. Therefore, the electrons injected from the cathode can be smoothly transmitted to the organic light-emitting layer. Therefore, a display device that can be driven at a low voltage and has greatly improved luminous efficiency and life can be provided.

[0035] The effects according to the present disclosure are not limited to the above-exemplified contents, and more various effects are included in this specification. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] The above and other aspects, features and other advantages of the present disclosure will be more clearly understood from the following detailed description in conjunction with the accompanying drawings, in which:

[0037] Figure 1 is a schematic cross-sectional view of an organic light emitting display device according to an exemplary embodiment of the present disclosure; and

[0038] Figure 2 yes Figure 1 Magnified view of portion “X” in FIG. DETAILED DESCRIPTION

[0039] By referring to the exemplary embodiments described in detail below and the accompanying drawings, the advantages and features of the present disclosure and the methods for achieving the advantages and features will be clear. However, the present disclosure is not limited to the exemplary embodiments disclosed herein, but will be implemented in various forms. Exemplary embodiments are provided only by way of example so that those skilled in the art can fully understand the disclosure of the present disclosure and the scope of the present disclosure. Therefore, the present disclosure will be limited only by the scope of the appended claims.

[0040] The shapes, sizes, ratios, angles, numbers, etc. shown in the drawings for describing the exemplary embodiments of the present disclosure are merely examples, and the present disclosure is not limited thereto. Throughout the specification, similar reference numerals generally represent similar elements. In addition, in the following description of the present disclosure, the detailed description of known related technologies may be omitted to avoid unnecessarily obscuring the subject matter of the present disclosure. Terms such as "including", "having" and "consisting of..." used herein are generally intended to allow the addition of other components, unless the terms are used together with the term "only". Unless otherwise expressly stated, any reference to the singular may include the plural.

[0041] Components are also interpreted as including ordinary margins of error, even if not explicitly stated.

[0042] When terms such as "on", "over", "below", and "adjacent" are used to describe the positional relationship between two parts, one or more parts may be located between the two parts unless these terms are used together with the terms "immediately" or "directly".

[0043] When an element or layer is referred to as being “on” another element or layer, the other layer or element may be directly on the other element or directly between the other element.

[0044] Although the terms "first", "second", etc. are used to describe various component parts, these components are not limited by these terms. These terms are only used to distinguish one component from another component. Therefore, the first component to be mentioned below can be the second component in the technical concept of the present disclosure.

[0045] Like reference numerals generally refer to like elements throughout the specification.

[0046] The size and thickness of each component shown in the drawings are illustrated for convenience of description, and the present disclosure is not limited to the size and thickness of the illustrated components.

[0047] The features of the various embodiments of the present disclosure may be partially or completely dependent on or combined with each other, and may be technically interlocked and operated in various ways, and the embodiments may be implemented independently of each other or in association with each other.

[0048] As used herein, the term "unsubstituted" means that the hydrogen atom is not substituted or the hydrogen atom is substituted with an isotope selected from protium, deuterium and tritium.

[0049] As used herein, the term "substituted" means that a hydrogen atom or atom group of a compound is replaced by a substituent. For example, the substituent can be selected from C1 to C 30 Alkyl, C2 to C 30 Alkenyl, C2 to C 24 Alkynyl, C3 to C 12 Cycloalkyl, C2 to C 30 Heterocycloalkyl, C7 to C 30 Aralkyl, C6 to C 30 Aryl, C5 to C 30 Heteroaralkyl, C1 to C 30 Alkoxy, C1 to C 30 Alkylamino, C6 to C 30 Arylamino, C7 to C 30 Arylalkylamino, C2 to C 24 Heteroarylamino, C1 to C 30 Alkylsilyl, C6 to C 30 Arylsilyl, C6 to C 30 Aryloxy, halogenated C1 to C 30 An alkyl group, a cyano group, a halogen group, a carboxyl group, a hydroxyl group, a carbonyl group, an amine group, a nitro group, and combinations thereof, but may not be limited thereto.

[0050] As used herein, the term "hetero" means that at least one of carbon atoms constituting a cyclic saturated or unsaturated hydrocarbon is substituted with a heteroatom such as N, O, S and Se.

[0051] As used herein, the term "alkyl" refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon. For example, the alkyl group may include methyl, ethyl, propyl, n-butyl, isobutyl, n-pentyl, hexyl, etc., but may not be limited thereto.

[0052] As used herein, the term "alkenyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having two or more carbon atoms and having at least one C=C bond. For example, the alkenyl group may include vinyl, allyl, isopropenyl, 2-butenyl, etc., but may not be limited thereto.

[0053] As used herein, the term "alkynyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having two or more carbon atoms and having at least one carbon-carbon triple bond. For example, the alkynyl group may include ethynyl, 2-propynyl, etc., but may not be limited thereto.

[0054] As used herein, the term "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon, and may have a form in which two or more rings are simply connected to each other in a side chain form or fused to each other. For example, the aryl group may include phenyl, naphthyl, phenanthrenyl, etc., but may not be limited thereto.

[0055] As used herein, the term "heteroaryl" refers to a monovalent substituent derived from an aromatic hydrocarbon in which at least one carbon in the ring is substituted with a heteroatom such as N, O, S or Se. In addition, the heteroaryl group may have a form in which two or more rings are simply connected to each other in the form of a side chain or fused to each other or to an aryl group. For example, the heteroaryl group may include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a phenanthroline ... oxazine, indolizine, benzothiazolyl, benzo Examples of the group consisting of oxazolyl, benzofuranyl, purinyl, quinolyl, carbazolyl, N-imidazolyl, 2-pyridyl, 2-pyrimidinyl and the like may include, but are not limited to, oxazolyl, benzofuranyl, purinyl, quinolyl, carbazolyl, N-imidazolyl, 2-pyridyl, 2-pyrimidinyl and the like.

[0056] As used herein, the term "aryloxy" refers to a monovalent substituent represented by the general formula ArO-, wherein Ar represents an aryl group. For example, the aryloxy group may include phenyloxy, naphthyloxy, diphenyloxy, etc., but may not be limited thereto.

[0057] As used herein, the term "alkoxy" refers to a monovalent substituent represented by the general formula RO-, wherein R represents a linear alkyl group, a branched alkyl group, or a cycloalkyl group having at least one carbon atom. For example, the alkoxy group may include a methoxy group, an ethoxy group, a n-propoxy group, a tert-butoxy group, an n-butoxy group, etc., but may not be limited thereto.

[0058] As used herein, the term "cycloalkyl" refers to a monovalent substituent derived from a cyclic saturated hydrocarbon having three or more carbon atoms, and may include a polycyclic form containing two or more cyclic saturated hydrocarbons. In addition, the cycloalkyl may include a condensed form of a cyclic group. For example, the cycloalkyl may include a cyclopropyl, a cyclopentyl, a cyclohexyl, a norbornyl, an adamantyl, etc., but may not be limited thereto.

[0059] As used herein, the term "heterocycloalkyl" refers to a monovalent substituent derived from a cyclic saturated hydrocarbon in which at least one carbon atom in the ring is substituted by a heteroatom such as N, O, S or Se, and may include a polycyclic form containing two or more heterocyclic saturated hydrocarbons. For example, the heterocycloalkyl may include morpholinyl, piperazinyl, etc., but may not be limited thereto.

[0060] As used herein, the terms "alkylamine" and "arylamine" refer to amines substituted with alkyl and aryl groups, respectively.

[0061] As used herein, the terms "alkylsilyl", "arylsilyl", "alkoxysilyl" and "cycloalkylsilyl" refer to silyl groups substituted with alkyl, aryl, alkoxy and cycloalkyl groups, respectively.

[0062] In the chemical formulas described herein, "*" refers to a bonding site.

[0063] Hereinafter, the present disclosure will be described with reference to chemical formulae and accompanying drawings.

[0064] According to one aspect of the present disclosure, the organic compound is represented by the following Chemical Formula 1:

[0065] [Chemical formula 1]

[0066]

[0067] In Chemical Formula 1, R1 is selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Preferably, R1 can be selected from hydrogen, unsubstituted C1 to C 10 Alkyl, unsubstituted C6 to C 20 Aryl and unsubstituted C5 to C 20 Heteroaryl.

[0068] In Chemical Formula 1, o is an integer of 0 to 4. For example, o may be 0 or 1.

[0069] In Chemical Formula 1, X1, X2, and X3 are each independently N or C, and at least two of X1, X2, and X3 are N.

[0070] In Chemical Formula 1, Y1 and Y2 are each independently a substituted or unsubstituted phenylene group or a single bond.

[0071] In Chemical Formula 1, Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 In addition, at least one of Ar1 and Ar2 is selected from a substituted or unsubstituted triazine group, a functional group represented by the following chemical formula 2, and a functional group represented by the following chemical formula 3. These functional groups include a sp 2 Hybridizes the nitrogen orbitals, thus increasing the speed of electron movement.

[0072] [Chemical formula 2]

[0073]

[0074] In Chemical Formula 2, Z1 is O or S.

[0075] In Chemical Formula 2, R2 is selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl.

[0076] In Chemical Formula 2, p is an integer of 0 to 4. Preferably, p may be 0 or 1.

[0077] [Chemical formula 3]

[0078]

[0079] In Chemical Formula 3, Z2 is O or S.

[0080] In Chemical Formula 3, R3 and R4 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Preferably, R3 may be hydrogen and R4 may be selected from hydrogen, unsubstituted C1 to C 10 Alkyl and unsubstituted C6 to C 15 Aryl.

