Novel compound and organic light-emitting device comprising same

Abstract

The present disclosure provides a novel compound and an organic light emitting device comprising the same.

Description

Technical Field

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0163416 filed in the Korean Intellectual Property Office on November 22, 2023, the disclosure of which is incorporated herein by reference in its entirety.

[0003] The present disclosure relates to novel compounds and organic light-emitting devices comprising the same. Background Art

[0004] Generally, organic light emitting diodes (OLEDs) are materials that convert electrical energy into light energy. They have been widely researched and have been shown to have wide viewing angles, excellent contrast, fast response times, excellent brightness, driving voltage, and response speed.

[0005] An organic light-emitting device typically has a structure including an anode, a cathode, and an organic material layer interposed between the anode and cathode. The organic material layer typically has a multilayer structure containing different materials to enhance the efficiency and stability of the organic light-emitting device. For example, the organic material layer may be formed from a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic material layer, and electrons are injected from the cathode into the organic material layer. When the injected holes and electrons meet, excitons are formed, and when the excitons fall back to the ground state, light is emitted.

[0006] There is an ongoing need to develop new organic materials for use in organic light emitting devices as described above.

[0007] [Prior art literature]

[0008] [Patent Document]

[0009] (Patent Document 0001) Korean Unexamined Patent Publication No. 10-2000-0051826 Summary of the Invention

[0010] Technical issues

[0011] An object of the present disclosure is to provide novel compounds and organic light-emitting devices comprising the same.

[0012] Technical Solution

[0013] Provided herein is a compound represented by the following Chemical Formula 1:

[0014] [Chemical Formula 1]

[0015]

[0016] In Chemical Formula 1,

[0017] Each X1is independently N or CH, provided that at least one of X1is N,

[0018] Each X2is independently N or CH, provided that at least one of X2is N,

[0019] Ar1to Ar4are each independently a substituted or unsubstituted C 6-60 aryl, or a substituted or unsubstituted C 2-60 heteroaryl,

[0020] provided that at least one of Ar1to Ar4is a biphenyl substituted with one or two cyano groups, Ar5and Ar6are each independently a substituted or unsubstituted C 6-20 aryl,

[0021] R1and R2are each independently hydrogen or deuterium, and

[0022] n and m are each independently an integer of 0 to 4, provided that n + m is an integer of 1 to 8,

[0023] wherein the compound represented by Chemical Formula 1 does not contain deuterium, or contains at least one deuterium.

[0024] Also provided herein is an organic light emitting device including: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers contains a compound represented by Chemical Formula 1.

[0025] Advantages

[0026] The compound represented by Chemical Formula 1 described above can be used as a material for an organic material layer in an organic light emitting device, and can improve efficiency, achieve a low driving voltage, and / or improve a lifespan characteristic in an organic light emitting device. In particular, the compound represented by Chemical Formula 1 can be used as a hole injection material, a hole transport material, a hole injection and transport material, a light emitting material, an electron transport material, or an electron injection material. BRIEF DESCRIPTION OF DRAWINGS

[0027] Figure 1 An example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 is shown.

[0028] Figure 2 An example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 is shown. DETAILED DESCRIPTION

[0029] Hereinafter, embodiments of the present disclosure will be described in more detail in order to facilitate the understanding of the disclosed subject matter.

[0030] In the present disclosure, the symbol or means a bond to another substituent.

[0031] In the present disclosure, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; an oxidized phosphonic group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; an alkylsulfonyl group; an arylsulfonyl group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylamine group; an aryl phosphine group; and a heterocyclic group including at least one of N, O, and S atoms, or a substituent substituted with two or more substituents connected to each other from among the above exemplified substituents. For example, "a substituent in which two or more substituents are connected to each other" can be a biphenyl group. That is, the biphenyl group can be an aryl group, or it can be interpreted as a substituent formed by connecting two phenyl groups.

[0032] In the present disclosure, the number of carbons of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, it can be a compound having the following structure, but is not limited thereto.

[0033]

[0034] In the present disclosure, the ester group can have a structure in which the oxygen of the ester group can be substituted with a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group can be a compound having the following structural formula, but is not limited thereto.

[0035]

[0036] In the present disclosure, the number of carbons of the imide group is not particularly limited, but is preferably 1 to 25.

[0037] Specifically, the imide group can be a compound having the following structural formula, but is not limited thereto.

