Compound and organic light-emitting device containing the same

Abstract

The present disclosure provides a heterocyclic compound and an organic light-emitting device including the same.

Description

Technical Field

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of Korean Patent Application No. 10-2018-0135443 filed on November 6, 2018, in the Korean Intellectual Property Office, and Korean Patent Application No. 10-2019-0140737 filed on November 6, 2019, in the Korean Intellectual Property Office, the disclosures of which are incorporated herein by reference in their entirety.

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

[0004] Generally, the organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic materials. Organic light emitting devices using the organic light emitting phenomenon have characteristics such as wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed, and therefore many studies have been conducted.

[0005] An organic light-emitting device generally has a structure including an anode, a cathode, and an organic material layer between the anode and the cathode. The organic material layer generally has a multilayer structure including different materials to enhance the efficiency and stability of the organic light-emitting device. For example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of an organic light-emitting device, if a voltage is applied between 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 each other, excitons are formed, and light is emitted when the excitons fall to the ground state again.

[0006] There is a continuing need to develop materials for organic materials used 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 a compound and an organic light-emitting device including the same.

[0012] Technical Solution

[0013] According to one embodiment of the present disclosure, a compound represented by the following Chemical Formula 1 is provided:

[0014] [Chemical formula 1]

[0015]

[0016] In Chemical Formula 1,

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

[0018] n and m are each independently an integer from 0 to 3, provided that the sum of n and m is 1 or greater, R1 and R2 are each independently a substituted or unsubstituted C 6-10 Aryl,

[0019] L is substituted or unsubstituted C 6-60 arylene, and

[0020] Ar is a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S. 5-60 Heteroaryl or tri(C 6-60 aryl)silyl.

[0021] According to another aspect of the present disclosure, an organic light-emitting device is provided, which includes: a first electrode; a second electrode arranged opposite to the first electrode; and one or more organic material layers arranged between the first electrode and the second electrode, wherein one or more of the organic material layers contains a compound represented by Chemical Formula 1.

[0022] Beneficial Effects

[0023] The compound represented by Chemical Formula 1 can be used as a material of an organic material layer of an organic light-emitting device, and can improve efficiency, achieve low driving voltage and / or improve life characteristics in the 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 THE DRAWINGS

[0024] 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.

[0025] 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, an electron blocking layer 7, a light emitting layer 3, an electron transport layer 8, an electron injection layer 9 and a cathode 4 is shown. DETAILED DESCRIPTION

[0026] Hereinafter, embodiments of the present disclosure will be described in more detail to facilitate understanding of the present invention.

[0027] The present disclosure provides a compound represented by Chemical Formula 1.

[0028] As used in this article, the symbol It refers to the bond to another substituent.

[0029] As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the following: deuterium; halogen group; cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkylthio group; arylthio group; alkylsulfonyl group; arylsulfonyl group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamino group; aralkylamino group; heteroarylamino group; arylamino group; arylphosphino group; and heterocyclic group containing at least one of N, O and S atoms, or unsubstituted or substituted with substituents in which two or more substituents are connected among the substituents exemplified above. For example, "substituents in which two or more substituents are connected" can be biphenyl. That is, the biphenyl group can be an aryl group, or it can also be interpreted as a substituent in which two phenyl groups are connected.

[0030] In the present disclosure, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group may be a group having the following structural formula, but is not limited thereto:

[0031]

[0032] In the present disclosure, the ester group may have a structure in which the oxygen of the ester group may be substituted by 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 may be a group having the following structural formula, but is not limited thereto:

[0033]

[0034] In the present disclosure, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group may be a group having the following structural formula, but is not limited thereto:

[0035]

[0036] In the present disclosure, the silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but is not limited thereto.

[0037] In the present disclosure, the boryl group specifically includes a trimethylboryl group, a triethylboryl group, a tert-butyldimethylboryl group, a triphenylboryl group, and a phenylboryl group, but is not limited thereto.

[0038] In the present disclosure, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0039] In the present disclosure, the alkyl group may be linear or branched, and its carbon number is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the carbon number 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, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-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, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0040] In the present disclosure, the alkenyl group may be linear or branched, and the carbon number thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another embodiment, the carbon number of the alkenyl group is 2 to 10. According to yet another embodiment, the carbon number of the alkenyl group is 2 to 6. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0041] In the present disclosure, the cycloalkyl group is not particularly limited, but its carbon number is preferably 3 to 60. According to one 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 yet 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.

[0042] 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 are not limited thereto.

[0043] 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.

[0044] 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, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, thiazolyl, isothiophene Azolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl and the like, but not limited thereto.