[0081] In Chemical Formula 3, q ​​is an integer of 0 to 3. Preferably, q may be 0 or 1.

[0082] For example, in Chemical Formula 1, X1 and X3 may be N, and X2 may be C. For another example, in Chemical Formula 1, X1 may be C, and X2 and X3 may be N.

[0083] For example, in Chemical Formula 1, Ar1 and Ar2 are each independently selected from a functional group represented by the following Chemical Formula A, but may not be limited thereto.

[0084] [Chemical formula A]

[0085]

[0086] In Formula A, each R5 is independently selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl, r is an integer from 0 to 2.

[0087] In addition, each R6 is independently selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 The heteroaryl group, s is an integer from 0 to 5.

[0088] In the above Chemical Formula A, R2, R3, R4, p and q are the same as those defined in Chemical Formulas 2 and 3.

[0089] In Chemical Formula 1, Ar1 and Ar2 may be the same as or different from each other. If Ar1 and Ar2 are different from each other, the organic compound exhibits excellent electron transport characteristics and stability.

[0090] For example, in Chemical Formula 1, at least one of Ar1 and Ar2 may be selected from a functional group represented by the following Chemical Formula B. In this case, the organic compound exhibits excellent electron transport characteristics and durability.

[0091] [Chemical formula B]

[0092]

[0093] In Chemical Formula B, Z1, Z2 and R4 are the same as those defined in Chemical Formulas 2 and 3, and R5 and r are the same as those defined in Chemical Formula A.

[0094] For another example, in Chemical Formula 1, at least one of Ar1 and Ar2 may be selected from a functional group represented by the following Chemical Formula C. In this case, the organic compound exhibits excellent electron transport characteristics and durability.

[0095] [Chemical formula C]

[0096]

[0097] In Chemical Formula C, R4 is the same as defined in Chemical Formula 3.

[0098] In Chemical Formula 1, if one of Ar1 and Ar2 is selected from the functional group represented by Chemical Formula B or C, the other may be selected from the functional group represented by Chemical Formula A, but may not be limited thereto.

[0099] For example, in Chemical Formula 1, X1 and X3 may be N, X2 may be C, and o may be 0. In this case, the organic compound may be quinoxaline represented by the following Chemical Formula 1-1.

[0100] [Chemical formula 1-1]

[0101]

[0102] In Chemical Formula 1-1, Y1, Y2, Ar1, and Ar2 are the same as those defined in Chemical Formula 1.

[0103] Preferably, in Chemical Formula 1-1, one of Ar1 and Ar2 may be selected from the functional group represented by Chemical Formula B, and the other may be selected from the functional group represented by Chemical Formula A. In this case, the organic compound may be selected from the group represented by the following Chemical Formula D.

[0104] [Chemical formula D]

[0105]

[0106]

[0107]

[0108] For example, in Chemical Formula 1-1, Y1 and Y2 are phenylene groups, and at least one of Ar1 and Ar2 may be selected from functional groups represented by the following chemical formulas.

[0109]

[0110] In the above chemical formula, R4 may be a phenyl group, and the organic compound may be selected from the group represented by the following chemical formula E, but may not be limited thereto.

[0111] [Chemical formula E]

[0112]

[0113] For another example, in Chemical Formula 1, X1 may be C, X2 and X3 may be N, and o may be 0. In this case, the organic compound may be quinazoline represented by the following Chemical Formula 1-2.

[0114] [Chemical formula 1-2]

[0115]

[0116] In Chemical Formula 1-2, Y1, Y2, Ar1 and Ar2 are the same as those defined in Chemical Formula 1.

[0117] Preferably, in Chemical Formula 1-2, one of Ar1 and Ar2 may be selected from the functional group represented by Chemical Formula B, and the other may be selected from the functional group represented by Chemical Formula A. In this case, the organic compound may be selected from the group represented by the following Chemical Formula F.

[0118] [Chemical formula F]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124] In Chemical Formula 1-2, Y1 and Y2 are phenylene groups, and at least one of Ar1 and Ar2 may be selected from functional groups represented by the following chemical formulas.

[0125]

[0126] In this case, the organic compound may be selected from the group represented by the following Chemical Formula G, but may not be limited thereto.

[0127] [Chemical formula G]

[0128]

[0129] For another example, in Chemical Formula 1-2, Y1 and Y2 are single bonds, and at least one of Ar1 and Ar2 may be a functional group represented by the following Chemical Formula.

[0130]

[0131] In the above chemical formula, R4 may be a phenyl group, and the organic compound may be selected from the group represented by the following Chemical Formula H, but may not be limited thereto.

[0132] [Chemical formula H]

[0133]

[0134] The organic compound represented by Chemical Formula 1 contains many sp 2 The nitrogen atom of the hybrid orbital can thus accelerate the movement of electrons. Therefore, the organic compound represented by Chemical Formula 1 can be used in organic layers that need to have electron transport properties in various organic electronic devices. For example, the organic compound represented by Chemical Formula 1 can be used in an organic layer disposed between the anode and the cathode of an organic light-emitting display device. For example, the organic compound represented by Chemical Formula 1 can be used in an electron transport layer in an organic layer. In this case, the electron movement speed can be improved, and therefore, the electrons injected from the cathode can be smoothly transferred to the organic light-emitting layer. Therefore, the recombination efficiency of holes and electrons in the organic light-emitting layer can be improved, and the driving power can be reduced.

[0135] The band gap of the organic compound represented by Chemical Formula 1 may be 3.6 eV to 4.1 eV. In this case, if the organic compound is applied to an organic light emitting element, electron transport characteristics may be improved without affecting light emitted from an organic light emitting layer.

[0136] The organic compound represented by Chemical Formula 1 may have a HOMO energy level of -6.4 eV to -5.7 eV and a LUMO energy level of -2.4 eV to -1.8 eV. Therefore, the electron injection barrier is reduced, and electrons and holes can be injected into the organic light-emitting layer in a balanced manner. As a result, the luminous efficiency of the organic light-emitting display device can be improved and the driving voltage can be reduced.

[0137] In addition, the organic compound represented by Chemical Formula 1 has excellent heat resistance. Therefore, it can be used in various organic electronic devices to improve the life span and durability of the devices.

[0138] Hereinafter, an organic light emitting display device according to an exemplary embodiment of the present disclosure will be described with reference to the accompanying drawings.

[0139] Figure 1 is a schematic cross-sectional view of an organic light emitting display device according to an exemplary embodiment of the present disclosure, Figure 2 yes Figure 1 Magnified view of portion “X” in FIG.

[0140] Reference Figure 1 and Figure 2 , the organic light emitting display device 100 includes a substrate 110, a thin film transistor 120, and an organic light emitting element 140. The organic light emitting element 140 includes a red organic light emitting element 140R formed in a red sub-pixel R, a green organic light emitting element 140G formed in a green sub-pixel G, and a blue organic light emitting element 140B formed in a blue sub-pixel B. The organic light emitting elements 140R, 140G, and 140B each include an anode 141, an organic layer, and a cathode 147.

[0141] The organic light-emitting display device 100 may be divided into an active region and an inactive region. In the active region, a plurality of pixels are arranged to display an image. In the active region, pixels each including a light-emitting region for displaying an image and a driving circuit for driving the pixels may be arranged. The inactive region surrounds the active region. The inactive region refers to a region where an image is not substantially displayed and various lines and a printed circuit board 110 for driving the pixels and the driving circuit arranged in the active region are arranged.

[0142] A plurality of pixels may be arranged in a matrix form, and each of the plurality of pixels includes a plurality of sub-pixels. Each sub-pixel is an element for displaying a monochrome color, and includes a light-emitting region in which light is emitted and a non-light-emitting region in which no light is emitted. Each of the plurality of sub-pixels may be any one of a red sub-pixel R, a green sub-pixel G, a blue sub-pixel B, and a white sub-pixel.

[0143] For ease of explanation, Figure 1 Only the red sub-pixel R, the green sub-pixel G, and the blue sub-pixel B among the plurality of sub-pixels are shown, but the present disclosure is not limited thereto. Figure 1 It is shown that the organic light emitting display device 100 according to an exemplary embodiment of the present disclosure is driven in a top emission type. However, the present disclosure is not limited to the top emission type.

[0144] In the following, reference will be made to Figure 1 and Figure 2 Elements of the organic light emitting display device 100 according to an exemplary embodiment of the present disclosure are described in detail.

[0145] The substrate 110 is configured to support various elements of the organic light-emitting display device 100 and may be formed of an insulating material. For example, the substrate 110 may be a glass substrate or a plastic substrate. For example, the plastic substrate 110 may be made of one selected from polyimide, polyethersulfone, polyethylene terephthalate, and polycarbonate, but may not be limited thereto.

[0146] The buffer layer 131 is disposed on the substrate 110 and is used to protect various elements of the organic light-emitting display device 100 from the penetration of oxygen or moisture from the outside. Figure 1 The buffer layer 131 is shown as a single layer, but the buffer layer 131 may be selectively formed as a multilayer as necessary.

[0147] The thin film transistor 120 including the gate electrode 121, the active layer 122, the source electrode 123 and the drain electrode 124 is disposed on the buffer layer 131. Specifically, the active layer 122 is disposed on the substrate 110, and the gate insulating layer 132 for insulating the active layer 122 and the gate electrode 121 is disposed on the active layer 122. In addition, the interlayer insulating layer 133 for insulating the gate electrode 121 from the source electrode 123 and the drain electrode 124 is disposed on the buffer layer 131. The source electrode 123 and the drain electrode 124, each of which is in contact with the active layer 122, are formed on the interlayer insulating layer 133.