[0038]

[0039] In the present disclosure, specific examples of the silyl group include trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyl dimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like, but are not limited thereto.

[0040] In the present disclosure, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

[0041] In the present disclosure, the alkyl group can be linear or branched, and the number of carbons thereof is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbons of the alkyl group is 1 to 20. According to another embodiment, the number of carbons of the alkyl group is 1 to 10. According to still another embodiment, the number of carbons of the alkyl group is 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, iso-hexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

[0042] In the present disclosure, the alkenyl group can be linear or branched, and the number of carbons thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbons of the alkenyl group is 2 to 20. According to another embodiment, the number of carbons of the alkenyl group is 2 to 10. According to still another embodiment, the number of carbons of the alkenyl group is 2 to 6. Specific examples thereof include ethenyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butanedienyl, allyl, 1-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2-diphenylethen-1-yl, 2-phenyl-2-(naphth-1-yl)ethen-1-yl, 2,2-bis(diphenyl-1-yl)ethen-1-yl, stilbenyl, styryl, and the like, but are not limited thereto.

[0043] In the present disclosure, the cycloalkyl group is not particularly limited, but its carbon number is preferably 3 to 60. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

[0044] In the present disclosure, the aryl group is not particularly limited, but its carbon number is preferably 6 to 60, and it may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. As a monocyclic aryl group, the aryl group may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. Polycyclic aryl groups include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, fluorenyl, etc., but not limited thereto.

[0045] In the present disclosure, the fluorenyl group may be substituted, and two substituents may be connected to each other to form a spirocyclic structure. In the case where the fluorenyl group is substituted, etc. However, the structure is not limited thereto.

[0046] In the present disclosure, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as a heteroatom, and the carbon number thereof is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo[omicron] oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, etc., but are not limited thereto.

[0047] In the present disclosure, the aryl group in aralkyl, aralkenyl, alkylaryl, and arylamine is the same as the examples of aryl group as defined above. In the present disclosure, the alkyl group in aralkyl, alkylaryl, and alkylamine is the same as the examples of alkyl group as defined above. In the present disclosure, the heteroaryl group in heteroarylamine can apply to the description of heterocyclyl as defined above. In the present disclosure, the alkenyl group in aralkenyl is the same as the examples of alkenyl group as defined above. In the present disclosure, the description of aryl group as defined above can apply with the difference that arylene is a divalent group. In the present disclosure, the description of heterocyclyl as defined above can apply with the difference that heteroarylene is a divalent group. In the present disclosure, the description of aryl group or cycloalkyl group as defined above can apply with the difference that the hydrocarbon ring is not a monovalent group but is formed by binding two substituents. In the present disclosure, the description of heterocyclyl as defined above can apply with the difference that the heterocyclyl is not a monovalent group but is formed by binding two substituents.

[0048] In Chemical Formula 1, one or more hydrogens can be replaced with deuterium.

[0049] Preferably, Ar1to Ar4are each independently phenyl, biphenyl, terphenyl, quaterphenyl, quinquephenyl, sexiphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, -(biphenyl)-(naphthyl), dibenzofuranyl, dibenzothiophenyl, 9-phenyl-carbazolyl, carbazol-9-yl, pyridyl, -(phenyl)-(pyridyl), benz oxazolyl, benzimidazolyl, benzothiazolyl, -(phenyl)-(benz oxazolyl), -(phenyl)-(benzimidazolyl), or -(phenyl)-(benzothiazolyl).

[0050] wherein Ar1to Ar4are each independently unsubstituted or substituted with at least one deuterium, C 1-5 haloalkyl, C 1-5 haloalkoxy, cyano, or C 6-20 aryl group.

[0051] Preferably, Ar1to Ar4are each independently unsubstituted or substituted with at least one deuterium, trifluoromethyl, trifluoromethoxy, cyano, or phenyl group.

[0052] Preferably, in the definition of Ar1to Ar4, biphenyl substituted with one or two cyano groups is selected from any one of the following each of which does not contain deuterium or contains at least one deuterium:

[0053]

[0054] Preferably, Ar5 and Ar6 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, naphthylnaphthyl, phenanthrenyl, pyrenyl, triphenylene, or fluoranthenyl,

[0055] wherein Ar5 and Ar6 are each independently unsubstituted or substituted with at least one deuterium, C 1-4 Alkyl, C 3-6 Cycloalkyl, cyano, pyridyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzo oxazolyl, benzothiazolyl, -(P=O)(C 1-4 alkyl)2 or -(P=O)(C 6-20 aryl)2 substituted.