[0045] In the present disclosure, the aryl in aralkyl, aralkenyl, alkylaryl, arylamine and arylsilyl is the same as the aforementioned example of aryl. In the present disclosure, the alkyl in aralkyl, alkylaryl and alkylamine is the same as the aforementioned example of alkyl. In the present disclosure, the heteroaryl in heteroarylamine can apply the aforementioned description of heterocyclic group. In the present disclosure, the alkenyl in aralkenyl is the same as the aforementioned example of alkenyl. In the present disclosure, the aforementioned description of aryl can be applied, except that arylene is a divalent group. In the present disclosure, the aforementioned description of heterocyclic group can be applied, except that heteroarylene is a divalent group. In the present disclosure, the aforementioned description of aryl or cycloalkyl can be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In the present disclosure, the aforementioned description of heterocyclic group can be applied, except that the heterocyclic ring is not a monovalent group but is formed by combining two substituents.

[0046] Preferably, Chemical Formula 1 may be the following Chemical Formula 1-1:

[0047] [Chemical formula 1-1]

[0048]

[0049] In Chemical Formula 1-1,

[0050] X, L, Ar, R1, R2, n and m are the same as defined above.

[0051] Preferably, the sum of n and m may be 1 or 2, and more preferably, the sum of n and m may be 1.

[0052] Preferably, R1 and R2 may be phenyl.

[0053] Preferably, all X's may be N's.

[0054] Preferably, L can be substituted or unsubstituted C 6-20 The arylene group is more preferably a phenylene group.

[0055] Preferably, Ar can be any one selected from the following:

[0056]

[0057] For example, the compound may be selected from the following compounds:

[0058]

[0059]

[0060]

[0061]

[0062] Meanwhile, the compound represented by Chemical Formula 1 may be prepared by a preparation method as shown in the following Reaction Scheme 1.

[0063] [Reaction Scheme 1]

[0064]

[0065] In Reaction Scheme 1, the definitions of the substituents are the same as those described above, and the preparation method can be further presented in the preparation examples described below.

[0066] In addition, the present disclosure provides 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 one or more of the organic material layers includes the compound represented by Chemical Formula 1.

[0067] The organic material layer of the organic light-emitting device of the present disclosure may have a single-layer structure, or it may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present disclosure may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and it may include a smaller number of organic material layers.

[0068] In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer for simultaneous hole injection and transport, wherein the hole injection layer, the hole transport layer, or the layer for simultaneous hole injection and transport may contain the compound represented by Chemical Formula 1.

[0069] In addition, the organic material layer may include a light emitting layer, wherein the light emitting layer may include the compound represented by Chemical Formula 1. In this case, the compound represented by Chemical Formula 1 may be used as a host material in the light emitting layer.

[0070] In addition, the light emitting layer may include two or more types of hosts. When the light emitting layer includes two or more types of hosts, at least one host may be a compound represented by Chemical Formula 1.

[0071] In addition, the organic material layer may include an electron transport layer or an electron injection layer, wherein the electron transport layer or the electron injection layer includes the compound represented by Chemical Formula 1.

[0072] In addition, the electron transport layer, the electron injection layer, or the layer for simultaneous electron transport and electron injection may include the compound represented by Chemical Formula 1.

[0073] In addition, the organic material layer may include a light emitting layer and an electron transport layer, wherein the electron transport layer may include the compound represented by Chemical Formula 1.

[0074] In addition, the organic light-emitting device according to the present disclosure may be a normal organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present disclosure may be an inverted organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

[0075] 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. In such a structure, the compound represented by Chemical Formula 1 may be contained in the light emitting layer.

[0076] 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, an electron blocking layer 7, a light-emitting layer 3, an electron transport layer 8, an electron injection layer 9, and a cathode 4 is shown. In such a structure, the compound represented by Chemical Formula 1 may be contained in at least one of the hole injection layer, the hole transport layer, the electron blocking layer, the light-emitting layer, the electron transport layer, and the electron injection layer, and preferably, it may be contained in the light-emitting layer.

[0077] The organic light-emitting device according to the present disclosure can be manufactured by 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.

[0078] For example, an 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 (e.g., 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, 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.

[0079] 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. Herein, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roller coating, etc., but is not limited thereto.

[0080] 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.

[0081] As an 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.

[0082] 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 compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; etc., but are not limited thereto.

[0083] 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 the cathode material 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; etc., but are not limited thereto.

[0084] The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably such a compound: it has the ability to transport holes, so it has the effect of injecting holes in the anode and 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 the ability to form a thin film is also excellent. Preferably, the HOMO (highest occupied molecular orbital) of the 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 metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, conductive polymers based on polyaniline and based on polythiophene, etc., but are not limited thereto.

[0085] 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 layer is suitably a material having a large 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 organic materials based on arylamine, conductive polymers, block copolymers in which conjugated parts and non-conjugated parts exist simultaneously, etc., but are not limited thereto.