[0148] The thin film transistor 120 is formed in each of the red sub-pixel R region, the green sub-pixel G region, and the blue sub-pixel B region. Figure 1Only the driving thin film transistor 120 is shown among various thin film transistors 120 that may be included in the organic light emitting display device 100. In addition, Figure 1 The thin film transistor 120 is shown to have a coplanar structure, but may not be limited thereto. The thin film transistor 120 may have an inverse staggered structure.

[0149] An overcoat layer 134 may be disposed on the thin film transistor 120. The overcoat layer 134 planarizes an upper portion of the substrate 110. The overcoat layer 134 may include a contact hole for electrically connecting the thin film transistor 120 to the anode 141 of the organic light emitting element.

[0150] The organic light emitting element 140 is disposed on the overcoat 134. The organic light emitting element 140 includes a red organic light emitting element 140R disposed in a red sub-pixel R, a green organic light emitting element 140G disposed in a green sub-pixel G, and a blue organic light emitting element 140B disposed in a blue sub-pixel B. The organic light emitting elements 140R, 140G, and 140B each include an anode 141, an organic layer, and a cathode 147. The organic layer is formed of an organic compound represented by Chemical Formula 1. The organic layer includes a hole injection layer 142, a hole transport layer 143, an organic light emitting layer 144, an electron transport layer 145, and an electron injection layer 146, but may not be limited thereto. For example, the organic compound represented by Chemical Formula 1 may be included in the electron transport layer 145 in the organic layer, but may not be limited thereto.

[0151] The anode 141 is disposed on the overcoat 134. The anode 141 is formed of a conductive material having a high work function for supplying holes to the organic light emitting layer 144. The anode 141 may be a transparent conductive layer formed of a transparent conductive oxide (TCO). For example, the anode 141 may be formed of one or more transparent conductive oxides selected from the group consisting of indium tin oxide (ITO), indium zinc oxide (IZO), indium tin zinc oxide (ITZO), tin oxide (SnO2), zinc oxide (ZnO), indium copper oxide (ICO), and aluminum: zinc oxide (Al:ZnO (AZO)), but may not be limited thereto.

[0152] The anode 141 may be formed for each of the red sub-pixel R region, the green sub-pixel G region, and the blue sub-pixel B region, respectively. The bank 135 is provided on the anode 141 and the overcoat 134 to divide the adjacent sub-pixel regions. In addition, the bank 135 may divide the pixel regions each including a plurality of sub-pixel regions. The bank 135 may be formed of an insulating material for insulating the anodes 141 respectively provided in the adjacent sub-pixels. In addition, the bank 135 may be formed as a black bank 135 having high absorbance, thereby suppressing color mixing between adjacent sub-pixels.

[0153] In the organic light-emitting display device 100 driven in a top emission mode, if the anode 141 is formed as a transparent conductive layer, a reflective layer can be formed below the anode 141. The reflective layer can be formed as a conductive layer with excellent reflectivity. Therefore, the reflective layer can reflect the light emitted from the organic light-emitting layer 144 of the organic light-emitting element 140 to the upper part of the organic light-emitting display device 100. For example, the reflective layer can be formed of an aluminum-palladium-copper alloy. The reflective layer can be electrically connected to the source electrode 123 of the thin film transistor 120 through the contact hole in the overcoat layer 134.

[0154] The hole injection layer 142 for injecting holes supplied from the anode 141 into the organic light emitting layer 144 is provided on the anode 141. The hole injection layer 142 is formed of a material for improving the interface characteristics between the anode 141 and the hole transport layer 143 and enabling holes to be smoothly injected into the organic light emitting layer 144.

[0155] For example, the hole injection layer 142 may be formed of one or more compounds selected from the group consisting of HAT-CN (dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10.11-hexanitrile), CuPc (copper phthalocyanine), PEDOT:PSS, NPD (N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-2,2'-dimethylbenzidine), etc., but may not be limited thereto. For another example, the hole injection layer 142 may be formed of radialene compounds each having at least one cyano group (CN) and a fluorine group (F). For example, the radialene compound may include one or more members selected from the group consisting of (2E,2'E,2"E)-2,2',2"-(cyclopropane-1,2,3-triylidene)tris(2-(perfluorophenyl)-acetonitrile), (2E,2'E,2"E)-2,2',2"-(cyclopropane-1,2,3-triylidene)tris(2-(perfluoropyridin-4-yl)-acetonitrile), (2E,2'E,2"E)-2,2',2"-(cyclopropane-1,2,3-triylidene)tris(2-(perfluoropyridin-4-yl)-acetonitrile), 1-(2-(4-cyanoperfluorophenyl)-acetonitrile), (2E,2'E,2"E)-2,2',2"-(cyclopropane-1,2,3-triylidene)tris(2-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-acetonitrile), and (2E,2'E,2"E)-2,2',2"-(cyclopropane-1,2,3-triylidene)tris(2-(2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)phenyl)-acetonitrile), but may not be limited thereto.

[0156] The hole transport layer 143 for smoothly transporting holes from the hole injection layer 142 to the organic light emitting layer 144 is disposed on the hole injection layer 142 .

[0157] For example, the hole transport layer 143 may be selected from N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), NPD, MTDATA, 1,3-bis(N-carbazolyl)benzene (mCP), CuPC, TCTA, tris(trifluorovinyl ether)-tris(4-carbazolyl-9-yl-phenyl)amine (TFV-TCTA), tris[4-(diethylamino)phenyl]amine, N-(biphenyl-4-yl)-9,9-diamine. Dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, tri-p-tolylamine, N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-amine, 4,4'-bis(N-carbazyl)-1,1'-biphenyl (CBP) and 1,1-bis(4-(N,N'-di(p-tolyl)amino)phenyl)cyclohexane (TAPC), but may not be limited thereto.

[0158] The organic light emitting layer 144 is disposed on the hole transport layer 143. The organic light emitting layer 144 emits light by causing electrons and holes therein to recombine. For example, the organic light emitting layer 144 of the blue organic light emitting element 140B emits blue light by causing electrons and holes therein to recombine. The organic light emitting layer 144 is formed by a host and a dopant. The host of the organic light emitting layer 144 is used to transfer energy to the dopant to improve luminous efficiency and color purity. The dopant is a dye organic material added to the host in a small amount. The wavelength of the light to be emitted can be controlled by changing the type of the dopant.

[0159] For example, the host material may be selected from anthracene compounds, indolecarbazole compounds, dibenzothiophene compounds, etc., but may not be limited thereto. Two or more host materials may be mixed and used to further improve light emission efficiency.

[0160] For example, the dopant of the organic light emitting layer 144 for emitting blue light may be selected from (4,6-F2ppy)2Irpic, 1,6-bis(diphenylamine)pyrene, TBPe (tetra(tert-butyl)perylene), m-FIrpic, N-FIrpic, FIrpic, spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO polymer and PPV polymer, but may not be limited thereto. For example, the dopant of the organic light emitting layer 144 for emitting red light may be selected from PIQIr(acac) (bis(1-phenylisoquinoline) iridium acetylacetonate), PQIr(acac) (bis(1-phenylquinoline) iridium acetylacetonate), PQIr (tris(1-phenylquinoline)iridium) and PtOEP (octaethylporphyrin platinum), but may not be limited thereto. For example, the dopant of the organic light emitting layer 144 for emitting green light may be Ir(ppy)3(tris(2-phenylpyridine)iridium(III))(FIrppy), but may not be limited thereto.

[0161] The electron transport layer 145 including the organic compound represented by Chemical Formula 1 is disposed on the organic light emitting layer 144. The electron transport layer 145 accelerates the transport of electrons to the organic light emitting layer 144. The electron transport layer 145 enables electrons supplied from the cathode 147 to be easily transferred to the organic light emitting layer 144. The electron transport layer 145 includes the organic compound represented by Chemical Formula 1, and thus exhibits excellent electron transport characteristics and high durability. Therefore, the organic light emitting display device 100 can have improved luminous efficiency and lifespan, and can be driven at a low voltage.

[0162] [Chemical formula 1]

[0163]

[0164] In Chemical Formula 1, X1, X2, X3, Y1, Y2, Ar1, Ar2, R1 and o are the same as those defined above. Other features of the organic compound represented by Chemical Formula 1 are the same as above, and therefore, redundant descriptions thereof will be omitted.

[0165] The organic compound represented by Chemical Formula 1 accelerates the movement of electrons. Therefore, the recombination efficiency of electrons and holes in the organic light-emitting layer 144 is improved, and thus, the luminous efficiency of the organic light-emitting display device 100 can be improved. The organic compound represented by Chemical Formula 1 has excellent stability. Therefore, the life of the organic light-emitting display device 100 can be improved.

[0166] If necessary, the electron transport layer 145 may further selectively include a compound selected from the following: Liq (8-hydroxyquinolyl-lithium), PBD (2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4- The invention may include, but is not limited to, triazole (TAZ), spiro-PBD, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), and BAlq (bis(2-methyl-8-hydroxyquinolinolato)-4-(phenylphenoxy)aluminum).