[0056] Preferably, Ar5 and Ar6 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, naphthylnaphthyl, phenanthrenyl, pyrenyl, triphenylene, or fluoranthenyl,

[0057] wherein Ar5 and Ar6 are each independently unsubstituted or substituted with at least one deuterium, tert-butyl, cyclohexyl, cyano, pyridyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiophene, The substituted groups are -(P=O)(methyl)2, -(P=O)(phenyl)2 and -(P=O)(phenyl)2.

[0058] Preferably, n+m is an integer from 1 to 4. When n+m is 1, n is 0 and m is 1, or n is 1 and m is 0. When n+m is 2, n is 0 and m is 2, or both n and m are 1, or n is 2 and m is 0. When n+m is 3, n is 0 and m is 3, or n is 1 and m is 2, or n is 2 and m is 1, or n is 3 and m is 0. When n+m is 4, n is 0 and m is 4, or n is 1 and m is 3, or both n and m are 2, or n is 3 and m is 1, or n is 4 and m is 0.

[0059] Representative examples of the compound represented by Chemical Formula 1 are as follows:

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101] Further, according to the present disclosure, there is provided a method for preparing a compound represented by Chemical Formula 1 as shown in the following Reaction Scheme 1.

[0102] [Reaction Scheme 1]

[0103]

[0104] In Reaction Scheme 1, the remaining substituents except Y1 to Y3 are the same as defined above, and Y1 to Y3 are each independently halogen, more preferably bromine or chlorine. More preferably, Y1 is bromine and Y2 is chlorine.

[0105] Steps 1 and 3 of Reaction Scheme 1 are Suzuki coupling reactions, which are preferably performed in the presence of a palladium catalyst and a base, and the reactive group used for the Suzuki coupling reaction can be changed as known in the art. Step 2 of Reaction Scheme 1 is a reaction for replacing halogen with a reactive group of Suzuki coupling reaction, which is preferably performed in the presence of a palladium catalyst and a base.

[0106] The preparation method can be further presented in the Preparation Examples described below.

[0107] Further, according to the present disclosure, there is provided an organic light emitting device including a compound represented by Chemical Formula 1. In one example, the present disclosure provides an organic light emitting device including: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Chemical Formula 1.

[0108] The organic material layer of the organic light emitting device of the present disclosure can have a single layer structure, or it can have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present disclosure can have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as the organic material layer. However, the structure of the organic light emitting device is not limited thereto, and it can include a smaller number of organic layers.

[0109] Further, the organic material layer can include a light emitting layer, wherein the light emitting layer comprises the compound represented by Chemical Formula 1. In particular, the compound according to the present disclosure can be used as a dopant of the light emitting layer.

[0110] Further, the organic layer can include an electron transport layer or an electron injection layer, wherein the electron transport layer or the electron injection layer comprises the compound represented by Chemical Formula 1.

[0111] Further, the electron transport layer, the electron injection layer, or a layer that simultaneously transports and injects electrons comprises the compound represented by Chemical Formula 1.

[0112] Further, the organic layer includes a light emitting layer and an electron transport layer, wherein the electron transport layer can comprise the compound represented by Chemical Formula 1.

[0113] Further, the organic light emitting device according to the present disclosure can be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present disclosure can be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, in the case of the inverted type organic light emitting device, the compound represented by Chemical Formula 1 can be contained in the organic material layer. Figure 1 and Figure 2 The structure of the organic light emitting device according to one embodiment of the present disclosure is illustrated in FIGS. 1 and 2.

[0114] Figure 1 An example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 is illustrated. In such a structure, the compound represented by Chemical Formula 1 can be contained in the organic material layer.

[0115] Figure 2 An example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 is illustrated. In such a structure, the compound represented by Chemical Formula 1 can be contained in at least one layer of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.

[0116] The organic light-emitting device according to the present disclosure can be manufactured using materials and methods known in the art, except that at least one of the organic material layers contains the compound represented by Chemical Formula 1. In addition, when the organic light-emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0117] For example, the organic light-emitting device according to the present disclosure can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting device can be manufactured by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the anode, and then depositing a material that can be used as a cathode on the organic material layer. In addition to such a method, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0118] In addition, when manufacturing an organic light-emitting device, the compound represented by Chemical Formula 1 can be formed into an organic layer by a solution coating method and a vacuum deposition method. The solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0119] In addition to such a method, an organic light emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Publication WO2003 / 012890). However, the manufacturing method is not limited thereto.