[0086] The electron blocking layer is formed on the hole transport layer, preferably arranged to be in contact with the light-emitting layer, and is used to adjust the hole mobility, prevent the excessive movement of electrons and increase the possibility of hole-electron combination, thereby improving the efficiency of the organic light-emitting device. The electron blocking layer contains an electron blocking material, and as such an electron blocking material, a material having a stable structure in which electrons may not flow to the outside of the light-emitting layer is suitable. Specific examples thereof may include organic materials based on arylamine, etc., but are not limited thereto.

[0087] The light-emitting material is preferably a material that can receive holes and electrons transmitted 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 azoles, benzothiazole-based and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorenes; rubrene; and the like, but are not limited thereto.

[0088] The light-emitting layer may include a host material and a dopant material. The host material may be a fused aromatic ring derivative, a heterocyclic compound, etc. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc. Examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0089] Examples of dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative is a substituted or unsubstituted fused aromatic ring derivative having an arylamino group, and examples thereof include pyrene, anthracene, Diindenopyrene, etc. Styrylamine compounds are compounds in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, wherein one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino are substituted or unsubstituted. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but are not limited thereto. In addition, metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0090] The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport material is suitably a material that can well receive electrons from the cathode and transfer the electrons to the light-emitting layer, and has a large electron mobility. Specific examples of electron transport materials include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the relevant technology. In particular, suitable examples of cathode materials are typical materials with low work function, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

[0091] 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 an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents the excitons generated by the light-emitting layer from moving to the hole injection layer, and is also excellent in the ability to form a thin film. Specific examples of the electron injection layer include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, etc., and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc., but not limited thereto.

[0092] Examples of metal complex compounds include 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but are not limited thereto.

[0093] The organic light emitting device according to the present disclosure may be a front-side emission type, a rear-side emission type, or a double-side emission type according to the materials used.

[0094] Furthermore, the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

[0095] The preparation of the compound represented by Chemical Formula 1 and an organic light-emitting device including the same will be described in detail in the following examples. However, these examples are presented only for illustrative purposes and are not intended to limit the scope of the present disclosure.

[0096] Synthesis Example 1: Synthesis of Intermediate Compound Sub-1

[0097]

[0098] 1-Bromo-4-fluoro-3-iodobenzene (50 g, 166.6 mmol) and (5-chloro-2-methoxyphenyl)boric acid (31.1 g, 166.6 mmol) were dissolved in 800 ml tetrahydrofuran (THF). 2 M sodium carbonate (Na2CO3) solution (250 mL) and tetrakis (triphenylphosphine) palladium (0) [Pd(PPh3)4] (3.8 g, 3 mol%) were added thereto and refluxed for 12 hours. After the reaction was completed, the reaction temperature was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. The toluene layer was separated, dried over magnesium sulfate and filtered. The filtrate was distilled under reduced pressure, and the resulting mixture was recrystallized three times using chloroform and ethanol to obtain compound R-1 (27.5 g, yield: 51%; MS: [M+H] + =314).

[0099]

[0100] Compound R-1 (25.0 g, 150 mmol) was dissolved in dichloromethane (300 ml) and then cooled to 0 ° C. Boron tribromide (7.9 ml, 83.2 mmol) was slowly added dropwise and then stirred for 12 hours. After the reaction was completed, the mixture was washed three times with water, dried over magnesium sulfate and filtered. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain compound R-2 (23.7 g, yield: 99%; MS: [M+H] + =300).

[0101]

[0102] Compound R-2 (20.0 g, 66.4 mmol) was dissolved in distilled dimethylformamide (DMF) (200 ml). It was cooled to 0 ° C, and sodium hydride (1.8 g, 72.9 mmol) was slowly added dropwise thereto. The mixture was stirred for 20 minutes and then stirred at 100 ° C for 1 hour. After the reaction was completed, the reaction temperature was cooled to room temperature, and 100 ml of ethanol was slowly added thereto. The mixture was distilled under reduced pressure and recrystallized from chloroform and ethyl acetate to obtain compound R-3 (15.2 g, yield: 81%; MS: [M+H] + =280).

[0103]

[0104] Under nitrogen atmosphere, R-3 (15g, 53.6mmol) and phenylboronic acid (6.5g, 53.6mmol) are added to 300ml tetrahydrofuran, and the mixture is stirred and refluxed. Then, potassium carbonate (22.2g, 160.8mmol) is dissolved in 22ml water, added thereto and fully stirred, then tetratriphenyl-phosphine palladium (1.9g, 1.6mmol) is added. After the reaction lasts for 2 hours, the reaction mixture is cooled to room temperature, and then the organic layer and the water layer are separated, and the organic layer is distilled. It is added to 298mL chloroform again, dissolved and washed with water twice. Then the organic layer is separated, anhydrous magnesium sulfate is added, stirred and then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare white solid compound R-4 (10.1g, 68%, MS:[M+H] + =279.1).