[0167] A hole blocking layer may be provided between the organic light emitting layer 144 and the electron transport layer 145. The hole blocking layer blocks the leakage of holes from the organic light emitting layer 144 to the electron transport layer 145, resulting in excellent recombination efficiency of holes and electrons in the organic light emitting layer 144. Therefore, an electron blocking layer may be provided on one surface of the organic light emitting layer 144, and a hole blocking layer may be provided on another surface. In this case, holes injected from the anode 141 and electrons injected from the cathode 147 are captured in the organic light emitting layer 144. Therefore, the recombination efficiency of electrons and holes may be further improved.

[0168] The electron injection layer 146 is disposed on the electron transport layer 145. The electron injection layer 146 enables electrons supplied from the cathode 147 to be smoothly injected into the electron transport layer 145. For example, the electron injection layer 146 may be formed to include one or more of BaF2, LiF, CsF, NaF, Li2O, BaO, Liq (lithium quinoline), and lithium benzoate, but may not be limited thereto.

[0169] The cathode 147 is disposed on the electron injection layer 146. The cathode 147 may be formed of a metal material having a low work function for supplying electrons to the organic light emitting layer 144. For example, the cathode 147 may be formed of a metal material selected from Ca, Ba, Al, Ag, and an alloy containing one or more thereof, but may not be limited thereto.

[0170] Reference Figure 1 , the cathode 147 is not patterned and is formed as a single layer on the anode 141. That is, the cathode 147 is formed as a single layer in the red sub-pixel R region, the green sub-pixel G region, and the blue sub-pixel B region. If the organic light-emitting display device 100 is driven in a top emission type, the cathode 147 may be formed to a very small thickness and thus may be substantially transparent.

[0171] The encapsulation layer is formed on the cathode 147 to inhibit moisture or oxygen from penetrating into the organic light emitting element from the outside. In addition, the encapsulation layer flattens the upper surface of the organic light emitting element. For example, the encapsulation layer can be formed as a thin film by laminating an inorganic layer of an inorganic insulating material and an organic layer of an organic material. For another example, the encapsulation layer can be formed by covering the organic light emitting element with a glass substrate 110 to which a getter sheet is attached and sealing them with a curable resin.

[0172] The organic light-emitting display device according to an exemplary embodiment of the present disclosure includes an organic compound represented by Chemical Formula 1 as an electron transport layer. Therefore, the electrons supplied from the cathode can be effectively transported to the organic light-emitting layer. In addition, the organic compound represented by Chemical Formula 1 has excellent stability. Therefore, the luminous efficiency, brightness and life of the organic light-emitting display device can be improved as a whole and the driving voltage can be reduced. Therefore, according to an exemplary embodiment of the present disclosure, an organic light-emitting display device that can be driven at low power and has high luminous efficiency and long life can be provided.

[0173] Hereinafter, the above-mentioned effects of the present disclosure will be described in more detail with reference to exemplary embodiments and comparative embodiments. However, the following exemplary embodiments are provided for illustrative purposes, but do not limit the scope of the present disclosure.

[0174] [Intermediate Preparation Implementation 1]

[0175]

[0176] 1) Synthesis of intermediate 1

[0177] 100.0 g of 4-bromobenzaldehyde (540.5 mmol), 9.1 g of thiamine hydrochloride (27.0 mmol), 22.6 ml of triethylamine (162.1 mmol), and 165 ml of ethanol were placed in a single-necked round-bottom flask and reacted at room temperature for 1 day under stirring. After the reaction was completed, the solvent was evaporated, and the organic layer was treated with water and ethyl acetate. The treated organic layer was dried over anhydrous magnesium sulfate (MgSO4) and then purified by column chromatography to obtain 68.2 g of a light yellow solid compound (Intermediate 1) (yield: 68.2%).

[0178] 2) Synthesis of Intermediate 2

[0179] 68.1g intermediate 1 (184.0mmol), 18.4g NH4NO3 (230.0mmol), 0.4g Cu(CH3COO)2H2O (1.8mmol), 195ml acetic acid / water (volume ratio of 4:1) were placed in a single-necked round-bottom flask, and heated and reacted under reflux for 1 day under stirring. After the reaction was completed, the reaction product was cooled to room temperature and filtered, and the solid product was then washed with water. Then, 100ml methanol was added thereto, stirred for 30 minutes, filtered and purified to obtain 62.1g light green solid compound (intermediate 2) (yield: 91.7%).

[0180] 3) Synthesis of Intermediate 3

[0181] 62.2g intermediate 2 (169mmol), 18.2g 2-aminoaniline (169mmol), 3.2g p-toluenesulfonic acid (16.9mmol), 3000ml methanol were placed in a single-necked round-bottom flask and reacted for 16 hours under reflux. After the reaction was completed, the reaction product was cooled to room temperature and the solvent was evaporated. Then, 300ml methanol was added thereto, stirred for 30 minutes, and filtered to obtain 73.8g white solid compound (intermediate 3) (yield: 99.2%).

[0182] 4) Synthesis of intermediate 4

[0183] 30g intermediate 3 (68.1mmol) and 55ml tetrahydrofuran are put into a 2-neck round-bottom flask and maintained at -78°C. Then, 2.58ml n-butyl lithium (64.6mmol) is slowly added thereto and maintained at -78°C for 1 hour. 87ml trimethyl borate (81.7mmol) is slowly added thereto and maintained at -78°C for 1 hour. Then, the solution is slowly raised to room temperature in temperature and then reacted for 16 hours under stirring. After adding 2M HCl (aqueous solution) to complete the reaction, water is added and 300ml dichloromethane is used to treat the organic layer twice. The treated organic layer is dried with anhydrous magnesium sulfate (MgSO4). Then, the solvent is removed by filtration and the product obtained is purified by silica gel column chromatography to obtain 21.1g white solid compound (intermediate 4) (yield: 76.4%).

[0184] 5) Synthesis of Intermediate 5

[0185] 21.1g intermediate 4 (52.1mmol), 15.3g 2-chloro-4,6-diphenyl-1,3,5-triazine (23.2mmol), 1.21g tetrakis (triphenylphosphine) palladium [Pd (PPh3) 4] (1.05mmol), 7.29g potassium carbonate (K2CO3) (52.7mmol), 100ml tetrahydrofuran and 50ml water were placed in a single-necked round-bottom flask and reacted at 80°C for 2 hours. After the reaction was completed, the reaction product was cooled to room temperature, water was added thereto, and 300ml chloroform (CHCl3) was used to treat the organic layer twice. The treated organic layer was dried with anhydrous magnesium sulfate (MgSO4). Then, the solvent was removed by filtration, and the resulting compound was purified by silica gel column chromatography. The purified compound was recrystallized with dichloromethane / hexane to obtain 18.7g beige solid compound (intermediate 5) (yield: 60.9%).

[0186] [Intermediate Preparation Implementation 2]

[0187]

[0188] 1) Synthesis of intermediate 6

[0189] 15.0 g 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (32.4 mmol), 12.3 g bis(pinacol)diboron (48.6 mmol), 529 mg Pd(dppf)Cl2.CH2Cl2 (0.647 mmol), 9.53 g potassium acetate (97.1 mmol) and 323 ml distilled water were added. alkane was placed in a single-necked round-bottom flask and reacted at 90°C under reflux for 12 hours. After the reaction was completed, the solvent was removed under reduced pressure. The resulting solid was dissolved in dichloromethane, then filtered through a diatomaceous earth filter and washed with dichloromethane. The solvent was removed under reduced pressure, and the resulting compound was crystallized with methanol to obtain 16.0 g of a solid compound (intermediate 6) (yield: 96.8%).

[0190] 2) Synthesis of intermediate 7

[0191] 7.5g 2,3-dichloroquinoxaline (37.8mmol), 12.2g intermediate 6 (28.0mmol), 1.6g Pd (PPh3) 4 (1.4mmol), 280ml toluene / ethanol (volume ratio 2: 1) and 28ml 2M potassium carbonate (K2CO3) (56mmol) are placed in a single-necked round-bottom flask and reacted under reflux. After the reaction is complete, the reaction product is cooled to room temperature and stirred for 1 hour. The generated solid is filtered and washed with toluene, distilled water and methanol in turn. Then, the product is dried to obtain 10.1g gray solid compound (intermediate 7) (yield: 76.5%).

[0192] [Intermediate Preparation Implementation 3]

[0193]

[0194] 1) Synthesis of intermediate 8

[0195] 11.0g intermediate 7 (23.3mmol), 5.5g (3-chlorophenyl) boronic acid (34.9mmol), 1.3g Pd (PPh3) 4 (1.2mmol), 155ml toluene / ethanol (volume ratio 2: 1) and 23ml 2M potassium carbonate (K2CO3) were placed in a single-necked round-bottom flask and reacted for 12 hours under reflux. After the reaction was completed, the reaction product was cooled to room temperature and stirred for 12 hours. The solid produced was filtered and washed with toluene, distilled water and methanol in turn. Then, the product was dried to obtain 9.6g white solid compound (intermediate 8) (yield: 75.2%).

[0196] [Intermediate Preparation Implementation 4]

[0197]

[0198] 1) Synthesis of intermediate 9

[0199] 30.0 g of 2-amino-4-bromophenol (0.16 mol), 16.2 ml of benzaldehyde (0.16 mol) and 200 ml of ethanol were placed in a single-necked round-bottom flask and reacted at room temperature for 12 hours under stirring. After the reaction was completed, the solvent was removed from the reaction product under reduced pressure to obtain Intermediate 9.