[0120] In one example, the first electrode is an anode and the second electrode is a cathode, or alternatively, the first electrode is a cathode and the second electrode is an anode.

[0121] As the anode material, it is generally preferred to use a material with a large work function so that holes can be smoothly injected into the organic material layer. Specific examples of anode materials include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and the like, but are not limited thereto.

[0122] As the cathode material, it is generally preferred to use a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; and the like, but are not limited thereto.

[0123] The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, and therefore has the effect of injecting holes in the anode and an excellent hole injection effect on the light-emitting layer or the light-emitting material, preventing the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and further being excellent in the ability to form a thin film. The HOMO (highest occupied molecular orbital) of the preferred hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metalloporphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, polyaniline and polythiophene conductive polymers, but are not limited thereto.

[0124] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport material is suitably a material having a high hole mobility that can receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include, but are not limited to, organic materials based on arylamines, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions.

[0125] The light-emitting material is preferably a material that can receive holes and electrons transferred from the hole transport layer and the electron transport layer, respectively, and combine the holes and electrons to emit light in the visible light region, and has good quantum efficiency for fluorescence or phosphorescence. Specific examples of the light-emitting material include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; diphenylethylene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo-based compounds. compounds of oxazole, benzothiazole and benzimidazole; polymers based on poly(p-phenylenevinylene) (PPV); spiro compounds; polyfluorene; rubrene; and the like, but are not limited thereto.

[0126] The light-emitting layer can contain a host material and a dopant material. The host material includes fused aromatic ring derivatives, heterocycle-containing compounds, and the like. Specific examples of the fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like. Examples of the heterocycle-containing compounds include carbazole derivatives, diphenyl furan derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

[0127] Examples of the dopant material include aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a substituted or unsubstituted fused aromatic ring derivative having an arylamino group, and examples thereof include pyrene having an arylamino group, anthracene, chrysene, indenopyrene, and the like. The styryl amine compound is a compound in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, in which one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups are substituted or unsubstituted. Specific examples thereof include styryl amine, styryl diamine, styryl triamine, styryl tetraamine, and the like, but are not limited thereto. Further, the metal complex includes iridium complexes, platinum complexes, and the like, but is not limited thereto.

[0128] The electron transport layer is a layer that can receive electrons from the electron injection layer and transport the electrons to the light-emitting layer, and the electron transport material is appropriately a material that can well receive electron injection from the cathode and transfer the electrons to the light-emitting layer, and has a large electron mobility. Specific examples of the electron transport material include an Al complex of 8-hydroxyquinoline; a complex containing Alq3; an organic radical compound; a hydroxyflavone-metal complex; and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to conventional techniques. In particular, appropriate examples of the cathode material are typical materials having a low work function, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum layer or a silver layer.

[0129] The electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound that has the ability to transport electrons, has an effect of injecting electrons from the cathode, and has an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents excitons generated by the light-emitting layer from moving to the hole injection layer, and the ability to form a thin film is also excellent. Specific examples of the electron injection layer include fluorenone, anthraquinone dimethane, biphenylquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylmethane, anthrone, and the like, and derivatives thereof; metal complex compounds; nitrogen-containing 5-membered ring derivatives; and the like, but are not limited thereto. ​​​

[0130] Examples of the metal complex compound include lithium 8-hydroxyquinolate, zinc bis(8-hydroxyquinolate), copper bis(8-hydroxyquinolate), manganese bis(8-hydroxyquinolate), aluminum tris(8-hydroxyquinolate), aluminum tris(2-methyl-8-hydroxyquinolate), gallium tris(8-hydroxyquinolate), beryllium bis(10-hydroxybenzo[h]quinolate), zinc bis(10-hydroxybenzo[h]quinolate), chlorogallium bis(2-methyl-8-quinolinate), gallium bis(2-methyl-8-quinolinate)(o-cresol), aluminum bis(2-methyl-8-quinolinate)(1-naphthol), gallium bis(2-methyl-8-quinolinate)(2-naphthol), etc., but are not limited thereto.