[0105]

[0106] R-4 (10 g, 36 mmol) and bis(pinacol)diboron (18.3 g, 71.9 mmol) were added to 200 ml of distilled water under nitrogen atmosphere. alkane, the mixture is stirred and refluxed. Then, potassium acetate (10.4g, 107.9mmol) is added thereto and fully stirred, then dibenzalacetone palladium (0.6g, 1.1mmol) and tricyclohexylphosphine (0.6g, 2.2mmol) are added. After the reaction lasts for 7 hours, the reaction mixture is cooled to room temperature, and the organic layer is then subjected to filtration treatment to remove salt, and the filtered organic layer is then distilled. It is added to 133mL chloroform again, dissolved and washed with water twice. The organic layer is then separated, anhydrous magnesium sulfate is added, stirred and then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethanol to prepare white solid compound R-5 (12g, 90%, MS: [M+H] +=371.2).

[0107]

[0108] R-5 (10 g, 27 mmol) and 2,4-dichloro-6-(dibenzo[b, d]furan-3-yl)-1,3,5-triazine (3.3 g, 27 mmol) were added to 200 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (11.2 g, 81 mmol) was then dissolved in 11 ml of water, added thereto and stirred thoroughly, and then tetrakistriphenylphosphine palladium (0.9 g, 0.8 mmol) was added. After the reaction lasted for 1 hour, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was then added to 283 mL of chloroform, dissolved and washed twice with water. The organic layer was then separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound Sub 1 (11 g, 78%, MS: [M+H] + =524.1).

[0109] Synthesis Example 2: Synthesis of Intermediate Compound Sub-2

[0110]

[0111] 1-Bromo-3-fluoro-4-iodobenzene (50 g, 166.6 mmol), (5-chloro-2-methoxyphenyl) boronic acid (31.1 g, 166.6 mmol) were dissolved in 800 ml tetrahydrofuran (THF). 2 M sodium carbonate (Na2CO3) solution (250 mL) and tetrakis (triphenylphosphine) palladium (0) [Pd(PPh3)4] (3.8 g, 3 mol%) were added thereto and refluxed for 12 hours. After the reaction was completed, the reaction temperature was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. The toluene layer was separated, dried over sodium sulfate and filtered. The filtrate was distilled under reduced pressure, and the resulting mixture was recrystallized three times using chloroform and ethanol to obtain compound M-1 (27.5 g, yield: 51%; MS: [M+H] + =314).

[0112]

[0113] Compound M-1 (25.0 g, 150 mmol) was dissolved in dichloromethane (300 ml) and then cooled to 0 ° C. Boron tribromide (7.9 ml, 83.2 mmol) was slowly added dropwise and then stirred for 12 hours. After the reaction was completed, the mixture was washed three times with water, dried over magnesium sulfate and filtered. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain compound M-2 (23.7 g, yield: 99%; MS: [M+H] + =300).

[0114]

[0115] Compound M-2 (20.0 g, 66.4 mmol) was dissolved in distilled dimethylformamide (DMF) (200 ml). It was cooled to 0 ° C, and sodium hydride (1.8 g, 72.9 mmol) was slowly added dropwise thereto. The mixture was stirred for 20 minutes and then stirred at 100 ° C for 1 hour. After the reaction was completed, the reaction temperature was cooled to room temperature, and 100 ml of ethanol was slowly added thereto. The mixture was distilled under reduced pressure and recrystallized from chloroform and ethyl acetate to obtain compound M-3 (15.2 g, yield: 81%; MS: [M+H] + =280).

[0116]

[0117] Under nitrogen atmosphere, M-3 (15g, 53.6mmol) and phenylboronic acid (6.5g, 53.6mmol) are added to 300ml tetrahydrofuran, and the mixture is stirred and refluxed. Then, potassium carbonate (22.2g, 160.8mmol) is dissolved in 22ml water, added thereto and fully stirred, then tetratriphenylphosphine palladium (1.9g, 1.6mmol) is added. After the reaction lasts for 2 hours, the reaction mixture is cooled to room temperature, then the organic layer and the water layer are separated, and the organic layer is distilled. It is added to 298mL chloroform again, dissolved and washed with water twice. Then the organic layer is separated, anhydrous magnesium sulfate is added, stirred and then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare white solid compound M-4 (10.5g, 71%, MS: [M+H] + =279.1).