[0200] 2) Synthesis of intermediate 10

[0201] After the intermediate 9 was dissolved in 800 ml of dichloromethane, 30.6 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (0.176 mol) was slowly added thereto at room temperature, and reacted at room temperature for 2 hours under stirring. After the reaction was completed, the reaction product was purified by silica gel column chromatography (dichloromethane) and solidified with methanol to obtain 41.0 g of a solid compound (intermediate 10) (yield: 93.2%).

[0202] 3) Synthesis of intermediate 11

[0203] 20.0g intermediate 10 (73.0mmol), 14.8g (3-chlorophenyl) boronic acid (94.9mmol), 4.2g Pd (PPh3) 4 (3.6mmol), 365ml toluene / ethanol (volume ratio 2: 1) and 110ml 2M potassium carbonate (K2CO3) (219mmol) are placed in a single-necked round-bottom flask and reacted under reflux. After the reaction is completed, the reaction product is cooled to room temperature, and the organic layer is treated with distilled water and dichloromethane. The treated organic layer is dried with anhydrous magnesium sulfate (MgSO4), and then the solvent is removed under reduced pressure. Then, the product is purified by silica gel column chromatography to obtain 21.6g light pink solid compound (intermediate 11) (yield: 96.8%).

[0204] 4) Synthesis of intermediate 12

[0205] 21.6 g of intermediate 11 (70.6 mmol), 26.9 g of bis(pinacol)diboron (106 mmol), 8.1 g of Pd(dppf)Cl2.CH2Cl2 (14.1 mmol), 34.6 g of potassium acetate (353 mmol) and 353 ml of distilled water were added. alkane was placed in a single-necked round-bottom flask and reacted under reflux. After the reaction was completed, the solvent was removed under reduced pressure. The resulting solid was dissolved in dichloromethane, then filtered through a diatomaceous earth filter and washed with dichloromethane. Then, the solvent was removed under reduced pressure, and the resulting product was crystallized with diethyl ether to obtain 21.4 g of a yellow solid compound (intermediate 12) (yield: 76.4%).

[0206] [Intermediate Preparation Implementation 5]

[0207]

[0208] Synthesis of intermediate 13

[0209] 20.0 g of intermediate 10 (72.96 mmol), 20.4 g of bis(pinacol)diboron (80.26 mmol), 2.98 g of Pd(dppf)Cl2.CH2Cl2 (3.65 mmol), 14.3 g of potassium acetate (145.92 mmol) and 730 ml of distilled water were added. Alkane was put into a single-necked round-bottom flask and reacted under reflux at 90° C. for 12 hours. After the reaction was completed, the resulting compound was purified by silica gel column chromatography to obtain 20.5 g of a white solid compound (Intermediate 13) (yield: 87.6%).

[0210] [Intermediate Preparation Implementation 6]

[0211]

[0212] 1) Synthesis of intermediate 14

[0213] 16.5g intermediate 3 (40.7mmol), 5.5g intermediate 13 (17.1mmol), 1.0g Pd (PPh3) 4 (0.9mmol), 5.9g potassium carbonate (K2CO3) (42.8mmol), 200ml tetrahydrofuran and 70ml distilled water were placed in a single-necked round-bottom flask and reacted for 3 hours under reflux. After the reaction was completed, the reaction product was cooled to room temperature, and 200ml ethyl acetate was added thereto to treat the organic layer. The solid obtained by concentrating the treated organic layer was purified by silica gel column chromatography to obtain 3.9g white solid compound (intermediate 14) (yield: 17.3%).

[0214] 2) Synthesis of intermediate 15

[0215] 2.5 g of intermediate 14 (4.5 mmol), 1.7 g of bis(pinacol)diboron (6.8 mmol), 0.2 g of Pd(dppf)Cl2.CH2Cl2 (0.2 mmol), 1.3 g of potassium acetate (13.5 mmol) and 50 ml of distilled water were added. The alkane was placed in a single-necked round-bottom flask and reacted under reflux for 2 hours. After the reaction was completed, the reaction product was cooled to room temperature and filtered through a diatomaceous earth filter. The solid obtained by concentrating the filtered organic layer was purified by silica gel column chromatography to obtain 2.0 g of a white solid compound (intermediate 15) (yield: 73.9%).

[0216] [Intermediate Preparation Implementation 7]

[0217]

[0218] Synthesis of intermediate 16

[0219] 30.0g dibenzo [b, d] furan-4-ylboronic acid (142mmol), 42.2g 2,4-dichloroquinazoline (212mmol), 8.2g Pd (PPh3) 4 (7.1mmol), 710ml toluene / ethanol (volume ratio is 2: 1) and 213ml 2M potassium carbonate (K2CO3) are put into a single-necked round-bottom flask and reacted under reflux. After the reaction is completed, the reaction product is cooled to room temperature and stirred for 1 hour. The solid produced is filtered and washed with toluene, distilled water and methanol successively. Then, the product obtained is dried to obtain 33.8g white solid compound (intermediate 16) (yield: 73.4%).

[0220] [Intermediate Preparation Implementation 8]

[0221]

[0222] Synthesis of intermediate 17

[0223] 31.5g phenanthrene-9-ylboric acid (142mmol), 42.2g 2,4-dichloroquinazoline (212mmol), 8.2g Pd(PPh3)4(7.1mmol), 710ml toluene / ethanol (volume ratio is 2:1) and 213ml 2M potassium carbonate (K2CO3) are put into a single-necked round-bottom flask, and reacted under reflux. After the reaction is complete, the reaction product is cooled to room temperature and stirred for 1 hour. The solid produced is washed with toluene, distilled water and methanol successively. Then, the product obtained is dried to obtain 29.8g white solid compound (intermediate 17) (yield: 61.6%).

[0224] [Intermediate Preparation Implementation Scheme 9]

[0225]

[0226] Synthesis of intermediate 18

[0227] By 10.0g intermediate 13 (31.1mmol), 9.3g 2,4-dichloroquinazoline (46.6mmol), 1.8g Pd (PPh3) 4 (1.5mmol), 156ml toluene / ethanol (volume ratio is 2: 1) and 47ml 2M potassium carbonate (K2CO3) put into single neck round bottom flask, and react under reflux.After reaction is completed, reaction product is cooled to room temperature and stirred for 1 hour.The solid produced is filtered, and washed with toluene, distilled water and methanol successively.Then, dry product therefrom to obtain 5.5g white solid compound (intermediate 18) (yield: 49.5%).

[0228] [Intermediate Preparation Embodiment 10]

[0229]

[0230] Synthesis of intermediate 19

[0231] By 13.5g intermediate 6 (31.1mmol), 9.3g 2,4-dichloroquinazoline (46.6mmol), 1.8g Pd (PPh3) 4 (1.5mmol), 156ml toluene / ethanol (volume ratio is 2:1) and 47ml 2M potassium carbonate (K2CO3) put into single neck round bottom flask, and react under reflux.After reaction is completed, reaction product is cooled to room temperature and stirred 1 hour.The solid produced is filtered, and washed with toluene, distilled water and methanol successively.Then, products therefrom is dried to obtain 5.0g white solid compound (intermediate 19) (productivity: 34.1%).

[0232] [Intermediate Preparation Embodiment 11]

[0233]

[0234] 1) Synthesis of intermediate 20

[0235] 26.2 g of 2-aminophenol (0.24 mol) and 300 ml of methanol were placed in a single-necked round-bottom flask, and 44.6 g of 4-bromobenzaldehyde (0.24 mol) was slowly and separately added thereto at room temperature. After reacting for 1 hour, the reaction product was concentrated under reduced pressure to obtain 66.4 g of a high-viscosity liquid compound (intermediate 20) (yield: 100%).

[0236] 2) Synthesis of Intermediate 21

[0237] 66.4g intermediate 20 (0.24mol) and 1.19L dichloromethane were placed in a single-necked round-bottom flask, and 59.6g DDQ (0.26mol) was added slowly and separately thereto at room temperature and reacted for 1 hour under stirring. After the reaction was completed, the reaction product was filtered through a silica plug, and the filtrate was then concentrated under reduced pressure. The concentrate was purified with ethyl acetate / methanol solvent to obtain 29.7g of a white solid compound (intermediate 21) (yield: 45.2%).

[0238] 3) Synthesis of intermediate 22

[0239] 20.0 g of intermediate 21 (72.96 mmol), 20.4 g of bis(pinacol)diboron (80.26 mmol), 2.98 g of Pd(dppf)Cl2.CH2Cl2 (3.65 mmol), 14.3 g of potassium acetate (145.92 mmol) and 730 ml of distilled water were added. Alkane was put into a single-necked round-bottom flask, and reacted under reflux at 90° C. for 12 hours. The obtained compound was purified by silica gel column chromatography to obtain 20.5 g of a white solid compound (Intermediate 22) (yield: 87.6%).

[0240] [Exemplary embodiment 1]

[0241]

[0242] Synthesis of organic compound 1

[0243] 6.0g intermediate 5 (10.1mmol), 1.60g phenylboric acid (13.1mmol), 0.58g tetrakis (triphenylphosphine) palladium [Pd (PPh3) 4] (0.50mmol), 3.48g potassium carbonate (K2CO3) (25.2mmol), 100ml tetrahydrofuran and 50ml water were placed in a single-necked round-bottom flask and reacted at 80°C for 6 hours. After the reaction was completed, the reaction product was cooled to room temperature, water was added thereto, and 300ml chloroform (CHCl3) was used to treat the organic layer twice. The treated organic layer was dried over anhydrous magnesium sulfate (MgSO4). Then, the solvent was removed by filtration, and the resulting product was purified by silica gel column chromatography. The purified compound was recrystallized with dichloromethane / hexane to obtain 2.0g beige solid compound 1 (yield: 45.2%).