[0131] The organic light emitting device according to the present disclosure can be a top emission type, a bottom emission type, or a double-sided emission type, depending on the materials used.

[0132] In addition, the compound represented by Chemical Formula 1 can be included in an organic solar cell or an organic transistor, in addition to the organic light emitting device.

[0133] The preparation of the compound represented by Chemical Formula 1 and the organic light emitting device including the same will be described in detail in the following examples. However, the examples are presented for the purpose of illustration only, and are not intended to limit the scope of the present disclosure.

[0134] [Examples]

[0135] Example 1: Preparation of Compound 1

[0136]

[0137] Step 1) Preparation of Compound 1-a

[0138] Under a nitrogen atmosphere, 3'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (50 g, 93.2 mmol) and 2-bromo-3-chloro-1,1'-biphenyl (24.9 g, 93.2 mmol) were added to tetrahydrofuran (1000 ml) and the mixture was stirred and refluxed. Then, potassium carbonate (38.6 g, 279.6 mmol) was dissolved in water (39 ml), added thereto and stirred well, and then tetrakis(triphenylphosphine)palladium(0) (3.2 g, 2.8 mmol) was added. After 2 hours of reaction, the reaction mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was added to toluene (1111 mL) and dissolved in toluene, and washed with water twice. Then, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to obtain Compound 1-a (50 g, yield: 90%) as a white solid.

[0139] MS: [M+H] + = 597.2

[0140] Step 3) Preparation of Compound 1

[0141] Under a nitrogen atmosphere, Compound 1-a (50 g, 83.7 mmol) and bis(pinacolato)diboron (21.3 g, 83.7 mmol) were added to 1,4-dioxane (1000 mL) and the mixture was stirred and refluxed. Then, potassium carbonate (53.3 g, 251.2 mmol) was added thereto and stirred well, and then bis(dibenzylideneacetone)palladium(0) (0.5 g, 0.8 mmol) and dicyclohexylphosphine (0.3 g, 1.7 mmol) were added. After 5 hours of reaction, the reaction mixture was cooled to room temperature, the organic layer was filtered to remove the salt, and then the filtered organic layer was distilled. This was added to chloroform (576 mL) and dissolved in chloroform, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to obtain Compound 1-b (35.7 g, yield: 62%) as a white solid.

[0142] MS: [M+H] + = 689.3

[0143] Step 3) Preparation of Compound 1

[0144] Compound 1-b (50 g, 72.6 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (25.3 g, 72.6 mmol) were added to tetrahydrofuran (1000 mL) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (30.1 g, 217.8 mmol) was dissolved in water (30 mL), added thereto, and stirred well, and then tetrakis(triphenylphosphine)palladium(0) (2.5 g, 2.2 mmol) was added. After 1 hour of reaction, the reaction mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was added to toluene (1152 mL) and dissolved in toluene, and washed with water twice. Then, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to obtain compound 1 (51.8 g, yield: 90%) as a white solid.

[0145] MS: [M+H] + = 794.3

[0146] Example 2: Preparation of compound 2

[0147]

[0148] Compound 2 was prepared in the same manner as in the preparation method of compound 1 of Example 1, except that 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 3'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 2-bromo-6-chloro-1,1'-biphenyl was used instead of 2-bromo-3-chloro-1,1'-biphenyl, and 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0149] MS: [M+H] + = 794.3

[0150] Example 3: Preparation of compound 3

[0151]

[0152] Compound 3 was prepared in the same manner as in the preparation of compound 1 of Example 1, except that 2'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was used instead of 3'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, and 1-(4-bromo-3-chlorophenyl)naphthalene was used instead of 2-bromo-3-chloro-1,1'-biphenyl.

[0153] MS: [M+H] + = 844.3

[0154] Example 4: Preparation of compound 4

[0155]

[0156] Compound 4 was prepared in the same manner as in the preparation of compound 1 of Example 1, except that 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0157] MS: [M+H] + = 895.3

[0158] Example 5: Preparation of compound 5

[0159]

[0160] Compound 5 was prepared in the same manner as in the preparation of compound 1 of Example 1, except that 3'-(4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was used instead of 3'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 3-bromo-5-chloro-1,1':3',1"-terphenyl was used instead of 2-bromo-3-chloro-1,1'-biphenyl, and 3-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9-phenyl-9H-carbazole was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0161] MS: [M+H] + = 1035.3

[0162] Example 6: Preparation of compound 6

[0163]