[0118]

[0119] M-4 (10 g, 36 mmol) and bis(pinacol)diboron (18.3 g, 71.9 mmol) were added to 200 ml of distilled water under nitrogen atmosphere. alkane, the mixture is stirred and refluxed. Then, potassium acetate (10.4g, 107.9mmol) is added thereto and fully stirred, then dibenzalacetone palladium (0.6g, 1.1mmol) and tricyclohexylphosphine (0.6g, 2.2mmol) are added. After the reaction lasts for 7 hours, the reaction mixture is cooled to room temperature, and the organic layer is then subjected to filtration treatment to remove salt, and the filtered organic layer is then distilled. It is added to 133mL chloroform again, dissolved and washed with water twice. The organic layer is then separated, anhydrous magnesium sulfate is added, stirred and then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethanol to prepare white solid compound M-5 (11.7g, 88%, MS: [M+H] + =371.2).

[0120]

[0121] M-5 (10 g, 27 mmol) and 2,4-dichloro-6-(dibenzo[b, d]furan-3-yl)-1,3,5-triazine (3.3 g, 27 mmol) were added to 200 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (11.2 g, 81 mmol) was then dissolved in 11 ml of water, added thereto and stirred thoroughly, and then tetrakistriphenylphosphine palladium (0.9 g, 0.8 mmol) was added. After the reaction lasted for 1 hour, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was then added to 283 mL of chloroform, dissolved and washed twice with water. The organic layer was then separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound Sub 2 (11.3 g, 80%, MS: [M+H] + =524.1).

[0122] Synthesis Example 3: Synthesis of Intermediate Compound Sub 3

[0123]

[0124] Intermediate 5-1a (40.4 g, yield 75%, MS: [M+H] + =239), except that (4-chloro-2-fluorophenyl)boronic acid was used instead of (3-chloro-2-fluorophenyl)boronic acid.

[0125]

[0126] Intermediate T2 (26.8 g, yield 72%, MS: [M+H] + =219), except that intermediate T1 is used instead of intermediate P1.

[0127]

[0128] Intermediate T3 (50.1 g, yield: 81%, MS: [M+H] + =500), except that intermediate T2 was used instead of intermediate P2.

[0129]

[0130] Under nitrogen atmosphere, T3 (30g, 60mmol) and phenylboronic acid (7.3g, 60mmol) are added in 600ml tetrahydrofuran, and the mixture is stirred and refluxed. Then, potassium acetate (24.9g, 180mmol) is added in 25ml water and fully stirred, and then tetrakis triphenylphosphine palladium (2.1g, 1.8mmol) is added. After the reaction lasts for 1 hour, the reaction mixture is cooled to room temperature, and then the organic layer and the water layer are separated, and the organic layer is distilled. It is added to 334mL chloroform again, dissolved and washed with water twice. Then the organic layer is separated, anhydrous magnesium sulfate is added, stirred and then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare white solid compound T4 (12.8g, 77%, MS: [M+H] + =279.1).

[0131]

[0132] T4 (10 g, 36 mmol) and bis(pinacol)diboron (18.3 g, 71.9 mmol) were added to 200 ml of distilled water under nitrogen atmosphere. alkane, then the mixture is stirred and refluxed. Then, potassium acetate (10.4g, 107.9mmol) is added thereto and fully stirred, then dibenzalacetone palladium (0.6g, 1.1mmol) and tricyclohexylphosphine (0.6g, 2.2mmol) are added. After the reaction lasts for 6 hours, the reaction mixture is cooled to room temperature, and the organic layer is then subjected to filtration treatment to remove salt, and the filtered organic layer is then distilled. It is added to 133mL chloroform again, dissolved and washed with water twice. The organic layer is then separated, anhydrous magnesium sulfate is added, stirred and then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethanol to prepare white solid compound T5 (11g, 83%, MS: [M+H]+ =371.2).

[0133]

[0134] T5 (15 g, 40.5 mmol) and 2,4-dichloro-6-(dibenzo[b, d]furan-3-yl)-1,3,5-triazine (12.8 g, 40.5 mmol) were added to 300 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.8 g, 121.6 mmol) was then dissolved in 17 ml of water, added thereto and stirred thoroughly, and then tetrakistriphenylphosphine palladium (1.4 g, 1.2 mmol) was added. After the reaction lasted for 2 hours, the reaction mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was then added to 424 mL of chloroform, dissolved and washed twice with water. The organic layer was then separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound Sub 3 (15.7 g, 74%, MS: [M+H] + =524.1).