[0244] LC-MS / FAB: m / z = 589.23 (C 41 H 27 N5=589.69)

[0245] [Exemplary embodiment 2]

[0246]

[0247] Synthesis of organic compound 2

[0248] Intermediate 5 was obtained by the same method as in exemplary embodiment 1. Then, 7g of intermediate 5 (11.8mmol), 2.25g of (4-cyanophenyl) boronic acid (15.3mmol), 0.68g of Pd (PPh3) 4 (0.59mmol), 4.07g of potassium carbonate (K2CO3) (29.5mmol), 100ml of tetrahydrofuran and 50ml of water were placed in a single-necked round-bottom flask and reacted at 80°C for 6 hours. After the reaction was completed, the reaction product was cooled to room temperature, water was added thereto, and the organic layer was treated twice with 300ml of chloroform (CHCl3). The treated organic layer was dried with anhydrous magnesium sulfate (MgSO4). Then, the compound obtained by removing the solvent was purified by silica gel column chromatography (hexane: dichloromethane = 2:1). The purified compound was first recrystallized with dichloromethane / hexane, and then secondly recrystallized with toluene to obtain 2.0g of beige solid compound 2 (yield: 27.5%).

[0249] LC-MS / FAB: m / z=614.22 (C 42 H 26 N6=614.70)

[0250] [Exemplary embodiment 3]

[0251]

[0252] Synthesis of organic compound 3

[0253] 2.0g intermediate 15 (3.3mmol), 1.1g 2-chloro-4,6-diphenyl-1,3,5-triazine (4.0mmol), 0.2g Pd (PPh3) 4 (0.2mmol), 1.4g potassium carbonate (K2CO3) (9.9mmol), 40ml toluene, 10ml ethanol and 10ml water were placed in a single-necked round-bottom flask and then reacted under reflux for 12 hours. After the reaction was completed, the reaction product was cooled to room temperature and filtered. The filtered solid was heated and dissolved in 50ml chlorobenzene and filtered through a silica pad. The filtrate was stirred and the generated solid was filtered to obtain 1.0g solid compound 3 (yield: 43.3%).

[0254] LC-MS / FAB: m / z=706.25 (C 48 H 30 N6O=706.79)

[0255] [Exemplary embodiment 4]

[0256]

[0257] Synthesis of organic compound 4

[0258] 5.0g intermediate 7 (10.6mmol), 4.2g (1,1'-biphenyl) -3-ylboronic acid (21.2mmol), 0.6g Pd (PPh3) 4 (0.5mmol), 71ml toluene / ethanol (volume ratio of 2: 1) and 11ml 2M potassium carbonate (K2CO3) were placed in a single-necked round-bottom flask and reacted for 3 hours under reflux. After the reaction was completed, distilled water was added thereto at room temperature. Then, the organic layer was treated with dichloromethane, and the treated organic layer was dried with anhydrous sodium sulfate (Na2SO4). Then, the solvent was removed by filtering under reduced pressure. The obtained solid was dissolved in chloroform and purified by silica gel column chromatography. 300ml methanol was added to the purified product and solidified for 12 hours under stirring to obtain 4.5g solid compound 4 (yield: 72.0%).

[0259] LC-MS / FAB: m / z = 589.23 (C 41 H 27 N5=589.69)

[0260] [Exemplary embodiment 5]

[0261]

[0262] Synthesis of organic compound 5

[0263] 5.5g intermediate 8 (10.0mmol), 1.6g (4-cyanophenyl) boronic acid (20.0mmol), 0.3g bis (dibenzylideneacetone) palladium (Pd (dba) 2) (0.5mmol), 0.4g 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (S-Phos) (1.0mmol), 6.3g potassium phosphate (K3PO4) (3.0mmol) and 50ml toluene / distilled water (volume ratio is 1:1) are placed in a single-necked round-bottom flask and reacted for 7 hours under reflux. After the reaction is completed, the reaction product is cooled to room temperature and stirred for 12 hours. The generated solid is filtered and washed with toluene, distilled water and acetone in sequence, and then dried. The dried solid is dissolved in 200ml chlorobenzene under reflux, then filtered through a diatomaceous earth filter, and washed with heated chlorobenzene. The filtrate is cooled to room temperature and then stirred for 12 hours. The generated solid was filtered and washed with acetone and methanol in sequence to obtain 2.0 g of white solid Compound 5 (yield: 32.5%).

[0264] LC-MS / FAB: m / z=614.22 (C 42 H 26 N6=614.70)

[0265] [Exemplary embodiment 6]

[0266]

[0267] Synthesis of organic compound 6

[0268] 10.1g intermediate 8 (21.4mmol), 11.9g intermediate 12 (30.0mmol), 0.61g Pd (dba) 2 (1.0mmol), 0.51g S-Phos (2.1mmol), 13.7g potassium phosphate (K3PO4) (64.2mmol) and 107ml toluene / distilled water (volume ratio of 1: 1) were placed in a single-necked round-bottom flask and reacted under reflux. After the reaction was completed, the organic layer was treated with distilled water and dichloromethane at room temperature. The treated organic layer was dried with anhydrous sodium sulfate (Na2SO4), and then the solvent was removed under reduced pressure. Then, the compound obtained by purification by silica gel column chromatography was dissolved in toluene under reflux, and slowly cooled to room temperature. The produced solid was filtered and dried to obtain 2.56g white solid compound 6 (yield: 17.1%).

[0269] LC-MS / FAB: m / z = 706.25 (C 48 H 30 N6O=706.79)

[0270] [Exemplary embodiment 7]

[0271]

[0272] Synthesis of organic compound 7

[0273] 7.0g intermediate 16 (21.2mmol), 10.2g intermediate 13 (31.8mmol), 1.2g Pd (PPh3) 4 (1.1mmol), 106ml toluene / ethanol (volume ratio of 2: 1) and 32ml 2M potassium carbonate (K2CO3) were placed in a single-necked round-bottom flask and reacted under reflux. After the reaction was completed, the reaction product was cooled to room temperature and stirred for 1 hour. The resulting solid was filtered and washed with toluene, distilled water and acetone in sequence, and then dried. The dried solid was dissolved in chlorobenzene under reflux, then filtered through a diatomaceous earth filter, washed with chlorobenzene and stirred at room temperature. The resulting solid was filtered and washed with acetone to obtain 4.2g white solid compound 7 (yield: 41.4%).

[0274] LC-MS / FAB: m / z = 489.15 (C 33 H 19 N3O2=489.52)

[0275] [Exemplary embodiment 8]

[0276]

[0277] Synthesis of organic compound 8

[0278] 4.4g intermediate 17 (12.7mmol), 6.1g intermediate 13 (19.1mmol), 0.7g Pd (PPh3) 4 (0.6mmol), 64ml toluene / ethanol (volume ratio of 2: 1) and 13ml 2M potassium carbonate (K2CO3) were mixed in a single-necked round-bottom flask and reacted for 1 hour under reflux. After the reaction was completed, the reaction product was cooled to room temperature and stirred for 1 hour. The resulting solid was filtered and washed with toluene, distilled water and acetone in sequence, and then dried. The dried solid was dissolved in 300ml chlorobenzene under reflux, then filtered through a diatomaceous earth filter, and washed with heated chlorobenzene. Then, the solvent was removed under reduced pressure. The resulting solid was solidified with methanol / ethyl acetate, filtered and washed with methanol to obtain 3.6g white solid compound 8 (yield: 56.7%).

[0279] LC-MS / FAB: m / z = 499.17 (C 35 H 21 N3O=499.56)

[0280] [Exemplary embodiment 9]

[0281]

[0282] Synthesis of organic compound 9

[0283] 3.5g intermediate 18 (9.8mmol), 3.1g dibenzo [b, d] furan-4-yl boronic acid (14.7mmol), 0.57g Pd (PPh3) 4 (0.49mmol), 49ml toluene / ethanol (volume ratio of 2: 1) and 15ml 2M potassium carbonate (K2CO3) (29.3mmol) were placed in a single-necked round-bottom flask and reacted under reflux. After the reaction was completed, the reaction product was cooled to room temperature and stirred for 1 hour. The resulting solid was filtered and washed with toluene, distilled water and methanol in sequence, and then dried. The dried solid was dissolved in chlorobenzene under reflux, then filtered through a diatomaceous earth filter, washed with chlorobenzene, and then stirred again at room temperature. The resulting solid was filtered and washed with acetone to obtain 2.5g white solid compound 9 (yield: 52.7%).

[0284] LC-MS / FAB: m / z = 489.15 (C 33 H 19 N3O2=489.52)

[0285] [Exemplary embodiment 10]

[0286]

[0287] Synthesis of organic compound 10

[0288] 5.0g intermediate 19 (10.6mmol), 5.1g intermediate 22 (15.9mmol), 0.6g Pd (PPh3) 4 (0.5mmol), 53ml toluene / ethanol (volume ratio of 2: 1) and 11ml 2M potassium carbonate (K2CO3) were placed in a single-necked round-bottom flask and reacted for 1 hour under reflux. After the reaction was completed, the reaction product was cooled to room temperature and stirred for 1 hour. The resulting solid was filtered and washed with toluene, distilled water and acetone / dichloromethane (volume ratio of 9: 1) and then dried. The dried solid was dissolved in 1000ml chlorobenzene under reflux, then filtered through a diatomaceous earth filter and washed with heated chlorobenzene. The filtrate was cooled to room temperature and stirred for 1 hour. The resulting solid was filtered and washed with 100ml methanol to obtain 3.8g white solid compound 10 (yield: 56.8%).