[0164] Compound 6 was prepared in the same manner as in the preparation of compound 1 of Example 1, except that 2-(dibenzo[b,d]furan-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 3'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 2-bromo-6-chloro-1,1'-biphenyl was used instead of 2-bromo-3-chloro-1,1'-biphenyl, and 4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3,4-dicarbonitrile was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0165] MS: [M+H] + = 909.3

[0166] Example 7: Preparation of compound 7

[0167]

[0168] Compound 7 was prepared in the same manner as in the preparation of compound 1 of Example 1, except that 2'-(4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-yl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was used instead of 3'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 1-(3-bromo-4-chlorophenyl)naphthalene was used instead of 2-bromo-3-chloro-1,1'-biphenyl, and 4-chloro-2,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0169] MS: [M+H] + = 919.3

[0170] Example 8: Preparation of compound 8

[0171]

[0172] Compound 8 was prepared in the same manner as in the preparation of compound 1 of example 1, except that 2-([1,1 '-biphenyl]-2-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1 ':2',1 "-terphenyl]-2-yl)-1,3,5-triazine was used instead of 3'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1 '-biphenyl]-4-carbonitrile, 2-bromo-6-chloro-1,1 '-biphenyl was used instead of 2-bromo-3-chloro-1,1 '-biphenyl, and 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1 '-biphenyl]-4-carbonitrile was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0173] MS: [M+H] + = 1022.3

[0174] Example 9: Preparation of compound 9

[0175]

[0176] Compound 9 was prepared in the same manner as in the preparation of compound 1 of example 1, except that 3-(3'-bromo-4'-chloro-[1,1 '-biphenyl]-3-yl)pyrimidine was used instead of 2-bromo-3-chloro-1,1 '-biphenyl.

[0177] MS: [M+H] + = 871.3

[0178] Example 10: Preparation of compound 10

[0179]

[0180] Compound 10 was prepared in the same manner as in the preparation of compound 1 of example 1, except that 4'-(6-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1 '-biphenyl]-2-yl)pyrimidin-4-yl)-[1,1 '-biphenyl]-4-carbonitrile was used instead of 3'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1 '-biphenyl]-4-carbonitrile, 4-bromo-3-chloro-1,1 '-biphenyl was used instead of 2-bromo-3-chloro-1,1 '-biphenyl, and 2-chloro-4,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0181] MS: [M+H] + = 868.3

[0182] Example 11: Preparation of compound 11

[0183]

[0184] Compound 11 was prepared in the same manner as in the preparation of compound 1 of Example 1, except that 2-([1,1':3',1"-terphenyl]-5'-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 3'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 3'-bromo-4'-chloro-5',6'-diphenyl-1,1':2',1"-terphenyl was used instead of 2-bromo-3-chloro-1,1'-biphenyl, and 4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0185] MS: [M+H] + = 1174.4

[0186] Example 12: Preparation of compound 12

[0187]

[0188] Compound 12 was prepared in the same manner as in the preparation of compound 1 of Example 1, except that 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 3'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 2'-bromo-3'-chloro-1,1':4',1"-terphenyl was used instead of 2-bromo-3-chloro-1,1'-biphenyl, and 4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3,5-dicarbonitrile was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0189] MS: [M+H] + = 895.3

[0190] Example 13: Preparation of compound 13

[0191]

[0192] Compound 13 was prepared in the same manner as in the preparation of compound 1 of example 1, except that 2,4-diphenyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine was used instead of 3'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 2-(4'-bromo-5'-chloro-[1,1':3',1"-terphenyl]-3-yl)benzo[d] azole instead of 2-bromo-3-chloro-1,1'-biphenyl, and 3'-(4-chloro-6-phenylpyrimidin-2-yl)-[1,1'-biphenyl]-4-carbonitrile instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0193] MS: [M+H] + = 985.3

[0194] Example 14: Preparation of compound 14

[0195]

[0196] Compound 14 was prepared in the same manner as in the preparation of compound 1 of example 1, except that 2-bromo-3-chloro-1,1'-biphenyl-2',3',4',5',6'-d5 was used instead of 2-bromo-3-chloro-1,1'-biphenyl.