[0135] Synthesis Example 4: Synthesis of Intermediate Compound Sub 4

[0136]

[0137] After 3-bromobenzene-1,2-diol (50 g, 0.26 mol) and (4-chloro-2-fluorophenyl)boric acid (46.1 g, 0.21 mol) were dissolved in tetrahydrofuran (500 mL) in a 2000 mL round-bottom flask under a nitrogen atmosphere, a 1.5 M potassium carbonate aqueous solution (400 mL) was added and bis(tri-tert-butylphosphine)palladium(0) (1.35 g, 2.36 mmol) was added. The mixture was heated and stirred for 1 hour. The temperature was lowered to room temperature, the aqueous layer was separated and removed, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure, recrystallized with hexane, and then dried to prepare compound P-1 (49.8 g, yield: 79%, MS: [M+H] + =239).

[0138]

[0139] In a 500 mL round-bottom flask, intermediate P-1 (49.8 g, 0.21 mol) and potassium carbonate (57.7 g, 0.42 mol) were dissolved in N-methyl-2-pyrrolidone (200 mL), and the mixture was heated and stirred for 2 hours. The temperature was lowered to room temperature, reverse precipitation was performed in water, and filtered. The product was completely dissolved in dichloromethane, then washed with water, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure, recrystallized with ethanol, and dried to prepare compound P-2 (31.8 g, yield: 70%, MS: [M+H] + =219).

[0140]

[0141] Compound P-2 (31.8 g, 0.15 mol) was dissolved in acetonitrile (150 mL) in a 500 mL round-bottom flask, and potassium carbonate (33.1 g, 0.24 mol) was dissolved in water (150 mL), added thereto, and then nonafluorobutanesulfonyl fluoride (28.7 mL, 0.16 mol) was slowly added dropwise at 0° C. over 30 minutes. Then, the mixture was stirred at room temperature for 3 hours. After the reaction was completed, the reaction mixture was filtered, completely dissolved in dichloromethane, then washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized with ethanol, and then dried to prepare compound P-3 (53.3 g, yield: 73%, MS: [M+H] + =501).

[0142]

[0143] Under nitrogen atmosphere, P-3 (30g, 60mmol) and phenylboronic acid (7.3g, 60mmol) are added in 600ml tetrahydrofuran, and the mixture is stirred and refluxed. Then, potassium acetate (24.9g, 180mmol) is added thereto and fully stirred, then tetrakis triphenylphosphine palladium (2.1g, 1.8mmol) is added. After the reaction lasts for 2 hours, the reaction mixture is cooled to room temperature, then the organic layer and the water layer are separated, and the organic layer is distilled. It is added to 334mL chloroform again, dissolved and washed with water twice. Then the organic layer is separated, anhydrous magnesium sulfate is added, stirred and then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare white solid compound P4 (10.7g, 64%, MS:[M+H] + =279.1).

[0144]

[0145] P4 (10 g, 36 mmol) and bis(pinacol)diboron (18.3 g, 71.9 mmol) were added to 200 ml of distilled water under nitrogen atmosphere. alkane, the mixture is stirred and refluxed. Then, potassium acetate (10.4g, 107.9mmol) is added thereto and fully stirred, then dibenzalacetone palladium (0.6g, 1.1mmol) and tricyclohexylphosphine (0.6g, 2.2mmol) are added. After the reaction lasts for 5 hours, the reaction mixture is cooled to room temperature, and the organic layer is then subjected to filtration treatment to remove salt, and the filtered organic layer is then distilled. It is added to 133mL chloroform again, dissolved and washed with water twice. The organic layer is then separated, anhydrous magnesium sulfate is added, stirred and then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethanol to prepare white solid compound P5 (8.5g, 64%, MS: [M+H] + =371.2).

[0146]

[0147] P5 (15 g, 40.5 mmol) and 2,4-dichloro-6-(dibenzo[b, d]furan-3-yl)-1,3,5-triazine (12.8 g, 40.5 mmol) were added to 300 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium acetate (16.8 g, 121.6 mmol) was then dissolved in 17 ml of water, added thereto and stirred thoroughly, and then tetrakistriphenylphosphine palladium (1.4 g, 1.2 mmol) was added. After the reaction lasted for 1 hour, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was then added to 424 mL of chloroform, dissolved and washed twice with water. The organic layer was then separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound Sub 4 (15.3 g, 72%, MS: [M+H] + =524.1).

[0148] Preparation Example 1: Preparation of Compound 1

[0149]

[0150] Sub 1 (10g, 19.1mmol) and (4-(triphenylsilyl)phenyl)boric acid (7.3g, 19.1mmol) were added to 200ml tetrahydrofuran under nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (7.9g, 57.3mmol) was dissolved in 8ml water, added thereto and stirred thoroughly, and then tetrakis triphenylphosphine palladium (0.7g, 0.6mmol) was added. After the reaction lasted for 1 hour, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was added to 315mL chloroform again, dissolved and washed twice with water. Then the organic layer was separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare white solid compound 1 (9.9g, 63%, MS: [M+H] + =824.3).