[0289] LC-MS / FAB: m / z = 630.22 (C 42 H 26 N6O=630.70)

[0290] [Manufacturing of organic light-emitting devices]

[0291] Organic light emitting elements were manufactured using organic compounds 1 to 10 prepared according to exemplary embodiments 1 to 10. Specifically, an ITO substrate including a reflective layer at its lower portion was prepared and then cleaned with UV / O3. The washed substrate was installed in a vacuum deposition chamber. Then, at about 10 -7 The hole injection layer is sequentially deposited by evaporation from a heated boat under vacuum. Hole transport layer Organic light emitting layer Electron transport layer Electron injection layer and cathode

[0292] As a hole injection layer, 97 wt % of a compound represented by the following chemical formula I and 3 wt % of a compound represented by the following chemical formula II were used. As a hole transport layer, a compound represented by the following chemical formula II was used. In addition, the compounds represented by the following chemical formulas III and IV were mixed at a ratio of 2: 1 and used as a host material. In addition, a compound represented by the following chemical formula V was used as a dopant to deposit an organic light-emitting layer (weight ratio of host: dopant = 85: 15). As an electron transport layer, organic compounds 1 to 10 prepared according to exemplary embodiments 1 to 10 were used. As an electron injection layer, LiF was used, and as a cathode, Al was used.

[0293] After the deposition of the above materials is completed, the substrate is moved from the deposition chamber to a drying box to form a film. Then, an encapsulation layer is formed using a UV-curable epoxy resin and a moisture absorbent.

[0294]

[0295] [Comparative Embodiment 1]

[0296] The organic light emitting element was manufactured by the same method as in the above-described manufacturing embodiment, except that an organic compound represented by the following Chemical Formula VI was used as an electron transport layer.

[0297] [Chemical Formula VI]

[0298]

[0299] [Comparative Embodiment 2]

[0300] The organic light emitting element was manufactured by the same method as in the above-described manufacturing embodiment, except that an organic compound represented by the following Chemical Formula VII was used as an electron transport layer.

[0301] [Chemical Formula VII]

[0302]

[0303] [Comparative Embodiment 3]

[0304] The organic light emitting element was manufactured by the same method as in the above-described manufacturing embodiment, except that an organic compound represented by the following Chemical Formula VIII was used as an electron transport layer.

[0305] [Chemical Formula VIII]

[0306]

[0307] [Experimental implementation plan]

[0308] The organic light emitting elements manufactured based on the compounds according to Exemplary Embodiments 1 to 10 and Comparative Embodiments 1 to 3 were evaluated in terms of driving voltage, luminous efficiency, and lifespan. A current source (KEITHLEY) and a photometer (PR650) were used at 10 mA / cm 2 The driving voltage and efficiency were measured at a current density of 10 mA / cm 2 The lifetime (T95) was evaluated by the time taken until the luminance of the organic light emitting element dropped by 5% of the initial luminance when the organic light emitting element was driven at a current density of 1.3 Å. The measurement results of driving voltage, efficiency and lifetime are shown in Table 1 below.

[0309] [Table 1]

[0310]

[0311]

[0312]

[0313] Referring to Table 1, it can be seen that the organic light emitting elements according to exemplary embodiments 1 to 10 are greatly improved in efficiency and lifespan compared to the organic light emitting elements according to comparative embodiments 1 to 3. In addition, it can be seen that the driving voltage of the organic light emitting elements according to exemplary embodiments 1 to 10 is equal to or lower than the driving voltage of the organic light emitting elements according to comparative embodiments 1 to 3. Therefore, it can be seen that the light emitting organic elements according to exemplary embodiments 1 to 10 can be driven at a low voltage.

[0314] According to the above experimental results, the organic compound represented by Chemical Formula 1 according to the exemplary embodiment of the present disclosure has excellent electron transport properties and heat resistance. In addition, it can be applied to the electron transport layer of the organic light-emitting element, thereby helping to improve the luminous efficiency and life of the organic light-emitting display device. In addition, it can reduce the driving voltage, and thus can achieve low-power driving.

[0315] Exemplary embodiments of the present disclosure may also be described as follows:

[0316] According to one aspect of the present disclosure, the organic compound is represented by the following Chemical Formula 1:

[0317] [Chemical formula 1]

[0318]

[0319] In the above chemical formula 1, R1 is selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0320] o is an integer from 0 to 4.

[0321] X1, X2 and X3 are each independently N or C, and at least two of X1, X2 and X3 are N,

[0322] Y1 and Y2 are each independently a substituted or unsubstituted phenylene group or a single bond,

[0323] Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0324] At least one of Ar1 and Ar2 is selected from a substituted or unsubstituted triazine group, a functional group represented by the following Chemical Formula 2, and a functional group represented by the following Chemical Formula 3,

[0325] [Chemical formula 2]

[0326]

[0327] [Chemical formula 3]

[0328] as well as

[0329] In the above chemical formulas 2 and 3,

[0330] Z1 and Z2 are each independently O or S,

[0331] R2, R3 and R4 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0332] p is an integer from 0 to 4, and

[0333] q is an integer from 0 to 3.

[0334] In the above Chemical Formula 1, Ar1 and Ar2 may each be independently selected from a functional group represented by the following Chemical Formula A:

[0335] [Chemical formula A]

[0336]

[0337] In the above chemical formula A, R5 can be selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0338] r can be an integer from 0 to 2,

[0339] R6 can be selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0340] s can be an integer from 0 to 5, and

[0341] R2, R3, R4, p and q may be the same as those defined in Chemical Formulas 2 and 3 above.

[0342] At least one of Ar1 and Ar2 may be selected from a functional group represented by the following Chemical Formula B:

[0343] [Chemical formula B]

[0344]

[0345] In the above Chemical Formula B, R5 and r may be the same as those defined in the above Chemical Formula A, and

[0346] Z1, Z2 and R4 may be the same as those defined in Chemical Formulas 2 and 3 above.

[0347] In the above Chemical Formula 1, Ar1 and Ar2 may be different from each other.

[0348] The organic compound represented by the above Chemical Formula 1 may be selected from organic compounds represented by the following Chemical Formula 1-1 or 1-2:

[0349] [Chemical formula 1-1]

[0350]

[0351] [Chemical formula 1-2]

[0352]

[0353] In the above Chemical Formulae 1-1 and 1-2, Y1, Y2, Ar1, and Ar2 may be the same as those defined in the above Chemical Formula 1, respectively.

[0354] In the above Chemical Formula 1-1, Y1 and Y2 may be phenylene groups, and at least one of Ar1 and Ar2 may be selected from functional groups represented by the following chemical formulas:

[0355]

[0356] In the above chemical formula, R4 may be the same as defined in the above Chemical Formula 3.

[0357] In the above Chemical Formula 1-2, Y1 and Y2 may be phenylene groups, and at least one of Ar1 and Ar2 may be selected from functional groups represented by the following chemical formulas:

[0358]

[0359] In the above Chemical Formula 1-2, Y1 and Y2 may be a single bond, and at least one of Ar1 and Ar2 may be a functional group represented by the following Chemical Formula:

[0360]

[0361] In the above chemical formula, R4 may be the same as defined in the above Chemical Formula 3.

[0362] The band gap of the organic compound may be 3.6 eV to 4.1 eV.

[0363] The organic compound has a HOMO energy level of -6.4 eV to -5.7 eV and a LUMO energy level of -2.4 eV to -1.8 eV.

[0364] According to another aspect of the present disclosure, an organic light-emitting display device includes a plurality of sub-pixels. At least one of the plurality of sub-pixels includes an organic light-emitting element. The organic light-emitting element includes an anode, an organic layer disposed on the anode and containing an organic compound represented by Chemical Formula 1, and a cathode disposed on the organic layer.

[0365] [Chemical formula 1]

[0366] as well as

[0367] In the above Chemical Formula 1, R1 is selected from hydrogen, deuterium, substituted or unsubstituted C1 to C10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0368] o is an integer from 0 to 4.

[0369] X1, X2 and X3 are each independently N or C, and at least two of X1, X2 and X3 are N,

[0370] Y1 and Y2 are each independently a substituted or unsubstituted phenylene group or a single bond,

[0371] Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0372] At least one of Ar1 and Ar2 is selected from a substituted or unsubstituted triazine group, a functional group represented by the following Chemical Formula 2, and a functional group represented by the following Chemical Formula 3,

[0373] [Chemical formula 2]

[0374]

[0375] [Chemical formula 3]

[0376] as well as

[0377] In the above chemical formulas 2 and 3,

[0378] Z1 and Z2 are each independently O or S,

[0379] R2, R3 and R4 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0380] p is an integer of 0-4, and q is an integer of 0-3.

[0381] The organic layer may include an organic light emitting layer disposed on the anode, and an electron transport layer disposed on the organic light emitting layer and including the organic compound represented by Chemical Formula 1.

[0382] This application also relates to the following aspects.