[0197] MS: [M+H] + = 799.3

[0198] Example 15: Preparation of compound 15

[0199]

[0200] Compound 15 was prepared in the same manner as in the preparation of compound 1 of example 1, except that 3'-(4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was used instead of 3'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 4-bromo-2-chloro-1,1'-biphenyl was used instead of 2-bromo-3-chloro-1,1'-biphenyl, and 2,4-di([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0201] MS: [M+H] + = 946.3

[0202] Example 16: Preparation of compound 16

[0203]

[0204] Compound 16 was prepared in the same manner as in the preparation of compound 1 of example 1, except that 3'-(4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was used instead of 3'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, 4-bromo-2-chloro-1,1'-biphenyl was used instead of 2-bromo-3-chloro-1,1'-biphenyl, and 3-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)benzonitrile was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0205] MS: [M+H] + = 819.3

[0206] Example 17: Preparation of compound 17

[0207]

[0208] Compound 17 was prepared in the same manner as in the preparation of compound 1 of Example 1, except that 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 3'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, (4'-bromo-2'-chloro-[1,1'-biphenyl]-4-yl)dimethylphosphine oxide was used instead of 2-bromo-3-chloro-1,1'-biphenyl, and 2'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0209] MS: [M+H] + = 870.3

[0210] Example 18: Preparation of Compound 18

[0211]

[0212] Compound 18 was prepared in the same manner as in the preparation of compound 1 of Example 1, except that 4'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile was used instead of 3'-(4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile, and 4'-bromo-2'-chloro-[1,1'-biphenyl]-4-carbonitrile was used instead of 2-bromo-3-chloro-1,1'-biphenyl.

[0213] MS: [M+H] + = 819.3

[0214] [Experimental Example]

[0215] Experimental Example 1

[0216] A substrate having a thickness of 100 nm was coated with a solution of 0.5 wt% of the compound of Example 1 in chloroform. The ITO (indium tin oxide) of the present invention is put into the distilled water that is wherein dissolved with detergent as the glass substrate of film, and carry out ultrasonic cleaning.Use the product manufactured by Fischer Co. as detergent, and as distilled water, use the distilled water that utilizes the filter manufactured by Millipore Co. to filter twice.After ITO was cleaned 30 minutes, distilled water was used to repeat twice ultrasonic cleaning 10 minutes.After completing with distilled water cleaning, with isopropyl alcohol, acetone and methanol solvent, substrate was carried out ultrasonic cleaning, it was dried, and then transferred to plasma cleaner.In addition, oxygen plasma was used that substrate was cleaned 5 minutes, and then transferred to vacuum deposition device.

[0217] On the thus prepared ITO transparent electrode, the following compound HI-A was thermally vacuum deposited onto To form a hole injection layer, the following compounds HAT and HT-A were sequentially vacuum-deposited on the hole injection layer to a thickness of 100 nm, ...200 nm, 300 nm, 400 nm, 500 nm, 600 nm, 700 nm, 800 nm, 900 nm, 1000 nm, 2000 nm, 3000 nm, 4000 nm and The following compounds BH and BD were vacuum deposited on the hole transport layer at a weight ratio of 25:1. The compound 1 prepared in the previous example 1 and the following compound LiQ were vacuum deposited on the light emitting layer at a weight ratio of 1:1. The thickness of the electron injection and transport layer is formed. Lithium fluoride (LiF) and aluminum are sequentially deposited on the electron injection and transport layer to have a thickness of and to form a cathode.

[0218]

[0219] During the above process, the deposition rate of the organic material is kept at / second to / sec, and the deposition rates of lithium fluoride and aluminum were kept at / second and / sec, and the vacuum degree during deposition was maintained at 5 × 10 -8 Up to 1×10 -7 support, thereby manufacturing an organic light-emitting device.

[0220] Experimental Examples 2 to 18

[0221] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compounds listed in the following Table 1 were used instead of Compound 1.

[0222] Comparison of Experimental Examples 1 and 2

[0223] An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that the compounds listed in Table 1 below were used instead of Compound 1. Compounds ET1 and ET2 used in Table 1 below are as follows.

[0224]

[0225] For the organic light emitting device manufactured above, the driving voltage, luminous efficiency, and color coordinates were measured at a current density of 10 mA / cm 2 , and the time (T90) required for the luminance to decrease to 90% of the initial luminance was measured at a current density of 20 mA / cm 2 . The results are shown in Table 1 below.

[0226] [Table 1]

[0227]

[0228] As shown in Table 1, it was determined that the organic light emitting device using the compound represented by Chemical Formula 1 of the present disclosure exhibited superior characteristics in terms of voltage, efficiency, and lifespan.