[0151] Preparation Example 2: Preparation of Compound 2

[0152]

[0153] Sub 1 (10 g, 19.1 mmol) and (3-(dibenzo[b, d]thiophene-4-yl)phenyl)boric acid (5.8 g, 19.1 mmol) were added to 200 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (7.9 g, 57.3 mmol) was then dissolved in 8 ml of water, added thereto and stirred thoroughly, and then tetrakistriphenylphosphine palladium (0.7 g, 0.6 mmol) was added. After the reaction continued for 2 hours, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was then added to 286 mL of chloroform, dissolved and washed twice with water. The organic layer was then separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare yellow solid compound 2 (10 g, 70%, MS: [M+H] + =748.2).

[0154] Preparation Example 3: Preparation of Compound 3

[0155]

[0156] Sub 1 (10 g, 19.1 mmol) and (3-(dibenzo[b, d]furan-4-yl)phenyl)boric acid (5.5 g, 19.1 mmol) were added to 200 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (7.9 g, 57.3 mmol) was then dissolved in 8 ml of water, added thereto and stirred thoroughly, and then tetrakistriphenylphosphine palladium (0.7 g, 0.6 mmol) was added. After the reaction lasted for 1 hour, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was then added to 280 mL of chloroform, dissolved and washed twice with water. The organic layer was then separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare yellow solid compound 3 (9.5 g, 68%, MS: [M+H] + =732.2).

[0157] Preparation Example 4: Preparation of Compound 4

[0158]

[0159] Sub 1 (10 g, 19.1 mmol) and (2-(9H-carbazole-9-yl)phenyl)boric acid (5.5 g, 19.1 mmol) were added to 200 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (7.9 g, 57.3 mmol) was then dissolved in 8 ml of water, added thereto and stirred thoroughly, and then tetrakistriphenylphosphine palladium (0.7 g, 0.6 mmol) was added. After the reaction continued for 1 hour, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was then added to 279 mL of chloroform, dissolved and washed twice with water. The organic layer was then separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare white solid compound 4 (10.2 g, 73%, MS: [M+H] + =731.2).

[0160] Preparation Example 5: Preparation of Compound 5

[0161]

[0162] Sub 1 (10 g, 19.1 mmol) and (3-(9H-carbazole-9-yl)phenyl)boric acid (5.5 g, 19.1 mmol) were added to 200 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (7.9 g, 57.3 mmol) was then dissolved in 8 ml of water, added thereto and stirred thoroughly, and then tetrakistriphenylphosphine palladium (0.7 g, 0.6 mmol) was added. After the reaction continued for 1 hour, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was then added to 279 mL of chloroform, dissolved and washed twice with water. The organic layer was then separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare white solid compound 5 (11.3 g, 81%, MS: [M+H] + =731.2).

[0163] Preparation Example 6: Preparation of Compound 6

[0164]

[0165] Sub 2 (10 g, 19.1 mmol) and (3-(dibenzo[b, d]furan-4-yl)phenyl)boric acid (5.5 g, 19.1 mmol) were added to 200 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (7.9 g, 57.3 mmol) was then dissolved in 8 ml of water, added thereto and stirred thoroughly, and then tetrakistriphenylphosphine palladium (0.7 g, 0.6 mmol) was added. After the reaction lasted for 1 hour, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was then added to 280 mL of chloroform, dissolved and washed twice with water. The organic layer was then separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare yellow solid compound 6 (9.8 g, 70%, MS: [M+H] + =732.2).

[0166] Preparation Example 7: Preparation of Compound 7

[0167]

[0168] Sub 3 (10 g, 19.1 mmol) and (3-(dibenzo[b, d]furan-4-yl)phenyl)boric acid (5.5 g, 19.1 mmol) were added to 200 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (7.9 g, 57.3 mmol) was then dissolved in 8 ml of water, added thereto and stirred thoroughly, and then tetrakistriphenylphosphine palladium (0.7 g, 0.6 mmol) was added. After the reaction lasted for 1 hour, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was then added to 280 mL of chloroform, dissolved and washed twice with water. The organic layer was then separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare yellow solid compound 7 (9.8 g, 70%, MS: [M+H] + =732.2).

[0169] Preparation Example 8: Preparation of Compound 8

[0170]

[0171] Sub 4 (10 g, 19.1 mmol) and (3-(dibenzo[b, d]furan-4-yl)phenyl)boric acid (5.5 g, 19.1 mmol) were added to 200 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (7.9 g, 57.3 mmol) was then dissolved in 8 ml of water, added thereto and stirred thoroughly, and then tetrakistriphenylphosphine palladium (0.7 g, 0.6 mmol) was added. After the reaction lasted for 1 hour, the reaction mixture was cooled to room temperature, and then the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was then added to 280 mL of chloroform, dissolved and washed twice with water. The organic layer was then separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare yellow solid compound 8 (7.1 g, 51%, MS: [M+H] + =732.2).