[0383] 1. An organic compound represented by the following chemical formula 1:

[0384] [Chemical formula 1]

[0385]

[0386] Wherein in the above chemical formula 1,

[0387] R1 is selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0388] o is an integer from 0 to 4,

[0389] X1, X2 and X3 are each independently N or C, and at least two of X1, X2 and X3 are N,

[0390] Y1 and Y2 are each independently a substituted or unsubstituted phenylene group or a single bond,

[0391] Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0392] At least one of Ar1 and Ar2 is selected from a substituted or unsubstituted triazine group, a functional group represented by the following Chemical Formula 2, and a functional group represented by the following Chemical Formula 3,

[0393] [Chemical formula 2]

[0394]

[0395] [Chemical formula 3]

[0396] as well as

[0397] In the above chemical formulas 2 and 3,

[0398] Z1 and Z2 are each independently O or S,

[0399] R2, R3 and R4 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0400] p is an integer from 0 to 4,

[0401] q is an integer from 0 to 3, and

[0402] Asterisks represent bonding sites.

[0403] 2. The organic compound according to item 1, wherein in the above Chemical Formula 1, Ar1 and Ar2 are each independently selected from a functional group represented by the following Chemical Formula A:

[0404] [Chemical formula A]

[0405] as well as

[0406] In the above chemical formula A, R5 is selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0407] r is an integer from 0 to 2,

[0408] R6 is selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0409] s is an integer from 0 to 5, and

[0410] R2, R3, R4, p and q are the same as those defined in Chemical Formulas 2 and 3 above.

[0411] 3. The organic compound according to item 2, wherein at least one of Ar1 and Ar2 is selected from a functional group represented by the following chemical formula B:

[0412] [Chemical formula B]

[0413] as well as

[0414] In the above Chemical Formula B, R5 and r are the same as those defined in the above Chemical Formula A, and

[0415] Z1, Z2 and R4 are the same as those defined in Chemical Formulae 2 and 3 above.

[0416] 4. The organic compound according to item 1, wherein in the above Chemical Formula 1, Ar1 and Ar2 are different from each other.

[0417] 5. The organic compound according to item 1, wherein the organic compound represented by the above Chemical Formula 1 is selected from the organic compounds represented by the following Chemical Formula 1-1 or 1-2:

[0418] [Chemical formula 1-1]

[0419]

[0420] [Chemical formula 1-2]

[0421] as well as

[0422] In the above Chemical Formulae 1-1 and 1-2, Y1, Y2, Ar1 and Ar2 are respectively the same as those defined in the above Chemical Formula 1.

[0423] 6. The organic compound according to item 5, wherein in the above Chemical Formula 1-1, Y1 and Y2 are phenylene groups, and at least one of Ar1 and Ar2 is selected from the functional groups represented by the following chemical formulas:

[0424] as well as

[0425] In the above chemical formula, R4 is the same as defined in the above Chemical Formula 3.

[0426] 7. The organic compound according to item 5, wherein in the above Chemical Formula 1-2, Y1 and Y2 are phenylene groups, and at least one of Ar1 and Ar2 is selected from the functional groups represented by the following Chemical Formulas:

[0427]

[0428] 8. The organic compound according to item 5, wherein in the above Chemical Formula 1-2, Y1 and Y2 are single bonds, and at least one of Ar1 and Ar2 is a functional group represented by the following Chemical Formula:

[0429] as well as

[0430] In the above chemical formula, R4 is the same as defined in the above Chemical Formula 3.

[0431] 9. The organic compound according to item 1, wherein the band gap of the organic compound is 3.6 eV to 4.1 eV.

[0432] 10. The organic compound according to item 1, wherein the organic compound has a HOMO energy level of -6.4 eV to -5.7 eV and a LUMO energy level of -2.4 eV to -1.8 eV.

[0433] 11. An organic light emitting display device, comprising:

[0434] A plurality of sub-pixels,

[0435] At least one of the plurality of sub-pixels comprises an organic light-emitting element, and the organic light-emitting element comprises:

[0436] anode;

[0437] an organic layer disposed on the anode and including an organic compound represented by Chemical Formula 1; and

[0438] a cathode disposed on the organic layer, and

[0439] [Chemical formula 1]

[0440] as well as

[0441] In the above chemical formula 1,

[0442] R1 is selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0443] o is an integer from 0 to 4,

[0444] X1, X2 and X3 are each independently N or C, and at least two of X1, X2 and X3 are N,

[0445] Y1 and Y2 are each independently a substituted or unsubstituted phenylene group or a single bond,

[0446] Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6 to C 30 Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0447] At least one of Ar1 and Ar2 is selected from a substituted or unsubstituted triazine group, a functional group represented by the following Chemical Formula 2, and a functional group represented by the following Chemical Formula 3,

[0448] [Chemical formula 2]

[0449]

[0450] [Chemical formula 3]

[0451] as well as

[0452] In the above chemical formulas 2 and 3,

[0453] Z1 and Z2 are each independently O or S,

[0454] R2, R3 and R4 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C6 to C 30Aryl and substituted or unsubstituted C3 to C 30 Heteroaryl,

[0455] p is an integer from 0 to 4,

[0456] q is an integer from 0 to 3, and

[0457] Asterisks represent bonding sites.

[0458] 12. The organic light-emitting display device according to item 11, wherein the organic layer includes an organic light-emitting layer disposed on the anode, and an electron transport layer disposed on the organic light-emitting layer and including an organic compound represented by Chemical Formula 1.

[0459] Although the exemplary embodiments of the present disclosure have been described in detail with reference to the accompanying drawings, the present disclosure is not limited thereto and can be presented in many different forms without departing from the technical concept of the present disclosure. Therefore, the exemplary embodiments of the present disclosure are provided for illustrative purposes only and are not intended to limit the technical concept of the present disclosure. The scope of the technical concept of the present disclosure is not limited thereto. Therefore, it should be understood that the above exemplary embodiments are exemplary in all aspects and do not limit the present disclosure. The scope of protection of the present disclosure should be interpreted based on the attached claims, and all technical concepts within their equivalent ranges should be interpreted as falling within the scope of the present disclosure.

Claims

1. An organic compound selected from the group consisting of the following chemical formulas 1-1 or 1-2: [Chemical formula 1-1] [Chemical formula 1-2] as well as In the above chemical formulas 1-1 and 1-2, Y1 and Y2 are each independently phenylene or a single bond, Ar1 and Ar2 are different from each other and are each independently selected from a functional group represented by the following chemical formula A: [Chemical formula A] and only one of Ar1 and Ar2 is selected from the functional group represented by the following Chemical Formula 2 and the functional group represented by the following Chemical Formula 3, [Chemical formula 2] [Chemical formula 3] as well as In the above formula, Z1 and Z2 are each independently O, R2, R3 and R4 are each independently selected from hydrogen, deuterium, C1 to C 10 Alkyl and C6 to C 30 Aryl, p is an integer from 0 to 4, q is an integer from 0 to 3, R5 is selected from C6 to C 30 Aryl, r is 2, and Asterisks represent bonding sites. Provided that the organic compound does not include 2. The organic compound according to claim 1, wherein in Chemical Formula 1-1, Y1 and Y2 are phenylene groups, and one of Ar1 and Ar2 is selected from functional groups represented by the following chemical formulas: as well as In the above chemical formula, R4 is the same as defined in Chemical Formula 3.

3. The organic compound according to claim 1, wherein in Chemical Formula 1-2, Y1 and Y2 are phenylene groups, and one of Ar1 and Ar2 is selected from functional groups represented by the following chemical formulas:

4. The organic compound according to claim 1, wherein in Chemical Formula 1-2, Y1 and Y2 are single bonds, and one of Ar1 and Ar2 is a functional group represented by the following chemical formula: as well as In the above chemical formula, R4 is the same as defined in Chemical Formula 3. The organic compound according to claim 1 , wherein a band gap of the organic compound is 3.6 eV to 4.1 eV. The organic compound according to claim 1 , wherein the organic compound has a HOMO energy level of −6.4 eV to −5.7 eV and a LUMO energy level of −2.4 eV to −1.8 eV.

7. An organic light emitting display device, comprising: A plurality of sub-pixels, At least one of the plurality of sub-pixels comprises an organic light-emitting element, and the organic light-emitting element comprises: anode; an organic layer disposed on the anode and including an organic compound represented by Chemical Formula 1-1 or 1-2; and a cathode disposed on the organic layer, and [Chemical formula 1-1] [Chemical formula 1-2] as well as In the above chemical formulas 1-1 and 1-2, Y1 and Y2 are each independently phenylene or a single bond, Ar1 and Ar2 are different from each other and are each independently selected from a functional group represented by the following chemical formula A: [Chemical formula A] and only one of Ar1 and Ar2 is selected from the functional group represented by the following Chemical Formula 2 and the functional group represented by the following Chemical Formula 3, [Chemical formula 2] [Chemical formula 3] as well as In the above formula, Z1 and Z2 are each independently O, R2, R3 and R4 are each independently selected from hydrogen, deuterium, C1 to C 10 Alkyl and C6 to C 30 Aryl, p is an integer from 0 to 4, q is an integer from 0 to 3, R5 is selected from C6 to C 30 Aryl, r is 2, and Asterisks represent bonding sites. Provided that the organic compound does not include 8 . The organic light emitting display device according to claim 7 , wherein the organic layer comprises an organic light emitting layer disposed on the anode, and an electron transport layer disposed on the organic light emitting layer and comprising an organic compound represented by Chemical Formula 1-1 or 1-2.

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