[0229] Specifically, Compounds 1 to 17 used in Experimental Examples 1 to 17 were directly connected to a biphenyl group, which was connected between two six-membered heterocyclic groups containing at least one N at the ortho and meta positions, which allowed smooth adjustment of electron mobility. In addition, since the biphenyl group was substituted with an aryl group in the linking group, causing structural distortion, this was advantageous for electron transport. In addition, at least one of Ar1 to Ar4 included a biphenyl group substituted with one or two cyano groups, which allowed smooth adjustment of electron injection and transport characteristics. Accordingly, it was determined that it exhibited superior characteristics in terms of voltage, efficiency, and lifespan compared to Comparative Example 1 used in Comparative Experimental Example 1.

[0230] In addition, it was determined that Compound 18 used in Experimental Example 18 introduced a cyano group substituted on the aryl group in the biphenyl linking group to smoothly adjust electron injection and transport, and thus, compared to Comparative Example 2 used in Comparative Experimental Example 2, in which a cyano group was directly substituted on the linking group, it was possible to improve the efficiency and lifespan characteristics of the organic light emitting device.

[0231] [Explanation of Reference Numerals]

[0232] 1: Substrate 2: Anode

[0233] 3: Light Emitting Layer 4: Cathode

[0234] 5: Hole Injection Layer 6: Hole Transport Layer

[0235] 7: Light Emitting Layer 8: Electron Transport Layer

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] Wherein in Chemical Formula 1, Each X1 is independently N or CH, provided that at least one of X1 is N, Each X2 is independently N or CH, provided that at least one of X2 is N, Ar1 to Ar4 are each independently substituted or unsubstituted C 6-60 aryl, or a substituted or unsubstituted C 2-60 heteroaryl, Provided that at least one of Ar1 to Ar4 is a biphenyl group substituted with one or two cyano groups, Ar5 and Ar6 are each independently substituted or unsubstituted C 6-20 Aryl, R1 and R2 are each independently hydrogen or deuterium, and n and m are each independently an integer from 0 to 4, provided that n+m is an integer from 1 to 8, The compound represented by Chemical Formula 1 does not contain deuterium, or contains at least one deuterium.

2. The compound according to claim 1, wherein Ar1 to Ar4 are each independently phenyl, biphenyl, terphenyl, quaterphenyl, pentyl, sexphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, -(biphenyl)-(naphthyl), dibenzofuran, dibenzothiophene, 9-phenyl-carbazolyl, carbazol-9-yl, pyridyl, -(phenyl)-(pyridyl), benzo oxazolyl, benzimidazolyl, benzothiazolyl, -(phenyl)-(benzo oxazolyl), -(phenyl)-(benzimidazolyl), or -(phenyl)-(benzothiazolyl), wherein Ar1 to Ar4 are each independently unsubstituted or substituted with at least one deuterium, C 1-5 Halogenated alkyl, C 1-5 Haloalkoxy, cyano, or C 6-20 Aryl substitution.

3. The compound according to claim 2, wherein Ar1 to Ar4 are each independently unsubstituted or substituted with at least one deuterium, trifluoromethyl, trifluoromethoxy, cyano, or phenyl group.

4. The compound according to claim 1, In the definitions of Ar1 to Ar4, the biphenyl group substituted with one or two cyano groups is selected from any one of the following groups, each of which does not contain deuterium or contains at least one deuterium:

5. The compound according to claim 1, wherein Ar5 and Ar6 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, naphthylnaphthyl, phenanthrenyl, pyrenyl, triphenylene, or fluoranthenyl, wherein Ar5 and Ar6 are each independently unsubstituted or substituted with at least one deuterium, C 1-4 Alkyl, C 3-6 Cycloalkyl, cyano, pyridyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzo oxazolyl, benzothiazolyl, -(P=O)(C 1-4 alkyl)2, or -(P=O)(C 6-20 aryl)2 substituted.

6. The compound according to claim 1, wherein n+m is an integer from 1 to 4.

7. The compound according to claim 1, wherein: The compound represented by Chemical Formula 1 is any one selected from the following:

8. An organic light-emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 7.

9. The organic light emitting device according to claim 8, wherein: The organic material layer containing the compound is an electron transport layer, an electron injection layer, or a layer that simultaneously transports and injects electrons.

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