[0172] [Experimental example]

[0173] <Example 1>

[0174] It is coated with a thickness of The ITO (indium tin oxide) of the glass substrate as film is put into the distilled water dissolved with detergent therein, and carry out ultrasonic cleaning.At this moment, use the product manufactured by Fischer Co. as detergent, and use the distilled water that utilizes the filter manufactured by Millipore Co. to filter twice as distilled water.After ITO is cleaned for 30 minutes, use distilled water to repeat twice ultrasonic cleaning for 10 minutes.After finishing with distilled water cleaning, substrate isopropyl alcohol, acetone and methanol solvent ultrasonic cleaning, dry, then transfer to plasma cleaner.In addition, substrate is cleaned for 5 minutes using oxygen plasma, then transfer to vacuum deposition device.

[0175] On the transparent ITO electrode thus prepared, the following HI-1 was thermally vacuum deposited to The following compound HT-1 was thermally vacuum deposited onto the hole injection layer. The hole transport layer was formed by vacuum depositing the following compound HT-2 on the layer deposited with HT-1. The compound 1 prepared in the previous preparation example 1, the following compound YGH-1 and the phosphorescent dopant YGD-1 were co-deposited at a weight ratio of 44:44:12 on the layer deposited with HT-2 to form an electron blocking layer. The following compound ET-1 was vacuum deposited on the luminescent layer. To form an electron transport layer, the following compound ET-2 and Li were vacuum deposited at a weight ratio of 98:2 on the electron transport layer to form a Aluminum is deposited on the electron injection layer to a thickness of to form a cathode.

[0176]

[0177] During the above process, the vapor deposition rate of the organic material is maintained at to The aluminum deposition rate was kept at The vacuum level during deposition was maintained at 1 × 10 -7 Up to 5×10 -8 Entrust.

[0178] <Experimental Examples 2 to 8>

[0179] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compounds shown in Table 1 below were used instead of Compound 1 of Preparation Example 1 in Experimental Example 1.

[0180] <Comparative Experimental Examples 1 to 3>

[0181] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that compounds shown in the following Table 1 were used instead of Compound 1 of Preparation Example 1 in Experimental Example 1. Compounds CE1 to CE3 shown in Table 1 are as follows.

[0182]

[0183] For the organic light-emitting devices manufactured in the experimental examples and the comparative experimental examples, the 2 The voltage and efficiency were measured at a current density of 50 mA / cm 2 The life span was measured at a current density of . The results are shown in Table 1 below. In this case, LT 95 It means the time required for the brightness to drop to 95% of the initial brightness.

[0184] [Table 1]

[0185]

[0186] As shown in Table 1, it was confirmed that when the compound of the present disclosure was used as an organic light emitting layer material, it exhibited excellent characteristics in terms of efficiency and lifespan compared with the comparative experimental example.

[0187] This is believed to be because the triazine group is substituted with a dibenzofuran substituent, thereby increasing electronic stability. In addition, when the dibenzofuran group is further substituted with an aryl substituent, it has an asymmetric structure and also increases efficiency and life due to the effect of suppressing crystallinity in the thin film when the device is installed.

[0188] [Explanation of Reference Numerals]

[0189] 1: Substrate 2: Anode

[0190] 3: Light-emitting layer 4: Cathode

[0191] 5: Hole injection layer 6: Hole transport layer

[0192] 7: Electron blocking layer 8: Electron transport layer

[0193] 9: Electron injection layer

Claims

1. A compound represented by the following chemical formula 1-1: [Chemical formula 1-1] In Chemical Formula 1-1, Each X is independently N or CH, provided that at least one of X is N, n and m are each independently an integer from 0 to 3, provided that the sum of n and m is 1 or greater, R1 and R2 are each independently substituted or unsubstituted C 6-10 Aryl, L is substituted or unsubstituted C 6-20 arylene, and Ar is any one selected from the following: in, When the above substituents are substituted, each substituent is substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; an amino group; and a phosphine oxide group.

2. The compound according to claim 1, wherein the sum of n and m is 1 or 2.

3. The compound according to claim 1, wherein R1 and R2 are phenyl. The compound according to claim 1 , wherein all X are N. The compound according to claim 1 , wherein L is phenylene.

6. The compound according to claim 1, wherein the compound represented by Chemical Formula 1-1 is selected from the following:

7. 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 one or more of the organic material layers comprises the compound according to any one of claims 1 to 6.

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